# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_address ;Department of Solid State Chemistry Novosibirsk State University Novosibirsk Russia 630090 ; _publ_contact_author_address ;Department of Solid State Chemistry Novosibirsk State University Novosibirsk Russia 630090 ; _publ_contact_author_email vasilyminkov@yahoo.com _publ_contact_author_fax '7 (383) 3634132' _publ_contact_author_phone '7 (383) 3634272' _publ_contact_author_name 'Dr Vasily S. Minkov' _publ_author_name 'Dr Vasily S. Minkov' data_DL-cys_ox_11_295K _database_code_depnum_ccdc_archive 'CCDC 868537' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium semioxalate' _chemical_formula_moiety 'C3 H8 N O2 S, C2 H O4' _chemical_formula_sum 'C5 H9 N O6 S' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 295(2) _chemical_formula_weight 211.20 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.66513(16) _cell_length_b 9.0127(4) _cell_length_c 9.7723(5) _cell_angle_alpha 109.318(4) _cell_angle_beta 102.263(3) _cell_angle_gamma 100.163(3) _cell_volume 443.35(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.365 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8529 _exptl_absorpt_correction_T_max 0.9679 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 13791 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2696 _reflns_number_gt 2368 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0494P)^2^+0.1035P] 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 2696 _refine_ls_number_parameters 124 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.069 _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 S1 S 0.86159(7) 0.39769(4) 0.24088(5) 0.04623(12) Uani 1 1 d D . . H1S H 0.764(4) 0.403(2) 0.1295(18) 0.055 Uiso 1 1 d D . . C1 C 0.5929(2) 0.38243(16) 0.31230(14) 0.0339(2) Uani 1 1 d . . . H12 H 0.6506 0.4061 0.4200 0.041 Uiso 1 1 calc R . . H11 H 0.5104 0.4646 0.2997 0.041 Uiso 1 1 calc R . . N1 N 0.51727(19) 0.08567(13) 0.25512(11) 0.0289(2) Uani 1 1 d . . . H2N H 0.3976 -0.0068 0.2240 0.035 Uiso 1 1 calc R . . H1N H 0.5976 0.1150 0.3527 0.035 Uiso 1 1 calc R . . H3N H 0.6252 0.0707 0.2009 0.035 Uiso 1 1 calc R . . C2 C 0.4027(2) 0.21610(14) 0.23464(12) 0.0268(2) Uani 1 1 d . . . H2 H 0.2679 0.2190 0.2831 0.032 Uiso 1 1 calc R . . O2 O 0.24647(17) 0.03158(12) -0.02463(10) 0.0361(2) Uani 1 1 d . . . O1 O 0.22714(19) 0.29040(12) 0.03559(11) 0.0405(2) Uani 1 1 d . . . H1O H 0.1447 0.2574 -0.0536 0.049 Uiso 1 1 calc R . . O3 O 0.64848(14) 0.19246(12) 0.57177(9) 0.0341(2) Uani 1 1 d . . . C3 C 0.28457(19) 0.16841(15) 0.06620(12) 0.0273(2) Uani 1 1 d . . . O5 O 1.28290(15) 0.21308(13) 0.69426(10) 0.0339(2) Uani 1 1 d . . . H5O H 1.3953 0.2077 0.6535 0.041 Uiso 1 1 calc R . . C4 C 0.84740(18) 0.19623(13) 0.65941(12) 0.0241(2) Uani 1 1 d . . . O4 O 0.87183(15) 0.19395(12) 0.78787(10) 0.0349(2) Uani 1 1 d . . . C5 C 1.07495(19) 0.19783(13) 0.59562(12) 0.0247(2) Uani 1 1 d . . . O6 O 1.05205(17) 0.18222(15) 0.46610(10) 0.0424(2) 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 S1 0.03346(18) 0.03765(19) 0.0642(3) 0.01711(17) 0.01629(16) 0.00341(13) C1 0.0346(6) 0.0331(6) 0.0279(5) 0.0062(4) 0.0059(5) 0.0090(5) N1 0.0284(4) 0.0351(5) 0.0239(4) 0.0143(4) 0.0058(3) 0.0065(4) C2 0.0231(5) 0.0363(6) 0.0218(5) 0.0117(4) 0.0067(4) 0.0086(4) O2 0.0326(4) 0.0434(5) 0.0268(4) 0.0084(4) 0.0055(3) 0.0107(4) O1 0.0441(5) 0.0440(5) 0.0302(4) 0.0171(4) -0.0006(4) 0.0124(4) O3 0.0183(4) 0.0594(6) 0.0275(4) 0.0199(4) 0.0060(3) 0.0116(4) C3 0.0189(4) 0.0403(6) 0.0235(5) 0.0137(4) 0.0064(4) 0.0070(4) O5 0.0193(4) 0.0561(6) 0.0333(4) 0.0230(4) 0.0094(3) 0.0138(4) C4 0.0182(4) 0.0314(5) 0.0235(5) 0.0122(4) 0.0061(4) 0.0050(4) O4 0.0237(4) 0.0587(6) 0.0284(4) 0.0246(4) 0.0085(3) 0.0094(4) C5 0.0195(4) 0.0308(5) 0.0258(5) 0.0128(4) 0.0071(4) 0.0068(4) O6 0.0288(4) 0.0754(7) 0.0286(4) 0.0239(5) 0.0118(3) 0.0156(4) _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 S1 C1 1.8064(14) . ? S1 H1S 1.133(14) . ? C1 C2 1.5214(17) . ? C1 H12 0.9700 . ? C1 H11 0.9700 . ? N1 C2 1.4875(15) . ? N1 H2N 0.8900 . ? N1 H1N 0.8900 . ? N1 H3N 0.8900 . ? C2 C3 1.5180(15) . ? C2 H2 0.9800 . ? O2 C3 1.2065(16) . ? O1 C3 1.3063(15) . ? O1 H1O 0.8200 . ? O3 C4 1.2497(12) . ? O5 C5 1.3071(12) . ? O5 H5O 0.8200 . ? C4 O4 1.2409(13) . ? C4 C5 1.5464(14) . ? C5 O6 1.2019(14) . ? 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 S1 H1S 97.2(10) . . ? C2 C1 S1 113.91(8) . . ? C2 C1 H12 108.8 . . ? S1 C1 H12 108.8 . . ? C2 C1 H11 108.8 . . ? S1 C1 H11 108.8 . . ? H12 C1 H11 107.7 . . ? C2 N1 H2N 109.5 . . ? C2 N1 H1N 109.5 . . ? H2N N1 H1N 109.5 . . ? C2 N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? N1 C2 C3 108.18(9) . . ? N1 C2 C1 111.07(9) . . ? C3 C2 C1 114.21(10) . . ? N1 C2 H2 107.7 . . ? C3 C2 H2 107.7 . . ? C1 C2 H2 107.7 . . ? C3 O1 H1O 109.5 . . ? O2 C3 O1 125.86(11) . . ? O2 C3 C2 122.13(11) . . ? O1 C3 C2 111.99(10) . . ? C5 O5 H5O 109.5 . . ? O4 C4 O3 125.47(10) . . ? O4 C4 C5 119.18(9) . . ? O3 C4 C5 115.31(9) . . ? O6 C5 O5 125.58(10) . . ? O6 C5 C4 121.04(9) . . ? O5 C5 C4 113.36(9) . . ? 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 S1 C1 C2 N1 60.50(11) . . . . ? S1 C1 C2 C3 -62.17(12) . . . . ? N1 C2 C3 O2 15.09(14) . . . . ? C1 C2 C3 O2 139.33(12) . . . . ? N1 C2 C3 O1 -166.39(9) . . . . ? C1 C2 C3 O1 -42.15(13) . . . . ? O4 C4 C5 O6 171.85(12) . . . . ? O3 C4 C5 O6 -6.09(17) . . . . ? O4 C4 C5 O5 -6.49(16) . . . . ? O3 C4 C5 O5 175.57(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.89 1.96 2.8024(13) 157.9 1 N1 H1N O6 0.89 2.45 3.0685(13) 126.6 1 N1 H2N O4 0.89 2.02 2.8865(14) 164.7 2_656 N1 H3N O2 0.89 2.02 2.8612(14) 158.1 2_655 O1 H1O O5 0.82 2.67 3.2709(13) 131.5 1_454 O1 H1O O4 0.82 1.79 2.5667(12) 157.6 1_454 O5 H5O O3 0.82 1.79 2.6074(11) 177.0 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.398 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.045 # END data_DL-cys_ox_11_275K _database_code_depnum_ccdc_archive 'CCDC 868538' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium semioxalate' _chemical_formula_moiety 'C3 H8 N O2 S, C2 H O4' _chemical_formula_sum 'C5 H9 N O6 S' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 275(2) _chemical_formula_weight 211.20 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.66521(18) _cell_length_b 8.9987(4) _cell_length_c 9.7696(5) _cell_angle_alpha 109.516(4) _cell_angle_beta 102.251(3) _cell_angle_gamma 100.096(3) _cell_volume 442.06(4) _cell_formula_units_Z 2 _cell_measurement_temperature 275(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.366 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8525 _exptl_absorpt_correction_T_max 0.9678 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 14650 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2686 _reflns_number_gt 2373 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0558P)^2^+0.0767P] 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 2686 _refine_ls_number_parameters 124 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.065 _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 S1 S 0.86288(6) 0.39752(4) 0.24215(5) 0.04275(12) Uani 1 1 d D . . H1S H 0.768(4) 0.406(2) 0.1297(18) 0.051 Uiso 1 1 d D . . N1 N 0.51749(18) 0.08508(13) 0.25535(11) 0.0270(2) Uani 1 1 d . . . H2N H 0.3975 -0.0073 0.2247 0.032 Uiso 1 1 calc R . . H1N H 0.5990 0.1147 0.3528 0.032 Uiso 1 1 calc R . . H3N H 0.6242 0.0694 0.2003 0.032 Uiso 1 1 calc R . . C1 C 0.5943(2) 0.38282(16) 0.31391(14) 0.0318(2) Uani 1 1 d . . . H12 H 0.6520 0.4065 0.4217 0.038 Uiso 1 1 calc R . . H11 H 0.5122 0.4655 0.3017 0.038 Uiso 1 1 calc R . . C2 C 0.4033(2) 0.21619(15) 0.23566(12) 0.0254(2) Uani 1 1 d . . . H2 H 0.2687 0.2193 0.2843 0.031 Uiso 1 1 calc R . . O2 O 0.24627(17) 0.03144(12) -0.02447(10) 0.0339(2) Uani 1 1 d . . . O1 O 0.22857(19) 0.29140(12) 0.03678(10) 0.0379(2) Uani 1 1 d . . . H1O H 0.1439 0.2583 -0.0520 0.045 Uiso 1 1 calc R . . O3 O 0.64829(14) 0.19225(12) 0.57234(9) 0.0319(2) Uani 1 1 d . . . C3 C 0.28486(19) 0.16867(15) 0.06685(12) 0.0257(2) Uani 1 1 d . . . O5 O 1.28386(15) 0.21400(12) 0.69548(10) 0.0317(2) Uani 1 1 d . . . H5O H 1.3968 0.2098 0.6550 0.038 Uiso 1 1 calc R . . C4 C 0.84772(19) 0.19673(13) 0.66037(12) 0.0228(2) Uani 1 1 d . . . O4 O 0.87253(15) 0.19521(12) 0.78930(10) 0.0326(2) Uani 1 1 d . . . C5 C 1.07532(19) 0.19793(14) 0.59634(12) 0.0235(2) Uani 1 1 d . . . O6 O 1.05197(17) 0.18113(14) 0.46645(10) 0.0394(2) 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 S1 0.03113(18) 0.03493(19) 0.0593(2) 0.01616(16) 0.01520(15) 0.00334(13) N1 0.0270(4) 0.0322(5) 0.0227(4) 0.0132(4) 0.0058(3) 0.0062(4) C1 0.0324(6) 0.0315(6) 0.0262(5) 0.0063(4) 0.0058(4) 0.0086(5) C2 0.0226(5) 0.0344(6) 0.0207(5) 0.0115(4) 0.0074(4) 0.0082(4) O2 0.0309(4) 0.0404(5) 0.0255(4) 0.0079(4) 0.0057(3) 0.0100(4) O1 0.0412(5) 0.0412(5) 0.0285(4) 0.0165(4) -0.0003(4) 0.0113(4) O3 0.0175(4) 0.0548(6) 0.0255(4) 0.0178(4) 0.0056(3) 0.0109(3) C3 0.0178(4) 0.0371(6) 0.0232(5) 0.0130(4) 0.0062(4) 0.0066(4) O5 0.0180(3) 0.0522(5) 0.0311(4) 0.0213(4) 0.0087(3) 0.0125(3) C4 0.0173(4) 0.0284(5) 0.0229(5) 0.0111(4) 0.0058(3) 0.0047(4) O4 0.0222(4) 0.0545(6) 0.0267(4) 0.0226(4) 0.0082(3) 0.0085(4) C5 0.0185(4) 0.0289(5) 0.0252(5) 0.0127(4) 0.0072(4) 0.0063(4) O6 0.0274(4) 0.0689(7) 0.0269(4) 0.0221(4) 0.0111(3) 0.0142(4) _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 S1 C1 1.8079(14) . ? S1 H1S 1.150(14) . ? N1 C2 1.4880(15) . ? N1 H2N 0.8900 . ? N1 H1N 0.8900 . ? N1 H3N 0.8900 . ? C1 C2 1.5223(17) . ? C1 H12 0.9700 . ? C1 H11 0.9700 . ? C2 C3 1.5203(15) . ? C2 H2 0.9800 . ? O2 C3 1.2063(15) . ? O1 C3 1.3070(15) . ? O1 H1O 0.8200 . ? O3 C4 1.2515(12) . ? O5 C5 1.3098(12) . ? O5 H5O 0.8200 . ? C4 O4 1.2425(13) . ? C4 C5 1.5478(14) . ? C5 O6 1.2018(14) . ? 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 S1 H1S 98.3(10) . . ? C2 N1 H2N 109.5 . . ? C2 N1 H1N 109.5 . . ? H2N N1 H1N 109.5 . . ? C2 N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? C2 C1 S1 113.90(8) . . ? C2 C1 H12 108.8 . . ? S1 C1 H12 108.8 . . ? C2 C1 H11 108.8 . . ? S1 C1 H11 108.8 . . ? H12 C1 H11 107.7 . . ? N1 C2 C3 108.18(9) . . ? N1 C2 C1 111.02(9) . . ? C3 C2 C1 114.17(10) . . ? N1 C2 H2 107.7 . . ? C3 C2 H2 107.7 . . ? C1 C2 H2 107.7 . . ? C3 O1 H1O 109.5 . . ? O2 C3 O1 125.91(10) . . ? O2 C3 C2 122.05(11) . . ? O1 C3 C2 112.03(10) . . ? C5 O5 H5O 109.5 . . ? O4 C4 O3 125.48(10) . . ? O4 C4 C5 119.17(9) . . ? O3 C4 C5 115.31(9) . . ? O6 C5 O6 0.0 1 . ? O6 C5 O5 125.63(10) . . ? O6 C5 C4 121.02(9) . . ? O5 C5 C4 113.32(9) . . ? 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 S1 C1 C2 N1 60.42(11) . . . . ? S1 C1 C2 C3 -62.19(12) . . . . ? N1 C2 C3 O2 15.17(15) . . . . ? C1 C2 C3 O2 139.32(12) . . . . ? N1 C2 C3 O1 -166.14(9) . . . . ? C1 C2 C3 O1 -42.00(13) . . . . ? O4 C4 C5 O6 171.67(12) . . . . ? O3 C4 C5 O6 -6.20(17) . . . . ? O4 C4 C5 O5 -6.57(15) . . . . ? O3 C4 C5 O5 175.57(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.89 1.96 2.8017(13) 157.2 1 N1 H1N O6 0.89 2.45 3.0676(13) 127.2 1 N1 H2N O4 0.89 2.02 2.8872(14) 165.5 2_656 N1 H3N O2 0.89 2.01 2.8586(13) 159.0 2_655 O1 H1O O5 0.82 2.67 3.2664(13) 130.4 1_454 O1 H1O O4 0.82 1.78 2.5658(12) 158.8 1_454 O5 H5O O3 0.82 1.79 2.6051(11) 176.4 1_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.395 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.050 # END data_DL-cys_ox_11_250K _database_code_depnum_ccdc_archive 'CCDC 868539' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium semioxalate' _chemical_formula_moiety 'C3 H8 N O2 S, C2 H O4' _chemical_formula_sum 'C5 H9 N O6 S' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 250(2) _chemical_formula_weight 211.20 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.66264(17) _cell_length_b 8.9788(4) _cell_length_c 9.7642(4) _cell_angle_alpha 109.682(4) _cell_angle_beta 102.236(3) _cell_angle_gamma 100.002(3) _cell_volume 440.33(3) _cell_formula_units_Z 2 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8520 _exptl_absorpt_correction_T_max 0.9677 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 14540 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2679 _reflns_number_gt 2368 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0479P)^2^+0.1081P] 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 2679 _refine_ls_number_parameters 124 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 S1 S 0.86435(6) 0.39741(4) 0.24338(4) 0.03833(11) Uani 1 1 d D . . H1S H 0.766(3) 0.407(2) 0.1301(17) 0.046 Uiso 1 1 d D . . N1 N 0.51774(18) 0.08457(12) 0.25590(11) 0.02487(19) Uani 1 1 d . . . H2N H 0.3963 -0.0093 0.2235 0.030 Uiso 1 1 calc R . . H1N H 0.5984 0.1139 0.3548 0.030 Uiso 1 1 calc R . . H3N H 0.6272 0.0693 0.2011 0.030 Uiso 1 1 calc R . . C1 C 0.5954(2) 0.38329(15) 0.31528(13) 0.0290(2) Uani 1 1 d . . . H12 H 0.6537 0.4072 0.4243 0.035 Uiso 1 1 calc R . . H11 H 0.5128 0.4673 0.3032 0.035 Uiso 1 1 calc R . . C2 C 0.40413(19) 0.21643(14) 0.23662(11) 0.0231(2) Uani 1 1 d . . . H2 H 0.2682 0.2199 0.2859 0.028 Uiso 1 1 calc R . . O2 O 0.24621(16) 0.03121(11) -0.02425(9) 0.03064(19) Uani 1 1 d . . . O1 O 0.22994(18) 0.29261(11) 0.03820(10) 0.0344(2) Uani 1 1 d . . . H1O H 0.1466 0.2594 -0.0523 0.041 Uiso 1 1 calc R . . O3 O 0.64857(14) 0.19209(12) 0.57303(9) 0.02898(19) Uani 1 1 d . . . C3 C 0.28576(19) 0.16924(14) 0.06791(12) 0.0234(2) Uani 1 1 d . . . O5 O 1.28454(14) 0.21469(12) 0.69661(9) 0.02871(19) Uani 1 1 d . . . H5O H 1.3979 0.2078 0.6550 0.034 Uiso 1 1 calc R . . C4 C 0.84805(18) 0.19702(13) 0.66131(11) 0.02095(19) Uani 1 1 d . . . O4 O 0.87333(15) 0.19656(12) 0.79078(9) 0.02976(19) Uani 1 1 d . . . C5 C 1.07556(19) 0.19796(13) 0.59725(12) 0.0215(2) Uani 1 1 d . . . O6 O 1.05216(17) 0.18024(13) 0.46668(10) 0.0355(2) 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 S1 0.02779(16) 0.03170(17) 0.0528(2) 0.01453(14) 0.01345(14) 0.00306(12) N1 0.0244(4) 0.0297(5) 0.0212(4) 0.0122(3) 0.0053(3) 0.0057(4) C1 0.0292(5) 0.0288(5) 0.0242(5) 0.0057(4) 0.0057(4) 0.0076(4) C2 0.0202(4) 0.0311(5) 0.0189(4) 0.0103(4) 0.0062(3) 0.0077(4) O2 0.0281(4) 0.0363(5) 0.0232(4) 0.0073(3) 0.0053(3) 0.0091(3) O1 0.0376(5) 0.0374(5) 0.0258(4) 0.0148(4) -0.0004(3) 0.0104(4) O3 0.0161(3) 0.0494(5) 0.0237(4) 0.0167(4) 0.0052(3) 0.0097(3) C3 0.0154(4) 0.0346(6) 0.0211(4) 0.0122(4) 0.0055(3) 0.0058(4) O5 0.0164(3) 0.0472(5) 0.0283(4) 0.0194(4) 0.0078(3) 0.0113(3) C4 0.0156(4) 0.0263(5) 0.0214(4) 0.0103(4) 0.0055(3) 0.0042(4) O4 0.0205(4) 0.0493(5) 0.0243(4) 0.0202(4) 0.0073(3) 0.0081(3) C5 0.0169(4) 0.0261(5) 0.0234(5) 0.0112(4) 0.0064(3) 0.0060(4) O6 0.0248(4) 0.0614(6) 0.0246(4) 0.0200(4) 0.0098(3) 0.0125(4) _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 S1 C1 1.8095(13) . ? S1 H1S 1.166(14) . ? N1 C2 1.4881(14) . ? N1 H2N 0.9000 . ? N1 H1N 0.9000 . ? N1 H3N 0.9000 . ? C1 C2 1.5219(16) . ? C1 H12 0.9800 . ? C1 H11 0.9800 . ? C2 C3 1.5184(14) . ? C2 H2 0.9900 . ? O2 C3 1.2094(15) . ? O1 C3 1.3078(14) . ? O1 H1O 0.8300 . ? O3 C4 1.2510(12) . ? O5 C5 1.3106(12) . ? O5 H5O 0.8300 . ? C4 O4 1.2433(12) . ? C4 C5 1.5467(14) . ? C5 O6 1.2053(13) . ? 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 S1 H1S 97.4(9) . . ? C2 N1 H2N 109.5 . . ? C2 N1 H1N 109.5 . . ? H2N N1 H1N 109.5 . . ? C2 N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? C2 C1 S1 113.88(8) . . ? C2 C1 H12 108.8 . . ? S1 C1 H12 108.8 . . ? C2 C1 H11 108.8 . . ? S1 C1 H11 108.8 . . ? H12 C1 H11 107.7 . . ? N1 C2 C3 108.28(9) . . ? N1 C2 C1 111.05(9) . . ? C3 C2 C1 114.11(9) . . ? N1 C2 H2 107.7 . . ? C3 C2 H2 107.7 . . ? C1 C2 H2 107.7 . . ? C3 O1 H1O 109.5 . . ? O2 C3 O1 125.80(10) . . ? O2 C3 C2 122.06(10) . . ? O1 C3 C2 112.12(10) . . ? C5 O5 H5O 109.5 . . ? O4 C4 O3 125.56(9) . . ? O4 C4 C5 119.13(9) . . ? O3 C4 C5 115.28(9) . . ? O6 C5 O5 125.53(10) . . ? O6 C5 C4 121.06(9) . . ? O5 C5 C4 113.38(9) . . ? 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 S1 C1 C2 N1 60.40(11) . . . . ? S1 C1 C2 C3 -62.31(11) . . . . ? N1 C2 C3 O2 15.25(14) . . . . ? C1 C2 C3 O2 139.47(11) . . . . ? N1 C2 C3 O1 -166.14(9) . . . . ? C1 C2 C3 O1 -41.93(12) . . . . ? O4 C4 C5 O6 171.75(11) . . . . ? O3 C4 C5 O6 -6.30(16) . . . . ? O4 C4 C5 O5 -6.43(15) . . . . ? O3 C4 C5 O5 175.52(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.90 1.94 2.7991(12) 157.9 1 N1 H1N O6 0.90 2.45 3.0656(13) 126.1 1 N1 H2N O4 0.90 2.01 2.8877(13) 164.8 2_656 N1 H3N O2 0.90 2.00 2.8573(13) 158.1 2_655 O1 H1O O5 0.83 2.65 3.2634(12) 131.5 1_454 O1 H1O O4 0.83 1.78 2.5654(12) 157.1 1_454 O5 H5O O3 0.83 1.77 2.6042(11) 177.4 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.419 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.049 # END data_DL-cys_ox_11_225K _database_code_depnum_ccdc_archive 'CCDC 868540' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium semioxalate' _chemical_formula_moiety 'C3 H8 N O2 S, C2 H O4' _chemical_formula_sum 'C5 H9 N O6 S' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 225(2) _chemical_formula_weight 211.20 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.66107(17) _cell_length_b 8.9574(5) _cell_length_c 9.7578(5) _cell_angle_alpha 109.831(5) _cell_angle_beta 102.228(4) _cell_angle_gamma 99.913(3) _cell_volume 438.59(4) _cell_formula_units_Z 2 _cell_measurement_temperature 225(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.369 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8515 _exptl_absorpt_correction_T_max 0.9675 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 13496 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2668 _reflns_number_gt 2319 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0511P)^2^+0.1064P] 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 2668 _refine_ls_number_parameters 124 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 S1 S 0.86550(6) 0.39734(4) 0.24443(5) 0.03441(11) Uani 1 1 d D . . H1S H 0.768(3) 0.404(2) 0.1294(18) 0.041 Uiso 1 1 d D . . N1 N 0.51791(19) 0.08408(13) 0.25610(12) 0.0225(2) Uani 1 1 d . . . H2N H 0.3962 -0.0098 0.2238 0.027 Uiso 1 1 calc R . . H1N H 0.5992 0.1136 0.3550 0.027 Uiso 1 1 calc R . . H3N H 0.6268 0.0683 0.2008 0.027 Uiso 1 1 calc R . . C1 C 0.5969(2) 0.38368(16) 0.31668(14) 0.0261(2) Uani 1 1 d . . . H12 H 0.6553 0.4073 0.4257 0.031 Uiso 1 1 calc R . . H11 H 0.5149 0.4684 0.3052 0.031 Uiso 1 1 calc R . . C2 C 0.4047(2) 0.21670(15) 0.23734(13) 0.0211(2) Uani 1 1 d . . . H2 H 0.2689 0.2205 0.2868 0.025 Uiso 1 1 calc R . . O2 O 0.24618(17) 0.03116(12) -0.02400(10) 0.0281(2) Uani 1 1 d . . . O1 O 0.23111(19) 0.29364(12) 0.03933(11) 0.0313(2) Uani 1 1 d . . . H1O H 0.1471 0.2605 -0.0511 0.038 Uiso 1 1 calc R . . O3 O 0.64862(15) 0.19190(12) 0.57359(10) 0.0264(2) Uani 1 1 d . . . C3 C 0.2863(2) 0.16948(15) 0.06854(13) 0.0212(2) Uani 1 1 d . . . O5 O 1.28518(15) 0.21533(12) 0.69768(10) 0.0262(2) Uani 1 1 d . . . H5O H 1.4000 0.2121 0.6570 0.031 Uiso 1 1 calc R . . C4 C 0.8481(2) 0.19749(14) 0.66208(13) 0.0191(2) Uani 1 1 d . . . O4 O 0.87393(16) 0.19783(12) 0.79209(10) 0.0270(2) Uani 1 1 d . . . C5 C 1.0758(2) 0.19781(14) 0.59770(13) 0.0195(2) Uani 1 1 d . . . O6 O 1.05199(17) 0.17935(14) 0.46692(11) 0.0318(2) 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 S1 0.02502(17) 0.02863(18) 0.0472(2) 0.01321(15) 0.01189(14) 0.00294(12) N1 0.0219(4) 0.0269(5) 0.0196(4) 0.0116(4) 0.0049(4) 0.0052(4) C1 0.0259(6) 0.0261(6) 0.0224(5) 0.0053(5) 0.0058(4) 0.0070(5) C2 0.0185(5) 0.0277(6) 0.0179(5) 0.0094(4) 0.0054(4) 0.0070(4) O2 0.0252(4) 0.0328(5) 0.0222(4) 0.0070(4) 0.0052(3) 0.0080(4) O1 0.0342(5) 0.0333(5) 0.0241(4) 0.0138(4) -0.0004(4) 0.0089(4) O3 0.0148(4) 0.0448(5) 0.0219(4) 0.0154(4) 0.0051(3) 0.0088(4) C3 0.0143(4) 0.0308(6) 0.0190(5) 0.0107(4) 0.0050(4) 0.0051(4) O5 0.0151(4) 0.0427(5) 0.0258(4) 0.0176(4) 0.0070(3) 0.0101(4) C4 0.0146(4) 0.0231(5) 0.0196(5) 0.0093(4) 0.0046(4) 0.0037(4) O4 0.0187(4) 0.0438(5) 0.0228(4) 0.0185(4) 0.0067(3) 0.0069(4) C5 0.0153(4) 0.0235(5) 0.0214(5) 0.0104(4) 0.0058(4) 0.0050(4) O6 0.0230(4) 0.0534(6) 0.0230(4) 0.0179(4) 0.0090(3) 0.0109(4) _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 S1 C1 1.8092(13) . ? S1 H1S 1.166(14) . ? N1 C2 1.4884(15) . ? N1 H2N 0.9000 . ? N1 H1N 0.9000 . ? N1 H3N 0.9000 . ? C1 C2 1.5223(18) . ? C1 H12 0.9800 . ? C1 H11 0.9800 . ? C2 C3 1.5177(16) . ? C2 H2 0.9900 . ? O2 C3 1.2080(16) . ? O1 C3 1.3085(15) . ? O1 H1O 0.8300 . ? O3 C4 1.2496(13) . ? O5 C5 1.3127(13) . ? O5 H5O 0.8300 . ? C4 O4 1.2448(13) . ? C4 C5 1.5492(15) . ? C5 O6 1.2042(14) . ? 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 S1 H1S 98.1(9) . . ? C2 N1 H2N 109.5 . . ? C2 N1 H1N 109.5 . . ? H2N N1 H1N 109.5 . . ? C2 N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? C2 C1 S1 113.90(8) . . ? C2 C1 H12 108.8 . . ? S1 C1 H12 108.8 . . ? C2 C1 H11 108.8 . . ? S1 C1 H11 108.8 . . ? H12 C1 H11 107.7 . . ? N1 C2 C3 108.24(10) . . ? N1 C2 C1 110.90(9) . . ? C3 C2 C1 114.25(10) . . ? N1 C2 H2 107.7 . . ? C3 C2 H2 107.7 . . ? C1 C2 H2 107.7 . . ? C3 O1 H1O 109.5 . . ? O2 C3 O1 125.83(11) . . ? O2 C3 C2 122.12(11) . . ? O1 C3 C2 112.04(10) . . ? C5 O5 H5O 109.5 . . ? O4 C4 O3 125.64(10) . . ? O4 C4 C5 119.06(9) . . ? O3 C4 C5 115.26(9) . . ? O6 C5 O5 125.71(10) . . ? O6 C5 C4 120.98(10) . . ? O5 C5 C4 113.28(9) . . ? 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 S1 C1 C2 N1 60.50(12) . . . . ? S1 C1 C2 C3 -62.15(12) . . . . ? N1 C2 C3 O2 15.31(15) . . . . ? C1 C2 C3 O2 139.40(12) . . . . ? N1 C2 C3 O1 -166.07(9) . . . . ? C1 C2 C3 O1 -41.98(13) . . . . ? O4 C4 C5 O6 171.79(12) . . . . ? O3 C4 C5 O6 -6.15(17) . . . . ? O4 C4 C5 O5 -6.54(16) . . . . ? O3 C4 C5 O5 175.52(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.90 1.95 2.7983(13) 157.6 1 N1 H1N O6 0.90 2.44 3.0639(14) 126.4 1 N1 H2N O4 0.90 2.01 2.8883(14) 165.3 2_656 N1 H3N O2 0.90 2.00 2.8545(14) 158.5 2_655 O1 H1O O5 0.83 2.65 3.2587(13) 131.2 1_454 O1 H1O O4 0.83 1.78 2.5645(13) 157.3 1_454 O5 H5O O3 0.83 1.77 2.6029(11) 175.5 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.447 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.060 # END data_DL-cys_ox_11_200K _database_code_depnum_ccdc_archive 'CCDC 868541' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium semioxalate' _chemical_formula_moiety 'C3 H8 N O2 S, C2 H O4' _chemical_formula_sum 'C5 H9 N O6 S' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 200(2) _chemical_formula_weight 211.20 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.66062(16) _cell_length_b 8.9394(4) _cell_length_c 9.7525(5) _cell_angle_alpha 109.967(4) _cell_angle_beta 102.224(3) _cell_angle_gamma 99.833(3) _cell_volume 437.16(4) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.370 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8510 _exptl_absorpt_correction_T_max 0.9674 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 14713 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2659 _reflns_number_gt 2378 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0502P)^2^+0.0945P] 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 2659 _refine_ls_number_parameters 124 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 S1 S 0.86655(5) 0.39724(4) 0.24524(4) 0.03005(10) Uani 1 1 d D . . H1S H 0.769(3) 0.404(2) 0.1280(16) 0.036 Uiso 1 1 d D . . N1 N 0.51824(17) 0.08356(11) 0.25631(10) 0.02003(17) Uani 1 1 d . . . H2N H 0.3951 -0.0116 0.2231 0.024 Uiso 1 1 calc R . . H1N H 0.6002 0.1130 0.3564 0.024 Uiso 1 1 calc R . . H3N H 0.6284 0.0677 0.2004 0.024 Uiso 1 1 calc R . . C1 C 0.5978(2) 0.38435(14) 0.31787(12) 0.0232(2) Uani 1 1 d . . . H12 H 0.6569 0.4084 0.4282 0.028 Uiso 1 1 calc R . . H11 H 0.5153 0.4703 0.3064 0.028 Uiso 1 1 calc R . . C2 C 0.40525(18) 0.21698(13) 0.23833(11) 0.01876(19) Uani 1 1 d . . . H2 H 0.2683 0.2210 0.2885 0.023 Uiso 1 1 calc R . . O2 O 0.24597(15) 0.03092(11) -0.02380(9) 0.02509(17) Uani 1 1 d . . . O1 O 0.23220(17) 0.29473(11) 0.04024(9) 0.02776(18) Uani 1 1 d . . . H1O H 0.1478 0.2613 -0.0515 0.033 Uiso 1 1 calc R . . O3 O 0.64845(13) 0.19175(11) 0.57404(9) 0.02366(17) Uani 1 1 d . . . C3 C 0.28675(18) 0.16984(14) 0.06925(11) 0.01925(19) Uani 1 1 d . . . O5 O 1.28567(14) 0.21597(11) 0.69851(9) 0.02343(17) Uani 1 1 d . . . H5O H 1.4016 0.2118 0.6571 0.028 Uiso 1 1 calc R . . C4 C 0.84864(17) 0.19788(12) 0.66299(11) 0.01713(18) Uani 1 1 d . . . O4 O 0.87428(14) 0.19889(11) 0.79333(9) 0.02400(17) Uani 1 1 d . . . C5 C 1.07637(18) 0.19794(12) 0.59840(11) 0.01761(18) Uani 1 1 d . . . O6 O 1.05213(15) 0.17862(12) 0.46702(9) 0.02823(19) 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 S1 0.02185(14) 0.02530(15) 0.04091(18) 0.01164(13) 0.01001(12) 0.00272(11) N1 0.0198(4) 0.0234(4) 0.0176(4) 0.0101(3) 0.0042(3) 0.0046(3) C1 0.0236(5) 0.0225(5) 0.0199(5) 0.0049(4) 0.0046(4) 0.0061(4) C2 0.0164(4) 0.0245(5) 0.0163(4) 0.0086(4) 0.0050(3) 0.0061(4) O2 0.0228(4) 0.0293(4) 0.0197(4) 0.0062(3) 0.0044(3) 0.0074(3) O1 0.0305(4) 0.0298(4) 0.0208(4) 0.0121(3) -0.0006(3) 0.0081(3) O3 0.0131(3) 0.0395(5) 0.0197(3) 0.0136(3) 0.0037(3) 0.0076(3) C3 0.0131(4) 0.0283(5) 0.0173(4) 0.0102(4) 0.0046(3) 0.0051(4) O5 0.0135(3) 0.0381(4) 0.0232(4) 0.0159(3) 0.0061(3) 0.0090(3) C4 0.0133(4) 0.0205(4) 0.0179(4) 0.0086(4) 0.0044(3) 0.0033(3) O4 0.0168(3) 0.0393(5) 0.0199(4) 0.0166(3) 0.0059(3) 0.0063(3) C5 0.0143(4) 0.0209(4) 0.0187(4) 0.0091(4) 0.0052(3) 0.0044(3) O6 0.0209(4) 0.0471(5) 0.0200(4) 0.0156(4) 0.0079(3) 0.0098(3) _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 S1 C1 1.8113(12) . ? S1 H1S 1.184(13) . ? N1 C2 1.4893(13) . ? N1 H2N 0.9100 . ? N1 H1N 0.9100 . ? N1 H3N 0.9100 . ? C1 C2 1.5235(15) . ? C1 H12 0.9900 . ? C1 H11 0.9900 . ? C2 C3 1.5188(14) . ? C2 H2 1.0000 . ? O2 C3 1.2094(14) . ? O1 C3 1.3109(13) . ? O1 H1O 0.8400 . ? O3 C4 1.2529(12) . ? O5 C5 1.3117(12) . ? O5 H5O 0.8400 . ? C4 O4 1.2452(12) . ? C4 C5 1.5500(13) . ? C5 O6 1.2068(13) . ? 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 S1 H1S 98.5(8) . . ? C2 N1 H2N 109.5 . . ? C2 N1 H1N 109.5 . . ? H2N N1 H1N 109.5 . . ? C2 N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? C2 C1 S1 113.86(7) . . ? C2 C1 H12 108.8 . . ? S1 C1 H12 108.8 . . ? C2 C1 H11 108.8 . . ? S1 C1 H11 108.8 . . ? H12 C1 H11 107.7 . . ? N1 C2 C3 108.14(8) . . ? N1 C2 C1 110.96(8) . . ? C3 C2 C1 114.14(9) . . ? N1 C2 H2 107.8 . . ? C3 C2 H2 107.8 . . ? C1 C2 H2 107.8 . . ? C3 O1 H1O 109.5 . . ? O2 C3 O1 125.78(10) . . ? O2 C3 C2 122.11(10) . . ? O1 C3 C2 112.09(9) . . ? C5 O5 H5O 109.5 . . ? O4 C4 O3 125.52(9) . . ? O4 C4 C5 119.20(8) . . ? O3 C4 C5 115.24(8) . . ? O6 C5 O5 125.74(9) . . ? O6 C5 C4 120.97(9) . . ? O5 C5 C4 113.26(8) . . ? 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 S1 C1 C2 N1 60.26(10) . . . . ? S1 C1 C2 C3 -62.22(10) . . . . ? N1 C2 C3 O2 15.49(13) . . . . ? C1 C2 C3 O2 139.50(10) . . . . ? N1 C2 C3 O1 -165.89(8) . . . . ? C1 C2 C3 O1 -41.88(12) . . . . ? O4 C4 C5 O6 171.73(11) . . . . ? O3 C4 C5 O6 -6.21(15) . . . . ? O4 C4 C5 O5 -6.51(14) . . . . ? O3 C4 C5 O5 175.55(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.91 1.93 2.7969(12) 157.4 1 N1 H1N O6 0.91 2.44 3.0625(12) 126.1 1 N1 H2N O4 0.91 2.00 2.8879(12) 165.2 2_656 N1 H3N O2 0.91 1.99 2.8521(12) 158.4 2_655 O1 H1O O5 0.84 2.64 3.2544(12) 131.4 1_454 O1 H1O O4 0.84 1.77 2.5630(11) 156.6 1_454 O5 H5O O3 0.84 1.76 2.6010(10) 176.1 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.449 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.054 # END data_DL-cys_ox_11_175K _database_code_depnum_ccdc_archive 'CCDC 868542' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium semioxalate' _chemical_formula_moiety 'C3 H8 N O2 S, C2 H O4' _chemical_formula_sum 'C5 H9 N O6 S' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 175(2) _chemical_formula_weight 211.20 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.65949(16) _cell_length_b 8.9271(4) _cell_length_c 9.7495(4) _cell_angle_alpha 110.093(4) _cell_angle_beta 102.220(3) _cell_angle_gamma 99.769(3) _cell_volume 436.06(3) _cell_formula_units_Z 2 _cell_measurement_temperature 175(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.371 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8507 _exptl_absorpt_correction_T_max 0.9673 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 13588 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2650 _reflns_number_gt 2361 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0473P)^2^+0.1103P] 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 2650 _refine_ls_number_parameters 124 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 S1 S 0.86745(6) 0.39725(4) 0.24594(4) 0.02685(10) Uani 1 1 d D . . H1S H 0.765(3) 0.401(2) 0.1276(16) 0.032 Uiso 1 1 d D . . N1 N 0.51842(17) 0.08330(12) 0.25666(11) 0.01802(18) Uani 1 1 d . . . H2N H 0.3955 -0.0124 0.2219 0.022 Uiso 1 1 calc R . . H1N H 0.5982 0.1121 0.3570 0.022 Uiso 1 1 calc R . . H3N H 0.6305 0.0684 0.2019 0.022 Uiso 1 1 calc R . . C1 C 0.5990(2) 0.38488(14) 0.31895(13) 0.0210(2) Uani 1 1 d . . . H12 H 0.6583 0.4089 0.4293 0.025 Uiso 1 1 calc R . . H11 H 0.5168 0.4712 0.3078 0.025 Uiso 1 1 calc R . . C2 C 0.40565(19) 0.21705(14) 0.23888(12) 0.0171(2) Uani 1 1 d . . . H2 H 0.2687 0.2213 0.2891 0.021 Uiso 1 1 calc R . . O2 O 0.24586(16) 0.03084(11) -0.02374(9) 0.02253(18) Uani 1 1 d . . . O1 O 0.23301(17) 0.29561(11) 0.04106(10) 0.02490(19) Uani 1 1 d . . . H1O H 0.1461 0.2619 -0.0503 0.030 Uiso 1 1 calc R . . O3 O 0.64849(14) 0.19171(11) 0.57448(9) 0.02140(18) Uani 1 1 d . . . C3 C 0.28722(19) 0.17032(14) 0.06975(12) 0.0174(2) Uani 1 1 d . . . O5 O 1.28615(14) 0.21634(11) 0.69936(9) 0.02103(17) Uani 1 1 d . . . H5O H 1.4024 0.2128 0.6581 0.025 Uiso 1 1 calc R . . C4 C 0.84903(19) 0.19825(13) 0.66377(12) 0.01566(19) Uani 1 1 d . . . O4 O 0.87491(15) 0.19992(11) 0.79440(9) 0.02191(18) Uani 1 1 d . . . C5 C 1.07651(19) 0.19793(13) 0.59895(12) 0.01626(19) Uani 1 1 d . . . O6 O 1.05199(16) 0.17800(12) 0.46727(9) 0.02510(19) 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 S1 0.01981(15) 0.02285(16) 0.03597(18) 0.01023(13) 0.00896(12) 0.00268(11) N1 0.0177(4) 0.0212(4) 0.0157(4) 0.0091(3) 0.0038(3) 0.0042(3) C1 0.0211(5) 0.0209(5) 0.0180(5) 0.0046(4) 0.0046(4) 0.0055(4) C2 0.0156(4) 0.0216(5) 0.0149(4) 0.0077(4) 0.0045(4) 0.0057(4) O2 0.0203(4) 0.0261(4) 0.0179(4) 0.0055(3) 0.0041(3) 0.0063(3) O1 0.0271(4) 0.0270(4) 0.0191(4) 0.0112(3) 0.0000(3) 0.0073(3) O3 0.0126(3) 0.0354(5) 0.0175(4) 0.0119(3) 0.0037(3) 0.0070(3) C3 0.0117(4) 0.0251(5) 0.0164(4) 0.0094(4) 0.0047(3) 0.0042(4) O5 0.0120(3) 0.0343(5) 0.0207(4) 0.0140(3) 0.0056(3) 0.0080(3) C4 0.0127(4) 0.0183(5) 0.0159(4) 0.0073(4) 0.0040(3) 0.0028(3) O4 0.0159(4) 0.0355(5) 0.0179(4) 0.0148(3) 0.0054(3) 0.0061(3) C5 0.0141(4) 0.0187(5) 0.0179(5) 0.0089(4) 0.0052(4) 0.0049(4) O6 0.0190(4) 0.0410(5) 0.0179(4) 0.0134(4) 0.0071(3) 0.0084(4) _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 S1 C1 1.8115(12) . ? S1 H1S 1.190(13) . ? N1 C2 1.4889(13) . ? N1 H2N 0.9100 . ? N1 H1N 0.9100 . ? N1 H3N 0.9100 . ? C1 C2 1.5265(16) . ? C1 H12 0.9900 . ? C1 H11 0.9900 . ? C2 C3 1.5188(14) . ? C2 H2 1.0000 . ? O2 C3 1.2112(14) . ? O1 C3 1.3109(14) . ? O1 H1O 0.8400 . ? O3 C4 1.2545(12) . ? O5 C5 1.3132(12) . ? O5 H5O 0.8400 . ? C4 O4 1.2453(12) . ? C4 C5 1.5496(14) . ? C5 O6 1.2077(13) . ? 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 S1 H1S 97.5(8) . . ? C2 N1 H2N 109.5 . . ? C2 N1 H1N 109.5 . . ? H2N N1 H1N 109.5 . . ? C2 N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? C2 C1 S1 113.81(8) . . ? C2 C1 H12 108.8 . . ? S1 C1 H12 108.8 . . ? C2 C1 H11 108.8 . . ? S1 C1 H11 108.8 . . ? H12 C1 H11 107.7 . . ? N1 C2 C3 108.31(9) . . ? N1 C2 C1 110.88(8) . . ? C3 C2 C1 114.04(9) . . ? N1 C2 H2 107.8 . . ? C3 C2 H2 107.8 . . ? C1 C2 H2 107.8 . . ? C3 O1 H1O 109.5 . . ? O2 C3 O1 125.80(10) . . ? O2 C3 C2 121.97(10) . . ? O1 C3 C2 112.21(9) . . ? C5 O5 H5O 109.5 . . ? O4 C4 O3 125.56(10) . . ? O4 C4 C5 119.23(9) . . ? O3 C4 C5 115.17(9) . . ? O6 C5 O5 125.79(10) . . ? O6 C5 C4 120.98(9) . . ? O5 C5 C4 113.20(9) . . ? 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 S1 C1 C2 N1 60.36(10) . . . . ? S1 C1 C2 C3 -62.21(11) . . . . ? N1 C2 C3 O2 15.63(14) . . . . ? C1 C2 C3 O2 139.60(11) . . . . ? N1 C2 C3 O1 -165.85(9) . . . . ? C1 C2 C3 O1 -41.89(12) . . . . ? O4 C4 C5 O6 171.76(11) . . . . ? O3 C4 C5 O6 -6.18(15) . . . . ? O4 C4 C5 O5 -6.47(14) . . . . ? O3 C4 C5 O5 175.59(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.91 1.93 2.7950(12) 158.3 1 N1 H1N O6 0.91 2.45 3.0604(12) 125.0 1 N1 H2N O4 0.91 2.00 2.8899(13) 164.2 2_656 N1 H3N O2 0.91 1.99 2.8511(13) 157.3 2_655 O1 H1O O5 0.84 2.65 3.2505(12) 130.1 1_454 O1 H1O O4 0.84 1.76 2.5609(11) 158.0 1_454 O5 H5O O3 0.84 1.76 2.6004(11) 175.6 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.435 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.054 # END data_DL-cys_ox_11_150K _database_code_depnum_ccdc_archive 'CCDC 868543' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium semioxalate' _chemical_formula_moiety 'C3 H8 N O2 S, C2 H O4' _chemical_formula_sum 'C5 H9 N O6 S' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 150(2) _chemical_formula_weight 211.20 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.65706(14) _cell_length_b 8.9064(4) _cell_length_c 9.7446(4) _cell_angle_alpha 110.208(4) _cell_angle_beta 102.193(3) _cell_angle_gamma 99.702(3) _cell_volume 434.47(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8502 _exptl_absorpt_correction_T_max 0.9672 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 13582 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2640 _reflns_number_gt 2364 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0463P)^2^+0.1287P] 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 2640 _refine_ls_number_parameters 124 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 S1 S 0.86836(5) 0.39719(4) 0.24655(4) 0.02306(9) Uani 1 1 d D . . H1S H 0.766(3) 0.400(2) 0.1267(16) 0.028 Uiso 1 1 d D . . N1 N 0.51849(17) 0.08273(12) 0.25680(10) 0.01593(17) Uani 1 1 d . . . H2N H 0.3952 -0.0130 0.2217 0.019 Uiso 1 1 calc R . . H1N H 0.5981 0.1113 0.3572 0.019 Uiso 1 1 calc R . . H3N H 0.6306 0.0677 0.2020 0.019 Uiso 1 1 calc R . . C1 C 0.5999(2) 0.38542(14) 0.32004(12) 0.0182(2) Uani 1 1 d . . . H12 H 0.6592 0.4093 0.4304 0.022 Uiso 1 1 calc R . . H11 H 0.5180 0.4723 0.3093 0.022 Uiso 1 1 calc R . . C2 C 0.40628(18) 0.21745(13) 0.23958(11) 0.01495(19) Uani 1 1 d . . . H2 H 0.2695 0.2219 0.2900 0.018 Uiso 1 1 calc R . . O2 O 0.24587(15) 0.03076(10) -0.02346(9) 0.01981(17) Uani 1 1 d . . . O1 O 0.23419(16) 0.29682(11) 0.04207(9) 0.02198(18) Uani 1 1 d . . . H1O H 0.1449 0.2630 -0.0488 0.026 Uiso 1 1 calc R . . O3 O 0.64831(14) 0.19165(11) 0.57491(9) 0.01856(17) Uani 1 1 d . . . C3 C 0.28749(18) 0.17053(14) 0.07036(12) 0.01545(19) Uani 1 1 d . . . O5 O 1.28649(14) 0.21692(11) 0.70013(9) 0.01856(17) Uani 1 1 d . . . H5O H 1.4036 0.2158 0.6595 0.022 Uiso 1 1 calc R . . C4 C 0.84916(18) 0.19894(13) 0.66464(11) 0.01373(18) Uani 1 1 d . . . O4 O 0.87498(14) 0.20102(11) 0.79552(9) 0.01912(17) Uani 1 1 d . . . C5 C 1.07655(18) 0.19804(13) 0.59943(12) 0.01438(18) Uani 1 1 d . . . O6 O 1.05204(15) 0.17728(11) 0.46734(9) 0.02187(18) 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 S1 0.01720(14) 0.01983(15) 0.03056(16) 0.00885(12) 0.00768(11) 0.00233(10) N1 0.0158(4) 0.0186(4) 0.0141(4) 0.0081(3) 0.0035(3) 0.0040(3) C1 0.0184(5) 0.0179(5) 0.0152(5) 0.0038(4) 0.0037(4) 0.0045(4) C2 0.0141(4) 0.0189(5) 0.0130(4) 0.0071(4) 0.0040(3) 0.0054(4) O2 0.0174(4) 0.0229(4) 0.0161(4) 0.0050(3) 0.0035(3) 0.0053(3) O1 0.0238(4) 0.0239(4) 0.0165(4) 0.0096(3) -0.0003(3) 0.0064(3) O3 0.0108(3) 0.0302(4) 0.0157(3) 0.0104(3) 0.0031(3) 0.0060(3) C3 0.0104(4) 0.0227(5) 0.0140(4) 0.0084(4) 0.0038(3) 0.0034(4) O5 0.0108(3) 0.0296(4) 0.0180(4) 0.0118(3) 0.0046(3) 0.0066(3) C4 0.0115(4) 0.0157(4) 0.0141(4) 0.0065(4) 0.0036(3) 0.0027(3) O4 0.0141(3) 0.0304(4) 0.0162(4) 0.0131(3) 0.0048(3) 0.0052(3) C5 0.0121(4) 0.0161(5) 0.0157(4) 0.0072(4) 0.0041(3) 0.0035(3) O6 0.0170(4) 0.0349(5) 0.0156(4) 0.0114(3) 0.0060(3) 0.0070(3) _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 S1 C1 1.8133(11) . ? S1 H1S 1.200(13) . ? N1 C2 1.4905(13) . ? N1 H2N 0.9100 . ? N1 H1N 0.9100 . ? N1 H3N 0.9100 . ? C1 C2 1.5255(15) . ? C1 H12 0.9900 . ? C1 H11 0.9900 . ? C2 C3 1.5188(14) . ? C2 H2 1.0000 . ? O2 C3 1.2103(14) . ? O1 C3 1.3136(13) . ? O1 H1O 0.8400 . ? O3 C4 1.2554(12) . ? O5 C5 1.3146(12) . ? O5 H5O 0.8400 . ? C4 O4 1.2459(12) . ? C4 C5 1.5504(13) . ? C5 O6 1.2091(13) . ? 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 S1 H1S 97.8(8) . . ? C2 N1 H2N 109.5 . . ? C2 N1 H1N 109.5 . . ? H2N N1 H1N 109.5 . . ? C2 N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? C2 C1 S1 113.71(7) . . ? C2 C1 H12 108.8 . . ? S1 C1 H12 108.8 . . ? C2 C1 H11 108.8 . . ? S1 C1 H11 108.8 . . ? H12 C1 H11 107.7 . . ? N1 C2 C3 108.21(8) . . ? N1 C2 C1 110.94(8) . . ? C3 C2 C1 114.19(9) . . ? N1 C2 H2 107.8 . . ? C3 C2 H2 107.8 . . ? C1 C2 H2 107.8 . . ? C3 O1 H1O 109.5 . . ? O2 C3 O1 125.85(10) . . ? O2 C3 C2 122.06(10) . . ? O1 C3 C2 112.08(9) . . ? C5 O5 H5O 109.5 . . ? O4 C4 O3 125.57(9) . . ? O4 C4 C5 119.32(9) . . ? O3 C4 C5 115.06(8) . . ? O6 C5 O5 125.76(9) . . ? O6 C5 C4 121.09(9) . . ? O5 C5 C4 113.13(8) . . ? 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 S1 C1 C2 N1 60.40(10) . . . . ? S1 C1 C2 C3 -62.20(10) . . . . ? N1 C2 C3 O2 15.48(13) . . . . ? C1 C2 C3 O2 139.55(10) . . . . ? N1 C2 C3 O1 -165.75(8) . . . . ? C1 C2 C3 O1 -41.68(12) . . . . ? O4 C4 C5 O6 171.60(10) . . . . ? O3 C4 C5 O6 -6.05(15) . . . . ? O4 C4 C5 O5 -6.62(14) . . . . ? O3 C4 C5 O5 175.74(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.91 1.93 2.7947(12) 158.2 1 N1 H1N O6 0.91 2.45 3.0598(12) 125.0 1 N1 H2N O4 0.91 2.00 2.8871(12) 164.3 2_656 N1 H3N O2 0.91 1.99 2.8488(12) 157.4 2_655 O1 H1O O5 0.84 2.65 3.2475(11) 128.9 1_454 O1 H1O O4 0.84 1.76 2.5626(11) 159.3 1_454 O5 H5O O3 0.84 1.76 2.5980(10) 173.6 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.471 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.057 # END data_DL-cys_ox_11_100K _database_code_depnum_ccdc_archive 'CCDC 868544' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium semioxalate' _chemical_formula_moiety 'C3 H8 N O2 S, C2 H O4' _chemical_formula_sum 'C5 H9 N O6 S' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(2) _chemical_formula_weight 211.20 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' O O 0.0106 0.0060 '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' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.65476(17) _cell_length_b 8.8702(4) _cell_length_c 9.7344(4) _cell_angle_alpha 110.377(4) _cell_angle_beta 102.167(3) _cell_angle_gamma 99.621(3) _cell_volume 431.74(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.375 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8494 _exptl_absorpt_correction_T_max 0.9670 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 13555 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 30.51 _reflns_number_total 2625 _reflns_number_gt 2306 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0492P)^2^+0.1427P] 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 2625 _refine_ls_number_parameters 124 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0868 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 S1 S 0.86970(6) 0.39725(4) 0.24750(4) 0.01741(10) Uani 1 1 d D . . H1S H 0.766(3) 0.404(2) 0.1313(17) 0.021 Uiso 1 1 d D . . N1 N 0.51889(19) 0.08213(13) 0.25717(12) 0.01255(19) Uani 1 1 d . . . H2N H 0.3957 -0.0143 0.2208 0.015 Uiso 1 1 calc R . . H1N H 0.5972 0.1101 0.3578 0.015 Uiso 1 1 calc R . . H3N H 0.6321 0.0677 0.2029 0.015 Uiso 1 1 calc R . . C1 C 0.6017(2) 0.38648(16) 0.32173(14) 0.0145(2) Uani 1 1 d . . . H12 H 0.6614 0.4104 0.4322 0.017 Uiso 1 1 calc R . . H11 H 0.5203 0.4741 0.3115 0.017 Uiso 1 1 calc R . . C2 C 0.4071(2) 0.21773(15) 0.24074(13) 0.0119(2) Uani 1 1 d . . . H2 H 0.2705 0.2225 0.2915 0.014 Uiso 1 1 calc R . . O2 O 0.24543(17) 0.03052(12) -0.02337(10) 0.01560(18) Uani 1 1 d . . . O1 O 0.23532(17) 0.29846(12) 0.04361(11) 0.01676(19) Uani 1 1 d . . . H1O H 0.1503 0.2652 -0.0483 0.020 Uiso 1 1 calc R . . O3 O 0.64811(16) 0.19147(12) 0.57553(10) 0.01482(18) Uani 1 1 d . . . C3 C 0.2881(2) 0.17137(15) 0.07123(13) 0.0123(2) Uani 1 1 d . . . O5 O 1.28705(16) 0.21756(12) 0.70119(10) 0.01455(18) Uani 1 1 d . . . H5O H 1.4030 0.2126 0.6596 0.017 Uiso 1 1 calc R . . C4 C 0.8494(2) 0.19936(15) 0.66562(14) 0.0115(2) Uani 1 1 d . . . O4 O 0.87556(16) 0.20258(12) 0.79718(10) 0.01497(18) Uani 1 1 d . . . C5 C 1.0769(2) 0.19792(15) 0.60016(14) 0.0117(2) Uani 1 1 d . . . O6 O 1.05220(17) 0.17626(12) 0.46760(10) 0.01677(19) 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 S1 0.01393(15) 0.01627(16) 0.02145(17) 0.00705(12) 0.00599(11) 0.00244(11) N1 0.0133(4) 0.0153(5) 0.0103(4) 0.0065(4) 0.0034(3) 0.0040(4) C1 0.0149(5) 0.0155(5) 0.0115(5) 0.0039(4) 0.0036(4) 0.0038(4) C2 0.0112(5) 0.0154(5) 0.0096(5) 0.0053(4) 0.0030(4) 0.0042(4) O2 0.0145(4) 0.0186(4) 0.0125(4) 0.0047(3) 0.0039(3) 0.0044(3) O1 0.0192(4) 0.0189(5) 0.0117(4) 0.0076(3) 0.0007(3) 0.0055(3) O3 0.0101(4) 0.0239(5) 0.0110(4) 0.0077(3) 0.0025(3) 0.0049(3) C3 0.0085(5) 0.0187(6) 0.0106(5) 0.0067(4) 0.0036(4) 0.0029(4) O5 0.0095(4) 0.0232(5) 0.0133(4) 0.0091(4) 0.0041(3) 0.0055(3) C4 0.0102(5) 0.0131(5) 0.0120(5) 0.0057(4) 0.0038(4) 0.0025(4) O4 0.0123(4) 0.0235(5) 0.0120(4) 0.0100(3) 0.0044(3) 0.0045(3) C5 0.0112(5) 0.0130(5) 0.0121(5) 0.0057(4) 0.0044(4) 0.0036(4) O6 0.0147(4) 0.0260(5) 0.0115(4) 0.0088(4) 0.0049(3) 0.0058(3) _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 S1 C1 1.8135(13) . ? S1 H1S 1.185(14) . ? N1 C2 1.4890(15) . ? N1 H2N 0.9100 . ? N1 H1N 0.9100 . ? N1 H3N 0.9100 . ? C1 C2 1.5281(17) . ? C1 H12 0.9900 . ? C1 H11 0.9900 . ? C2 C3 1.5204(16) . ? C2 H2 1.0000 . ? O2 C3 1.2131(16) . ? O1 C3 1.3121(15) . ? O1 H1O 0.8400 . ? O3 C4 1.2570(14) . ? O5 C5 1.3146(14) . ? O5 H5O 0.8400 . ? C4 O4 1.2475(14) . ? C4 C5 1.5513(16) . ? C5 O6 1.2099(15) . ? 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 S1 H1S 96.6(9) . . ? C2 N1 H2N 109.5 . . ? C2 N1 H1N 109.5 . . ? H2N N1 H1N 109.5 . . ? C2 N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? C2 C1 S1 113.62(8) . . ? C2 C1 H12 108.8 . . ? S1 C1 H12 108.8 . . ? C2 C1 H11 108.8 . . ? S1 C1 H11 108.8 . . ? H12 C1 H11 107.7 . . ? N1 C2 C3 108.34(9) . . ? N1 C2 C1 110.88(9) . . ? C3 C2 C1 114.02(10) . . ? N1 C2 H2 107.8 . . ? C3 C2 H2 107.8 . . ? C1 C2 H2 107.8 . . ? C3 O1 H1O 109.5 . . ? O2 C3 O1 125.87(11) . . ? O2 C3 C2 121.88(11) . . ? O1 C3 C2 112.23(10) . . ? C5 O5 H5O 109.5 . . ? O4 C4 O3 125.55(11) . . ? O4 C4 C5 119.32(10) . . ? O3 C4 C5 115.09(10) . . ? O6 C5 O5 125.80(11) . . ? O6 C5 C4 121.07(10) . . ? O5 C5 C4 113.11(10) . . ? 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 S1 C1 C2 N1 60.32(12) . . . . ? S1 C1 C2 C3 -62.28(12) . . . . ? N1 C2 C3 O2 15.71(15) . . . . ? C1 C2 C3 O2 139.68(12) . . . . ? N1 C2 C3 O1 -165.67(9) . . . . ? C1 C2 C3 O1 -41.70(13) . . . . ? O4 C4 C5 O6 171.73(12) . . . . ? O3 C4 C5 O6 -6.00(17) . . . . ? O4 C4 C5 O5 -6.55(16) . . . . ? O3 C4 C5 O5 175.72(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.91 1.92 2.7918(13) 158.6 1 N1 H1N O6 0.91 2.45 3.0580(14) 124.3 1 N1 H2N O4 0.91 2.00 2.8848(14) 163.8 2_656 N1 H3N O2 0.91 1.99 2.8451(14) 156.8 2_655 O1 H1O O5 0.84 2.63 3.2445(13) 131.2 1_454 O1 H1O O4 0.84 1.77 2.5612(13) 156.4 1_454 O5 H5O O3 0.84 1.76 2.5946(12) 176.4 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.578 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.071 # END # Attachment '- CIFs_DL-cys_ox_21_Mod.txt' data_DL-cys_ox_21_295K _database_code_depnum_ccdc_archive 'CCDC 868545' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium oxalate' _chemical_formula_moiety 'C3 H8 N O2 S, 0.5(C2 O4)' _chemical_formula_sum 'C4 H8 N O4 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 295(2) _chemical_formula_weight 166.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2748(2) _cell_length_b 6.6507(3) _cell_length_c 10.4397(3) _cell_angle_alpha 86.836(3) _cell_angle_beta 76.833(3) _cell_angle_gamma 70.093(4) _cell_volume 335.20(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.437 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8515 _exptl_absorpt_correction_T_max 0.9138 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 7295 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 30.50 _reflns_number_total 2040 _reflns_number_gt 1810 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0460P)^2^+0.1037P] 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 2040 _refine_ls_number_parameters 96 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0939 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.121 _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 C1 C 0.9330(3) 0.8015(2) 0.36583(13) 0.0309(3) Uani 1 1 d . . . H11 H 0.8810 0.7019 0.3217 0.037 Uiso 1 1 calc R . . H12 H 0.7902 0.8561 0.4446 0.037 Uiso 1 1 calc R . . C2 C 0.9488(2) 0.98610(18) 0.27558(10) 0.0215(2) Uani 1 1 d . . . H2 H 1.0041 1.0840 0.3210 0.026 Uiso 1 1 calc R . . C3 C 0.6680(2) 1.11067(17) 0.24435(11) 0.0222(2) Uani 1 1 d . . . C4 C 1.1335(2) 0.41414(16) 0.01379(10) 0.0197(2) Uani 1 1 d . . . N1 N 1.16120(19) 0.90846(15) 0.15146(9) 0.02208(19) Uani 1 1 d . . . H1N H 1.1557 1.0167 0.0969 0.027 Uiso 1 1 calc R . . H2N H 1.1267 0.8067 0.1138 0.027 Uiso 1 1 calc R . . H3N H 1.3281 0.8556 0.1696 0.027 Uiso 1 1 calc R . . O1 O 0.68656(17) 1.22641(15) 0.14032(9) 0.0291(2) Uani 1 1 d . . . H1O H 0.5310 1.2964 0.1307 0.035 Uiso 1 1 calc R . . O2 O 0.45467(19) 1.10425(18) 0.31486(11) 0.0395(2) Uani 1 1 d . . . O3 O 1.23663(18) 0.46993(14) 0.09778(9) 0.0295(2) Uani 1 1 d . . . O4 O 1.22310(17) 0.23864(13) -0.04533(9) 0.02745(19) Uani 1 1 d . . . S1 S 1.25855(8) 0.66011(6) 0.41239(4) 0.04201(13) Uani 1 1 d D . . H1S H 1.276(4) 0.486(3) 0.388(2) 0.050 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 C1 0.0272(6) 0.0341(6) 0.0286(6) 0.0103(5) -0.0075(4) -0.0074(5) C2 0.0184(4) 0.0232(5) 0.0213(5) 0.0009(4) -0.0059(4) -0.0040(4) C3 0.0176(4) 0.0223(5) 0.0252(5) -0.0001(4) -0.0057(4) -0.0041(4) C4 0.0152(4) 0.0178(4) 0.0245(5) 0.0042(4) -0.0054(3) -0.0034(3) N1 0.0174(4) 0.0218(4) 0.0247(4) 0.0016(3) -0.0044(3) -0.0039(3) O1 0.0176(4) 0.0323(4) 0.0316(4) 0.0094(3) -0.0071(3) -0.0013(3) O2 0.0199(4) 0.0479(6) 0.0448(6) 0.0138(4) -0.0028(4) -0.0088(4) O3 0.0255(4) 0.0252(4) 0.0366(5) -0.0021(3) -0.0174(3) 0.0003(3) O4 0.0222(4) 0.0193(4) 0.0373(5) -0.0027(3) -0.0090(3) -0.0005(3) S1 0.0406(2) 0.0402(2) 0.0439(2) 0.01384(15) -0.02291(16) -0.00518(15) _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 C2 1.5193(17) . ? C1 S1 1.8163(13) . ? C1 H11 0.9700 . ? C1 H12 0.9700 . ? C2 N1 1.4896(13) . ? C2 C3 1.5303(14) . ? C2 H2 0.9800 . ? C3 O2 1.2090(14) . ? C3 O1 1.3009(14) . ? C4 O4 1.2400(13) . ? C4 O3 1.2622(13) . ? C4 C4 1.5568(19) 2_765 ? N1 H1N 0.8900 . ? N1 H2N 0.8900 . ? N1 H3N 0.8900 . ? O1 H1O 0.8200 . ? S1 H1S 1.167(14) . ? 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 C2 C1 S1 112.49(9) . . ? C2 C1 H11 109.1 . . ? S1 C1 H11 109.1 . . ? C2 C1 H12 109.1 . . ? S1 C1 H12 109.1 . . ? H11 C1 H12 107.8 . . ? N1 C2 C1 110.91(9) . . ? N1 C2 C3 110.12(8) . . ? C1 C2 C3 111.49(9) . . ? N1 C2 H2 108.1 . . ? C1 C2 H2 108.1 . . ? C3 C2 H2 108.1 . . ? O2 C3 O1 125.37(11) . . ? O2 C3 C2 121.45(11) . . ? O1 C3 C2 113.12(9) . . ? O4 C4 O3 126.22(10) . . ? O4 C4 C4 118.83(12) . 2_765 ? O3 C4 C4 114.95(11) . 2_765 ? C2 N1 H1N 109.5 . . ? C2 N1 H2N 109.5 . . ? H1N N1 H2N 109.5 . . ? C2 N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? C3 O1 H1O 109.5 . . ? C1 S1 H1S 98.6(10) . . ? 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 S1 C1 C2 N1 60.26(11) . . . . ? S1 C1 C2 C3 -176.64(8) . . . . ? N1 C2 C3 O2 145.26(11) . . . . ? C1 C2 C3 O2 21.70(15) . . . . ? N1 C2 C3 O1 -37.50(13) . . . . ? C1 C2 C3 O1 -161.06(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.89 2.09 2.9722(13) 169.0 1_565 N1 H3N O4 0.89 2.32 3.0081(12) 134.7 2_865 N1 H2N O3 0.89 2.12 2.8753(13) 142.2 . N1 H2N O1 0.89 2.60 3.0700(13) 113.5 2_775 N1 H2N O4 0.89 2.24 2.9644(13) 138.6 2_765 O1 H1O O3 0.82 1.69 2.4972(12) 170.2 1_465 S1 H1S O2 1.167(14) 2.485(15) 3.6201(13) 163.7(14) 1_645 N1 H3N O2 0.89 2.64 3.1341(15) 116.0 1_655 C2 H2 O2 0.98 2.41 3.1411(15) 130.8 1_655 C1 H12 O2 0.97 2.53 3.4554(17) 159.3 2_676 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.486 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.051 # END data_DL-cys_ox_21_275K _database_code_depnum_ccdc_archive 'CCDC 868546' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium oxalate' _chemical_formula_moiety 'C3 H8 N O2 S, 0.5(C2 O4)' _chemical_formula_sum 'C4 H8 N O4 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 275(2) _chemical_formula_weight 166.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2705(3) _cell_length_b 6.6419(4) _cell_length_c 10.4243(5) _cell_angle_alpha 86.895(4) _cell_angle_beta 76.869(4) _cell_angle_gamma 70.160(5) _cell_volume 334.18(3) _cell_formula_units_Z 2 _cell_measurement_temperature 275(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.438 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8511 _exptl_absorpt_correction_T_max 0.9136 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 5553 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 31.00 _reflns_number_total 2119 _reflns_number_gt 1764 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0549P)^2^+0.0827P] 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 2119 _refine_ls_number_parameters 96 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.1041 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.070 _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 C3 C 0.6684(2) 1.1110(2) 0.24447(12) 0.0221(2) Uani 1 1 d . . . C2 C 0.9491(2) 0.9866(2) 0.27558(12) 0.0214(2) Uani 1 1 d . . . H2 H 1.0043 1.0846 0.3213 0.026 Uiso 1 1 calc R . . C1 C 0.9331(3) 0.8014(2) 0.36590(14) 0.0298(3) Uani 1 1 d . . . H11 H 0.8810 0.7017 0.3216 0.036 Uiso 1 1 calc R . . H12 H 0.7903 0.8559 0.4449 0.036 Uiso 1 1 calc R . . C4 C 1.1333(2) 0.41431(18) 0.01391(12) 0.0197(2) Uani 1 1 d . . . N1 N 1.1617(2) 0.90899(17) 0.15152(10) 0.0219(2) Uani 1 1 d . . . H3N H 1.3286 0.8565 0.1698 0.026 Uiso 1 1 calc R . . H1N H 1.1562 1.0173 0.0968 0.026 Uiso 1 1 calc R . . H2N H 1.1276 0.8068 0.1138 0.026 Uiso 1 1 calc R . . O1 O 0.68674(18) 1.22695(16) 0.14027(9) 0.0283(2) Uani 1 1 d . . . H1O H 0.5311 1.2951 0.1299 0.034 Uiso 1 1 calc R . . O2 O 0.4547(2) 1.10431(19) 0.31512(12) 0.0379(3) Uani 1 1 d . . . O3 O 1.2368(2) 0.47029(15) 0.09788(10) 0.0288(2) Uani 1 1 d . . . O4 O 1.22350(19) 0.23839(14) -0.04549(10) 0.0265(2) Uani 1 1 d . . . S1 S 1.25896(9) 0.66018(7) 0.41232(4) 0.04036(14) Uani 1 1 d D . . H1S H 1.274(4) 0.484(3) 0.395(2) 0.048 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 C3 0.0178(5) 0.0212(5) 0.0250(5) -0.0005(4) -0.0051(4) -0.0031(4) C2 0.0182(5) 0.0233(5) 0.0208(5) 0.0007(4) -0.0047(4) -0.0043(4) C1 0.0260(6) 0.0317(7) 0.0284(6) 0.0098(5) -0.0068(5) -0.0064(5) C4 0.0157(4) 0.0176(5) 0.0244(5) 0.0042(4) -0.0053(4) -0.0037(4) N1 0.0179(4) 0.0214(5) 0.0243(5) 0.0015(4) -0.0044(4) -0.0044(4) O1 0.0179(4) 0.0309(5) 0.0309(5) 0.0093(4) -0.0069(4) -0.0018(4) O2 0.0207(4) 0.0452(6) 0.0427(6) 0.0128(5) -0.0033(4) -0.0088(4) O3 0.0251(4) 0.0248(5) 0.0348(5) -0.0021(4) -0.0157(4) -0.0001(4) O4 0.0223(4) 0.0190(4) 0.0353(5) -0.0021(4) -0.0084(4) -0.0014(3) S1 0.0392(2) 0.0387(2) 0.0418(2) 0.01287(16) -0.02114(17) -0.00525(17) _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 C3 O2 1.2112(15) . ? C3 O1 1.3016(15) . ? C3 C2 1.5282(16) . ? C2 N1 1.4886(15) . ? C2 C1 1.5220(19) . ? C2 H2 0.9800 . ? C1 S1 1.8162(14) . ? C1 H11 0.9700 . ? C1 H12 0.9700 . ? C4 O4 1.2419(14) . ? C4 O3 1.2616(15) . ? C4 C4 1.555(2) 2_765 ? N1 H3N 0.8900 . ? N1 H1N 0.8900 . ? N1 H2N 0.8900 . ? O1 H1O 0.8200 . ? S1 H1S 1.168(15) . ? 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 O2 C3 O1 125.32(12) . . ? O2 C3 C2 121.48(12) . . ? O1 C3 C2 113.15(10) . . ? N1 C2 C1 110.85(10) . . ? N1 C2 C3 110.27(9) . . ? C1 C2 C3 111.42(10) . . ? N1 C2 H2 108.1 . . ? C1 C2 H2 108.1 . . ? C3 C2 H2 108.1 . . ? C2 C1 S1 112.37(9) . . ? C2 C1 H11 109.1 . . ? S1 C1 H11 109.1 . . ? C2 C1 H12 109.1 . . ? S1 C1 H12 109.1 . . ? H11 C1 H12 107.9 . . ? O4 C4 O3 126.11(11) . . ? O4 C4 C4 118.83(13) . 2_765 ? O3 C4 C4 115.06(13) . 2_765 ? C2 N1 H3N 109.5 . . ? C2 N1 H1N 109.5 . . ? H3N N1 H1N 109.5 . . ? C2 N1 H2N 109.5 . . ? H3N N1 H2N 109.5 . . ? H1N N1 H2N 109.5 . . ? C3 O1 H1O 109.5 . . ? C1 S1 H1S 99.7(10) . . ? 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 C3 C2 N1 145.21(13) . . . . ? O1 C3 C2 N1 -37.43(14) . . . . ? O2 C3 C2 C1 21.67(17) . . . . ? O1 C3 C2 C1 -160.97(11) . . . . ? N1 C2 C1 S1 60.16(13) . . . . ? C3 C2 C1 S1 -176.63(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.89 2.09 2.9669(15) 169.0 1_565 N1 H3N O4 0.89 2.31 3.0025(14) 134.6 2_865 N1 H2N O3 0.89 2.12 2.8729(14) 142.4 . N1 H2N O1 0.89 2.60 3.0675(14) 113.7 2_775 N1 H2N O4 0.89 2.24 2.9645(14) 138.3 2_765 O1 H1O O3 0.82 1.69 2.4958(13) 169.4 1_465 S1 H1S O2 1.168(15) 2.489(16) 3.6148(14) 161.4(15) 1_645 N1 H3N O2 0.89 2.63 3.1258(16) 116.2 1_655 C2 H2 O2 0.98 2.41 3.1351(16) 130.6 1_655 C1 H12 O2 0.97 2.52 3.4488(18) 159.5 2_676 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.468 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.056 # END data_DL-cys_ox_21_250K _database_code_depnum_ccdc_archive 'CCDC 868547' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium oxalate' _chemical_formula_moiety 'C3 H8 N O2 S, 0.5(C2 O4)' _chemical_formula_sum 'C4 H8 N O4 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 250(2) _chemical_formula_weight 166.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2672(3) _cell_length_b 6.6328(4) _cell_length_c 10.4111(4) _cell_angle_alpha 86.956(4) _cell_angle_beta 76.887(4) _cell_angle_gamma 70.227(5) _cell_volume 333.24(3) _cell_formula_units_Z 2 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.440 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8507 _exptl_absorpt_correction_T_max 0.9133 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 5161 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 30.02 _reflns_number_total 1949 _reflns_number_gt 1680 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0532P)^2^+0.1003P] 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 1949 _refine_ls_number_parameters 96 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 C1 C 0.9332(3) 0.8018(2) 0.36603(14) 0.0279(3) Uani 1 1 d . . . H11 H 0.8801 0.7012 0.3212 0.033 Uiso 1 1 calc R . . H12 H 0.7892 0.8570 0.4460 0.033 Uiso 1 1 calc R . . C2 C 0.9496(2) 0.9870(2) 0.27580(12) 0.0202(2) Uani 1 1 d . . . H2 H 1.0054 1.0861 0.3221 0.024 Uiso 1 1 calc R . . C3 C 0.6685(3) 1.1116(2) 0.24443(12) 0.0204(2) Uani 1 1 d . . . C4 C 1.1334(2) 0.41408(19) 0.01376(12) 0.0185(2) Uani 1 1 d . . . N1 N 1.1622(2) 0.90936(18) 0.15146(10) 0.0204(2) Uani 1 1 d . . . H1N H 1.1552 1.0186 0.0958 0.024 Uiso 1 1 calc R . . H2N H 1.1287 0.8048 0.1137 0.024 Uiso 1 1 calc R . . H3N H 1.3312 0.8577 0.1698 0.024 Uiso 1 1 calc R . . O1 O 0.68716(19) 1.22765(16) 0.14016(10) 0.0260(2) Uani 1 1 d . . . H1O H 0.5297 1.2958 0.1292 0.031 Uiso 1 1 calc R . . O2 O 0.4547(2) 1.10493(19) 0.31528(12) 0.0347(3) Uani 1 1 d . . . O3 O 1.2369(2) 0.47061(16) 0.09795(10) 0.0265(2) Uani 1 1 d . . . O4 O 1.22352(19) 0.23812(15) -0.04573(10) 0.0247(2) Uani 1 1 d . . . S1 S 1.25955(8) 0.66017(7) 0.41226(4) 0.03711(14) Uani 1 1 d D . . H1S H 1.275(4) 0.482(3) 0.397(2) 0.045 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 C1 0.0244(6) 0.0296(7) 0.0267(6) 0.0093(5) -0.0065(5) -0.0059(5) C2 0.0173(5) 0.0221(6) 0.0196(5) 0.0010(4) -0.0050(4) -0.0040(4) C3 0.0172(5) 0.0192(6) 0.0230(6) -0.0005(4) -0.0050(4) -0.0032(4) C4 0.0149(5) 0.0169(5) 0.0224(5) 0.0041(4) -0.0045(4) -0.0038(4) N1 0.0165(4) 0.0201(5) 0.0224(5) 0.0012(4) -0.0039(4) -0.0039(4) O1 0.0164(4) 0.0284(5) 0.0283(5) 0.0083(4) -0.0065(4) -0.0013(4) O2 0.0192(5) 0.0415(6) 0.0389(6) 0.0113(5) -0.0029(4) -0.0081(4) O3 0.0230(4) 0.0231(5) 0.0319(5) -0.0016(4) -0.0143(4) 0.0000(4) O4 0.0210(4) 0.0177(4) 0.0324(5) -0.0017(4) -0.0074(4) -0.0014(3) S1 0.0359(2) 0.0358(2) 0.0384(2) 0.01181(16) -0.01926(17) -0.00485(17) _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 C2 1.5202(19) . ? C1 S1 1.8176(14) . ? C1 H11 0.9800 . ? C1 H12 0.9800 . ? C2 N1 1.4893(15) . ? C2 C3 1.5313(17) . ? C2 H2 0.9900 . ? C3 O2 1.2114(16) . ? C3 O1 1.3018(16) . ? C4 O4 1.2408(15) . ? C4 O3 1.2634(15) . ? C4 C4 1.556(2) 2_765 ? N1 H1N 0.9000 . ? N1 H2N 0.9000 . ? N1 H3N 0.9000 . ? O1 H1O 0.8300 . ? S1 H1S 1.175(15) . ? 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 C2 C1 S1 112.33(10) . . ? C2 C1 H11 109.1 . . ? S1 C1 H11 109.1 . . ? C2 C1 H12 109.1 . . ? S1 C1 H12 109.1 . . ? H11 C1 H12 107.9 . . ? N1 C2 C1 110.90(11) . . ? N1 C2 C3 110.16(10) . . ? C1 C2 C3 111.41(10) . . ? N1 C2 H2 108.1 . . ? C1 C2 H2 108.1 . . ? C3 C2 H2 108.1 . . ? O2 C3 O1 125.41(12) . . ? O2 C3 C2 121.38(12) . . ? O1 C3 C2 113.14(10) . . ? O4 C4 O3 126.20(11) . . ? O4 C4 C4 118.96(13) . 2_765 ? O3 C4 C4 114.84(13) . 2_765 ? C2 N1 H1N 109.5 . . ? C2 N1 H2N 109.5 . . ? H1N N1 H2N 109.5 . . ? C2 N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? C3 O1 H1O 109.5 . . ? C1 S1 H1S 100.4(10) . . ? 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 S1 C1 C2 N1 60.10(13) . . . . ? S1 C1 C2 C3 -176.81(9) . . . . ? N1 C2 C3 O2 145.32(13) . . . . ? C1 C2 C3 O2 21.80(17) . . . . ? N1 C2 C3 O1 -37.47(14) . . . . ? C1 C2 C3 O1 -160.98(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.90 2.07 2.9621(15) 168.5 1_565 N1 H3N O4 0.90 2.30 2.9989(14) 134.7 2_865 N1 H2N O3 0.90 2.10 2.8691(15) 142.9 . N1 H2N O1 0.90 2.59 3.0636(14) 113.3 2_775 N1 H2N O4 0.90 2.24 2.9615(14) 137.4 2_765 O1 H1O O3 0.83 1.68 2.4951(13) 169.1 1_465 S1 H1S O2 1.175(15) 2.474(16) 3.6058(14) 161.0(15) 1_645 N1 H3N O2 0.90 2.62 3.1216(17) 116.4 1_655 C2 H2 O2 0.99 2.40 3.1301(17) 130.4 1_655 C1 H12 O2 0.98 2.51 3.4428(19) 159.4 2_676 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.474 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.056 # END data_DL-cys_ox_21_225K _database_code_depnum_ccdc_archive 'CCDC 868548' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium oxalate' _chemical_formula_moiety 'C3 H8 N O2 S, 0.5(C2 O4)' _chemical_formula_sum 'C4 H8 N O4 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 225(2) _chemical_formula_weight 166.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2644(3) _cell_length_b 6.6233(4) _cell_length_c 10.3965(4) _cell_angle_alpha 87.021(4) _cell_angle_beta 76.908(4) _cell_angle_gamma 70.282(5) _cell_volume 332.26(3) _cell_formula_units_Z 2 _cell_measurement_temperature 225(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.441 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8503 _exptl_absorpt_correction_T_max 0.9131 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 5482 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 30.99 _reflns_number_total 2102 _reflns_number_gt 1797 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0540P)^2^+0.0804P] 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 2102 _refine_ls_number_parameters 96 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 C1 C 0.9335(3) 0.8021(2) 0.36629(13) 0.0255(3) Uani 1 1 d . . . H11 H 0.8798 0.7014 0.3215 0.031 Uiso 1 1 calc R . . H12 H 0.7897 0.8575 0.4464 0.031 Uiso 1 1 calc R . . C2 C 0.9498(2) 0.98738(19) 0.27591(11) 0.0182(2) Uani 1 1 d . . . H2 H 1.0055 1.0868 0.3224 0.022 Uiso 1 1 calc R . . C3 C 0.6690(2) 1.11202(19) 0.24454(11) 0.0188(2) Uani 1 1 d . . . C4 C 1.1333(2) 0.41425(18) 0.01378(11) 0.0167(2) Uani 1 1 d . . . N1 N 1.1630(2) 0.90973(16) 0.15153(10) 0.0184(2) Uani 1 1 d . . . H1N H 1.1572 1.0194 0.0961 0.022 Uiso 1 1 calc R . . H2N H 1.1289 0.8057 0.1132 0.022 Uiso 1 1 calc R . . H3N H 1.3317 0.8572 0.1702 0.022 Uiso 1 1 calc R . . O1 O 0.68752(18) 1.22838(15) 0.14004(9) 0.0236(2) Uani 1 1 d . . . H1O H 0.5302 1.2945 0.1282 0.028 Uiso 1 1 calc R . . O2 O 0.45458(19) 1.10518(18) 0.31553(11) 0.0314(2) Uani 1 1 d . . . O3 O 1.23709(18) 0.47094(15) 0.09809(9) 0.0241(2) Uani 1 1 d . . . O4 O 1.22371(18) 0.23772(14) -0.04602(9) 0.02228(19) Uani 1 1 d . . . S1 S 1.25996(8) 0.66020(6) 0.41223(4) 0.03365(13) Uani 1 1 d D . . H1S H 1.268(4) 0.481(2) 0.399(2) 0.040 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 C1 0.0228(5) 0.0269(6) 0.0240(6) 0.0086(5) -0.0056(5) -0.0056(5) C2 0.0155(5) 0.0192(5) 0.0181(5) 0.0010(4) -0.0043(4) -0.0033(4) C3 0.0158(5) 0.0173(5) 0.0215(5) 0.0001(4) -0.0048(4) -0.0030(4) C4 0.0135(4) 0.0151(5) 0.0200(5) 0.0037(4) -0.0040(4) -0.0031(4) N1 0.0150(4) 0.0182(4) 0.0202(4) 0.0011(3) -0.0034(3) -0.0037(3) O1 0.0152(4) 0.0254(5) 0.0259(4) 0.0075(3) -0.0060(3) -0.0015(3) O2 0.0173(4) 0.0373(6) 0.0355(5) 0.0099(4) -0.0028(4) -0.0072(4) O3 0.0211(4) 0.0208(4) 0.0290(5) -0.0012(3) -0.0128(4) -0.0004(3) O4 0.0189(4) 0.0161(4) 0.0289(4) -0.0017(3) -0.0062(3) -0.0013(3) S1 0.0325(2) 0.0326(2) 0.0345(2) 0.01069(14) -0.01707(15) -0.00433(15) _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 C2 1.5202(18) . ? C1 S1 1.8169(13) . ? C1 H11 0.9800 . ? C1 H12 0.9800 . ? C2 N1 1.4894(14) . ? C2 C3 1.5298(16) . ? C2 H2 0.9900 . ? C3 O2 1.2143(14) . ? C3 O1 1.3036(14) . ? C4 O4 1.2435(14) . ? C4 O3 1.2637(14) . ? C4 C4 1.554(2) 2_765 ? N1 H1N 0.9000 . ? N1 H2N 0.9000 . ? N1 H3N 0.9000 . ? O1 H1O 0.8300 . ? S1 H1S 1.185(14) . ? 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 C2 C1 S1 112.34(9) . . ? C2 C1 H11 109.1 . . ? S1 C1 H11 109.1 . . ? C2 C1 H12 109.1 . . ? S1 C1 H12 109.1 . . ? H11 C1 H12 107.9 . . ? N1 C2 C1 110.93(10) . . ? N1 C2 C3 110.27(9) . . ? C1 C2 C3 111.47(10) . . ? N1 C2 H2 108.0 . . ? C1 C2 H2 108.0 . . ? C3 C2 H2 108.0 . . ? O2 C3 O1 125.34(11) . . ? O2 C3 C2 121.38(11) . . ? O1 C3 C2 113.21(10) . . ? O4 C4 O3 126.16(10) . . ? O4 C4 C4 118.91(12) . 2_765 ? O3 C4 C4 114.93(12) . 2_765 ? C2 N1 H1N 109.5 . . ? C2 N1 H2N 109.5 . . ? H1N N1 H2N 109.5 . . ? C2 N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? C3 O1 H1O 109.5 . . ? C1 S1 H1S 99.2(10) . . ? 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 S1 C1 C2 N1 59.78(12) . . . . ? S1 C1 C2 C3 -176.91(8) . . . . ? N1 C2 C3 O2 145.34(12) . . . . ? C1 C2 C3 O2 21.66(16) . . . . ? N1 C2 C3 O1 -37.36(13) . . . . ? C1 C2 C3 O1 -161.04(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.90 2.07 2.9575(14) 168.9 1_565 N1 H3N O4 0.90 2.29 2.9933(13) 134.4 2_865 N1 H2N O3 0.90 2.10 2.8656(14) 142.4 . N1 H2N O1 0.90 2.58 3.0605(13) 113.8 2_775 N1 H2N O4 0.90 2.23 2.9608(13) 137.7 2_765 O1 H1O O3 0.83 1.68 2.4938(12) 168.1 1_465 S1 H1S O2 1.185(14) 2.471(15) 3.5986(12) 158.1(14) 1_645 N1 H3N O2 0.90 2.61 3.1137(15) 116.1 1_655 C2 H2 O2 0.99 2.39 3.1254(15) 130.3 1_655 C1 H12 O2 0.98 2.50 3.4345(17) 159.5 2_676 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.474 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.057 # END data_DL-cys_ox_21_200K _database_code_depnum_ccdc_archive 'CCDC 868549' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium oxalate' _chemical_formula_moiety 'C3 H8 N O2 S, 0.5(C2 O4)' _chemical_formula_sum 'C4 H8 N O4 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 200(2) _chemical_formula_weight 166.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2615(3) _cell_length_b 6.6145(4) _cell_length_c 10.3827(4) _cell_angle_alpha 87.080(4) _cell_angle_beta 76.924(4) _cell_angle_gamma 70.335(5) _cell_volume 331.32(3) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.442 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8499 _exptl_absorpt_correction_T_max 0.9129 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 5288 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 30.50 _reflns_number_total 2017 _reflns_number_gt 1777 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0500P)^2^+0.1006P] 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 2017 _refine_ls_number_parameters 96 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0951 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 C1 C 0.9331(3) 0.8023(2) 0.36635(13) 0.0232(3) Uani 1 1 d . . . H11 H 0.8789 0.7005 0.3209 0.028 Uiso 1 1 calc R . . H12 H 0.7879 0.8581 0.4475 0.028 Uiso 1 1 calc R . . C2 C 0.9498(2) 0.98797(19) 0.27605(11) 0.0168(2) Uani 1 1 d . . . H2 H 1.0059 1.0885 0.3232 0.020 Uiso 1 1 calc R . . C3 C 0.6690(2) 1.11245(19) 0.24456(12) 0.0171(2) Uani 1 1 d . . . C4 C 1.1336(2) 0.41431(18) 0.01369(11) 0.0154(2) Uani 1 1 d . . . N1 N 1.1633(2) 0.91019(17) 0.15142(10) 0.0168(2) Uani 1 1 d . . . H1N H 1.1573 1.0211 0.0953 0.020 Uiso 1 1 calc R . . H2N H 1.1290 0.8047 0.1126 0.020 Uiso 1 1 calc R . . H3N H 1.3339 0.8573 0.1703 0.020 Uiso 1 1 calc R . . O1 O 0.68779(18) 1.22905(15) 0.14008(9) 0.0214(2) Uani 1 1 d . . . H1O H 0.5284 1.2977 0.1289 0.026 Uiso 1 1 calc R . . O2 O 0.45466(19) 1.10542(17) 0.31571(10) 0.0282(2) Uani 1 1 d . . . O3 O 1.23727(18) 0.47126(15) 0.09822(9) 0.0218(2) Uani 1 1 d . . . O4 O 1.22361(18) 0.23757(14) -0.04616(9) 0.02020(19) Uani 1 1 d . . . S1 S 1.26041(8) 0.66022(6) 0.41227(4) 0.03029(12) Uani 1 1 d D . . H1S H 1.265(4) 0.483(2) 0.396(2) 0.036 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 C1 0.0202(5) 0.0246(6) 0.0223(6) 0.0075(5) -0.0051(5) -0.0049(5) C2 0.0141(5) 0.0178(5) 0.0165(5) 0.0008(4) -0.0035(4) -0.0029(4) C3 0.0148(5) 0.0159(5) 0.0194(5) -0.0004(4) -0.0043(4) -0.0030(4) C4 0.0124(4) 0.0142(5) 0.0183(5) 0.0034(4) -0.0034(4) -0.0034(4) N1 0.0136(4) 0.0168(4) 0.0185(5) 0.0016(3) -0.0034(3) -0.0035(3) O1 0.0135(4) 0.0236(5) 0.0232(4) 0.0065(3) -0.0052(3) -0.0014(3) O2 0.0165(4) 0.0332(5) 0.0311(5) 0.0085(4) -0.0024(4) -0.0065(4) O3 0.0188(4) 0.0191(4) 0.0261(4) -0.0012(3) -0.0113(3) -0.0001(3) O4 0.0173(4) 0.0146(4) 0.0264(4) -0.0009(3) -0.0059(3) -0.0016(3) S1 0.02908(19) 0.0298(2) 0.0308(2) 0.00955(14) -0.01527(14) -0.00402(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 C1 C2 1.5208(18) . ? C1 S1 1.8199(13) . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? C2 N1 1.4907(14) . ? C2 C3 1.5295(16) . ? C2 H2 1.0000 . ? C3 O2 1.2143(15) . ? C3 O1 1.3035(15) . ? C4 O4 1.2431(14) . ? C4 O3 1.2641(14) . ? C4 C4 1.555(2) 2_765 ? N1 H1N 0.9100 . ? N1 H2N 0.9100 . ? N1 H3N 0.9100 . ? O1 H1O 0.8400 . ? S1 H1S 1.183(14) . ? 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 C2 C1 S1 112.25(9) . . ? C2 C1 H11 109.2 . . ? S1 C1 H11 109.2 . . ? C2 C1 H12 109.2 . . ? S1 C1 H12 109.2 . . ? H11 C1 H12 107.9 . . ? N1 C2 C1 110.89(10) . . ? N1 C2 C3 110.26(9) . . ? C1 C2 C3 111.42(10) . . ? N1 C2 H2 108.0 . . ? C1 C2 H2 108.0 . . ? C3 C2 H2 108.0 . . ? O2 C3 O1 125.45(11) . . ? O2 C3 C2 121.31(11) . . ? O1 C3 C2 113.17(10) . . ? O4 C4 O3 126.24(11) . . ? O4 C4 C4 118.83(13) . 2_765 ? O3 C4 C4 114.93(12) . 2_765 ? C2 N1 H1N 109.5 . . ? C2 N1 H2N 109.5 . . ? H1N N1 H2N 109.5 . . ? C2 N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? C3 O1 H1O 109.5 . . ? C1 S1 H1S 97.9(10) . . ? 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 S1 C1 C2 N1 59.78(12) . . . . ? S1 C1 C2 C3 -176.99(8) . . . . ? N1 C2 C3 O2 145.38(12) . . . . ? C1 C2 C3 O2 21.79(16) . . . . ? N1 C2 C3 O1 -37.46(13) . . . . ? C1 C2 C3 O1 -161.05(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.91 2.05 2.9518(14) 168.8 1_565 N1 H3N O4 0.91 2.28 2.9911(13) 134.3 2_865 N1 H2N O3 0.91 2.09 2.8621(14) 142.2 . N1 H2N O1 0.91 2.58 3.0574(13) 113.7 2_775 N1 H2N O4 0.91 2.22 2.9578(13) 137.3 2_765 O1 H1O O3 0.84 1.66 2.4928(12) 169.1 1_465 S1 H1S O2 1.183(14) 2.467(15) 3.5922(12) 158.0(14) 1_645 N1 H3N O2 0.91 2.60 3.1092(15) 116.0 1_655 C2 H2 O2 1.00 2.38 3.1220(15) 129.9 1_655 C1 H12 O2 0.99 2.48 3.4282(17) 159.5 2_676 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.521 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.059 # END data_DL-cys_ox_21_175K _database_code_depnum_ccdc_archive 'CCDC 868550' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium oxalate' _chemical_formula_moiety 'C3 H8 N O2 S, 0.5(C2 O4)' _chemical_formula_sum 'C4 H8 N O4 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 175(2) _chemical_formula_weight 166.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2589(3) _cell_length_b 6.6056(4) _cell_length_c 10.3687(4) _cell_angle_alpha 87.155(4) _cell_angle_beta 76.947(4) _cell_angle_gamma 70.385(5) _cell_volume 330.39(3) _cell_formula_units_Z 2 _cell_measurement_temperature 175(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.443 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8496 _exptl_absorpt_correction_T_max 0.9126 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 5566 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 31.25 _reflns_number_total 2151 _reflns_number_gt 1863 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0474P)^2^+0.1158P] 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 2151 _refine_ls_number_parameters 96 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0941 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 C3 C 0.6692(2) 1.11279(19) 0.24455(11) 0.0156(2) Uani 1 1 d . . . C2 C 0.9500(2) 0.98838(19) 0.27613(11) 0.0154(2) Uani 1 1 d . . . H2 H 1.0061 1.0891 0.3235 0.018 Uiso 1 1 calc R . . C1 C 0.9333(3) 0.8023(2) 0.36644(13) 0.0212(2) Uani 1 1 d . . . H11 H 0.8791 0.7003 0.3208 0.025 Uiso 1 1 calc R . . H12 H 0.7880 0.8581 0.4477 0.025 Uiso 1 1 calc R . . C4 C 1.1335(2) 0.41420(18) 0.01380(11) 0.0141(2) Uani 1 1 d . . . N1 N 1.1637(2) 0.91055(16) 0.15150(10) 0.01527(19) Uani 1 1 d . . . H3N H 1.3343 0.8584 0.1704 0.018 Uiso 1 1 calc R . . H1N H 1.1571 1.0214 0.0952 0.018 Uiso 1 1 calc R . . H2N H 1.1300 0.8043 0.1128 0.018 Uiso 1 1 calc R . . O1 O 0.68836(18) 1.22953(15) 0.13999(9) 0.01938(19) Uani 1 1 d . . . H1O H 0.5291 1.2984 0.1287 0.023 Uiso 1 1 calc R . . O2 O 0.45457(19) 1.10580(17) 0.31580(10) 0.0253(2) Uani 1 1 d . . . O3 O 1.23755(18) 0.47179(15) 0.09838(9) 0.01971(19) Uani 1 1 d . . . O4 O 1.22390(18) 0.23719(14) -0.04638(9) 0.01825(18) Uani 1 1 d . . . S1 S 1.26076(7) 0.66031(6) 0.41228(3) 0.02722(11) Uani 1 1 d D . . H1S H 1.273(4) 0.481(2) 0.3963(19) 0.033 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 C3 0.0136(5) 0.0146(5) 0.0176(5) -0.0005(4) -0.0039(4) -0.0030(4) C2 0.0130(4) 0.0172(5) 0.0147(5) 0.0009(4) -0.0034(4) -0.0032(4) C1 0.0185(5) 0.0227(6) 0.0204(5) 0.0077(5) -0.0050(4) -0.0049(5) C4 0.0116(4) 0.0131(5) 0.0166(5) 0.0032(4) -0.0029(4) -0.0033(4) N1 0.0128(4) 0.0151(4) 0.0166(4) 0.0012(3) -0.0031(3) -0.0031(3) O1 0.0128(4) 0.0210(4) 0.0210(4) 0.0059(3) -0.0050(3) -0.0013(3) O2 0.0149(4) 0.0298(5) 0.0280(5) 0.0074(4) -0.0024(4) -0.0060(4) O3 0.0172(4) 0.0174(4) 0.0235(4) -0.0010(3) -0.0102(3) -0.0005(3) O4 0.0158(4) 0.0135(4) 0.0233(4) -0.0009(3) -0.0048(3) -0.0015(3) S1 0.02617(18) 0.02690(19) 0.02754(18) 0.00858(13) -0.01352(13) -0.00368(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 C3 O2 1.2151(14) . ? C3 O1 1.3038(14) . ? C3 C2 1.5301(16) . ? C2 N1 1.4895(14) . ? C2 C1 1.5222(17) . ? C2 H2 1.0000 . ? C1 S1 1.8201(13) . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? C4 O4 1.2440(14) . ? C4 O3 1.2659(14) . ? C4 C4 1.556(2) 2_765 ? N1 H3N 0.9100 . ? N1 H1N 0.9100 . ? N1 H2N 0.9100 . ? O1 H1O 0.8400 . ? S1 H1S 1.181(14) . ? 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 O2 C3 O1 125.51(11) . . ? O2 C3 C2 121.32(11) . . ? O1 C3 C2 113.09(10) . . ? N1 C2 C1 110.85(10) . . ? N1 C2 C3 110.29(9) . . ? C1 C2 C3 111.38(10) . . ? N1 C2 H2 108.1 . . ? C1 C2 H2 108.1 . . ? C3 C2 H2 108.1 . . ? C2 C1 S1 112.17(9) . . ? C2 C1 H11 109.2 . . ? S1 C1 H11 109.2 . . ? C2 C1 H12 109.2 . . ? S1 C1 H12 109.2 . . ? H11 C1 H12 107.9 . . ? O4 C4 O3 126.27(11) . . ? O4 C4 C4 118.84(12) . 2_765 ? O3 C4 C4 114.89(12) . 2_765 ? C2 N1 H3N 109.5 . . ? C2 N1 H1N 109.5 . . ? H3N N1 H1N 109.5 . . ? C2 N1 H2N 109.5 . . ? H3N N1 H2N 109.5 . . ? H1N N1 H2N 109.5 . . ? C3 O1 H1O 109.5 . . ? C1 S1 H1S 99.5(9) . . ? 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 C3 C2 N1 145.43(11) . . . . ? O1 C3 C2 N1 -37.52(13) . . . . ? O2 C3 C2 C1 21.91(16) . . . . ? O1 C3 C2 C1 -161.04(10) . . . . ? N1 C2 C1 S1 59.75(12) . . . . ? C3 C2 C1 S1 -177.05(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.91 2.05 2.9481(14) 168.6 1_565 N1 H3N O4 0.91 2.28 2.9872(13) 134.3 2_865 N1 H2N O3 0.91 2.08 2.8565(14) 142.5 . N1 H2N O1 0.91 2.57 3.0543(13) 113.7 2_775 N1 H2N O4 0.91 2.23 2.9562(13) 136.9 2_765 O1 H1O O3 0.84 1.66 2.4928(12) 169.3 1_465 S1 H1S O2 1.181(14) 2.453(15) 3.5851(12) 159.9(14) 1_645 N1 H3N O2 0.91 2.59 3.1026(15) 116.3 1_655 C2 H2 O2 1.00 2.38 3.1172(15) 129.8 1_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 31.25 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.504 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.061 # END data_DL-cys_ox_21_150K _database_code_depnum_ccdc_archive 'CCDC 868551' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium oxalate' _chemical_formula_moiety 'C3 H8 N O2 S, 0.5(C2 O4)' _chemical_formula_sum 'C4 H8 N O4 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 150(2) _chemical_formula_weight 166.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2563(3) _cell_length_b 6.5980(3) _cell_length_c 10.3562(4) _cell_angle_alpha 87.226(4) _cell_angle_beta 76.973(4) _cell_angle_gamma 70.438(5) _cell_volume 329.58(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.675 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.445 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8492 _exptl_absorpt_correction_T_max 0.9124 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 5247 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 30.50 _reflns_number_total 2009 _reflns_number_gt 1783 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0449P)^2^+0.1301P] 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 2009 _refine_ls_number_parameters 96 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 C1 C 0.9330(3) 0.8026(2) 0.36652(13) 0.0191(2) Uani 1 1 d . . . H11 H 0.8789 0.7005 0.3207 0.023 Uiso 1 1 calc R . . H12 H 0.7877 0.8583 0.4479 0.023 Uiso 1 1 calc R . . C2 C 0.9503(2) 0.98880(19) 0.27636(11) 0.0138(2) Uani 1 1 d . . . H2 H 1.0062 1.0896 0.3240 0.017 Uiso 1 1 calc R . . C3 C 0.6697(2) 1.11317(19) 0.24471(11) 0.0139(2) Uani 1 1 d . . . C4 C 1.1337(2) 0.41439(18) 0.01356(11) 0.0128(2) Uani 1 1 d . . . N1 N 1.1643(2) 0.91105(17) 0.15152(10) 0.01386(19) Uani 1 1 d . . . H1N H 1.1564 1.0216 0.0948 0.017 Uiso 1 1 calc R . . H2N H 1.1321 0.8035 0.1131 0.017 Uiso 1 1 calc R . . H3N H 1.3351 0.8605 0.1704 0.017 Uiso 1 1 calc R . . O1 O 0.68878(18) 1.23012(15) 0.13992(9) 0.01699(19) Uani 1 1 d . . . H1O H 0.5296 1.2969 0.1277 0.020 Uiso 1 1 calc R . . O2 O 0.45436(19) 1.10618(17) 0.31582(10) 0.0223(2) Uani 1 1 d . . . O3 O 1.23774(18) 0.47215(15) 0.09838(9) 0.01752(19) Uani 1 1 d . . . O4 O 1.22429(18) 0.23691(14) -0.04674(9) 0.01622(18) Uani 1 1 d . . . S1 S 1.26083(7) 0.66058(6) 0.41242(3) 0.02413(11) Uani 1 1 d D . . H1S H 1.270(4) 0.481(2) 0.3975(19) 0.029 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 C1 0.0167(5) 0.0204(6) 0.0184(5) 0.0069(4) -0.0047(4) -0.0041(5) C2 0.0115(5) 0.0156(5) 0.0127(5) 0.0007(4) -0.0027(4) -0.0027(4) C3 0.0124(5) 0.0128(5) 0.0155(5) -0.0007(4) -0.0035(4) -0.0024(4) C4 0.0101(4) 0.0125(5) 0.0145(5) 0.0033(4) -0.0023(4) -0.0030(4) N1 0.0115(4) 0.0137(4) 0.0152(4) 0.0007(3) -0.0026(3) -0.0030(4) O1 0.0112(4) 0.0187(4) 0.0181(4) 0.0051(3) -0.0044(3) -0.0011(3) O2 0.0134(4) 0.0265(5) 0.0246(5) 0.0063(4) -0.0020(3) -0.0057(4) O3 0.0151(4) 0.0160(4) 0.0205(4) -0.0004(3) -0.0087(3) -0.0007(3) O4 0.0139(4) 0.0121(4) 0.0206(4) -0.0004(3) -0.0041(3) -0.0015(3) S1 0.02308(17) 0.02414(19) 0.02411(18) 0.00767(13) -0.01171(13) -0.00323(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 C1 C2 1.5216(17) . ? C1 S1 1.8216(13) . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? C2 N1 1.4908(14) . ? C2 C3 1.5289(16) . ? C2 H2 1.0000 . ? C3 O2 1.2170(14) . ? C3 O1 1.3057(14) . ? C4 O4 1.2455(14) . ? C4 O3 1.2666(14) . ? C4 C4 1.554(2) 2_765 ? N1 H1N 0.9100 . ? N1 H2N 0.9100 . ? N1 H3N 0.9100 . ? O1 H1O 0.8400 . ? S1 H1S 1.185(14) . ? 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 C2 C1 S1 112.05(9) . . ? C2 C1 H11 109.2 . . ? S1 C1 H11 109.2 . . ? C2 C1 H12 109.2 . . ? S1 C1 H12 109.2 . . ? H11 C1 H12 107.9 . . ? N1 C2 C1 110.90(10) . . ? N1 C2 C3 110.30(9) . . ? C1 C2 C3 111.32(10) . . ? N1 C2 H2 108.1 . . ? C1 C2 H2 108.1 . . ? C3 C2 H2 108.1 . . ? O2 C3 O1 125.33(11) . . ? O2 C3 C2 121.44(11) . . ? O1 C3 C2 113.16(10) . . ? O4 C4 O3 126.22(11) . . ? O4 C4 C4 118.91(13) . 2_765 ? O3 C4 C4 114.86(13) . 2_765 ? C2 N1 H1N 109.5 . . ? C2 N1 H2N 109.5 . . ? H1N N1 H2N 109.5 . . ? C2 N1 H3N 109.5 . . ? H1N N1 H3N 109.5 . . ? H2N N1 H3N 109.5 . . ? C3 O1 H1O 109.5 . . ? C1 S1 H1S 99.2(9) . . ? 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 S1 C1 C2 N1 59.74(12) . . . . ? S1 C1 C2 C3 -177.05(8) . . . . ? N1 C2 C3 O2 145.42(11) . . . . ? C1 C2 C3 O2 21.86(16) . . . . ? N1 C2 C3 O1 -37.39(13) . . . . ? C1 C2 C3 O1 -160.95(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.91 2.05 2.9449(14) 168.1 1_565 N1 H3N O4 0.91 2.27 2.9812(13) 134.5 2_865 N1 H2N O3 0.91 2.07 2.8545(14) 143.4 . N1 H2N O1 0.91 2.57 3.0518(13) 113.7 2_775 N1 H2N O4 0.91 2.23 2.9564(13) 136.0 2_765 O1 H1O O3 0.84 1.66 2.4928(12) 168.2 1_465 S1 H1S O2 1.185(14) 2.450(15) 3.5805(11) 158.7(13) 1_645 N1 H3N O2 0.91 2.57 3.0939(14) 116.8 1_655 C2 H2 O2 1.00 2.38 3.1114(15) 129.6 1_655 C1 H12 O2 0.99 2.47 3.4179(16) 159.5 2_676 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.490 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.061 # END data_DL-cys_ox_21_125K _database_code_depnum_ccdc_archive 'CCDC 868552' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium oxalate' _chemical_formula_moiety 'C3 H8 N O2 S, 0.5(C2 O4)' _chemical_formula_sum 'C4 H8 N O4 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 125(2) _chemical_formula_weight 166.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2540(3) _cell_length_b 6.5904(3) _cell_length_c 10.3425(4) _cell_angle_alpha 87.327(4) _cell_angle_beta 77.009(4) _cell_angle_gamma 70.477(5) _cell_volume 328.73(3) _cell_formula_units_Z 2 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.446 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8489 _exptl_absorpt_correction_T_max 0.9122 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 5236 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 30.49 _reflns_number_total 2004 _reflns_number_gt 1783 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0413P)^2^+0.1514P] 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 2004 _refine_ls_number_parameters 96 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0852 _refine_ls_wR_factor_gt 0.0834 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 C3 C 0.6694(2) 1.11380(19) 0.24461(12) 0.0129(2) Uani 1 1 d . . . C2 C 0.9501(2) 0.98947(19) 0.27656(11) 0.0127(2) Uani 1 1 d . . . H2 H 1.0057 1.0905 0.3245 0.015 Uiso 1 1 calc R . . C1 C 0.9328(3) 0.8028(2) 0.36660(12) 0.0170(2) Uani 1 1 d . . . H11 H 0.8789 0.7006 0.3205 0.020 Uiso 1 1 calc R . . H12 H 0.7872 0.8585 0.4480 0.020 Uiso 1 1 calc R . . C4 C 1.1338(2) 0.41437(18) 0.01365(11) 0.0114(2) Uani 1 1 d . . . N1 N 1.1649(2) 0.91157(16) 0.15166(10) 0.01239(19) Uani 1 1 d . . . H3N H 1.3357 0.8627 0.1707 0.015 Uiso 1 1 calc R . . H1N H 1.1557 1.0218 0.0946 0.015 Uiso 1 1 calc R . . H2N H 1.1343 0.8027 0.1136 0.015 Uiso 1 1 calc R . . O1 O 0.68920(17) 1.23092(15) 0.13989(9) 0.01512(18) Uani 1 1 d . . . H1O H 0.5301 1.2989 0.1280 0.018 Uiso 1 1 calc R . . O2 O 0.45419(19) 1.10665(16) 0.31577(10) 0.0198(2) Uani 1 1 d . . . O3 O 1.23816(18) 0.47254(15) 0.09843(9) 0.01562(18) Uani 1 1 d . . . O4 O 1.22431(17) 0.23670(14) -0.04683(9) 0.01450(18) Uani 1 1 d . . . S1 S 1.26081(7) 0.66105(6) 0.41262(3) 0.02124(10) Uani 1 1 d D . . H1S H 1.266(4) 0.483(2) 0.3962(18) 0.025 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 C3 0.0117(5) 0.0115(5) 0.0147(5) -0.0008(4) -0.0037(4) -0.0021(4) C2 0.0101(5) 0.0150(5) 0.0113(5) 0.0001(4) -0.0017(4) -0.0026(4) C1 0.0148(5) 0.0175(6) 0.0169(5) 0.0061(4) -0.0041(4) -0.0034(5) C4 0.0091(4) 0.0107(5) 0.0132(5) 0.0025(4) -0.0015(4) -0.0025(4) N1 0.0105(4) 0.0122(4) 0.0132(4) 0.0007(3) -0.0021(3) -0.0025(3) O1 0.0100(4) 0.0166(4) 0.0162(4) 0.0045(3) -0.0038(3) -0.0011(3) O2 0.0122(4) 0.0235(5) 0.0216(5) 0.0050(4) -0.0020(3) -0.0052(4) O3 0.0134(4) 0.0142(4) 0.0182(4) -0.0004(3) -0.0070(3) -0.0008(3) O4 0.0124(4) 0.0110(4) 0.0180(4) -0.0004(3) -0.0033(3) -0.0011(3) S1 0.02023(17) 0.02143(18) 0.02110(17) 0.00650(12) -0.00993(12) -0.00297(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 C3 O2 1.2169(15) . ? C3 O1 1.3056(14) . ? C3 C2 1.5300(16) . ? C2 N1 1.4916(14) . ? C2 C1 1.5225(17) . ? C2 H2 1.0000 . ? C1 S1 1.8225(13) . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? C4 O4 1.2453(14) . ? C4 O3 1.2668(14) . ? C4 C4 1.555(2) 2_765 ? N1 H3N 0.9100 . ? N1 H1N 0.9100 . ? N1 H2N 0.9100 . ? O1 H1O 0.8400 . ? S1 H1S 1.186(14) . ? 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 O2 C3 O1 125.51(11) . . ? O2 C3 C2 121.33(11) . . ? O1 C3 C2 113.09(10) . . ? N1 C2 C1 110.84(10) . . ? N1 C2 C3 110.33(9) . . ? C1 C2 C3 111.34(10) . . ? N1 C2 H2 108.1 . . ? C1 C2 H2 108.1 . . ? C3 C2 H2 108.1 . . ? C2 C1 S1 111.99(8) . . ? C2 C1 H11 109.2 . . ? S1 C1 H11 109.2 . . ? C2 C1 H12 109.2 . . ? S1 C1 H12 109.2 . . ? H11 C1 H12 107.9 . . ? O4 C4 O3 126.23(11) . . ? O4 C4 C4 118.85(13) . 2_765 ? O3 C4 C4 114.91(12) . 2_765 ? C2 N1 H3N 109.5 . . ? C2 N1 H1N 109.5 . . ? H3N N1 H1N 109.5 . . ? C2 N1 H2N 109.5 . . ? H3N N1 H2N 109.5 . . ? H1N N1 H2N 109.5 . . ? C3 O1 H1O 109.5 . . ? C1 S1 H1S 98.0(9) . . ? 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 C3 C2 N1 145.49(11) . . . . ? O1 C3 C2 N1 -37.48(13) . . . . ? O2 C3 C2 C1 21.98(16) . . . . ? O1 C3 C2 C1 -160.99(10) . . . . ? N1 C2 C1 S1 59.68(11) . . . . ? C3 C2 C1 S1 -177.10(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.91 2.05 2.9415(13) 167.7 1_565 N1 H3N O4 0.91 2.27 2.9780(13) 134.4 2_865 N1 H2N O3 0.91 2.06 2.8515(14) 144.3 . N1 H2N O1 0.91 2.57 3.0505(13) 113.6 2_775 N1 H2N O4 0.91 2.24 2.9567(13) 135.2 2_765 O1 H1O O3 0.84 1.66 2.4913(12) 169.0 1_465 S1 H1S O2 1.186(14) 2.448(15) 3.5760(11) 158.2(13) 1_645 N1 H3N O2 0.91 2.56 3.0845(14) 117.5 1_655 C2 H2 O2 1.00 2.38 3.1073(15) 129.3 1_655 C1 H12 O2 0.99 2.47 3.4133(16) 159.4 2_676 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.544 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.062 # END data_DL-cys_ox_21_100K _database_code_depnum_ccdc_archive 'CCDC 868553' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'DL-cysteinium oxalate' _chemical_formula_moiety 'C3 H8 N O2 S, 0.5(C2 O4)' _chemical_formula_sum 'C4 H8 N O4 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(2) _chemical_formula_weight 166.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2521(2) _cell_length_b 6.5844(3) _cell_length_c 10.3311(2) _cell_angle_alpha 87.440(3) _cell_angle_beta 77.032(3) _cell_angle_gamma 70.505(3) _cell_volume 328.02(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 174 _exptl_absorpt_coefficient_mu 0.447 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8486 _exptl_absorpt_correction_T_max 0.9120 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 7491 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0111 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 31.50 _reflns_number_total 2180 _reflns_number_gt 2059 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0352P)^2^+0.1634P] 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 2180 _refine_ls_number_parameters 96 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0273 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 C3 C 0.66972(18) 1.11449(14) 0.24450(9) 0.00983(15) Uani 1 1 d . . . C2 C 0.95000(18) 0.99014(14) 0.27683(8) 0.00977(15) Uani 1 1 d . . . H2 H 1.0054 1.0912 0.3251 0.012 Uiso 1 1 calc R . . C1 C 0.93180(19) 0.80343(16) 0.36664(9) 0.01357(17) Uani 1 1 d . . . H11 H 0.8788 0.7008 0.3201 0.016 Uiso 1 1 calc R . . H12 H 0.7857 0.8591 0.4480 0.016 Uiso 1 1 calc R . . C4 C 1.13401(17) 0.41451(14) 0.01361(9) 0.00886(15) Uani 1 1 d . . . N1 N 1.16507(15) 0.91212(12) 0.15188(8) 0.00969(14) Uani 1 1 d . . . H3N H 1.3356 0.8616 0.1712 0.012 Uiso 1 1 calc R . . H1N H 1.1576 1.0228 0.0953 0.012 Uiso 1 1 calc R . . H2N H 1.1332 0.8043 0.1130 0.012 Uiso 1 1 calc R . . O1 O 0.68958(14) 1.23175(11) 0.13982(7) 0.01200(13) Uani 1 1 d . . . H1O H 0.5302 1.3031 0.1295 0.014 Uiso 1 1 calc R . . O2 O 0.45364(14) 1.10771(12) 0.31562(7) 0.01546(14) Uani 1 1 d . . . O3 O 1.23841(14) 0.47309(11) 0.09851(7) 0.01225(13) Uani 1 1 d . . . O4 O 1.22452(14) 0.23634(11) -0.04713(7) 0.01151(13) Uani 1 1 d . . . S1 S 1.26022(5) 0.66217(4) 0.41312(2) 0.01654(8) Uani 1 1 d D . . H1S H 1.262(3) 0.485(2) 0.3992(15) 0.020 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 C3 0.0086(3) 0.0095(3) 0.0108(4) -0.0005(3) -0.0026(3) -0.0020(3) C2 0.0078(3) 0.0108(4) 0.0093(3) 0.0005(3) -0.0016(3) -0.0015(3) C1 0.0119(4) 0.0145(4) 0.0130(4) 0.0051(3) -0.0032(3) -0.0030(3) C4 0.0067(3) 0.0086(3) 0.0106(3) 0.0025(3) -0.0018(3) -0.0020(3) N1 0.0075(3) 0.0098(3) 0.0106(3) 0.0006(2) -0.0013(2) -0.0018(2) O1 0.0077(3) 0.0132(3) 0.0130(3) 0.0039(2) -0.0029(2) -0.0008(2) O2 0.0088(3) 0.0187(3) 0.0174(3) 0.0040(3) -0.0012(2) -0.0042(2) O3 0.0107(3) 0.0110(3) 0.0146(3) -0.0002(2) -0.0063(2) -0.0007(2) O4 0.0097(3) 0.0085(3) 0.0148(3) -0.0004(2) -0.0026(2) -0.0010(2) S1 0.01558(12) 0.01698(12) 0.01635(12) 0.00533(8) -0.00791(9) -0.00226(9) _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 C3 O2 1.2192(11) . ? C3 O1 1.3058(11) . ? C3 C2 1.5299(12) . ? C2 N1 1.4911(11) . ? C2 C1 1.5225(13) . ? C2 H2 1.0000 . ? C1 S1 1.8254(10) . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? C4 O4 1.2473(11) . ? C4 O3 1.2673(11) . ? C4 C4 1.5555(17) 2_765 ? N1 H3N 0.9100 . ? N1 H1N 0.9100 . ? N1 H2N 0.9100 . ? O1 H1O 0.8400 . ? S1 H1S 1.179(12) . ? 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 O2 C3 O1 125.36(8) . . ? O2 C3 C2 121.35(8) . . ? O1 C3 C2 113.21(7) . . ? N1 C2 C1 110.87(7) . . ? N1 C2 C3 110.24(7) . . ? C1 C2 C3 111.27(7) . . ? N1 C2 H2 108.1 . . ? C1 C2 H2 108.1 . . ? C3 C2 H2 108.1 . . ? C2 C1 S1 111.76(6) . . ? C2 C1 H11 109.3 . . ? S1 C1 H11 109.3 . . ? C2 C1 H12 109.3 . . ? S1 C1 H12 109.3 . . ? H11 C1 H12 107.9 . . ? O4 C4 O3 126.32(8) . . ? O4 C4 C4 118.72(10) . 2_765 ? O3 C4 C4 114.96(9) . 2_765 ? C2 N1 H3N 109.5 . . ? C2 N1 H1N 109.5 . . ? H3N N1 H1N 109.5 . . ? C2 N1 H2N 109.5 . . ? H3N N1 H2N 109.5 . . ? H1N N1 H2N 109.5 . . ? C3 O1 H1O 109.5 . . ? C1 S1 H1S 97.7(8) . . ? 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 C3 C2 N1 145.58(9) . . . . ? O1 C3 C2 N1 -37.52(10) . . . . ? O2 C3 C2 C1 22.16(12) . . . . ? O1 C3 C2 C1 -160.95(8) . . . . ? N1 C2 C1 S1 59.92(9) . . . . ? C3 C2 C1 S1 -177.01(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O4 0.91 2.04 2.9406(10) 168.2 1_565 N1 H3N O4 0.91 2.27 2.9750(10) 134.2 2_865 N1 H2N O3 0.91 2.07 2.8483(10) 143.2 . N1 H2N O1 0.91 2.56 3.0499(10) 114.2 2_775 N1 H2N O4 0.91 2.23 2.9558(10) 135.9 2_765 O1 H1O O3 0.84 1.66 2.4905(9) 170.8 1_465 S1 H1S O2 1.179(12) 2.461(13) 3.5733(8) 156.5(11) 1_645 N1 H3N O2 0.91 2.56 3.0765(11) 116.8 1_655 C2 H2 O2 1.00 2.37 3.1027(11) 129.2 1_655 C1 H12 O2 0.99 2.47 3.4081(12) 159.0 2_676 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 31.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.569 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.058 # END # Attachment '- CIFs_NAC_Mod.txt' data_NAC_295K _database_code_depnum_ccdc_archive 'CCDC 868554' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common N-Acetyl-L-Cysteine _chemical_formula_moiety 'C5 H9 N O3 S' _chemical_formula_sum 'C5 H9 N O3 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 295(2) _chemical_formula_weight 163.20 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_int_tables_number 1 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.08996(15) _cell_length_b 5.8843(2) _cell_length_c 6.5214(2) _cell_angle_alpha 96.452(3) _cell_angle_beta 103.859(3) _cell_angle_gamma 102.076(3) _cell_volume 182.703(11) _cell_formula_units_Z 1 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 86 _exptl_absorpt_coefficient_mu 0.390 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8565 _exptl_absorpt_correction_T_max 0.9511 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 13790 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 40.24 _reflns_number_total 4604 _reflns_number_gt 4192 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0417P)^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 0.65(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(3) _refine_ls_number_reflns 4604 _refine_ls_number_parameters 96 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0729 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 S1 S 0.19846(2) -0.06982(2) 0.78215(2) 0.03503(6) Uani 1 1 d D . . H1S H 0.266(3) 0.031(2) 0.9687(19) 0.042 Uiso 1 1 d D . . O3 O 0.98604(15) 0.43326(14) 1.09450(10) 0.03944(14) Uani 1 1 d . . . O1 O 0.27562(15) 0.44354(12) 0.47947(9) 0.03868(15) Uani 1 1 d . . . H1O H 0.2120 0.4589 0.3552 0.046 Uiso 1 1 calc R . . N1 N 0.59043(13) 0.45980(11) 0.86764(9) 0.02583(10) Uani 1 1 d . . . H1N H 0.4520 0.5247 0.8440 0.031 Uiso 1 1 calc R . . C4 C 0.78436(16) 0.52422(13) 1.05618(11) 0.02712(12) Uani 1 1 d . . . C2 C 0.60984(13) 0.28173(12) 0.70187(10) 0.02387(10) Uani 1 1 d . . . H1 H 0.8031 0.3184 0.6927 0.029 Uiso 1 1 calc R . . O2 O 0.4223(2) 0.15462(16) 0.32691(12) 0.0538(2) Uani 1 1 d . . . C1 C 0.54608(15) 0.03280(13) 0.75469(12) 0.02820(12) Uani 1 1 d . . . H11 H 0.6795 0.0288 0.8875 0.034 Uiso 1 1 calc R . . H12 H 0.5728 -0.0757 0.6424 0.034 Uiso 1 1 calc R . . C3 C 0.42450(16) 0.28737(13) 0.48270(11) 0.02780(12) Uani 1 1 d . . . C5 C 0.7505(2) 0.71467(16) 1.21349(13) 0.03835(17) Uani 1 1 d . . . H51 H 0.8810 0.8598 1.2173 0.046 Uiso 1 1 calc R . . H52 H 0.7848 0.6714 1.3534 0.046 Uiso 1 1 calc R . . H53 H 0.5638 0.7347 1.1706 0.046 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.03171(8) 0.03876(10) 0.03020(8) 0.00055(6) 0.00767(6) 0.00266(6) O3 0.0360(3) 0.0528(4) 0.0242(2) 0.0031(2) -0.0083(2) 0.0199(3) O1 0.0466(3) 0.0467(3) 0.0203(2) -0.0002(2) -0.0069(2) 0.0277(3) N1 0.0268(2) 0.0280(2) 0.01836(19) 0.00050(16) -0.00431(17) 0.01124(18) C4 0.0296(3) 0.0299(3) 0.0170(2) 0.00444(18) -0.00263(19) 0.0067(2) C2 0.0234(2) 0.0277(2) 0.0190(2) 0.00288(18) 0.00038(18) 0.00964(19) O2 0.0804(6) 0.0598(5) 0.0216(2) -0.0060(3) -0.0009(3) 0.0420(5) C1 0.0281(3) 0.0274(3) 0.0304(3) 0.0060(2) 0.0050(2) 0.0125(2) C3 0.0326(3) 0.0311(3) 0.0174(2) 0.0017(2) 0.0002(2) 0.0117(2) C5 0.0494(5) 0.0361(4) 0.0225(3) -0.0029(2) 0.0007(3) 0.0098(3) _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 S1 C1 1.8045(8) . ? S1 H1S 1.225(12) . ? O3 C4 1.2409(10) . ? O1 C3 1.3066(9) . ? O1 H1O 0.8200 . ? N1 C4 1.3368(9) . ? N1 C2 1.4548(8) . ? N1 H1N 0.8600 . ? C4 C5 1.4985(12) . ? C2 C3 1.5205(9) . ? C2 C1 1.5289(10) . ? C2 H1 0.9800 . ? O2 C3 1.2063(9) . ? C1 H11 0.9700 . ? C1 H12 0.9700 . ? C5 H51 0.9600 . ? C5 H52 0.9600 . ? C5 H53 0.9600 . ? 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 S1 H1S 92.1(7) . . ? C3 O1 H1O 109.5 . . ? C4 N1 C2 121.05(6) . . ? C4 N1 H1N 119.5 . . ? C2 N1 H1N 119.5 . . ? O3 C4 N1 120.77(7) . . ? O3 C4 C5 122.25(7) . . ? N1 C4 C5 116.95(7) . . ? N1 C2 C3 112.18(5) . . ? N1 C2 C1 112.75(6) . . ? C3 C2 C1 109.90(6) . . ? N1 C2 H1 107.2 . . ? C3 C2 H1 107.2 . . ? C1 C2 H1 107.2 . . ? C2 C1 S1 114.63(5) . . ? C2 C1 H11 108.6 . . ? S1 C1 H11 108.6 . . ? C2 C1 H12 108.6 . . ? S1 C1 H12 108.6 . . ? H11 C1 H12 107.6 . . ? O2 C3 O1 124.44(7) . . ? O2 C3 C2 120.37(7) . . ? O1 C3 C2 115.19(6) . . ? C4 C5 H51 109.5 . . ? C4 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? C4 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 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 C2 N1 C4 O3 -0.07(12) . . . . ? C2 N1 C4 C5 178.05(7) . . . . ? C4 N1 C2 C3 -162.78(7) . . . . ? C4 N1 C2 C1 72.50(8) . . . . ? N1 C2 C1 S1 61.54(7) . . . . ? C3 C2 C1 S1 -64.41(7) . . . . ? N1 C2 C3 O2 178.06(9) . . . . ? C1 C2 C3 O2 -55.67(11) . . . . ? N1 C2 C3 O1 -1.65(10) . . . . ? C1 C2 C3 O1 124.63(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O3 0.82 1.78 2.5758(8) 163.0 1_454 S1 H1S O2 1.225(12) 2.260(12) 3.4699(7) 169.0(10) 1_556 N1 H1N S1 0.86 2.96 3.7519(6) 153.5 1_565 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 40.24 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.271 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.046 # END data_NAC_250K _database_code_depnum_ccdc_archive 'CCDC 868555' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common N-Acetyl-L-Cysteine _chemical_formula_moiety 'C5 H9 N O3 S' _chemical_formula_sum 'C5 H9 N O3 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 250(2) _chemical_formula_weight 163.20 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_int_tables_number 1 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.07618(15) _cell_length_b 5.8583(2) _cell_length_c 6.5043(2) _cell_angle_alpha 96.300(3) _cell_angle_beta 103.661(3) _cell_angle_gamma 102.203(3) _cell_volume 181.091(11) _cell_formula_units_Z 1 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 86 _exptl_absorpt_coefficient_mu 0.393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8554 _exptl_absorpt_correction_T_max 0.9506 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 13845 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 40.24 _reflns_number_total 4561 _reflns_number_gt 4283 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0444P)^2^+0.0024P] 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 0.84(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(3) _refine_ls_number_reflns 4561 _refine_ls_number_parameters 96 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0746 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 S1 S 0.19805(2) -0.07031(2) 0.78222(2) 0.03035(6) Uani 1 1 d D . . H1S H 0.268(4) 0.040(3) 0.968(2) 0.036 Uiso 1 1 d D . . O1 O 0.27618(15) 0.44599(12) 0.47893(9) 0.03300(14) Uani 1 1 d . . . H1O H 0.2103 0.4604 0.3529 0.040 Uiso 1 1 calc R . . N1 N 0.59143(13) 0.46148(11) 0.86754(9) 0.02250(10) Uani 1 1 d . . . H1N H 0.4510 0.5271 0.8437 0.027 Uiso 1 1 calc R . . C1 C 0.54736(15) 0.03302(13) 0.75480(12) 0.02443(11) Uani 1 1 d . . . H11 H 0.6818 0.0289 0.8892 0.029 Uiso 1 1 calc R . . H12 H 0.5750 -0.0768 0.6415 0.029 Uiso 1 1 calc R . . O2 O 0.4241(2) 0.15543(16) 0.32588(11) 0.0450(2) Uani 1 1 d . . . C2 C 0.61157(13) 0.28345(12) 0.70144(10) 0.02090(10) Uani 1 1 d . . . H1 H 0.8073 0.3211 0.6917 0.025 Uiso 1 1 calc R . . O3 O 0.98710(15) 0.43354(14) 1.09432(10) 0.03363(13) Uani 1 1 d . . . C3 C 0.42562(16) 0.28895(13) 0.48227(10) 0.02433(11) Uani 1 1 d . . . C4 C 0.78529(16) 0.52596(14) 1.05641(11) 0.02345(11) Uani 1 1 d . . . C5 C 0.7520(2) 0.71666(16) 1.21423(13) 0.03285(16) Uani 1 1 d . . . H51 H 0.8848 0.8639 1.2179 0.039 Uiso 1 1 calc R . . H52 H 0.7864 0.6722 1.3557 0.039 Uiso 1 1 calc R . . H53 H 0.5633 0.7375 1.1714 0.039 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.02757(8) 0.03344(10) 0.02632(8) 0.00065(6) 0.00660(6) 0.00237(6) O1 0.0398(3) 0.0401(3) 0.01777(19) 0.00027(19) -0.00515(19) 0.0237(3) N1 0.0236(2) 0.0244(2) 0.01616(18) 0.00030(16) -0.00292(16) 0.00967(19) C1 0.0242(3) 0.0238(3) 0.0266(3) 0.0053(2) 0.0045(2) 0.0106(2) O2 0.0663(5) 0.0502(4) 0.0190(2) -0.0051(2) -0.0003(3) 0.0344(4) C2 0.0206(2) 0.0240(2) 0.0170(2) 0.00273(17) 0.00078(17) 0.00815(19) O3 0.0306(3) 0.0447(3) 0.0215(2) 0.0028(2) -0.00618(19) 0.0168(3) C3 0.0285(3) 0.0267(3) 0.0159(2) 0.00137(19) 0.00064(19) 0.0097(2) C4 0.0256(3) 0.0256(3) 0.01534(19) 0.00377(18) -0.00163(18) 0.0061(2) C5 0.0414(4) 0.0312(3) 0.0204(3) -0.0025(2) 0.0011(3) 0.0083(3) _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 S1 C1 1.8060(8) . ? S1 H1S 1.241(13) . ? O1 C3 1.3091(9) . ? O1 H1O 0.8300 . ? N1 C4 1.3380(9) . ? N1 C2 1.4544(8) . ? N1 H1N 0.8700 . ? C1 C2 1.5304(10) . ? C1 H11 0.9800 . ? C1 H12 0.9800 . ? O2 C3 1.2107(9) . ? C2 C3 1.5204(9) . ? C2 H1 0.9900 . ? O3 C4 1.2441(10) . ? C4 C5 1.4967(12) . ? C5 H51 0.9700 . ? C5 H52 0.9700 . ? C5 H53 0.9700 . ? 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 S1 H1S 91.1(8) . . ? C3 O1 H1O 109.5 . . ? C4 N1 C2 121.10(6) . . ? C4 N1 H1N 119.5 . . ? C2 N1 H1N 119.5 . . ? C2 C1 S1 114.53(5) . . ? C2 C1 H11 108.6 . . ? S1 C1 H11 108.6 . . ? C2 C1 H12 108.6 . . ? S1 C1 H12 108.6 . . ? H11 C1 H12 107.6 . . ? N1 C2 C3 112.20(5) . . ? N1 C2 C1 112.61(5) . . ? C3 C2 C1 109.79(6) . . ? N1 C2 H1 107.3 . . ? C3 C2 H1 107.3 . . ? C1 C2 H1 107.3 . . ? O2 C3 O1 124.48(7) . . ? O2 C3 C2 120.27(7) . . ? O1 C3 C2 115.25(6) . . ? O3 C4 N1 120.53(7) . . ? O3 C4 C5 122.25(7) . . ? N1 C4 C5 117.19(7) . . ? C4 C5 H51 109.5 . . ? C4 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? C4 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 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 C4 N1 C2 C3 -163.01(7) . . . . ? C4 N1 C2 C1 72.51(8) . . . . ? S1 C1 C2 N1 61.64(7) . . . . ? S1 C1 C2 C3 -64.16(7) . . . . ? N1 C2 C3 O2 178.12(9) . . . . ? C1 C2 C3 O2 -55.85(11) . . . . ? N1 C2 C3 O1 -1.34(10) . . . . ? C1 C2 C3 O1 124.69(7) . . . . ? C2 N1 C4 O3 -0.35(12) . . . . ? C2 N1 C4 C5 177.89(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O3 0.83 1.76 2.5686(8) 163.6 1_454 S1 H1S O2 1.241(13) 2.247(13) 3.4620(7) 165.4(11) 1_556 N1 H1N S1 0.87 2.94 3.7343(6) 153.6 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 40.24 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.257 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.048 # END data_NAC_200K _database_code_depnum_ccdc_archive 'CCDC 868556' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common N-Acetyl-L-Cysteine _chemical_formula_moiety 'C5 H9 N O3 S' _chemical_formula_sum 'C5 H9 N O3 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 200(2) _chemical_formula_weight 163.20 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_int_tables_number 1 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.06381(14) _cell_length_b 5.83621(18) _cell_length_c 6.4864(2) _cell_angle_alpha 96.162(3) _cell_angle_beta 103.409(3) _cell_angle_gamma 102.331(3) _cell_volume 179.669(10) _cell_formula_units_Z 1 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 86 _exptl_absorpt_coefficient_mu 0.396 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8544 _exptl_absorpt_correction_T_max 0.9503 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 14620 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 40.23 _reflns_number_total 4511 _reflns_number_gt 4384 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0382P)^2^+0.0031P] 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 0.45(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.07(3) _refine_ls_number_reflns 4511 _refine_ls_number_parameters 96 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0263 _refine_ls_R_factor_gt 0.0252 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 S1 S 0.19771(2) -0.070718(19) 0.782283(19) 0.02445(5) Uani 1 1 d D . . H1S H 0.263(3) 0.038(2) 0.9700(19) 0.029 Uiso 1 1 d D . . O1 O 0.27678(13) 0.44818(10) 0.47870(8) 0.02654(11) Uani 1 1 d . . . H1O H 0.2033 0.4579 0.3508 0.032 Uiso 1 1 calc R . . N1 N 0.59207(11) 0.46318(10) 0.86754(8) 0.01830(8) Uani 1 1 d . . . H1N H 0.4499 0.5298 0.8438 0.022 Uiso 1 1 calc R . . C1 C 0.54871(13) 0.03318(11) 0.75481(11) 0.01976(9) Uani 1 1 d . . . H11 H 0.6841 0.0289 0.8908 0.024 Uiso 1 1 calc R . . H12 H 0.5774 -0.0778 0.6402 0.024 Uiso 1 1 calc R . . O2 O 0.42600(18) 0.15657(13) 0.32517(10) 0.03623(16) Uani 1 1 d . . . C2 C 0.61295(12) 0.28509(10) 0.70113(9) 0.01695(8) Uani 1 1 d . . . H1 H 0.8111 0.3238 0.6909 0.020 Uiso 1 1 calc R . . O3 O 0.98836(13) 0.43410(11) 1.09413(9) 0.02694(10) Uani 1 1 d . . . C3 C 0.42702(14) 0.29048(11) 0.48162(9) 0.01957(9) Uani 1 1 d . . . C4 C 0.78631(14) 0.52721(12) 1.05637(10) 0.01919(9) Uani 1 1 d . . . C5 C 0.75328(18) 0.71850(13) 1.21478(11) 0.02659(13) Uani 1 1 d . . . H51 H 0.8882 0.8678 1.2183 0.032 Uiso 1 1 calc R . . H52 H 0.7875 0.6729 1.3579 0.032 Uiso 1 1 calc R . . H53 H 0.5626 0.7400 1.1719 0.032 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.02220(7) 0.02686(8) 0.02130(7) 0.00044(5) 0.00528(5) 0.00186(5) O1 0.0320(3) 0.0319(2) 0.01477(17) 0.00018(16) -0.00393(16) 0.0187(2) N1 0.01899(19) 0.01987(19) 0.01328(17) -0.00002(14) -0.00246(14) 0.00762(15) C1 0.0196(2) 0.0191(2) 0.0214(2) 0.00397(17) 0.00357(18) 0.00816(18) O2 0.0530(4) 0.0404(3) 0.01575(19) -0.0046(2) -0.0004(2) 0.0272(3) C2 0.01691(19) 0.0190(2) 0.01400(18) 0.00213(15) 0.00073(15) 0.00637(16) O3 0.0246(2) 0.0362(3) 0.01717(19) 0.00206(17) -0.00494(16) 0.0139(2) C3 0.0231(2) 0.0214(2) 0.01292(18) 0.00140(16) 0.00076(17) 0.00766(19) C4 0.0214(2) 0.0206(2) 0.01268(18) 0.00296(15) -0.00119(16) 0.00508(18) C5 0.0332(3) 0.0253(3) 0.0167(2) -0.00230(19) 0.0007(2) 0.0067(2) _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 S1 C1 1.8079(6) . ? S1 H1S 1.245(12) . ? O1 C3 1.3124(8) . ? O1 H1O 0.8400 . ? N1 C4 1.3391(8) . ? N1 C2 1.4545(8) . ? N1 H1N 0.8800 . ? C1 C2 1.5319(8) . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? O2 C3 1.2109(8) . ? C2 C3 1.5216(8) . ? C2 H1 1.0000 . ? O3 C4 1.2457(9) . ? C4 C5 1.4978(11) . ? C5 H51 0.9800 . ? C5 H52 0.9800 . ? C5 H53 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 S1 H1S 92.1(7) . . ? C3 O1 H1O 109.5 . . ? C4 N1 C2 120.91(5) . . ? C4 N1 H1N 119.5 . . ? C2 N1 H1N 119.5 . . ? C2 C1 S1 114.29(4) . . ? C2 C1 H11 108.7 . . ? S1 C1 H11 108.7 . . ? C2 C1 H12 108.7 . . ? S1 C1 H12 108.7 . . ? H11 C1 H12 107.6 . . ? N1 C2 C3 112.27(5) . . ? N1 C2 C1 112.64(5) . . ? C3 C2 C1 109.72(5) . . ? N1 C2 H1 107.3 . . ? C3 C2 H1 107.3 . . ? C1 C2 H1 107.3 . . ? O2 C3 O1 124.61(6) . . ? O2 C3 C2 120.27(6) . . ? O1 C3 C2 115.12(5) . . ? O3 C4 N1 120.67(6) . . ? O3 C4 C5 122.16(6) . . ? N1 C4 C5 117.15(6) . . ? C4 C5 H51 109.5 . . ? C4 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? C4 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 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 C4 N1 C2 C3 -163.09(6) . . . . ? C4 N1 C2 C1 72.45(7) . . . . ? S1 C1 C2 N1 61.76(6) . . . . ? S1 C1 C2 C3 -64.10(6) . . . . ? N1 C2 C3 O2 178.24(7) . . . . ? C1 C2 C3 O2 -55.70(9) . . . . ? N1 C2 C3 O1 -1.31(8) . . . . ? C1 C2 C3 O1 124.75(6) . . . . ? C2 N1 C4 O3 -0.52(10) . . . . ? C2 N1 C4 C5 177.75(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O3 0.84 1.74 2.5646(7) 167.4 1_454 S1 H1S O2 1.245(12) 2.236(12) 3.4569(6) 165.8(10) 1_556 N1 H1N S1 0.88 2.91 3.7181(5) 153.7 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 40.23 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.248 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.045 # END data_NAC_150K _database_code_depnum_ccdc_archive 'CCDC 868557' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common N-Acetyl-L-Cysteine _chemical_formula_moiety 'C5 H9 N O3 S' _chemical_formula_sum 'C5 H9 N O3 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 150(2) _chemical_formula_weight 163.20 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_int_tables_number 1 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.05300(17) _cell_length_b 5.81773(18) _cell_length_c 6.4717(2) _cell_angle_alpha 96.051(3) _cell_angle_beta 103.212(3) _cell_angle_gamma 102.439(3) _cell_volume 178.456(11) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 86 _exptl_absorpt_coefficient_mu 0.399 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8535 _exptl_absorpt_correction_T_max 0.9499 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _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 14340 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 41.15 _reflns_number_total 4725 _reflns_number_gt 4639 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0366P)^2^+0.0044P] 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 0.26(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.08(2) _refine_ls_number_reflns 4725 _refine_ls_number_parameters 96 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0244 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0621 _refine_ls_wR_factor_gt 0.0615 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 S1 S 0.197459(18) -0.070998(17) 0.782338(16) 0.01946(4) Uani 1 1 d D . . H1S H 0.256(3) 0.047(2) 0.9621(18) 0.023 Uiso 1 1 d D . . O1 O 0.27736(12) 0.44990(10) 0.47840(7) 0.02112(9) Uani 1 1 d . . . H1O H 0.1944 0.4524 0.3507 0.025 Uiso 1 1 calc R . . N1 N 0.59295(11) 0.46449(9) 0.86750(7) 0.01476(7) Uani 1 1 d . . . H1N H 0.4505 0.5311 0.8440 0.018 Uiso 1 1 calc R . . C1 C 0.54993(12) 0.03326(10) 0.75478(10) 0.01596(8) Uani 1 1 d . . . H11 H 0.6849 0.0289 0.8910 0.019 Uiso 1 1 calc R . . H12 H 0.5791 -0.0779 0.6402 0.019 Uiso 1 1 calc R . . O2 O 0.42767(16) 0.15771(11) 0.32425(9) 0.02882(13) Uani 1 1 d . . . C2 C 0.61443(11) 0.28643(10) 0.70065(8) 0.01370(7) Uani 1 1 d . . . H1 H 0.8130 0.3256 0.6900 0.016 Uiso 1 1 calc R . . O3 O 0.98947(11) 0.43496(10) 1.09383(8) 0.02136(9) Uani 1 1 d . . . C3 C 0.42835(13) 0.29202(10) 0.48115(9) 0.01584(8) Uani 1 1 d . . . C4 C 0.78716(13) 0.52844(11) 1.05655(9) 0.01532(8) Uani 1 1 d . . . C5 C 0.75415(16) 0.72012(12) 1.21515(10) 0.02120(11) Uani 1 1 d . . . H51 H 0.8897 0.8698 1.2185 0.025 Uiso 1 1 calc R . . H52 H 0.7878 0.6740 1.3584 0.025 Uiso 1 1 calc R . . H53 H 0.5634 0.7420 1.1724 0.025 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01775(6) 0.02133(6) 0.01702(6) 0.00040(4) 0.00423(4) 0.00162(4) O1 0.0254(2) 0.0252(2) 0.01216(15) -0.00001(14) -0.00292(14) 0.01472(18) N1 0.01549(17) 0.01563(17) 0.01108(15) -0.00007(12) -0.00179(12) 0.00610(14) C1 0.01569(19) 0.01552(19) 0.01733(19) 0.00325(15) 0.00297(16) 0.00635(16) O2 0.0423(3) 0.0320(3) 0.01263(16) -0.00366(17) -0.00020(18) 0.0215(3) C2 0.01401(17) 0.01520(18) 0.01125(16) 0.00163(13) 0.00077(13) 0.00517(14) O3 0.01979(19) 0.0284(2) 0.01403(16) 0.00183(15) -0.00352(14) 0.01123(17) C3 0.0186(2) 0.0170(2) 0.01093(17) 0.00090(15) 0.00078(15) 0.00624(16) C4 0.0170(2) 0.01666(19) 0.01003(16) 0.00202(13) -0.00068(14) 0.00397(15) C5 0.0268(3) 0.0201(2) 0.0137(2) -0.00160(17) 0.00127(19) 0.0058(2) _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 S1 C1 1.8095(6) . ? S1 H1S 1.224(12) . ? O1 C3 1.3135(8) . ? O1 H1O 0.8400 . ? N1 C4 1.3402(7) . ? N1 C2 1.4550(7) . ? N1 H1N 0.8800 . ? C1 C2 1.5338(8) . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? O2 C3 1.2131(7) . ? C2 C3 1.5217(7) . ? C2 H1 1.0000 . ? O3 C4 1.2464(8) . ? C4 C5 1.4973(9) . ? C5 H51 0.9800 . ? C5 H52 0.9800 . ? C5 H53 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 S1 H1S 92.3(7) . . ? C3 O1 H1O 109.5 . . ? C4 N1 C2 120.92(5) . . ? C4 N1 H1N 119.5 . . ? C2 N1 H1N 119.5 . . ? C2 C1 S1 114.13(4) . . ? C2 C1 H11 108.7 . . ? S1 C1 H11 108.7 . . ? C2 C1 H12 108.7 . . ? S1 C1 H12 108.7 . . ? H11 C1 H12 107.6 . . ? N1 C2 C3 112.28(4) . . ? N1 C2 C1 112.53(4) . . ? C3 C2 C1 109.72(5) . . ? N1 C2 H1 107.3 . . ? C3 C2 H1 107.3 . . ? C1 C2 H1 107.3 . . ? O2 C3 O1 124.61(6) . . ? O2 C3 C2 120.22(6) . . ? O1 C3 C2 115.17(5) . . ? O3 C4 N1 120.58(6) . . ? O3 C4 C5 122.20(6) . . ? N1 C4 C5 117.19(6) . . ? C4 C5 H51 109.5 . . ? C4 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? C4 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 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 C4 N1 C2 C3 -163.19(5) . . . . ? C4 N1 C2 C1 72.43(7) . . . . ? S1 C1 C2 N1 61.86(5) . . . . ? S1 C1 C2 C3 -63.93(5) . . . . ? N1 C2 C3 O2 178.34(6) . . . . ? C1 C2 C3 O2 -55.73(8) . . . . ? N1 C2 C3 O1 -1.28(8) . . . . ? C1 C2 C3 O1 124.65(6) . . . . ? C2 N1 C4 O3 -0.56(9) . . . . ? C2 N1 C4 C5 177.58(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O3 0.84 1.73 2.5618(6) 173.1 1_454 S1 H1S O2 1.224(12) 2.274(12) 3.4508(6) 160.2(9) 1_556 N1 H1N S1 0.88 2.90 3.7064(5) 153.8 1_565 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 41.15 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.261 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.044 # END data_NAC_100K _database_code_depnum_ccdc_archive 'CCDC 868558' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common N-Acetyl-L-Cysteine _chemical_formula_moiety 'C5 H9 N O3 S' _chemical_formula_sum 'C5 H9 N O3 S' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(2) _chemical_formula_weight 163.20 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_int_tables_number 1 _chemical_absolute_configuration rmad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.04324(14) _cell_length_b 5.80332(17) _cell_length_c 6.4627(2) _cell_angle_alpha 95.944(3) _cell_angle_beta 103.086(3) _cell_angle_gamma 102.516(3) _cell_volume 177.525(10) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 86 _exptl_absorpt_coefficient_mu 0.401 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8528 _exptl_absorpt_correction_T_max 0.9497 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction, 2008)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type ? _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 14623 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 41.15 _reflns_number_total 4713 _reflns_number_gt 4651 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0367P)^2^+0.0079P] 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 0.09(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.09(2) _refine_ls_number_reflns 4713 _refine_ls_number_parameters 96 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0236 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0608 _refine_ls_wR_factor_gt 0.0604 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 S1 S 0.197243(17) -0.071240(16) 0.782369(16) 0.01524(4) Uani 1 1 d D . . H1S H 0.250(3) 0.049(2) 0.9584(19) 0.018 Uiso 1 1 d D . . O1 O 0.27791(11) 0.45167(9) 0.47831(7) 0.01669(8) Uani 1 1 d . . . H1O H 0.1894 0.4501 0.3511 0.020 Uiso 1 1 calc R . . N1 N 0.59371(11) 0.46582(9) 0.86745(7) 0.01185(7) Uani 1 1 d . . . H1N H 0.4511 0.5327 0.8441 0.014 Uiso 1 1 calc R . . C1 C 0.55104(12) 0.03362(10) 0.75477(9) 0.01278(8) Uani 1 1 d . . . H11 H 0.6859 0.0291 0.8911 0.015 Uiso 1 1 calc R . . H12 H 0.5807 -0.0775 0.6402 0.015 Uiso 1 1 calc R . . O2 O 0.42911(14) 0.15861(11) 0.32362(8) 0.02248(11) Uani 1 1 d . . . C2 C 0.61557(11) 0.28762(10) 0.70041(8) 0.01105(7) Uani 1 1 d . . . H1 H 0.8145 0.3272 0.6895 0.013 Uiso 1 1 calc R . . O3 O 0.99040(11) 0.43538(10) 1.09361(8) 0.01679(8) Uani 1 1 d . . . C3 C 0.42948(12) 0.29319(10) 0.48087(9) 0.01263(8) Uani 1 1 d . . . C4 C 0.78799(12) 0.52936(11) 1.05639(9) 0.01230(8) Uani 1 1 d . . . C5 C 0.75522(15) 0.72161(12) 1.21556(10) 0.01692(10) Uani 1 1 d . . . H51 H 0.8913 0.8716 1.2187 0.020 Uiso 1 1 calc R . . H52 H 0.7887 0.6750 1.3589 0.020 Uiso 1 1 calc R . . H53 H 0.5643 0.7438 1.1731 0.020 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01392(5) 0.01657(6) 0.01350(5) 0.00040(4) 0.00330(4) 0.00130(4) O1 0.0199(2) 0.01989(19) 0.00993(15) 0.00025(13) -0.00206(13) 0.01141(16) N1 0.01262(16) 0.01263(17) 0.00875(15) -0.00016(12) -0.00133(12) 0.00499(13) C1 0.01265(19) 0.01223(18) 0.01397(19) 0.00257(14) 0.00259(15) 0.00479(15) O2 0.0327(3) 0.0249(2) 0.01026(16) -0.00305(15) 0.00001(17) 0.0165(2) C2 0.01135(17) 0.01216(18) 0.00920(16) 0.00124(13) 0.00079(13) 0.00414(14) O3 0.01562(18) 0.0220(2) 0.01155(15) 0.00150(14) -0.00240(13) 0.00887(15) C3 0.0148(2) 0.01340(19) 0.00900(17) 0.00089(14) 0.00077(15) 0.00486(16) C4 0.0137(2) 0.01307(18) 0.00841(16) 0.00177(13) -0.00028(14) 0.00301(15) C5 0.0209(3) 0.0160(2) 0.01131(19) -0.00124(16) 0.00084(17) 0.00445(19) _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 S1 C1 1.8116(6) . ? S1 H1S 1.212(11) . ? O1 C3 1.3163(7) . ? O1 H1O 0.8400 . ? N1 C4 1.3399(7) . ? N1 C2 1.4557(7) . ? N1 H1N 0.8800 . ? C1 C2 1.5341(8) . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? O2 C3 1.2153(7) . ? C2 C3 1.5214(7) . ? C2 H1 1.0000 . ? O3 C4 1.2469(8) . ? C4 C5 1.4998(9) . ? C5 H51 0.9800 . ? C5 H52 0.9800 . ? C5 H53 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 S1 H1S 93.0(7) . . ? C3 O1 H1O 109.5 . . ? C4 N1 C2 120.83(5) . . ? C4 N1 H1N 119.6 . . ? C2 N1 H1N 119.6 . . ? C2 C1 S1 114.03(4) . . ? C2 C1 H11 108.7 . . ? S1 C1 H11 108.7 . . ? C2 C1 H12 108.7 . . ? S1 C1 H12 108.7 . . ? H11 C1 H12 107.6 . . ? N1 C2 C3 112.33(4) . . ? N1 C2 C1 112.54(4) . . ? C3 C2 C1 109.68(5) . . ? N1 C2 H1 107.3 . . ? C3 C2 H1 107.3 . . ? C1 C2 H1 107.3 . . ? O2 C3 O1 124.65(6) . . ? O2 C3 C2 120.26(5) . . ? O1 C3 C2 115.09(5) . . ? O3 C4 N1 120.63(6) . . ? O3 C4 C5 122.13(5) . . ? N1 C4 C5 117.21(6) . . ? C4 C5 H51 109.5 . . ? C4 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? C4 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 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 C4 N1 C2 C3 -163.28(5) . . . . ? C4 N1 C2 C1 72.35(7) . . . . ? S1 C1 C2 N1 61.93(5) . . . . ? S1 C1 C2 C3 -63.88(5) . . . . ? N1 C2 C3 O2 178.34(6) . . . . ? C1 C2 C3 O2 -55.72(8) . . . . ? N1 C2 C3 O1 -1.24(7) . . . . ? C1 C2 C3 O1 124.70(6) . . . . ? C2 N1 C4 O3 -0.64(9) . . . . ? C2 N1 C4 C5 177.51(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O3 0.84 1.72 2.5597(6) 176.5 1_454 S1 H1S O2 1.212(11) 2.295(12) 3.4478(5) 157.8(10) 1_556 N1 H1N S1 0.88 2.88 3.6952(5) 154.0 1_565 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 41.15 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.265 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.045 # END