# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_NAC_I _audit_creation_method SHELXL-97 _chemical_name_systematic N-acetyl-L-cysteine _chemical_name_common NAC _chemical_melting_point '379 K' _chemical_formula_moiety 'C5 H9 N O3 S' _chemical_formula_sum 'C5 H9 N O3 S' _chemical_formula_weight 163.19 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.1041(7) _cell_length_b 5.9092(8) _cell_length_c 6.5261(10) _cell_angle_alpha 96.484(12) _cell_angle_beta 103.696(13) _cell_angle_gamma 101.969(11) _cell_volume 184.34(4) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 768 _cell_measurement_theta_min 4.4030 _cell_measurement_theta_max 28.8070 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 86 _exptl_absorpt_coefficient_mu 0.386 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.24651 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details Multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _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 1129 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 26.37 _reflns_number_total 937 _reflns_number_gt 887 _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^)+(0.1155P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(14) _refine_ls_number_reflns 937 _refine_ls_number_parameters 97 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1426 _refine_ls_wR_factor_gt 0.1418 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.61981(9) 0.41269(9) 0.49025(9) 0.0364(4) Uani 1 1 d . . . O1 O 0.6978(8) 0.9253(6) 0.1883(5) 0.0411(9) Uani 1 1 d . . . H1 H 0.6065 0.9190 0.0652 0.062 Uiso 1 1 calc R . . O3 O 1.4068(8) 0.9151(7) 0.8019(6) 0.0407(9) Uani 1 1 d . . . N1 N 1.0118(8) 0.9416(6) 0.5769(6) 0.0279(8) Uani 1 1 d . . . H6 H 0.8741 1.0067 0.5535 0.033 Uiso 1 1 calc R . . C3 C 0.9673(9) 0.5150(7) 0.4627(7) 0.0285(9) Uani 1 1 d . . . H3 H 1.0999 0.5108 0.5951 0.034 Uiso 1 1 calc R . . H4 H 0.9945 0.4071 0.3505 0.034 Uiso 1 1 calc R . . C1 C 0.8446(10) 0.7689(7) 0.1919(8) 0.0299(10) Uani 1 1 d . . . C4 C 1.2060(11) 1.0060(9) 0.7650(8) 0.0294(10) Uani 1 1 d . . . O2 O 0.8450(12) 0.6379(7) 0.0362(7) 0.0538(12) Uani 1 1 d . . . C2 C 1.0306(9) 0.7619(7) 0.4103(7) 0.0256(9) Uani 1 1 d . . . H2 H 1.2229 0.7978 0.4000 0.031 Uiso 1 1 calc R . . C5 C 1.1729(13) 1.1973(9) 0.9218(9) 0.0396(11) Uani 1 1 d . . . H9 H 1.3025 1.3414 0.9241 0.059 Uiso 1 1 calc R . . H7 H 1.2081 1.1555 1.0620 0.059 Uiso 1 1 calc R . . H8 H 0.9868 1.2173 0.8797 0.059 Uiso 1 1 calc R . . H5 H 0.709(16) 0.517(11) 0.665(12) 0.05(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0328(6) 0.0412(6) 0.0327(6) 0.0016(4) 0.0081(4) 0.0069(4) O1 0.047(2) 0.054(2) 0.0237(18) 0.0014(15) -0.0064(16) 0.0350(19) O3 0.037(2) 0.058(2) 0.0250(17) 0.0044(15) -0.0074(15) 0.0266(18) N1 0.0286(18) 0.0350(18) 0.0208(18) 0.0023(14) -0.0019(15) 0.0203(16) C3 0.029(2) 0.031(2) 0.031(2) 0.0069(16) 0.0081(18) 0.0184(17) C1 0.033(3) 0.030(2) 0.026(2) 0.0034(18) 0.003(2) 0.0117(19) C4 0.034(2) 0.033(2) 0.021(2) 0.0093(16) -0.0010(18) 0.0125(19) O2 0.080(3) 0.058(2) 0.0254(18) -0.0025(17) 0.0031(19) 0.041(2) C2 0.0220(19) 0.0309(19) 0.025(2) 0.0039(15) 0.0028(16) 0.0134(17) C5 0.047(3) 0.039(2) 0.028(2) 0.0006(19) 0.003(2) 0.011(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 C3 1.810(5) . ? S1 H5 1.17(7) . ? O1 C1 1.303(6) . ? O1 H1 0.8200 . ? O3 C4 1.240(7) . ? N1 C4 1.341(7) . ? N1 C2 1.466(5) . ? N1 H6 0.8600 . ? C3 C2 1.523(6) . ? C3 H3 0.9700 . ? C3 H4 0.9700 . ? C1 O2 1.207(7) . ? C1 C2 1.524(6) . ? C4 C5 1.501(8) . ? C2 H2 0.9800 . ? C5 H9 0.9600 . ? C5 H7 0.9600 . ? C5 H8 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 C3 S1 H5 85(4) . . ? C1 O1 H1 109.5 . . ? C4 N1 C2 121.0(4) . . ? C4 N1 H6 119.5 . . ? C2 N1 H6 119.5 . . ? C2 C3 S1 114.7(3) . . ? C2 C3 H3 108.6 . . ? S1 C3 H3 108.6 . . ? C2 C3 H4 108.6 . . ? S1 C3 H4 108.6 . . ? H3 C3 H4 107.6 . . ? O2 C1 O1 124.5(5) . . ? O2 C1 C2 119.8(5) . . ? O1 C1 C2 115.7(4) . . ? O3 C4 N1 120.6(5) . . ? O3 C4 C5 122.5(5) . . ? N1 C4 C5 116.8(5) . . ? N1 C2 C3 113.1(4) . . ? N1 C2 C1 111.7(4) . . ? C3 C2 C1 110.0(3) . . ? N1 C2 H2 107.3 . . ? C3 C2 H2 107.3 . . ? C1 C2 H2 107.3 . . ? C4 C5 H9 109.5 . . ? C4 C5 H7 109.5 . . ? H9 C5 H7 109.5 . . ? C4 C5 H8 109.5 . . ? H9 C5 H8 109.5 . . ? H7 C5 H8 109.5 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.575 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.094 _database_code_depnum_ccdc_archive 'CCDC 939816' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_NAC_II _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'N-Acetyl-L-cysteine' ; _chemical_name_common NAC _chemical_melting_point '374 K' _chemical_formula_moiety 'C5 H9 N O3 S' _chemical_formula_sum 'C5 H9 N O3 S' _chemical_formula_weight 163.19 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.0684(6) _cell_length_b 7.6372(9) _cell_length_c 16.005(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 741.74(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 512 _cell_measurement_theta_min 2.9494 _cell_measurement_theta_max 26.3073 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.384 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.68426 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details Multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _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 2080 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0590 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1341 _reflns_number_gt 1057 _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^)+(0.0280P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.08(15) _refine_ls_number_reflns 1341 _refine_ls_number_parameters 97 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 -0.07346(16) 0.90462(15) 0.28124(7) 0.0549(3) Uani 1 1 d . . . O1 O 0.1375(4) 0.6264(3) 0.43728(17) 0.0448(6) Uani 1 1 d . . . H1 H 0.1900 0.5277 0.4339 0.067 Uiso 1 1 calc R . . O3 O 0.2339(4) 1.2937(3) 0.43372(16) 0.0450(7) Uani 1 1 d . . . C2 C 0.2019(5) 0.9273(5) 0.4213(2) 0.0350(9) Uani 1 1 d . . . H2 H 0.2031 0.9526 0.4813 0.042 Uiso 1 1 calc R . . N1 N 0.3623(4) 1.0409(4) 0.38172(19) 0.0384(8) Uani 1 1 d . . . H6 H 0.4580 0.9931 0.3493 0.046 Uiso 1 1 calc R . . O2 O 0.4551(4) 0.7067(3) 0.37904(19) 0.0552(8) Uani 1 1 d . . . C4 C 0.3726(6) 1.2142(5) 0.3918(2) 0.0347(8) Uani 1 1 d . . . C3 C -0.0311(5) 0.9542(5) 0.3899(2) 0.0433(9) Uani 1 1 d . . . H3 H -0.0723 1.0752 0.3995 0.052 Uiso 1 1 calc R . . H4 H -0.1295 0.8815 0.4228 0.052 Uiso 1 1 calc R . . C1 C 0.2811(6) 0.7412(5) 0.4095(2) 0.0349(9) Uani 1 1 d . . . C5 C 0.5605(6) 1.3018(5) 0.3501(2) 0.0463(10) Uani 1 1 d . . . H9 H 0.6736 1.3259 0.3904 0.069 Uiso 1 1 calc R . . H7 H 0.5113 1.4096 0.3255 0.069 Uiso 1 1 calc R . . H8 H 0.6182 1.2267 0.3072 0.069 Uiso 1 1 calc R . . H5 H 0.038(8) 1.015(8) 0.252(3) 0.15(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0555(6) 0.0497(6) 0.0596(6) -0.0013(6) -0.0131(6) 0.0030(6) O1 0.0502(13) 0.0246(13) 0.0597(16) 0.0044(14) 0.0089(13) 0.0038(14) O3 0.0535(15) 0.0272(14) 0.0544(17) -0.0015(13) 0.0174(15) 0.0048(13) C2 0.0411(19) 0.024(2) 0.040(2) -0.0015(16) -0.0010(17) 0.0053(18) N1 0.0371(17) 0.0256(16) 0.0526(19) -0.0045(14) 0.0049(15) 0.0016(14) O2 0.0486(16) 0.0292(14) 0.088(2) -0.0033(15) 0.0137(16) 0.0087(14) C4 0.039(2) 0.0262(18) 0.039(2) 0.0046(17) -0.0065(18) 0.0009(19) C3 0.041(2) 0.031(2) 0.058(2) -0.0002(19) 0.005(2) 0.0062(17) C1 0.042(2) 0.027(2) 0.0359(19) -0.0008(16) -0.0055(17) 0.0036(19) C5 0.044(2) 0.031(2) 0.065(3) 0.0032(19) -0.001(2) 0.007(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 C3 1.799(4) . ? S1 H5 1.18(6) . ? O1 C1 1.314(4) . ? O1 H1 0.8200 . ? O3 C4 1.235(4) . ? C2 N1 1.450(4) . ? C2 C1 1.512(5) . ? C2 C3 1.515(4) . ? C2 H2 0.9800 . ? N1 C4 1.335(4) . ? N1 H6 0.8600 . ? O2 C1 1.193(4) . ? C4 C5 1.482(5) . ? C3 H3 0.9700 . ? C3 H4 0.9700 . ? C5 H9 0.9600 . ? C5 H7 0.9600 . ? C5 H8 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 C3 S1 H5 99(2) . . ? C1 O1 H1 109.5 . . ? N1 C2 C1 107.1(3) . . ? N1 C2 C3 113.6(3) . . ? C1 C2 C3 112.5(3) . . ? N1 C2 H2 107.8 . . ? C1 C2 H2 107.8 . . ? C3 C2 H2 107.8 . . ? C4 N1 C2 124.9(3) . . ? C4 N1 H6 117.6 . . ? C2 N1 H6 117.6 . . ? O3 C4 N1 121.4(3) . . ? O3 C4 C5 123.2(3) . . ? N1 C4 C5 115.4(3) . . ? C2 C3 S1 115.2(2) . . ? C2 C3 H3 108.5 . . ? S1 C3 H3 108.5 . . ? C2 C3 H4 108.5 . . ? S1 C3 H4 108.5 . . ? H3 C3 H4 107.5 . . ? O2 C1 O1 125.3(3) . . ? O2 C1 C2 122.7(3) . . ? O1 C1 C2 112.0(3) . . ? C4 C5 H9 109.5 . . ? C4 C5 H7 109.5 . . ? H9 C5 H7 109.5 . . ? C4 C5 H8 109.5 . . ? H9 C5 H8 109.5 . . ? H7 C5 H8 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.266 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 939817'