# 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 ? _publ_contact_author_email sunx0053@umn.edu _publ_contact_author_name 'Changquan Sun' loop_ _publ_author_name 'Sathyanarayana Perumalla' 'Limin Shi' 'Changquan Sun' data_11048_0m _database_code_depnum_ccdc_archive 'CCDC 835705' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Acetaminophen hydrochloride hydrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 Cl N O3' _chemical_formula_weight 205.64 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.2761(6) _cell_length_b 22.345(2) _cell_length_c 6.8833(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.2570(10) _cell_angle_gamma 90.00 _cell_volume 957.56(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5012 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 28.24 _exptl_crystal_description Plates _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.374 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8772 _exptl_absorpt_correction_T_max 0.9426 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10318 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.84 _reflns_number_total 2043 _reflns_number_gt 1853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0376P)^2^+0.2988P] 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 2043 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0272 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.002 _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 Cl1 Cl 0.39914(5) 0.320966(13) 0.53254(5) 0.03390(12) Uani 1 1 d . . . O4 O 1.14861(18) -0.14149(4) 0.77012(16) 0.0357(2) Uani 1 1 d . . . O7 O 0.67269(15) 0.11502(4) 0.63529(14) 0.0304(2) Uani 1 1 d . . . O100 O 0.37965(17) 0.18330(5) 0.48849(18) 0.0363(2) Uani 1 1 d . . . C2 C 0.8720(2) 0.00176(6) 0.72010(18) 0.0276(3) Uani 1 1 d . . . N1 N 1.01647(18) 0.10527(4) 0.76777(15) 0.0266(2) Uani 1 1 d . . . C4 C 1.1207(2) -0.08079(5) 0.76756(17) 0.0270(3) Uani 1 1 d . . . C1 C 1.0410(2) 0.04170(5) 0.76175(16) 0.0241(2) Uani 1 1 d . . . C3 C 0.9136(2) -0.05918(6) 0.72274(19) 0.0295(3) Uani 1 1 d . . . C6 C 1.2499(2) 0.02027(6) 0.80230(18) 0.0289(3) Uani 1 1 d . . . C8 C 0.8737(3) 0.20524(6) 0.7241(2) 0.0352(3) Uani 1 1 d . . . C7 C 0.8519(2) 0.13910(5) 0.70803(17) 0.0261(3) Uani 1 1 d . . . C5 C 1.2903(2) -0.04070(6) 0.80556(19) 0.0292(3) Uani 1 1 d . . . H5 H 1.433(3) -0.0540(7) 0.833(2) 0.040(4) Uiso 1 1 d . . . H2 H 0.727(3) 0.0154(7) 0.691(2) 0.040(4) Uiso 1 1 d . . . H1 H 1.124(3) 0.1233(7) 0.822(2) 0.036(4) Uiso 1 1 d . . . H6 H 1.367(2) 0.0488(7) 0.832(2) 0.032(4) Uiso 1 1 d . . . H8C H 0.756(3) 0.2215(9) 0.782(3) 0.060(5) Uiso 1 1 d . . . H7 H 0.573(3) 0.1415(9) 0.588(3) 0.060(6) Uiso 1 1 d . . . H4 H 1.265(3) -0.1469(9) 0.820(3) 0.056(6) Uiso 1 1 d . . . H3 H 0.808(3) -0.0869(8) 0.695(2) 0.039(4) Uiso 1 1 d . . . H8B H 1.012(3) 0.2166(8) 0.802(3) 0.055(5) Uiso 1 1 d . . . H10B H 0.388(3) 0.2192(11) 0.516(3) 0.055(6) Uiso 1 1 d . . . H10A H 0.374(4) 0.1835(9) 0.364(4) 0.065(6) Uiso 1 1 d . . . H8A H 0.864(3) 0.2217(10) 0.601(3) 0.073(6) 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 Cl1 0.0388(2) 0.02285(17) 0.0377(2) -0.00069(11) -0.00431(14) 0.00220(12) O4 0.0379(6) 0.0204(5) 0.0483(6) -0.0004(4) 0.0032(5) 0.0025(4) O7 0.0321(5) 0.0223(4) 0.0357(5) -0.0013(4) -0.0006(4) 0.0014(4) O100 0.0431(6) 0.0232(5) 0.0396(6) -0.0029(4) -0.0065(5) 0.0017(4) C2 0.0281(6) 0.0252(6) 0.0295(6) 0.0004(5) 0.0038(5) 0.0001(5) N1 0.0301(6) 0.0208(5) 0.0279(5) -0.0022(4) -0.0002(4) -0.0028(4) C4 0.0356(7) 0.0214(6) 0.0245(6) -0.0005(4) 0.0060(5) 0.0009(5) C1 0.0317(6) 0.0202(5) 0.0204(5) -0.0012(4) 0.0033(5) 0.0004(5) C3 0.0301(7) 0.0234(6) 0.0352(7) -0.0009(5) 0.0047(5) -0.0046(5) C6 0.0295(7) 0.0254(6) 0.0305(6) -0.0026(5) -0.0005(5) -0.0027(5) C8 0.0420(8) 0.0221(6) 0.0400(8) -0.0007(5) -0.0010(6) 0.0004(5) C7 0.0338(6) 0.0233(6) 0.0215(5) -0.0008(4) 0.0049(5) -0.0009(5) C5 0.0290(7) 0.0268(6) 0.0313(6) -0.0018(5) 0.0014(5) 0.0028(5) _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 O4 C4 1.3676(15) . ? O4 H4 0.78(2) . ? O7 C7 1.2895(15) . ? O7 H7 0.89(2) . ? O100 H10B 0.82(2) . ? O100 H10A 0.85(2) . ? C2 C3 1.3861(18) . ? C2 C1 1.3881(18) . ? C2 H2 0.959(17) . ? N1 C7 1.3040(17) . ? N1 C1 1.4298(15) . ? N1 H1 0.834(17) . ? C4 C3 1.3843(19) . ? C4 C5 1.3905(18) . ? C1 C6 1.3906(18) . ? C3 H3 0.909(17) . ? C6 C5 1.3854(18) . ? C6 H6 0.973(16) . ? C8 C7 1.4871(18) . ? C8 H8C 0.95(2) . ? C8 H8B 1.00(2) . ? C8 H8A 0.92(2) . ? C5 H5 0.938(17) . ? 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 C4 O4 H4 105.8(16) . . ? C7 O7 H7 113.6(13) . . ? H10B O100 H10A 102.9(18) . . ? C3 C2 C1 119.43(12) . . ? C3 C2 H2 119.2(10) . . ? C1 C2 H2 121.4(10) . . ? C7 N1 C1 130.60(11) . . ? C7 N1 H1 115.2(11) . . ? C1 N1 H1 114.1(11) . . ? O4 C4 C3 117.65(12) . . ? O4 C4 C5 122.86(12) . . ? C3 C4 C5 119.48(12) . . ? C2 C1 C6 119.77(11) . . ? C2 C1 N1 124.21(12) . . ? C6 C1 N1 116.02(11) . . ? C4 C3 C2 121.02(12) . . ? C4 C3 H3 116.5(10) . . ? C2 C3 H3 122.5(11) . . ? C5 C6 C1 120.51(12) . . ? C5 C6 H6 120.6(9) . . ? C1 C6 H6 118.8(9) . . ? C7 C8 H8C 109.9(12) . . ? C7 C8 H8B 111.1(11) . . ? H8C C8 H8B 110.4(16) . . ? C7 C8 H8A 109.5(14) . . ? H8C C8 H8A 105.6(18) . . ? H8B C8 H8A 110.2(17) . . ? O7 C7 N1 119.86(11) . . ? O7 C7 C8 120.75(12) . . ? N1 C7 C8 119.40(12) . . ? C6 C5 C4 119.76(12) . . ? C6 C5 H5 118.9(10) . . ? C4 C5 H5 121.4(10) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.84 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.193 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.046 # Attachment '- 2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 844983' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-hydroxybenzenaminium chloride' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 Cl N O' _chemical_formula_weight 145.58 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.4919(6) _cell_length_b 6.1159(6) _cell_length_c 16.8700(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.0320(10) _cell_angle_gamma 90.00 _cell_volume 669.80(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6108 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 27.56 _exptl_crystal_description Needles _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.480 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.9143 _exptl_absorpt_correction_T_max 0.9315 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Apex II platform CCD' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1682 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.56 _reflns_number_total 1542 _reflns_number_gt 1527 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0428P)^2^+0.1243P] 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 0.017(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1542 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0228 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0660 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 Cl1 Cl 0.25785(6) 0.28401(4) 0.480064(17) 0.02472(11) Uani 1 1 d . . . O4 O 0.2474(2) 0.69488(16) 0.37727(5) 0.0267(2) Uani 1 1 d . . . N1 N 0.2453(3) 0.70164(18) 0.04607(6) 0.0224(2) Uani 1 1 d . . . C4 C 0.2501(3) 0.69060(19) 0.29627(6) 0.0191(2) Uani 1 1 d . . . C1 C 0.2481(2) 0.69753(19) 0.13320(6) 0.0181(2) Uani 1 1 d . . . C2 C 0.1827(2) 0.8810(2) 0.17431(7) 0.0198(2) Uani 1 1 d . . . C6 C 0.3171(2) 0.5122(2) 0.17168(7) 0.0200(3) Uani 1 1 d . . . C5 C 0.31786(19) 0.5087(2) 0.25424(7) 0.0201(3) Uani 1 1 d . . . C3 C 0.1840(2) 0.8774(2) 0.25657(7) 0.0203(3) Uani 1 1 d . . . H3 H 0.138(3) 1.005(3) 0.2843(10) 0.021(4) Uiso 1 1 d . . . H2 H 0.141(3) 1.008(3) 0.1471(10) 0.033(5) Uiso 1 1 d . . . H5 H 0.357(3) 0.384(3) 0.2822(11) 0.029(4) Uiso 1 1 d . . . H1C H 0.247(3) 0.572(3) 0.0274(9) 0.032(4) Uiso 1 1 d . . . H6 H 0.364(3) 0.392(3) 0.1447(10) 0.023(4) Uiso 1 1 d . . . H1B H 0.135(3) 0.777(4) 0.0286(16) 0.029(5) Uiso 1 1 d . . . H1A H 0.353(4) 0.760(5) 0.028(2) 0.058(8) Uiso 1 1 d . . . H4 H 0.266(4) 0.576(4) 0.3950(10) 0.044(5) 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 Cl1 0.02609(16) 0.02218(17) 0.02591(16) 0.00422(9) -0.00003(19) 0.00020(12) O4 0.0396(5) 0.0255(5) 0.0150(4) 0.0015(3) -0.0001(6) -0.0037(5) N1 0.0289(5) 0.0231(5) 0.0151(5) 0.0001(4) -0.0009(6) -0.0010(6) C4 0.0177(5) 0.0239(6) 0.0159(5) 0.0012(4) -0.0007(6) -0.0047(6) C1 0.0171(5) 0.0228(6) 0.0144(5) 0.0008(4) 0.0006(6) 0.0000(6) C2 0.0194(5) 0.0188(6) 0.0211(6) 0.0024(4) -0.0004(5) 0.0015(4) C6 0.0206(6) 0.0187(6) 0.0206(6) -0.0013(4) 0.0012(5) 0.0021(4) C5 0.0198(5) 0.0193(6) 0.0213(6) 0.0046(4) -0.0012(5) 0.0003(4) C3 0.0200(5) 0.0202(6) 0.0207(5) -0.0022(4) 0.0007(5) 0.0003(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 O4 C4 1.3668(13) . ? N1 C1 1.4703(13) . ? C4 C5 1.3906(18) . ? C4 C3 1.3919(18) . ? C1 C6 1.3807(17) . ? C1 C2 1.3862(17) . ? C2 C3 1.3879(16) . ? C6 C5 1.3930(16) . ? 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 O4 C4 C5 121.96(11) . . ? O4 C4 C3 117.46(11) . . ? C5 C4 C3 120.59(10) . . ? C6 C1 C2 121.92(10) . . ? C6 C1 N1 119.21(11) . . ? C2 C1 N1 118.87(11) . . ? C1 C2 C3 119.04(12) . . ? C1 C6 C5 118.93(12) . . ? C4 C5 C6 119.77(12) . . ? C2 C3 C4 119.74(12) . . ? 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 C6 C1 C2 C3 -0.9(2) . . . . ? N1 C1 C2 C3 179.62(14) . . . . ? C2 C1 C6 C5 1.0(2) . . . . ? N1 C1 C6 C5 -179.51(14) . . . . ? O4 C4 C5 C6 179.80(15) . . . . ? C3 C4 C5 C6 -0.8(2) . . . . ? C1 C6 C5 C4 -0.1(2) . . . . ? C1 C2 C3 C4 -0.1(2) . . . . ? O4 C4 C3 C2 -179.66(15) . . . . ? C5 C4 C3 C2 0.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.271 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.056