# Electronic Supplementary Material (ESI) for RSC Advances # 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_shelxl #TrackingRef '130322.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 Br N2 O3 S' _chemical_formula_weight 469.35 _chemical_absolute_configuration ad 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' Br Br -0.2901 2.4595 '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 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 9.0110(3) _cell_length_b 10.3134(5) _cell_length_c 22.7196(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2111.42(15) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 1984 _cell_measurement_theta_min 2.8795 _cell_measurement_theta_max 29.0197 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 2.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5309 _exptl_absorpt_correction_T_max 0.5754 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Gemini S Ultra, Agilent Technologies' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8864 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 26.36 _reflns_number_total 4253 _reflns_number_gt 2935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Agilent Technologies)' _computing_cell_refinement 'CrysAlisPro (Agilent Technologies)' _computing_data_reduction 'CrysAlisPro (Agilent Technologies)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0649P)^2^+0.6428P] 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 constr _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 -0.016(14) _refine_ls_number_reflns 4253 _refine_ls_number_parameters 263 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1422 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.048 _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 Br1 Br 1.04571(8) 1.26981(7) 0.98352(3) 0.0693(3) Uani 1 1 d . . . S1 S 1.46274(17) 1.46588(17) 1.16921(7) 0.0541(4) Uani 1 1 d . . . N1 N 1.3309(4) 1.5579(5) 1.14033(19) 0.0437(11) Uani 1 1 d . . . O1 O 1.4586(5) 1.3455(5) 1.13857(19) 0.0738(13) Uani 1 1 d . . . N2 N 1.0740(4) 1.6005(4) 1.2038(2) 0.0429(11) Uani 1 1 d . . . C10 C 1.0548(6) 1.3729(6) 1.0523(2) 0.0464(13) Uani 1 1 d . . . C8 C 1.1941(5) 1.4994(6) 1.1209(2) 0.0395(13) Uani 1 1 d . . . O2 O 1.5943(4) 1.5429(6) 1.1685(2) 0.0790(16) Uani 1 1 d . . . C13 C 1.0627(6) 1.5248(5) 1.1522(2) 0.0396(12) Uani 1 1 d . . . C9 C 1.1881(6) 1.4220(6) 1.0708(2) 0.0455(15) Uani 1 1 d . . . H9 H 1.2744 1.4036 1.0500 0.055 Uiso 1 1 calc R . . C18 C 1.3087(6) 1.6902(6) 1.1675(3) 0.0555(14) Uani 1 1 d U . . H18 H 1.4027 1.7186 1.1850 0.067 Uiso 1 1 calc R . . C4 C 1.4145(5) 1.4385(6) 1.2433(3) 0.0474(14) Uani 1 1 d . . . C19 C 1.2657(7) 1.7836(8) 1.1202(3) 0.0751(15) Uani 1 1 d U . . C11 C 0.9244(6) 1.4006(6) 1.0826(3) 0.0525(16) Uani 1 1 d . . . H11 H 0.8341 1.3674 1.0696 0.063 Uiso 1 1 calc R . . C16 C 1.1797(6) 1.7270(7) 1.2701(3) 0.0579(16) Uani 1 1 d . . . H16 H 1.2451 1.7826 1.2892 0.069 Uiso 1 1 calc R . . C5 C 1.3010(7) 1.3535(7) 1.2565(3) 0.0599(17) Uani 1 1 d . . . H5 H 1.2541 1.3077 1.2266 0.072 Uiso 1 1 calc R . . O3 O 1.3494(7) 1.7866(7) 1.0697(3) 0.1099(16) Uani 1 1 d U . . C12 C 0.9309(6) 1.4778(6) 1.1318(2) 0.0459(14) Uani 1 1 d . . . H12 H 0.8437 1.4983 1.1517 0.055 Uiso 1 1 calc R . . C17 C 1.1954(6) 1.6790(5) 1.2151(3) 0.0434(14) Uani 1 1 d . . . C14 C 0.9836(6) 1.5986(6) 1.2518(3) 0.0559(16) Uani 1 1 d . . . H14 H 0.8956 1.5523 1.2556 0.067 Uiso 1 1 calc R . . C6 C 1.2576(8) 1.3367(8) 1.3136(4) 0.076(2) Uani 1 1 d . . . H6 H 1.1812 1.2793 1.3224 0.091 Uiso 1 1 calc R . . C3 C 1.4847(7) 1.5076(7) 1.2875(3) 0.0630(18) Uani 1 1 d . . . H3 H 1.5612 1.5650 1.2789 0.076 Uiso 1 1 calc R . . C20 C 1.1700(10) 1.8779(10) 1.1229(5) 0.103(2) Uani 1 1 d U . . H20 H 1.1082 1.8998 1.1542 0.124 Uiso 1 1 calc R . . C22 C 1.2762(11) 1.8873(11) 1.0379(5) 0.116(2) Uani 1 1 d U . . H22 H 1.2988 1.9099 0.9993 0.139 Uiso 1 1 calc R . . C15 C 1.0461(8) 1.6773(7) 1.2932(3) 0.0673(18) Uani 1 1 d . . . H15 H 1.0073 1.6951 1.3303 0.081 Uiso 1 1 calc R . . C2 C 1.4381(9) 1.4890(8) 1.3450(3) 0.077(2) Uani 1 1 d . . . H2 H 1.4840 1.5352 1.3751 0.093 Uiso 1 1 calc R . . C21 C 1.1817(11) 1.9397(11) 1.0670(4) 0.113(2) Uani 1 1 d U . . H21 H 1.1249 2.0100 1.0547 0.135 Uiso 1 1 calc R . . C1 C 1.3265(9) 1.4045(9) 1.3585(4) 0.082(2) Uani 1 1 d U . . C7 C 1.2717(11) 1.3881(11) 1.4228(4) 0.117(3) Uani 1 1 d U . . H7A H 1.1864 1.4422 1.4292 0.175 Uiso 1 1 calc R . . H7B H 1.3493 1.4129 1.4495 0.175 Uiso 1 1 calc R . . H7C H 1.2454 1.2992 1.4295 0.175 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 Br1 0.0807(5) 0.0707(5) 0.0564(4) -0.0184(4) -0.0157(3) -0.0008(4) S1 0.0343(7) 0.0733(11) 0.0547(8) -0.0152(8) 0.0000(7) 0.0134(8) N1 0.034(2) 0.053(3) 0.044(3) -0.006(2) -0.001(2) 0.000(2) O1 0.070(3) 0.082(3) 0.069(3) -0.027(3) -0.007(3) 0.033(3) N2 0.035(3) 0.048(3) 0.046(3) -0.006(2) 0.006(2) 0.006(2) C10 0.049(3) 0.049(3) 0.041(3) -0.001(3) -0.007(3) -0.003(3) C8 0.029(3) 0.041(3) 0.048(3) 0.003(3) 0.001(2) 0.005(2) O2 0.028(2) 0.123(5) 0.086(3) 0.001(3) 0.004(2) -0.002(2) C13 0.038(3) 0.039(3) 0.042(3) 0.006(2) 0.000(2) 0.008(3) C9 0.046(3) 0.057(4) 0.033(3) 0.001(3) 0.000(2) 0.011(3) C18 0.033(3) 0.066(4) 0.067(4) -0.027(2) 0.000(3) -0.004(3) C4 0.042(3) 0.048(4) 0.052(3) -0.004(3) -0.009(2) 0.009(3) C19 0.059(4) 0.073(4) 0.093(3) -0.013(3) -0.011(2) -0.021(3) C11 0.048(4) 0.054(4) 0.056(4) 0.002(3) -0.012(3) -0.010(3) C16 0.060(4) 0.061(4) 0.053(3) -0.015(4) 0.002(3) 0.007(3) C5 0.057(4) 0.060(5) 0.063(4) -0.003(4) -0.014(3) -0.002(3) O3 0.115(2) 0.109(2) 0.105(2) 0.0032(17) 0.0111(16) 0.0009(17) C12 0.033(3) 0.054(4) 0.051(3) 0.002(3) 0.006(2) 0.005(3) C17 0.039(3) 0.037(3) 0.054(4) -0.003(3) 0.002(2) 0.009(2) C14 0.052(3) 0.062(4) 0.054(4) -0.001(3) 0.016(3) 0.008(3) C6 0.070(5) 0.069(5) 0.088(6) 0.012(4) 0.000(4) -0.014(4) C3 0.059(4) 0.066(5) 0.064(4) -0.014(4) -0.017(3) 0.007(3) C20 0.103(3) 0.098(3) 0.109(2) 0.0058(18) 0.0008(18) 0.0087(18) C22 0.122(3) 0.117(3) 0.109(2) 0.0084(17) 0.0011(17) -0.0029(19) C15 0.080(4) 0.075(5) 0.047(3) -0.014(3) 0.006(4) 0.012(4) C2 0.082(5) 0.093(6) 0.057(4) -0.016(4) -0.024(4) 0.007(5) C21 0.114(3) 0.110(3) 0.113(3) 0.0114(17) -0.0042(18) 0.0011(18) C1 0.073(5) 0.080(6) 0.093(4) 0.002(5) -0.015(4) 0.013(4) C7 0.119(4) 0.121(4) 0.110(3) 0.004(2) 0.005(2) -0.001(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 Br1 C10 1.891(5) . ? S1 O1 1.424(5) . ? S1 O2 1.427(5) . ? S1 N1 1.656(5) . ? S1 C4 1.760(6) . ? N1 C8 1.442(7) . ? N1 C18 1.511(8) . ? N2 C14 1.362(7) . ? N2 C17 1.386(7) . ? N2 C13 1.411(7) . ? C10 C9 1.370(8) . ? C10 C11 1.391(8) . ? C8 C9 1.391(8) . ? C8 C13 1.406(7) . ? C13 C12 1.364(7) . ? C9 H9 0.9300 . ? C18 C17 1.490(8) . ? C18 C19 1.495(10) . ? C18 H18 0.9800 . ? C4 C5 1.380(8) . ? C4 C3 1.386(8) . ? C19 C20 1.301(11) . ? C19 O3 1.373(9) . ? C11 C12 1.375(8) . ? C11 H11 0.9300 . ? C16 C17 1.352(8) . ? C16 C15 1.410(9) . ? C16 H16 0.9300 . ? C5 C6 1.365(9) . ? C5 H5 0.9300 . ? O3 C22 1.428(11) . ? C12 H12 0.9300 . ? C14 C15 1.364(8) . ? C14 H14 0.9300 . ? C6 C1 1.384(11) . ? C6 H6 0.9300 . ? C3 C2 1.384(9) . ? C3 H3 0.9300 . ? C20 C21 1.427(12) . ? C20 H20 0.9300 . ? C22 C21 1.206(12) . ? C22 H22 0.9300 . ? C15 H15 0.9300 . ? C2 C1 1.366(11) . ? C2 H2 0.9300 . ? C21 H21 0.9300 . ? C1 C7 1.551(12) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 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 O1 S1 O2 120.1(3) . . ? O1 S1 N1 106.7(3) . . ? O2 S1 N1 105.8(3) . . ? O1 S1 C4 108.7(3) . . ? O2 S1 C4 107.7(3) . . ? N1 S1 C4 107.0(2) . . ? C8 N1 C18 113.0(4) . . ? C8 N1 S1 119.7(4) . . ? C18 N1 S1 116.8(4) . . ? C14 N2 C17 109.4(5) . . ? C14 N2 C13 127.9(5) . . ? C17 N2 C13 122.3(4) . . ? C9 C10 C11 120.9(5) . . ? C9 C10 Br1 120.0(4) . . ? C11 C10 Br1 119.2(4) . . ? C9 C8 C13 119.2(5) . . ? C9 C8 N1 121.6(4) . . ? C13 C8 N1 119.2(5) . . ? C12 C13 C8 119.8(5) . . ? C12 C13 N2 122.8(5) . . ? C8 C13 N2 117.5(5) . . ? C10 C9 C8 119.8(5) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C17 C18 C19 113.1(5) . . ? C17 C18 N1 108.5(5) . . ? C19 C18 N1 108.8(5) . . ? C17 C18 H18 108.8 . . ? C19 C18 H18 108.8 . . ? N1 C18 H18 108.8 . . ? C5 C4 C3 120.4(6) . . ? C5 C4 S1 119.6(5) . . ? C3 C4 S1 119.9(5) . . ? C20 C19 O3 112.8(9) . . ? C20 C19 C18 128.3(8) . . ? O3 C19 C18 118.2(7) . . ? C12 C11 C10 119.1(5) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C17 C16 C15 107.5(6) . . ? C17 C16 H16 126.2 . . ? C15 C16 H16 126.2 . . ? C6 C5 C4 120.0(6) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C19 O3 C22 100.7(7) . . ? C13 C12 C11 121.3(5) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C16 C17 N2 107.6(5) . . ? C16 C17 C18 135.5(6) . . ? N2 C17 C18 116.8(5) . . ? N2 C14 C15 107.3(5) . . ? N2 C14 H14 126.4 . . ? C15 C14 H14 126.4 . . ? C5 C6 C1 120.5(7) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? C2 C3 C4 118.3(7) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C19 C20 C21 104.1(9) . . ? C19 C20 H20 128.0 . . ? C21 C20 H20 128.0 . . ? C21 C22 O3 112.0(11) . . ? C21 C22 H22 124.0 . . ? O3 C22 H22 124.0 . . ? C14 C15 C16 108.2(5) . . ? C14 C15 H15 125.9 . . ? C16 C15 H15 125.9 . . ? C1 C2 C3 121.6(7) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C22 C21 C20 109.9(11) . . ? C22 C21 H21 125.1 . . ? C20 C21 H21 125.1 . . ? C2 C1 C6 119.1(8) . . ? C2 C1 C7 121.1(8) . . ? C6 C1 C7 119.8(8) . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 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 O1 S1 N1 C8 35.3(5) . . . . ? O2 S1 N1 C8 164.3(4) . . . . ? C4 S1 N1 C8 -81.0(4) . . . . ? O1 S1 N1 C18 177.5(4) . . . . ? O2 S1 N1 C18 -53.5(5) . . . . ? C4 S1 N1 C18 61.2(5) . . . . ? C18 N1 C8 C9 145.1(5) . . . . ? S1 N1 C8 C9 -71.4(6) . . . . ? C18 N1 C8 C13 -32.7(7) . . . . ? S1 N1 C8 C13 110.8(5) . . . . ? C9 C8 C13 C12 -2.6(8) . . . . ? N1 C8 C13 C12 175.3(5) . . . . ? C9 C8 C13 N2 178.1(5) . . . . ? N1 C8 C13 N2 -4.1(7) . . . . ? C14 N2 C13 C12 27.8(8) . . . . ? C17 N2 C13 C12 -160.4(5) . . . . ? C14 N2 C13 C8 -152.8(5) . . . . ? C17 N2 C13 C8 19.0(7) . . . . ? C11 C10 C9 C8 0.8(8) . . . . ? Br1 C10 C9 C8 179.0(4) . . . . ? C13 C8 C9 C10 0.7(8) . . . . ? N1 C8 C9 C10 -177.1(5) . . . . ? C8 N1 C18 C17 53.5(6) . . . . ? S1 N1 C18 C17 -91.2(5) . . . . ? C8 N1 C18 C19 -70.0(6) . . . . ? S1 N1 C18 C19 145.3(4) . . . . ? O1 S1 C4 C5 -40.6(5) . . . . ? O2 S1 C4 C5 -172.3(5) . . . . ? N1 S1 C4 C5 74.3(5) . . . . ? O1 S1 C4 C3 142.9(5) . . . . ? O2 S1 C4 C3 11.3(6) . . . . ? N1 S1 C4 C3 -102.2(5) . . . . ? C17 C18 C19 C20 20.8(11) . . . . ? N1 C18 C19 C20 141.5(8) . . . . ? C17 C18 C19 O3 -169.7(6) . . . . ? N1 C18 C19 O3 -49.0(7) . . . . ? C9 C10 C11 C12 -0.4(9) . . . . ? Br1 C10 C11 C12 -178.6(4) . . . . ? C3 C4 C5 C6 -0.2(10) . . . . ? S1 C4 C5 C6 -176.6(6) . . . . ? C20 C19 O3 C22 -7.6(9) . . . . ? C18 C19 O3 C22 -178.6(6) . . . . ? C8 C13 C12 C11 3.0(8) . . . . ? N2 C13 C12 C11 -177.7(5) . . . . ? C10 C11 C12 C13 -1.5(9) . . . . ? C15 C16 C17 N2 -0.1(7) . . . . ? C15 C16 C17 C18 -179.0(7) . . . . ? C14 N2 C17 C16 -0.5(6) . . . . ? C13 N2 C17 C16 -173.6(5) . . . . ? C14 N2 C17 C18 178.6(5) . . . . ? C13 N2 C17 C18 5.5(7) . . . . ? C19 C18 C17 C16 -100.9(8) . . . . ? N1 C18 C17 C16 138.3(7) . . . . ? C19 C18 C17 N2 80.3(7) . . . . ? N1 C18 C17 N2 -40.5(7) . . . . ? C17 N2 C14 C15 0.9(7) . . . . ? C13 N2 C14 C15 173.5(5) . . . . ? C4 C5 C6 C1 0.1(11) . . . . ? C5 C4 C3 C2 0.0(9) . . . . ? S1 C4 C3 C2 176.4(5) . . . . ? O3 C19 C20 C21 6.2(10) . . . . ? C18 C19 C20 C21 176.1(7) . . . . ? C19 O3 C22 C21 6.4(11) . . . . ? N2 C14 C15 C16 -0.9(7) . . . . ? C17 C16 C15 C14 0.6(7) . . . . ? C4 C3 C2 C1 0.4(11) . . . . ? O3 C22 C21 C20 -3.0(13) . . . . ? C19 C20 C21 C22 -1.8(12) . . . . ? C3 C2 C1 C6 -0.5(12) . . . . ? C3 C2 C1 C7 -177.9(8) . . . . ? C5 C6 C1 C2 0.3(12) . . . . ? C5 C6 C1 C7 177.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.483 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 931821'