N-{4-[(3-Methylphenyl)sulfamoyl]phenyl}benzamide

This is an electronic reprint of the original article. This reprint may differ from the original in pagination and typographic detail. Author(s): Title: Year: Version: Please cite the original version: All material supplied via JYX is protected by copyright and other intellectual property rights, and duplication or sale of all or part of any of the repository collections is not permitted, except that material may be duplicated by you for your research use or educational purposes in electronic or print form. You must obtain permission for any other use. Electronic or print copies may not be offered, whether for sale or otherwise to anyone who is not an authorised user. N-{4-[(3-Methylphenyl)sulfamoyl]phenyl}benzamide Lahtinen, Manu; Damodara, Jyonthi; Upadhyaya, Poornima; Nonappa, Nonappa; Kolehmainen, Erkki Lahtinen, M., Damodara, J., Upadhyaya, P., Nonappa, N., & Kolehmainen, E. (2011). N-{4-[(3-Methylphenyl)sulfamoyl]phenyl}benzamide. Acta Crystallographica Section E, 67(11), o2866. https://doi.org/10.1107/S1600536811040384 2011 N-{4-[(3-Methylphenyl)sulfamoyl]- phenyl}benzamide Manu Lahtinen, a Jyothi Damodara, b * Poornima Upadhyaya, b Nonappa a and Erkki Kolehmainen a a University of Jyva ¨skyla ¨, Department of Chemistry, PO Box 35, FI-40014 JY, Finland, and b Department of Chemistry, St. Joseph Engineering College, Vamanjoor, Mangalore 575 028, India Correspondence e-mail: [email protected] Received 28 September 2011; accepted 30 September 2011 Key indicators: single-crystal X-ray study; T= 123 K; mean (C–C) = 0.003 A ˚; Rfactor = 0.037; wR factor = 0.088; data-to-parameter ratio = 12.9. In the title compound, C 20 H 18 N 2 O 3 S, the dihedral angle between the central benzene ring and the amide group is 24.1 (3)and that between this ring and the aromatic ring of the tolyl group is 68.2 (16). In the crystal, adjacent molecules are linked by N—HO hydrogen bonds into a linear chain running along [100]. Weak C—HO contacts also occur. Extensive weak –interactions exist from both face-to-face and face-to-edge interactions occur between the aromatic rings [centroid–centroid distances = 3.612 (2) and 4.843 (2) A ˚]. Related literature For related structures, see: Aziz-ur-Rehman et al. (2010a,b,c); Khan et al. (2010); Shad et al. (2008, 2009); Yasmeen et al. (2010); Gowda et al. (2007). Experimental Crystal data C 20 H 18 N 2 O 3 S M r = 366.42 Triclinic, P1 a= 8.5344 (2) A ˚ b= 8.8477 (3) A ˚ c= 12.4383 (4) A ˚ = 77.924 (2) = 75.382 (2) = 86.537 (2) V= 888.67 (5) A ˚ 3 Z=2 Mo Kradiation = 0.21 mm 1 T= 123 K 0.32 0.20 0.16 mm Data collection Nonius KappaCCD diffractometer with Bruker APEXII detector Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.675, T max = 0.746 11971 measured reflections 3122 independent reflections 2591 reflections with I>2(I) R int = 0.040 Refinement R[F 2 >2(F 2 )] = 0.037 wR(F 2 ) = 0.088 S= 1.04 3122 reflections 242 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement  max = 0.22 e A ˚ 3  min =0.41 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚,). D—HAD—H HADAD—HA N7—H7O27 i 0.86 (2) 1.99 (2) 2.813 (2) 160 (2) N25—H25O17 ii 0.84 (2) 2.38 (2) 3.062 (2) 140 (2) C4—H4O18 0.95 2.40 3.047 (3) 125 Symmetry codes: (i) x;yþ2;zþ2; (ii) x1;y;z. Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997; Otwinowski et al. 2003); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5238). References Aziz-ur-Rehman, Rafique, H., Akkurt, M., Dilber, N., Abbasi, M. A. & Khan, I. U. (2010a). Acta Cryst. E66, o1728. Aziz-ur-Rehman, Sajjad, M. A., Akkurt, M., Sharif, S., Abbasi, M. A. & Khan, I. U. (2010b). Acta Cryst. E66, o1769. Aziz-ur-Rehman, Shahzaman, Akkurt, M., Abbasi, M. A. & Khan, I. U. (2010c). Acta Cryst. E66, o2855. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2339. Khan, I. U., Sharif, S., Akkurt, M., Sajjad, A. & Ahmad, J. (2010). Acta Cryst. E66, o786. Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z., Borek, D., Majewski, W. & Minor, W. (2003). Acta Cryst. A59, 228–234. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Shad, H. A., Chohan, Z. H., Tahir, M. N. & Khan, I. U. (2008). Acta Cryst. E64, o635. Shad, H. A., Tahir, M. N. & Chohan, Z. H. (2009). Acta Cryst. E65, o98–o99. Sheldrick, G. M. (1996). SADABS. University of Go ¨ttingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Yasmeen, S., Murtaza, S., Akkurt, M., Khan, I. U. & Sharif, S. (2010). Acta Cryst. E66, o2264. organic compounds o2866 Lahtinen et al. doi:10.1107/S1600536811040384 Acta Cryst. (2011). E67, o2866 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 supporting information sup-1 Acta Cryst. (2011). E67, o2866 supporting information Acta Cryst. (2011). E67, o2866 [doi:10.1107/S1600536811040384] N-{4-[(3-Methylphenyl)sulfamoyl]phenyl}benzamide Manu Lahtinen, Jyothi Damodara, Poornima Upadhyaya, Nonappa and Erkki Kolehmainen S1. Comment Sulfonamides are very important class of compounds because of their antibacterial and enzyme inhibitor properties as well as their extensive use in medicine. As a contribution to a structural study of sulfonamide derivatives (Khan et al., 2010; Aziz-ur-Rehman et al., 2010a,b,c; Yasmeen et al., 2010; Gowda et al. 2007), we report here the title compound, N-{4-[(3-methylphenyl)sulfamoyl]phenyl}benzamide (I). Compound (I) crystallizes in triclinic space group P-1 (No. 2) without any solvent molecules and having a single molecule in an asymmetric unit (Fig. 1). The sulfonyl and amide groups show characteristic geometries (tetrahedral and planar conformation, respectively) having typical bond distances and angles for these groups (see Tables). The dihedral angles between the central phenyl group [C(19)>C(24)] and amide group N(25)—C(26)—O(27) is about 24° and the tilting of terminal groups bonded to the sulfonamide is about 111°. The molecules are packed in infinite chains along tne a-axis enabling the hydrogen bond network to occur via a axis, whereas along c axis the packing is more columnar forming "box"-like shapes cornered by the sulfonyl groups (Fig. 2). The infinite hydrogen bond networks, along a axis, occur via N(7)—H(7)···O(27) and N(25)—H(25)···O(17) donor-acceptors with d(D···A) bond distances of 2.813 (2) and 3.062 (2) Å in angles of about 160° and 140°, respectively. Three weaker intramolecular hydrogen bonds exist between aromatic ring H atoms (H4, H20 H23) and O atoms O(27) and O(18) having d(D···A) distances of about 2.9–3.0 Å and having fairly unfavorable contact angles varying 105–125°. In addition extensive weak π-π interactions exist in the structure as both face-to-face and face-to-edge interactions occurs between the phenyl rings (Fig. 3). S2. Experimental 4-Amino-N-(3-methylphenyl)benzenesulfonamide (0.5 g, 1.91 mmol) was taken in 20 ml dry EtOH and then benzoyl chloride (0.22 ml, 1.91 mmol) was added dropwise. The reaction medium was maintained at basic condition by adding pyridine to neutralize the produced HCl. The mixture was refluxed at 343 K for 2 h to complete the reaction. The progress of the reaction was monitored by TLC. A white precipitate obtained was filtered and purified in acetone to constant melting point. Few crystals suitable for a single-crystal structure determination were recrystallized from ethanolacetone solution. S3. Refinement Hydrogen atoms were either calculated to their positions as riding atoms (C host) or taken from the electron density map (N host) using isotropic displacement parameters that were fixed to be 1.2 or 1.5 times larger than those of the attached non-hydrogen atom. supporting information sup-2 Acta Cryst. (2011). E67, o2866 Figure 1 The molecular structure of title compound showing 50% propability displacement ellipsoids and the atomic numbering. Figure 2 Molecular packing along a-, b- and c-axes from left to right, respectively. Figure 3 Examples of extensive π-π interaction networks between neighbouring molecules. N-{4-[(3-Methylphenyl)sulfamoyl]phenyl}benzamide Crystal data C20H18N2O3S Mr = 366.42 Triclinic, P1 a = 8.5344 (2) Å b = 8.8477 (3) Å c = 12.4383 (4) Å α = 77.924 (2)° β = 75.382 (2)° supporting information sup-3 Acta Cryst. (2011). E67, o2866 γ = 86.537 (2)° V = 888.67 (5) Å3 Z = 2 F(000) = 384 Dx = 1.369 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 4151 reflections θ = 0.4–28.3° µ = 0.21 mm−1 T = 123 K Block, colourless 0.32 × 0.20 × 0.16 mm Data collection Nonius KappaCCD diffractometer with Bruker APEXII detector Radiation source: fine-focus sealed tube Graphite monochromator φ and ω scans Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.675, Tmax = 0.746 11971 measured reflections 3122 independent reflections 2591 reflections with I > 2σ(I) Rint = 0.040 θmax = 25.0°, θmin = 2.5° h = −10→10 k = −10→10 l = −14→14 Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.037 wR(F2) = 0.088 S = 1.04 3122 reflections 242 parameters 2 restraints Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H atoms treated by a mixture of independent and constrained refinement w = 1/[σ2(Fo2) + (0.0225P)2 + 0.7958P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.001 Δρmax = 0.22 e Å−3 Δρmin = −0.41 e Å−3 Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) xyzU iso*/Ueq C28 −0.6233 (2) 0.8118 (2) 1.16798 (16) 0.0171 (4) C29 −0.6766 (2) 0.6615 (2) 1.21654 (17) 0.0204 (4) H29 −0.6033 0.5769 1.2093 0.024* C30 −0.8372 (2) 0.6356 (3) 1.27566 (18) 0.0246 (5) H30 −0.8736 0.5333 1.3098 0.030* C31 −0.9443 (2) 0.7590 (3) 1.28473 (17) 0.0257 (5) H31 −1.0549 0.7407 1.3229 0.031* C32 −0.8910 (2) 0.9090 (3) 1.23850 (18) 0.0260 (5) H32 −0.9646 0.9933 1.2458 0.031* C33 −0.7305 (2) 0.9358 (2) 1.18166 (17) 0.0204 (4) supporting information sup-4 Acta Cryst. (2011). E67, o2866 H33 −0.6932 1.0387 1.1519 0.025* C26 −0.4514 (2) 0.8461 (2) 1.10486 (16) 0.0167 (4) C22 −0.2076 (2) 0.7276 (2) 0.99572 (16) 0.0152 (4) C23 −0.0888 (2) 0.7983 (2) 1.02747 (17) 0.0180 (4) H23 −0.1190 0.8589 1.0843 0.022* C24 0.0732 (2) 0.7796 (2) 0.97568 (17) 0.0176 (4) H24 0.1545 0.8273 0.9968 0.021* C19 0.1162 (2) 0.6904 (2) 0.89228 (16) 0.0155 (4) C20 −0.0010 (2) 0.6204 (2) 0.86079 (17) 0.0176 (4) H20 0.0293 0.5595 0.8042 0.021* C21 −0.1630 (2) 0.6395 (2) 0.91227 (16) 0.0177 (4) H21 −0.2439 0.5923 0.8904 0.021* C5 0.3326 (2) 0.9120 (2) 0.65597 (16) 0.0192 (4) C6 0.3642 (2) 1.0699 (2) 0.62394 (17) 0.0220 (4) H6 0.4185 1.1168 0.6663 0.026* C1 0.3176 (2) 1.1604 (3) 0.53119 (18) 0.0276 (5) C1B 0.3540 (3) 1.3306 (3) 0.4984 (2) 0.0390 (6) H1B1 0.4356 1.3519 0.4260 0.058* H1B2 0.3955 1.3617 0.5571 0.058* H1B3 0.2548 1.3890 0.4909 0.058* C2 0.2371 (3) 1.0896 (3) 0.47118 (19) 0.0326 (6) H2 0.2038 1.1492 0.4078 0.039* C3 0.2051 (3) 0.9333 (3) 0.50290 (19) 0.0321 (5) H3 0.1492 0.8870 0.4612 0.039* C4 0.2530 (2) 0.8425 (3) 0.59478 (17) 0.0251 (5) H4 0.2317 0.7347 0.6153 0.030* N25 −0.37393 (19) 0.73597 (19) 1.04858 (14) 0.0174 (4) N7 0.39203 (18) 0.82946 (19) 0.74938 (14) 0.0172 (4) O27 −0.38543 (16) 0.96655 (15) 1.10373 (12) 0.0208 (3) O17 0.41159 (15) 0.63241 (15) 0.91408 (11) 0.0196 (3) O18 0.33106 (15) 0.55489 (15) 0.75619 (12) 0.0204 (3) S16 0.32251 (5) 0.66440 (5) 0.82764 (4) 0.01601 (14) H7 0.415 (2) 0.887 (2) 0.7913 (17) 0.019* H25 −0.430 (2) 0.668 (2) 1.0390 (18) 0.019* Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23 C28 0.0168 (10) 0.0206 (10) 0.0157 (10) 0.0016 (8) −0.0056 (8) −0.0060 (8) C29 0.0170 (10) 0.0216 (10) 0.0235 (11) 0.0017 (8) −0.0045 (8) −0.0075 (9) C30 0.0206 (11) 0.0283 (12) 0.0251 (12) −0.0053 (9) −0.0024 (9) −0.0081 (9) C31 0.0157 (10) 0.0428 (13) 0.0197 (11) −0.0004 (9) −0.0019 (8) −0.0114 (10) C32 0.0205 (11) 0.0363 (13) 0.0235 (12) 0.0122 (9) −0.0070 (9) −0.0126 (10) C33 0.0226 (10) 0.0221 (10) 0.0172 (10) 0.0051 (8) −0.0064 (8) −0.0051 (8) C26 0.0179 (10) 0.0181 (10) 0.0147 (10) 0.0022 (8) −0.0062 (8) −0.0023 (8) C22 0.0150 (9) 0.0134 (9) 0.0158 (10) −0.0007 (7) −0.0032 (7) 0.0000 (8) C23 0.0201 (10) 0.0163 (10) 0.0192 (10) 0.0025 (8) −0.0060 (8) −0.0066 (8) C24 0.0164 (10) 0.0160 (10) 0.0218 (11) −0.0003 (8) −0.0069 (8) −0.0044 (8) supporting information sup-5 Acta Cryst. (2011). E67, o2866 C19 0.0139 (9) 0.0161 (9) 0.0146 (10) −0.0002 (7) −0.0017 (7) −0.0007 (8) C20 0.0180 (10) 0.0172 (10) 0.0185 (10) −0.0002 (8) −0.0038 (8) −0.0060 (8) C21 0.0164 (10) 0.0169 (10) 0.0215 (11) −0.0022 (8) −0.0067 (8) −0.0042 (8) C5 0.0127 (9) 0.0245 (11) 0.0169 (10) 0.0040 (8) −0.0001 (8) −0.0022 (8) C6 0.0177 (10) 0.0236 (11) 0.0201 (11) 0.0026 (8) 0.0021 (8) −0.0033 (9) C1 0.0200 (11) 0.0306 (12) 0.0227 (12) 0.0089 (9) 0.0048 (9) 0.0012 (9) C1B 0.0414 (14) 0.0288 (13) 0.0329 (14) 0.0107 (11) 0.0030 (11) 0.0064 (11) C2 0.0221 (11) 0.0484 (15) 0.0206 (12) 0.0082 (10) −0.0036 (9) 0.0031 (10) C3 0.0228 (11) 0.0491 (15) 0.0244 (12) −0.0033 (10) −0.0073 (9) −0.0048 (11) C4 0.0209 (11) 0.0307 (12) 0.0226 (12) −0.0027 (9) −0.0044 (9) −0.0034 (9) N25 0.0131 (8) 0.0159 (8) 0.0241 (9) −0.0008 (7) −0.0027 (7) −0.0083 (7) N7 0.0161 (8) 0.0172 (9) 0.0190 (9) −0.0018 (7) −0.0052 (7) −0.0038 (7) O27 0.0210 (7) 0.0163 (7) 0.0256 (8) −0.0022 (6) −0.0036 (6) −0.0073 (6) O17 0.0158 (7) 0.0213 (7) 0.0223 (8) 0.0018 (6) −0.0071 (6) −0.0032 (6) O18 0.0183 (7) 0.0191 (7) 0.0249 (8) 0.0006 (6) −0.0026 (6) −0.0100 (6) S16 0.0132 (2) 0.0155 (2) 0.0188 (3) 0.00087 (18) −0.00303 (18) −0.00364 (19) Geometric parameters (Å, º) C28—C29 1.392 (3) C20—C21 1.386 (3) C28—C33 1.396 (3) C20—H20 0.9500 C28—C26 1.495 (3) C21—H21 0.9500 C29—C30 1.390 (3) C5—C4 1.388 (3) C29—H29 0.9500 C5—C6 1.394 (3) C30—C31 1.385 (3) C5—N7 1.428 (3) C30—H30 0.9500 C6—C1 1.391 (3) C31—C32 1.386 (3) C6—H6 0.9500 C31—H31 0.9500 C1—C2 1.389 (3) C32—C33 1.383 (3) C1—C1B 1.506 (3) C32—H32 0.9500 C1B—H1B1 0.9800 C33—H33 0.9500 C1B—H1B2 0.9800 C26—O27 1.231 (2) C1B—H1B3 0.9800 C26—N25 1.360 (2) C2—C3 1.380 (3) C22—C21 1.390 (3) C2—H2 0.9500 C22—C23 1.400 (3) C3—C4 1.390 (3) C22—N25 1.410 (2) C3—H3 0.9500 C23—C24 1.386 (3) C4—H4 0.9500 C23—H23 0.9500 N25—H25 0.835 (15) C24—C19 1.396 (3) N7—S16 1.6280 (16) C24—H24 0.9500 N7—H7 0.861 (15) C19—C20 1.383 (3) O17—S16 1.4400 (14) C19—S16 1.7642 (18) O18—S16 1.4328 (14) C29—C28—C33 119.77 (18) C22—C21—H21 119.8 C29—C28—C26 121.93 (17) C4—C5—C6 119.79 (19) C33—C28—C26 118.25 (18) C4—C5—N7 123.68 (18) C30—C29—C28 119.81 (18) C6—C5—N7 116.48 (18) C30—C29—H29 120.1 C1—C6—C5 121.3 (2) supporting information sup-6 Acta Cryst. (2011). E67, o2866 C28—C29—H29 120.1 C1—C6—H6 119.3 C31—C30—C29 120.0 (2) C5—C6—H6 119.3 C31—C30—H30 120.0 C2—C1—C6 118.3 (2) C29—C30—H30 120.0 C2—C1—C1B 121.6 (2) C30—C31—C32 120.40 (19) C6—C1—C1B 120.1 (2) C30—C31—H31 119.8 C1—C1B—H1B1 109.5 C32—C31—H31 119.8 C1—C1B—H1B2 109.5 C33—C32—C31 119.89 (19) H1B1—C1B—H1B2 109.5 C33—C32—H32 120.1 C1—C1B—H1B3 109.5 C31—C32—H32 120.1 H1B1—C1B—H1B3 109.5 C32—C33—C28 120.08 (19) H1B2—C1B—H1B3 109.5 C32—C33—H33 120.0 C3—C2—C1 120.6 (2) C28—C33—H33 120.0 C3—C2—H2 119.7 O27—C26—N25 122.61 (17) C1—C2—H2 119.7 O27—C26—C28 121.90 (17) C2—C3—C4 121.2 (2) N25—C26—C28 115.48 (16) C2—C3—H3 119.4 C21—C22—C23 119.99 (17) C4—C3—H3 119.4 C21—C22—N25 117.37 (16) C5—C4—C3 118.8 (2) C23—C22—N25 122.59 (17) C5—C4—H4 120.6 C24—C23—C22 119.69 (18) C3—C4—H4 120.6 C24—C23—H23 120.2 C26—N25—C22 127.54 (16) C22—C23—H23 120.2 C26—N25—H25 118.0 (15) C23—C24—C19 119.67 (17) C22—N25—H25 114.2 (15) C23—C24—H24 120.2 C5—N7—S16 124.74 (13) C19—C24—H24 120.2 C5—N7—H7 114.5 (14) C20—C19—C24 120.72 (17) S16—N7—H7 109.6 (14) C20—C19—S16 119.57 (15) O18—S16—O17 118.60 (8) C24—C19—S16 119.70 (14) O18—S16—N7 109.02 (8) C19—C20—C21 119.61 (18) O17—S16—N7 104.61 (8) C19—C20—H20 120.2 O18—S16—C19 107.45 (8) C21—C20—H20 120.2 O17—S16—C19 108.77 (8) C20—C21—C22 120.32 (17) N7—S16—C19 107.99 (8) C20—C21—H21 119.8 C33—C28—C29—C30 1.8 (3) C5—C6—C1—C2 0.6 (3) C26—C28—C29—C30 179.18 (18) C5—C6—C1—C1B −179.75 (18) C28—C29—C30—C31 0.9 (3) C6—C1—C2—C3 −0.3 (3) C29—C30—C31—C32 −2.2 (3) C1B—C1—C2—C3 −180.0 (2) C30—C31—C32—C33 0.8 (3) C1—C2—C3—C4 −0.4 (3) C31—C32—C33—C28 1.9 (3) C6—C5—C4—C3 −0.6 (3) C29—C28—C33—C32 −3.2 (3) N7—C5—C4—C3 −177.87 (18) C26—C28—C33—C32 179.34 (18) C2—C3—C4—C5 0.9 (3) C29—C28—C26—O27 −148.36 (19) O27—C26—N25—C22 9.8 (3) C33—C28—C26—O27 29.1 (3) C28—C26—N25—C22 −170.63 (17) C29—C28—C26—N25 32.1 (3) C21—C22—N25—C26 −158.59 (19) C33—C28—C26—N25 −150.49 (18) C23—C22—N25—C26 24.1 (3) C21—C22—C23—C24 −0.3 (3) C4—C5—N7—S16 −24.1 (3) N25—C22—C23—C24 177.01 (17) C6—C5—N7—S16 158.56 (14) supporting information sup-7 Acta Cryst. (2011). E67, o2866 C22—C23—C24—C19 0.0 (3) C5—N7—S16—O18 55.80 (17) C23—C24—C19—C20 0.0 (3) C5—N7—S16—O17 −176.39 (15) C23—C24—C19—S16 −179.17 (14) C5—N7—S16—C19 −60.64 (17) C24—C19—C20—C21 0.3 (3) C20—C19—S16—O18 −5.69 (18) S16—C19—C20—C21 179.41 (15) C24—C19—S16—O18 173.47 (15) C19—C20—C21—C22 −0.5 (3) C20—C19—S16—O17 −135.24 (15) C23—C22—C21—C20 0.5 (3) C24—C19—S16—O17 43.92 (18) N25—C22—C21—C20 −176.90 (17) C20—C19—S16—N7 111.78 (16) C4—C5—C6—C1 −0.1 (3) C24—C19—S16—N7 −69.07 (17) N7—C5—C6—C1 177.35 (17) Hydrogen-bond geometry (Å, º) D—H···AD—H H···AD···AD—H···A N7—H7···O27i0.86 (2) 1.99 (2) 2.813 (2) 160 (2) N25—H25···O17ii 0.84 (2) 2.38 (2) 3.062 (2) 140 (2) C4—H4···O18 0.95 2.40 3.047 (3) 125 C20—H20···O18 0.95 2.49 2.884 (2) 105 C23—H23···O27 0.95 2.39 2.907 (2) 114 Symmetry codes: (i) −x, −y+2, −z+2; (ii) x−1, y, z.