N -(2-Hydroxy-1,1-dimethylethyl)benzenesulfonamide

organic compounds Acta Crystallographica Section E Data collection Structure Reports Online Bruker APEXII CCD diffractometer 10723 measured reflections ISSN 1600-5368 2857 independent reflections 2331 reflections with I > 2(I) Rint = 0.024 Refinement N-(2-Hydroxy-1,1-dimethylethyl)benzenesulfonamide Aziz-ur-Rehman,a‡ Nadia Abbas,a Mehmet Akkurt,b* Muhammad Athar Abbasi,a Shahzad Sharifa and Islam Ullah Khana R[F 2 > 2(F 2)] = 0.039 wR(F 2) = 0.119 S = 1.04 2857 reflections 176 parameters 8 restraints H-atom parameters constrained
max = 0.31 e Å3
min = 0.34 e Å3 Table 1 Hydrogen-bond geometry (Å,  ). a Department of Chemistry, Government College University, Lahore 54000, Pakistan, and bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey Correspondence e-mail: [email protected] D—H  A Received 26 October 2010; accepted 28 October 2010 Symmetry codes: x; y þ 32; z þ 12. Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.003 Å; disorder in main residue; R factor = 0.039; wR factor = 0.119; data-to-parameter ratio = 16.2. In the title molecule, C10H15NO3S, the S atom is bonded in a distorted tetrahedral geometry. In the crystal structure, intermolecular N—H  O, O—H  O and weak C—H  O hydrogen bonds connect the molecules to form a twodimensional network parallel to (100). The 2-methylpropan1-ol group is disordered over two orientations with occupancies of 0.570 (3) and 0.430 (3). i N1—H1A  O3B O3B—H3B  O2ii C10B—H10D  O1iii (i) D—H H  A D  A D—H  A 0.86 0.82 0.97 2.14 2.02 2.54 2.840 (9) 2.777 (10) 3.478 (3) 139 152 162 x þ 2; y  12; z þ 32; (ii) x þ 2; y þ 1; z þ 1; (iii) Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON. The authors are grateful to the Higher Education Commission of Pakistan for providing financial support. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5159). Related literature For general background to sulfonamide derivatives, see: Ozbek et al. (2007); Parari et al. (2008). For our previous structural studies on sulfonamide derivatives, see: Asiri et al. (2009); Aziz-ur-Rehman et al. (2010). References Asiri, A. M., Akkurt, M., Khan, S. A., Arshad, M. N., Khan, I. U. & Sharif, H. M. A. (2009). Acta Cryst. E65, o1246–o1247. Aziz-ur-Rehman, Sajjad, M. A., Akkurt, M., Sharif, S., Abbasi, M. A. & Khan, I. U. (2010). Acta Cryst. E66, o1769. Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. Ozbek, N., Katircioglu, H., Karacan, N. & Baykal, T. (2007). Bioorg. Med. Chem. 15, 5105–5109. Parari, M. K., Panda, G., Srivastava, K. & Puri, S. K. (2008). Bioorg. Med. Chem. Lett. 18, 776–781. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155. Experimental Crystal data C10H15NO3S Mr = 229.30 Monoclinic, P21 =c a = 12.4094 (3) Å b = 9.0042 (2) Å c = 10.4525 (2) Å  = 93.731 (1) V = 1165.45 (4) Å3 Z=4 Mo K radiation  = 0.27 mm1 T = 296 K 0.24  0.16  0.07 mm ‡ Additional corresponding author, e-mail: [email protected]. o3028 Aziz-ur-Rehman et al. doi:10.1107/S1600536810044144 Acta Cryst. (2010). E66, o3028 supplementary materials supplementary materials Acta Cryst. (2010). E66, o3028 [ doi:10.1107/S1600536810044144 ] N-(2-Hydroxy-1,1-dimethylethyl)benzenesulfonamide Aziz-ur-Rehman, N. Abbas, M. Akkurt, M. A. Abbasi, S. Sharif and I. U. Khan Comment The sulfonamide moiety is found in a number of synthetic as well as natural compounds and renders various biological acitivities in these compounds (Ozbek et al., 2007, Parari et al., 2008). In continuation of our structural studies on various sulfonamide derivatives (Asiri et al., 2009, Aziz-ur-Rehman et al., 2010) herein we report the crystal structure of the title compound (I). The molecular structure of (I) is shown in Fig. 1 and reveals a distorted tetrahedral geometry around the S atom [maximum deviation from the ideal sp3 hybridized geometry for O—S—O = 119.29 (8)°]. There are weak intramolecular C—H···O contacts within the molecule. In the crystal structure, intermolecular N—H···O, O—H···O and weak C—H···O hydrogen bonds connect the molecules to form a two-dimensional network parallel to (100) (Fig. 2). Experimental A mixture of benzenesulfonyl chloride (10.0 mmol; 1.28 ml), 2-amino-2-methyl propanol (10.0 mmol; 0.95 ml), aqueous sodium carbonate (10%; 15.0 ml) and water (20 ml) was stirred for one and half hours at room temperature. The crude mixture was washed with distilled water and dried. The product was dissolved in methanol and recrystallized by slow evaporation of the solvent, to generate colourless crystals of N-(2-hydroxy-1,1-dimethylethyl)benzenesulfonamide in 65% yield. Refinement All H atoms were positioned geometrically with N—H = 0.86, O—H = 0.82 and C—H = 0.93–0.97 Å and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(Cmethyl,O). The 2-methylpropan-1-ol group of the title molecule show disoder over two sets of sites with an occupancy ratio of 0.570 (3):0.430 (3). Figures Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. The disorder is not shown. Fig. 2. Part of the crystal structure of (I) H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity and only the major component of the disorder is shown. sup-1 supplementary materials N-(2-Hydroxy-1,1-dimethylethyl)benzenesulfonamide Crystal data C10H15NO3S F(000) = 488 Mr = 229.30 Dx = 1.307 Mg m−3 Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å Hall symbol: -P 2ybc a = 12.4094 (3) Å Cell parameters from 5041 reflections θ = 2.8–28.2° b = 9.0042 (2) Å µ = 0.27 mm−1 T = 296 K Block, colourless c = 10.4525 (2) Å β = 93.731 (1)° V = 1165.45 (4) Å3 Z=4 0.24 × 0.16 × 0.07 mm Data collection Bruker APEXII CCD diffractometer 2331 reflections with I > 2σ(I) Radiation source: sealed tube Rint = 0.024 graphite θmax = 28.3°, θmin = 3.4° φ and ω scans 10723 measured reflections 2857 independent reflections h = −16→16 k = −12→10 l = −13→11 Refinement R[F2 > 2σ(F2)] = 0.039 Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites wR(F2) = 0.119 H-atom parameters constrained Refinement on F2 Least-squares matrix: full S = 1.04 w = 1/[σ2(Fo2) + (0.0674P)2 + 0.1878P] where P = (Fo2 + 2Fc2)/3 2857 reflections (Δ/σ)max = 0.001 176 parameters Δρmax = 0.31 e Å−3 8 restraints Δρmin = −0.33 e Å−3 Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted Rfactors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The sup-2 supplementary materials observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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) S1 O1 O2 O3B N1 C1 C2 C3 C4 C5 C6 C7 C8B C9B C10B O3A C8A C9A C10A H3B H4 H5 H8B1 H8B2 H8B3 H9B1 H10C H10D H9B2 H9B3 H1 H1A H2 H3 H8A1 H8A2 H8A3 H3A H9A1 H9A2 H9A3 x y z Uiso*/Ueq 0.81238 (3) 0.76229 (12) 0.88776 (11) 0.9863 (5) 0.87618 (9) 0.60374 (15) 0.52364 (17) 0.54859 (17) 0.65240 (17) 0.73310 (14) 0.70811 (11) 0.83869 (12) 0.7250 (3) 0.9096 (4) 0.8755 (2) 0.9831 (10) 0.7815 (4) 0.7497 (4) 0.9310 (3) 1.00300 0.66860 0.80410 0.68280 0.71190 0.70510 0.98460 0.83670 0.85420 0.89140 0.89580 0.58690 0.93950 0.45240 0.49430 0.71950 0.75910 0.83100 0.99830 0.68990 0.77850 0.72560 0.43637 (4) 0.56081 (15) 0.34876 (16) 0.7719 (10) 0.48927 (13) 0.3406 (3) 0.2428 (3) 0.1204 (3) 0.0938 (2) 0.1902 (2) 0.31395 (16) 0.59545 (16) 0.5962 (4) 0.5645 (4) 0.7543 (3) 0.7515 (14) 0.4982 (5) 0.7001 (5) 0.6663 (4) 0.72570 0.01040 0.17220 0.61690 0.67140 0.50100 0.56600 0.77980 0.82490 0.46890 0.63970 0.42360 0.45220 0.26060 0.05440 0.45040 0.56040 0.42430 0.69890 0.64200 0.75770 0.76540 0.53924 (3) 0.47567 (14) 0.47376 (13) 0.7102 (11) 0.66870 (11) 0.5338 (2) 0.5643 (3) 0.6369 (3) 0.6815 (2) 0.65250 (18) 0.57831 (14) 0.76557 (14) 0.7901 (4) 0.8934 (3) 0.7249 (3) 0.7318 (14) 0.8656 (4) 0.7058 (4) 0.8205 (3) 0.64690 0.73160 0.68260 0.71190 0.85230 0.82230 0.87620 0.64430 0.78860 0.92650 0.95540 0.48350 0.68430 0.53530 0.65610 0.82410 0.93360 0.90030 0.67140 0.67100 0.63860 0.77070 0.0453 (1) 0.0735 (5) 0.0715 (5) 0.0594 (14) 0.0397 (3) 0.0764 (7) 0.1035 (10) 0.0838 (8) 0.0694 (7) 0.0581 (5) 0.0437 (4) 0.0444 (4) 0.0746 (13) 0.0733 (13) 0.0519 (9) 0.085 (3) 0.0567 (11) 0.0597 (12) 0.0494 (11) 0.0890* 0.0830* 0.0700* 0.1120* 0.1120* 0.1120* 0.1100* 0.0620* 0.0620* 0.1100* 0.1100* 0.0920* 0.0480* 0.1240* 0.1010* 0.0850* 0.0850* 0.0850* 0.1280* 0.0890* 0.0890* 0.0890* Occ. (<1) 0.570 (3) 0.570 (3) 0.570 (3) 0.570 (3) 0.430 (3) 0.430 (3) 0.430 (3) 0.430 (3) 0.570 (3) 0.570 (3) 0.570 (3) 0.570 (3) 0.570 (3) 0.570 (3) 0.570 (3) 0.570 (3) 0.570 (3) 0.430 (3) 0.430 (3) 0.430 (3) 0.430 (3) 0.430 (3) 0.430 (3) 0.430 (3) sup-3 supplementary materials H10A H10B 0.91060 0.98080 0.72980 0.59190 0.88990 0.85660 0.0590* 0.0590* 0.430 (3) 0.430 (3) Atomic displacement parameters (Å2) S1 O1 O2 O3B N1 C1 C2 C3 C4 C5 C6 C7 C8B C9B C10B O3A C8A C9A C10A U11 0.0485 (2) 0.0798 (9) 0.0709 (8) 0.053 (2) 0.0355 (6) 0.0514 (9) 0.0492 (11) 0.0632 (12) 0.0739 (12) 0.0491 (8) 0.0440 (7) 0.0521 (8) 0.0581 (18) 0.102 (3) 0.0560 (17) 0.100 (5) 0.070 (2) 0.068 (2) 0.0512 (19) U22 0.0503 (2) 0.0732 (9) 0.0829 (9) 0.0512 (19) 0.0386 (6) 0.0801 (13) 0.116 (2) 0.0812 (14) 0.0561 (10) 0.0577 (9) 0.0453 (7) 0.0413 (7) 0.078 (2) 0.076 (2) 0.0421 (14) 0.080 (5) 0.053 (2) 0.055 (2) 0.056 (2) U33 0.0378 (2) 0.0657 (8) 0.0644 (8) 0.077 (3) 0.0455 (6) 0.0952 (15) 0.142 (2) 0.1073 (17) 0.0788 (13) 0.0672 (10) 0.0417 (7) 0.0414 (7) 0.092 (3) 0.0411 (15) 0.0591 (16) 0.080 (5) 0.0499 (19) 0.056 (2) 0.0415 (18) U12 −0.0069 (2) −0.0128 (7) −0.0190 (7) −0.0173 (17) 0.0017 (4) −0.0080 (9) −0.0234 (12) −0.0282 (11) −0.0114 (9) −0.0033 (7) −0.0050 (6) 0.0049 (6) −0.0108 (17) −0.0045 (19) −0.0018 (12) −0.055 (4) −0.0027 (18) 0.0252 (19) −0.0101 (15) U13 0.0083 (2) −0.0080 (7) 0.0321 (6) 0.0263 (17) 0.0061 (5) −0.0131 (9) −0.0186 (12) 0.0084 (11) 0.0095 (10) 0.0012 (7) 0.0026 (6) 0.0152 (6) 0.0389 (18) −0.0006 (16) 0.0151 (12) 0.040 (3) 0.0259 (18) 0.0035 (18) 0.0059 (14) Geometric parameters (Å, °) S1—O1 S1—O2 S1—N1 S1—C6 O3A—C10A O3B—C10B O3A—H3A O3B—H3B N1—C7 N1—H1A C1—C6 C1—C2 C2—C3 C3—C4 C4—C5 C5—C6 C7—C9A C7—C10B C7—C8A C7—C8B C7—C10A sup-4 1.4247 (14) 1.4315 (14) 1.5954 (12) 1.7677 (14) 1.394 (14) 1.402 (7) 0.8200 0.8200 1.4890 (19) 0.8600 1.369 (2) 1.381 (3) 1.362 (4) 1.362 (3) 1.374 (3) 1.381 (2) 1.552 (5) 1.569 (3) 1.569 (5) 1.450 (4) 1.401 (4) C1—H1 C2—H2 C3—H3 C4—H4 C5—H5 C8A—H8A2 C8A—H8A1 C8A—H8A3 C8B—H8B1 C8B—H8B2 C8B—H8B3 C9A—H9A3 C9A—H9A1 C9A—H9A2 C9B—H9B1 C9B—H9B2 C9B—H9B3 C10A—H10B C10A—H10A C10B—H10D C10B—H10C 0.9300 0.9300 0.9300 0.9300 0.9300 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 0.9600 0.9700 0.9700 0.9700 0.9700 U23 0.0011 (1) 0.0318 (7) −0.0308 (7) −0.0205 (18) −0.0065 (5) 0.0279 (12) 0.0368 (19) 0.0083 (13) 0.0117 (9) 0.0100 (8) −0.0020 (6) −0.0027 (6) −0.029 (2) −0.0051 (15) −0.0096 (12) −0.042 (4) 0.0017 (17) −0.0043 (17) −0.0122 (16) supplementary materials C7—C9B 1.576 (4) S1···H8B1 S1···H9A1 S1···H9A2 O1···C8B 2.9800 2.8100 3.1100 3.364 (4) H8A1···C6 H1A···H3A H1A···H9B1 H1A···H10B 2.8400 2.3400 2.2900 2.2300 O1···C10B 3.364 (3) H1A···O3Bv 2.1400 O1···C9A 2.726 (4) i 2.777 (10) O2···O3B v H1A···C10B v 3.0100 2.2000 H1A···O3A i 2.907 (14) H1A···C10A 3.0400 ii 2.912 (13) H1A···O3A 2.7900 O2···O3A O3A···N1 v vi O3A···N1 2.767 (13) H2···H8B2 O3A···O2 O3B···N1 i 2.907 (14) H8A2···H9A3 2.5300 2.908 (9) H8A2···H10A 2.4900 O3B···O2i 2.777 (10) H3···C8Bvi 2.8400 ii O3B···N1 ii O3B···C9B O1···H1 vi 2.840 (9) H3···H8B3 3.157 (10) H8A3···H10B 2.5100 vii 2.5500 2.5500 2.4600 2.6600 2.7600 H8A3···O2 H3A···N1 O1···H9A3 2.6700 H3A···H1A 2.3400 O1···H4iv O1···H8B1 iii 2.4200 2.8100 H3A···O2i 2.1800 iii 2.7900 H3B···O2 i 2.0200 iii 2.8200 H3B···N1 O1···H8B2 O1···H10A O1···H9A1 2.4000 O1···H10C 2.7600 iii O1···H10D O1···H9A2 2.5400 H4···C9A 2.6700 xi H4···H9A3 xi vii 2.9900 2.3400 2.8100 2.4600 H4···O1 H9A1···S1 iv 2.6600 H9A1···O1 2.4000 iv 2.9000 H9A1···H8A1 2.3700 O2···H8A3 O2···H9B2 i 2.1800 O2···H3A H5···O3B 2.8100 v 2.9100 v 2.8200 i 2.0200 H5···O3A ii O3A···H5 O3A···H9A2 2.8200 H9A2···S1 3.1100 2.6600 H9A2···O1 2.4600 ii 2.2000 H9A2···O3A O2···H3B O3A···H1A x 2.6600 O3A···H1A 2.7900 O3B···H9B1 2.5400 O3B···H1A ii 2.1400 H9A3···O1 O3B···H5ii 2.9100 H9A3···H10A 2.5600 O3B···H9B2ii 2.7900 H8B1···C6 3.0900 O3B···H9B1ii 2.8300 H8B1···H10C 2.5400 N1···O3Av N1···O3B 2.912 (13) H8B1···S1 2.9800 2.908 (9) H8B1···O1 2.7600 2.840 (9) H8B2···H9B3 2.4800 v N1···O3B H9A3···H4 H9A3···H8A2 xii 2.3400 2.5300 2.6700 sup-5 supplementary materials N1···O3A 2.767 (13) N1···H3A 2.4200 H8B2···H10D 2.3700 viii H8B2···H2 2.5500 N1···H3B 2.6700 H8B2···O1xii 2.7900 C3···C8Bvi 3.535 (4) H8B3···C6 3.0600 C5···C8A 3.583 (5) H8B3···H3viii 2.5500 C5···C8Aiv C6···C8B C6···C8A 3.531 (5) H8B3···H9B2 2.5100 3.368 (4) 3.499 (5) H9B1···H1A H9B1···O3B 2.2900 2.5400 C8A···C5vii 3.531 (5) H9B1···H9B2ix 2.5100 v 2.8300 ix H9B1···C9B H10A···H8A2 H10A···H9A3 2.9100 2.8200 2.726 (4) H10A···O1xii H10B···H1A C9B···O3B 3.157 (10) H10B···H8A3 2.4600 C9B···C9Bix C10B···O1 C5···H8A1 3.271 (6) H10C···H9B3iii H10C···O1 H10C···H8B1 2.2700 C6···H8B1 3.0900 2.5400 C6···H8B3 C6···H8A1 3.0600 2.8400 H10D···O1xii H10D···H8B2 H10D···H9B3 C8B···H3viii 2.8400 H9B2···O3Bv 2.7900 C9A···H4x 2.9900 H9B2···H8B3 2.5100 C9B···H9B2ix 3.0200 H9B2···C9Bix 3.0200 C9B···H9B1ix 2.9100 H9B2···H9B1ix 2.5100 C10A···H1Aii 3.0400 H9B2···O2vii 2.9000 C10B···H1Aii 3.0100 H9B3···H8B2 2.4800 3.0000 H9B3···H10D 2.4400 C8A···C6 3.499 (5) C8A···C5 3.583 (5) C8B···C6 C8B···O1 3.368 (4) 3.364 (4) C8B···C3viii C9A···O1 3.535 (4) v 3.364 (3) 2.9600 iii C10B···H9B3 H1···O1 2.5100 H8A1···C5 2.9600 H8A1···H9A1 2.3700 O1—S1—O2 O1—S1—N1 O1—S1—C6 O2—S1—N1 O2—S1—C6 N1—S1—C6 C10A—O3A—H3A C10B—O3B—H3B S1—N1—C7 S1—N1—H1A C7—N1—H1A C2—C1—C6 119.29 (8) 109.76 (7) 107.13 (8) 105.45 (7) 106.13 (8) 108.70 (7) 109.00 109.00 127.50 (10) 116.00 116.00 119.3 (2) sup-6 H9B1···O3B 2.4900 2.5600 2.2300 2.7600 2.5400 2.3700 2.4400 xii 3.0000 xii H9B3···H10C 2.2700 C5—C4—H4 C3—C4—H4 C4—C5—H5 C6—C5—H5 H8A1—C8A—H8A3 H8A2—C8A—H8A3 C7—C8A—H8A1 C7—C8A—H8A2 C7—C8A—H8A3 H8A1—C8A—H8A2 C7—C8B—H8B1 C7—C8B—H8B2 120.00 120.00 120.00 120.00 110.00 109.00 109.00 109.00 109.00 110.00 109.00 109.00 H9B3···C10B supplementary materials C1—C2—C3 C2—C3—C4 C3—C4—C5 C4—C5—C6 S1—C6—C1 S1—C6—C5 C1—C6—C5 N1—C7—C10B N1—C7—C10A N1—C7—C8A N1—C7—C9A C9B—C7—C10B C8A—C7—C9A C8A—C7—C10A C9A—C7—C10A N1—C7—C8B C8B—C7—C9B C8B—C7—C10B N1—C7—C9B O3A—C10A—C7 O3B—C10B—C7 C2—C1—H1 C6—C1—H1 C3—C2—H2 C1—C2—H2 C2—C3—H3 C4—C3—H3 120.2 (2) 120.6 (2) 120.0 (2) 119.56 (16) 120.19 (14) 119.46 (11) 120.35 (16) 106.97 (15) 106.72 (18) 105.65 (19) 111.21 (19) 103.6 (2) 105.5 (3) 112.0 (2) 115.5 (2) 118.28 (19) 110.3 (3) 110.33 (19) 106.32 (17) 112.3 (6) 116.0 (4) 120.00 120.00 120.00 120.00 120.00 120.00 H8B1—C8B—H8B3 C7—C8B—H8B3 H8B1—C8B—H8B2 H8B2—C8B—H8B3 C7—C9A—H9A1 H9A2—C9A—H9A3 C7—C9A—H9A3 H9A1—C9A—H9A2 C7—C9A—H9A2 H9A1—C9A—H9A3 C7—C9B—H9B2 C7—C9B—H9B3 C7—C9B—H9B1 H9B1—C9B—H9B3 H9B2—C9B—H9B3 H9B1—C9B—H9B2 C7—C10A—H10A C7—C10A—H10B H10A—C10A—H10B O3A—C10A—H10A O3A—C10A—H10B O3B—C10B—H10D H10C—C10B—H10D C7—C10B—H10C C7—C10B—H10D O3B—C10B—H10C 109.00 109.00 109.00 110.00 110.00 110.00 109.00 109.00 109.00 109.00 109.00 109.00 109.00 110.00 109.00 110.00 109.00 109.00 108.00 109.00 109.00 108.00 107.00 108.00 108.00 108.00 O1—S1—N1—C7 43.70 (14) C2—C1—C6—C5 0.3 (3) O2—S1—N1—C7 173.39 (12) C2—C1—C6—S1 179.33 (19) C6—S1—N1—C7 −73.17 (13) C6—C1—C2—C3 −0.6 (4) N1—S1—C6—C1 126.00 (15) C1—C2—C3—C4 0.8 (4) O1—S1—C6—C1 7.45 (17) C2—C3—C4—C5 −0.5 (4) O2—S1—C6—C1 −121.01 (15) C3—C4—C5—C6 0.2 (3) N1—S1—C6—C5 −54.93 (15) C4—C5—C6—C1 0.0 (3) O1—S1—C6—C5 −173.48 (13) C4—C5—C6—S1 −179.10 (14) O2—S1—C6—C5 58.06 (15) N1—C7—C10B—O3B −56.0 (6) S1—N1—C7—C9B 159.68 (18) C8B—C7—C10B—O3B 174.2 (6) S1—N1—C7—C8B 35.1 (2) C9B—C7—C10B—O3B 56.1 (6) S1—N1—C7—C10B −90.15 (16) Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, y+1/2, −z+3/2; (iii) x, −y+3/2, z−1/2; (iv) x, −y+1/2, z−1/2; (v) −x+2, y−1/2, −z+3/2; (vi) −x+1, y−1/2, −z+3/2; (vii) x, −y+1/2, z+1/2; (viii) −x+1, y+1/2, −z+3/2; (ix) −x+2, −y+1, −z+2; (x) x, y+1, z; (xi) x, y−1, z; (xii) x, −y+3/2, z+1/2. Hydrogen-bond geometry (Å, °) D—H···A D—H H···A D···A D—H···A v 0.86 2.14 2.840 (9) 139 i 0.82 2.02 2.777 (10) 152 0.93 2.51 2.886 (3) 105 N1—H1A···O3B O3B—H3B···O2 C1—H1···O1 sup-7 supplementary materials C9B—H9B1···O3B xii 0.96 2.54 2.881 (11) 101 0.97 2.54 3.478 (3) 162 C10B—H10D···O1 Symmetry codes: (v) −x+2, y−1/2, −z+3/2; (i) −x+2, −y+1, −z+1; (xii) x, −y+3/2, z+1/2. sup-8 supplementary materials Fig. 1 sup-9 View publication stats supplementary materials Fig. 2 sup-10