N,N-Diethyl-2-(4-methyl-benzene-sulfonamido)-benzamide.

The asymmetric unit of the title compound, C(18)H(22)N(2)O(3)S, contains two mol-ecules, exhibiting similar conformations [C-S-N-C torsion angles of -82.2 (2) and -70.4 (2)°, and dihedral angles between the mean planes of the aromatic rings of 56.6 (6) and 51.6 (6)° in mol-ecules I and II, respectively]. However, the two independent mol-ecules show distinctly different hydrogen-bonding patterns. In the crystal, molecules I form inversion dimers via pairs of N-H⋯O hydrogen bonds, whereas for molecules II the N-H⋯O hydrogen bond is intramolecular. The hydrogen-bonded dimers of I further propagate along the b-axis direction through π-π inter-actions [the distance between ring centroids is 3.8424 (8) Å].

Related literature

For the synthesis of the title compound, see: Bakker et al. (1997 ▶); Kaul et al. (2002 ▶). For the biological activity of compounds having the sulfonamide –SO2NH– group, see: Lu & Tucker (2007 ▶); Tappe et al. (2008 ▶); Chegwidden et al. (2000 ▶); Purushottamachar et al. (2008 ▶). For structural and conformational studies of mol­ecules featuring the sulfonamide moiety, see: Parkin et al. (2008 ▶); Perlovich et al. (2009 ▶, 2011 ▶); Altamura et al. (2009 ▶); Vega-Hissi et al. (2011 ▶).

Experimental

Crystal data

C18H22N2O3S

M = 346.43

Triclinic,

a = 9.4674 (6) Å

b = 12.2882 (9) Å

c = 16.0569 (12) Å

α = 108.426 (7)°

β = 97.357 (6)°

γ = 100.245 (6)°

V = 1709.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 150 K

0.54 × 0.43 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur3 CCD diffractometer

Absorption correction: multi-scan (ABSPACK in CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.894, T max = 1.000

17890 measured reflections

7512 independent reflections

4728 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.118

S = 0.96

7512 reflections

441 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97, WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1995 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681204264X/ld2075sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204264X/ld2075Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204264X/ld2075Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H22N2O3S	Z = 4
Mr = 346.43	F(000) = 736
Triclinic, P1	Dx = 1.346 Mg m−3
a = 9.4674 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2882 (9) Å	θ = 4.1–28.6°
c = 16.0569 (12) Å	µ = 0.21 mm−1
α = 108.426 (7)°	T = 150 K
β = 97.357 (6)°	Parallelepiped, colourless
γ = 100.245 (6)°	0.54 × 0.43 × 0.38 mm
V = 1709.7 (2) Å3

Oxford Diffraction Xcalibur3 CCD diffractometer	7512 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4728 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.4547 pixels mm-1	θmax = 28.7°, θmin = 4.1°
ω scans	h = −12→11
Absorption correction: multi-scan (ABSPACK in CrysAlis RED; Oxford Diffraction, 2006)	k = −15→16
Tmin = 0.894, Tmax = 1.000	l = −21→21
17890 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0677P)2] where P = (Fo2 + 2Fc2)/3
7512 reflections	(Δ/σ)max = 0.001
441 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	1.22768 (5)	0.28575 (4)	−0.00356 (3)	0.02970 (14)
O1	1.18234 (15)	0.23441 (12)	−0.09887 (8)	0.0365 (3)
O2	1.36507 (14)	0.36978 (12)	0.03457 (9)	0.0365 (3)
O3	1.03929 (14)	−0.01020 (12)	0.08734 (9)	0.0329 (3)
N1	1.23284 (17)	0.17480 (15)	0.03138 (10)	0.0278 (4)
HN1	1.158 (2)	0.1167 (18)	0.0058 (13)	0.033*
N2	0.98318 (16)	0.13823 (13)	0.19374 (10)	0.0257 (4)
C1	1.0900 (2)	0.35179 (16)	0.03962 (12)	0.0268 (4)
C2	1.1191 (2)	0.42734 (17)	0.12797 (13)	0.0311 (5)
H2	1.2108	0.4429	0.1638	0.037*
C3	1.0114 (2)	0.47931 (17)	0.16265 (13)	0.0331 (5)
H3	1.0315	0.5296	0.2220	0.040*
C4	0.8731 (2)	0.45770 (17)	0.11021 (13)	0.0308 (5)
C5	0.8479 (2)	0.38376 (18)	0.02171 (14)	0.0348 (5)
H5	0.7570	0.3698	−0.0146	0.042*
C6	0.9537 (2)	0.33011 (18)	−0.01428 (13)	0.0334 (5)
H6	0.9339	0.2802	−0.0737	0.040*
C7	1.30951 (19)	0.18780 (16)	0.11830 (12)	0.0262 (4)
C8	1.23673 (19)	0.14737 (16)	0.17723 (12)	0.0257 (4)
C9	1.3163 (2)	0.15919 (17)	0.26008 (12)	0.0304 (5)
H9	1.2691	0.1312	0.2991	0.037*
C10	1.4645 (2)	0.21191 (18)	0.28524 (13)	0.0343 (5)
H10	1.5162	0.2206	0.3411	0.041*
C11	1.5345 (2)	0.25127 (18)	0.22645 (13)	0.0332 (5)
H11	1.6340	0.2868	0.2431	0.040*
C12	1.4591 (2)	0.23881 (17)	0.14310 (13)	0.0305 (5)
H12	1.5082	0.2644	0.1037	0.037*
C13	0.7557 (2)	0.51226 (19)	0.14887 (15)	0.0397 (5)
H13A	0.6650	0.4798	0.1062	0.060*
H13B	0.7826	0.5960	0.1626	0.060*
H13C	0.7444	0.4959	0.2026	0.060*
C14	1.0785 (2)	0.08570 (17)	0.14925 (12)	0.0250 (4)
C15	0.82675 (19)	0.07980 (17)	0.16405 (13)	0.0293 (4)
H15A	0.7766	0.1054	0.2133	0.035*
H15B	0.8154	−0.0048	0.1472	0.035*
C16	0.7572 (2)	0.10750 (18)	0.08525 (13)	0.0326 (5)
H16A	0.6554	0.0680	0.0677	0.049*
H16B	0.8054	0.0810	0.0360	0.049*
H16C	0.7666	0.1911	0.1020	0.049*
C17	1.0220 (2)	0.25858 (16)	0.25954 (12)	0.0291 (4)
H17A	0.9527	0.3020	0.2443	0.035*
H17B	1.1183	0.2979	0.2561	0.035*
C18	1.0228 (2)	0.26194 (18)	0.35513 (13)	0.0373 (5)
H18A	1.0486	0.3424	0.3951	0.056*
H18B	1.0930	0.2208	0.3712	0.056*
H18C	0.9272	0.2247	0.3594	0.056*
S1'	0.36428 (5)	0.62169 (4)	0.38496 (3)	0.02947 (14)
O1'	0.25700 (14)	0.66660 (13)	0.43239 (9)	0.0389 (4)
O2'	0.34408 (14)	0.49807 (12)	0.34048 (9)	0.0356 (3)
O3'	0.71780 (14)	0.88703 (11)	0.52660 (9)	0.0346 (3)
N1'	0.51694 (17)	0.66700 (15)	0.46038 (11)	0.0279 (4)
HN1'	0.534 (2)	0.7376 (18)	0.4848 (14)	0.033*
N2'	0.81608 (16)	0.90225 (13)	0.40820 (10)	0.0263 (4)
C1'	0.39078 (18)	0.69322 (17)	0.30717 (12)	0.0273 (4)
C2'	0.45199 (19)	0.64421 (18)	0.23389 (13)	0.0297 (4)
H2'	0.4787	0.5727	0.2251	0.036*
C3'	0.4727 (2)	0.70303 (18)	0.17430 (13)	0.0316 (5)
H3'	0.5144	0.6706	0.1256	0.038*
C4'	0.43286 (19)	0.80900 (18)	0.18556 (13)	0.0314 (5)
C5'	0.3715 (2)	0.85577 (19)	0.25892 (14)	0.0369 (5)
H5'	0.3431	0.9265	0.2671	0.044*
C6'	0.3517 (2)	0.79973 (18)	0.32016 (13)	0.0345 (5)
H6'	0.3124	0.8333	0.3697	0.041*
C7'	0.64714 (19)	0.63062 (17)	0.43794 (12)	0.0246 (4)
C8'	0.76801 (19)	0.71269 (16)	0.43306 (12)	0.0251 (4)
C9'	0.8955 (2)	0.67471 (17)	0.41748 (12)	0.0279 (4)
H9'	0.9765	0.7277	0.4145	0.034*
C10'	0.9044 (2)	0.56046 (18)	0.40639 (13)	0.0319 (5)
H10'	0.9906	0.5369	0.3963	0.038*
C11'	0.7839 (2)	0.48063 (17)	0.41038 (13)	0.0316 (5)
H11'	0.7894	0.4033	0.4025	0.038*
C12'	0.6555 (2)	0.51581 (17)	0.42602 (13)	0.0293 (4)
H12'	0.5750	0.4620	0.4285	0.035*
C13'	0.4544 (2)	0.8733 (2)	0.12051 (14)	0.0437 (6)
H13D	0.5286	0.8482	0.0885	0.066*
H13E	0.4842	0.9567	0.1528	0.066*
H13F	0.3642	0.8559	0.0789	0.066*
C14'	0.76384 (19)	0.84015 (17)	0.45779 (12)	0.0263 (4)
C15'	0.8238 (2)	1.02962 (17)	0.44075 (13)	0.0318 (5)
H15C	0.9033	1.0690	0.4203	0.038*
H15D	0.8465	1.0589	0.5057	0.038*
C16'	0.6845 (2)	1.0613 (2)	0.40996 (15)	0.0457 (6)
H16D	0.6968	1.1454	0.4334	0.069*
H16E	0.6056	1.0244	0.4312	0.069*
H16F	0.6624	1.0344	0.3457	0.069*
C17'	0.8356 (2)	0.85147 (18)	0.31525 (12)	0.0305 (5)
H17C	0.7752	0.8800	0.2772	0.037*
H17D	0.8015	0.7664	0.2952	0.037*
C18'	0.9930 (2)	0.8811 (2)	0.30377 (14)	0.0443 (6)
H18D	0.9980	0.8455	0.2420	0.066*
H18E	1.0534	0.8515	0.3400	0.066*
H18F	1.0270	0.9651	0.3220	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.0316 (3)	0.0309 (3)	0.0249 (3)	0.0009 (2)	0.0054 (2)	0.0110 (2)
O1	0.0445 (8)	0.0397 (9)	0.0227 (7)	0.0037 (7)	0.0059 (6)	0.0109 (7)
O2	0.0314 (7)	0.0366 (8)	0.0390 (8)	−0.0025 (6)	0.0063 (6)	0.0153 (7)
O3	0.0342 (7)	0.0305 (8)	0.0278 (7)	0.0052 (6)	0.0064 (6)	0.0029 (7)
N1	0.0266 (8)	0.0268 (10)	0.0249 (9)	−0.0003 (7)	0.0016 (7)	0.0071 (8)
N2	0.0283 (8)	0.0233 (9)	0.0245 (8)	0.0048 (7)	0.0064 (7)	0.0069 (7)
C1	0.0323 (10)	0.0229 (10)	0.0241 (10)	−0.0005 (8)	0.0027 (8)	0.0113 (9)
C2	0.0320 (11)	0.0308 (12)	0.0274 (11)	0.0020 (9)	−0.0003 (9)	0.0111 (9)
C3	0.0401 (12)	0.0313 (12)	0.0259 (11)	0.0053 (9)	0.0046 (9)	0.0097 (10)
C4	0.0377 (11)	0.0225 (11)	0.0340 (12)	0.0039 (9)	0.0046 (9)	0.0150 (10)
C5	0.0301 (11)	0.0346 (12)	0.0383 (12)	0.0048 (9)	−0.0028 (9)	0.0159 (10)
C6	0.0372 (11)	0.0312 (12)	0.0268 (11)	0.0021 (9)	−0.0005 (9)	0.0090 (10)
C7	0.0280 (10)	0.0261 (11)	0.0225 (10)	0.0079 (8)	0.0044 (8)	0.0052 (9)
C8	0.0284 (10)	0.0219 (10)	0.0263 (10)	0.0073 (8)	0.0053 (8)	0.0069 (9)
C9	0.0367 (11)	0.0311 (12)	0.0254 (10)	0.0115 (9)	0.0082 (9)	0.0096 (9)
C10	0.0358 (11)	0.0357 (12)	0.0276 (11)	0.0132 (9)	−0.0023 (9)	0.0063 (10)
C11	0.0238 (10)	0.0357 (12)	0.0338 (11)	0.0071 (9)	0.0004 (9)	0.0055 (10)
C12	0.0294 (10)	0.0304 (11)	0.0317 (11)	0.0075 (9)	0.0089 (9)	0.0093 (10)
C13	0.0403 (12)	0.0358 (13)	0.0450 (13)	0.0087 (10)	0.0081 (10)	0.0168 (11)
C14	0.0305 (10)	0.0246 (11)	0.0216 (10)	0.0052 (8)	0.0050 (8)	0.0108 (9)
C15	0.0265 (10)	0.0307 (11)	0.0315 (11)	0.0053 (8)	0.0098 (9)	0.0108 (9)
C16	0.0302 (10)	0.0376 (12)	0.0325 (11)	0.0104 (9)	0.0082 (9)	0.0137 (10)
C17	0.0333 (11)	0.0253 (11)	0.0313 (11)	0.0103 (9)	0.0095 (9)	0.0101 (9)
C18	0.0493 (13)	0.0328 (12)	0.0299 (11)	0.0142 (10)	0.0081 (10)	0.0086 (10)
S1'	0.0235 (2)	0.0323 (3)	0.0314 (3)	0.0011 (2)	0.0062 (2)	0.0119 (2)
O1'	0.0278 (7)	0.0482 (9)	0.0444 (9)	0.0060 (7)	0.0164 (7)	0.0190 (8)
O2'	0.0335 (7)	0.0288 (8)	0.0369 (8)	−0.0040 (6)	0.0007 (6)	0.0093 (7)
O3'	0.0431 (8)	0.0284 (8)	0.0290 (8)	0.0027 (6)	0.0121 (7)	0.0067 (7)
N1'	0.0286 (9)	0.0247 (9)	0.0289 (9)	0.0024 (8)	0.0072 (7)	0.0090 (8)
N2'	0.0269 (8)	0.0237 (9)	0.0255 (9)	−0.0003 (7)	0.0012 (7)	0.0096 (7)
C1'	0.0190 (9)	0.0322 (11)	0.0278 (10)	0.0023 (8)	0.0008 (8)	0.0100 (9)
C2'	0.0238 (10)	0.0305 (11)	0.0316 (11)	0.0048 (8)	0.0037 (9)	0.0082 (10)
C3'	0.0273 (10)	0.0388 (13)	0.0276 (11)	0.0041 (9)	0.0049 (9)	0.0119 (10)
C4'	0.0240 (10)	0.0355 (12)	0.0316 (11)	−0.0006 (9)	−0.0020 (9)	0.0144 (10)
C5'	0.0406 (12)	0.0336 (12)	0.0381 (12)	0.0125 (10)	0.0042 (10)	0.0138 (11)
C6'	0.0345 (11)	0.0387 (13)	0.0312 (11)	0.0134 (10)	0.0085 (9)	0.0100 (10)
C7'	0.0242 (9)	0.0288 (11)	0.0199 (9)	0.0034 (8)	0.0026 (8)	0.0095 (9)
C8'	0.0266 (10)	0.0249 (11)	0.0200 (10)	−0.0006 (8)	0.0006 (8)	0.0079 (9)
C9'	0.0262 (10)	0.0291 (11)	0.0264 (10)	0.0008 (8)	0.0035 (8)	0.0105 (9)
C10'	0.0272 (10)	0.0349 (12)	0.0312 (11)	0.0062 (9)	0.0034 (9)	0.0097 (10)
C11'	0.0366 (11)	0.0260 (11)	0.0304 (11)	0.0069 (9)	0.0023 (9)	0.0090 (9)
C12'	0.0298 (10)	0.0268 (11)	0.0299 (11)	−0.0005 (8)	0.0024 (9)	0.0133 (9)
C13'	0.0447 (13)	0.0475 (14)	0.0386 (13)	0.0027 (11)	0.0016 (11)	0.0216 (11)
C14'	0.0241 (10)	0.0251 (11)	0.0256 (10)	0.0005 (8)	0.0008 (8)	0.0076 (9)
C15'	0.0361 (11)	0.0240 (11)	0.0303 (11)	−0.0016 (9)	0.0020 (9)	0.0092 (9)
C16'	0.0511 (14)	0.0364 (13)	0.0467 (14)	0.0125 (11)	0.0002 (11)	0.0128 (11)
C17'	0.0304 (10)	0.0321 (12)	0.0246 (10)	−0.0013 (9)	0.0012 (9)	0.0102 (9)
C18'	0.0385 (12)	0.0611 (16)	0.0281 (11)	0.0002 (11)	0.0080 (10)	0.0141 (11)

S1—O1	1.4315 (13)	S1'—O2'	1.4248 (14)
S1—O2	1.4324 (13)	S1'—O1'	1.4311 (14)
S1—N1	1.6358 (17)	S1'—N1'	1.6446 (17)
S1—C1	1.758 (2)	S1'—C1'	1.758 (2)
O3—C14	1.235 (2)	O3'—C14'	1.246 (2)
N1—C7	1.435 (2)	N1'—C7'	1.434 (2)
N1—HN1	0.86 (2)	N1'—HN1'	0.81 (2)
N2—C14	1.350 (2)	N2'—C14'	1.346 (2)
N2—C17	1.469 (2)	N2'—C15'	1.470 (2)
N2—C15	1.470 (2)	N2'—C17'	1.475 (2)
C1—C2	1.388 (3)	C1'—C6'	1.383 (3)
C1—C6	1.390 (3)	C1'—C2'	1.391 (3)
C2—C3	1.381 (3)	C2'—C3'	1.382 (3)
C2—H2	0.9300	C2'—H2'	0.9300
C3—C4	1.395 (3)	C3'—C4'	1.384 (3)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C5	1.386 (3)	C4'—C5'	1.386 (3)
C4—C13	1.500 (3)	C4'—C13'	1.509 (3)
C5—C6	1.384 (3)	C5'—C6'	1.380 (3)
C5—H5	0.9300	C5'—H5'	0.9300
C6—H6	0.9300	C6'—H6'	0.9300
C7—C12	1.393 (3)	C7'—C12'	1.381 (3)
C7—C8	1.400 (3)	C7'—C8'	1.413 (2)
C8—C9	1.393 (3)	C8'—C9'	1.393 (3)
C8—C14	1.493 (2)	C8'—C14'	1.498 (3)
C9—C10	1.385 (3)	C9'—C10'	1.377 (3)
C9—H9	0.9300	C9'—H9'	0.9300
C10—C11	1.378 (3)	C10'—C11'	1.388 (3)
C10—H10	0.9300	C10'—H10'	0.9300
C11—C12	1.382 (3)	C11'—C12'	1.388 (3)
C11—H11	0.9300	C11'—H11'	0.9300
C12—H12	0.9300	C12'—H12'	0.9300
C13—H13A	0.9600	C13'—H13D	0.9600
C13—H13B	0.9600	C13'—H13E	0.9600
C13—H13C	0.9600	C13'—H13F	0.9600
C15—C16	1.513 (3)	C15'—C16'	1.508 (3)
C15—H15A	0.9700	C15'—H15C	0.9700
C15—H15B	0.9700	C15'—H15D	0.9700
C16—H16A	0.9600	C16'—H16D	0.9600
C16—H16B	0.9600	C16'—H16E	0.9600
C16—H16C	0.9600	C16'—H16F	0.9600
C17—C18	1.521 (3)	C17'—C18'	1.518 (3)
C17—H17A	0.9700	C17'—H17C	0.9700
C17—H17B	0.9700	C17'—H17D	0.9700
C18—H18A	0.9600	C18'—H18D	0.9600
C18—H18B	0.9600	C18'—H18E	0.9600
C18—H18C	0.9600	C18'—H18F	0.9600
O1—S1—O2	119.57 (8)	O2'—S1'—O1'	120.27 (8)
O1—S1—N1	105.49 (8)	O2'—S1'—N1'	107.60 (8)
O2—S1—N1	107.66 (8)	O1'—S1'—N1'	104.98 (8)
O1—S1—C1	108.16 (9)	O2'—S1'—C1'	108.68 (9)
O2—S1—C1	107.99 (9)	O1'—S1'—C1'	107.76 (9)
N1—S1—C1	107.40 (8)	N1'—S1'—C1'	106.80 (8)
C7—N1—S1	123.27 (13)	C7'—N1'—S1'	120.56 (13)
C7—N1—HN1	118.4 (13)	C7'—N1'—HN1'	110.6 (14)
S1—N1—HN1	113.0 (13)	S1'—N1'—HN1'	110.0 (15)
C14—N2—C17	124.10 (15)	C14'—N2'—C15'	117.36 (15)
C14—N2—C15	117.84 (15)	C14'—N2'—C17'	125.41 (16)
C17—N2—C15	117.24 (14)	C15'—N2'—C17'	115.80 (15)
C2—C1—C6	120.03 (18)	C6'—C1'—C2'	120.19 (18)
C2—C1—S1	119.44 (14)	C6'—C1'—S1'	119.29 (14)
C6—C1—S1	120.52 (15)	C2'—C1'—S1'	120.51 (15)
C3—C2—C1	119.89 (18)	C3'—C2'—C1'	119.20 (19)
C3—C2—H2	120.1	C3'—C2'—H2'	120.4
C1—C2—H2	120.1	C1'—C2'—H2'	120.4
C2—C3—C4	121.13 (18)	C2'—C3'—C4'	121.49 (18)
C2—C3—H3	119.4	C2'—C3'—H3'	119.3
C4—C3—H3	119.4	C4'—C3'—H3'	119.3
C5—C4—C3	117.83 (18)	C3'—C4'—C5'	118.20 (18)
C5—C4—C13	121.32 (18)	C3'—C4'—C13'	121.76 (18)
C3—C4—C13	120.85 (18)	C5'—C4'—C13'	120.04 (19)
C6—C5—C4	122.02 (18)	C6'—C5'—C4'	121.47 (19)
C6—C5—H5	119.0	C6'—C5'—H5'	119.3
C4—C5—H5	119.0	C4'—C5'—H5'	119.3
C5—C6—C1	119.07 (18)	C5'—C6'—C1'	119.44 (18)
C5—C6—H6	120.5	C5'—C6'—H6'	120.3
C1—C6—H6	120.5	C1'—C6'—H6'	120.3
C12—C7—C8	119.84 (17)	C12'—C7'—C8'	120.49 (17)
C12—C7—N1	119.24 (17)	C12'—C7'—N1'	118.96 (16)
C8—C7—N1	120.90 (16)	C8'—C7'—N1'	120.45 (16)
C9—C8—C7	118.94 (17)	C9'—C8'—C7'	118.05 (17)
C9—C8—C14	120.59 (17)	C9'—C8'—C14'	121.72 (16)
C7—C8—C14	120.36 (16)	C7'—C8'—C14'	119.60 (16)
C10—C9—C8	121.10 (18)	C10'—C9'—C8'	121.49 (17)
C10—C9—H9	119.4	C10'—C9'—H9'	119.3
C8—C9—H9	119.4	C8'—C9'—H9'	119.3
C11—C10—C9	119.21 (19)	C9'—C10'—C11'	119.66 (18)
C11—C10—H10	120.4	C9'—C10'—H10'	120.2
C9—C10—H10	120.4	C11'—C10'—H10'	120.2
C10—C11—C12	121.06 (18)	C12'—C11'—C10'	120.24 (18)
C10—C11—H11	119.5	C12'—C11'—H11'	119.9
C12—C11—H11	119.5	C10'—C11'—H11'	119.9
C11—C12—C7	119.83 (18)	C7'—C12'—C11'	120.06 (17)
C11—C12—H12	120.1	C7'—C12'—H12'	120.0
C7—C12—H12	120.1	C11'—C12'—H12'	120.0
C4—C13—H13A	109.5	C4'—C13'—H13D	109.5
C4—C13—H13B	109.5	C4'—C13'—H13E	109.5
H13A—C13—H13B	109.5	H13D—C13'—H13E	109.5
C4—C13—H13C	109.5	C4'—C13'—H13F	109.5
H13A—C13—H13C	109.5	H13D—C13'—H13F	109.5
H13B—C13—H13C	109.5	H13E—C13'—H13F	109.5
O3—C14—N2	122.48 (16)	O3'—C14'—N2'	121.77 (17)
O3—C14—C8	119.72 (16)	O3'—C14'—C8'	118.54 (16)
N2—C14—C8	117.80 (16)	N2'—C14'—C8'	119.61 (16)
N2—C15—C16	111.74 (15)	N2'—C15'—C16'	113.69 (16)
N2—C15—H15A	109.3	N2'—C15'—H15C	108.8
C16—C15—H15A	109.3	C16'—C15'—H15C	108.8
N2—C15—H15B	109.3	N2'—C15'—H15D	108.8
C16—C15—H15B	109.3	C16'—C15'—H15D	108.8
H15A—C15—H15B	107.9	H15C—C15'—H15D	107.7
C15—C16—H16A	109.5	C15'—C16'—H16D	109.5
C15—C16—H16B	109.5	C15'—C16'—H16E	109.5
H16A—C16—H16B	109.5	H16D—C16'—H16E	109.5
C15—C16—H16C	109.5	C15'—C16'—H16F	109.5
H16A—C16—H16C	109.5	H16D—C16'—H16F	109.5
H16B—C16—H16C	109.5	H16E—C16'—H16F	109.5
N2—C17—C18	113.09 (16)	N2'—C17'—C18'	113.74 (15)
N2—C17—H17A	109.0	N2'—C17'—H17C	108.8
C18—C17—H17A	109.0	C18'—C17'—H17C	108.8
N2—C17—H17B	109.0	N2'—C17'—H17D	108.8
C18—C17—H17B	109.0	C18'—C17'—H17D	108.8
H17A—C17—H17B	107.8	H17C—C17'—H17D	107.7
C17—C18—H18A	109.5	C17'—C18'—H18D	109.5
C17—C18—H18B	109.5	C17'—C18'—H18E	109.5
H18A—C18—H18B	109.5	H18D—C18'—H18E	109.5
C17—C18—H18C	109.5	C17'—C18'—H18F	109.5
H18A—C18—H18C	109.5	H18D—C18'—H18F	109.5
H18B—C18—H18C	109.5	H18E—C18'—H18F	109.5
C1—S1—N1—C7	−82.2 (2)	C1'—S1'—N1'—C7'	−70.4 (2)
HN1—N1—S1—O1	−44 (1)	HN1'—N1'—S1'—O1'	−54 (2)
C7—N1—S1—O2	33.9 (2)	C7'—N1'—S1'—O2'	46.1 (2)
C6—C1—S1—O1	11.7 (2)	C6'—C1'—S1'—O1'	20.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1′—HN1′···O3′	0.81 (2)	2.15 (2)	2.809 (2)	139 (2)
N1—HN1···O3i	0.86 (2)	2.15 (2)	2.969 (2)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1′—HN1′⋯O3′	0.81 (2)	2.15 (2)	2.809 (2)	139 (2)
N1—HN1⋯O3i	0.86 (2)	2.15 (2)	2.969 (2)	159 (2)

Symmetry code: (i) .