N,N-Diethyl-2-(4-methyl­benzene­sulfonamido)­benzamide

Altamura, M.; Fedi, V.; Nannicini, R.; Paoli, P.; Rossi, P.

doi:10.1107/S160053681204264X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3144-o3145

doi:10.1107/S160053681204264X

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N,N-Diethyl-2-(4-methylbenzenesulfonamido)benzamide

Maria Altamura,^a Valentina Fedi,^a Rossano Nannicini,^a Paola Paoli ^b ^* and Patrizia Rossi ^b

^aChemistry Department, Menarini Ricerche S.p.A., Via dei Sette Santi 3, I-50131 Firenze, Italy, and ^bDip. Energetica "Sergio Stecco", University of Firenze, Via S. Marta 3, I-50139 Firenze, Italy
^*Correspondence e-mail: paolapaoli@unifi.it

(Received 20 September 2012; accepted 11 October 2012; online 20 October 2012)

The asymmetric unit of the title compound, C₁₈H₂₂N₂O₃S, contains two molecules, 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 molecules I and II, respectively]. However, the two independent molecules 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 interactions [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_r = 346.43
Triclinic, $[P \overline 1]$
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 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) 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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.118
S = 0.96
7512 reflections
441 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) -x+2, -y, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681204264X/ld2075sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681204264X/ld2075Isup3.cml

checkCIF report

Comment top

The sulfonamide moiety is a common pharmacophore in many biologically active compounds, such as HIV inhibitors (Lu & Tucker, 2007), antimicrobial drugs (Tappe et al., 2008), carbonic anhydrase inhibitors (Chegwidden et al., 2000), and anti-tumor agents (Purushottamachar et al., 2008). Because the structural and conformational properties of a compound usually are related to its biological properties, their study would provide useful information to design new effective drugs. In this regard, there are many recent publications reporting structural data on related sulfonamides (Parkin et al., 2008, Altamura et al., 2009, Perlovich et al., 2009, Perlovich et al., 2011,Vega-Hissi et al., 2011).

The asymmetric unit of the title compound contains two independent molecules, I and II, which are almost superimposable (Table 1). As expected, a staggered conformation about the N—S bond is adopted, with the N lone pair bisecting the OŜO angle, and with the p orbital at the ipso carbon bisecting the same angle (Table 1, Fig. 1). The sulfonamide nitrogen atom is almost planar-trigonal in molecule I (Σ<N=355 (1)°), while in II it is definitely more pyramidal (Σ<N=341 (1)°). The conformation of molecule II is stabilized by an intramolecular H-bond involving the H atom of the sulfonamide grouping (HN1') and the oxygen atom O3' of the amide moiety (Table 2). In the crystal packing, molecules I form dimers instead, which are held together by a couple of N—H···O=C hydrogen bonds (Table 2, Fig. 2). Dimers propagate along the b axis direction through π-π stacking interactions involving two symmetry related C1—C6 rings (centroid-centroid distance 3.8424 (8) Å, symmetry code: -x + 2, -y + 1, -z). No further significant intermolecular interactions are present in the crystal structure.

Related literature top

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 top

For the synthesis of the title compound, see: Bakker et al. (1997); Kaul et al., (2002). Crystals of N,N-diethyl-2-(4-methylphenylsulfonamido)benzamide suitable for single-crystal X-ray diffraction analysis were obtained by slow evaporation of an ethanol/water solution of N,N-diethyl-2-(4-methylphenylsulfonamido)benzamide.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); 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 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The symmetrically independent molecule I (molecule II has a similar shape and the same labelling scheme). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal structure of the title compound as viewed along the a-axis (molecules I are shown in blue and molecules II - in red). Intermolecular NH···O hydrogen bonding is shown as dashed lines.

N,N-Diethyl-2-(4-methylbenzenesulfonamido)benzamide top

Crystal data top

C₁₈H₂₂N₂O₃S	Z = 4
M_r = 346.43	F(000) = 736
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0677P)²] where P = (F_o² + 2F_c²)/3
7512 reflections	(Δ/σ)_max = 0.001
441 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₈H₂₂N₂O₃S	γ = 100.245 (6)°
M_r = 346.43	V = 1709.7 (2) Å³
Triclinic, P1	Z = 4
a = 9.4674 (6) Å	Mo Kα radiation
b = 12.2882 (9) Å	µ = 0.21 mm⁻¹
c = 16.0569 (12) Å	T = 150 K
α = 108.426 (7)°	0.54 × 0.43 × 0.38 mm
β = 97.357 (6)°

Data collection top

Oxford Diffraction Xcalibur3 CCD diffractometer	7512 independent reflections
Absorption correction: multi-scan (ABSPACK in CrysAlis RED; Oxford Diffraction, 2006)	4728 reflections with I > 2σ(I)
T_min = 0.894, T_max = 1.000	R_int = 0.025
17890 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.42 e Å⁻³
7512 reflections	Δρ_min = −0.32 e Å⁻³
441 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₂O₃S
M_r	346.43
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	9.4674 (6), 12.2882 (9), 16.0569 (12)
α, β, γ (°)	108.426 (7), 97.357 (6), 100.245 (6)
V (Å³)	1709.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.54 × 0.43 × 0.38

Data collection
Diffractometer	Oxford Diffraction Xcalibur3 CCD diffractometer
Absorption correction	Multi-scan (ABSPACK in CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.894, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17890, 7512, 4728
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.118, 0.96
No. of reflections	7512
No. of parameters	441
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.32

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Selected torsion angles (º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z.

Acknowledgements

The authors acknowledge the CRIST (Centro di Cristallografia Strutturale, University of Firenze), where the data collection was performed.

References

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