N-Benzyl-5-(dimethyl­amino)­naphthalene-1-sulfonamide

Bhatt, P.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536811033083

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages o2458-o2459

doi:10.1107/S1600536811033083

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N-Benzyl-5-(dimethylamino)naphthalene-1-sulfonamide

Pralav Bhatt,^a Thavendran Govender,^b Hendrik G. Kruger ^a and Glenn E. M. Maguire ^a ^*

^aSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa, and ^bSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa
^*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 12 August 2011; accepted 15 August 2011; online 27 August 2011)

The structure of the title compound, C₁₉H₂₀N₂O₂S, displays intermolecular N—H⋯O hydrogen bonding, which generates inversion dimers. There is no π–π stacking in the crystal structure. The dihedral angle between the phenyl ring and naphthalene ring system is 59.16 (11)°.

Related literature

For the use of dansyl fluorescent analogs as insecticides and synergists, see: Himel et al. (1971 ). Dansyl probes have also been covalently incorporated into a variety of polymeric networks, see: Shea et al. (1989 ). Dansyl chromophoric compounds have been investigated for intramolecular energy transfer in aromatic ring systems, see: Schael et al. (1998 ) and for host–guest interations shown by fluoresence studies of dansyl-labelled calix[6]arene, see: Schonefeld et al. (2006 ). For related structures, see: Illos et al. (2005 ); Hongmei et al. (2009 ); Hong-Wei et al. (2009 ); Chui et al. (2010 ).

Experimental

Crystal data

C₁₉H₂₀N₂O₂S
M_r = 340.43
Monoclinic, C 2/c
a = 16.6635 (5) Å
b = 9.5722 (2) Å
c = 22.8942 (7) Å
β = 108.779 (1)°
V = 3457.38 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.30 × 0.24 × 0.22 mm

Data collection

Nonius KappaCCD diffractometer
4275 measured reflections
4275 independent reflections
3747 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.096
S = 1.03
4275 reflections
223 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86 (2)	2.12 (2)	2.9351 (14)	158 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811033083/hg5080sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033083/hg5080Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033083/hg5080Isup3.cml

checkCIF report

Comment top

Dansyl fluorescent analogs have been reported as insecticides and synergists (Himel et al.,1971). Dansyl probes have also been covalently incorporated into a variety of polymeric networks (Shea et al.,1989). Dansyl chromophoric compounds were investigated for intramolecular energy transfer in aromatic ring systems (Schael et al.,1998). Dansyl labelled calix[6]arene are reported to show host–guest interations using fluoresence studies (Schonefeld et al., 2006).

The title compound is a novel benzylated dansyl derivative (Fig. 1.).

There are a number of examples in literature where amino-sulfonamides dansyl structures have shown intermolecular hydrogen bonding. These arrangments can be described in two broad categories. First, where hydrogen bonds occur between the sulfonyl oxygen and the nitrogen of two adjacent molecules in a alternating chain arrangement (Hongmei et al., 2009, Chui et al.,2010). Second, where they interact with an adjacent molecule in a head to tail manner, (Illos et al., 2005, Hong-Wei et al., 2009). Our system falls into the latter category. Our structure thus displays N1—H1···O2, 2.9351 (14) Å intermolecular hydrogen bonding, generating inversion dimers (Fig. 2). There is no π–π stacking in the crystal.

Related literature top

For the use of dansyl fluorescent analogs as insecticides and synergists, see: Himel et al. (1971). Dansyl probes have also been covalently incorporated into a variety of polymeric networks, see: Shea et al. (1989). Dansyl chromophoric compounds have been investigated for intramolecular energy transfer in aromatic ring systems, see: Schael et al. (1998) and for host–guest interations shown by fluoresence studies of dansyl-labelled calix[6]arene, see: Schonefeld et al. (2006). For related structures, see: Illos et al. (2005); Hongmei et al. (2009); Hong-Wei et al. (2009); Chui et al. (2010).

Experimental top

To a dry THF 5 ml benzyl amine (107 mg, 1 mM) was added triethyl amine (303 mg, 3 mM). Dansyl chloride (269 mg, 1 mM) was then added and the resulting solution was stirred until the reaction was completed (TLC R_f = 0.27 in 60% ethyl acetate/hexane). The reaction contents were filtered. The filtrate was evaporated under reduced pressure yielding a yellow oil. To this residue was added 20 ml of dichloromethane and then the organic layer was washed with water and then separated. After drying over anhydrous magnesium sulfate the solvent was evaporated once again under reduced pressure to yield a yellow crystalline solid (240 mg, 71%). M.p. = 408 K.

Crystals suitable for X-ray analysis were grown in ethyl acetate/hexane at room temperature.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atomic numbering scheme. The H atoms have been omitted for clarity. Displacement elipsoids are drawn at 40% probability.
	Fig. 2. The hydrogen bonding interactions of the title compound along the [110] axis. All H atoms except those involved in hydrogen bonding interactions have been omitted for clarity.

N-Benzyl-5-(dimethylamino)naphthalene-1-sulfonamide top

Crystal data top

C₁₉H₂₀N₂O₂S	F(000) = 1440
M_r = 340.43	D_x = 1.308 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4275 reflections
a = 16.6635 (5) Å	θ = 2.5–28.3°
b = 9.5722 (2) Å	µ = 0.20 mm⁻¹
c = 22.8942 (7) Å	T = 173 K
β = 108.779 (1)°	Block, colourless
V = 3457.38 (16) Å³	0.30 × 0.24 × 0.22 mm
Z = 8

Data collection top

Nonius KappaCCD diffractometer	3747 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 28.3°, θ_min = 2.5°
1.2° ϕ scans and ω scans	h = 0→22
4275 measured reflections	k = 0→12
4275 independent reflections	l = −30→28

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0451P)² + 3.0274P] where P = (F_o² + 2F_c²)/3
4275 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.37 e Å⁻³
1 restraint	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₉H₂₀N₂O₂S	V = 3457.38 (16) Å³
M_r = 340.43	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 16.6635 (5) Å	µ = 0.20 mm⁻¹
b = 9.5722 (2) Å	T = 173 K
c = 22.8942 (7) Å	0.30 × 0.24 × 0.22 mm
β = 108.779 (1)°

Data collection top

Nonius KappaCCD diffractometer	3747 reflections with I > 2σ(I)
4275 measured reflections	R_int = 0.000
4275 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.37 e Å⁻³
4275 reflections	Δρ_min = −0.40 e Å⁻³
223 parameters

Special details top

Experimental. Half sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40 mm; combination of ϕ and ω scans of 1.0°, 60 s per °, 2 iterations.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.20046 (2)	0.47743 (3)	0.473136 (13)	0.02444 (9)
O1	0.18380 (7)	0.60223 (10)	0.50185 (4)	0.0342 (2)
O2	0.16204 (6)	0.34869 (10)	0.48342 (4)	0.0307 (2)
N1	0.30155 (7)	0.45093 (11)	0.49739 (5)	0.0276 (2)
H1	0.3140 (12)	0.3655 (16)	0.4932 (8)	0.050 (5)*
N2	0.12696 (7)	0.39094 (13)	0.17747 (5)	0.0300 (2)
C1	0.43601 (8)	0.58023 (13)	0.54635 (6)	0.0268 (3)
C2	0.49467 (9)	0.68229 (15)	0.54407 (7)	0.0348 (3)
H2	0.4855	0.7356	0.5075	0.042*
C3	0.56607 (9)	0.70685 (17)	0.59432 (8)	0.0424 (4)
H3	0.6051	0.7775	0.5924	0.051*
C4	0.58056 (10)	0.62813 (18)	0.64761 (8)	0.0435 (4)
H4	0.6299	0.6438	0.6820	0.052*
C5	0.52285 (10)	0.52681 (18)	0.65038 (7)	0.0426 (4)
H5	0.5326	0.4730	0.6869	0.051*
C6	0.45021 (9)	0.50297 (15)	0.59985 (7)	0.0348 (3)
H6	0.4106	0.4337	0.6022	0.042*
C7	0.35869 (8)	0.56091 (13)	0.49002 (6)	0.0286 (3)
H7A	0.3271	0.6502	0.4809	0.034*
H7B	0.3774	0.5378	0.4543	0.034*
C8	0.16952 (7)	0.51250 (12)	0.39278 (5)	0.0221 (2)
C9	0.14023 (8)	0.64467 (13)	0.37456 (6)	0.0262 (2)
H9	0.1360	0.7110	0.4043	0.031*
C10	0.11642 (8)	0.68209 (13)	0.31179 (6)	0.0286 (3)
H10	0.0963	0.7738	0.2993	0.034*
C11	0.12215 (8)	0.58726 (13)	0.26895 (6)	0.0263 (3)
H11	0.1070	0.6146	0.2269	0.032*
C12	0.15032 (7)	0.44820 (13)	0.28577 (5)	0.0226 (2)
C13	0.15527 (7)	0.34835 (14)	0.24015 (5)	0.0250 (2)
C14	0.18974 (8)	0.21871 (14)	0.25901 (6)	0.0295 (3)
H14	0.1961	0.1540	0.2293	0.035*
C15	0.21569 (8)	0.18099 (14)	0.32193 (6)	0.0301 (3)
H15	0.2390	0.0908	0.3339	0.036*
C16	0.20798 (8)	0.27152 (13)	0.36610 (6)	0.0261 (2)
H16	0.2239	0.2427	0.4080	0.031*
C17	0.17616 (7)	0.40859 (12)	0.34938 (5)	0.0217 (2)
C18	0.03465 (9)	0.40632 (18)	0.15059 (7)	0.0391 (3)
H18A	0.0086	0.3139	0.1402	0.059*
H18B	0.0214	0.4634	0.1132	0.059*
H18C	0.0124	0.4519	0.1805	0.059*
C19	0.16041 (11)	0.31121 (19)	0.13632 (7)	0.0440 (4)
H19A	0.2222	0.3041	0.1543	0.066*
H19B	0.1460	0.3585	0.0963	0.066*
H19C	0.1356	0.2174	0.1306	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03185 (16)	0.02196 (15)	0.01989 (15)	0.00216 (11)	0.00886 (11)	0.00062 (10)
O1	0.0511 (6)	0.0282 (5)	0.0261 (5)	0.0076 (4)	0.0164 (4)	−0.0023 (4)
O2	0.0370 (5)	0.0270 (5)	0.0301 (5)	−0.0001 (4)	0.0139 (4)	0.0051 (4)
N1	0.0310 (5)	0.0205 (5)	0.0262 (5)	0.0004 (4)	0.0021 (4)	0.0006 (4)
N2	0.0290 (5)	0.0407 (6)	0.0206 (5)	0.0027 (5)	0.0082 (4)	−0.0020 (4)
C1	0.0280 (6)	0.0226 (6)	0.0286 (6)	0.0030 (5)	0.0076 (5)	−0.0041 (5)
C2	0.0314 (7)	0.0320 (7)	0.0420 (8)	0.0005 (5)	0.0130 (6)	−0.0016 (6)
C3	0.0302 (7)	0.0378 (8)	0.0578 (10)	−0.0039 (6)	0.0122 (7)	−0.0103 (7)
C4	0.0307 (7)	0.0461 (9)	0.0453 (9)	0.0016 (6)	0.0003 (6)	−0.0161 (7)
C5	0.0422 (8)	0.0462 (9)	0.0314 (7)	0.0025 (7)	0.0006 (6)	−0.0014 (6)
C6	0.0356 (7)	0.0328 (7)	0.0310 (7)	−0.0022 (6)	0.0039 (6)	0.0001 (5)
C7	0.0338 (6)	0.0233 (6)	0.0262 (6)	−0.0009 (5)	0.0063 (5)	0.0012 (5)
C8	0.0232 (5)	0.0235 (6)	0.0197 (5)	0.0009 (4)	0.0068 (4)	0.0004 (4)
C9	0.0303 (6)	0.0235 (6)	0.0259 (6)	0.0029 (5)	0.0106 (5)	−0.0003 (5)
C10	0.0317 (6)	0.0243 (6)	0.0290 (6)	0.0056 (5)	0.0086 (5)	0.0048 (5)
C11	0.0267 (6)	0.0293 (6)	0.0222 (5)	0.0013 (5)	0.0068 (5)	0.0047 (5)
C12	0.0198 (5)	0.0263 (6)	0.0221 (5)	0.0002 (4)	0.0073 (4)	0.0000 (4)
C13	0.0211 (5)	0.0317 (6)	0.0227 (5)	−0.0004 (5)	0.0076 (4)	−0.0027 (5)
C14	0.0296 (6)	0.0301 (7)	0.0288 (6)	0.0025 (5)	0.0093 (5)	−0.0078 (5)
C15	0.0310 (6)	0.0237 (6)	0.0332 (7)	0.0049 (5)	0.0068 (5)	−0.0023 (5)
C16	0.0270 (6)	0.0240 (6)	0.0252 (6)	0.0018 (5)	0.0055 (5)	0.0003 (5)
C17	0.0193 (5)	0.0232 (6)	0.0224 (5)	−0.0002 (4)	0.0064 (4)	−0.0007 (4)
C18	0.0320 (7)	0.0515 (9)	0.0283 (7)	0.0022 (6)	0.0020 (5)	−0.0016 (6)
C19	0.0523 (9)	0.0567 (10)	0.0288 (7)	0.0067 (8)	0.0212 (7)	−0.0047 (7)

Geometric parameters (Å, º) top

S1—O1	1.4331 (9)	C8—C9	1.3718 (17)
S1—O2	1.4425 (9)	C8—C17	1.4351 (16)
S1—N1	1.6150 (11)	C9—C10	1.4084 (17)
S1—C8	1.7754 (12)	C9—H9	0.9500
N1—C7	1.4651 (17)	C10—C11	1.3622 (18)
N1—H1	0.857 (14)	C10—H10	0.9500
N2—C13	1.4184 (16)	C11—C12	1.4227 (17)
N2—C19	1.4558 (17)	C11—H11	0.9500
N2—C18	1.4687 (17)	C12—C17	1.4306 (16)
C1—C6	1.3843 (19)	C12—C13	1.4375 (16)
C1—C2	1.3948 (19)	C13—C14	1.3771 (19)
C1—C7	1.5125 (17)	C14—C15	1.4113 (18)
C2—C3	1.383 (2)	C14—H14	0.9500
C2—H2	0.9500	C15—C16	1.3687 (18)
C3—C4	1.387 (2)	C15—H15	0.9500
C3—H3	0.9500	C16—C17	1.4207 (17)
C4—C5	1.382 (2)	C16—H16	0.9500
C4—H4	0.9500	C18—H18A	0.9800
C5—C6	1.398 (2)	C18—H18B	0.9800
C5—H5	0.9500	C18—H18C	0.9800
C6—H6	0.9500	C19—H19A	0.9800
C7—H7A	0.9900	C19—H19B	0.9800
C7—H7B	0.9900	C19—H19C	0.9800

O1—S1—O2	118.40 (6)	C8—C9—C10	120.04 (11)
O1—S1—N1	107.93 (6)	C8—C9—H9	120.0
O2—S1—N1	106.16 (6)	C10—C9—H9	120.0
O1—S1—C8	106.45 (6)	C11—C10—C9	120.21 (12)
O2—S1—C8	109.54 (6)	C11—C10—H10	119.9
N1—S1—C8	107.99 (6)	C9—C10—H10	119.9
C7—N1—S1	119.48 (9)	C10—C11—C12	121.47 (11)
C7—N1—H1	118.9 (13)	C10—C11—H11	119.3
S1—N1—H1	112.0 (13)	C12—C11—H11	119.3
C13—N2—C19	115.60 (11)	C11—C12—C17	119.24 (11)
C13—N2—C18	114.53 (11)	C11—C12—C13	121.10 (11)
C19—N2—C18	110.42 (11)	C17—C12—C13	119.64 (11)
C6—C1—C2	119.02 (13)	C14—C13—N2	123.05 (11)
C6—C1—C7	123.03 (12)	C14—C13—C12	119.15 (11)
C2—C1—C7	117.94 (12)	N2—C13—C12	117.75 (11)
C3—C2—C1	120.89 (14)	C13—C14—C15	120.69 (11)
C3—C2—H2	119.6	C13—C14—H14	119.7
C1—C2—H2	119.6	C15—C14—H14	119.7
C2—C3—C4	119.91 (14)	C16—C15—C14	121.42 (12)
C2—C3—H3	120.0	C16—C15—H15	119.3
C4—C3—H3	120.0	C14—C15—H15	119.3
C5—C4—C3	119.67 (14)	C15—C16—C17	120.09 (11)
C5—C4—H4	120.2	C15—C16—H16	120.0
C3—C4—H4	120.2	C17—C16—H16	120.0
C4—C5—C6	120.44 (15)	C16—C17—C12	118.87 (11)
C4—C5—H5	119.8	C16—C17—C8	123.98 (11)
C6—C5—H5	119.8	C12—C17—C8	117.14 (11)
C1—C6—C5	120.06 (14)	N2—C18—H18A	109.5
C1—C6—H6	120.0	N2—C18—H18B	109.5
C5—C6—H6	120.0	H18A—C18—H18B	109.5
N1—C7—C1	113.36 (10)	N2—C18—H18C	109.5
N1—C7—H7A	108.9	H18A—C18—H18C	109.5
C1—C7—H7A	108.9	H18B—C18—H18C	109.5
N1—C7—H7B	108.9	N2—C19—H19A	109.5
C1—C7—H7B	108.9	N2—C19—H19B	109.5
H7A—C7—H7B	107.7	H19A—C19—H19B	109.5
C9—C8—C17	121.86 (11)	N2—C19—H19C	109.5
C9—C8—S1	116.47 (9)	H19A—C19—H19C	109.5
C17—C8—S1	121.66 (9)	H19B—C19—H19C	109.5

O1—S1—N1—C7	−55.53 (11)	C10—C11—C12—C17	−2.33 (18)
O2—S1—N1—C7	176.58 (9)	C10—C11—C12—C13	179.29 (11)
C8—S1—N1—C7	59.17 (11)	C19—N2—C13—C14	−19.34 (19)
C6—C1—C2—C3	−0.1 (2)	C18—N2—C13—C14	110.75 (14)
C7—C1—C2—C3	178.98 (13)	C19—N2—C13—C12	158.21 (12)
C1—C2—C3—C4	0.8 (2)	C18—N2—C13—C12	−71.70 (15)
C2—C3—C4—C5	−0.9 (2)	C11—C12—C13—C14	174.43 (12)
C3—C4—C5—C6	0.2 (2)	C17—C12—C13—C14	−3.94 (17)
C2—C1—C6—C5	−0.6 (2)	C11—C12—C13—N2	−3.22 (17)
C7—C1—C6—C5	−179.62 (13)	C17—C12—C13—N2	178.41 (10)
C4—C5—C6—C1	0.5 (2)	N2—C13—C14—C15	−179.01 (12)
S1—N1—C7—C1	137.24 (10)	C12—C13—C14—C15	3.47 (19)
C6—C1—C7—N1	−1.11 (18)	C13—C14—C15—C16	−0.4 (2)
C2—C1—C7—N1	179.83 (11)	C14—C15—C16—C17	−2.3 (2)
O1—S1—C8—C9	2.04 (12)	C15—C16—C17—C12	1.77 (18)
O2—S1—C8—C9	131.16 (10)	C15—C16—C17—C8	−177.02 (12)
N1—S1—C8—C9	−113.64 (10)	C11—C12—C17—C16	−177.06 (11)
O1—S1—C8—C17	−178.94 (10)	C13—C12—C17—C16	1.34 (16)
O2—S1—C8—C17	−49.82 (11)	C11—C12—C17—C8	1.81 (16)
N1—S1—C8—C17	65.38 (11)	C13—C12—C17—C8	−179.79 (10)
C17—C8—C9—C10	−0.62 (19)	C9—C8—C17—C16	178.42 (12)
S1—C8—C9—C10	178.40 (10)	S1—C8—C17—C16	−0.55 (16)
C8—C9—C10—C11	0.16 (19)	C9—C8—C17—C12	−0.39 (17)
C9—C10—C11—C12	1.33 (19)	S1—C8—C17—C12	−179.35 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86 (2)	2.12 (2)	2.9351 (14)	158 (2)

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀N₂O₂S
M_r	340.43
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	16.6635 (5), 9.5722 (2), 22.8942 (7)
β (°)	108.779 (1)
V (Å³)	3457.38 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.24 × 0.22

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4275, 4275, 3747
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.03
No. of reflections	4275
No. of parameters	223
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.40

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.857 (16)	2.124 (16)	2.9351 (14)	157.8 (17)

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Acknowledgements

The authors wish to thank Dr Hong Su from the University of the Cape Town for her assistance with the data collection and refinement.

References

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