N-Benzyl-5-(dimethyl-amino)-naphthalene-1-sulfonamide.

The structure of the title compound, C(19)H(20)N(2)O(2)S, displays inter-molecular 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 = 340.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.03

4275 reflections

223 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.40 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033083/hg5080sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811033083/hg5080Isup3.cml

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

C19H20N2O2S	F(000) = 1440
Mr = 340.43	Dx = 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

Nonius KappaCCD diffractometer	3747 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
graphite	θmax = 28.3°, θmin = 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 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(Fo2) + (0.0451P)2 + 3.0274P] where P = (Fo2 + 2Fc2)/3
4275 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.37 e Å−3
1 restraint	Δρmin = −0.40 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .