N-(2-Amino-ethyl)-5-(dimethyl-amino)naphthalene-1-sulfonamide.

In the title compound, C(14)H(19)N(3)O(2)S, the N atom of the dimethyl-amino group and the S atom are displaced by 0.078 (2) and 0.084 (2) Å, respectively, from the naphthalene ring plane. The 2-amino-ethyl group has a coiled conformation with an N-C-C-NH(2) torsion angle of 53.6 (4)°. In the crystal structure, inter-molecular N-H⋯N and weak C-H⋯O hydrogen bonds link mol-ecules into chains along [001].

Related literature

For applications of ligands containing the 5-(dimethyl­amino)naphthalene-1-sulfonyl (dans­yl) group, see: Corradini et al. (1996 ▶, 1997 ▶); Christoforou et al. (2006 ▶).

Experimental

Crystal data

C14H19N3O2S

M = 293.38

Orthorhombic,

a = 15.5221 (15) Å

b = 11.5423 (11) Å

c = 8.1360 (8) Å

V = 1457.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.956, T max = 0.956

7478 measured reflections

3140 independent reflections

3012 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.11

3140 reflections

192 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1332 Friedel pairs

Flack parameter: −0.03 (8)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; 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: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901962X/lh2821sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901962X/lh2821Isup2.hkl

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

C14H19N3O2S	F(000) = 624
Mr = 293.38	Dx = 1.337 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4085 reflections
a = 15.5221 (15) Å	θ = 2.2–28.0°
b = 11.5423 (11) Å	µ = 0.23 mm−1
c = 8.1360 (8) Å	T = 298 K
V = 1457.7 (2) Å3	Block, colorless
Z = 4	0.20 × 0.20 × 0.20 mm

Bruker SMART CCD diffractometer	3140 independent reflections
Radiation source: fine-focus sealed tube	3012 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −19→13
Tmin = 0.956, Tmax = 0.956	k = −14→14
7478 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.0989P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
3140 reflections	Δρmax = 0.24 e Å−3
192 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 1332 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (8)

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
C1	0.6783 (2)	0.2592 (3)	1.2600 (5)	0.0711 (9)
H1A	0.6195	0.2620	1.2236	0.107*
H1B	0.6797	0.2519	1.3775	0.107*
H1C	0.7065	0.1937	1.2111	0.107*
C2	0.67195 (17)	0.4676 (3)	1.2579 (4)	0.0615 (7)
H2A	0.7030	0.5368	1.2300	0.092*
H2B	0.6616	0.4659	1.3742	0.092*
H2C	0.6180	0.4665	1.2004	0.092*
C3	0.75553 (12)	0.36601 (19)	1.0498 (3)	0.0381 (5)
C4	0.72410 (14)	0.43583 (19)	0.9255 (3)	0.0451 (5)
H4	0.6796	0.4874	0.9477	0.054*
C5	0.75833 (15)	0.4299 (2)	0.7670 (3)	0.0480 (6)
H5	0.7350	0.4767	0.6853	0.058*
C6	0.82454 (15)	0.3580 (2)	0.7281 (3)	0.0445 (5)
H6	0.8451	0.3547	0.6208	0.053*
C7	0.86251 (12)	0.28748 (17)	0.8530 (3)	0.0323 (4)
C8	0.93538 (13)	0.21356 (16)	0.8264 (3)	0.0309 (4)
C9	0.96977 (14)	0.14947 (18)	0.9519 (3)	0.0366 (4)
H9	1.0158	0.0999	0.9311	0.044*
C10	0.93643 (14)	0.15783 (18)	1.1106 (3)	0.0379 (4)
H10	0.9610	0.1151	1.1954	0.045*
C11	0.86816 (12)	0.22823 (16)	1.1418 (3)	0.0363 (4)
H11	0.8473	0.2345	1.2486	0.044*
C12	0.82814 (12)	0.29230 (16)	1.0143 (3)	0.0322 (4)
C14	1.10343 (19)	0.3731 (3)	0.6827 (4)	0.0689 (9)
H14A	1.1354	0.4225	0.6080	0.083*
H14B	1.1400	0.3079	0.7107	0.083*
C15	1.0839 (2)	0.4406 (3)	0.8375 (5)	0.0833 (11)
H15A	1.0609	0.3874	0.9188	0.100*
H15B	1.1375	0.4712	0.8805	0.100*
N1	0.72278 (13)	0.36630 (17)	1.2108 (3)	0.0467 (5)
O1	0.92413 (13)	0.18510 (17)	0.5084 (2)	0.0558 (5)
O2	1.05529 (12)	0.12231 (15)	0.6510 (2)	0.0553 (4)
N2	1.02722 (14)	0.33007 (18)	0.5987 (3)	0.0495 (5)
H2D	1.0054 (19)	0.358 (3)	0.508 (5)	0.059*
N3	1.0237 (3)	0.5358 (3)	0.8182 (5)	0.0993 (13)
H3A	0.980 (3)	0.499 (5)	0.773 (8)	0.119*
H3B	1.044 (3)	0.588 (4)	0.752 (7)	0.119*
S1	0.98740 (3)	0.20448 (4)	0.63277 (8)	0.03840 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0693 (17)	0.0655 (18)	0.079 (2)	0.0010 (15)	0.0311 (15)	0.0156 (17)
C2	0.0547 (14)	0.0663 (17)	0.0635 (18)	0.0210 (13)	0.0108 (12)	−0.0083 (14)
C3	0.0340 (10)	0.0365 (11)	0.0439 (12)	0.0001 (8)	−0.0005 (9)	−0.0006 (9)
C4	0.0377 (10)	0.0406 (12)	0.0570 (14)	0.0071 (9)	−0.0008 (10)	0.0082 (11)
C5	0.0472 (12)	0.0486 (13)	0.0482 (14)	0.0062 (10)	−0.0097 (10)	0.0171 (11)
C6	0.0533 (12)	0.0461 (12)	0.0343 (11)	−0.0003 (10)	−0.0053 (9)	0.0120 (10)
C7	0.0331 (9)	0.0315 (9)	0.0323 (10)	−0.0037 (7)	−0.0041 (8)	0.0023 (8)
C8	0.0369 (10)	0.0294 (9)	0.0264 (10)	−0.0018 (8)	0.0014 (8)	−0.0008 (8)
C9	0.0418 (10)	0.0344 (11)	0.0336 (10)	0.0061 (8)	−0.0015 (9)	0.0015 (8)
C10	0.0450 (10)	0.0387 (10)	0.0299 (11)	0.0066 (8)	−0.0045 (8)	0.0077 (8)
C11	0.0434 (10)	0.0367 (9)	0.0286 (9)	0.0018 (7)	0.0003 (9)	0.0037 (9)
C12	0.0328 (9)	0.0303 (10)	0.0335 (10)	−0.0049 (7)	−0.0015 (8)	0.0030 (8)
C14	0.0647 (16)	0.0609 (16)	0.081 (3)	−0.0208 (14)	0.0173 (15)	−0.0189 (15)
C15	0.099 (2)	0.077 (2)	0.075 (2)	−0.034 (2)	0.012 (2)	−0.0264 (19)
N1	0.0462 (10)	0.0458 (11)	0.0482 (11)	0.0089 (9)	0.0133 (9)	0.0015 (9)
O1	0.0778 (12)	0.0595 (11)	0.0302 (8)	−0.0089 (9)	−0.0003 (8)	−0.0045 (8)
O2	0.0729 (10)	0.0498 (9)	0.0432 (9)	0.0162 (8)	0.0174 (9)	−0.0028 (8)
N2	0.0641 (13)	0.0425 (10)	0.0420 (14)	−0.0092 (9)	0.0122 (9)	0.0037 (9)
N3	0.158 (4)	0.0527 (18)	0.087 (2)	−0.0261 (19)	0.036 (2)	−0.0248 (16)
S1	0.0538 (3)	0.0341 (2)	0.0274 (2)	−0.00129 (19)	0.0066 (3)	−0.0034 (3)

C1—N1	1.472 (3)	C8—S1	1.773 (2)
C1—H1A	0.9600	C9—C10	1.395 (3)
C1—H1B	0.9600	C9—H9	0.9300
C1—H1C	0.9600	C10—C11	1.359 (3)
C2—N1	1.461 (3)	C10—H10	0.9300
C2—H2A	0.9600	C11—C12	1.417 (3)
C2—H2B	0.9600	C11—H11	0.9300
C2—H2C	0.9600	C14—N2	1.454 (4)
C3—C4	1.382 (3)	C14—C15	1.511 (5)
C3—N1	1.405 (3)	C14—H14A	0.9700
C3—C12	1.441 (3)	C14—H14B	0.9700
C4—C5	1.396 (3)	C15—N3	1.450 (5)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.358 (3)	C15—H15B	0.9700
C5—H5	0.9300	O1—S1	1.4278 (19)
C6—C7	1.429 (3)	O2—S1	1.4255 (18)
C6—H6	0.9300	N2—S1	1.600 (2)
C7—C12	1.417 (3)	N2—H2D	0.87 (3)
C7—C8	1.433 (3)	N3—H3A	0.88 (5)
C8—C9	1.369 (3)	N3—H3B	0.87 (5)
N1—C1—H1A	109.5	C9—C10—H10	119.9
N1—C1—H1B	109.5	C10—C11—C12	121.1 (2)
H1A—C1—H1B	109.5	C10—C11—H11	119.4
N1—C1—H1C	109.5	C12—C11—H11	119.4
H1A—C1—H1C	109.5	C11—C12—C7	119.47 (18)
H1B—C1—H1C	109.5	C11—C12—C3	120.3 (2)
N1—C2—H2A	109.5	C7—C12—C3	120.20 (18)
N1—C2—H2B	109.5	N2—C14—C15	113.9 (3)
H2A—C2—H2B	109.5	N2—C14—H14A	108.8
N1—C2—H2C	109.5	C15—C14—H14A	108.8
H2A—C2—H2C	109.5	N2—C14—H14B	108.8
H2B—C2—H2C	109.5	C15—C14—H14B	108.8
C4—C3—N1	123.6 (2)	H14A—C14—H14B	107.7
C4—C3—C12	118.3 (2)	N3—C15—C14	115.5 (3)
N1—C3—C12	118.11 (19)	N3—C15—H15A	108.4
C3—C4—C5	120.8 (2)	C14—C15—H15A	108.4
C3—C4—H4	119.6	N3—C15—H15B	108.4
C5—C4—H4	119.6	C14—C15—H15B	108.4
C6—C5—C4	122.3 (2)	H15A—C15—H15B	107.5
C6—C5—H5	118.9	C3—N1—C2	116.2 (2)
C4—C5—H5	118.9	C3—N1—C1	114.9 (2)
C5—C6—C7	119.6 (2)	C2—N1—C1	110.3 (2)
C5—C6—H6	120.2	C14—N2—S1	122.8 (2)
C7—C6—H6	120.2	C14—N2—H2D	126 (2)
C12—C7—C6	118.73 (19)	S1—N2—H2D	109 (2)
C12—C7—C8	117.42 (17)	C15—N3—H3A	100 (3)
C6—C7—C8	123.8 (2)	C15—N3—H3B	111 (3)
C9—C8—C7	121.08 (19)	H3A—N3—H3B	111 (5)
C9—C8—S1	116.94 (16)	O2—S1—O1	118.56 (12)
C7—C8—S1	121.94 (15)	O2—S1—N2	109.58 (12)
C8—C9—C10	120.57 (19)	O1—S1—N2	106.55 (12)
C8—C9—H9	119.7	O2—S1—C8	106.46 (10)
C10—C9—H9	119.7	O1—S1—C8	109.01 (10)
C11—C10—C9	120.2 (2)	N2—S1—C8	106.04 (10)
C11—C10—H10	119.9
N1—C3—C4—C5	−178.7 (2)	C4—C3—C12—C11	173.49 (19)
C12—C3—C4—C5	3.9 (3)	N1—C3—C12—C11	−4.0 (3)
C3—C4—C5—C6	−1.4 (4)	C4—C3—C12—C7	−3.6 (3)
C4—C5—C6—C7	−1.5 (4)	N1—C3—C12—C7	178.89 (18)
C5—C6—C7—C12	1.7 (3)	N2—C14—C15—N3	−53.6 (4)
C5—C6—C7—C8	−176.60 (19)	C4—C3—N1—C2	−18.4 (3)
C12—C7—C8—C9	0.6 (3)	C12—C3—N1—C2	159.0 (2)
C6—C7—C8—C9	178.9 (2)	C4—C3—N1—C1	112.6 (3)
C12—C7—C8—S1	−177.20 (14)	C12—C3—N1—C1	−70.0 (3)
C6—C7—C8—S1	1.1 (3)	C15—C14—N2—S1	−91.9 (3)
C7—C8—C9—C10	−2.3 (3)	C14—N2—S1—O2	−40.1 (2)
S1—C8—C9—C10	175.56 (16)	C14—N2—S1—O1	−169.58 (19)
C8—C9—C10—C11	1.3 (3)	C14—N2—S1—C8	74.4 (2)
C9—C10—C11—C12	1.5 (3)	C9—C8—S1—O2	3.06 (19)
C10—C11—C12—C7	−3.2 (3)	C7—C8—S1—O2	−179.09 (16)
C10—C11—C12—C3	179.68 (19)	C9—C8—S1—O1	132.05 (17)
C6—C7—C12—C11	−176.28 (19)	C7—C8—S1—O1	−50.11 (19)
C8—C7—C12—C11	2.1 (3)	C9—C8—S1—N2	−113.59 (18)
C6—C7—C12—C3	0.8 (3)	C7—C8—S1—N2	64.25 (19)
C8—C7—C12—C3	179.24 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.48	3.093 (3)	123
N3—H3A···N2	0.88 (5)	2.52 (6)	2.972 (4)	113 (4)
C11—H11···O1i	0.93	2.49	3.146 (3)	128
N2—H2D···N3ii	0.87 (3)	2.02 (4)	2.869 (4)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.48	3.093 (3)	123
N3—H3A⋯N2	0.88 (5)	2.52 (6)	2.972 (4)	113 (4)
C11—H11⋯O1i	0.93	2.49	3.146 (3)	128
N2—H2D⋯N3ii	0.87 (3)	2.02 (4)	2.869 (4)	163 (3)

Symmetry codes: (i) ; (ii) .