1-[5-(Dimethyl-amino)-1-naphthylsulfon-yl]imidazolidine-2-thione.

In the title mol-ecule, C(15)H(17)N(3)O(2)S(2), the dihedral angle between the naphthalene ring system and the imidazole ring is 89.63 (2)°. The crystal structure is stablized by weak inter-molecuar C-H⋯π and N-H⋯π inter-actions.

Related literature

For the applications of compounds containing a 5-(dimethyl­amino)­naphthalene-1-sulfonyl group, see: Corradini et al. (1996 ▶, 1997 ▶); Christoforou et al. (2006 ▶). For a related structure, see: Zhang et al. (2009 ▶). For the synthetic procedure, see: Corradini et al. (1996 ▶).

Experimental

Crystal data

C15H17N3O2S2

M = 335.44

Monoclinic,

a = 15.364 (4) Å

b = 6.9814 (18) Å

c = 15.470 (4) Å

β = 113.967 (4)°

V = 1516.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 298 K

0.33 × 0.32 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.955, T max = 0.965

8935 measured reflections

3302 independent reflections

2605 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.145

S = 1.04

3302 reflections

204 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S1600536810029788/lh5094sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029788/lh5094Isup2.hkl

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

C15H17N3O2S2	F(000) = 700
Mr = 335.44	Dx = 1.465 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2682 reflections
a = 15.364 (4) Å	θ = 2.4–28.1°
b = 6.9814 (18) Å	µ = 0.36 mm−1
c = 15.470 (4) Å	T = 298 K
β = 113.967 (4)°	Block, yellow
V = 1516.3 (7) Å3	0.33 × 0.32 × 0.28 mm
Z = 4

Bruker SMART CCD diffractometer	3302 independent reflections
Radiation source: fine-focus sealed tube	2605 reflections with I > 2σ(I)
graphite	Rint = 0.104
φ and ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −17→19
Tmin = 0.955, Tmax = 0.965	k = −8→8
8935 measured reflections	l = −19→19

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.071P)2] where P = (Fo2 + 2Fc2)/3
3302 reflections	(Δ/σ)max = 0.001
204 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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	0.61885 (15)	0.6070 (3)	0.72722 (15)	0.0306 (5)
C2	0.68621 (19)	0.7474 (3)	0.76019 (18)	0.0379 (6)
H2	0.6868	0.8466	0.7203	0.045*
C3	0.75453 (19)	0.7430 (3)	0.85392 (19)	0.0434 (6)
H3	0.8011	0.8375	0.8746	0.052*
C4	0.75429 (17)	0.6051 (3)	0.91479 (17)	0.0384 (6)
H4	0.7983	0.6099	0.9774	0.046*
C5	0.68768 (15)	0.4529 (3)	0.88431 (15)	0.0271 (5)
C6	0.68432 (16)	0.2951 (3)	0.94243 (16)	0.0299 (5)
C7	0.62594 (17)	0.1403 (3)	0.90561 (16)	0.0342 (5)
H7	0.6253	0.0398	0.9448	0.041*
C8	0.56701 (17)	0.1343 (3)	0.80839 (17)	0.0370 (6)
H8	0.5298	0.0267	0.7828	0.044*
C9	0.56426 (17)	0.2841 (3)	0.75203 (17)	0.0336 (5)
H9	0.5235	0.2792	0.6883	0.040*
C10	0.62191 (14)	0.4484 (3)	0.78765 (15)	0.0271 (5)
C11	0.45077 (18)	0.6337 (5)	0.6290 (2)	0.0536 (7)
H11A	0.4425	0.5578	0.6769	0.080*
H11B	0.4051	0.5953	0.5678	0.080*
H11C	0.4416	0.7665	0.6391	0.080*
C12	0.5635 (2)	0.7304 (4)	0.5667 (2)	0.0576 (8)
H12A	0.5604	0.8616	0.5837	0.086*
H12B	0.5157	0.7072	0.5043	0.086*
H12C	0.6253	0.7046	0.5677	0.086*
C13	0.7299 (2)	0.6395 (4)	1.1372 (2)	0.0589 (8)
H13A	0.7391	0.7055	1.0863	0.071*
H13B	0.7896	0.6394	1.1929	0.071*
C14	0.6522 (2)	0.7308 (4)	1.1575 (2)	0.0515 (7)
H14A	0.6764	0.7806	1.2216	0.062*
H14B	0.6223	0.8341	1.1135	0.062*
C15	0.60716 (16)	0.4138 (3)	1.11357 (15)	0.0336 (5)
N1	0.54715 (14)	0.6055 (3)	0.63401 (13)	0.0381 (5)
N2	0.69536 (13)	0.4434 (3)	1.10932 (13)	0.0328 (4)
N3	0.58699 (18)	0.5772 (3)	1.14554 (17)	0.0496 (6)
H3A	0.534 (2)	0.590 (4)	1.154 (2)	0.059*
O1	0.74468 (12)	0.1037 (2)	1.09977 (12)	0.0422 (4)
O2	0.84230 (11)	0.3748 (3)	1.09114 (11)	0.0414 (4)
S1	0.75069 (4)	0.29031 (8)	1.06638 (4)	0.03206 (19)
S2	0.53971 (5)	0.22082 (10)	1.08475 (6)	0.0524 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0297 (12)	0.0365 (13)	0.0286 (12)	0.0012 (10)	0.0150 (9)	0.0006 (9)
C2	0.0425 (14)	0.0352 (13)	0.0384 (13)	−0.0015 (10)	0.0190 (11)	0.0049 (10)
C3	0.0452 (16)	0.0396 (14)	0.0437 (15)	−0.0167 (11)	0.0165 (12)	−0.0017 (11)
C4	0.0372 (14)	0.0423 (14)	0.0316 (12)	−0.0092 (11)	0.0097 (10)	−0.0028 (10)
C5	0.0263 (11)	0.0309 (11)	0.0263 (11)	0.0000 (9)	0.0129 (8)	−0.0013 (9)
C6	0.0266 (11)	0.0343 (12)	0.0291 (11)	0.0026 (9)	0.0118 (9)	0.0001 (9)
C7	0.0402 (13)	0.0308 (12)	0.0339 (12)	−0.0022 (10)	0.0173 (10)	−0.0006 (10)
C8	0.0413 (14)	0.0339 (13)	0.0393 (13)	−0.0111 (11)	0.0200 (11)	−0.0103 (10)
C9	0.0303 (12)	0.0416 (13)	0.0295 (12)	−0.0041 (10)	0.0126 (9)	−0.0060 (10)
C10	0.0232 (10)	0.0328 (12)	0.0280 (11)	0.0021 (9)	0.0130 (9)	−0.0015 (9)
C11	0.0345 (15)	0.072 (2)	0.0477 (16)	0.0080 (14)	0.0092 (12)	0.0107 (14)
C12	0.0583 (19)	0.073 (2)	0.0356 (15)	−0.0115 (15)	0.0130 (13)	0.0146 (13)
C13	0.0640 (19)	0.0383 (15)	0.083 (2)	−0.0096 (14)	0.0386 (17)	−0.0153 (15)
C14	0.070 (2)	0.0387 (15)	0.0469 (16)	0.0002 (13)	0.0246 (15)	−0.0069 (12)
C15	0.0395 (13)	0.0371 (13)	0.0266 (11)	0.0071 (10)	0.0158 (10)	0.0067 (10)
N1	0.0322 (11)	0.0490 (12)	0.0302 (10)	0.0000 (9)	0.0099 (8)	0.0070 (9)
N2	0.0342 (11)	0.0307 (10)	0.0343 (11)	−0.0012 (8)	0.0145 (8)	−0.0036 (8)
N3	0.0595 (15)	0.0440 (13)	0.0595 (15)	0.0068 (11)	0.0389 (13)	−0.0025 (11)
O1	0.0509 (11)	0.0343 (9)	0.0399 (10)	0.0105 (8)	0.0169 (8)	0.0090 (7)
O2	0.0284 (9)	0.0521 (11)	0.0391 (10)	0.0026 (8)	0.0092 (7)	0.0035 (8)
S1	0.0314 (3)	0.0339 (3)	0.0303 (3)	0.0052 (2)	0.0119 (2)	0.0030 (2)
S2	0.0465 (4)	0.0484 (4)	0.0687 (5)	−0.0096 (3)	0.0300 (4)	0.0000 (3)

C1—C2	1.365 (3)	C11—H11B	0.9600
C1—N1	1.415 (3)	C11—H11C	0.9600
C1—C10	1.437 (3)	C12—N1	1.456 (3)
C2—C3	1.403 (4)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.348 (3)	C12—H12C	0.9600
C3—H3	0.9300	C13—N2	1.468 (3)
C4—C5	1.417 (3)	C13—C14	1.496 (4)
C4—H4	0.9300	C13—H13A	0.9700
C5—C10	1.425 (3)	C13—H13B	0.9700
C5—C6	1.436 (3)	C14—N3	1.428 (3)
C6—C7	1.372 (3)	C14—H14A	0.9700
C6—S1	1.769 (2)	C14—H14B	0.9700
C7—C8	1.406 (3)	C15—N3	1.329 (3)
C7—H7	0.9300	C15—N2	1.398 (3)
C8—C9	1.351 (3)	C15—S2	1.647 (2)
C8—H8	0.9300	N2—S1	1.6628 (19)
C9—C10	1.417 (3)	N3—H3A	0.88 (3)
C9—H9	0.9300	O1—S1	1.4182 (17)
C11—N1	1.464 (3)	O2—S1	1.4275 (17)
C11—H11A	0.9600
C2—C1—N1	123.0 (2)	N1—C12—H12A	109.5
C2—C1—C10	119.4 (2)	N1—C12—H12B	109.5
N1—C1—C10	117.6 (2)	H12A—C12—H12B	109.5
C1—C2—C3	120.4 (2)	N1—C12—H12C	109.5
C1—C2—H2	119.8	H12A—C12—H12C	109.5
C3—C2—H2	119.8	H12B—C12—H12C	109.5
C4—C3—C2	121.7 (2)	N2—C13—C14	103.6 (2)
C4—C3—H3	119.2	N2—C13—H13A	111.0
C2—C3—H3	119.2	C14—C13—H13A	111.0
C3—C4—C5	120.7 (2)	N2—C13—H13B	111.0
C3—C4—H4	119.7	C14—C13—H13B	111.0
C5—C4—H4	119.7	H13A—C13—H13B	109.0
C4—C5—C10	118.31 (19)	N3—C14—C13	103.3 (2)
C4—C5—C6	124.9 (2)	N3—C14—H14A	111.1
C10—C5—C6	116.72 (19)	C13—C14—H14A	111.1
C7—C6—C5	121.9 (2)	N3—C14—H14B	111.1
C7—C6—S1	115.27 (17)	C13—C14—H14B	111.1
C5—C6—S1	122.80 (17)	H14A—C14—H14B	109.1
C6—C7—C8	119.7 (2)	N3—C15—N2	105.5 (2)
C6—C7—H7	120.1	N3—C15—S2	125.9 (2)
C8—C7—H7	120.1	N2—C15—S2	128.54 (17)
C9—C8—C7	120.3 (2)	C1—N1—C12	115.8 (2)
C9—C8—H8	119.8	C1—N1—C11	113.87 (19)
C7—C8—H8	119.8	C12—N1—C11	110.3 (2)
C8—C9—C10	121.7 (2)	C15—N2—C13	111.46 (19)
C8—C9—H9	119.2	C15—N2—S1	125.90 (16)
C10—C9—H9	119.2	C13—N2—S1	122.26 (17)
C9—C10—C5	119.38 (19)	C15—N3—C14	115.8 (2)
C9—C10—C1	121.37 (19)	C15—N3—H3A	121 (2)
C5—C10—C1	119.17 (19)	C14—N3—H3A	123.1 (19)
N1—C11—H11A	109.5	O1—S1—O2	119.00 (10)
N1—C11—H11B	109.5	O1—S1—N2	108.99 (10)
H11A—C11—H11B	109.5	O2—S1—N2	103.62 (10)
N1—C11—H11C	109.5	O1—S1—C6	108.55 (11)
H11A—C11—H11C	109.5	O2—S1—C6	110.75 (10)
H11B—C11—H11C	109.5	N2—S1—C6	104.94 (10)
N1—C1—C2—C3	178.9 (2)	C2—C1—N1—C12	16.4 (3)
C10—C1—C2—C3	−3.7 (4)	C10—C1—N1—C12	−161.2 (2)
C1—C2—C3—C4	−2.1 (4)	C2—C1—N1—C11	−113.0 (3)
C2—C3—C4—C5	3.6 (4)	C10—C1—N1—C11	69.5 (3)
C3—C4—C5—C10	0.7 (3)	N3—C15—N2—C13	−2.2 (3)
C3—C4—C5—C6	177.1 (2)	S2—C15—N2—C13	177.2 (2)
C4—C5—C6—C7	−171.7 (2)	N3—C15—N2—S1	−175.13 (17)
C10—C5—C6—C7	4.8 (3)	S2—C15—N2—S1	4.3 (3)
C4—C5—C6—S1	11.1 (3)	C14—C13—N2—C15	−1.1 (3)
C10—C5—C6—S1	−172.47 (15)	C14—C13—N2—S1	172.14 (18)
C5—C6—C7—C8	−0.3 (3)	N2—C15—N3—C14	5.0 (3)
S1—C6—C7—C8	177.21 (17)	S2—C15—N3—C14	−174.4 (2)
C6—C7—C8—C9	−3.2 (3)	C13—C14—N3—C15	−5.7 (3)
C7—C8—C9—C10	1.9 (4)	C15—N2—S1—O1	−44.0 (2)
C8—C9—C10—C5	2.9 (3)	C13—N2—S1—O1	143.8 (2)
C8—C9—C10—C1	179.8 (2)	C15—N2—S1—O2	−171.64 (17)
C4—C5—C10—C9	170.7 (2)	C13—N2—S1—O2	16.1 (2)
C6—C5—C10—C9	−6.0 (3)	C15—N2—S1—C6	72.1 (2)
C4—C5—C10—C1	−6.3 (3)	C13—N2—S1—C6	−100.1 (2)
C6—C5—C10—C1	177.01 (18)	C7—C6—S1—O1	12.6 (2)
C2—C1—C10—C9	−169.1 (2)	C5—C6—S1—O1	−169.92 (17)
N1—C1—C10—C9	8.5 (3)	C7—C6—S1—O2	145.02 (18)
C2—C1—C10—C5	7.8 (3)	C5—C6—S1—O2	−37.5 (2)
N1—C1—C10—C5	−174.59 (19)	C7—C6—S1—N2	−103.77 (18)
N2—C13—C14—N3	3.7 (3)	C5—C6—S1—N2	73.67 (19)

Cg1 and Cg2 are the centroids of the C1–C5/C10 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1i	0.93	2.88	3.667 (3)	143
N3—H3A···Cg2ii	0.88 (3)	2.58 (3)	3.433 (3)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C5/C10 and C5–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1i	0.93	2.88	3.667 (3)	143
N3—H3A⋯Cg2ii	0.88 (3)	2.58 (3)	3.433 (3)	165 (2)

Symmetry codes: (i) ; (ii) .