5-(1H-Imidazol-1-ylsulfon-yl)-N,N-dimethyl-naphthalen-1-amine.

In the title mol-ecule, C(15)H(15)N(3)O(2)S, the dihedral angle between the naphthalene ring system and the imidazole ring is 86.1 (2)°. In the crystal structure, weak inter-molecular C-H⋯O and C-H⋯N hydrogen bonds, as well as weak C-H⋯π inter-actions, connect mol-ecules, forming a two-dimensional network.

Related literature

For background information, see: Corradini et al. (1997 ▶); Kavallieratos et al. (2005 ▶); Koike et al. (1996 ▶). For the synthesis, see: Hilderbrand et al. (2004 ▶).

Experimental

Crystal data

C15H15N3O2S

M = 301.36

Orthorhombic,

a = 16.3707 (16) Å

b = 7.7928 (7) Å

c = 22.088 (2) Å

V = 2817.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 150 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.944, T max = 0.977

9800 measured reflections

2577 independent reflections

2196 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.07

2577 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.31 e Å−3

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, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680804066X/lh2737sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804066X/lh2737Isup2.hkl

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

C15H15N3O2S	F(000) = 1264
Mr = 301.36	Dx = 1.421 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3852 reflections
a = 16.3707 (16) Å	θ = 2.2–28.2°
b = 7.7928 (7) Å	µ = 0.24 mm−1
c = 22.088 (2) Å	T = 150 K
V = 2817.8 (5) Å3	Block, red
Z = 8	0.20 × 0.10 × 0.10 mm

Bruker SMART CCD diffractometer	2577 independent reflections
Radiation source: fine-focus sealed tube	2196 reflections with I > 2σ(I)
graphite	Rint = 0.058
φ and ω scans	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→19
Tmin = 0.944, Tmax = 0.977	k = −7→9
9800 measured reflections	l = −26→25

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.6727P] where P = (Fo2 + 2Fc2)/3
2577 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.31 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	0.11008 (13)	−0.0608 (3)	0.10523 (10)	0.0274 (5)
H1A	0.1612	−0.1147	0.0922	0.041*
H1B	0.0721	−0.0558	0.0710	0.041*
H1C	0.0858	−0.1285	0.1380	0.041*
C2	0.18098 (13)	0.2027 (3)	0.08508 (9)	0.0319 (5)
H2A	0.1877	0.3221	0.0981	0.048*
H2B	0.1574	0.2002	0.0443	0.048*
H2C	0.2343	0.1457	0.0846	0.048*
C3	0.14436 (11)	0.1301 (3)	0.18942 (8)	0.0216 (4)
C4	0.21791 (12)	0.1896 (3)	0.21123 (9)	0.0247 (5)
H4	0.2602	0.2184	0.1836	0.030*
C5	0.23134 (11)	0.2084 (3)	0.27371 (9)	0.0255 (5)
H5	0.2825	0.2507	0.2874	0.031*
C6	0.17273 (11)	0.1673 (3)	0.31536 (9)	0.0234 (4)
H6	0.1840	0.1773	0.3574	0.028*
C7	0.09481 (11)	0.1098 (2)	0.29548 (9)	0.0193 (4)
C8	0.02739 (11)	0.0735 (2)	0.33507 (9)	0.0193 (4)
C9	−0.04868 (11)	0.0311 (3)	0.31351 (9)	0.0214 (4)
H9	−0.0917	0.0063	0.3410	0.026*
C10	−0.06277 (11)	0.0244 (3)	0.25099 (9)	0.0221 (4)
H10	−0.1159	−0.0007	0.2360	0.026*
C11	−0.00036 (11)	0.0539 (2)	0.21174 (9)	0.0207 (4)
H11	−0.0107	0.0476	0.1695	0.025*
C12	0.08007 (11)	0.0938 (2)	0.23193 (9)	0.0201 (4)
C13	0.06482 (12)	−0.2592 (3)	0.42799 (9)	0.0235 (5)
H13	0.0112	−0.2976	0.4187	0.028*
C14	0.13037 (12)	−0.3564 (3)	0.44095 (9)	0.0280 (5)
H14	0.1302	−0.4783	0.4420	0.034*
C15	0.17381 (12)	−0.0973 (3)	0.44626 (9)	0.0238 (5)
H15	0.2077	0.0005	0.4514	0.029*
N1	0.12680 (9)	0.1138 (2)	0.12696 (7)	0.0224 (4)
N2	0.09210 (9)	−0.0906 (2)	0.43108 (7)	0.0189 (4)
N3	0.19833 (10)	−0.2548 (2)	0.45265 (8)	0.0295 (4)
O1	−0.04379 (8)	0.04896 (19)	0.43910 (6)	0.0269 (4)
O2	0.08176 (8)	0.22535 (18)	0.43451 (6)	0.0274 (4)
S1	0.03535 (3)	0.08123 (6)	0.41480 (2)	0.02021 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0290 (10)	0.0248 (13)	0.0283 (11)	0.0020 (9)	0.0010 (9)	−0.0029 (9)
C2	0.0303 (11)	0.0407 (14)	0.0248 (10)	−0.0036 (10)	0.0055 (9)	0.0055 (10)
C3	0.0222 (9)	0.0177 (11)	0.0251 (10)	0.0019 (8)	0.0009 (8)	0.0024 (8)
C4	0.0194 (9)	0.0245 (12)	0.0302 (11)	−0.0013 (8)	0.0048 (8)	0.0025 (9)
C5	0.0178 (9)	0.0250 (12)	0.0337 (11)	−0.0014 (8)	−0.0041 (8)	−0.0010 (9)
C6	0.0226 (9)	0.0224 (12)	0.0251 (10)	−0.0001 (8)	−0.0045 (8)	−0.0002 (8)
C7	0.0199 (9)	0.0163 (11)	0.0218 (10)	0.0023 (8)	−0.0009 (7)	0.0015 (8)
C8	0.0220 (9)	0.0158 (11)	0.0201 (10)	0.0016 (8)	−0.0015 (7)	0.0013 (8)
C9	0.0208 (9)	0.0197 (11)	0.0238 (10)	−0.0010 (8)	0.0026 (8)	0.0008 (8)
C10	0.0181 (9)	0.0211 (11)	0.0270 (11)	−0.0021 (8)	−0.0042 (8)	−0.0001 (9)
C11	0.0227 (10)	0.0205 (12)	0.0190 (9)	0.0003 (8)	−0.0044 (8)	0.0015 (8)
C12	0.0192 (9)	0.0164 (11)	0.0247 (11)	0.0015 (8)	−0.0011 (8)	0.0021 (8)
C13	0.0246 (10)	0.0234 (12)	0.0226 (10)	−0.0060 (9)	−0.0018 (8)	−0.0014 (8)
C14	0.0337 (11)	0.0187 (12)	0.0316 (11)	−0.0002 (9)	−0.0014 (9)	−0.0017 (9)
C15	0.0200 (9)	0.0247 (12)	0.0266 (11)	−0.0024 (8)	−0.0030 (8)	0.0002 (8)
N1	0.0231 (8)	0.0233 (10)	0.0209 (9)	−0.0022 (7)	0.0025 (7)	0.0018 (7)
N2	0.0207 (8)	0.0179 (9)	0.0182 (8)	0.0004 (6)	−0.0016 (6)	−0.0003 (6)
N3	0.0247 (9)	0.0259 (11)	0.0377 (10)	0.0024 (7)	−0.0056 (7)	0.0012 (8)
O1	0.0232 (7)	0.0357 (9)	0.0216 (7)	0.0041 (6)	0.0028 (5)	−0.0006 (6)
O2	0.0325 (8)	0.0221 (8)	0.0276 (7)	0.0006 (6)	−0.0025 (6)	−0.0041 (6)
S1	0.0221 (3)	0.0203 (3)	0.0183 (3)	0.00270 (19)	−0.00034 (18)	−0.00119 (19)

C1—N1	1.468 (3)	C8—C9	1.374 (3)
C1—H1A	0.9800	C8—S1	1.767 (2)
C1—H1B	0.9800	C9—C10	1.401 (3)
C1—H1C	0.9800	C9—H9	0.9500
C2—N1	1.457 (2)	C10—C11	1.359 (3)
C2—H2A	0.9800	C10—H10	0.9500
C2—H2B	0.9800	C11—C12	1.424 (3)
C2—H2C	0.9800	C11—H11	0.9500
C3—C4	1.377 (3)	C13—C14	1.344 (3)
C3—N1	1.415 (2)	C13—N2	1.389 (3)
C3—C12	1.438 (3)	C13—H13	0.9500
C4—C5	1.405 (3)	C14—N3	1.390 (3)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.367 (3)	C15—N3	1.299 (3)
C5—H5	0.9500	C15—N2	1.380 (2)
C6—C7	1.422 (3)	C15—H15	0.9500
C6—H6	0.9500	N2—S1	1.6692 (16)
C7—C12	1.430 (3)	O1—S1	1.4249 (14)
C7—C8	1.436 (3)	O2—S1	1.4241 (14)
N1—C1—H1A	109.5	C10—C9—H9	120.0
N1—C1—H1B	109.5	C11—C10—C9	119.90 (17)
H1A—C1—H1B	109.5	C11—C10—H10	120.0
N1—C1—H1C	109.5	C9—C10—H10	120.0
H1A—C1—H1C	109.5	C10—C11—C12	122.14 (18)
H1B—C1—H1C	109.5	C10—C11—H11	118.9
N1—C2—H2A	109.5	C12—C11—H11	118.9
N1—C2—H2B	109.5	C11—C12—C7	118.84 (17)
H2A—C2—H2B	109.5	C11—C12—C3	120.99 (17)
N1—C2—H2C	109.5	C7—C12—C3	120.00 (16)
H2A—C2—H2C	109.5	C14—C13—N2	105.42 (17)
H2B—C2—H2C	109.5	C14—C13—H13	127.3
C4—C3—N1	123.28 (17)	N2—C13—H13	127.3
C4—C3—C12	118.54 (17)	C13—C14—N3	110.95 (19)
N1—C3—C12	118.04 (16)	C13—C14—H14	124.5
C3—C4—C5	121.01 (18)	N3—C14—H14	124.5
C3—C4—H4	119.5	N3—C15—N2	111.22 (17)
C5—C4—H4	119.5	N3—C15—H15	124.4
C6—C5—C4	121.79 (18)	N2—C15—H15	124.4
C6—C5—H5	119.1	C3—N1—C2	116.91 (16)
C4—C5—H5	119.1	C3—N1—C1	116.09 (16)
C5—C6—C7	119.71 (18)	C2—N1—C1	110.30 (16)
C5—C6—H6	120.1	C15—N2—C13	106.73 (16)
C7—C6—H6	120.1	C15—N2—S1	128.48 (14)
C6—C7—C12	118.84 (17)	C13—N2—S1	124.69 (13)
C6—C7—C8	124.31 (17)	C15—N3—C14	105.70 (17)
C12—C7—C8	116.79 (16)	O2—S1—O1	120.60 (9)
C9—C8—C7	122.21 (18)	O2—S1—N2	105.66 (8)
C9—C8—S1	114.88 (14)	O1—S1—N2	106.46 (9)
C7—C8—S1	122.91 (14)	O2—S1—C8	111.78 (9)
C8—C9—C10	119.99 (17)	O1—S1—C8	107.60 (8)
C8—C9—H9	120.0	N2—S1—C8	103.20 (8)
N1—C3—C4—C5	178.02 (18)	N2—C13—C14—N3	0.5 (2)
C12—C3—C4—C5	2.5 (3)	C4—C3—N1—C2	−15.4 (3)
C3—C4—C5—C6	0.5 (3)	C12—C3—N1—C2	160.21 (18)
C4—C5—C6—C7	−2.3 (3)	C4—C3—N1—C1	117.6 (2)
C5—C6—C7—C12	0.9 (3)	C12—C3—N1—C1	−66.8 (2)
C5—C6—C7—C8	−176.03 (19)	N3—C15—N2—C13	0.0 (2)
C6—C7—C8—C9	174.8 (2)	N3—C15—N2—S1	−176.46 (14)
C12—C7—C8—C9	−2.2 (3)	C14—C13—N2—C15	−0.3 (2)
C6—C7—C8—S1	−4.7 (3)	C14—C13—N2—S1	176.33 (14)
C12—C7—C8—S1	178.26 (14)	N2—C15—N3—C14	0.3 (2)
C7—C8—C9—C10	−0.8 (3)	C13—C14—N3—C15	−0.5 (2)
S1—C8—C9—C10	178.69 (15)	C15—N2—S1—O2	−14.58 (19)
C8—C9—C10—C11	2.4 (3)	C13—N2—S1—O2	169.57 (15)
C9—C10—C11—C12	−0.7 (3)	C15—N2—S1—O1	−143.94 (17)
C10—C11—C12—C7	−2.5 (3)	C13—N2—S1—O1	40.22 (18)
C10—C11—C12—C3	−177.88 (19)	C15—N2—S1—C8	102.91 (18)
C6—C7—C12—C11	−173.40 (18)	C13—N2—S1—C8	−72.93 (17)
C8—C7—C12—C11	3.8 (3)	C9—C8—S1—O2	−137.71 (15)
C6—C7—C12—C3	2.1 (3)	C7—C8—S1—O2	41.82 (18)
C8—C7—C12—C3	179.25 (17)	C9—C8—S1—O1	−3.13 (18)
C4—C3—C12—C11	171.62 (19)	C7—C8—S1—O1	176.40 (16)
N1—C3—C12—C11	−4.2 (3)	C9—C8—S1—N2	109.19 (16)
C4—C3—C12—C7	−3.7 (3)	C7—C8—S1—N2	−71.28 (17)
N1—C3—C12—C7	−179.52 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.95	2.42	3.057 (2)	125
C15—H15···N3i	0.95	2.45	3.395 (3)	173
C14—H14···O2ii	0.95	2.45	3.358 (3)	161
C13—H13···N1iii	0.95	2.57	3.506 (2)	169
C10—H10···Cgiv	0.95	2.82	3.302 (2)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2	0.95	2.42	3.057 (2)	125
C15—H15⋯N3i	0.95	2.45	3.395 (3)	173
C14—H14⋯O2ii	0.95	2.45	3.358 (3)	161
C13—H13⋯N1iii	0.95	2.57	3.506 (2)	169
C10—H10⋯Cgiv	0.95	2.82	3.302 (2)	113

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg is the centroid of the C3–C7/C12 ring.