8-Quinolyl 5-(dimethyl-amino)-naphthalene-1-sulfonate.

In the title compound, C(21)H(18)N(2)O(3)S, the dihedral angle between the naphthalene and quinoline ring systems is 55.53 (2)°, and the torsion angle involving the connecting C-S-O-C atoms is 87.60 (3)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds connect mol-ecules into chains along [100] and there are π-π stacking inter-actions between pairs of chains with a centroid-centroid distance of 3.5485 (15) Å.

Related literature

For background information and the applications of compounds containing the 5-(dimethyl­amino)­naphthalene-1-sulfonyl group, see: Li et al. (1975 ▶); Walkup & Imperiali (1997 ▶); Chen & Chen (2004 ▶).

Experimental

Crystal data

C21H18N2O3S

M = 378.43

Triclinic,

a = 9.5556 (12) Å

b = 10.1237 (12) Å

c = 11.4182 (14) Å

α = 108.736 (2)°

β = 100.426 (2)°

γ = 111.860 (2)°

V = 912.30 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.20 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 = 0.961, T max = 0.980

5269 measured reflections

3526 independent reflections

2959 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.132

S = 1.04

3526 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.34 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/S160053681002979X/lh5093sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002979X/lh5093Isup2.hkl

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

C21H18N2O3S	Z = 2
Mr = 378.43	F(000) = 396
Triclinic, P1	Dx = 1.378 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5556 (12) Å	Cell parameters from 2502 reflections
b = 10.1237 (12) Å	θ = 1.7–22.5°
c = 11.4182 (14) Å	µ = 0.20 mm−1
α = 108.736 (2)°	T = 298 K
β = 100.426 (2)°	Block, yellow
γ = 111.860 (2)°	0.20 × 0.20 × 0.20 mm
V = 912.30 (19) Å3

Bruker SMART CCD diffractometer	3526 independent reflections
Radiation source: fine-focus sealed tube	2959 reflections with I > 2σ(I)
graphite	Rint = 0.054
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −11→11
Tmin = 0.961, Tmax = 0.980	k = −12→12
5269 measured reflections	l = −14→14

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0622P)2 + 0.1786P] where P = (Fo2 + 2Fc2)/3
3526 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.34 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	0.3811 (4)	−0.3563 (4)	0.4404 (3)	0.0808 (9)
H1A	0.3092	−0.3111	0.4357	0.121*
H1B	0.3945	−0.3739	0.5185	0.121*
H1C	0.3375	−0.4546	0.3645	0.121*
C2	0.6414 (4)	−0.3214 (4)	0.4384 (3)	0.0776 (8)
H2A	0.5946	−0.4150	0.3577	0.116*
H2B	0.6564	−0.3480	0.5116	0.116*
H2C	0.7433	−0.2490	0.4419	0.116*
C3	0.5317 (3)	−0.1772 (2)	0.3569 (2)	0.0460 (5)
C4	0.4046 (3)	−0.2372 (3)	0.2452 (2)	0.0549 (6)
H4	0.3129	−0.3287	0.2251	0.066*
C5	0.4103 (3)	−0.1632 (3)	0.1607 (2)	0.0543 (6)
H5	0.3217	−0.2059	0.0857	0.065*
C6	0.5421 (3)	−0.0303 (3)	0.1855 (2)	0.0469 (5)
H6	0.5452	0.0133	0.1251	0.056*
C7	0.6746 (2)	0.0422 (2)	0.30273 (19)	0.0386 (4)
C8	0.8158 (2)	0.1871 (2)	0.34276 (19)	0.0407 (5)
C9	0.9371 (3)	0.2558 (3)	0.4599 (2)	0.0498 (5)
H9	1.0277	0.3491	0.4818	0.060*
C10	0.9242 (3)	0.1849 (3)	0.5467 (2)	0.0593 (6)
H10	1.0052	0.2328	0.6279	0.071*
C11	0.7943 (3)	0.0466 (3)	0.5135 (2)	0.0550 (6)
H11	0.7878	0.0016	0.5729	0.066*
C12	0.6684 (2)	−0.0309 (2)	0.39138 (19)	0.0423 (5)
C13	1.0085 (2)	0.1803 (2)	0.12403 (19)	0.0406 (4)
C14	1.0695 (3)	0.1102 (3)	0.1871 (2)	0.0514 (5)
H14	1.0128	0.0581	0.2302	0.062*
C15	1.2188 (3)	0.1174 (3)	0.1866 (2)	0.0616 (6)
H15	1.2622	0.0718	0.2315	0.074*
C16	1.3009 (3)	0.1902 (3)	0.1213 (2)	0.0599 (6)
H16	1.3999	0.1942	0.1221	0.072*
C17	1.2370 (3)	0.2596 (3)	0.0523 (2)	0.0487 (5)
C18	1.3112 (3)	0.3301 (3)	−0.0238 (2)	0.0623 (7)
H18	1.4073	0.3321	−0.0306	0.075*
C19	1.2415 (3)	0.3946 (3)	−0.0863 (3)	0.0643 (7)
H19	1.2891	0.4411	−0.1366	0.077*
C20	1.0978 (3)	0.3904 (3)	−0.0744 (2)	0.0584 (6)
H20	1.0533	0.4377	−0.1164	0.070*
C21	1.0888 (2)	0.2580 (2)	0.05481 (18)	0.0399 (4)
N1	0.5359 (2)	−0.2493 (2)	0.4443 (2)	0.0572 (5)
N2	1.0200 (2)	0.3242 (2)	−0.00774 (17)	0.0479 (4)
O1	0.6994 (2)	0.2943 (2)	0.18886 (19)	0.0656 (5)
O2	0.9897 (2)	0.42788 (18)	0.30555 (16)	0.0607 (4)
O3	0.85533 (16)	0.16883 (17)	0.11789 (13)	0.0442 (4)
S1	0.84187 (7)	0.28769 (6)	0.24117 (5)	0.04560 (19)

	U11	U22	U33	U12	U13	U23
C1	0.084 (2)	0.085 (2)	0.118 (2)	0.0459 (17)	0.0604 (19)	0.073 (2)
C2	0.081 (2)	0.089 (2)	0.100 (2)	0.0529 (17)	0.0357 (17)	0.0648 (19)
C3	0.0476 (12)	0.0491 (12)	0.0530 (12)	0.0252 (10)	0.0223 (10)	0.0291 (10)
C4	0.0446 (13)	0.0498 (13)	0.0624 (14)	0.0144 (10)	0.0138 (11)	0.0260 (11)
C5	0.0417 (12)	0.0600 (14)	0.0521 (13)	0.0197 (11)	0.0044 (10)	0.0239 (11)
C6	0.0462 (12)	0.0550 (13)	0.0448 (11)	0.0258 (10)	0.0115 (10)	0.0268 (10)
C7	0.0400 (11)	0.0433 (11)	0.0403 (10)	0.0227 (9)	0.0167 (9)	0.0212 (9)
C8	0.0438 (11)	0.0435 (11)	0.0417 (11)	0.0228 (9)	0.0208 (9)	0.0198 (9)
C9	0.0454 (12)	0.0483 (12)	0.0469 (12)	0.0162 (10)	0.0157 (10)	0.0165 (10)
C10	0.0515 (14)	0.0681 (15)	0.0400 (12)	0.0201 (12)	0.0035 (10)	0.0171 (11)
C11	0.0587 (14)	0.0654 (15)	0.0412 (12)	0.0257 (12)	0.0126 (10)	0.0289 (11)
C12	0.0443 (12)	0.0480 (11)	0.0427 (11)	0.0245 (10)	0.0167 (9)	0.0240 (9)
C13	0.0396 (11)	0.0424 (11)	0.0377 (10)	0.0196 (9)	0.0132 (9)	0.0138 (9)
C14	0.0632 (15)	0.0557 (13)	0.0456 (12)	0.0330 (12)	0.0221 (11)	0.0249 (10)
C15	0.0694 (17)	0.0730 (16)	0.0583 (14)	0.0493 (14)	0.0174 (13)	0.0295 (13)
C16	0.0451 (13)	0.0693 (15)	0.0659 (15)	0.0349 (12)	0.0163 (12)	0.0208 (13)
C17	0.0404 (11)	0.0451 (11)	0.0524 (12)	0.0182 (9)	0.0171 (10)	0.0124 (10)
C18	0.0472 (14)	0.0584 (14)	0.0719 (16)	0.0169 (11)	0.0325 (12)	0.0189 (13)
C19	0.0682 (17)	0.0630 (15)	0.0685 (16)	0.0237 (13)	0.0401 (14)	0.0347 (13)
C20	0.0682 (16)	0.0602 (14)	0.0589 (14)	0.0313 (13)	0.0294 (12)	0.0334 (12)
C21	0.0376 (11)	0.0390 (10)	0.0380 (10)	0.0170 (9)	0.0127 (8)	0.0114 (8)
N1	0.0615 (13)	0.0614 (12)	0.0719 (13)	0.0315 (10)	0.0320 (10)	0.0466 (11)
N2	0.0497 (11)	0.0542 (11)	0.0505 (10)	0.0262 (9)	0.0226 (9)	0.0291 (9)
O1	0.0683 (11)	0.0834 (12)	0.0966 (13)	0.0545 (10)	0.0485 (10)	0.0642 (11)
O2	0.0660 (11)	0.0423 (8)	0.0713 (10)	0.0186 (8)	0.0341 (9)	0.0231 (8)
O3	0.0389 (8)	0.0519 (8)	0.0446 (8)	0.0201 (7)	0.0182 (6)	0.0227 (7)
S1	0.0499 (3)	0.0456 (3)	0.0582 (3)	0.0270 (3)	0.0298 (3)	0.0300 (3)

C1—N1	1.454 (3)	C10—H10	0.9300
C1—H1A	0.9600	C11—C12	1.412 (3)
C1—H1B	0.9600	C11—H11	0.9300
C1—H1C	0.9600	C13—C14	1.358 (3)
C2—N1	1.448 (3)	C13—O3	1.411 (2)
C2—H2A	0.9600	C13—C21	1.415 (3)
C2—H2B	0.9600	C14—C15	1.403 (3)
C2—H2C	0.9600	C14—H14	0.9300
C3—C4	1.364 (3)	C15—C16	1.360 (4)
C3—N1	1.417 (3)	C15—H15	0.9300
C3—C12	1.433 (3)	C16—C17	1.410 (3)
C4—C5	1.396 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—C21	1.416 (3)
C5—C6	1.356 (3)	C17—C18	1.418 (3)
C5—H5	0.9300	C18—C19	1.353 (4)
C6—C7	1.413 (3)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.391 (4)
C7—C12	1.430 (3)	C19—H19	0.9300
C7—C8	1.434 (3)	C20—N2	1.320 (3)
C8—C9	1.362 (3)	C20—H20	0.9300
C8—S1	1.766 (2)	C21—N2	1.363 (3)
C9—C10	1.396 (3)	O1—S1	1.4188 (17)
C9—H9	0.9300	O2—S1	1.4183 (17)
C10—C11	1.356 (3)	O3—S1	1.5933 (15)
N1—C1—H1A	109.5	C11—C12—C3	121.60 (18)
N1—C1—H1B	109.5	C7—C12—C3	119.32 (18)
H1A—C1—H1B	109.5	C14—C13—O3	120.52 (19)
N1—C1—H1C	109.5	C14—C13—C21	122.3 (2)
H1A—C1—H1C	109.5	O3—C13—C21	117.06 (17)
H1B—C1—H1C	109.5	C13—C14—C15	119.3 (2)
N1—C2—H2A	109.5	C13—C14—H14	120.3
N1—C2—H2B	109.5	C15—C14—H14	120.3
H2A—C2—H2B	109.5	C16—C15—C14	120.8 (2)
N1—C2—H2C	109.5	C16—C15—H15	119.6
H2A—C2—H2C	109.5	C14—C15—H15	119.6
H2B—C2—H2C	109.5	C15—C16—C17	120.5 (2)
C4—C3—N1	123.8 (2)	C15—C16—H16	119.7
C4—C3—C12	119.17 (18)	C17—C16—H16	119.7
N1—C3—C12	117.06 (19)	C16—C17—C21	119.7 (2)
C3—C4—C5	120.9 (2)	C16—C17—C18	123.8 (2)
C3—C4—H4	119.5	C21—C17—C18	116.5 (2)
C5—C4—H4	119.5	C19—C18—C17	119.8 (2)
C6—C5—C4	121.6 (2)	C19—C18—H18	120.1
C6—C5—H5	119.2	C17—C18—H18	120.1
C4—C5—H5	119.2	C18—C19—C20	119.0 (2)
C5—C6—C7	120.30 (19)	C18—C19—H19	120.5
C5—C6—H6	119.8	C20—C19—H19	120.5
C7—C6—H6	119.8	N2—C20—C19	124.7 (2)
C6—C7—C12	118.50 (18)	N2—C20—H20	117.6
C6—C7—C8	125.16 (18)	C19—C20—H20	117.6
C12—C7—C8	116.32 (18)	N2—C21—C13	119.30 (18)
C9—C8—C7	122.78 (18)	N2—C21—C17	123.32 (19)
C9—C8—S1	116.00 (16)	C13—C21—C17	117.37 (19)
C7—C8—S1	121.22 (15)	C3—N1—C2	113.78 (19)
C8—C9—C10	119.4 (2)	C3—N1—C1	116.1 (2)
C8—C9—H9	120.3	C2—N1—C1	110.5 (2)
C10—C9—H9	120.3	C20—N2—C21	116.59 (19)
C11—C10—C9	120.4 (2)	C13—O3—S1	117.87 (12)
C11—C10—H10	119.8	O2—S1—O1	119.57 (11)
C9—C10—H10	119.8	O2—S1—O3	108.77 (8)
C10—C11—C12	121.9 (2)	O1—S1—O3	104.37 (10)
C10—C11—H11	119.0	O2—S1—C8	109.32 (10)
C12—C11—H11	119.0	O1—S1—C8	110.89 (10)
C11—C12—C7	119.01 (19)	O3—S1—C8	102.41 (8)
N1—C3—C4—C5	−177.7 (2)	C16—C17—C18—C19	−179.7 (2)
C12—C3—C4—C5	3.9 (3)	C21—C17—C18—C19	1.6 (3)
C3—C4—C5—C6	0.6 (4)	C17—C18—C19—C20	0.1 (4)
C4—C5—C6—C7	−3.7 (4)	C18—C19—C20—N2	−1.5 (4)
C5—C6—C7—C12	2.2 (3)	C14—C13—C21—N2	179.21 (19)
C5—C6—C7—C8	−176.3 (2)	O3—C13—C21—N2	3.3 (3)
C6—C7—C8—C9	176.8 (2)	C14—C13—C21—C17	0.5 (3)
C12—C7—C8—C9	−1.7 (3)	O3—C13—C21—C17	−175.38 (17)
C6—C7—C8—S1	−3.1 (3)	C16—C17—C21—N2	179.12 (19)
C12—C7—C8—S1	178.40 (14)	C18—C17—C21—N2	−2.1 (3)
C7—C8—C9—C10	−1.0 (3)	C16—C17—C21—C13	−2.2 (3)
S1—C8—C9—C10	178.88 (17)	C18—C17—C21—C13	176.51 (18)
C8—C9—C10—C11	1.8 (4)	C4—C3—N1—C2	107.4 (3)
C9—C10—C11—C12	0.2 (4)	C12—C3—N1—C2	−74.3 (3)
C10—C11—C12—C7	−3.0 (3)	C4—C3—N1—C1	−22.5 (3)
C10—C11—C12—C3	179.9 (2)	C12—C3—N1—C1	155.8 (2)
C6—C7—C12—C11	−175.00 (19)	C19—C20—N2—C21	1.0 (4)
C8—C7—C12—C11	3.6 (3)	C13—C21—N2—C20	−177.77 (19)
C6—C7—C12—C3	2.2 (3)	C17—C21—N2—C20	0.9 (3)
C8—C7—C12—C3	−179.18 (17)	C14—C13—O3—S1	82.5 (2)
C4—C3—C12—C11	171.9 (2)	C21—C13—O3—S1	−101.55 (17)
N1—C3—C12—C11	−6.6 (3)	C13—O3—S1—O2	28.05 (16)
C4—C3—C12—C7	−5.2 (3)	C13—O3—S1—O1	156.75 (14)
N1—C3—C12—C7	176.32 (17)	C13—O3—S1—C8	−87.57 (15)
O3—C13—C14—C15	177.12 (19)	C9—C8—S1—O2	−0.92 (19)
C21—C13—C14—C15	1.4 (3)	C7—C8—S1—O2	178.98 (15)
C13—C14—C15—C16	−1.6 (4)	C9—C8—S1—O1	−134.83 (17)
C14—C15—C16—C17	−0.2 (4)	C7—C8—S1—O1	45.06 (19)
C15—C16—C17—C21	2.1 (3)	C9—C8—S1—O3	114.31 (17)
C15—C16—C17—C18	−176.5 (2)	C7—C8—S1—O3	−65.80 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1i	0.93	2.52	3.411 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1i	0.93	2.52	3.411 (3)	160

Symmetry code: (i) .