The crystal structure of 2-[5-(di-methyl-amino)-naphthalene-1-sulfonamido]-phenyl 5-(di-methyl-amino)-naphthalene-1-sulfonate.

The complete mol-ecule of the title compound, C30H29N3O5S2, is generated by a crystallographic twofold axis: the O atom and NH group attached to the central benzene ring are statistically disordered. The dihedral angle between the naphthalene ring system and the central benzene ring is 52.99 (6)°, while the pendant naphthalene ring systems subtend a dihedral angle of 68.17 (4)°. An intra-molecular C-H⋯O hydrogen bond closes an S(6) ring. In the crystal, the mol-ecules are linked by weak C-H⋯O hydrogen bonds.

Related literature

For the use of dansyl tags to monitor biological activity in enzyme systems, see: Brown et al. (1970 ▸); Liu et al. (2010 ▸). Dansyl-conjugated liposome has been used to modulate the fluorescence resonance energy transfer (FRET) mechanism, see: Li et al. (2006 ▸). Dansyl fluoro­genic sensors have been used for the recognition and detection of targets such as cationic and anionic species, see: Cao et al. (2014 ▸); Jisha et al. (2009 ▸); Bhalla et al. (2007 ▸). For crystal structures of dansyl derivatives, see: Bhatt et al. (2011 ▸); Zhang et al. (2009 ▸) and of metal–calix[4]arene complexes bearing two dansyl carboxamide units, see: Buie et al. (2008 ▸).

Experimental

Crystal data

C30H29N3O5S2

M = 575.68

Monoclinic,

a = 12.7594 (13) Å

b = 13.3481 (14) Å

c = 16.4331 (17) Å

β = 98.349 (4)°

V = 2769.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.26 × 0.22 × 0.22 mm

Data collection

Bruker D8 QUEST CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.698, T max = 0.746

17644 measured reflections

3444 independent reflections

2246 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.113

S = 1.03

3444 reflections

186 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015016199/gw2153sup1.cif

Structure factors: contains datablock(s) bw6. DOI: 10.1107/S2056989015016199/gw2153Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016199/gw2153Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015016199/gw2153Isup4.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015016199/gw2153fig1.tif

The mol­ecular structure of the title compound with 30% probability ellipsoids and atom numbering. Hydrogen atoms are omitted for clarity.

Click here for additional data file.

. DOI: 10.1107/S2056989015016199/gw2153fig2.tif

The crystal packing of the title compound, viewed along the [110] direction.

CCDC reference: 1421273

Additional supporting information: crystallographic information; 3D view; checkCIF report

C30H29N3O5S2	F(000) = 1208
Mr = 575.68	Dx = 1.381 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7594 (13) Å	Cell parameters from 4957 reflections
b = 13.3481 (14) Å	θ = 3.1–25.7°
c = 16.4331 (17) Å	µ = 0.24 mm−1
β = 98.349 (4)°	T = 296 K
V = 2769.1 (5) Å3	Block, light green
Z = 4	0.26 × 0.22 × 0.22 mm

Bruker D8 QUEST CMOS diffractometer	3444 independent reflections
Radiation source: microfocus sealed x-ray tube, Incoatec Iµus	2246 reflections with I > 2σ(I)
GraphiteDouble Bounce Multilayer Mirror monochromator	Rint = 0.041
Detector resolution: 10.5 pixels mm-1	θmax = 28.3°, θmin = 3.1°
ω and φ scans	h = −15→16
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −17→17
Tmin = 0.698, Tmax = 0.746	l = −21→21
17644 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0488P)2 + 1.1669P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3444 reflections	Δρmax = 0.26 e Å−3
186 parameters	Δρmin = −0.23 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.69732 (3)	0.73580 (4)	0.32645 (3)	0.05431 (17)
N1	0.603 (2)	0.709 (2)	0.2569 (14)	0.0418 (18)	0.5
H1	0.5801	0.7537	0.2215	0.050*	0.5
O2	0.77825 (10)	0.66139 (12)	0.33521 (10)	0.0736 (5)
O3	0.72349 (11)	0.83601 (11)	0.30878 (10)	0.0711 (4)
N2	0.35617 (13)	0.82675 (13)	0.57539 (10)	0.0609 (5)
C11	0.55450 (13)	0.61136 (13)	0.25005 (10)	0.0433 (4)
C5	0.49120 (13)	0.77874 (12)	0.49182 (10)	0.0427 (4)
C6	0.54736 (13)	0.79731 (12)	0.42414 (10)	0.0413 (4)
C1	0.62854 (13)	0.72779 (13)	0.41220 (11)	0.0450 (4)
C10	0.40779 (14)	0.84536 (14)	0.50673 (12)	0.0495 (4)
C12	0.60785 (15)	0.52183 (15)	0.24889 (12)	0.0543 (5)
H12	0.6806	0.5215	0.2481	0.065*
C7	0.51636 (15)	0.87928 (13)	0.37174 (11)	0.0500 (4)
H7	0.5533	0.8940	0.3285	0.060*
C4	0.51413 (16)	0.69084 (14)	0.53896 (12)	0.0531 (5)
H4	0.4748	0.6766	0.5810	0.064*
C2	0.65034 (16)	0.64565 (15)	0.46148 (12)	0.0582 (5)
H2	0.7046	0.6022	0.4527	0.070*
C9	0.37880 (17)	0.92039 (15)	0.45129 (13)	0.0612 (5)
H9	0.3220	0.9615	0.4583	0.073*
C8	0.43259 (17)	0.93625 (15)	0.38477 (13)	0.0611 (5)
H8	0.4104	0.9876	0.3480	0.073*
C13	0.55357 (17)	0.43329 (16)	0.24897 (14)	0.0665 (6)
H13	0.5895	0.3728	0.2476	0.080*
C3	0.59130 (17)	0.62698 (15)	0.52481 (13)	0.0635 (6)
H3	0.6052	0.5702	0.5574	0.076*
C14	0.41854 (19)	0.83896 (17)	0.65611 (13)	0.0707 (6)
H14A	0.4905	0.8197	0.6537	0.106*
H14B	0.3898	0.7975	0.6951	0.106*
H14C	0.4165	0.9078	0.6727	0.106*
C15	0.25143 (19)	0.8715 (2)	0.57308 (17)	0.0878 (8)
H15A	0.2587	0.9419	0.5846	0.132*
H15B	0.2153	0.8401	0.6136	0.132*
H15C	0.2114	0.8620	0.5195	0.132*
O1	0.6121 (16)	0.7010 (16)	0.2444 (11)	0.0418 (18)	0.5

	U11	U22	U33	U12	U13	U23
S1	0.0322 (2)	0.0701 (4)	0.0622 (3)	−0.0032 (2)	0.0121 (2)	−0.0040 (3)
N1	0.035 (3)	0.051 (3)	0.043 (5)	0.0008 (19)	0.017 (2)	−0.002 (3)
O2	0.0366 (7)	0.1019 (12)	0.0833 (10)	0.0177 (7)	0.0120 (7)	−0.0060 (9)
O3	0.0528 (8)	0.0783 (10)	0.0848 (10)	−0.0260 (7)	0.0188 (7)	−0.0017 (8)
N2	0.0564 (10)	0.0708 (12)	0.0595 (10)	0.0057 (8)	0.0213 (8)	−0.0053 (8)
C11	0.0430 (9)	0.0499 (10)	0.0401 (9)	−0.0004 (8)	0.0161 (8)	0.0007 (8)
C5	0.0422 (9)	0.0435 (10)	0.0411 (9)	0.0018 (7)	0.0023 (7)	−0.0002 (7)
C6	0.0387 (9)	0.0416 (9)	0.0426 (9)	−0.0021 (7)	0.0023 (7)	−0.0026 (7)
C1	0.0367 (9)	0.0517 (10)	0.0454 (10)	0.0024 (8)	0.0017 (7)	−0.0020 (8)
C10	0.0474 (10)	0.0508 (11)	0.0509 (11)	0.0029 (8)	0.0088 (8)	−0.0037 (8)
C12	0.0515 (11)	0.0591 (13)	0.0566 (11)	0.0084 (9)	0.0225 (9)	0.0023 (9)
C7	0.0572 (11)	0.0458 (10)	0.0478 (10)	0.0015 (9)	0.0101 (9)	0.0054 (8)
C4	0.0616 (12)	0.0523 (11)	0.0459 (10)	0.0048 (9)	0.0098 (9)	0.0076 (9)
C2	0.0543 (11)	0.0605 (12)	0.0585 (12)	0.0223 (9)	0.0033 (9)	0.0026 (10)
C9	0.0606 (12)	0.0543 (12)	0.0702 (13)	0.0212 (10)	0.0144 (10)	0.0039 (10)
C8	0.0715 (14)	0.0484 (11)	0.0626 (12)	0.0162 (10)	0.0074 (10)	0.0128 (9)
C13	0.0791 (14)	0.0509 (12)	0.0752 (14)	0.0108 (10)	0.0306 (13)	0.0021 (11)
C3	0.0775 (14)	0.0554 (12)	0.0570 (12)	0.0212 (11)	0.0078 (11)	0.0144 (10)
C14	0.0904 (17)	0.0706 (15)	0.0549 (13)	0.0006 (12)	0.0233 (12)	−0.0004 (11)
C15	0.0640 (14)	0.111 (2)	0.0949 (19)	0.0165 (14)	0.0343 (14)	−0.0055 (15)
O1	0.035 (3)	0.051 (3)	0.043 (5)	0.0008 (19)	0.017 (2)	−0.002 (3)

S1—N1	1.58 (3)	C12—H12	0.9300
S1—O2	1.4248 (14)	C12—C13	1.370 (3)
S1—O3	1.4189 (15)	C7—H7	0.9300
S1—C1	1.7681 (18)	C7—C8	1.354 (3)
S1—O1	1.67 (2)	C4—H4	0.9300
N1—H1	0.8600	C4—C3	1.348 (3)
N1—C11	1.44 (3)	C2—H2	0.9300
N2—C10	1.409 (2)	C2—C3	1.393 (3)
N2—C14	1.454 (3)	C9—H9	0.9300
N2—C15	1.459 (3)	C9—C8	1.389 (3)
C11—C11i	1.391 (3)	C8—H8	0.9300
C11—C12	1.377 (2)	C13—C13i	1.372 (4)
C11—O1	1.41 (2)	C13—H13	0.9300
C5—C6	1.429 (2)	C3—H3	0.9300
C5—C10	1.435 (2)	C14—H14A	0.9600
C5—C4	1.413 (2)	C14—H14B	0.9600
C6—C1	1.425 (2)	C14—H14C	0.9600
C6—C7	1.413 (2)	C15—H15A	0.9600
C1—C2	1.367 (3)	C15—H15B	0.9600
C10—C9	1.368 (3)	C15—H15C	0.9600
N1—S1—C1	98.6 (8)	C6—C7—H7	120.1
O2—S1—N1	112.1 (9)	C8—C7—C6	119.74 (17)
O2—S1—C1	108.28 (9)	C8—C7—H7	120.1
O2—S1—O1	105.4 (6)	C5—C4—H4	119.0
O3—S1—N1	104.3 (10)	C3—C4—C5	121.93 (18)
O3—S1—O2	119.29 (9)	C3—C4—H4	119.0
O3—S1—C1	112.27 (9)	C1—C2—H2	120.0
O3—S1—O1	104.0 (7)	C1—C2—C3	120.02 (18)
O1—S1—C1	106.6 (6)	C3—C2—H2	120.0
S1—N1—H1	118.6	C10—C9—H9	119.4
C11—N1—S1	122.8 (18)	C10—C9—C8	121.27 (18)
C11—N1—H1	118.6	C8—C9—H9	119.4
C10—N2—C14	116.97 (16)	C7—C8—C9	122.05 (18)
C10—N2—C15	116.09 (18)	C7—C8—H8	119.0
C14—N2—C15	110.84 (18)	C9—C8—H8	119.0
C11i—C11—N1	115.0 (10)	C12—C13—C13i	120.37 (12)
C11i—C11—O1	121.9 (8)	C12—C13—H13	119.8
C12—C11—N1	125.1 (10)	C13i—C13—H13	119.8
C12—C11—C11i	119.76 (11)	C4—C3—C2	120.24 (18)
C12—C11—O1	118.1 (8)	C4—C3—H3	119.9
C6—C5—C10	119.56 (15)	C2—C3—H3	119.9
C4—C5—C6	118.90 (16)	N2—C14—H14A	109.5
C4—C5—C10	121.37 (17)	N2—C14—H14B	109.5
C1—C6—C5	116.78 (15)	N2—C14—H14C	109.5
C7—C6—C5	118.75 (16)	H14A—C14—H14B	109.5
C7—C6—C1	124.40 (16)	H14A—C14—H14C	109.5
C6—C1—S1	121.67 (13)	H14B—C14—H14C	109.5
C2—C1—S1	116.02 (14)	N2—C15—H15A	109.5
C2—C1—C6	122.00 (17)	N2—C15—H15B	109.5
N2—C10—C5	118.17 (16)	N2—C15—H15C	109.5
C9—C10—N2	123.36 (17)	H15A—C15—H15B	109.5
C9—C10—C5	118.38 (17)	H15A—C15—H15C	109.5
C11—C12—H12	120.1	H15B—C15—H15C	109.5
C13—C12—C11	119.85 (18)	C11—O1—S1	117.7 (13)
C13—C12—H12	120.1
S1—N1—C11—C11i	124.2 (13)	C6—C5—C4—C3	3.7 (3)
S1—N1—C11—C12	−51.6 (18)	C6—C1—C2—C3	1.1 (3)
S1—C1—C2—C3	−172.60 (16)	C6—C7—C8—C9	3.7 (3)
N1—S1—C1—C6	−67.6 (10)	C1—S1—N1—C11	−66.4 (15)
N1—S1—C1—C2	106.1 (10)	C1—S1—O1—C11	−48.7 (12)
N1—C11—C12—C13	174.6 (11)	C1—C6—C7—C8	174.71 (18)
O2—S1—N1—C11	47.5 (16)	C1—C2—C3—C4	−1.5 (3)
O2—S1—C1—C6	175.57 (14)	C10—C5—C6—C1	−179.37 (15)
O2—S1—C1—C2	−10.74 (18)	C10—C5—C6—C7	−2.3 (3)
O2—S1—O1—C11	66.2 (11)	C10—C5—C4—C3	179.07 (19)
O3—S1—N1—C11	177.9 (12)	C10—C9—C8—C7	−0.5 (3)
O3—S1—C1—C6	41.79 (17)	C12—C11—O1—S1	−72.7 (11)
O3—S1—C1—C2	−144.52 (15)	C7—C6—C1—S1	−2.0 (2)
O3—S1—O1—C11	−167.5 (9)	C7—C6—C1—C2	−175.27 (19)
N2—C10—C9—C8	179.6 (2)	C4—C5—C6—C1	−4.0 (2)
C11i—C11—C12—C13	−1.0 (3)	C4—C5—C6—C7	173.16 (17)
C11i—C11—O1—S1	112.6 (11)	C4—C5—C10—N2	6.6 (3)
C11—C12—C13—C13i	−0.6 (4)	C4—C5—C10—C9	−170.03 (19)
C5—C6—C1—S1	174.98 (12)	C14—N2—C10—C5	66.8 (2)
C5—C6—C1—C2	1.7 (3)	C14—N2—C10—C9	−116.8 (2)
C5—C6—C7—C8	−2.2 (3)	C15—N2—C10—C5	−159.33 (19)
C5—C10—C9—C8	−4.0 (3)	C15—N2—C10—C9	17.1 (3)
C5—C4—C3—C2	−1.0 (3)	O1—S1—C1—C6	−71.5 (8)
C6—C5—C10—N2	−178.08 (16)	O1—S1—C1—C2	102.2 (8)
C6—C5—C10—C9	5.3 (3)	O1—C11—C12—C13	−175.8 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3	0.93	2.37	3.030 (2)	128
C13—H13···O3ii	0.93	2.73	3.386 (2)	129

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C7H7O3	0.93	2.37	3.030(2)	128
C13H13O3i	0.93	2.73	3.386(2)	129

Symmetry code: (i) .