The crystal structure of 2-[5-(di­methyl­amino)­naphthalene-1-sulfonamido]­phenyl 5-(di­methyl­amino)­naphthalene-1-sulfonate

Chainok, K.; Duangthongyou, T.; Tuntulani, T.; Chuenka, A.; Wannalerse, B.

doi:10.1107/S2056989015016199

organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o721-o722

doi:10.1107/S2056989015016199

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The crystal structure of 2-[5-(dimethylamino)naphthalene-1-sulfonamido]phenyl 5-(dimethylamino)naphthalene-1-sulfonate

Kittipong Chainok,^a Tanwawan Duangthongyou,^b Thawatchai Tuntulani,^c Apinya Chuenka ^d and Boontana Wannalerse ^d ^*

^aDepartment of Physics, Faculty of Science and Technology, Thammasat University, Khlong Luang, Pathum Thani, 12120, Thailand, ^bDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand, ^cSupramolecular Chemistry Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand, and ^dDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok 10903, Thailand
^*Correspondence e-mail: fscibnw@ku.ac.th

Edited by T. N. Guru Row, Indian Institute of Science, India (Received 16 July 2015; accepted 31 August 2015; online 12 September 2015)

The complete molecule 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 intramolecular C—H⋯O hydrogen bond closes an S(6) ring. In the crystal, the molecules are linked by weak C—H⋯O hydrogen bonds.

Keywords: crystal structure; dansyl derivatives; disorder; hydrogen bonding; π-stacking.

CCDC reference: 1421273

1. 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 ).

2. Experimental

2.1. Crystal data

C₃₀H₂₉N₃O₅S₂
M_r = 575.68
Monoclinic, C 2/c
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.113
S = 1.03
3444 reflections
186 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O3ⁱ	0.93	2.73	3.386 (2)	129
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

CCDC reference: 1421273

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

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

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

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

checkCIF report

Introduction top

Dansyl derivatives can be widely used as fluorescence probes in biological and environmental systems. Dansyl tags have been increasingly used to monitor biological activities in the enzyme system for providing the accurate information (Brown et al., 1970; Liu et al., 2010). An example is dansyl-conjugated liposome for modulating fluorescence resonance energy transfer (FRET) mechanism (Li et al. 2006). Furthermore, dansyl fluorogenic sensors were prepared for recognition and detection of many targets such as cationic and anionic species (Cao et al., 2014; Jisha et al., 2009; Bhalla et al., 2007). Crystal structures of dansyl derivatives (Bhatt et al., 2011; Zhang et al., 2009) and metal complexes of calix[4]arene bearing two dansyl carboxamide units have been reported (Buie et al., 2008).

Synthesis and crystallization top

The title compound was synthesized by condensation of 2-aminophenol (0.55 g, 5.04 mmol) and dansyl chloride (2.72 g, 10.08 mmol) using potassium carbonate (17.27 g, 12.50 mmol) as a base in acetonitrile (30 ml). The solution was heated and stirred under N₂ atmosphere for 24 h. The solvent was then removed by a rotary evaporator. Water (10 ml) was added to the residue and the organic phase was extracted with dichloromethane (3 x 20 ml). The organic layer was dried with Na₂SO₄. The product was purified by column chromatography using dichloromethane as an eluent. The solvent was evaporated to afford a yellow crystalline solid in 55% yield. Single crystals suitable for X-ray measurements were obtained by recrystallization using the mixture solution of dichloromethane and hexane (1:1, v/v) at room temperature.

Refinement top

Atom O1 and the N1H1 group attached to the central benzene ring are statistically disordered and were refined with the occupancies of the N, H and O atoms fixed at 0.5. All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å for aryl and 0.96 Å for methyl H atoms, U_iso (H) = 1.2U_eq (C) for aryl and 1.5U_eq (C) for methyl H atoms. The N-bound H-atom was refined with N—H = 0.86 Å, and with U_iso(H) = 1.2U_eq(N).

Related literature top

For the use of dansyl tags to monitor biological activity in enzyme systems, see: Brown et al. (1970); Liu et al. (2010). For the use of dansyl-conjugated liposome to modulate the fluorescence resonance energy transfer (FRET) mechanism, see: Li et al. (2006). Dansyl fluorogenic sensors have been prepared 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 complexes of calix[4]arene bearing two dansyl carboxamide units, see: Buie et al. (2008)

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); 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 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability ellipsoids and atom numbering. Hydrogen atoms are omitted for clarity.
	Fig. 2. The crystal packing of the title compound, viewed along the [110] direction.

2-[5-(Dimethylamino)naphthalene-1-sulfonamido]phenyl 5-(dimethylamino)naphthalene-1-sulfonate top

Crystal data top

C₃₀H₂₉N₃O₅S₂	F(000) = 1208
M_r = 575.68	D_x = 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

Data collection top

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	R_int = 0.041
Detector resolution: 10.5 pixels mm^-1	θ_max = 28.3°, θ_min = 3.1°
ω and φ scans	h = −15→16
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −17→17
T_min = 0.698, T_max = 0.746	l = −21→21
17644 measured reflections

Refinement top

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(F_o²) + (0.0488P)² + 1.1669P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3444 reflections	Δρ_max = 0.26 e Å⁻³
186 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints

Crystal data top

C₃₀H₂₉N₃O₅S₂	V = 2769.1 (5) Å³
M_r = 575.68	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 12.7594 (13) Å	µ = 0.24 mm⁻¹
b = 13.3481 (14) Å	T = 296 K
c = 16.4331 (17) Å	0.26 × 0.22 × 0.22 mm
β = 98.349 (4)°

Data collection top

Bruker D8 QUEST CMOS diffractometer	3444 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	2246 reflections with I > 2σ(I)
T_min = 0.698, T_max = 0.746	R_int = 0.041
17644 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
3444 reflections	Δρ_min = −0.23 e Å⁻³
186 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) −x+3/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3	0.93	2.37	3.030 (2)	127.7
C13—H13···O3ⁱ	0.93	2.73	3.386 (2)	128.6

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

The authors thank the Thailand Research Fund (MRG 5580182), the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Education, Ministry of Education, Kasetsart University Research and Development Institute and the Department of Chemistry, Faculty of Science, Kasetsart University for financial support.

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Volume 71| Part 10| October 2015| Pages o721-o722

doi:10.1107/S2056989015016199

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

The crystal structure of 2-[5-(di­methyl­amino)­naphthalene-1-sulfonamido]­phenyl 5-(di­methyl­amino)­naphthalene-1-sulfonate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

The crystal structure of 2-[5-(dimethylamino)naphthalene-1-sulfonamido]phenyl 5-(dimethylamino)naphthalene-1-sulfonate