1-{[(E)-(4-{[(2Z)-2,3-Di-hydro-1,3-thia-zol-2-yl-idene]sulfamo-yl}phen-yl)iminium-yl]meth-yl}naphthalen-2-olate.

In the title zwitterionic compound, C20H15N3O3S2, the 2-hy-droxy-naphthalene-1-carbaldehyde group A, the anilinic unit B and the 1,3-thia-zol-2(3H)-imine group C are each approximately planar with r.m.s. deviation of 0.0721, 0.0412 and 0.0125 Å, respectively. The dihedral angles between A/B, A/C and B/C are 24.70 (10), 79.97 (7) and 83.14 (6)°, respectively. There is an intra-molecular S(6) motif involving the imine N-H and the naphtho-late O atom. In the crystal, inversion-related mol-ecules form dimers as a result of N-H⋯N and N-H⋯O hydrogen bonds with R 2 (2)(8) and R 1 (2)(4) motifs, respectively. Weak π-π inter-actions between the benzene and naphthyl rings of inversion-related mol-ecules have ring centroid-centroid distances of 3.638 (2) and 4.041 (2) Å. A C-H⋯π inter-action occurs between the thia-zol ring and the benzene ring of an adjacent mol-ecule.

Related literature

For related structures, see: El-Ghamry et al. (2008 ▸); Hebbachi et al. (2013 ▸); Zhang (2009 ▸).

Experimental

Crystal data

C20H15N3O3S2

M = 409.47

Triclinic,

a = 9.127 (2) Å

b = 10.1417 (12) Å

c = 11.355 (3) Å

α = 114.526 (6)°

β = 91.556 (5)°

γ = 102.044 (5)°

V = 927.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.32 × 0.26 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T min = 0.910, T max = 0.948

13121 measured reflections

3554 independent reflections

2086 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.127

S = 1.01

3554 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (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: SHELXL2014/7 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015009640/pk2552sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009640/pk2552Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015009640/pk2552Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015009640/pk2552fig1.tif

View of the title compound with the atom numbering scheme. Thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown as small circles of arbitrary radius. The dotted lines show intra­molecular H-bonding.

Click here for additional data file.

PLATON . DOI: 10.1107/S2056989015009640/pk2552fig2.tif

A partial packing plot (PLATON; Spek, 2009), which shows that mol­ecules form dimers and are inter­linked forming various ring motifs.

CCDC reference: 1401829

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

C20H15N3O3S2	Z = 2
Mr = 409.47	F(000) = 424
Triclinic, P1	Dx = 1.466 Mg m−3
a = 9.127 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1417 (12) Å	Cell parameters from 2086 reflections
c = 11.355 (3) Å	θ = 2.3–26.0°
α = 114.526 (6)°	µ = 0.31 mm−1
β = 91.556 (5)°	T = 296 K
γ = 102.044 (5)°	Plate, light orange
V = 927.5 (3) Å3	0.32 × 0.26 × 0.18 mm

Bruker Kappa APEXII CCD diffractometer	3554 independent reflections
Radiation source: fine-focus sealed tube	2086 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 7.80 pixels mm-1	θmax = 26.0°, θmin = 2.3°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→10
Tmin = 0.910, Tmax = 0.948	l = −13→13
13121 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0596P)2] where P = (Fo2 + 2Fc2)/3
3554 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.24 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
S1	0.26196 (9)	0.20802 (8)	0.46258 (8)	0.0436 (2)
S2	0.57914 (9)	0.19236 (8)	0.58749 (9)	0.0571 (3)
O1	−0.0869 (3)	0.3290 (3)	1.1505 (2)	0.0747 (7)
O2	0.1538 (2)	0.2532 (2)	0.4023 (2)	0.0580 (6)
O3	0.2907 (2)	0.0638 (2)	0.38835 (19)	0.0498 (5)
N1	−0.0117 (3)	0.1888 (3)	0.9256 (2)	0.0512 (7)
H1	0.0035	0.2699	0.9964	0.061*
N2	0.4105 (3)	0.3410 (2)	0.5032 (2)	0.0449 (6)
N3	0.6639 (3)	0.4405 (2)	0.5815 (2)	0.0481 (7)
H3A	0.6652	0.5187	0.5689	0.058*
C1	−0.1806 (4)	0.2077 (4)	1.1338 (3)	0.0561 (9)
C2	−0.2866 (5)	0.2126 (4)	1.2278 (4)	0.0728 (11)
H2	−0.2825	0.3016	1.3007	0.087*
C3	−0.3895 (4)	0.0895 (4)	1.2094 (4)	0.0691 (10)
H3	−0.4586	0.0968	1.2692	0.083*
C4	−0.4008 (4)	−0.0546 (4)	1.1024 (3)	0.0526 (8)
C5	−0.5088 (4)	−0.1806 (4)	1.0914 (4)	0.0661 (10)
H5	−0.5771	−0.1709	1.1520	0.079*
C6	−0.5151 (4)	−0.3180 (5)	0.9924 (4)	0.0789 (11)
H6	−0.5871	−0.4017	0.9852	0.095*
C7	−0.4126 (4)	−0.3300 (4)	0.9034 (4)	0.0730 (11)
H7	−0.4144	−0.4235	0.8372	0.088*
C8	−0.3080 (4)	−0.2069 (4)	0.9106 (3)	0.0586 (9)
H8	−0.2418	−0.2186	0.8482	0.070*
C9	−0.2989 (3)	−0.0644 (3)	1.0099 (3)	0.0471 (8)
C10	−0.1920 (3)	0.0706 (3)	1.0238 (3)	0.0444 (7)
C11	−0.1073 (3)	0.0693 (3)	0.9224 (3)	0.0477 (8)
H11	−0.1189	−0.0206	0.8487	0.057*
C12	0.0678 (3)	0.1932 (3)	0.8206 (3)	0.0432 (7)
C13	0.0942 (3)	0.0669 (3)	0.7250 (3)	0.0480 (8)
H13	0.0687	−0.0233	0.7316	0.058*
C14	0.1589 (3)	0.0737 (3)	0.6188 (3)	0.0456 (8)
H14	0.1759	−0.0126	0.5534	0.055*
C15	0.1990 (3)	0.2078 (3)	0.6081 (3)	0.0402 (7)
C16	0.1789 (3)	0.3370 (3)	0.7084 (3)	0.0541 (8)
H16	0.2080	0.4282	0.7039	0.065*
C17	0.1152 (3)	0.3290 (3)	0.8155 (3)	0.0529 (8)
H17	0.1042	0.4158	0.8843	0.063*
C18	0.5396 (3)	0.3322 (3)	0.5515 (3)	0.0396 (7)
C19	0.7905 (4)	0.4204 (4)	0.6338 (3)	0.0587 (9)
H19	0.8842	0.4882	0.6581	0.070*
C20	0.7636 (4)	0.2935 (4)	0.6456 (3)	0.0630 (9)
H20	0.8354	0.2625	0.6809	0.076*

	U11	U22	U33	U12	U13	U23
S1	0.0429 (5)	0.0418 (4)	0.0496 (5)	0.0035 (3)	0.0057 (4)	0.0262 (4)
S2	0.0582 (6)	0.0460 (5)	0.0718 (6)	0.0055 (4)	−0.0039 (4)	0.0340 (4)
O1	0.0905 (19)	0.0571 (14)	0.0641 (16)	0.0136 (14)	0.0200 (13)	0.0156 (12)
O2	0.0507 (14)	0.0628 (13)	0.0693 (15)	0.0066 (11)	−0.0034 (11)	0.0410 (12)
O3	0.0565 (14)	0.0419 (11)	0.0489 (13)	0.0080 (10)	0.0141 (10)	0.0191 (10)
N1	0.0498 (17)	0.0543 (16)	0.0462 (16)	0.0106 (13)	0.0084 (13)	0.0193 (13)
N2	0.0409 (15)	0.0411 (14)	0.0596 (17)	0.0020 (11)	0.0073 (13)	0.0319 (12)
N3	0.0494 (17)	0.0361 (13)	0.0606 (17)	0.0035 (12)	0.0112 (13)	0.0255 (12)
C1	0.068 (2)	0.052 (2)	0.053 (2)	0.0151 (18)	0.0109 (18)	0.0261 (17)
C2	0.100 (3)	0.067 (2)	0.063 (3)	0.033 (2)	0.037 (2)	0.0310 (19)
C3	0.077 (3)	0.090 (3)	0.062 (2)	0.038 (2)	0.035 (2)	0.044 (2)
C4	0.048 (2)	0.078 (2)	0.048 (2)	0.0256 (18)	0.0149 (16)	0.0382 (18)
C5	0.056 (2)	0.093 (3)	0.069 (3)	0.017 (2)	0.0168 (19)	0.054 (2)
C6	0.066 (3)	0.085 (3)	0.087 (3)	−0.003 (2)	0.005 (2)	0.049 (3)
C7	0.077 (3)	0.068 (2)	0.063 (3)	0.004 (2)	0.015 (2)	0.0234 (19)
C8	0.056 (2)	0.065 (2)	0.051 (2)	0.0091 (18)	0.0108 (17)	0.0242 (18)
C9	0.045 (2)	0.062 (2)	0.0433 (19)	0.0161 (16)	0.0071 (15)	0.0295 (16)
C10	0.0411 (19)	0.0555 (19)	0.0433 (19)	0.0162 (15)	0.0104 (15)	0.0254 (15)
C11	0.043 (2)	0.0460 (18)	0.052 (2)	0.0091 (15)	0.0041 (16)	0.0198 (15)
C12	0.0356 (18)	0.0515 (18)	0.0451 (19)	0.0085 (14)	0.0058 (14)	0.0241 (15)
C13	0.046 (2)	0.0468 (18)	0.060 (2)	0.0105 (15)	0.0152 (16)	0.0312 (16)
C14	0.047 (2)	0.0458 (17)	0.049 (2)	0.0104 (14)	0.0159 (15)	0.0252 (15)
C15	0.0320 (17)	0.0415 (16)	0.0461 (18)	0.0048 (13)	0.0063 (13)	0.0198 (14)
C16	0.052 (2)	0.0432 (18)	0.064 (2)	0.0038 (15)	0.0133 (17)	0.0230 (16)
C17	0.054 (2)	0.0410 (17)	0.054 (2)	0.0090 (15)	0.0138 (17)	0.0120 (15)
C18	0.044 (2)	0.0334 (15)	0.0400 (17)	0.0041 (14)	0.0088 (14)	0.0165 (13)
C19	0.042 (2)	0.055 (2)	0.070 (2)	0.0014 (16)	0.0001 (17)	0.0240 (18)
C20	0.048 (2)	0.061 (2)	0.075 (2)	0.0089 (17)	−0.0123 (17)	0.0276 (18)

S1—O2	1.437 (2)	C5—H5	0.9300
S1—O3	1.4373 (19)	C6—C7	1.382 (5)
S1—N2	1.599 (2)	C6—H6	0.9300
S1—C15	1.765 (3)	C7—C8	1.375 (4)
S2—C20	1.726 (3)	C7—H7	0.9300
S2—C18	1.731 (3)	C8—C9	1.400 (4)
O1—C1	1.280 (4)	C8—H8	0.9300
N1—C11	1.323 (3)	C9—C10	1.451 (4)
N1—C12	1.424 (4)	C10—C11	1.401 (4)
N1—H1	0.8600	C11—H11	0.9300
N2—C18	1.322 (3)	C12—C13	1.366 (4)
N3—C18	1.325 (3)	C12—C17	1.381 (4)
N3—C19	1.375 (4)	C13—C14	1.379 (4)
N3—H3A	0.8600	C13—H13	0.9300
C1—C10	1.412 (4)	C14—C15	1.389 (4)
C1—C2	1.453 (4)	C14—H14	0.9300
C2—C3	1.329 (5)	C15—C16	1.386 (4)
C2—H2	0.9300	C16—C17	1.388 (4)
C3—C4	1.442 (4)	C16—H16	0.9300
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.398 (4)	C19—C20	1.322 (4)
C4—C9	1.408 (4)	C19—H19	0.9300
C5—C6	1.367 (5)	C20—H20	0.9300
O2—S1—O3	117.41 (13)	C9—C8—H8	119.3
O2—S1—N2	103.97 (12)	C8—C9—C4	116.5 (3)
O3—S1—N2	112.68 (13)	C8—C9—C10	124.6 (3)
O2—S1—C15	108.18 (13)	C4—C9—C10	118.9 (3)
O3—S1—C15	106.92 (12)	C11—C10—C1	118.7 (3)
N2—S1—C15	107.23 (13)	C11—C10—C9	120.1 (3)
C20—S2—C18	90.63 (15)	C1—C10—C9	121.0 (3)
C11—N1—C12	125.0 (3)	N1—C11—C10	123.7 (3)
C11—N1—H1	117.5	N1—C11—H11	118.1
C12—N1—H1	117.5	C10—C11—H11	118.1
C18—N2—S1	121.34 (19)	C13—C12—C17	120.2 (3)
C18—N3—C19	116.1 (2)	C13—C12—N1	121.6 (3)
C18—N3—H3A	122.0	C17—C12—N1	118.2 (3)
C19—N3—H3A	122.0	C12—C13—C14	119.7 (3)
O1—C1—C10	123.0 (3)	C12—C13—H13	120.2
O1—C1—C2	118.7 (3)	C14—C13—H13	120.2
C10—C1—C2	118.2 (3)	C13—C14—C15	120.9 (3)
C3—C2—C1	119.8 (3)	C13—C14—H14	119.6
C3—C2—H2	120.1	C15—C14—H14	119.6
C1—C2—H2	120.1	C16—C15—C14	119.2 (3)
C2—C3—C4	124.1 (3)	C16—C15—S1	121.3 (2)
C2—C3—H3	118.0	C14—C15—S1	119.4 (2)
C4—C3—H3	118.0	C15—C16—C17	119.4 (3)
C5—C4—C9	121.1 (3)	C15—C16—H16	120.3
C5—C4—C3	121.0 (3)	C17—C16—H16	120.3
C9—C4—C3	117.8 (3)	C12—C17—C16	120.5 (3)
C6—C5—C4	120.7 (3)	C12—C17—H17	119.8
C6—C5—H5	119.6	C16—C17—H17	119.8
C4—C5—H5	119.6	N2—C18—N3	121.3 (3)
C5—C6—C7	118.7 (3)	N2—C18—S2	129.4 (2)
C5—C6—H6	120.6	N3—C18—S2	109.3 (2)
C7—C6—H6	120.6	C20—C19—N3	112.2 (3)
C8—C7—C6	121.4 (3)	C20—C19—H19	123.9
C8—C7—H7	119.3	N3—C19—H19	123.9
C6—C7—H7	119.3	C19—C20—S2	111.8 (3)
C7—C8—C9	121.4 (3)	C19—C20—H20	124.1
C7—C8—H8	119.3	S2—C20—H20	124.1
O2—S1—N2—C18	−173.8 (2)	C9—C10—C11—N1	177.4 (3)
O3—S1—N2—C18	−45.6 (3)	C11—N1—C12—C13	−23.2 (4)
C15—S1—N2—C18	71.8 (3)	C11—N1—C12—C17	155.2 (3)
O1—C1—C2—C3	177.0 (3)	C17—C12—C13—C14	−4.5 (5)
C10—C1—C2—C3	0.7 (5)	N1—C12—C13—C14	173.9 (3)
C1—C2—C3—C4	2.6 (6)	C12—C13—C14—C15	0.6 (5)
C2—C3—C4—C5	177.8 (4)	C13—C14—C15—C16	2.6 (4)
C2—C3—C4—C9	−1.8 (5)	C13—C14—C15—S1	−173.1 (2)
C9—C4—C5—C6	2.2 (5)	O2—S1—C15—C16	−60.6 (3)
C3—C4—C5—C6	−177.5 (3)	O3—S1—C15—C16	172.1 (2)
C4—C5—C6—C7	0.0 (6)	N2—S1—C15—C16	51.0 (3)
C5—C6—C7—C8	−1.7 (6)	O2—S1—C15—C14	115.0 (2)
C6—C7—C8—C9	1.2 (6)	O3—S1—C15—C14	−12.4 (3)
C7—C8—C9—C4	0.9 (5)	N2—S1—C15—C14	−133.4 (2)
C7—C8—C9—C10	−179.9 (3)	C14—C15—C16—C17	−1.9 (4)
C5—C4—C9—C8	−2.6 (4)	S1—C15—C16—C17	173.7 (2)
C3—C4—C9—C8	177.1 (3)	C13—C12—C17—C16	5.2 (5)
C5—C4—C9—C10	178.2 (3)	N1—C12—C17—C16	−173.2 (3)
C3—C4—C9—C10	−2.1 (4)	C15—C16—C17—C12	−1.9 (5)
O1—C1—C10—C11	−6.1 (5)	S1—N2—C18—N3	177.9 (2)
C2—C1—C10—C11	170.0 (3)	S1—N2—C18—S2	−2.8 (4)
O1—C1—C10—C9	179.3 (3)	C19—N3—C18—N2	178.6 (3)
C2—C1—C10—C9	−4.6 (5)	C19—N3—C18—S2	−0.9 (3)
C8—C9—C10—C11	11.7 (5)	C20—S2—C18—N2	−178.0 (3)
C4—C9—C10—C11	−169.2 (3)	C20—S2—C18—N3	1.4 (2)
C8—C9—C10—C1	−173.8 (3)	C18—N3—C19—C20	−0.4 (4)
C4—C9—C10—C1	5.3 (4)	N3—C19—C20—S2	1.5 (4)
C12—N1—C11—C10	−175.4 (3)	C18—S2—C20—C19	−1.7 (3)
C1—C10—C11—N1	2.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.87	2.550 (3)	134
N3—H3A···S1i	0.86	2.88	3.729 (2)	168
N3—H3A···O2i	0.86	2.44	3.131 (3)	138
N3—H3A···N2i	0.86	2.13	2.943 (3)	158
C13—H13···O2ii	0.93	2.60	3.257 (4)	128
C19—H19···O1iii	0.93	2.57	3.373 (4)	145
C20—H20···Cg4iv	0.93	2.99	3.853 (4)	156

Table 1

Hydrogen-bond geometry (, )

Cg4 is the centroid of the C12C17 ring.

DHA	DH	HA	D A	DHA
N1H1O1	0.86	1.87	2.550(3)	134
N3H3AS1i	0.86	2.88	3.729(2)	168
N3H3AO2i	0.86	2.44	3.131(3)	138
N3H3AN2i	0.86	2.13	2.943(3)	158
C13H13O2ii	0.93	2.60	3.257(4)	128
C19H19O1iii	0.93	2.57	3.373(4)	145
C20H20Cg4iv	0.93	2.99	3.853(4)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .