1-{[(E)-(4-{[(2Z)-2,3-Di­hydro-1,3-thia­zol-2-yl­idene]sulfamo­yl}phen­yl)iminium­yl]meth­yl}naphthalen-2-olate

Shahid, M.; Tahir, M.N.; Salim, M.; Munawar, M.A.; Shad, H.A.

doi:10.1107/S2056989015009640

organic compounds

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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages o421-o422

doi:10.1107/S2056989015009640

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1-{[(E)-(4-{[(2Z)-2,3-Dihydro-1,3-thiazol-2-ylidene]sulfamoyl}phenyl)iminiumyl]methyl}naphthalen-2-olate

Muhammad Shahid,^a Muhammad Nawaz Tahir,^b ^* Muhammad Salim,^a Munawar Ali Munawar ^a and Hazoor Ahmad Shad ^c

^aDepartment of Chemistry, University of the Punjab, Lahore, Punjab, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Punjab, Pakistan, and ^cDepartment of Chemistry, University of Sargodha, Sargodha, Punjab, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

Edited by S. Parkin, University of Kentucky, USA (Received 9 May 2015; accepted 19 May 2015; online 23 May 2015)

In the title zwitterionic compound, C₂₀H₁₅N₃O₃S₂, the 2-hydroxynaphthalene-1-carbaldehyde group A, the anilinic unit B and the 1,3-thiazol-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 intramolecular S(6) motif involving the imine N—H and the naphtholate O atom. In the crystal, inversion-related molecules form dimers as a result of N—H⋯N and N—H⋯O hydrogen bonds with R₂²(8) and R₁²(4) motifs, respectively. Weak π–π interactions between the benzene and naphthyl rings of inversion-related molecules have ring centroid–centroid distances of 3.638 (2) and 4.041 (2) Å. A C—H⋯π interaction occurs between the thiazol ring and the benzene ring of an adjacent molecule.

Keywords: crystal structure; zwitterionic compound; sulfathiazole; hydrogen bonding; C—H⋯π interactions; π–π interactions.

CCDC reference: 1401829

1. Related literature

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

2. Experimental

2.1. Crystal data

C₂₀H₁₅N₃O₃S₂
M_r = 409.47
Triclinic, $[P \overline 1]$
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.127
S = 1.01
3554 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C12—C17 ring.

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⋯Cg4^iv	0.93	2.99	3.853 (4)	156
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y, -z+1; (iii) -x+1, -y+1, -z+2; (iv) x+1, y, z.

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.

Supporting information

CCDC reference: 1401829

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015009640/pk2552sup1.cif

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

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

checkCIF report

Comment top

The crystal structures of 1-(4-(diaminomethyleneaminosulfonyl)phenyl iminiomethyl)-2-naphtholate N,N-dimethylformamide solvate (El-Ghamry, 2008), N-(2,3-dihydro-1,3-thiazol-2-ylidene)-4-((2-hydroxybenzylidene)amino) benzenesulfonamide (Zhang, 2009) and 1-(4-((4-((E)-(2-hydroxynaphthalen-1-yl) methylideneamino)phenyl)sulfanyl)phenyl)ethanone unknown solvate (Hebbachi, 2013) have been published, and are related to the title compound (I, Fig. 1). (I) was synthesized to study its biological properties and to explore complexation with different metals.

The title compound crystallizes as a zwitterion. In (I), the 2-hydroxynaphthalene-1-carbaldehyde moiety A (C1–C11/O1), the anilinic moiety B (N1/C12—C17) and the 1,3-thiazol-2(3H) -imine group C (N2/N3/S1/C18/C19/C20) are 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. The sulfonyl group D (S1/O2/O3) is oriented at a dihedral angle of 69.14 (10)° and 55.43 (13)° with B and C, respectively. There exist intermolecular H-bonding of N—H···O type (Table 1, Fig. 1) forming S (6) loop (Bernstein et al., 1995). The molecules are dimerized due to N—H···N type of H-bonding (Table 1, Fig. 2). R₁²(4) and R₂²(8) rings (Table 1, Fig. 2) (Bernstein et al., 1995) are formed. There exist strong π···π interactions at a distance of 3.638 (2) Å between the centroids of Cg2— Cg3ⁱ and Cg3—Cg2ⁱ [i = - 1 - x, - y, 2 - z], where Cg2 and Cg3 are the centroids of E (C4—C9) and F (C1—C4/C9/C10), respectively. Similarly π···π interactions exists between the centeroids of [Cg3—Cg4ⁱⁱ and Cg4—Cg3ⁱⁱ: ii = - x, - y, 2 - z] at a distance of 4.041 (2) Å. There also exist C—H···π interactions (Table 1). All π···π and C—H···π interactions participate in stabilizing the structure.

Related literature top

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

Experimental top

Equimolar quantities of 2-hydroxynaphthalene-1-carbaldehyde and 4-amino-N-(1,3-thiazol-2-yl)benzenesulfonamide (Sulfathiazole) were refluxed in methanol for 6 h. The solution was kept at room temperature for crystallization which affoarded light orange plates after 72 h.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (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 (Spek, 2009).

Figures top

	Fig. 1. 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.
	Fig. 2. A partial packing plot (PLATON; Spek, 2009), which shows that molecules form dimers and are interlinked forming various ring motifs.

1-{[(E)-(4-{[(2Z)-2,3-Dihydro-1,3-thiazol-2-ylidene]sulfamoyl}phenyl)iminiumyl]methyl}naphthalen-2-olate top

Crystal data top

C₂₀H₁₅N₃O₃S₂	Z = 2
M_r = 409.47	F(000) = 424
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0596P)²] where P = (F_o² + 2F_c²)/3
3554 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₀H₁₅N₃O₃S₂	γ = 102.044 (5)°
M_r = 409.47	V = 927.5 (3) Å³
Triclinic, P1	Z = 2
a = 9.127 (2) Å	Mo Kα radiation
b = 10.1417 (12) Å	µ = 0.31 mm⁻¹
c = 11.355 (3) Å	T = 296 K
α = 114.526 (6)°	0.32 × 0.26 × 0.18 mm
β = 91.556 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3554 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2086 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.948	R_int = 0.052
13121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
3554 reflections	Δρ_min = −0.24 e Å⁻³
253 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.

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C12—C17 ring.

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···Cg4^iv	0.93	2.99	3.853 (4)	156

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z+2; (iv) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C12—C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.87	2.550 (3)	134.2
N3—H3A···S1ⁱ	0.86	2.88	3.729 (2)	167.9
N3—H3A···O2ⁱ	0.86	2.44	3.131 (3)	138.3
N3—H3A···N2ⁱ	0.86	2.13	2.943 (3)	158.3
C13—H13···O2ⁱⁱ	0.93	2.60	3.257 (4)	127.7
C19—H19···O1ⁱⁱⁱ	0.93	2.57	3.373 (4)	145.3
C20—H20···Cg4^iv	0.93	2.99	3.853 (4)	156

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z+2; (iv) x+1, y, z.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

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Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 71| Part 6| June 2015| Pages o421-o422

doi:10.1107/S2056989015009640

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

1-{[(E)-(4-{[(2Z)-2,3-Di­hydro-1,3-thia­zol-2-yl­­idene]sulfamo­yl}phen­yl)iminium­yl]meth­yl}naphthalen-2-olate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

1-{[(E)-(4-{[(2Z)-2,3-Dihydro-1,3-thiazol-2-ylidene]sulfamoyl}phenyl)iminiumyl]methyl}naphthalen-2-olate