Benzene-1,2-diaminium bis­(4-methyl­benzene-1-sulfonate)

Narvekar, K.U.; Srinivasan, B.R.

doi:10.1107/S2414314620001005

organic compounds

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ISSN: 2414-3146

Volume 5| Part 1| January 2020| x200100

https://doi.org/10.1107/S2414314620001005

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Benzene-1,2-diaminium bis(4-methylbenzene-1-sulfonate)

Kedar U. Narvekar ^a and Bikshandarkoil R. Srinivasan ^a ^*

^aSchool of Chemical Sciences, Goa University PO, Goa 403206, India
^*Correspondence e-mail: srini@unigoa.ac.in

Edited by R. J. Butcher, Howard University, USA (Received 2 January 2020; accepted 25 January 2020; online 31 January 2020)

The structure of the title salt, C₆H₁₀N₂²⁺·2C₇H₇O₃S⁻, consists of a unique benzene-1,2-diaminium dication charge balanced by a pair of crystallographically independent 4-methylbenzene-1-sulfonate anions. The cations and anions are interlinked by several N—H⋯O hydrogen bonds.

Keywords: crystal structure; benzene-1,2-diaminium dication; 4-methylbenzene-1-sulfonate anion; organic salt.

CCDC reference: 1979912

Structure description

The aromatic diamine, benzene-1,2-diamine also known as o-phenylenediamine, can function as a neutral ligand and bind to a metal via both amine N atoms (Koizumi & Fukuju, 2011 ; Guillén et al., 2018 ) or by a single nitrogen in a monodentate fashion (Nelson et al., 1982 ; Dickman, 2000 ). In addition, benzene-1,2-diamine can function as a charge-balancing dication in which both the amine N atoms are protonated (Raghavaiah et al., 2006 ; Powers & Geiger, 2019 ) or as a monocation (Raghavaiah et al., 2005 ; Mishra & Pallepogu, 2018 ). The structural diversity of the compounds of benzene-1,2-diamine in neutral or cationic form is highlighted by the results of a survey of the Cambridge Structural Database (CSD; Groom et al., 2016 ), which had more than 220 hits for the above three types of compounds. Of these, a total of 79 deposits do not contain any metal ions and correspond to crystal structures containing only diprotonated benzene-1,2-diaminium cations (47 hits) and monoprotonated 2-aminoanilinium cations (55 hits). An example of a molecular salt of 4-methylbenzene-1-sulfonic acid containing both mono and diprotonated cations, namely 2-aminoanilinium benzene-1,2-diaminium tris(4-methylbenzene-1-sulfonate) (2) has been reported recently (Amirthakumar et al., 2018 ).

In this report, we describe the crystal structure of the title compound, which was obtained by an aqueous reaction of the aromatic diamine with 4-methylbenzene-1-sulfonic acid in a 1:2 molar ratio, unlike 2, which was isolated from a 1:1 reaction. The asymmetric unit of the title compound consists of an unique benzene-1,2-diaminium dication charge-balanced by a pair of crystallographically independent 4-methylbenzene-1-sulfonate anions (Fig. 1) with all atoms located on general positions. The geometric parameters of the unique dication and the crystallographically independent anions are in normal ranges and are in agreement with reported data (Powers & Geiger, 2019).

Figure 1
The crystal structure of 1 showing the atom-labelling scheme. Blue dotted lines indicate hydrogen bonds. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radii.

All six oxygen atoms attached to the sulfur atom of the sulfonate moiety of the anion function as hydrogen-bond acceptors while the H atoms attached to the N atoms of the dication function as hydrogen-bond donors, resulting in a total of eight N—H⋯O hydrogen bonds of which six are intermolecular (Table 1). It is interesting to note that the dications and the unique anions are interlinked only via N—H⋯O hydrogen bonds, unlike in 2 for which both N—H⋯O and C—H⋯O hydrogen bonds were reported. Each anion is linked to three symmetry-related dications (Fig. 2) while each dication is hydrogen-bonded to six symmetry-related anions. The net result of the hydrogen-bonding interactions is the interlinking of the cations with the anions, resulting in alternating layers of cations and anions parallel to [010] (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O21	0.89	1.92	2.8062 (19)	175
N1—H1B⋯O11ⁱ	0.89	2.07	2.7509 (19)	133
N1—H1B⋯O22ⁱⁱ	0.89	2.31	2.9017 (18)	124
N1—H1C⋯O13ⁱⁱⁱ	0.89	1.89	2.7733 (19)	170
N2—H2A⋯O13ⁱⁱⁱ	0.89	2.46	2.9128 (19)	112
N2—H2A⋯O23^iv	0.89	1.97	2.7820 (18)	151
N2—H2B⋯O22ⁱⁱ	0.89	1.98	2.8611 (19)	173
N2—H2C⋯O12	0.89	1.84	2.7224 (19)	175
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) x, y-1, z.

Figure 2
The hydrogen-bonding scheme around the two unique anions (left and right). For clarity, the H atoms of the aromatic ring are not shown. The hydrogen-bonding environment of the dication (middle) shows only the acceptor oxygen atoms of the unique anions. Symmetry codes: (i) x, y + 1, z; (ii) −x + 1, −y + 1, −z + 1; (iii) −x + 1, −y, −z + 1; (iv) x, y − 1, z.

Figure 3
A view along b axis of the unit-cell packing showing the interlinking of the dications with the monocations via N—H⋯O hydrogen bonds which are shown as dashed lines. For clarity, the H atoms attached to the C atoms are not shown.

Synthesis and crystallization

Freshly recrystallized benzene-1,2-diamine (108 mg, 1 mmol) was dissolved in double-distilled water (10–15 ml) by heating the mixture. Into this, an aqueous solution of 4-methylbenzene-1-sulfonic acid (380 mg, 2 mmol) was added. The reaction mixture was heated to boiling and a pinch of activated charcoal was added. The hot solution was filtered and the clear filtrate was left aside for crystallization. After a few days, crystals of the title compound 1 slowly separated. The crystals were filtered and air dried. Yield 50%.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₁₀N₂²⁺·2C₇H₇O₃S⁻
M_r	452.53
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	29.1537 (9), 8.8739 (3), 19.9919 (6)
β (°)	123.621 (1)
V (Å³)	4306.9 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.29
Crystal size (mm)	0.56 × 0.15 × 0.12

Data collection
Diffractometer	Bruker D8 Quest ECO
Absorption correction	Multi-scan (SADABS; Bruker, 2018 )
T_min, T_max	0.696, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	59056, 6568, 4705
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.126, 1.07
No. of reflections	6568
No. of parameters	276
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.39
Computer programs: APEX3 and SAINT (Bruker, 2018), SHELXT2014 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and shelXle (Hübschle et al., 2011 ).

Structural data

CCDC reference: 1979912

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314620001005/bv4029sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620001005/bv4029Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314620001005/bv4029Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: shelXle (Hübschle et al., 2011).

Benzene-1,2-diaminium bis(4-methylbenzene-1-sulfonate) top

Crystal data top

C₆H₁₀N₂²⁺·2C₇H₇O₃S⁻	F(000) = 1904
M_r = 452.53	D_x = 1.396 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 29.1537 (9) Å	Cell parameters from 9968 reflections
b = 8.8739 (3) Å	θ = 2.9–29.9°
c = 19.9919 (6) Å	µ = 0.29 mm⁻¹
β = 123.621 (1)°	T = 293 K
V = 4306.9 (2) Å³	Block, colourless
Z = 8	0.56 × 0.14 × 0.12 mm

Data collection top

Bruker D8 Quest ECO diffractometer	4705 reflections with I > 2σ(I)
Radiation source: Sealed Tube	R_int = 0.046
φ and ω scans	θ_max = 30.5°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2018)	h = −41→41
T_min = 0.696, T_max = 0.746	k = −12→12
59056 measured reflections	l = −28→28
6568 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0525P)² + 2.9966P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.126	(Δ/σ)_max = 0.001
S = 1.07	Δρ_max = 0.34 e Å⁻³
6568 reflections	Δρ_min = −0.39 e Å⁻³
276 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0026 (3)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All hydrogen atoms were located in appropriate positions and were included in calculated positions and refined with a riding model for both C—H and N—H protons. C–H distances ranged from = 0.93 and 0.96 Å for aromatic and methyl H atoms, respectively, and 0.89 for NH₃⁺ H atoms with U_iso(H) = 1.2 U_eq(C-aromatic) and U_iso(H) = 1.5 U_eq(C-methyl, NH₃⁺).

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

	x	y	z	U_iso*/U_eq
N1	0.52597 (6)	0.42385 (15)	0.43447 (8)	0.0399 (3)
H1A	0.516000	0.511465	0.408451	0.060*
H1B	0.552390	0.439398	0.485886	0.060*
H1C	0.497014	0.381592	0.430938	0.060*
N2	0.54019 (6)	0.10069 (15)	0.46813 (8)	0.0374 (3)
H2A	0.505767	0.066255	0.439229	0.056*
H2B	0.543473	0.168126	0.503495	0.056*
H2C	0.563230	0.024462	0.494094	0.056*
C1	0.54643 (6)	0.32416 (17)	0.39869 (9)	0.0349 (3)
C2	0.55343 (6)	0.17140 (17)	0.41510 (9)	0.0344 (3)
C3	0.57224 (8)	0.0796 (2)	0.37927 (12)	0.0505 (4)
H3	0.576521	−0.023317	0.389900	0.061*
C4	0.58462 (11)	0.1411 (3)	0.32770 (14)	0.0661 (6)
H4	0.597256	0.079592	0.303508	0.079*
C5	0.57830 (11)	0.2935 (3)	0.31201 (15)	0.0664 (6)
H5	0.586983	0.334936	0.277609	0.080*
C6	0.55909 (9)	0.3848 (2)	0.34726 (12)	0.0529 (4)
H6	0.554660	0.487571	0.336310	0.064*
S11	0.60971 (2)	−0.26457 (4)	0.57918 (2)	0.03904 (11)
O11	0.61408 (5)	−0.40103 (15)	0.54362 (8)	0.0562 (3)
O12	0.61358 (6)	−0.12891 (15)	0.54200 (8)	0.0563 (3)
O13	0.56134 (5)	−0.26132 (16)	0.58310 (9)	0.0573 (4)
C11	0.81185 (11)	−0.2503 (3)	0.92035 (15)	0.0827 (8)
H11A	0.833550	−0.338591	0.929269	0.124*
H11B	0.801302	−0.248348	0.958103	0.124*
H11C	0.833111	−0.161970	0.927333	0.124*
C12	0.76068 (8)	−0.2532 (2)	0.83564 (12)	0.0540 (5)
C13	0.71405 (8)	−0.1716 (2)	0.81418 (11)	0.0541 (5)
H13	0.713844	−0.113580	0.852757	0.065*
C14	0.66758 (7)	−0.1744 (2)	0.73639 (11)	0.0460 (4)
H14	0.636634	−0.118206	0.722766	0.055*
C15	0.66778 (6)	−0.26174 (17)	0.67934 (10)	0.0363 (3)
C16	0.71387 (7)	−0.3444 (2)	0.69966 (12)	0.0523 (4)
H16	0.713945	−0.403424	0.661270	0.063*
C17	0.76014 (8)	−0.3390 (3)	0.77780 (13)	0.0616 (5)
H17	0.791258	−0.394165	0.791294	0.074*
S21	0.45059 (2)	0.76496 (4)	0.35286 (2)	0.03714 (11)
O21	0.49995 (5)	0.70837 (16)	0.36096 (8)	0.0547 (3)
O22	0.44084 (6)	0.69248 (16)	0.40921 (7)	0.0559 (3)
O23	0.44971 (6)	0.92776 (14)	0.35764 (8)	0.0565 (4)
C21	0.26881 (15)	0.5602 (4)	0.01997 (17)	0.1233 (14)
H21A	0.233080	0.582893	0.009049	0.185*
H21B	0.272805	0.452969	0.018852	0.185*
H21C	0.272661	0.606499	−0.020056	0.185*
C22	0.31300 (11)	0.6205 (3)	0.10249 (13)	0.0742 (7)
C23	0.30782 (11)	0.6004 (3)	0.16652 (16)	0.0813 (7)
H23	0.275944	0.556751	0.157815	0.098*
C24	0.34940 (9)	0.6443 (3)	0.24375 (13)	0.0609 (5)
H24	0.345911	0.627550	0.286660	0.073*
C25	0.39576 (7)	0.71265 (18)	0.25587 (9)	0.0387 (3)
C26	0.40091 (9)	0.7360 (2)	0.19192 (11)	0.0496 (4)
H26	0.432285	0.782254	0.200184	0.060*
C27	0.35939 (11)	0.6905 (3)	0.11584 (12)	0.0665 (6)
H27	0.362871	0.707427	0.072940	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0434 (7)	0.0323 (6)	0.0424 (7)	0.0035 (5)	0.0229 (6)	−0.0005 (5)
N2	0.0435 (7)	0.0346 (6)	0.0376 (7)	0.0003 (5)	0.0246 (6)	0.0022 (5)
C1	0.0357 (7)	0.0340 (7)	0.0356 (7)	−0.0015 (6)	0.0202 (6)	−0.0014 (6)
C2	0.0390 (8)	0.0329 (7)	0.0352 (7)	−0.0019 (6)	0.0230 (6)	−0.0009 (6)
C3	0.0707 (12)	0.0390 (9)	0.0597 (11)	0.0038 (8)	0.0473 (10)	−0.0019 (8)
C4	0.0979 (17)	0.0598 (12)	0.0792 (15)	0.0033 (11)	0.0732 (14)	−0.0036 (11)
C5	0.0924 (16)	0.0672 (13)	0.0737 (14)	−0.0001 (12)	0.0673 (14)	0.0091 (11)
C6	0.0669 (12)	0.0435 (9)	0.0623 (11)	−0.0018 (8)	0.0444 (10)	0.0082 (8)
S11	0.03285 (19)	0.0358 (2)	0.0398 (2)	0.00174 (14)	0.01463 (16)	−0.00139 (15)
O11	0.0498 (7)	0.0493 (7)	0.0513 (7)	0.0054 (6)	0.0165 (6)	−0.0134 (6)
O12	0.0558 (8)	0.0497 (7)	0.0522 (7)	0.0056 (6)	0.0227 (6)	0.0147 (6)
O13	0.0324 (6)	0.0628 (9)	0.0694 (9)	−0.0034 (5)	0.0237 (6)	−0.0094 (7)
C11	0.0602 (14)	0.095 (2)	0.0504 (12)	0.0003 (12)	0.0039 (11)	−0.0007 (12)
C12	0.0433 (9)	0.0557 (11)	0.0440 (10)	−0.0025 (8)	0.0122 (8)	0.0027 (8)
C13	0.0534 (11)	0.0615 (12)	0.0427 (9)	−0.0035 (9)	0.0236 (8)	−0.0089 (8)
C14	0.0403 (8)	0.0516 (10)	0.0449 (9)	0.0032 (7)	0.0229 (7)	−0.0038 (7)
C15	0.0320 (7)	0.0356 (7)	0.0390 (8)	−0.0009 (6)	0.0182 (6)	0.0017 (6)
C16	0.0413 (9)	0.0563 (11)	0.0504 (10)	0.0096 (8)	0.0199 (8)	−0.0063 (8)
C17	0.0403 (10)	0.0659 (13)	0.0586 (12)	0.0134 (9)	0.0149 (9)	−0.0009 (10)
S21	0.0452 (2)	0.03159 (19)	0.03394 (19)	0.00202 (14)	0.02151 (17)	0.00074 (13)
O21	0.0502 (7)	0.0599 (8)	0.0523 (7)	0.0147 (6)	0.0274 (6)	0.0096 (6)
O22	0.0741 (9)	0.0606 (8)	0.0383 (6)	−0.0077 (7)	0.0345 (7)	−0.0003 (6)
O23	0.0581 (8)	0.0318 (6)	0.0582 (8)	0.0003 (5)	0.0188 (7)	−0.0062 (5)
C21	0.131 (3)	0.089 (2)	0.0642 (16)	−0.005 (2)	0.0007 (17)	−0.0314 (16)
C22	0.0841 (16)	0.0541 (12)	0.0475 (11)	0.0005 (11)	0.0132 (11)	−0.0131 (9)
C23	0.0700 (15)	0.0772 (17)	0.0764 (16)	−0.0281 (13)	0.0279 (13)	−0.0191 (13)
C24	0.0641 (12)	0.0657 (13)	0.0564 (11)	−0.0176 (10)	0.0355 (10)	−0.0091 (10)
C25	0.0486 (9)	0.0326 (7)	0.0356 (7)	0.0005 (6)	0.0237 (7)	−0.0019 (6)
C26	0.0659 (12)	0.0465 (10)	0.0406 (9)	0.0041 (8)	0.0320 (9)	0.0042 (7)
C27	0.0919 (17)	0.0610 (12)	0.0383 (9)	0.0128 (12)	0.0309 (11)	0.0004 (9)

Geometric parameters (Å, º) top

N1—C1	1.4570 (19)	C13—C14	1.386 (3)
N2—C2	1.4561 (18)	C14—C15	1.382 (2)
C1—C6	1.380 (2)	C15—C16	1.380 (2)
C1—C2	1.383 (2)	C16—C17	1.389 (3)
C2—C3	1.383 (2)	S21—O21	1.4462 (14)
C3—C4	1.380 (3)	S21—O23	1.4490 (13)
C4—C5	1.378 (3)	S21—O22	1.4554 (13)
C5—C6	1.380 (3)	S21—C25	1.7602 (17)
S11—O11	1.4451 (13)	C21—C22	1.521 (3)
S11—O12	1.4517 (14)	C22—C27	1.373 (4)
S11—O13	1.4553 (14)	C22—C23	1.381 (4)
S11—C15	1.7671 (16)	C23—C24	1.390 (3)
C11—C12	1.515 (3)	C24—C25	1.375 (3)
C12—C17	1.377 (3)	C25—C26	1.383 (2)
C12—C13	1.382 (3)	C26—C27	1.379 (3)

C6—C1—C2	119.60 (15)	C16—C15—C14	120.25 (16)
C6—C1—N1	118.71 (15)	C16—C15—S11	119.46 (13)
C2—C1—N1	121.69 (13)	C14—C15—S11	120.27 (12)
C3—C2—C1	120.23 (14)	C15—C16—C17	119.57 (18)
C3—C2—N2	117.66 (14)	C12—C17—C16	121.09 (18)
C1—C2—N2	122.10 (13)	O21—S21—O23	113.06 (9)
C4—C3—C2	119.78 (17)	O21—S21—O22	111.63 (9)
C5—C4—C3	120.09 (18)	O23—S21—O22	111.81 (9)
C4—C5—C6	120.07 (18)	O21—S21—C25	105.80 (8)
C5—C6—C1	120.23 (18)	O23—S21—C25	107.28 (8)
O11—S11—O12	112.95 (9)	O22—S21—C25	106.77 (8)
O11—S11—O13	113.27 (8)	C27—C22—C23	118.7 (2)
O12—S11—O13	111.32 (8)	C27—C22—C21	121.4 (3)
O11—S11—C15	106.21 (7)	C23—C22—C21	119.9 (3)
O12—S11—C15	105.73 (8)	C22—C23—C24	121.2 (2)
O13—S11—C15	106.72 (8)	C25—C24—C23	119.1 (2)
C17—C12—C13	118.48 (17)	C24—C25—C26	120.16 (17)
C17—C12—C11	119.6 (2)	C24—C25—S21	121.00 (14)
C13—C12—C11	121.9 (2)	C26—C25—S21	118.79 (14)
C12—C13—C14	121.40 (18)	C27—C26—C25	119.8 (2)
C15—C14—C13	119.22 (17)	C22—C27—C26	121.0 (2)

C6—C1—C2—C3	−0.9 (2)	C14—C15—C16—C17	−0.2 (3)
N1—C1—C2—C3	179.13 (16)	S11—C15—C16—C17	178.16 (16)
C6—C1—C2—N2	−179.29 (16)	C13—C12—C17—C16	−0.2 (3)
N1—C1—C2—N2	0.8 (2)	C11—C12—C17—C16	179.8 (2)
C1—C2—C3—C4	0.7 (3)	C15—C16—C17—C12	0.5 (3)
N2—C2—C3—C4	179.15 (19)	C27—C22—C23—C24	−2.5 (4)
C2—C3—C4—C5	0.0 (4)	C21—C22—C23—C24	175.2 (3)
C3—C4—C5—C6	−0.6 (4)	C22—C23—C24—C25	1.8 (4)
C4—C5—C6—C1	0.4 (4)	C23—C24—C25—C26	−0.6 (3)
C2—C1—C6—C5	0.4 (3)	C23—C24—C25—S21	−177.95 (19)
N1—C1—C6—C5	−179.68 (19)	O21—S21—C25—C24	131.47 (17)
C17—C12—C13—C14	−0.3 (3)	O23—S21—C25—C24	−107.57 (17)
C11—C12—C13—C14	179.6 (2)	O22—S21—C25—C24	12.44 (18)
C12—C13—C14—C15	0.6 (3)	O21—S21—C25—C26	−45.95 (16)
C13—C14—C15—C16	−0.3 (3)	O23—S21—C25—C26	75.00 (16)
C13—C14—C15—S11	−178.67 (15)	O22—S21—C25—C26	−164.99 (14)
O11—S11—C15—C16	22.07 (17)	C24—C25—C26—C27	0.0 (3)
O12—S11—C15—C16	−98.17 (16)	S21—C25—C26—C27	177.46 (15)
O13—S11—C15—C16	143.20 (15)	C23—C22—C27—C26	1.9 (4)
O11—S11—C15—C14	−159.58 (14)	C21—C22—C27—C26	−175.7 (2)
O12—S11—C15—C14	80.18 (15)	C25—C26—C27—C22	−0.7 (3)
O13—S11—C15—C14	−38.45 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O21	0.89	1.92	2.8062 (19)	175
N1—H1B···O11ⁱ	0.89	2.07	2.7509 (19)	133
N1—H1B···O22ⁱⁱ	0.89	2.31	2.9017 (18)	124
N1—H1C···O13ⁱⁱⁱ	0.89	1.89	2.7733 (19)	170
N2—H2A···O13ⁱⁱⁱ	0.89	2.46	2.9128 (19)	112
N2—H2A···O23^iv	0.89	1.97	2.7820 (18)	151
N2—H2B···O22ⁱⁱ	0.89	1.98	2.8611 (19)	173
N2—H2C···O12	0.89	1.84	2.7224 (19)	175

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

Acknowledgements

The authors acknowledge the Department of Science & Technology (DST) New Delhi, for the sanction of a Bruker D8 Quest Eco single-crystal X-ray diffractometer under the DST–FIST program.

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