2-(4-Methyl­sulfanylphen­yl)-1H-benzimidazol-3-ium bromide

Ziaulla, M.; Manjunatha, M.N.; Sankolli, R.; Nagasundara, K.R.; Begum, N.S.

doi:10.1107/S1600536811000146

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o341-o342

doi:10.1107/S1600536811000146

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2-(4-Methylsulfanylphenyl)-1H-benzimidazol-3-ium bromide

Mohamed Ziaulla,^a M. N. Manjunatha,^a Ravish Sankolli,^b K. R. Nagasundara ^a and Noor Shahina Begum ^a ^*

^aDepartment of Chemistry, Bangalore University, Bangalore 560 001, India, and ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India
^*Correspondence e-mail: noorsb@rediffmail.com

(Received 1 January 2011; accepted 4 January 2011; online 12 January 2011)

In the cation of the title compound, C₁₄H₁₃N₂S⁺·Br⁻, the essentially planar benzimidazole system (r.m.s. deviation = 0.0082 Å) is substituted with a 4-methylsulfanylphenyl ring. The dihedral angle between the benzimidazole system and the 4-methylsulfanylphenyl ring is 2.133 (2)°. The crystal structure is characterized by strong and highly directional intermolecular N—H⋯Br hydrogen bonds involving the bromide ion. Moreover, C—H⋯S interactions result in chains of molecules along the c axis. The supramolecular assembly is further stabilized by π–π stacking interactions between the benzimidazole system and 4-methylsulfanylphenyl rings [centroid–centroid distance = 3.477 (4) Å].

Related literature

For general background to benzimidazoles and their derivatives, see: Huang & Scarborough (1999 ); Preston (1974 ); Zarrinmayeh et al. (1998 ); Zhu et al. (2000 ). For related structures, see: Goker et al. (1995 ); Ozbey et al. (1998 ); Vasudevan et al. (1994 ). For hydrogen bonding, see: Bernstein et al. (1995 ); Nardelli (1983 ).

Experimental

Crystal data

C₁₄H₁₃N₂S⁺·Br⁻
M_r = 321.23
Monoclinic, P 2₁ /c
a = 5.3289 (2) Å
b = 24.0195 (12) Å
c = 10.9544 (5) Å
β = 100.113 (2)°
V = 1380.35 (11) Å³
Z = 4
Mo Kα radiation
μ = 3.11 mm⁻¹
T = 296 K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.575, T_max = 0.636
23823 measured reflections
3009 independent reflections
2273 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.069
S = 1.03
3009 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Br1	0.74 (2)	2.51 (2)	3.247 (2)	171 (2)
N2—H2N⋯Br1ⁱ	0.77 (3)	2.50 (2)	3.231 (2)	159
C5—H5⋯S1ⁱⁱ	0.97 (3)	2.98 (3)	3.736 (3)	135
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000146/pb2053sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000146/pb2053Isup2.hkl

checkCIF report

Comment top

Benzimidazoles and their derivatives exhibit a number of important pharmacological properties, such as antihistaminic, anti-ulcerative, antiallergic, and antipyretic. In addition, benzimidazole derivatives are effective against the human cytomegalo virus (HCMV) (Zhu et al., 2000) and are also efficient selective neuropeptide Y Y1 receptor antagonists (Zarrinmayeh et al., 1998). Most of the described methods for the synthesisof benzimidazoles make use of volatile organic solvents and involve solid-phase synthesis via o-nitroanilines (Preston et al., 1974; Huang et al., 1999) or the condensation of o-phenylenediamines with carboxylic acid derivatives, aldehydes and aryl halides. In the title compound, there is one benzimidazole thiomethyl phenyl cation and one Br^- anion in the asymmetric unit. The expected proton transfer from HBr to benzimidazole thiomethyl phenyl occurs at atom N1 of the benzimidazole ring. Consequently,atom N1 shows quaternary character and bears a positive charge. In the molecule, the benzimidazole and thiomethyl phenyl rings are planar inclined at an dihedral angle 2.133 (2)° between them. The molecular structure is primarily stabilized by strong intramolecular N—H···Br hydrogen bond. The bond lengths and angles for the benzimidazole moiety of the molecule are in good agreement, within experimental errors, with those observed in other benzimidazole derivatives (Goker et al., 1995; Ozbey et al., 1998; Vasudevan et al.,1994).Further, the crystal structure is stabilized by intermolecular interactions into three dimensional framework structure by the combination of C—H···S and N—H···Br. The C—H···S and N—H···Br interactions together generates tetramers linking the molecules into chain like pattern along crystallographic c-axis. Additionally,the supramolecular assembly is further stabilized by π-π-stacking interactions between the benzimidazole and thiomethyl phenyl rings. The C3—C10 (x, 0.5 - y, 1/2 + z) disposed at a distance of 3.477 (4) Å.

Related literature top

For general background to benzimidazoles and their derivatives, see: Huang & Scarborough (1999); Preston (1974); Zarrinmayeh et al. (1998); Zhu et al. (2000). For related structures, see: Goker et al. (1995); Ozbey et al. (1998); Vasudevan et al. (1994). For hydrogen bonding, see: Bernstein et al. (1995); Nardelli (1983).

Experimental top

A ethanol solution (20 ml) of zinc bromide (2.25 mg, 1.0 mmol) was treated with 2-(p-thiomethylphenyl)benzimidazole (4.80 mg, 2.0 mmol) in ethanol (20 ml). The mixture was then treated with 48% HBr (2–3 ml) followed by liquid Br2 (2–3 ml). The mixture was refluxed for 6 hrs on a steam bath filtered and allowed to stand at room temperature for two days. Coloured crystals separated and these were washed with ethanol and dried. (yield 4.00 mg; 83%).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. ORTEP (Farrugia, 1997) view of the title compound, showing 50% probability ellipsoids and the atom numbering scheme.
	Fig. 2. A unit cell packing of the title compound showing intermolecular interactions with dotted lines. H-atoms not involved in hydrogen bonding have been excluded.

2-(4-Methylsulfanylphenyl)-1H-benzimidazol-3-ium bromide top

Crystal data top

C₁₄H₁₃N₂S⁺·Br⁻	F(000) = 648
M_r = 321.23	D_x = 1.546 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3009 reflections
a = 5.3289 (2) Å	θ = 1.7–27.0°
b = 24.0195 (12) Å	µ = 3.11 mm⁻¹
c = 10.9544 (5) Å	T = 296 K
β = 100.113 (2)°	Block, yellow
V = 1380.35 (11) Å³	0.20 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEX CCD detector diffractometer	3009 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2273 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan Bruker Kappa APEX	h = −6→6
T_min = 0.575, T_max = 0.636	k = −30→30
23823 measured reflections	l = −13→13

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0338P)² + 0.3109P] where P = (F_o² + 2F_c²)/3
3009 reflections	(Δ/σ)_max = 0.001
215 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₄H₁₃N₂S⁺·Br⁻	V = 1380.35 (11) Å³
M_r = 321.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.3289 (2) Å	µ = 3.11 mm⁻¹
b = 24.0195 (12) Å	T = 296 K
c = 10.9544 (5) Å	0.20 × 0.18 × 0.16 mm
β = 100.113 (2)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	3009 independent reflections
Absorption correction: multi-scan Bruker Kappa APEX	2273 reflections with I > 2σ(I)
T_min = 0.575, T_max = 0.636	R_int = 0.039
23823 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.35 e Å⁻³
3009 reflections	Δρ_min = −0.29 e Å⁻³
215 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
Br1	0.27225 (4)	0.295277 (10)	0.33608 (2)	0.04982 (10)
S1	0.57379 (16)	−0.00128 (3)	0.21720 (8)	0.0710 (2)
N1	0.6485 (4)	0.28057 (8)	0.13508 (19)	0.0421 (5)
N2	0.9186 (4)	0.25577 (8)	0.01982 (17)	0.0408 (4)
C1	0.9109 (4)	0.31328 (10)	0.0161 (2)	0.0415 (5)
C2	1.0437 (5)	0.35189 (11)	−0.0424 (2)	0.0555 (6)
C3	0.9910 (6)	0.40696 (12)	−0.0233 (3)	0.0644 (7)
C4	0.8149 (6)	0.42307 (12)	0.0504 (3)	0.0659 (8)
C5	0.6847 (5)	0.38481 (11)	0.1084 (3)	0.0555 (6)
C6	0.7381 (4)	0.32913 (10)	0.0906 (2)	0.0430 (5)
C7	0.7610 (4)	0.23676 (9)	0.09243 (19)	0.0387 (5)
C8	0.7198 (4)	0.17861 (9)	0.1213 (2)	0.0391 (5)
C9	0.5449 (5)	0.16389 (11)	0.1960 (2)	0.0516 (6)
C10	0.5058 (5)	0.10930 (11)	0.2220 (2)	0.0558 (6)
C11	0.6392 (5)	0.06710 (10)	0.1762 (2)	0.0453 (5)
C12	0.8139 (6)	0.08164 (11)	0.1013 (3)	0.0586 (7)
C13	0.8530 (5)	0.13648 (11)	0.0746 (3)	0.0548 (7)
C14	0.7734 (8)	−0.04379 (14)	0.1398 (4)	0.0721 (9)
H1N	0.562 (5)	0.2802 (10)	0.181 (2)	0.042 (7)*
H9	0.464 (5)	0.1907 (12)	0.233 (2)	0.062 (8)*
H2N	0.991 (5)	0.2357 (11)	−0.017 (2)	0.049 (8)*
H12	0.909 (5)	0.0539 (11)	0.070 (2)	0.065 (8)*
H14C	0.736 (6)	−0.0776 (16)	0.159 (3)	0.086 (11)*
H14B	0.947 (7)	−0.0359 (13)	0.169 (3)	0.090 (11)*
H5	0.567 (5)	0.3946 (12)	0.163 (2)	0.075 (9)*
H4	0.781 (6)	0.4619 (13)	0.063 (3)	0.085 (10)*
H2	1.159 (5)	0.3398 (11)	−0.092 (2)	0.058 (7)*
H13	0.975 (5)	0.1462 (12)	0.022 (3)	0.079 (9)*
H10	0.389 (5)	0.0996 (11)	0.276 (2)	0.064 (7)*
H3	1.080 (5)	0.4350 (12)	−0.060 (2)	0.070 (8)*
H14A	0.736 (6)	−0.0374 (14)	0.054 (3)	0.097 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.05371 (15)	0.05390 (17)	0.04775 (15)	0.00057 (11)	0.02515 (10)	0.00017 (11)
S1	0.0965 (6)	0.0390 (4)	0.0891 (5)	−0.0055 (3)	0.0480 (4)	0.0060 (3)
N1	0.0446 (11)	0.0397 (11)	0.0476 (11)	−0.0021 (8)	0.0233 (9)	−0.0012 (9)
N2	0.0441 (10)	0.0396 (11)	0.0436 (11)	−0.0006 (9)	0.0212 (9)	−0.0029 (9)
C1	0.0442 (12)	0.0399 (12)	0.0414 (12)	−0.0043 (10)	0.0105 (10)	−0.0003 (10)
C2	0.0593 (16)	0.0521 (16)	0.0598 (15)	−0.0093 (12)	0.0233 (13)	0.0045 (13)
C3	0.0741 (19)	0.0474 (16)	0.0755 (18)	−0.0129 (14)	0.0231 (15)	0.0080 (14)
C4	0.077 (2)	0.0386 (16)	0.082 (2)	−0.0056 (13)	0.0140 (16)	−0.0001 (14)
C5	0.0626 (16)	0.0411 (15)	0.0655 (16)	0.0024 (12)	0.0185 (13)	−0.0077 (13)
C6	0.0433 (12)	0.0414 (13)	0.0450 (12)	−0.0031 (10)	0.0099 (9)	−0.0011 (10)
C7	0.0380 (11)	0.0407 (13)	0.0392 (11)	−0.0013 (10)	0.0121 (9)	0.0001 (10)
C8	0.0400 (12)	0.0394 (13)	0.0392 (11)	−0.0015 (10)	0.0109 (9)	0.0009 (10)
C9	0.0621 (16)	0.0380 (13)	0.0626 (15)	0.0046 (11)	0.0331 (13)	0.0005 (12)
C10	0.0620 (16)	0.0484 (15)	0.0665 (16)	−0.0018 (12)	0.0377 (13)	0.0054 (13)
C11	0.0512 (13)	0.0386 (13)	0.0483 (13)	−0.0036 (10)	0.0147 (10)	0.0016 (10)
C12	0.0705 (18)	0.0389 (15)	0.0762 (18)	0.0019 (12)	0.0400 (15)	−0.0019 (13)
C13	0.0615 (16)	0.0436 (15)	0.0689 (16)	0.0011 (12)	0.0377 (14)	−0.0004 (12)
C14	0.091 (3)	0.0407 (18)	0.089 (3)	0.0024 (16)	0.028 (2)	−0.0003 (16)

Geometric parameters (Å, º) top

S1—C11	1.754 (2)	C5—C6	1.388 (3)
S1—C14	1.791 (4)	C5—H5	0.97 (3)
N1—C7	1.335 (3)	C7—C8	1.457 (3)
N1—C6	1.381 (3)	C8—C13	1.384 (3)
N1—H1N	0.74 (3)	C8—C9	1.390 (3)
N2—C7	1.334 (3)	C9—C10	1.365 (4)
N2—C1	1.382 (3)	C9—H9	0.91 (3)
N2—H2N	0.77 (3)	C10—C11	1.382 (3)
C1—C6	1.386 (3)	C10—H10	0.96 (3)
C1—C2	1.390 (3)	C11—C12	1.389 (3)
C2—C3	1.376 (4)	C12—C13	1.373 (4)
C2—H2	0.93 (3)	C12—H12	0.94 (3)
C3—C4	1.395 (4)	C13—H13	0.97 (3)
C3—H3	0.95 (3)	C14—H14C	0.87 (4)
C4—C5	1.373 (4)	C14—H14B	0.94 (3)
C4—H4	0.96 (3)	C14—H14A	0.94 (3)

C11—S1—C14	104.57 (15)	N2—C7—C8	126.29 (19)
C7—N1—C6	109.73 (19)	N1—C7—C8	125.82 (18)
C7—N1—H1N	127.0 (19)	C13—C8—C9	118.2 (2)
C6—N1—H1N	123.0 (19)	C13—C8—C7	120.93 (19)
C7—N2—C1	109.94 (18)	C9—C8—C7	120.9 (2)
C7—N2—H2N	121.6 (19)	C10—C9—C8	120.6 (2)
C1—N2—H2N	128.3 (19)	C10—C9—H9	118.9 (17)
N2—C1—C6	106.04 (19)	C8—C9—H9	120.3 (17)
N2—C1—C2	131.7 (2)	C9—C10—C11	121.5 (2)
C6—C1—C2	122.2 (2)	C9—C10—H10	120.0 (16)
C3—C2—C1	115.9 (3)	C11—C10—H10	118.4 (16)
C3—C2—H2	124.1 (16)	C10—C11—C12	118.1 (2)
C1—C2—H2	120.0 (16)	C10—C11—S1	117.15 (18)
C2—C3—C4	122.1 (3)	C12—C11—S1	124.79 (19)
C2—C3—H3	119.2 (17)	C13—C12—C11	120.6 (2)
C4—C3—H3	118.7 (17)	C13—C12—H12	119.2 (17)
C5—C4—C3	121.9 (3)	C11—C12—H12	120.2 (17)
C5—C4—H4	117.2 (19)	C12—C13—C8	121.1 (2)
C3—C4—H4	121.0 (19)	C12—C13—H13	120.1 (17)
C4—C5—C6	116.5 (3)	C8—C13—H13	118.9 (18)
C4—C5—H5	123.9 (18)	S1—C14—H14C	104 (2)
C6—C5—H5	119.5 (18)	S1—C14—H14B	111 (2)
N1—C6—C1	106.4 (2)	H14C—C14—H14B	111 (3)
N1—C6—C5	132.2 (2)	S1—C14—H14A	110 (2)
C1—C6—C5	121.4 (2)	H14C—C14—H14A	112 (3)
N2—C7—N1	107.9 (2)	H14B—C14—H14A	109 (3)

C7—N2—C1—C6	−0.2 (3)	C6—N1—C7—C8	178.60 (19)
C7—N2—C1—C2	177.8 (3)	N2—C7—C8—C13	1.4 (3)
N2—C1—C2—C3	−178.5 (2)	N1—C7—C8—C13	−178.0 (2)
C6—C1—C2—C3	−0.8 (4)	N2—C7—C8—C9	−178.3 (2)
C1—C2—C3—C4	0.0 (4)	N1—C7—C8—C9	2.2 (3)
C2—C3—C4—C5	0.3 (5)	C13—C8—C9—C10	−0.2 (4)
C3—C4—C5—C6	0.3 (4)	C7—C8—C9—C10	179.5 (2)
C7—N1—C6—C1	0.8 (3)	C8—C9—C10—C11	0.6 (4)
C7—N1—C6—C5	−179.2 (3)	C9—C10—C11—C12	−0.7 (4)
N2—C1—C6—N1	−0.4 (2)	C9—C10—C11—S1	179.5 (2)
C2—C1—C6—N1	−178.6 (2)	C14—S1—C11—C10	178.8 (2)
N2—C1—C6—C5	179.6 (2)	C14—S1—C11—C12	−1.0 (3)
C2—C1—C6—C5	1.4 (4)	C10—C11—C12—C13	0.4 (4)
C4—C5—C6—N1	178.9 (3)	S1—C11—C12—C13	−179.8 (2)
C4—C5—C6—C1	−1.1 (4)	C11—C12—C13—C8	−0.1 (5)
C1—N2—C7—N1	0.7 (3)	C9—C8—C13—C12	−0.1 (4)
C1—N2—C7—C8	−178.83 (19)	C7—C8—C13—C12	−179.8 (2)
C6—N1—C7—N2	−0.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Br1	0.74 (2)	2.51 (2)	3.247 (2)	171 (2)
N2—H2N···Br1ⁱ	0.77 (3)	2.50 (2)	3.231 (2)	159
C5—H5···S1ⁱⁱ	0.97 (3)	2.98 (3)	3.736 (3)	135

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₂S⁺·Br⁻
M_r	321.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.3289 (2), 24.0195 (12), 10.9544 (5)
β (°)	100.113 (2)
V (Å³)	1380.35 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.11
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD detector diffractometer
Absorption correction	Multi-scan Bruker Kappa APEX
T_min, T_max	0.575, 0.636
No. of measured, independent and observed [I > 2σ(I)] reflections	23823, 3009, 2273
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.069, 1.03
No. of reflections	3009
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.29

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Br1	0.74 (2)	2.51 (2)	3.247 (2)	171 (2)
N2—H2N···Br1ⁱ	0.77 (3)	2.50 (2)	3.231 (2)	159
C5—H5···S1ⁱⁱ	0.97 (3)	2.98 (3)	3.736 (3)	135

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

Acknowledgements

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance and the Department of Science and Technology (DST), India, for the data collection facility under the IRHPA–DST program. MNM thanks the M. S. Ramaiah Institute of Technology, Bangalore, for their support and encouragement.

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