6-(4-Bromo­phen­yl)-2-(4-fluoro­benz­yl)imidazo[2,1-b][1,3,4]thia­diazole

Banu, A.; Begum, N.S.; Lamani, R.S.; Khazi, I.M.

doi:10.1107/S1600536811007343

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o779

doi:10.1107/S1600536811007343

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6-(4-Bromophenyl)-2-(4-fluorobenzyl)imidazo[2,1-b][1,3,4]thiadiazole

Afshan Banu,^a Noor Shahina Begum,^a ^* Ravi S. Lamani ^b and I. M. Khazi ^b

^aDepartment of Chemistry, Bangalore University, Bangalore 560 001, India, and ^bDepartment of Chemistry, Karnatak University, Dharwad 580 003, India
^*Correspondence e-mail: noorsb@rediffmail.com

(Received 10 February 2011; accepted 26 February 2011; online 5 March 2011)

In the title compound, C₁₇H₁₁BrFN₃S, the imidazothiadiazole and bromophenyl rings are individually almost planar, with maximum deviations of 0.0215 (4) and 0.0044 (4) Å, respectively, and are inclined at an angle of 27.34 (3)° with respect to each other. The dihedral angle between the mean planes of the fluorobenzyl and imidazothiadiazole rings is 79.54 (3)°. The crystal structure is stabilized by intermolecular C—H⋯N interactions resulting in chains of molecules along the b axis.

Related literature

For general background to imidazothiadiazole derivatives, see: Palagiano et al. (1995 ). Accumulation of fluorine on carbon leads to increased oxidative and thermal stability, see: Strunecka et al. (2004 ); Park et al. (2001 ). For related structures, see: Yang et al. (2006 ).

Experimental

Crystal data

C₁₇H₁₁BrFN₃S
M_r = 388.26
Monoclinic, P 2₁ /n
a = 10.505 (4) Å
b = 5.617 (2) Å
c = 25.877 (11) Å
β = 91.566 (7)°
V = 1526.2 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.84 mm⁻¹
T = 296 K
0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.629, T_max = 0.659
8589 measured reflections
3308 independent reflections
2419 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.129
S = 1.13
3308 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯N3ⁱ	0.97	2.57	3.423 (5)	147
C4—H4⋯N3ⁱⁱ	0.93	2.74	3.488 (5)	137
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z.

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/S1600536811007343/pv2388sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007343/pv2388Isup2.hkl

checkCIF report

Comment top

Many imidazothiadiazole derivatives have been reported to possess diverse medicinal properties such as anthelmintic, antimicrobial, anti-inflammatory, antipyretic, analgesic properties and many other activities of therapeutic significance (Palagiano et al., 1995). Moreover, the presence of fluoro substituent in a molecule enhances biological activity. Accumulation of fluorine on carbon leads to increased oxidative and thermal stability (Strunecka et al., 2004; Park et al., 2001). In this article we report the synthesis and crystal struuture of a novel imidazothiadiazole derivative, (I).

In the title compound (Fig. 1), the imidazothiadiazole and bromophenyl rings are individually planar with maximum deviations of 0.0215 (4) and 0.0044 (4) Å, for C2 and C9, respectively; the mean-planes of imidazothiadiazole and bromophenyl rings make a dihedral angle of 27.34 (3)° with respect to each other. Similar deviations from planarity of the corresponding rings have been reported earlier (Yang et al., 2006). The dihedral angle between fluorobenzyl and imidazothiadiazole rings is 79.54 (3)° which is almost orthogonal. The thiadiazole moiety displays differences in the bond lengths S1-C2 [1.758 (4) Å] and S1-C3 [1.731 (4) Å] indicating that the resonance effect caused by the imidazole ring is stronger than that caused by the thiadiazole ring. The molecular structure is stabilized by strong (C1—H1B···N3) and ratherd weak (C4—H4···N3) intermolecular interactions resulting in chains of molecules lying along the b-axis (Table 1 and Fig. 2).

Related literature top

For general background to imidazothiadiazole derivatives, see: Palagiano et al. (1995). Accumulation of fluorine on carbon leads to increased oxidative and thermal stability, see: Strunecka et al. (2004); Park et al. (2001). For related structures, see: Yang et al. (2006).

Experimental top

A mixture of equimolar quantities of 2-amino-(4-fluorobenyl)-1,3,4-thiadiazole (2.69, 0.013 mol) and phenacyl bromide (0.01 mol) was refluxed in dry ethanol for 18 hrs. The excess of solvent was distilled off and the solid hydrobromide salt that separated was collected by filtration, suspended in water and neutralized by aqueous sodium carbonate solution to get free base 6-(4-bromophenyl)-2-(4-fluorobenzyl)imidazo[2,1-b][1,3,4]thiadiazole. It was filtered, washed with water, dried and recrystallized from ethanol.

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-3 (Farrugia, 1997) view of the title compound, showing 50% probability ellipsoids and the atom numbering scheme.
	Fig. 2. A part of the unit cell of the title compound showing intermolecular interactions with dotted lines. H-atoms not involved in hydrogen bonding have been excluded for clarity.

6-(4-Bromophenyl)-2-(4-fluorobenzyl)imidazo[2,1-b][1,3,4]thiadiazole top

Crystal data top

C₁₇H₁₁BrFN₃S	F(000) = 776
M_r = 388.26	D_x = 1.690 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3308 reflections
a = 10.505 (4) Å	θ = 2.1–27.0°
b = 5.617 (2) Å	µ = 2.84 mm⁻¹
c = 25.877 (11) Å	T = 296 K
β = 91.566 (7)°	Block, yellow
V = 1526.2 (11) Å³	0.18 × 0.16 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEX CCD detector diffractometer	3308 independent reflections
Radiation source: fine-focus sealed tube	2419 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→12
T_min = 0.629, T_max = 0.659	k = −6→7
8589 measured reflections	l = −31→33

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.063P)²] where P = (F_o² + 2F_c²)/3
3308 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

C₁₇H₁₁BrFN₃S	V = 1526.2 (11) Å³
M_r = 388.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.505 (4) Å	µ = 2.84 mm⁻¹
b = 5.617 (2) Å	T = 296 K
c = 25.877 (11) Å	0.18 × 0.16 × 0.16 mm
β = 91.566 (7)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	3308 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2419 reflections with I > 2σ(I)
T_min = 0.629, T_max = 0.659	R_int = 0.054
8589 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.13	Δρ_max = 0.86 e Å⁻³
3308 reflections	Δρ_min = −0.73 e Å⁻³
208 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.1898 (4)	0.6339 (6)	0.36994 (13)	0.0319 (8)
H1A	0.2138	0.4879	0.3877	0.038*
H1B	0.1102	0.6044	0.3512	0.038*
C2	0.2894 (3)	0.6920 (6)	0.33203 (13)	0.0278 (8)
C3	0.4220 (3)	0.8748 (6)	0.26794 (13)	0.0264 (7)
C4	0.5421 (3)	0.5636 (6)	0.25094 (13)	0.0277 (7)
H4	0.5781	0.4124	0.2508	0.033*
C5	0.6754 (3)	0.7708 (6)	0.18420 (13)	0.0253 (7)
C6	0.5751 (3)	0.7565 (6)	0.22174 (13)	0.0258 (8)
C7	0.7627 (3)	0.5856 (6)	0.17813 (13)	0.0291 (8)
H7	0.7562	0.4509	0.1988	0.035*
C8	0.8573 (3)	0.5950 (7)	0.14292 (14)	0.0335 (8)
H8	0.9144	0.4694	0.1400	0.040*
C9	0.8671 (3)	0.7945 (7)	0.11170 (14)	0.0342 (9)
C10	0.7837 (3)	0.9808 (7)	0.11643 (14)	0.0358 (9)
H10	0.7912	1.1151	0.0957	0.043*
C11	0.6881 (3)	0.9679 (6)	0.15221 (14)	0.0323 (8)
H11	0.6312	1.0939	0.1549	0.039*
C12	0.1684 (3)	0.8245 (6)	0.40960 (14)	0.0281 (8)
C13	0.0714 (3)	0.9915 (7)	0.40327 (14)	0.0336 (9)
H13	0.0187	0.9835	0.3739	0.040*
C14	0.0508 (3)	1.1678 (6)	0.43889 (14)	0.0321 (8)
H14	−0.0145	1.2781	0.4341	0.038*
C15	0.1308 (3)	1.1748 (6)	0.48200 (14)	0.0321 (8)
C16	0.2275 (3)	1.0156 (7)	0.49006 (14)	0.0367 (9)
H16	0.2803	1.0256	0.5194	0.044*
C17	0.2456 (3)	0.8396 (6)	0.45377 (14)	0.0346 (9)
H17	0.3107	0.7292	0.4590	0.042*
N1	0.3702 (3)	0.5374 (5)	0.31627 (11)	0.0317 (7)
N2	0.4447 (3)	0.6431 (5)	0.28024 (10)	0.0248 (6)
N3	0.4997 (3)	0.9534 (5)	0.23239 (11)	0.0274 (6)
S1	0.29995 (9)	0.97928 (16)	0.30528 (4)	0.0325 (2)
F1	0.1127 (2)	1.3452 (4)	0.51794 (9)	0.0436 (6)
Br1	0.99661 (4)	0.80778 (9)	0.062488 (15)	0.04750 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.039 (2)	0.033 (2)	0.0235 (18)	−0.0102 (16)	0.0011 (15)	0.0006 (15)
C2	0.0358 (19)	0.0223 (18)	0.0250 (18)	−0.0053 (15)	−0.0072 (15)	0.0042 (15)
C3	0.0315 (18)	0.0192 (17)	0.0279 (18)	−0.0006 (13)	−0.0079 (14)	0.0015 (14)
C4	0.0299 (18)	0.0196 (17)	0.0334 (19)	0.0015 (14)	−0.0052 (14)	0.0006 (15)
C5	0.0254 (17)	0.0286 (18)	0.0213 (17)	−0.0046 (14)	−0.0089 (13)	−0.0002 (14)
C6	0.0290 (18)	0.0197 (17)	0.0280 (19)	−0.0023 (13)	−0.0098 (14)	−0.0011 (14)
C7	0.0346 (19)	0.0265 (18)	0.0257 (18)	−0.0016 (15)	−0.0071 (15)	0.0010 (15)
C8	0.0309 (19)	0.036 (2)	0.033 (2)	0.0015 (16)	−0.0093 (15)	−0.0029 (17)
C9	0.0318 (19)	0.043 (2)	0.0275 (19)	−0.0122 (17)	−0.0065 (15)	−0.0046 (17)
C10	0.041 (2)	0.034 (2)	0.032 (2)	−0.0139 (17)	−0.0044 (16)	0.0087 (16)
C11	0.0339 (19)	0.0259 (19)	0.037 (2)	−0.0026 (15)	−0.0061 (16)	0.0064 (16)
C12	0.0257 (17)	0.0280 (19)	0.0303 (19)	−0.0032 (14)	−0.0011 (14)	0.0045 (15)
C13	0.0281 (18)	0.038 (2)	0.034 (2)	−0.0018 (16)	−0.0095 (15)	0.0107 (17)
C14	0.0289 (18)	0.035 (2)	0.032 (2)	0.0088 (16)	0.0037 (14)	0.0109 (16)
C15	0.0358 (19)	0.033 (2)	0.0276 (19)	0.0004 (16)	0.0081 (15)	0.0028 (16)
C16	0.037 (2)	0.042 (2)	0.030 (2)	0.0086 (17)	−0.0110 (16)	−0.0009 (17)
C17	0.0317 (19)	0.037 (2)	0.034 (2)	0.0110 (16)	−0.0053 (15)	0.0007 (16)
N1	0.0389 (17)	0.0267 (16)	0.0293 (17)	−0.0049 (13)	−0.0045 (13)	0.0036 (13)
N2	0.0315 (15)	0.0229 (15)	0.0198 (14)	−0.0028 (11)	−0.0027 (11)	0.0037 (11)
N3	0.0318 (15)	0.0231 (15)	0.0271 (15)	0.0007 (12)	−0.0040 (12)	0.0045 (12)
S1	0.0370 (5)	0.0238 (5)	0.0368 (5)	0.0019 (4)	0.0014 (4)	0.0039 (4)
F1	0.0542 (14)	0.0404 (13)	0.0364 (13)	0.0138 (11)	0.0056 (10)	−0.0061 (10)
Br1	0.0394 (3)	0.0716 (4)	0.0315 (2)	−0.0207 (2)	0.00146 (17)	−0.0057 (2)

Geometric parameters (Å, º) top

C1—C2	1.490 (5)	C8—H8	0.9300
C1—C12	1.504 (5)	C9—C10	1.373 (5)
C1—H1A	0.9700	C9—Br1	1.890 (4)
C1—H1B	0.9700	C10—C11	1.386 (5)
C2—N1	1.288 (4)	C10—H10	0.9300
C2—S1	1.761 (3)	C11—H11	0.9300
C3—N3	1.322 (4)	C12—C17	1.386 (5)
C3—N2	1.360 (4)	C12—C13	1.391 (5)
C3—S1	1.729 (4)	C13—C14	1.374 (5)
C4—N2	1.365 (4)	C13—H13	0.9300
C4—C6	1.371 (5)	C14—C15	1.379 (5)
C4—H4	0.9300	C14—H14	0.9300
C5—C11	1.391 (5)	C15—F1	1.351 (4)
C5—C7	1.399 (5)	C15—C16	1.366 (5)
C5—C6	1.455 (5)	C16—C17	1.380 (5)
C6—N3	1.392 (4)	C16—H16	0.9300
C7—C8	1.368 (5)	C17—H17	0.9300
C7—H7	0.9300	N1—N2	1.369 (4)
C8—C9	1.387 (5)

C2—C1—C12	114.5 (3)	C9—C10—C11	119.7 (3)
C2—C1—H1A	108.6	C9—C10—H10	120.1
C12—C1—H1A	108.6	C11—C10—H10	120.1
C2—C1—H1B	108.6	C10—C11—C5	121.5 (3)
C12—C1—H1B	108.6	C10—C11—H11	119.3
H1A—C1—H1B	107.6	C5—C11—H11	119.3
N1—C2—C1	122.8 (3)	C17—C12—C13	117.8 (3)
N1—C2—S1	116.4 (3)	C17—C12—C1	120.7 (3)
C1—C2—S1	120.8 (3)	C13—C12—C1	121.5 (3)
N3—C3—N2	112.0 (3)	C14—C13—C12	122.4 (3)
N3—C3—S1	139.2 (3)	C14—C13—H13	118.8
N2—C3—S1	108.8 (2)	C12—C13—H13	118.8
N2—C4—C6	104.6 (3)	C13—C14—C15	117.4 (3)
N2—C4—H4	127.7	C13—C14—H14	121.3
C6—C4—H4	127.7	C15—C14—H14	121.3
C11—C5—C7	116.8 (3)	F1—C15—C16	118.5 (3)
C11—C5—C6	121.6 (3)	F1—C15—C14	118.9 (3)
C7—C5—C6	121.5 (3)	C16—C15—C14	122.7 (3)
C4—C6—N3	111.4 (3)	C15—C16—C17	118.7 (3)
C4—C6—C5	127.6 (3)	C15—C16—H16	120.6
N3—C6—C5	121.0 (3)	C17—C16—H16	120.6
C8—C7—C5	122.5 (3)	C16—C17—C12	121.1 (3)
C8—C7—H7	118.8	C16—C17—H17	119.4
C5—C7—H7	118.8	C12—C17—H17	119.4
C7—C8—C9	119.1 (4)	C2—N1—N2	108.5 (3)
C7—C8—H8	120.5	C3—N2—C4	108.2 (3)
C9—C8—H8	120.5	C3—N2—N1	118.3 (3)
C10—C9—C8	120.4 (4)	C4—N2—N1	133.5 (3)
C10—C9—Br1	120.2 (3)	C3—N3—C6	103.8 (3)
C8—C9—Br1	119.4 (3)	C3—S1—C2	87.94 (17)

C12—C1—C2—N1	139.7 (3)	C13—C14—C15—C16	0.1 (6)
C12—C1—C2—S1	−41.6 (4)	F1—C15—C16—C17	179.3 (3)
N2—C4—C6—N3	−0.1 (4)	C14—C15—C16—C17	−0.4 (6)
N2—C4—C6—C5	179.0 (3)	C15—C16—C17—C12	0.7 (6)
C11—C5—C6—C4	171.4 (3)	C13—C12—C17—C16	−0.5 (6)
C7—C5—C6—C4	−7.8 (5)	C1—C12—C17—C16	179.2 (3)
C11—C5—C6—N3	−9.6 (5)	C1—C2—N1—N2	177.4 (3)
C7—C5—C6—N3	171.3 (3)	S1—C2—N1—N2	−1.3 (4)
C11—C5—C7—C8	0.5 (5)	N3—C3—N2—C4	−0.5 (4)
C6—C5—C7—C8	179.7 (3)	S1—C3—N2—C4	−179.3 (2)
C5—C7—C8—C9	−0.5 (5)	N3—C3—N2—N1	−179.4 (3)
C7—C8—C9—C10	0.6 (5)	S1—C3—N2—N1	1.8 (3)
C7—C8—C9—Br1	−179.4 (2)	C6—C4—N2—C3	0.3 (3)
C8—C9—C10—C11	−0.8 (5)	C6—C4—N2—N1	179.0 (3)
Br1—C9—C10—C11	179.2 (3)	C2—N1—N2—C3	−0.4 (4)
C9—C10—C11—C5	0.9 (5)	C2—N1—N2—C4	−178.9 (3)
C7—C5—C11—C10	−0.7 (5)	N2—C3—N3—C6	0.4 (4)
C6—C5—C11—C10	−179.9 (3)	S1—C3—N3—C6	178.7 (3)
C2—C1—C12—C17	−83.6 (4)	C4—C6—N3—C3	−0.2 (4)
C2—C1—C12—C13	96.2 (4)	C5—C6—N3—C3	−179.4 (3)
C17—C12—C13—C14	0.2 (5)	N3—C3—S1—C2	179.7 (4)
C1—C12—C13—C14	−179.6 (3)	N2—C3—S1—C2	−1.9 (2)
C12—C13—C14—C15	0.1 (5)	N1—C2—S1—C3	2.0 (3)
C13—C14—C15—F1	−179.7 (3)	C1—C2—S1—C3	−176.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···N3ⁱ	0.97	2.57	3.423 (5)	147
C4—H4···N3ⁱⁱ	0.93	2.74	3.488 (5)	137

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁BrFN₃S
M_r	388.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.505 (4), 5.617 (2), 25.877 (11)
β (°)	91.566 (7)
V (Å³)	1526.2 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.84
Crystal size (mm)	0.18 × 0.16 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.629, 0.659
No. of measured, independent and observed [I > 2σ(I)] reflections	8589, 3308, 2419
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.129, 1.13
No. of reflections	3308
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.73

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
C1—H1B···N3ⁱ	0.97	2.57	3.423 (5)	147
C4—H4···N3ⁱⁱ	0.93	2.74	3.488 (5)	137

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

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.

References

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