Ethyl 3-oxo-2-[(4-sulfamoylphen­yl)hydra­zono]butyrate

Upadhyay, K.K.; Rai, P.; Upadhyay, S.; Nethaji, M.

doi:10.1107/S1600536809036927

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2499

doi:10.1107/S1600536809036927

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Ethyl 3-oxo-2-[(4-sulfamoylphenyl)hydrazono]butyrate

K. K. Upadhyay,^a ^* Priyanka Rai,^b Shalini Upadhyay ^a and M. Nethaji ^c

^aDepartment of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi 221 005, India, ^bDepartment of Chemistry, Udai Pratap College (Autonomuos), Varanasi 221 002, India, and ^cDepartment of Inorganic and Physical Chemistry, Indian Institute of Sciences, Bangalore 560 012, India
^*Correspondence e-mail: drkaushalbhu@yahoo.co.in

(Received 10 August 2009; accepted 12 September 2009; online 19 September 2009)

In the title compound, C₁₂H₁₅N₃O₅S, an intramolecular N—H⋯O hydrogen bond between the hydrazine unit and one of the carbonyl groups may influence the molecular conformation. In the crystal structure, intermolecular N—H⋯O hydrogen bonds, including one which is bifurcated, link the molecules into a two-dimensional network.

Related literature

For background to sulfa drugs and their derivatives, see: Abbate et al. (2004 ); Badr (2008 ); Hanafy et al. (2007 ); Novinson et al. (1976 ); Supuran et al. (2003 ); Upadhyay et al. (2009 ); Zhong et al. (2007 ). For the synthesis of the title compound, see: Prakash & Gambhir (1964 ).

Experimental

Crystal data

C₁₂H₁₅N₃O₅S
M_r = 313.33
Monoclinic, P 2₁ /n
a = 7.490 (6) Å
b = 14.819 (12) Å
c = 12.689 (10) Å
β = 95.219 (14)°
V = 1402.6 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.940, T_max = 0.951
11777 measured reflections
3274 independent reflections
2177 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.222
S = 0.87
3274 reflections
200 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	1.95	2.597 (5)	131
N3—H3B⋯O6ⁱ	0.77 (5)	2.33 (4)	2.941 (6)	137 (4)
N3—H3B⋯O5ⁱ	0.77 (5)	2.52 (5)	3.208 (6)	149 (5)
N3—H3A⋯O4ⁱⁱ	0.85 (5)	2.21 (5)	3.003 (6)	154 (4)
Symmetry codes: (i) -x, -y, -z+2; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036927/lh2879sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036927/lh2879Isup2.hkl

checkCIF report

Comment top

Sulfadrugs and their derivatives have attracted much attention due to their wide spectrum of pharamaceutical (Abbate et al., 2004; Badr, 2008; Supuran et al., 2003) and biological applications (Hanafy et al., 2007, Zhong et al., 2007). Recently we reported details of a diazo derivative of sulfathiazole (Upadhyay et al.,2009) as a naked eye sensor for Hg(II) in DMSO. Although the title compound (I) has been reported in the literature (Prakash & Gambhir, 1964) its crystal structure determination has not been undertaken until now.

The molecular structure of the title compound is shown in Fig. 1. An intramolecular N—H···O hydrogen bond between the hydrazine unit and one carbonyl groups may influence the molecular conformation. In the crystal structure, intermolecular N—H···O hydrogen bonds, including one which which is bifurcated, link molecules in a two-dimensional network (see Fig. 2).

Related literature top

For background to sulfa drugs and their derivatives, see: Abbate et al. (2004); Badr (2008); Hanafy et al. (2007); Novinson et al. (1976); Supuran et al. (2003); Upadhyay et al. (2009); Zhong et al. (2007). For the synthesis of the title compound, see: Prakash & Gambhir (1964).

Experimental top

Compound (I) was synthesized using the literature procedure (Novinson et al., 1976) as follows. Sulphanilamide (2 mmol, 344 mg) and sodium nitrite (~4 mmol, 300 mg) were dissolved separately in conc. HCl (2 ml) and distilled water (10 ml), respectively, followed by cooling on crushed ice. The cooled sodium nitrite solution was added to the sulphanilamide solution with constant stirring while maintaining the temperature. The resulting yellow solution was added to a mixture of ethyl aceto acetate (2 mmol, 0.25 ml) and sodium acetate (~37 mmol, 3 g) in distilled water (15 ml) with continuous stirring. The stirring was continued further for 2 h maintaining the temperature of the reaction vessel between 293–298 K. The resulting solids were filtered, washed with water, ethanol and finally, by diethyl ether. The crude product was recrystallized from a water–ethanol mixture (50% v/v) and dried in vacuo. Crystals were grown by layering a supersaturated solution of (I) in ethanol with diethylether and leaving for a few days.

Yield 76%. Spectroscopic anaylysis: ¹HNMR (DMSO-d₆, TMS, δp.p.m.) 11.60 (1H, –HN—N=C<), 7.85–7.54 (m, 4H, Ar—H), 7.34 (s, 2H, NH₂),4.35–4.26 (2H, CH₂), 2.50–2.42(3H, CH₃ of C₂H₅), 1.33–1.26 (3H, CH₃). ¹³C NMR (DMSO-d₆, TMS, δ p.p.m.) 193.90 (>C=O),162.33 [C(OEt)=O], 145.16,138.31(C=C), 133.35, 127.36, 115.89, 114.76 (Ar—C), 61.37 (–CH₂), 25.28,13.83 (–CH₃).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of compound (I) showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of (I) showing intramolecular and intermolecular hydrogen bonds as hashed lines.

Ethyl 3-oxo-2-[(4-sulfamoylphenyl)hydrazono]butyrate top

Crystal data top

C₁₂H₁₅N₃O₅S	F(000) = 656
M_r = 313.33	D_x = 1.484 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 398 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.490 (6) Å	Cell parameters from 598 reflections
b = 14.819 (12) Å	θ = 2.5–27.5°
c = 12.689 (10) Å	µ = 0.26 mm⁻¹
β = 95.219 (14)°	T = 293 K
V = 1402.6 (19) Å³	Rectangular, colourless
Z = 4	0.24 × 0.22 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	3274 independent reflections
Radiation source: fine-focus sealed tube	2177 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 0.3 pixels mm^-1	θ_max = 28.2°, θ_min = 2.1°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −17→19
T_min = 0.940, T_max = 0.951	l = −16→16
11777 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full with fixed elements per cycle	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.222	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ²(F_o²) + (0.1321P)² + 2.1941P] where P = (F_o² + 2F_c²)/3
3274 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₂H₁₅N₃O₅S	V = 1402.6 (19) Å³
M_r = 313.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.490 (6) Å	µ = 0.26 mm⁻¹
b = 14.819 (12) Å	T = 293 K
c = 12.689 (10) Å	0.24 × 0.22 × 0.20 mm
β = 95.219 (14)°

Data collection top

Bruker SMART APEX diffractometer	3274 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2177 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.951	R_int = 0.052
11777 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.222	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	Δρ_max = 0.59 e Å⁻³
3274 reflections	Δρ_min = −0.32 e Å⁻³
200 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
C1	0.2438 (5)	0.0661 (2)	0.9456 (3)	0.0391 (8)
C2	0.2126 (5)	0.1343 (2)	1.0159 (3)	0.0429 (8)
H2	0.1983	0.1209	1.0862	0.051*
C3	0.2030 (5)	0.2223 (2)	0.9809 (3)	0.0433 (8)
H3	0.1809	0.2684	1.0278	0.052*
C4	0.2258 (5)	0.2424 (2)	0.8772 (2)	0.0372 (7)
C5	0.2609 (6)	0.1745 (2)	0.8081 (3)	0.0518 (10)
H5	0.2790	0.1883	0.7384	0.062*
C6	0.2693 (6)	0.0861 (2)	0.8420 (3)	0.0536 (10)
H6	0.2920	0.0401	0.7951	0.064*
C7	0.2498 (5)	−0.1296 (2)	1.1080 (3)	0.0400 (8)
C8	0.2482 (5)	−0.1381 (2)	1.2239 (3)	0.0451 (9)
C9	0.2452 (7)	−0.0539 (3)	1.2876 (3)	0.0659 (13)
H9A	0.2411	−0.0691	1.3609	0.099*
H9B	0.1412	−0.0190	1.2639	0.099*
H9C	0.3513	−0.0193	1.2791	0.099*
C10	0.2599 (5)	−0.2072 (2)	1.0344 (3)	0.0466 (9)
C11	0.2122 (7)	−0.3643 (3)	0.9952 (4)	0.0624 (12)
H11A	0.1498	−0.4147	1.0240	0.075*
H11B	0.1458	−0.3458	0.9296	0.075*
C12	0.3910 (8)	−0.3914 (3)	0.9752 (5)	0.0868 (17)
H12A	0.4491	−0.3427	0.9419	0.130*
H12B	0.3847	−0.4431	0.9294	0.130*
H12C	0.4583	−0.4064	1.0409	0.130*
H3A	0.042 (6)	0.330 (3)	0.688 (4)	0.055 (13)*
H3B	−0.064 (6)	0.334 (3)	0.769 (4)	0.049 (14)*
N1	0.2500 (4)	−0.02524 (19)	0.9754 (2)	0.0469 (8)
H1	0.2567	−0.0667	0.9286	0.056*
N2	0.2454 (4)	−0.0464 (2)	1.0745 (2)	0.0417 (7)
N3	0.0211 (6)	0.3532 (2)	0.7471 (3)	0.0481 (8)
O1	0.1619 (4)	0.40903 (16)	0.9163 (2)	0.0565 (8)
O2	0.3416 (4)	0.37652 (19)	0.7692 (2)	0.0581 (8)
O4	0.2924 (5)	−0.19684 (19)	0.9443 (2)	0.0711 (10)
O5	0.2233 (5)	−0.28696 (17)	1.0729 (2)	0.0620 (8)
O6	0.2547 (5)	−0.21135 (18)	1.2667 (2)	0.0703 (9)
S1	0.19753 (14)	0.35341 (5)	0.82925 (7)	0.0425 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.049 (2)	0.0279 (16)	0.0399 (17)	0.0027 (14)	0.0025 (15)	0.0052 (13)
C2	0.062 (2)	0.0381 (18)	0.0278 (15)	0.0020 (16)	0.0020 (15)	0.0040 (13)
C3	0.064 (2)	0.0317 (17)	0.0343 (16)	0.0012 (15)	0.0031 (15)	−0.0030 (13)
C4	0.052 (2)	0.0285 (15)	0.0305 (15)	−0.0009 (14)	0.0022 (14)	0.0018 (12)
C5	0.090 (3)	0.0346 (18)	0.0333 (17)	0.0059 (19)	0.0183 (18)	0.0050 (14)
C6	0.094 (3)	0.0294 (17)	0.0392 (19)	0.0098 (19)	0.0148 (19)	0.0008 (14)
C7	0.050 (2)	0.0328 (17)	0.0372 (17)	−0.0006 (14)	0.0043 (15)	0.0048 (13)
C8	0.055 (2)	0.0417 (19)	0.0383 (18)	−0.0101 (16)	0.0017 (16)	0.0054 (15)
C9	0.107 (4)	0.049 (2)	0.043 (2)	−0.015 (2)	0.010 (2)	−0.0031 (18)
C10	0.064 (2)	0.0351 (18)	0.0416 (19)	0.0099 (16)	0.0103 (17)	0.0076 (15)
C11	0.087 (3)	0.043 (2)	0.059 (3)	−0.006 (2)	0.021 (2)	0.0042 (18)
C12	0.091 (4)	0.053 (3)	0.112 (5)	0.004 (3)	−0.009 (3)	0.000 (3)
N1	0.073 (2)	0.0307 (15)	0.0374 (15)	0.0042 (14)	0.0051 (14)	0.0063 (12)
N2	0.0537 (18)	0.0352 (15)	0.0361 (14)	−0.0017 (13)	0.0032 (12)	0.0083 (12)
N3	0.065 (2)	0.0373 (17)	0.0423 (18)	0.0005 (16)	0.0055 (16)	0.0075 (14)
O1	0.088 (2)	0.0294 (12)	0.0521 (15)	−0.0011 (13)	0.0082 (14)	−0.0060 (11)
O2	0.0708 (19)	0.0462 (15)	0.0591 (17)	−0.0080 (13)	0.0152 (14)	0.0121 (13)
O4	0.134 (3)	0.0380 (15)	0.0465 (15)	0.0136 (16)	0.0350 (18)	0.0071 (12)
O5	0.113 (2)	0.0307 (13)	0.0460 (15)	0.0019 (14)	0.0270 (15)	0.0046 (11)
O6	0.129 (3)	0.0427 (16)	0.0384 (14)	−0.0148 (17)	0.0026 (16)	0.0117 (12)
S1	0.0625 (6)	0.0252 (4)	0.0400 (5)	−0.0026 (4)	0.0053 (4)	0.0042 (3)

Geometric parameters (Å, º) top

C1—C6	1.379 (5)	C9—H9B	0.9600
C1—C2	1.382 (5)	C9—H9C	0.9600
C1—N1	1.404 (4)	C10—O4	1.200 (4)
C2—C3	1.378 (5)	C10—O5	1.317 (4)
C2—H2	0.9300	C11—C12	1.443 (7)
C3—C4	1.375 (5)	C11—O5	1.509 (5)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.376 (5)	C11—H11B	0.9700
C4—S1	1.760 (3)	C12—H12A	0.9600
C5—C6	1.379 (5)	C12—H12B	0.9600
C5—H5	0.9300	C12—H12C	0.9600
C6—H6	0.9300	N1—N2	1.300 (4)
C7—N2	1.304 (4)	N1—H1	0.8600
C7—C8	1.477 (5)	N3—S1	1.607 (4)
C7—C10	1.488 (5)	N3—H3A	0.85 (5)
C8—O6	1.213 (4)	N3—H3B	0.77 (4)
C8—C9	1.488 (5)	O1—S1	1.423 (3)
C9—H9A	0.9600	O2—S1	1.419 (3)

C6—C1—C2	120.3 (3)	O4—C10—O5	122.4 (4)
C6—C1—N1	117.4 (3)	O4—C10—C7	121.7 (3)
C2—C1—N1	122.3 (3)	O5—C10—C7	115.9 (3)
C3—C2—C1	119.5 (3)	C12—C11—O5	109.3 (4)
C3—C2—H2	120.3	C12—C11—H11A	109.8
C1—C2—H2	120.3	O5—C11—H11A	109.8
C4—C3—C2	120.4 (3)	C12—C11—H11B	109.8
C4—C3—H3	119.8	O5—C11—H11B	109.8
C2—C3—H3	119.8	H11A—C11—H11B	108.3
C3—C4—C5	120.0 (3)	C11—C12—H12A	109.5
C3—C4—S1	120.8 (3)	C11—C12—H12B	109.5
C5—C4—S1	119.1 (3)	H12A—C12—H12B	109.5
C4—C5—C6	120.1 (3)	C11—C12—H12C	109.5
C4—C5—H5	119.9	H12A—C12—H12C	109.5
C6—C5—H5	119.9	H12B—C12—H12C	109.5
C1—C6—C5	119.7 (3)	N2—N1—C1	119.3 (3)
C1—C6—H6	120.1	N2—N1—H1	120.3
C5—C6—H6	120.1	C1—N1—H1	120.3
N2—C7—C8	113.7 (3)	N1—N2—C7	122.7 (3)
N2—C7—C10	121.9 (3)	S1—N3—H3A	111 (3)
C8—C7—C10	124.4 (3)	S1—N3—H3B	115 (3)
O6—C8—C7	121.2 (3)	H3A—N3—H3B	113 (5)
O6—C8—C9	120.6 (3)	C10—O5—C11	116.1 (3)
C7—C8—C9	118.1 (3)	O2—S1—O1	118.86 (18)
C8—C9—H9A	109.5	O2—S1—N3	105.8 (2)
C8—C9—H9B	109.5	O1—S1—N3	107.7 (2)
H9A—C9—H9B	109.5	O2—S1—C4	109.76 (17)
C8—C9—H9C	109.5	O1—S1—C4	107.32 (16)
H9A—C9—H9C	109.5	N3—S1—C4	106.76 (17)
H9B—C9—H9C	109.5

C6—C1—C2—C3	1.5 (6)	N2—C7—C10—O5	−165.3 (4)
N1—C1—C2—C3	−178.1 (3)	C8—C7—C10—O5	16.2 (6)
C1—C2—C3—C4	−0.6 (6)	C6—C1—N1—N2	172.9 (4)
C2—C3—C4—C5	−0.9 (6)	C2—C1—N1—N2	−7.5 (5)
C2—C3—C4—S1	175.3 (3)	C1—N1—N2—C7	179.7 (3)
C3—C4—C5—C6	1.5 (6)	C8—C7—N2—N1	178.4 (3)
S1—C4—C5—C6	−174.8 (3)	C10—C7—N2—N1	−0.2 (6)
C2—C1—C6—C5	−1.0 (6)	O4—C10—O5—C11	−4.0 (6)
N1—C1—C6—C5	178.7 (4)	C7—C10—O5—C11	173.1 (3)
C4—C5—C6—C1	−0.5 (7)	C12—C11—O5—C10	77.1 (5)
N2—C7—C8—O6	−178.8 (4)	C3—C4—S1—O2	133.9 (3)
C10—C7—C8—O6	−0.3 (6)	C5—C4—S1—O2	−49.9 (4)
N2—C7—C8—C9	−1.0 (5)	C3—C4—S1—O1	3.4 (4)
C10—C7—C8—C9	177.5 (4)	C5—C4—S1—O1	179.6 (3)
N2—C7—C10—O4	11.8 (6)	C3—C4—S1—N3	−111.9 (3)
C8—C7—C10—O4	−166.7 (4)	C5—C4—S1—N3	64.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	1.95	2.597 (5)	131
N3—H3B···O6ⁱ	0.77 (5)	2.33 (4)	2.941 (6)	137 (4)
N3—H3B···O5ⁱ	0.77 (5)	2.52 (5)	3.208 (6)	149 (5)
N3—H3A···O4ⁱⁱ	0.85 (5)	2.21 (5)	3.003 (6)	154 (4)

Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅N₃O₅S
M_r	313.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.490 (6), 14.819 (12), 12.689 (10)
β (°)	95.219 (14)
V (Å³)	1402.6 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.940, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	11777, 3274, 2177
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.665

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.222, 0.87
No. of reflections	3274
No. of parameters	200
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.32

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	1.95	2.597 (5)	131.00
N3—H3B···O6ⁱ	0.77 (5)	2.33 (4)	2.941 (6)	137 (4)
N3—H3B···O5ⁱ	0.77 (5)	2.52 (5)	3.208 (6)	149 (5)
N3—H3A···O4ⁱⁱ	0.85 (5)	2.21 (5)	3.003 (6)	154 (4)

Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1/2, y+1/2, −z+3/2.

Acknowledgements

KKU and SU are grateful to the CSIR, New Delhi, for financial support.

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