N-(3-Chloro­benzo­yl)-2-nitro­benzene­sulfonamide

Suchetan, P.A.; Foro, S.; Gowda, B.T.; Prakash, M.S.

doi:10.1107/S160053681200640X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o786

doi:10.1107/S160053681200640X

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N-(3-Chlorobenzoyl)-2-nitrobenzenesulfonamide

P. A. Suchetan,^a Sabine Foro,^b B. Thimme Gowda ^a ^* and M. Shet Prakash ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cDepartment of Chemistry, University College of Science, Tumkur University, Tumkur 572 102, India
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 8 February 2012; accepted 13 February 2012; online 17 February 2012)

In the title compound, C₁₃H₉ClN₂O₅S, the N—C bond in the C—SO₂—NH—C segment has a gauche torsion with respect to the S=O bonds. The conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn, and that between the C=O and the meta-Cl atom in the benzoyl ring is anti. The molecule is twisted at the S—N bond, with a torsion angle of 65.41 (38)°. The dihedral angle between the sulfonyl benzene ring and the –SO₂—NH—C—O segment is 75.0 (1)°, and that between the sulfonyl and the benzoyl benzene ring is 89.1 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) hydrogen bonds.

Related literature

For our studies of the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (1999 , 2006 ); N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ); N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2012 ); N-chloroarylamides, see: Jyothi & Gowda (2004 ) and N-bromoarylsulfonamides, see: Usha & Gowda (2006 )..

Experimental

Crystal data

C₁₃H₉ClN₂O₅S
M_r = 340.73
Orthorhombic, P b c a
a = 12.2046 (8) Å
b = 12.6121 (9) Å
c = 18.433 (1) Å
V = 2837.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 293 K
0.28 × 0.28 × 0.08 mm

Data collection

Oxford Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.886, T_max = 0.966
11298 measured reflections
2889 independent reflections
1911 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.147
S = 1.20
2889 reflections
202 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 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⋯O1ⁱ	0.86 (2)	2.41 (3)	3.193 (4)	153 (4)
Symmetry code: (i) -x, -y+2, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681200640X/nc2268sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200640X/nc2268Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200640X/nc2268Isup3.cml

checkCIF report

Comment top

As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 1999, 2006), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2012), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(3-chlorobenzoyl)-2-nitrobenzenesulfonamide has been determined (Fig.1).

The conformation between the N—H and C═O bonds in the C—SO₂—NH—C(O) segment is anti and the N—C bond in the segment has gauche torsion with respect to the S═O bonds (Fig. 1), similar to that observed in N-(2-chlorobenzoyl)-2-nitrobenzenesulfonamide (I) (Suchetan et al., 2012). In the title compound, the conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn, similar to that observed in (I). Further, the conformation of the C═O is anti to the meta-Cl atom in the benzoyl ring, similar to that observed between the C═O and the ortho-Cl atom in (I).

The molecule is twisted at the S—N bond with the torsional angle of 65.41 (38)°, compared to the value of -59.68 (17)° in (I).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 75.0 (1)°, compared to the value of 77.5 (1)° in (I). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 89.1 (1)°, compared to the value of 71.2 (1)° in (I).

In the crystal structure two molecules each are linked by pairs of intermolecular N—H···O (S) hydrogen bonds into dimers that are located around centers of inversion (Fig. 2 and Table 1).

Related literature top

For our studies of the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (1999, 2006); N-(aryl)-methanesulfonamides, see: Gowda et al. (2007); N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2012); N-chloroarylamides, see: Jyothi & Gowda (2004) and N-bromoarylsulfonamides, see: Usha & Gowda (2006)..

Experimental top

The title compound was prepared by refluxing a mixture of 3-chlorobenzoic acid (0.02 mole), 2-nitrobenzenesulfonamide (0.02 mole) and excess phosphorous oxychloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(3-chlorobenzoyl)-2-nitrobenzenesulfonamide, obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.

Rod like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of the solvent from its toluene solution at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. View of the inversion-related dimers linked by pairs of N—H···O(S) hydrogen bonds (Hydrogen bonding is shown as dashed lines)..

N-(3-Chlorobenzoyl)-2-nitrobenzenesulfonamide top

Crystal data top

C₁₃H₉ClN₂O₅S	F(000) = 1392
M_r = 340.73	D_x = 1.595 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1818 reflections
a = 12.2046 (8) Å	θ = 2.6–27.9°
b = 12.6121 (9) Å	µ = 0.44 mm⁻¹
c = 18.433 (1) Å	T = 293 K
V = 2837.3 (3) Å³	Rod, colourless
Z = 8	0.28 × 0.28 × 0.08 mm

Data collection top

Oxford Xcalibur diffractometer with Sapphire CCD detector	2889 independent reflections
Radiation source: fine-focus sealed tube	1911 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→15
T_min = 0.886, T_max = 0.966	k = −15→11
11298 measured reflections	l = −22→23

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ²(F_o²) + (0.0362P)² + 4.7309P] where P = (F_o² + 2F_c²)/3
2889 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.34 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₉ClN₂O₅S	V = 2837.3 (3) Å³
M_r = 340.73	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.2046 (8) Å	µ = 0.44 mm⁻¹
b = 12.6121 (9) Å	T = 293 K
c = 18.433 (1) Å	0.28 × 0.28 × 0.08 mm

Data collection top

Oxford Xcalibur diffractometer with Sapphire CCD detector	2889 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1911 reflections with I > 2σ(I)
T_min = 0.886, T_max = 0.966	R_int = 0.051
11298 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	1 restraint
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	Δρ_max = 0.34 e Å⁻³
2889 reflections	Δρ_min = −0.29 e Å⁻³
202 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	−0.0112 (3)	0.7252 (3)	0.0676 (2)	0.0347 (9)
C2	−0.0862 (3)	0.7030 (3)	0.0131 (2)	0.0402 (10)
C3	−0.1369 (4)	0.6063 (4)	0.0079 (3)	0.0503 (12)
H3	−0.1854	0.5924	−0.0298	0.060*
C4	−0.1152 (4)	0.5307 (4)	0.0590 (3)	0.0552 (13)
H4	−0.1498	0.4652	0.0563	0.066*
C5	−0.0427 (4)	0.5506 (4)	0.1143 (3)	0.0537 (13)
H5	−0.0286	0.4986	0.1488	0.064*
C6	0.0092 (4)	0.6469 (3)	0.1188 (2)	0.0450 (11)
H6	0.0582	0.6598	0.1564	0.054*
C7	−0.0490 (3)	0.9234 (3)	0.1845 (2)	0.0389 (10)
C8	−0.1239 (3)	1.0094 (3)	0.2089 (2)	0.0354 (9)
C9	−0.1284 (3)	1.1061 (3)	0.1738 (2)	0.0390 (10)
H9	−0.0812	1.1205	0.1354	0.047*
C10	−0.2036 (4)	1.1812 (3)	0.1960 (2)	0.0400 (10)
C11	−0.2730 (4)	1.1613 (4)	0.2528 (2)	0.0456 (11)
H11	−0.3240	1.2119	0.2672	0.055*
C12	−0.2663 (4)	1.0654 (4)	0.2884 (2)	0.0499 (12)
H12	−0.3127	1.0518	0.3273	0.060*
C13	−0.1921 (4)	0.9897 (3)	0.2670 (2)	0.0452 (11)
H13	−0.1879	0.9254	0.2915	0.054*
N1	−0.0153 (3)	0.9315 (3)	0.11212 (18)	0.0400 (9)
H1N	−0.050 (3)	0.966 (3)	0.0794 (18)	0.048*
N2	−0.1148 (3)	0.7825 (3)	−0.0428 (2)	0.0528 (10)
O1	0.0765 (2)	0.8844 (2)	−0.00038 (15)	0.0478 (8)
O2	0.1576 (2)	0.8265 (2)	0.11536 (16)	0.0514 (8)
O3	−0.0201 (3)	0.8509 (2)	0.22210 (16)	0.0538 (8)
O4	−0.1559 (3)	0.8640 (3)	−0.0218 (2)	0.0730 (11)
O5	−0.0955 (3)	0.7592 (3)	−0.10577 (18)	0.0747 (11)
Cl1	−0.20968 (12)	1.29932 (10)	0.14917 (7)	0.0697 (4)
S1	0.06425 (8)	0.84464 (8)	0.07160 (6)	0.0381 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.036 (2)	0.030 (2)	0.038 (2)	0.0025 (18)	0.0033 (19)	0.0001 (18)
C2	0.037 (2)	0.044 (3)	0.040 (2)	0.007 (2)	0.0002 (19)	0.011 (2)
C3	0.042 (3)	0.054 (3)	0.055 (3)	−0.004 (2)	−0.008 (2)	0.004 (2)
C4	0.063 (3)	0.037 (3)	0.066 (3)	−0.011 (2)	−0.001 (3)	0.007 (2)
C5	0.068 (3)	0.041 (3)	0.052 (3)	0.005 (2)	−0.005 (3)	0.013 (2)
C6	0.052 (3)	0.043 (3)	0.040 (2)	0.007 (2)	−0.010 (2)	0.003 (2)
C7	0.044 (3)	0.037 (2)	0.035 (2)	−0.004 (2)	0.0004 (19)	0.0011 (19)
C8	0.039 (2)	0.036 (2)	0.031 (2)	−0.003 (2)	0.0033 (18)	−0.0040 (17)
C9	0.043 (3)	0.041 (2)	0.033 (2)	−0.004 (2)	0.0097 (19)	−0.0018 (18)
C10	0.049 (3)	0.033 (2)	0.037 (2)	−0.004 (2)	0.001 (2)	−0.0022 (18)
C11	0.047 (3)	0.048 (3)	0.042 (2)	0.002 (2)	0.009 (2)	−0.013 (2)
C12	0.060 (3)	0.050 (3)	0.040 (2)	−0.008 (3)	0.018 (2)	−0.005 (2)
C13	0.061 (3)	0.037 (2)	0.037 (2)	−0.006 (2)	0.009 (2)	−0.0048 (19)
N1	0.048 (2)	0.040 (2)	0.0329 (19)	0.0065 (18)	0.0043 (16)	0.0036 (16)
N2	0.049 (2)	0.057 (3)	0.053 (3)	−0.004 (2)	−0.012 (2)	0.016 (2)
O1	0.0518 (19)	0.0507 (18)	0.0411 (16)	−0.0011 (15)	0.0137 (14)	0.0022 (14)
O2	0.0366 (17)	0.060 (2)	0.0577 (19)	0.0028 (16)	−0.0076 (15)	−0.0045 (16)
O3	0.068 (2)	0.0485 (19)	0.0450 (17)	0.0083 (18)	0.0041 (16)	0.0094 (16)
O4	0.090 (3)	0.052 (2)	0.077 (3)	0.018 (2)	−0.007 (2)	0.0162 (19)
O5	0.087 (3)	0.098 (3)	0.0394 (19)	−0.011 (2)	−0.0108 (19)	0.0131 (19)
Cl1	0.0894 (11)	0.0479 (7)	0.0718 (9)	0.0188 (7)	0.0221 (7)	0.0146 (6)
S1	0.0379 (6)	0.0399 (6)	0.0365 (5)	0.0018 (5)	0.0035 (5)	−0.0007 (5)

Geometric parameters (Å, º) top

C1—C6	1.388 (5)	C8—C9	1.382 (5)
C1—C2	1.389 (6)	C9—C10	1.381 (6)
C1—S1	1.767 (4)	C9—H9	0.9300
C2—C3	1.371 (6)	C10—C11	1.369 (6)
C2—N2	1.479 (5)	C10—Cl1	1.723 (4)
C3—C4	1.366 (6)	C11—C12	1.378 (6)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.373 (6)	C12—C13	1.374 (6)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.372 (6)	C13—H13	0.9300
C5—H5	0.9300	N1—S1	1.643 (4)
C6—H6	0.9300	N1—H1N	0.857 (19)
C7—O3	1.201 (5)	N2—O4	1.207 (5)
C7—N1	1.399 (5)	N2—O5	1.221 (5)
C7—C8	1.489 (6)	O1—S1	1.426 (3)
C8—C13	1.379 (5)	O2—S1	1.414 (3)

C6—C1—C2	117.8 (4)	C8—C9—H9	120.2
C6—C1—S1	119.0 (3)	C11—C10—C9	120.8 (4)
C2—C1—S1	123.1 (3)	C11—C10—Cl1	121.0 (3)
C3—C2—C1	121.9 (4)	C9—C10—Cl1	118.2 (3)
C3—C2—N2	116.7 (4)	C10—C11—C12	119.2 (4)
C1—C2—N2	121.5 (4)	C10—C11—H11	120.4
C4—C3—C2	119.0 (4)	C12—C11—H11	120.4
C4—C3—H3	120.5	C13—C12—C11	120.8 (4)
C2—C3—H3	120.5	C13—C12—H12	119.6
C3—C4—C5	120.7 (4)	C11—C12—H12	119.6
C3—C4—H4	119.7	C12—C13—C8	119.7 (4)
C5—C4—H4	119.7	C12—C13—H13	120.2
C6—C5—C4	120.2 (4)	C8—C13—H13	120.2
C6—C5—H5	119.9	C7—N1—S1	123.9 (3)
C4—C5—H5	119.9	C7—N1—H1N	124 (3)
C5—C6—C1	120.4 (4)	S1—N1—H1N	108 (3)
C5—C6—H6	119.8	O4—N2—O5	126.1 (4)
C1—C6—H6	119.8	O4—N2—C2	116.9 (4)
O3—C7—N1	121.3 (4)	O5—N2—C2	117.0 (4)
O3—C7—C8	124.1 (4)	O2—S1—O1	120.19 (19)
N1—C7—C8	114.5 (4)	O2—S1—N1	108.94 (18)
C13—C8—C9	119.9 (4)	O1—S1—N1	104.51 (18)
C13—C8—C7	118.3 (4)	O2—S1—C1	107.76 (19)
C9—C8—C7	121.7 (4)	O1—S1—C1	108.41 (19)
C10—C9—C8	119.5 (4)	N1—S1—C1	106.23 (18)
C10—C9—H9	120.2

C6—C1—C2—C3	−1.8 (6)	Cl1—C10—C11—C12	179.3 (3)
S1—C1—C2—C3	174.5 (3)	C10—C11—C12—C13	−0.7 (7)
C6—C1—C2—N2	178.6 (4)	C11—C12—C13—C8	−0.4 (7)
S1—C1—C2—N2	−5.0 (6)	C9—C8—C13—C12	1.7 (6)
C1—C2—C3—C4	1.8 (7)	C7—C8—C13—C12	−176.5 (4)
N2—C2—C3—C4	−178.7 (4)	O3—C7—N1—S1	0.6 (6)
C2—C3—C4—C5	−0.7 (7)	C8—C7—N1—S1	−178.1 (3)
C3—C4—C5—C6	−0.2 (7)	C3—C2—N2—O4	119.2 (5)
C4—C5—C6—C1	0.1 (7)	C1—C2—N2—O4	−61.2 (6)
C2—C1—C6—C5	0.9 (6)	C3—C2—N2—O5	−60.2 (6)
S1—C1—C6—C5	−175.6 (3)	C1—C2—N2—O5	119.4 (5)
O3—C7—C8—C13	−22.3 (6)	C7—N1—S1—O2	−50.4 (4)
N1—C7—C8—C13	156.3 (4)	C7—N1—S1—O1	179.9 (3)
O3—C7—C8—C9	159.5 (4)	C7—N1—S1—C1	65.4 (4)
N1—C7—C8—C9	−21.9 (6)	C6—C1—S1—O2	17.3 (4)
C13—C8—C9—C10	−1.7 (6)	C2—C1—S1—O2	−159.0 (3)
C7—C8—C9—C10	176.4 (4)	C6—C1—S1—O1	148.9 (3)
C8—C9—C10—C11	0.5 (6)	C2—C1—S1—O1	−27.4 (4)
C8—C9—C10—Cl1	−178.1 (3)	C6—C1—S1—N1	−99.3 (3)
C9—C10—C11—C12	0.7 (7)	C2—C1—S1—N1	84.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86 (2)	2.41 (3)	3.193 (4)	153 (4)

Symmetry code: (i) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₉ClN₂O₅S
M_r	340.73
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	12.2046 (8), 12.6121 (9), 18.433 (1)
V (Å³)	2837.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.28 × 0.28 × 0.08

Data collection
Diffractometer	Oxford Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.886, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	11298, 2889, 1911
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.147, 1.20
No. of reflections	2889
No. of parameters	202
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.29

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.857 (19)	2.41 (3)	3.193 (4)	153 (4)

Symmetry code: (i) −x, −y+2, −z.

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under a UGC-BSR one-time grant to faculty.

References

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