N,N′-Bis(4-chloro­phen­yl)maleamide

Shakuntala, K.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811017636

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1415

doi:10.1107/S1600536811017636

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N,N′-Bis(4-chlorophenyl)maleamide

K. Shakuntala,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

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

(Received 9 May 2011; accepted 10 May 2011; online 14 May 2011)

In the crystal of the title compound, C₁₆H₁₂Cl₂N₂O₂, the two C=O groups are anti to each other, while one of them is syn and the other is anti to their adjacent C—H bonds. The two benzene rings are oriented at an interplanar angle of 56.4 (1)°, while the dihedral angles between the central amide group (N–C–C–C–C–N) and these rings are 3.6 (1) and 54.1 (1)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into infinite chains along the a axis.

Related literature

For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2004 , 2011 ) and on the structures of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₂Cl₂N₂O₂
M_r = 335.18
Monoclinic, P 2₁ /n
a = 9.2397 (7) Å
b = 13.0154 (8) Å
c = 13.1239 (9) Å
β = 107.916 (9)°
V = 1501.73 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 293 K
0.44 × 0.44 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.830, T_max = 0.872
6063 measured reflections
3065 independent reflections
2523 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.091
S = 1.06
3065 reflections
205 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.84 (1)	2.05 (2)	2.8836 (16)	169 (2)
N2—H2N⋯O1	0.86 (1)	1.83 (2)	2.6639 (17)	162 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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/S1600536811017636/bq2300sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017636/bq2300Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017636/bq2300Isup3.cml

checkCIF report

Comment top

The amide moiety is an important constituent of many biologically significant compounds. As a part of studying the effect of substitutions on the structures of this class of compounds (Gowda et al., 2004, 2007, 2011), the crystal structure of N,N-bis(4-chlorophenyl)-maleamide has been determined (I) (Fig. 1). In the structure, the conformations of N—H and C=O bonds in both the amide groups of the C—NH—CO—CH ═CH—CO—NH—C segment are anti to each other. The two C=O bonds are also anti to each other, while one of them is syn to the adjacent C—H bond and the other is anti to its adjacent C—H bond, similar to that observed in N,N-bis(phenyl)-maleamide (II) (Gowda et al., 2011).

Further, C1—N1—C7—C8 and C11—N2—C10—C9 segments are nearly linear. The torsion angles of C2—C1—N1—C7 and C6—C1—N1—C7 are -7.0 (3)° and 174.2 (2)°, respectively, compared to the values of 174.4 (3)° and -4.9 (4)° in (II). The torsion angles of C12—C11—N2—C10 and C16—C11—N2—C10 are 122.7 (2)° and -59.1 (2)°, in contrast to the values of 40.4 (4)° and -143.9 (3)° in (II).

The two phenyl rings in (I) make an interplanar angle of 56.4 (1)°, compared to the value of 41.2 (1)° in (II). The two benzene rings (C1 to C6 and C11 to C16) make the dihedral angles of 3.6 (1)° and 54.1 (1)°, respectively, with the central amide group (N1—C7—C8—C9—C10—N2), compared to the corresponding values of 8.0 (1)° and 38.3 (1)° in (II).

The crystal structure exhibits both the intramolecular and intermolecular N–H···O hydrogen bonding (Table 1). The packing of molecules through intermolecular N–H···O hydrogen bonds is shown in Fig. 2.

Related literature top

For our study of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2004, 2011) and on the structures of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007).

Experimental top

A mixture of maleic acid (0.2 mol) and phosphorous oxy chloride (0.3 mol) were refluxed for 3 hrs on a water bath at 95° C. 4-Chloroaniline was added dropwise with stirring and continuing heating for about 30 min. It was later kept aside for 12 hrs for completion of the reaction. The reaction mixture was then added to ice. The precipitated product was washed with water, dilute HCl, dilute NaOH and again with water. The product was filtered, dried and recrystallized from DMF.

Prism like dark-grey single crystals of the title compound used in X-ray diffraction studies were obtained by a slow evaporation of its DMF 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 (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonding is shown as dashed line.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

N,N'-bis(4-chlorophenyl)but-2-enediamide top

Crystal data top

C₁₆H₁₂Cl₂N₂O₂	F(000) = 688
M_r = 335.18	D_x = 1.482 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3188 reflections
a = 9.2397 (7) Å	θ = 2.8–27.9°
b = 13.0154 (8) Å	µ = 0.44 mm⁻¹
c = 13.1239 (9) Å	T = 293 K
β = 107.916 (9)°	Prism, dark grey
V = 1501.73 (18) Å³	0.44 × 0.44 × 0.32 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3065 independent reflections
Radiation source: fine-focus sealed tube	2523 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→10
T_min = 0.830, T_max = 0.872	k = −14→16
6063 measured reflections	l = −16→11

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0494P)² + 0.3163P] where P = (F_o² + 2F_c²)/3
3065 reflections	(Δ/σ)_max = 0.001
205 parameters	Δρ_max = 0.22 e Å⁻³
2 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₆H₁₂Cl₂N₂O₂	V = 1501.73 (18) Å³
M_r = 335.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2397 (7) Å	µ = 0.44 mm⁻¹
b = 13.0154 (8) Å	T = 293 K
c = 13.1239 (9) Å	0.44 × 0.44 × 0.32 mm
β = 107.916 (9)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3065 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2523 reflections with I > 2σ(I)
T_min = 0.830, T_max = 0.872	R_int = 0.011
6063 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	2 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.22 e Å⁻³
3065 reflections	Δρ_min = −0.24 e Å⁻³
205 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
Cl1	1.02985 (5)	−0.18771 (4)	0.07433 (4)	0.05576 (15)
Cl2	0.34374 (6)	0.72529 (3)	−0.01488 (4)	0.06130 (16)
O1	0.49648 (15)	0.13865 (8)	0.14544 (12)	0.0566 (4)
O2	0.10969 (14)	0.32142 (8)	0.19093 (9)	0.0449 (3)
N1	0.49484 (15)	−0.03027 (10)	0.18426 (11)	0.0380 (3)
H1N	0.4540 (19)	−0.0748 (13)	0.2131 (13)	0.046*
N2	0.30826 (16)	0.29745 (10)	0.12704 (11)	0.0393 (3)
H2N	0.3780 (18)	0.2545 (14)	0.1250 (14)	0.047*
C1	0.62405 (17)	−0.06341 (11)	0.15703 (12)	0.0349 (3)
C2	0.7035 (2)	−0.00167 (13)	0.10578 (14)	0.0479 (4)
H2	0.6734	0.0660	0.0888	0.057*
C3	0.8268 (2)	−0.04074 (14)	0.08021 (14)	0.0479 (4)
H3	0.8799	0.0007	0.0462	0.057*
C4	0.87128 (18)	−0.14080 (13)	0.10489 (12)	0.0399 (4)
C5	0.79395 (19)	−0.20323 (12)	0.15518 (13)	0.0430 (4)
H5	0.8240	−0.2711	0.1711	0.052*
C6	0.67118 (18)	−0.16405 (11)	0.18174 (13)	0.0391 (3)
H6	0.6196	−0.2057	0.2166	0.047*
C7	0.43672 (17)	0.06548 (11)	0.17594 (12)	0.0367 (3)
C8	0.29546 (19)	0.07352 (12)	0.20689 (13)	0.0410 (4)
H8	0.2649	0.0130	0.2319	0.049*
C9	0.20588 (19)	0.15430 (12)	0.20424 (13)	0.0423 (4)
H9	0.1231	0.1380	0.2274	0.051*
C10	0.20609 (17)	0.26486 (11)	0.17309 (11)	0.0346 (3)
C11	0.31503 (17)	0.40084 (11)	0.09296 (12)	0.0346 (3)
C12	0.44804 (17)	0.45625 (12)	0.13303 (12)	0.0369 (3)
H12	0.5318	0.4261	0.1825	0.044*
C13	0.45728 (18)	0.55621 (12)	0.10004 (12)	0.0386 (3)
H13	0.5469	0.5935	0.1267	0.046*
C14	0.33194 (18)	0.59989 (11)	0.02710 (12)	0.0371 (3)
C15	0.19922 (18)	0.54565 (13)	−0.01497 (13)	0.0432 (4)
H15	0.1160	0.5759	−0.0649	0.052*
C16	0.19120 (19)	0.44518 (12)	0.01807 (13)	0.0421 (4)
H16	0.1024	0.4075	−0.0102	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0450 (2)	0.0601 (3)	0.0653 (3)	0.0114 (2)	0.0217 (2)	−0.0056 (2)
Cl2	0.0756 (3)	0.0331 (2)	0.0800 (3)	0.0011 (2)	0.0311 (3)	0.0178 (2)
O1	0.0608 (8)	0.0259 (6)	0.1020 (10)	0.0056 (5)	0.0528 (7)	0.0123 (6)
O2	0.0515 (7)	0.0384 (6)	0.0541 (7)	0.0094 (5)	0.0300 (5)	0.0004 (5)
N1	0.0443 (7)	0.0262 (6)	0.0500 (7)	0.0015 (5)	0.0242 (6)	0.0079 (5)
N2	0.0467 (8)	0.0271 (6)	0.0530 (8)	0.0088 (6)	0.0282 (6)	0.0076 (6)
C1	0.0381 (8)	0.0284 (7)	0.0394 (8)	0.0016 (6)	0.0139 (6)	0.0004 (6)
C2	0.0580 (10)	0.0334 (8)	0.0624 (10)	0.0103 (8)	0.0336 (9)	0.0138 (8)
C3	0.0537 (10)	0.0436 (9)	0.0549 (10)	0.0034 (8)	0.0293 (8)	0.0084 (8)
C4	0.0377 (8)	0.0421 (9)	0.0393 (8)	0.0044 (7)	0.0108 (6)	−0.0068 (7)
C5	0.0449 (9)	0.0310 (8)	0.0511 (9)	0.0061 (7)	0.0116 (7)	−0.0008 (7)
C6	0.0435 (8)	0.0282 (7)	0.0463 (8)	−0.0024 (6)	0.0147 (7)	0.0022 (6)
C7	0.0425 (8)	0.0262 (7)	0.0460 (8)	0.0014 (6)	0.0206 (7)	0.0033 (6)
C8	0.0500 (9)	0.0293 (7)	0.0523 (9)	0.0001 (7)	0.0285 (8)	0.0075 (7)
C9	0.0490 (9)	0.0373 (8)	0.0515 (9)	0.0015 (7)	0.0315 (8)	0.0064 (7)
C10	0.0415 (8)	0.0313 (7)	0.0353 (7)	0.0034 (6)	0.0180 (6)	−0.0005 (6)
C11	0.0433 (8)	0.0271 (7)	0.0403 (8)	0.0060 (6)	0.0231 (6)	0.0030 (6)
C12	0.0389 (8)	0.0381 (8)	0.0364 (8)	0.0076 (7)	0.0154 (6)	0.0060 (6)
C13	0.0417 (8)	0.0358 (8)	0.0421 (8)	−0.0028 (7)	0.0183 (7)	−0.0009 (6)
C14	0.0489 (9)	0.0269 (7)	0.0430 (8)	0.0043 (6)	0.0252 (7)	0.0052 (6)
C15	0.0414 (8)	0.0396 (9)	0.0486 (9)	0.0087 (7)	0.0140 (7)	0.0113 (7)
C16	0.0386 (8)	0.0350 (8)	0.0525 (9)	−0.0001 (7)	0.0136 (7)	0.0040 (7)

Geometric parameters (Å, º) top

Cl1—C4	1.7440 (16)	C5—H5	0.9300
Cl2—C14	1.7367 (15)	C6—H6	0.9300
O1—C7	1.2280 (18)	C7—C8	1.485 (2)
O2—C10	1.2322 (18)	C8—C9	1.332 (2)
N1—C7	1.3481 (19)	C8—H8	0.9300
N1—C1	1.4149 (19)	C9—C10	1.496 (2)
N1—H1N	0.843 (14)	C9—H9	0.9300
N2—C10	1.3369 (19)	C11—C12	1.382 (2)
N2—C11	1.4255 (19)	C11—C16	1.384 (2)
N2—H2N	0.860 (14)	C12—C13	1.382 (2)
C1—C6	1.387 (2)	C12—H12	0.9300
C1—C2	1.393 (2)	C13—C14	1.378 (2)
C2—C3	1.380 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.375 (2)
C3—C4	1.374 (2)	C15—C16	1.387 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.377 (2)	C16—H16	0.9300
C5—C6	1.383 (2)

C7—N1—C1	127.41 (13)	C9—C8—C7	129.78 (14)
C7—N1—H1N	116.8 (13)	C9—C8—H8	115.1
C1—N1—H1N	115.7 (13)	C7—C8—H8	115.1
C10—N2—C11	123.13 (13)	C8—C9—C10	135.51 (14)
C10—N2—H2N	116.6 (13)	C8—C9—H9	112.2
C11—N2—H2N	119.9 (13)	C10—C9—H9	112.2
C6—C1—C2	118.92 (14)	O2—C10—N2	123.26 (14)
C6—C1—N1	117.23 (13)	O2—C10—C9	117.45 (13)
C2—C1—N1	123.84 (14)	N2—C10—C9	119.29 (13)
C3—C2—C1	120.13 (15)	C12—C11—C16	119.78 (14)
C3—C2—H2	119.9	C12—C11—N2	119.54 (14)
C1—C2—H2	119.9	C16—C11—N2	120.66 (14)
C4—C3—C2	120.08 (16)	C11—C12—C13	120.37 (14)
C4—C3—H3	120.0	C11—C12—H12	119.8
C2—C3—H3	120.0	C13—C12—H12	119.8
C3—C4—C5	120.71 (15)	C14—C13—C12	119.10 (15)
C3—C4—Cl1	119.28 (13)	C14—C13—H13	120.5
C5—C4—Cl1	120.00 (13)	C12—C13—H13	120.5
C4—C5—C6	119.34 (15)	C15—C14—C13	121.49 (14)
C4—C5—H5	120.3	C15—C14—Cl2	119.37 (12)
C6—C5—H5	120.3	C13—C14—Cl2	119.12 (12)
C5—C6—C1	120.82 (15)	C14—C15—C16	119.04 (15)
C5—C6—H6	119.6	C14—C15—H15	120.5
C1—C6—H6	119.6	C16—C15—H15	120.5
O1—C7—N1	122.38 (14)	C11—C16—C15	120.21 (15)
O1—C7—C8	123.75 (14)	C11—C16—H16	119.9
N1—C7—C8	113.87 (13)	C15—C16—H16	119.9

C7—N1—C1—C6	174.16 (15)	C11—N2—C10—O2	−0.6 (3)
C7—N1—C1—C2	−7.0 (3)	C11—N2—C10—C9	178.80 (14)
C6—C1—C2—C3	0.1 (3)	C8—C9—C10—O2	−173.19 (19)
N1—C1—C2—C3	−178.74 (16)	C8—C9—C10—N2	7.4 (3)
C1—C2—C3—C4	0.2 (3)	C10—N2—C11—C12	122.66 (17)
C2—C3—C4—C5	0.0 (3)	C10—N2—C11—C16	−59.1 (2)
C2—C3—C4—Cl1	−178.68 (14)	C16—C11—C12—C13	1.0 (2)
C3—C4—C5—C6	−0.6 (2)	N2—C11—C12—C13	179.29 (13)
Cl1—C4—C5—C6	178.10 (12)	C11—C12—C13—C14	0.3 (2)
C4—C5—C6—C1	0.9 (2)	C12—C13—C14—C15	−1.3 (2)
C2—C1—C6—C5	−0.7 (2)	C12—C13—C14—Cl2	−179.70 (11)
N1—C1—C6—C5	178.25 (14)	C13—C14—C15—C16	0.9 (2)
C1—N1—C7—O1	−2.6 (3)	Cl2—C14—C15—C16	179.31 (12)
C1—N1—C7—C8	177.38 (14)	C12—C11—C16—C15	−1.4 (2)
O1—C7—C8—C9	3.0 (3)	N2—C11—C16—C15	−179.66 (14)
N1—C7—C8—C9	−176.98 (17)	C14—C15—C16—C11	0.5 (2)
C7—C8—C9—C10	−0.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.84 (1)	2.05 (2)	2.8836 (16)	169 (2)
N2—H2N···O1	0.86 (1)	1.83 (2)	2.6639 (17)	162 (2)

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂Cl₂N₂O₂
M_r	335.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.2397 (7), 13.0154 (8), 13.1239 (9)
β (°)	107.916 (9)
V (Å³)	1501.73 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.44 × 0.44 × 0.32

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.830, 0.872
No. of measured, independent and observed [I > 2σ(I)] reflections	6063, 3065, 2523
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.091, 1.06
No. of reflections	3065
No. of parameters	205
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24

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···O2ⁱ	0.843 (14)	2.052 (15)	2.8836 (16)	168.9 (17)
N2—H2N···O1	0.860 (14)	1.833 (15)	2.6639 (17)	161.7 (18)

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

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