2-(3-Eth­oxy-2-hy­droxy­benz­ylidene)-N-phenyl­hydrazinecarboxamide

Sithambaresan, M.; Kurup, M.R.P.

doi:10.1107/S1600536811041857

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2972

doi:10.1107/S1600536811041857

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2-(3-Ethoxy-2-hydroxybenzylidene)-N-phenylhydrazinecarboxamide

M. Sithambaresan ^a ^* and M. R. Prathapachandra Kurup ^b

^aDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and ^bDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682022, India
^*Correspondence e-mail: eesans@yahoo.com

(Received 4 October 2011; accepted 11 October 2011; online 22 October 2011)

The title compound, C₁₆H₁₇N₃O₃, exists in the E configuration with respect to the azomethine double bond. The molecule is close to planar, with a dihedral angle of 6.7 (1)° between the aromatic rings. The phenolic O atom functions as donor and acceptor by forming intramolecular O—H⋯O and intermolecular N—H⋯O hydrogen bonds, respectively. Two-dimensional packing is fashioned through an intermolecular hydrogen bonding network in an offset manner.

Related literature

For background to N-phenylhydrazinecarboxamides and their complexes, see: Reena et al. (2008 ). For the synthesis of related compounds, see: Siji et al. (2010 ). For related structures, see: Kayed et al. (2011 ); Kala et al. (2007 ); Kurup et al. (2011 ); Reena & Kurup (2010 ).

Experimental

Crystal data

C₁₆H₁₇N₃O₃
M_r = 299.33
Monoclinic, C 2/c
a = 30.1352 (13) Å
b = 5.5552 (3) Å
c = 18.2232 (8) Å
β = 92.753 (2)°
V = 3047.2 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.50 × 0.30 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.967, T_max = 0.991
10811 measured reflections
2687 independent reflections
2066 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.137
S = 1.06
2687 reflections
213 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯O2ⁱ	0.86 (2)	2.13 (2)	2.8799 (19)	145.9 (18)
N3—H3′⋯N1	0.85 (1)	2.25 (2)	2.6604 (17)	110.0 (14)
O2—H2⋯O3ⁱ	0.87 (2)	2.28 (2)	2.8867 (16)	127.1 (18)
O2—H2⋯O1	0.87 (2)	2.14 (2)	2.6206 (16)	114.2 (17)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041857/ng5242sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041857/ng5242Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041857/ng5242Isup3.cml

checkCIF report

Comment top

The compound crystallizes into a monoclinic space group C2/c. The molecule is almost planar with maximum deviation of 0.218 (1) Å for the atom N1. The dihedral angle between the two aromatic rings is 6.70°. The molecule exists in the E configuration with respect to C7=N1 bond (Fig. 1). A torsion angle value of -176.4 (1)° corresponding to O3–C8–N2–N1 moiety confirms the trans configuration of the O3 atom with respect to hydrazine nitrogen atom N1. As a result, the atom N1 lies cis to N3, with an N1–N2–C8–N3 torsion angle of 3.6 (2). This arrangement favours the intramolecular hydrogen bond interaction between N1 and H attached to N3 atom. Similarly O1 and O2 lie cis to each other with an torsion angle of -0.4 (2) and it favours the intramolecular hydrogen bond interaction between O1 and the H on O2 atom. These two intramolecular hydrogen bonding interactions play an important role by stabilizing this conformation. The C8–N2 bond distance [1.3656 (19) Å] is appreciably close to that of C–N single bond [1.351 (2) Å], confirming the keto form of the ligand (Reena & Kurup, 2010). The existence of 2-(3-ethoxy-2-hydroxybenzyl)-N-phenylhydrazinecarboxamide in the keto form in the solid state is evidenced by the C8–O2 bond distance of 1.2233 (19) Å, which is very close to a formal C=O bond length [1.21 Å] (Kala et al., 2007).

The neighbouring molecules are interconnected by intermolecular hydrogen bonding (Table 1). The molecular array involes two types of hydrogen bonding interactions where the O1 and O3 function as acceptors while the atom O2 acts as donor and acceptor.

In the crystal lattice (Fig. 2), two-dimensional packing is fashioned by the network of intermolecular hydrogen bonding interactions. The repeating units of two adjacent molecules are aligned in offset manner. The distance between two consecutive parallel rings is more than 5 Å and therefore there are very weak π···π or C–H···π interactions between the adjacent molecules. However, the hydrogen bonding plays key role in packing of molecules in the unit cell.

Related literature top

For background to N-phenylhydrazinecarboxamides and their complexes, see: Reena et al. (2008). For the synthesis of related compounds, see: Siji et al. (2010). For related structures, see: Kayed et al. (2011); Kala et al. (2007); Kurup et al. (2011); Reena & Kurup (2010).

Experimental top

The title compound was prepared by adapting a reported procedure (Siji et al., 2010). A methanolic solution (30 ml) of N-phenylhydrazinecarboxamide (1.511 g, 10 mmol) was added to a solution of 3-ethoxy-2-hydroxybenzaldehyde (1.662 g, 10 mmol) in methanol and the reaction mixture was refluxed for 2 h after adding a few drops of dilute acetic acid. On cooling the solution, very pale yellow block-shaped crystals suitable for single-crystal analysis were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP diagram of 2-(3-ethoxy-2-hydroxybenzyl)-N-phenylhydrazinecarboxamide with 50% probability ellipsoid.
	Fig. 2. Packing diagram of 2-(3-ethoxy-2-hydroxybenzyl)-N-phenylhydrazinecarboxamide along b axis.

2-(3-Ethoxy-2-hydroxybenzylidene)-N-phenylhydrazinecarboxamide top

Crystal data top

C₁₆H₁₇N₃O₃	F(000) = 1264.0
M_r = 299.33	D_x = 1.305 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3454 reflections
a = 30.1352 (13) Å	θ = 1.4–27.5°
b = 5.5552 (3) Å	µ = 0.09 mm⁻¹
c = 18.2232 (8) Å	T = 296 K
β = 92.753 (2)°	Block, pale yellow
V = 3047.2 (2) Å³	0.50 × 0.30 × 0.10 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	2687 independent reflections
Radiation source: fine-focus sealed tube	2066 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −35→35
T_min = 0.967, T_max = 0.991	k = −4→6
10811 measured reflections	l = −21→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0783P)² + 0.6395P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.003
2687 reflections	Δρ_max = 0.16 e Å⁻³
213 parameters	Δρ_min = −0.13 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 1996), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0055 (9)

Crystal data top

C₁₆H₁₇N₃O₃	V = 3047.2 (2) Å³
M_r = 299.33	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.1352 (13) Å	µ = 0.09 mm⁻¹
b = 5.5552 (3) Å	T = 296 K
c = 18.2232 (8) Å	0.50 × 0.30 × 0.10 mm
β = 92.753 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2687 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2066 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.991	R_int = 0.035
10811 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	2 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.16 e Å⁻³
2687 reflections	Δρ_min = −0.13 e Å⁻³
213 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
O1	0.37161 (4)	−0.1876 (2)	0.50043 (7)	0.0781 (4)
O2	0.42932 (4)	0.1621 (2)	0.48991 (6)	0.0703 (4)
O3	0.61791 (4)	0.7085 (2)	0.64595 (7)	0.0800 (4)
N1	0.53666 (4)	0.2594 (3)	0.62904 (7)	0.0621 (4)
N2	0.56032 (5)	0.4651 (3)	0.61776 (8)	0.0726 (4)
N3	0.61370 (4)	0.3406 (2)	0.70231 (8)	0.0626 (4)
C1	0.43561 (5)	0.0007 (3)	0.54552 (8)	0.0563 (4)
C2	0.40572 (5)	−0.1888 (3)	0.55286 (9)	0.0611 (4)
C3	0.41199 (6)	−0.3509 (3)	0.60918 (10)	0.0719 (5)
H3	0.3924	−0.4784	0.6139	0.086*
C4	0.44794 (6)	−0.3228 (3)	0.65907 (10)	0.0773 (5)
H4	0.4521	−0.4315	0.6976	0.093*
C5	0.47737 (6)	−0.1374 (3)	0.65230 (9)	0.0691 (5)
H5	0.5013	−0.1219	0.6861	0.083*
C6	0.47181 (5)	0.0285 (3)	0.59510 (8)	0.0567 (4)
C7	0.50174 (5)	0.2319 (3)	0.58751 (8)	0.0616 (4)
H7	0.4952	0.3456	0.5511	0.074*
C8	0.59928 (5)	0.5163 (3)	0.65588 (9)	0.0616 (4)
C9	0.65140 (5)	0.3413 (3)	0.75132 (8)	0.0542 (4)
C10	0.68369 (5)	0.5188 (3)	0.75262 (9)	0.0626 (4)
H10	0.6812	0.6481	0.7203	0.075*
C11	0.71966 (5)	0.5025 (3)	0.80230 (10)	0.0691 (5)
H11	0.7413	0.6217	0.8030	0.083*
C12	0.72396 (6)	0.3148 (3)	0.85037 (10)	0.0743 (5)
H12	0.7484	0.3057	0.8834	0.089*
C13	0.69195 (7)	0.1402 (3)	0.84939 (11)	0.0818 (6)
H13	0.6946	0.0122	0.8822	0.098*
C14	0.65571 (6)	0.1520 (3)	0.80001 (10)	0.0702 (5)
H14	0.6342	0.0319	0.7997	0.084*
C15	0.33793 (6)	−0.3673 (4)	0.50345 (11)	0.0823 (6)
H15A	0.3258	−0.3702	0.5518	0.099*
H15B	0.3502	−0.5248	0.4935	0.099*
C16	0.30266 (7)	−0.3044 (5)	0.44677 (14)	0.1099 (8)
H16A	0.2900	−0.1514	0.4584	0.165*
H16B	0.2799	−0.4256	0.4458	0.165*
H16C	0.3153	−0.2956	0.3995	0.165*
H2	0.4079 (6)	0.112 (4)	0.4600 (11)	0.093 (6)*
H3'	0.5986 (5)	0.2112 (18)	0.7011 (10)	0.074 (5)*
H2'	0.5514 (7)	0.570 (4)	0.5859 (12)	0.096 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0642 (7)	0.0915 (9)	0.0775 (8)	−0.0189 (6)	−0.0083 (6)	0.0033 (6)
O2	0.0683 (7)	0.0755 (8)	0.0652 (7)	−0.0102 (6)	−0.0178 (6)	0.0151 (6)
O3	0.0740 (7)	0.0724 (8)	0.0912 (9)	−0.0133 (6)	−0.0211 (6)	0.0243 (7)
N1	0.0565 (7)	0.0674 (8)	0.0616 (8)	−0.0023 (6)	−0.0046 (6)	0.0058 (6)
N2	0.0641 (8)	0.0762 (10)	0.0754 (9)	−0.0100 (7)	−0.0171 (7)	0.0225 (8)
N3	0.0582 (7)	0.0607 (8)	0.0676 (8)	−0.0071 (6)	−0.0094 (6)	0.0085 (7)
C1	0.0559 (8)	0.0610 (9)	0.0521 (8)	0.0027 (7)	0.0015 (6)	0.0008 (7)
C2	0.0578 (8)	0.0666 (10)	0.0591 (9)	−0.0032 (8)	0.0058 (7)	−0.0045 (8)
C3	0.0784 (11)	0.0679 (11)	0.0700 (10)	−0.0114 (9)	0.0102 (9)	0.0017 (8)
C4	0.0940 (13)	0.0763 (12)	0.0616 (10)	−0.0024 (10)	0.0035 (9)	0.0163 (9)
C5	0.0743 (10)	0.0764 (11)	0.0558 (9)	0.0008 (9)	−0.0055 (8)	0.0073 (8)
C6	0.0573 (8)	0.0618 (9)	0.0508 (8)	0.0019 (7)	0.0007 (6)	0.0000 (7)
C7	0.0592 (8)	0.0702 (10)	0.0546 (8)	−0.0008 (8)	−0.0053 (7)	0.0076 (7)
C8	0.0572 (8)	0.0668 (10)	0.0600 (9)	−0.0011 (8)	−0.0045 (7)	0.0079 (8)
C9	0.0538 (8)	0.0535 (8)	0.0551 (8)	0.0036 (7)	−0.0007 (6)	−0.0019 (7)
C10	0.0634 (9)	0.0609 (9)	0.0627 (9)	−0.0027 (7)	−0.0062 (7)	0.0058 (7)
C11	0.0637 (9)	0.0672 (11)	0.0751 (10)	−0.0052 (8)	−0.0108 (8)	−0.0029 (8)
C12	0.0738 (10)	0.0710 (11)	0.0758 (11)	0.0095 (9)	−0.0216 (9)	−0.0042 (9)
C13	0.0960 (13)	0.0626 (11)	0.0844 (12)	0.0049 (10)	−0.0221 (10)	0.0147 (9)
C14	0.0728 (10)	0.0567 (10)	0.0796 (11)	−0.0039 (8)	−0.0104 (9)	0.0088 (8)
C15	0.0652 (10)	0.0861 (13)	0.0963 (14)	−0.0172 (9)	0.0108 (9)	−0.0240 (11)
C16	0.0634 (11)	0.157 (2)	0.1087 (16)	−0.0202 (13)	−0.0018 (11)	−0.0364 (16)

Geometric parameters (Å, º) top

O1—C2	1.3693 (19)	C5—H5	0.9300
O1—C15	1.426 (2)	C6—C7	1.456 (2)
O2—C1	1.3598 (18)	C7—H7	0.9300
O2—H2	0.870 (15)	C9—C14	1.378 (2)
O3—C8	1.2239 (19)	C9—C10	1.385 (2)
N1—C7	1.2758 (19)	C10—C11	1.381 (2)
N1—N2	1.368 (2)	C10—H10	0.9300
N2—C8	1.365 (2)	C11—C12	1.364 (3)
N2—H2'	0.86 (2)	C11—H11	0.9300
N3—C8	1.350 (2)	C12—C13	1.368 (3)
N3—C9	1.4109 (19)	C12—H12	0.9300
N3—H3'	0.8500 (11)	C13—C14	1.383 (2)
C1—C6	1.391 (2)	C13—H13	0.9300
C1—C2	1.396 (2)	C14—H14	0.9300
C2—C3	1.371 (2)	C15—C16	1.488 (3)
C3—C4	1.389 (2)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.369 (2)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.396 (2)	C16—H16C	0.9600

C2—O1—C15	118.77 (14)	N3—C8—N2	114.31 (15)
C1—O2—H2	109.1 (15)	C14—C9—C10	119.20 (15)
C7—N1—N2	115.60 (13)	C14—C9—N3	116.98 (14)
C8—N2—N1	122.63 (14)	C10—C9—N3	123.82 (14)
C8—N2—H2'	116.0 (14)	C11—C10—C9	119.55 (15)
N1—N2—H2'	121.4 (14)	C11—C10—H10	120.2
C8—N3—C9	128.31 (14)	C9—C10—H10	120.2
C8—N3—H3'	116.1 (12)	C12—C11—C10	121.22 (16)
C9—N3—H3'	115.5 (12)	C12—C11—H11	119.4
O2—C1—C6	119.17 (14)	C10—C11—H11	119.4
O2—C1—C2	120.09 (13)	C11—C12—C13	119.26 (16)
C6—C1—C2	120.74 (14)	C11—C12—H12	120.4
O1—C2—C3	126.67 (15)	C13—C12—H12	120.4
O1—C2—C1	113.30 (14)	C12—C13—C14	120.60 (16)
C3—C2—C1	120.02 (15)	C12—C13—H13	119.7
C2—C3—C4	119.42 (16)	C14—C13—H13	119.7
C2—C3—H3	120.3	C9—C14—C13	120.16 (16)
C4—C3—H3	120.3	C9—C14—H14	119.9
C5—C4—C3	120.92 (16)	C13—C14—H14	119.9
C5—C4—H4	119.5	O1—C15—C16	107.15 (18)
C3—C4—H4	119.5	O1—C15—H15A	110.3
C4—C5—C6	120.61 (16)	C16—C15—H15A	110.3
C4—C5—H5	119.7	O1—C15—H15B	110.3
C6—C5—H5	119.7	C16—C15—H15B	110.3
C1—C6—C5	118.29 (15)	H15A—C15—H15B	108.5
C1—C6—C7	119.64 (13)	C15—C16—H16A	109.5
C5—C6—C7	122.04 (14)	C15—C16—H16B	109.5
N1—C7—C6	122.26 (14)	H16A—C16—H16B	109.5
N1—C7—H7	118.9	C15—C16—H16C	109.5
C6—C7—H7	118.9	H16A—C16—H16C	109.5
O3—C8—N3	125.98 (14)	H16B—C16—H16C	109.5
O3—C8—N2	119.71 (15)

C7—N1—N2—C8	−177.55 (15)	C1—C6—C7—N1	−176.32 (14)
C15—O1—C2—C3	1.3 (3)	C5—C6—C7—N1	5.7 (2)
C15—O1—C2—C1	−177.82 (14)	C9—N3—C8—O3	3.1 (3)
O2—C1—C2—O1	−0.5 (2)	C9—N3—C8—N2	−177.15 (15)
C6—C1—C2—O1	178.87 (13)	N1—N2—C8—O3	−176.50 (15)
O2—C1—C2—C3	−179.69 (15)	N1—N2—C8—N3	3.7 (2)
C6—C1—C2—C3	−0.4 (2)	C8—N3—C9—C14	171.60 (17)
O1—C2—C3—C4	−178.35 (16)	C8—N3—C9—C10	−8.7 (3)
C1—C2—C3—C4	0.8 (3)	C14—C9—C10—C11	0.3 (2)
C2—C3—C4—C5	−0.7 (3)	N3—C9—C10—C11	−179.42 (14)
C3—C4—C5—C6	0.2 (3)	C9—C10—C11—C12	−0.2 (3)
O2—C1—C6—C5	179.23 (14)	C10—C11—C12—C13	−0.2 (3)
C2—C1—C6—C5	−0.1 (2)	C11—C12—C13—C14	0.4 (3)
O2—C1—C6—C7	1.2 (2)	C10—C9—C14—C13	−0.1 (3)
C2—C1—C6—C7	−178.15 (13)	N3—C9—C14—C13	179.66 (16)
C4—C5—C6—C1	0.2 (2)	C12—C13—C14—C9	−0.3 (3)
C4—C5—C6—C7	178.16 (16)	C2—O1—C15—C16	172.82 (16)
N2—N1—C7—C6	−176.88 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···O2ⁱ	0.86 (2)	2.13 (2)	2.8799 (19)	145.9 (18)
N3—H3′···N1	0.85 (1)	2.25 (2)	2.6604 (17)	110 (1)
O2—H2···O3ⁱ	0.87 (2)	2.28 (2)	2.8867 (16)	127 (2)
O2—H2···O1	0.87 (2)	2.14 (2)	2.6206 (16)	114 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₃O₃
M_r	299.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	30.1352 (13), 5.5552 (3), 18.2232 (8)
β (°)	92.753 (2)
V (Å³)	3047.2 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.30 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10811, 2687, 2066
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.137, 1.06
No. of reflections	2687
No. of parameters	213
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)	0.16, −0.13

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2'···O2ⁱ	0.86 (2)	2.13 (2)	2.8799 (19)	145.9 (18)
N3—H3'···N1	0.8500 (11)	2.247 (17)	2.6604 (17)	110.0 (14)
O2—H2···O3ⁱ	0.870 (15)	2.28 (2)	2.8867 (16)	127.1 (18)
O2—H2···O1	0.870 (15)	2.14 (2)	2.6206 (16)	114.2 (17)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors are thankful to the SAIF, CUSAT, Kochi-22, for providing the single-crystal XRD data.

References

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