N′-[(E)-4-Benz­yloxy-2-hy­droxy­benzyl­idene]benzohydrazide

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

doi:10.1107/S1600536812036306

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2785

doi:10.1107/S1600536812036306

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N′-[(E)-4-Benzyloxy-2-hydroxybenzylidene]benzohydrazide

P. R. Reshma,^a M. Sithambaresan ^b ^* and M. R. Prathapachandra Kurup ^a

^aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
^*Correspondence e-mail: eesans@yahoo.com

(Received 12 August 2012; accepted 20 August 2012; online 25 August 2012)

The title compound, C₂₁H₁₈N₂O₃, exists in the E conformation with respect to the azomethane C=N double bond. The central benzene ring is almost coplanar with one of the substituent benzene rings [dihedral angle = 1.74 (5)°] and is approximately orthogonal to the other benzene ring of the molecule [dihedral angle = 86.61 (7)°]. An intramolecular O—H⋯N hydrogen bond occurs. The crystal packing is dominated by N—H⋯O hydrogen bonds, which lead to an infinite chain running parallel to [010].

Related literature

For the biological activity of hydrazones, see: Patil et al. (2010 ); Zhang et al. (2010 ). For the synthesis of related compounds, see: Emmanuel et al. (2011 ); Mangalam & Kurup (2011 ). For related structures, see: Lin & Sang (2009 ); Mohd Lair et al. (2009 ).

Experimental

Crystal data

C₂₁H₁₈N₂O₃
M_r = 346.37
Monoclinic, P 2₁
a = 10.8053 (6) Å
b = 4.8952 (2) Å
c = 16.3601 (10) Å
β = 95.813 (2)°
V = 860.90 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.969, T_max = 0.978
9033 measured reflections
1705 independent reflections
1593 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.082
S = 1.12
1705 reflections
243 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯O3ⁱ	0.85 (1)	2.09 (1)	2.903 (2)	160 (2)
O2—H2′′⋯N1	0.87 (2)	1.79 (2)	2.592 (2)	152 (3)
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036306/fj2591sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036306/fj2591Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812036306/fj2591Isup3.cml

checkCIF report

Comment top

Hydrazone compounds have received much attention due to their potential applications in biological chemistry (Patil et al., 2010; Zhang et al., 2010). As a continuous work on the hydrazone compounds, a new hydrazone compound, N'-{(E)-[4-(benzyloxy)-2-hydroxyphenyl]methylidene}benzohydrazide, was prepared and structurally characterized. The ORTEP view of the title compound is shown in Fig. 1.

The compound crystallizes in monoclinic space group P2₁. The molecule adopts an E configuration with respect to C14=N1 bond (Lin & Sang 2009; Mohd Lair et al., 2009) and it exists in amido form with C15=O3 bond length of 1.224 (3) Å which is very close to a formal C=O bond length [1.21 Å]. The aromatic ring C8—C13 is almost coplanar with the ring C16—C21 with dihedral angle of 1.74 (5)° whilst the ring C1—C6 is approximately orthogonal (86.61 (7)°) to the ring C16—C21.

While the intramolecular hydrogen bond O(2)—H(2'')···N(1) increases the rigidity of the molecule, intermolecular N(2)—H(2')···O(3) hydrogen bond (Table 1) links the adjacent molecules forming an infinite one-dimensional supramolecular chain running parallel to the [010] direction in the unit cell (Fig. 2). Benzohydrazone molecules within these chains also interact through very weak π···π interactions with a shortest centroid-centroid distance of 4.8950 (15) Å that not only augment the stronger N—H···O hydrogen bond but also interconnects the infinite chains forming three-dimensional network in the lattice. The parallel arrangement of the molecules along b axis is shown in Fig. 3.

Related literature top

For the biological activity of hydrazones, see: Patil et al. (2010); Zhang et al. (2010). For the synthesis of related compounds, see: Emmanuel et al. (2011); Mangalam & Kurup (2011). For related structures, see: Lin & Sang (2009); Mohd Lair et al. (2009).

Experimental top

The title compound was prepared by adapting a reported procedure (Emmanuel et al., 2011; Mangalam & Kurup, 2011) by refluxing a mixture of methanolic solutions of benzhydrazide (0.136 g,1 mmol) and 4-benzyloxysalicylaldehyde (0.2282 g,1 mmol) for 4 h. The formed crystals were collected, washed with few drops of methanol and dried over P₄O₁₀ in vacuo. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation from its methanolic solution.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. ORTEP view of the unique part of the compound, drawn with 50% probability displacement ellipsoids for the non-H atoms.

Fig. 2. Graphical representation showing one-dimensional supramolecular hydrogen bonding network in the crystal structure of C₂₁H₁₈N₂O₃.

Fig. 3. Packing diagram of the compound showing the parallel arrangement of the molecules along b axis.

N'-[(E)-4-Benzyloxy-2-hydroxybenzylidene]benzohydrazide top

Crystal data top

C₂₁H₁₈N₂O₃	F(000) = 364
M_r = 346.37	D_x = 1.336 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5951 reflections
a = 10.8053 (6) Å	θ = 2.4–28.1°
b = 4.8952 (2) Å	µ = 0.09 mm⁻¹
c = 16.3601 (10) Å	T = 296 K
β = 95.813 (2)°	Block, colorless
V = 860.90 (8) Å³	0.35 × 0.30 × 0.25 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	1705 independent reflections
Radiation source: fine-focus sealed tube	1593 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω and ϕ scan	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −5→5
T_min = 0.969, T_max = 0.978	l = −19→19
9033 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0492P)² + 0.0573P] where P = (F_o² + 2F_c²)/3
1705 reflections	(Δ/σ)_max = 0.005
243 parameters	Δρ_max = 0.12 e Å⁻³
3 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₁H₁₈N₂O₃	V = 860.90 (8) Å³
M_r = 346.37	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.8053 (6) Å	µ = 0.09 mm⁻¹
b = 4.8952 (2) Å	T = 296 K
c = 16.3601 (10) Å	0.35 × 0.30 × 0.25 mm
β = 95.813 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1705 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1593 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.978	R_int = 0.024
9033 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	3 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.12 e Å⁻³
1705 reflections	Δρ_min = −0.14 e Å⁻³
243 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	0.08187 (12)	0.6299 (3)	1.18699 (7)	0.0525 (4)
O2	0.19313 (15)	0.4504 (4)	0.91841 (8)	0.0610 (4)
O3	0.43474 (14)	0.3828 (3)	0.76116 (9)	0.0575 (4)
N1	0.37436 (15)	0.7368 (4)	0.87075 (9)	0.0471 (4)
N2	0.44743 (17)	0.8127 (3)	0.81016 (10)	0.0458 (4)
C1	−0.1620 (2)	0.5457 (6)	1.27899 (13)	0.0681 (7)
H1	−0.1984	0.6716	1.2413	0.082*
C2	−0.2072 (2)	0.5169 (8)	1.35467 (15)	0.0812 (9)
H2A	−0.2737	0.6235	1.3677	0.097*
C3	−0.1550 (3)	0.3347 (7)	1.40967 (15)	0.0779 (8)
H3	−0.1853	0.3174	1.4607	0.093*
C4	−0.0583 (3)	0.1761 (8)	1.39081 (16)	0.0890 (9)
H4	−0.0228	0.0501	1.4288	0.107*
C5	−0.0126 (2)	0.2025 (7)	1.31467 (15)	0.0750 (7)
H5	0.0528	0.0928	1.3015	0.090*
C6	−0.06386 (17)	0.3899 (5)	1.25910 (11)	0.0500 (5)
C7	−0.01383 (18)	0.4243 (5)	1.17735 (11)	0.0531 (5)
H7A	0.0203	0.2531	1.1600	0.064*
H7B	−0.0798	0.4808	1.1361	0.064*
C8	0.14629 (15)	0.6828 (4)	1.12181 (10)	0.0424 (4)
C9	0.13243 (17)	0.5416 (4)	1.04847 (11)	0.0464 (5)
H9	0.0725	0.4054	1.0401	0.056*
C10	0.20779 (17)	0.6026 (4)	0.98724 (10)	0.0431 (4)
C11	0.29517 (17)	0.8163 (4)	0.99739 (10)	0.0421 (4)
C12	0.30438 (17)	0.9593 (5)	1.07174 (11)	0.0501 (5)
H12	0.3604	1.1034	1.0794	0.060*
C13	0.23345 (17)	0.8937 (5)	1.13355 (11)	0.0493 (5)
H13	0.2431	0.9886	1.1830	0.059*
C14	0.37200 (17)	0.8897 (5)	0.93334 (11)	0.0470 (4)
H14	0.4195	1.0484	0.9380	0.056*
C15	0.47098 (17)	0.6182 (4)	0.75527 (11)	0.0427 (4)
C16	0.54733 (16)	0.7030 (4)	0.68911 (11)	0.0433 (4)
C17	0.5333 (2)	0.5618 (5)	0.61561 (12)	0.0565 (6)
H17	0.4738	0.4244	0.6077	0.068*
C18	0.6065 (2)	0.6223 (6)	0.55402 (13)	0.0671 (6)
H18	0.5957	0.5273	0.5046	0.080*
C19	0.6950 (2)	0.8216 (6)	0.56521 (14)	0.0673 (7)
H19	0.7449	0.8610	0.5236	0.081*
C20	0.7105 (2)	0.9643 (6)	0.63802 (14)	0.0655 (6)
H20	0.7709	1.0998	0.6455	0.079*
C21	0.63653 (18)	0.9069 (5)	0.70001 (13)	0.0532 (5)
H21	0.6466	1.0048	0.7489	0.064*
H2'	0.4593 (19)	0.9831 (9)	0.8048 (13)	0.047 (6)*
H2''	0.249 (2)	0.514 (7)	0.8883 (16)	0.100 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0541 (7)	0.0627 (10)	0.0425 (6)	−0.0105 (7)	0.0144 (5)	−0.0043 (7)
O2	0.0859 (10)	0.0528 (10)	0.0474 (7)	−0.0177 (8)	0.0207 (7)	−0.0110 (7)
O3	0.0747 (9)	0.0345 (8)	0.0668 (9)	−0.0058 (7)	0.0238 (7)	0.0026 (7)
N1	0.0560 (9)	0.0423 (10)	0.0454 (8)	0.0030 (8)	0.0161 (7)	0.0061 (8)
N2	0.0602 (9)	0.0320 (9)	0.0478 (8)	0.0002 (7)	0.0184 (7)	0.0059 (7)
C1	0.0652 (12)	0.0807 (18)	0.0605 (12)	0.0120 (13)	0.0162 (10)	0.0076 (13)
C2	0.0728 (15)	0.103 (2)	0.0724 (15)	0.0086 (16)	0.0311 (12)	−0.0023 (17)
C3	0.0884 (17)	0.090 (2)	0.0604 (13)	−0.0181 (17)	0.0300 (12)	0.0016 (15)
C4	0.106 (2)	0.094 (2)	0.0688 (15)	0.0056 (19)	0.0186 (14)	0.0313 (17)
C5	0.0768 (15)	0.0803 (19)	0.0712 (14)	0.0118 (14)	0.0235 (12)	0.0150 (14)
C6	0.0466 (10)	0.0556 (12)	0.0488 (9)	−0.0096 (10)	0.0094 (8)	−0.0032 (10)
C7	0.0530 (10)	0.0581 (14)	0.0497 (10)	−0.0071 (11)	0.0115 (8)	−0.0053 (10)
C8	0.0418 (9)	0.0464 (12)	0.0396 (9)	0.0028 (8)	0.0060 (7)	0.0006 (9)
C9	0.0505 (10)	0.0439 (11)	0.0454 (10)	−0.0058 (9)	0.0078 (8)	0.0003 (9)
C10	0.0536 (10)	0.0382 (10)	0.0377 (8)	0.0020 (9)	0.0059 (7)	0.0002 (8)
C11	0.0447 (9)	0.0407 (11)	0.0414 (9)	0.0028 (8)	0.0061 (7)	0.0016 (8)
C12	0.0504 (10)	0.0492 (13)	0.0508 (10)	−0.0105 (10)	0.0055 (8)	−0.0052 (9)
C13	0.0542 (10)	0.0547 (12)	0.0391 (9)	−0.0051 (10)	0.0055 (7)	−0.0061 (10)
C14	0.0487 (9)	0.0425 (11)	0.0507 (10)	−0.0011 (9)	0.0091 (8)	0.0022 (10)
C15	0.0482 (10)	0.0349 (10)	0.0460 (9)	0.0024 (9)	0.0089 (7)	0.0057 (9)
C16	0.0482 (10)	0.0364 (10)	0.0465 (9)	0.0053 (8)	0.0097 (8)	0.0052 (8)
C17	0.0673 (12)	0.0523 (14)	0.0515 (11)	−0.0063 (11)	0.0139 (9)	−0.0026 (10)
C18	0.0844 (15)	0.0710 (17)	0.0487 (11)	−0.0028 (15)	0.0210 (10)	−0.0012 (12)
C19	0.0731 (14)	0.0721 (17)	0.0613 (13)	0.0023 (13)	0.0296 (11)	0.0135 (13)
C20	0.0601 (12)	0.0620 (16)	0.0779 (15)	−0.0129 (12)	0.0245 (10)	0.0058 (13)
C21	0.0565 (10)	0.0488 (12)	0.0558 (10)	−0.0040 (10)	0.0131 (8)	0.0003 (10)

Geometric parameters (Å, º) top

O1—C8	1.356 (2)	C8—C9	1.380 (3)
O1—C7	1.440 (3)	C8—C13	1.397 (3)
O2—C10	1.346 (2)	C9—C10	1.386 (3)
O2—H2''	0.871 (18)	C9—H9	0.9300
O3—C15	1.224 (3)	C10—C11	1.407 (3)
N1—C14	1.271 (2)	C11—C12	1.398 (3)
N1—N2	1.379 (2)	C11—C14	1.447 (2)
N2—C15	1.350 (3)	C12—C13	1.367 (3)
N2—H2'	0.8500 (11)	C12—H12	0.9300
C1—C6	1.372 (3)	C13—H13	0.9300
C1—C2	1.383 (3)	C14—H14	0.9300
C1—H1	0.9300	C15—C16	1.485 (2)
C2—C3	1.349 (4)	C16—C17	1.382 (3)
C2—H2A	0.9300	C16—C21	1.386 (3)
C3—C4	1.363 (4)	C17—C18	1.375 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.392 (3)	C18—C19	1.365 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.369 (4)	C19—C20	1.376 (3)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.502 (2)	C20—C21	1.382 (3)
C7—H7A	0.9700	C20—H20	0.9300
C7—H7B	0.9700	C21—H21	0.9300

C8—O1—C7	117.87 (14)	O2—C10—C9	117.22 (18)
C10—O2—H2''	104 (2)	O2—C10—C11	122.05 (16)
C14—N1—N2	118.70 (17)	C9—C10—C11	120.73 (17)
C15—N2—N1	116.64 (16)	C12—C11—C10	117.55 (16)
C15—N2—H2'	125.7 (15)	C12—C11—C14	120.68 (18)
N1—N2—H2'	116.2 (15)	C10—C11—C14	121.77 (17)
C6—C1—C2	120.5 (2)	C13—C12—C11	121.99 (19)
C6—C1—H1	119.8	C13—C12—H12	119.0
C2—C1—H1	119.8	C11—C12—H12	119.0
C3—C2—C1	120.2 (3)	C12—C13—C8	119.49 (17)
C3—C2—H2A	119.9	C12—C13—H13	120.3
C1—C2—H2A	119.9	C8—C13—H13	120.3
C2—C3—C4	120.3 (2)	N1—C14—C11	119.8 (2)
C2—C3—H3	119.9	N1—C14—H14	120.1
C4—C3—H3	119.9	C11—C14—H14	120.1
C3—C4—C5	120.0 (3)	O3—C15—N2	121.87 (17)
C3—C4—H4	120.0	O3—C15—C16	121.75 (18)
C5—C4—H4	120.0	N2—C15—C16	116.34 (18)
C6—C5—C4	120.0 (3)	C17—C16—C21	119.04 (17)
C6—C5—H5	120.0	C17—C16—C15	118.32 (18)
C4—C5—H5	120.0	C21—C16—C15	122.54 (18)
C5—C6—C1	119.1 (2)	C18—C17—C16	120.6 (2)
C5—C6—C7	120.6 (2)	C18—C17—H17	119.7
C1—C6—C7	120.4 (2)	C16—C17—H17	119.7
O1—C7—C6	107.46 (16)	C19—C18—C17	120.2 (2)
O1—C7—H7A	110.2	C19—C18—H18	119.9
C6—C7—H7A	110.2	C17—C18—H18	119.9
O1—C7—H7B	110.2	C18—C19—C20	120.06 (19)
C6—C7—H7B	110.2	C18—C19—H19	120.0
H7A—C7—H7B	108.5	C20—C19—H19	120.0
O1—C8—C9	124.68 (17)	C19—C20—C21	120.2 (2)
O1—C8—C13	115.18 (16)	C19—C20—H20	119.9
C9—C8—C13	120.13 (16)	C21—C20—H20	119.9
C8—C9—C10	120.04 (18)	C20—C21—C16	119.9 (2)
C8—C9—H9	120.0	C20—C21—H21	120.1
C10—C9—H9	120.0	C16—C21—H21	120.1

C14—N1—N2—C15	164.71 (18)	C10—C11—C12—C13	1.2 (3)
C6—C1—C2—C3	−0.1 (4)	C14—C11—C12—C13	−179.66 (19)
C1—C2—C3—C4	−0.6 (5)	C11—C12—C13—C8	−1.9 (3)
C2—C3—C4—C5	0.3 (5)	O1—C8—C13—C12	178.99 (18)
C3—C4—C5—C6	0.7 (5)	C9—C8—C13—C12	0.2 (3)
C4—C5—C6—C1	−1.4 (4)	N2—N1—C14—C11	179.39 (16)
C4—C5—C6—C7	178.8 (3)	C12—C11—C14—N1	170.89 (18)
C2—C1—C6—C5	1.0 (4)	C10—C11—C14—N1	−10.0 (3)
C2—C1—C6—C7	−179.1 (3)	N1—N2—C15—O3	−3.6 (3)
C8—O1—C7—C6	175.83 (17)	N1—N2—C15—C16	178.67 (15)
C5—C6—C7—O1	−90.4 (3)	O3—C15—C16—C17	28.2 (3)
C1—C6—C7—O1	89.8 (2)	N2—C15—C16—C17	−154.05 (19)
C7—O1—C8—C9	−4.4 (3)	O3—C15—C16—C21	−148.1 (2)
C7—O1—C8—C13	176.89 (17)	N2—C15—C16—C21	29.7 (3)
O1—C8—C9—C10	−176.51 (17)	C21—C16—C17—C18	−0.1 (3)
C13—C8—C9—C10	2.1 (3)	C15—C16—C17—C18	−176.5 (2)
C8—C9—C10—O2	177.42 (18)	C16—C17—C18—C19	0.7 (4)
C8—C9—C10—C11	−2.9 (3)	C17—C18—C19—C20	−0.6 (4)
O2—C10—C11—C12	−179.1 (2)	C18—C19—C20—C21	−0.1 (4)
C9—C10—C11—C12	1.2 (3)	C19—C20—C21—C16	0.6 (4)
O2—C10—C11—C14	1.8 (3)	C17—C16—C21—C20	−0.5 (3)
C9—C10—C11—C14	−177.93 (18)	C15—C16—C21—C20	175.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···O3ⁱ	0.85 (1)	2.09 (1)	2.903 (2)	160 (2)
O2—H2′′···N1	0.87 (2)	1.79 (2)	2.592 (2)	152 (3)

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈N₂O₃
M_r	346.37
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	10.8053 (6), 4.8952 (2), 16.3601 (10)
β (°)	95.813 (2)
V (Å³)	860.90 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.969, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	9033, 1705, 1593
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.082, 1.12
No. of reflections	1705
No. of parameters	243
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.14

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 2010), 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'···O3ⁱ	0.8500 (11)	2.090 (8)	2.903 (2)	160 (2)
O2—H2''···N1	0.871 (18)	1.79 (2)	2.592 (2)	152 (3)

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

Acknowledgements

The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for providing the single-crystal X-ray diffraction data. PRR thanks the Council of Scientific and Industrial Research, New Delhi, India, for a Junior Research Fellowship.

References

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