N′-[(1E)-4-Diethyl­amino-2-hy­droxy­benz­idene]benzohydrazide

Prabhu, M.; Meenakshi, C.; Chakkaravarthi, G.; Rajagopal, G.

doi:10.1107/S160053681103652X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2633

https://doi.org/10.1107/S160053681103652X

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N′-[(1E)-4-Diethylamino-2-hydroxybenzidene]benzohydrazide

M. Prabhu,^a C. Meenakshi,^b G. Chakkaravarthi ^c ^* and G. Rajagopal ^d ^*

^aShasun Pharmaceuticals Ltd, Chennai 600 048, India, ^bDepartment of Chemistry, Government Arts College for Women (Autonomous), Madurai 625 002, India, ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^dDepartment of Chemistry, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

(Received 3 September 2011; accepted 7 September 2011; online 14 September 2011)

In the title compound, C₁₈H₂₁N₃O₂, the dihedral angle between the phenyl and benzene rings is 36.85 (10)°. The methyl C atom of one of the ethyl groups is disordered over two positions with site occupancies of 0.810 (8) and 0.190 (8). The molecular structure is stabilized by a classical intramolecular O—H⋯N hydrogen bond. The crystal structure exhibits weak intermolecular N—H⋯O, C—H⋯O and C—H⋯π interactions.

Related literature

For the biological activity of Schiff base ligands, see: Kelley et al. (1995 ); Pandeya et al. (1999 ); Singh & Dash (1988 ); Tarafder et al. (2002 ). For related strucutures, see: Bahron et al. (2010 ); Manvizhi et al. (2010 ).

Experimental

Crystal data

C₁₈H₂₁N₃O₂
M_r = 311.38
Monoclinic, P 2₁ /c
a = 10.591 (5) Å
b = 16.733 (6) Å
c = 9.671 (5) Å
β = 102.316 (5)°
V = 1674.4 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.977, T_max = 0.984
9666 measured reflections
3884 independent reflections
2466 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.203
S = 1.05
3884 reflections
222 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N2	0.82	1.92	2.643 (3)	147
N1—H1⋯O1ⁱ	0.86	2.10	2.926 (3)	160
C8—H8⋯O1ⁱ	0.93	2.50	3.293 (3)	144
C3—H3⋯Cg2ⁱⁱ	0.93	2.97	3.468 (5)	115
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: https://doi.org/10.1107/S160053681103652X/rk2298sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681103652X/rk2298Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681103652X/rk2298Isup3.cml

checkCIF report

Comment top

In view of the biological actitivities of Schiff base ligands which are known to exhibit anti–viral, anti–cancer, anti–bacterial, anti–fungal, anti–inflammatory, anti–convulsant and anti–HIV activities (Pandeya et al., 1999; Singh & Dash, 1988; Kelley et al., 1995; Tarafder et al., 2002), we report herein the molecular and crystal structures of the title compound.

The geometric parameters of the molecule of title compound (Fig.1) agree well with the reported similar structures (Bahron et al., 2010; Manvizhi et al., 2010). The dihedral angle between the phenyl ring (C1–C6) and the benzene ring (C9–C14) is 36.85 (10)°. The methyl C18 atom in the ethyl groups is disordered over two positions with site occupancies of 0.810 (8) and 0.190 (8).

The molecular structure is stabilized by weak intramolecular O2—H2A···N2 hydrogen bond and the crystal structure exhibit weak intermolecular N1—H1···O1ⁱ, C8—H8···O1ⁱ and C3—H3···π (Cg2ⁱⁱ is the centroid of C9–C14 ring) interactions (Fig. 2 & Table 1). Symmetry codes (i) and (ii) are indicated in Table 1.

Related literature top

For the biological activity of Schiff base ligands, see: Kelley et al. (1995); Pandeya et al. (1999); Singh & Dash (1988); Tarafder et al. (2002). For related strucutures, see: Bahron et al. (2010); Manvizhi et al. (2010).

Experimental top

The benzoic acid hydrazide (5 mmol) in methanol (10 ml) was stirred in a round bottom flask followed by drop wise addition of methanolic solution of 4–(diethylamino)salicylaldehyde (5 mmol). The reaction mixture was then refluxed for three hours and upon cooling to 273 K. A pale yellow crystalline solid precipitates from the mixture was separated out. Crystalline product was washed with ice cold ethanol and dried in vacuo over anhydrous CaCl₂. Single crystals suitable for the X–ray diffraction were obtained by slow evaporation of a solution of the title compound in DMF at room temperature. Melting point 500 K.

Structure description top

For the biological activity of Schiff base ligands, see: Kelley et al. (1995); Pandeya et al. (1999); Singh & Dash (1988); Tarafder et al. (2002). For related strucutures, see: Bahron et al. (2010); Manvizhi et al. (2010).

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. The molecular structure of title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. For disordered ethyl group only major moiety is presented. H atoms are shown as a small spheres of arbitrary radius.
	Fig. 2. The crystal structure of title compound, viewed down a axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

N'-[(1E)-4-Diethylamino-2-hydroxybenzylidene]benzohydrazide top

Crystal data top

C₁₈H₂₁N₃O₂	F(000) = 664
M_r = 311.38	D_x = 1.235 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 500 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.591 (5) Å	Cell parameters from 4483 reflections
b = 16.733 (6) Å	θ = 2.9–29.1°
c = 9.671 (5) Å	µ = 0.08 mm⁻¹
β = 102.316 (5)°	T = 295 K
V = 1674.4 (13) Å³	Block, pale yellow
Z = 4	0.28 × 0.24 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3884 independent reflections
Radiation source: fine–focus sealed tube	2466 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
φ– and ω–scans	θ_max = 29.2°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −14→13
T_min = 0.977, T_max = 0.984	k = −22→18
9666 measured reflections	l = −12→13

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)] = 0.072	H-atom parameters constrained
wR(F²) = 0.203	w = 1/[σ²(F_o²) + (0.0782P)² + 0.8512P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3884 reflections	Δρ_max = 0.43 e Å⁻³
222 parameters	Δρ_min = −0.40 e Å⁻³
6 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (3)

Crystal data top

C₁₈H₂₁N₃O₂	V = 1674.4 (13) Å³
M_r = 311.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.591 (5) Å	µ = 0.08 mm⁻¹
b = 16.733 (6) Å	T = 295 K
c = 9.671 (5) Å	0.28 × 0.24 × 0.20 mm
β = 102.316 (5)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3884 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2466 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.984	R_int = 0.031
9666 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	6 restraints
wR(F²) = 0.203	H-atom parameters constrained
S = 1.05	Δρ_max = 0.43 e Å⁻³
3884 reflections	Δρ_min = −0.40 e Å⁻³
222 parameters

Special details top

Geometry. All s.u.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
C1	0.3790 (2)	0.27667 (16)	0.7824 (2)	0.0476 (6)
C2	0.2753 (3)	0.2435 (2)	0.8285 (3)	0.0669 (8)
H2	0.2877	0.1980	0.8850	0.080*
C3	0.1545 (3)	0.2771 (3)	0.7914 (5)	0.0950 (13)
H3	0.0849	0.2538	0.8207	0.114*
C4	0.1374 (4)	0.3448 (4)	0.7114 (4)	0.1128 (17)
H4	0.0554	0.3672	0.6850	0.135*
C5	0.2401 (5)	0.3807 (3)	0.6692 (4)	0.1231 (19)
H5	0.2282	0.4282	0.6182	0.148*
C6	0.3614 (3)	0.3455 (2)	0.7031 (3)	0.0831 (11)
H6	0.4305	0.3684	0.6722	0.100*
C7	0.5058 (2)	0.23618 (14)	0.8256 (2)	0.0416 (5)
C8	0.7610 (2)	0.19544 (16)	0.6584 (2)	0.0477 (6)
H8	0.7314	0.2260	0.5776	0.057*
C9	0.8774 (2)	0.14947 (15)	0.6699 (2)	0.0436 (6)
C10	0.9440 (2)	0.15018 (17)	0.5596 (2)	0.0510 (6)
H10	0.9133	0.1823	0.4812	0.061*
C11	1.0526 (2)	0.10543 (18)	0.5627 (3)	0.0559 (7)
H11	1.0945	0.1082	0.4875	0.067*
C12	1.1017 (2)	0.05524 (17)	0.6782 (3)	0.0524 (6)
C13	1.0364 (2)	0.05409 (16)	0.7911 (3)	0.0512 (6)
H13	1.0676	0.0222	0.8697	0.061*
C14	0.9275 (2)	0.09940 (15)	0.7862 (2)	0.0449 (6)
C15	1.2777 (3)	0.0098 (2)	0.5648 (3)	0.0690 (8)
H15A	1.2157	0.0150	0.4757	0.083*
H15B	1.3226	−0.0406	0.5630	0.083*
C16	1.3733 (3)	0.0763 (2)	0.5773 (4)	0.0863 (10)
H16A	1.3298	0.1264	0.5793	0.129*
H16B	1.4140	0.0751	0.4976	0.129*
H16C	1.4377	0.0700	0.6630	0.129*
C17	1.2575 (4)	−0.0495 (4)	0.7989 (4)	0.1165 (17)
H17A	1.1854	−0.0671	0.8385	0.140*	0.810 (8)
H17B	1.2922	−0.0961	0.7605	0.140*	0.810 (8)
H17C	1.3506	−0.0446	0.8124	0.140*	0.190 (8)
H17D	1.2359	−0.0233	0.8803	0.140*	0.190 (8)
N1	0.58174 (18)	0.23775 (13)	0.73010 (19)	0.0478 (5)
H1	0.5590	0.2647	0.6531	0.057*
N2	0.69687 (17)	0.19532 (13)	0.7574 (2)	0.0473 (5)
N3	1.2080 (2)	0.00784 (18)	0.6801 (3)	0.0766 (8)
O1	0.53870 (16)	0.20183 (12)	0.93992 (16)	0.0574 (5)
O2	0.86897 (17)	0.09411 (12)	0.89825 (18)	0.0628 (6)
H2A	0.8054	0.1234	0.8849	0.094*
C18	1.3519 (5)	−0.0184 (4)	0.9069 (6)	0.121 (2)	0.810 (8)
H18A	1.3185	0.0276	0.9465	0.182*	0.810 (8)
H18B	1.4256	−0.0031	0.8699	0.182*	0.810 (8)
H18C	1.3772	−0.0581	0.9791	0.182*	0.810 (8)
C18A	1.241 (2)	−0.1276 (11)	0.827 (2)	0.122 (7)	0.190 (8)
H18D	1.2950	−0.1413	0.9165	0.183*	0.190 (8)
H18E	1.2651	−0.1598	0.7539	0.183*	0.190 (8)
H18F	1.1524	−0.1373	0.8287	0.183*	0.190 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0438 (13)	0.0650 (16)	0.0350 (10)	0.0059 (11)	0.0108 (9)	−0.0109 (11)
C2	0.0472 (15)	0.072 (2)	0.085 (2)	−0.0064 (14)	0.0217 (14)	−0.0232 (16)
C3	0.0463 (17)	0.121 (3)	0.119 (3)	−0.001 (2)	0.0213 (19)	−0.053 (3)
C4	0.071 (2)	0.185 (5)	0.080 (2)	0.063 (3)	0.0093 (19)	−0.023 (3)
C5	0.127 (3)	0.170 (4)	0.083 (2)	0.097 (3)	0.047 (2)	0.046 (3)
C6	0.086 (2)	0.106 (3)	0.0680 (18)	0.044 (2)	0.0400 (17)	0.0290 (18)
C7	0.0392 (11)	0.0510 (14)	0.0347 (10)	−0.0056 (10)	0.0080 (9)	−0.0076 (10)
C8	0.0398 (12)	0.0637 (16)	0.0396 (11)	0.0020 (11)	0.0084 (9)	0.0022 (11)
C9	0.0342 (11)	0.0578 (15)	0.0393 (11)	−0.0021 (10)	0.0088 (9)	0.0000 (10)
C10	0.0419 (12)	0.0728 (18)	0.0390 (11)	0.0034 (12)	0.0102 (10)	0.0084 (11)
C11	0.0470 (14)	0.0810 (19)	0.0441 (13)	0.0054 (13)	0.0199 (10)	0.0039 (12)
C12	0.0401 (13)	0.0704 (18)	0.0479 (13)	0.0053 (12)	0.0122 (10)	0.0003 (12)
C13	0.0427 (12)	0.0659 (17)	0.0462 (12)	0.0059 (12)	0.0122 (10)	0.0089 (12)
C14	0.0386 (12)	0.0583 (15)	0.0398 (11)	−0.0051 (11)	0.0129 (9)	0.0006 (10)
C15	0.0591 (16)	0.081 (2)	0.0721 (18)	0.0123 (16)	0.0255 (14)	−0.0058 (16)
C16	0.079 (2)	0.093 (3)	0.089 (2)	−0.003 (2)	0.0219 (18)	0.006 (2)
C17	0.080 (2)	0.200 (5)	0.078 (2)	0.077 (3)	0.0359 (17)	0.044 (2)
N1	0.0394 (10)	0.0662 (14)	0.0391 (9)	0.0089 (9)	0.0115 (8)	0.0044 (9)
N2	0.0364 (10)	0.0636 (14)	0.0422 (10)	0.0034 (9)	0.0094 (8)	−0.0003 (9)
N3	0.0568 (14)	0.110 (2)	0.0699 (15)	0.0288 (14)	0.0290 (12)	0.0117 (13)
O1	0.0563 (10)	0.0785 (13)	0.0387 (9)	0.0050 (9)	0.0128 (7)	0.0050 (8)
O2	0.0574 (11)	0.0875 (14)	0.0505 (10)	0.0146 (10)	0.0272 (8)	0.0179 (9)
C18	0.108 (4)	0.140 (5)	0.121 (4)	0.037 (3)	0.036 (2)	0.043 (3)
C18A	0.110 (17)	0.195 (10)	0.058 (11)	0.065 (16)	0.010 (10)	0.029 (14)

Geometric parameters (Å, º) top

C1—C6	1.374 (4)	C14—O2	1.362 (3)
C1—C2	1.387 (4)	C15—N3	1.464 (3)
C1—C7	1.483 (3)	C15—C16	1.492 (5)
C2—C3	1.373 (5)	C15—H15A	0.9700
C2—H2	0.9300	C15—H15B	0.9700
C3—C4	1.363 (6)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.378 (7)	C16—H16C	0.9600
C4—H4	0.9300	C17—C18A	1.353 (16)
C5—C6	1.387 (5)	C17—C18	1.384 (7)
C5—H5	0.9300	C17—N3	1.502 (5)
C6—H6	0.9300	C17—H17A	0.9700
C7—O1	1.229 (3)	C17—H17B	0.9700
C7—N1	1.348 (3)	C17—H17C	0.9700
C8—N2	1.287 (3)	C17—H17D	0.9700
C8—C9	1.437 (3)	N1—N2	1.387 (3)
C8—H8	0.9300	N1—H1	0.8600
C9—C10	1.399 (3)	O2—H2A	0.8200
C9—C14	1.412 (3)	C18—H17C	1.0114
C10—C11	1.367 (3)	C18—H17D	1.2036
C10—H10	0.9300	C18—H18A	0.9600
C11—C12	1.406 (4)	C18—H18B	0.9600
C11—H11	0.9300	C18—H18C	0.9600
C12—N3	1.374 (3)	C18A—H18D	0.9600
C12—C13	1.411 (3)	C18A—H18E	0.9600
C13—C14	1.372 (3)	C18A—H18F	0.9600
C13—H13	0.9300

C6—C1—C2	119.5 (3)	H16A—C16—H16B	109.5
C6—C1—C7	123.2 (2)	C15—C16—H16C	109.5
C2—C1—C7	117.3 (2)	H16A—C16—H16C	109.5
C3—C2—C1	120.7 (4)	H16B—C16—H16C	109.5
C3—C2—H2	119.7	C18A—C17—C18	108.4 (9)
C1—C2—H2	119.7	C18A—C17—N3	136.9 (10)
C4—C3—C2	119.5 (4)	C18—C17—N3	114.5 (5)
C4—C3—H3	120.3	C18A—C17—H17A	59.0
C2—C3—H3	120.3	C18—C17—H17A	108.6
C3—C4—C5	120.9 (3)	N3—C17—H17A	108.6
C3—C4—H4	119.6	C18A—C17—H17B	51.1
C5—C4—H4	119.6	C18—C17—H17B	108.6
C4—C5—C6	119.6 (4)	N3—C17—H17B	108.6
C4—C5—H5	120.2	H17A—C17—H17B	107.6
C6—C5—H5	120.2	C18A—C17—H17C	102.8
C1—C6—C5	119.8 (3)	C18—C17—H17C	46.9
C1—C6—H6	120.1	N3—C17—H17C	103.2
C5—C6—H6	120.1	H17A—C17—H17C	146.7
O1—C7—N1	122.0 (2)	H17B—C17—H17C	70.2
O1—C7—C1	122.2 (2)	C18A—C17—H17D	102.4
N1—C7—C1	115.8 (2)	C18—C17—H17D	58.4
N2—C8—C9	121.5 (2)	N3—C17—H17D	103.2
N2—C8—H8	119.3	H17A—C17—H17D	58.3
C9—C8—H8	119.3	H17B—C17—H17D	148.1
C10—C9—C14	116.5 (2)	H17C—C17—H17D	105.2
C10—C9—C8	120.0 (2)	C7—N1—N2	119.22 (19)
C14—C9—C8	123.4 (2)	C7—N1—H1	120.4
C11—C10—C9	122.5 (2)	N2—N1—H1	120.4
C11—C10—H10	118.7	C8—N2—N1	116.09 (19)
C9—C10—H10	118.7	C12—N3—C15	121.5 (2)
C10—C11—C12	120.7 (2)	C12—N3—C17	122.0 (2)
C10—C11—H11	119.6	C15—N3—C17	116.5 (2)
C12—C11—H11	119.6	C14—O2—H2A	109.5
N3—C12—C11	121.2 (2)	H17C—C18—H17D	87.7
N3—C12—C13	121.1 (2)	C17—C18—H18A	109.5
C11—C12—C13	117.6 (2)	H17C—C18—H18A	140.6
C14—C13—C12	120.8 (2)	H17D—C18—H18A	72.1
C14—C13—H13	119.6	C17—C18—H18B	109.5
C12—C13—H13	119.6	H17C—C18—H18B	68.6
O2—C14—C13	117.3 (2)	H17D—C18—H18B	144.4
O2—C14—C9	121.0 (2)	C17—C18—H18C	109.5
C13—C14—C9	121.7 (2)	H17C—C18—H18C	107.8
N3—C15—C16	113.5 (3)	H17D—C18—H18C	102.8
N3—C15—H15A	108.9	C17—C18A—H18D	109.5
C16—C15—H15A	108.9	C17—C18A—H18E	109.5
N3—C15—H15B	108.9	H18D—C18A—H18E	109.5
C16—C15—H15B	108.9	C17—C18A—H18F	109.5
H15A—C15—H15B	107.7	H18D—C18A—H18F	109.5
C15—C16—H16A	109.5	H18E—C18A—H18F	109.5
C15—C16—H16B	109.5

C6—C1—C2—C3	2.3 (4)	C12—C13—C14—O2	179.0 (2)
C7—C1—C2—C3	−179.3 (3)	C12—C13—C14—C9	−0.8 (4)
C1—C2—C3—C4	−1.6 (5)	C10—C9—C14—O2	−179.5 (2)
C2—C3—C4—C5	−1.0 (6)	C8—C9—C14—O2	−2.3 (4)
C3—C4—C5—C6	2.9 (7)	C10—C9—C14—C13	0.3 (4)
C2—C1—C6—C5	−0.4 (5)	C8—C9—C14—C13	177.5 (2)
C7—C1—C6—C5	−178.7 (3)	O1—C7—N1—N2	4.1 (3)
C4—C5—C6—C1	−2.1 (6)	C1—C7—N1—N2	−174.4 (2)
C6—C1—C7—O1	145.2 (3)	C9—C8—N2—N1	−175.9 (2)
C2—C1—C7—O1	−33.2 (3)	C7—N1—N2—C8	176.0 (2)
C6—C1—C7—N1	−36.4 (3)	C11—C12—N3—C15	2.4 (4)
C2—C1—C7—N1	145.3 (2)	C13—C12—N3—C15	−178.8 (3)
N2—C8—C9—C10	179.3 (2)	C11—C12—N3—C17	−176.6 (4)
N2—C8—C9—C14	2.1 (4)	C13—C12—N3—C17	2.2 (5)
C14—C9—C10—C11	−0.3 (4)	C16—C15—N3—C12	82.8 (4)
C8—C9—C10—C11	−177.6 (3)	C16—C15—N3—C17	−98.1 (4)
C9—C10—C11—C12	0.8 (4)	C18A—C17—N3—C12	93.6 (15)
C10—C11—C12—N3	177.6 (3)	C18—C17—N3—C12	−92.3 (4)
C10—C11—C12—C13	−1.2 (4)	C18A—C17—N3—C15	−85.5 (15)
N3—C12—C13—C14	−177.6 (3)	C18—C17—N3—C15	88.6 (4)
C11—C12—C13—C14	1.2 (4)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.82	1.92	2.643 (3)	147
N1—H1···O1ⁱ	0.86	2.10	2.926 (3)	160
C8—H8···O1ⁱ	0.93	2.50	3.293 (3)	144
C3—H3···Cg2ⁱⁱ	0.93	2.97	3.468 (5)	115

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁N₃O₂
M_r	311.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.591 (5), 16.733 (6), 9.671 (5)
β (°)	102.316 (5)
V (Å³)	1674.4 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.977, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9666, 3884, 2466
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.203, 1.05
No. of reflections	3884
No. of parameters	222
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.40

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

Cg2 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.82	1.92	2.643 (3)	147
N1—H1···O1ⁱ	0.86	2.10	2.926 (3)	160
C8—H8···O1ⁱ	0.93	2.50	3.293 (3)	144
C3—H3···Cg2ⁱⁱ	0.93	2.97	3.468 (5)	115

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

Acknowledgements

The authors wish to acknowledge Pondichery University for the data collection.

References

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