(E)-N′-(4-Meth­oxy­benzyl­idene)-2-m-tolyl­acetohydrazide

Praveen, A.S.; Jasinski, J.P.; Keeley, A.C.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536812047113

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3435

doi:10.1107/S1600536812047113

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(E)-N′-(4-Methoxybenzylidene)-2-m-tolylacetohydrazide

A. S. Praveen,^a Jerry P. Jasinski,^b ^* Amanda C. Keeley,^b H. S. Yathirajan ^a and B. Narayana ^c

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 12 November 2012; accepted 15 November 2012; online 24 November 2012)

In the title molecule, C₁₇H₁₈N₂O₂, the benzene rings form a dihedral angle of 83.0 (7)°. In the crystal, N—H⋯O hydrogen bonds, in an R²₂(8) graph-set motif, link molecules into centrocymmetric dimers, and weak C—H⋯π interactions further link these dimers into columns in [100].

Related literature

For the biological activity of Schiff bases, see: Desai et al. (2001 ); El-Masry et al. (2000 ); Hodnett & Dunn (1970 ); Pandey et al. (1999 ); Singh & Dash (1988 ). For Schiff bases employed as ligands for complexation of metal ions, see: Aydogan et al. (2001 ). For Schiff bases with applications in dyes and pigments, see: Taggi et al. (2002 ). For related structures, see: Akkurt et al. (2011 ); Lv et al. (2009a ,b ); Yu & Lv (2010 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₈N₂O₂
M_r = 282.33
Triclinic, $[P \overline 1]$
a = 6.4961 (8) Å
b = 9.8047 (10) Å
c = 12.7464 (13) Å
α = 112.130 (9)°
β = 95.507 (10)°
γ = 96.601 (9)°
V = 738.45 (14) Å³
Z = 2
Cu Kα radiation
μ = 0.68 mm⁻¹
T = 173 K
0.34 × 0.14 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.735, T_max = 1.000
4418 measured reflections
2840 independent reflections
2032 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.158
S = 1.04
2840 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.04	2.902 (2)	178
C15—H15⋯Cgⁱⁱ	0.93	2.63	3.557 (2)	173
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+2, -y, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536812047113/cv5364sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047113/cv5364Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812047113/cv5364Isup3.cml

checkCIF report

Comment top

Schiff bases are known to have biological activities such as antimicrobial (El-Masry et al., 2000; Pandey et al., 1999), antifungal (Singh et al., 1988), antitumor (Hodnett et al., 1970; Desai et al., 2001), and as herbicides. Schiff bases have also been employed as ligands for complexation of metal ions (Aydogan et al., 2001). On the industrial scale, they have wide range of applications such as dyes and pigments (Taggi et al., 2002). The crystal structures of some Schiff base hydrazines, viz., N'-(2-methoxybenzylidene) acetohydrazide (Yu & Lv, 2010), 2-[6-(4-chlorophenyl)imidazo[2,1-b][1,3] thiazol-2-yl]-N'-[(E)-4-methoxybenzylidene]acetohydrazide (Akkurt et al., 2011), N'-(3-methoxybenzylidene)acetohydrazide and N'-(3,4-dimethoxybenzylidene)acetohydrazide (Lv et al., 2009a,b). In view of the importance of hydrazides, the crystal structure of title compound (I) is reported.

In the title molecule, C₁₇H₁₈N₂O₂, two benzene rings form a dihedral angle of 83.0 (7)° (Fig. 1). Bond lengths are in normal ranges (Allen, 1987). In the crystal, N—H···O hydrogen bonds (Table 1), in an R²₂(8) graph set motif, link molecules into centrocymmetric dimers, and weak C–H···π interactions (Table 1) link further these dimers into columns in [100] (Fig. 2).

Related literature top

For the biological activity of Schiff bases, see: Desai et al. (2001); El-Masry et al. (2000); Hodnett & Dunn (1970); Pandey et al. (1999); Singh & Dash (1988). For Schiff bases employed as ligands for complexation of metal ions, see: Aydogan et al. (2001). For Schiff bases with applications in dyes and pigments, see: Taggi et al. (2002). For related structures, see: Akkurt et al. (2011); Lv et al. (2009a,b); Yu & Lv (2010). For standard bond lengths, see: Allen et al. (1987).

Experimental top

To a stirred solution of 2-m-tolylacetohydrazide (1 g, 6.09 mmol) in ethanol (10 mL), 4-methoxybenzaldehyde (0.79 g, 6.09 mmol) was added (Fig. 3) and strirred at room temperature for 30 minutes. Precipitated solid was filtered and dried. The single crystal was grown from ethyl acetate by slow evaporation method and yield of the compound was 94% (m.p.: 403-405 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed along the a axis. Dashed lines indicate N—H···O hydrogen bonds. The remaining H atoms have been removed for clarity.
	Fig. 3. Synthesis of the title compound.

(E)-N'-(4-Methoxybenzylidene)-2-m-tolylacetohydrazide top

Crystal data top

C₁₇H₁₈N₂O₂	Z = 2
M_r = 282.33	F(000) = 300
Triclinic, P1	D_x = 1.270 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.4961 (8) Å	Cell parameters from 1237 reflections
b = 9.8047 (10) Å	θ = 3.8–72.4°
c = 12.7464 (13) Å	µ = 0.68 mm⁻¹
α = 112.130 (9)°	T = 173 K
β = 95.507 (10)°	Chunk, colorless
γ = 96.601 (9)°	0.34 × 0.14 × 0.06 mm
V = 738.45 (14) Å³

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2840 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2032 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 16.0416 pixels mm^-1	θ_max = 72.6°, θ_min = 3.8°
ω scans	h = −8→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→8
T_min = 0.735, T_max = 1.000	l = −11→15
4418 measured reflections

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)] = 0.052	H-atom parameters constrained
wR(F²) = 0.158	w = 1/[σ²(F_o²) + (0.064P)² + 0.071P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2840 reflections	Δρ_max = 0.21 e Å⁻³
193 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0097 (12)

Crystal data top

C₁₇H₁₈N₂O₂	γ = 96.601 (9)°
M_r = 282.33	V = 738.45 (14) Å³
Triclinic, P1	Z = 2
a = 6.4961 (8) Å	Cu Kα radiation
b = 9.8047 (10) Å	µ = 0.68 mm⁻¹
c = 12.7464 (13) Å	T = 173 K
α = 112.130 (9)°	0.34 × 0.14 × 0.06 mm
β = 95.507 (10)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	2840 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2032 reflections with I > 2σ(I)
T_min = 0.735, T_max = 1.000	R_int = 0.034
4418 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.04	Δρ_max = 0.21 e Å⁻³
2840 reflections	Δρ_min = −0.20 e Å⁻³
193 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.4694 (2)	0.19694 (16)	0.05426 (13)	0.0429 (4)
O2	1.6491 (2)	−0.04156 (17)	−0.38486 (13)	0.0482 (4)
N1	0.7161 (2)	0.09164 (19)	−0.04553 (14)	0.0363 (4)
H1	0.6645	0.0052	−0.0486	0.044*
N2	0.8879 (2)	0.10557 (19)	−0.09800 (14)	0.0365 (4)
C1	0.6266 (3)	0.2111 (2)	0.01087 (17)	0.0376 (5)
C2	0.7332 (4)	0.3634 (2)	0.02237 (19)	0.0447 (5)
H2A	0.8138	0.3528	−0.0397	0.054*
H2B	0.6288	0.4255	0.0188	0.054*
C3	0.8763 (3)	0.4349 (2)	0.13628 (19)	0.0397 (5)
C4	1.0802 (4)	0.4059 (2)	0.1471 (2)	0.0488 (6)
H4	1.1354	0.3504	0.0826	0.059*
C5	1.2004 (4)	0.4600 (3)	0.2543 (3)	0.0584 (7)
H5	1.3365	0.4402	0.2617	0.070*
C6	1.1199 (4)	0.5432 (3)	0.3507 (3)	0.0596 (7)
H6	1.2023	0.5784	0.4222	0.071*
C7	0.9182 (4)	0.5748 (2)	0.3419 (2)	0.0487 (6)
C8	0.7994 (3)	0.5198 (2)	0.2336 (2)	0.0419 (5)
H8	0.6640	0.5408	0.2262	0.050*
C9	0.9579 (3)	−0.0161 (2)	−0.14981 (17)	0.0353 (5)
H9	0.8927	−0.1052	−0.1490	0.042*
C10	1.1381 (3)	−0.0163 (2)	−0.20977 (16)	0.0336 (4)
C11	1.2404 (3)	0.1120 (2)	−0.21651 (17)	0.0365 (5)
H11	1.1929	0.2020	−0.1818	0.044*
C12	1.4114 (3)	0.1087 (2)	−0.27377 (18)	0.0376 (5)
H12	1.4781	0.1958	−0.2771	0.045*
C13	1.4832 (3)	−0.0259 (2)	−0.32644 (17)	0.0362 (5)
C14	1.3827 (3)	−0.1543 (2)	−0.31983 (18)	0.0403 (5)
H14	1.4310	−0.2441	−0.3541	0.048*
C15	1.2124 (3)	−0.1503 (2)	−0.26320 (17)	0.0379 (5)
H15	1.1458	−0.2377	−0.2603	0.045*
C16	1.7630 (3)	0.0894 (3)	−0.3878 (2)	0.0523 (6)
H16A	1.6733	0.1318	−0.4272	0.078*
H16B	1.8807	0.0643	−0.4272	0.078*
H16C	1.8118	0.1605	−0.3109	0.078*
C17	0.8251 (5)	0.6648 (3)	0.4450 (2)	0.0709 (8)
H17A	0.7722	0.7457	0.4325	0.106*
H17B	0.9312	0.7039	0.5114	0.106*
H17C	0.7128	0.6020	0.4568	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0382 (8)	0.0476 (9)	0.0442 (8)	0.0160 (7)	0.0149 (7)	0.0148 (7)
O2	0.0452 (9)	0.0510 (10)	0.0483 (9)	0.0128 (7)	0.0216 (7)	0.0144 (7)
N1	0.0370 (9)	0.0360 (9)	0.0391 (9)	0.0108 (7)	0.0137 (7)	0.0150 (7)
N2	0.0349 (9)	0.0411 (10)	0.0373 (9)	0.0126 (7)	0.0123 (7)	0.0163 (8)
C1	0.0375 (11)	0.0448 (12)	0.0347 (10)	0.0177 (9)	0.0081 (9)	0.0164 (9)
C2	0.0544 (13)	0.0416 (12)	0.0501 (13)	0.0228 (10)	0.0188 (10)	0.0245 (10)
C3	0.0438 (12)	0.0301 (10)	0.0523 (13)	0.0117 (9)	0.0164 (10)	0.0204 (9)
C4	0.0453 (13)	0.0380 (12)	0.0692 (16)	0.0117 (10)	0.0231 (12)	0.0232 (11)
C5	0.0348 (12)	0.0457 (14)	0.096 (2)	0.0049 (10)	0.0052 (13)	0.0307 (14)
C6	0.0587 (16)	0.0412 (13)	0.0705 (18)	−0.0021 (11)	−0.0082 (13)	0.0199 (12)
C7	0.0599 (14)	0.0317 (11)	0.0513 (14)	0.0062 (10)	0.0098 (11)	0.0127 (10)
C8	0.0418 (12)	0.0312 (10)	0.0584 (14)	0.0134 (9)	0.0173 (10)	0.0194 (10)
C9	0.0378 (11)	0.0337 (10)	0.0366 (10)	0.0095 (8)	0.0089 (8)	0.0144 (8)
C10	0.0347 (10)	0.0361 (10)	0.0310 (10)	0.0106 (8)	0.0071 (8)	0.0126 (8)
C11	0.0397 (11)	0.0330 (10)	0.0391 (11)	0.0134 (8)	0.0097 (9)	0.0135 (9)
C12	0.0389 (11)	0.0360 (11)	0.0403 (11)	0.0089 (8)	0.0086 (9)	0.0160 (9)
C13	0.0348 (10)	0.0428 (11)	0.0310 (10)	0.0098 (8)	0.0075 (8)	0.0130 (9)
C14	0.0429 (12)	0.0357 (11)	0.0405 (11)	0.0149 (9)	0.0126 (9)	0.0091 (9)
C15	0.0426 (11)	0.0320 (10)	0.0400 (11)	0.0095 (8)	0.0103 (9)	0.0132 (9)
C16	0.0429 (13)	0.0643 (16)	0.0530 (14)	0.0051 (11)	0.0186 (11)	0.0249 (12)
C17	0.096 (2)	0.0541 (16)	0.0542 (16)	0.0169 (15)	0.0162 (15)	0.0096 (13)

Geometric parameters (Å, º) top

O1—C1	1.225 (2)	C7—C17	1.508 (3)
O2—C13	1.358 (2)	C8—H8	0.9300
O2—C16	1.422 (3)	C9—C10	1.457 (3)
N1—C1	1.352 (2)	C9—H9	0.9300
N1—N2	1.374 (2)	C10—C11	1.390 (3)
N1—H1	0.8600	C10—C15	1.399 (3)
N2—C9	1.286 (2)	C11—C12	1.383 (3)
C1—C2	1.520 (3)	C11—H11	0.9300
C2—C3	1.513 (3)	C12—C13	1.394 (3)
C2—H2A	0.9700	C12—H12	0.9300
C2—H2B	0.9700	C13—C14	1.386 (3)
C3—C8	1.385 (3)	C14—C15	1.374 (3)
C3—C4	1.391 (3)	C14—H14	0.9300
C4—C5	1.383 (4)	C15—H15	0.9300
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.383 (4)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C6—C7	1.384 (3)	C17—H17A	0.9600
C6—H6	0.9300	C17—H17B	0.9600
C7—C8	1.389 (3)	C17—H17C	0.9600

C13—O2—C16	117.66 (17)	N2—C9—H9	119.5
C1—N1—N2	121.37 (17)	C10—C9—H9	119.5
C1—N1—H1	119.3	C11—C10—C15	118.04 (18)
N2—N1—H1	119.3	C11—C10—C9	122.64 (18)
C9—N2—N1	115.66 (17)	C15—C10—C9	119.32 (18)
O1—C1—N1	121.0 (2)	C12—C11—C10	121.44 (18)
O1—C1—C2	121.47 (18)	C12—C11—H11	119.3
N1—C1—C2	117.52 (18)	C10—C11—H11	119.3
C3—C2—C1	108.30 (17)	C11—C12—C13	119.67 (19)
C3—C2—H2A	110.0	C11—C12—H12	120.2
C1—C2—H2A	110.0	C13—C12—H12	120.2
C3—C2—H2B	110.0	O2—C13—C14	116.24 (18)
C1—C2—H2B	110.0	O2—C13—C12	124.44 (19)
H2A—C2—H2B	108.4	C14—C13—C12	119.32 (19)
C8—C3—C4	118.9 (2)	C15—C14—C13	120.69 (19)
C8—C3—C2	119.98 (19)	C15—C14—H14	119.7
C4—C3—C2	120.8 (2)	C13—C14—H14	119.7
C5—C4—C3	119.6 (2)	C14—C15—C10	120.84 (19)
C5—C4—H4	120.2	C14—C15—H15	119.6
C3—C4—H4	120.2	C10—C15—H15	119.6
C4—C5—C6	120.6 (2)	O2—C16—H16A	109.5
C4—C5—H5	119.7	O2—C16—H16B	109.5
C6—C5—H5	119.7	H16A—C16—H16B	109.5
C5—C6—C7	120.8 (3)	O2—C16—H16C	109.5
C5—C6—H6	119.6	H16A—C16—H16C	109.5
C7—C6—H6	119.6	H16B—C16—H16C	109.5
C6—C7—C8	117.9 (2)	C7—C17—H17A	109.5
C6—C7—C17	122.3 (3)	C7—C17—H17B	109.5
C8—C7—C17	119.8 (2)	H17A—C17—H17B	109.5
C3—C8—C7	122.1 (2)	C7—C17—H17C	109.5
C3—C8—H8	119.0	H17A—C17—H17C	109.5
C7—C8—H8	119.0	H17B—C17—H17C	109.5
N2—C9—C10	120.92 (18)

C1—N1—N2—C9	−179.39 (18)	C17—C7—C8—C3	−179.1 (2)
N2—N1—C1—O1	177.62 (17)	N1—N2—C9—C10	179.35 (16)
N2—N1—C1—C2	−4.8 (3)	N2—C9—C10—C11	−1.4 (3)
O1—C1—C2—C3	83.1 (2)	N2—C9—C10—C15	178.72 (18)
N1—C1—C2—C3	−94.5 (2)	C15—C10—C11—C12	−0.2 (3)
C1—C2—C3—C8	−88.4 (2)	C9—C10—C11—C12	179.85 (18)
C1—C2—C3—C4	85.9 (2)	C10—C11—C12—C13	0.2 (3)
C8—C3—C4—C5	1.0 (3)	C16—O2—C13—C14	−176.56 (19)
C2—C3—C4—C5	−173.3 (2)	C16—O2—C13—C12	3.1 (3)
C3—C4—C5—C6	−0.3 (3)	C11—C12—C13—O2	179.91 (18)
C4—C5—C6—C7	−0.3 (4)	C11—C12—C13—C14	−0.5 (3)
C5—C6—C7—C8	0.3 (4)	O2—C13—C14—C15	−179.62 (18)
C5—C6—C7—C17	179.8 (2)	C12—C13—C14—C15	0.7 (3)
C4—C3—C8—C7	−1.2 (3)	C13—C14—C15—C10	−0.7 (3)
C2—C3—C8—C7	173.23 (19)	C11—C10—C15—C14	0.5 (3)
C6—C7—C8—C3	0.5 (3)	C9—C10—C15—C14	−179.58 (18)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.04	2.902 (2)	178
C15—H15···Cgⁱⁱ	0.93	2.63	3.557 (2)	173

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₂
M_r	282.33
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.4961 (8), 9.8047 (10), 12.7464 (13)
α, β, γ (°)	112.130 (9), 95.507 (10), 96.601 (9)
V (Å³)	738.45 (14)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.34 × 0.14 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.735, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4418, 2840, 2032
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.158, 1.04
No. of reflections	2840
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.04	2.902 (2)	177.6
C15—H15···Cgⁱⁱ	0.93	2.63	3.557 (2)	173.0

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

Acknowledgements

ASP thanks UOM for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

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