4-Eth­oxy­benzohydrazide

Farman, M.; Khanum, S.; Hameed, S.; Jones, P.G.; Ahmad, T.

doi:10.1107/S1600536812038998

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages o2955-o2956

https://doi.org/10.1107/S1600536812038998

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4-Ethoxybenzohydrazide

Muhammad Farman,^a ^* Saira Khanum,^a Shahid Hameed,^a Peter G. Jones ^b and Tanveer Ahmad ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany
^*Correspondence e-mail: farman@qau.edu.pk

(Received 10 August 2012; accepted 12 September 2012; online 19 September 2012)

The title compound, C₉H₁₂N₂O₂, is approximately planar (r.m.s. deviation = 0.13 Å for all non-H atoms). The carbonyl O atom is involved as acceptor in three different hydrogen-bond interactions. One N—H⋯O and the C—H⋯O(carbonyl) contact together with a weak C—H⋯O(ethoxy) interaction link the molecules into sheets parallel to (102). These are further linked into a three-dimensional network via the remaining C—H⋯O(carbonyl) hydrogen bond and a C(methylene)—H⋯π interaction

Related literature

For the methoxy analogue of the title compound, see: Ashiq et al. (2009 ). For biological properties of hydrazides, see: Gohil et al. (2010 ); Bordoloi et al. (2009 ); Kumar et al. (2009 ). For the use of hydrazides as precursors for the syntheses of heterocyclic compounds, see: Akhtar et al. (2010 ); Akhtar, Hameed, Al-Masoudi et al. (2008 ); Akhtar, Hameed, Khan et al. (2008 ); Khan, Akhtar et al. (2010 ); Khan, Hameed et al. (2010 ); Serwar et al. (2009 ); Syed et al. (2011 ); Zahid et al. (2009 ); Zia et al. (2012 ). For a description of the Cambridge Structural Database, see: Allen (2002 ); For details of the preparation, see: Furniss et al. (1989 ).

Experimental

Crystal data

C₉H₁₂N₂O₂
M_r = 180.21
Monoclinic, P 2₁ /c
a = 10.8848 (3) Å
b = 10.0453 (2) Å
c = 8.4420 (3) Å
β = 110.669 (4)°
V = 863.64 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
42766 measured reflections
2874 independent reflections
2478 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.106
S = 1.10
2874 reflections
131 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H03⋯O1ⁱ	0.865 (13)	2.083 (13)	2.9290 (9)	165.6 (11)
C6—H6⋯O1ⁱ	0.95	2.39	3.3149 (9)	165
C3—H3⋯O2ⁱⁱ	0.95	2.61	3.5428 (9)	168
N1—H01⋯O1ⁱⁱⁱ	0.933 (13)	2.212 (14)	3.1207 (9)	164.1 (12)
C8—H8B⋯Cg^iv	0.99	2.65	3.499 (1)	145
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+2; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812038998/lr2080sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038998/lr2080Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812038998/lr2080Isup3.cml

checkCIF report

Comment top

Hydrazides represent one of the most biologically active classes of compounds reported in the chemical literature; they display a wide variety of biological activities such as antimicrobial (Kumar et al., 2009) anticancer (Gohil et al., 2010) and antigenotoxic (Bordoloi et al., 2009). They have been employed as synthetic precursors for a number of hetero-cyclic compounds such as oxadiazoles, triazoles and thiadiazoles (Zia et al., 2012; Syed et al., 2011; Akhtar et al., 2010; Akhtar, Hameed, Al-Masoudi et al., 2008; Akhtar, Hameed, Khan et al., 2008; Khan, Akhtar et al. , 2010; Khan, Hameed et al. , 2010; Serwar et al., 2009; Zahid et al., 2009). The title compound (1) was synthesized as an intermediate for its subsequent conversion to 1,2,4-triazoles and 1,3,4-thiadiazoles in order to explore their potential as antibacterial or antifungal agents or urease inhibitors.

The structure of (1) is shown in Fig. 1. Molecular dimensions may be regarded as normal, e.g. the N—N bond length of 1.4117 (9) Å; a search of the Cambridge Structural Database (CSD, CONQUEST Version 1.14; Allen, 2002) for the benzohydrazine fragment gave 37 hits (41 molecules) with an average N—N bond length of 1.415 (5) Å. The molecule is approximately planar, with an r.m.s. deviation of 0.13 Å for all non-H atoms. The angle between the phenyl and CON₂ planes is 14.65 (6)°. The hydrogen atoms of the NH₂ group lie to either side of the CON₂ plane, with torsion angles C7—N2—N1—H01 61.8 (9)° and C7—N2—N1—H02 - 53.1 (8)°.

The carbonyl oxygen is involved as acceptor in three different hydrogen bond interactions. Two of them form a bifurcated N2—H03···O1⁽ⁱ⁾, C6—H6···O1⁽ⁱ⁾system, these interactions together with a very weak C3—H3···O2⁽ⁱⁱ⁾ (ethoxy) hydrogen bond link the molecules into sheets parallel to (102). These layers are further linked into a three-dimensional network via the remaining N1—H01···O1⁽ⁱⁱⁱ⁾ (carbonyl) hydrogen bond and a C8—H8B···Cg^(iv) π interaction, where Cg is the centroid of the C1-C6 benzene ring [symmetry codes: (i) -x, y+1/2,-z+3/2;(ii) -x+1,-y+1,-z+1; (iii)-x, -y+1,-z+2 and (iv) x, -y+3/2, z-1/2]. The hydrogen H02 is not involved in hydrogen bonding interactions.

Compound (1) is not isotypic to its methoxy analogue (Ashiq et al., 2009), which crystallizes in P2₁2₁2₁.

Related literature top

For the methoxy analogue of the title compound, see: Ashiq et al. (2009). For biological properties of hydrazides, see: Gohil et al. (2010); Bordoloi et al. (2009); Kumar et al. (2009). For the use of hydrazides as precursors for the syntheses of heterocyclic compounds, see: Akhtar et al. (2010); Akhtar, Hameed, Al-Masoudi et al. (2008); Akhtar, Hameed, Khan et al. (2008); Khan, Akhtar et al. (2010); Khan, Hameed et al. (2010); Serwar et al. (2009); Syed et al. (2011); Zahid et al. (2009); Zia et al. (2012). For a description of the Cambridge Structural Database, see: Allen (2002); For details of the preparation, see: Furniss et al. (1989).

Experimental top

3.6 g of methyl p-ethoxybenzoate was added to 40 ml freshly distilled methanol in a round-bottomed flask. The content was stirred until completely dissolved and the flask was fitted with a reflux condenser bearing a calcium chloride guard tube. Then 2.0 g of 80% hydrazine hydrate was added slowly. The reaction was monitored by thin layer chromatography. Upon completion of the reaction, the content was concentrated in vacuo (Furniss et al., 1989). The resulting crude solid was filtered, washed with water and agitated with freshly distilled acetone for 1 h. The product was then recrystallized from aqueous ethanol.

Structure description top

Compound (1) is not isotypic to its methoxy analogue (Ashiq et al., 2009), which crystallizes in P2₁2₁2₁.

For the methoxy analogue of the title compound, see: Ashiq et al. (2009). For biological properties of hydrazides, see: Gohil et al. (2010); Bordoloi et al. (2009); Kumar et al. (2009). For the use of hydrazides as precursors for the syntheses of heterocyclic compounds, see: Akhtar et al. (2010); Akhtar, Hameed, Al-Masoudi et al. (2008); Akhtar, Hameed, Khan et al. (2008); Khan, Akhtar et al. (2010); Khan, Hameed et al. (2010); Serwar et al. (2009); Syed et al. (2011); Zahid et al. (2009); Zia et al. (2012). For a description of the Cambridge Structural Database, see: Allen (2002); For details of the preparation, see: Furniss et al. (1989).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Ellipsoids represent 50% probability levels.
	Fig. 2. A view of the packing scheme, showing the layers parallel to (102). Thick dashed bonds represent classical H bonds and thin dashed bonds represent weak hydrogen bonds.

4-Ethoxybenzohydrazide top

Crystal data top

C₉H₁₂N₂O₂	F(000) = 384
M_r = 180.21	D_x = 1.386 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 403 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.8848 (3) Å	Cell parameters from 23790 reflections
b = 10.0453 (2) Å	θ = 2.6–32.6°
c = 8.4420 (3) Å	µ = 0.10 mm⁻¹
β = 110.669 (4)°	T = 100 K
V = 863.64 (4) Å³	Block, colourless
Z = 4	0.3 × 0.2 × 0.2 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2478 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.024
Graphite monochromator	θ_max = 31.5°, θ_min = 2.9°
Detector resolution: 16.1419 pixels mm^-1	h = −15→15
ω scan	k = −14→14
42766 measured reflections	l = −12→12
2874 independent 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0734P)² + 0.0351P] where P = (F_o² + 2F_c²)/3
2874 reflections	(Δ/σ)_max = 0.002
131 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₉H₁₂N₂O₂	V = 863.64 (4) Å³
M_r = 180.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8848 (3) Å	µ = 0.10 mm⁻¹
b = 10.0453 (2) Å	T = 100 K
c = 8.4420 (3) Å	0.3 × 0.2 × 0.2 mm
β = 110.669 (4)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2478 reflections with I > 2σ(I)
42766 measured reflections	R_int = 0.024
2874 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.48 e Å⁻³
2874 reflections	Δρ_min = −0.22 e Å⁻³
131 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.5814 (0.0029) x - 0.3102 (0.0031) y + 6.4744 (0.0016) z = 4.7086 (0.0021)

* 0.0107 (0.0005) C1 * -0.0025 (0.0005) C2 * -0.0096 (0.0005) C3 * 0.0135 (0.0005) C4 * -0.0052 (0.0005) C5 * -0.0070 (0.0005) C6 0.1090 (0.0011) C7 0.1528 (0.0013) C8 0.3370 (0.0017) C9 0.4145 (0.0012) O1 0.0757 (0.0010) O2 - 0.0498 (0.0016) N1 - 0.1309 (0.0013) N2

Rms deviation of fitted atoms = 0.0089

3.5873 (0.0049) x + 2.2383 (0.0045) y + 6.2646 (0.0032) z = 6.0909 (0.0020)

Angle to previous plane (with approximate e.s.d.) = 14.65 (0.06)

* 0.0002 (0.0004) C7 * -0.0001 (0.0002) O1 * 0.0001 (0.0002) N1 * -0.0002 (0.0004) N2

Rms deviation of fitted atoms = 0.0001

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
C1	0.14875 (7)	0.60114 (7)	0.67544 (8)	0.01178 (14)
C2	0.21991 (7)	0.50128 (7)	0.62925 (9)	0.01315 (14)
H2	0.1982	0.4104	0.6363	0.016*
C3	0.32166 (7)	0.53422 (7)	0.57344 (9)	0.01377 (14)
H3	0.3685	0.4660	0.5411	0.017*
C4	0.35534 (7)	0.66779 (7)	0.56479 (9)	0.01238 (14)
C5	0.28323 (7)	0.76797 (7)	0.60658 (9)	0.01476 (15)
H5	0.3040	0.8589	0.5977	0.018*
C6	0.18082 (7)	0.73392 (7)	0.66132 (9)	0.01406 (15)
H6	0.1319	0.8023	0.6896	0.017*
C7	0.04616 (7)	0.56096 (7)	0.74544 (9)	0.01238 (14)
C8	0.50091 (7)	0.82661 (7)	0.51338 (10)	0.01446 (15)
H8A	0.5170	0.8694	0.6245	0.017*
H8B	0.4315	0.8771	0.4259	0.017*
C9	0.62551 (8)	0.82519 (8)	0.47285 (10)	0.01797 (16)
H9A	0.6925	0.7725	0.5582	0.027*
H9B	0.6572	0.9165	0.4733	0.027*
H9C	0.6076	0.7856	0.3608	0.027*
N1	−0.13631 (7)	0.63025 (7)	0.82516 (9)	0.01874 (15)
H01	−0.0919 (13)	0.6029 (13)	0.9364 (17)	0.039 (3)*
H02	−0.1806 (12)	0.5584 (13)	0.7605 (16)	0.033 (3)*
N2	−0.03653 (6)	0.65623 (6)	0.75869 (8)	0.01518 (14)
H03	−0.0305 (11)	0.7382 (13)	0.7308 (14)	0.026 (3)*
O1	0.03801 (5)	0.44481 (5)	0.79156 (7)	0.01735 (13)
O2	0.46083 (5)	0.69025 (5)	0.51711 (7)	0.01480 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0120 (3)	0.0097 (3)	0.0148 (3)	0.0001 (2)	0.0061 (2)	0.0006 (2)
C2	0.0147 (3)	0.0096 (3)	0.0165 (3)	−0.0004 (2)	0.0072 (2)	−0.0006 (2)
C3	0.0156 (3)	0.0104 (3)	0.0175 (3)	0.0008 (2)	0.0086 (3)	−0.0006 (2)
C4	0.0129 (3)	0.0112 (3)	0.0149 (3)	0.0005 (2)	0.0073 (2)	0.0006 (2)
C5	0.0167 (3)	0.0095 (3)	0.0216 (3)	0.0006 (2)	0.0112 (3)	0.0012 (2)
C6	0.0151 (3)	0.0103 (3)	0.0198 (3)	0.0012 (2)	0.0100 (3)	0.0008 (2)
C7	0.0122 (3)	0.0109 (3)	0.0147 (3)	−0.0008 (2)	0.0057 (2)	−0.0002 (2)
C8	0.0163 (3)	0.0102 (3)	0.0197 (3)	−0.0009 (2)	0.0099 (3)	0.0001 (2)
C9	0.0170 (3)	0.0150 (3)	0.0261 (4)	−0.0019 (2)	0.0128 (3)	−0.0007 (3)
N1	0.0168 (3)	0.0200 (3)	0.0247 (3)	0.0005 (2)	0.0139 (3)	0.0032 (3)
N2	0.0152 (3)	0.0117 (3)	0.0232 (3)	0.0008 (2)	0.0125 (2)	0.0025 (2)
O1	0.0196 (3)	0.0106 (3)	0.0260 (3)	0.00006 (19)	0.0133 (2)	0.0031 (2)
O2	0.0159 (3)	0.0105 (2)	0.0229 (3)	−0.00056 (18)	0.0128 (2)	0.00054 (19)

Geometric parameters (Å, º) top

C1—C6	1.3944 (10)	C2—H2	0.9500
C1—C2	1.4041 (10)	C3—H3	0.9500
C1—C7	1.4916 (10)	C5—H5	0.9500
C2—C3	1.3879 (10)	C6—H6	0.9500
C3—C4	1.3997 (10)	C8—H8A	0.9900
C4—O2	1.3630 (8)	C8—H8B	0.9900
C4—C5	1.3959 (10)	C9—H9A	0.9800
C5—C6	1.3917 (10)	C9—H9B	0.9800
C7—O1	1.2431 (8)	C9—H9C	0.9800
C7—N2	1.3452 (9)	N1—H01	0.933 (13)
C8—O2	1.4413 (9)	N1—H02	0.931 (13)
C8—C9	1.5114 (10)	N2—H03	0.865 (13)
N1—N2	1.4117 (9)

C6—C1—C2	118.70 (6)	C6—C5—H5	120.2
C6—C1—C7	122.53 (6)	C4—C5—H5	120.2
C2—C1—C7	118.70 (6)	C5—C6—H6	119.4
C3—C2—C1	120.56 (6)	C1—C6—H6	119.4
C2—C3—C4	120.09 (6)	O2—C8—H8A	110.2
O2—C4—C5	124.25 (6)	C9—C8—H8A	110.2
O2—C4—C3	115.95 (6)	O2—C8—H8B	110.2
C5—C4—C3	119.79 (6)	C9—C8—H8B	110.2
C6—C5—C4	119.63 (7)	H8A—C8—H8B	108.5
C5—C6—C1	121.17 (6)	C8—C9—H9A	109.5
O1—C7—N2	121.19 (6)	C8—C9—H9B	109.5
O1—C7—C1	121.62 (6)	H9A—C9—H9B	109.5
N2—C7—C1	117.19 (6)	C8—C9—H9C	109.5
O2—C8—C9	107.38 (6)	H9A—C9—H9C	109.5
C7—N2—N1	122.19 (6)	H9B—C9—H9C	109.5
C4—O2—C8	117.18 (5)	N2—N1—H01	104.9 (8)
C3—C2—H2	119.7	N2—N1—H02	102.9 (7)
C1—C2—H2	119.7	H01—N1—H02	109.8 (11)
C2—C3—H3	120.0	C7—N2—H03	122.5 (8)
C4—C3—H3	120.0	N1—N2—H03	115.3 (8)

C6—C1—C2—C3	1.10 (10)	C6—C1—C7—O1	−164.06 (7)
C7—C1—C2—C3	−176.01 (6)	C2—C1—C7—O1	12.93 (10)
C1—C2—C3—C4	0.82 (11)	C6—C1—C7—N2	15.13 (10)
C2—C3—C4—O2	176.66 (6)	C2—C1—C7—N2	−167.88 (6)
C2—C3—C4—C5	−2.32 (11)	O1—C7—N2—N1	0.05 (11)
O2—C4—C5—C6	−177.01 (6)	C1—C7—N2—N1	−179.15 (6)
C3—C4—C5—C6	1.89 (11)	C5—C4—O2—C8	1.26 (10)
C4—C5—C6—C1	0.05 (11)	C3—C4—O2—C8	−177.68 (6)
C2—C1—C6—C5	−1.54 (11)	C9—C8—O2—C4	174.98 (6)
C7—C1—C6—C5	175.46 (6)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 benzene ring

D—H···A	D—H	H···A	D···A	D—H···A
N2—H03···O1ⁱ	0.865 (13)	2.083 (13)	2.9290 (9)	165.6 (11)
C6—H6···O1ⁱ	0.95	2.39	3.3149 (9)	165
C3—H3···O2ⁱⁱ	0.95	2.61	3.5428 (9)	168
N1—H01···O1ⁱⁱⁱ	0.933 (13)	2.212 (14)	3.1207 (9)	164.1 (12)
C8—H8B···Cg^iv	0.99	2.65	3.499 (1)	145

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+2; (iv) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₉H₁₂N₂O₂
M_r	180.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.8848 (3), 10.0453 (2), 8.4420 (3)
β (°)	110.669 (4)
V (Å³)	863.64 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	42766, 2874, 2478
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.735

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.106, 1.10
No. of reflections	2874
No. of parameters	131
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.22

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 benzene ring

D—H···A	D—H	H···A	D···A	D—H···A
N2—H03···O1ⁱ	0.865 (13)	2.083 (13)	2.9290 (9)	165.6 (11)
C6—H6···O1ⁱ	0.95	2.39	3.3149 (9)	165.1
C3—H3···O2ⁱⁱ	0.95	2.61	3.5428 (9)	168.1
N1—H01···O1ⁱⁱⁱ	0.933 (13)	2.212 (14)	3.1207 (9)	164.1 (12)
C8—H8B···Cg^iv	0.99	2.65	3.499 (1)	145

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+2; (iv) x, −y+3/2, z−1/2.

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Volume 68| Part 10| October 2012| Pages o2955-o2956

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