2-[(E)-Phen­yl(2-phenyl­hydrazin-1-yl­idene)meth­yl]phenol

Howie, R.A.; Wardell, J.L.; Wardell, S.M.S.V.; Tiekink, E.R.T.

doi:10.1107/S1600536812005387

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o796-o797

doi:10.1107/S1600536812005387

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2-[(E)-Phenyl(2-phenylhydrazin-1-ylidene)methyl]phenol

R. Alan Howie,^a James L. Wardell,^b ‡ Solange M. S. V. Wardell ^c and Edward R. T. Tiekink ^d ^*

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, ^bCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Avenida Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil, ^cCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 6 February 2012; accepted 7 February 2012; online 24 February 2012)

In the title hydrazone derivative, C₁₉H₁₆N₂O, a twist is found between the hydroxyphenyl and N-bound phenyl rings [dihedral angle = 24.37 (7)°]. The C-bound phenyl ring is almost perpendicular to each of these planes [dihedral angles = 75.30 (7) and 86.00 (7)°, respectively]. The conformation about the imine bond [1.2935 (17) Å] is E. The hydroxy group forms an intramolecular hydrogen bond with the imine N atom. Zigzag chains along [001] mediated by N—H⋯O hydrogen bonds feature in the crystal packing.

Related literature

For background on the influence of substituents upon the supramolecular structures of hydrazones, see: Glidewell et al. (2004 ); Ferguson et al. (2005 ); Wardell et al. (2007 ); Baddeley, de Souza França et al. (2009 ); Baddeley, Howie et al. (2009 ); de Souza et al. (2010 ); Howie, da Silva Lima et al. (2010 ); Howie, de Souza et al. (2010 ); Nogueira et al. (2011 ); Howie et al. (2011 ).

Experimental

Crystal data

C₁₉H₁₆N₂O
M_r = 288.34
Monoclinic, P 2₁ /c
a = 9.6796 (3) Å
b = 15.3312 (5) Å
c = 10.3593 (2) Å
β = 108.149 (2)°
V = 1460.84 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 120 K
0.49 × 0.38 × 0.18 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.857, T_max = 0.985
16532 measured reflections
3337 independent reflections
2624 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.141
S = 1.06
3337 reflections
205 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.85 (1)	1.76 (1)	2.5678 (14)	157 (2)
N2—H2N⋯O1ⁱ	0.89 (2)	2.43 (2)	3.2517 (16)	155 (1)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812005387/bt5814sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005387/bt5814Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005387/bt5814Isup3.cml

checkCIF report

Comment top

For some time, we have been interested in the influence of substituents upon the supramolecular structures of hydrazones, especially of those having potential biological activities. These include substituted phenylhydrazines with substituted benzaldehydes (Glidewell et al., 2004; Ferguson et al., 2005) and 2-hydroxyacetophenone (Baddeley, de Souza França et al., 2009). Hydrazones derived from substituted benzaldehydes and (pyrazinecarbonyl)hydrazine (Baddeley, Howie et al., 2009; Howie, da Silva Lima et al., 2010), 2-hydrazinyl-benzothiazole (Nogueira et al., 2011), 7-chloroquinoline-4-hydrazide (Howie, de Souza et al., 2010; de Souza et al., 2010) and 2-hydrazinylacyl-N-isonicotine (Wardell et al., 2007) have also been investigated along with L-serinyl derivatives, (S)-2-hydroxy-1-[N-(benzylidene)-hydrazinylcarbonyl]ethylcarbamate esters (Howie et al., 2011). In continuation of these studies, herein the crystal and molecular structure of (E)-2-hydroxybenzophenone phenylhydrazone (I) is described.

In (I), Fig. 1, the hydroxy-benzene and N-bound phenyl rings are twisted, forming a dihedral angle of 24.37 (7)°. These planes form dihedral angles of 75.30 (7) and 86.00 (7)°, respectively, with the C-bound phenyl ring indicating an almost perpendicular relationship. The hydroxy group forms an intramolecular hydrogen bond with the imine-N1 atom, Table 1. The configuration about the imine bond N1═C7 [1.2935 (17) Å] is E.

The most prominent feature of the crystal packing is the formation of zigzag chains along [001] generated by glide symmetry and mediated by N—H···O hydrogen bonds, Fig. 2 and Table 1. Chains pack in the crystal structure with no specific intermolecular interactions between them, Fig. 3.

Related literature top

For background on the influence of substituents upon the supramolecular structures of hydrazones, see: Glidewell et al. (2004); Ferguson et al. (2005); Wardell et al. (2007); Baddeley, de Souza França et al. (2009); Baddeley, Howie et al. (2009); de Souza et al. (2010); Howie, da Silva Lima et al. (2010); Howie, de Souza et al. (2010); Nogueira et al. (2011); Howie et al. (2011).

Experimental top

A solution of phenylhydrazine and 2-hydroxybenzophenone (1 mmol each) in ethanol (20 ml) was refluxed for 1 h, rotary evaporated and the residue recrystallized from ethanol. IR (KBr, cm^-1): ν 3302, 1600, 1557. Analysis found: C 78.78, H 5.81, N 9.47%; calculated for C₁₉H₁₆N₂O: C 79.14, H 5.59, N 9.71%.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular zigzag chain in (I) sustained by N—H···O (orange dashed lines) hydrogen bonds.
	Fig. 3. A view in projection down the c axis of the packing of supramolecular chains in (I). The N—H···O hydrogen bonds are shown as orange dashed lines. One chain is highlighted in space-filling mode.

2-[(E)-Phenyl(2-phenylhydrazin-1-ylidene)methyl]phenol top

Crystal data top

C₁₉H₁₆N₂O	F(000) = 608
M_r = 288.34	D_x = 1.311 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9588 reflections
a = 9.6796 (3) Å	θ = 2.9–27.5°
b = 15.3312 (5) Å	µ = 0.08 mm⁻¹
c = 10.3593 (2) Å	T = 120 K
β = 108.149 (2)°	Slab, yellow
V = 1460.84 (7) Å³	0.49 × 0.38 × 0.18 mm
Z = 4

Data collection top

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	3337 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	2624 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
ϕ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −19→19
T_min = 0.857, T_max = 0.985	l = −13→13
16532 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0846P)² + 0.1552P] where P = (F_o² + 2F_c²)/3
3337 reflections	(Δ/σ)_max < 0.001
205 parameters	Δρ_max = 0.31 e Å⁻³
2 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₉H₁₆N₂O	V = 1460.84 (7) Å³
M_r = 288.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6796 (3) Å	µ = 0.08 mm⁻¹
b = 15.3312 (5) Å	T = 120 K
c = 10.3593 (2) Å	0.49 × 0.38 × 0.18 mm
β = 108.149 (2)°

Data collection top

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	3337 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2624 reflections with I > 2σ(I)
T_min = 0.857, T_max = 0.985	R_int = 0.044
16532 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	2 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.31 e Å⁻³
3337 reflections	Δρ_min = −0.40 e Å⁻³
205 parameters

Special details top

Geometry. All s.u.'s (except the s.u. 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
O1	0.55543 (11)	0.62061 (7)	0.67432 (9)	0.0305 (3)
H1O	0.5167 (19)	0.6457 (11)	0.5981 (12)	0.046*
N1	0.49781 (12)	0.67646 (7)	0.42953 (11)	0.0245 (3)
N2	0.42408 (13)	0.73657 (8)	0.33672 (11)	0.0279 (3)
H2N	0.4722 (16)	0.7602 (10)	0.2854 (14)	0.033*
C1	0.68370 (14)	0.57283 (9)	0.51935 (12)	0.0219 (3)
C2	0.65661 (15)	0.56890 (9)	0.64615 (13)	0.0245 (3)
C3	0.73482 (15)	0.51112 (9)	0.74555 (13)	0.0275 (3)
H3	0.7182	0.5098	0.8312	0.033*
C4	0.83577 (16)	0.45602 (9)	0.72145 (14)	0.0294 (3)
H4	0.8872	0.4163	0.7900	0.035*
C5	0.86344 (16)	0.45784 (9)	0.59745 (14)	0.0268 (3)
H5	0.9333	0.4196	0.5808	0.032*
C6	0.78782 (15)	0.51608 (9)	0.49900 (13)	0.0245 (3)
H6	0.8073	0.5176	0.4146	0.029*
C7	0.60591 (14)	0.63406 (8)	0.41159 (12)	0.0225 (3)
C8	0.65557 (15)	0.64475 (9)	0.28938 (13)	0.0233 (3)
C9	0.57166 (16)	0.61134 (10)	0.16460 (13)	0.0295 (3)
H9	0.4805	0.5848	0.1559	0.035*
C10	0.62186 (17)	0.61703 (10)	0.05272 (14)	0.0332 (4)
H10	0.5659	0.5929	−0.0319	0.040*
C11	0.75214 (18)	0.65735 (10)	0.06393 (14)	0.0342 (4)
H11	0.7858	0.6608	−0.0128	0.041*
C12	0.83445 (17)	0.69288 (10)	0.18688 (15)	0.0331 (4)
H12	0.9230	0.7221	0.1939	0.040*
C13	0.78680 (16)	0.68548 (9)	0.29963 (14)	0.0286 (3)
H13	0.8444	0.7084	0.3845	0.034*
C14	0.31426 (15)	0.78382 (9)	0.36540 (12)	0.0246 (3)
C15	0.26578 (17)	0.86137 (10)	0.29652 (14)	0.0335 (4)
H15	0.3084	0.8820	0.2312	0.040*
C16	0.15586 (17)	0.90856 (11)	0.32279 (15)	0.0362 (4)
H16	0.1232	0.9613	0.2749	0.043*
C17	0.09268 (16)	0.87973 (10)	0.41823 (14)	0.0319 (4)
H17	0.0173	0.9124	0.4362	0.038*
C18	0.14125 (15)	0.80271 (10)	0.48685 (14)	0.0282 (3)
H18	0.0990	0.7827	0.5528	0.034*
C19	0.25048 (15)	0.75439 (9)	0.46098 (13)	0.0253 (3)
H19	0.2820	0.7013	0.5082	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0325 (6)	0.0394 (6)	0.0258 (5)	0.0046 (4)	0.0178 (4)	−0.0006 (4)
N1	0.0247 (6)	0.0277 (6)	0.0239 (5)	0.0032 (5)	0.0118 (5)	0.0002 (4)
N2	0.0281 (7)	0.0352 (7)	0.0262 (6)	0.0094 (5)	0.0171 (5)	0.0058 (5)
C1	0.0214 (7)	0.0247 (7)	0.0218 (6)	−0.0030 (5)	0.0098 (5)	−0.0021 (5)
C2	0.0230 (7)	0.0287 (7)	0.0250 (6)	−0.0044 (5)	0.0122 (5)	−0.0049 (5)
C3	0.0298 (8)	0.0326 (8)	0.0222 (6)	−0.0068 (6)	0.0112 (5)	−0.0002 (6)
C4	0.0298 (8)	0.0279 (7)	0.0299 (7)	−0.0031 (6)	0.0086 (6)	0.0047 (6)
C5	0.0258 (7)	0.0236 (7)	0.0329 (7)	0.0014 (5)	0.0117 (6)	−0.0011 (6)
C6	0.0265 (7)	0.0251 (7)	0.0246 (6)	−0.0029 (5)	0.0120 (5)	−0.0025 (5)
C7	0.0225 (7)	0.0250 (7)	0.0229 (6)	−0.0002 (5)	0.0115 (5)	−0.0020 (5)
C8	0.0250 (7)	0.0248 (7)	0.0238 (6)	0.0054 (5)	0.0130 (5)	0.0016 (5)
C9	0.0269 (8)	0.0367 (8)	0.0272 (7)	0.0016 (6)	0.0120 (6)	−0.0014 (6)
C10	0.0355 (9)	0.0428 (9)	0.0235 (7)	0.0085 (7)	0.0124 (6)	0.0001 (6)
C11	0.0452 (9)	0.0344 (8)	0.0323 (7)	0.0119 (7)	0.0256 (7)	0.0080 (6)
C12	0.0353 (9)	0.0301 (8)	0.0442 (8)	0.0019 (6)	0.0274 (7)	0.0032 (6)
C13	0.0286 (8)	0.0283 (7)	0.0330 (7)	0.0018 (6)	0.0156 (6)	−0.0020 (6)
C14	0.0225 (7)	0.0314 (7)	0.0218 (6)	0.0029 (6)	0.0094 (5)	−0.0035 (5)
C15	0.0356 (9)	0.0429 (9)	0.0278 (7)	0.0102 (7)	0.0181 (6)	0.0083 (6)
C16	0.0359 (9)	0.0428 (9)	0.0347 (8)	0.0160 (7)	0.0180 (7)	0.0112 (7)
C17	0.0266 (8)	0.0409 (9)	0.0320 (7)	0.0093 (6)	0.0147 (6)	0.0006 (6)
C18	0.0254 (8)	0.0346 (8)	0.0291 (7)	−0.0012 (6)	0.0151 (6)	−0.0023 (6)
C19	0.0248 (7)	0.0263 (7)	0.0271 (7)	−0.0004 (5)	0.0114 (6)	−0.0007 (5)

Geometric parameters (Å, º) top

O1—C2	1.3605 (17)	C9—C10	1.3920 (19)
O1—H1O	0.853 (9)	C9—H9	0.9500
N1—C7	1.2935 (17)	C10—C11	1.376 (2)
N1—N2	1.3621 (16)	C10—H10	0.9500
N2—C14	1.3928 (17)	C11—C12	1.386 (2)
N2—H2N	0.886 (9)	C11—H11	0.9500
C1—C6	1.3963 (19)	C12—C13	1.3875 (19)
C1—C2	1.4186 (17)	C12—H12	0.9500
C1—C7	1.4734 (18)	C13—H13	0.9500
C2—C3	1.390 (2)	C14—C15	1.391 (2)
C3—C4	1.372 (2)	C14—C19	1.3950 (19)
C3—H3	0.9500	C15—C16	1.382 (2)
C4—C5	1.3917 (19)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.387 (2)
C5—C6	1.3812 (19)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.383 (2)
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.4966 (17)	C18—C19	1.3838 (19)
C8—C13	1.390 (2)	C18—H18	0.9500
C8—C9	1.3924 (19)	C19—H19	0.9500

C2—O1—H1O	101.7 (13)	C8—C9—H9	120.1
C7—N1—N2	120.53 (11)	C11—C10—C9	120.41 (13)
N1—N2—C14	117.92 (10)	C11—C10—H10	119.8
N1—N2—H2N	116.2 (11)	C9—C10—H10	119.8
C14—N2—H2N	119.7 (11)	C10—C11—C12	120.21 (13)
C6—C1—C2	117.62 (12)	C10—C11—H11	119.9
C6—C1—C7	120.35 (11)	C12—C11—H11	119.9
C2—C1—C7	122.03 (12)	C13—C12—C11	119.65 (14)
O1—C2—C3	118.34 (12)	C13—C12—H12	120.2
O1—C2—C1	121.80 (12)	C11—C12—H12	120.2
C3—C2—C1	119.86 (13)	C12—C13—C8	120.53 (13)
C4—C3—C2	120.79 (12)	C12—C13—H13	119.7
C4—C3—H3	119.6	C8—C13—H13	119.7
C2—C3—H3	119.6	C15—C14—N2	119.55 (12)
C3—C4—C5	120.54 (13)	C15—C14—C19	119.18 (12)
C3—C4—H4	119.7	N2—C14—C19	121.27 (12)
C5—C4—H4	119.7	C16—C15—C14	120.26 (13)
C6—C5—C4	118.98 (13)	C16—C15—H15	119.9
C6—C5—H5	120.5	C14—C15—H15	119.9
C4—C5—H5	120.5	C15—C16—C17	120.74 (14)
C5—C6—C1	122.19 (12)	C15—C16—H16	119.6
C5—C6—H6	118.9	C17—C16—H16	119.6
C1—C6—H6	118.9	C18—C17—C16	118.93 (13)
N1—C7—C1	117.18 (11)	C18—C17—H17	120.5
N1—C7—C8	123.63 (12)	C16—C17—H17	120.5
C1—C7—C8	119.19 (11)	C19—C18—C17	121.03 (13)
C13—C8—C9	119.42 (12)	C19—C18—H18	119.5
C13—C8—C7	120.76 (12)	C17—C18—H18	119.5
C9—C8—C7	119.79 (12)	C18—C19—C14	119.87 (13)
C10—C9—C8	119.73 (14)	C18—C19—H19	120.1
C10—C9—H9	120.1	C14—C19—H19	120.1

C7—N1—N2—C14	−176.29 (12)	N1—C7—C8—C9	−72.19 (18)
C6—C1—C2—O1	−178.88 (12)	C1—C7—C8—C9	108.42 (15)
C7—C1—C2—O1	1.1 (2)	C13—C8—C9—C10	1.7 (2)
C6—C1—C2—C3	1.25 (19)	C7—C8—C9—C10	−176.44 (13)
C7—C1—C2—C3	−178.79 (12)	C8—C9—C10—C11	−1.6 (2)
O1—C2—C3—C4	178.47 (12)	C9—C10—C11—C12	−0.2 (2)
C1—C2—C3—C4	−1.7 (2)	C10—C11—C12—C13	1.8 (2)
C2—C3—C4—C5	1.0 (2)	C11—C12—C13—C8	−1.7 (2)
C3—C4—C5—C6	0.1 (2)	C9—C8—C13—C12	−0.1 (2)
C4—C5—C6—C1	−0.5 (2)	C7—C8—C13—C12	178.04 (12)
C2—C1—C6—C5	−0.2 (2)	N1—N2—C14—C15	161.37 (13)
C7—C1—C6—C5	179.83 (12)	N1—N2—C14—C19	−19.38 (19)
N2—N1—C7—C1	177.56 (11)	N2—C14—C15—C16	179.33 (14)
N2—N1—C7—C8	−1.8 (2)	C19—C14—C15—C16	0.1 (2)
C6—C1—C7—N1	171.04 (12)	C14—C15—C16—C17	0.3 (2)
C2—C1—C7—N1	−8.92 (19)	C15—C16—C17—C18	−0.1 (2)
C6—C1—C7—C8	−9.52 (19)	C16—C17—C18—C19	−0.4 (2)
C2—C1—C7—C8	170.52 (12)	C17—C18—C19—C14	0.7 (2)
N1—C7—C8—C13	109.69 (16)	C15—C14—C19—C18	−0.5 (2)
C1—C7—C8—C13	−69.71 (17)	N2—C14—C19—C18	−179.78 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.85 (1)	1.76 (1)	2.5678 (14)	157 (2)
N2—H2N···O1ⁱ	0.89 (2)	2.43 (2)	3.2517 (16)	155 (1)

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₂O
M_r	288.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	9.6796 (3), 15.3312 (5), 10.3593 (2)
β (°)	108.149 (2)
V (Å³)	1460.84 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.49 × 0.38 × 0.18

Data collection
Diffractometer	Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.857, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	16532, 3337, 2624
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.141, 1.06
No. of reflections	3337
No. of parameters	205
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)	0.31, −0.40

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.853 (13)	1.763 (13)	2.5678 (14)	156.6 (18)
N2—H2N···O1ⁱ	0.886 (15)	2.427 (15)	3.2517 (16)	155.0 (13)

Symmetry code: (i) x, −y+3/2, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

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