N′-[(2E)-3-Phenyl­prop-2-eno­yl]benzo­hydrazide

Carvalho, S.A.; Silva, E.F. da; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536809048156

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3118

doi:10.1107/S1600536809048156

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N′-[(2E)-3-Phenylprop-2-enoyl]benzohydrazide

Samir A. Carvalho,^a,^b Edson F. da Silva,^b Edward R. T. Tiekink,^c ^* James L. Wardell ^d ‡ and Solange M. S. V. Wardell ^e

^aInstituto de Química, Universidade Federal do Rio de Janeiro, 21949-900, Rio de Janeiro, RJ, Brazil, ^bDepartamento de Síntese Orgánica, Instituto de Tecnologia em Fármacos FIOCRUZ, Manguinhos, Rua Sizenando Nabuco 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil, and ^eCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 12 November 2009; accepted 13 November 2009; online 18 November 2009)

In the title compound, C₁₆H₁₄N₂O₂, the conformation about the C=C bond is E, and the two amide groups are effectively orthogonal [the C—N—N—C torsion angle is 104.5 (2)°]. In the crystal structure, the amide groups groups associate via N–H⋯O hydrogen bonding, forming supramolecular tapes with undulating topology along the c-axis direction.

Related literature

For the biological activity of trans-cinnamic acid derivatives, see: Bezerra et al. (2006 ); Chung & Shin (2007 ); Naz et al. (2006 ); Rastogi et al. (1998 ); Reddy et al. (1995 ). For recent studies directed towards developing drugs for the treatment of tuberculosis, see: Carvalho et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₄N₂O₂
M_r = 266.29
Monoclinic, P 2₁ /c
a = 15.9696 (7) Å
b = 10.4563 (5) Å
c = 8.3162 (2) Å
β = 102.072 (3)°
V = 1357.95 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 120 K
0.48 × 0.20 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.636, T_max = 0.746
17862 measured reflections
3110 independent reflections
2010 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.172
S = 1.10
3110 reflections
187 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1ⁱ	0.89 (2)	1.95 (2)	2.827 (2)	168 (2)
N2—HN2⋯O2ⁱⁱ	0.86 (2)	2.01 (2)	2.852 (2)	168 (2)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536809048156/hg2591sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048156/hg2591Isup2.hkl

checkCIF report

Comment top

Tuberculosis (TB) remains among the world's great public health challenges. Worldwide resurgence of TB is due to two major problems: the AIDS epidemic, which started in the mid-1980's, and the outbreak of multi-drug resistant (MDR) TB. The deadly combination of TB and HIV has led to a quadrupling of TB cases in several African and Asian countries [http://www.who.int/tdr/diseases/tb/default.htm]. MDR-TB, defined as resistance to at least isoniazid and rifamycin, two current first-line drugs, has increased morbidity and mortality with an overall increase in health care costs. The first-line treatment has some disadvantages such as important side-effects and weak sterility problems, and must be administered for 6–9 months. When standard treatments fail, second-line TB drugs are used, but these drugs have a far lower efficacy and require even longer administration periods (18–24 months) with higher cost (US $2500–3000 per treatment), higher rates of adverse effects, and low cure rates (around 60%). It is estimated that 4% of all worldwide TB patients are resistant to at least one of the current first-line drugs. TB is responsible for 20% of all deaths in adults, and each year there are about nine million new cases, of which 15% are children, and two million of deaths, of which 450.000 are children. Due to the increase of MDR-TB and AIDS cases worldwide and the lack of new drugs, there is an urgent need for new drugs to fight this disease. In our continuing research for new potent and anti-malarial agents, we reported on a new class of isonicotinic and benzoic acid N'-(3-phenyl-acryloyl)-hydrazide derivatives as attractive anti-tubercular agents (Carvalho et al., 2008) and now report the structure of N'-[(2E)-3-phenylprop-2-enoyl]benzohydrazide, (I). The choice of trans-cinnamic acid derivatives in this study follows on from earlier reports of their significant biological activities (Bezerra et al., 2006; Chung & Shin, 2007; Naz et al., 2006; Rastogi et al., 1998; Reddy et al., 1995).

In (I), the conformation about the C7═C8 bond is E, Fig. 1. There is significant twisting in the molecule, in particular about about the central N1–N2 bond as seen in the value of the C9/N1/N2/C10 torsion angle of 104.5 (2) °. This has the consequence that the amide groups are effectively orthogonal to each other, a feature that facilitates the formation of N–H···O hydrogen bond leading to the formation of undulating supramolecular tapes in the c direction, Fig. 2 and Table 1.

Related literature top

For the biological activiy of trans-cinnamic acid derivatives, see: Bezerra et al. (2006); Chung & Shin (2007); Naz et al. (2006); Rastogi et al. (1998); Reddy et al. (1995). For recent studies directed towards developing drugs for the treatment of tuberculosis, see: Carvalho et al. (2008).

Experimental top

4-Nitrophenyl (2E)-3-phenyl-2-propenoate (2.0 g), prepared by successive treatments of trans-cinnamic acid with thionyl chloride and 4-nitrophenol, was added to a solution of PhCONHNH₂ (1.1 equiv.) in pyridine (40 ml). After refluxing the reaction mixture for 6 h, the excess of pyridine was removed under vacuum and water (20 ml) was added. The precipitate was filtered under vacuum, and washed with water to furnish (I) in 78% yield. The crystals used in the structure determination were grown from ethanol solution, m. pt. 482–483 K. ¹H NMR (500.00 MHz, DMSO-d6) δ: 6.78 (1H, d, J = 16.0 Hz, Ph—CH), 7.42 (3H, m, aryl-H), 7.52 (2H, m, aryl-H), 7.60 (1H, d, J = 16.0 Hz, CHCO), 7.63 (3H, m, aryl-H), 7.93 (2H, d, J = 7.5 Hz, aryl-H, 10.25 (1H, s, NH), 10.56 (1H, s, NH) p.p.m. ¹³C NMR (125 MHz, DMSO-d6) δ: 165.48, 164.45, 140.34, 134.59, 132.45, 131.92, 129.91, 129.07, 127.78, 121.52, 119.45 p.p.m.

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: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular tape with undulating topology in (I). The N–H···O hydrogen bonding is shown as orange dashed lines

(I) top

Crystal data top

C₁₆H₁₄N₂O₂	F(000) = 560
M_r = 266.29	D_x = 1.303 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6527 reflections
a = 15.9696 (7) Å	θ = 2.9–27.5°
b = 10.4563 (5) Å	µ = 0.09 mm⁻¹
c = 8.3162 (2) Å	T = 120 K
β = 102.072 (3)°	Block, light-red
V = 1357.95 (9) Å³	0.48 × 0.20 × 0.08 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	3110 independent reflections
Radiation source: Enraf–Nonius FR591 rotating anode	2010 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.086
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ϕ and ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −13→13
T_min = 0.636, T_max = 0.746	l = −9→10
17862 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0894P)²] where P = (F_o² + 2F_c²)/3
3110 reflections	(Δ/σ)_max < 0.001
187 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₆H₁₄N₂O₂	V = 1357.95 (9) Å³
M_r = 266.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.9696 (7) Å	µ = 0.09 mm⁻¹
b = 10.4563 (5) Å	T = 120 K
c = 8.3162 (2) Å	0.48 × 0.20 × 0.08 mm
β = 102.072 (3)°

Data collection top

Nonius KappaCCD area-detector diffractometer	3110 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2010 reflections with I > 2σ(I)
T_min = 0.636, T_max = 0.746	R_int = 0.086
17862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.45 e Å⁻³
3110 reflections	Δρ_min = −0.42 e Å⁻³
187 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	0.20786 (9)	0.62832 (14)	0.42536 (16)	0.0272 (4)
O2	0.36866 (9)	0.61547 (14)	0.11169 (15)	0.0249 (4)
N1	0.25365 (10)	0.74825 (18)	0.2337 (2)	0.0239 (4)
HN1	0.2442 (14)	0.779 (2)	0.132 (3)	0.029*
N2	0.33940 (11)	0.73943 (18)	0.3148 (2)	0.0248 (4)
HN2	0.3532 (14)	0.774 (2)	0.410 (3)	0.030*
C1	−0.04530 (13)	0.6129 (2)	0.1175 (2)	0.0233 (5)
C2	−0.07212 (14)	0.6812 (2)	−0.0287 (3)	0.0305 (5)
H2	−0.0322	0.7330	−0.0692	0.037*
C3	−0.15601 (14)	0.6745 (2)	−0.1150 (3)	0.0328 (6)
H3	−0.1733	0.7219	−0.2138	0.039*
C4	−0.21495 (13)	0.5991 (2)	−0.0583 (3)	0.0291 (5)
H4	−0.2725	0.5948	−0.1177	0.035*
C5	−0.18951 (14)	0.5302 (2)	0.0851 (3)	0.0301 (5)
H5	−0.2297	0.4782	0.1244	0.036*
C6	−0.10529 (13)	0.5366 (2)	0.1725 (2)	0.0264 (5)
H6	−0.0884	0.4885	0.2709	0.032*
C7	0.04268 (13)	0.6196 (2)	0.2143 (2)	0.0236 (5)
H7	0.0550	0.5693	0.3115	0.028*
C8	0.10735 (12)	0.6886 (2)	0.1809 (2)	0.0236 (5)
H8	0.0983	0.7412	0.0857	0.028*
C9	0.19296 (12)	0.6835 (2)	0.2911 (2)	0.0211 (4)
C10	0.39296 (12)	0.66689 (19)	0.2472 (2)	0.0203 (5)
C11	0.48306 (12)	0.65355 (19)	0.3422 (2)	0.0208 (5)
C12	0.52237 (13)	0.7406 (2)	0.4602 (2)	0.0226 (5)
H12	0.4913	0.8126	0.4859	0.027*
C13	0.60701 (13)	0.7227 (2)	0.5409 (2)	0.0272 (5)
H13	0.6338	0.7826	0.6213	0.033*
C14	0.65253 (14)	0.6170 (2)	0.5038 (2)	0.0280 (5)
H14	0.7105	0.6050	0.5582	0.034*
C15	0.61300 (13)	0.5296 (2)	0.3873 (2)	0.0278 (5)
H15	0.6438	0.4569	0.3631	0.033*
C16	0.52891 (13)	0.5473 (2)	0.3060 (2)	0.0255 (5)
H16	0.5024	0.4873	0.2255	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0249 (8)	0.0309 (9)	0.0232 (7)	0.0004 (6)	−0.0008 (6)	0.0013 (6)
O2	0.0223 (8)	0.0286 (9)	0.0214 (7)	−0.0042 (6)	−0.0009 (5)	−0.0019 (6)
N1	0.0140 (9)	0.0337 (11)	0.0212 (8)	−0.0004 (8)	−0.0030 (6)	0.0011 (8)
N2	0.0164 (9)	0.0348 (11)	0.0202 (8)	−0.0005 (8)	−0.0033 (6)	−0.0027 (8)
C1	0.0197 (11)	0.0247 (12)	0.0245 (10)	0.0021 (9)	0.0024 (8)	−0.0015 (8)
C2	0.0213 (11)	0.0354 (13)	0.0335 (11)	−0.0057 (10)	0.0026 (9)	0.0068 (10)
C3	0.0247 (12)	0.0371 (14)	0.0323 (12)	−0.0049 (10)	−0.0038 (9)	0.0084 (10)
C4	0.0174 (11)	0.0292 (13)	0.0369 (12)	0.0000 (9)	−0.0029 (9)	−0.0022 (9)
C5	0.0244 (12)	0.0288 (12)	0.0368 (12)	−0.0087 (10)	0.0056 (9)	−0.0024 (10)
C6	0.0249 (11)	0.0270 (12)	0.0264 (10)	−0.0020 (9)	0.0031 (8)	0.0006 (9)
C7	0.0216 (11)	0.0270 (12)	0.0212 (10)	0.0030 (9)	0.0025 (8)	−0.0012 (8)
C8	0.0218 (11)	0.0262 (11)	0.0209 (10)	0.0041 (9)	0.0004 (8)	−0.0011 (8)
C9	0.0183 (10)	0.0222 (11)	0.0213 (10)	0.0015 (9)	0.0005 (7)	−0.0048 (8)
C10	0.0193 (11)	0.0218 (11)	0.0188 (10)	−0.0031 (8)	0.0014 (7)	0.0041 (8)
C11	0.0181 (10)	0.0231 (11)	0.0204 (10)	−0.0020 (8)	0.0019 (7)	0.0043 (8)
C12	0.0189 (10)	0.0268 (12)	0.0218 (9)	−0.0014 (9)	0.0037 (7)	−0.0001 (8)
C13	0.0202 (11)	0.0328 (13)	0.0264 (10)	−0.0028 (9)	−0.0002 (8)	−0.0034 (9)
C14	0.0181 (10)	0.0357 (13)	0.0274 (11)	0.0019 (9)	−0.0017 (8)	0.0010 (9)
C15	0.0249 (12)	0.0277 (12)	0.0298 (11)	0.0069 (9)	0.0034 (8)	0.0038 (9)
C16	0.0253 (12)	0.0252 (12)	0.0242 (10)	−0.0008 (9)	0.0015 (8)	0.0003 (8)

Geometric parameters (Å, º) top

O1—C9	1.235 (2)	C6—H6	0.9500
O2—C10	1.235 (2)	C7—C8	1.336 (3)
N1—C9	1.348 (3)	C7—H7	0.9500
N1—N2	1.397 (2)	C8—C9	1.479 (3)
N1—HN1	0.89 (2)	C8—H8	0.9500
N2—C10	1.351 (3)	C10—C11	1.496 (3)
N2—HN2	0.86 (2)	C11—C12	1.388 (3)
C1—C6	1.395 (3)	C11—C16	1.398 (3)
C1—C2	1.398 (3)	C12—C13	1.390 (3)
C1—C7	1.467 (3)	C12—H12	0.9500
C2—C3	1.383 (3)	C13—C14	1.392 (3)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.384 (3)	C14—C15	1.384 (3)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.379 (3)	C15—C16	1.384 (3)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.390 (3)	C16—H16	0.9500
C5—H5	0.9500

C9—N1—N2	120.03 (17)	C7—C8—C9	120.44 (18)
C9—N1—HN1	121.9 (14)	C7—C8—H8	119.8
N2—N1—HN1	116.0 (14)	C9—C8—H8	119.8
C10—N2—N1	118.56 (16)	O1—C9—N1	122.52 (17)
C10—N2—HN2	124.2 (16)	O1—C9—C8	123.72 (18)
N1—N2—HN2	117.0 (15)	N1—C9—C8	113.74 (17)
C6—C1—C2	118.08 (18)	O2—C10—N2	121.24 (17)
C6—C1—C7	119.48 (18)	O2—C10—C11	121.69 (17)
C2—C1—C7	122.44 (19)	N2—C10—C11	117.06 (16)
C3—C2—C1	120.8 (2)	C12—C11—C16	119.57 (18)
C3—C2—H2	119.6	C12—C11—C10	123.71 (18)
C1—C2—H2	119.6	C16—C11—C10	116.71 (18)
C2—C3—C4	120.41 (19)	C11—C12—C13	120.21 (19)
C2—C3—H3	119.8	C11—C12—H12	119.9
C4—C3—H3	119.8	C13—C12—H12	119.9
C5—C4—C3	119.58 (19)	C12—C13—C14	119.99 (19)
C5—C4—H4	120.2	C12—C13—H13	120.0
C3—C4—H4	120.2	C14—C13—H13	120.0
C4—C5—C6	120.3 (2)	C15—C14—C13	119.76 (19)
C4—C5—H5	119.9	C15—C14—H14	120.1
C6—C5—H5	119.9	C13—C14—H14	120.1
C5—C6—C1	120.80 (19)	C14—C15—C16	120.5 (2)
C5—C6—H6	119.6	C14—C15—H15	119.8
C1—C6—H6	119.6	C16—C15—H15	119.8
C8—C7—C1	127.24 (19)	C15—C16—C11	119.97 (19)
C8—C7—H7	116.4	C15—C16—H16	120.0
C1—C7—H7	116.4	C11—C16—H16	120.0

C9—N1—N2—C10	104.5 (2)	C7—C8—C9—N1	173.98 (19)
C6—C1—C2—C3	0.7 (3)	N1—N2—C10—O2	4.4 (3)
C7—C1—C2—C3	−178.7 (2)	N1—N2—C10—C11	−176.55 (16)
C1—C2—C3—C4	−0.3 (4)	O2—C10—C11—C12	156.22 (19)
C2—C3—C4—C5	−0.1 (3)	N2—C10—C11—C12	−22.8 (3)
C3—C4—C5—C6	0.1 (3)	O2—C10—C11—C16	−23.0 (3)
C4—C5—C6—C1	0.3 (3)	N2—C10—C11—C16	158.00 (18)
C2—C1—C6—C5	−0.7 (3)	C16—C11—C12—C13	0.5 (3)
C7—C1—C6—C5	178.8 (2)	C10—C11—C12—C13	−178.68 (17)
C6—C1—C7—C8	−179.0 (2)	C11—C12—C13—C14	−0.2 (3)
C2—C1—C7—C8	0.4 (3)	C12—C13—C14—C15	−0.5 (3)
C1—C7—C8—C9	−179.37 (19)	C13—C14—C15—C16	0.8 (3)
N2—N1—C9—O1	9.3 (3)	C14—C15—C16—C11	−0.5 (3)
N2—N1—C9—C8	−172.41 (17)	C12—C11—C16—C15	−0.1 (3)
C7—C8—C9—O1	−7.8 (3)	C10—C11—C16—C15	179.11 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1ⁱ	0.89 (2)	1.95 (2)	2.827 (2)	168 (2)
N2—HN2···O2ⁱⁱ	0.86 (2)	2.01 (2)	2.852 (2)	168 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₂
M_r	266.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	15.9696 (7), 10.4563 (5), 8.3162 (2)
β (°)	102.072 (3)
V (Å³)	1357.95 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.20 × 0.08

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.636, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	17862, 3110, 2010
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.172, 1.10
No. of reflections	3110
No. of parameters	187
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.42

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1ⁱ	0.89 (2)	1.95 (2)	2.827 (2)	168 (2)
N2—HN2···O2ⁱⁱ	0.86 (2)	2.01 (2)	2.852 (2)	168 (2)

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

References

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