Crystal structure of poly[di-μ-aqua-{5-[(1Z)-2-(4-chloro­phen­yl)-1-cyano­ethenyl]-1,2,3,4-tetra­zol-1-ido-κN1}sodium]

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; El-Saghier, A.M.M.; Albayati, M.R.

doi:10.1107/S2056989015006325

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 5| May 2015| Pages m102-m103

https://doi.org/10.1107/S2056989015006325

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Crystal structure of poly[di-μ-aqua-{5-[(1Z)-2-(4-chlorophenyl)-1-cyanoethenyl]-1,2,3,4-tetrazol-1-ido-κN¹}sodium]

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Ahmed M. M. El-Saghier ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eDepartment of Chemistry, Faculty of Science, Sohag University, Sohag 82524, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 26 March 2015; accepted 28 March 2015; online 9 April 2015)

In the title compound, [Na(C₁₀H₅ClN₅)(H₂O)₂]_n, infinite chains of [Na(H₂O)₂]⁺ cations having a diamond-shaped cross-section and running parallel to the b axis are formed. O—H⋯N hydrogen bonds to the anions generate layers parallel to (100) which have the chlorobenzenecyanoethenyl substituents protruding from both surfaces. The sodium ion makes a short contact of 2.4801 (13) Å with the N atom of the tetrazolide ring which is syn to the cyano N atom.

Keywords: crystal structure; sodium salt; tetrazoles; hydrogen bonding.

CCDC reference: 1056677

1. Related literature

For chemical behaviour of tetrazoles, see: Smith et al. (1991 ); Duncia et al. (1990 ). For various industrial applications of different tetrazole derivatives, see: Modarresi et al. (2009 ); Singh et al. (1980 ). For medicinal activities of compounds with a tetrazole scaffold, see: Myznikov et al. (2007 ); Schocken et al. (1989 ); Mekni & Bakloiti (2008 ); Lim et al. (2007 ).

2. Experimental

2.1. Crystal data

[Na(C₁₀H₅ClN₅)(H₂O)₂]
M_r = 289.66
Monoclinic, P 2₁ /c
a = 22.0438 (4) Å
b = 3.8343 (1) Å
c = 15.0141 (3) Å
β = 92.427 (1)°
V = 1267.89 (5) Å³
Z = 4
Cu Kα radiation
μ = 3.08 mm⁻¹
T = 150 K
0.29 × 0.11 × 0.04 mm

2.2. Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.73, T_max = 0.89
9115 measured reflections
2560 independent reflections
2249 reflections with I > 2σ(I)
R_int = 0.026

2.3. Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.086
S = 1.03
2560 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N3ⁱ	0.84	2.04	2.8443 (17)	160
O1—H1B⋯N2ⁱⁱ	0.84	2.02	2.8593 (17)	175
O2—H2B⋯N5	0.84	2.44	3.1009 (19)	136
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 1056677

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015006325/tk5364sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015006325/tk5364Isup2.hkl

checkCIF report

Comment top

Tetrazole compounds have been largely associated with a wide range of applications in medicine, biochemistry and agriculture (Modarresi et al., 2009; Singh et al., 1980). The medicinal activity of the tetrazole functionality is due to its ability to serve as a bioequivalent (bioisostere) of the carboxylic acid group (Smith et al., 1991; Duncia et al., 1990). They are also used as anti-hypertensive, anti-allergic, anti-biotic and anti-convulsant agents (Myznikov et al., 2007; Schocken et al., 1989; Mekni & Bakloiti, 2008; Lim et al., 2007). As part of our on-going study of bio-active molecules we herein report the synthesis and X-ray structure of the title compound as a building block precursor in the synthesis of new tetrazole scaffold compounds.

The title compound, Fig. 1, comprises infinite chains of [Na(H₂O)₂]⁺ cations having a diamond-shaped cross-section (Fig. 2) and running parallel to the b axis. These are associated on all four sides by tetrazoluide anions via O—H···N hydrogen bonds (Table 1) to generate layers parallel to (100) which have the chlorobenzenecyanoethenyl substituents protruding from both surfaces (Figs 3 and 4). Additionally, the sodium ion makes a contact of 2.4801 (13) Å with N4 of the tetrazolide ring which is significantly shorter than the sum of the ionic radius of Na⁺ and the van der Waals radius of N (2.71 Å). The C—N and N—N bond lengths in the ring (1.314 (2)–1.345 (2) Å) suggest significant delocalization of the negative charge. The hydrogen bonding interactions may restrict the cation to approach this site as opposed to the face of the ring. The tetrazolide and benzene rings, respectively, make dihedral angle of 4.8 (2) and 25.8 (2)° with the plane defined by C2–C4.

Related literature top

For chemical behaviour of tetrazoles, see: Smith et al. (1991); Duncia et al. (1990). For various industrial applications of different tetrazole derivatives, see: Modarresi et al. (2009); Singh et al. (1980). For medicinal activities of compounds with a tetrazole scaffold, see: Myznikov et al. (2007); Schocken et al. (1989); Mekni & Bakloiti (2008); Lim et al. (2007).

Experimental top

The title compound has been obtained as an unexpected product from a multi-component reaction of 1 mmol (94 mg) of amino-pyridine, 4-chloro-benzaldehyde (1 mmol, 141.5 mg), malononitrile (1 mmol, 66 mg), sodium acetate (0.15 mmol, 12.3 mg) and sodium azide (1 mmol, 65 mg). The reaction mixture was refluxed in ethanol/water (1:1) and monitored by TLC until completion after 3 hours. On cooling, the solid precipitate was collected, dried under vacuum and recrystallized from ethanol to afford suitable crystals for X-ray diffraction.

Structure description top

For chemical behaviour of tetrazoles, see: Smith et al. (1991); Duncia et al. (1990). For various industrial applications of different tetrazole derivatives, see: Modarresi et al. (2009); Singh et al. (1980). For medicinal activities of compounds with a tetrazole scaffold, see: Myznikov et al. (2007); Schocken et al. (1989); Mekni & Bakloiti (2008); Lim et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Title compound with numbering scheme and 50% probability ellipsoids.
	Fig. 2. A portion of the {[Na(H₂O)₂]⁺}_n chain (symmetry operations: (i) x, 1 + y, z, (ii) 2 - x, 1/2 + y, 3/2 - z, (iii) x, -1 + y, z, (iv) 2 - x, -1/2 + y, 3/2 - z, (v) 2 - x, -3/2 + y, 3/2 - z, (vi) x, -2 + y, z).
	Fig. 3. Packing viewed along the b axis.
	Fig. 4. Elevation view of the chain structure.

Poly[di-µ-aqua-{5-[(1Z)-2-(4-chlorophenyl)-1-cyanoethenyl]-1,2,3,4-tetrazol-1-ido-κN¹}sodium] top

Crystal data top

[Na(C₁₀H₅ClN₅)(H₂O)₂]	F(000) = 592
M_r = 289.66	D_x = 1.517 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 22.0438 (4) Å	Cell parameters from 6311 reflections
b = 3.8343 (1) Å	θ = 4.0–74.5°
c = 15.0141 (3) Å	µ = 3.08 mm⁻¹
β = 92.427 (1)°	T = 150 K
V = 1267.89 (5) Å³	Plate, colourless
Z = 4	0.29 × 0.11 × 0.04 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2560 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2249 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.026
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.5°, θ_min = 2.0°
ω scans	h = −27→25
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −4→4
T_min = 0.73, T_max = 0.89	l = −18→18
9115 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)] = 0.032	Hydrogen site location: mixed
wR(F²) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0487P)² + 0.4982P] where P = (F_o² + 2F_c²)/3
2560 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Na(C₁₀H₅ClN₅)(H₂O)₂]	V = 1267.89 (5) Å³
M_r = 289.66	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 22.0438 (4) Å	µ = 3.08 mm⁻¹
b = 3.8343 (1) Å	T = 150 K
c = 15.0141 (3) Å	0.29 × 0.11 × 0.04 mm
β = 92.427 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2560 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	2249 reflections with I > 2σ(I)
T_min = 0.73, T_max = 0.89	R_int = 0.026
9115 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.03	Δρ_max = 0.36 e Å⁻³
2560 reflections	Δρ_min = −0.37 e Å⁻³
172 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.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å) while those attached to oxygen were placed in locations derived from a difference map and their parameters adjusted to give O—H = 0.84 Å. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.49516 (2)	0.10717 (11)	0.35718 (3)	0.03137 (13)
N1	0.86367 (6)	1.0318 (4)	0.43087 (8)	0.0206 (3)
N2	0.91834 (6)	1.1473 (4)	0.46047 (8)	0.0220 (3)
N3	0.92611 (6)	1.0749 (4)	0.54572 (8)	0.0221 (3)
N4	0.87680 (6)	0.9091 (4)	0.57424 (8)	0.0209 (3)
N5	0.74923 (7)	0.5087 (5)	0.65661 (10)	0.0382 (4)
C1	0.83943 (7)	0.8871 (4)	0.50194 (9)	0.0176 (3)
C2	0.77918 (7)	0.7259 (4)	0.50140 (9)	0.0194 (3)
C3	0.76111 (7)	0.6066 (5)	0.58710 (10)	0.0242 (3)
C4	0.74473 (7)	0.6828 (4)	0.42591 (10)	0.0210 (3)
H4	0.7629	0.7579	0.3729	0.025*
C5	0.68365 (7)	0.5378 (4)	0.41324 (10)	0.0204 (3)
C6	0.66615 (7)	0.4117 (4)	0.32820 (10)	0.0240 (3)
H6	0.6941	0.4214	0.2818	0.029*
C7	0.60884 (7)	0.2734 (4)	0.31088 (10)	0.0244 (3)
H7	0.5977	0.1835	0.2535	0.029*
C8	0.56795 (7)	0.2681 (4)	0.37836 (11)	0.0232 (3)
C9	0.58373 (7)	0.3933 (5)	0.46302 (10)	0.0254 (3)
H9	0.5553	0.3870	0.5088	0.030*
C10	0.64131 (7)	0.5273 (4)	0.47993 (10)	0.0243 (3)
H10	0.6523	0.6135	0.5377	0.029*
Na1	0.92711 (3)	0.78850 (17)	0.72191 (4)	0.02362 (16)
O1	0.99226 (5)	0.9704 (3)	0.84267 (6)	0.0211 (2)
H1A	1.0146	0.8147	0.8659	0.025*
H1B	0.9717	1.0768	0.8799	0.025*
O2	0.86926 (5)	0.2859 (3)	0.75583 (7)	0.0251 (3)
H2A	0.8664	0.3340	0.8101	0.030*
H2B	0.8326	0.2395	0.7434	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0220 (2)	0.0323 (2)	0.0393 (2)	−0.00816 (16)	−0.00439 (15)	−0.00037 (17)
N1	0.0179 (6)	0.0247 (7)	0.0192 (6)	−0.0011 (5)	0.0002 (5)	0.0004 (5)
N2	0.0194 (6)	0.0248 (7)	0.0216 (6)	−0.0015 (5)	0.0001 (5)	0.0001 (5)
N3	0.0196 (6)	0.0251 (7)	0.0214 (6)	−0.0024 (5)	−0.0017 (5)	−0.0011 (5)
N4	0.0190 (6)	0.0243 (7)	0.0191 (6)	−0.0017 (5)	−0.0008 (5)	−0.0003 (5)
N5	0.0268 (8)	0.0584 (11)	0.0292 (7)	−0.0056 (8)	−0.0005 (6)	0.0161 (7)
C1	0.0171 (7)	0.0178 (7)	0.0179 (6)	0.0020 (6)	0.0007 (5)	−0.0010 (5)
C2	0.0181 (7)	0.0181 (7)	0.0221 (7)	0.0018 (6)	0.0019 (5)	0.0021 (6)
C3	0.0161 (7)	0.0301 (9)	0.0260 (8)	−0.0015 (6)	−0.0029 (6)	0.0041 (7)
C4	0.0195 (7)	0.0214 (7)	0.0222 (7)	0.0002 (6)	0.0022 (5)	0.0008 (6)
C5	0.0187 (7)	0.0187 (7)	0.0237 (7)	0.0013 (6)	−0.0009 (5)	0.0008 (6)
C6	0.0226 (8)	0.0262 (8)	0.0230 (7)	0.0024 (7)	0.0007 (6)	0.0003 (6)
C7	0.0243 (8)	0.0235 (8)	0.0250 (7)	0.0014 (7)	−0.0049 (6)	−0.0027 (6)
C8	0.0190 (7)	0.0190 (8)	0.0311 (8)	−0.0018 (6)	−0.0039 (6)	0.0020 (6)
C9	0.0201 (8)	0.0300 (9)	0.0263 (7)	0.0005 (7)	0.0028 (6)	0.0013 (7)
C10	0.0232 (8)	0.0262 (8)	0.0233 (7)	0.0001 (7)	−0.0014 (6)	−0.0028 (6)
Na1	0.0246 (3)	0.0255 (3)	0.0205 (3)	0.0022 (3)	−0.0020 (2)	−0.0011 (2)
O1	0.0211 (5)	0.0246 (6)	0.0176 (5)	0.0045 (4)	0.0001 (4)	−0.0001 (4)
O2	0.0252 (6)	0.0323 (6)	0.0175 (5)	0.0033 (5)	−0.0022 (4)	−0.0019 (5)

Geometric parameters (Å, º) top

Cl1—C8	1.7359 (16)	C7—C8	1.384 (2)
N1—C1	1.3343 (19)	C7—H7	0.9500
N1—N2	1.3419 (18)	C8—C9	1.389 (2)
N2—N3	1.3138 (17)	C9—C10	1.383 (2)
N3—N4	1.3449 (18)	C9—H9	0.9500
N4—C1	1.3374 (19)	C10—H10	0.9500
N4—Na1	2.4801 (13)	Na1—O2ⁱ	2.3619 (13)
N5—C3	1.150 (2)	Na1—O1	2.3697 (12)
C1—C2	1.465 (2)	Na1—O2	2.3780 (14)
C2—C4	1.348 (2)	Na1—O1ⁱⁱ	2.3941 (12)
C2—C3	1.438 (2)	O1—Na1ⁱⁱⁱ	2.3941 (12)
C4—C5	1.462 (2)	O1—H1A	0.8399
C4—H4	0.9500	O1—H1B	0.8398
C5—C10	1.398 (2)	O2—Na1^iv	2.3619 (13)
C5—C6	1.404 (2)	O2—H2A	0.8399
C6—C7	1.385 (2)	O2—H2B	0.8401
C6—H6	0.9500

C1—N1—N2	104.89 (12)	C9—C10—C5	120.98 (15)
N3—N2—N1	109.33 (12)	C9—C10—H10	119.5
N2—N3—N4	109.65 (12)	C5—C10—H10	119.5
C1—N4—N3	104.47 (12)	O2ⁱ—Na1—O1	84.99 (4)
C1—N4—Na1	161.92 (11)	O2ⁱ—Na1—O2	107.99 (5)
N3—N4—Na1	92.06 (8)	O1—Na1—O2	112.82 (4)
N1—C1—N4	111.66 (13)	O2ⁱ—Na1—O1ⁱⁱ	156.29 (5)
N1—C1—C2	124.39 (13)	O1—Na1—O1ⁱⁱ	91.35 (4)
N4—C1—C2	123.95 (13)	O2—Na1—O1ⁱⁱ	95.05 (4)
C4—C2—C3	123.10 (14)	O2ⁱ—Na1—N4	79.46 (4)
C4—C2—C1	122.35 (13)	O1—Na1—N4	149.61 (5)
C3—C2—C1	114.51 (13)	O2—Na1—N4	96.83 (4)
N5—C3—C2	177.07 (17)	O1ⁱⁱ—Na1—N4	92.55 (4)
C2—C4—C5	129.74 (14)	O2ⁱ—Na1—N3	84.63 (4)
C2—C4—H4	115.1	O1—Na1—N3	125.07 (5)
C5—C4—H4	115.1	O2—Na1—N3	121.70 (4)
C10—C5—C6	118.38 (14)	O1ⁱⁱ—Na1—N3	78.35 (4)
C10—C5—C4	123.85 (14)	N4—Na1—N3	27.99 (4)
C6—C5—C4	117.74 (14)	Na1—O1—Na1ⁱⁱⁱ	106.04 (4)
C7—C6—C5	121.07 (14)	Na1—O1—H1A	115.7
C7—C6—H6	119.5	Na1ⁱⁱⁱ—O1—H1A	95.6
C5—C6—H6	119.5	Na1—O1—H1B	109.0
C8—C7—C6	119.03 (14)	Na1ⁱⁱⁱ—O1—H1B	116.9
C8—C7—H7	120.5	H1A—O1—H1B	113.0
C6—C7—H7	120.5	Na1^iv—O2—Na1	107.98 (5)
C7—C8—C9	121.26 (15)	Na1^iv—O2—H2A	116.7
C7—C8—Cl1	119.77 (12)	Na1—O2—H2A	95.3
C9—C8—Cl1	118.96 (12)	Na1^iv—O2—H2B	107.7
C10—C9—C8	119.26 (15)	Na1—O2—H2B	130.0
C10—C9—H9	120.4	H2A—O2—H2B	98.7
C8—C9—H9	120.4

C1—N1—N2—N3	−0.19 (17)	C3—C2—C4—C5	4.3 (3)
N1—N2—N3—N4	0.17 (17)	C1—C2—C4—C5	−178.16 (15)
N1—N2—N3—Na1	31.8 (5)	C2—C4—C5—C10	23.5 (3)
N2—N3—N4—C1	−0.08 (17)	C2—C4—C5—C6	−158.45 (17)
N2—N3—N4—Na1	172.51 (11)	C10—C5—C6—C7	−1.3 (2)
N2—N1—C1—N4	0.14 (17)	C4—C5—C6—C7	−179.43 (15)
N2—N1—C1—C2	179.72 (14)	C5—C6—C7—C8	1.5 (2)
N3—N4—C1—N1	−0.04 (17)	C6—C7—C8—C9	−1.0 (2)
Na1—N4—C1—N1	−155.5 (3)	C6—C7—C8—Cl1	178.18 (13)
N3—N4—C1—C2	−179.62 (14)	C7—C8—C9—C10	0.3 (3)
Na1—N4—C1—C2	24.9 (4)	Cl1—C8—C9—C10	−178.91 (13)
N1—C1—C2—C4	6.0 (2)	C8—C9—C10—C5	−0.1 (3)
N4—C1—C2—C4	−174.48 (15)	C6—C5—C10—C9	0.6 (2)
N1—C1—C2—C3	−176.27 (15)	C4—C5—C10—C9	178.56 (15)
N4—C1—C2—C3	3.3 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3ⁱⁱ	0.84	2.04	2.8443 (17)	160
O1—H1B···N2^v	0.84	2.02	2.8593 (17)	175
O2—H2B···N5	0.84	2.44	3.1009 (19)	136

Symmetry codes: (ii) −x+2, y−1/2, −z+3/2; (v) x, −y+5/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3ⁱ	0.84	2.04	2.8443 (17)	160
O1—H1B···N2ⁱⁱ	0.84	2.02	2.8593 (17)	175
O2—H2B···N5	0.84	2.44	3.1009 (19)	136

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x, −y+5/2, z+1/2.

Acknowledgements

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Duncia, J. V., Chiu, A. T., Carini, D. J., Gregory, G. B., Johnson, A. L., Price, W. A., Wells, G. J., Wong, P. C., Calabrese, J. C. & Timmermans, P. B. M. W. M. (1990). J. Med. Chem. 33, 1312–1329. CrossRef CAS PubMed Web of Science Google Scholar
Lim, S. J., Sunohara, Y. & Matsumoto, H. (2007). J. Pestic. Sci. 32, 249–254. Web of Science CrossRef CAS Google Scholar
Mekni, N. & Baklouti, A. (2008). J. Fluor. Chem. 129, 1073–1075. Web of Science CrossRef CAS Google Scholar
Modarresi, A. A. R. & Nasrollahzadeh, M. (2009). Turk J. Chem. 33, 267–280. Google Scholar
Myznikov, L. V., Hrabalek, A. & Koldobskii, G. I. (2007). Chem. Heterocycl. Compd, 43, 1–9. CrossRef CAS Google Scholar
Schocken, M. J., Creekmore, R. W., Theodoridis, G., Nystrom, G. J. & Robinson, R. A. (1989). Appl. Environ. Microbiol. 55, 1220–1222. PubMed CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Singh, H., Chawla, A. S., Kapoor, V. K., Paul, D. & Malhotra, R. K. (1980). Prog. Med. Chem. 17, 151–183. CrossRef CAS PubMed Google Scholar
Smith, G. D., Zabrocki, J., Flak, T. A. & Marshall, G. R. (1991). Int. J. Pept. Protein Res. 37, 191–197. CrossRef PubMed CAS Google Scholar

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