N-Benzyl-2-hy­droxy­ethanaminium cyanurate

Contreras-Espejel, C.A.; García-Eleno, M.A.; Santacruz-Juárez, E.; Reyes-Martínez, R.; Morales-Morales, D.

doi:10.1107/S1600536813029383

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1741-o1742

doi:10.1107/S1600536813029383

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N-Benzyl-2-hydroxyethanaminium cyanurate

Carlos Abraham Contreras-Espejel,^a Marco A. García-Eleno,^a Ericka Santacruz-Juárez,^b ^* Reyna Reyes-Martínez ^a and David Morales-Morales ^a

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, D.F., 04510, Mexico, and ^bUniversidad Politécnica de Tlaxcala Km. 9.5 Carretera Federal Tlaxcala-Puebla, Av. Universidad Politécnica No. 1 Xalcaltzingo, Tepeyanco, Tlaxcala, C.P., 90180, Mexico
^*Correspondence e-mail: ericka.santacruz@uptlax.edu.mx

(Received 6 September 2013; accepted 24 October 2013; online 6 November 2013)

In the cation of the title compound C₉H₁₄ON⁺·C₃H₂O₃N₃⁻, the benzylamine C—N bond subtends a dihedral angle of 78.3 (2)° with the phenyl ring. The cyanurate anion is in the usual keto-form and shows an r.m.s. deviation from planarity of 0.010 Å. In the crystal, the cyanurate anions form N—H⋯O hydrogen-bonded zigzag ribbons along [001]. These ribbons are crosslinked by the organocations via O—H⋯N and N—H⋯O hydrogen bonds, forming bilayers parallel to (010) which are held together along [010] by slipped π–π interactions between pairs of cyanurate anions [shortest contact distances C⋯C = 3.479 (2), O⋯N = 3.400 (2); centroid–centroid distance= 4.5946 (9) Å] and between cyanurate and phenyl rings [centroid–centroid distance = 3.7924 (12) Å, ring–ring angle = 11.99 (10)°].

CCDC reference: 968571

Related literature

For adducts of cyanuric acid, see: Sivashankar (2000 ); Ranganathan et al. (2000 ); Prior et al. (2013 ). For cyanurate and trithiocyanurate salts, see: Krepps et al. (2001 ); Barszcz et al. (2006 ); Yang (2010 ); Nichol & Clegg (2006 ); Hou & Yang (2011 ); El-Gamel et al. (2008 ). For a common hydrogen-bond motif in cyanurates and trithiocyanurates, see: Falvello et al. (1997 ); Sivashankar (2000); Hou & Yang (2011).

Experimental

Crystal data

C₉H₁₄NO⁺·C₃H₂N₃O₃⁻
M_r = 280.29
Monoclinic, C 2/c
a = 21.0855 (3) Å
b = 14.0236 (2) Å
c = 10.0626 (1) Å
β = 115.474 (1)°
V = 2686.18 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.47 × 0.12 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ) T_min = 0.68, T_max = 0.75
16557 measured reflections
2753 independent reflections
1913 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.115
S = 1.02
2753 reflections
197 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2ⁱ	0.921 (19)	1.841 (19)	2.7609 (17)	176.5 (16)
N5—H5⋯O4ⁱⁱ	0.879 (19)	1.97 (2)	2.8434 (17)	172.9 (17)
O1—H1⋯N1	0.91 (2)	1.82 (2)	2.7103 (17)	169 (2)
N2—H2A⋯O2ⁱⁱⁱ	0.942 (19)	1.979 (19)	2.8612 (17)	155.2 (16)
N2—H2B⋯O1ⁱⁱⁱ	0.939 (19)	2.003 (19)	2.835 (2)	146.6 (16)
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 968571

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813029383/qk2061sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029383/qk2061Isup2.hkl

checkCIF report

Comment top

Cyanuric acid and trithiocyanuric acid are based on planar six-membered rings and are used as building blocks of supramolecular assemblies held together via a variety of intermolecular hydrogen bonds. In undissociated form they contain in the solid state three hydrogen donors (N—H) and three hydrogen acceptors (O, S). In this form cyanuric acid generates adducts with pyridine (Sivashankar, 2000), 4,4'-bipyridyl (Ranganathan et al., 2000) and melamine (Prior et al., 2013). And both, cyanuric and trithiocyanuric acid are found in mono- and di-anionic form in various organic salts (Krepps et al., 2001; Barszcz et al., 2006), particularly as ammonium salts such as tripropylammonium (Yang, 2010), 1-dimethylammonio-8-dimethylaminonaphthalene (Nichol & Clegg, 2006), and guanidinium (El-Gamel et al., 2008). Here we report the synthesis and crystal structure of the salt N-benzyl-2-hydroxyethanaminium cyanurate, [C₉H₁₄ON]⁺[C₃H₂O₃N₃]^-.

The asymmetric unit of the title compound is formed by one molecule of the cyanurate anion and one molecule of the N-benzyl-2-hydroxyethanaminium cation (Fig. 1). The cyanurate anions are mutually linked via two pairs of centrosymmetric hydrogen bonds (N3—H3···O2ⁱ and its inverse, N5—H5···O4ⁱⁱand its inverse) to form zig-zag ribbons along [001], a motif frequently encountered in cyanuric acid, cyanurate salts, and cyanurate metal complexes (Falvello et al., 1997; Sivashankar, 2000; Hou et al., 2011). Each N-benzyl-2-hydroxyethanaminium cation links two adjacent cyanurate zig-zag ribbons via the hydrogen bonds O1—H1···N1 and N2—H2A···O2ⁱⁱⁱ two form a 2-dimensional infinite bilayer parallel to (010) (Fig. 2). This bilayer is reinforced by the intercationic hydrogen bond N2—H2B···O1ⁱⁱⁱ and by an inclined π-π interaction between the cyanurate and the phenyl ring (Cg—Cg = 3.7924 (12) Å, ring-ring angle = 11.99 (10)°). Adjacent bilayers are held together along [010] by slipped π-π interactions between centrosymmetric pairs of cyanurate anions (shortest contact distances C4···C4(1-x,-y,1-z) = 3.479 (2) Å, O1···N3(1-x,-y,1-z) = 3.400 (2) Å; Cg—Cg = 4.5946 (9) Å). The incorporation of the N-benzyl-2-hydroxyethanaminium cation into the bilayer determines the conformation of the cation, which shows torsion angles of C10—C9—C15—N2 = 78.3 (2), C9—C15—N2—C8 = -168.71 (14), and C15—N2—C8—O1 = 59.3 (2)° for side chain atoms. The cyanurate ion is almost planar (r.m.s. and maximum deviations from planarity are 0.010 Å and 0.037 (15) Å (N5)).

Related literature top

For adducts of cyanuric acid, see: Sivashankar (2000); Ranganathan et al. (2000); Prior et al. (2013). For cyanurate and trithiocyanurate salts, see: Krepps et al. (2001); Barszcz et al. (2006); Yang (2010); Nichol & Clegg (2006); Hou & Yang (2011); El-Gamel et al. (2008). For a common hydrogen-bond motif in cyanurates and trithiocyanurates, see: Falvello et al. (1997); Sivashankar (2000); Hou & Yang (2011).

Experimental top

A mixture of triethylamine (1.5 g, 14.8 mmol) and 2-(benzylamino)ethanol (2 g, 13.5 mmol) was added slowly to methanolic solution of cyanuric chloride (0.83 g, 4.4 mmol) in an ice bath under stirring. The resulting solution was set to reflux for three days, and then allowed to cool down until the formation of a crystalline material was observed. The colourless crystalline material was filtered and washed with acetone and cold methanol.

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Asymmetric unit of the title compound with ellipsoids drawn at 40% probability.
	Fig. 2. Hydrogen bond pattern in crystal structure of the title compound. Hydrogen bonds are shown as dashed lines.

N-Benzyl-2-hydroxyethanaminium cyanurate top

Crystal data top

C₉H₁₄NO⁺·C₃H₂N₃O₃⁻	F(000) = 1184
M_r = 280.29	D_x = 1.386 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.0855 (3) Å	Cell parameters from 4964 reflections
b = 14.0236 (2) Å	θ = 2.5–26.0°
c = 10.0626 (1) Å	µ = 0.11 mm⁻¹
β = 115.474 (1)°	T = 298 K
V = 2686.18 (6) Å³	Needle, colourless
Z = 8	0.47 × 0.12 × 0.09 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2753 independent reflections
Radiation source: fine-focus sealed tube	1913 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 8.333 pixels mm^-1	θ_max = 26.4°, θ_min = 1.8°
ω–scans	h = −26→26
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −17→16
T_min = 0.68, T_max = 0.75	l = −12→12
16557 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0505P)² + 1.1375P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2753 reflections	Δρ_max = 0.20 e Å⁻³
197 parameters	Δρ_min = −0.17 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: 0.0026 (3)

Crystal data top

C₉H₁₄NO⁺·C₃H₂N₃O₃⁻	V = 2686.18 (6) Å³
M_r = 280.29	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.0855 (3) Å	µ = 0.11 mm⁻¹
b = 14.0236 (2) Å	T = 298 K
c = 10.0626 (1) Å	0.47 × 0.12 × 0.09 mm
β = 115.474 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	2753 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2012)	1913 reflections with I > 2σ(I)
T_min = 0.68, T_max = 0.75	R_int = 0.041
16557 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.20 e Å⁻³
2753 reflections	Δρ_min = −0.17 e Å⁻³
197 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.

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

	x	y	z	U_iso*/U_eq
N1	0.35291 (6)	0.12658 (10)	0.30864 (13)	0.0383 (3)
O2	0.40501 (6)	0.13333 (10)	0.15312 (11)	0.0519 (4)
C2	0.40936 (8)	0.12819 (12)	0.28065 (16)	0.0368 (4)
N3	0.47580 (7)	0.12493 (11)	0.39537 (13)	0.0400 (4)
H3	0.5148 (10)	0.1258 (12)	0.3762 (19)	0.048*
C4	0.48802 (8)	0.11770 (12)	0.53885 (16)	0.0388 (4)
O4	0.54804 (6)	0.11518 (10)	0.63875 (11)	0.0541 (4)
N5	0.42916 (7)	0.11362 (11)	0.56146 (14)	0.0408 (4)
H5	0.4334 (9)	0.1104 (12)	0.652 (2)	0.049*
C6	0.36125 (8)	0.12036 (11)	0.44990 (16)	0.0364 (4)
O6	0.31188 (6)	0.11963 (9)	0.48328 (13)	0.0506 (3)
O1	0.22892 (6)	0.14867 (9)	0.06812 (13)	0.0496 (3)
H1	0.2670 (12)	0.1384 (15)	0.154 (2)	0.074*
N2	0.20910 (8)	0.34336 (11)	0.13192 (16)	0.0455 (4)
H2A	0.1669 (10)	0.3632 (13)	0.054 (2)	0.055*
H2B	0.2401 (10)	0.3266 (13)	0.091 (2)	0.055*
C7	0.17466 (9)	0.17499 (14)	0.1081 (2)	0.0538 (5)
H7A	0.1647	0.1220	0.1582	0.065*
H7B	0.1323	0.1886	0.0198	0.065*
C8	0.19408 (9)	0.26071 (13)	0.20647 (19)	0.0487 (5)
H8A	0.1558	0.2766	0.2316	0.058*
H8B	0.2352	0.2465	0.2969	0.058*
C9	0.31829 (9)	0.40676 (12)	0.33215 (19)	0.0445 (4)
C10	0.36875 (11)	0.41489 (17)	0.2800 (2)	0.0652 (6)
H10	0.3559	0.4333	0.1830	0.078*
C11	0.43848 (12)	0.3958 (2)	0.3712 (3)	0.0856 (8)
H11	0.4722	0.4009	0.3351	0.103*
C12	0.45783 (11)	0.3696 (2)	0.5138 (3)	0.0829 (8)
H12	0.5047	0.3570	0.5750	0.099*
C13	0.40907 (12)	0.36203 (19)	0.5662 (2)	0.0805 (7)
H13	0.4225	0.3441	0.6635	0.097*
C14	0.33930 (10)	0.38063 (15)	0.4766 (2)	0.0615 (6)
H14	0.3062	0.3754	0.5143	0.074*
C15	0.24244 (10)	0.42631 (13)	0.2327 (2)	0.0549 (5)
H15A	0.2391	0.4828	0.1743	0.066*
H15B	0.2172	0.4387	0.2918	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0261 (6)	0.0615 (9)	0.0268 (7)	−0.0001 (6)	0.0109 (5)	−0.0007 (6)
O2	0.0327 (6)	0.0998 (10)	0.0227 (6)	0.0031 (6)	0.0116 (5)	0.0033 (6)
C2	0.0296 (8)	0.0541 (10)	0.0249 (8)	0.0008 (7)	0.0099 (6)	−0.0006 (7)
N3	0.0254 (7)	0.0706 (10)	0.0246 (7)	0.0000 (6)	0.0112 (5)	0.0005 (6)
C4	0.0319 (8)	0.0575 (11)	0.0269 (8)	−0.0007 (7)	0.0126 (7)	−0.0008 (7)
O4	0.0298 (6)	0.1026 (11)	0.0256 (6)	−0.0008 (6)	0.0079 (5)	0.0018 (6)
N5	0.0328 (7)	0.0683 (10)	0.0222 (7)	−0.0014 (6)	0.0124 (6)	0.0005 (6)
C6	0.0320 (8)	0.0486 (10)	0.0303 (8)	−0.0014 (7)	0.0148 (7)	−0.0030 (7)
O6	0.0345 (6)	0.0849 (10)	0.0386 (6)	−0.0021 (6)	0.0215 (5)	−0.0028 (6)
O1	0.0426 (7)	0.0633 (8)	0.0348 (7)	0.0070 (6)	0.0090 (5)	0.0004 (6)
N2	0.0357 (8)	0.0533 (9)	0.0366 (8)	0.0066 (7)	0.0052 (6)	0.0049 (7)
C7	0.0346 (9)	0.0589 (12)	0.0596 (12)	−0.0028 (8)	0.0123 (8)	0.0033 (9)
C8	0.0418 (10)	0.0574 (12)	0.0499 (10)	0.0061 (8)	0.0225 (8)	0.0072 (8)
C9	0.0467 (10)	0.0429 (10)	0.0424 (10)	−0.0047 (8)	0.0179 (8)	−0.0090 (8)
C10	0.0614 (13)	0.0930 (16)	0.0436 (11)	−0.0183 (11)	0.0248 (10)	−0.0094 (10)
C11	0.0518 (13)	0.139 (2)	0.0730 (16)	−0.0237 (14)	0.0335 (12)	−0.0226 (15)
C12	0.0456 (12)	0.123 (2)	0.0627 (15)	−0.0081 (12)	0.0067 (11)	−0.0152 (14)
C13	0.0634 (14)	0.123 (2)	0.0427 (12)	−0.0133 (14)	0.0113 (11)	0.0012 (12)
C14	0.0524 (11)	0.0904 (16)	0.0414 (10)	−0.0084 (10)	0.0197 (9)	−0.0079 (10)
C15	0.0548 (11)	0.0468 (11)	0.0568 (11)	0.0088 (9)	0.0180 (9)	−0.0008 (9)

Geometric parameters (Å, º) top

N1—C2	1.3361 (19)	C7—H7A	0.9700
N1—C6	1.3580 (19)	C7—H7B	0.9700
O2—C2	1.2487 (18)	C8—H8A	0.9700
C2—N3	1.3807 (19)	C8—H8B	0.9700
N3—C4	1.3569 (19)	C9—C14	1.375 (3)
N3—H3	0.921 (19)	C9—C10	1.379 (3)
C4—O4	1.2324 (18)	C9—C15	1.503 (2)
C4—N5	1.3559 (19)	C10—C11	1.384 (3)
N5—C6	1.392 (2)	C10—H10	0.9300
N5—H5	0.879 (19)	C11—C12	1.363 (3)
C6—O6	1.2237 (18)	C11—H11	0.9300
O1—C7	1.415 (2)	C12—C13	1.346 (3)
O1—H1	0.91 (2)	C12—H12	0.9300
N2—C8	1.487 (2)	C13—C14	1.380 (3)
N2—C15	1.504 (2)	C13—H13	0.9300
N2—H2A	0.942 (19)	C14—H14	0.9300
N2—H2B	0.939 (19)	C15—H15A	0.9700
C7—C8	1.498 (3)	C15—H15B	0.9700

C2—N1—C6	119.72 (13)	N2—C8—H8A	109.6
O2—C2—N1	122.64 (14)	C7—C8—H8A	109.6
O2—C2—N3	117.44 (14)	N2—C8—H8B	109.6
N1—C2—N3	119.92 (13)	C7—C8—H8B	109.6
C4—N3—C2	123.52 (13)	H8A—C8—H8B	108.1
C4—N3—H3	116.4 (11)	C14—C9—C10	118.30 (18)
C2—N3—H3	120.0 (11)	C14—C9—C15	121.32 (17)
O4—C4—N5	123.70 (14)	C10—C9—C15	120.38 (17)
O4—C4—N3	121.90 (14)	C9—C10—C11	120.35 (19)
N5—C4—N3	114.39 (14)	C9—C10—H10	119.8
C4—N5—C6	124.08 (13)	C11—C10—H10	119.8
C4—N5—H5	119.0 (11)	C12—C11—C10	120.1 (2)
C6—N5—H5	116.8 (11)	C12—C11—H11	119.9
O6—C6—N1	123.05 (14)	C10—C11—H11	119.9
O6—C6—N5	118.67 (14)	C13—C12—C11	120.0 (2)
N1—C6—N5	118.28 (13)	C13—C12—H12	120.0
C7—O1—H1	105.3 (14)	C11—C12—H12	120.0
C8—N2—C15	113.71 (14)	C12—C13—C14	120.6 (2)
C8—N2—H2A	108.8 (11)	C12—C13—H13	119.7
C15—N2—H2A	109.5 (11)	C14—C13—H13	119.7
C8—N2—H2B	111.4 (12)	C9—C14—C13	120.62 (19)
C15—N2—H2B	106.1 (11)	C9—C14—H14	119.7
H2A—N2—H2B	107.0 (15)	C13—C14—H14	119.7
O1—C7—C8	111.87 (14)	C9—C15—N2	111.28 (14)
O1—C7—H7A	109.2	C9—C15—H15A	109.4
C8—C7—H7A	109.2	N2—C15—H15A	109.4
O1—C7—H7B	109.2	C9—C15—H15B	109.4
C8—C7—H7B	109.2	N2—C15—H15B	109.4
H7A—C7—H7B	107.9	H15A—C15—H15B	108.0
N2—C8—C7	110.42 (14)

C6—N1—C2—O2	179.62 (16)	O1—C7—C8—N2	59.3 (2)
C6—N1—C2—N3	−0.9 (2)	C14—C9—C10—C11	0.8 (3)
O2—C2—N3—C4	−178.86 (16)	C15—C9—C10—C11	−179.3 (2)
N1—C2—N3—C4	1.7 (3)	C9—C10—C11—C12	−0.6 (4)
C2—N3—C4—O4	−179.83 (16)	C10—C11—C12—C13	0.2 (4)
C2—N3—C4—N5	0.2 (2)	C11—C12—C13—C14	−0.1 (4)
O4—C4—N5—C6	177.24 (17)	C10—C9—C14—C13	−0.7 (3)
N3—C4—N5—C6	−2.7 (2)	C15—C9—C14—C13	179.37 (19)
C2—N1—C6—O6	179.16 (15)	C12—C13—C14—C9	0.4 (4)
C2—N1—C6—N5	−1.5 (2)	C14—C9—C15—N2	−101.8 (2)
C4—N5—C6—O6	−177.10 (16)	C10—C9—C15—N2	78.3 (2)
C4—N5—C6—N1	3.5 (2)	C8—N2—C15—C9	74.5 (2)
C15—N2—C8—C7	−168.71 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2ⁱ	0.921 (19)	1.841 (19)	2.7609 (17)	176.5 (16)
N5—H5···O4ⁱⁱ	0.879 (19)	1.97 (2)	2.8434 (17)	172.9 (17)
O1—H1···N1	0.91 (2)	1.82 (2)	2.7103 (17)	169 (2)
N2—H2A···O2ⁱⁱⁱ	0.942 (19)	1.979 (19)	2.8612 (17)	155.2 (16)
N2—H2B···O1ⁱⁱⁱ	0.939 (19)	2.003 (19)	2.835 (2)	146.6 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2ⁱ	0.921 (19)	1.841 (19)	2.7609 (17)	176.5 (16)
N5—H5···O4ⁱⁱ	0.879 (19)	1.97 (2)	2.8434 (17)	172.9 (17)
O1—H1···N1	0.91 (2)	1.82 (2)	2.7103 (17)	169 (2)
N2—H2A···O2ⁱⁱⁱ	0.942 (19)	1.979 (19)	2.8612 (17)	155.2 (16)
N2—H2B···O1ⁱⁱⁱ	0.939 (19)	2.003 (19)	2.835 (2)	146.6 (16)

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

Acknowledgements

RRM and DMM thank Dr Ruben A. Toscano for technical assistance. Support of this research by CONACyT (CB 2010–154732) and PAPIIT (IN201711–3) is acknowledged. ESJ thanks PROMEP "Apoyo a perfil deseable".

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