Crystal structure and Hirshfeld surface analysis of N-[(Z)-(2-hy­droxy­phen­yl)methyl­idene]aniline N-oxide

Mohamed, S.K.; Said, A.I.; Mague, J.T.; Aly, M.F.; Akkurt, M.; Elgarhy, S.M.I.

doi:10.1107/S2056989021004813

research communications

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ISSN: 2056-9890

Volume 77| Part 6| June 2021| Pages 596-599

https://doi.org/10.1107/S2056989021004813

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Crystal structure and Hirshfeld surface analysis of N-[(Z)-(2-hydroxyphenyl)methylidene]aniline N-oxide

Shaaban K. Mohamed,^a,^b ^* Awad I. Said,^c Joel T. Mague,^d Moustafa F. Aly,^e Mehmet Akkurt ^f and Sahar M. I. Elgarhy ^g

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cChemistry Department, Faculty of Science, Assuit University, Egypt, ^dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^eChemistry Department, Faculty of Science, South Valley University, Egypt, ^fDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^gFaculty of Science, Department of Bio Chemistry, Beni Suef University, Beni Suef, Egypt
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by D. Gray, University of Illinois Urbana-Champaign, USA (Received 25 January 2021; accepted 6 May 2021; online 11 May 2021)

The conformation of the title compound, C₁₃H₁₁NO₂, is partially determined by a strong, intramolecular O—H⋯O hydrogen bond. The crystal packing consists of strongly corrugated layers parallel to the ac plane and associated through C—H⋯π(ring) interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most significant contributions to the crystal packing are from H⋯H (44.1%), C⋯H/H⋯C (29.4%) and O⋯H/H⋯O (17.3%) contacts.

Keywords: crystal structure; hydrogen bond; N-oxide; C—H⋯π(ring); nitrones; Hirshfeld surface analysis.

CCDC reference: 2082055

1. Chemical context

Nitrones are a very important class of organic compounds as a result of their medicinal and pharmaceutical applications. They show antifungal (Salman et al., 2013 ), antibacterial (Chakraborty et al., 2010 ), neuroprotective (Chioua et al., 2012 ) and anticancer (Floyd et al., 2011 ) activities. In addition, nitrone compounds are widely used as antioxidant agents (Al-Mowali et al., 2014 ) because of their ability to scavenge free radicals. Based on these findings and following our interest in this area, we report herein the crystal structure of the title compound.

2. Structural commentary

The molecular structure of the title compound (Fig. 1) is almost planar, with maximum deviations of 0.398 (2) Å for O1 and −0.756 (2) Å for O2. The N1—O2 distance of 1.331 (2) Å is normal for a single bond and agrees well with those observed in other amine N-oxides. The dihedral angle between the aromatic rings (C1–C6 and C8–C13) is 1.94 (12) °. The torsion angles C2—C1—C7—N1, C1—C7—N1—C8, C1—C7—N1—O2, C7—N1—C8—C9 and O2—N1—C8–C-9 are −30.2 (3), −179.7 (2), −0.4 (3), 27.3 (3) and −152.0 (2)°, respectively. The conformation of the title compound is partially determined by a strong, intramolecular O1—H1⋯O2 hydrogen bond (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 aromatic rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.97	1.53	2.479 (2)	167
C7—H7⋯O2ⁱ	0.95	2.43	3.368 (3)	167
C10—H10⋯O1ⁱⁱ	0.95	2.53	3.227 (3)	131
C11—H11⋯Cg1ⁱⁱⁱ	0.95	2.94	3.662 (3)	136
C4—H4⋯Cg2^iv	0.95	2.77	3.545 (3)	140
Symmetry codes: (i) ; (ii) $[x-1, -y, z-{\script{1\over 2}}]$ ; (iii) $[x, -y, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+1, z+{\script{1\over 2}}]$ .

Figure 1
The title molecule with labelling scheme and 50% probability ellipsoids. The intramolecular hydrogen bond is shown by a dashed line.

3. Supramolecular features

In the crystal, C7—H7⋯O2ⁱ hydrogen bonds (Table 1) link the molecules, forming chains along the a-axis direction. The chains are linked into strongly corrugated sheets parallel to the ac plane by C10—H10⋯O2ⁱⁱ hydrogen bonds and C11—H11⋯Cg1ⁱⁱⁱ interactions (Cg1 is the centroid of the C1–C6 hydroxyphenyl ring; Table 1 and Fig. 2). The sheets are stacked along the b-axis direction by C4—H4⋯Cg2^iv interactions (Cg2 is the centroid of the C8–C13 phenyl ring; Table 1 and Figs. 2 and 3).

Figure 2
Detail of the intermolecular C—H⋯O hydrogen bonds and the C—H⋯π(ring) interactions (black and green dashed lines, respectively) viewed along the b-axis direction.

Figure 3
Packing viewed along the (120) direction with intermolecular interactions shown as in Fig. 2

4. Hirshfeld surface analysis

A Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ) was carried out using CrystalExplorer17.5 (Turner et al., 2017 ) to visualize the intermolecular interactions in the title compound. The Hirshfeld surface mapped over d_norm (Fig. 4) shows the expected bright-red spots near atoms O1, O2, H7 and H10, which are involved in the C—H⋯O hydrogen-bonding interactions. The bright-red spot near O1 indicates its role as a hydrogen-bond acceptor to (C10)H10 (Fig. 4) and another red region near O2 correlates with the C7—H7⋯O2 interaction.

Figure 4
A view of the three-dimensional Hirshfeld surface with the C—H⋯O interactions for the title compound, plotted over d_norm in the range −0.2242 to 1.2146 a.u. (a) front view, (b) back view.

The two-dimensional fingerprint plots show the relative contributions of the various types of contacts to the Hirshfeld surface for the title compound (McKinnon et al., 2007 ). The plots (Fig. 5) reveal that H⋯H and C⋯H/H⋯C interactions make the greatest contributions to the surface contacts, while O⋯H/H⋯O, C⋯C, N⋯H/H⋯N, N⋯C/C⋯N and O⋯C/C⋯O contacts are less significant (Tables 2 and 3).

Table 2
Summary of short interatomic contacts (Å) in the title compound

Contact	Distance	Symmetry operation
O2⋯H7	2.43	1 + x, y, z
O1⋯H10	2.53	1 + x, −y, $[{1\over 2}]$ + z
O2⋯H12	2.87	x, 1 + y, z
C3⋯H12	3.02	x, −y, $[{1\over 2}]$ + z
H4⋯C11	2.86	x, 1 − y, $[{1\over 2}]$ + z
H6⋯H13	2.46	−1 + x, 1 + y, z

Table 3
Percentage contributions of interatomic contacts to the Hirshfeld surface for the title compound

Contact	Percentage contribution
H⋯H	44.1
C⋯H/H⋯C	29.4
O⋯H/H⋯O	17.3
C⋯C	5.3
N⋯C/C⋯N	1.7
N⋯H/H⋯N	1.5
O⋯C/C⋯O	0.7

Figure 5
A view of the two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C and (d) O⋯H/H⋯O interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

5. Database survey

The four most closely related structures are (Z)-N-[(1,3-diphenyl-1H-pyrazol-4-yl)methanimine]-N-oxido (DEPVOM; Mohamed et al., 2018 ), (Z)-1,2-bis(3-bromophenyl)diazene 1-oxide (SIYHAK01; Goswami et al., 2018 ), (Z)-N-benzylidene-1-phenylmethanamine oxide hydrogen peroxide solvate (JELQOJ; Churakov et al., 2017 ) and (Z)-N-(2-chlorobenzylidene)aniline N-oxide (ERIXEJ; Fu et al., 2011 ).

In the crystal of DEPVOM, (101) layers are generated by C—H⋯O hydrogen bonds coupled with C—H⋯π(ring) and offset π–π stacking interactions. In the crystal of SIYHAK01, C—H⋯O and C—H⋯Br hydrogen bonds together with offset π–π interactions stack the molecules along the a-axis direction. In the crystal of JELQOJ, the organic and peroxide molecules are linked through both peroxide O—H donor groups to oxide O-atom acceptors, giving one-dimensional chains extending along the b-axis direction. Weak intermolecular C—H⋯O hydrogen-bonding interactions are also present. In the crystal of ERIXEJ, the molecule is stabilized by an intramolecular C—H⋯O hydrogen bond. The geometry about the C=N bond is Z [C—C—N—O torsion angle = −4.2 (3)°] and the phenyl and benzene rings are trans-oriented around the C=N bond. The phenyl and benzene rings make a dihedral angle of 56.99 (2)°.

6. Synthesis and crystallization

(Z)-(2-Hydroxyphenyl)methylidene]benzenimine N-oxide (nitrone) was prepared according to the reported procedures (Mobinikhaledi et al., 2005 ). 0.7 ml (6 mmol) of salicyaldehyde were added to a warmed solution of 0.8 g (6 mmol) N-phenylhydroxyamine in ethanol followed by stirring for 5 minutes, then standing at room temperature in the dark overnight gave the nitrone, which was recrystallized from ethanol in 53% yield; m.p. 387–388 K.

7. Refinement

Crystal and refinement details are presented in Table 4. The H atom of the OH group was found in difference-Fourier maps, and its positional parameters were fixed using the AFIX 3 instruction in SHELXL and were refined with the isotropic displacement parameter U_iso(H) = 1.5U_eq(O). The C-bound H atoms were positioned geometrically, with C—H = 0.95 Å, and constrained to ride on their parent atoms, withU_iso(H) = 1.2U_eq(C). Attempts to determine the absolute structure did not produce a definitive result, viz.: Flack x = 0.2 (3) by classical fit to all intensities 0.30 (14) from 611 selected quotients (Parsons' method). A round of TWIN/BASF refinement gave BASF = 0.2 (4) with no improvement in the model.

Table 4
Experimental details

Crystal data
Chemical formula	C₁₃H₁₁NO₂
M_r	213.23
Crystal system, space group	Monoclinic, Pc
Temperature (K)	150
a, b, c (Å)	5.5391 (1), 5.7873 (2), 16.0859 (4)
β (°)	99.067 (1)
V (Å³)	509.21 (2)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.77
Crystal size (mm)	0.19 × 0.17 × 0.15

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.77, 0.89
No. of measured, independent and observed [I > 2σ(I)] reflections	3578, 1654, 1607
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.084, 1.06
No. of reflections	1654
No. of parameters	145
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18
Absolute structure	Flack x determined using 611 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 ).
Absolute structure parameter	0.30 (13)
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), DIAMOND (Brandenburg & Putz, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2082055

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989021004813/ey2006sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021004813/ey2006Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989021004813/ey2006Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

N-[(Z)-(2-Hydroxyphenyl)methylidene]aniline N-oxide top

Crystal data top

C₁₃H₁₁NO₂	F(000) = 224
M_r = 213.23	D_x = 1.391 Mg m⁻³
Monoclinic, Pc	Cu Kα radiation, λ = 1.54178 Å
a = 5.5391 (1) Å	Cell parameters from 3430 reflections
b = 5.7873 (2) Å	θ = 5.6–72.4°
c = 16.0859 (4) Å	µ = 0.77 mm⁻¹
β = 99.067 (1)°	T = 150 K
V = 509.21 (2) Å³	Block, yellow
Z = 2	0.19 × 0.17 × 0.15 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	1654 independent reflections
Radiation source: INCOATEC IµS micro–focus source	1607 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.023
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.4°, θ_min = 5.6°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −7→7
T_min = 0.77, T_max = 0.89	l = −19→19
3578 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.033	w = 1/[σ²(F_o²) + (0.0441P)² + 0.084P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.084	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.18 e Å⁻³
1654 reflections	Δρ_min = −0.18 e Å⁻³
145 parameters	Absolute structure: Flack x determined using 611 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013).
2 restraints	Absolute structure parameter: 0.30 (13)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
O1	0.8449 (3)	0.3532 (3)	0.64513 (12)	0.0342 (4)
H1	0.841875	0.289527	0.589214	0.051*
O2	0.7828 (3)	0.2215 (3)	0.49662 (12)	0.0338 (4)
N1	0.5424 (3)	0.1864 (3)	0.48272 (13)	0.0267 (4)
C1	0.4520 (4)	0.4953 (4)	0.57874 (14)	0.0260 (5)
C2	0.6705 (4)	0.5169 (4)	0.63617 (15)	0.0280 (5)
C3	0.7030 (4)	0.7093 (4)	0.68930 (16)	0.0328 (5)
H3	0.852651	0.728354	0.726592	0.039*
C4	0.5207 (5)	0.8717 (4)	0.68821 (18)	0.0348 (5)
H4	0.545906	1.001606	0.724635	0.042*
C5	0.3009 (4)	0.8470 (4)	0.63443 (17)	0.0349 (6)
H5	0.174797	0.958261	0.634589	0.042*
C6	0.2662 (4)	0.6611 (4)	0.58092 (16)	0.0304 (5)
H6	0.114410	0.643651	0.544695	0.036*
C7	0.3908 (4)	0.3082 (4)	0.51888 (15)	0.0270 (5)
H7	0.222390	0.270734	0.504648	0.032*
C8	0.4586 (4)	0.0034 (4)	0.42327 (14)	0.0263 (5)
C9	0.2257 (4)	0.0070 (4)	0.37527 (15)	0.0304 (5)
H9	0.116018	0.130115	0.380872	0.036*
C10	0.1571 (4)	−0.1720 (4)	0.31930 (17)	0.0340 (5)
H10	−0.001169	−0.171673	0.286384	0.041*
C11	0.3176 (5)	−0.3521 (4)	0.31083 (16)	0.0327 (5)
H11	0.269918	−0.473587	0.271973	0.039*
C12	0.5480 (5)	−0.3533 (4)	0.35956 (18)	0.0324 (5)
H12	0.657396	−0.477040	0.354374	0.039*
C13	0.6199 (4)	−0.1748 (4)	0.41587 (16)	0.0301 (5)
H13	0.778043	−0.175337	0.448865	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0260 (9)	0.0382 (9)	0.0363 (9)	0.0038 (6)	−0.0010 (7)	0.0001 (7)
O2	0.0137 (7)	0.0461 (9)	0.0418 (9)	−0.0015 (7)	0.0047 (7)	−0.0028 (8)
N1	0.0170 (9)	0.0340 (9)	0.0290 (10)	−0.0013 (7)	0.0031 (7)	0.0025 (8)
C1	0.0253 (12)	0.0287 (11)	0.0250 (12)	−0.0010 (8)	0.0073 (10)	0.0032 (8)
C2	0.0232 (12)	0.0314 (11)	0.0301 (12)	0.0004 (8)	0.0057 (10)	0.0066 (9)
C3	0.0308 (13)	0.0359 (12)	0.0320 (12)	−0.0082 (10)	0.0059 (10)	−0.0024 (10)
C4	0.0380 (14)	0.0300 (11)	0.0397 (13)	−0.0066 (9)	0.0166 (11)	−0.0022 (10)
C5	0.0346 (14)	0.0328 (12)	0.0403 (15)	0.0032 (9)	0.0150 (11)	0.0065 (10)
C6	0.0232 (11)	0.0362 (12)	0.0321 (12)	0.0026 (9)	0.0054 (9)	0.0071 (10)
C7	0.0185 (10)	0.0327 (11)	0.0293 (11)	0.0009 (8)	0.0028 (9)	0.0049 (9)
C8	0.0241 (11)	0.0292 (11)	0.0258 (13)	−0.0022 (8)	0.0044 (10)	0.0029 (8)
C9	0.0218 (11)	0.0379 (12)	0.0316 (13)	0.0017 (9)	0.0053 (10)	−0.0012 (9)
C10	0.0246 (11)	0.0448 (13)	0.0329 (12)	−0.0037 (9)	0.0052 (10)	−0.0013 (11)
C11	0.0328 (12)	0.0340 (12)	0.0328 (13)	−0.0066 (9)	0.0096 (10)	−0.0021 (10)
C12	0.0336 (12)	0.0307 (11)	0.0341 (12)	0.0044 (9)	0.0096 (10)	0.0023 (10)
C13	0.0249 (11)	0.0350 (12)	0.0307 (13)	0.0025 (8)	0.0056 (9)	0.0053 (9)

Geometric parameters (Å, º) top

O1—C2	1.345 (3)	C5—H5	0.9500
O1—H1	0.9697	C6—H6	0.9500
O2—N1	1.331 (2)	C7—H7	0.9500
N1—C7	1.302 (3)	C8—C13	1.382 (3)
N1—C8	1.454 (3)	C8—C9	1.395 (3)
C1—C2	1.407 (3)	C9—C10	1.386 (4)
C1—C6	1.411 (3)	C9—H9	0.9500
C1—C7	1.453 (3)	C10—C11	1.391 (4)
C2—C3	1.398 (4)	C10—H10	0.9500
C3—C4	1.377 (4)	C11—C12	1.389 (4)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.385 (4)	C12—C13	1.390 (4)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.372 (4)	C13—H13	0.9500

C2—O1—H1	105.1	N1—C7—C1	126.9 (2)
C7—N1—O2	122.78 (18)	N1—C7—H7	116.6
C7—N1—C8	121.79 (18)	C1—C7—H7	116.6
O2—N1—C8	115.43 (17)	C13—C8—C9	121.2 (2)
C2—C1—C6	118.6 (2)	C13—C8—N1	117.2 (2)
C2—C1—C7	125.97 (19)	C9—C8—N1	121.66 (19)
C6—C1—C7	115.4 (2)	C10—C9—C8	118.9 (2)
O1—C2—C3	118.3 (2)	C10—C9—H9	120.5
O1—C2—C1	122.5 (2)	C8—C9—H9	120.5
C3—C2—C1	119.1 (2)	C9—C10—C11	120.6 (2)
C4—C3—C2	120.8 (2)	C9—C10—H10	119.7
C4—C3—H3	119.6	C11—C10—H10	119.7
C2—C3—H3	119.6	C12—C11—C10	119.6 (2)
C3—C4—C5	120.5 (2)	C12—C11—H11	120.2
C3—C4—H4	119.7	C10—C11—H11	120.2
C5—C4—H4	119.7	C11—C12—C13	120.5 (2)
C6—C5—C4	119.6 (2)	C11—C12—H12	119.8
C6—C5—H5	120.2	C13—C12—H12	119.8
C4—C5—H5	120.2	C8—C13—C12	119.2 (2)
C5—C6—C1	121.2 (2)	C8—C13—H13	120.4
C5—C6—H6	119.4	C12—C13—H13	120.4
C1—C6—H6	119.4

C6—C1—C2—O1	172.1 (2)	C6—C1—C7—N1	153.4 (2)
C7—C1—C2—O1	−4.2 (3)	C7—N1—C8—C13	−153.0 (2)
C6—C1—C2—C3	−4.4 (3)	O2—N1—C8—C13	27.7 (3)
C7—C1—C2—C3	179.3 (2)	C7—N1—C8—C9	27.3 (3)
O1—C2—C3—C4	−174.0 (2)	O2—N1—C8—C9	−152.0 (2)
C1—C2—C3—C4	2.6 (3)	C13—C8—C9—C10	−0.1 (3)
C2—C3—C4—C5	0.1 (4)	N1—C8—C9—C10	179.6 (2)
C3—C4—C5—C6	−1.0 (4)	C8—C9—C10—C11	−0.2 (4)
C4—C5—C6—C1	−0.9 (4)	C9—C10—C11—C12	0.6 (4)
C2—C1—C6—C5	3.6 (3)	C10—C11—C12—C13	−0.7 (4)
C7—C1—C6—C5	−179.7 (2)	C9—C8—C13—C12	0.0 (3)
O2—N1—C7—C1	−0.4 (3)	N1—C8—C13—C12	−179.8 (2)
C8—N1—C7—C1	−179.7 (2)	C11—C12—C13—C8	0.4 (4)
C2—C1—C7—N1	−30.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 aromatic rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.97	1.53	2.479 (2)	167
C7—H7···O2ⁱ	0.95	2.43	3.368 (3)	167
C10—H10···O1ⁱⁱ	0.95	2.53	3.227 (3)	131
C11—H11···Cg1ⁱⁱⁱ	0.95	2.94	3.662 (3)	136
C4—H4···Cg2^iv	0.95	2.77	3.545 (3)	140

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

Summary of short interatomic contacts (Å) in the title compound top

Contact	Distance	Symmetry operation
O2···H7	2.43	1 + x, y, z
O1···H10	2.53	1 + x, -y, 1/2 + z
O2···H12	2.87	x, 1 + y, z
C3···H12	3.02	x, -y, 1/2 + z
H4···C11	2.86	x, 1 - y, 1/2 + z
H6···H13	2.46	-1 + x, 1 + y, z

Percentage contributions of interatomic contacts to the Hirshfeld surface for the title compound top

Contact	Percentage contribution
H···H	44.1
C···H/H···C	29.4
O···H/H···O	17.3
C···C	5.3
N···C/C···N	1.7
N···H/H···N	1.5
O···C/C···O	0.7

Funding information

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.

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