2-(Naphthalen-2-yl­oxy)-N′-[2-(naphthalen-2-yl­oxy)acet­yl]acetohydrazide monohydrate

El-Hiti, G.A.; Abdel-Wahab, B.F.; Baashen, M.A.; Yousif, E.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S241431462100314X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 6| Part 3| March 2021| x210314

https://doi.org/10.1107/S241431462100314X

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2-(Naphthalen-2-yloxy)-N′-[2-(naphthalen-2-yloxy)acetyl]acetohydrazide monohydrate

Gamal A El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b Mohammed A. Baashen,^c Emad Yousif,^d Amany S. Hegazy ^e and Benson M. Kariuki ^e

^aCornea Research Chair, Department of Optometry, College of Applied, Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, ^bApplied Organic Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt, ^cDepartment of Chemistry, College of Science and Humanities, Shaqra University, Al-Dawadmi 11911, Saudi Arabia, ^dDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad, 64021, Iraq, and ^eSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
^*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 24 March 2021; accepted 25 March 2021; online 31 March 2021)

The title compound, C₂₄H₂₀N₂O₄·H₂O, crystallizes with half a molecule of 2-(naphthalen-2-yloxy)-N′-[2-(naphthalen-2-yloxy)acetyl]acetohydrazide and half a water molecule in the asymmetric unit. In the crystal, molecules form planes parallel to (011). Two molecules are connected by water molecules via O—H⋯O and N—H⋯O hydrogen bonds.

Keywords: crystal structure; hydrazide; naphthalene; acylhydrazines.

CCDC reference: 2072979

Structure description

Diacylhydrazines can be used as environmentally friendly insecticides against lepidopteran larvae and ground-dwelling coleopterans (Morou et al., 2013 ; Suzuki et al., 2017 ; Wang et al., 2017 ). In addition, they are precursors in the synthesis of electroluminescent devices (Huang et al., 2009 ; Wu & Chen, 2009 , 2010 ).

The asymmetric unit comprises half a molecule of 2-(naphthalen-2-yloxy)-N′-[2-(naphthalen-2-yloxy)acetyl]acetohydrazide and half a molecule of water, both centred on the twofold rotation axis parallel to the c axis. An ORTEP representation is shown in Fig. 1. Similar to 2-[(naphthalen-2-yl)oxy]acetamide (Huang et al., 2020 ), the 2-[(naphthalen-2-yl)oxy]acetamidyl unit of the title compound is planar, and the twist angle between the two halves is 64.9 (1)°.

Figure 1
The molecular structure of the title compound showing 50% displacement ellipsoids.

In the crystal, the molecules form planes parallel to (011) (Fig. 2). Two 2-(naphthalen-2-yloxy)-N′-[2-(naphthalen-2-yloxy)acetyl]acetohydrazide molecules are connected by a water molecule via O—H⋯O and N—H⋯O bonds (Fig. 3, Table 1). One water molecule donates O—H⋯O hydrogen bonds to two neighbouring molecules (related by twofold rotation), leading to the formation of a helix parallel to the c axis (green dashed lines in Fig. 3). The same pair of molecules is also connected by N—H⋯O bonds, resulting in a second parallel helical arrangement (red dashed lines in Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86	2.19	2.954 (6)	149
O3—H1O⋯O2ⁱ	0.92 (6)	1.87 (6)	2.796 (5)	177 (6)
Symmetry code: (i) x, y+1, z+1.

Figure 2
The crystal structure viewed down the b axis.

Figure 3
A segment of the crystal structure showing O—H⋯O hydrogen bonds as green dashed lines and N—H⋯O interactions as red dashed lines.

Synthesis and crystallization

A mixture of ethyl 2-cyano-3-ethoxyacrylate (0.34 g, 2.0 mmol) and 2-(naphthalen-2-yloxy)acetohydrazide (0.43 g, 2.0 mmol) in dry ethanol (10 mL) was heated with stirring under reflux for 2 h. The solid formed on cooling to room temperature. It was collected by filtration, washed with ethanol, dried and recrystallized from dimethylformamide to give colourless crystals, m.p. > 300°C (lit. m.p. > 300°C; Abdel-Wahab et al., 2017 ) of the title compound in 76% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂O₄·H₂O
M_r	418.43
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	293
a, b, c (Å)	37.196 (4), 4.8441 (4), 5.5840 (4)
V (Å³)	1006.12 (15)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.80
Crystal size (mm)	0.37 × 0.05 × 0.02

Data collection
Diffractometer	Rigaku Oxford Diffraction SuperNova, Dual, Cu at home/near, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.687, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7482, 2079, 1456
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.632

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.172, 1.05
No. of reflections	2079
No. of parameters	145
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.19
Absolute structure	Flack x determined using 424 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.1 (3)
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2020 ) and CHEMDRAW Ultra (Cambridge Soft, 2016 ).

Structural data

CCDC reference: 2072979

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S241431462100314X/bt4110sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462100314X/bt4110Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431462100314X/bt4110Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2020); software used to prepare material for publication: CHEMDRAW Ultra (Cambridge Soft, 2016).

2-(Naphthalen-2-yloxy)-N'-[2-(naphthalen-2-yloxy)acetyl]acetohydrazide monohydrate top

Crystal data top

C₂₄H₂₀N₂O₄·H₂O	D_x = 1.381 Mg m⁻³
M_r = 418.43	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2	Cell parameters from 1274 reflections
a = 37.196 (4) Å	θ = 4.7–73.7°
b = 4.8441 (4) Å	µ = 0.80 mm⁻¹
c = 5.5840 (4) Å	T = 293 K
V = 1006.12 (15) Å³	Needle, colourless
Z = 2	0.37 × 0.05 × 0.02 mm
F(000) = 440

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at home/near, Atlas diffractometer	1456 reflections with I > 2σ(I)
ω scans	R_int = 0.063
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015)	θ_max = 76.9°, θ_min = 4.8°
T_min = 0.687, T_max = 1.000	h = −47→44
7482 measured reflections	k = −6→5
2079 independent reflections	l = −4→6

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.062	w = 1/[σ²(F_o²) + (0.0593P)² + 0.4016P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.172	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.31 e Å⁻³
2079 reflections	Δρ_min = −0.19 e Å⁻³
145 parameters	Absolute structure: Flack x determined using 424 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.1 (3)

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.

Refinement. The coordinates for the water hydrogen atom was refined freely. The rest of the hydrogen atoms were positioned geometrically and refined using a riding model. All U_iso(H) were constrained to be 1.2 times U_eq(C,N).

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

	x	y	z	U_iso*/U_eq
C1	0.39660 (13)	0.5528 (10)	0.8789 (8)	0.0464 (10)
C2	0.39748 (15)	0.7245 (12)	1.0831 (9)	0.0555 (12)
H2	0.416807	0.717218	1.188528	0.067*
C3	0.36943 (15)	0.9021 (12)	1.1238 (9)	0.0571 (13)
H3	0.370140	1.016895	1.257183	0.068*
C4	0.33940 (14)	0.9153 (10)	0.9681 (9)	0.0501 (11)
C5	0.31024 (16)	1.0968 (12)	1.0072 (11)	0.0616 (14)
H5	0.310336	1.210702	1.141216	0.074*
C6	0.28194 (15)	1.1080 (12)	0.8520 (11)	0.0635 (14)
H6	0.262865	1.227610	0.880591	0.076*
C7	0.28187 (15)	0.9368 (12)	0.6482 (12)	0.0642 (14)
H7	0.262674	0.944144	0.541710	0.077*
C8	0.30967 (15)	0.7608 (12)	0.6059 (10)	0.0595 (13)
H8	0.309150	0.649189	0.470417	0.071*
C9	0.33923 (14)	0.7443 (11)	0.7632 (9)	0.0480 (11)
C10	0.36861 (14)	0.5619 (11)	0.7222 (9)	0.0488 (11)
H10	0.368669	0.448574	0.587834	0.059*
C11	0.42712 (13)	0.2082 (10)	0.6538 (9)	0.0499 (11)
H11A	0.427237	0.319235	0.509307	0.060*
H11B	0.405620	0.094828	0.651848	0.060*
C12	0.45969 (14)	0.0248 (10)	0.6558 (8)	0.0477 (10)
O2	0.46226 (11)	−0.1567 (8)	0.5050 (8)	0.0639 (10)
O3	0.500000	0.500000	1.1908 (10)	0.0627 (14)
O1	0.42622 (10)	0.3845 (8)	0.8567 (7)	0.0549 (9)
N1	0.48388 (11)	0.0727 (9)	0.8289 (7)	0.0494 (9)
H1	0.479501	0.192285	0.938948	0.059*
H1O	0.4869 (17)	0.609 (14)	1.295 (11)	0.069 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.051 (3)	0.044 (2)	0.045 (2)	0.004 (2)	0.0000 (19)	0.0022 (18)
C2	0.061 (3)	0.055 (3)	0.050 (3)	0.003 (2)	−0.009 (2)	0.000 (2)
C3	0.068 (3)	0.056 (3)	0.047 (3)	0.008 (2)	−0.004 (2)	−0.011 (2)
C4	0.057 (3)	0.043 (2)	0.050 (3)	0.004 (2)	0.004 (2)	0.002 (2)
C5	0.074 (3)	0.053 (3)	0.058 (3)	0.010 (3)	0.011 (3)	−0.003 (3)
C6	0.057 (3)	0.058 (3)	0.075 (4)	0.013 (3)	0.007 (3)	0.004 (3)
C7	0.055 (3)	0.060 (3)	0.078 (4)	0.007 (3)	−0.006 (3)	0.008 (3)
C8	0.056 (3)	0.057 (3)	0.066 (3)	0.003 (2)	−0.009 (2)	−0.006 (2)
C9	0.052 (3)	0.042 (2)	0.050 (2)	0.001 (2)	0.0030 (19)	0.0036 (19)
C10	0.056 (3)	0.044 (2)	0.046 (2)	0.004 (2)	−0.0023 (19)	−0.0042 (18)
C11	0.055 (3)	0.047 (2)	0.048 (3)	0.003 (2)	−0.003 (2)	−0.003 (2)
C12	0.055 (3)	0.045 (2)	0.042 (2)	0.001 (2)	0.001 (2)	0.0014 (19)
O2	0.068 (2)	0.060 (2)	0.063 (2)	0.0081 (19)	−0.003 (2)	−0.0190 (19)
O3	0.075 (4)	0.060 (3)	0.053 (3)	0.015 (3)	0.000	0.000
O1	0.0528 (19)	0.0537 (19)	0.058 (2)	0.0103 (15)	−0.0078 (16)	−0.0032 (17)
N1	0.050 (2)	0.054 (2)	0.045 (2)	0.0109 (18)	0.0001 (18)	−0.0065 (18)

Geometric parameters (Å, º) top

C1—C10	1.361 (7)	C7—H7	0.9300
C1—O1	1.376 (6)	C8—C9	1.410 (7)
C1—C2	1.412 (7)	C8—H8	0.9300
C2—C3	1.371 (8)	C9—C10	1.424 (7)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.417 (7)	C11—O1	1.419 (6)
C3—H3	0.9300	C11—C12	1.502 (7)
C4—C9	1.413 (7)	C11—H11A	0.9700
C4—C5	1.413 (7)	C11—H11B	0.9700
C5—C6	1.364 (9)	C12—O2	1.221 (6)
C5—H5	0.9300	C12—N1	1.341 (6)
C6—C7	1.408 (9)	O3—H1O	0.92 (6)
C6—H6	0.9300	N1—N1ⁱ	1.391 (8)
C7—C8	1.361 (8)	N1—H1	0.8600

C10—C1—O1	125.0 (4)	C7—C8—H8	119.3
C10—C1—C2	121.2 (5)	C9—C8—H8	119.3
O1—C1—C2	113.8 (4)	C8—C9—C4	118.4 (5)
C3—C2—C1	119.1 (5)	C8—C9—C10	122.3 (5)
C3—C2—H2	120.5	C4—C9—C10	119.4 (5)
C1—C2—H2	120.5	C1—C10—C9	120.3 (5)
C2—C3—C4	121.8 (5)	C1—C10—H10	119.9
C2—C3—H3	119.1	C9—C10—H10	119.9
C4—C3—H3	119.1	O1—C11—C12	111.7 (4)
C9—C4—C5	119.1 (5)	O1—C11—H11A	109.3
C9—C4—C3	118.3 (5)	C12—C11—H11A	109.3
C5—C4—C3	122.6 (5)	O1—C11—H11B	109.3
C6—C5—C4	121.3 (5)	C12—C11—H11B	109.3
C6—C5—H5	119.4	H11A—C11—H11B	107.9
C4—C5—H5	119.4	O2—C12—N1	124.7 (5)
C5—C6—C7	119.4 (5)	O2—C12—C11	118.9 (5)
C5—C6—H6	120.3	N1—C12—C11	116.4 (4)
C7—C6—H6	120.3	C1—O1—C11	116.6 (4)
C8—C7—C6	120.5 (5)	C12—N1—N1ⁱ	119.4 (4)
C8—C7—H7	119.7	C12—N1—H1	120.3
C6—C7—H7	119.7	N1ⁱ—N1—H1	120.3
C7—C8—C9	121.3 (5)

Symmetry code: (i) −x+1, −y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	2.19	2.954 (6)	149
O3—H1O···O2ⁱⁱ	0.92 (6)	1.87 (6)	2.796 (5)	177 (6)

Symmetry code: (ii) x, y+1, z+1.

Funding information

The authors are grateful to the Deanship of Scientific Research, King Saud University for funding through the Vice Deanship of Scientific Research Chairs.

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