3-Eth­oxy-5-phenyl-1H-1,2,4-triazole

Hebishy, A.M.; Elgemeie, G.H.; Salama, H.T.; Jones, P.G.

doi:10.1107/S241431461900378X

organic compounds

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ISSN: 2414-3146

Volume 4| Part 4| April 2019| x190378

https://doi.org/10.1107/S241431461900378X

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3-Ethoxy-5-phenyl-1H-1,2,4-triazole

Ali M. Hebishy,^a Galal H. Elgemeie,^a Hagar T. Salama ^a and Peter G. Jones ^b ^*

^aChemistry Department, Faculty of Science, Helwan University, Cairo, Egypt, and ^bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany
^*Correspondence e-mail: p.jones@tu-bs.de

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 14 March 2019; accepted 19 March 2019; online 2 April 2019)

The title compound, C₁₀H₁₁N₃O, crystallizes in the triclinic space group P $[\overline{1}]$ with Z′ = 2. The two independent molecules (A and B) differ in the orientation of the phenyl rings with respect to the plane of the triazine ring, with an interplanar angle of 11.45 (6)° in molecule A and 19.71 (5)° in molecule B, in the opposite sense. In the crystal, classical N—H⋯N hydrogen bonds cross-link the molecules to form chains parallel to the b axis. Two additional `weak' C—H⋯O hydrogen bonds link the chains to form layers parallel to (101).

Keywords: crystal structure; 1,2,4-triazole; pyrazole; synthesis; hydrogen bonding.

CCDC reference: 1904090

Structure description

Cyanoketene S,S-acetals and cyanoketene N,S-acetals are important synthetic intermediates (Elgemeie et al., 2015 , 2016 , 2017 , 2018 ) that have been used as building blocks to assemble a wide range of heterocyclic compounds (Azzam et al. 2017a ,b , 2019 ; Azzam & Elgemeie, 2019 ); they are also of general interest in medicinal chemistry (Abu-Zaied & Elgemeie, 2017 , 2018 ; Elgemeie et al. 2017c ). Recently, we have reported the synthesis of various antimetabolic agents starting from cyanoketene N,S-acetals (Elgemeie et al. 2006 , 2009 ), cyanoketene S,S-acetals (Elgemeie et al., 2003a , 2017d ), and cyanoketene N,N-acetals (Elgemeie et al., 2003b ). As a part of this programme, the reaction of (E)-ethyl 3-benzamido-2-cyano-3-(methylthio)acrylate (1) with hydrazine was investigated (Fig. 1). This gave a product whose mass spectrum was not consistent with the proposed pyrazole structure (3). Other spectroscopic measurements did not allow us to identify the product unambiguously and therefore the X-ray crystal structure was determined, confirming the exclusive presence of the triazole derivative (7) as sole product in the solid state. The formation of (7) is assumed to proceed via initial addition of the basic N atom of hydrazine to the double bond of (1), followed by formation of adduct (4) and elimination of ethyl cyanoacetate. From adduct (4), the favoured, kinetically and thermodynamically controlled product (7) is formed.

Figure 1
Reaction scheme.

Compound (7) crystallizes with two molecules (A and B) in the asymmetric unit, linked by the hydrogen bond N1—H01⋯N4′ (Table 1 and Fig. 2). The triazine rings of the two molecules subtend an interplanar angle of 74.75 (4)°. The asymmetric unit was chosen so that the molecules are linked by a hydrogen bond, but the best least-squares fit (r.m.s. deviation 0.057 Å excluding C12, C13, C15, C16) is obtained when one molecule is inverted (Fig. 3). The molecules differ in the orientation of the phenyl ring, whereby the interplanar angle to the triazine ring is 11.45 (6)° in molecule A (unprimed atoms) but 19.71 (5)° in molecule B (in the opposite sense).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H01⋯N4′	0.94 (2)	1.94 (2)	2.866 (1)	170 (1)
N1′—H01′⋯N4ⁱ	0.90 (2)	2.02 (2)	2.916 (1)	176 (1)
C13—H13⋯O1′ⁱⁱ	0.95	2.55	3.478 (2)	165
C15′—H15′⋯N2ⁱⁱⁱ	0.95	2.52	3.463 (2)	172
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z; (iii) -x, -y, -z+1.

Figure 2
A view of the molecular structures of the two independent molecules of compound (7), with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates a classical hydrogen bond (Table 1

Figure 3
Least-squares fit of all non-hydrogen atoms, except C12, C13, C15 and C16, of inverted molecule A (dashed lines) on molecule B.

In the crystal, molecules are linked by two classical hydrogen bonds, N1—H01⋯N4′ (within the asymmetric unit) and N1′—H01⋯N4 (by b-axis translation), to form chains parallel to the b axis. Weak intermolecular hydrogen bonds, C13—H13⋯O1′ and C15′—H15′⋯N2 (for operators see Table 1) cross-link these chains to form layers parallel to (101) (Table 1 and Fig. 4).

Figure 4
Packing diagram of compound (7), viewed perpendicular to plane (101). Classical hydrogen bonds are indicated by thick dashed lines, C—H⋯X interactions by thin dashed lines (see Table 1

). Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

The Cambridge Structural Database (Groom et al., 2016 ) contains no other example of a 1,2,4-triazine, unsubstituted at N1, with an oxygen substituent at C3. There are eight examples of a 1,2,4-triazine with a phenyl substituent at C5: refcodes DIWZOA (Othman et al., 2014a ), DOLCAJ (Dolzhenko et al., 2009 ), HIYTAM (Othman et al., 2014a ), IBOMAP (two polymorphs of the 3,5-diphenyl derivative; Brough et al., 2011 and Sudheendran et al., 2014 ), LAGCAX (Carlsen et al., 1991 ), SISNIS (Buzykin et al., 2006 ), URELIN (Zhu et al., 2011 ), XUHBEJ (De Rosa et al., 2014 ).

Synthesis and crystallization

Hydrazine hydrate (1 mmol) was added to a solution of (E)-ethyl 3-benzamido-2-cyano-3-(methylthio)acrylate (1) (1 mmol) in ethanol (20 ml) containing a few drops of piperidine. The mixture was heated under reflux with continuous stirring for 2 h, then poured onto ice. The solid product was filtered off, dried and recrystallized from ethanol to afford compound (7) as colourless crystals (yield 60%, m.p. 393 K). ¹H NMR (400 MHz, DMSO): δ 1.37 (t, 3H, CH₃), 4.34 (q, 2H, CH₂), 7.47–7.93 (m, 5H, Ph), 13.72 (s, H, NH-triazole). Analysis: calculated for C₁₀H₁₁N₃O (189.21): C, 63.48; H, 5.86; N, 22.21. Found: C, 63.25; H, 5.62; N, 22.44.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₁₁N₃O
M_r	189.22
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	8.0664 (4), 10.0476 (5), 12.5229 (5)
α, β, γ (°)	79.554 (4), 81.137 (4), 70.517 (5)
V (Å³)	936.17 (8)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.74
Crystal size (mm)	0.20 × 0.10 × 0.05

Data collection
Diffractometer	Oxford Diffraction Xcalibur Atlas Nova
Absorption correction	Multi-scan (SADABS; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarton, England.]$ )
T_min, T_max	0.937, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	30281, 3894, 3397
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.090, 1.05
No. of reflections	3894
No. of parameters	263
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.27
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarton, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL2017 (Sheldrick, 2015 ) and XP (Siemens, 1994 ).

Structural data

CCDC reference: 1904090

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S241431461900378X/su4171sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461900378X/su4171Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461900378X/su4171Isup3.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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL2017 (Sheldrick, 2015).

3-Ethoxy-5-phenyl-1H-1,2,4-triazole top

Crystal data top

C₁₀H₁₁N₃O	Z = 4
M_r = 189.22	F(000) = 400
Triclinic, P1	D_x = 1.343 Mg m⁻³
a = 8.0664 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 10.0476 (5) Å	Cell parameters from 16098 reflections
c = 12.5229 (5) Å	θ = 3.6–76.1°
α = 79.554 (4)°	µ = 0.74 mm⁻¹
β = 81.137 (4)°	T = 100 K
γ = 70.517 (5)°	Lath, colourless
V = 936.17 (8) Å³	0.20 × 0.10 × 0.05 mm

Data collection top

Oxford Diffraction Xcalibur Atlas Nova diffractometer	3894 independent reflections
Radiation source: micro-focus sealed X-ray tube	3397 reflections with I > 2σ(I)
Detector resolution: 10.3543 pixels mm^-1	R_int = 0.043
ω–scan	θ_max = 76.3°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Rigaku OD, 2015)	h = −10→10
T_min = 0.937, T_max = 1.000	k = −12→11
30281 measured reflections	l = −15→15

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)] = 0.034	Hydrogen site location: mixed
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0463P)² + 0.2414P] where P = (F_o² + 2F_c²)/3
3894 reflections	(Δ/σ)_max < 0.001
263 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.6131 (0.0016) x + 0.4132 (0.0052) y - 0.6162 (0.0069) z = 2.2732 (0.0040)

* 0.0019 (0.0006) N1 * 0.0006 (0.0006) N2 * -0.0028 (0.0006) C3 * 0.0038 (0.0006) N4 * -0.0035 (0.0006) C5

Rms deviation of fitted atoms = 0.0028

6.9734 (0.0022) x - 1.5826 (0.0053) y - 1.2344 (0.0061) z = 0.9885 (0.0034)

Angle to previous plane (with approximate esd) = 11.449 ( 0.057 )

* 0.0008 (0.0008) C11 * -0.0011 (0.0009) C12 * 0.0011 (0.0009) C13 * -0.0008 (0.0009) C14 * 0.0004 (0.0009) C15 * -0.0004 (0.0009) C16

Rms deviation of fitted atoms = 0.0008

3.3871 (0.0042) x + 1.0816 (0.0053) y + 11.8627 (0.0024) z = 4.1527 (0.0012)

Angle to previous plane (with approximate esd) = 77.006 ( 0.042 )

* 0.0001 (0.0006) N1' * -0.0006 (0.0006) N2' * 0.0009 (0.0007) C3' * -0.0008 (0.0006) N4' * 0.0004 (0.0006) C5'

Rms deviation of fitted atoms = 0.0006

3.7369 (0.0034) x + 4.3701 (0.0047) y + 11.6356 (0.0025) z = 4.0750 (0.0012)

Angle to previous plane (with approximate esd) = 19.712 ( 0.046 )

* -0.0014 (0.0008) C11' * 0.0001 (0.0008) C12' * 0.0008 (0.0009) C13' * -0.0005 (0.0009) C14' * -0.0008 (0.0009) C15' * 0.0017 (0.0008) C16'

Rms deviation of fitted atoms = 0.0010

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

	x	y	z	U_iso*/U_eq
N1	0.30398 (12)	0.33959 (10)	0.29129 (7)	0.0186 (2)
H01	0.309 (2)	0.2538 (18)	0.2700 (13)	0.033 (4)*
N2	0.31227 (12)	0.34480 (10)	0.39915 (7)	0.0189 (2)
C3	0.30430 (14)	0.47855 (12)	0.39607 (9)	0.0173 (2)
N4	0.29269 (12)	0.55939 (10)	0.29610 (7)	0.0184 (2)
C5	0.29156 (14)	0.46660 (12)	0.23169 (9)	0.0176 (2)
C6	0.31423 (15)	0.44416 (12)	0.58656 (9)	0.0205 (2)
H6A	0.367766	0.477794	0.638132	0.025*
H6B	0.390314	0.346689	0.574971	0.025*
C7	0.13224 (15)	0.44054 (13)	0.63501 (9)	0.0245 (2)
H7A	0.055441	0.537604	0.643488	0.037*
H7B	0.140288	0.381170	0.706524	0.037*
H7C	0.082810	0.400500	0.586489	0.037*
C11	0.27486 (14)	0.49708 (12)	0.11405 (9)	0.0191 (2)
C12	0.29281 (16)	0.62379 (13)	0.05453 (9)	0.0236 (2)
H12	0.314085	0.691340	0.090316	0.028*
C13	0.27955 (17)	0.65127 (13)	−0.05738 (10)	0.0259 (3)
H13	0.292318	0.737445	−0.097986	0.031*
C14	0.24777 (16)	0.55318 (13)	−0.10967 (9)	0.0251 (3)
H14	0.238324	0.572415	−0.185999	0.030*
C15	0.22973 (18)	0.42703 (14)	−0.05082 (10)	0.0286 (3)
H15	0.208292	0.359830	−0.086908	0.034*
C16	0.24296 (17)	0.39880 (13)	0.06086 (10)	0.0256 (3)
H16	0.230276	0.312403	0.101083	0.031*
O1	0.30570 (10)	0.53820 (8)	0.48320 (6)	0.01994 (18)
N1'	0.34778 (13)	−0.16318 (10)	0.26565 (8)	0.0196 (2)
H01'	0.325 (2)	−0.2465 (18)	0.2761 (12)	0.030 (4)*
N2'	0.51220 (13)	−0.15849 (10)	0.21821 (8)	0.0208 (2)
C3'	0.49143 (15)	−0.02159 (12)	0.21179 (9)	0.0196 (2)
N4'	0.33042 (13)	0.06147 (10)	0.25005 (7)	0.0197 (2)
C5'	0.24252 (15)	−0.03317 (12)	0.28387 (8)	0.0185 (2)
C6'	0.78367 (15)	−0.05107 (13)	0.12871 (10)	0.0240 (2)
H6'1	0.808590	−0.147414	0.171531	0.029*
H6'2	0.879139	−0.012801	0.135839	0.029*
C7'	0.78071 (18)	−0.06106 (14)	0.01023 (10)	0.0293 (3)
H7'1	0.686086	−0.098850	0.003246	0.044*
H7'2	0.894582	−0.124760	−0.017045	0.044*
H7'3	0.759557	0.033952	−0.032440	0.044*
C11'	0.05810 (15)	−0.00021 (12)	0.33152 (8)	0.0192 (2)
C12'	−0.05513 (16)	0.13969 (12)	0.31547 (10)	0.0238 (2)
H12'	−0.012250	0.212809	0.274291	0.029*
C13'	−0.23009 (16)	0.17204 (13)	0.35957 (10)	0.0263 (3)
H13'	−0.306704	0.267400	0.348484	0.032*
C14'	−0.29414 (16)	0.06579 (13)	0.41993 (10)	0.0248 (3)
H14'	−0.414184	0.088374	0.449939	0.030*
C15'	−0.18179 (16)	−0.07356 (13)	0.43617 (10)	0.0248 (2)
H15'	−0.225243	−0.146391	0.477316	0.030*
C16'	−0.00612 (16)	−0.10682 (12)	0.39246 (9)	0.0227 (2)
H16'	0.070371	−0.202176	0.404035	0.027*
O1'	0.61578 (11)	0.04083 (9)	0.17153 (7)	0.02334 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0236 (5)	0.0149 (5)	0.0175 (4)	−0.0067 (4)	−0.0006 (3)	−0.0030 (3)
N2	0.0221 (4)	0.0173 (5)	0.0173 (4)	−0.0064 (4)	−0.0009 (3)	−0.0029 (3)
C3	0.0169 (5)	0.0172 (5)	0.0179 (5)	−0.0059 (4)	0.0001 (4)	−0.0032 (4)
N4	0.0201 (4)	0.0162 (4)	0.0189 (4)	−0.0065 (4)	−0.0003 (3)	−0.0023 (3)
C5	0.0170 (5)	0.0151 (5)	0.0201 (5)	−0.0053 (4)	0.0003 (4)	−0.0025 (4)
C6	0.0223 (5)	0.0222 (6)	0.0169 (5)	−0.0072 (4)	−0.0023 (4)	−0.0017 (4)
C7	0.0237 (6)	0.0266 (6)	0.0224 (5)	−0.0088 (5)	0.0002 (4)	−0.0018 (4)
C11	0.0196 (5)	0.0177 (5)	0.0191 (5)	−0.0053 (4)	−0.0002 (4)	−0.0028 (4)
C12	0.0315 (6)	0.0178 (5)	0.0221 (5)	−0.0088 (5)	−0.0018 (4)	−0.0030 (4)
C13	0.0345 (6)	0.0185 (6)	0.0225 (6)	−0.0083 (5)	−0.0006 (5)	0.0008 (4)
C14	0.0310 (6)	0.0242 (6)	0.0180 (5)	−0.0065 (5)	−0.0024 (4)	−0.0016 (4)
C15	0.0426 (7)	0.0235 (6)	0.0232 (6)	−0.0133 (5)	−0.0065 (5)	−0.0040 (5)
C16	0.0364 (6)	0.0206 (6)	0.0224 (6)	−0.0132 (5)	−0.0038 (5)	−0.0008 (4)
O1	0.0254 (4)	0.0186 (4)	0.0173 (4)	−0.0088 (3)	−0.0012 (3)	−0.0034 (3)
N1'	0.0228 (5)	0.0154 (5)	0.0210 (4)	−0.0077 (4)	0.0003 (3)	−0.0028 (3)
N2'	0.0231 (5)	0.0182 (5)	0.0216 (4)	−0.0083 (4)	0.0004 (4)	−0.0030 (4)
C3'	0.0246 (5)	0.0181 (5)	0.0176 (5)	−0.0091 (4)	−0.0010 (4)	−0.0025 (4)
N4'	0.0249 (5)	0.0160 (5)	0.0188 (4)	−0.0079 (4)	−0.0006 (3)	−0.0026 (3)
C5'	0.0257 (5)	0.0145 (5)	0.0159 (5)	−0.0070 (4)	−0.0030 (4)	−0.0016 (4)
C6'	0.0232 (5)	0.0223 (6)	0.0267 (6)	−0.0088 (5)	0.0002 (4)	−0.0033 (4)
C7'	0.0347 (6)	0.0254 (6)	0.0260 (6)	−0.0094 (5)	0.0032 (5)	−0.0043 (5)
C11'	0.0239 (5)	0.0176 (5)	0.0170 (5)	−0.0074 (4)	−0.0026 (4)	−0.0030 (4)
C12'	0.0269 (6)	0.0173 (6)	0.0267 (6)	−0.0081 (5)	−0.0023 (4)	0.0000 (4)
C13'	0.0256 (6)	0.0186 (6)	0.0321 (6)	−0.0045 (5)	−0.0026 (5)	−0.0016 (5)
C14'	0.0231 (5)	0.0244 (6)	0.0257 (6)	−0.0073 (5)	0.0000 (4)	−0.0031 (5)
C15'	0.0291 (6)	0.0205 (6)	0.0247 (6)	−0.0107 (5)	0.0014 (4)	−0.0008 (4)
C16'	0.0273 (6)	0.0164 (5)	0.0232 (5)	−0.0063 (4)	−0.0011 (4)	−0.0017 (4)
O1'	0.0261 (4)	0.0192 (4)	0.0264 (4)	−0.0113 (3)	0.0036 (3)	−0.0049 (3)

Geometric parameters (Å, º) top

N1—C5	1.3372 (14)	N1'—C5'	1.3372 (14)
N1—N2	1.3739 (13)	N1'—N2'	1.3795 (13)
N1—H01	0.935 (17)	N1'—H01'	0.898 (17)
N2—C3	1.3176 (15)	N2'—C3'	1.3179 (15)
C3—O1	1.3399 (13)	C3'—O1'	1.3428 (14)
C3—N4	1.3610 (14)	C3'—N4'	1.3576 (15)
N4—C5	1.3418 (14)	N4'—C5'	1.3407 (15)
C5—C11	1.4670 (15)	C5'—C11'	1.4656 (15)
C6—O1	1.4537 (13)	C6'—O1'	1.4477 (14)
C6—C7	1.5092 (15)	C6'—C7'	1.5095 (17)
C6—H6A	0.9900	C6'—H6'1	0.9900
C6—H6B	0.9900	C6'—H6'2	0.9900
C7—H7A	0.9800	C7'—H7'1	0.9800
C7—H7B	0.9800	C7'—H7'2	0.9800
C7—H7C	0.9800	C7'—H7'3	0.9800
C11—C12	1.3940 (16)	C11'—C12'	1.3958 (16)
C11—C16	1.3949 (17)	C11'—C16'	1.3964 (16)
C12—C13	1.3921 (16)	C12'—C13'	1.3861 (17)
C12—H12	0.9500	C12'—H12'	0.9500
C13—C14	1.3857 (18)	C13'—C14'	1.3903 (17)
C13—H13	0.9500	C13'—H13'	0.9500
C14—C15	1.3864 (17)	C14'—C15'	1.3893 (17)
C14—H14	0.9500	C14'—H14'	0.9500
C15—C16	1.3892 (16)	C15'—C16'	1.3896 (17)
C15—H15	0.9500	C15'—H15'	0.9500
C16—H16	0.9500	C16'—H16'	0.9500

C5—N1—N2	110.54 (9)	C5'—N1'—N2'	110.63 (9)
C5—N1—H01	130.1 (10)	C5'—N1'—H01'	130.4 (10)
N2—N1—H01	119.4 (10)	N2'—N1'—H01'	118.8 (10)
C3—N2—N1	101.40 (9)	C3'—N2'—N1'	100.98 (9)
N2—C3—O1	124.72 (10)	N2'—C3'—O1'	125.44 (10)
N2—C3—N4	116.09 (10)	N2'—C3'—N4'	116.40 (10)
O1—C3—N4	119.19 (10)	O1'—C3'—N4'	118.16 (10)
C5—N4—C3	102.22 (9)	C5'—N4'—C3'	102.35 (9)
N1—C5—N4	109.75 (9)	N1'—C5'—N4'	109.64 (10)
N1—C5—C11	123.83 (10)	N1'—C5'—C11'	124.66 (10)
N4—C5—C11	126.40 (10)	N4'—C5'—C11'	125.69 (10)
O1—C6—C7	110.87 (9)	O1'—C6'—C7'	110.59 (10)
O1—C6—H6A	109.5	O1'—C6'—H6'1	109.5
C7—C6—H6A	109.5	C7'—C6'—H6'1	109.5
O1—C6—H6B	109.5	O1'—C6'—H6'2	109.5
C7—C6—H6B	109.5	C7'—C6'—H6'2	109.5
H6A—C6—H6B	108.1	H6'1—C6'—H6'2	108.1
C6—C7—H7A	109.5	C6'—C7'—H7'1	109.5
C6—C7—H7B	109.5	C6'—C7'—H7'2	109.5
H7A—C7—H7B	109.5	H7'1—C7'—H7'2	109.5
C6—C7—H7C	109.5	C6'—C7'—H7'3	109.5
H7A—C7—H7C	109.5	H7'1—C7'—H7'3	109.5
H7B—C7—H7C	109.5	H7'2—C7'—H7'3	109.5
C12—C11—C16	119.61 (10)	C12'—C11'—C16'	119.52 (11)
C12—C11—C5	120.15 (10)	C12'—C11'—C5'	119.52 (10)
C16—C11—C5	120.24 (10)	C16'—C11'—C5'	120.96 (10)
C13—C12—C11	119.94 (11)	C13'—C12'—C11'	120.06 (11)
C13—C12—H12	120.0	C13'—C12'—H12'	120.0
C11—C12—H12	120.0	C11'—C12'—H12'	120.0
C14—C13—C12	120.13 (11)	C12'—C13'—C14'	120.41 (11)
C14—C13—H13	119.9	C12'—C13'—H13'	119.8
C12—C13—H13	119.9	C14'—C13'—H13'	119.8
C13—C14—C15	120.14 (11)	C15'—C14'—C13'	119.69 (11)
C13—C14—H14	119.9	C15'—C14'—H14'	120.2
C15—C14—H14	119.9	C13'—C14'—H14'	120.2
C14—C15—C16	120.06 (12)	C14'—C15'—C16'	120.25 (11)
C14—C15—H15	120.0	C14'—C15'—H15'	119.9
C16—C15—H15	120.0	C16'—C15'—H15'	119.9
C15—C16—C11	120.12 (11)	C15'—C16'—C11'	120.06 (11)
C15—C16—H16	119.9	C15'—C16'—H16'	120.0
C11—C16—H16	119.9	C11'—C16'—H16'	120.0
C3—O1—C6	115.05 (9)	C3'—O1'—C6'	116.23 (9)

C5—N1—N2—C3	−0.12 (11)	C5'—N1'—N2'—C3'	0.07 (12)
N1—N2—C3—O1	179.17 (10)	N1'—N2'—C3'—O1'	179.42 (10)
N1—N2—C3—N4	−0.36 (12)	N1'—N2'—C3'—N4'	−0.15 (12)
N2—C3—N4—C5	0.68 (12)	N2'—C3'—N4'—C5'	0.17 (13)
O1—C3—N4—C5	−178.88 (9)	O1'—C3'—N4'—C5'	−179.43 (10)
N2—N1—C5—N4	0.55 (12)	N2'—N1'—C5'—N4'	0.03 (12)
N2—N1—C5—C11	−178.03 (9)	N2'—N1'—C5'—C11'	178.84 (10)
C3—N4—C5—N1	−0.70 (12)	C3'—N4'—C5'—N1'	−0.11 (12)
C3—N4—C5—C11	177.83 (10)	C3'—N4'—C5'—C11'	−178.90 (10)
N1—C5—C11—C12	−169.05 (11)	N1'—C5'—C11'—C12'	−159.54 (11)
N4—C5—C11—C12	12.60 (17)	N4'—C5'—C11'—C12'	19.07 (17)
N1—C5—C11—C16	10.20 (17)	N1'—C5'—C11'—C16'	20.26 (17)
N4—C5—C11—C16	−168.14 (11)	N4'—C5'—C11'—C16'	−161.13 (11)
C16—C11—C12—C13	−0.25 (18)	C16'—C11'—C12'—C13'	−0.19 (17)
C5—C11—C12—C13	179.02 (10)	C5'—C11'—C12'—C13'	179.61 (11)
C11—C12—C13—C14	0.28 (18)	C11'—C12'—C13'—C14'	−0.02 (19)
C12—C13—C14—C15	−0.25 (19)	C12'—C13'—C14'—C15'	0.09 (19)
C13—C14—C15—C16	0.2 (2)	C13'—C14'—C15'—C16'	0.07 (18)
C14—C15—C16—C11	−0.2 (2)	C14'—C15'—C16'—C11'	−0.28 (18)
C12—C11—C16—C15	0.18 (18)	C12'—C11'—C16'—C15'	0.34 (17)
C5—C11—C16—C15	−179.08 (11)	C5'—C11'—C16'—C15'	−179.46 (10)
N2—C3—O1—C6	−0.91 (15)	N2'—C3'—O1'—C6'	2.20 (16)
N4—C3—O1—C6	178.61 (9)	N4'—C3'—O1'—C6'	−178.24 (9)
C7—C6—O1—C3	−84.57 (11)	C7'—C6'—O1'—C3'	87.32 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···N4′	0.94 (2)	1.94 (2)	2.866 (1)	170 (1)
N1′—H01′···N4ⁱ	0.90 (2)	2.02 (2)	2.916 (1)	176 (1)
C13—H13···O1′ⁱⁱ	0.95	2.55	3.478 (2)	165
C15′—H15′···N2ⁱⁱⁱ	0.95	2.52	3.463 (2)	172

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

References

Abu-Zaied, M. A. & Elgemeie, G. H. (2017). Nucleosides Nucleotides Nucleic Acids, 36, 713–725. Web of Science CAS PubMed Google Scholar
Abu-Zaied, M. A. & Elgemeie, G. H. (2018). Nucleosides Nucleotides Nucleic Acids, 37, 67–77. Web of Science CAS PubMed Google Scholar
Azzam, R. A. & Elgemeie, G. H. (2019). Med. Chem. Res. 28, 62–70. Web of Science CrossRef CAS Google Scholar
Azzam, R. A., Elgemeie, G. H., Elsayed, R. E. & Jones, P. G. (2017b). Acta Cryst. E73, 1820–1822. Web of Science CSD CrossRef IUCr Journals Google Scholar
Azzam, R. A., Elgemeie, G. H., Osman, R. R. & Jones, P. G. (2019). Acta Cryst. E75, 367–371. Web of Science CSD CrossRef IUCr Journals Google Scholar
Azzam, R. A., Elgemeie, G. H., Ramadan, R. & Jones, P. G. (2017a). Acta Cryst. E73, 752–754. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brough, P., Gambarelli, S., Jacquot, J.-F., Grand, A., Pécaut, J. & Rey, P. (2011). Chem. Eur. J. 17, 11250–11257. Web of Science CSD CrossRef CAS PubMed Google Scholar
Buzykin, B. I., Mironova, E. V., Nabiullin, V. N., Gubaidullin, A. T. & Litvinov, I. A. (2006). Russ. J. Gen. Chem. 76, 1471–1486. Web of Science CrossRef CAS Google Scholar
Carlsen, P. H. J., Gautun, O. R., Samuelsen, E. J., Mårdalen, J., Helgesson, G. & Jagner, S. (1991). Phys. Scr. 44, 214–216. CrossRef CAS Web of Science Google Scholar
De Rosa, M., Arnold, D. & Yennawar, H. (2014). Tetrahedron Lett. 55, 5491–5494. Web of Science CSD CrossRef CAS Google Scholar
Dolzhenko, A. V., Tan, G. K., Koh, L. L., Dolzhenko, A. V. & Chui, W. K. (2009). Acta Cryst. E65, o126. Web of Science CSD CrossRef IUCr Journals Google Scholar
Elgemeie, G. H., Abou-Zeid, M., Alsaid, S., Hebishy, A. & Essa, H. (2015). Nucleosides Nucleotides Nucleic Acids, 34, 659–673. Web of Science CrossRef CAS PubMed Google Scholar
Elgemeie, G. H., Abu-Zaied, M. A. & Nawwar, G. H. (2018). Nucleosides Nucleotides Nucleic Acids, 37, 112–123. Web of Science CrossRef CAS PubMed Google Scholar
Elgemeie, G. H., Abu-Zaied, M. & Azzam, R. (2016). Nucleosides Nucleotides Nucleic Acids, 35, 211–222. Web of Science CrossRef CAS PubMed Google Scholar
Elgemeie, G. H., Altalbawy, F., Alfaidi, M., Azab, R. & Hassan, A. (2017). Drug Des. Dev. Ther. 11, 3389–3399. Web of Science CrossRef CAS Google Scholar
Elgemeie, G. H., El-Ezbawy, S. R. & Sood, S. A. (2003a). Synth. Commun. 33, 2095–2101. Web of Science CrossRef CAS Google Scholar
Elgemeie, G. H., Elghandour, A. H. & Abd Elaziz, G. W. (2003b). Synth. Commun. 33, 1659–1664. Web of Science CrossRef CAS Google Scholar
Elgemeie, G. H., Elsayed, S. H. & Hassan, A. S. (2009). Synth. Commun. 39, 1781–1792. Web of Science CrossRef CAS Google Scholar
Elgemeie, G. H., Elzanaty, A. M., Elghandour, A. H. & Ahmed, S. A. (2006). Synth. Commun. 36, 825–834. Web of Science CrossRef CAS Google Scholar
Elgemeie, G. H., Fathy, N., Zaghary, W. & Farag, A. (2017c). Nucleosides Nucleotides Nucleic Acids, 36, 198–212. Web of Science CrossRef CAS PubMed Google Scholar
Elgemeie, G. H., Salah, A. M., Abbas, N. S., Hussein, H. A. & Mohamed, R. A. (2017d). Nucleosides Nucleotides Nucleic Acids, 36, 213–223. Web of Science CrossRef CAS PubMed Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Othman, R. Ben , Marchivie, M., Suzenet, F. & Routier, S. (2014b). Acta Cryst. E70, o622--o623. Google Scholar
Othman, R., Massip, S., Marchivie, M., Jarry, C., Vercouillie, J., Chalon, S., Guillaumet, G., Suzenet, F. & Routier, S. (2014b). Eur. J. Org. Chem. pp. 3225–3231. Web of Science CSD CrossRef Google Scholar
Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Siemens (1994). XP. Siemens Analytical X-Ray Instruments, Madison, Wisconsin, USA. Google Scholar
Sudheendran, K., Schmidt, D., Frey, W., Conrad, J. & Beifuss, U. (2014). Tetrahedron, 70, 1635–1645. Web of Science CSD CrossRef CAS Google Scholar
Zhu, A.-X., Liu, J.-N., Li, Z., Wang, H.-C. & Du, Y.-C. (2011). Acta Cryst. E67, o1208. Web of Science CSD CrossRef IUCr Journals Google Scholar

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