Crystal structure of ethyl 2-{4-[(2-oxo-3-phenyl-1,2-di­hydro­quinoxalin-1-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate

Nadeem Abad; Mohcine Missioui; Abdulsalam Alsubari; Joel T Mague; El Mokhtar Essassi; Youssef Ramli

doi:10.1107/S2414314622006939

. 2022 Jul 14;7(Pt 7):0. doi: 10.1107/S2414314622006939

Crystal structure of ethyl 2-{4-[(2-oxo-3-phenyl-1,2-dihydroquinoxalin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}acetate

Nadeem Abad ^a,^b, Mohcine Missioui ^a, Abdulsalam Alsubari ^c,^*, Joel T Mague ^d, El Mokhtar Essassi ^b, Youssef Ramli ^a,^‡

Editor: I Brito^e

PMCID: PMC9635411 PMID: 36341047

The quinoxaline portion of the title molecule is not quite planar and the conformation of the entire molecule is ‘U-shaped’, which is consolidated by an intramolecular antiparallel carbonyl electrostatic interaction. In the crystal, the molecules form corrugated layers through C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π(ring) and π-stacking interactions.

Keywords: crystal structure, quinoxaline, triazole, hydrogen bond, π-stacking

Abstract

The quinoxaline portion of the title molecule, C₂₁H₁₉N₅O₃, is not quite planar as indicated by a dihedral angle of 3.38 (7)° between the constituent rings. The molecule is ‘U-shaped’, which is consolidated by an intramolecular antiparallel carbonyl electrostatic interaction with C··O distances of 2.8905 (16) and 3.0221 (15) Å, in the crystal forms corrugated layers through C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π(ring) and π-stacking interactions.

Structure description

Quinoxaline derivatives exhibit a wide range of biological applications including antimicrobial (Teja et al., 2016 ▸), anti-inflammatory (Guirado et al., 2012 ▸), anticancer (Abbas et al., 2015 ▸), antidiabetic (Kulkarni et al., 2012 ▸) and antihistaminic (Sridevi et al., 2010 ▸) effects. As a continuation of our research on the synthesis and biological properties of quinoxaline derivatives (Missioui et al., 2022a ▸,b ▸,c ▸), the title compound (Fig. 1 ▸) was prepared and its crystal structure is reported here.

The title molecule with the labeling scheme and 50% probability ellipsoids. The π interaction between the C19=O2 carbonyl group and the C1/C6/N1/C7/C8/N2 ring is shown by an orange dashed line.

The quinoxaline portion is not quite planar as indicated by a dihedral angle of 3.38 (7)° between the constituent rings. The dihedral angle between the C9–C14 and C1/C6/N1/C7/C8/N2 rings is 9.05 (8)° while that between the latter ring and the triazole ring is 78.47 (3)°. The molecule adopts a ‘U-shaped’ conformation, which is consolidated by an intramolecular antiparallel carbonyl electrostatic interaction (Allen et al., 1998 ▸) between the C8=O1 and C19=O2 groups with C19⋯O1 = 2.890 Å and C8⋯O2 = 3.022 Å. In the crystal, C12—H12⋯N3 hydrogen bonds (Table 1 ▸) lead to the formation of chains extending along the c-axis direction, which are linked into corrugated layers by C5—H5⋯N4 and C15—H15B⋯O2 hydrogen bonds and by C15—15A⋯Cg1 interactions (Table 1 ▸ and Fig. 2 ▸). These are accompanied by weak π-stacking interactions between C1/C6/N1/C7/C8/N2 and C1–C6 rings related by the symmetry operation x − Inline graphic , y, −z − [centroid–centroid distance = 3.8105 (7) Å, dihedral angle = 6.13 (6)°].

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the triazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N4ⁱ	0.973 (16)	2.462 (16)	3.2183 (17)	134.3 (12)
C12—H12⋯N3ⁱⁱ	0.988 (19)	2.572 (19)	3.4094 (18)	142.5 (15)
C15—H15A⋯Cg1ⁱⁱⁱ	0.997 (16)	2.657 (15)	3.3580 (14)	127.5 (10)
C15—H15B⋯O2^iv	0.986 (15)	2.464 (15)	3.2459 (16)	135.9 (11)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Packing viewed along the a-axis direction. C—H⋯O and C—H⋯N hydrogen bonds are shown, respectively, by black and light-blue dashed lines while the π-stacking interactions are shown by orange dashed lines.

Synthesis and crystallization

To a solution of 3-phenyl-1-(prop-2-yn-1-yl)quinoxalin-2(1H)-one (0.68 mmol) in ethanol (15 ml) was added ethyl 2-azidoacetate (1.03 mmol). The reaction mixture was stirred under reflux for 72 h. After completion of the reaction (monitored by TLC), the solution was concentrated and the residue was purified by column chromatography on silica gel by using a hexane/ethyl acetate mixture (9:1) as eluent. The solid product obtained was crystallized from ethanol solution to afford colorless crystals. Yield 80%, m.p. = 408–410 K. ¹H MNR (300 MHz, CDCl₃) δ (p.p.m.):1.22–1.26 (t, 3H, CH₃, J = 6 Hz); 4.12-4.19 (q, 2H, O—CH₂, J = 6 Hz); 5.57 (s, 2H, N—CH₂CO₂); 5.60 (s, 2H, N—CH₂); 7.72 (s, H,CH_triazole); 7.44–8.31 (m, 9H_arom); ¹³C MNR (75 MHz,CDCl₃) δ (p.p.m.):13.95 (CH₃); 34.99 (O—CH₂); 50.01(N—CH₂C=O); 62.48 (N—CH₂); 113.48, 124.61, 128.19 (traizole), 129.52, 130.70, 130.85, 131.16, 131.79, (CH_arom); 132.79, 133.53, 134.34, 135.52, 153.69 (C_q); 154.32 (C=O_arom);166.80 (C=O_acetate)

Refinement

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

Table 2. Experimental details.

Crystal data
Chemical formula	C₂₁H₁₉N₅O₃
M _r	389.41
Crystal system, space group	Orthorhombic, P b c a
Temperature (K)	150
a, b, c (Å)	8.8585 (3), 18.0405 (5), 23.1961 (7)
V (Å³)	3707.0 (2)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	0.79
Crystal size (mm)	0.21 × 0.10 × 0.02

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 ▸)
T _min, T _max	0.89, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	26694, 3662, 3086
R _int	0.047
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F ² > 2σ(F ²)], wR(F ²), S	0.035, 0.087, 1.05
No. of reflections	3662
No. of parameters	339
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

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Computer programs: APEX3 and SAINT (Bruker, 2016 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL2018/1 (Sheldrick, 2015b ▸), DIAMOND (Brandenburg & Putz, 2012 ▸) and SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2414314622006939/bx4022sup1.cif

x-07-00000-sup1.cif^{(839.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314622006939/bx4022Isup2.hkl

x-07-00000-Isup2.hkl^{(292.5KB, hkl)}

Click here for additional data file.^{(6.9KB, cml)}

Supporting information file. DOI: 10.1107/S2414314622006939/bx4022Isup3.cml

CCDC reference: 2184531

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

Author contributions are as follows. Conceptualization, YR and NA; methodology, MM and AS; investigation, NA and MM; writing (original draft), JTM and YR; writing (review and editing of the manuscript), YR; formal analysis, AA and YR; supervision, YR and EME; crystal-structure determination and validation, JTM; synthesis, NA.

full crystallographic data

Crystal data

C₂₁H₁₉N₅O₃	D_x = 1.395 Mg m⁻³
M_r = 389.41	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbca	Cell parameters from 9932 reflections
a = 8.8585 (3) Å	θ = 3.8–72.3°
b = 18.0405 (5) Å	µ = 0.79 mm⁻¹
c = 23.1961 (7) Å	T = 150 K
V = 3707.0 (2) Å³	Plate, colourless
Z = 8	0.21 × 0.10 × 0.02 mm
F(000) = 1632

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Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3662 independent reflections
Radiation source: INCOATEC IµS micro–focus source	3086 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.047
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.5°, θ_min = 3.8°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −22→22
T_min = 0.89, T_max = 0.98	l = −28→27
26694 measured reflections

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Refinement

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	All H-atom parameters refined
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0384P)² + 1.2273P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3662 reflections	Δρ_max = 0.24 e Å⁻³
339 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL 2018/1 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00064 (5)

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Special details

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. 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 > 2sigma(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.All H atom positional and Uiso values were freely refined.

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

	x	y	z	U_iso*/U_eq
O1	0.43111 (11)	0.52576 (5)	0.37440 (4)	0.0275 (2)
O2	0.09359 (10)	0.46632 (5)	0.36206 (4)	0.0270 (2)
O3	0.20937 (11)	0.40033 (5)	0.43166 (4)	0.0303 (2)
N1	0.18289 (12)	0.67590 (6)	0.34317 (5)	0.0226 (2)
N2	0.34767 (11)	0.56638 (5)	0.28730 (4)	0.0193 (2)
N3	0.16535 (13)	0.36820 (6)	0.19501 (5)	0.0252 (2)
N4	0.16515 (13)	0.34789 (6)	0.24943 (5)	0.0250 (2)
N5	0.26117 (12)	0.39291 (6)	0.27772 (5)	0.0208 (2)
C1	0.26318 (14)	0.61609 (6)	0.25427 (5)	0.0195 (3)
C2	0.26183 (16)	0.61555 (7)	0.19390 (6)	0.0238 (3)
H2	0.3228 (19)	0.5802 (9)	0.1724 (7)	0.034 (4)*
C3	0.17264 (16)	0.66602 (7)	0.16465 (6)	0.0264 (3)
H3	0.1743 (18)	0.6650 (9)	0.1222 (7)	0.033 (4)*
C4	0.08259 (16)	0.71695 (7)	0.19408 (6)	0.0260 (3)
H4	0.0164 (19)	0.7523 (9)	0.1731 (7)	0.034 (4)*
C5	0.08467 (15)	0.71842 (7)	0.25326 (6)	0.0236 (3)
H5	0.0237 (18)	0.7530 (9)	0.2755 (7)	0.031 (4)*
C6	0.17717 (14)	0.66902 (7)	0.28405 (5)	0.0207 (3)
C7	0.26837 (14)	0.63234 (7)	0.37345 (5)	0.0211 (3)
C8	0.35681 (14)	0.57104 (7)	0.34670 (5)	0.0208 (3)
C9	0.27185 (16)	0.64586 (7)	0.43697 (6)	0.0248 (3)
C10	0.1715 (2)	0.69806 (8)	0.45951 (6)	0.0356 (3)
H10	0.101 (2)	0.7214 (11)	0.4333 (8)	0.053 (6)*
C11	0.1707 (2)	0.71453 (9)	0.51787 (7)	0.0435 (4)
H11	0.098 (2)	0.7522 (12)	0.5330 (9)	0.062 (6)*
C12	0.2704 (2)	0.67988 (9)	0.55500 (6)	0.0408 (4)
H12	0.268 (2)	0.6896 (11)	0.5969 (8)	0.050 (5)*
C13	0.3689 (2)	0.62824 (10)	0.53366 (7)	0.0434 (4)
H13	0.442 (2)	0.6034 (12)	0.5596 (9)	0.063 (6)*
C14	0.37072 (19)	0.61077 (9)	0.47502 (7)	0.0369 (4)
H14	0.443 (2)	0.5717 (11)	0.4606 (8)	0.051 (5)*
C15	0.42864 (14)	0.50430 (7)	0.25935 (6)	0.0206 (3)
H15A	0.5028 (17)	0.4856 (8)	0.2882 (6)	0.025 (4)*
H15B	0.4831 (17)	0.5225 (8)	0.2251 (6)	0.022 (4)*
C16	0.32363 (14)	0.44361 (6)	0.24135 (5)	0.0191 (3)
H16	0.2784 (19)	0.4473 (9)	0.1516 (7)	0.036 (4)*
C17	0.26194 (15)	0.42622 (7)	0.18895 (6)	0.0226 (3)
C18	0.28965 (15)	0.37793 (7)	0.33815 (6)	0.0232 (3)
H18A	0.3932 (19)	0.3894 (9)	0.3470 (7)	0.030 (4)*
H18B	0.2764 (17)	0.3237 (9)	0.3441 (6)	0.026 (4)*
C19	0.18500 (14)	0.42063 (7)	0.37736 (5)	0.0221 (3)
C20	0.11923 (18)	0.43913 (9)	0.47469 (6)	0.0329 (3)
H20A	0.1346 (19)	0.4932 (10)	0.4678 (7)	0.036 (4)*
H20B	0.0111 (19)	0.4247 (9)	0.4681 (7)	0.032 (4)*
C21	0.1730 (2)	0.41458 (12)	0.53292 (7)	0.0456 (4)
H21A	0.165 (2)	0.3587 (12)	0.5382 (9)	0.062 (6)*
H21B	0.111 (2)	0.4381 (11)	0.5639 (9)	0.057 (6)*
H21C	0.277 (2)	0.4295 (11)	0.5392 (8)	0.052 (6)*

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Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0328 (5)	0.0238 (5)	0.0258 (5)	0.0042 (4)	−0.0065 (4)	0.0000 (4)
O2	0.0241 (5)	0.0317 (5)	0.0251 (5)	0.0058 (4)	−0.0013 (4)	0.0000 (4)
O3	0.0350 (5)	0.0339 (5)	0.0219 (5)	0.0116 (4)	0.0037 (4)	0.0036 (4)
N1	0.0247 (5)	0.0210 (5)	0.0222 (5)	0.0002 (4)	−0.0005 (5)	−0.0029 (4)
N2	0.0204 (5)	0.0169 (5)	0.0204 (5)	−0.0001 (4)	−0.0007 (4)	−0.0021 (4)
N3	0.0228 (6)	0.0248 (6)	0.0280 (6)	0.0015 (4)	−0.0014 (5)	−0.0069 (4)
N4	0.0232 (5)	0.0218 (5)	0.0301 (6)	−0.0013 (4)	−0.0003 (5)	−0.0062 (4)
N5	0.0212 (5)	0.0189 (5)	0.0224 (5)	−0.0007 (4)	0.0010 (4)	−0.0026 (4)
C1	0.0197 (6)	0.0167 (5)	0.0222 (6)	−0.0030 (5)	−0.0013 (5)	0.0005 (5)
C2	0.0270 (7)	0.0221 (6)	0.0223 (6)	−0.0021 (5)	0.0022 (5)	−0.0002 (5)
C3	0.0328 (7)	0.0249 (6)	0.0215 (7)	−0.0052 (6)	−0.0021 (6)	0.0031 (5)
C4	0.0280 (7)	0.0198 (6)	0.0302 (7)	−0.0029 (5)	−0.0068 (6)	0.0041 (5)
C5	0.0230 (6)	0.0184 (6)	0.0295 (7)	−0.0002 (5)	−0.0029 (5)	−0.0013 (5)
C6	0.0219 (6)	0.0185 (6)	0.0216 (6)	−0.0028 (5)	−0.0010 (5)	−0.0014 (5)
C7	0.0231 (6)	0.0189 (6)	0.0213 (6)	−0.0031 (5)	−0.0003 (5)	−0.0013 (5)
C8	0.0217 (6)	0.0195 (6)	0.0213 (6)	−0.0032 (5)	−0.0016 (5)	−0.0012 (5)
C9	0.0306 (7)	0.0215 (6)	0.0225 (7)	−0.0046 (5)	−0.0001 (6)	−0.0022 (5)
C10	0.0537 (10)	0.0285 (7)	0.0246 (7)	0.0063 (7)	0.0022 (7)	−0.0013 (6)
C11	0.0717 (12)	0.0329 (8)	0.0260 (8)	0.0098 (8)	0.0073 (8)	−0.0043 (6)
C12	0.0684 (12)	0.0340 (8)	0.0201 (7)	−0.0059 (8)	0.0021 (7)	−0.0038 (6)
C13	0.0540 (10)	0.0499 (10)	0.0263 (8)	0.0030 (8)	−0.0102 (7)	−0.0036 (7)
C14	0.0395 (8)	0.0450 (9)	0.0263 (8)	0.0067 (7)	−0.0072 (6)	−0.0068 (6)
C15	0.0179 (6)	0.0198 (6)	0.0241 (6)	0.0009 (5)	0.0017 (5)	−0.0031 (5)
C16	0.0173 (5)	0.0178 (5)	0.0222 (6)	0.0026 (5)	0.0025 (5)	−0.0024 (5)
C17	0.0211 (6)	0.0240 (6)	0.0226 (6)	0.0029 (5)	0.0008 (5)	−0.0044 (5)
C18	0.0251 (7)	0.0219 (6)	0.0226 (7)	0.0024 (5)	0.0014 (5)	0.0008 (5)
C19	0.0219 (6)	0.0232 (6)	0.0212 (6)	−0.0020 (5)	0.0006 (5)	0.0004 (5)
C20	0.0366 (8)	0.0404 (8)	0.0218 (7)	0.0107 (7)	0.0051 (6)	0.0006 (6)
C21	0.0474 (10)	0.0652 (12)	0.0241 (8)	0.0154 (9)	0.0001 (7)	0.0041 (7)

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Geometric parameters (Å, º)

O1—C8	1.2301 (16)	C9—C14	1.395 (2)
O2—C19	1.2088 (16)	C9—C10	1.397 (2)
O3—C19	1.3293 (16)	C10—C11	1.386 (2)
O3—C20	1.4574 (17)	C10—H10	0.97 (2)
N1—C7	1.2978 (17)	C11—C12	1.383 (2)
N1—C6	1.3780 (16)	C11—H11	1.00 (2)
N2—C8	1.3827 (16)	C12—C13	1.369 (2)
N2—C1	1.3970 (16)	C12—H12	0.988 (19)
N2—C15	1.4797 (15)	C13—C14	1.396 (2)
N3—N4	1.3144 (16)	C13—H13	0.99 (2)
N3—C17	1.3592 (18)	C14—H14	1.01 (2)
N4—N5	1.3468 (15)	C15—C16	1.4962 (17)
N5—C16	1.3618 (16)	C15—H15A	0.997 (16)
N5—C18	1.4497 (17)	C15—H15B	0.986 (15)
C1—C2	1.4005 (18)	C16—C17	1.3691 (18)
C1—C6	1.4034 (17)	C17—H16	0.957 (17)
C2—C3	1.3832 (19)	C18—C19	1.5100 (18)
C2—H2	0.974 (17)	C18—H18A	0.963 (17)
C3—C4	1.395 (2)	C18—H18B	0.995 (16)
C3—H3	0.984 (16)	C20—C21	1.499 (2)
C4—C5	1.3732 (19)	C20—H20A	0.997 (18)
C4—H4	0.994 (17)	C20—H20B	1.005 (17)
C5—C6	1.4055 (18)	C21—H21A	1.02 (2)
C5—H5	0.973 (16)	C21—H21B	1.00 (2)
C7—C8	1.4905 (17)	C21—H21C	0.97 (2)
C7—C9	1.4937 (17)

C19—O3—C20	115.32 (11)	C13—C12—C11	119.30 (14)
C7—N1—C6	120.37 (11)	C13—C12—H12	119.4 (11)
C8—N2—C1	122.62 (10)	C11—C12—H12	121.2 (11)
C8—N2—C15	117.02 (10)	C12—C13—C14	120.87 (16)
C1—N2—C15	120.34 (10)	C12—C13—H13	120.3 (12)
N4—N3—C17	108.35 (11)	C14—C13—H13	118.8 (12)
N3—N4—N5	107.40 (10)	C9—C14—C13	120.44 (15)
N4—N5—C16	111.08 (10)	C9—C14—H14	120.3 (11)
N4—N5—C18	117.95 (10)	C13—C14—H14	119.2 (11)
C16—N5—C18	130.82 (11)	N2—C15—C16	112.02 (10)
N2—C1—C2	123.27 (11)	N2—C15—H15A	106.4 (9)
N2—C1—C6	117.23 (11)	C16—C15—H15A	110.4 (9)
C2—C1—C6	119.49 (12)	N2—C15—H15B	109.8 (8)
C3—C2—C1	119.38 (12)	C16—C15—H15B	108.9 (8)
C3—C2—H2	119.8 (10)	H15A—C15—H15B	109.3 (12)
C1—C2—H2	120.8 (10)	N5—C16—C17	103.54 (11)
C2—C3—C4	121.35 (12)	N5—C16—C15	124.84 (11)
C2—C3—H3	118.0 (10)	C17—C16—C15	131.57 (12)
C4—C3—H3	120.7 (10)	N3—C17—C16	109.62 (12)
C5—C4—C3	119.61 (12)	N3—C17—H16	119.7 (10)
C5—C4—H4	119.1 (10)	C16—C17—H16	130.7 (10)
C3—C4—H4	121.3 (10)	N5—C18—C19	112.36 (11)
C4—C5—C6	120.24 (12)	N5—C18—H18A	109.3 (10)
C4—C5—H5	122.3 (9)	C19—C18—H18A	110.3 (10)
C6—C5—H5	117.4 (9)	N5—C18—H18B	107.3 (9)
N1—C6—C1	122.08 (11)	C19—C18—H18B	110.2 (9)
N1—C6—C5	118.04 (11)	H18A—C18—H18B	107.1 (13)
C1—C6—C5	119.86 (12)	O2—C19—O3	125.10 (12)
N1—C7—C8	122.05 (11)	O2—C19—C18	125.61 (12)
N1—C7—C9	116.55 (11)	O3—C19—C18	109.29 (11)
C8—C7—C9	121.40 (11)	O3—C20—C21	107.51 (13)
O1—C8—N2	120.76 (12)	O3—C20—H20A	106.6 (10)
O1—C8—C7	123.81 (12)	C21—C20—H20A	112.9 (10)
N2—C8—C7	115.41 (11)	O3—C20—H20B	107.1 (9)
C14—C9—C10	117.95 (13)	C21—C20—H20B	111.4 (9)
C14—C9—C7	124.25 (13)	H20A—C20—H20B	111.0 (14)
C10—C9—C7	117.79 (12)	C20—C21—H21A	112.3 (12)
C11—C10—C9	120.89 (15)	C20—C21—H21B	110.4 (12)
C11—C10—H10	121.1 (12)	H21A—C21—H21B	107.3 (16)
C9—C10—H10	118.0 (12)	C20—C21—H21C	110.8 (12)
C12—C11—C10	120.55 (16)	H21A—C21—H21C	108.7 (17)
C12—C11—H11	120.0 (12)	H21B—C21—H21C	107.2 (16)
C10—C11—H11	119.4 (12)

C17—N3—N4—N5	0.03 (14)	N1—C7—C9—C14	−171.75 (14)
N3—N4—N5—C16	0.56 (13)	C8—C7—C9—C14	9.3 (2)
N3—N4—N5—C18	−175.36 (10)	N1—C7—C9—C10	6.99 (18)
C8—N2—C1—C2	175.04 (12)	C8—C7—C9—C10	−172.00 (13)
C15—N2—C1—C2	−6.76 (18)	C14—C9—C10—C11	0.2 (2)
C8—N2—C1—C6	−4.48 (17)	C7—C9—C10—C11	−178.63 (15)
C15—N2—C1—C6	173.72 (11)	C9—C10—C11—C12	0.5 (3)
N2—C1—C2—C3	178.84 (12)	C10—C11—C12—C13	−0.9 (3)
C6—C1—C2—C3	−1.65 (19)	C11—C12—C13—C14	0.6 (3)
C1—C2—C3—C4	−0.7 (2)	C10—C9—C14—C13	−0.5 (2)
C2—C3—C4—C5	1.5 (2)	C7—C9—C14—C13	178.27 (15)
C3—C4—C5—C6	0.1 (2)	C12—C13—C14—C9	0.1 (3)
C7—N1—C6—C1	−0.69 (19)	C8—N2—C15—C16	103.20 (13)
C7—N1—C6—C5	−178.96 (12)	C1—N2—C15—C16	−75.10 (14)
N2—C1—C6—N1	4.56 (18)	N4—N5—C16—C17	−0.90 (13)
C2—C1—C6—N1	−174.98 (12)	C18—N5—C16—C17	174.34 (12)
N2—C1—C6—C5	−177.20 (11)	N4—N5—C16—C15	176.59 (11)
C2—C1—C6—C5	3.26 (18)	C18—N5—C16—C15	−8.2 (2)
C4—C5—C6—N1	175.80 (12)	N2—C15—C16—N5	−76.76 (15)
C4—C5—C6—C1	−2.51 (19)	N2—C15—C16—C17	99.98 (15)
C6—N1—C7—C8	−3.34 (18)	N4—N3—C17—C16	−0.61 (14)
C6—N1—C7—C9	177.67 (11)	N5—C16—C17—N3	0.91 (13)
C1—N2—C8—O1	179.23 (11)	C15—C16—C17—N3	−176.34 (12)
C15—N2—C8—O1	0.97 (17)	N4—N5—C18—C19	−92.47 (13)
C1—N2—C8—C7	0.80 (17)	C16—N5—C18—C19	92.57 (15)
C15—N2—C8—C7	−177.45 (10)	C20—O3—C19—O2	−1.8 (2)
N1—C7—C8—O1	−175.08 (12)	C20—O3—C19—C18	178.01 (12)
C9—C7—C8—O1	3.85 (19)	N5—C18—C19—O2	−4.81 (19)
N1—C7—C8—N2	3.29 (18)	N5—C18—C19—O3	175.42 (10)
C9—C7—C8—N2	−177.78 (11)	C19—O3—C20—C21	−174.39 (14)

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Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the triazole ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N4ⁱ	0.973 (16)	2.462 (16)	3.2183 (17)	134.3 (12)
C12—H12···N3ⁱⁱ	0.988 (19)	2.572 (19)	3.4094 (18)	142.5 (15)
C15—H15A···Cg1ⁱⁱⁱ	0.997 (16)	2.657 (15)	3.3580 (14)	127.5 (10)
C15—H15B···O2^iv	0.986 (15)	2.464 (15)	3.2459 (16)	135.9 (11)

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

Funding Statement

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

Abbas, H. S., Al-Marhabi, A. R., Eissa, S. I. & Ammar, Y. A. (2015). Bioorg. Med. Chem. 23, 6560–6572. [DOI] [PubMed]
Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329.
Brandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany.
Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Guirado, A., López Sánchez, J. I., Ruiz-Alcaraz, A. J., Bautista, D. & Gálvez, J. (2012). Eur. J. Med. Chem. 54, 87–94. [DOI] [PubMed]
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. [DOI] [PMC free article] [PubMed]
Kulkarni, N. V., Revankar, V. K., Kirasur, B. N. & Hugar, M. H. (2012). Med. Chem. Res. 21, 663–671.
Missioui, M., Lgaz, H., Guerrab, W., Lee, H., Warad, I., Mague, J. T., Ali, I. H., Essassi, E. M. & Ramli, Y. (2022a). J. Mol. Struct. 1253, 132132–143.
Missioui, M., Said, M. A., Demirtaş, G., Mague, J. T., Al-Sulami, A., Al-Kaff, N. S. & Ramli, Y. (2022b). Arab. J. Chem. 15, 103595–613. [DOI] [PMC free article] [PubMed]
Missioui, M., Said, M. A., Demirtaş, G., Mague, J. T. & Ramli, Y. (2022c). J. Mol. Struct. 1247, 131420–433.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
Sridevi, K. B. C. H., Naidu, A. & Sudhakaran, R. (2010). Eur. J. Chem. 7, 234–238.
Teja, R., Kapu, S., Kadiyala, S., Dhanapal, V. & Raman, A. N. (2016). J. Saudi Chem. Soc. 20, S387–S392.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2414314622006939/bx4022sup1.cif

x-07-00000-sup1.cif^{(839.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314622006939/bx4022Isup2.hkl

x-07-00000-Isup2.hkl^{(292.5KB, hkl)}

Click here for additional data file.^{(6.9KB, cml)}

Supporting information file. DOI: 10.1107/S2414314622006939/bx4022Isup3.cml

CCDC reference: 2184531

Additional supporting information: crystallographic information; 3D view; checkCIF report

[bb3] Abbas, H. S., Al-Marhabi, A. R., Eissa, S. I. & Ammar, Y. A. (2015). Bioorg. Med. Chem. 23, 6560–6572. [DOI] [PubMed]

[bb1] Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329.

[bb5] Brandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany.

[bb6] Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

[bb7] Guirado, A., López Sánchez, J. I., Ruiz-Alcaraz, A. J., Bautista, D. & Gálvez, J. (2012). Eur. J. Med. Chem. 54, 87–94. [DOI] [PubMed]

[bb8] Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. [DOI] [PMC free article] [PubMed]

[bb9] Kulkarni, N. V., Revankar, V. K., Kirasur, B. N. & Hugar, M. H. (2012). Med. Chem. Res. 21, 663–671.

[bb11] Missioui, M., Lgaz, H., Guerrab, W., Lee, H., Warad, I., Mague, J. T., Ali, I. H., Essassi, E. M. & Ramli, Y. (2022a). J. Mol. Struct. 1253, 132132–143.

[bb13] Missioui, M., Said, M. A., Demirtaş, G., Mague, J. T., Al-Sulami, A., Al-Kaff, N. S. & Ramli, Y. (2022b). Arab. J. Chem. 15, 103595–613. [DOI] [PMC free article] [PubMed]

[bb14] Missioui, M., Said, M. A., Demirtaş, G., Mague, J. T. & Ramli, Y. (2022c). J. Mol. Struct. 1247, 131420–433.

[bb18] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb19] Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.

[bb20] Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.

[bb21] Sridevi, K. B. C. H., Naidu, A. & Sudhakaran, R. (2010). Eur. J. Chem. 7, 234–238.

[bb22] Teja, R., Kapu, S., Kadiyala, S., Dhanapal, V. & Raman, A. N. (2016). J. Saudi Chem. Soc. 20, S387–S392.

PERMALINK

Crystal structure of ethyl 2-{4-[(2-oxo-3-phenyl-1,2-dihydroquinoxalin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}acetate

Nadeem Abad

Mohcine Missioui

Abdulsalam Alsubari

Joel T Mague

El Mokhtar Essassi

Youssef Ramli

Roles

Abstract

Structure description