Ethyl 2-(2-oxo-3-phenyl-1,2-di­hydro­quinoxalin-1-yl)acetate

Abad, N.; El Bakri, Y.; Sebhaoui, J.; Ramli, Y.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314618005199

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 4| April 2018| x180519

https://doi.org/10.1107/S2414314618005199

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Ethyl 2-(2-oxo-3-phenyl-1,2-dihydroquinoxalin-1-yl)acetate

Nadeem Abad,^a ^* Youness El Bakri,^a Jihad Sebhaoui,^a Youssef Ramli,^b El Mokhtar Essassi ^a and Joel T. Mague ^c

^aLaboratoire de Chimie Organique Hétérocyclique, Centre de Recherche des Sciences des Médicaments, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, ^bLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, University Mohammed V, Rabat, Morocco, and ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: ab.nadeem2018@gmail.com

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 30 March 2018; accepted 2 April 2018; online 6 April 2018)

In the title compound, C₁₈H₁₆N₂O₃, the dihydroquinoxaline moiety is planar (r.m.s. deviation = 0.0115 Å) and the majority of the ester substituent is nearly perpendicular to its mean plane. In the crystal, the molecules form oblique stacks along the b-axis direction through slipped π–π stacking interactions between adjacent dihydroquinoxaline units. C—H⋯O hydrogen bonds between the ester substituents on adjacent stacks form thick layers with the stacks on their outside surfaces. These layers extend along the c-axis direction and are coupled through C—H⋯π(ring) interactions. The structure was refined as a two-component twin.

Keywords: crystal structure; hydrogen bond; π-stacking; dihydroquinoxaline.

CCDC reference: 1834198

Structure description

Quinoxaline derivatives are important compounds in medicinal chemistry possessing a wide variety of biological properties such as anticancer (Abbas et al., 2015 ; Ingle et al., 2013 ), antimicrobial (Attia et al., 2013 ; Vieira et al., 2014 ; Teja et al., 2016 ), anti-inflammatory (Guirado et al., 2012 ; Burguete et al., 2001 ), antidepressant (Mahesh et al., 2011 ), antiviral (Henen et al., 2012 ; El-Tombary & El-Hawash, 2014 ), antidiabetic (Kulkarni et al., 2012 ), antihypertensive (Gupta et al., 2011 ) and antihistaminic activities (Sridevi et al., 2010 ). In addition, it has been reported that the quinoxaline moiety is also an integral part of natural and synthetic antibiotics such as triostin A and echinomycin, known to inhibit the growth of Gram positive bacteria. As a continuation of our studies of quinoxaline derivatives (Ramli et al., 2018 ), we report the synthesis and structure of the title compound (Fig. 1).

Figure 1
The title molecule with labelling scheme and 50% probability ellipsoids.

The dihydroquinoxaline moiety is planar to within 0.0221 (13) Å (r.m.s. deviation = 0.0115 Å). The pendant phenyl ring is inclined to this plane by 19.63 (7)°, while the N2/C15/C16/C17/O2/O3 unit, which is planar to within 0.0078 (16) Å (r.m.s. deviation = 0.005 Å), is inclined by 88.62 (7)°. In the crystal, the molecules form oblique stacks along the b-axis direction through slipped π–π-stacking interactions between the C1–C6 and C1/C6/N1/C7/C8/N2 rings with centroid–centroid separations of 3.8364 (10) Å. This is reinforced by C2—H2⋯O2 hydrogen bonds. Adjacent stacks are associated by C17—H17B⋯O2 and C18—H18B⋯O3 interactions, forming thick layers extending along the c-axis direction (Table 1 and Fig. 2). Finally, these layers are `stitched' together by a series of C12—H12⋯Cg3 interactions (Table 1 and Fig. 3; Cg3 is the centroid of ring C9–C14).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.97 (2)	2.46 (2)	3.345 (2)	150.7 (17)
C17—H17B⋯O2ⁱⁱ	0.98 (2)	2.65 (2)	3.616 (3)	168.4 (18)
C18—H18B⋯O3ⁱⁱⁱ	0.99 (3)	2.60 (3)	3.482 (2)	148.3 (19)
C12—H12⋯Cg3^iv	0.99 (2)	2.96 (2)	3.713 (2)	133.4 (15)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
Detail of the intermolecular interactions viewed along the c-axis direction. C—H⋯O hydrogen bonds are shown by black dashed lines while C—H⋯π(ring) and π–π-stacking interactions are shown, respectively, by green and orange dashed lines.

Figure 3
Packing viewed along the b-axis direction with intermolecular interactions depicted as in Fig. 2

Synthesis and crystallization

To a solution of 2-oxo-3-phenyl-1,2-dihydroquinoxaline (0.7 g, 3 mmol) in N,N-dimethylformamide (20 ml) were added ethyl bromoacetate (0.25 ml, 2.25 mmol), potassium carbonate K₂CO₃ (0.1 g, 2.25 mmol) and a catalytic quantity of tetra-n-butylammonium bromide. The mixture was stirred at room temperature for 12 h. The solution was filtered and the solvent removed under reduced pressure. The residue obtained, after evaporation of solvent, was chromatographed on a silica gel column using a hexane/ethyl acetate 9:1 mixture as eluent. The solid obtained was recrystallized from ethanol to afford colourless crystals (yield: 90%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The structure was refined as a two-component twin.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₃
M_r	308.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	18.1710 (5), 4.9012 (1), 16.9492 (5)
β (°)	91.923 (1)
V (Å³)	1508.64 (7)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.77
Crystal size (mm)	0.32 × 0.11 × 0.04

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (TWINABS; Sheldrick, 2009 )
T_min, T_max	0.79, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	19783, 19783, 14579
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 1.02
No. of reflections	19783
No. of parameters	274
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24
Computer programs: APEX3 and SAINT (Bruker, 2016 ), CELL_NOW (Sheldrick, 2008a ), SHELXT (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008b ).

Structural data

CCDC reference: 1834198

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618005199/vm4035sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618005199/vm4035Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618005199/vm4035Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314618005199/vm4035Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016) and CELL_NOW (Sheldrick, 2008a); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Ethyl 2-(2-oxo-3-phenyl-1,2-dihydroquinoxalin-1-yl)acetate top

Crystal data top

C₁₈H₁₆N₂O₃	F(000) = 648
M_r = 308.33	D_x = 1.357 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 18.1710 (5) Å	Cell parameters from 9923 reflections
b = 4.9012 (1) Å	θ = 2.4–72.4°
c = 16.9492 (5) Å	µ = 0.77 mm⁻¹
β = 91.923 (1)°	T = 150 K
V = 1508.64 (7) Å³	Plate, colourless
Z = 4	0.32 × 0.11 × 0.04 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	19783 independent reflections
Radiation source: INCOATEC IµS micro-focus source	14579 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.4°, θ_min = 2.4°
ω scans	h = −22→21
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −6→5
T_min = 0.79, T_max = 0.97	l = −20→20
19783 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	All H-atom parameters refined
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0459P)² + 0.2438P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
19783 reflections	Δρ_max = 0.20 e Å⁻³
274 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0050 (8)

Special details top

Experimental. Analysis of 1517 reflections having I/σ(I) > 12 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the monoclinic system and to consist of two components related by a 35.5° rotation about the b axis. The raw data were processed using the multi-component version ofSAINT under control of the two-component orientation filegenerated by CELL_NOW.

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. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq
O1	0.25922 (7)	0.7640 (3)	0.31580 (8)	0.0417 (4)
O2	0.41992 (7)	0.6916 (3)	0.43879 (8)	0.0438 (4)
O3	0.46812 (6)	0.4139 (3)	0.34884 (7)	0.0364 (3)
N1	0.15573 (8)	0.6338 (3)	0.48696 (8)	0.0277 (3)
N2	0.28105 (7)	0.4569 (3)	0.41319 (8)	0.0285 (3)
C1	0.26404 (9)	0.3412 (3)	0.48550 (10)	0.0282 (4)
C2	0.30684 (10)	0.1373 (4)	0.52219 (11)	0.0352 (4)
H2	0.3510 (13)	0.067 (4)	0.4983 (13)	0.043 (6)*
C3	0.28523 (11)	0.0297 (4)	0.59278 (12)	0.0395 (4)
H3	0.3145 (13)	−0.117 (5)	0.6175 (13)	0.050 (6)*
C4	0.22231 (11)	0.1216 (4)	0.62916 (11)	0.0393 (4)
H4	0.2080 (12)	0.036 (5)	0.6796 (14)	0.045 (6)*
C5	0.18037 (10)	0.3237 (4)	0.59365 (11)	0.0348 (4)
H5	0.1341 (12)	0.395 (4)	0.6164 (12)	0.041 (5)*
C6	0.20033 (9)	0.4357 (3)	0.52132 (9)	0.0280 (4)
C7	0.17228 (9)	0.7415 (3)	0.41992 (9)	0.0260 (4)
C8	0.23990 (9)	0.6628 (3)	0.37802 (10)	0.0294 (4)
C9	0.11989 (9)	0.9429 (3)	0.38455 (9)	0.0268 (4)
C10	0.04810 (10)	0.9459 (4)	0.41234 (10)	0.0308 (4)
H10	0.0352 (11)	0.811 (4)	0.4512 (12)	0.038 (5)*
C11	−0.00326 (10)	1.1326 (4)	0.38378 (10)	0.0335 (4)
H11	−0.0533 (13)	1.128 (4)	0.4046 (12)	0.040 (5)*
C12	0.01550 (10)	1.3195 (4)	0.32662 (10)	0.0339 (4)
H12	−0.0217 (12)	1.452 (4)	0.3059 (12)	0.036 (5)*
C13	0.08591 (10)	1.3174 (4)	0.29784 (10)	0.0332 (4)
H13	0.1002 (11)	1.449 (4)	0.2570 (12)	0.039 (5)*
C14	0.13792 (10)	1.1303 (3)	0.32583 (10)	0.0299 (4)
H14	0.1874 (12)	1.132 (4)	0.3037 (12)	0.040 (5)*
C15	0.34349 (10)	0.3597 (4)	0.36944 (11)	0.0324 (4)
H15A	0.3325 (12)	0.389 (5)	0.3142 (15)	0.046 (6)*
H15B	0.3514 (12)	0.167 (5)	0.3776 (12)	0.040 (5)*
C16	0.41371 (9)	0.5107 (3)	0.39143 (10)	0.0297 (4)
C17	0.54066 (10)	0.5371 (5)	0.36140 (13)	0.0422 (5)
H17A	0.5341 (14)	0.739 (6)	0.3615 (15)	0.062 (7)*
H17B	0.5591 (13)	0.475 (5)	0.4136 (14)	0.047 (6)*
C18	0.58651 (11)	0.4416 (5)	0.29504 (12)	0.0407 (5)
H18A	0.6373 (14)	0.517 (5)	0.3032 (14)	0.052 (6)*
H18B	0.5656 (14)	0.506 (5)	0.2434 (16)	0.058 (7)*
H18C	0.5870 (13)	0.234 (5)	0.2945 (13)	0.049 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0402 (8)	0.0435 (8)	0.0427 (7)	0.0049 (6)	0.0176 (6)	0.0057 (6)
O2	0.0317 (7)	0.0435 (8)	0.0567 (8)	−0.0015 (6)	0.0059 (6)	−0.0212 (6)
O3	0.0226 (6)	0.0414 (7)	0.0457 (7)	−0.0027 (5)	0.0081 (5)	−0.0121 (5)
N1	0.0241 (7)	0.0285 (7)	0.0306 (7)	0.0023 (6)	0.0025 (5)	−0.0011 (5)
N2	0.0208 (7)	0.0292 (7)	0.0357 (7)	0.0009 (6)	0.0047 (6)	−0.0064 (6)
C1	0.0241 (8)	0.0259 (8)	0.0345 (8)	−0.0009 (6)	−0.0003 (7)	−0.0063 (6)
C2	0.0271 (9)	0.0319 (9)	0.0465 (10)	0.0047 (7)	−0.0029 (8)	−0.0067 (7)
C3	0.0369 (11)	0.0332 (10)	0.0477 (11)	0.0064 (8)	−0.0097 (8)	0.0004 (8)
C4	0.0419 (11)	0.0375 (10)	0.0382 (10)	0.0031 (8)	−0.0017 (8)	0.0049 (8)
C5	0.0328 (10)	0.0363 (9)	0.0354 (9)	0.0040 (8)	0.0030 (7)	0.0016 (7)
C6	0.0246 (8)	0.0268 (8)	0.0327 (8)	0.0018 (7)	0.0000 (6)	−0.0031 (6)
C7	0.0237 (8)	0.0249 (8)	0.0296 (8)	−0.0015 (6)	0.0023 (6)	−0.0043 (6)
C8	0.0254 (8)	0.0293 (9)	0.0336 (9)	−0.0018 (7)	0.0048 (7)	−0.0041 (6)
C9	0.0263 (8)	0.0260 (8)	0.0279 (8)	0.0006 (7)	0.0000 (6)	−0.0048 (6)
C10	0.0294 (9)	0.0320 (9)	0.0310 (8)	0.0029 (7)	0.0030 (7)	−0.0009 (7)
C11	0.0290 (9)	0.0374 (10)	0.0340 (9)	0.0060 (7)	0.0007 (7)	−0.0032 (7)
C12	0.0359 (10)	0.0316 (9)	0.0337 (9)	0.0065 (8)	−0.0062 (7)	−0.0035 (7)
C13	0.0378 (10)	0.0297 (9)	0.0317 (9)	−0.0025 (7)	−0.0037 (7)	0.0006 (7)
C14	0.0296 (9)	0.0297 (9)	0.0302 (8)	−0.0040 (7)	−0.0006 (7)	−0.0029 (6)
C15	0.0240 (9)	0.0326 (10)	0.0409 (10)	0.0018 (7)	0.0071 (7)	−0.0097 (7)
C16	0.0251 (9)	0.0290 (8)	0.0352 (8)	0.0036 (7)	0.0043 (7)	−0.0031 (7)
C17	0.0234 (9)	0.0502 (12)	0.0533 (12)	−0.0070 (8)	0.0052 (8)	−0.0082 (9)
C18	0.0258 (10)	0.0550 (13)	0.0415 (10)	0.0020 (9)	0.0049 (8)	0.0111 (9)

Geometric parameters (Å, º) top

O1—C8	1.227 (2)	C9—C10	1.402 (2)
O2—C16	1.199 (2)	C9—C14	1.401 (2)
O3—C16	1.3311 (19)	C10—C11	1.383 (3)
O3—C17	1.459 (2)	C10—H10	0.97 (2)
N1—C7	1.297 (2)	C11—C12	1.384 (3)
N1—C6	1.381 (2)	C11—H11	0.99 (2)
N2—C8	1.379 (2)	C12—C13	1.385 (3)
N2—C1	1.395 (2)	C12—H12	0.99 (2)
N2—C15	1.456 (2)	C13—C14	1.389 (3)
C1—C2	1.399 (3)	C13—H13	0.99 (2)
C1—C6	1.404 (2)	C14—H14	0.99 (2)
C2—C3	1.377 (3)	C15—C16	1.511 (2)
C2—H2	0.97 (2)	C15—H15A	0.96 (2)
C3—C4	1.392 (3)	C15—H15B	0.96 (2)
C3—H3	0.98 (2)	C17—C18	1.497 (3)
C4—C5	1.376 (3)	C17—H17A	1.00 (3)
C4—H4	0.99 (2)	C17—H17B	0.98 (2)
C5—C6	1.402 (2)	C18—H18A	1.00 (2)
C5—H5	1.00 (2)	C18—H18B	0.99 (3)
C7—C9	1.484 (2)	C18—H18C	1.02 (3)
C7—C8	1.490 (2)

C16—O3—C17	117.19 (14)	C9—C10—H10	118.1 (12)
C7—N1—C6	120.36 (14)	C10—C11—C12	120.25 (17)
C8—N2—C1	122.99 (13)	C10—C11—H11	118.7 (12)
C8—N2—C15	116.08 (14)	C12—C11—H11	121.1 (12)
C1—N2—C15	120.92 (15)	C11—C12—C13	119.59 (17)
N2—C1—C2	123.01 (15)	C11—C12—H12	120.0 (12)
N2—C1—C6	117.13 (15)	C13—C12—H12	120.4 (12)
C2—C1—C6	119.86 (16)	C12—C13—C14	120.72 (16)
C3—C2—C1	119.29 (17)	C12—C13—H13	120.7 (12)
C3—C2—H2	119.3 (13)	C14—C13—H13	118.6 (12)
C1—C2—H2	121.4 (13)	C13—C14—C9	120.18 (16)
C2—C3—C4	121.57 (17)	C13—C14—H14	118.8 (12)
C2—C3—H3	119.0 (13)	C9—C14—H14	121.0 (12)
C4—C3—H3	119.4 (13)	N2—C15—C16	112.34 (14)
C5—C4—C3	119.35 (18)	N2—C15—H15A	107.9 (13)
C5—C4—H4	121.5 (13)	C16—C15—H15A	108.3 (14)
C3—C4—H4	119.1 (13)	N2—C15—H15B	111.2 (13)
C4—C5—C6	120.56 (17)	C16—C15—H15B	108.9 (13)
C4—C5—H5	122.9 (12)	H15A—C15—H15B	108.1 (18)
C6—C5—H5	116.5 (12)	O2—C16—O3	124.89 (16)
N1—C6—C5	118.60 (15)	O2—C16—C15	125.96 (15)
N1—C6—C1	122.05 (15)	O3—C16—C15	109.15 (14)
C5—C6—C1	119.35 (16)	O3—C17—C18	106.48 (16)
N1—C7—C9	117.39 (14)	O3—C17—H17A	107.7 (15)
N1—C7—C8	122.08 (15)	C18—C17—H17A	112.4 (15)
C9—C7—C8	120.51 (14)	O3—C17—H17B	106.3 (13)
O1—C8—N2	120.03 (15)	C18—C17—H17B	113.4 (13)
O1—C8—C7	124.68 (16)	H17A—C17—H17B	110 (2)
N2—C8—C7	115.28 (14)	C17—C18—H18A	108.4 (14)
C10—C9—C14	118.30 (15)	C17—C18—H18B	110.8 (14)
C10—C9—C7	117.58 (14)	H18A—C18—H18B	109.1 (19)
C14—C9—C7	124.11 (15)	C17—C18—H18C	108.9 (13)
C11—C10—C9	120.94 (16)	H18A—C18—H18C	111.2 (19)
C11—C10—H10	120.9 (13)	H18B—C18—H18C	108.3 (19)

C8—N2—C1—C2	−178.28 (16)	N1—C7—C8—O1	−177.72 (16)
C15—N2—C1—C2	3.2 (2)	C9—C7—C8—O1	4.1 (3)
C8—N2—C1—C6	2.4 (2)	N1—C7—C8—N2	3.6 (2)
C15—N2—C1—C6	−176.20 (15)	C9—C7—C8—N2	−174.59 (14)
N2—C1—C2—C3	−178.57 (16)	N1—C7—C9—C10	−18.0 (2)
C6—C1—C2—C3	0.8 (3)	C8—C7—C9—C10	160.34 (15)
C1—C2—C3—C4	−0.9 (3)	N1—C7—C9—C14	161.55 (15)
C2—C3—C4—C5	0.4 (3)	C8—C7—C9—C14	−20.1 (2)
C3—C4—C5—C6	0.3 (3)	C14—C9—C10—C11	−1.3 (2)
C7—N1—C6—C5	−179.75 (16)	C7—C9—C10—C11	178.23 (15)
C7—N1—C6—C1	−0.7 (2)	C9—C10—C11—C12	0.4 (3)
C4—C5—C6—N1	178.56 (16)	C10—C11—C12—C13	0.4 (3)
C4—C5—C6—C1	−0.5 (3)	C11—C12—C13—C14	−0.2 (3)
N2—C1—C6—N1	0.3 (2)	C12—C13—C14—C9	−0.8 (3)
C2—C1—C6—N1	−179.10 (15)	C10—C9—C14—C13	1.5 (2)
N2—C1—C6—C5	179.30 (15)	C7—C9—C14—C13	−177.98 (15)
C2—C1—C6—C5	−0.1 (2)	C8—N2—C15—C16	91.54 (19)
C6—N1—C7—C9	176.98 (14)	C1—N2—C15—C16	−89.81 (19)
C6—N1—C7—C8	−1.3 (2)	C17—O3—C16—O2	0.4 (3)
C1—N2—C8—O1	177.16 (15)	C17—O3—C16—C15	179.47 (16)
C15—N2—C8—O1	−4.2 (2)	N2—C15—C16—O2	−0.3 (3)
C1—N2—C8—C7	−4.1 (2)	N2—C15—C16—O3	−179.37 (15)
C15—N2—C8—C7	174.49 (14)	C16—O3—C17—C18	−167.13 (16)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.97 (2)	2.46 (2)	3.345 (2)	150.7 (17)
C17—H17B···O2ⁱⁱ	0.98 (2)	2.65 (2)	3.616 (3)	168.4 (18)
C18—H18B···O3ⁱⁱⁱ	0.99 (3)	2.60 (3)	3.482 (2)	148.3 (19)
C12—H12···Cg3^iv	0.99 (2)	2.96 (2)	3.713 (2)	133.4 (15)

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

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.

References

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Volume 3| Part 4| April 2018| x180519

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 2-(2-oxo-3-phenyl-1,2-di­hydro­quinoxalin-1-yl)acetate

Structure description

Synthesis and crystallization

Refinement

Structural data

Funding information

References

organic compounds

Ethyl 2-(2-oxo-3-phenyl-1,2-dihydroquinoxalin-1-yl)acetate