All interatomic distances in the title compound, C
20H
21N
3O
4, are normal. The heteroatom ring of the quinoxalinone system exists in a conformation intermediate between half-chair and sofa. The (4-ethoxyphenyl)amino moiety is nearly planar. The aminooxoethyl part can also be considered planar. There is one weak intramolecular C—H
O hydrogen bond in the structure. The structure is assembled by intermolecular N—H
O hydrogen bonds, to form a two-dimensional framework. One further C—H
O short intermolecular interaction is present in the structure.
Supporting information
CCDC reference: 180772
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.074
- wR factor = 0.248
- Data-to-parameter ratio = 15.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
RADNW_01 Alert C The radiation wavelength lies outside the expected range
for the supplied radiation type. Expected range 1.54175-1.54180
Wavelength given = 1.54052
REFLT_03
From the CIF: _diffrn_reflns_theta_max 80.59
From the CIF: _reflns_number_total 3916
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 4201
Completeness (_total/calc) 93.22%
Alert C: < 95% complete
General Notes
RADNW_01 The radiation wavelength given implies that Cu Kalpha1 has
been used. Please check that this is correct.
Wavelength given = 1.54052
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: KM-4 Software (Kuma, 1993); cell refinement: KM-4 Software; data reduction: DATAPROC (Gałdecki et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia, 1997).
4-(2-Acetyl-2-(4-ethoxyphenyl)amino-1-oxoethyl)-1,2,3,4-
tetrahydro-2-quinoxalinone
top
Crystal data top
C20H21N3O4 | F(000) = 776 |
Mr = 367.40 | Dx = 1.283 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54052 Å |
a = 8.289 (1) Å | Cell parameters from 99 reflections |
b = 12.117 (2) Å | θ = 5–60° |
c = 19.225 (3) Å | µ = 0.75 mm−1 |
β = 99.88 (1)° | T = 293 K |
V = 1902.3 (5) Å3 | Sphere, colourless |
Z = 4 | 0.51 mm (radius) |
Data collection top
Kuma KM-4 diffractometer | 1952 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 80.6°, θmin = 4.3° |
ω–2θ scans | h = −9→9 |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | k = 0→15 |
Tmin = 0.692, Tmax = 0.715 | l = −24→0 |
4204 measured reflections | 2 standard reflections every 100 reflections |
3916 independent reflections | intensity decay: −4.0% |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.248 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.1581P)2] where P = (Fo2 + 2Fc2)/3 |
3916 reflections | (Δ/σ)max = 0.006 |
250 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 >
σ(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N12 | 0.6189 (3) | 0.7165 (2) | 0.13601 (15) | 0.0485 (6) | |
C21 | 0.5487 (4) | 0.7771 (3) | 0.1819 (2) | 0.0564 (8) | |
O13 | 0.4613 (3) | 0.7330 (2) | 0.21980 (14) | 0.0674 (7) | |
C22 | 0.5818 (6) | 0.8990 (3) | 0.1872 (3) | 0.0767 (12) | |
H22A | 0.6972 | 0.9119 | 0.1907 | 0.092* | |
H22B | 0.5453 | 0.9279 | 0.2283 | 0.092* | |
H22C | 0.5241 | 0.9351 | 0.1458 | 0.092* | |
C12 | 0.5837 (4) | 0.5990 (2) | 0.13085 (18) | 0.0459 (7) | |
H12A | 0.5941 | 0.5677 | 0.1779 | 0.055* | |
H12B | 0.6624 | 0.5626 | 0.1066 | 0.055* | |
C11 | 0.4122 (4) | 0.5786 (3) | 0.09102 (17) | 0.0479 (7) | |
O11 | 0.3327 (3) | 0.6527 (2) | 0.05875 (16) | 0.0746 (8) | |
N1 | 0.3484 (3) | 0.4755 (2) | 0.09372 (14) | 0.0465 (6) | |
C8 | 0.1713 (4) | 0.4615 (3) | 0.06975 (19) | 0.0574 (9) | |
H8A | 0.1532 | 0.4065 | 0.0325 | 0.069* | |
H8B | 0.1248 | 0.5306 | 0.0504 | 0.069* | |
C7 | 0.0872 (4) | 0.4264 (3) | 0.1285 (2) | 0.0615 (10) | |
O1 | −0.0516 (3) | 0.4530 (3) | 0.1315 (2) | 0.0998 (11) | |
N2 | 0.1776 (4) | 0.3617 (3) | 0.17842 (19) | 0.0591 (8) | |
H3 | 0.135 (5) | 0.325 (4) | 0.204 (2) | 0.077 (14)* | |
C6 | 0.3362 (4) | 0.3262 (3) | 0.17427 (17) | 0.0478 (7) | |
C1 | 0.4261 (4) | 0.3832 (2) | 0.13107 (17) | 0.0459 (7) | |
C2 | 0.5806 (4) | 0.3460 (3) | 0.1232 (2) | 0.0559 (9) | |
H2 | 0.6379 | 0.3806 | 0.0918 | 0.067* | |
C3 | 0.6476 (5) | 0.2573 (3) | 0.1625 (3) | 0.0719 (12) | |
H3A | 0.7519 | 0.2329 | 0.1583 | 0.086* | |
C4 | 0.5623 (5) | 0.2043 (3) | 0.2081 (2) | 0.0703 (11) | |
H4 | 0.6106 | 0.1458 | 0.2353 | 0.084* | |
C5 | 0.4061 (5) | 0.2371 (3) | 0.2136 (2) | 0.0612 (9) | |
H5 | 0.3478 | 0.1998 | 0.2436 | 0.073* | |
C13 | 0.6987 (4) | 0.7639 (3) | 0.08156 (18) | 0.0550 (8) | |
C18 | 0.8668 (5) | 0.7447 (3) | 0.0833 (2) | 0.0610 (9) | |
H18 | 0.9247 | 0.7028 | 0.1198 | 0.073* | |
C17 | 0.9453 (5) | 0.7855 (4) | 0.0335 (2) | 0.0733 (11) | |
H17 | 1.0555 | 0.7695 | 0.0346 | 0.088* | |
C16 | 0.8651 (5) | 0.8491 (4) | −0.0176 (2) | 0.0724 (12) | |
C15 | 0.7003 (7) | 0.8703 (4) | −0.0238 (2) | 0.0884 (15) | |
H15 | 0.6462 | 0.9126 | −0.0610 | 0.106* | |
C14 | 0.6124 (6) | 0.8251 (3) | 0.0289 (2) | 0.0774 (12) | |
H14 | 0.5009 | 0.8378 | 0.0265 | 0.093* | |
O12 | 0.9570 (4) | 0.8877 (3) | −0.06865 (19) | 0.1013 (11) | |
C19 | 0.8841 (8) | 0.9603 (4) | −0.1158 (3) | 0.1053 (18) | |
H19A | 0.8537 | 1.0256 | −0.0918 | 0.126* | |
H19B | 0.7854 | 0.9283 | −0.1425 | 0.126* | |
C20 | 1.0017 (7) | 0.9920 (4) | −0.1656 (3) | 0.0962 (16) | |
H20A | 0.9531 | 1.0489 | −0.1972 | 0.115* | |
H20B | 1.0235 | 0.9285 | −0.1923 | 0.115* | |
H20C | 1.1024 | 1.0186 | −0.1385 | 0.115* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N12 | 0.0395 (15) | 0.0437 (13) | 0.0646 (16) | −0.0056 (10) | 0.0153 (12) | −0.0047 (12) |
C21 | 0.050 (2) | 0.0485 (17) | 0.073 (2) | −0.0019 (15) | 0.0162 (17) | 0.0002 (17) |
O13 | 0.0607 (16) | 0.0601 (15) | 0.0901 (18) | −0.0025 (12) | 0.0379 (14) | 0.0010 (13) |
C22 | 0.090 (3) | 0.0451 (19) | 0.102 (3) | −0.0049 (19) | 0.039 (3) | −0.008 (2) |
C12 | 0.0352 (16) | 0.0406 (15) | 0.0628 (19) | −0.0038 (12) | 0.0110 (13) | 0.0005 (13) |
C11 | 0.0434 (18) | 0.0477 (17) | 0.0531 (17) | −0.0012 (13) | 0.0098 (14) | 0.0023 (14) |
O11 | 0.0546 (15) | 0.0594 (15) | 0.103 (2) | −0.0041 (11) | −0.0069 (14) | 0.0292 (14) |
N1 | 0.0294 (13) | 0.0459 (13) | 0.0627 (15) | −0.0012 (10) | 0.0035 (11) | 0.0017 (12) |
C8 | 0.0340 (18) | 0.062 (2) | 0.071 (2) | −0.0068 (14) | −0.0042 (15) | 0.0063 (17) |
C7 | 0.0266 (17) | 0.066 (2) | 0.090 (3) | −0.0063 (15) | 0.0063 (16) | 0.005 (2) |
O1 | 0.0327 (15) | 0.113 (3) | 0.155 (3) | 0.0056 (15) | 0.0225 (17) | 0.032 (2) |
N2 | 0.0405 (17) | 0.0590 (17) | 0.080 (2) | −0.0048 (13) | 0.0158 (15) | 0.0079 (16) |
C6 | 0.0338 (16) | 0.0477 (16) | 0.0605 (18) | −0.0039 (13) | 0.0039 (13) | −0.0067 (14) |
C1 | 0.0368 (17) | 0.0382 (14) | 0.0611 (18) | −0.0029 (12) | 0.0035 (13) | −0.0066 (13) |
C2 | 0.0377 (18) | 0.0460 (16) | 0.085 (2) | −0.0005 (13) | 0.0132 (16) | −0.0083 (17) |
C3 | 0.0398 (19) | 0.0516 (19) | 0.121 (3) | 0.0065 (15) | 0.005 (2) | −0.005 (2) |
C4 | 0.060 (2) | 0.0447 (18) | 0.098 (3) | 0.0034 (16) | −0.011 (2) | 0.0023 (19) |
C5 | 0.058 (2) | 0.0508 (19) | 0.072 (2) | −0.0066 (16) | 0.0013 (17) | 0.0069 (17) |
C13 | 0.059 (2) | 0.0455 (17) | 0.062 (2) | −0.0134 (15) | 0.0143 (17) | −0.0052 (15) |
C18 | 0.055 (2) | 0.062 (2) | 0.070 (2) | −0.0146 (16) | 0.0243 (18) | −0.0118 (17) |
C17 | 0.066 (3) | 0.077 (3) | 0.081 (3) | −0.009 (2) | 0.025 (2) | −0.009 (2) |
C16 | 0.065 (3) | 0.078 (3) | 0.081 (3) | −0.032 (2) | 0.030 (2) | −0.012 (2) |
C15 | 0.121 (4) | 0.068 (3) | 0.068 (3) | −0.022 (3) | −0.006 (3) | 0.011 (2) |
C14 | 0.081 (3) | 0.068 (2) | 0.082 (3) | −0.015 (2) | 0.010 (2) | 0.010 (2) |
O12 | 0.104 (3) | 0.101 (3) | 0.102 (2) | −0.008 (2) | 0.025 (2) | 0.017 (2) |
C19 | 0.141 (5) | 0.070 (3) | 0.090 (3) | −0.023 (3) | −0.020 (3) | −0.008 (3) |
C20 | 0.132 (5) | 0.082 (3) | 0.085 (3) | −0.022 (3) | 0.048 (3) | 0.007 (2) |
Geometric parameters (Å, º) top
N12—C21 | 1.354 (4) | C2—C3 | 1.375 (5) |
N12—C13 | 1.449 (4) | C2—H2 | 0.9300 |
N12—C12 | 1.454 (4) | C3—C4 | 1.375 (6) |
C21—O13 | 1.234 (4) | C3—H3A | 0.9300 |
C21—C22 | 1.502 (5) | C4—C5 | 1.376 (5) |
C22—H22A | 0.9600 | C4—H4 | 0.9300 |
C22—H22B | 0.9600 | C5—H5 | 0.9300 |
C22—H22C | 0.9600 | C13—C14 | 1.356 (5) |
C12—C11 | 1.515 (4) | C13—C18 | 1.407 (5) |
C12—H12A | 0.9700 | C18—C17 | 1.342 (5) |
C12—H12B | 0.9700 | C18—H18 | 0.9300 |
C11—O11 | 1.219 (4) | C17—C16 | 1.332 (6) |
C11—N1 | 1.361 (4) | C17—H17 | 0.9300 |
N1—C1 | 1.422 (4) | C16—C15 | 1.375 (7) |
N1—C8 | 1.470 (4) | C16—O12 | 1.421 (5) |
C8—C7 | 1.487 (5) | C15—C14 | 1.452 (6) |
C8—H8A | 0.9700 | C15—H15 | 0.9300 |
C8—H8B | 0.9700 | C14—H14 | 0.9300 |
C7—O1 | 1.206 (4) | O12—C19 | 1.331 (6) |
C7—N2 | 1.361 (5) | C19—C20 | 1.528 (7) |
N2—C6 | 1.398 (4) | C19—H19A | 0.9700 |
N2—H3 | 0.78 (4) | C19—H19B | 0.9700 |
C6—C5 | 1.387 (5) | C20—H20A | 0.9600 |
C6—C1 | 1.391 (4) | C20—H20B | 0.9600 |
C1—C2 | 1.391 (4) | C20—H20C | 0.9600 |
| | | |
C21—N12—C13 | 123.8 (3) | C3—C2—H2 | 120.4 |
C21—N12—C12 | 118.2 (3) | C1—C2—H2 | 120.4 |
C13—N12—C12 | 116.8 (3) | C2—C3—C4 | 120.8 (3) |
O13—C21—N12 | 120.8 (3) | C2—C3—H3A | 119.6 |
O13—C21—C22 | 120.4 (3) | C4—C3—H3A | 119.6 |
N12—C21—C22 | 118.9 (3) | C3—C4—C5 | 120.5 (3) |
C21—C22—H22A | 109.5 | C3—C4—H4 | 119.7 |
C21—C22—H22B | 109.5 | C5—C4—H4 | 119.7 |
H22A—C22—H22B | 109.5 | C4—C5—C6 | 119.5 (3) |
C21—C22—H22C | 109.5 | C4—C5—H5 | 120.2 |
H22A—C22—H22C | 109.5 | C6—C5—H5 | 120.2 |
H22B—C22—H22C | 109.5 | C14—C13—C18 | 120.1 (4) |
N12—C12—C11 | 110.8 (3) | C14—C13—N12 | 120.6 (3) |
N12—C12—H12A | 109.5 | C18—C13—N12 | 119.3 (3) |
C11—C12—H12A | 109.5 | C17—C18—C13 | 121.4 (4) |
N12—C12—H12B | 109.5 | C17—C18—H18 | 119.3 |
C11—C12—H12B | 109.5 | C13—C18—H18 | 119.3 |
H12A—C12—H12B | 108.1 | C16—C17—C18 | 119.8 (4) |
O11—C11—N1 | 121.1 (3) | C16—C17—H17 | 120.1 |
O11—C11—C12 | 121.0 (3) | C18—C17—H17 | 120.1 |
N1—C11—C12 | 117.9 (3) | C17—C16—C15 | 122.4 (4) |
C11—N1—C1 | 126.5 (2) | C17—C16—O12 | 116.1 (4) |
C11—N1—C8 | 117.9 (3) | C15—C16—O12 | 121.3 (4) |
C1—N1—C8 | 114.1 (3) | C16—C15—C14 | 118.6 (4) |
N1—C8—C7 | 111.6 (3) | C16—C15—H15 | 120.7 |
N1—C8—H8A | 109.3 | C14—C15—H15 | 120.7 |
C7—C8—H8A | 109.3 | C13—C14—C15 | 117.6 (4) |
N1—C8—H8B | 109.3 | C13—C14—H14 | 121.2 |
C7—C8—H8B | 109.3 | C15—C14—H14 | 121.2 |
H8A—C8—H8B | 108.0 | C19—O12—C16 | 117.0 (5) |
O1—C7—N2 | 122.3 (4) | O12—C19—C20 | 109.2 (5) |
O1—C7—C8 | 122.4 (4) | O12—C19—H19A | 109.8 |
N2—C7—C8 | 115.3 (3) | C20—C19—H19A | 109.8 |
C7—N2—C6 | 123.1 (3) | O12—C19—H19B | 109.8 |
C7—N2—H3 | 121 (3) | C20—C19—H19B | 109.8 |
C6—N2—H3 | 113 (3) | H19A—C19—H19B | 108.3 |
C5—C6—C1 | 119.8 (3) | C19—C20—H20A | 109.5 |
C5—C6—N2 | 121.1 (3) | C19—C20—H20B | 109.5 |
C1—C6—N2 | 119.1 (3) | H20A—C20—H20B | 109.5 |
C2—C1—C6 | 120.1 (3) | C19—C20—H20C | 109.5 |
C2—C1—N1 | 123.1 (3) | H20A—C20—H20C | 109.5 |
C6—C1—N1 | 116.7 (3) | H20B—C20—H20C | 109.5 |
C3—C2—C1 | 119.1 (3) | | |
| | | |
C1—C6—N2—C7 | 20.2 (5) | C8—N1—C11—C12 | 166.0 (3) |
C6—N2—C7—C8 | −2.5 (5) | N1—C11—C12—N12 | −167.1 (3) |
N2—C7—C8—N1 | −32.3 (4) | C11—C12—N12—C21 | 74.5 (4) |
C7—C8—N1—C1 | 51.6 (4) | C11—C12—N12—C13 | −93.1 (3) |
C8—N1—C1—C6 | −35.7 (4) | C12—N12—C13—C18 | −75.5 (4) |
N1—C1—C6—N2 | 0.1 (4) | C12—N12—C13—C14 | 103.6 (4) |
C1—N1—C11—O11 | −178.0 (3) | C15—C16—O12—C19 | 11.1 (6) |
C8—N1—C11—O11 | −12.6 (5) | C17—C16—O12—C19 | −173.2 (4) |
C1—N1—C11—C12 | 0.6 (5) | C16—O12—C19—C20 | 179.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···O11 | 0.97 | 2.26 | 2.702 (4) | 107 |
N2—H3···O13i | 0.78 (4) | 2.11 (4) | 2.891 (4) | 174 (4) |
C20—H20B···O13ii | 0.96 | 2.58 | 3.486 (6) | 158 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1/2, −y+3/2, z−1/2. |