All interatomic distances in the title compound, C
19H
21N
3O
2, are normal. The heterocycle of the quinoxalinone system exhibits a half-chair conformation. The value of the total puckering amplitude
QT is 0.391 (5) Å. The benzylaminomethyl part of the side branch is close to planar. This weighted-least-squares plane makes a dihedral angle of 67.45 (14)° with the quinoxalinone plane. In the structure, there are C—H
N and C—H
O intramolecular hydrogen bonds. The molecules are held together by N—H
O intramolecular hydrogen bonds, resulting in a dimeric structure. The dimers are linked by weak C—H
O intermolecular hydrogen bonds, resulting in a three-dimensional layered hydrogen-bonded network.
Supporting information
CCDC reference: 183816
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.008 Å
- R factor = 0.088
- wR factor = 0.273
- Data-to-parameter ratio = 17.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
RFACR_01 Alert C The value of the weighted R factor is > 0.25
Weighted R factor given 0.273
PLAT_420 Alert C D-H Without Acceptor N(12) - H(12N) ?
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); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 1990).
4-(2-Benzylamino-1-oxoethyl)-1,2,3,4-tetrahydro-6,7-dimethylquinoxalin-2-one
top
Crystal data top
C19H21N3O2 | F(000) = 688 |
Mr = 323.39 | Dx = 1.271 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.523 (3) Å | Cell parameters from 99 reflections |
b = 14.521 (3) Å | θ = 4–22° |
c = 7.520 (2) Å | µ = 0.08 mm−1 |
β = 94.45 (3)° | T = 291 K |
V = 1690.0 (7) Å3 | Plate, colourless |
Z = 4 | 0.35 × 0.11 × 0.07 mm |
Data collection top
Kuma KM-4 diffractometer | 1256 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.059 |
Graphite monochromator | θmax = 27.6°, θmin = 1.9° |
ω–2θ scans | h = −20→20 |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | k = −18→0 |
Tmin = 0.942, Tmax = 0.997 | l = −9→0 |
4189 measured reflections | 2 standard reflections every 100 reflections |
3892 independent reflections | intensity decay: 7.3% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.088 | Hydrogen site location: mixed |
wR(F2) = 0.273 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.1058P)2] where P = (Fo2 + 2Fc2)/3 |
3892 reflections | (Δ/σ)max < 0.001 |
221 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.22 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 | |
N1 | 0.6838 (3) | 0.8568 (3) | 0.1946 (6) | 0.0456 (11) | |
O1 | 0.5246 (3) | 0.8753 (3) | 0.5121 (5) | 0.0637 (12) | |
N2 | 0.5711 (3) | 0.9806 (3) | 0.3194 (6) | 0.0478 (12) | |
H2N | 0.5380 | 1.0187 | 0.3662 | 0.035 (14)* | |
C2 | 0.7017 (3) | 0.9575 (4) | −0.0657 (7) | 0.0458 (14) | |
H2 | 0.7340 | 0.9125 | −0.1180 | 0.055* | |
C1 | 0.6670 (3) | 0.9393 (3) | 0.0970 (7) | 0.0421 (13) | |
C5 | 0.5962 (3) | 1.0859 (3) | 0.0764 (7) | 0.0421 (13) | |
H5 | 0.5587 | 1.1282 | 0.1223 | 0.050* | |
O11 | 0.7692 (2) | 0.7428 (3) | 0.3095 (6) | 0.0657 (12) | |
C3 | 0.6884 (3) | 1.0420 (4) | −0.1499 (6) | 0.0415 (13) | |
C6 | 0.6108 (3) | 1.0025 (4) | 0.1626 (7) | 0.0406 (13) | |
N12 | 0.9199 (3) | 0.8478 (3) | 0.2993 (6) | 0.0524 (12) | |
H12N | 0.9328 | 0.7865 | 0.3070 | 0.09 (2)* | |
C7 | 0.5653 (4) | 0.8952 (4) | 0.3807 (8) | 0.0485 (14) | |
C10 | 0.6235 (4) | 1.2027 (4) | −0.1574 (8) | 0.0566 (16) | |
H10A | 0.5993 | 1.1970 | −0.2783 | 0.085* | |
H10B | 0.6783 | 1.2334 | −0.1557 | 0.085* | |
H10C | 0.5850 | 1.2378 | −0.0898 | 0.085* | |
C14 | 0.9884 (3) | 0.8781 (4) | 0.6013 (8) | 0.0470 (14) | |
C4 | 0.6358 (3) | 1.1081 (3) | −0.0760 (7) | 0.0405 (13) | |
C11 | 0.7639 (3) | 0.8162 (4) | 0.2294 (7) | 0.0465 (14) | |
C12 | 0.8449 (3) | 0.8640 (4) | 0.1738 (7) | 0.0514 (15) | |
H12A | 0.8574 | 0.8419 | 0.0568 | 0.062* | |
H12B | 0.8342 | 0.9297 | 0.1648 | 0.062* | |
C13 | 0.9091 (4) | 0.8882 (4) | 0.4706 (8) | 0.0574 (16) | |
H13A | 0.8602 | 0.8595 | 0.5211 | 0.069* | |
H13B | 0.8961 | 0.9532 | 0.4548 | 0.069* | |
C9 | 0.7303 (4) | 1.0605 (4) | −0.3209 (8) | 0.0642 (18) | |
H9A | 0.6879 | 1.0841 | −0.4090 | 0.096* | |
H9B | 0.7541 | 1.0043 | −0.3634 | 0.096* | |
H9C | 0.7757 | 1.1050 | −0.2991 | 0.096* | |
C15 | 0.9830 (5) | 0.8997 (4) | 0.7768 (9) | 0.0703 (19) | |
H15 | 0.9304 | 0.9203 | 0.8129 | 0.084* | |
C8 | 0.6106 (4) | 0.8212 (4) | 0.2840 (8) | 0.0574 (16) | |
H8A | 0.6308 | 0.7740 | 0.3686 | 0.069* | |
H8B | 0.5698 | 0.7928 | 0.1964 | 0.069* | |
C19 | 1.0677 (4) | 0.8508 (4) | 0.5506 (9) | 0.0667 (18) | |
H19 | 1.0734 | 0.8364 | 0.4315 | 0.080* | |
C18 | 1.1391 (4) | 0.8442 (5) | 0.6711 (11) | 0.081 (2) | |
H18 | 1.1923 | 0.8261 | 0.6338 | 0.098* | |
C16 | 1.0522 (6) | 0.8924 (5) | 0.9036 (9) | 0.083 (2) | |
H16 | 1.0460 | 0.9058 | 1.0229 | 0.099* | |
C17 | 1.1303 (5) | 0.8648 (5) | 0.8479 (12) | 0.086 (2) | |
H17 | 1.1779 | 0.8600 | 0.9305 | 0.104* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.047 (3) | 0.038 (2) | 0.054 (3) | 0.002 (2) | 0.018 (2) | 0.005 (2) |
O1 | 0.076 (3) | 0.059 (3) | 0.060 (3) | −0.008 (2) | 0.036 (2) | 0.004 (2) |
N2 | 0.056 (3) | 0.044 (3) | 0.045 (3) | −0.001 (2) | 0.017 (2) | −0.003 (2) |
C2 | 0.052 (3) | 0.046 (3) | 0.041 (3) | 0.001 (3) | 0.013 (3) | −0.001 (3) |
C1 | 0.050 (3) | 0.033 (3) | 0.043 (3) | 0.000 (3) | 0.004 (3) | −0.003 (3) |
C5 | 0.039 (3) | 0.038 (3) | 0.049 (3) | 0.004 (2) | 0.005 (3) | −0.008 (3) |
O11 | 0.062 (3) | 0.046 (2) | 0.089 (3) | −0.001 (2) | 0.003 (2) | 0.022 (2) |
C3 | 0.043 (3) | 0.049 (3) | 0.032 (3) | −0.001 (3) | 0.003 (2) | −0.001 (3) |
C6 | 0.041 (3) | 0.043 (3) | 0.039 (3) | −0.003 (2) | 0.008 (2) | −0.003 (3) |
N12 | 0.054 (3) | 0.051 (3) | 0.053 (3) | 0.006 (2) | 0.007 (2) | 0.000 (2) |
C7 | 0.047 (3) | 0.051 (4) | 0.050 (3) | −0.009 (3) | 0.017 (3) | −0.003 (3) |
C10 | 0.057 (4) | 0.051 (4) | 0.062 (4) | 0.006 (3) | 0.011 (3) | 0.011 (3) |
C14 | 0.045 (3) | 0.040 (3) | 0.056 (4) | −0.006 (3) | 0.007 (3) | −0.003 (3) |
C4 | 0.043 (3) | 0.038 (3) | 0.041 (3) | 0.000 (2) | 0.004 (3) | −0.003 (3) |
C11 | 0.054 (4) | 0.033 (3) | 0.053 (4) | −0.005 (3) | 0.007 (3) | 0.008 (3) |
C12 | 0.049 (3) | 0.053 (4) | 0.052 (3) | −0.002 (3) | 0.001 (3) | 0.011 (3) |
C13 | 0.057 (4) | 0.052 (4) | 0.064 (4) | 0.004 (3) | 0.012 (3) | −0.006 (3) |
C9 | 0.075 (4) | 0.068 (4) | 0.053 (4) | 0.015 (3) | 0.028 (3) | 0.014 (3) |
C15 | 0.078 (5) | 0.066 (4) | 0.069 (5) | −0.001 (4) | 0.017 (4) | −0.009 (4) |
C8 | 0.056 (4) | 0.047 (3) | 0.071 (4) | −0.005 (3) | 0.022 (3) | 0.000 (3) |
C19 | 0.067 (4) | 0.073 (5) | 0.060 (4) | 0.002 (4) | 0.005 (4) | 0.008 (3) |
C18 | 0.052 (4) | 0.096 (6) | 0.095 (6) | −0.001 (4) | −0.004 (4) | 0.016 (5) |
C16 | 0.105 (6) | 0.085 (5) | 0.056 (4) | −0.009 (5) | −0.006 (5) | −0.004 (4) |
C17 | 0.088 (6) | 0.076 (5) | 0.090 (6) | −0.012 (4) | −0.025 (5) | 0.010 (5) |
Geometric parameters (Å, º) top
N1—C11 | 1.383 (6) | C10—H10C | 0.9600 |
N1—C1 | 1.418 (6) | C14—C15 | 1.365 (8) |
N1—C8 | 1.460 (6) | C14—C19 | 1.376 (7) |
O1—C7 | 1.247 (6) | C14—C13 | 1.521 (8) |
N2—C7 | 1.329 (6) | C11—C12 | 1.523 (7) |
N2—C6 | 1.408 (6) | C12—H12A | 0.9700 |
N2—H2N | 0.8491 | C12—H12B | 0.9700 |
C2—C3 | 1.389 (7) | C13—H13A | 0.9700 |
C2—C1 | 1.399 (7) | C13—H13B | 0.9700 |
C2—H2 | 0.9300 | C9—H9A | 0.9600 |
C1—C6 | 1.384 (7) | C9—H9B | 0.9600 |
C5—C4 | 1.380 (7) | C9—H9C | 0.9600 |
C5—C6 | 1.385 (7) | C15—C16 | 1.384 (9) |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
O11—C11 | 1.223 (6) | C8—H8A | 0.9700 |
C3—C4 | 1.402 (7) | C8—H8B | 0.9700 |
C3—C9 | 1.510 (7) | C19—C18 | 1.380 (8) |
N12—C13 | 1.437 (7) | C19—H19 | 0.9300 |
N12—C12 | 1.460 (6) | C18—C17 | 1.380 (10) |
N12—H12N | 0.9138 | C18—H18 | 0.9300 |
C7—C8 | 1.503 (7) | C16—C17 | 1.372 (10) |
C10—C4 | 1.510 (7) | C16—H16 | 0.9300 |
C10—H10A | 0.9600 | C17—H17 | 0.9300 |
C10—H10B | 0.9600 | | |
| | | |
C11—N1—C1 | 125.8 (4) | N1—C11—C12 | 120.1 (4) |
C11—N1—C8 | 118.8 (4) | N12—C12—C11 | 112.6 (4) |
C1—N1—C8 | 114.8 (4) | N12—C12—H12A | 109.1 |
C7—N2—C6 | 123.2 (5) | C11—C12—H12A | 109.1 |
C7—N2—H2N | 113.8 | N12—C12—H12B | 109.1 |
C6—N2—H2N | 121.2 | C11—C12—H12B | 109.1 |
C3—C2—C1 | 120.8 (5) | H12A—C12—H12B | 107.8 |
C3—C2—H2 | 119.6 | N12—C13—C14 | 113.3 (5) |
C1—C2—H2 | 119.6 | N12—C13—H13A | 108.9 |
C6—C1—C2 | 118.8 (5) | C14—C13—H13A | 108.9 |
C6—C1—N1 | 118.1 (4) | N12—C13—H13B | 108.9 |
C2—C1—N1 | 123.0 (5) | C14—C13—H13B | 108.9 |
C4—C5—C6 | 121.7 (5) | H13A—C13—H13B | 107.7 |
C4—C5—H5 | 119.1 | C3—C9—H9A | 109.5 |
C6—C5—H5 | 119.1 | C3—C9—H9B | 109.5 |
C2—C3—C4 | 119.6 (5) | H9A—C9—H9B | 109.5 |
C2—C3—C9 | 119.2 (5) | C3—C9—H9C | 109.5 |
C4—C3—C9 | 121.2 (5) | H9A—C9—H9C | 109.5 |
C1—C6—C5 | 119.9 (5) | H9B—C9—H9C | 109.5 |
C1—C6—N2 | 118.5 (5) | C14—C15—C16 | 123.1 (7) |
C5—C6—N2 | 121.6 (5) | C14—C15—H15 | 118.5 |
C13—N12—C12 | 111.8 (4) | C16—C15—H15 | 118.5 |
C13—N12—H12N | 112.4 | N1—C8—C7 | 112.3 (4) |
C12—N12—H12N | 110.9 | N1—C8—H8A | 109.1 |
O1—C7—N2 | 123.0 (5) | C7—C8—H8A | 109.1 |
O1—C7—C8 | 120.1 (5) | N1—C8—H8B | 109.1 |
N2—C7—C8 | 116.9 (5) | C7—C8—H8B | 109.1 |
C4—C10—H10A | 109.5 | H8A—C8—H8B | 107.9 |
C4—C10—H10B | 109.5 | C14—C19—C18 | 121.9 (6) |
H10A—C10—H10B | 109.5 | C14—C19—H19 | 119.0 |
C4—C10—H10C | 109.5 | C18—C19—H19 | 119.0 |
H10A—C10—H10C | 109.5 | C19—C18—C17 | 118.9 (7) |
H10B—C10—H10C | 109.5 | C19—C18—H18 | 120.6 |
C15—C14—C19 | 117.2 (6) | C17—C18—H18 | 120.6 |
C15—C14—C13 | 119.7 (5) | C17—C16—C15 | 118.0 (7) |
C19—C14—C13 | 123.1 (5) | C17—C16—H16 | 121.0 |
C5—C4—C3 | 118.7 (5) | C15—C16—H16 | 121.0 |
C5—C4—C10 | 119.9 (5) | C16—C17—C18 | 120.9 (7) |
C3—C4—C10 | 121.4 (5) | C16—C17—H17 | 119.6 |
O11—C11—N1 | 119.4 (5) | C18—C17—H17 | 119.6 |
O11—C11—C12 | 120.4 (5) | | |
| | | |
N1—C1—C6—N2 | −1.9 (7) | C8—N1—C11—C12 | −166.0 (5) |
C1—C6—N2—C7 | −19.1 (7) | C1—N1—C11—C12 | 4.9 (8) |
C6—N2—C7—C8 | 5.5 (8) | N1—C11—C12—N12 | 145.6 (5) |
N2—C7—C8—N1 | 26.3 (7) | C11—C12—N12—C13 | −65.3 (6) |
C7—C8—N1—C1 | −45.7 (6) | C12—N12—C13—C14 | −176.3 (4) |
C8—N1—C1—C6 | 34.2 (7) | N12—C13—C14—C15 | −169.5 (5) |
C8—N1—C11—O11 | 12.0 (8) | N12—C13—C14—C19 | 12.9 (8) |
C1—N1—C11—O11 | −177.1 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O11 | 0.97 | 2.27 | 2.705 (7) | 106 |
C19—H19···N12 | 0.93 | 2.51 | 2.857 (8) | 102 |
N2—H2N···O1i | 0.85 | 2.07 | 2.913 (6) | 171 |
C2—H2···O11ii | 0.93 | 2.39 | 3.255 (7) | 154 |
C12—H12A···O11ii | 0.97 | 2.54 | 3.285 (7) | 134 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, −y+3/2, z−1/2. |