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All interatomic distances in the title compound, C19H21N3O2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004993/bt6126sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004993/bt6126IIsup2.hkl
Contains datablock II

CCDC reference: 183816

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](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


Yellow Alert 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

Computing details top

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
C19H21N3O2F(000) = 688
Mr = 323.39Dx = 1.271 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.523 (3) ÅCell parameters from 99 reflections
b = 14.521 (3) Åθ = 4–22°
c = 7.520 (2) ŵ = 0.08 mm1
β = 94.45 (3)°T = 291 K
V = 1690.0 (7) Å3Plate, colourless
Z = 40.35 × 0.11 × 0.07 mm
Data collection top
Kuma KM-4
diffractometer
1256 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.059
Graphite monochromatorθmax = 27.6°, θmin = 1.9°
ω–2θ scansh = 2020
Absorption correction: numerical
(X-RED; Stoe & Cie, 1999)
k = 180
Tmin = 0.942, Tmax = 0.997l = 90
4189 measured reflections2 standard reflections every 100 reflections
3892 independent reflections intensity decay: 7.3%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.088Hydrogen site location: mixed
wR(F2) = 0.273H 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 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
N10.6838 (3)0.8568 (3)0.1946 (6)0.0456 (11)
O10.5246 (3)0.8753 (3)0.5121 (5)0.0637 (12)
N20.5711 (3)0.9806 (3)0.3194 (6)0.0478 (12)
H2N0.53801.01870.36620.035 (14)*
C20.7017 (3)0.9575 (4)0.0657 (7)0.0458 (14)
H20.73400.91250.11800.055*
C10.6670 (3)0.9393 (3)0.0970 (7)0.0421 (13)
C50.5962 (3)1.0859 (3)0.0764 (7)0.0421 (13)
H50.55871.12820.12230.050*
O110.7692 (2)0.7428 (3)0.3095 (6)0.0657 (12)
C30.6884 (3)1.0420 (4)0.1499 (6)0.0415 (13)
C60.6108 (3)1.0025 (4)0.1626 (7)0.0406 (13)
N120.9199 (3)0.8478 (3)0.2993 (6)0.0524 (12)
H12N0.93280.78650.30700.09 (2)*
C70.5653 (4)0.8952 (4)0.3807 (8)0.0485 (14)
C100.6235 (4)1.2027 (4)0.1574 (8)0.0566 (16)
H10A0.59931.19700.27830.085*
H10B0.67831.23340.15570.085*
H10C0.58501.23780.08980.085*
C140.9884 (3)0.8781 (4)0.6013 (8)0.0470 (14)
C40.6358 (3)1.1081 (3)0.0760 (7)0.0405 (13)
C110.7639 (3)0.8162 (4)0.2294 (7)0.0465 (14)
C120.8449 (3)0.8640 (4)0.1738 (7)0.0514 (15)
H12A0.85740.84190.05680.062*
H12B0.83420.92970.16480.062*
C130.9091 (4)0.8882 (4)0.4706 (8)0.0574 (16)
H13A0.86020.85950.52110.069*
H13B0.89610.95320.45480.069*
C90.7303 (4)1.0605 (4)0.3209 (8)0.0642 (18)
H9A0.68791.08410.40900.096*
H9B0.75411.00430.36340.096*
H9C0.77571.10500.29910.096*
C150.9830 (5)0.8997 (4)0.7768 (9)0.0703 (19)
H150.93040.92030.81290.084*
C80.6106 (4)0.8212 (4)0.2840 (8)0.0574 (16)
H8A0.63080.77400.36860.069*
H8B0.56980.79280.19640.069*
C191.0677 (4)0.8508 (4)0.5506 (9)0.0667 (18)
H191.07340.83640.43150.080*
C181.1391 (4)0.8442 (5)0.6711 (11)0.081 (2)
H181.19230.82610.63380.098*
C161.0522 (6)0.8924 (5)0.9036 (9)0.083 (2)
H161.04600.90581.02290.099*
C171.1303 (5)0.8648 (5)0.8479 (12)0.086 (2)
H171.17790.86000.93050.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.047 (3)0.038 (2)0.054 (3)0.002 (2)0.018 (2)0.005 (2)
O10.076 (3)0.059 (3)0.060 (3)0.008 (2)0.036 (2)0.004 (2)
N20.056 (3)0.044 (3)0.045 (3)0.001 (2)0.017 (2)0.003 (2)
C20.052 (3)0.046 (3)0.041 (3)0.001 (3)0.013 (3)0.001 (3)
C10.050 (3)0.033 (3)0.043 (3)0.000 (3)0.004 (3)0.003 (3)
C50.039 (3)0.038 (3)0.049 (3)0.004 (2)0.005 (3)0.008 (3)
O110.062 (3)0.046 (2)0.089 (3)0.001 (2)0.003 (2)0.022 (2)
C30.043 (3)0.049 (3)0.032 (3)0.001 (3)0.003 (2)0.001 (3)
C60.041 (3)0.043 (3)0.039 (3)0.003 (2)0.008 (2)0.003 (3)
N120.054 (3)0.051 (3)0.053 (3)0.006 (2)0.007 (2)0.000 (2)
C70.047 (3)0.051 (4)0.050 (3)0.009 (3)0.017 (3)0.003 (3)
C100.057 (4)0.051 (4)0.062 (4)0.006 (3)0.011 (3)0.011 (3)
C140.045 (3)0.040 (3)0.056 (4)0.006 (3)0.007 (3)0.003 (3)
C40.043 (3)0.038 (3)0.041 (3)0.000 (2)0.004 (3)0.003 (3)
C110.054 (4)0.033 (3)0.053 (4)0.005 (3)0.007 (3)0.008 (3)
C120.049 (3)0.053 (4)0.052 (3)0.002 (3)0.001 (3)0.011 (3)
C130.057 (4)0.052 (4)0.064 (4)0.004 (3)0.012 (3)0.006 (3)
C90.075 (4)0.068 (4)0.053 (4)0.015 (3)0.028 (3)0.014 (3)
C150.078 (5)0.066 (4)0.069 (5)0.001 (4)0.017 (4)0.009 (4)
C80.056 (4)0.047 (3)0.071 (4)0.005 (3)0.022 (3)0.000 (3)
C190.067 (4)0.073 (5)0.060 (4)0.002 (4)0.005 (4)0.008 (3)
C180.052 (4)0.096 (6)0.095 (6)0.001 (4)0.004 (4)0.016 (5)
C160.105 (6)0.085 (5)0.056 (4)0.009 (5)0.006 (5)0.004 (4)
C170.088 (6)0.076 (5)0.090 (6)0.012 (4)0.025 (5)0.010 (5)
Geometric parameters (Å, º) top
N1—C111.383 (6)C10—H10C0.9600
N1—C11.418 (6)C14—C151.365 (8)
N1—C81.460 (6)C14—C191.376 (7)
O1—C71.247 (6)C14—C131.521 (8)
N2—C71.329 (6)C11—C121.523 (7)
N2—C61.408 (6)C12—H12A0.9700
N2—H2N0.8491C12—H12B0.9700
C2—C31.389 (7)C13—H13A0.9700
C2—C11.399 (7)C13—H13B0.9700
C2—H20.9300C9—H9A0.9600
C1—C61.384 (7)C9—H9B0.9600
C5—C41.380 (7)C9—H9C0.9600
C5—C61.385 (7)C15—C161.384 (9)
C5—H50.9300C15—H150.9300
O11—C111.223 (6)C8—H8A0.9700
C3—C41.402 (7)C8—H8B0.9700
C3—C91.510 (7)C19—C181.380 (8)
N12—C131.437 (7)C19—H190.9300
N12—C121.460 (6)C18—C171.380 (10)
N12—H12N0.9138C18—H180.9300
C7—C81.503 (7)C16—C171.372 (10)
C10—C41.510 (7)C16—H160.9300
C10—H10A0.9600C17—H170.9300
C10—H10B0.9600
C11—N1—C1125.8 (4)N1—C11—C12120.1 (4)
C11—N1—C8118.8 (4)N12—C12—C11112.6 (4)
C1—N1—C8114.8 (4)N12—C12—H12A109.1
C7—N2—C6123.2 (5)C11—C12—H12A109.1
C7—N2—H2N113.8N12—C12—H12B109.1
C6—N2—H2N121.2C11—C12—H12B109.1
C3—C2—C1120.8 (5)H12A—C12—H12B107.8
C3—C2—H2119.6N12—C13—C14113.3 (5)
C1—C2—H2119.6N12—C13—H13A108.9
C6—C1—C2118.8 (5)C14—C13—H13A108.9
C6—C1—N1118.1 (4)N12—C13—H13B108.9
C2—C1—N1123.0 (5)C14—C13—H13B108.9
C4—C5—C6121.7 (5)H13A—C13—H13B107.7
C4—C5—H5119.1C3—C9—H9A109.5
C6—C5—H5119.1C3—C9—H9B109.5
C2—C3—C4119.6 (5)H9A—C9—H9B109.5
C2—C3—C9119.2 (5)C3—C9—H9C109.5
C4—C3—C9121.2 (5)H9A—C9—H9C109.5
C1—C6—C5119.9 (5)H9B—C9—H9C109.5
C1—C6—N2118.5 (5)C14—C15—C16123.1 (7)
C5—C6—N2121.6 (5)C14—C15—H15118.5
C13—N12—C12111.8 (4)C16—C15—H15118.5
C13—N12—H12N112.4N1—C8—C7112.3 (4)
C12—N12—H12N110.9N1—C8—H8A109.1
O1—C7—N2123.0 (5)C7—C8—H8A109.1
O1—C7—C8120.1 (5)N1—C8—H8B109.1
N2—C7—C8116.9 (5)C7—C8—H8B109.1
C4—C10—H10A109.5H8A—C8—H8B107.9
C4—C10—H10B109.5C14—C19—C18121.9 (6)
H10A—C10—H10B109.5C14—C19—H19119.0
C4—C10—H10C109.5C18—C19—H19119.0
H10A—C10—H10C109.5C19—C18—C17118.9 (7)
H10B—C10—H10C109.5C19—C18—H18120.6
C15—C14—C19117.2 (6)C17—C18—H18120.6
C15—C14—C13119.7 (5)C17—C16—C15118.0 (7)
C19—C14—C13123.1 (5)C17—C16—H16121.0
C5—C4—C3118.7 (5)C15—C16—H16121.0
C5—C4—C10119.9 (5)C16—C17—C18120.9 (7)
C3—C4—C10121.4 (5)C16—C17—H17119.6
O11—C11—N1119.4 (5)C18—C17—H17119.6
O11—C11—C12120.4 (5)
N1—C1—C6—N21.9 (7)C8—N1—C11—C12166.0 (5)
C1—C6—N2—C719.1 (7)C1—N1—C11—C124.9 (8)
C6—N2—C7—C85.5 (8)N1—C11—C12—N12145.6 (5)
N2—C7—C8—N126.3 (7)C11—C12—N12—C1365.3 (6)
C7—C8—N1—C145.7 (6)C12—N12—C13—C14176.3 (4)
C8—N1—C1—C634.2 (7)N12—C13—C14—C15169.5 (5)
C8—N1—C11—O1112.0 (8)N12—C13—C14—C1912.9 (8)
C1—N1—C11—O11177.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O110.972.272.705 (7)106
C19—H19···N120.932.512.857 (8)102
N2—H2N···O1i0.852.072.913 (6)171
C2—H2···O11ii0.932.393.255 (7)154
C12—H12A···O11ii0.972.543.285 (7)134
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+3/2, z1/2.
 

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