4-[(4-Ethoxy­phen­yl)amino­acet­yl]-6,7-dimethyl-1,2,3,4-tetra­hydro­quinoxalin-2-one

All the inter­atomic distances in the title compound, C₂₂H₂₅N₃O₄, are normal. The heteroatom ring of the quinoxalinone system shows a half-chair conformation, slightly distorted towards a sofa. In the crystal structure, the mol­ecules dimerize via a pair of N—H...O hydrogen bonds. The dimers are linked by C—H...O and possible C—H—π inter­actions into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.058
• wR factor = 0.132
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   C7      ..       5.50 su
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C10

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990) and Mercury (Version 1.4; Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

4-[(4-Ethoxyphenyl)aminoacetyl]-6,7-dimethyl-1,2,3,4-tetrahydroquinoxalin-2-one

Crystal data

C22H25N3O4	Z = 2
Mr = 395.45	F(000) = 420
Triclinic, P1	Dx = 1.274 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.634 (1) Å	Cell parameters from 99 reflections
b = 10.547 (2) Å	θ = 4–20°
c = 15.276 (3) Å	µ = 0.09 mm^−1
α = 94.21 (3)°	T = 291 K
β = 90.10 (3)°	Plate, colourless
γ = 104.64 (3)°	0.35 × 0.11 × 0.07 mm
V = 1031.1 (4) Å^3

Data collection

Kuma KM-4 diffractometer	1787 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Graphite monochromator	θmax = 27.6°, θmin = 2.0°
ω/2θ scans	h = −8→0
Absorption correction: ψ scan (North et al., 1968)	k = −13→10
Tmin = 0.971, Tmax = 0.996	l = −19→19
4993 measured reflections	3 standard reflections every 100 reflections
4518 independent reflections	intensity decay: 4.2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.0454P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.87	(Δ/σ)max = 0.001
4518 reflections	Δρmax = 0.18 e Å^−3
267 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9887 (5)	0.9581 (3)	0.82931 (17)	0.0363 (8)
C2	0.8261 (5)	1.0042 (3)	0.79713 (18)	0.0400 (8)
H2	0.7222	0.9472	0.7621	0.048*
C3	0.8153 (5)	1.1332 (3)	0.81613 (18)	0.0405 (8)
C4	0.9703 (5)	1.2188 (3)	0.86945 (19)	0.0421 (8)
C5	1.1261 (5)	1.1703 (3)	0.90551 (18)	0.0407 (8)
H5	1.2264	1.2256	0.9431	0.049*
C6	1.1344 (4)	1.0416 (3)	0.88655 (18)	0.0366 (7)
N1	1.0147 (4)	0.8300 (2)	0.80888 (14)	0.0346 (6)
N2	1.2919 (4)	0.9930 (2)	0.92377 (15)	0.0408 (6)
H2N	1.3899	1.0479	0.9691	0.049*
C7	1.2760 (5)	0.8640 (3)	0.92870 (19)	0.0425 (8)
C8	1.0887 (5)	0.7717 (3)	0.88250 (18)	0.0431 (8)
H8A	1.1248	0.6916	0.8611	0.052*
H8B	0.9774	0.7487	0.9241	0.052*
C9	0.6412 (5)	1.1802 (3)	0.7762 (2)	0.0582 (10)
H9A	0.5452	1.1073	0.7449	0.087*
H9B	0.6982	1.2457	0.7363	0.087*
H9C	0.5696	1.2173	0.8219	0.087*
C10	0.9687 (5)	1.3604 (3)	0.8897 (2)	0.0593 (10)
H10A	1.0860	1.4035	0.9271	0.089*
H10B	0.8421	1.3647	0.9187	0.089*
H10C	0.9769	1.4032	0.8360	0.089*
O1	1.4033 (3)	0.8214 (2)	0.96877 (13)	0.0543 (6)
C11	1.0227 (5)	0.7720 (3)	0.72581 (18)	0.0386 (8)
C12	1.0090 (5)	0.8558 (3)	0.65028 (17)	0.0465 (9)
H12A	0.8636	0.8494	0.6368	0.056*
H12B	1.0757	0.9470	0.6680	0.056*
O11	1.0429 (3)	0.6606 (2)	0.71376 (13)	0.0527 (6)
N12	1.1077 (4)	0.8151 (2)	0.57192 (15)	0.0418 (7)
O12	0.6251 (4)	0.5847 (2)	0.27590 (14)	0.0621 (7)
C13	0.9791 (4)	0.7520 (3)	0.49737 (18)	0.0352 (7)
C14	0.9677 (5)	0.8216 (3)	0.42518 (18)	0.0430 (8)
H14	1.0426	0.9090	0.4254	0.052*
C15	0.8465 (5)	0.7626 (3)	0.35295 (19)	0.0457 (8)
H15	0.8394	0.8106	0.3048	0.055*
C16	0.7351 (5)	0.6326 (3)	0.3515 (2)	0.0432 (8)
C17	0.7420 (5)	0.5628 (3)	0.4241 (2)	0.0524 (9)
H17	0.6650	0.4760	0.4244	0.063*
C18	0.8655 (5)	0.6237 (3)	0.4971 (2)	0.0473 (9)
H18	0.8707	0.5768	0.5459	0.057*
C19	0.5230 (5)	0.4480 (3)	0.2657 (2)	0.0642 (11)
H19A	0.4082	0.4275	0.3059	0.077*
H19B	0.6198	0.3960	0.2779	0.077*
C20	0.4436 (6)	0.4186 (4)	0.1720 (2)	0.0821 (13)
H20A	0.3396	0.4652	0.1622	0.123*
H20B	0.3835	0.3259	0.1611	0.123*
H20C	0.5570	0.4460	0.1330	0.123*
C21	1.3195 (5)	0.8367 (3)	0.5745 (2)	0.0466 (8)
C22	1.4213 (5)	0.7971 (4)	0.4931 (2)	0.0672 (11)
H22A	1.4324	0.8628	0.4518	0.101*
H22B	1.3388	0.7144	0.4675	0.101*
H22C	1.5579	0.7888	0.5079	0.101*
O13	1.4194 (4)	0.8874 (2)	0.64085 (15)	0.0720 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0403 (19)	0.046 (2)	0.0243 (15)	0.0143 (16)	−0.0003 (14)	−0.0020 (14)
C2	0.0363 (18)	0.051 (2)	0.0309 (16)	0.0095 (16)	−0.0030 (14)	−0.0025 (15)
C3	0.0389 (19)	0.054 (2)	0.0353 (17)	0.0221 (17)	0.0078 (15)	0.0073 (16)
C4	0.046 (2)	0.045 (2)	0.0374 (17)	0.0165 (17)	0.0057 (16)	0.0013 (15)
C5	0.047 (2)	0.041 (2)	0.0326 (17)	0.0113 (16)	−0.0060 (15)	−0.0062 (14)
C6	0.0343 (18)	0.044 (2)	0.0333 (16)	0.0137 (16)	−0.0013 (14)	0.0006 (15)
N1	0.0420 (15)	0.0360 (15)	0.0274 (13)	0.0138 (12)	−0.0055 (12)	−0.0003 (11)
N2	0.0427 (16)	0.0420 (17)	0.0373 (14)	0.0121 (13)	−0.0157 (12)	−0.0036 (12)
C7	0.052 (2)	0.045 (2)	0.0292 (16)	0.0117 (18)	−0.0038 (16)	−0.0033 (15)
C8	0.052 (2)	0.0416 (19)	0.0334 (17)	0.0088 (17)	−0.0078 (15)	0.0018 (14)
C9	0.051 (2)	0.067 (2)	0.065 (2)	0.029 (2)	−0.0040 (19)	0.0040 (19)
C10	0.066 (2)	0.050 (2)	0.065 (2)	0.021 (2)	0.000 (2)	0.0028 (19)
O1	0.0589 (15)	0.0575 (15)	0.0506 (13)	0.0241 (13)	−0.0222 (12)	−0.0023 (12)
C11	0.0391 (19)	0.045 (2)	0.0332 (17)	0.0151 (16)	−0.0051 (14)	−0.0042 (15)
C12	0.061 (2)	0.056 (2)	0.0279 (16)	0.0262 (18)	−0.0001 (16)	−0.0017 (15)
O11	0.0715 (17)	0.0467 (15)	0.0439 (13)	0.0249 (13)	−0.0071 (12)	−0.0044 (11)
N12	0.0466 (17)	0.0537 (17)	0.0279 (13)	0.0193 (14)	−0.0025 (12)	−0.0025 (12)
O12	0.0707 (17)	0.0566 (16)	0.0538 (15)	0.0099 (14)	−0.0258 (13)	−0.0073 (12)
C13	0.0371 (18)	0.0425 (19)	0.0292 (15)	0.0168 (16)	−0.0006 (14)	−0.0009 (14)
C14	0.048 (2)	0.043 (2)	0.0360 (17)	0.0077 (17)	−0.0011 (15)	0.0043 (15)
C15	0.048 (2)	0.054 (2)	0.0336 (17)	0.0102 (18)	−0.0077 (16)	0.0046 (16)
C16	0.043 (2)	0.048 (2)	0.0377 (18)	0.0129 (17)	−0.0071 (16)	−0.0068 (16)
C17	0.053 (2)	0.041 (2)	0.060 (2)	0.0074 (17)	−0.0125 (19)	0.0045 (17)
C18	0.057 (2)	0.043 (2)	0.0415 (18)	0.0106 (18)	−0.0068 (17)	0.0084 (15)
C19	0.050 (2)	0.059 (3)	0.080 (3)	0.010 (2)	−0.012 (2)	−0.011 (2)
C20	0.064 (3)	0.095 (3)	0.076 (3)	0.013 (2)	−0.020 (2)	−0.031 (2)
C21	0.041 (2)	0.056 (2)	0.043 (2)	0.0114 (18)	−0.0057 (17)	0.0048 (17)
C22	0.043 (2)	0.100 (3)	0.063 (2)	0.025 (2)	0.0066 (19)	0.008 (2)
O13	0.0619 (16)	0.088 (2)	0.0586 (16)	0.0082 (15)	−0.0251 (14)	−0.0072 (14)

Geometric parameters (Å, º)

C1—C6	1.389 (4)	C12—N12	1.455 (3)
C1—C2	1.393 (4)	C12—H12A	0.9700
C1—N1	1.418 (3)	C12—H12B	0.9700
C2—C3	1.390 (4)	N12—C21	1.365 (4)
C2—H2	0.9300	N12—C13	1.437 (3)
C3—C4	1.399 (4)	O12—C16	1.359 (3)
C3—C9	1.511 (4)	O12—C19	1.426 (4)
C4—C5	1.393 (4)	C13—C18	1.372 (4)
C4—C10	1.505 (4)	C13—C14	1.381 (4)
C5—C6	1.382 (4)	C14—C15	1.376 (4)
C5—H5	0.9300	C14—H14	0.9300
C6—N2	1.410 (3)	C15—C16	1.383 (4)
N1—C11	1.375 (3)	C15—H15	0.9300
N1—C8	1.461 (3)	C16—C17	1.382 (4)
N2—C7	1.345 (4)	C17—C18	1.397 (4)
N2—H2N	0.9930	C17—H17	0.9300
C7—O1	1.234 (3)	C18—H18	0.9300
C7—C8	1.508 (4)	C19—C20	1.508 (4)
C8—H8A	0.9700	C19—H19A	0.9700
C8—H8B	0.9700	C19—H19B	0.9700
C9—H9A	0.9600	C20—H20A	0.9600
C9—H9B	0.9600	C20—H20B	0.9600
C9—H9C	0.9600	C20—H20C	0.9600
C10—H10A	0.9600	C21—O13	1.221 (3)
C10—H10B	0.9600	C21—C22	1.499 (4)
C10—H10C	0.9600	C22—H22A	0.9600
C11—O11	1.217 (3)	C22—H22B	0.9600
C11—C12	1.520 (4)	C22—H22C	0.9600
C6—C1—C2	118.4 (3)	N12—C12—H12A	109.2
C6—C1—N1	117.1 (3)	C11—C12—H12A	109.2
C2—C1—N1	124.5 (3)	N12—C12—H12B	109.2
C3—C2—C1	121.6 (3)	C11—C12—H12B	109.2
C3—C2—H2	119.2	H12A—C12—H12B	107.9
C1—C2—H2	119.2	C21—N12—C13	123.6 (3)
C2—C3—C4	119.3 (3)	C21—N12—C12	117.4 (3)
C2—C3—C9	119.6 (3)	C13—N12—C12	119.0 (2)
C4—C3—C9	121.0 (3)	C16—O12—C19	118.4 (3)
C5—C4—C3	118.8 (3)	C18—C13—C14	119.3 (3)
C5—C4—C10	119.9 (3)	C18—C13—N12	121.0 (3)
C3—C4—C10	121.3 (3)	C14—C13—N12	119.7 (3)
C6—C5—C4	121.2 (3)	C15—C14—C13	120.5 (3)
C6—C5—H5	119.4	C15—C14—H14	119.7
C4—C5—H5	119.4	C13—C14—H14	119.7
C5—C6—C1	120.4 (3)	C14—C15—C16	120.4 (3)
C5—C6—N2	120.9 (3)	C14—C15—H15	119.8
C1—C6—N2	118.8 (3)	C16—C15—H15	119.8
C11—N1—C1	125.7 (2)	O12—C16—C17	125.6 (3)
C11—N1—C8	118.2 (2)	O12—C16—C15	114.9 (3)
C1—N1—C8	114.4 (2)	C17—C16—C15	119.5 (3)
C7—N2—C6	123.0 (3)	C16—C17—C18	119.6 (3)
C7—N2—H2N	111.9	C16—C17—H17	120.2
C6—N2—H2N	120.3	C18—C17—H17	120.2
O1—C7—N2	123.3 (3)	C13—C18—C17	120.6 (3)
O1—C7—C8	120.9 (3)	C13—C18—H18	119.7
N2—C7—C8	115.8 (3)	C17—C18—H18	119.7
N1—C8—C7	112.0 (3)	O12—C19—C20	106.9 (3)
N1—C8—H8A	109.2	O12—C19—H19A	110.3
C7—C8—H8A	109.2	C20—C19—H19A	110.3
N1—C8—H8B	109.2	O12—C19—H19B	110.3
C7—C8—H8B	109.2	C20—C19—H19B	110.3
H8A—C8—H8B	107.9	H19A—C19—H19B	108.6
C3—C9—H9A	109.5	C19—C20—H20A	109.5
C3—C9—H9B	109.5	C19—C20—H20B	109.5
H9A—C9—H9B	109.5	H20A—C20—H20B	109.5
C3—C9—H9C	109.5	C19—C20—H20C	109.5
H9A—C9—H9C	109.5	H20A—C20—H20C	109.5
H9B—C9—H9C	109.5	H20B—C20—H20C	109.5
C4—C10—H10A	109.5	O13—C21—N12	120.5 (3)
C4—C10—H10B	109.5	O13—C21—C22	122.2 (3)
H10A—C10—H10B	109.5	N12—C21—C22	117.3 (3)
C4—C10—H10C	109.5	C21—C22—H22A	109.5
H10A—C10—H10C	109.5	C21—C22—H22B	109.5
H10B—C10—H10C	109.5	H22A—C22—H22B	109.5
O11—C11—N1	121.6 (3)	C21—C22—H22C	109.5
O11—C11—C12	122.1 (3)	H22A—C22—H22C	109.5
N1—C11—C12	116.2 (3)	H22B—C22—H22C	109.5
N12—C12—C11	112.0 (3)
C6—C1—C2—C3	4.5 (4)	C8—N1—C11—O11	17.0 (4)
N1—C1—C2—C3	−176.7 (3)	C1—N1—C11—C12	2.0 (4)
C1—C2—C3—C4	−0.5 (4)	C8—N1—C11—C12	−161.9 (3)
C1—C2—C3—C9	177.2 (3)	O11—C11—C12—N12	−24.5 (4)
C2—C3—C4—C5	−3.1 (4)	N1—C11—C12—N12	154.4 (2)
C9—C3—C4—C5	179.3 (3)	C11—C12—N12—C21	−68.7 (4)
C2—C3—C4—C10	178.2 (3)	C11—C12—N12—C13	109.7 (3)
C9—C3—C4—C10	0.5 (4)	C21—N12—C13—C18	103.2 (4)
C3—C4—C5—C6	2.7 (4)	C12—N12—C13—C18	−75.1 (4)
C10—C4—C5—C6	−178.5 (3)	C21—N12—C13—C14	−77.5 (4)
C4—C5—C6—C1	1.3 (4)	C12—N12—C13—C14	104.2 (3)
C4—C5—C6—N2	−179.6 (3)	C18—C13—C14—C15	−1.0 (4)
C2—C1—C6—C5	−4.8 (4)	N12—C13—C14—C15	179.6 (3)
N1—C1—C6—C5	176.2 (3)	C13—C14—C15—C16	−0.3 (5)
C2—C1—C6—N2	176.0 (3)	C19—O12—C16—C17	−6.4 (5)
N1—C1—C6—N2	−2.9 (4)	C19—O12—C16—C15	173.8 (3)
C6—C1—N1—C11	−126.9 (3)	C14—C15—C16—O12	−178.6 (3)
C2—C1—N1—C11	54.2 (4)	C14—C15—C16—C17	1.6 (5)
C6—C1—N1—C8	37.6 (4)	O12—C16—C17—C18	178.6 (3)
C2—C1—N1—C8	−141.3 (3)	C15—C16—C17—C18	−1.6 (5)
C5—C6—N2—C7	160.4 (3)	C14—C13—C18—C17	1.1 (5)
C1—C6—N2—C7	−20.5 (4)	N12—C13—C18—C17	−179.6 (3)
C6—N2—C7—O1	−172.6 (3)	C16—C17—C18—C13	0.2 (5)
C6—N2—C7—C8	6.8 (4)	C16—O12—C19—C20	−171.3 (3)
C11—N1—C8—C7	116.4 (3)	C13—N12—C21—O13	−177.8 (3)
C1—N1—C8—C7	−49.3 (3)	C12—N12—C21—O13	0.5 (5)
O1—C7—C8—N1	−153.4 (3)	C13—N12—C21—C22	2.8 (5)
N2—C7—C8—N1	27.3 (4)	C12—N12—C21—C22	−178.8 (3)
C1—N1—C11—O11	−179.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1^i	0.99	1.88	2.852 (3)	166
C8—H8A···O11	0.97	2.30	2.736 (3)	107
C19—H19B···O11^ii	0.97	2.46	3.380 (4)	158
C15—H15···Cg1^iii	0.93	2.83	3.652 (5)	148
C22—H22C···Cg2^iv	0.96	2.72	3.474 (5)	136

Symmetry codes: (i) −x+3, −y+2, −z+2; (ii) −x+2, −y+1, −z+1; (iii) −x+2, −y+2, −z+1; (iv) x+1, y, z.