2,6-Di­methyl­quinolin-4(1H)-one

The structure of 2,6-di­methyl­quinolin-4(1H)-one, C₁₁H₁₁NO, has been determined as part of our study on the synthesis and crystallography of quinoline and quinazoline derivatives. It crystallizes in the monoclinic space group P2₁/c. The mol­ecule is planar, with the dihedral angle between the planes of the two rings being 2 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.134
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full too Low ..............      24.97 Deg.

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST95 (Nardelli, 1995).

2,6-dimethylquinolin-4(1H)-one

Crystal data

C11H11NO	F(000) = 368
Mr = 173.21	Dx = 1.243 Mg m^−3
Monoclinic, P21/c	Melting point: 533 K
Hall symbol: -P2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.068 (7) Å	Cell parameters from 25 reflections
b = 8.352 (3) Å	θ = 6.2–11.5°
c = 12.253 (5) Å	µ = 0.08 mm^−1
β = 94.15 (4)°	T = 293 K
V = 925.6 (9) Å^3	Plate-like, yellow
Z = 4	0.4 × 0.3 × 0.1 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.009
Radiation source: fine-focus sealed tube, Laboratory X-ray Generator	θmax = 25.0°, θmin = 2.3°
Graphite monochromator	h = 0→10
ω/2θ scans	k = 0→9
1737 measured reflections	l = −14→14
1629 independent reflections	2 standard reflections every 60 min
1306 reflections with I > 2σ(I)	intensity decay: <2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0684P)^2 + 0.2584P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1629 reflections	Δρmax = 0.24 e Å^−3
121 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, fc^*=kfc[1+0.001xfc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (5)

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
O1	0.71725 (14)	0.42824 (15)	−0.03411 (9)	0.0533 (4)
N1	0.71513 (14)	0.20258 (17)	0.26042 (11)	0.0432 (4)
H1	0.7136	0.1556	0.3228	0.052*
C2	0.59707 (18)	0.2905 (2)	0.22294 (14)	0.0441 (4)
C3	0.59554 (18)	0.3650 (2)	0.12367 (14)	0.0457 (4)
H3	0.5118	0.4223	0.0988	0.055*
C4	0.71705 (18)	0.3583 (2)	0.05716 (12)	0.0406 (4)
C5	0.97234 (18)	0.2492 (2)	0.04407 (13)	0.0439 (4)
H5	0.9769	0.3018	−0.0225	0.053*
C6	1.09121 (19)	0.1596 (2)	0.08344 (15)	0.0473 (5)
C7	1.08045 (19)	0.0802 (2)	0.18367 (15)	0.0520 (5)
H7	1.1597	0.0183	0.2115	0.062*
C8	0.95775 (19)	0.0909 (2)	0.24175 (14)	0.0481 (5)
H8	0.9534	0.0356	0.3073	0.058*
C9	0.83806 (17)	0.18606 (19)	0.20141 (12)	0.0390 (4)
C10	0.84381 (17)	0.26447 (19)	0.10086 (12)	0.0382 (4)
C11	1.2274 (2)	0.1455 (3)	0.02081 (18)	0.0648 (6)
H11a	1.1990	0.1223	−0.0545	0.097*
H11b	1.2888	0.0607	0.0513	0.097*
H11c	1.2812	0.2445	0.0257	0.097*
C12	0.4717 (2)	0.3012 (3)	0.29634 (18)	0.0631 (6)
H12a	0.4408	0.1953	0.3149	0.095*
H12b	0.3904	0.3572	0.2591	0.095*
H12c	0.5039	0.3580	0.3619	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0615 (8)	0.0603 (8)	0.0378 (6)	0.0120 (6)	0.0018 (5)	0.0052 (6)
N1	0.0448 (8)	0.0476 (8)	0.0377 (7)	0.0007 (6)	0.0066 (6)	0.0035 (6)
C2	0.0396 (9)	0.0452 (9)	0.0478 (10)	−0.0013 (7)	0.0061 (7)	−0.0036 (8)
C3	0.0390 (9)	0.0500 (10)	0.0474 (9)	0.0046 (7)	−0.0008 (7)	−0.0015 (8)
C4	0.0455 (9)	0.0411 (9)	0.0344 (8)	0.0010 (7)	−0.0016 (7)	−0.0045 (6)
C5	0.0469 (10)	0.0474 (10)	0.0377 (8)	−0.0005 (8)	0.0058 (7)	−0.0024 (7)
C6	0.0415 (9)	0.0475 (10)	0.0531 (10)	0.0011 (7)	0.0054 (7)	−0.0092 (8)
C7	0.0438 (10)	0.0534 (11)	0.0580 (11)	0.0124 (8)	−0.0005 (8)	0.0000 (8)
C8	0.0504 (10)	0.0504 (10)	0.0433 (9)	0.0080 (8)	0.0006 (8)	0.0050 (8)
C9	0.0395 (9)	0.0395 (9)	0.0380 (8)	0.0002 (7)	0.0028 (7)	−0.0040 (7)
C10	0.0403 (9)	0.0391 (9)	0.0351 (8)	0.0002 (7)	0.0009 (6)	−0.0053 (6)
C11	0.0475 (11)	0.0724 (14)	0.0762 (14)	0.0037 (10)	0.0158 (10)	−0.0114 (11)
C12	0.0512 (11)	0.0705 (13)	0.0701 (13)	0.0058 (10)	0.0210 (10)	0.0061 (10)

Geometric parameters (Å, º)

O1—C4	1.2618 (19)	C6—C11	1.505 (3)
N1—C2	1.351 (2)	C7—C8	1.366 (3)
N1—C9	1.379 (2)	C7—H7	0.9300
N1—H1	0.8600	C8—C9	1.406 (2)
C2—C3	1.366 (2)	C8—H8	0.9300
C2—C12	1.502 (3)	C9—C10	1.400 (2)
C3—C4	1.418 (2)	C11—H11a	0.9600
C3—H3	0.9300	C11—H11b	0.9600
C4—C10	1.461 (2)	C11—H11c	0.9600
C5—C6	1.371 (2)	C12—H12a	0.9600
C5—C10	1.406 (2)	C12—H12b	0.9600
C5—H5	0.9300	C12—H12c	0.9600
C6—C7	1.405 (3)
C2—N1—C9	121.81 (14)	C7—C8—C9	119.38 (16)
C2—N1—H1	119.1	C7—C8—H8	120.3
C9—N1—H1	119.1	C9—C8—H8	120.3
N1—C2—C3	120.48 (15)	N1—C9—C10	119.86 (14)
N1—C2—C12	116.38 (16)	N1—C9—C8	120.34 (15)
C3—C2—C12	123.13 (17)	C10—C9—C8	119.80 (15)
C2—C3—C4	122.37 (16)	C9—C10—C5	118.58 (15)
C2—C3—H3	118.8	C9—C10—C4	119.69 (15)
C4—C3—H3	118.8	C5—C10—C4	121.73 (15)
O1—C4—C3	122.82 (15)	C6—C11—H11a	109.5
O1—C4—C10	121.44 (15)	C6—C11—H11b	109.5
C3—C4—C10	115.74 (15)	H11a—C11—H11b	109.5
C6—C5—C10	122.28 (16)	C6—C11—H11c	109.5
C6—C5—H5	118.9	H11a—C11—H11c	109.5
C10—C5—H5	118.9	H11b—C11—H11c	109.5
C5—C6—C7	117.55 (16)	C2—C12—H12a	109.5
C5—C6—C11	121.09 (17)	C2—C12—H12b	109.5
C7—C6—C11	121.36 (17)	H12a—C12—H12b	109.5
C8—C7—C6	122.37 (16)	C2—C12—H12c	109.5
C8—C7—H7	118.8	H12a—C12—H12c	109.5
C6—C7—H7	118.8	H12b—C12—H12c	109.5
C9—N1—C2—C3	0.7 (2)	C7—C8—C9—N1	−177.91 (16)
C9—N1—C2—C12	−178.84 (16)	C7—C8—C9—C10	2.1 (2)
N1—C2—C3—C4	−1.8 (3)	N1—C9—C10—C5	178.15 (15)
C12—C2—C3—C4	177.69 (17)	C8—C9—C10—C5	−1.8 (2)
C2—C3—C4—O1	−179.21 (16)	N1—C9—C10—C4	−2.4 (2)
C2—C3—C4—C10	0.8 (2)	C8—C9—C10—C4	177.66 (15)
C10—C5—C6—C7	0.6 (3)	C6—C5—C10—C9	0.5 (2)
C10—C5—C6—C11	−179.98 (16)	C6—C5—C10—C4	−179.02 (15)
C5—C6—C7—C8	−0.4 (3)	O1—C4—C10—C9	−178.72 (14)
C11—C6—C7—C8	−179.78 (18)	C3—C4—C10—C9	1.3 (2)
C6—C7—C8—C9	−0.9 (3)	O1—C4—C10—C5	0.8 (2)
C2—N1—C9—C10	1.4 (2)	C3—C4—C10—C5	−179.25 (15)
C2—N1—C9—C8	−178.62 (15)