2,6-Dimethyl­quinoline

The title compound, C₁₁H₁₁N, excluding the methyl H atoms, is planar. The H atoms of the methyl groups are disordered over two sites of equal occupancy.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.101
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.87
           From the CIF: _reflns_number_total               1202
           Count of symmetry unique reflns         1201
           Completeness (_total/calc)            100.08%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present         no

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

   1 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
   0 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

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S1. Comment

The derivatives of quinoline are of great significance as a result of their various bioactivities. For example, they can be used as antagonists, matrix metalloproteinase inhibitors and glucocorticoid mimetics (Geneste, et al. 2006; Beadle, et al., 2005; Schäfer, et al., 2003). In this paper we present the crystal structure of the title compound, 2,6-dimethylquinoline, (I).

The two methyl groups are coplanar with the quinoline ring, which is almost planar, with an r. m. s. derivation of 0.0111 (2) Å. The H atoms of the methyl groups are disordered 50:50 over two sites.

Related literature

For related literature, see: Beadle et al. (2005); Geneste et al. (2006); Schäfer et al. (2003).

S2. Experimental

The title compound was bought from Shanghai Kuilin Chemical Co., Ltd. as the synthetic raw material. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a CH₂Cl₂ solution.

S3. Refinement

All H atoms were positioned geometrically and refined as riding with C—H = 0.95 and 0.98 Å. For the CH groups, U_iso(H) values are set equal to 1.2U_eq(carrier atom) and for the methyl groups they are set equal to 1.5U_eq(carrier atom). The H atoms of the methyl groups are disordered over two sites [both occupancies 0.50:0.50].

Computing details

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures

Fig. 1. View of a molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level.

2,6-dimethylquinoline

Crystal data

C11H11N	Dx = 1.224 Mg m^−3
Mr = 157.21	Melting point: 328 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2085 reflections
a = 5.9497 (3) Å	θ = 3.0–25.0°
b = 10.6987 (8) Å	µ = 0.07 mm^−1
c = 13.4021 (12) Å	T = 113 K
V = 853.10 (11) Å^3	Plate, colourless
Z = 4	0.20 × 0.16 × 0.14 mm
F(000) = 336

Data collection

Rigaku Saturn diffractometer	1202 independent reflections
Radiation source: rotating anode	1098 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.048
Detector resolution: 7.31 pixels mm^-1	θmax = 27.9°, θmin = 2.4°
ω scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 1999)	k = −14→14
Tmin = 0.986, Tmax = 0.990	l = −17→17
10784 measured reflections

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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0508P)^2 + 0.0963P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
1202 reflections	Δρmax = 0.19 e Å^−3
111 parameters	Δρmin = −0.14 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: 0.046 (7)

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	Occ. (<1)
N1	1.0066 (2)	0.52180 (13)	0.07529 (10)	0.0232 (4)
C1	0.9191 (3)	0.46134 (15)	−0.00134 (13)	0.0226 (4)
C2	0.7025 (3)	0.48864 (16)	−0.04071 (13)	0.0228 (4)
H2	0.6453	0.4420	−0.0954	0.027*
C3	0.5771 (3)	0.58242 (15)	0.00067 (12)	0.0216 (4)
H3	0.4325	0.6019	−0.0251	0.026*
C4	0.6660 (3)	0.65016 (15)	0.08253 (12)	0.0192 (4)
C5	0.8820 (3)	0.61591 (15)	0.11774 (12)	0.0201 (4)
C6	0.9720 (3)	0.68026 (16)	0.20107 (13)	0.0240 (4)
H6	1.1162	0.6582	0.2259	0.029*
C7	0.8528 (3)	0.77392 (17)	0.24591 (13)	0.0258 (4)
H7	0.9168	0.8167	0.3011	0.031*
C8	0.6361 (3)	0.80873 (15)	0.21201 (13)	0.0231 (4)
C9	0.5470 (3)	0.74754 (15)	0.13096 (12)	0.0211 (4)
H9	0.4028	0.7710	0.1070	0.025*
C10	1.0594 (4)	0.35966 (16)	−0.04720 (15)	0.0314 (5)
H10A	1.2025	0.3532	−0.0113	0.047*	0.50
H10B	1.0884	0.3796	−0.1174	0.047*	0.50
H10C	0.9789	0.2800	−0.0428	0.047*	0.50
H10D	0.9774	0.3220	−0.1030	0.047*	0.50
H10E	1.0914	0.2956	0.0031	0.047*	0.50
H10F	1.2010	0.3952	−0.0716	0.047*	0.50
C11	0.5081 (4)	0.90984 (16)	0.26553 (14)	0.0306 (5)
H11A	0.5989	0.9418	0.3209	0.046*	0.50
H11B	0.3671	0.8755	0.2915	0.046*	0.50
H11C	0.4749	0.9780	0.2190	0.046*	0.50
H11D	0.3617	0.9217	0.2334	0.046*	0.50
H11E	0.5935	0.9881	0.2627	0.046*	0.50
H11F	0.4857	0.8856	0.3353	0.046*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0235 (7)	0.0234 (7)	0.0227 (7)	0.0014 (7)	0.0019 (6)	0.0027 (6)
C1	0.0255 (9)	0.0203 (8)	0.0220 (8)	−0.0001 (7)	0.0037 (7)	0.0034 (7)
C2	0.0262 (9)	0.0208 (8)	0.0213 (9)	−0.0043 (8)	0.0002 (7)	0.0000 (7)
C3	0.0189 (8)	0.0243 (8)	0.0218 (8)	−0.0024 (7)	0.0001 (7)	0.0023 (7)
C4	0.0199 (8)	0.0193 (8)	0.0185 (8)	−0.0021 (7)	0.0019 (7)	0.0029 (7)
C5	0.0198 (8)	0.0204 (8)	0.0200 (8)	−0.0005 (7)	0.0023 (7)	0.0039 (7)
C6	0.0211 (9)	0.0305 (9)	0.0205 (9)	−0.0022 (8)	−0.0020 (7)	0.0027 (7)
C7	0.0285 (10)	0.0270 (9)	0.0219 (9)	−0.0045 (8)	−0.0014 (8)	−0.0006 (7)
C8	0.0278 (9)	0.0202 (8)	0.0213 (9)	−0.0017 (7)	0.0048 (8)	0.0014 (7)
C9	0.0196 (8)	0.0213 (8)	0.0225 (8)	0.0002 (7)	0.0028 (7)	0.0035 (7)
C10	0.0348 (11)	0.0266 (9)	0.0327 (10)	0.0047 (9)	0.0031 (9)	−0.0022 (8)
C11	0.0381 (10)	0.0259 (9)	0.0279 (10)	0.0033 (9)	0.0055 (8)	−0.0024 (7)

Geometric parameters (Å, º)

N1—C1	1.321 (2)	C8—C9	1.375 (2)
N1—C5	1.374 (2)	C8—C11	1.505 (2)
C1—C2	1.423 (2)	C9—H9	0.9500
C1—C10	1.503 (2)	C10—H10A	0.9800
C2—C3	1.368 (2)	C10—H10B	0.9800
C2—H2	0.9500	C10—H10C	0.9800
C3—C4	1.417 (2)	C10—H10D	0.9800
C3—H3	0.9500	C10—H10E	0.9800
C4—C9	1.417 (2)	C10—H10F	0.9800
C4—C5	1.418 (2)	C11—H11A	0.9800
C5—C6	1.417 (2)	C11—H11B	0.9800
C6—C7	1.367 (2)	C11—H11C	0.9800
C6—H6	0.9500	C11—H11D	0.9800
C7—C8	1.417 (3)	C11—H11E	0.9800
C7—H7	0.9500	C11—H11F	0.9800
C1—N1—C5	117.92 (15)	H10A—C10—H10D	141.1
N1—C1—C2	123.02 (16)	H10B—C10—H10D	56.3
N1—C1—C10	116.98 (16)	H10C—C10—H10D	56.3
C2—C1—C10	120.00 (17)	C1—C10—H10E	109.5
C3—C2—C1	119.62 (17)	H10A—C10—H10E	56.3
C3—C2—H2	120.2	H10B—C10—H10E	141.1
C1—C2—H2	120.2	H10C—C10—H10E	56.3
C2—C3—C4	119.05 (17)	H10D—C10—H10E	109.5
C2—C3—H3	120.5	C1—C10—H10F	109.5
C4—C3—H3	120.5	H10A—C10—H10F	56.3
C9—C4—C3	122.98 (15)	H10B—C10—H10F	56.3
C9—C4—C5	119.38 (15)	H10C—C10—H10F	141.1
C3—C4—C5	117.63 (15)	H10D—C10—H10F	109.5
N1—C5—C6	118.59 (16)	H10E—C10—H10F	109.5
N1—C5—C4	122.76 (16)	C8—C11—H11A	109.5
C6—C5—C4	118.65 (15)	C8—C11—H11B	109.5
C7—C6—C5	120.43 (17)	H11A—C11—H11B	109.5
C7—C6—H6	119.8	C8—C11—H11C	109.5
C5—C6—H6	119.8	H11A—C11—H11C	109.5
C6—C7—C8	121.59 (17)	H11B—C11—H11C	109.5
C6—C7—H7	119.2	C8—C11—H11D	109.5
C8—C7—H7	119.2	H11A—C11—H11D	141.1
C9—C8—C7	118.64 (16)	H11B—C11—H11D	56.3
C9—C8—C11	121.58 (17)	H11C—C11—H11D	56.3
C7—C8—C11	119.77 (17)	C8—C11—H11E	109.5
C8—C9—C4	121.29 (16)	H11A—C11—H11E	56.3
C8—C9—H9	119.4	H11B—C11—H11E	141.1
C4—C9—H9	119.4	H11C—C11—H11E	56.3
C1—C10—H10A	109.5	H11D—C11—H11E	109.5
C1—C10—H10B	109.5	C8—C11—H11F	109.5
H10A—C10—H10B	109.5	H11A—C11—H11F	56.3
C1—C10—H10C	109.5	H11B—C11—H11F	56.3
H10A—C10—H10C	109.5	H11C—C11—H11F	141.1
H10B—C10—H10C	109.5	H11D—C11—H11F	109.5
C1—C10—H10D	109.5	H11E—C11—H11F	109.5
C5—N1—C1—C2	−0.6 (2)	C9—C4—C5—C6	0.3 (2)
C5—N1—C1—C10	179.40 (14)	C3—C4—C5—C6	−178.47 (15)
N1—C1—C2—C3	0.8 (2)	N1—C5—C6—C7	−179.55 (15)
C10—C1—C2—C3	−179.16 (15)	C4—C5—C6—C7	−0.4 (2)
C1—C2—C3—C4	−0.3 (2)	C5—C6—C7—C8	0.8 (3)
C2—C3—C4—C9	−179.10 (15)	C6—C7—C8—C9	−1.1 (3)
C2—C3—C4—C5	−0.4 (2)	C6—C7—C8—C11	178.20 (16)
C1—N1—C5—C6	178.96 (15)	C7—C8—C9—C4	1.0 (2)
C1—N1—C5—C4	−0.2 (2)	C11—C8—C9—C4	−178.31 (15)
C9—C4—C5—N1	179.40 (14)	C3—C4—C9—C8	178.10 (15)
C3—C4—C5—N1	0.6 (2)	C5—C4—C9—C8	−0.6 (2)