4,4,5,5-Tetra-methyl-2-[4-(2-pyrid-yl)phen-yl]-3,4-dihydro-imidazole-1-oxyl-3-oxide.

In the title compound, C(18)H(20)N(3)O(2), the pyridine and phenyl rings are coplanar [dihedral angle = 3.5 (3)°]. The phenyl ring makes a dihedral angle of 29.6 (1)° with the imidazole ring. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound see: Ullman et al. (1974 ▶). For recent synthetic use of the title compound and its derivatives, see: Li et al. (2009 ▶); Xu et al. (2008 ▶); Masuda et al. (2009 ▶); Train et al. (2009 ▶).

Experimental

Crystal data

C18H20N3O2

M = 310.37

Monoclinic,

a = 8.5150 (17) Å

b = 22.286 (5) Å

c = 9.1360 (18) Å

β = 109.45 (3)°

V = 1634.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.983, T max = 0.983

12953 measured reflections

2819 independent reflections

1896 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.146

S = 1.09

2819 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: Mercury (Macrae et al., 2006 ▶) and CAMERON (Watkin et al., 1996 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013221/bt2927sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013221/bt2927Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H20N3O2	F(000) = 660
Mr = 310.37	Dx = 1.261 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.5150 (17) Å	Cell parameters from 2819 reflections
b = 22.286 (5) Å	θ = 3.0–25.0°
c = 9.1360 (18) Å	µ = 0.08 mm−1
β = 109.45 (3)°	T = 293 K
V = 1634.8 (6) Å3	Block, blue
Z = 4	0.20 × 0.20 × 0.20 mm

Bruker SMART APEX CCD diffractometer	2819 independent reflections
Radiation source: fine-focus sealed tube	1896 reflections with I > 2σ(I)
graphite	Rint = 0.063
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −26→26
Tmin = 0.983, Tmax = 0.983	l = −10→10
12953 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0512P)2 + 0.5834P] where P = (Fo2 + 2Fc2)/3
2819 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.0559 (3)	0.57868 (12)	0.7773 (3)	0.0406 (7)
C2	0.3900 (3)	0.72221 (12)	0.7712 (3)	0.0370 (6)
C4	0.3958 (3)	0.66754 (12)	0.6990 (3)	0.0432 (7)
H4	0.4731	0.6620	0.6483	0.052*
C5	0.5033 (3)	0.77122 (11)	0.7688 (3)	0.0377 (6)
C6	0.2755 (3)	0.72855 (12)	0.8480 (3)	0.0469 (7)
H6	0.2695	0.7646	0.8972	0.056*
C7	0.1736 (3)	0.62798 (11)	0.7782 (3)	0.0365 (6)
C8	0.2889 (3)	0.62182 (12)	0.7019 (3)	0.0440 (7)
H8	0.2939	0.5859	0.6516	0.053*
C9	0.1706 (3)	0.68223 (12)	0.8522 (3)	0.0482 (8)
H9	0.0959	0.6873	0.9058	0.058*
C10	0.7488 (3)	0.82333 (12)	0.7781 (3)	0.0422 (7)
C11	0.6108 (3)	0.86972 (12)	0.7722 (3)	0.0412 (7)
C12	−0.1592 (4)	0.48645 (15)	0.7597 (4)	0.0699 (10)
H12	−0.2267	0.4533	0.7561	0.084*
C13	0.8852 (4)	0.81846 (14)	0.9347 (4)	0.0612 (9)
H13A	0.8362	0.8120	1.0140	0.092*
H13B	0.9490	0.8549	0.9558	0.092*
H13C	0.9569	0.7854	0.9333	0.092*
C14	0.8263 (4)	0.82919 (15)	0.6510 (4)	0.0671 (10)
H14A	0.9077	0.7981	0.6628	0.101*
H14B	0.8789	0.8677	0.6585	0.101*
H14C	0.7411	0.8254	0.5514	0.101*
C15	−0.0669 (5)	0.58456 (16)	0.8416 (5)	0.0849 (13)
H15	−0.0773	0.6201	0.8908	0.102*
C16	0.6523 (4)	0.91381 (15)	0.9054 (4)	0.0726 (11)
H16A	0.5576	0.9390	0.8945	0.109*
H16B	0.7450	0.9382	0.9045	0.109*
H16C	0.6808	0.8923	1.0017	0.109*
C18	0.5432 (4)	0.90355 (16)	0.6188 (4)	0.0720 (10)
H18A	0.5157	0.8755	0.5343	0.108*
H18B	0.6262	0.9310	0.6094	0.108*
H18C	0.4452	0.9254	0.6161	0.108*
C19	−0.0414 (4)	0.48541 (14)	0.6919 (4)	0.0678 (10)
H19	−0.0351	0.4514	0.6352	0.081*
C20	−0.1762 (6)	0.53756 (18)	0.8335 (6)	0.1057 (16)
H20	−0.2595	0.5410	0.8779	0.127*
N1	0.6539 (3)	0.76539 (10)	0.7555 (3)	0.0437 (6)
N2	0.4734 (3)	0.82976 (10)	0.7821 (3)	0.0455 (6)
N3	0.0669 (3)	0.52930 (11)	0.6995 (3)	0.0597 (7)
O1	0.7257 (3)	0.71598 (9)	0.7424 (3)	0.0689 (7)
O2	0.3395 (3)	0.85231 (9)	0.7914 (3)	0.0739 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0425 (16)	0.0374 (17)	0.0416 (17)	0.0011 (12)	0.0136 (14)	0.0010 (13)
C2	0.0350 (15)	0.0354 (16)	0.0390 (16)	0.0010 (12)	0.0101 (13)	0.0015 (12)
C4	0.0427 (16)	0.0451 (18)	0.0463 (18)	−0.0018 (13)	0.0209 (14)	−0.0052 (13)
C5	0.0364 (15)	0.0377 (17)	0.0398 (17)	0.0032 (12)	0.0139 (13)	−0.0007 (12)
C6	0.0516 (18)	0.0376 (17)	0.0558 (19)	−0.0034 (14)	0.0236 (16)	−0.0099 (14)
C7	0.0369 (15)	0.0352 (16)	0.0352 (16)	−0.0006 (11)	0.0089 (13)	0.0004 (12)
C8	0.0514 (18)	0.0369 (16)	0.0439 (18)	−0.0014 (14)	0.0162 (15)	−0.0075 (13)
C9	0.0455 (17)	0.0437 (18)	0.063 (2)	−0.0035 (13)	0.0289 (16)	−0.0064 (14)
C10	0.0409 (16)	0.0403 (16)	0.0478 (18)	−0.0064 (12)	0.0180 (14)	−0.0031 (13)
C11	0.0434 (16)	0.0317 (15)	0.0478 (18)	−0.0064 (12)	0.0141 (14)	−0.0004 (13)
C12	0.076 (2)	0.049 (2)	0.096 (3)	−0.0207 (18)	0.044 (2)	−0.0010 (19)
C13	0.0499 (18)	0.063 (2)	0.063 (2)	−0.0012 (15)	0.0082 (17)	0.0014 (17)
C14	0.086 (3)	0.065 (2)	0.068 (2)	−0.0102 (18)	0.049 (2)	−0.0028 (17)
C15	0.117 (3)	0.056 (2)	0.119 (3)	−0.034 (2)	0.090 (3)	−0.033 (2)
C16	0.059 (2)	0.067 (2)	0.089 (3)	−0.0061 (17)	0.021 (2)	−0.036 (2)
C18	0.068 (2)	0.067 (2)	0.081 (3)	0.0073 (18)	0.025 (2)	0.0286 (19)
C19	0.065 (2)	0.0379 (19)	0.106 (3)	−0.0094 (16)	0.036 (2)	−0.0121 (18)
C20	0.138 (4)	0.079 (3)	0.147 (4)	−0.049 (3)	0.110 (4)	−0.036 (3)
N1	0.0433 (14)	0.0372 (14)	0.0532 (16)	−0.0005 (11)	0.0194 (12)	−0.0037 (11)
N2	0.0397 (14)	0.0350 (14)	0.0647 (17)	0.0016 (11)	0.0212 (12)	0.0003 (11)
N3	0.0569 (17)	0.0402 (16)	0.090 (2)	−0.0082 (12)	0.0358 (15)	−0.0159 (13)
O1	0.0569 (14)	0.0418 (13)	0.121 (2)	0.0004 (10)	0.0471 (14)	−0.0134 (12)
O2	0.0542 (14)	0.0416 (13)	0.139 (2)	0.0080 (11)	0.0504 (14)	0.0038 (12)

C1—N3	1.331 (3)	C12—C19	1.343 (4)
C1—C15	1.365 (4)	C12—C20	1.356 (5)
C1—C7	1.486 (4)	C12—H12	0.9300
C2—C6	1.385 (3)	C13—H13A	0.9600
C2—C4	1.394 (4)	C13—H13B	0.9600
C2—C5	1.463 (4)	C13—H13C	0.9600
C4—C8	1.373 (4)	C14—H14A	0.9600
C4—H4	0.9300	C14—H14B	0.9600
C5—N1	1.334 (3)	C14—H14C	0.9600
C5—N2	1.343 (3)	C15—C20	1.387 (5)
C6—C9	1.374 (4)	C15—H15	0.9300
C6—H6	0.9300	C16—H16A	0.9600
C7—C8	1.388 (4)	C16—H16B	0.9600
C7—C9	1.389 (4)	C16—H16C	0.9600
C8—H8	0.9300	C18—H18A	0.9600
C9—H9	0.9300	C18—H18B	0.9600
C10—N1	1.501 (3)	C18—H18C	0.9600
C10—C13	1.517 (4)	C19—N3	1.331 (4)
C10—C14	1.520 (4)	C19—H19	0.9300
C10—C11	1.552 (4)	C20—H20	0.9300
C11—N2	1.497 (3)	N1—O1	1.284 (3)
C11—C16	1.512 (4)	N2—O2	1.274 (3)
C11—C18	1.525 (4)
N3—C1—C15	120.7 (3)	C10—C13—H13B	109.5
N3—C1—C7	116.5 (2)	H13A—C13—H13B	109.5
C15—C1—C7	122.6 (3)	C10—C13—H13C	109.5
C6—C2—C4	118.1 (2)	H13A—C13—H13C	109.5
C6—C2—C5	120.7 (2)	H13B—C13—H13C	109.5
C4—C2—C5	121.2 (2)	C10—C14—H14A	109.5
C8—C4—C2	120.8 (3)	C10—C14—H14B	109.5
C8—C4—H4	119.6	H14A—C14—H14B	109.5
C2—C4—H4	119.6	C10—C14—H14C	109.5
N1—C5—N2	108.7 (2)	H14A—C14—H14C	109.5
N1—C5—C2	126.0 (2)	H14B—C14—H14C	109.5
N2—C5—C2	125.3 (2)	C1—C15—C20	120.1 (3)
C9—C6—C2	120.8 (3)	C1—C15—H15	120.0
C9—C6—H6	119.6	C20—C15—H15	120.0
C2—C6—H6	119.6	C11—C16—H16A	109.5
C8—C7—C9	117.5 (2)	C11—C16—H16B	109.5
C8—C7—C1	120.9 (2)	H16A—C16—H16B	109.5
C9—C7—C1	121.6 (2)	C11—C16—H16C	109.5
C4—C8—C7	121.4 (2)	H16A—C16—H16C	109.5
C4—C8—H8	119.3	H16B—C16—H16C	109.5
C7—C8—H8	119.3	C11—C18—H18A	109.5
C6—C9—C7	121.5 (3)	C11—C18—H18B	109.5
C6—C9—H9	119.3	H18A—C18—H18B	109.5
C7—C9—H9	119.3	C11—C18—H18C	109.5
N1—C10—C13	106.1 (2)	H18A—C18—H18C	109.5
N1—C10—C14	108.6 (2)	H18B—C18—H18C	109.5
C13—C10—C14	109.6 (2)	N3—C19—C12	125.1 (3)
N1—C10—C11	101.6 (2)	N3—C19—H19	117.5
C13—C10—C11	114.5 (2)	C12—C19—H19	117.5
C14—C10—C11	115.6 (2)	C12—C20—C15	118.7 (3)
N2—C11—C16	108.4 (2)	C12—C20—H20	120.7
N2—C11—C18	106.6 (2)	C15—C20—H20	120.7
C16—C11—C18	109.5 (3)	O1—N1—C5	126.4 (2)
N2—C11—C10	101.5 (2)	O1—N1—C10	120.0 (2)
C16—C11—C10	115.7 (2)	C5—N1—C10	113.2 (2)
C18—C11—C10	114.3 (2)	O2—N2—C5	126.2 (2)
C19—C12—C20	117.6 (3)	O2—N2—C11	120.3 (2)
C19—C12—H12	121.2	C5—N2—C11	113.4 (2)
C20—C12—H12	121.2	C19—N3—C1	117.7 (3)
C10—C13—H13A	109.5
C6—C2—C4—C8	1.1 (4)	C7—C1—C15—C20	178.2 (4)
C5—C2—C4—C8	−180.0 (2)	C20—C12—C19—N3	4.3 (6)
C6—C2—C5—N1	152.3 (3)	C19—C12—C20—C15	−3.0 (7)
C4—C2—C5—N1	−26.6 (4)	C1—C15—C20—C12	−0.7 (7)
C6—C2—C5—N2	−26.5 (4)	N2—C5—N1—O1	179.1 (2)
C4—C2—C5—N2	154.6 (3)	C2—C5—N1—O1	0.1 (4)
C4—C2—C6—C9	−0.1 (4)	N2—C5—N1—C10	6.8 (3)
C5—C2—C6—C9	−179.1 (3)	C2—C5—N1—C10	−172.3 (2)
N3—C1—C7—C8	−0.4 (4)	C13—C10—N1—O1	−65.1 (3)
C15—C1—C7—C8	−175.3 (3)	C14—C10—N1—O1	52.6 (3)
N3—C1—C7—C9	178.3 (3)	C11—C10—N1—O1	175.0 (2)
C15—C1—C7—C9	3.4 (4)	C13—C10—N1—C5	107.8 (3)
C2—C4—C8—C7	−1.0 (4)	C14—C10—N1—C5	−134.5 (3)
C9—C7—C8—C4	−0.2 (4)	C11—C10—N1—C5	−12.1 (3)
C1—C7—C8—C4	178.5 (3)	N1—C5—N2—O2	177.4 (3)
C2—C6—C9—C7	−1.0 (4)	C2—C5—N2—O2	−3.6 (4)
C8—C7—C9—C6	1.1 (4)	N1—C5—N2—C11	2.2 (3)
C1—C7—C9—C6	−177.5 (3)	C2—C5—N2—C11	−178.8 (2)
N1—C10—C11—N2	11.7 (2)	C16—C11—N2—O2	52.8 (3)
C13—C10—C11—N2	−102.1 (2)	C18—C11—N2—O2	−65.0 (3)
C14—C10—C11—N2	129.1 (2)	C10—C11—N2—O2	175.1 (2)
N1—C10—C11—C16	128.8 (3)	C16—C11—N2—C5	−131.6 (3)
C13—C10—C11—C16	15.0 (4)	C18—C11—N2—C5	110.5 (3)
C14—C10—C11—C16	−113.7 (3)	C10—C11—N2—C5	−9.4 (3)
N1—C10—C11—C18	−102.6 (3)	C12—C19—N3—C1	−1.6 (5)
C13—C10—C11—C18	143.6 (3)	C15—C1—N3—C19	−2.5 (5)
C14—C10—C11—C18	14.8 (3)	C7—C1—N3—C19	−177.5 (3)
N3—C1—C15—C20	3.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.93	2.43	3.322 (4)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.93	2.43	3.322 (4)	161

Symmetry code: (i) .