2-[1-(4-Chloro-benzo-yl)pyrrolidin-2-yl]-4,4,5,5-tetra-methyl-4,5-dihydro-imidazole-1-oxyl-3-oxide.

In the title compound, C(18)H(23)ClN(3)O(3), the imidazole ring system has an envelope conformation, whereas the nitronyl nitroxide unit displays a half-chair or twisted conformation. In the crystal, C-H⋯O hydrogen bonds build up a three-dimensional network.

Related literature

For the biological activity of nitronyl nitroxides, see: Soule et al. (2007 ▶ and for their coordination properties, see: Masuda et al. (2009 ▶). For related structures, see: Iqbal et al. (2009 ▶); Wang et al. (2009 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H23ClN3O3

M = 364.84

Monoclinic,

a = 11.6202 (19) Å

b = 8.2694 (13) Å

c = 20.315 (3) Å

β = 105.636 (2)°

V = 1879.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.34 × 0.29 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.928, T max = 0.960

9089 measured reflections

3342 independent reflections

1791 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.152

S = 1.03

3342 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001462/dn2639sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001462/dn2639Isup2.hkl

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

C18H23ClN3O3	F(000) = 772
Mr = 364.84	Dx = 1.289 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1006 reflections
a = 11.6202 (19) Å	θ = 2.3–19.1°
b = 8.2694 (13) Å	µ = 0.23 mm−1
c = 20.315 (3) Å	T = 296 K
β = 105.636 (2)°	Block, purple
V = 1879.8 (5) Å3	0.34 × 0.29 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	3342 independent reflections
Radiation source: fine-focus sealed tube	1791 reflections with I > 2σ(I)
graphite	Rint = 0.051
φ and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −13→13
Tmin = 0.928, Tmax = 0.960	k = −9→5
9089 measured reflections	l = −24→22

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0548P)2] where P = (Fo2 + 2Fc2)/3
3342 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cl1	0.24418 (8)	−0.02934 (14)	0.22799 (5)	0.0934 (4)
O1	0.61663 (17)	0.1756 (3)	0.04529 (10)	0.0602 (6)
O2	0.84803 (18)	0.2887 (2)	−0.03089 (10)	0.0613 (6)
O3	0.7771 (2)	0.5304 (3)	0.15800 (11)	0.0793 (8)
N1	0.7572 (2)	0.1723 (3)	0.14502 (11)	0.0496 (6)
N2	0.81945 (18)	0.3955 (3)	0.00771 (11)	0.0462 (6)
N3	0.7868 (2)	0.5102 (3)	0.09729 (12)	0.0522 (7)
C1	0.3608 (3)	0.0241 (4)	0.19376 (17)	0.0586 (9)
C2	0.3684 (3)	−0.0441 (4)	0.13384 (17)	0.0601 (9)
H2A	0.3113	−0.1182	0.1111	0.072*
C3	0.4613 (3)	−0.0021 (3)	0.10737 (15)	0.0537 (8)
H3A	0.4661	−0.0471	0.0662	0.064*
C4	0.5484 (2)	0.1070 (3)	0.14140 (14)	0.0472 (7)
C5	0.5373 (3)	0.1743 (4)	0.20168 (15)	0.0561 (8)
H5	0.5942	0.2480	0.2250	0.067*
C6	0.4434 (3)	0.1341 (4)	0.22772 (16)	0.0609 (9)
H6	0.4362	0.1812	0.2680	0.073*
C7	0.6433 (3)	0.1542 (3)	0.10742 (15)	0.0479 (7)
C8	0.8104 (3)	0.1429 (4)	0.21806 (14)	0.0617 (9)
H8A	0.7748	0.0491	0.2335	0.074*
H8B	0.8008	0.2360	0.2451	0.074*
C9	0.9400 (3)	0.1137 (5)	0.22247 (16)	0.0697 (10)
H9A	0.9537	0.0020	0.2121	0.084*
H9B	0.9904	0.1401	0.2676	0.084*
C10	0.9636 (3)	0.2265 (4)	0.16896 (16)	0.0635 (9)
H10A	1.0315	0.1900	0.1537	0.076*
H10B	0.9787	0.3357	0.1866	0.076*
C11	0.8480 (2)	0.2188 (4)	0.11055 (14)	0.0486 (8)
H11	0.8553	0.1332	0.0786	0.058*
C12	0.8187 (2)	0.3736 (4)	0.07277 (13)	0.0438 (7)
C13	0.7659 (3)	0.5550 (4)	−0.01959 (15)	0.0510 (8)
C14	0.7768 (3)	0.6477 (4)	0.04813 (15)	0.0531 (8)
C15	0.8360 (3)	0.6285 (4)	−0.06555 (17)	0.0779 (11)
H15A	0.9181	0.6412	−0.0402	0.117*
H15B	0.8029	0.7322	−0.0816	0.117*
H15C	0.8311	0.5585	−0.1039	0.117*
C16	0.6380 (3)	0.5167 (4)	−0.05963 (18)	0.0816 (12)
H16A	0.6388	0.4451	−0.0967	0.122*
H16B	0.5976	0.6150	−0.0775	0.122*
H16C	0.5971	0.4657	−0.0300	0.122*
C17	0.8923 (3)	0.7448 (4)	0.07346 (18)	0.0801 (11)
H17A	0.8999	0.7809	0.1193	0.120*
H17B	0.8901	0.8367	0.0443	0.120*
H17C	0.9593	0.6777	0.0727	0.120*
C18	0.6703 (3)	0.7508 (5)	0.05121 (19)	0.0856 (12)
H18A	0.5987	0.6872	0.0375	0.128*
H18B	0.6643	0.8415	0.0210	0.128*
H18C	0.6807	0.7887	0.0971	0.128*

	U11	U22	U33	U12	U13	U23
Cl1	0.0622 (6)	0.1224 (10)	0.1045 (8)	−0.0041 (5)	0.0375 (6)	0.0165 (6)
O1	0.0588 (13)	0.0744 (16)	0.0446 (13)	−0.0067 (11)	0.0091 (10)	0.0026 (10)
O2	0.0730 (14)	0.0614 (16)	0.0543 (13)	0.0069 (11)	0.0252 (11)	−0.0072 (11)
O3	0.114 (2)	0.0787 (18)	0.0516 (14)	0.0164 (14)	0.0341 (13)	−0.0040 (12)
N1	0.0472 (15)	0.0576 (17)	0.0428 (14)	−0.0007 (12)	0.0099 (12)	0.0103 (11)
N2	0.0456 (13)	0.0504 (16)	0.0447 (15)	0.0033 (12)	0.0155 (11)	−0.0006 (12)
N3	0.0622 (16)	0.0504 (17)	0.0464 (16)	0.0085 (12)	0.0185 (13)	0.0005 (13)
C1	0.0430 (18)	0.068 (2)	0.065 (2)	0.0065 (16)	0.0152 (16)	0.0131 (18)
C2	0.0481 (19)	0.052 (2)	0.075 (2)	−0.0038 (15)	0.0087 (17)	0.0014 (17)
C3	0.0515 (19)	0.053 (2)	0.0521 (19)	0.0012 (16)	0.0069 (16)	−0.0061 (15)
C4	0.0467 (17)	0.0432 (19)	0.0498 (18)	0.0038 (14)	0.0100 (14)	0.0042 (14)
C5	0.0522 (19)	0.059 (2)	0.055 (2)	−0.0026 (15)	0.0107 (16)	−0.0082 (16)
C6	0.055 (2)	0.075 (3)	0.0533 (19)	0.0059 (18)	0.0165 (16)	−0.0048 (17)
C7	0.0521 (19)	0.0430 (19)	0.0470 (18)	0.0001 (14)	0.0107 (15)	−0.0006 (14)
C8	0.058 (2)	0.077 (3)	0.0484 (19)	0.0023 (17)	0.0103 (15)	0.0142 (16)
C9	0.056 (2)	0.088 (3)	0.062 (2)	0.0021 (18)	0.0107 (16)	0.0231 (19)
C10	0.0503 (18)	0.070 (2)	0.067 (2)	0.0038 (16)	0.0088 (16)	0.0188 (17)
C11	0.0472 (17)	0.049 (2)	0.0495 (18)	0.0049 (14)	0.0131 (14)	0.0086 (14)
C12	0.0428 (16)	0.049 (2)	0.0401 (17)	0.0037 (14)	0.0116 (13)	0.0050 (15)
C13	0.0522 (18)	0.048 (2)	0.0488 (18)	0.0073 (15)	0.0074 (14)	0.0112 (14)
C14	0.0546 (19)	0.047 (2)	0.058 (2)	0.0111 (15)	0.0157 (15)	0.0076 (15)
C15	0.104 (3)	0.070 (3)	0.068 (2)	0.001 (2)	0.039 (2)	0.0161 (18)
C16	0.067 (2)	0.084 (3)	0.076 (2)	0.0130 (19)	−0.011 (2)	0.0042 (19)
C17	0.087 (3)	0.068 (3)	0.086 (3)	−0.015 (2)	0.024 (2)	−0.0091 (19)
C18	0.087 (3)	0.082 (3)	0.089 (3)	0.040 (2)	0.027 (2)	0.008 (2)

Cl1—C1	1.738 (3)	C9—C10	1.513 (4)
O1—C7	1.229 (3)	C9—H9A	0.9700
O2—N2	1.283 (3)	C9—H9B	0.9700
O3—N3	1.279 (3)	C10—C11	1.535 (4)
N1—C7	1.346 (3)	C10—H10A	0.9700
N1—C8	1.466 (3)	C10—H10B	0.9700
N1—C11	1.467 (3)	C11—C12	1.484 (4)
N2—C12	1.336 (3)	C11—H11	0.9800
N2—C13	1.500 (4)	C13—C15	1.521 (4)
N3—C12	1.328 (3)	C13—C16	1.523 (4)
N3—C14	1.497 (4)	C13—C14	1.550 (4)
C1—C2	1.366 (4)	C14—C18	1.517 (4)
C1—C6	1.367 (4)	C14—C17	1.529 (4)
C2—C3	1.374 (4)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.392 (4)	C15—H15C	0.9600
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.382 (4)	C16—H16B	0.9600
C4—C7	1.502 (4)	C16—H16C	0.9600
C5—C6	1.376 (4)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C8—C9	1.503 (4)	C18—H18A	0.9600
C8—H8A	0.9700	C18—H18B	0.9600
C8—H8B	0.9700	C18—H18C	0.9600
C7—N1—C8	129.7 (2)	H10A—C10—H10B	109.0
C7—N1—C11	118.8 (2)	N1—C11—C12	112.2 (2)
C8—N1—C11	111.4 (2)	N1—C11—C10	103.5 (2)
O2—N2—C12	125.7 (2)	C12—C11—C10	113.3 (2)
O2—N2—C13	122.0 (2)	N1—C11—H11	109.2
C12—N2—C13	111.9 (2)	C12—C11—H11	109.2
O3—N3—C12	125.4 (2)	C10—C11—H11	109.2
O3—N3—C14	122.2 (2)	N3—C12—N2	109.4 (2)
C12—N3—C14	112.1 (2)	N3—C12—C11	126.1 (3)
C2—C1—C6	121.2 (3)	N2—C12—C11	124.5 (3)
C2—C1—Cl1	119.8 (3)	N2—C13—C15	110.0 (2)
C6—C1—Cl1	119.0 (3)	N2—C13—C16	105.2 (2)
C1—C2—C3	119.4 (3)	C15—C13—C16	111.2 (3)
C1—C2—H2A	120.3	N2—C13—C14	100.4 (2)
C3—C2—H2A	120.3	C15—C13—C14	114.7 (3)
C2—C3—C4	120.8 (3)	C16—C13—C14	114.3 (3)
C2—C3—H3A	119.6	N3—C14—C18	108.5 (3)
C4—C3—H3A	119.6	N3—C14—C17	105.7 (2)
C5—C4—C3	118.2 (3)	C18—C14—C17	110.0 (3)
C5—C4—C7	123.9 (3)	N3—C14—C13	100.9 (2)
C3—C4—C7	117.7 (3)	C18—C14—C13	116.2 (3)
C6—C5—C4	121.1 (3)	C17—C14—C13	114.3 (3)
C6—C5—H5	119.5	C13—C15—H15A	109.5
C4—C5—H5	119.5	C13—C15—H15B	109.5
C1—C6—C5	119.3 (3)	H15A—C15—H15B	109.5
C1—C6—H6	120.4	C13—C15—H15C	109.5
C5—C6—H6	120.4	H15A—C15—H15C	109.5
O1—C7—N1	120.3 (3)	H15B—C15—H15C	109.5
O1—C7—C4	119.8 (3)	C13—C16—H16A	109.5
N1—C7—C4	120.0 (2)	C13—C16—H16B	109.5
N1—C8—C9	103.3 (2)	H16A—C16—H16B	109.5
N1—C8—H8A	111.1	C13—C16—H16C	109.5
C9—C8—H8A	111.1	H16A—C16—H16C	109.5
N1—C8—H8B	111.1	H16B—C16—H16C	109.5
C9—C8—H8B	111.1	C14—C17—H17A	109.5
H8A—C8—H8B	109.1	C14—C17—H17B	109.5
C8—C9—C10	103.4 (2)	H17A—C17—H17B	109.5
C8—C9—H9A	111.1	C14—C17—H17C	109.5
C10—C9—H9A	111.1	H17A—C17—H17C	109.5
C8—C9—H9B	111.1	H17B—C17—H17C	109.5
C10—C9—H9B	111.1	C14—C18—H18A	109.5
H9A—C9—H9B	109.1	C14—C18—H18B	109.5
C9—C10—C11	103.9 (2)	H18A—C18—H18B	109.5
C9—C10—H10A	111.0	C14—C18—H18C	109.5
C11—C10—H10A	111.0	H18A—C18—H18C	109.5
C9—C10—H10B	111.0	H18B—C18—H18C	109.5
C11—C10—H10B	111.0
C6—C1—C2—C3	0.4 (5)	C14—N3—C12—C11	173.7 (2)
Cl1—C1—C2—C3	−179.5 (2)	O2—N2—C12—N3	178.9 (2)
C1—C2—C3—C4	0.9 (4)	C13—N2—C12—N3	−9.2 (3)
C2—C3—C4—C5	−1.3 (4)	O2—N2—C12—C11	−1.8 (4)
C2—C3—C4—C7	−176.6 (3)	C13—N2—C12—C11	170.2 (2)
C3—C4—C5—C6	0.4 (4)	N1—C11—C12—N3	49.2 (4)
C7—C4—C5—C6	175.4 (3)	C10—C11—C12—N3	−67.6 (4)
C2—C1—C6—C5	−1.3 (5)	N1—C11—C12—N2	−130.0 (3)
Cl1—C1—C6—C5	178.6 (2)	C10—C11—C12—N2	113.2 (3)
C4—C5—C6—C1	0.9 (5)	O2—N2—C13—C15	−46.3 (3)
C8—N1—C7—O1	−175.4 (3)	C12—N2—C13—C15	141.3 (2)
C11—N1—C7—O1	0.4 (4)	O2—N2—C13—C16	73.5 (3)
C8—N1—C7—C4	4.3 (4)	C12—N2—C13—C16	−98.8 (3)
C11—N1—C7—C4	−179.9 (2)	O2—N2—C13—C14	−167.6 (2)
C5—C4—C7—O1	−135.9 (3)	C12—N2—C13—C14	20.1 (3)
C3—C4—C7—O1	39.1 (4)	O3—N3—C14—C18	−45.1 (4)
C5—C4—C7—N1	44.4 (4)	C12—N3—C14—C18	141.5 (3)
C3—C4—C7—N1	−140.7 (3)	O3—N3—C14—C17	72.9 (3)
C7—N1—C8—C9	156.1 (3)	C12—N3—C14—C17	−100.5 (3)
C11—N1—C8—C9	−20.0 (3)	O3—N3—C14—C13	−167.8 (3)
N1—C8—C9—C10	35.2 (3)	C12—N3—C14—C13	18.9 (3)
C8—C9—C10—C11	−37.6 (3)	N2—C13—C14—N3	−21.4 (3)
C7—N1—C11—C12	57.7 (3)	C15—C13—C14—N3	−139.2 (3)
C8—N1—C11—C12	−125.8 (3)	C16—C13—C14—N3	90.6 (3)
C7—N1—C11—C10	−179.8 (2)	N2—C13—C14—C18	−138.5 (3)
C8—N1—C11—C10	−3.3 (3)	C15—C13—C14—C18	103.7 (3)
C9—C10—C11—N1	25.2 (3)	C16—C13—C14—C18	−26.5 (4)
C9—C10—C11—C12	147.0 (3)	N2—C13—C14—C17	91.5 (3)
O3—N3—C12—N2	179.9 (3)	C15—C13—C14—C17	−26.3 (4)
C14—N3—C12—N2	−7.0 (3)	C16—C13—C14—C17	−156.4 (3)
O3—N3—C12—C11	0.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.93	2.54	3.458 (4)	170
C3—H3A···O1i	0.93	2.45	3.314 (4)	154
C8—H8A···O3ii	0.97	2.44	3.101 (4)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.93	2.54	3.458 (4)	170
C3—H3A⋯O1i	0.93	2.45	3.314 (4)	154
C8—H8A⋯O3ii	0.97	2.44	3.101 (4)	125

Symmetry codes: (i) ; (ii) .