2-[1-(4-Chloro­benzo­yl)pyrrolidin-2-yl]-4,4,5,5-tetra­methyl-4,5-dihydro­imidazole-1-oxyl-3-oxide

Tian, M.; Xiang, Z.; Zhou, S.-Y.; Jing, L.-L.; Wang, H.-B.; Sun, X.-L.

doi:10.1107/S1600536811001462

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o425

doi:10.1107/S1600536811001462

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2-[1-(4-Chlorobenzoyl)pyrrolidin-2-yl]-4,4,5,5-tetramethyl-4,5-dihydroimidazole-1-oxyl-3-oxide

Min Tian,^a Zhuo Xiang,^a Si-Yuan Zhou,^b Lin-Lin Jing,^c Hai-Bo Wang ^a and Xiao-Li Sun ^a ^*

^aDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China, ^bDepartment of Pharmaceutics, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China, and ^cDepartment of Pharmacy, Lanzhou General Hospital, Lanzhou Command, Lanzhou 730050, People's Republic of China
^*Correspondence e-mail: xiaoli_sun@yahoo.cn

(Received 17 December 2010; accepted 11 January 2011; online 15 January 2011)

In the title compound, C₁₈H₂₃ClN₃O₃, 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_r = 364.84
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.152
S = 1.03
3342 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) -x+1, -y, -z; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

Nitronyl nitroxides, stable organic radicals, display interesting properties in many fields as magnetism, anticancer, antiradiation and antioxidation etc (Soule et al., 2007). Nitronyl nitroxides have received considerable attention recently (Iqbal et al., 2009; Wang et al., 2009). The title compound can also be used for coordination with many metal cations, such as Mn²⁺, Cu²⁺ and Ni²⁺ leading to some molecule based magentic materials (Masuda, et al., 2009).

In the title compound, the indole ring system has an envelope conformation with puckering parameters Q(2)= 0.370 (4)Å and ϕ= 78.0 (5)° (Cremer & Pople, 1975) whereas the nitronyl nitroxide moiety displays a half-chair or twisted conformation with Q(2)= 0.228 (3)Å and ϕ= 308.6 (7)°. Occurence of C-H···O hydrogen bonds build up a three dimensional network (Table 1).

Related literature top

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 top

2,3-Dimethyl-2,3-bis(hydroxylamino) butane (1.48 g, 10.0 mmol) and 1-(4-chlorobenzoyl)pyrrolidine-2-carbaldehyde (2.38 g, 10.0 mmol) were dissolved in methanol. The reaction was stirred for 10 h at reflux temperature, then cooled to room temperature and filtered. The cake was suspended in dichloromethane (150.0 ml) and cooled at ice bath for 10 min,Then the reaction mixture was added to an aqueous solution of NaIO₄ and stirred for 15 min to give a amaranthine solution. The aqueous phase was extracted with CH₂Cl₂ and the organic layer was combined and dried over MgSO₄. Then the solvent was removed to give a amaranthine residue which was purified by a flash column chromatography with the elution of n-hexane/ethyl acetate (1:1) to yield the title compound (I) as a dark amaranthine powder. Single crystals of compound (I) were obtained from the 1/1 mixed solution of n-heptane and dichloromethane.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. Molecular structure of the title compound (I), showing the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

2-[1-(4-Chlorobenzoyl)pyrrolidin-2-yl]-4,4,5,5-tetramethyl-4,5- dihydroimidazole-1-oxyl-3-oxide top

Crystal data top

C₁₈H₂₃ClN₃O₃	F(000) = 772
M_r = 364.84	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0548P)²] where P = (F_o² + 2F_c²)/3
3342 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₈H₂₃ClN₃O₃	V = 1879.8 (5) Å³
M_r = 364.84	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.6202 (19) Å	µ = 0.23 mm⁻¹
b = 8.2694 (13) Å	T = 296 K
c = 20.315 (3) Å	0.34 × 0.29 × 0.18 mm
β = 105.636 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3342 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	1791 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.960	R_int = 0.051
9089 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
3342 reflections	Δρ_min = −0.18 e Å⁻³
230 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z; (ii) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃ClN₃O₃
M_r	364.84
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.6202 (19), 8.2694 (13), 20.315 (3)
β (°)	105.636 (2)
V (Å³)	1879.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.34 × 0.29 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.928, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	9089, 3342, 1791
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.152, 1.03
No. of reflections	3342
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008b) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z; (ii) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

We thank the Natural Science Foundation of China (grant Nos. 81001398, 30901883, 20802091) for financial support.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Iqbal, A. L., Anirban, P. & Sambhu, N. D. (2009). J. Phys. Chem. A, 113, 1595–4673. Web of Science CrossRef PubMed Google Scholar
Masuda, Y., Kurats, M., Suzuki, S., Kozaki, M., Shiomi, D., Sato, K., Takui, T., Hosokoshi, Y., Miyazaki, Y., Inada, A. & Okada, K. (2009). J. Am. Chem. Soc. 131, 4670-4673. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soule, B. P., Hyodo, F., Matsumoto, K., Simone, N. L., Cook, J. A., Krishna, M. C. & Mitchell, J. B. (2007). Free Radic. Biol. Med. 42, 1632–1650. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H.-B., Jing, L.-L., Gao, P. & Sun, X.-L. (2009). Acta Cryst. E65, o2090. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o425

doi:10.1107/S1600536811001462

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-[1-(4-Chloro­benzo­yl)pyrrolidin-2-yl]-4,4,5,5-tetra­methyl-4,5-di­hydro­imidazole-1-oxyl-3-oxide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[1-(4-Chlorobenzoyl)pyrrolidin-2-yl]-4,4,5,5-tetramethyl-4,5-dihydroimidazole-1-oxyl-3-oxide