2-[1-(tert-But­oxy­carbonyl)­pyrrolidin-2-yl]-4,4,5,5-tetra­methyl-4,5-dihydro-1H-imidazole-1-oxyl 3-oxide

Jiang, R.; Wang, H.-B.; Gao, P.; Jing, L.-L.; Sun, X.-L.

doi:10.1107/S1600536810020672

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o1954

https://doi.org/10.1107/S1600536810020672

Open

access

2-[1-(tert-Butoxycarbonyl)pyrrolidin-2-yl]-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-1-oxyl 3-oxide

Ru Jiang,^a Hai-Bo Wang,^a Peng Gao,^a Lin-Lin Jing ^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
^*Correspondence e-mail: xiaoli_sun@yahoo.cn

(Received 13 May 2010; accepted 31 May 2010; online 7 July 2010)

In the title compound, C₁₆H₂₈N₃O₄, the plane of the pyrrolidine ring system is twisted with respect to the plane of the nitronyl nitroxide unit, making a dihedral angle of 79.80 (6)°. The crystal structure is stabilized by C—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Ullman et al. (1974 ). For the properties of nitronyl nitroxide radicals, see: Iqbal et al. (2009 ); Qin et al. (2009 ); Tanaka et al. (2007 ); Soule et al. (2007 ). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₆H₂₈N₃O₄
M_r = 326.41
Monoclinic, P 2₁
a = 6.1016 (12) Å
b = 10.392 (2) Å
c = 14.488 (3) Å
β = 101.312 (3)°
V = 900.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.36 × 0.28 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
4494 measured reflections
1686 independent reflections
1347 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.104
S = 0.97
1686 reflections
215 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1	0.96	2.47	3.043 (5)	118
C3—H3C⋯O1	0.96	2.43	3.025 (4)	120
C16—H17C⋯O3ⁱ	0.96	2.48	3.390 (4)	157
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+2]$ .

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: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek,2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810020672/dn2566sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810020672/dn2566Isup2.hkl

checkCIF report

Comment top

Nitronyl nitroxide radical is a class of important functionalized molecule, which has characteristics of magnetism, anticancer, antiradiation and antioxidation, etc (Iqbal, et al., 2009; Qin, et al., 2009; Tanaka, et al., 2007; Soule, et al., 2007). The title compound has been be used for coordination with many metalcations, such as Mn²⁺, Cu²⁺ and Ni²⁺leading to form some molecule based magentic materials. The molecular structure of the title compound is shown in Fig1. The pyrrolidine ring and the nitronyl nitroxide ring are twisted with respect to each other making a dihedral angle of 79.80 (6)°. The crystal structure is stabilized by C—H···O hydrogen bonds (Table 1).

Related literature top

For the preparation of the title compound, see: Ullman et al. (1974). For the properties of nitronyl nitroxide radicals, see: Iqbal et al. (2009); Qin et al. (2009); Tanaka et al. (2007); Soule et al. (2007). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

2,3-Dimethyl-2,3-bis(hydroxylamino) butane (1.48 g, 10.0 mmol) and tert-butyl-2-(hydroxymethyl) pyrrolidine-1-carboxylate (2.01 g, 10.0 mmol) were dissolved in methanol (Ullman, et al., 1974). The reaction was stirred for 15 h at reflux temperature, then cooled to room temperature and filtered. The white powder was washed by methanol and suspended in a mixed solution of dichloromethane (30.0 ml) and water (30.0 ml). Then the reaction mixture was added to an aqueous solution of NaIO₄ and stirred for 15 min in ice bath to give a blue 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 dark red residue which was purified by a flash column chromatography with the elution of n-hexane/ ethyl acetate (1:3) to yield the title compound (I) as a dark blue powder. Single crystals of compound (I) were obtained from the mixed solution of n-heptane and dichloromethane (the ratio of volume is 1 to 1).

Structure description top

For the preparation of the title compound, see: Ullman et al. (1974). For the properties of nitronyl nitroxide radicals, see: Iqbal et al. (2009); Qin et al. (2009); Tanaka et al. (2007); Soule et al. (2007). For puckering parameters, see: Cremer & Pople (1975).

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) 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.

2-[1-(tert-Butoxycarbonyl)pyrrolidin-2-yl]-4,4,5,5-tetramethyl-4,5- dihydro-1H-imidazole-1-oxyl 3-oxide top

Crystal data top

C₁₆H₂₈N₃O₄	F(000) = 354
M_r = 326.41	D_x = 1.203 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1546 reflections
a = 6.1016 (12) Å	θ = 2.4–21.6°
b = 10.392 (2) Å	µ = 0.09 mm⁻¹
c = 14.488 (3) Å	T = 296 K
β = 101.312 (3)°	Block, red
V = 900.8 (3) Å³	0.36 × 0.28 × 0.17 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1347 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 25.1°, θ_min = 2.4°
phi and ω scans	h = −7→7
4494 measured reflections	k = −6→12
1686 independent reflections	l = −16→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0673P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
1686 reflections	Δρ_max = 0.18 e Å⁻³
215 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (5)

Crystal data top

C₁₆H₂₈N₃O₄	V = 900.8 (3) Å³
M_r = 326.41	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.1016 (12) Å	µ = 0.09 mm⁻¹
b = 10.392 (2) Å	T = 296 K
c = 14.488 (3) Å	0.36 × 0.28 × 0.17 mm
β = 101.312 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1347 reflections with I > 2σ(I)
4494 measured reflections	R_int = 0.048
1686 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.104	H-atom parameters constrained
S = 0.97	Δρ_max = 0.18 e Å⁻³
1686 reflections	Δρ_min = −0.20 e Å⁻³
215 parameters

Special details top

Experimental. The absolute structure cannot be determined beacuse there are no atoms heaver than silicon in the molecular.

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.0929 (4)	0.3494 (3)	0.78508 (14)	0.0442 (6)
N2	0.3330 (4)	0.4804 (2)	0.86782 (15)	0.0434 (6)
N3	0.1712 (4)	0.6757 (2)	0.71424 (15)	0.0471 (6)
O1	0.3991 (4)	0.7310 (3)	0.61493 (15)	0.0669 (7)
O2	−0.0793 (3)	0.3080 (2)	0.72759 (14)	0.0615 (6)
O3	0.4286 (4)	0.5857 (2)	0.90224 (15)	0.0621 (6)
O4	0.2361 (4)	0.5320 (2)	0.61039 (13)	0.0575 (6)
C1	0.2011 (6)	0.3558 (4)	0.5093 (2)	0.0656 (9)
H1A	0.2562	0.3044	0.5640	0.098*
H1B	0.2408	0.3160	0.4550	0.098*
H1C	0.0414	0.3625	0.5004	0.098*
C2	0.5524 (6)	0.4831 (4)	0.5354 (3)	0.0718 (10)
H2A	0.6115	0.5689	0.5434	0.108*
H2B	0.5934	0.4448	0.4809	0.108*
H2C	0.6123	0.4327	0.5900	0.108*
C3	0.1978 (7)	0.5764 (4)	0.4421 (2)	0.0799 (12)
H3A	0.0387	0.5782	0.4375	0.120*
H3B	0.2316	0.5450	0.3842	0.120*
H3C	0.2569	0.6617	0.4541	0.120*
C4	0.3028 (5)	0.4878 (3)	0.52248 (18)	0.0488 (8)
C5	0.2803 (5)	0.6526 (3)	0.64280 (19)	0.0482 (7)
C6	0.1631 (6)	0.8032 (3)	0.7549 (2)	0.0556 (8)
H6A	0.1705	0.8699	0.7088	0.067*
H6B	0.2842	0.8153	0.8086	0.067*
C7	−0.0620 (7)	0.8035 (3)	0.7848 (3)	0.0690 (10)
H9A	−0.0623	0.8630	0.8364	0.083*
H9B	−0.1810	0.8269	0.7327	0.083*
C8	−0.0877 (6)	0.6663 (3)	0.8153 (2)	0.0576 (9)
H10A	−0.2443	0.6437	0.8084	0.069*
H10B	−0.0150	0.6542	0.8806	0.069*
C9	0.0256 (4)	0.5839 (3)	0.74985 (18)	0.0417 (7)
H11	−0.0878	0.5518	0.6974	0.050*
C10	0.1523 (4)	0.4731 (3)	0.79995 (17)	0.0385 (6)
C11	0.2665 (5)	0.2596 (3)	0.8383 (2)	0.0506 (8)
C12	0.4042 (6)	0.2131 (4)	0.7676 (2)	0.0705 (11)
H15A	0.3088	0.1683	0.7172	0.106*
H15B	0.5194	0.1560	0.7983	0.106*
H15C	0.4709	0.2856	0.7427	0.106*
C13	0.1549 (6)	0.1467 (4)	0.8763 (3)	0.0692 (10)
H16A	0.0599	0.1775	0.9170	0.104*
H16B	0.2669	0.0909	0.9110	0.104*
H16C	0.0670	0.0999	0.8249	0.104*
C14	0.3947 (4)	0.3532 (3)	0.91403 (18)	0.0450 (7)
C15	0.6454 (5)	0.3379 (4)	0.9356 (2)	0.0635 (9)
H18A	0.7020	0.3464	0.8786	0.095*
H18B	0.6833	0.2544	0.9625	0.095*
H18C	0.7105	0.4031	0.9795	0.095*
C16	0.3053 (5)	0.3565 (4)	1.00551 (19)	0.0596 (9)
H17A	0.1457	0.3658	0.9911	0.089*
H17B	0.3702	0.4279	1.0432	0.089*
H17C	0.3439	0.2778	1.0396	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0490 (13)	0.0398 (15)	0.0440 (12)	−0.0025 (12)	0.0091 (10)	0.0019 (11)
N2	0.0451 (13)	0.0403 (15)	0.0455 (12)	−0.0073 (13)	0.0104 (10)	0.0000 (12)
N3	0.0717 (15)	0.0350 (13)	0.0405 (11)	−0.0039 (13)	0.0252 (11)	−0.0009 (11)
O1	0.0936 (17)	0.0510 (14)	0.0679 (13)	−0.0193 (14)	0.0449 (12)	−0.0023 (12)
O2	0.0602 (12)	0.0519 (15)	0.0653 (12)	−0.0125 (11)	−0.0050 (10)	−0.0020 (11)
O3	0.0670 (13)	0.0529 (15)	0.0627 (12)	−0.0176 (13)	0.0034 (10)	−0.0058 (12)
O4	0.0907 (15)	0.0449 (13)	0.0470 (11)	−0.0064 (13)	0.0380 (10)	−0.0074 (10)
C1	0.087 (2)	0.058 (2)	0.0559 (17)	−0.002 (2)	0.0249 (15)	−0.0131 (17)
C2	0.072 (2)	0.069 (3)	0.078 (2)	0.002 (2)	0.0212 (16)	−0.020 (2)
C3	0.113 (3)	0.077 (3)	0.0487 (17)	0.017 (2)	0.0119 (17)	0.0065 (19)
C4	0.0631 (17)	0.052 (2)	0.0350 (13)	0.0042 (16)	0.0191 (11)	−0.0044 (14)
C5	0.0683 (19)	0.0390 (18)	0.0405 (13)	−0.0040 (16)	0.0183 (13)	−0.0013 (14)
C6	0.085 (2)	0.0382 (17)	0.0477 (15)	−0.0046 (18)	0.0227 (15)	−0.0050 (14)
C7	0.102 (3)	0.048 (2)	0.0658 (19)	0.009 (2)	0.0381 (18)	0.0000 (17)
C8	0.072 (2)	0.051 (2)	0.0579 (17)	0.0066 (18)	0.0331 (15)	0.0045 (16)
C9	0.0506 (15)	0.0379 (16)	0.0382 (12)	−0.0024 (14)	0.0123 (11)	0.0002 (13)
C10	0.0457 (14)	0.0363 (16)	0.0358 (12)	−0.0047 (14)	0.0141 (11)	0.0014 (13)
C11	0.0507 (17)	0.043 (2)	0.0583 (17)	0.0013 (15)	0.0113 (13)	0.0030 (14)
C12	0.073 (2)	0.069 (3)	0.072 (2)	0.013 (2)	0.0214 (17)	−0.014 (2)
C13	0.077 (2)	0.045 (2)	0.084 (2)	−0.0033 (19)	0.0152 (18)	0.0179 (19)
C14	0.0482 (15)	0.0446 (18)	0.0428 (14)	0.0008 (15)	0.0104 (11)	0.0058 (14)
C15	0.0514 (16)	0.071 (3)	0.0672 (18)	0.0057 (18)	0.0081 (14)	0.0002 (19)
C16	0.0642 (17)	0.071 (2)	0.0466 (15)	0.0057 (19)	0.0187 (13)	0.0097 (17)

Geometric parameters (Å, º) top

N1—O2	1.281 (3)	C6—H6B	0.9700
N1—C10	1.341 (4)	C7—C8	1.511 (5)
N1—C11	1.506 (4)	C7—H9A	0.9700
N2—O3	1.293 (3)	C7—H9B	0.9700
N2—C10	1.328 (3)	C8—C9	1.538 (4)
N2—C14	1.495 (4)	C8—H10A	0.9700
N3—C5	1.357 (4)	C8—H10B	0.9700
N3—C6	1.455 (4)	C9—C10	1.494 (4)
N3—C9	1.464 (4)	C9—H11	0.9800
O1—C5	1.211 (4)	C11—C13	1.513 (5)
O4—C5	1.347 (4)	C11—C12	1.526 (4)
O4—C4	1.484 (3)	C11—C14	1.557 (4)
C1—C4	1.502 (5)	C12—H15A	0.9600
C1—H1A	0.9600	C12—H15B	0.9600
C1—H1B	0.9600	C12—H15C	0.9600
C1—H1C	0.9600	C13—H16A	0.9600
C2—C4	1.499 (5)	C13—H16B	0.9600
C2—H2A	0.9600	C13—H16C	0.9600
C2—H2B	0.9600	C14—C15	1.509 (4)
C2—H2C	0.9600	C14—C16	1.529 (4)
C3—C4	1.523 (4)	C15—H18A	0.9600
C3—H3A	0.9600	C15—H18B	0.9600
C3—H3B	0.9600	C15—H18C	0.9600
C3—H3C	0.9600	C16—H17A	0.9600
C6—C7	1.518 (5)	C16—H17B	0.9600
C6—H6A	0.9700	C16—H17C	0.9600

O2—N1—C10	126.0 (2)	C7—C8—H10A	110.7
O2—N1—C11	122.0 (3)	C9—C8—H10A	110.7
C10—N1—C11	111.8 (2)	C7—C8—H10B	110.7
O3—N2—C10	125.4 (2)	C9—C8—H10B	110.7
O3—N2—C14	121.35 (19)	H10A—C8—H10B	108.8
C10—N2—C14	112.4 (2)	N3—C9—C10	112.4 (2)
C5—N3—C6	122.0 (3)	N3—C9—C8	103.4 (2)
C5—N3—C9	125.2 (2)	C10—C9—C8	112.4 (2)
C6—N3—C9	112.3 (2)	N3—C9—H11	109.5
C5—O4—C4	121.2 (2)	C10—C9—H11	109.5
C4—C1—H1A	109.5	C8—C9—H11	109.5
C4—C1—H1B	109.5	N2—C10—N1	109.4 (2)
H1A—C1—H1B	109.5	N2—C10—C9	126.2 (3)
C4—C1—H1C	109.5	N1—C10—C9	124.3 (2)
H1A—C1—H1C	109.5	N1—C11—C13	110.2 (2)
H1B—C1—H1C	109.5	N1—C11—C12	106.1 (2)
C4—C2—H2A	109.5	C13—C11—C12	110.2 (3)
C4—C2—H2B	109.5	N1—C11—C14	100.3 (2)
H2A—C2—H2B	109.5	C13—C11—C14	115.4 (3)
C4—C2—H2C	109.5	C12—C11—C14	113.9 (2)
H2A—C2—H2C	109.5	C11—C12—H15A	109.5
H2B—C2—H2C	109.5	C11—C12—H15B	109.5
C4—C3—H3A	109.5	H15A—C12—H15B	109.5
C4—C3—H3B	109.5	C11—C12—H15C	109.5
H3A—C3—H3B	109.5	H15A—C12—H15C	109.5
C4—C3—H3C	109.5	H15B—C12—H15C	109.5
H3A—C3—H3C	109.5	C11—C13—H16A	109.5
H3B—C3—H3C	109.5	C11—C13—H16B	109.5
O4—C4—C2	110.3 (2)	H16A—C13—H16B	109.5
O4—C4—C1	102.5 (2)	C11—C13—H16C	109.5
C2—C4—C1	111.7 (3)	H16A—C13—H16C	109.5
O4—C4—C3	108.9 (3)	H16B—C13—H16C	109.5
C2—C4—C3	112.3 (3)	N2—C14—C15	110.0 (3)
C1—C4—C3	110.7 (3)	N2—C14—C16	105.5 (3)
O1—C5—O4	127.0 (3)	C15—C14—C16	110.0 (2)
O1—C5—N3	123.4 (3)	N2—C14—C11	100.9 (2)
O4—C5—N3	109.6 (3)	C15—C14—C11	115.4 (3)
N3—C6—C7	102.8 (3)	C16—C14—C11	114.1 (2)
N3—C6—H6A	111.2	C14—C15—H18A	109.5
C7—C6—H6A	111.2	C14—C15—H18B	109.5
N3—C6—H6B	111.2	H18A—C15—H18B	109.5
C7—C6—H6B	111.2	C14—C15—H18C	109.5
H6A—C6—H6B	109.1	H18A—C15—H18C	109.5
C8—C7—C6	103.5 (3)	H18B—C15—H18C	109.5
C8—C7—H9A	111.1	C14—C16—H17A	109.5
C6—C7—H9A	111.1	C14—C16—H17B	109.5
C8—C7—H9B	111.1	H17A—C16—H17B	109.5
C6—C7—H9B	111.1	C14—C16—H17C	109.5
H9A—C7—H9B	109.0	H17A—C16—H17C	109.5
C7—C8—C9	105.0 (2)	H17B—C16—H17C	109.5

C5—O4—C4—C2	66.4 (4)	C11—N1—C10—C9	173.9 (2)
C5—O4—C4—C1	−174.5 (3)	N3—C9—C10—N2	50.4 (3)
C5—O4—C4—C3	−57.3 (4)	C8—C9—C10—N2	−65.8 (4)
C4—O4—C5—O1	−10.5 (5)	N3—C9—C10—N1	−132.5 (3)
C4—O4—C5—N3	169.9 (2)	C8—C9—C10—N1	111.3 (3)
C6—N3—C5—O1	8.7 (5)	O2—N1—C11—C13	−43.4 (4)
C9—N3—C5—O1	179.8 (3)	C10—N1—C11—C13	141.6 (3)
C6—N3—C5—O4	−171.7 (3)	O2—N1—C11—C12	75.8 (3)
C9—N3—C5—O4	−0.7 (4)	C10—N1—C11—C12	−99.2 (3)
C5—N3—C6—C7	148.7 (3)	O2—N1—C11—C14	−165.5 (2)
C9—N3—C6—C7	−23.4 (3)	C10—N1—C11—C14	19.5 (3)
N3—C6—C7—C8	34.8 (3)	O3—N2—C14—C15	−48.6 (3)
C6—C7—C8—C9	−34.1 (3)	C10—N2—C14—C15	141.3 (2)
C5—N3—C9—C10	69.1 (3)	O3—N2—C14—C16	70.0 (3)
C6—N3—C9—C10	−119.1 (3)	C10—N2—C14—C16	−100.1 (3)
C5—N3—C9—C8	−169.4 (3)	O3—N2—C14—C11	−171.0 (2)
C6—N3—C9—C8	2.4 (3)	C10—N2—C14—C11	19.0 (3)
C7—C8—C9—N3	19.9 (3)	N1—C11—C14—N2	−21.2 (2)
C7—C8—C9—C10	141.4 (3)	C13—C11—C14—N2	−139.5 (3)
O3—N2—C10—N1	−177.0 (2)	C12—C11—C14—N2	91.6 (3)
C14—N2—C10—N1	−7.4 (3)	N1—C11—C14—C15	−139.7 (3)
O3—N2—C10—C9	0.5 (4)	C13—C11—C14—C15	102.0 (3)
C14—N2—C10—C9	170.0 (2)	C12—C11—C14—C15	−26.8 (4)
O2—N1—C10—N2	176.7 (2)	N1—C11—C14—C16	91.4 (3)
C11—N1—C10—N2	−8.6 (3)	C13—C11—C14—C16	−26.9 (4)
O2—N1—C10—C9	−0.8 (4)	C12—C11—C14—C16	−155.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1	0.96	2.47	3.043 (5)	118
C3—H3C···O1	0.96	2.43	3.025 (4)	120
C9—H11···O2	0.98	2.57	2.942 (4)	102
C16—H17C···O3ⁱ	0.96	2.48	3.390 (4)	157

Symmetry code: (i) −x+1, y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₈N₃O₄
M_r	326.41
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	6.1016 (12), 10.392 (2), 14.488 (3)
β (°)	101.312 (3)
V (Å³)	900.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.28 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4494, 1686, 1347
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.104, 0.97
No. of reflections	1686
No. of parameters	215
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1	0.96	2.47	3.043 (5)	118
C3—H3C···O1	0.96	2.43	3.025 (4)	120
C16—H17C···O3ⁱ	0.96	2.48	3.390 (4)	157

Symmetry code: (i) −x+1, y−1/2, −z+2.

Acknowledgements

We thank the Natural Science Foundation of China (grant Nos. 20972189, 20802092, 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
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
Qin, X. Y., Ding, G. R. & Sun, X. L. (2009). J. Chem. Res. pp. 511–514. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). 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
Tanaka, K., Furuichi, K., Kozaki, M., Suzuki, S., Shiomi, D., Sato, K., Takui, T. & Okada, K. (2007). Polyhedron, 26, 2021–2026. Web of Science CSD CrossRef CAS Google Scholar
Ullman, E. F., Osiecki, J. H., Boocock, D. G. B. & Darcy, R. (1974). J. Am. Chem. Soc. 96, 7049–7053. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o1954

https://doi.org/10.1107/S1600536810020672

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

2-[1-(tert-But­­oxy­carbonyl)­pyrrolidin-2-yl]-4,4,5,5-tetra­methyl-4,5-di­hydro-1H-imidazole-1-oxyl 3-oxide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[1-(tert-Butoxycarbonyl)pyrrolidin-2-yl]-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-1-oxyl 3-oxide