4,4,5,5-Tetramethyl-2-(4-pyridinio)imidazoline-1-oxyl-3-oxide chloride.

The title compound C(12)H(17)N(3)O(2) (+)·Cl(-) consists of a discrete [NITpPyH](+) cation [NITpPy = 2-(4'-pyrid-yl)-4,4,5,5-tetra-methyl-imidazoline-1-oxyl-3-oxide] and a chloride anion. The NITpPy mol-ecule is protonated at the N atom of the pyridyl ring. The anions and cations are connected via N-H⋯Cl hydrogen bonds.

Related literature

For the design and synthesis of mol­ecule-based magnetic materials, see: Bogani et al. (2005 ▶); Wang et al. (2004 ▶). For nitronyl nitroxide radicals (NITR), see: Fettouhi et al. (2003 ▶). For related literature, see: Stroh et al. (1999 ▶); Hirel et al. (2001 ▶); Chang et al. (2005 ▶); Wang et al. (2003 ▶). For the synthesis of the title compound see: Ullman et al. (1970 ▶, 1972 ▶)

Experimental

Crystal data

C12H17N3O2 +·Cl−

M = 270.74

Monoclinic,

a = 10.863 (14) Å

b = 11.927 (15) Å

c = 11.130 (15) Å

β = 102.81 (2)°

V = 1406 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 291 (2) K

0.30 × 0.26 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.923, T max = 0.939

7172 measured reflections

2609 independent reflections

2120 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.140

S = 1.03

2609 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808043158/bx2189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043158/bx2189Isup2.hkl

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

C12H17N3O2+·Cl−	F(000) = 572
Mr = 270.74	Dx = 1.279 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3005 reflections
a = 10.863 (14) Å	θ = 2.5–27.3°
b = 11.927 (15) Å	µ = 0.27 mm−1
c = 11.130 (15) Å	T = 291 K
β = 102.81 (2)°	BLOCK, black
V = 1406 (3) Å3	0.30 × 0.26 × 0.23 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2609 independent reflections
Radiation source: fine-focus sealed tube	2120 reflections with I > 2σ(I)
graphite	Rint = 0.037
phi and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→11
Tmin = 0.923, Tmax = 0.939	k = −13→14
7172 measured reflections	l = −13→13

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0696P)2 + 0.6783P] where P = (Fo2 + 2Fc2)/3
2609 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.22 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.05896 (6)	0.43910 (4)	0.31130 (6)	0.0548 (2)
O1	0.64998 (19)	1.16127 (15)	0.74894 (19)	0.0700 (6)
O2	0.78794 (19)	0.86362 (13)	0.53807 (17)	0.0633 (5)
N1	0.92752 (17)	1.26424 (15)	0.43535 (17)	0.0452 (5)
H1D	0.9687	1.3101	0.3992	0.054*
N2	0.67191 (18)	1.06169 (14)	0.71219 (17)	0.0425 (4)
N3	0.73993 (17)	0.92068 (14)	0.61433 (16)	0.0395 (4)
C1	0.8082 (2)	1.23103 (17)	0.5864 (2)	0.0437 (5)
H1	0.7700	1.2586	0.6473	0.052*
C2	0.8735 (2)	1.30278 (18)	0.5247 (2)	0.0479 (6)
H2	0.8799	1.3784	0.5454	0.057*
C3	0.9190 (2)	1.15584 (18)	0.4007 (2)	0.0437 (5)
H3	0.9562	1.1321	0.3375	0.052*
C4	0.8550 (2)	1.07904 (17)	0.45867 (19)	0.0391 (5)
H4	0.8484	1.0045	0.4336	0.047*
C5	0.80009 (18)	1.11518 (16)	0.55597 (18)	0.0343 (4)
C6	0.73824 (19)	1.03513 (16)	0.62469 (18)	0.0348 (5)
C7	0.6107 (2)	0.95916 (19)	0.7557 (2)	0.0446 (5)
C8	0.6900 (2)	0.86274 (18)	0.7158 (2)	0.0479 (6)
C9	0.6147 (3)	0.9682 (3)	0.8936 (3)	0.0755 (9)
H9A	0.7009	0.9699	0.9387	0.113*
H9B	0.5727	0.9047	0.9193	0.113*
H9C	0.5729	1.0358	0.9093	0.113*
C10	0.4731 (3)	0.9600 (3)	0.6823 (3)	0.0760 (9)
H10A	0.4336	1.0290	0.6972	0.114*
H10B	0.4285	0.8981	0.7078	0.114*
H10C	0.4713	0.9533	0.5959	0.114*
C11	0.8094 (3)	0.8328 (3)	0.8176 (3)	0.0673 (8)
H11A	0.8630	0.7836	0.7837	0.101*
H11B	0.7839	0.7962	0.8849	0.101*
H11C	0.8546	0.9002	0.8465	0.101*
C12	0.6206 (4)	0.7561 (2)	0.6664 (3)	0.0855 (11)
H12A	0.5572	0.7731	0.5938	0.128*
H12B	0.5814	0.7245	0.7279	0.128*
H12C	0.6795	0.7031	0.6462	0.128*

	U11	U22	U33	U12	U13	U23
Cl1	0.0756 (5)	0.0354 (3)	0.0595 (4)	−0.0077 (2)	0.0278 (3)	0.0030 (2)
O1	0.0900 (14)	0.0420 (9)	0.0963 (15)	0.0035 (9)	0.0597 (12)	−0.0127 (9)
O2	0.0960 (14)	0.0354 (8)	0.0746 (12)	−0.0055 (8)	0.0536 (11)	−0.0104 (8)
N1	0.0455 (11)	0.0403 (10)	0.0500 (11)	−0.0080 (8)	0.0114 (9)	0.0098 (8)
N2	0.0454 (11)	0.0370 (9)	0.0502 (11)	0.0003 (7)	0.0215 (9)	−0.0023 (7)
N3	0.0471 (11)	0.0319 (8)	0.0438 (10)	−0.0033 (7)	0.0197 (8)	−0.0025 (7)
C1	0.0529 (14)	0.0357 (11)	0.0439 (12)	−0.0023 (9)	0.0134 (10)	−0.0043 (9)
C2	0.0575 (15)	0.0315 (10)	0.0526 (14)	−0.0059 (9)	0.0082 (11)	−0.0007 (9)
C3	0.0432 (13)	0.0431 (11)	0.0476 (12)	0.0019 (9)	0.0159 (10)	0.0056 (9)
C4	0.0428 (12)	0.0329 (10)	0.0439 (12)	−0.0007 (8)	0.0142 (10)	0.0002 (8)
C5	0.0331 (11)	0.0316 (9)	0.0378 (11)	−0.0006 (8)	0.0065 (8)	0.0010 (8)
C6	0.0356 (11)	0.0329 (10)	0.0377 (11)	−0.0004 (8)	0.0115 (9)	−0.0010 (8)
C7	0.0433 (13)	0.0459 (12)	0.0495 (13)	−0.0048 (9)	0.0206 (10)	0.0017 (9)
C8	0.0563 (14)	0.0375 (11)	0.0575 (14)	−0.0053 (10)	0.0288 (12)	0.0041 (9)
C9	0.102 (3)	0.0758 (19)	0.0605 (17)	0.0035 (17)	0.0428 (17)	0.0043 (14)
C10	0.0460 (16)	0.080 (2)	0.102 (3)	−0.0054 (14)	0.0163 (16)	0.0114 (17)
C11	0.0678 (18)	0.0642 (16)	0.0743 (18)	0.0131 (13)	0.0250 (15)	0.0262 (14)
C12	0.103 (3)	0.0554 (16)	0.116 (3)	−0.0362 (17)	0.064 (2)	−0.0199 (17)

O1—N2	1.295 (3)	C7—C9	1.529 (4)
O2—N3	1.285 (2)	C7—C10	1.536 (4)
N1—C2	1.343 (3)	C7—C8	1.559 (3)
N1—C3	1.346 (3)	C8—C12	1.518 (4)
N1—H1D	0.8600	C8—C11	1.563 (4)
N2—C6	1.371 (3)	C9—H9A	0.9600
N2—C7	1.522 (3)	C9—H9B	0.9600
N3—C6	1.370 (3)	C9—H9C	0.9600
N3—C8	1.523 (3)	C10—H10A	0.9600
C1—C2	1.387 (3)	C10—H10B	0.9600
C1—C5	1.421 (3)	C10—H10C	0.9600
C1—H1	0.9300	C11—H11A	0.9600
C2—H2	0.9300	C11—H11B	0.9600
C3—C4	1.392 (3)	C11—H11C	0.9600
C3—H3	0.9300	C12—H12A	0.9600
C4—C5	1.415 (3)	C12—H12B	0.9600
C4—H4	0.9300	C12—H12C	0.9600
C5—C6	1.475 (3)
C2—N1—C3	121.81 (19)	C10—C7—C8	112.8 (2)
C2—N1—H1D	119.1	C12—C8—N3	110.0 (2)
C3—N1—H1D	119.1	C12—C8—C7	117.4 (2)
O1—N2—C6	126.78 (18)	N3—C8—C7	100.76 (18)
O1—N2—C7	120.83 (19)	C12—C8—C11	109.7 (3)
C6—N2—C7	112.09 (17)	N3—C8—C11	105.4 (2)
O2—N3—C6	126.73 (17)	C7—C8—C11	112.6 (2)
O2—N3—C8	120.85 (18)	C7—C9—H9A	109.5
C6—N3—C8	112.09 (17)	C7—C9—H9B	109.5
C2—C1—C5	119.6 (2)	H9A—C9—H9B	109.5
C2—C1—H1	120.2	C7—C9—H9C	109.5
C5—C1—H1	120.2	H9A—C9—H9C	109.5
N1—C2—C1	120.7 (2)	H9B—C9—H9C	109.5
N1—C2—H2	119.6	C7—C10—H10A	109.5
C1—C2—H2	119.6	C7—C10—H10B	109.5
N1—C3—C4	120.6 (2)	H10A—C10—H10B	109.5
N1—C3—H3	119.7	C7—C10—H10C	109.5
C4—C3—H3	119.7	H10A—C10—H10C	109.5
C3—C4—C5	119.5 (2)	H10B—C10—H10C	109.5
C3—C4—H4	120.2	C8—C11—H11A	109.5
C5—C4—H4	120.2	C8—C11—H11B	109.5
C4—C5—C1	117.69 (18)	H11A—C11—H11B	109.5
C4—C5—C6	121.17 (19)	C8—C11—H11C	109.5
C1—C5—C6	121.13 (19)	H11A—C11—H11C	109.5
N3—C6—N2	108.00 (17)	H11B—C11—H11C	109.5
N3—C6—C5	125.80 (18)	C8—C12—H12A	109.5
N2—C6—C5	126.18 (19)	C8—C12—H12B	109.5
N2—C7—C9	110.2 (2)	H12A—C12—H12B	109.5
N2—C7—C10	105.5 (2)	C8—C12—H12C	109.5
C9—C7—C10	109.9 (2)	H12A—C12—H12C	109.5
N2—C7—C8	101.19 (18)	H12B—C12—H12C	109.5
C9—C7—C8	116.3 (2)
C3—N1—C2—C1	1.1 (3)	C6—N2—C7—C9	143.3 (2)
C5—C1—C2—N1	1.0 (3)	O1—N2—C7—C10	76.0 (3)
C2—N1—C3—C4	−1.1 (3)	C6—N2—C7—C10	−98.1 (2)
N1—C3—C4—C5	−0.9 (3)	O1—N2—C7—C8	−166.4 (2)
C3—C4—C5—C1	2.9 (3)	C6—N2—C7—C8	19.6 (2)
C3—C4—C5—C6	−176.24 (19)	O2—N3—C8—C12	−40.2 (3)
C2—C1—C5—C4	−2.9 (3)	C6—N3—C8—C12	146.0 (2)
C2—C1—C5—C6	176.2 (2)	O2—N3—C8—C7	−164.7 (2)
O2—N3—C6—N2	176.6 (2)	C6—N3—C8—C7	21.4 (2)
C8—N3—C6—N2	−10.0 (2)	O2—N3—C8—C11	78.0 (3)
O2—N3—C6—C5	−4.9 (3)	C6—N3—C8—C11	−95.8 (2)
C8—N3—C6—C5	168.50 (19)	N2—C7—C8—C12	−141.9 (2)
O1—N2—C6—N3	179.6 (2)	C9—C7—C8—C12	98.7 (3)
C7—N2—C6—N3	−6.8 (2)	C10—C7—C8—C12	−29.7 (3)
O1—N2—C6—C5	1.1 (4)	N2—C7—C8—N3	−22.6 (2)
C7—N2—C6—C5	174.72 (19)	C9—C7—C8—N3	−142.0 (2)
C4—C5—C6—N3	8.4 (3)	C10—C7—C8—N3	89.7 (2)
C1—C5—C6—N3	−170.7 (2)	N2—C7—C8—C11	89.3 (2)
C4—C5—C6—N2	−173.4 (2)	C9—C7—C8—C11	−30.1 (3)
C1—C5—C6—N2	7.5 (3)	C10—C7—C8—C11	−158.4 (2)
O1—N2—C7—C9	−42.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl1i	0.86	2.17	3.028 (3)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯Cl1i	0.86	2.17	3.028 (3)	174

Symmetry code: (i) .