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

Chang, J.L.; Gao, Z.Y.; Jiang, K.

doi:10.1107/S1600536808043158

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o200

doi:10.1107/S1600536808043158

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

Jiu Li Chang,^a Zhi Yong Gao ^a and Kai Jiang ^a ^*

^aCollege of Chemistry and Environmental Science, Henan Normal University, Xinxiang, 453002, People's Republic of China
^*Correspondence e-mail: gaozhy201@sohu.com

(Received 11 December 2008; accepted 18 December 2008; online 24 December 2008)

The title compound C₁₂H₁₇N₃O₂⁺·Cl⁻ consists of a discrete [NITpPyH]⁺ cation [NITpPy = 2-(4′-pyridyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide] and a chloride anion. The NITpPy molecule 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_r = 270.74
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.140
S = 1.03
2609 reflections
167 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) x+1, y+1, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

The design and synthesis of molecule-based magnetic materials is one of the major subjects of materials science in which the combination of metal ions and organic radicals are used to construct assembled systems (Bogani et al., 2005; Wang et al., 2004). Nitronyl nitroxide radicals (NITR), independently or in combination with metal ions, have been one of the most widely studied systems in molecular magnetism for understanding the radical-radical or metal-radical as well as for synthesizing organic ferromagnets and metal-radical magnetic materials (Fettouhi et al., 2003). However, to our knowledge so far few charge transfer complexes of nitronyl nitroxide radicals used as proton receptor have been reported. In order to better understand the behavior of proton transfer in charge transfer complexes, the synthesis and crystal structure of the title compound have been investigated. The structure of the title compound is shown in Fig. 1. The NITpPy molecule is protonated at N atom of the pyridyl ring by accepting a proton from the acid solution. The transfer of protons result in a intermolecular hydrogen bond between NITpPy and chloride.The anions and cations are connected via N—H···Cl hydrogen bonds. The nitronyl nitroxide fragment O—N—C—N—O is almost coplanar, but make a dihedral angle of 8.6 (2)° with the pyridyl ring.

Related literature top

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 top

NITpPy was synthesized according to a literature procedure (Ullman et al.,1970; Ullman et al., 1972). Single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from acetonitrile solution and HCl 10:1 (v/v) solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).

Figures top

Fig. 1. ORTEP drawing of the title compound with atom labeling. The thermal ellipsoids are drawn at 30% probability level.

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

Crystal data top

C₁₂H₁₇N₃O₂⁺·Cl⁻	F(000) = 572
M_r = 270.74	D_x = 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

Data collection top

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

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0696P)² + 0.6783P] where P = (F_o² + 2F_c²)/3
2609 reflections	(Δ/σ)_max = 0.001
167 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₂H₁₇N₃O₂⁺·Cl⁻	V = 1406 (3) Å³
M_r = 270.74	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.863 (14) Å	µ = 0.27 mm⁻¹
b = 11.927 (15) Å	T = 291 K
c = 11.130 (15) Å	0.30 × 0.26 × 0.23 mm
β = 102.81 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2609 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2120 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.939	R_int = 0.037
7172 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	Δρ_max = 0.44 e Å⁻³
2609 reflections	Δρ_min = −0.22 e Å⁻³
167 parameters

Special details top

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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₇N₃O₂⁺·Cl⁻
M_r	270.74
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	10.863 (14), 11.927 (15), 11.130 (15)
β (°)	102.81 (2)
V (Å³)	1406 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.26 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.923, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	7172, 2609, 2120
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.140, 1.03
No. of reflections	2609
No. of parameters	167
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.22

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl1ⁱ	0.86	2.17	3.028 (3)	174.0

Symmetry code: (i) x+1, y+1, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20471026) and the Natural Science Foundation of Henan Province (No. 0311021200).

References

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