2-(2-Pyrrolidinio)-1H-benzimidazol-3-ium dinitrate.

In the title compound, C(11)H(15)N(3) (2+)·2NO(3) (-), one of the imidazole N atoms and the N atom of the pyrrolidine ring are protonated. The pyrrolidine ring adopts an envelope conformation, with the C atom carrying the benzoimidazolium substituent as the flap atom. In the crystal structure, cations and anions are linked through N-H⋯O hydrogen bonds, forming chains that run parallel to the c axis.

Related literature

For background to the applications of proline derivatives, see: Fu et al. (2007 ▶); Aminabhavi et al. (1986 ▶). For the structures of metal complexes with ligands similar to the title compound, see: Dai & Fu (2008a ▶,b ▶); Fu & Ye (2007 ▶).

Experimental

Crystal data

C11H15N3 2+·2NO3 −

M = 313.28

Monoclinic,

a = 22.078 (2) Å

b = 11.154 (1) Å

c = 14.670 (1) Å

β = 127.18 (1)°

V = 2878.3 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.35 × 0.30 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.959, T max = 0.982

14543 measured reflections

3276 independent reflections

2195 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.144

S = 1.09

3276 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018558/sj2610sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018558/sj2610Isup2.hkl

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

C11H15N32+·2NO3−	F(000) = 1312
Mr = 313.28	Dx = 1.446 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3275 reflections
a = 22.078 (2) Å	θ = 3.2–27.5°
b = 11.154 (1) Å	µ = 0.12 mm−1
c = 14.670 (1) Å	T = 298 K
β = 127.18 (1)°	Block, colourless
V = 2878.3 (4) Å3	0.35 × 0.30 × 0.15 mm
Z = 8

Rigaku Mercury2 diffractometer	3276 independent reflections
Radiation source: fine-focus sealed tube	2195 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −28→28
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −14→14
Tmin = 0.959, Tmax = 0.982	l = −18→19
14543 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0493P)2 + 2.1933P] where P = (Fo2 + 2Fc2)/3
3276 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.19 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 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.

	x	y	z	Uiso*/Ueq
N3	0.66938 (10)	0.39290 (15)	0.56483 (15)	0.0433 (4)
H3A	0.6966	0.3290	0.5937	0.052*
N4	0.63804 (11)	0.58040 (17)	0.53606 (17)	0.0513 (5)
H4A	0.6414	0.6572	0.5428	0.062*
N5	0.83307 (9)	0.45350 (16)	0.71441 (14)	0.0429 (4)
H5A	0.8163	0.4119	0.6506	0.052*
H5B	0.8425	0.4016	0.7686	0.052*
C1	0.57133 (13)	0.5163 (2)	0.4595 (2)	0.0500 (6)
C2	0.49697 (15)	0.5521 (3)	0.3784 (3)	0.0709 (8)
H2	0.4832	0.6325	0.3664	0.085*
C3	0.44437 (16)	0.4628 (3)	0.3162 (3)	0.0778 (9)
H3	0.3939	0.4834	0.2599	0.093*
C4	0.46486 (16)	0.3430 (3)	0.3353 (2)	0.0725 (8)
H4	0.4273	0.2856	0.2920	0.087*
C5	0.53812 (15)	0.3057 (2)	0.4155 (2)	0.0593 (7)
H5	0.5513	0.2250	0.4276	0.071*
C6	0.59181 (12)	0.3961 (2)	0.47789 (19)	0.0448 (5)
C7	0.69499 (12)	0.50468 (19)	0.59632 (18)	0.0418 (5)
C8	0.77457 (13)	0.54335 (19)	0.6904 (2)	0.0465 (6)
H8	0.7785	0.5530	0.7602	0.056*
C9	0.80026 (15)	0.6590 (2)	0.6698 (2)	0.0616 (7)
H9A	0.7799	0.7281	0.6831	0.074*
H9B	0.7852	0.6626	0.5926	0.074*
C10	0.88635 (15)	0.6521 (2)	0.7577 (2)	0.0617 (7)
H10A	0.9112	0.7044	0.7367	0.074*
H10B	0.9022	0.6745	0.8331	0.074*
C11	0.90467 (14)	0.5220 (2)	0.7552 (2)	0.0556 (6)
H11A	0.9471	0.4953	0.8308	0.067*
H11B	0.9174	0.5107	0.7030	0.067*
O1	0.64618 (11)	0.82051 (14)	0.60914 (14)	0.0612 (5)
O2	0.58007 (14)	0.83408 (18)	0.42662 (16)	0.0852 (7)
O3	0.59348 (11)	0.98868 (15)	0.52487 (15)	0.0672 (5)
N1	0.60605 (11)	0.88315 (18)	0.51830 (16)	0.0492 (5)
O4	0.74570 (10)	0.68205 (14)	0.85048 (13)	0.0533 (4)
O5	0.81397 (9)	0.66960 (14)	1.03479 (13)	0.0513 (4)
O6	0.74016 (11)	0.52300 (15)	0.93113 (17)	0.0698 (5)
N2	0.76639 (11)	0.62317 (16)	0.93912 (16)	0.0447 (5)

	U11	U22	U33	U12	U13	U23
N3	0.0448 (10)	0.0328 (9)	0.0462 (10)	0.0007 (8)	0.0243 (9)	−0.0039 (8)
N4	0.0516 (12)	0.0344 (10)	0.0625 (13)	0.0033 (9)	0.0316 (11)	−0.0006 (9)
N5	0.0440 (10)	0.0434 (10)	0.0335 (9)	−0.0035 (8)	0.0193 (8)	−0.0069 (8)
C1	0.0441 (13)	0.0517 (14)	0.0519 (14)	0.0021 (11)	0.0278 (12)	0.0013 (11)
C2	0.0538 (17)	0.0731 (19)	0.0754 (19)	0.0149 (14)	0.0336 (15)	0.0152 (15)
C3	0.0405 (15)	0.110 (3)	0.0671 (19)	0.0017 (17)	0.0243 (14)	0.0035 (18)
C4	0.0516 (17)	0.092 (2)	0.0664 (18)	−0.0206 (16)	0.0319 (15)	−0.0162 (17)
C5	0.0569 (16)	0.0599 (16)	0.0629 (16)	−0.0148 (13)	0.0371 (14)	−0.0149 (13)
C6	0.0439 (13)	0.0464 (13)	0.0459 (13)	−0.0027 (10)	0.0280 (11)	−0.0055 (10)
C7	0.0455 (13)	0.0349 (11)	0.0445 (12)	−0.0014 (9)	0.0270 (11)	−0.0066 (9)
C8	0.0518 (13)	0.0391 (12)	0.0487 (13)	−0.0036 (10)	0.0304 (12)	−0.0098 (10)
C9	0.0662 (17)	0.0392 (13)	0.0772 (18)	−0.0109 (12)	0.0421 (15)	−0.0112 (13)
C10	0.0657 (16)	0.0575 (16)	0.0641 (16)	−0.0226 (13)	0.0404 (14)	−0.0202 (13)
C11	0.0496 (14)	0.0642 (16)	0.0529 (14)	−0.0100 (12)	0.0310 (12)	−0.0077 (12)
O1	0.0807 (12)	0.0462 (10)	0.0502 (10)	0.0166 (9)	0.0361 (10)	0.0115 (8)
O2	0.1258 (19)	0.0759 (14)	0.0539 (12)	−0.0102 (13)	0.0543 (13)	−0.0108 (10)
O3	0.0808 (13)	0.0431 (10)	0.0649 (12)	0.0163 (9)	0.0373 (10)	0.0099 (8)
N1	0.0563 (12)	0.0456 (12)	0.0463 (11)	0.0003 (9)	0.0313 (10)	0.0037 (9)
O4	0.0766 (12)	0.0444 (9)	0.0399 (9)	0.0054 (8)	0.0357 (9)	0.0043 (7)
O5	0.0596 (10)	0.0485 (9)	0.0389 (9)	−0.0026 (8)	0.0261 (8)	0.0033 (7)
O6	0.0716 (12)	0.0441 (10)	0.0778 (13)	−0.0113 (9)	0.0367 (11)	0.0063 (9)
N2	0.0514 (11)	0.0372 (10)	0.0485 (11)	0.0065 (9)	0.0318 (10)	0.0053 (9)

N3—C7	1.331 (3)	C5—H5	0.9300
N3—C6	1.386 (3)	C7—C8	1.499 (3)
N3—H3A	0.8600	C8—C9	1.511 (3)
N4—C7	1.316 (3)	C8—H8	0.9800
N4—C1	1.393 (3)	C9—C10	1.523 (4)
N4—H4A	0.8600	C9—H9A	0.9700
N5—C8	1.499 (3)	C9—H9B	0.9700
N5—C11	1.516 (3)	C10—C11	1.514 (4)
N5—H5A	0.9000	C10—H10A	0.9700
N5—H5B	0.9000	C10—H10B	0.9700
C1—C2	1.382 (4)	C11—H11A	0.9700
C1—C6	1.388 (3)	C11—H11B	0.9700
C2—C3	1.375 (4)	O1—N1	1.274 (2)
C2—H2	0.9300	O2—N1	1.227 (2)
C3—C4	1.384 (4)	O3—N1	1.226 (2)
C3—H3	0.9300	O4—N2	1.270 (2)
C4—C5	1.369 (4)	O5—N2	1.249 (2)
C4—H4	0.9300	O6—N2	1.231 (2)
C5—C6	1.396 (3)
C7—N3—C6	108.93 (18)	N3—C7—C8	127.21 (19)
C7—N3—H3A	125.5	N5—C8—C7	112.84 (17)
C6—N3—H3A	125.5	N5—C8—C9	104.12 (19)
C7—N4—C1	109.12 (19)	C7—C8—C9	115.8 (2)
C7—N4—H4A	125.4	N5—C8—H8	107.9
C1—N4—H4A	125.4	C7—C8—H8	107.9
C8—N5—C11	107.51 (17)	C9—C8—H8	107.9
C8—N5—H5A	110.2	C8—C9—C10	102.4 (2)
C11—N5—H5A	110.2	C8—C9—H9A	111.3
C8—N5—H5B	110.2	C10—C9—H9A	111.3
C11—N5—H5B	110.2	C8—C9—H9B	111.3
H5A—N5—H5B	108.5	C10—C9—H9B	111.3
C2—C1—C6	121.6 (2)	H9A—C9—H9B	109.2
C2—C1—N4	132.3 (2)	C11—C10—C9	104.05 (19)
C6—C1—N4	106.1 (2)	C11—C10—H10A	110.9
C3—C2—C1	116.8 (3)	C9—C10—H10A	110.9
C3—C2—H2	121.6	C11—C10—H10B	110.9
C1—C2—H2	121.6	C9—C10—H10B	110.9
C2—C3—C4	121.5 (3)	H10A—C10—H10B	109.0
C2—C3—H3	119.2	C10—C11—N5	105.2 (2)
C4—C3—H3	119.2	C10—C11—H11A	110.7
C5—C4—C3	122.7 (3)	N5—C11—H11A	110.7
C5—C4—H4	118.7	C10—C11—H11B	110.7
C3—C4—H4	118.7	N5—C11—H11B	110.7
C4—C5—C6	116.0 (3)	H11A—C11—H11B	108.8
C4—C5—H5	122.0	O3—N1—O2	122.4 (2)
C6—C5—H5	122.0	O3—N1—O1	119.45 (19)
N3—C6—C1	106.27 (19)	O2—N1—O1	118.1 (2)
N3—C6—C5	132.2 (2)	O6—N2—O5	120.74 (19)
C1—C6—C5	121.5 (2)	O6—N2—O4	120.96 (19)
N4—C7—N3	109.58 (19)	O5—N2—O4	118.29 (18)
N4—C7—C8	123.10 (19)
C7—N4—C1—C2	−180.0 (3)	C1—N4—C7—N3	−0.9 (3)
C7—N4—C1—C6	0.2 (3)	C1—N4—C7—C8	−177.2 (2)
C6—C1—C2—C3	−0.4 (4)	C6—N3—C7—N4	1.2 (3)
N4—C1—C2—C3	179.8 (3)	C6—N3—C7—C8	177.4 (2)
C1—C2—C3—C4	1.0 (4)	C11—N5—C8—C7	149.12 (19)
C2—C3—C4—C5	−0.9 (5)	C11—N5—C8—C9	22.8 (2)
C3—C4—C5—C6	0.1 (4)	N4—C7—C8—N5	−157.4 (2)
C7—N3—C6—C1	−1.0 (2)	N3—C7—C8—N5	26.9 (3)
C7—N3—C6—C5	−180.0 (2)	N4—C7—C8—C9	−37.6 (3)
C2—C1—C6—N3	−179.4 (2)	N3—C7—C8—C9	146.7 (2)
N4—C1—C6—N3	0.5 (2)	N5—C8—C9—C10	−38.4 (2)
C2—C1—C6—C5	−0.3 (4)	C7—C8—C9—C10	−162.8 (2)
N4—C1—C6—C5	179.6 (2)	C8—C9—C10—C11	39.8 (3)
C4—C5—C6—N3	179.2 (2)	C9—C10—C11—N5	−25.8 (3)
C4—C5—C6—C1	0.4 (4)	C8—N5—C11—C10	2.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4i	0.86	1.93	2.788 (2)	177
N3—H3A···O5i	0.86	2.50	3.020 (2)	120
N5—H5B···O1i	0.90	1.89	2.771 (2)	167
N5—H5B···O3i	0.90	2.64	3.149 (2)	117
N5—H5A···O5ii	0.90	1.90	2.768 (2)	162
N4—H4A···O1	0.86	2.04	2.850 (2)	157
N4—H4A···O2	0.86	2.42	3.121 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O4i	0.86	1.93	2.788 (2)	177
N3—H3A⋯O5i	0.86	2.50	3.020 (2)	120
N5—H5B⋯O1i	0.90	1.89	2.771 (2)	167
N5—H5B⋯O3i	0.90	2.64	3.149 (2)	117
N5—H5A⋯O5ii	0.90	1.90	2.768 (2)	162
N4—H4A⋯O1	0.86	2.04	2.850 (2)	157
N4—H4A⋯O2	0.86	2.42	3.121 (3)	139

Symmetry codes: (i) ; (ii) .