4-Ethoxy-imino-N'-methoxy-pyrrolidin-1-ium-3-carboximidamidium dichloride.

The title compound, C(8)H(18)N(4)O(2) (2+)·2Cl(-), contains two oxime groups. The methyl oxime group has a Z configuration, and the ethyl oxime group is disordered, with both Z and E configurations in occupancies of 0.840 (8) and 0.160 (8), respectively. In the crystal structure, there are a number of N-H⋯Cl hydrogen bonds.

Related literature

For properties of quinolone derivatives, see: Ball et al. (1998 ▶); Ray et al. (2005 ▶). For the synthesis of new quinolones, see: Anderson & Osheroff (2001 ▶); Choi et al. (2004 ▶); Wang, Guo et al. (2008 ▶). For some crystal structures of quinolones, see: Wang, Liu et al. (2008 ▶).

Experimental

Crystal data

C8H18N4O2 2+·2Cl−

M = 273.16

Orthorhombic,

a = 12.7355 (14) Å

b = 8.8506 (12) Å

c = 26.334 (2) Å

V = 2968.3 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 298 K

0.23 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.907, T max = 0.922

14370 measured reflections

2597 independent reflections

1986 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.210

S = 1.08

2597 reflections

170 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT and SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004772/pk2146sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004772/pk2146Isup2.hkl

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

C8H18N4O22+·2Cl−	F(000) = 1152
Mr = 273.16	Dx = 1.223 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2n 2ab	Cell parameters from 3944 reflections
a = 12.7355 (14) Å	θ = 2.2–24.1°
b = 8.8506 (12) Å	µ = 0.43 mm−1
c = 26.334 (2) Å	T = 298 K
V = 2968.3 (6) Å3	Block, colorless
Z = 8	0.23 × 0.20 × 0.19 mm

Bruker SMART CCD area-detector diffractometer	2597 independent reflections
Radiation source: fine-focus sealed tube	1986 reflections with I > 2σ(I)
graphite	Rint = 0.062
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
Tmin = 0.907, Tmax = 0.922	k = −10→10
14370 measured reflections	l = −29→31

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0819P)2 + 7.7771P] where P = (Fo2 + 2Fc2)/3
2597 reflections	(Δ/σ)max = 0.001
170 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.33 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	Occ. (<1)
Cl1	0.67028 (9)	0.08761 (14)	0.52171 (5)	0.0516 (4)
Cl2	0.18814 (10)	0.22720 (17)	0.63480 (6)	0.0636 (5)
N1	0.3711 (3)	0.1103 (5)	0.57222 (17)	0.0528 (11)
H1A	0.3640	0.0382	0.5484	0.063*
H1B	0.3090	0.1220	0.5881	0.063*
N2	0.5131 (3)	0.5960 (4)	0.59228 (17)	0.0543 (11)
H2	0.4590	0.6173	0.6105	0.065*
N3	0.6142 (3)	0.4217 (5)	0.55190 (18)	0.0573 (12)
H3A	0.6593	0.4897	0.5437	0.069*
H3B	0.6239	0.3293	0.5429	0.069*
N4	0.559 (2)	0.2442 (19)	0.6611 (11)	0.065 (4)	0.840 (8)
N4'	0.570 (12)	0.212 (14)	0.657 (6)	0.065 (4)	0.160 (8)
O1	0.5835 (3)	0.7083 (4)	0.57752 (15)	0.0579 (10)
O2	0.5905 (4)	0.1079 (6)	0.6834 (2)	0.0762 (17)	0.840 (8)
O2'	0.581 (2)	0.352 (3)	0.6806 (10)	0.071 (8)	0.160 (8)
C1	0.4045 (4)	0.2533 (6)	0.5489 (2)	0.0503 (12)
H1C	0.3451	0.3066	0.5343	0.060*
H1D	0.4564	0.2359	0.5226	0.060*
C2	0.4513 (4)	0.3417 (5)	0.59299 (19)	0.0446 (11)
H2A	0.3944	0.3920	0.6115	0.053*
C3	0.4953 (4)	0.2171 (5)	0.62580 (18)	0.0454 (11)
C4	0.4533 (4)	0.0679 (6)	0.6089 (2)	0.0545 (13)
H4A	0.5075	0.0076	0.5929	0.065*
H4B	0.4240	0.0119	0.6372	0.065*
C5	0.5316 (4)	0.4584 (5)	0.57781 (19)	0.0443 (11)
C6	0.6473 (6)	0.7496 (7)	0.6196 (3)	0.0761 (18)
H6A	0.6036	0.7852	0.6468	0.091*
H6B	0.6949	0.8283	0.6096	0.091*
H6C	0.6866	0.6633	0.6309	0.091*
C7	0.6511 (8)	0.1432 (11)	0.7286 (3)	0.089 (3)	0.840 (8)
H7A	0.6104	0.2054	0.7517	0.106*	0.840 (8)
H7B	0.7149	0.1970	0.7197	0.106*	0.840 (8)
C8	0.6770 (12)	−0.0062 (15)	0.7528 (5)	0.142 (5)	0.840 (8)
H8A	0.6131	−0.0580	0.7613	0.171*	0.840 (8)
H8B	0.7174	0.0105	0.7830	0.171*	0.840 (8)
H8C	0.7169	−0.0665	0.7294	0.171*	0.840 (8)
C7'	0.648 (4)	0.337 (6)	0.7247 (18)	0.089 (3)	0.160 (8)
H7'1	0.6934	0.2488	0.7214	0.106*	0.160 (8)
H7'2	0.6072	0.3274	0.7555	0.106*	0.160 (8)
C8'	0.713 (6)	0.482 (7)	0.725 (2)	0.12 (2)	0.160 (8)
H8'1	0.7592	0.4822	0.7541	0.148*	0.160 (8)
H8'2	0.6673	0.5680	0.7270	0.148*	0.160 (8)
H8'3	0.7545	0.4884	0.6947	0.148*	0.160 (8)

	U11	U22	U33	U12	U13	U23
Cl1	0.0413 (7)	0.0468 (7)	0.0667 (8)	0.0032 (5)	−0.0018 (6)	−0.0150 (6)
Cl2	0.0396 (7)	0.0652 (9)	0.0862 (10)	−0.0009 (6)	0.0023 (6)	−0.0207 (8)
N1	0.040 (2)	0.053 (3)	0.065 (3)	−0.010 (2)	0.003 (2)	−0.020 (2)
N2	0.049 (2)	0.039 (2)	0.074 (3)	−0.002 (2)	0.011 (2)	−0.006 (2)
N3	0.044 (2)	0.038 (2)	0.090 (3)	−0.0026 (19)	0.018 (2)	−0.007 (2)
N4	0.067 (7)	0.060 (11)	0.068 (6)	−0.008 (7)	−0.015 (5)	0.001 (8)
N4'	0.067 (7)	0.060 (11)	0.068 (6)	−0.008 (7)	−0.015 (5)	0.001 (8)
O1	0.058 (2)	0.0403 (19)	0.076 (3)	−0.0096 (17)	0.011 (2)	0.0023 (18)
O2	0.086 (4)	0.065 (3)	0.077 (3)	−0.009 (3)	−0.027 (3)	0.008 (3)
O2'	0.078 (18)	0.065 (18)	0.072 (17)	−0.006 (14)	−0.016 (14)	−0.016 (15)
C1	0.035 (2)	0.059 (3)	0.057 (3)	0.002 (2)	−0.005 (2)	−0.004 (2)
C2	0.036 (2)	0.040 (3)	0.058 (3)	−0.001 (2)	0.005 (2)	−0.002 (2)
C3	0.040 (3)	0.049 (3)	0.047 (3)	−0.009 (2)	−0.004 (2)	0.000 (2)
C4	0.049 (3)	0.046 (3)	0.068 (3)	−0.004 (2)	0.000 (3)	−0.002 (3)
C5	0.036 (2)	0.041 (3)	0.056 (3)	0.004 (2)	−0.001 (2)	−0.004 (2)
C6	0.070 (4)	0.065 (4)	0.093 (5)	−0.016 (3)	0.007 (4)	−0.014 (3)
C7	0.094 (6)	0.090 (6)	0.082 (5)	0.004 (5)	−0.034 (5)	0.001 (5)
C8	0.177 (14)	0.139 (10)	0.110 (9)	0.045 (9)	−0.059 (9)	0.010 (8)
C7'	0.094 (6)	0.090 (6)	0.082 (5)	0.004 (5)	−0.034 (5)	0.001 (5)
C8'	0.14 (5)	0.13 (5)	0.10 (4)	0.01 (4)	−0.02 (4)	−0.03 (4)

N1—C1	1.470 (7)	C2—C3	1.509 (7)
N1—C4	1.473 (7)	C2—H2A	0.9800
N1—H1A	0.9000	C3—C4	1.493 (7)
N1—H1B	0.9000	C4—H4A	0.9700
N2—C5	1.297 (6)	C4—H4B	0.9700
N2—O1	1.393 (5)	C6—H6A	0.9600
N2—H2	0.8600	C6—H6B	0.9600
N3—C5	1.296 (6)	C6—H6C	0.9600
N3—H3A	0.8600	C7—C8	1.504 (14)
N3—H3B	0.8600	C7—H7A	0.9700
N4—C3	1.26 (3)	C7—H7B	0.9700
N4—O2	1.40 (2)	C8—H8A	0.9600
N4'—C3	1.26 (16)	C8—H8B	0.9600
N4'—O2'	1.39 (12)	C8—H8C	0.9600
O1—C6	1.423 (8)	C7'—C8'	1.53 (8)
O2—C7	1.454 (9)	C7'—H7'1	0.9700
O2'—C7'	1.45 (5)	C7'—H7'2	0.9700
C1—C2	1.521 (7)	C8'—H8'1	0.9600
C1—H1C	0.9700	C8'—H8'2	0.9600
C1—H1D	0.9700	C8'—H8'3	0.9600
C2—C5	1.507 (7)
C1—N1—C4	106.7 (4)	N1—C4—H4B	111.2
C1—N1—H1A	110.4	C3—C4—H4B	111.2
C4—N1—H1A	110.4	H4A—C4—H4B	109.1
C1—N1—H1B	110.4	N3—C5—N2	122.5 (5)
C4—N1—H1B	110.4	N3—C5—C2	121.2 (4)
H1A—N1—H1B	108.6	N2—C5—C2	116.3 (4)
C5—N2—O1	118.1 (4)	O1—C6—H6A	109.5
C5—N2—H2	120.9	O1—C6—H6B	109.5
O1—N2—H2	120.9	H6A—C6—H6B	109.5
C5—N3—H3A	120.0	O1—C6—H6C	109.5
C5—N3—H3B	120.0	H6A—C6—H6C	109.5
H3A—N3—H3B	120.0	H6B—C6—H6C	109.5
C3—N4—O2	109.2 (14)	O2—C7—C8	105.9 (8)
C3—N4'—O2'	109 (9)	O2—C7—H7A	110.6
N2—O1—C6	109.5 (4)	C8—C7—H7A	110.6
N4—O2—C7	108.0 (11)	O2—C7—H7B	110.6
N4'—O2'—C7'	109 (7)	C8—C7—H7B	110.6
N1—C1—C2	103.8 (4)	H7A—C7—H7B	108.7
N1—C1—H1C	111.0	C7—C8—H8A	109.5
C2—C1—H1C	111.0	C7—C8—H8B	109.5
N1—C1—H1D	111.0	H8A—C8—H8B	109.5
C2—C1—H1D	111.0	C7—C8—H8C	109.5
H1C—C1—H1D	109.0	H8A—C8—H8C	109.5
C5—C2—C3	113.7 (4)	H8B—C8—H8C	109.5
C5—C2—C1	114.6 (4)	O2'—C7'—C8'	104 (4)
C3—C2—C1	101.9 (4)	O2'—C7'—H7'1	110.9
C5—C2—H2A	108.8	C8'—C7'—H7'1	110.9
C3—C2—H2A	108.8	O2'—C7'—H7'2	110.9
C1—C2—H2A	108.8	C8'—C7'—H7'2	110.9
N4—C3—C4	128.4 (10)	H7'1—C7'—H7'2	108.9
N4'—C3—C4	116 (6)	C7'—C8'—H8'1	109.5
N4—C3—C2	121.6 (10)	C7'—C8'—H8'2	109.5
N4'—C3—C2	133 (7)	H8'1—C8'—H8'2	109.5
C4—C3—C2	110.0 (4)	C7'—C8'—H8'3	109.5
N1—C4—C3	103.0 (4)	H8'1—C8'—H8'3	109.5
N1—C4—H4A	111.2	H8'2—C8'—H8'3	109.5
C3—C4—H4A	111.2
C5—N2—O1—C6	−104.6 (6)	C5—C2—C3—C4	−137.4 (4)
C3—N4—O2—C7	−171.4 (14)	C1—C2—C3—C4	−13.5 (5)
C3—N4'—O2'—C7'	167 (9)	C1—N1—C4—C3	30.2 (5)
C4—N1—C1—C2	−39.6 (5)	N4—C3—C4—N1	171.6 (16)
N1—C1—C2—C5	154.7 (4)	N4'—C3—C4—N1	−179 (8)
N1—C1—C2—C3	31.5 (5)	C2—C3—C4—N1	−9.5 (5)
O2—N4—C3—C4	1(3)	O1—N2—C5—N3	2.4 (8)
O2—N4—C3—C2	−177.3 (9)	O1—N2—C5—C2	−177.8 (4)
O2'—N4'—C3—N4	−13 (25)	C3—C2—C5—N3	60.0 (6)
O2'—N4'—C3—C4	−163 (7)	C1—C2—C5—N3	−56.7 (6)
O2'—N4'—C3—C2	31 (17)	C3—C2—C5—N2	−119.7 (5)
C5—C2—C3—N4	41.6 (15)	C1—C2—C5—N2	123.6 (5)
C1—C2—C3—N4	165.4 (14)	N4—O2—C7—C8	176.7 (14)
C5—C2—C3—N4'	29 (9)	N4'—O2'—C7'—C8'	143 (8)
C1—C2—C3—N4'	153 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···Cl1	0.86	2.29	3.144 (4)	173
N3—H3A···Cl1i	0.86	2.41	3.213 (4)	156
N2—H2···Cl2ii	0.86	2.21	3.029 (4)	160
N1—H1B···Cl2	0.90	2.18	3.035 (4)	159
N1—H1A···Cl1iii	0.90	2.20	3.076 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯Cl1	0.86	2.29	3.144 (4)	173
N3—H3A⋯Cl1i	0.86	2.41	3.213 (4)	156
N2—H2⋯Cl2ii	0.86	2.21	3.029 (4)	160
N1—H1B⋯Cl2	0.90	2.18	3.035 (4)	159
N1—H1A⋯Cl1iii	0.90	2.20	3.076 (4)	165

Symmetry codes: (i) ; (ii) ; (iii) .