4-Ethoxy­imino-N′-methoxy­pyrrolidin-1-ium-3-carboximidamidium dichloride

Guo, Q.; Sun, L.; Guo, H.; Liu, M.

doi:10.1107/S1600536809004772

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o580

doi:10.1107/S1600536809004772

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4-Ethoxyimino-N′-methoxypyrrolidin-1-ium-3-carboximidamidium dichloride

Qiang Guo,^a Lanying Sun,^a Huiyuan Guo ^a and Mingliang Liu ^a ^*

^aInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050, People's Republic of China
^*Correspondence e-mail: lmllyx@yahoo.com.cn

(Received 11 January 2009; accepted 10 February 2009; online 21 February 2009)

The title compound, C₈H₁₈N₄O₂²⁺·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

C₈H₁₈N₄O₂²⁺·2Cl⁻
M_r = 273.16
Orthorhombic, P b c n
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[F² > 2σ(F²)] = 0.077
wR(F²) = 0.210
S = 1.08
2597 reflections
170 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) -x+1, -y, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

Since the discovery of norfloxacin, fluoroquinolone antibacterial agents have emerged as one of the dominant classes of chemotherapeutic drugs for the treatment of various bacterial infections (Ball et al., 1998; Ray et al., 2005). The most intensive structural variations have been carried out on the basic group at the C-7 position. In general, 5- and 6-membered nitrogen heterocycles including piperazinyl, pyrrolidinyl and piperidinyl type side chains have been proven to be the optimal substituents, as evidenced by the compounds currently on the market (Anderson & Osheroff, 2001; Choi et al., 2004). Recently, as part of an ongoing program to find potent new fluoroquinolones displaying strong Gram-positive activity, we have focused our attention on introducing new functional groups to the pyrrolidine ring. We report here the crystal structure of the title compound, which is intended for use as a novel substituent at the C-7 position of fluoroquinolones.

There are two oximes in the molecule of the title compound (Fig. 1). The methyloxime has the Z configuration, and the ethyloxime is disordered, with both Z and E configurations at occupancy factors of 0.840 (8) and 0.160 (8), respectively. In the molecule the N3—C5(1.296 (6) Å) bond length is significantly shorter than the normal C—N single bond (1.47 Å), indicating some delocalization over the N3-C5-N2 group. The five-membered pyrrolidine ring adopts an envelope conformation. In the crystal structure, there are a number of N–H···Cl hydrogen bonds. (Table 1)

Related literature top

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 top

To a stirring solution of N'-methoxy-(1-N-tert-butoxycarbonyl-4- ethoxyimino) pyrrolidine-3-carboximidamide (15.0 g, 50.0 mmol) in methanol (80 ml) was pumped into dry hydrogen chloride for 2 h at room temperature. After the removal of the methanol under reduced pressure, the residue was treated with ethyl acetate (80 ml), and filtered. The filter cake was washed with ethyl acetate and ether, respectively, dried in vacuo to give the title compound as a white solid (11.5 g, 84.2%; mp: 375–376 K). Single crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol/ ethyl acetate (1:1 v/v). ¹H NMR(DMSO-d₆, δ):1.14–1.17(3H, m, CH₃), 3.44–3.58(m, 1H, pyrrolidine), 3.53(2H, br, NH₂⁺), 3.66(3H, s, OCH₃), 3.68–3.79(2H, m, OCH₂), 4.03–4.11(4H, m, pyrrolidine), 9.88–9.93(3H, br, NH₂, NH⁺). MS(ESI, m/z): 201(M+H)⁺.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999) 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 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure showing 40% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Crystal packing of the title compound viewed down the b axis.

4-Ethoxyimino-N'-methoxypyrrolidin-1-ium-3-carboximidamidium dichloride top

Crystal data top

C₈H₁₈N₄O₂²⁺·2Cl⁻	F(000) = 1152
M_r = 273.16	D_x = 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

Data collection top

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

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.210	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0819P)² + 7.7771P] where P = (F_o² + 2F_c²)/3
2597 reflections	(Δ/σ)_max = 0.001
170 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₈H₁₈N₄O₂²⁺·2Cl⁻	V = 2968.3 (6) Å³
M_r = 273.16	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 12.7355 (14) Å	µ = 0.43 mm⁻¹
b = 8.8506 (12) Å	T = 298 K
c = 26.334 (2) Å	0.23 × 0.20 × 0.19 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2597 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1986 reflections with I > 2σ(I)
T_min = 0.907, T_max = 0.922	R_int = 0.062
14370 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.210	H-atom parameters constrained
S = 1.08	Δρ_max = 0.44 e Å⁻³
2597 reflections	Δρ_min = −0.33 e Å⁻³
170 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	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y+1/2, z; (ii) −x+1/2, y+1/2, z; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₈H₁₈N₄O₂²⁺·2Cl⁻
M_r	273.16
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	12.7355 (14), 8.8506 (12), 26.334 (2)
V (Å³)	2968.3 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.23 × 0.20 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.907, 0.922
No. of measured, independent and observed [I > 2σ(I)] reflections	14370, 2597, 1986
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.210, 1.08
No. of reflections	2597
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.33

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999) and SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···Cl1	0.86	2.29	3.144 (4)	173.2
N3—H3A···Cl1ⁱ	0.86	2.41	3.213 (4)	156.2
N2—H2···Cl2ⁱⁱ	0.86	2.21	3.029 (4)	159.8
N1—H1B···Cl2	0.90	2.18	3.035 (4)	158.7
N1—H1A···Cl1ⁱⁱⁱ	0.90	2.20	3.076 (4)	164.7

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+1/2, y+1/2, z; (iii) −x+1, −y, −z+1.

Acknowledgements

This work was supported by the IMB Research Foundation.

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