Metronidazolium perchlorate.

IN THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND [SYSTEMATIC NAME: 1-(2-hy-droxy-eth-yl)-2-methyl-5-nitro-1H-imidazol-3-ium perchlorate], C(6)H(10)N(3)O(3) (+)·ClO(4) (-), the cations are linked by inter-molecular N-H⋯O hydrogen bonds into zigzag chains along the c axis. The cations and anions are connected by O-H⋯O and C-H⋯O hydrogen bonds. A weak intra-molecular C-H⋯O hydrogen bond is also observed.

Related literature

For metronidazole, see: Castelli et al. (2000 ▶); Contrerasa et al. (2009 ▶). For a related structure, see: Wang et al. (2006 ▶).

Experimental

Crystal data

C6H10N3O3 +·ClO4 −

M = 271.62

Monoclinic,

a = 7.8541 (13) Å

b = 10.6791 (17) Å

c = 13.032 (2) Å

β = 93.904 (2)°

V = 1090.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 296 K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.862, T max = 0.928

9191 measured reflections

2509 independent reflections

2219 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.159

S = 1.04

2509 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038055/is2601sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038055/is2601Isup2.hkl

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

C6H10N3O3+·ClO4−	F(000) = 560
Mr = 271.62	Dx = 1.654 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5428 reflections
a = 7.8541 (13) Å	θ = 2.5–27.5°
b = 10.6791 (17) Å	µ = 0.38 mm−1
c = 13.032 (2) Å	T = 296 K
β = 93.904 (2)°	Prism, colourless
V = 1090.5 (3) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2509 independent reflections
Radiation source: fine-focus sealed tube	2219 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.862, Tmax = 0.928	k = −13→13
9191 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.085P)2 + 0.8145P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2509 reflections	Δρmax = 0.60 e Å−3
155 parameters	Δρmin = −0.43 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.190 (12)

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
O1	0.7469 (2)	0.70762 (17)	0.58597 (12)	0.0486 (4)
H1	0.8599	0.7118	0.5945	0.073*
O2	0.4144 (3)	0.4116 (2)	0.66132 (15)	0.0639 (6)
O3	0.2449 (3)	0.4469 (2)	0.78337 (19)	0.0727 (6)
N1	0.6726 (2)	0.55501 (15)	0.76908 (12)	0.0340 (4)
N2	0.6393 (3)	0.64689 (18)	0.91461 (14)	0.0437 (5)
H2	0.6580	0.6952	0.9643	0.066*
N3	0.3813 (3)	0.45742 (19)	0.74353 (16)	0.0487 (5)
C1	0.7048 (3)	0.5773 (2)	0.58035 (16)	0.0451 (5)
H1A	0.7611	0.5397	0.5240	0.054*
H1B	0.5827	0.5686	0.5656	0.054*
C2	0.7567 (3)	0.5070 (2)	0.67880 (16)	0.0404 (5)
H2A	0.7283	0.4191	0.6694	0.048*
H2B	0.8794	0.5131	0.6922	0.048*
C3	0.7495 (3)	0.6272 (2)	0.84260 (15)	0.0384 (5)
C4	0.4896 (3)	0.5882 (2)	0.88970 (17)	0.0441 (5)
H4A	0.3928	0.5879	0.9270	0.053*
C5	0.5098 (3)	0.53022 (19)	0.79949 (16)	0.0379 (5)
C6	0.9254 (3)	0.6762 (3)	0.8466 (2)	0.0550 (6)
H6A	0.9791	0.6507	0.7860	0.083*
H6B	0.9887	0.6439	0.9065	0.083*
H6C	0.9228	0.7660	0.8500	0.083*
Cl1	1.22616 (7)	0.74741 (5)	0.59693 (4)	0.0442 (3)
O4	1.3343 (4)	0.7477 (2)	0.6879 (2)	0.0994 (10)
O5	1.1033 (4)	0.6500 (3)	0.5984 (3)	0.1022 (10)
O6	1.3237 (5)	0.7180 (3)	0.5116 (2)	0.1074 (11)
O7	1.1515 (5)	0.8663 (3)	0.5795 (2)	0.1214 (14)

	U11	U22	U33	U12	U13	U23
O1	0.0558 (10)	0.0482 (10)	0.0408 (8)	−0.0064 (7)	−0.0038 (7)	0.0107 (7)
O2	0.0773 (14)	0.0622 (12)	0.0503 (11)	−0.0159 (10)	−0.0096 (9)	−0.0110 (9)
O3	0.0564 (12)	0.0751 (14)	0.0870 (16)	−0.0189 (10)	0.0074 (11)	0.0038 (12)
N1	0.0444 (9)	0.0313 (8)	0.0258 (8)	0.0031 (7)	−0.0008 (6)	0.0019 (6)
N2	0.0642 (12)	0.0368 (9)	0.0302 (9)	0.0026 (8)	0.0033 (8)	−0.0042 (7)
N3	0.0558 (12)	0.0405 (10)	0.0487 (11)	−0.0059 (9)	−0.0055 (9)	0.0065 (8)
C1	0.0627 (14)	0.0457 (12)	0.0266 (9)	−0.0026 (10)	0.0012 (9)	−0.0006 (8)
C2	0.0534 (12)	0.0381 (11)	0.0297 (9)	0.0067 (9)	0.0044 (8)	−0.0019 (8)
C3	0.0510 (12)	0.0356 (10)	0.0279 (9)	0.0016 (8)	−0.0038 (8)	0.0012 (7)
C4	0.0549 (13)	0.0390 (11)	0.0391 (11)	0.0050 (9)	0.0086 (9)	0.0025 (9)
C5	0.0452 (11)	0.0335 (10)	0.0347 (10)	0.0013 (8)	−0.0006 (8)	0.0037 (8)
C6	0.0545 (14)	0.0615 (16)	0.0476 (13)	−0.0111 (12)	−0.0074 (10)	−0.0048 (11)
Cl1	0.0468 (4)	0.0427 (4)	0.0425 (4)	−0.0003 (2)	−0.0022 (2)	−0.0002 (2)
O4	0.126 (2)	0.0840 (18)	0.0799 (17)	0.0238 (15)	−0.0504 (17)	−0.0069 (13)
O5	0.0761 (16)	0.097 (2)	0.137 (3)	−0.0317 (15)	0.0297 (16)	−0.0074 (18)
O6	0.137 (3)	0.106 (2)	0.0864 (19)	−0.013 (2)	0.0566 (19)	0.0002 (16)
O7	0.157 (3)	0.0654 (16)	0.129 (2)	0.0509 (17)	−0.084 (2)	−0.0367 (15)

O1—C1	1.431 (3)	C1—H1B	0.9700
O1—H1	0.8881	C2—H2A	0.9700
O2—N3	1.222 (3)	C2—H2B	0.9700
O3—N3	1.227 (3)	C3—C6	1.475 (3)
N1—C3	1.341 (3)	C4—C5	1.348 (3)
N1—C5	1.390 (3)	C4—H4A	0.9300
N1—C2	1.479 (3)	C6—H6A	0.9600
N2—C3	1.336 (3)	C6—H6B	0.9600
N2—C4	1.353 (3)	C6—H6C	0.9600
N2—H2	0.8328	Cl1—O4	1.410 (3)
N3—C5	1.434 (3)	Cl1—O7	1.411 (2)
C1—C2	1.518 (3)	Cl1—O5	1.420 (3)
C1—H1A	0.9700	Cl1—O6	1.427 (3)
C1—O1—H1	106.3	N2—C3—N1	108.12 (19)
C3—N1—C5	106.50 (17)	N2—C3—C6	124.7 (2)
C3—N1—C2	124.35 (18)	N1—C3—C6	127.2 (2)
C5—N1—C2	129.02 (18)	C5—C4—N2	105.7 (2)
C3—N2—C4	110.65 (18)	C5—C4—H4A	127.2
C3—N2—H2	123.8	N2—C4—H4A	127.2
C4—N2—H2	125.3	C4—C5—N1	109.1 (2)
O2—N3—O3	125.3 (2)	C4—C5—N3	124.9 (2)
O2—N3—C5	118.6 (2)	N1—C5—N3	126.03 (19)
O3—N3—C5	116.1 (2)	C3—C6—H6A	109.5
O1—C1—C2	112.96 (18)	C3—C6—H6B	109.5
O1—C1—H1A	109.0	H6A—C6—H6B	109.5
C2—C1—H1A	109.0	C3—C6—H6C	109.5
O1—C1—H1B	109.0	H6A—C6—H6C	109.5
C2—C1—H1B	109.0	H6B—C6—H6C	109.5
H1A—C1—H1B	107.8	O4—Cl1—O7	110.68 (15)
N1—C2—C1	113.07 (18)	O4—Cl1—O5	111.2 (2)
N1—C2—H2A	109.0	O7—Cl1—O5	112.8 (2)
C1—C2—H2A	109.0	O4—Cl1—O6	109.3 (2)
N1—C2—H2B	109.0	O7—Cl1—O6	108.2 (2)
C1—C2—H2B	109.0	O5—Cl1—O6	104.49 (19)
H2A—C2—H2B	107.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	0.89	2.02	2.860 (4)	157
N2—H2···O1i	0.83	1.98	2.803 (3)	169
C1—H1B···O2	0.97	2.52	3.126 (3)	121
C6—H6B···O7i	0.96	2.52	3.441 (4)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5	0.89	2.02	2.860 (4)	157
N2—H2⋯O1i	0.83	1.98	2.803 (3)	169
C1—H1B⋯O2	0.97	2.52	3.126 (3)	121
C6—H6B⋯O7i	0.96	2.52	3.441 (4)	161

Symmetry code: (i) .