Crystal structure of 2-{[1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yl-oxy]carbon-yl}benzoic acid.

In the title compound, C15H15N3O6, the dihedral angle between the planes of the benzene and imidazole rings is 34.93 (10)°. An intra-molecular C-H⋯O hydrogen bond is observed. In the crystal, O-H⋯N hydrogen bonds link the mol-ecules into chains parallel to the c axis.

Related literature

For the applications and biological activities of nitro­imidazole and its derivatives, see: Maeda et al. (1953 ▶); Larina & Lopyrev (2009 ▶); Zhang et al. (2014 ▶); Gillis & Wiseman (1996 ▶). For the crystal structure of related compounds, see: Xiao et al. (2008 ▶); Shahid et al. (2014 ▶).

Experimental

Crystal data

C15H15N3O6

M = 333.30

Monoclinic,

a = 11.189 (3) Å

b = 6.9489 (17) Å

c = 19.979 (5) Å

β = 98.056 (10)°

V = 1538.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.50 × 0.50 × 0.38 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.946, T max = 0.958

20047 measured reflections

2865 independent reflections

2515 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.119

S = 1.07

2865 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814023927/rz5138sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814023927/rz5138Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814023927/rz5138Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814023927/rz5138fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at 50% probability level.

Click here for additional data file.

b . DOI: 10.1107/S1600536814023927/rz5138fig2.tif

Crystal packing of the title compound viewed down the b axis. Only hydrogen atoms involved in O—H⋯N hydrogen bonds (dashed lines) are shown.

CCDC reference: 1031694

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H15N3O6	Dx = 1.439 Mg m−3
Mr = 333.30	Melting point = 461–463 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.189 (3) Å	Cell parameters from 9799 reflections
b = 6.9489 (17) Å	θ = 3.1–28.3°
c = 19.979 (5) Å	µ = 0.11 mm−1
β = 98.056 (10)°	T = 296 K
V = 1538.0 (6) Å3	Block, colourless
Z = 4	0.50 × 0.50 × 0.38 mm
F(000) = 696

Bruker SMART APEX CCD area-detector diffractometer	2865 independent reflections
Radiation source: fine-focus sealed tube	2515 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
φ and ω scans	θmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
Tmin = 0.946, Tmax = 0.958	k = −8→8
20047 measured reflections	l = −24→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0414P)2 + 0.8462P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2865 reflections	Δρmax = 0.31 e Å−3
222 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0086 (17)

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.06727 (13)	0.4222 (2)	0.34680 (7)	0.0516 (4)
O2	0.23305 (12)	0.4311 (2)	0.29641 (7)	0.0545 (4)
O3	0.28516 (14)	0.5351 (2)	0.15189 (11)	0.0768 (6)
O4	0.26149 (10)	0.22096 (17)	0.17394 (6)	0.0375 (3)
O5	0.58254 (14)	0.2723 (3)	0.08232 (9)	0.0720 (5)
O6	0.57286 (14)	0.3388 (2)	−0.02413 (9)	0.0636 (5)
N1	0.23187 (14)	0.1045 (2)	−0.03904 (8)	0.0441 (4)
N2	0.35718 (12)	0.0837 (2)	0.05685 (7)	0.0329 (3)
N3	0.52989 (14)	0.2715 (2)	0.02452 (9)	0.0469 (4)
C1	0.12441 (16)	0.4255 (3)	0.29324 (9)	0.0382 (4)
C2	0.04179 (15)	0.4222 (2)	0.22764 (9)	0.0346 (4)
C3	−0.08314 (16)	0.4269 (3)	0.22600 (10)	0.0429 (4)
H3A	−0.1161	0.4322	0.2662	0.051*
C4	−0.15808 (17)	0.4237 (3)	0.16484 (11)	0.0501 (5)
H4A	−0.2414	0.4246	0.1640	0.060*
C5	−0.10993 (18)	0.4191 (3)	0.10507 (10)	0.0514 (5)
H5A	−0.1608	0.4188	0.0640	0.062*
C6	0.01374 (17)	0.4148 (3)	0.10593 (10)	0.0447 (5)
H6A	0.0458	0.4120	0.0654	0.054*
C7	0.09033 (15)	0.4146 (2)	0.16701 (9)	0.0349 (4)
C8	0.22351 (16)	0.4028 (3)	0.16476 (9)	0.0386 (4)
C9	0.39058 (15)	0.1846 (3)	0.17704 (9)	0.0382 (4)
H9A	0.4320	0.3015	0.1653	0.046*
C10	0.40426 (15)	0.0266 (3)	0.12629 (8)	0.0356 (4)
H10A	0.4890	−0.0063	0.1286	0.043*
H10B	0.3616	−0.0872	0.1382	0.043*
C11	0.24736 (15)	0.0342 (3)	0.02342 (9)	0.0353 (4)
C12	0.33437 (17)	0.2007 (3)	−0.04698 (9)	0.0447 (5)
H12A	0.3487	0.2640	−0.0861	0.054*
C13	0.41269 (15)	0.1901 (3)	0.01123 (9)	0.0364 (4)
C14	0.4392 (2)	0.1213 (4)	0.24794 (10)	0.0598 (6)
H14A	0.4299	0.2239	0.2790	0.090*
H14B	0.5231	0.0895	0.2502	0.090*
H14C	0.3953	0.0104	0.2597	0.090*
C15	0.15837 (17)	−0.0872 (3)	0.05232 (10)	0.0472 (5)
H15A	0.0877	−0.1030	0.0195	0.071*
H15B	0.1366	−0.0263	0.0920	0.071*
H15C	0.1932	−0.2110	0.0641	0.071*
H1D	0.122 (3)	0.417 (4)	0.3880 (16)	0.086 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0439 (7)	0.0761 (10)	0.0338 (7)	0.0032 (7)	0.0023 (6)	−0.0029 (7)
O2	0.0375 (8)	0.0856 (11)	0.0385 (7)	0.0068 (7)	−0.0017 (5)	−0.0163 (7)
O3	0.0471 (9)	0.0618 (10)	0.1214 (16)	0.0013 (8)	0.0111 (9)	0.0439 (10)
O4	0.0314 (6)	0.0397 (7)	0.0410 (7)	0.0046 (5)	0.0036 (5)	−0.0054 (5)
O5	0.0431 (8)	0.0934 (13)	0.0748 (11)	−0.0162 (8)	−0.0079 (8)	0.0043 (10)
O6	0.0605 (9)	0.0540 (9)	0.0847 (12)	−0.0030 (7)	0.0398 (9)	−0.0002 (8)
N1	0.0427 (9)	0.0556 (10)	0.0325 (8)	0.0053 (7)	0.0001 (6)	0.0022 (7)
N2	0.0314 (7)	0.0358 (7)	0.0310 (7)	0.0046 (6)	0.0019 (5)	−0.0011 (6)
N3	0.0384 (9)	0.0403 (9)	0.0641 (11)	0.0026 (7)	0.0148 (8)	−0.0033 (8)
C1	0.0386 (10)	0.0386 (9)	0.0361 (9)	0.0061 (7)	0.0011 (7)	−0.0065 (7)
C2	0.0361 (9)	0.0308 (8)	0.0354 (9)	0.0042 (7)	−0.0001 (7)	−0.0030 (7)
C3	0.0366 (9)	0.0469 (11)	0.0448 (10)	0.0057 (8)	0.0047 (8)	−0.0063 (8)
C4	0.0311 (9)	0.0573 (12)	0.0591 (12)	0.0067 (9)	−0.0037 (8)	−0.0077 (10)
C5	0.0462 (11)	0.0580 (12)	0.0445 (11)	0.0091 (9)	−0.0133 (8)	−0.0067 (9)
C6	0.0462 (11)	0.0503 (11)	0.0356 (9)	0.0089 (9)	−0.0011 (8)	−0.0017 (8)
C7	0.0356 (9)	0.0305 (8)	0.0368 (9)	0.0043 (7)	−0.0014 (7)	−0.0005 (7)
C8	0.0390 (10)	0.0418 (10)	0.0338 (9)	0.0023 (8)	0.0013 (7)	0.0070 (7)
C9	0.0296 (9)	0.0463 (10)	0.0367 (9)	0.0053 (7)	−0.0021 (7)	−0.0069 (8)
C10	0.0334 (9)	0.0404 (9)	0.0312 (9)	0.0086 (7)	−0.0021 (7)	0.0013 (7)
C11	0.0323 (8)	0.0395 (9)	0.0331 (9)	0.0058 (7)	0.0007 (7)	−0.0038 (7)
C12	0.0480 (11)	0.0508 (11)	0.0365 (10)	0.0058 (9)	0.0102 (8)	0.0077 (8)
C13	0.0343 (9)	0.0355 (9)	0.0404 (9)	0.0035 (7)	0.0093 (7)	−0.0001 (7)
C14	0.0537 (12)	0.0858 (17)	0.0354 (10)	0.0165 (12)	−0.0089 (9)	−0.0103 (10)
C15	0.0399 (10)	0.0554 (12)	0.0451 (10)	−0.0058 (9)	0.0013 (8)	0.0002 (9)

O1—C1	1.321 (2)	C4—H4A	0.9300
O1—H1D	0.96 (3)	C5—C6	1.382 (3)
O2—C1	1.209 (2)	C5—H5A	0.9300
O3—C8	1.199 (2)	C6—C7	1.389 (2)
O4—C8	1.337 (2)	C6—H6A	0.9300
O4—C9	1.459 (2)	C7—C8	1.499 (2)
O5—N3	1.221 (2)	C9—C14	1.510 (3)
O6—N3	1.235 (2)	C9—C10	1.517 (2)
N1—C11	1.329 (2)	C9—H9A	0.9800
N1—C12	1.356 (3)	C10—H10A	0.9700
N2—C11	1.358 (2)	C10—H10B	0.9700
N2—C13	1.386 (2)	C11—C15	1.482 (3)
N2—C10	1.468 (2)	C12—C13	1.356 (3)
N3—C13	1.418 (2)	C12—H12A	0.9300
C1—C2	1.494 (2)	C14—H14A	0.9600
C2—C3	1.394 (2)	C14—H14B	0.9600
C2—C7	1.396 (3)	C14—H14C	0.9600
C3—C4	1.382 (3)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.377 (3)	C15—H15C	0.9600
C1—O1—H1D	111.9 (17)	O4—C9—C14	108.32 (15)
C8—O4—C9	117.58 (14)	O4—C9—C10	106.80 (13)
C11—N1—C12	106.87 (15)	C14—C9—C10	111.08 (16)
C11—N2—C13	105.64 (14)	O4—C9—H9A	110.2
C11—N2—C10	125.19 (15)	C14—C9—H9A	110.2
C13—N2—C10	129.14 (14)	C10—C9—H9A	110.2
O5—N3—O6	123.59 (18)	N2—C10—C9	112.30 (14)
O5—N3—C13	119.33 (17)	N2—C10—H10A	109.1
O6—N3—C13	117.08 (18)	C9—C10—H10A	109.1
O2—C1—O1	123.72 (16)	N2—C10—H10B	109.1
O2—C1—C2	122.70 (16)	C9—C10—H10B	109.1
O1—C1—C2	113.58 (15)	H10A—C10—H10B	107.9
C3—C2—C7	119.43 (16)	N1—C11—N2	111.01 (16)
C3—C2—C1	121.00 (16)	N1—C11—C15	124.67 (16)
C7—C2—C1	119.57 (15)	N2—C11—C15	124.30 (16)
C4—C3—C2	120.16 (18)	N1—C12—C13	109.17 (16)
C4—C3—H3A	119.9	N1—C12—H12A	125.4
C2—C3—H3A	119.9	C13—C12—H12A	125.4
C5—C4—C3	120.29 (18)	C12—C13—N2	107.31 (15)
C5—C4—H4A	119.9	C12—C13—N3	127.45 (17)
C3—C4—H4A	119.9	N2—C13—N3	125.24 (16)
C4—C5—C6	120.17 (18)	C9—C14—H14A	109.5
C4—C5—H5A	119.9	C9—C14—H14B	109.5
C6—C5—H5A	119.9	H14A—C14—H14B	109.5
C5—C6—C7	120.27 (18)	C9—C14—H14C	109.5
C5—C6—H6A	119.9	H14A—C14—H14C	109.5
C7—C6—H6A	119.9	H14B—C14—H14C	109.5
C6—C7—C2	119.67 (16)	C11—C15—H15A	109.5
C6—C7—C8	117.84 (16)	C11—C15—H15B	109.5
C2—C7—C8	122.49 (15)	H15A—C15—H15B	109.5
O3—C8—O4	124.94 (17)	C11—C15—H15C	109.5
O3—C8—C7	124.65 (17)	H15A—C15—H15C	109.5
O4—C8—C7	110.22 (15)	H15B—C15—H15C	109.5
O2—C1—C2—C3	−176.28 (18)	C8—O4—C9—C10	−127.65 (16)
O1—C1—C2—C3	3.6 (2)	C11—N2—C10—C9	−99.49 (19)
O2—C1—C2—C7	3.6 (3)	C13—N2—C10—C9	82.8 (2)
O1—C1—C2—C7	−176.53 (16)	O4—C9—C10—N2	61.80 (19)
C7—C2—C3—C4	0.1 (3)	C14—C9—C10—N2	179.71 (16)
C1—C2—C3—C4	−179.99 (17)	C12—N1—C11—N2	0.6 (2)
C2—C3—C4—C5	−1.1 (3)	C12—N1—C11—C15	−177.69 (17)
C3—C4—C5—C6	0.9 (3)	C13—N2—C11—N1	−0.60 (19)
C4—C5—C6—C7	0.2 (3)	C10—N2—C11—N1	−178.73 (15)
C5—C6—C7—C2	−1.1 (3)	C13—N2—C11—C15	177.73 (17)
C5—C6—C7—C8	177.87 (18)	C10—N2—C11—C15	−0.4 (3)
C3—C2—C7—C6	1.0 (3)	C11—N1—C12—C13	−0.4 (2)
C1—C2—C7—C6	−178.91 (16)	N1—C12—C13—N2	0.0 (2)
C3—C2—C7—C8	−177.98 (16)	N1—C12—C13—N3	−179.84 (17)
C1—C2—C7—C8	2.1 (3)	C11—N2—C13—C12	0.33 (19)
C9—O4—C8—O3	8.2 (3)	C10—N2—C13—C12	178.35 (16)
C9—O4—C8—C7	−176.63 (13)	C11—N2—C13—N3	−179.79 (16)
C6—C7—C8—O3	77.9 (3)	C10—N2—C13—N3	−1.8 (3)
C2—C7—C8—O3	−103.1 (2)	O5—N3—C13—C12	169.8 (2)
C6—C7—C8—O4	−97.27 (19)	O6—N3—C13—C12	−10.0 (3)
C2—C7—C8—O4	81.7 (2)	O5—N3—C13—N2	−10.1 (3)
C8—O4—C9—C14	112.64 (19)	O6—N3—C13—N2	170.11 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O5	0.98	2.53	3.115 (3)	118
O1—H1D···N1i	0.96 (3)	1.78 (3)	2.730 (2)	175 (3)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C9H9AO5	0.98	2.53	3.115(3)	118
O1H1DN1i	0.96(3)	1.78(3)	2.730(2)	175(3)

Symmetry code: (i) .