5-Nitro-2-trifluoro-methyl-1H-benzimidazole monohydrate.

In the crystal structure of the title compound, C(8)H(4)F(3)N(3)O(2)·H(2)O, the main mol-ecule and the water mol-ecule are linked by an N-H⋯O hydrogen bond. O-H⋯N, O-H⋯O and C-H⋯O hydrogen bonds further link the mol-ecules into sheets.

Related literature

The title compound was studied as part of a search for ferroelectric complexes. For background to ferroelectric complexes, see: Zhang et al. (2009 ▶, 2010 ▶); Ye et al. (2009 ▶). For related structures, see: Liu (2011a ▶,b ▶).

Experimental

Crystal data

C8H4F3N3O2·H2O

M = 249.16

Monoclinic,

a = 7.6209 (15) Å

b = 10.393 (2) Å

c = 13.093 (3) Å

β = 97.63 (3)°

V = 1027.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 293 K

0.36 × 0.32 × 0.28 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.903, T max = 0.921

10402 measured reflections

2344 independent reflections

1451 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.221

S = 1.05

2344 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.32 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: PLATON (Spek, 2009) ▶; software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017060/go2048sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017060/go2048Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017060/go2048Isup3.cml

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

C8H4F3N3O2·H2O	Z = 4
Mr = 249.16	F(000) = 504
Monoclinic, P21/n	Dx = 1.610 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.6209 (15) Å	θ = 3.4–27.5°
b = 10.393 (2) Å	µ = 0.16 mm−1
c = 13.093 (3) Å	T = 293 K
β = 97.63 (3)°	Block, colourless
V = 1027.9 (4) Å3	0.36 × 0.32 × 0.28 mm

Rigaku Mercury2 diffractometer	2344 independent reflections
Radiation source: fine-focus sealed tube	1451 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
CCD_Profile_fitting scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −9→9
Tmin = 0.903, Tmax = 0.921	k = −13→13
10402 measured reflections	l = −16→16

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1019P)2 + 0.6421P] where P = (Fo2 + 2Fc2)/3
2344 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
F1	0.7199 (4)	0.8890 (3)	0.31003 (18)	0.1071 (10)
F2	0.7951 (5)	0.9620 (2)	0.4602 (3)	0.1403 (15)
F3	0.5316 (4)	0.9177 (3)	0.4078 (3)	0.1320 (13)
O1	0.9829 (5)	0.3172 (3)	0.7630 (3)	0.0971 (11)
O2	0.8506 (5)	0.1639 (3)	0.6747 (3)	0.1086 (12)
N1	0.6638 (3)	0.6404 (2)	0.38970 (18)	0.0471 (6)
H1A	0.6092	0.6413	0.3279	0.057*
N2	0.8035 (3)	0.7156 (2)	0.53963 (18)	0.0469 (6)
N3	0.8922 (4)	0.2768 (3)	0.6865 (3)	0.0687 (9)
C1	0.7950 (4)	0.5815 (3)	0.5434 (2)	0.0414 (7)
C2	0.8576 (4)	0.4973 (3)	0.6230 (2)	0.0493 (7)
H2	0.9157	0.5264	0.6857	0.059*
C3	0.7071 (4)	0.5333 (3)	0.4496 (2)	0.0426 (7)
C4	0.8283 (4)	0.3683 (3)	0.6032 (2)	0.0507 (8)
C5	0.7237 (4)	0.7440 (3)	0.4469 (2)	0.0449 (7)
C6	0.6781 (4)	0.4023 (3)	0.4317 (2)	0.0517 (8)
H6	0.6194	0.3722	0.3695	0.062*
C7	0.7404 (4)	0.3194 (3)	0.5103 (3)	0.0566 (8)
H7	0.7242	0.2311	0.5018	0.068*
C8	0.6956 (5)	0.8789 (3)	0.4077 (3)	0.0575 (8)
O3	0.4481 (4)	0.6193 (2)	0.20564 (17)	0.0755 (9)
H3A	0.4159	0.6728	0.1499	0.113*
H3B	0.4169	0.5518	0.1909	0.113*

	U11	U22	U33	U12	U13	U23
F1	0.182 (3)	0.0760 (16)	0.0689 (15)	0.0252 (17)	0.0363 (17)	0.0271 (13)
F2	0.216 (4)	0.0534 (15)	0.126 (2)	−0.0328 (19)	−0.072 (2)	0.0178 (15)
F3	0.113 (2)	0.090 (2)	0.203 (3)	0.0460 (17)	0.059 (2)	0.063 (2)
O1	0.115 (3)	0.081 (2)	0.084 (2)	0.0147 (18)	−0.0250 (19)	0.0302 (17)
O2	0.141 (3)	0.0490 (17)	0.131 (3)	0.0068 (18)	−0.002 (2)	0.0273 (17)
N1	0.0566 (15)	0.0497 (15)	0.0322 (12)	−0.0006 (12)	−0.0049 (10)	−0.0002 (10)
N2	0.0561 (15)	0.0411 (13)	0.0406 (13)	−0.0014 (11)	−0.0048 (11)	−0.0018 (10)
N3	0.075 (2)	0.0540 (19)	0.077 (2)	0.0149 (16)	0.0096 (17)	0.0202 (16)
C1	0.0439 (15)	0.0405 (15)	0.0387 (14)	−0.0014 (12)	0.0009 (12)	−0.0026 (12)
C2	0.0520 (17)	0.0517 (18)	0.0412 (15)	−0.0007 (14)	−0.0047 (13)	0.0020 (13)
C3	0.0439 (15)	0.0479 (17)	0.0355 (14)	−0.0031 (12)	0.0030 (11)	−0.0035 (12)
C4	0.0540 (17)	0.0450 (17)	0.0532 (18)	0.0084 (14)	0.0077 (14)	0.0076 (14)
C5	0.0513 (16)	0.0460 (16)	0.0363 (14)	0.0009 (13)	0.0015 (12)	−0.0007 (12)
C6	0.0626 (19)	0.0472 (18)	0.0448 (16)	−0.0064 (14)	0.0050 (14)	−0.0128 (13)
C7	0.066 (2)	0.0400 (17)	0.065 (2)	−0.0043 (15)	0.0136 (16)	−0.0068 (15)
C8	0.067 (2)	0.0504 (19)	0.0530 (19)	0.0026 (16)	0.0013 (16)	0.0036 (16)
O3	0.115 (2)	0.0493 (13)	0.0507 (14)	0.0082 (13)	−0.0307 (14)	−0.0022 (11)

F1—C8	1.320 (4)	C1—C3	1.410 (4)
F2—C8	1.287 (4)	C2—C4	1.378 (5)
F3—C8	1.313 (4)	C2—H2	0.9300
O1—N3	1.214 (4)	C3—C6	1.394 (4)
O2—N3	1.219 (4)	C4—C7	1.403 (5)
N1—C5	1.355 (4)	C5—C8	1.499 (4)
N1—C3	1.377 (4)	C6—C7	1.377 (5)
N1—H1A	0.8596	C6—H6	0.9300
N2—C5	1.317 (4)	C7—H7	0.9300
N2—C1	1.397 (4)	O3—H3A	0.9240
N3—C4	1.481 (4)	O3—H3B	0.7573
C1—C2	1.396 (4)
C5—N1—C3	106.8 (2)	C7—C4—N3	118.6 (3)
C5—N1—H1A	126.6	N2—C5—N1	114.3 (3)
C3—N1—H1A	126.5	N2—C5—C8	123.5 (3)
C5—N2—C1	103.8 (2)	N1—C5—C8	122.1 (3)
O1—N3—O2	123.2 (3)	C7—C6—C3	117.0 (3)
O1—N3—C4	118.7 (3)	C7—C6—H6	121.5
O2—N3—C4	118.0 (4)	C3—C6—H6	121.5
C2—C1—N2	129.8 (3)	C6—C7—C4	119.9 (3)
C2—C1—C3	120.2 (3)	C6—C7—H7	120.1
N2—C1—C3	110.0 (2)	C4—C7—H7	120.1
C4—C2—C1	116.0 (3)	F2—C8—F3	106.7 (4)
C4—C2—H2	122.0	F2—C8—F1	108.4 (3)
C1—C2—H2	122.0	F3—C8—F1	103.5 (3)
N1—C3—C6	132.3 (3)	F2—C8—C5	113.4 (3)
N1—C3—C1	105.0 (2)	F3—C8—C5	112.3 (3)
C6—C3—C1	122.7 (3)	F1—C8—C5	111.9 (3)
C2—C4—C7	124.3 (3)	H3A—O3—H3B	108.4
C2—C4—N3	117.2 (3)
C5—N2—C1—C2	−179.8 (3)	C1—N2—C5—N1	0.0 (3)
C5—N2—C1—C3	−0.1 (3)	C1—N2—C5—C8	178.3 (3)
N2—C1—C2—C4	179.8 (3)	C3—N1—C5—N2	0.1 (3)
C3—C1—C2—C4	0.2 (4)	C3—N1—C5—C8	−178.2 (3)
C5—N1—C3—C6	179.5 (3)	N1—C3—C6—C7	−180.0 (3)
C5—N1—C3—C1	−0.2 (3)	C1—C3—C6—C7	−0.3 (5)
C2—C1—C3—N1	179.9 (3)	C3—C6—C7—C4	0.1 (5)
N2—C1—C3—N1	0.2 (3)	C2—C4—C7—C6	0.3 (5)
C2—C1—C3—C6	0.1 (4)	N3—C4—C7—C6	179.4 (3)
N2—C1—C3—C6	−179.5 (3)	N2—C5—C8—F2	17.5 (5)
C1—C2—C4—C7	−0.5 (5)	N1—C5—C8—F2	−164.4 (3)
C1—C2—C4—N3	−179.6 (3)	N2—C5—C8—F3	−103.5 (4)
O1—N3—C4—C2	−7.8 (5)	N1—C5—C8—F3	74.6 (4)
O2—N3—C4—C2	172.1 (3)	N2—C5—C8—F1	140.6 (3)
O1—N3—C4—C7	173.0 (3)	N1—C5—C8—F1	−41.3 (4)
O2—N3—C4—C7	−7.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.86	1.90	2.740 (3)	166
O3—H3A···N2i	0.92	1.96	2.872 (3)	169
O3—H3B···O2ii	0.76	2.30	3.050 (4)	170
C6—H6···O1ii	0.93	2.55	3.380 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.86	1.90	2.740 (3)	166
O3—H3A⋯N2i	0.92	1.96	2.872 (3)	169
O3—H3B⋯O2ii	0.76	2.30	3.050 (4)	170
C6—H6⋯O1ii	0.93	2.55	3.380 (4)	148

Symmetry codes: (i) ; (ii) .