Crystal structure of aqua-bis-[2-(1H-benzimidazol-2-yl-κN (3))aniline-κN]zinc dinitrate.

The cation of the complex title salt, [Zn(C13H11N3)2(H2O)](NO3)2, lies about a twofold rotation axis, which passes through the Zn(II) atom and the O atom of the aqua ligand. The Zn(II) atom adopts a distorted trigonal-bipyramidal geometry defined by two N atoms in axial positions [angle = 166.24 (7)°], and two N and one O atom in the equatorial plane [range of angles: 115.17 (7)-122.42 (3)°]. The dihedral angle between the imidazole and aniline rings is 23.86 (5)°. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the components into a three-dimensional network.

Related literature

For the synthesis of the title complex and derivatives, see: Esparza-Ruiz et al. (2011 ▸); Eltayeb et al. (2011 ▸). For background to benz­imidazoles and their applications, see: Chassaing et al. (2008 ▸); Podunavac-Kuzmonovic et al. (1999 ▸); Sánchez-Guadarrama et al. (2009 ▸); Xue et al. (2011 ▸).

Experimental

Crystal data

[Zn(C13H11N3)2(H2O)](NO3)2

M = 625.9

Monoclinic,

a = 16.2892 (9) Å

b = 15.0782 (8) Å

c = 11.6840 (6) Å

β = 110.0178 (8)°

V = 2696.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.97 mm−1

T = 296 K

0.21 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▸) T min = 0.546, T max = 0.726

13558 measured reflections

3347 independent reflections

3007 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.078

S = 1.06

3347 reflections

207 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2002 ▸); cell refinement: SAINT (Bruker, 2002 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015004636/tk5361sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015004636/tk5361Isup2.hkl

Click here for additional data file.

x y z . DOI: 10.1107/S2056989015004636/tk5361fig1.tif

Mol­ecular structure of the title complex, showing the atom-numbering scheme and 30% probability ellipsoids. [Symmetry code: (i): −x + 1, y, −z + ]

Click here for additional data file.

. DOI: 10.1107/S2056989015004636/tk5361fig2.tif

Part of the crystal structure of the title complex, showing the 3-D network of mol­ecules linked by inter­molecular N—H⋯O and O—H⋯O hydrogen bonds (dashed lines).

CCDC reference: 1052527

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

[Zn(C13H11N3)2(H2O)](NO3)2	F(000) = 1288
Mr = 625.9	Dx = 1.542 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6738 reflections
a = 16.2892 (9) Å	θ = 2.7–28.0°
b = 15.0782 (8) Å	µ = 0.97 mm−1
c = 11.6840 (6) Å	T = 296 K
β = 110.0178 (8)°	Block, yellow
V = 2696.4 (2) Å3	0.21 × 0.2 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3007 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
φ and ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −21→21
Tmin = 0.546, Tmax = 0.726	k = −19→20
13558 measured reflections	l = −15→11
3347 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0439P)2 + 1.0441P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3347 reflections	Δρmax = 0.35 e Å−3
207 parameters	Δρmin = −0.20 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.

	x	y	z	Uiso*/Ueq
Zn1	0.5	0.15270 (2)	0.25	0.03249 (9)
N2	0.59261 (7)	0.22530 (8)	0.37818 (10)	0.0317 (2)
C3	0.61501 (9)	0.22740 (10)	0.50420 (12)	0.0331 (3)
C4	0.60111 (11)	0.16542 (11)	0.58370 (15)	0.0436 (4)
H4	0.5726	0.1121	0.5556	0.052*
C5	0.63145 (12)	0.18640 (14)	0.70620 (15)	0.0522 (4)
H5	0.6242	0.1458	0.7619	0.063*
C6	0.67293 (11)	0.26740 (13)	0.74848 (14)	0.0499 (4)
H6	0.6914	0.2797	0.8314	0.06*
C7	0.68716 (10)	0.32919 (11)	0.67076 (14)	0.0413 (3)
H7	0.7143	0.3831	0.6989	0.05*
C8	0.65875 (9)	0.30678 (10)	0.54755 (12)	0.0338 (3)
N9	0.66310 (9)	0.35081 (9)	0.44630 (12)	0.0348 (3)
H9	0.6898 (13)	0.3906 (14)	0.4450 (18)	0.045 (5)*
C10	0.62329 (8)	0.29990 (9)	0.34760 (12)	0.0309 (3)
C11	0.61314 (9)	0.32625 (10)	0.22259 (13)	0.0346 (3)
C12	0.61377 (12)	0.41579 (12)	0.19286 (16)	0.0496 (4)
H12	0.6228	0.4586	0.2533	0.059*
C13	0.60111 (15)	0.44164 (14)	0.07450 (18)	0.0645 (6)
H13	0.601	0.5015	0.0551	0.077*
C14	0.58865 (16)	0.37784 (16)	−0.01468 (18)	0.0660 (6)
H14	0.5801	0.395	−0.0944	0.079*
C15	0.58871 (13)	0.28936 (13)	0.01287 (15)	0.0524 (4)
H15	0.5804	0.2473	−0.0483	0.063*
C16	0.60098 (9)	0.26197 (11)	0.13089 (13)	0.0372 (3)
N17	0.59641 (9)	0.17030 (9)	0.15649 (13)	0.0397 (3)
H17A	0.5924 (14)	0.1410 (14)	0.092 (2)	0.053 (6)*
H17B	0.6415 (14)	0.1544 (11)	0.2191 (19)	0.040 (5)*
O18	0.5	0.02352 (11)	0.25	0.0668 (7)
H18	0.5330 (14)	−0.0001 (16)	0.3054 (19)	0.066 (7)*
N19	0.67858 (9)	−0.01854 (9)	0.48037 (12)	0.0434 (3)
O20	0.60669 (8)	−0.05918 (8)	0.44950 (11)	0.0528 (3)
O21	0.73467 (10)	−0.03031 (13)	0.58020 (13)	0.0808 (5)
O22	0.69082 (10)	0.03590 (10)	0.40974 (15)	0.0712 (4)

	U11	U22	U33	U12	U13	U23
Zn1	0.03883 (14)	0.02325 (12)	0.03001 (13)	0	0.00485 (9)	0
N2	0.0331 (5)	0.0301 (6)	0.0296 (5)	−0.0014 (4)	0.0078 (4)	−0.0025 (4)
C3	0.0311 (6)	0.0359 (7)	0.0303 (6)	0.0021 (5)	0.0081 (5)	−0.0015 (5)
C4	0.0476 (9)	0.0412 (8)	0.0396 (8)	−0.0031 (6)	0.0120 (7)	0.0035 (6)
C5	0.0563 (10)	0.0629 (11)	0.0368 (8)	−0.0011 (8)	0.0153 (7)	0.0108 (8)
C6	0.0474 (9)	0.0708 (12)	0.0292 (7)	−0.0006 (8)	0.0102 (6)	−0.0037 (7)
C7	0.0373 (7)	0.0496 (9)	0.0343 (7)	−0.0013 (6)	0.0090 (6)	−0.0097 (6)
C8	0.0288 (6)	0.0392 (7)	0.0320 (7)	0.0017 (5)	0.0087 (5)	−0.0040 (5)
N9	0.0362 (6)	0.0332 (6)	0.0344 (6)	−0.0076 (5)	0.0114 (5)	−0.0069 (5)
C10	0.0281 (6)	0.0316 (7)	0.0326 (6)	0.0000 (5)	0.0102 (5)	−0.0045 (5)
C11	0.0344 (7)	0.0377 (7)	0.0328 (7)	−0.0055 (5)	0.0130 (5)	−0.0027 (5)
C12	0.0633 (11)	0.0425 (9)	0.0426 (8)	−0.0154 (8)	0.0177 (8)	−0.0028 (7)
C13	0.0902 (15)	0.0509 (11)	0.0520 (11)	−0.0227 (10)	0.0240 (10)	0.0093 (8)
C14	0.0855 (15)	0.0755 (14)	0.0402 (9)	−0.0255 (12)	0.0256 (9)	0.0052 (9)
C15	0.0620 (11)	0.0649 (11)	0.0364 (8)	−0.0171 (9)	0.0246 (7)	−0.0087 (8)
C16	0.0336 (7)	0.0448 (8)	0.0364 (7)	−0.0050 (6)	0.0162 (6)	−0.0060 (6)
N17	0.0429 (7)	0.0391 (7)	0.0367 (7)	0.0044 (5)	0.0129 (6)	−0.0102 (5)
O18	0.0787 (14)	0.0254 (8)	0.0592 (12)	0	−0.0243 (10)	0
N19	0.0440 (7)	0.0394 (7)	0.0416 (7)	−0.0037 (5)	0.0079 (5)	−0.0051 (5)
O20	0.0555 (7)	0.0511 (7)	0.0437 (6)	−0.0187 (6)	0.0066 (5)	0.0105 (5)
O21	0.0619 (9)	0.1084 (14)	0.0499 (8)	0.0073 (8)	−0.0093 (7)	−0.0063 (8)
O22	0.0671 (9)	0.0601 (9)	0.0866 (11)	−0.0203 (7)	0.0266 (8)	0.0165 (7)

Zn1—O18	1.9479 (17)	N9—H9	0.74 (2)
Zn1—N2i	2.0421 (11)	C10—C11	1.467 (2)
Zn1—N2	2.0421 (11)	C11—C12	1.395 (2)
Zn1—N17i	2.2147 (14)	C11—C16	1.408 (2)
Zn1—N17	2.2147 (14)	C12—C13	1.383 (3)
N2—C10	1.3285 (18)	C12—H12	0.93
N2—C3	1.3908 (17)	C13—C14	1.381 (3)
C3—C4	1.390 (2)	C13—H13	0.93
C3—C8	1.396 (2)	C14—C15	1.372 (3)
C4—C5	1.382 (2)	C14—H14	0.93
C4—H4	0.93	C15—C16	1.387 (2)
C5—C6	1.401 (3)	C15—H15	0.93
C5—H5	0.93	C16—N17	1.422 (2)
C6—C7	1.375 (2)	N17—H17A	0.86 (2)
C6—H6	0.93	N17—H17B	0.87 (2)
C7—C8	1.395 (2)	O18—H18	0.77 (2)
C7—H7	0.93	N19—O21	1.2235 (18)
C8—N9	1.379 (2)	N19—O22	1.228 (2)
N9—C10	1.3518 (18)	N19—O20	1.2601 (17)
O18—Zn1—N2i	122.42 (3)	C8—N9—H9	127.4 (15)
O18—Zn1—N2	122.42 (3)	N2—C10—N9	111.48 (12)
N2i—Zn1—N2	115.17 (7)	N2—C10—C11	124.91 (12)
O18—Zn1—N17i	96.88 (4)	N9—C10—C11	123.58 (13)
N2i—Zn1—N17i	80.04 (5)	C12—C11—C16	119.21 (14)
N2—Zn1—N17i	92.55 (5)	C12—C11—C10	120.13 (14)
O18—Zn1—N17	96.88 (4)	C16—C11—C10	120.65 (14)
N2i—Zn1—N17	92.55 (5)	C13—C12—C11	120.70 (17)
N2—Zn1—N17	80.04 (5)	C13—C12—H12	119.6
N17i—Zn1—N17	166.24 (7)	C11—C12—H12	119.6
C10—N2—C3	106.20 (11)	C14—C13—C12	119.43 (18)
C10—N2—Zn1	120.54 (9)	C14—C13—H13	120.3
C3—N2—Zn1	130.45 (10)	C12—C13—H13	120.3
C4—C3—N2	130.43 (14)	C15—C14—C13	120.80 (17)
C4—C3—C8	120.91 (13)	C15—C14—H14	119.6
N2—C3—C8	108.66 (12)	C13—C14—H14	119.6
C5—C4—C3	117.13 (16)	C14—C15—C16	120.73 (17)
C5—C4—H4	121.4	C14—C15—H15	119.6
C3—C4—H4	121.4	C16—C15—H15	119.6
C4—C5—C6	121.54 (16)	C15—C16—C11	119.12 (15)
C4—C5—H5	119.2	C15—C16—N17	119.91 (15)
C6—C5—H5	119.2	C11—C16—N17	120.88 (14)
C7—C6—C5	121.85 (15)	C16—N17—Zn1	108.50 (9)
C7—C6—H6	119.1	C16—N17—H17A	107.9 (14)
C5—C6—H6	119.1	Zn1—N17—H17A	121.4 (14)
C6—C7—C8	116.50 (15)	C16—N17—H17B	110.7 (11)
C6—C7—H7	121.7	Zn1—N17—H17B	95.1 (13)
C8—C7—H7	121.7	H17A—N17—H17B	112.7 (18)
N9—C8—C7	132.26 (14)	Zn1—O18—H18	117.5 (18)
N9—C8—C3	105.73 (12)	O21—N19—O22	119.85 (16)
C7—C8—C3	122.00 (14)	O21—N19—O20	121.32 (16)
C10—N9—C8	107.93 (12)	O22—N19—O20	118.78 (14)
C10—N9—H9	123.6 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O21ii	0.74 (2)	2.51 (2)	3.248 (2)	173 (2)
N9—H9···O22ii	0.74 (2)	2.37 (2)	2.944 (2)	134.7 (19)
N17—H17A···O20iii	0.86 (2)	2.14 (2)	2.9937 (17)	169 (2)
O18—H18···O20	0.77 (2)	1.92 (2)	2.6897 (14)	175 (2)
O18—H18···O22	0.77 (2)	2.50 (2)	3.0345 (16)	128 (2)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N9H9O21i	0.74(2)	2.51(2)	3.248(2)	173(2)
N9H9O22i	0.74(2)	2.37(2)	2.944(2)	134.7(19)
N17H17AO20ii	0.86(2)	2.14(2)	2.9937(17)	169(2)
O18H18O20	0.77(2)	1.92(2)	2.6897(14)	175(2)
O18H18O22	0.77(2)	2.50(2)	3.0345(16)	128(2)

Symmetry codes: (i) ; (ii) .