(2-{[2-(1H-Benzimidazol-2-yl-κN)phen-yl]imino-methyl-κN}-5-methyl-phenolato-κO)chloridozinc(II).

In the title mononuclear complex, [Zn(C(21)H(16)N(3)O)Cl], the Zn(II) ion is coordinated in a distorted tetra-hedral geometry by two benzimidazole N atoms and one phenolate O atom from the tridentate Schiff base ligand and a chloride ligand. The benzimidazole ring system forms dihedral angles of 26.68 (9) and 56.16 (9)° with the adjacent benzene ring and the methyl-phenolate group benzene ring, respectively. In the crystal, mol-ecules are linked by N-H⋯Cl hydrogen bonds into chains along [100]. Furthermore, weak C-H⋯O and C-H⋯π inter-actions, in addition to π-π inter-actions with centroid-centroid distances in the range 3.5826 (13)-3.9681 (13) Å, are also observed.

Related literature

For standard bond-length data, see: Allen et al. (1987 ▶). For background to benzimidazoles and their applications, see: Chassaing et al. (2008 ▶); Kucukbay et al. (2003 ▶); Podunavac-Kuzmanovic & Cvetkovic (2010 ▶); Podunavac-Kuzmanovic et al. (1999 ▶); Podunavac-Kuzmanovic & Markov (2006 ▶); Xue et al. (2011 ▶). For related structures, see: Eltayeb et al. (2007 ▶, 2009 ▶); Eltayeb, Teoh, Chantrapromma & Fun (2011 ▶); Eltayeb, Teoh, Yeap & Fun (2011 ▶); Maldonado-Rogado et al. (2007 ▶); Tong & Ye (2004 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

[Zn(C21n class="Species">H16N3O)Cl]

M = 427.21

Monoclinic,

a = 8.6338 (1) Å

b = 19.4952 (2) Å

c = 10.9687 (1) Å

β = 99.675 (1)°

V = 1819.97 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.51 mm−1

T = 100 K

0.26 × 0.18 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.694, T max = 0.878

22729 measured reflections

5678 independent reflections

3773 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.088

S = 1.03

5678 reflections

249 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030170/lh6598sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030170/lh6598Isup2.hkl

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

[Zn(C21H16N3O)Cl]	F(000) = 872
Mr = 427.21	Dx = 1.559 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5678 reflections
a = 8.6338 (1) Å	θ = 2.1–30.7°
b = 19.4952 (2) Å	µ = 1.51 mm−1
c = 10.9687 (1) Å	T = 100 K
β = 99.675 (1)°	Block, yellow
V = 1819.97 (3) Å3	0.26 × 0.18 × 0.09 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	5678 independent reflections
Radiation source: sealed tube	3773 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 30.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.694, Tmax = 0.878	k = −28→26
22729 measured reflections	l = −12→15

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0283P)2 + 0.6885P] where P = (Fo2 + 2Fc2)/3
5678 reflections	(Δ/σ)max = 0.001
249 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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 > 2sigma(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
Zn1	0.66403 (3)	0.062335 (13)	0.71581 (2)	0.03608 (9)
Cl1	0.50460 (7)	0.00213 (4)	0.81468 (7)	0.05647 (19)
O1	0.56252 (18)	0.11090 (8)	0.57283 (14)	0.0414 (4)
N1	0.86821 (19)	0.01439 (9)	0.71573 (16)	0.0330 (4)
N2	1.1246 (2)	−0.00194 (10)	0.76330 (18)	0.0375 (4)
N3	0.7792 (2)	0.14557 (9)	0.79697 (16)	0.0349 (4)
C1	0.9123 (2)	−0.03570 (11)	0.63665 (19)	0.0336 (5)
C2	0.8211 (3)	−0.07198 (12)	0.5421 (2)	0.0413 (5)
H2A	0.7133	−0.0651	0.5221	0.050*
C3	0.8977 (3)	−0.11859 (13)	0.4794 (2)	0.0504 (6)
H3A	0.8401	−0.1447	0.4167	0.060*
C4	1.0616 (3)	−0.12755 (13)	0.5080 (2)	0.0496 (6)
H4A	1.1098	−0.1590	0.4628	0.060*
C5	1.1522 (3)	−0.09105 (12)	0.6007 (2)	0.0445 (6)
H5A	1.2606	−0.0967	0.6190	0.053*
C6	1.0740 (3)	−0.04558 (11)	0.6655 (2)	0.0358 (5)
C7	0.9989 (2)	0.03287 (11)	0.79017 (19)	0.0318 (5)
C8	1.0111 (2)	0.08132 (11)	0.89379 (19)	0.0332 (5)
C9	1.1357 (3)	0.07388 (12)	0.9935 (2)	0.0388 (5)
H9A	1.2078	0.0386	0.9919	0.047*
C10	1.1532 (3)	0.11775 (13)	1.0936 (2)	0.0456 (6)
H10A	1.2370	0.1123	1.1582	0.055*
C11	1.0461 (3)	0.16957 (14)	1.0971 (2)	0.0520 (7)
H11A	1.0567	0.1986	1.1653	0.062*
C12	0.9230 (3)	0.17893 (13)	1.0006 (2)	0.0451 (6)
H12A	0.8517	0.2144	1.0042	0.054*
C13	0.9045 (2)	0.13597 (11)	0.89831 (19)	0.0351 (5)
C14	0.7407 (2)	0.20702 (12)	0.7581 (2)	0.0374 (5)
H14A	0.7912	0.2430	0.8042	0.045*
C15	0.6287 (2)	0.22529 (11)	0.6517 (2)	0.0362 (5)
C16	0.6017 (3)	0.29611 (12)	0.6307 (2)	0.0438 (6)
H16A	0.6503	0.3273	0.6890	0.053*
C17	0.5065 (3)	0.32035 (13)	0.5274 (2)	0.0470 (6)
H17A	0.4893	0.3673	0.5172	0.056*
C18	0.4349 (3)	0.27452 (12)	0.4370 (2)	0.0411 (5)
C19	0.4615 (3)	0.20532 (12)	0.4549 (2)	0.0408 (5)
H19A	0.4170	0.1753	0.3928	0.049*
C20	0.5529 (2)	0.17729 (12)	0.5628 (2)	0.0365 (5)
C21	0.3284 (3)	0.29989 (14)	0.3235 (2)	0.0541 (7)
H21A	0.3299	0.2681	0.2569	0.081*
H21B	0.3640	0.3440	0.3006	0.081*
H21C	0.2232	0.3038	0.3405	0.081*
H1N1	1.208 (3)	0.0047 (13)	0.793 (2)	0.051 (8)*

	U11	U22	U33	U12	U13	U23
Zn1	0.02462 (12)	0.03720 (15)	0.04474 (16)	0.00021 (11)	0.00096 (10)	0.00267 (12)
Cl1	0.0295 (3)	0.0641 (4)	0.0770 (5)	−0.0005 (3)	0.0123 (3)	0.0210 (4)
O1	0.0393 (8)	0.0357 (9)	0.0447 (9)	−0.0003 (7)	−0.0063 (7)	0.0032 (7)
N1	0.0269 (8)	0.0347 (10)	0.0367 (9)	−0.0008 (7)	0.0029 (7)	0.0039 (8)
N2	0.0252 (9)	0.0420 (11)	0.0433 (11)	0.0027 (9)	0.0000 (8)	0.0006 (9)
N3	0.0280 (8)	0.0382 (10)	0.0372 (10)	0.0010 (8)	0.0018 (7)	−0.0020 (8)
C1	0.0344 (11)	0.0308 (11)	0.0357 (11)	0.0002 (9)	0.0062 (9)	0.0037 (9)
C2	0.0374 (12)	0.0410 (14)	0.0442 (13)	−0.0029 (10)	0.0030 (10)	0.0003 (11)
C3	0.0646 (17)	0.0414 (14)	0.0440 (14)	−0.0089 (13)	0.0054 (12)	−0.0046 (12)
C4	0.0651 (17)	0.0369 (14)	0.0507 (15)	0.0040 (12)	0.0211 (13)	−0.0006 (11)
C5	0.0437 (13)	0.0407 (13)	0.0505 (14)	0.0077 (11)	0.0118 (11)	0.0068 (12)
C6	0.0337 (11)	0.0356 (12)	0.0388 (12)	0.0015 (9)	0.0079 (9)	0.0054 (10)
C7	0.0262 (9)	0.0350 (11)	0.0340 (11)	0.0007 (9)	0.0043 (8)	0.0070 (9)
C8	0.0288 (10)	0.0352 (12)	0.0356 (11)	−0.0040 (9)	0.0055 (8)	0.0050 (9)
C9	0.0322 (11)	0.0425 (13)	0.0401 (12)	−0.0009 (10)	0.0014 (9)	0.0066 (10)
C10	0.0396 (12)	0.0573 (16)	0.0365 (12)	−0.0095 (12)	−0.0038 (10)	0.0043 (11)
C11	0.0538 (15)	0.0623 (17)	0.0377 (13)	−0.0100 (14)	0.0017 (11)	−0.0110 (12)
C12	0.0430 (13)	0.0491 (15)	0.0429 (13)	0.0009 (11)	0.0061 (10)	−0.0089 (11)
C13	0.0281 (10)	0.0392 (12)	0.0367 (11)	−0.0046 (9)	0.0021 (8)	0.0006 (10)
C14	0.0331 (11)	0.0389 (13)	0.0400 (12)	0.0001 (10)	0.0060 (9)	−0.0046 (10)
C15	0.0327 (11)	0.0366 (12)	0.0398 (12)	0.0038 (9)	0.0075 (9)	0.0011 (10)
C16	0.0417 (13)	0.0394 (13)	0.0497 (14)	0.0029 (11)	0.0056 (11)	−0.0042 (11)
C17	0.0442 (13)	0.0387 (14)	0.0581 (15)	0.0063 (11)	0.0084 (12)	0.0055 (12)
C18	0.0344 (11)	0.0458 (14)	0.0440 (13)	0.0070 (10)	0.0089 (10)	0.0078 (11)
C19	0.0370 (12)	0.0460 (14)	0.0385 (12)	−0.0024 (10)	0.0036 (9)	−0.0001 (10)
C20	0.0272 (10)	0.0426 (13)	0.0402 (12)	0.0003 (9)	0.0070 (9)	−0.0010 (10)
C21	0.0474 (14)	0.0585 (17)	0.0544 (15)	0.0114 (13)	0.0022 (12)	0.0111 (13)

Zn1—O1	1.9137 (15)	C8—C13	1.415 (3)
Zn1—N1	1.9954 (17)	C9—C10	1.380 (3)
Zn1—N3	2.0292 (18)	C9—H9A	0.9300
Zn1—Cl1	2.2249 (7)	C10—C11	1.375 (3)
O1—C20	1.300 (3)	C10—H10A	0.9300
N1—C7	1.327 (2)	C11—C12	1.380 (3)
N1—C1	1.401 (3)	C11—H11A	0.9300
N2—C7	1.354 (3)	C12—C13	1.388 (3)
N2—C6	1.381 (3)	C12—H12A	0.9300
N2—H1N1	0.75 (3)	C14—C15	1.430 (3)
N3—C14	1.296 (3)	C14—H14A	0.9300
N3—C13	1.427 (2)	C15—C16	1.413 (3)
C1—C2	1.386 (3)	C15—C20	1.428 (3)
C1—C6	1.392 (3)	C16—C17	1.367 (3)
C2—C3	1.375 (3)	C16—H16A	0.9300
C2—H2A	0.9300	C17—C18	1.399 (3)
C3—C4	1.408 (4)	C17—H17A	0.9300
C3—H3A	0.9300	C18—C19	1.377 (3)
C4—C5	1.373 (3)	C18—C21	1.501 (3)
C4—H4A	0.9300	C19—C20	1.417 (3)
C5—C6	1.381 (3)	C19—H19A	0.9300
C5—H5A	0.9300	C21—H21A	0.9600
C7—C8	1.468 (3)	C21—H21B	0.9600
C8—C9	1.406 (3)	C21—H21C	0.9600
O1—Zn1—N1	120.95 (7)	C10—C9—H9A	119.3
O1—Zn1—N3	95.00 (7)	C8—C9—H9A	119.3
N1—Zn1—N3	90.39 (7)	C11—C10—C9	119.6 (2)
O1—Zn1—Cl1	115.14 (5)	C11—C10—H10A	120.2
N1—Zn1—Cl1	111.84 (5)	C9—C10—H10A	120.2
N3—Zn1—Cl1	120.39 (6)	C10—C11—C12	120.7 (2)
C20—O1—Zn1	125.15 (14)	C10—C11—H11A	119.7
C7—N1—C1	106.20 (17)	C12—C11—H11A	119.7
C7—N1—Zn1	122.18 (15)	C11—C12—C13	120.6 (2)
C1—N1—Zn1	131.21 (13)	C11—C12—H12A	119.7
C7—N2—C6	108.47 (18)	C13—C12—H12A	119.7
C7—N2—H1N1	124 (2)	C12—C13—C8	119.72 (19)
C6—N2—H1N1	127 (2)	C12—C13—N3	121.3 (2)
C14—N3—C13	119.79 (18)	C8—C13—N3	118.95 (19)
C14—N3—Zn1	120.98 (14)	N3—C14—C15	126.9 (2)
C13—N3—Zn1	119.23 (14)	N3—C14—H14A	116.6
C2—C1—C6	121.4 (2)	C15—C14—H14A	116.6
C2—C1—N1	129.8 (2)	C16—C15—C20	119.0 (2)
C6—C1—N1	108.80 (18)	C16—C15—C14	116.5 (2)
C3—C2—C1	116.9 (2)	C20—C15—C14	124.3 (2)
C3—C2—H2A	121.6	C17—C16—C15	122.2 (2)
C1—C2—H2A	121.6	C17—C16—H16A	118.9
C2—C3—C4	121.4 (2)	C15—C16—H16A	118.9
C2—C3—H3A	119.3	C16—C17—C18	119.9 (2)
C4—C3—H3A	119.3	C16—C17—H17A	120.0
C5—C4—C3	121.8 (2)	C18—C17—H17A	120.0
C5—C4—H4A	119.1	C19—C18—C17	118.8 (2)
C3—C4—H4A	119.1	C19—C18—C21	120.3 (2)
C4—C5—C6	116.5 (2)	C17—C18—C21	120.9 (2)
C4—C5—H5A	121.7	C18—C19—C20	123.6 (2)
C6—C5—H5A	121.7	C18—C19—H19A	118.2
C5—C6—N2	132.6 (2)	C20—C19—H19A	118.2
C5—C6—C1	122.0 (2)	O1—C20—C19	118.2 (2)
N2—C6—C1	105.41 (19)	O1—C20—C15	125.38 (19)
N1—C7—N2	111.11 (19)	C19—C20—C15	116.4 (2)
N1—C7—C8	126.48 (19)	C18—C21—H21A	109.5
N2—C7—C8	122.33 (18)	C18—C21—H21B	109.5
C9—C8—C13	117.9 (2)	H21A—C21—H21B	109.5
C9—C8—C7	118.8 (2)	C18—C21—H21C	109.5
C13—C8—C7	123.31 (18)	H21A—C21—H21C	109.5
C10—C9—C8	121.5 (2)	H21B—C21—H21C	109.5
N1—Zn1—O1—C20	−107.74 (18)	N1—C7—C8—C9	152.4 (2)
N3—Zn1—O1—C20	−14.28 (18)	N2—C7—C8—C9	−24.0 (3)
Cl1—Zn1—O1—C20	112.73 (17)	N1—C7—C8—C13	−28.3 (3)
O1—Zn1—N1—C7	116.26 (16)	N2—C7—C8—C13	155.4 (2)
N3—Zn1—N1—C7	20.19 (17)	C13—C8—C9—C10	0.7 (3)
Cl1—Zn1—N1—C7	−103.02 (16)	C7—C8—C9—C10	−179.9 (2)
O1—Zn1—N1—C1	−55.4 (2)	C8—C9—C10—C11	0.7 (4)
N3—Zn1—N1—C1	−151.41 (18)	C9—C10—C11—C12	−1.2 (4)
Cl1—Zn1—N1—C1	85.37 (18)	C10—C11—C12—C13	0.3 (4)
O1—Zn1—N3—C14	13.98 (18)	C11—C12—C13—C8	1.1 (4)
N1—Zn1—N3—C14	135.10 (18)	C11—C12—C13—N3	−179.0 (2)
Cl1—Zn1—N3—C14	−109.09 (17)	C9—C8—C13—C12	−1.6 (3)
O1—Zn1—N3—C13	−166.00 (15)	C7—C8—C13—C12	179.0 (2)
N1—Zn1—N3—C13	−44.88 (16)	C9—C8—C13—N3	178.56 (19)
Cl1—Zn1—N3—C13	70.93 (16)	C7—C8—C13—N3	−0.8 (3)
C7—N1—C1—C2	179.7 (2)	C14—N3—C13—C12	40.8 (3)
Zn1—N1—C1—C2	−7.7 (3)	Zn1—N3—C13—C12	−139.24 (19)
C7—N1—C1—C6	−0.9 (2)	C14—N3—C13—C8	−139.4 (2)
Zn1—N1—C1—C6	171.74 (15)	Zn1—N3—C13—C8	40.6 (2)
C6—C1—C2—C3	0.7 (3)	C13—N3—C14—C15	174.0 (2)
N1—C1—C2—C3	−180.0 (2)	Zn1—N3—C14—C15	−6.0 (3)
C1—C2—C3—C4	−1.6 (3)	N3—C14—C15—C16	177.5 (2)
C2—C3—C4—C5	1.0 (4)	N3—C14—C15—C20	−7.2 (4)
C3—C4—C5—C6	0.7 (4)	C20—C15—C16—C17	−0.6 (4)
C4—C5—C6—N2	179.1 (2)	C14—C15—C16—C17	175.0 (2)
C4—C5—C6—C1	−1.6 (3)	C15—C16—C17—C18	−1.4 (4)
C7—N2—C6—C5	178.7 (2)	C16—C17—C18—C19	0.5 (4)
C7—N2—C6—C1	−0.7 (2)	C16—C17—C18—C21	179.3 (2)
C2—C1—C6—C5	1.0 (3)	C17—C18—C19—C20	2.6 (4)
N1—C1—C6—C5	−178.5 (2)	C21—C18—C19—C20	−176.2 (2)
C2—C1—C6—N2	−179.6 (2)	Zn1—O1—C20—C19	−174.38 (15)
N1—C1—C6—N2	1.0 (2)	Zn1—O1—C20—C15	6.2 (3)
C1—N1—C7—N2	0.4 (2)	C18—C19—C20—O1	176.0 (2)
Zn1—N1—C7—N2	−173.03 (14)	C18—C19—C20—C15	−4.5 (3)
C1—N1—C7—C8	−176.3 (2)	C16—C15—C20—O1	−177.2 (2)
Zn1—N1—C7—C8	10.3 (3)	C14—C15—C20—O1	7.6 (4)
C6—N2—C7—N1	0.2 (2)	C16—C15—C20—C19	3.4 (3)
C6—N2—C7—C8	177.05 (19)	C14—C15—C20—C19	−171.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N1···Cl1i	0.75 (3)	2.53 (3)	3.2352 (19)	157 (2)
C2—H2A···O1ii	0.93	2.59	3.425 (3)	149
C12—H12A···Cg1iii	0.93	2.96	3.762 (3)	145
C21—H21C···Cg2iv	0.96	2.92	3.741 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C15–C20 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N1⋯Cl1i	0.75 (3)	2.53 (3)	3.2352 (19)	157 (2)
C2—H2A⋯O1ii	0.93	2.59	3.425 (3)	149
C12—H12A⋯Cg1iii	0.93	2.96	3.762 (3)	145
C21—H21C⋯Cg2iv	0.96	2.92	3.741 (3)	144

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .