Dibromido{2-[(4-fluoro-phen-yl)imino-meth-yl]pyridine-κ(2)N,N'}zinc.

In the title complex, [ZnBr(2)(C(12)H(9)FN(2))], the Zn(II) atom has a distorted tetra-hedral Br(2)N(2) coordination sphere. The organic ligand is bidentate, coordinating the Zn(II) atom via two imine N atoms. The benzene and pyridine rings are oriented at a dihedral angle of 10.49 (1)°. In the crystal, weak C-H⋯F and C-H⋯Br hydrogen bonds are observed.

Related literature

For background information, see: Dehghanpour et al. (2009 ▶). For related structures, see: Dehghanpour et al. (2007 ▶); Salehzadeh et al. (2011 ▶); Khalaj et al. (2009 ▶).

Experimental

Crystal data

[ZnBr2(C12H9FN2)]

M = 425.40

Monoclinic,

a = 7.7351 (10) Å

b = 9.5372 (13) Å

c = 18.501 (2) Å

β = 96.052 (3)°

V = 1357.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 7.69 mm−1

T = 100 K

0.17 × 0.06 × 0.04 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2005 ▶) T min = 0.435, T max = 0.734

18332 measured reflections

2956 independent reflections

2469 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.072

S = 1.00

2956 reflections

163 parameters

H-atom parameters constrained

Δρmax = 2.44 e Å−3

Δρmin = −0.77 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812031091/pv2564sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031091/pv2564Isup2.hkl

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

[ZnBr2(C12H9FN2)]	F(000) = 816
Mr = 425.40	Dx = 2.082 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3858 reflections
a = 7.7351 (10) Å	θ = 2.2–29.7°
b = 9.5372 (13) Å	µ = 7.69 mm−1
c = 18.501 (2) Å	T = 100 K
β = 96.052 (3)°	Prism, colourless
V = 1357.2 (3) Å3	0.17 × 0.06 × 0.04 mm
Z = 4

Bruker APEXII area-detector diffractometer	2956 independent reflections
Radiation source: fine-focus sealed tube	2469 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −9→9
Tmin = 0.435, Tmax = 0.734	k = −12→12
18332 measured reflections	l = −23→23

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0358P)2 + 2.3621P] where P = (Fo2 + 2Fc2)/3
2956 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 2.44 e Å−3
0 restraints	Δρmin = −0.77 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.

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
Br1	−0.00870 (4)	0.67594 (4)	0.09661 (2)	0.01923 (10)
Br2	0.50834 (4)	0.69666 (4)	0.11656 (2)	0.02040 (10)
Zn1	0.24082 (5)	0.76510 (4)	0.05390 (2)	0.01606 (11)
N2	0.2404 (4)	0.9803 (3)	0.03443 (16)	0.0159 (6)
C1	0.2874 (4)	0.8917 (4)	−0.08143 (19)	0.0166 (7)
F1	0.1273 (3)	1.3856 (3)	0.23727 (12)	0.0320 (6)
C8	0.2592 (5)	1.2286 (4)	0.0745 (2)	0.0193 (8)
H8A	0.3069	1.2546	0.0324	0.023*
C9	0.2290 (5)	1.3290 (4)	0.1259 (2)	0.0227 (8)
H9A	0.2547	1.4229	0.1187	0.027*
C2	0.3253 (5)	0.9156 (4)	−0.1518 (2)	0.0223 (8)
H2A	0.3411	1.0063	−0.1683	0.027*
C10	0.1598 (5)	1.2862 (4)	0.1881 (2)	0.0232 (8)
C6	0.2678 (4)	1.0072 (4)	−0.03110 (19)	0.0180 (7)
H6A	0.2753	1.0996	−0.0466	0.022*
C12	0.1525 (5)	1.0492 (4)	0.1500 (2)	0.0205 (8)
H12A	0.1290	0.9552	0.1582	0.025*
C4	0.3159 (5)	0.6678 (4)	−0.1709 (2)	0.0259 (9)
H4A	0.3237	0.5900	−0.2006	0.031*
C7	0.2183 (4)	1.0901 (4)	0.08600 (19)	0.0160 (7)
C3	0.3393 (5)	0.8013 (5)	−0.1973 (2)	0.0264 (9)
H3A	0.3642	0.8144	−0.2450	0.032*
C5	0.2804 (5)	0.6514 (4)	−0.0995 (2)	0.0232 (8)
H5A	0.2662	0.5615	−0.0817	0.028*
C11	0.1222 (5)	1.1492 (4)	0.2015 (2)	0.0240 (8)
H11A	0.0771	1.1237	0.2443	0.029*
N1	0.2661 (4)	0.7613 (3)	−0.05549 (16)	0.0176 (6)

	U11	U22	U33	U12	U13	U23
Br1	0.01582 (18)	0.01869 (19)	0.0241 (2)	−0.00193 (13)	0.00645 (13)	0.00462 (15)
Br2	0.01554 (18)	0.0241 (2)	0.0222 (2)	0.00173 (14)	0.00489 (13)	0.00680 (15)
Zn1	0.0172 (2)	0.0141 (2)	0.0177 (2)	−0.00006 (16)	0.00594 (15)	0.00254 (16)
N2	0.0161 (15)	0.0135 (15)	0.0183 (15)	−0.0001 (12)	0.0029 (11)	−0.0010 (12)
C1	0.0130 (16)	0.0193 (19)	0.0175 (17)	0.0004 (14)	0.0011 (13)	0.0007 (15)
F1	0.0414 (14)	0.0251 (13)	0.0298 (13)	0.0036 (11)	0.0046 (10)	−0.0122 (10)
C8	0.0170 (17)	0.0229 (19)	0.0182 (18)	0.0014 (15)	0.0020 (14)	0.0022 (15)
C9	0.026 (2)	0.0112 (18)	0.030 (2)	0.0010 (14)	−0.0023 (16)	−0.0023 (16)
C2	0.0223 (19)	0.022 (2)	0.023 (2)	0.0031 (15)	0.0046 (15)	0.0059 (16)
C10	0.0210 (19)	0.025 (2)	0.0231 (19)	0.0029 (16)	−0.0008 (15)	−0.0089 (17)
C6	0.0142 (17)	0.0202 (19)	0.0198 (18)	0.0021 (14)	0.0026 (13)	0.0039 (15)
C12	0.0218 (19)	0.0165 (18)	0.0238 (19)	−0.0012 (15)	0.0058 (15)	0.0024 (15)
C4	0.028 (2)	0.027 (2)	0.023 (2)	0.0038 (17)	0.0005 (16)	−0.0125 (17)
C7	0.0113 (16)	0.0175 (18)	0.0192 (18)	0.0041 (13)	0.0016 (13)	−0.0037 (14)
C3	0.028 (2)	0.036 (2)	0.0157 (18)	0.0081 (18)	0.0056 (15)	0.0008 (17)
C5	0.0207 (19)	0.020 (2)	0.030 (2)	−0.0019 (15)	0.0052 (16)	−0.0001 (16)
C11	0.026 (2)	0.028 (2)	0.0185 (19)	0.0001 (16)	0.0077 (15)	−0.0019 (16)
N1	0.0155 (15)	0.0181 (16)	0.0198 (15)	0.0003 (12)	0.0045 (12)	−0.0007 (13)

Br1—Zn1	2.3225 (6)	C2—C3	1.389 (6)
Br2—Zn1	2.3550 (6)	C2—H2A	0.9300
Zn1—N1	2.054 (3)	C10—C11	1.366 (6)
Zn1—N2	2.084 (3)	C6—H6A	0.9300
N2—C6	1.279 (5)	C12—C11	1.385 (5)
N2—C7	1.439 (4)	C12—C7	1.393 (5)
C1—N1	1.350 (5)	C12—H12A	0.9300
C1—C2	1.383 (5)	C4—C3	1.383 (6)
C1—C6	1.461 (5)	C4—C5	1.385 (6)
F1—C10	1.356 (4)	C4—H4A	0.9300
C8—C7	1.380 (5)	C3—H3A	0.9300
C8—C9	1.386 (5)	C5—N1	1.339 (5)
C8—H8A	0.9300	C5—H5A	0.9300
C9—C10	1.381 (6)	C11—H11A	0.9300
C9—H9A	0.9300
N1—Zn1—N2	81.13 (12)	N2—C6—C1	119.4 (3)
N1—Zn1—Br1	119.84 (8)	N2—C6—H6A	120.3
N2—Zn1—Br1	115.66 (8)	C1—C6—H6A	120.3
N1—Zn1—Br2	108.07 (8)	C11—C12—C7	119.7 (4)
N2—Zn1—Br2	110.09 (8)	C11—C12—H12A	120.1
Br1—Zn1—Br2	116.72 (2)	C7—C12—H12A	120.1
C6—N2—C7	121.7 (3)	C3—C4—C5	119.2 (4)
C6—N2—Zn1	111.4 (3)	C3—C4—H4A	120.4
C7—N2—Zn1	126.9 (2)	C5—C4—H4A	120.4
N1—C1—C2	122.1 (3)	C8—C7—C12	120.6 (3)
N1—C1—C6	116.3 (3)	C8—C7—N2	123.3 (3)
C2—C1—C6	121.5 (3)	C12—C7—N2	116.1 (3)
C7—C8—C9	119.8 (3)	C4—C3—C2	119.1 (4)
C7—C8—H8A	120.1	C4—C3—H3A	120.5
C9—C8—H8A	120.1	C2—C3—H3A	120.5
C10—C9—C8	118.4 (4)	N1—C5—C4	121.9 (4)
C10—C9—H9A	120.8	N1—C5—H5A	119.0
C8—C9—H9A	120.8	C4—C5—H5A	119.0
C1—C2—C3	118.7 (4)	C10—C11—C12	118.6 (4)
C1—C2—H2A	120.7	C10—C11—H11A	120.7
C3—C2—H2A	120.7	C12—C11—H11A	120.7
F1—C10—C11	119.3 (4)	C5—N1—C1	118.9 (3)
F1—C10—C9	117.9 (3)	C5—N1—Zn1	129.5 (3)
C11—C10—C9	122.8 (4)	C1—N1—Zn1	111.2 (2)
N1—Zn1—N2—C6	−4.7 (3)	C6—N2—C7—C12	166.6 (3)
Br1—Zn1—N2—C6	−123.7 (2)	Zn1—N2—C7—C12	−15.4 (4)
Br2—Zn1—N2—C6	101.4 (2)	C5—C4—C3—C2	−0.6 (6)
N1—Zn1—N2—C7	177.1 (3)	C1—C2—C3—C4	−0.3 (6)
Br1—Zn1—N2—C7	58.2 (3)	C3—C4—C5—N1	0.8 (6)
Br2—Zn1—N2—C7	−76.8 (3)	F1—C10—C11—C12	178.6 (3)
C7—C8—C9—C10	0.7 (5)	C9—C10—C11—C12	−0.9 (6)
N1—C1—C2—C3	0.9 (5)	C7—C12—C11—C10	−0.7 (6)
C6—C1—C2—C3	−178.9 (3)	C4—C5—N1—C1	−0.2 (5)
C8—C9—C10—F1	−178.6 (3)	C4—C5—N1—Zn1	−172.7 (3)
C8—C9—C10—C11	0.9 (6)	C2—C1—N1—C5	−0.7 (5)
C7—N2—C6—C1	−179.3 (3)	C6—C1—N1—C5	179.2 (3)
Zn1—N2—C6—C1	2.4 (4)	C2—C1—N1—Zn1	173.1 (3)
N1—C1—C6—N2	3.2 (5)	C6—C1—N1—Zn1	−7.0 (4)
C2—C1—C6—N2	−176.9 (3)	N2—Zn1—N1—C5	179.3 (3)
C9—C8—C7—C12	−2.3 (5)	Br1—Zn1—N1—C5	−66.1 (3)
C9—C8—C7—N2	178.0 (3)	Br2—Zn1—N1—C5	71.0 (3)
C11—C12—C7—C8	2.3 (5)	N2—Zn1—N1—C1	6.3 (2)
C11—C12—C7—N2	−178.0 (3)	Br1—Zn1—N1—C1	120.9 (2)
C6—N2—C7—C8	−13.7 (5)	Br2—Zn1—N1—C1	−102.0 (2)
Zn1—N2—C7—C8	164.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···Br1	0.93	3.04	3.866 (4)	148
C2—H2A···F1i	0.93	2.50	3.081 (4)	121
C5—H5A···Br1ii	0.93	3.01	3.767 (4)	140
C6—H6A···Br1iii	0.93	3.05	3.756 (4)	134
C3—H3A···Br2iv	0.93	2.90	3.810 (4)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯Br1	0.93	3.04	3.866 (4)	148
C2—H2A⋯F1i	0.93	2.50	3.081 (4)	121
C5—H5A⋯Br1ii	0.93	3.01	3.767 (4)	140
C6—H6A⋯Br1iii	0.93	3.05	3.756 (4)	134
C3—H3A⋯Br2iv	0.93	2.90	3.810 (4)	166

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