[N,N'-Bis(2,6-dichloro-benzyl-idene)propane-1,3-diamine-κ(2)N,N']dibromidozinc.

In the title compound, [ZnBr(2)(C(17)H(14)Cl(4)N(2))], the Zn(II) ion is bonded to two bromide ions and two N atoms of the diimine ligand and displays a moderately distorted tetra-hedral coordination geometry. The Schiff base ligand acts as a chelating ligand and coordinates to the Zn(II) atom via two N atoms.

Related literature

For related structures, see: Khalaj et al. (2008 ▶, 2009 ▶); Saleh­zadeh et al. (2011 ▶); Khalaji et al. (2010 ▶, 2011 ▶, 2012 ▶). For properties and application of complexes of symmetric bidentate Schiff base ligands, see: Komatsu et al. (2007 ▶); Montazerozohori et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[ZnBr2(C17H14Cl4N2)]

M = 613.3

Monoclinic,

a = 17.0433 (3) Å

b = 9.3216 (2) Å

c = 13.6038 (2) Å

β = 97.313 (2)°

V = 2143.67 (7) Å3

Z = 4

Mo Kα radiation

μ = 5.38 mm−1

T = 120 K

0.33 × 0.28 × 0.10 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.5, T max = 1

32456 measured reflections

5469 independent reflections

4344 reflections with I > 3σ(I)

R int = 0.032

Refinement

R[F 2 > 3σ(F 2)] = 0.023

wR(F 2) = 0.053

S = 1.32

5469 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027997/bt5947sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027997/bt5947Isup2.hkl

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

[ZnBr2(C17H14Cl4N2)]	F(000) = 1192
Mr = 613.3	Dx = 1.900 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 14022 reflections
a = 17.0433 (3) Å	θ = 3.0–29.3°
b = 9.3216 (2) Å	µ = 5.38 mm−1
c = 13.6038 (2) Å	T = 120 K
β = 97.313 (2)°	Block, colourless
V = 2143.67 (7) Å3	0.33 × 0.28 × 0.10 mm
Z = 4

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	5469 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4344 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 10.3784 pixels mm-1	θmax = 29.4°, θmin = 3.0°
Rotation method data acquisition using ω scans	h = −21→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
Tmin = 0.5, Tmax = 1	l = −18→17
32456 measured reflections

Refinement on F2	56 constraints
R[F2 > 2σ(F2)] = 0.023	H-atom parameters constrained
wR(F2) = 0.053	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
S = 1.32	(Δ/σ)max = 0.002
5469 reflections	Δρmax = 0.55 e Å−3
235 parameters	Δρmin = −0.43 e Å−3
0 restraints

Experimental. Absorption correction: CrysAlisPro (Agilent Technologies, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
Zn1	0.778715 (13)	−0.01264 (2)	0.739863 (16)	0.01974 (7)
Br1	0.815993 (14)	−0.06312 (2)	0.909367 (15)	0.03043 (7)
Br2	0.768458 (12)	0.22386 (2)	0.682623 (15)	0.02510 (7)
Cl1	0.57897 (3)	−0.18717 (6)	0.46139 (4)	0.03164 (17)
Cl2	0.49527 (3)	−0.02131 (6)	0.81149 (4)	0.03069 (16)
Cl3	0.78647 (4)	−0.01110 (6)	0.42235 (4)	0.03640 (18)
Cl4	1.01713 (4)	−0.02162 (7)	0.73027 (4)	0.0435 (2)
N1	0.67043 (10)	−0.11134 (16)	0.70285 (12)	0.0204 (5)
N2	0.83223 (9)	−0.16701 (17)	0.66248 (11)	0.0190 (5)
C1	0.72353 (12)	−0.3466 (2)	0.66028 (16)	0.0272 (6)
C2	0.67041 (12)	−0.2659 (2)	0.72376 (16)	0.0273 (6)
C3	0.60879 (12)	−0.0487 (2)	0.66383 (14)	0.0216 (6)
C4	0.52967 (11)	−0.1151 (2)	0.63559 (15)	0.0219 (6)
C5	0.50947 (12)	−0.1818 (2)	0.54428 (15)	0.0252 (6)
C6	0.43508 (13)	−0.2408 (2)	0.51740 (17)	0.0321 (7)
C7	0.37960 (13)	−0.2328 (2)	0.58284 (17)	0.0342 (7)
C8	0.39751 (12)	−0.1666 (2)	0.67387 (17)	0.0306 (7)
C9	0.47174 (12)	−0.1085 (2)	0.69829 (15)	0.0240 (6)
C10	0.81108 (12)	−0.3168 (2)	0.68397 (14)	0.0218 (6)
C11	0.87837 (12)	−0.1473 (2)	0.59844 (14)	0.0232 (6)
C12	0.90508 (12)	−0.0029 (2)	0.57246 (14)	0.0223 (6)
C13	0.86796 (12)	0.0692 (2)	0.48978 (15)	0.0248 (6)
C14	0.89235 (13)	0.2026 (2)	0.46228 (17)	0.0308 (7)
C15	0.95599 (13)	0.2659 (2)	0.51856 (16)	0.0312 (7)
C16	0.99483 (13)	0.1988 (2)	0.60108 (16)	0.0300 (7)
C17	0.96911 (12)	0.0647 (2)	0.62674 (15)	0.0260 (6)
H1a	0.714222	−0.447812	0.664797	0.0326*
H1b	0.706896	−0.326754	0.591541	0.0326*
H2a	0.617401	−0.302232	0.710663	0.0327*
H2b	0.688664	−0.281934	0.792584	0.0327*
H3	0.613239	0.052004	0.650974	0.0259*
H6	0.422365	−0.286607	0.45416	0.0386*
H7	0.328059	−0.273674	0.564947	0.0411*
H8	0.358864	−0.161171	0.719285	0.0367*
H10a	0.827835	−0.337727	0.752531	0.0262*
H10b	0.840072	−0.381379	0.64704	0.0262*
H11	0.896906	−0.229113	0.56525	0.0278*
H14	0.865572	0.250488	0.405122	0.037*
H15	0.973645	0.35864	0.499922	0.0375*
H16	1.038872	0.244152	0.639989	0.036*

	U11	U22	U33	U12	U13	U23
Zn1	0.01828 (12)	0.01772 (12)	0.02378 (12)	−0.00064 (9)	0.00483 (9)	−0.00078 (9)
Br1	0.04287 (14)	0.02484 (11)	0.02295 (11)	−0.00147 (9)	0.00178 (9)	0.00022 (8)
Br2	0.02661 (12)	0.01722 (10)	0.03323 (12)	0.00196 (8)	0.01065 (9)	0.00062 (8)
Cl1	0.0296 (3)	0.0355 (3)	0.0303 (3)	0.0012 (2)	0.0057 (2)	−0.0026 (2)
Cl2	0.0303 (3)	0.0317 (3)	0.0313 (3)	0.0085 (2)	0.0086 (2)	0.0035 (2)
Cl3	0.0359 (3)	0.0301 (3)	0.0389 (3)	0.0017 (2)	−0.0119 (3)	−0.0036 (2)
Cl4	0.0394 (4)	0.0537 (4)	0.0335 (3)	−0.0191 (3)	−0.0102 (3)	0.0086 (3)
N1	0.0173 (8)	0.0191 (8)	0.0252 (8)	0.0008 (7)	0.0047 (7)	0.0012 (7)
N2	0.0159 (8)	0.0209 (8)	0.0194 (8)	0.0000 (7)	−0.0008 (7)	−0.0022 (7)
C1	0.0230 (11)	0.0162 (10)	0.0405 (12)	−0.0015 (8)	−0.0033 (9)	0.0002 (9)
C2	0.0165 (10)	0.0208 (10)	0.0439 (13)	−0.0020 (8)	0.0016 (9)	0.0114 (9)
C3	0.0220 (11)	0.0187 (10)	0.0251 (10)	0.0001 (8)	0.0067 (9)	−0.0002 (8)
C4	0.0161 (10)	0.0181 (10)	0.0312 (10)	0.0046 (8)	0.0019 (8)	0.0056 (8)
C5	0.0222 (11)	0.0218 (10)	0.0315 (11)	0.0032 (8)	0.0038 (9)	0.0042 (9)
C6	0.0275 (12)	0.0282 (11)	0.0387 (13)	−0.0011 (9)	−0.0034 (10)	0.0014 (10)
C7	0.0188 (11)	0.0308 (12)	0.0508 (15)	−0.0022 (9)	−0.0042 (10)	0.0084 (11)
C8	0.0193 (11)	0.0291 (11)	0.0444 (13)	0.0042 (9)	0.0078 (10)	0.0108 (10)
C9	0.0224 (11)	0.0212 (10)	0.0283 (10)	0.0059 (8)	0.0029 (9)	0.0060 (9)
C10	0.0210 (10)	0.0171 (9)	0.0270 (10)	0.0031 (8)	0.0015 (8)	0.0025 (8)
C11	0.0194 (10)	0.0253 (10)	0.0243 (10)	0.0003 (8)	0.0006 (8)	−0.0043 (9)
C12	0.0207 (10)	0.0235 (10)	0.0238 (10)	0.0017 (8)	0.0075 (8)	−0.0045 (8)
C13	0.0222 (11)	0.0244 (10)	0.0275 (10)	0.0028 (8)	0.0026 (9)	−0.0071 (9)
C14	0.0345 (13)	0.0234 (11)	0.0352 (12)	0.0092 (9)	0.0067 (10)	0.0022 (9)
C15	0.0307 (12)	0.0211 (10)	0.0444 (13)	−0.0022 (9)	0.0147 (11)	−0.0012 (10)
C16	0.0254 (12)	0.0305 (12)	0.0355 (12)	−0.0097 (9)	0.0090 (10)	−0.0074 (10)
C17	0.0230 (11)	0.0325 (11)	0.0228 (10)	−0.0038 (9)	0.0042 (9)	−0.0024 (9)

Zn1—Br1	2.3599 (3)	C6—C7	1.381 (3)
Zn1—Br2	2.3371 (3)	C6—H6	0.96
Zn1—N1	2.0662 (16)	C7—C8	1.383 (3)
Zn1—N2	2.0628 (16)	C7—H7	0.96
N1—C2	1.469 (2)	C8—C9	1.377 (3)
N1—C3	1.259 (2)	C8—H8	0.96
N2—C10	1.481 (2)	C10—H10a	0.96
N2—C11	1.259 (3)	C10—H10b	0.96
C1—C2	1.526 (3)	C11—C12	1.478 (3)
C1—C10	1.512 (3)	C11—H11	0.96
C1—H1a	0.96	C12—C13	1.391 (3)
C1—H1b	0.96	C12—C17	1.388 (3)
C2—H2a	0.96	C13—C14	1.379 (3)
C2—H2b	0.96	C14—C15	1.378 (3)
C3—C4	1.489 (3)	C14—H14	0.96
C3—H3	0.96	C15—C16	1.379 (3)
C4—C5	1.393 (3)	C15—H15	0.96
C4—C9	1.386 (3)	C16—C17	1.384 (3)
C5—C6	1.388 (3)	C16—H16	0.96
Br1—Zn1—Br2	120.866 (11)	C5—C6—H6	120.45
Br1—Zn1—N1	105.69 (5)	C7—C6—H6	120.45
Br1—Zn1—N2	106.14 (4)	C6—C7—C8	120.7 (2)
Br2—Zn1—N1	108.19 (4)	C6—C7—H7	119.65
Br2—Zn1—N2	120.47 (4)	C8—C7—H7	119.65
N1—Zn1—N2	90.24 (6)	C7—C8—C9	118.9 (2)
Zn1—N1—C2	114.32 (12)	C7—C8—H8	120.57
Zn1—N1—C3	124.61 (13)	C9—C8—H8	120.57
C2—N1—C3	121.05 (16)	C4—C9—C8	122.59 (19)
Zn1—N2—C10	115.00 (12)	N2—C10—C1	112.92 (15)
Zn1—N2—C11	127.37 (14)	N2—C10—H10a	109.47
C10—N2—C11	117.60 (17)	N2—C10—H10b	109.47
C2—C1—C10	115.44 (16)	C1—C10—H10a	109.47
C2—C1—H1a	109.47	C1—C10—H10b	109.47
C2—C1—H1b	109.47	H10a—C10—H10b	105.79
C10—C1—H1a	109.47	N2—C11—C12	122.46 (18)
C10—C1—H1b	109.47	N2—C11—H11	118.77
H1a—C1—H1b	102.77	C12—C11—H11	118.77
N1—C2—C1	111.04 (17)	C11—C12—C13	120.71 (17)
N1—C2—H2a	109.47	C11—C12—C17	122.07 (17)
N1—C2—H2b	109.47	C13—C12—C17	117.19 (18)
C1—C2—H2a	109.47	C12—C13—C14	122.22 (18)
C1—C2—H2b	109.47	C13—C14—C15	118.60 (19)
H2a—C2—H2b	107.85	C13—C14—H14	120.7
N1—C3—C4	126.59 (18)	C15—C14—H14	120.7
N1—C3—H3	116.71	C14—C15—C16	121.4 (2)
C4—C3—H3	116.71	C14—C15—H15	119.32
C3—C4—C5	121.91 (19)	C16—C15—H15	119.32
C3—C4—C9	121.04 (17)	C15—C16—C17	118.73 (19)
C5—C4—C9	117.01 (18)	C15—C16—H16	120.63
C4—C5—C6	121.7 (2)	C17—C16—H16	120.63
C5—C6—C7	119.1 (2)	C12—C17—C16	121.89 (18)

Table 1

Selected bond lengths (Å)

Zn1—Br1	2.3599 (3)
Zn1—Br2	2.3371 (3)
Zn1—N1	2.0662 (16)
Zn1—N2	2.0628 (16)