Bis{4-chloro-2-[2-(1H-indol-3-yl)ethyl-imino-meth-yl]phenolato-κN,O}zinc(II).

The Zn atom in the title compound, [Zn(C(17)H(14)ClN(2)O)(2)], is N,O-chelated by two deprotonated Schiff base monoanionic ligands in a tetra-hedral coordination geometry. The Zn atom lies on a special position of site symmetry 2.

Related literature

For the structure of the unsubstituted [(C17H15N2O)2Zn], see Chen et al. (2007 ▶); Ng (2008 ▶).

Experimental

Crystal data

[Zn(C17H14ClN2O)2]

M = 660.87

Monoclinic,

a = 25.8989 (3) Å

b = 5.4960 (1) Å

c = 20.6138 (3) Å

β = 91.801 (1)°

V = 2932.73 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.06 mm−1

T = 128 (2) K

0.50 × 0.30 × 0.17 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.714, T max = 0.840

17664 measured reflections

3352 independent reflections

3023 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.100

S = 1.21

3352 reflections

251 parameters

14 restraints

All H-atom parameters refined

Δρmax = 0.55 e Å−3

Δρmin = −0.56 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002213/hg2370sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002213/hg2370Isup2.hkl

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

[Zn(C17H14ClN2O)2]	F(000) = 1360
Mr = 660.87	Dx = 1.497 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9956 reflections
a = 25.8989 (3) Å	θ = 2.5–31.2°
b = 5.4960 (1) Å	µ = 1.06 mm−1
c = 20.6138 (3) Å	T = 128 K
β = 91.801 (1)°	Block, colorless
V = 2932.73 (8) Å3	0.50 × 0.30 × 0.17 mm
Z = 4

Bruker APEXII diffractometer	3352 independent reflections
Radiation source: medium-focus sealed tube	3023 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −33→33
Tmin = 0.714, Tmax = 0.840	k = −6→7
17664 measured reflections	l = −26→26

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	All H-atom parameters refined
S = 1.21	w = 1/[σ2(Fo2) + (0.0632P)2 + 1.1156P] where P = (Fo2 + 2Fc2)/3
3352 reflections	(Δ/σ)max = 0.001
251 parameters	Δρmax = 0.55 e Å−3
14 restraints	Δρmin = −0.56 e Å−3

	x	y	z	Uiso*/Ueq
Zn1	0.5000	0.49480 (5)	0.7500	0.01823 (11)
Cl1	0.39490 (2)	0.33657 (10)	0.42675 (2)	0.03469 (14)
O1	0.46240 (5)	0.6771 (2)	0.68555 (6)	0.0256 (3)
N1	0.53085 (5)	0.2579 (3)	0.68736 (6)	0.0167 (3)
C1	0.45075 (6)	0.5975 (3)	0.62688 (7)	0.0175 (3)
N2	0.71557 (6)	−0.2875 (3)	0.76815 (7)	0.0235 (3)
C2	0.41428 (7)	0.7308 (3)	0.58836 (8)	0.0226 (3)
C3	0.39787 (7)	0.6548 (3)	0.52766 (8)	0.0230 (3)
C4	0.41765 (7)	0.4409 (4)	0.50234 (8)	0.0216 (3)
C5	0.45433 (7)	0.3096 (3)	0.53648 (8)	0.0206 (3)
C6	0.47188 (6)	0.3836 (3)	0.59882 (7)	0.0167 (3)
C7	0.51092 (6)	0.2301 (3)	0.63013 (8)	0.0181 (3)
C8	0.56967 (6)	0.0809 (3)	0.71064 (8)	0.0186 (3)
C9	0.62386 (7)	0.1885 (4)	0.70984 (11)	0.0305 (4)
C10	0.66211 (7)	0.0247 (3)	0.74448 (10)	0.0233 (4)
C11	0.68435 (7)	−0.1805 (3)	0.72056 (9)	0.0245 (4)
C12	0.68028 (6)	0.0477 (3)	0.81090 (9)	0.0209 (3)
C13	0.67219 (7)	0.2182 (4)	0.86012 (10)	0.0296 (4)
C15	0.69689 (9)	0.1852 (4)	0.91969 (10)	0.0359 (5)
C16	0.72995 (9)	−0.0135 (4)	0.93160 (11)	0.0344 (5)
C17	0.73904 (7)	−0.1845 (4)	0.88415 (9)	0.0279 (4)
C18	0.71359 (6)	−0.1517 (3)	0.82397 (8)	0.0205 (3)
H2N	0.7331 (9)	−0.421 (3)	0.7639 (13)	0.042 (7)*
H2	0.3996 (9)	0.884 (3)	0.6056 (11)	0.036 (6)*
H3	0.3712 (7)	0.753 (4)	0.5031 (10)	0.033 (6)*
H5	0.4670 (8)	0.155 (3)	0.5170 (11)	0.036 (6)*
H7	0.5240 (7)	0.097 (3)	0.6024 (8)	0.017 (5)*
H81	0.5617 (8)	0.033 (3)	0.7554 (6)	0.018 (5)*
H82	0.5676 (9)	−0.067 (3)	0.6831 (10)	0.028 (5)*
H91	0.6237 (11)	0.351 (3)	0.7316 (12)	0.052 (8)*
H92	0.6344 (10)	0.217 (5)	0.6640 (6)	0.048 (8)*
H11	0.6818 (9)	−0.251 (4)	0.6764 (6)	0.034 (6)*
H13	0.6501 (8)	0.365 (3)	0.8521 (11)	0.038 (6)*
H15	0.6893 (9)	0.299 (4)	0.9553 (9)	0.037 (6)*
H16	0.7477 (10)	−0.026 (5)	0.9748 (8)	0.045 (8)*
H17	0.7634 (8)	−0.323 (3)	0.8917 (12)	0.041 (7)*

	U11	U22	U33	U12	U13	U23
Zn1	0.02395 (17)	0.01667 (17)	0.01391 (15)	0.000	−0.00209 (10)	0.000
Cl1	0.0418 (3)	0.0423 (3)	0.0191 (2)	0.0051 (2)	−0.01249 (18)	−0.00457 (18)
O1	0.0394 (7)	0.0195 (6)	0.0173 (6)	0.0091 (5)	−0.0061 (5)	−0.0035 (5)
N1	0.0163 (6)	0.0165 (7)	0.0174 (6)	0.0011 (5)	−0.0005 (5)	0.0026 (5)
C1	0.0215 (7)	0.0158 (8)	0.0153 (7)	0.0005 (6)	−0.0003 (6)	0.0006 (6)
N2	0.0211 (7)	0.0231 (8)	0.0262 (7)	0.0056 (6)	−0.0016 (6)	−0.0016 (6)
C2	0.0264 (9)	0.0193 (8)	0.0222 (8)	0.0065 (7)	0.0000 (6)	0.0018 (6)
C3	0.0227 (8)	0.0247 (9)	0.0212 (8)	0.0039 (7)	−0.0029 (6)	0.0072 (7)
C4	0.0236 (8)	0.0268 (8)	0.0142 (7)	−0.0009 (7)	−0.0026 (6)	−0.0005 (6)
C5	0.0231 (8)	0.0214 (8)	0.0172 (7)	0.0029 (6)	−0.0001 (6)	−0.0021 (6)
C6	0.0185 (7)	0.0168 (8)	0.0148 (7)	0.0013 (6)	−0.0005 (5)	0.0007 (6)
C7	0.0186 (7)	0.0173 (8)	0.0186 (7)	0.0030 (6)	0.0006 (6)	−0.0001 (6)
C8	0.0183 (7)	0.0173 (8)	0.0201 (7)	0.0020 (6)	−0.0025 (6)	0.0032 (6)
C9	0.0186 (8)	0.0281 (10)	0.0444 (11)	−0.0022 (7)	−0.0044 (7)	0.0164 (9)
C10	0.0154 (7)	0.0226 (9)	0.0319 (10)	−0.0029 (6)	−0.0015 (7)	0.0075 (7)
C11	0.0206 (8)	0.0281 (9)	0.0246 (8)	−0.0026 (7)	−0.0040 (6)	0.0022 (7)
C12	0.0152 (7)	0.0179 (8)	0.0298 (9)	−0.0013 (6)	0.0030 (6)	0.0036 (7)
C13	0.0264 (9)	0.0199 (9)	0.0431 (11)	−0.0029 (7)	0.0094 (8)	−0.0036 (8)
C15	0.0408 (11)	0.0315 (11)	0.0359 (10)	−0.0118 (9)	0.0098 (8)	−0.0126 (9)
C16	0.0399 (11)	0.0382 (12)	0.0249 (10)	−0.0122 (8)	−0.0022 (8)	0.0001 (8)
C17	0.0265 (9)	0.0293 (10)	0.0275 (9)	−0.0020 (7)	−0.0043 (7)	0.0047 (7)
C18	0.0179 (7)	0.0194 (8)	0.0241 (8)	−0.0010 (6)	0.0010 (6)	0.0018 (6)

Zn1—O1	1.907 (1)	C7—H7	0.994 (9)
Zn1—O1i	1.907 (1)	C8—C9	1.523 (2)
Zn1—N1	2.016 (1)	C8—H81	0.989 (9)
Zn1—N1i	2.016 (1)	C8—H82	0.994 (10)
Cl1—C4	1.745 (2)	C9—C10	1.502 (2)
O1—C1	1.312 (2)	C9—H91	0.998 (10)
N1—C7	1.282 (2)	C9—H92	1.004 (10)
N1—C8	1.469 (2)	C10—C11	1.366 (3)
C1—C2	1.419 (2)	C10—C12	1.439 (3)
C1—C6	1.427 (2)	C11—H11	0.990 (10)
N2—C18	1.374 (2)	C12—C13	1.402 (3)
N2—C11	1.383 (2)	C12—C18	1.415 (2)
N2—H2N	0.870 (10)	C13—C15	1.379 (3)
C2—C3	1.374 (2)	C13—H13	0.998 (10)
C2—H2	0.994 (10)	C15—C16	1.405 (3)
C3—C4	1.391 (3)	C15—H15	0.990 (10)
C3—H3	1.001 (10)	C16—C17	1.382 (3)
C4—C5	1.370 (2)	C16—H16	0.992 (10)
C5—C6	1.410 (2)	C17—C18	1.398 (2)
C5—H5	0.999 (10)	C17—H17	0.996 (10)
C6—C7	1.453 (2)
O1—Zn1—O1i	116.62 (8)	N1—C8—H81	108.7 (12)
O1—Zn1—N1	95.57 (5)	C9—C8—H81	109.5 (12)
O1—Zn1—N1i	125.55 (6)	N1—C8—H82	109.4 (14)
O1i—Zn1—N1	125.55 (6)	C9—C8—H82	110.3 (13)
O1i—Zn1—N1i	95.57 (5)	H81—C8—H82	107.8 (18)
N1—Zn1—N1i	99.56 (8)	C10—C9—C8	110.87 (15)
C1—O1—Zn1	124.38 (11)	C10—C9—H91	109.5 (17)
C7—N1—C8	118.25 (14)	C8—C9—H91	109.0 (16)
C7—N1—Zn1	120.68 (11)	C10—C9—H92	110.3 (16)
C8—N1—Zn1	119.96 (10)	C8—C9—H92	110.3 (15)
O1—C1—C2	118.25 (15)	H91—C9—H92	107 (2)
O1—C1—C6	124.63 (15)	C11—C10—C12	106.68 (16)
C2—C1—C6	117.12 (14)	C11—C10—C9	127.04 (19)
C18—N2—C11	109.06 (15)	C12—C10—C9	126.20 (17)
C18—N2—H2N	125.3 (18)	C10—C11—N2	109.81 (16)
C11—N2—H2N	125.7 (18)	C10—C11—H11	129.7 (14)
C3—C2—C1	122.28 (16)	N2—C11—H11	120.4 (14)
C3—C2—H2	118.2 (14)	C13—C12—C18	118.94 (17)
C1—C2—H2	119.6 (14)	C13—C12—C10	134.06 (17)
C2—C3—C4	119.47 (15)	C18—C12—C10	106.99 (15)
C2—C3—H3	119.0 (14)	C15—C13—C12	118.76 (19)
C4—C3—H3	121.5 (14)	C15—C13—H13	120.0 (14)
C5—C4—C3	120.68 (16)	C12—C13—H13	121.2 (14)
C5—C4—Cl1	119.65 (14)	C13—C15—C16	121.40 (19)
C3—C4—Cl1	119.66 (13)	C13—C15—H15	118.7 (15)
C4—C5—C6	120.98 (16)	C16—C15—H15	119.8 (15)
C4—C5—H5	118.2 (14)	C17—C16—C15	121.4 (2)
C6—C5—H5	120.8 (14)	C17—C16—H16	120.4 (16)
C5—C6—C1	119.38 (14)	C15—C16—H16	118.2 (16)
C5—C6—C7	115.93 (14)	C16—C17—C18	117.02 (18)
C1—C6—C7	124.69 (14)	C16—C17—H17	121.9 (15)
N1—C7—C6	126.44 (15)	C18—C17—H17	121.1 (15)
N1—C7—H7	118.8 (12)	N2—C18—C17	130.10 (17)
C6—C7—H7	114.6 (12)	N2—C18—C12	107.45 (15)
N1—C8—C9	111.15 (14)	C17—C18—C12	122.43 (17)
O1i—Zn1—O1—C1	153.77 (15)	C1—C6—C7—N1	2.3 (3)
N1—Zn1—O1—C1	19.16 (14)	C7—N1—C8—C9	104.80 (18)
N1i—Zn1—O1—C1	−86.78 (15)	Zn1—N1—C8—C9	−87.15 (16)
O1—Zn1—N1—C7	−18.84 (14)	N1—C8—C9—C10	169.91 (16)
O1i—Zn1—N1—C7	−147.38 (12)	C8—C9—C10—C11	79.8 (2)
N1i—Zn1—N1—C7	108.67 (14)	C8—C9—C10—C12	−96.6 (2)
O1—Zn1—N1—C8	173.41 (12)	C12—C10—C11—N2	−0.1 (2)
O1i—Zn1—N1—C8	44.87 (14)	C9—C10—C11—N2	−177.12 (16)
N1i—Zn1—N1—C8	−59.09 (10)	C18—N2—C11—C10	0.3 (2)
Zn1—O1—C1—C2	167.80 (12)	C11—C10—C12—C13	178.99 (19)
Zn1—O1—C1—C6	−11.6 (2)	C9—C10—C12—C13	−4.0 (3)
O1—C1—C2—C3	−176.76 (17)	C11—C10—C12—C18	−0.05 (19)
C6—C1—C2—C3	2.7 (3)	C9—C10—C12—C18	176.96 (16)
C1—C2—C3—C4	−0.4 (3)	C18—C12—C13—C15	−0.2 (3)
C2—C3—C4—C5	−1.9 (3)	C10—C12—C13—C15	−179.14 (19)
C2—C3—C4—Cl1	177.25 (14)	C12—C13—C15—C16	0.4 (3)
C3—C4—C5—C6	1.8 (3)	C13—C15—C16—C17	−0.1 (3)
Cl1—C4—C5—C6	−177.31 (13)	C15—C16—C17—C18	−0.4 (3)
C4—C5—C6—C1	0.5 (3)	C11—N2—C18—C17	−178.80 (18)
C4—C5—C6—C7	−179.84 (16)	C11—N2—C18—C12	−0.31 (19)
O1—C1—C6—C5	176.72 (16)	C16—C17—C18—N2	178.95 (18)
C2—C1—C6—C5	−2.7 (2)	C16—C17—C18—C12	0.7 (3)
O1—C1—C6—C7	−2.9 (3)	C13—C12—C18—N2	−178.99 (16)
C2—C1—C6—C7	177.69 (15)	C10—C12—C18—N2	0.22 (19)
C8—N1—C7—C6	179.43 (15)	C13—C12—C18—C17	−0.4 (3)
Zn1—N1—C7—C6	11.5 (2)	C10—C12—C18—C17	178.85 (16)
C5—C6—C7—N1	−177.31 (16)

Zn1—O1	1.907 (1)
Zn1—N1	2.016 (1)

O1—Zn1—O1i	116.62 (8)
O1—Zn1—N1	95.57 (5)
O1—Zn1—N1i	125.55 (6)
N1—Zn1—N1i	99.56 (8)

Symmetry code: (i) .