Dichloridobis(2-{1-[2-(1H-indol-3-yl)ethyl­iminio]eth­yl}phenolate-κO)zinc(II)–2-{1-[2-(1H-indol-3-yl)ethyl­iminio]eth­yl}phenolate (1/2)

Ali, H.M.; Mohamed Mustafa, M.I.; Rizal, M.R.; Ng, S.W.

doi:10.1107/S1600536808011161

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m718-m719

doi:10.1107/S1600536808011161

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Dichloridobis(2-{1-[2-(1H-indol-3-yl)ethyliminio]ethyl}phenolate-κO)zinc(II)–2-{1-[2-(1H-indol-3-yl)ethyliminio]ethyl}phenolate (1/2)

Hapipah M. Ali,^a Mohamed Ibrahim Mohamed Mustafa,^a Mohd. Razali Rizal ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 26 February 2008; accepted 20 April 2008; online 26 April 2008)

In the mononuclear complex molecule of the title compond, [ZnCl₂(C₁₈H₁₈N₂O)₂]·2C₁₈H₁₈N₂O, the Zn atom, which lies on a twofold rotation axis, is coordinated by phenolate O atoms in a tetrahedral coordination geometry. The coordinated Schiff base uses its indole NH donor site to form a hydrogen bond to the negatively charged phenolate O atom of the uncoordinated zwitterionic Schiff base. There is an intramolecular N—H⋯O hydrogen bond in the coordinated and uncoordinated Schiff bases. The indole NH site of the uncoordinated Schiff base does not engage in a hydrogen-bond interaction. The CH₂—CH₂ group in the uncoordinated Schiff base is disordered equally over two positions.

Related literature

For a related neutral Schiff base, see: Rodriguez et al. (1987 ). For a related but zwitterionic Schiff base, see: Ali et al. (2007 ). For zinc derivatives of such deprotonated Schiff bases, see: Ali et al. (2008 ); Chen et al. (2007 ).

Experimental

Crystal data

[ZnCl₂(C₁₈H₁₈N₂O)₂]·2C₁₈H₁₈N₂O
M_r = 1249.65
Monoclinic, C 2
a = 25.8073 (4) Å
b = 9.1754 (1) Å
c = 14.3265 (2) Å
β = 112.566 (1)°
V = 3132.67 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 295 (2) K
0.10 × 0.06 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.866, T_max = 0.974
36333 measured reflections
7190 independent reflections
6008 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.091
S = 1.00
7190 reflections
413 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ), 3669 Friedel pairs
Flack parameter: 0.000 (8)

Table 1
Selected geometric parameters (Å, °)

Zn1—O1	1.987 (2)
Zn1—Cl1	2.2260 (6)

O1—Zn1—O1ⁱ	99.84 (9)
O1—Zn1—Cl1	110.51 (5)
O1—Zn1—Cl1ⁱ	110.14 (5)
Cl1—Zn1—Cl1ⁱ	114.72 (3)
Symmetry code: (i) -x+1, y, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1	0.86 (1)	1.81 (2)	2.557 (3)	144 (3)
N2—H2n⋯O2	0.86 (1)	2.01 (1)	2.851 (3)	164 (3)
N3—H3n⋯O2	0.87 (1)	1.83 (3)	2.503 (4)	133 (4)
Symmetry codes: .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011161/sg2225sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011161/sg2225Isup2.hkl

checkCIF report

Comment top

The reaction of zinc acetate with 2-[2-(1H-indol-3-yl)ethyliminomethy]phenol, a neutral Schiff base (Rodriguez et al., 1987) furnishes the expected zinc complex with the deprotonated ligand in which the deprotonated ligand N,O-chelates to the metal center (Chen et al., 2007). Similarly, the reaction of zinc acetate with the 4-methyl substituted Schiff base (the methyl substituent is para to the negatively-charged phenoxy group) affords the corresponding tetrahdral zinc compound; the structure of the Schiff base itself is not known.

On the other hand, the 4-methyl substituted Schiff base of 2-[2-(1H-indol-3-yl)ethylimino-1-ethy]phenol exists in the zwitterionic form; the presence of methyl group on the imino –C=N– double-bond probably induces charge separation (Ali et al., 2007). 2-[2-(1H-Indol-3-yl)ethylimino-1-ethy]phenol in the title cocrystal is a zwitterionic species; it coordinates to zinc chloride, so that the coordination geometry at the metal center is an Cl₂O₂Zn tetraheron. The compound crystallizes as a cocrystal (Scheme I, Fig. 1). Both the coordinated and free zwitterionis have an intramolecular N···O hydrogen bond. The coordinated Schiff base uses its N–H_indolyl donor site to form a hydrogen bond to the negatively-charged phenolato-O atom of the free Schiff base. The N–H_indolyl site of the free Schiff base does not engage in a hydrogen-bonding interaction.

Related literature top

For a related neutral Schiff base, see: Rodriguez et al. (1987). F for a related but zwitterionic Schiff base, see: Ali et al. (20070. For zinc derivatives of such deprotonated Schiff bases, see: Ali et al. (2008); Chen et al. (2007).

Experimental top

The Schiff base was synthesized by condensing 2-(1H-indol-3-yl)ethylamine with 2-hydroxyacetophenone. The compound (0.50 g, 1.79 mmol) and zinc chloride (1.21 g, 0.89 mol) were heated in ethanol (10 ml) for an hour along with a small quantity (0.02 g) of sodium hydride. The compound was recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. Thermal ellipsoid plot of ZnCl₂(C₁₈H₁₈N₂O)₂^.2C₁₈H₁₈N₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radiius. The symmetry-related zwitterionic Schiff base is not shown. Dashed lines denote hydrogen bonds. The mononuclear molecule lies on a twofold rotation axis.

Dichloridobis(2-{1-[2-(1H-indol-3-yl)ethyliminio]ethyl}phenolate- κO)zinc(II)–2-{1-[2-(1H-indol-3-yl)ethyliminio]ethyl}phenolate (1/2) top

Crystal data top

[ZnCl₂(C₁₈H₁₈N₂O)₂]·2C₁₈H₁₈N₂O	F(000) = 1312
M_r = 1249.65	D_x = 1.325 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 8552 reflections
a = 25.8073 (4) Å	θ = 2.4–23.8°
b = 9.1754 (1) Å	µ = 0.54 mm⁻¹
c = 14.3265 (2) Å	T = 295 K
β = 112.566 (1)°	Irregular block, yellow
V = 3132.67 (7) Å³	0.10 × 0.06 × 0.05 mm
Z = 2

Data collection top

Bruker SMART APEXII diffractometer	7190 independent reflections
Radiation source: fine-focus sealed tube	6008 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −33→32
T_min = 0.866, T_max = 0.974	k = −11→11
36333 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0481P)² + 0.6205P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
7190 reflections	Δρ_max = 0.36 e Å⁻³
413 parameters	Δρ_min = −0.30 e Å⁻³
10 restraints	Absolute structure: Flack (1983), 3669 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.000 (8)

Crystal data top

[ZnCl₂(C₁₈H₁₈N₂O)₂]·2C₁₈H₁₈N₂O	V = 3132.67 (7) Å³
M_r = 1249.65	Z = 2
Monoclinic, C2	Mo Kα radiation
a = 25.8073 (4) Å	µ = 0.54 mm⁻¹
b = 9.1754 (1) Å	T = 295 K
c = 14.3265 (2) Å	0.10 × 0.06 × 0.05 mm
β = 112.566 (1)°

Data collection top

Bruker SMART APEXII diffractometer	7190 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6008 reflections with I > 2σ(I)
T_min = 0.866, T_max = 0.974	R_int = 0.039
36333 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	Δρ_max = 0.36 e Å⁻³
S = 1.00	Δρ_min = −0.30 e Å⁻³
7190 reflections	Absolute structure: Flack (1983), 3669 Friedel pairs
413 parameters	Absolute structure parameter: 0.000 (8)
10 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.5000	0.50003 (3)	0.0000	0.03995 (10)
Cl1	0.42528 (3)	0.63088 (6)	−0.09253 (5)	0.05459 (17)
O1	0.48035 (7)	0.36059 (16)	0.08739 (12)	0.0449 (4)
O2	0.42302 (10)	0.7684 (3)	0.31515 (19)	0.0846 (7)
N1	0.39707 (9)	0.1849 (2)	0.02989 (16)	0.0455 (5)
H1N	0.4136 (10)	0.2679 (17)	0.034 (2)	0.055*
N2	0.34836 (9)	0.5756 (2)	0.16913 (19)	0.0602 (6)
H2N	0.3665 (11)	0.646 (2)	0.2068 (19)	0.072*
N3	0.52785 (12)	0.7793 (3)	0.3958 (2)	0.0850 (9)
H3N	0.4975 (11)	0.731 (4)	0.388 (3)	0.102*
N4	0.67920 (12)	0.2805 (3)	0.5240 (2)	0.0729 (7)
H4N	0.6967 (13)	0.221 (3)	0.5714 (19)	0.087*
C1	0.51286 (10)	0.2466 (2)	0.12619 (16)	0.0387 (5)
C2	0.57066 (11)	0.2636 (3)	0.18025 (18)	0.0492 (6)
H2	0.5858	0.3570	0.1916	0.059*
C3	0.60560 (11)	0.1461 (3)	0.2170 (2)	0.0541 (6)
H3	0.6438	0.1611	0.2525	0.065*
C4	0.58430 (10)	0.0056 (4)	0.20174 (17)	0.0552 (6)
H4	0.6081	−0.0740	0.2250	0.066*
C5	0.52764 (11)	−0.0147 (3)	0.15191 (17)	0.0499 (6)
H5	0.5134	−0.1090	0.1424	0.060*
C6	0.49053 (10)	0.1031 (2)	0.11484 (16)	0.0386 (5)
C7	0.43083 (10)	0.0765 (3)	0.06467 (18)	0.0424 (6)
C8	0.40747 (13)	−0.0742 (3)	0.0536 (2)	0.0578 (7)
H8A	0.3680	−0.0695	0.0396	0.087*
H8B	0.4262	−0.1274	0.1151	0.087*
H8C	0.4132	−0.1226	−0.0011	0.087*
C9	0.33622 (11)	0.1796 (3)	−0.0260 (2)	0.0558 (7)
H9A	0.3186	0.1324	0.0148	0.067*
H9B	0.3277	0.1231	−0.0874	0.067*
C10	0.31327 (11)	0.3332 (3)	−0.0526 (2)	0.0588 (7)
H10A	0.3338	0.3826	−0.0877	0.071*
H10B	0.2742	0.3278	−0.0984	0.071*
C11	0.31755 (10)	0.4211 (3)	0.03838 (19)	0.0480 (6)
C12	0.35561 (10)	0.5266 (3)	0.0851 (2)	0.0553 (7)
H12	0.3828	0.5606	0.0629	0.066*
C13	0.28431 (9)	0.4020 (2)	0.09671 (18)	0.0446 (5)
C14	0.23988 (10)	0.3105 (3)	0.0911 (2)	0.0571 (7)
H14	0.2253	0.2449	0.0379	0.069*
C15	0.21779 (12)	0.3177 (4)	0.1644 (3)	0.0705 (9)
H15	0.1883	0.2565	0.1604	0.085*
C16	0.23887 (14)	0.4148 (4)	0.2439 (3)	0.0765 (10)
H16	0.2231	0.4177	0.2924	0.092*
C17	0.28259 (11)	0.5073 (4)	0.2531 (2)	0.0671 (7)
H17	0.2967	0.5719	0.3070	0.081*
C18	0.30495 (9)	0.5006 (3)	0.17897 (18)	0.0499 (5)
C19	0.42330 (12)	0.9098 (3)	0.31308 (19)	0.0585 (7)
C20	0.37283 (12)	0.9902 (5)	0.2698 (2)	0.0741 (9)
H20	0.3388	0.9407	0.2442	0.089*
C21	0.37302 (18)	1.1387 (5)	0.2649 (2)	0.0867 (12)
H21	0.3391	1.1882	0.2358	0.104*
C22	0.4216 (2)	1.2159 (5)	0.3016 (3)	0.0863 (12)
H22	0.4210	1.3170	0.2974	0.104*
C23	0.47149 (15)	1.1436 (3)	0.3450 (2)	0.0668 (8)
H23	0.5047	1.1968	0.3701	0.080*
C24	0.47389 (10)	0.9900 (4)	0.35243 (16)	0.0504 (6)
C25	0.52729 (12)	0.9180 (4)	0.3974 (2)	0.0599 (7)
C26	0.58061 (12)	1.0014 (6)	0.4431 (2)	0.0827 (9)
H26A	0.6118	0.9377	0.4533	0.124*
H26B	0.5834	1.0412	0.5069	0.124*
H26C	0.5810	1.0793	0.3986	0.124*
C27	0.5727 (6)	0.672 (2)	0.4535 (10)	0.089 (4)	0.50
H27A	0.6085	0.7217	0.4843	0.107*	0.50
H27B	0.5636	0.6270	0.5065	0.107*	0.50
C28	0.5756 (7)	0.560 (2)	0.3803 (13)	0.070 (3)	0.50
H28A	0.5819	0.6077	0.3251	0.084*	0.50
H28B	0.5401	0.5087	0.3524	0.084*	0.50
C27'	0.5826 (6)	0.7006 (19)	0.4208 (10)	0.089 (4)	0.50
H27C	0.6029	0.7411	0.3822	0.107*	0.50
H27D	0.6057	0.7110	0.4921	0.107*	0.50
C28'	0.5698 (6)	0.544 (2)	0.3950 (14)	0.070 (3)	0.50
H28C	0.5510	0.5343	0.3223	0.084*	0.50
H28D	0.5446	0.5093	0.4257	0.084*	0.50
C29	0.62217 (12)	0.4534 (3)	0.4312 (2)	0.0615 (7)
C30	0.63045 (14)	0.3544 (4)	0.5058 (2)	0.0734 (9)
H30	0.6065	0.3392	0.5394	0.088*
C31	0.66965 (11)	0.4438 (3)	0.40353 (18)	0.0511 (6)
C32	0.68572 (11)	0.5145 (3)	0.33287 (18)	0.0600 (7)
H32	0.6629	0.5859	0.2911	0.072*
C33	0.73566 (13)	0.4775 (4)	0.3255 (2)	0.0691 (8)
H33	0.7470	0.5266	0.2798	0.083*
C34	0.76939 (14)	0.3683 (4)	0.3852 (3)	0.0743 (9)
H34	0.8028	0.3447	0.3782	0.089*
C35	0.75462 (13)	0.2946 (3)	0.4541 (2)	0.0708 (9)
H35	0.7772	0.2211	0.4938	0.085*
C36	0.70474 (11)	0.3333 (3)	0.4627 (2)	0.0547 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.04012 (19)	0.02675 (16)	0.0496 (2)	0.000	0.01350 (16)	0.000
Cl1	0.0518 (4)	0.0378 (3)	0.0632 (4)	0.0119 (3)	0.0098 (3)	0.0003 (3)
O1	0.0435 (9)	0.0329 (7)	0.0567 (10)	−0.0008 (7)	0.0175 (8)	0.0039 (7)
O2	0.0729 (15)	0.0688 (15)	0.0839 (16)	−0.0066 (12)	−0.0012 (13)	−0.0150 (12)
N1	0.0477 (12)	0.0389 (10)	0.0508 (12)	−0.0063 (9)	0.0199 (10)	−0.0071 (9)
N2	0.0487 (12)	0.0463 (12)	0.0773 (16)	−0.0069 (10)	0.0150 (12)	−0.0127 (11)
N3	0.0659 (17)	0.0699 (18)	0.0893 (19)	0.0228 (14)	−0.0037 (15)	−0.0205 (15)
N4	0.0775 (18)	0.0613 (15)	0.0666 (17)	0.0077 (14)	0.0130 (14)	0.0143 (13)
C1	0.0482 (13)	0.0333 (11)	0.0359 (11)	−0.0014 (9)	0.0176 (10)	0.0008 (9)
C2	0.0507 (14)	0.0436 (12)	0.0486 (13)	−0.0034 (11)	0.0140 (11)	0.0014 (11)
C3	0.0478 (14)	0.0616 (16)	0.0481 (14)	0.0046 (12)	0.0132 (12)	0.0063 (12)
C4	0.0586 (14)	0.0498 (13)	0.0556 (13)	0.0180 (16)	0.0203 (11)	0.0127 (15)
C5	0.0703 (16)	0.0344 (12)	0.0517 (13)	0.0056 (13)	0.0310 (12)	0.0038 (11)
C6	0.0501 (13)	0.0326 (10)	0.0379 (11)	−0.0004 (10)	0.0223 (10)	−0.0021 (9)
C7	0.0588 (15)	0.0348 (12)	0.0398 (12)	−0.0054 (11)	0.0257 (11)	−0.0087 (10)
C8	0.0727 (19)	0.0385 (13)	0.0617 (16)	−0.0087 (13)	0.0255 (15)	−0.0106 (12)
C9	0.0436 (14)	0.0582 (16)	0.0607 (16)	−0.0075 (12)	0.0145 (12)	−0.0154 (13)
C10	0.0482 (15)	0.0677 (17)	0.0509 (15)	0.0049 (13)	0.0084 (12)	−0.0019 (13)
C11	0.0375 (12)	0.0447 (13)	0.0550 (14)	0.0059 (10)	0.0101 (11)	0.0052 (11)
C12	0.0438 (13)	0.0489 (17)	0.0743 (17)	−0.0022 (11)	0.0238 (12)	0.0045 (13)
C13	0.0348 (12)	0.0366 (11)	0.0531 (14)	0.0066 (9)	0.0066 (10)	0.0057 (10)
C14	0.0355 (13)	0.0498 (14)	0.0729 (18)	0.0018 (11)	0.0060 (13)	0.0089 (13)
C15	0.0380 (14)	0.075 (2)	0.095 (2)	0.0076 (14)	0.0222 (15)	0.0353 (19)
C16	0.0598 (19)	0.102 (3)	0.076 (2)	0.0266 (19)	0.0349 (17)	0.031 (2)
C17	0.0615 (16)	0.0736 (18)	0.0622 (15)	0.0206 (19)	0.0192 (13)	0.0061 (18)
C18	0.0412 (11)	0.0427 (10)	0.0610 (13)	0.0091 (13)	0.0144 (10)	0.0040 (14)
C19	0.0562 (16)	0.0687 (18)	0.0448 (14)	0.0091 (14)	0.0130 (13)	−0.0077 (13)
C20	0.0525 (15)	0.112 (3)	0.0531 (15)	0.023 (2)	0.0152 (12)	0.005 (2)
C21	0.091 (3)	0.113 (3)	0.0546 (19)	0.056 (3)	0.0264 (19)	0.016 (2)
C22	0.125 (4)	0.067 (2)	0.071 (2)	0.039 (2)	0.043 (3)	0.0180 (18)
C23	0.085 (2)	0.0625 (18)	0.0589 (17)	0.0018 (16)	0.0335 (16)	−0.0014 (14)
C24	0.0519 (13)	0.0588 (14)	0.0414 (11)	0.0137 (15)	0.0191 (10)	−0.0012 (13)
C25	0.0546 (16)	0.0717 (18)	0.0478 (14)	0.0089 (14)	0.0134 (12)	−0.0180 (13)
C26	0.0597 (17)	0.117 (3)	0.0654 (17)	−0.004 (2)	0.0172 (14)	−0.019 (2)
C27	0.092 (5)	0.085 (7)	0.060 (8)	0.042 (6)	−0.005 (4)	−0.012 (5)
C28	0.062 (3)	0.076 (4)	0.067 (5)	0.018 (3)	0.019 (2)	−0.008 (3)
C27'	0.092 (5)	0.085 (7)	0.060 (8)	0.042 (6)	−0.005 (4)	−0.012 (5)
C28'	0.062 (3)	0.076 (4)	0.067 (5)	0.018 (3)	0.019 (2)	−0.008 (3)
C29	0.0613 (17)	0.0576 (16)	0.0543 (15)	0.0111 (13)	0.0097 (13)	−0.0100 (12)
C30	0.070 (2)	0.075 (2)	0.072 (2)	−0.0018 (17)	0.0247 (17)	−0.0056 (17)
C31	0.0500 (14)	0.0413 (11)	0.0441 (13)	0.0061 (11)	−0.0018 (11)	−0.0081 (10)
C32	0.0681 (16)	0.0497 (14)	0.0455 (12)	0.0093 (15)	0.0032 (11)	−0.0018 (13)
C33	0.0711 (18)	0.070 (2)	0.0570 (15)	−0.0006 (16)	0.0145 (14)	−0.0038 (15)
C34	0.0569 (18)	0.079 (2)	0.076 (2)	0.0046 (16)	0.0129 (16)	−0.0055 (18)
C35	0.0528 (17)	0.0591 (17)	0.079 (2)	0.0162 (14)	0.0013 (15)	0.0040 (15)
C36	0.0544 (16)	0.0406 (14)	0.0524 (15)	0.0036 (12)	0.0019 (12)	0.0017 (11)

Geometric parameters (Å, º) top

Zn1—O1ⁱ	1.987 (2)	C15—C16	1.383 (5)
Zn1—O1	1.987 (2)	C15—H15	0.9300
Zn1—Cl1ⁱ	2.2260 (6)	C16—C17	1.377 (5)
Zn1—Cl1	2.2260 (6)	C16—H16	0.9300
O1—C1	1.323 (3)	C17—C18	1.391 (3)
O2—C19	1.298 (4)	C17—H17	0.9300
N1—C7	1.290 (3)	C19—C24	1.414 (4)
N1—C9	1.464 (3)	C19—C20	1.416 (4)
N1—H1N	0.86 (1)	C20—C21	1.365 (6)
N2—C12	1.363 (4)	C20—H20	0.9300
N2—C18	1.367 (3)	C21—C22	1.358 (6)
N2—H2N	0.86 (1)	C21—H21	0.9300
N3—C25	1.273 (4)	C22—C23	1.367 (5)
N3—C27	1.500 (7)	C22—H22	0.9300
N3—C27'	1.502 (7)	C23—C24	1.413 (4)
N3—H3N	0.87 (1)	C23—H23	0.9300
N4—C30	1.364 (4)	C24—C25	1.438 (4)
N4—C36	1.373 (4)	C25—C26	1.489 (5)
N4—H4N	0.86 (1)	C26—H26A	0.9600
C1—C2	1.401 (3)	C26—H26B	0.9600
C1—C6	1.421 (3)	C26—H26C	0.9600
C2—C3	1.374 (4)	C27—C28	1.491 (9)
C2—H2	0.9300	C27—H27A	0.9700
C3—C4	1.386 (4)	C27—H27B	0.9700
C3—H3	0.9300	C28—C29	1.506 (8)
C4—C5	1.372 (3)	C28—H28A	0.9700
C4—H4	0.9300	C28—H28B	0.9700
C5—C6	1.406 (3)	C27'—C28'	1.485 (9)
C5—H5	0.9300	C27'—H27C	0.9700
C6—C7	1.449 (3)	C27'—H27D	0.9700
C7—C8	1.492 (3)	C28'—C29	1.502 (8)
C8—H8A	0.9600	C28'—H28C	0.9700
C8—H8B	0.9600	C28'—H28D	0.9700
C8—H8C	0.9600	C29—C30	1.355 (4)
C9—C10	1.520 (4)	C29—C31	1.428 (4)
C9—H9A	0.9700	C30—H30	0.9300
C9—H9B	0.9700	C31—C32	1.392 (4)
C10—C11	1.500 (4)	C31—C36	1.406 (3)
C10—H10A	0.9700	C32—C33	1.375 (4)
C10—H10B	0.9700	C32—H32	0.9300
C11—C12	1.358 (3)	C33—C34	1.386 (4)
C11—C13	1.420 (4)	C33—H33	0.9300
C12—H12	0.9300	C34—C35	1.365 (5)
C13—C14	1.398 (3)	C34—H34	0.9300
C13—C18	1.418 (4)	C35—C36	1.386 (4)
C14—C15	1.374 (4)	C35—H35	0.9300
C14—H14	0.9300

O1—Zn1—O1ⁱ	99.84 (9)	N2—C18—C17	130.8 (3)
O1—Zn1—Cl1	110.51 (5)	N2—C18—C13	107.3 (2)
O1ⁱ—Zn1—Cl1ⁱ	110.51 (5)	C17—C18—C13	122.0 (3)
O1—Zn1—Cl1ⁱ	110.14 (5)	O2—C19—C24	121.6 (3)
O1ⁱ—Zn1—Cl1	110.14 (5)	O2—C19—C20	121.2 (3)
Cl1—Zn1—Cl1ⁱ	114.72 (3)	C24—C19—C20	117.2 (3)
C1—O1—Zn1	120.01 (14)	C21—C20—C19	121.5 (4)
C7—N1—C9	127.5 (2)	C21—C20—H20	119.3
C7—N1—H1N	114 (2)	C19—C20—H20	119.3
C9—N1—H1N	118 (2)	C20—C21—C22	121.4 (3)
C12—N2—C18	108.7 (2)	C20—C21—H21	119.3
C12—N2—H2N	125 (2)	C22—C21—H21	119.3
C18—N2—H2N	126 (2)	C21—C22—C23	119.5 (4)
C25—N3—C27	130.9 (9)	C21—C22—H22	120.3
C25—N3—C27'	119.5 (9)	C23—C22—H22	120.3
C27—N3—C27'	25.6 (9)	C22—C23—C24	121.6 (3)
C25—N3—H3N	120 (3)	C22—C23—H23	119.2
C27—N3—H3N	102 (3)	C24—C23—H23	119.2
C27'—N3—H3N	121 (3)	C19—C24—C23	118.8 (3)
C30—N4—C36	109.6 (3)	C19—C24—C25	121.3 (3)
C30—N4—H4N	130 (2)	C23—C24—C25	119.9 (3)
C36—N4—H4N	120 (2)	N3—C25—C24	117.8 (3)
O1—C1—C2	120.9 (2)	N3—C25—C26	120.5 (3)
O1—C1—C6	121.4 (2)	C24—C25—C26	121.7 (3)
C2—C1—C6	117.8 (2)	C25—C26—H26A	109.5
C3—C2—C1	121.8 (2)	C25—C26—H26B	109.5
C3—C2—H2	119.1	H26A—C26—H26B	109.5
C1—C2—H2	119.1	C25—C26—H26C	109.5
C2—C3—C4	120.5 (2)	H26A—C26—H26C	109.5
C2—C3—H3	119.8	H26B—C26—H26C	109.5
C4—C3—H3	119.8	C28—C27—N3	107.4 (8)
C5—C4—C3	119.2 (3)	C28—C27—H27A	110.2
C5—C4—H4	120.4	N3—C27—H27A	110.2
C3—C4—H4	120.4	C28—C27—H27B	110.2
C4—C5—C6	121.9 (3)	N3—C27—H27B	110.2
C4—C5—H5	119.1	H27A—C27—H27B	108.5
C6—C5—H5	119.1	C27—C28—C29	110.8 (10)
C5—C6—C1	118.8 (2)	C27—C28—H28A	109.5
C5—C6—C7	119.9 (2)	C29—C28—H28A	109.5
C1—C6—C7	121.3 (2)	C27—C28—H28B	109.5
N1—C7—C6	119.6 (2)	C29—C28—H28B	109.5
N1—C7—C8	119.2 (2)	H28A—C28—H28B	108.1
C6—C7—C8	121.2 (2)	C28'—C27'—N3	107.8 (10)
C7—C8—H8A	109.5	C28'—C27'—H27C	110.2
C7—C8—H8B	109.5	N3—C27'—H27C	110.2
H8A—C8—H8B	109.5	C28'—C27'—H27D	110.2
C7—C8—H8C	109.5	N3—C27'—H27D	110.2
H8A—C8—H8C	109.5	H27C—C27'—H27D	108.5
H8B—C8—H8C	109.5	C27'—C28'—C29	111.4 (11)
N1—C9—C10	109.8 (2)	C27'—C28'—H28C	109.3
N1—C9—H9A	109.7	C29—C28'—H28C	109.3
C10—C9—H9A	109.7	C27'—C28'—H28D	109.3
N1—C9—H9B	109.7	C29—C28'—H28D	109.3
C10—C9—H9B	109.7	H28C—C28'—H28D	108.0
H9A—C9—H9B	108.2	C30—C29—C31	106.5 (3)
C11—C10—C9	112.9 (2)	C30—C29—C28	132.3 (8)
C11—C10—H10A	109.0	C31—C29—C28	121.1 (8)
C9—C10—H10A	109.0	C30—C29—C28'	119.6 (8)
C11—C10—H10B	109.0	C31—C29—C28'	133.9 (8)
C9—C10—H10B	109.0	C28—C29—C28'	12.8 (15)
H10A—C10—H10B	107.8	C29—C30—N4	109.8 (3)
C12—C11—C13	106.5 (2)	C29—C30—H30	125.1
C12—C11—C10	127.6 (3)	N4—C30—H30	125.1
C13—C11—C10	125.8 (2)	C32—C31—C36	118.1 (3)
C11—C12—N2	110.6 (2)	C32—C31—C29	134.4 (2)
C11—C12—H12	124.7	C36—C31—C29	107.5 (3)
N2—C12—H12	124.7	C33—C32—C31	119.4 (3)
C14—C13—C18	118.0 (2)	C33—C32—H32	120.3
C14—C13—C11	135.1 (2)	C31—C32—H32	120.3
C18—C13—C11	106.9 (2)	C32—C33—C34	121.1 (3)
C15—C14—C13	119.9 (3)	C32—C33—H33	119.5
C15—C14—H14	120.0	C34—C33—H33	119.5
C13—C14—H14	120.0	C35—C34—C33	121.3 (3)
C14—C15—C16	120.8 (3)	C35—C34—H34	119.3
C14—C15—H15	119.6	C33—C34—H34	119.3
C16—C15—H15	119.6	C34—C35—C36	117.6 (3)
C17—C16—C15	121.6 (3)	C34—C35—H35	121.2
C17—C16—H16	119.2	C36—C35—H35	121.2
C15—C16—H16	119.2	N4—C36—C35	131.0 (3)
C16—C17—C18	117.7 (3)	N4—C36—C31	106.5 (2)
C16—C17—H17	121.2	C35—C36—C31	122.5 (3)
C18—C17—H17	121.2

O1ⁱ—Zn1—O1—C1	44.94 (13)	C21—C22—C23—C24	0.1 (5)
Cl1ⁱ—Zn1—O1—C1	−71.31 (16)	O2—C19—C24—C23	178.0 (3)
Cl1—Zn1—O1—C1	160.91 (14)	C20—C19—C24—C23	−1.1 (4)
Zn1—O1—C1—C2	52.2 (3)	O2—C19—C24—C25	−0.6 (4)
Zn1—O1—C1—C6	−127.91 (18)	C20—C19—C24—C25	−179.7 (2)
O1—C1—C2—C3	−176.8 (2)	C22—C23—C24—C19	0.6 (4)
C6—C1—C2—C3	3.3 (4)	C22—C23—C24—C25	179.2 (3)
C1—C2—C3—C4	−0.2 (4)	C27—N3—C25—C24	−165.0 (6)
C2—C3—C4—C5	−1.9 (4)	C27'—N3—C25—C24	166.8 (6)
C3—C4—C5—C6	0.7 (4)	C27—N3—C25—C26	15.9 (8)
C4—C5—C6—C1	2.4 (3)	C27'—N3—C25—C26	−12.3 (7)
C4—C5—C6—C7	−178.6 (2)	C19—C24—C25—N3	3.7 (4)
O1—C1—C6—C5	175.8 (2)	C23—C24—C25—N3	−174.9 (3)
C2—C1—C6—C5	−4.3 (3)	C19—C24—C25—C26	−177.3 (2)
O1—C1—C6—C7	−3.1 (3)	C23—C24—C25—C26	4.2 (4)
C2—C1—C6—C7	176.7 (2)	C25—N3—C27—C28	−135.0 (9)
C9—N1—C7—C6	177.4 (2)	C27'—N3—C27—C28	−63 (3)
C9—N1—C7—C8	−3.4 (4)	N3—C27—C28—C29	176.6 (14)
C5—C6—C7—N1	−179.3 (2)	C25—N3—C27'—C28'	−169.8 (9)
C1—C6—C7—N1	−0.3 (3)	C27—N3—C27'—C28'	66 (4)
C5—C6—C7—C8	1.5 (4)	N3—C27'—C28'—C29	−171.8 (10)
C1—C6—C7—C8	−179.5 (2)	C27—C28—C29—C30	64.7 (16)
C7—N1—C9—C10	−179.8 (2)	C27—C28—C29—C31	−114.6 (11)
N1—C9—C10—C11	−67.5 (3)	C27—C28—C29—C28'	69 (7)
C9—C10—C11—C12	102.8 (3)	C27'—C28'—C29—C30	113.1 (11)
C9—C10—C11—C13	−72.5 (3)	C27'—C28'—C29—C31	−67.4 (16)
C13—C11—C12—N2	−0.2 (3)	C27'—C28'—C29—C28	−64 (7)
C10—C11—C12—N2	−176.2 (2)	C31—C29—C30—N4	−2.0 (3)
C18—N2—C12—C11	0.5 (3)	C28—C29—C30—N4	178.6 (12)
C12—C11—C13—C14	−178.4 (3)	C28'—C29—C30—N4	177.6 (10)
C10—C11—C13—C14	−2.3 (4)	C36—N4—C30—C29	1.6 (4)
C12—C11—C13—C18	−0.1 (3)	C30—C29—C31—C32	179.5 (3)
C10—C11—C13—C18	176.0 (2)	C28—C29—C31—C32	−1.0 (11)
C18—C13—C14—C15	−0.3 (3)	C28'—C29—C31—C32	0.0 (13)
C11—C13—C14—C15	177.8 (3)	C30—C29—C31—C36	1.6 (3)
C13—C14—C15—C16	0.1 (4)	C28—C29—C31—C36	−178.9 (10)
C14—C15—C16—C17	−0.2 (4)	C28'—C29—C31—C36	−177.9 (12)
C15—C16—C17—C18	0.3 (4)	C36—C31—C32—C33	−2.0 (4)
C12—N2—C18—C17	177.8 (3)	C29—C31—C32—C33	−179.8 (3)
C12—N2—C18—C13	−0.5 (3)	C31—C32—C33—C34	1.9 (4)
C16—C17—C18—N2	−178.6 (3)	C32—C33—C34—C35	−0.7 (5)
C16—C17—C18—C13	−0.5 (4)	C33—C34—C35—C36	−0.3 (5)
C14—C13—C18—N2	179.0 (2)	C30—N4—C36—C35	179.4 (3)
C11—C13—C18—N2	0.4 (3)	C30—N4—C36—C31	−0.6 (3)
C14—C13—C18—C17	0.5 (4)	C34—C35—C36—N4	−179.9 (3)
C11—C13—C18—C17	−178.1 (2)	C34—C35—C36—C31	0.1 (4)
O2—C19—C20—C21	−178.1 (3)	C32—C31—C36—N4	−179.0 (2)
C24—C19—C20—C21	0.9 (4)	C29—C31—C36—N4	−0.6 (3)
C19—C20—C21—C22	−0.2 (5)	C32—C31—C36—C35	1.1 (4)
C20—C21—C22—C23	−0.3 (5)	C29—C31—C36—C35	179.4 (3)

Symmetry code: (i) −x+1, y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1	0.86 (1)	1.81 (2)	2.557 (3)	144 (3)
N2—H2n···O2	0.86 (1)	2.01 (1)	2.851 (3)	164 (3)
N3—H3n···O2	0.87 (1)	1.83 (3)	2.503 (4)	133 (4)

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₈H₁₈N₂O)₂]·2C₁₈H₁₈N₂O
M_r	1249.65
Crystal system, space group	Monoclinic, C2
Temperature (K)	295
a, b, c (Å)	25.8073 (4), 9.1754 (1), 14.3265 (2)
β (°)	112.566 (1)
V (Å³)	3132.67 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.10 × 0.06 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.866, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	36333, 7190, 6008
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.091, 1.00
No. of reflections	7190
No. of parameters	413
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.30
Absolute structure	Flack (1983), 3669 Friedel pairs
Absolute structure parameter	0.000 (8)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected geometric parameters (Å, º) top

Zn1—O1	1.987 (2)	Zn1—Cl1	2.2260 (6)

O1—Zn1—O1ⁱ	99.84 (9)	O1—Zn1—Cl1ⁱ	110.14 (5)
O1—Zn1—Cl1	110.51 (5)	Cl1—Zn1—Cl1ⁱ	114.72 (3)

Symmetry code: (i) −x+1, y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1	0.86 (1)	1.81 (2)	2.557 (3)	144 (3)
N2—H2n···O2	0.86 (1)	2.01 (1)	2.851 (3)	164 (3)
N3—H3n···O2	0.87 (1)	1.83 (3)	2.503 (4)	133 (4)

Acknowledgements

We thank the Science Fund (12–02-03–2031) for supporting this study, and the University of Malaya for the purchase of the diffractometer.

References

Ali, H. M., Emmy Maryati, O. & Ng, S. W. (2007). Acta Cryst. E63, o3458. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m421. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, J., Xu, X.-Y., Gao, J., Li, Y.-H. & Xu, G.-X. (2007). Chin. J. Struct. Chem. 26, 632–636. CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rodriguez, M. L., Medina de la Rosa, E., Gili, P., Zarza, P. M., Reyes, M. G. M., Medina, A. & Díaz González, M. C. (1987). Acta Cryst. C43, 134–136. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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Volume 64| Part 5| May 2008| Pages m718-m719

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­chloridobis(2-{1-[2-(1H-indol-3-yl)ethyl­iminio]eth­yl}phenolate-κO)zinc(II)–2-{1-[2-(1H-indol-3-yl)ethyl­iminio]eth­yl}phenolate (1/2)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Dichloridobis(2-{1-[2-(1H-indol-3-yl)ethyliminio]ethyl}phenolate-κO)zinc(II)–2-{1-[2-(1H-indol-3-yl)ethyliminio]ethyl}phenolate (1/2)