A triclinic polymorph of dichlorido(2-{[2-(isopropyl­ammonio)­eth­yl]imino­methyl-κN}-5-meth­oxy­phenolato-κO1)zinc

Pei, A.-T.

doi:10.1107/S1600536812014341

metal-organic compounds

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Volume 68| Part 5| May 2012| Page m587

doi:10.1107/S1600536812014341

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A triclinic polymorph of dichlorido(2-{[2-(isopropylammonio)ethyl]iminomethyl-κN}-5-methoxyphenolato-κO¹)zinc

Ai-Tian Pei ^a ^*

^aZibo Vocational Institute, Zibo 255314, People's Republic of China
^*Correspondence e-mail: aitianpei@126.com

(Received 29 March 2012; accepted 3 April 2012; online 13 April 2012)

The title compound, [ZnCl₂(C₁₃H₂₀N₂O₂)], was first reported in the monoclinic space group P2₁/n [Han et al. (2010 ). Acta Cryst. E66, m469]. This investigation reveals a triclinic polymorph in the space group P-1 with an asymmetric unit that contains two independent molecules of the mononuclear zinc(II) complex. In each molecule, the Zn^II atoms are coordinated in a bidentate fashion by the phenolate O and imine N atoms of the Schiff base ligand. Two Cl⁻ anions complete the tetrahedral coordination in each case. The most obvious difference between the two forms is that the Zn—L (L = O, N, Cl) bond lengths in both unique molecules are longer than those found in the monoclinic polymorph, or indeed in other similar complexes. In the crystal, molecules are linked through N—H⋯O and N—H⋯Cl hydrogen bonds, forming chains along the b axis.

Related literature

For the structures of zinc complexes with Schiff base ligands, see: Munro et al. (2009 ); Granifo et al. (2006 ). For a monoclinic polymorph of the title compound in the space group P2₁/n, see: Han et al. (2010). For bond lengths in related zinc complexes, see: Ali et al. (2008 ); Zhu (2008 ); Wang (2007 ).

Experimental

Crystal data

[ZnCl₂(C₁₃H₂₀N₂O₂)]
M_r = 372.58
Triclinic, $[P \overline 1]$
a = 6.491 (3) Å
b = 12.351 (2) Å
c = 22.803 (3) Å
α = 90.707 (2)°
β = 96.201 (2)°
γ = 90.660 (2)°
V = 1817.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.65 mm⁻¹
T = 298 K
0.13 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.814, T_max = 0.880
8230 measured reflections
5775 independent reflections
4093 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.181
S = 1.08
5775 reflections
367 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	1.995 (4)
Zn1—N1	2.061 (4)
Zn1—Cl2	2.3252 (18)
Zn1—Cl1	2.3628 (17)
Zn2—O3	1.994 (4)
Zn2—N3	2.095 (5)
Zn2—Cl3	2.2994 (16)
Zn2—Cl4	2.3575 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O1ⁱ	0.90	2.03	2.904 (6)	163
N4—H4A⋯Cl2ⁱ	0.90	2.73	3.466 (5)	140
N2—H2B⋯Cl3	0.90	2.74	3.484 (5)	140
N2—H2A⋯O3	0.90	2.03	2.892 (6)	161
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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 local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812014341/sj5230sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014341/sj5230Isup2.hkl

checkCIF report

Comment top

The structures of zinc complexes with Schiff bases have received a great deal of attention (Munro et al., 2009; Granifo et al., 2006). The title compound was first reported in the monoclinic space group P2₁/n (Han et al., 2010). The author reports here a triclinic modification, I, in the space group P -1 with an asymmetric unit that contains two independent mononuclear zinc complex molecules (Fig. 1). In each molecule the Zn atoms are coordinated in a bidentate fashion by phenolate O and imine N atoms of the Schiff base ligand. Two Cl^- anions complete the tetrahedral coordination sphere in each case. The Zn1–O1, 1.995 (4)Å, Zn2–O3, 1.994 (4) Å, Zn1–N1, 2.061 (3)Å, Zn2–N3, 2.095 (3)Å, Zn1–Cl1, 2.3268, Zn1–Cl2, 2.3252 (18), Zn2–Cl3 2.2994 (16) and Zn2 Cl4 2.3575 (16) bond distances in the two independent molecules are comparable to one another but are generally longer than those observed in the monoclinic polymorph. This has Zn–O, 1.9425 (19) Å, Zn–N, 1.997 (2) Zn–Cl1 2.2554 (10) and Zn–Cl2, 2.2290 (9)Å. The bond lengths in I are also longer than those reported in other zinc Schiff base complexes (Ali et al., 2008; Zhu, 2008; Wang, 2007). These differences may be due to packing effects. In the crystal, molecules are linked through N—H···O and N—H···Cl hydrogen bonds (Table 2), to form chains along the b axis (Fig. 2).

Related literature top

For the structures of zinc complexes with Schiff base ligands, see: Munro et al. (2009); Granifo et al. (2006). For a monoclinic polymorph of the title compound in the space group P2₁/n, see: Han et al. (2010). For bond lengths in related zinc complexes, see: Ali et al. (2008); Zhu (2008); Wang (2007).

Experimental top

4-Methoxysalicylaldehyde (0.1 mmol, 15.2 mg), N-isopropylethane-1,2-diamine (0.1 mmol, 10.2 mg), and zinc chloride (0.1 mmol, 13.7 mg) were dissolved in methanol (15 ml). The mixture was stirred at reflux for 30 min and cooled to room temperature. Small and colorless block-like single crystals were obtained by slow evaporation of the solution in air.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The molecular packing of the title compound, viewed down the a axis. Hydrogen bonds are drawn as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

dichlorido(2-{[2-(isopropylammonio)ethyl]iminomethyl- κN}-5-methoxyphenolato-κO¹)zinc top

Crystal data top

[ZnCl₂(C₁₃H₂₀N₂O₂)]	Z = 4
M_r = 372.58	F(000) = 768
Triclinic, P1	D_x = 1.362 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.491 (3) Å	Cell parameters from 3080 reflections
b = 12.351 (2) Å	θ = 2.5–24.5°
c = 22.803 (3) Å	µ = 1.65 mm⁻¹
α = 90.707 (2)°	T = 298 K
β = 96.201 (2)°	Block, colorless
γ = 90.660 (2)°	0.13 × 0.10 × 0.08 mm
V = 1817.1 (9) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5775 independent reflections
Radiation source: fine-focus sealed tube	4093 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −7→7
T_min = 0.814, T_max = 0.880	k = −14→14
8230 measured reflections	l = −27→24

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0975P)² + 0.557P] where P = (F_o² + 2F_c²)/3
5775 reflections	(Δ/σ)_max < 0.001
367 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

[ZnCl₂(C₁₃H₂₀N₂O₂)]	γ = 90.660 (2)°
M_r = 372.58	V = 1817.1 (9) Å³
Triclinic, P1	Z = 4
a = 6.491 (3) Å	Mo Kα radiation
b = 12.351 (2) Å	µ = 1.65 mm⁻¹
c = 22.803 (3) Å	T = 298 K
α = 90.707 (2)°	0.13 × 0.10 × 0.08 mm
β = 96.201 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5775 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4093 reflections with I > 2σ(I)
T_min = 0.814, T_max = 0.880	R_int = 0.027
8230 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.181	H-atom parameters constrained
S = 1.08	Δρ_max = 0.63 e Å⁻³
5775 reflections	Δρ_min = −0.57 e Å⁻³
367 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Zn1	0.74321 (12)	0.83418 (5)	0.23642 (3)	0.0441 (2)
Cl1	0.9409 (3)	0.81988 (11)	0.32920 (7)	0.0474 (4)
Cl2	0.4987 (2)	0.97077 (12)	0.22753 (8)	0.0521 (4)
O1	0.9277 (7)	0.8554 (3)	0.17284 (19)	0.0498 (11)
O2	1.4088 (9)	0.7419 (4)	0.0412 (2)	0.0766 (16)
N1	0.6280 (7)	0.6838 (4)	0.2085 (2)	0.0397 (12)
N2	0.5954 (8)	0.5896 (3)	0.3369 (2)	0.0392 (11)
H2A	0.5568	0.5194	0.3339	0.047*
H2B	0.7167	0.5959	0.3214	0.047*
C1	0.8974 (9)	0.6630 (4)	0.1382 (3)	0.0423 (14)
C2	0.9929 (9)	0.7736 (4)	0.1399 (2)	0.0396 (14)
C3	1.1644 (10)	0.7914 (5)	0.1059 (3)	0.0481 (16)
H3	1.2275	0.8595	0.1070	0.058*
C4	1.2390 (11)	0.7097 (5)	0.0713 (3)	0.0508 (16)
C5	1.1530 (13)	0.6025 (6)	0.0688 (3)	0.065 (2)
H5	1.2054	0.5479	0.0465	0.078*
C6	0.9840 (12)	0.5833 (5)	0.1021 (3)	0.063 (2)
H6	0.9252	0.5142	0.1003	0.076*
C7	0.7202 (10)	0.6298 (5)	0.1696 (3)	0.0448 (15)
H7	0.6669	0.5608	0.1604	0.054*
C8	0.4381 (10)	0.6345 (5)	0.2314 (3)	0.0523 (17)
H8A	0.4358	0.5571	0.2238	0.063*
H8B	0.3149	0.6645	0.2101	0.063*
C9	0.4320 (10)	0.6553 (5)	0.2982 (3)	0.0443 (15)
H9A	0.2951	0.6364	0.3086	0.053*
H9B	0.4555	0.7318	0.3067	0.053*
C10	0.6342 (12)	0.6199 (6)	0.4030 (3)	0.0606 (19)
H10	0.6890	0.6942	0.4057	0.073*
C11	0.8045 (14)	0.5466 (7)	0.4341 (4)	0.088 (3)
H11A	0.7653	0.4720	0.4274	0.131*
H11B	0.8198	0.5621	0.4758	0.131*
H11C	0.9336	0.5606	0.4185	0.131*
C12	0.4325 (15)	0.6195 (8)	0.4329 (4)	0.095 (3)
H12A	0.3364	0.6690	0.4131	0.142*
H12B	0.4624	0.6413	0.4735	0.142*
H12C	0.3728	0.5478	0.4306	0.142*
C13	1.4981 (15)	0.6614 (8)	0.0035 (4)	0.097 (3)
H13A	1.5361	0.5983	0.0262	0.146*
H13B	1.6189	0.6918	−0.0112	0.146*
H13C	1.3977	0.6416	−0.0290	0.146*
Zn2	0.75666 (12)	0.33416 (5)	0.26356 (3)	0.0443 (2)
Cl3	1.0020 (2)	0.47085 (11)	0.27261 (8)	0.0523 (4)
Cl4	0.5584 (2)	0.31981 (11)	0.17081 (7)	0.0475 (4)
O3	0.5732 (7)	0.3560 (3)	0.32735 (19)	0.0482 (11)
O4	0.0905 (9)	0.2412 (4)	0.4588 (2)	0.0797 (17)
N3	0.8731 (7)	0.1838 (3)	0.2917 (2)	0.0390 (12)
N4	0.9042 (8)	0.0893 (4)	0.1632 (2)	0.0422 (12)
H4A	0.7834	0.0954	0.1789	0.051*
H4B	0.9398	0.0191	0.1652	0.051*
C14	0.6016 (10)	0.1639 (5)	0.3615 (3)	0.0453 (15)
C15	0.5066 (9)	0.2740 (4)	0.3594 (3)	0.0415 (15)
C16	0.3387 (10)	0.2910 (5)	0.3940 (3)	0.0495 (16)
H16	0.2789	0.3591	0.3939	0.059*
C17	0.2592 (11)	0.2094 (5)	0.4285 (3)	0.0544 (18)
C18	0.3474 (12)	0.1040 (6)	0.4310 (3)	0.061 (2)
H18	0.2961	0.0503	0.4539	0.074*
C19	0.5152 (12)	0.0830 (5)	0.3975 (3)	0.063 (2)
H19	0.5722	0.0142	0.3989	0.075*
C20	0.7798 (10)	0.1295 (5)	0.3312 (3)	0.0454 (16)
H20	0.8328	0.0616	0.3409	0.054*
C21	1.0593 (10)	0.1347 (5)	0.2682 (3)	0.0521 (17)
H21A	1.0568	0.0572	0.2745	0.063*
H21B	1.1838	0.1641	0.2904	0.063*
C22	1.0700 (10)	0.1552 (5)	0.2021 (3)	0.0443 (15)
H22A	1.0505	0.2317	0.1945	0.053*
H22B	1.2062	0.1360	0.1919	0.053*
C23	0.8673 (12)	0.1201 (5)	0.0974 (3)	0.0581 (18)
H23	0.8154	0.1943	0.0958	0.070*
C24	0.6975 (15)	0.0471 (7)	0.0662 (4)	0.088 (3)
H24A	0.7425	−0.0267	0.0676	0.132*
H24B	0.6691	0.0685	0.0259	0.132*
H24C	0.5740	0.0535	0.0856	0.132*
C25	1.0646 (15)	0.1192 (8)	0.0672 (4)	0.092 (3)
H25A	1.1609	0.1720	0.0858	0.138*
H25B	1.0327	0.1364	0.0263	0.138*
H25C	1.1251	0.0487	0.0705	0.138*
C26	0.0028 (15)	0.1620 (7)	0.4963 (4)	0.093 (3)
H26A	−0.0352	0.0973	0.4738	0.140*
H26B	−0.1179	0.1915	0.5112	0.140*
H26C	0.1036	0.1450	0.5288	0.140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0476 (5)	0.0345 (4)	0.0517 (5)	−0.0044 (3)	0.0124 (4)	−0.0003 (3)
Cl1	0.0494 (10)	0.0459 (8)	0.0460 (9)	−0.0042 (7)	0.0015 (7)	0.0037 (6)
Cl2	0.0399 (10)	0.0434 (8)	0.0735 (11)	0.0052 (7)	0.0088 (8)	−0.0091 (7)
O1	0.055 (3)	0.036 (2)	0.062 (3)	−0.0052 (19)	0.025 (2)	−0.0056 (19)
O2	0.091 (4)	0.074 (3)	0.073 (4)	0.014 (3)	0.045 (3)	0.006 (3)
N1	0.035 (3)	0.040 (3)	0.044 (3)	−0.003 (2)	0.001 (2)	0.006 (2)
N2	0.041 (3)	0.037 (2)	0.040 (3)	−0.001 (2)	0.005 (2)	0.001 (2)
C1	0.038 (4)	0.042 (3)	0.046 (3)	0.000 (3)	0.000 (3)	0.000 (3)
C2	0.046 (4)	0.035 (3)	0.037 (3)	0.006 (3)	0.000 (3)	0.006 (2)
C3	0.048 (4)	0.046 (3)	0.052 (4)	0.002 (3)	0.011 (3)	0.008 (3)
C4	0.057 (5)	0.060 (4)	0.039 (4)	0.019 (3)	0.015 (3)	0.009 (3)
C5	0.079 (6)	0.055 (4)	0.066 (5)	0.008 (4)	0.028 (4)	−0.010 (3)
C6	0.075 (5)	0.044 (4)	0.071 (5)	−0.005 (3)	0.012 (4)	−0.013 (3)
C7	0.048 (4)	0.036 (3)	0.050 (4)	−0.007 (3)	0.004 (3)	−0.005 (3)
C8	0.050 (4)	0.057 (4)	0.049 (4)	−0.016 (3)	0.003 (3)	0.004 (3)
C9	0.035 (4)	0.042 (3)	0.057 (4)	0.001 (3)	0.010 (3)	0.007 (3)
C10	0.070 (5)	0.059 (4)	0.053 (4)	−0.011 (4)	0.011 (4)	−0.009 (3)
C11	0.092 (7)	0.110 (7)	0.058 (5)	0.004 (5)	−0.005 (5)	0.001 (5)
C12	0.092 (7)	0.123 (8)	0.073 (6)	−0.013 (6)	0.033 (5)	−0.025 (5)
C13	0.105 (8)	0.115 (7)	0.082 (7)	0.027 (6)	0.052 (6)	0.003 (5)
Zn2	0.0480 (5)	0.0349 (4)	0.0518 (5)	−0.0010 (3)	0.0141 (4)	−0.0034 (3)
Cl3	0.0424 (10)	0.0413 (8)	0.0741 (11)	−0.0101 (7)	0.0106 (8)	0.0054 (7)
Cl4	0.0507 (10)	0.0458 (8)	0.0448 (9)	0.0017 (7)	0.0011 (7)	−0.0079 (6)
O3	0.054 (3)	0.034 (2)	0.060 (3)	−0.0038 (19)	0.024 (2)	−0.0033 (19)
O4	0.092 (4)	0.076 (3)	0.079 (4)	−0.016 (3)	0.049 (3)	−0.009 (3)
N3	0.034 (3)	0.036 (2)	0.045 (3)	0.005 (2)	0.000 (2)	−0.006 (2)
N4	0.051 (3)	0.037 (2)	0.040 (3)	−0.004 (2)	0.010 (2)	−0.004 (2)
C14	0.043 (4)	0.047 (3)	0.046 (4)	−0.004 (3)	0.007 (3)	−0.004 (3)
C15	0.036 (4)	0.045 (3)	0.043 (3)	−0.007 (3)	0.003 (3)	−0.014 (3)
C16	0.050 (4)	0.046 (3)	0.053 (4)	−0.001 (3)	0.007 (3)	−0.010 (3)
C17	0.065 (5)	0.052 (4)	0.048 (4)	−0.017 (3)	0.012 (3)	−0.007 (3)
C18	0.070 (5)	0.063 (4)	0.055 (4)	−0.016 (4)	0.023 (4)	0.006 (3)
C19	0.073 (5)	0.046 (4)	0.070 (5)	−0.004 (3)	0.008 (4)	0.010 (3)
C20	0.051 (4)	0.038 (3)	0.046 (4)	0.001 (3)	0.000 (3)	−0.004 (3)
C21	0.043 (4)	0.058 (4)	0.053 (4)	−0.002 (3)	0.001 (3)	−0.019 (3)
C22	0.037 (4)	0.040 (3)	0.058 (4)	0.000 (3)	0.013 (3)	−0.004 (3)
C23	0.073 (5)	0.047 (4)	0.054 (4)	0.003 (3)	0.003 (4)	0.005 (3)
C24	0.103 (7)	0.101 (6)	0.057 (5)	−0.015 (5)	−0.006 (5)	−0.009 (4)
C25	0.096 (7)	0.123 (8)	0.061 (5)	0.000 (6)	0.025 (5)	0.012 (5)
C26	0.096 (8)	0.101 (7)	0.088 (7)	−0.029 (6)	0.044 (6)	0.000 (5)

Geometric parameters (Å, º) top

Zn1—O1	1.995 (4)	Zn2—O3	1.994 (4)
Zn1—N1	2.061 (4)	Zn2—N3	2.095 (5)
Zn1—Cl2	2.3252 (18)	Zn2—Cl3	2.2994 (16)
Zn1—Cl1	2.3628 (17)	Zn2—Cl4	2.3575 (16)
O1—C2	1.351 (6)	O3—C15	1.350 (7)
O2—C4	1.416 (8)	O4—C17	1.414 (8)
O2—C13	1.471 (9)	O4—C26	1.458 (8)
N1—C7	1.304 (7)	N3—C20	1.323 (7)
N1—C8	1.514 (7)	N3—C21	1.505 (8)
N2—C10	1.543 (8)	N4—C22	1.537 (7)
N2—C9	1.547 (7)	N4—C23	1.548 (8)
N2—H2A	0.9000	N4—H4A	0.9000
N2—H2B	0.8999	N4—H4B	0.9000
C1—C6	1.433 (9)	C14—C19	1.448 (9)
C1—C7	1.475 (8)	C14—C20	1.474 (9)
C1—C2	1.492 (7)	C14—C15	1.498 (8)
C2—C3	1.440 (8)	C15—C16	1.430 (8)
C3—C4	1.395 (8)	C16—C17	1.412 (9)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.429 (9)	C17—C18	1.428 (10)
C5—C6	1.419 (10)	C18—C19	1.420 (10)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.546 (9)	C21—C22	1.540 (9)
C8—H8A	0.9700	C21—H21A	0.9700
C8—H8B	0.9700	C21—H21B	0.9700
C9—H9A	0.9700	C22—H22A	0.9700
C9—H9B	0.9700	C22—H22B	0.9700
C10—C12	1.539 (11)	C23—C25	1.518 (11)
C10—C11	1.553 (11)	C23—C24	1.524 (10)
C10—H10	0.9800	C23—H23	0.9800
C11—H11A	0.9600	C24—H24A	0.9600
C11—H11B	0.9600	C24—H24B	0.9600
C11—H11C	0.9600	C24—H24C	0.9600
C12—H12A	0.9600	C25—H25A	0.9600
C12—H12B	0.9600	C25—H25B	0.9600
C12—H12C	0.9600	C25—H25C	0.9600
C13—H13A	0.9600	C26—H26A	0.9600
C13—H13B	0.9600	C26—H26B	0.9600
C13—H13C	0.9600	C26—H26C	0.9600

O1—Zn1—N1	96.96 (18)	O3—Zn2—N3	96.87 (18)
O1—Zn1—Cl2	107.23 (13)	O3—Zn2—Cl3	107.48 (12)
N1—Zn1—Cl2	114.06 (15)	N3—Zn2—Cl3	113.43 (14)
O1—Zn1—Cl1	110.63 (14)	O3—Zn2—Cl4	110.55 (14)
N1—Zn1—Cl1	109.73 (14)	N3—Zn2—Cl4	111.53 (13)
Cl2—Zn1—Cl1	116.43 (6)	Cl3—Zn2—Cl4	115.33 (6)
C2—O1—Zn1	123.6 (3)	C15—O3—Zn2	123.1 (3)
C4—O2—C13	118.2 (6)	C17—O4—C26	118.0 (6)
C7—N1—C8	118.9 (5)	C20—N3—C21	118.6 (5)
C7—N1—Zn1	119.1 (4)	C20—N3—Zn2	119.2 (4)
C8—N1—Zn1	122.0 (4)	C21—N3—Zn2	122.2 (4)
C10—N2—C9	117.6 (5)	C22—N4—C23	116.8 (4)
C10—N2—H2A	107.9	C22—N4—H4A	108.1
C9—N2—H2A	107.8	C23—N4—H4A	108.2
C10—N2—H2B	107.9	C22—N4—H4B	108.1
C9—N2—H2B	107.9	C23—N4—H4B	108.1
H2A—N2—H2B	107.2	H4A—N4—H4B	107.3
C6—C1—C7	117.8 (5)	C19—C14—C20	115.8 (6)
C6—C1—C2	116.7 (6)	C19—C14—C15	117.8 (6)
C7—C1—C2	125.5 (5)	C20—C14—C15	126.3 (5)
O1—C2—C3	119.7 (5)	O3—C15—C16	119.6 (5)
O1—C2—C1	122.5 (5)	O3—C15—C14	123.4 (5)
C3—C2—C1	117.8 (5)	C16—C15—C14	117.0 (5)
C4—C3—C2	122.1 (6)	C17—C16—C15	123.2 (6)
C4—C3—H3	118.9	C17—C16—H16	118.4
C2—C3—H3	118.9	C15—C16—H16	118.4
C3—C4—O2	114.2 (6)	C16—C17—O4	114.8 (6)
C3—C4—C5	121.9 (6)	C16—C17—C18	120.7 (6)
O2—C4—C5	123.9 (6)	O4—C17—C18	124.5 (6)
C6—C5—C4	116.9 (6)	C19—C18—C17	118.4 (6)
C6—C5—H5	121.6	C19—C18—H18	120.8
C4—C5—H5	121.6	C17—C18—H18	120.8
C5—C6—C1	124.6 (6)	C18—C19—C14	122.9 (6)
C5—C6—H6	117.7	C18—C19—H19	118.5
C1—C6—H6	117.7	C14—C19—H19	118.5
N1—C7—C1	129.1 (5)	N3—C20—C14	127.6 (6)
N1—C7—H7	115.5	N3—C20—H20	116.2
C1—C7—H7	115.5	C14—C20—H20	116.2
N1—C8—C9	112.8 (5)	N3—C21—C22	113.5 (5)
N1—C8—H8A	109.0	N3—C21—H21A	108.9
C9—C8—H8A	109.0	C22—C21—H21A	108.9
N1—C8—H8B	109.0	N3—C21—H21B	108.9
C9—C8—H8B	109.0	C22—C21—H21B	108.9
H8A—C8—H8B	107.8	H21A—C21—H21B	107.7
C8—C9—N2	112.9 (5)	N4—C22—C21	111.8 (5)
C8—C9—H9A	109.0	N4—C22—H22A	109.3
N2—C9—H9A	109.0	C21—C22—H22A	109.3
C8—C9—H9B	109.0	N4—C22—H22B	109.3
N2—C9—H9B	109.0	C21—C22—H22B	109.3
H9A—C9—H9B	107.8	H22A—C22—H22B	107.9
C12—C10—N2	112.0 (6)	C25—C23—C24	112.7 (6)
C12—C10—C11	113.4 (7)	C25—C23—N4	112.8 (6)
N2—C10—C11	110.1 (6)	C24—C23—N4	109.3 (6)
C12—C10—H10	107.0	C25—C23—H23	107.3
N2—C10—H10	107.0	C24—C23—H23	107.3
C11—C10—H10	107.0	N4—C23—H23	107.3
C10—C11—H11A	109.5	C23—C24—H24A	109.5
C10—C11—H11B	109.5	C23—C24—H24B	109.5
H11A—C11—H11B	109.5	H24A—C24—H24B	109.5
C10—C11—H11C	109.5	C23—C24—H24C	109.5
H11A—C11—H11C	109.5	H24A—C24—H24C	109.5
H11B—C11—H11C	109.5	H24B—C24—H24C	109.5
C10—C12—H12A	109.5	C23—C25—H25A	109.5
C10—C12—H12B	109.5	C23—C25—H25B	109.5
H12A—C12—H12B	109.5	H25A—C25—H25B	109.5
C10—C12—H12C	109.5	C23—C25—H25C	109.5
H12A—C12—H12C	109.5	H25A—C25—H25C	109.5
H12B—C12—H12C	109.5	H25B—C25—H25C	109.5
O2—C13—H13A	109.5	O4—C26—H26A	109.5
O2—C13—H13B	109.5	O4—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
O2—C13—H13C	109.5	O4—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O1ⁱ	0.90	2.03	2.904 (6)	163
N4—H4A···Cl2ⁱ	0.90	2.73	3.466 (5)	140
N2—H2B···Cl3	0.90	2.74	3.484 (5)	140
N2—H2A···O3	0.90	2.03	2.892 (6)	161

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₃H₂₀N₂O₂)]
M_r	372.58
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.491 (3), 12.351 (2), 22.803 (3)
α, β, γ (°)	90.707 (2), 96.201 (2), 90.660 (2)
V (Å³)	1817.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.65
Crystal size (mm)	0.13 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.814, 0.880
No. of measured, independent and observed [I > 2σ(I)] reflections	8230, 5775, 4093
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.181, 1.08
No. of reflections	5775
No. of parameters	367
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.57

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and local programs.

Selected bond lengths (Å) top

Zn1—O1	1.995 (4)	Zn2—O3	1.994 (4)
Zn1—N1	2.061 (4)	Zn2—N3	2.095 (5)
Zn1—Cl2	2.3252 (18)	Zn2—Cl3	2.2994 (16)
Zn1—Cl1	2.3628 (17)	Zn2—Cl4	2.3575 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O1ⁱ	0.90	2.03	2.904 (6)	162.6
N4—H4A···Cl2ⁱ	0.90	2.73	3.466 (5)	140.3
N2—H2B···Cl3	0.90	2.74	3.484 (5)	140.4
N2—H2A···O3	0.90	2.03	2.892 (6)	160.9

Symmetry code: (i) x, y−1, z.

References

Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718–m719. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Granifo, J., Garland, M. T. & Baggio, R. (2006). Acta Cryst. C62, m56–m59. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Han, Z.-Q., Wang, Y. & Han, S. (2010). Acta Cryst. E66, m469. Web of Science CrossRef IUCr Journals Google Scholar
Munro, O. Q., Gillham, K. & Akerman, M. P. (2009). Acta Cryst. C65, m317–m320. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). 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
Wang, S.-X. (2007). Acta Cryst. E63, m706–m707. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, X.-W. (2008). Acta Cryst. E64, m1456–m1457. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Page m587

doi:10.1107/S1600536812014341

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