Bis[2-(2-naphthyl­imino­meth­yl)phenolato-κ2N,O]zinc(II)

Dong, J.-F.; Li, L.-Z.; Xu, L.-L.; Xu, T.; Wang, D.-Q.

doi:10.1107/S1600536807024452

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Bis[2-(2-naphthyliminomethyl)phenolato-κ²N,O]zinc(II)

J.-F. Dong, L.-Z. Li, L.-L. Xu, T. Xu and D.-Q. Wang

In the title complex, [Zn(C₁₇H₁₂NO)₂], the Zn^II ion is coordinated by two N,O-bidentate ligand molecules in a distorted tetrahedral geometry. The crystal packing may be stabilized by weak C—H

Cg interactions [Cg is a ring centroid; H

Cg = 2.95 Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024452/hb2423sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024452/hb2423Isup2.hkl Contains datablock I

CCDC reference: 651158

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.017 Å
R factor = 0.123
wR factor = 0.323
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ...         17

Alert level C
RFACG01_ALERT_3_C  The value of the R factor is > 0.10
            R factor given   0.123
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.323
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.109
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT082_ALERT_2_C High R1 Value ..................................       0.12
PLAT084_ALERT_2_C High R2 Value ..................................       0.32
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C33

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1         (2)       2.09

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

As part of our ongoing studies of Schiff bases, we report here the synthesis and crystal structure of the title compound, (I), (Fig. 1), a new zinc(II) complex with a bidentate Schiff base ligand derived from the condensation of salicylaldehyde and 2-naphthylamine.

The coordination around zinc is a distorted tetrahedon involving two O and N atoms of the ligands (Table 1). These bond lengths and angle values are similar to the reported values for related structures (Hokelek et al., 2000, Tatar et al., 1999).

In the crystal of (I), the relatively short intermolecular distances H17···Cg(1)ⁱ of 2.945Å and H4···Cg(2)ⁱⁱ of 2.947Å (symmetry code: (i) 1/2 + x, 1/2 - y, -1/2 + z; (ii) x - 1, y, z; Cg(1) and Cg(2) are the centroids of the C25–34 and C29–34 rings, respectively) indicate the presence of weak C—H···π interactions (Fig. 2), which stabilize the crystal packing along with van der Waals forces.

Related literature top

For related literature, see: Hokelek et al. (2000); Lipscomb & Strater (1996); Tatar et al. (1999).

Experimental top

2-Naphthylamine (1 mmol, 143.19 mg) was dissolved in hot methanol (10 ml) and added in portions to a methanol solution (3 ml) of salicylaldehyde (1 mmol, 0.11 ml). The mixture was then stirred at 323 K for 2 h. Subsequently, an aqueous solution (2 ml) of zinc acetate dihydrate (1 mmol, 219.5 mg) was added dropwise and stirred for another 5 h. The solution was held at room temperature for ten days, whereupon yellow blocks of (I) were obtained.

Structure description top

For related literature, see: Hokelek et al. (2000); Lipscomb & Strater (1996); Tatar et al. (1999).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids (arbitrary spheres for the H atoms).
	Fig. 2. The C—H···π interactions (dashed lines) in the crystal structure of (I).

Bis[2-(2-naphthyliminomethyl)phenolato-κ²N,O]zinc(II) top

Crystal data top

[Zn(C₁₇H₁₂NO)₂]	F(000) = 1152
M_r = 557.92	D_x = 1.437 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2565 reflections
a = 5.7616 (11) Å	θ = 2.6–19.3°
b = 26.912 (3) Å	µ = 0.99 mm⁻¹
c = 16.635 (2) Å	T = 298 K
β = 90.791 (2)°	Block, yellow
V = 2579.0 (6) Å³	0.27 × 0.18 × 0.11 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	4398 independent reflections
Radiation source: fine-focus sealed tube	2620 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.109
ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.776, T_max = 0.899	k = −28→32
12472 measured reflections	l = −19→19

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)] = 0.123	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.323	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.1741P)² + 8.9475P] where P = (F_o² + 2F_c²)/3
4398 reflections	(Δ/σ)_max = 0.002
352 parameters	Δρ_max = 1.51 e Å⁻³
0 restraints	Δρ_min = −1.04 e Å⁻³

Crystal data top

[Zn(C₁₇H₁₂NO)₂]	V = 2579.0 (6) Å³
M_r = 557.92	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.7616 (11) Å	µ = 0.99 mm⁻¹
b = 26.912 (3) Å	T = 298 K
c = 16.635 (2) Å	0.27 × 0.18 × 0.11 mm
β = 90.791 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	4398 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2620 reflections with I > 2σ(I)
T_min = 0.776, T_max = 0.899	R_int = 0.109
12472 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.123	0 restraints
wR(F²) = 0.323	H-atom parameters constrained
S = 1.01	Δρ_max = 1.51 e Å⁻³
4398 reflections	Δρ_min = −1.04 e Å⁻³
352 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	0.3650 (2)	0.23346 (4)	0.67332 (7)	0.0501 (5)
N1	0.5696 (14)	0.2282 (3)	0.5763 (5)	0.0467 (19)
N2	0.5939 (14)	0.2372 (3)	0.7685 (4)	0.0414 (18)
O1	0.1839 (13)	0.1768 (3)	0.6500 (5)	0.0590 (19)
O2	0.1955 (14)	0.2908 (3)	0.7000 (4)	0.063 (2)
C1	0.5715 (19)	0.1862 (5)	0.5369 (7)	0.060 (3)
H1	0.6808	0.1837	0.4965	0.072*
C2	0.4265 (19)	0.1437 (4)	0.5480 (6)	0.053 (3)
C3	0.241 (2)	0.1414 (4)	0.6000 (7)	0.057 (3)
C4	0.113 (3)	0.0972 (4)	0.5990 (7)	0.078 (4)
H4	−0.0140	0.0947	0.6325	0.094*
C5	0.166 (3)	0.0577 (5)	0.5514 (9)	0.093 (5)
H5	0.0776	0.0289	0.5535	0.112*
C6	0.351 (3)	0.0606 (5)	0.5001 (9)	0.092 (5)
H6	0.3887	0.0338	0.4676	0.111*
C7	0.477 (2)	0.1028 (5)	0.4975 (8)	0.077 (4)
H7	0.5996	0.1050	0.4619	0.092*
C8	0.6637 (17)	0.3146 (4)	0.5780 (6)	0.049 (2)
H8	0.5256	0.3200	0.6049	0.058*
C9	0.7230 (17)	0.2665 (4)	0.5553 (6)	0.048 (2)
C10	0.9323 (19)	0.2581 (4)	0.5148 (8)	0.062 (3)
H10	0.9727	0.2263	0.4984	0.074*
C11	1.0722 (18)	0.2967 (4)	0.5005 (6)	0.052 (3)
H11	1.2127	0.2906	0.4755	0.062*
C12	1.0190 (17)	0.3456 (4)	0.5209 (6)	0.051 (3)
C13	0.8093 (17)	0.3550 (3)	0.5608 (5)	0.042 (2)
C14	0.750 (2)	0.4042 (4)	0.5842 (7)	0.066 (3)
H14	0.6116	0.4102	0.6108	0.079*
C15	0.895 (2)	0.4423 (4)	0.5673 (7)	0.065 (3)
H15	0.8556	0.4746	0.5817	0.078*
C16	1.103 (2)	0.4333 (5)	0.5287 (7)	0.069 (3)
H16	1.2050	0.4595	0.5193	0.083*
C17	1.160 (2)	0.3868 (5)	0.5046 (8)	0.067 (3)
H17	1.2959	0.3820	0.4764	0.080*
C18	0.6095 (19)	0.2797 (4)	0.8069 (6)	0.054 (3)
H18	0.7286	0.2820	0.8450	0.065*
C19	0.4681 (19)	0.3230 (4)	0.7979 (6)	0.054 (3)
C20	0.2714 (19)	0.3266 (4)	0.7466 (6)	0.052 (3)
C21	0.148 (2)	0.3713 (4)	0.7471 (7)	0.067 (3)
H21	0.0154	0.3746	0.7152	0.080*
C22	0.221 (3)	0.4108 (5)	0.7944 (9)	0.087 (4)
H22	0.1343	0.4399	0.7943	0.104*
C23	0.415 (3)	0.4082 (4)	0.8406 (8)	0.078 (4)
H23	0.4631	0.4359	0.8699	0.094*
C24	0.542 (2)	0.3650 (5)	0.8446 (8)	0.076 (4)
H24	0.6739	0.3631	0.8773	0.091*
C25	0.6688 (18)	0.1505 (4)	0.7680 (6)	0.051 (2)
H25	0.5266	0.1467	0.7416	0.061*
C26	0.7456 (16)	0.1970 (4)	0.7892 (6)	0.047 (2)
C27	0.9610 (18)	0.2040 (4)	0.8274 (6)	0.054 (3)
H27	1.0126	0.2359	0.8398	0.065*
C28	1.0951 (19)	0.1636 (5)	0.8463 (6)	0.058 (3)
H28	1.2370	0.1679	0.8727	0.069*
C29	1.018 (2)	0.1153 (5)	0.8255 (6)	0.062 (3)
C30	0.8047 (19)	0.1086 (4)	0.7862 (7)	0.056 (3)
C31	0.734 (2)	0.0605 (5)	0.7634 (8)	0.072 (3)
H31	0.5922	0.0563	0.7368	0.086*
C32	0.869 (3)	0.0196 (5)	0.7795 (9)	0.084 (4)
H32	0.8206	−0.0118	0.7634	0.100*
C33	1.084 (3)	0.0262 (6)	0.8213 (10)	0.098 (5)
H33	1.1775	−0.0011	0.8337	0.118*
C34	1.151 (2)	0.0726 (6)	0.8427 (9)	0.083 (4)
H34	1.2920	0.0766	0.8700	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0603 (8)	0.0492 (7)	0.0408 (6)	−0.0029 (6)	0.0011 (5)	−0.0036 (5)
N1	0.047 (5)	0.042 (5)	0.051 (5)	0.002 (4)	0.004 (4)	0.001 (4)
N2	0.055 (5)	0.037 (4)	0.032 (4)	0.001 (4)	0.003 (3)	−0.004 (3)
O1	0.066 (5)	0.043 (4)	0.068 (5)	−0.007 (4)	0.009 (4)	−0.012 (4)
O2	0.079 (5)	0.055 (5)	0.054 (4)	0.008 (4)	−0.009 (4)	−0.009 (4)
C1	0.046 (6)	0.072 (8)	0.064 (7)	0.002 (6)	0.005 (5)	−0.002 (6)
C2	0.057 (7)	0.050 (6)	0.053 (6)	0.006 (5)	−0.004 (5)	−0.002 (5)
C3	0.058 (7)	0.046 (6)	0.066 (7)	−0.007 (5)	−0.011 (5)	0.011 (5)
C4	0.121 (12)	0.055 (7)	0.060 (7)	−0.033 (7)	0.009 (7)	−0.003 (6)
C5	0.167 (16)	0.040 (7)	0.073 (9)	−0.028 (8)	−0.003 (10)	0.009 (6)
C6	0.148 (15)	0.043 (7)	0.086 (10)	0.014 (8)	−0.024 (10)	−0.020 (7)
C7	0.079 (9)	0.073 (9)	0.078 (8)	0.007 (7)	0.000 (7)	−0.014 (7)
C8	0.046 (6)	0.057 (6)	0.044 (5)	0.014 (5)	0.007 (4)	−0.007 (5)
C9	0.037 (5)	0.057 (6)	0.049 (5)	−0.009 (5)	−0.002 (4)	0.003 (5)
C10	0.046 (6)	0.061 (7)	0.079 (8)	−0.003 (5)	0.018 (5)	−0.014 (6)
C11	0.045 (6)	0.073 (8)	0.038 (5)	0.009 (6)	0.003 (4)	−0.003 (5)
C12	0.039 (6)	0.063 (7)	0.050 (6)	−0.006 (5)	0.000 (4)	0.017 (5)
C13	0.054 (6)	0.037 (5)	0.034 (5)	0.000 (4)	−0.006 (4)	−0.001 (4)
C14	0.060 (7)	0.069 (8)	0.070 (8)	0.006 (6)	−0.002 (6)	−0.013 (6)
C15	0.084 (9)	0.039 (6)	0.073 (8)	0.001 (6)	−0.008 (7)	0.004 (5)
C16	0.080 (9)	0.061 (8)	0.066 (7)	−0.015 (7)	−0.007 (6)	0.020 (6)
C17	0.053 (7)	0.070 (8)	0.079 (8)	−0.014 (6)	0.003 (6)	0.017 (6)
C18	0.057 (7)	0.059 (7)	0.047 (6)	−0.011 (5)	−0.012 (5)	−0.004 (5)
C19	0.060 (7)	0.058 (6)	0.045 (6)	−0.002 (5)	−0.001 (5)	−0.009 (5)
C20	0.061 (7)	0.048 (6)	0.046 (6)	0.000 (5)	0.013 (5)	0.003 (5)
C21	0.074 (8)	0.064 (8)	0.062 (7)	0.017 (6)	−0.001 (6)	−0.002 (6)
C22	0.124 (13)	0.050 (8)	0.086 (10)	0.015 (8)	0.008 (9)	−0.006 (7)
C23	0.113 (12)	0.037 (6)	0.084 (9)	−0.001 (7)	−0.008 (8)	−0.015 (6)
C24	0.084 (9)	0.061 (8)	0.082 (9)	−0.003 (7)	−0.008 (7)	−0.027 (6)
C25	0.046 (6)	0.049 (6)	0.057 (6)	−0.001 (5)	0.006 (5)	0.010 (5)
C26	0.039 (6)	0.060 (7)	0.043 (5)	0.003 (5)	0.006 (4)	0.007 (5)
C27	0.043 (6)	0.062 (7)	0.058 (6)	−0.002 (5)	0.014 (5)	0.006 (5)
C28	0.049 (7)	0.085 (9)	0.039 (5)	0.000 (6)	0.002 (4)	−0.001 (5)
C29	0.066 (8)	0.073 (8)	0.046 (6)	0.017 (6)	0.009 (5)	0.018 (5)
C30	0.042 (6)	0.058 (7)	0.070 (7)	0.001 (5)	0.011 (5)	0.002 (5)
C31	0.078 (9)	0.066 (8)	0.071 (8)	−0.005 (7)	0.017 (6)	0.006 (6)
C32	0.094 (11)	0.046 (7)	0.112 (11)	0.009 (7)	0.022 (9)	0.021 (7)
C33	0.101 (12)	0.087 (11)	0.108 (12)	0.033 (9)	0.015 (10)	0.042 (9)
C34	0.066 (9)	0.091 (11)	0.091 (10)	0.018 (8)	−0.002 (7)	0.028 (8)

Geometric parameters (Å, º) top

Zn1—O2	1.884 (8)	C15—C16	1.390 (17)
Zn1—O1	1.885 (7)	C15—H15	0.9300
Zn1—N1	2.016 (8)	C16—C17	1.355 (17)
Zn1—N2	2.049 (8)	C16—H16	0.9300
N1—C1	1.307 (14)	C17—H17	0.9300
N1—C9	1.404 (12)	C18—C19	1.428 (15)
N2—C18	1.314 (13)	C18—H18	0.9300
N2—C26	1.429 (12)	C19—C20	1.413 (15)
O1—C3	1.309 (13)	C19—C24	1.433 (15)
O2—C20	1.308 (13)	C20—C21	1.396 (14)
C1—C2	1.431 (15)	C21—C22	1.382 (18)
C1—H1	0.9300	C21—H21	0.9300
C2—C3	1.385 (15)	C22—C23	1.347 (19)
C2—C7	1.418 (16)	C22—H22	0.9300
C3—C4	1.398 (15)	C23—C24	1.374 (17)
C4—C5	1.364 (18)	C23—H23	0.9300
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.38 (2)	C25—C26	1.373 (14)
C5—H5	0.9300	C25—C30	1.403 (14)
C6—C7	1.347 (19)	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.399 (14)
C7—H7	0.9300	C27—C28	1.367 (15)
C8—C9	1.392 (13)	C27—H27	0.9300
C8—C13	1.406 (13)	C28—C29	1.417 (17)
C8—H8	0.9300	C28—H28	0.9300
C9—C10	1.408 (14)	C29—C30	1.393 (16)
C10—C11	1.338 (15)	C29—C34	1.409 (17)
C10—H10	0.9300	C30—C31	1.408 (16)
C11—C12	1.393 (14)	C31—C32	1.370 (17)
C11—H11	0.9300	C31—H31	0.9300
C12—C13	1.410 (14)	C32—C33	1.43 (2)
C12—C17	1.402 (15)	C32—H32	0.9300
C13—C14	1.424 (14)	C33—C34	1.35 (2)
C14—C15	1.355 (16)	C33—H33	0.9300
C14—H14	0.9300	C34—H34	0.9300

O2—Zn1—O1	115.1 (3)	C16—C15—H15	119.8
O2—Zn1—N1	123.8 (3)	C17—C16—C15	120.5 (11)
O1—Zn1—N1	96.1 (3)	C17—C16—H16	119.7
O2—Zn1—N2	96.2 (3)	C15—C16—H16	119.7
O1—Zn1—N2	123.2 (3)	C16—C17—C12	122.3 (12)
N1—Zn1—N2	104.2 (3)	C16—C17—H17	118.9
C1—N1—C9	119.9 (9)	C12—C17—H17	118.9
C1—N1—Zn1	118.1 (7)	N2—C18—C19	128.7 (9)
C9—N1—Zn1	121.7 (6)	N2—C18—H18	115.7
C18—N2—C26	120.3 (9)	C19—C18—H18	115.7
C18—N2—Zn1	117.2 (7)	C20—C19—C18	124.8 (9)
C26—N2—Zn1	122.3 (6)	C20—C19—C24	120.2 (11)
C3—O1—Zn1	125.2 (7)	C18—C19—C24	115.0 (10)
C20—O2—Zn1	125.0 (7)	O2—C20—C21	118.2 (10)
N1—C1—C2	128.2 (10)	O2—C20—C19	124.5 (10)
N1—C1—H1	115.9	C21—C20—C19	117.3 (10)
C2—C1—H1	115.9	C22—C21—C20	120.9 (12)
C3—C2—C1	125.0 (10)	C22—C21—H21	119.5
C3—C2—C7	120.1 (11)	C20—C21—H21	119.5
C1—C2—C7	114.8 (11)	C23—C22—C21	121.9 (13)
O1—C3—C2	124.5 (10)	C23—C22—H22	119.1
O1—C3—C4	119.3 (11)	C21—C22—H22	119.1
C2—C3—C4	116.2 (11)	C22—C23—C24	120.4 (12)
C5—C4—C3	123.2 (13)	C22—C23—H23	119.8
C5—C4—H4	118.4	C24—C23—H23	119.8
C3—C4—H4	118.4	C23—C24—C19	119.1 (12)
C6—C5—C4	119.8 (13)	C23—C24—H24	120.4
C6—C5—H5	120.1	C19—C24—H24	120.4
C4—C5—H5	120.1	C26—C25—C30	120.0 (10)
C7—C6—C5	119.4 (12)	C26—C25—H25	120.0
C7—C6—H6	120.3	C30—C25—H25	120.0
C5—C6—H6	120.3	C25—C26—C27	121.3 (10)
C6—C7—C2	121.3 (13)	C25—C26—N2	115.7 (9)
C6—C7—H7	119.4	C27—C26—N2	122.9 (9)
C2—C7—H7	119.4	C28—C27—C26	119.5 (10)
C9—C8—C13	121.0 (9)	C28—C27—H27	120.3
C9—C8—H8	119.5	C26—C27—H27	120.3
C13—C8—H8	119.5	C27—C28—C29	119.9 (11)
C8—C9—N1	117.2 (9)	C27—C28—H28	120.0
C8—C9—C10	119.6 (9)	C29—C28—H28	120.0
N1—C9—C10	123.2 (9)	C30—C29—C28	120.3 (10)
C11—C10—C9	118.9 (10)	C30—C29—C34	117.7 (12)
C11—C10—H10	120.5	C28—C29—C34	121.9 (12)
C9—C10—H10	120.5	C25—C30—C29	118.8 (10)
C10—C11—C12	123.6 (10)	C25—C30—C31	121.5 (11)
C10—C11—H11	118.2	C29—C30—C31	119.7 (11)
C12—C11—H11	118.2	C32—C31—C30	121.6 (14)
C11—C12—C13	118.5 (9)	C32—C31—H31	119.2
C11—C12—C17	124.8 (10)	C30—C31—H31	119.2
C13—C12—C17	116.7 (10)	C31—C32—C33	119.0 (14)
C8—C13—C12	118.3 (9)	C31—C32—H32	120.5
C8—C13—C14	121.1 (9)	C33—C32—H32	120.5
C12—C13—C14	120.6 (10)	C34—C33—C32	119.0 (13)
C15—C14—C13	119.6 (11)	C34—C33—H33	120.5
C15—C14—H14	120.2	C32—C33—H33	120.5
C13—C14—H14	120.2	C33—C34—C29	123.1 (14)
C14—C15—C16	120.3 (11)	C33—C34—H34	118.5
C14—C15—H15	119.8	C29—C34—H34	118.5

Experimental details

Crystal data
Chemical formula	[Zn(C₁₇H₁₂NO)₂]
M_r	557.92
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	5.7616 (11), 26.912 (3), 16.635 (2)
β (°)	90.791 (2)
V (Å³)	2579.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.27 × 0.18 × 0.11

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.776, 0.899
No. of measured, independent and observed [I > 2σ(I)] reflections	12472, 4398, 2620
R_int	0.109
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.123, 0.323, 1.01
No. of reflections	4398
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.51, −1.04

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Selected bond lengths (Å) top

Zn1—O2	1.884 (8)	Zn1—N1	2.016 (8)
Zn1—O1	1.885 (7)	Zn1—N2	2.049 (8)

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