Retracted: [N,N'-Bis(2-hydroxy­naphthyl­methyl­ene)-1,2-ethanediaminato]zinc(II)

The title compound, [Zn(C₂₄H₁₈N₂O₂)], is a mononuclear zinc(II) complex. The crystal is isostructural with the previously studied Ni and Co analogues. The Zn atom has a slightly distorted square-planar coordination formed by two O and two N atoms of the tetra­dentate Schiff base ligand.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.137
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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.

(I)

Crystal data

[Zn(C24H18N2O2)]	F(000) = 888
Mr = 431.77	Dx = 1.553 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.681 (1) Å	Cell parameters from 2849 reflections
b = 8.184 (1) Å	θ = 2.7–26.9°
c = 12.957 (1) Å	µ = 1.35 mm^−1
β = 99.92 (1)°	T = 298 K
V = 1846.9 (3) Å^3	Block, colourless
Z = 4	0.33 × 0.30 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4153 independent reflections
Radiation source: fine-focus sealed tube	3029 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→22
Tmin = 0.663, Tmax = 0.755	k = −10→9
9152 measured reflections	l = −15→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0753P)^2] where P = (Fo^2 + 2Fc^2)/3
4153 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.022954 (19)	0.33477 (4)	0.07297 (3)	0.03501 (15)
O1	0.09689 (11)	0.4212 (3)	0.17690 (15)	0.0333 (5)
O2	−0.04847 (11)	0.4332 (3)	0.14147 (14)	0.0324 (5)
N1	0.09373 (14)	0.2323 (3)	0.00696 (18)	0.0318 (5)
N2	−0.05060 (14)	0.2595 (3)	−0.03401 (18)	0.0300 (5)
C1	0.21010 (18)	0.3180 (4)	0.1207 (2)	0.0334 (7)
C2	0.17118 (17)	0.4107 (4)	0.1863 (2)	0.0328 (7)
C3	0.21539 (18)	0.5026 (4)	0.2698 (2)	0.0398 (7)
H3	0.1902	0.5695	0.3110	0.048*
C4	0.29259 (19)	0.4941 (4)	0.2898 (3)	0.0449 (8)
H4	0.3194	0.5548	0.3449	0.054*
C5	0.33438 (19)	0.3949 (5)	0.2290 (3)	0.0445 (8)
C6	0.4156 (2)	0.3808 (6)	0.2523 (3)	0.0608 (11)
H6	0.4424	0.4371	0.3095	0.073*
C7	0.4547 (2)	0.2885 (6)	0.1941 (4)	0.0714 (13)
H7	0.5079	0.2803	0.2112	0.086*
C8	0.4150 (2)	0.2051 (5)	0.1079 (4)	0.0633 (11)
H8	0.4421	0.1414	0.0672	0.076*
C9	0.3373 (2)	0.2154 (5)	0.0822 (3)	0.0509 (9)
H9	0.3123	0.1596	0.0236	0.061*
C10	0.29369 (18)	0.3085 (4)	0.1422 (3)	0.0388 (7)
C11	0.16768 (18)	0.2337 (4)	0.0334 (2)	0.0347 (7)
H11	0.1956	0.1743	−0.0083	0.042*
C12	0.05967 (19)	0.1355 (4)	−0.0862 (3)	0.0393 (7)
H12A	0.0558	0.0215	−0.0673	0.047*
H12B	0.0916	0.1430	−0.1398	0.047*
C13	−0.01894 (18)	0.2038 (4)	−0.1267 (2)	0.0378 (7)
H13A	−0.0155	0.2945	−0.1738	0.045*
H13B	−0.0516	0.1203	−0.1643	0.045*
C14	−0.12390 (18)	0.2639 (4)	−0.0405 (2)	0.0342 (7)
H14	−0.1533	0.2178	−0.0998	0.041*
C15	−0.16416 (18)	0.3333 (3)	0.0351 (2)	0.0313 (6)
C16	−0.12240 (17)	0.4222 (4)	0.1194 (2)	0.0321 (6)
C17	−0.16514 (18)	0.5123 (4)	0.1856 (2)	0.0384 (7)
H17	−0.1386	0.5729	0.2410	0.046*
C18	−0.24248 (19)	0.5110 (4)	0.1694 (3)	0.0466 (8)
H18	−0.2679	0.5728	0.2131	0.056*
C19	−0.28649 (19)	0.4178 (4)	0.0873 (3)	0.0452 (8)
C20	−0.3675 (2)	0.4170 (5)	0.0708 (3)	0.0600 (11)
H20	−0.3928	0.4788	0.1145	0.072*
C21	−0.4088 (2)	0.3293 (6)	−0.0065 (4)	0.0721 (14)
H21	−0.4622	0.3300	−0.0161	0.087*
C22	−0.3710 (2)	0.2374 (6)	−0.0722 (3)	0.0614 (11)
H22	−0.3997	0.1767	−0.1259	0.074*
C23	−0.2926 (2)	0.2340 (5)	−0.0598 (3)	0.0496 (9)
H23	−0.2688	0.1700	−0.1041	0.060*
C24	−0.24742 (18)	0.3271 (4)	0.0200 (3)	0.0372 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0384 (2)	0.0396 (2)	0.0272 (2)	0.00038 (16)	0.00605 (15)	−0.00013 (15)
O1	0.0340 (11)	0.0419 (12)	0.0236 (10)	0.0007 (9)	0.0038 (8)	−0.0029 (9)
O2	0.0336 (11)	0.0404 (12)	0.0228 (10)	0.0012 (9)	0.0041 (8)	−0.0037 (9)
N1	0.0410 (14)	0.0326 (13)	0.0226 (12)	0.0007 (11)	0.0080 (10)	0.0000 (11)
N2	0.0374 (14)	0.0304 (13)	0.0220 (12)	−0.0007 (11)	0.0049 (10)	−0.0001 (10)
C1	0.0357 (16)	0.0351 (16)	0.0301 (16)	0.0000 (13)	0.0069 (12)	0.0066 (13)
C2	0.0368 (16)	0.0343 (16)	0.0269 (15)	−0.0020 (13)	0.0039 (12)	0.0060 (13)
C3	0.0465 (19)	0.0407 (18)	0.0320 (17)	−0.0055 (15)	0.0060 (14)	−0.0034 (14)
C4	0.0433 (19)	0.050 (2)	0.0388 (18)	−0.0114 (16)	0.0004 (14)	−0.0026 (16)
C5	0.0394 (18)	0.046 (2)	0.046 (2)	−0.0061 (15)	0.0024 (15)	0.0083 (17)
C6	0.038 (2)	0.073 (3)	0.068 (3)	−0.0071 (19)	−0.0014 (18)	−0.002 (2)
C7	0.0315 (19)	0.082 (3)	0.099 (4)	0.003 (2)	0.007 (2)	0.001 (3)
C8	0.042 (2)	0.073 (3)	0.077 (3)	0.0123 (19)	0.016 (2)	−0.001 (2)
C9	0.043 (2)	0.058 (2)	0.053 (2)	0.0048 (17)	0.0122 (17)	0.0010 (19)
C10	0.0364 (17)	0.0382 (18)	0.0420 (19)	0.0023 (13)	0.0080 (14)	0.0104 (15)
C11	0.0400 (17)	0.0374 (17)	0.0286 (16)	0.0048 (14)	0.0116 (13)	0.0027 (13)
C12	0.0454 (18)	0.0406 (18)	0.0322 (17)	0.0027 (14)	0.0078 (14)	−0.0078 (14)
C13	0.0485 (19)	0.0433 (19)	0.0213 (15)	−0.0043 (14)	0.0057 (13)	−0.0070 (13)
C14	0.0418 (18)	0.0327 (16)	0.0261 (15)	−0.0041 (13)	0.0003 (13)	0.0039 (13)
C15	0.0364 (16)	0.0292 (15)	0.0279 (15)	0.0001 (12)	0.0043 (12)	0.0053 (12)
C16	0.0381 (17)	0.0308 (16)	0.0279 (15)	0.0058 (13)	0.0074 (12)	0.0103 (13)
C17	0.0434 (18)	0.0383 (18)	0.0342 (17)	0.0073 (14)	0.0084 (13)	−0.0004 (14)
C18	0.0475 (19)	0.045 (2)	0.049 (2)	0.0100 (16)	0.0143 (16)	0.0000 (17)
C19	0.0374 (18)	0.046 (2)	0.053 (2)	0.0054 (15)	0.0111 (15)	0.0129 (17)
C20	0.043 (2)	0.065 (3)	0.074 (3)	0.0098 (19)	0.017 (2)	0.011 (2)
C21	0.0306 (19)	0.081 (3)	0.100 (4)	−0.002 (2)	0.000 (2)	0.019 (3)
C22	0.047 (2)	0.070 (3)	0.064 (3)	−0.012 (2)	−0.0025 (19)	0.003 (2)
C23	0.0424 (19)	0.055 (2)	0.049 (2)	−0.0059 (17)	0.0012 (16)	0.0055 (18)
C24	0.0379 (17)	0.0372 (17)	0.0350 (17)	−0.0015 (13)	0.0027 (13)	0.0100 (14)

Geometric parameters (Å, º)

Zn1—N1	1.836 (2)	C9—H9	0.9300
Zn1—N2	1.836 (2)	C11—H11	0.9300
Zn1—O1	1.848 (2)	C12—C13	1.506 (4)
Zn1—O2	1.849 (2)	C12—H12A	0.9700
O1—C2	1.301 (3)	C12—H12B	0.9700
O2—C16	1.292 (3)	C13—H13A	0.9700
N1—C11	1.293 (4)	C13—H13B	0.9700
N1—C12	1.482 (4)	C14—C15	1.425 (4)
N2—C14	1.285 (4)	C14—H14	0.9300
N2—C13	1.481 (4)	C15—C16	1.410 (4)
C1—C2	1.404 (4)	C15—C24	1.452 (4)
C1—C11	1.424 (4)	C16—C17	1.440 (4)
C1—C10	1.458 (4)	C17—C18	1.347 (4)
C2—C3	1.434 (4)	C17—H17	0.9300
C3—C4	1.347 (4)	C18—C19	1.427 (5)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.424 (5)	C19—C20	1.412 (5)
C4—H4	0.9300	C19—C24	1.412 (5)
C5—C10	1.415 (5)	C20—C21	1.342 (6)
C5—C6	1.420 (5)	C20—H20	0.9300
C6—C7	1.341 (6)	C21—C22	1.391 (6)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.392 (6)	C22—C23	1.368 (5)
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.360 (5)	C23—C24	1.415 (5)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.409 (5)
N1—Zn1—N2	86.91 (11)	C1—C11—H11	117.1
N1—Zn1—O1	93.49 (10)	N1—C12—C13	107.8 (2)
N2—Zn1—O1	176.90 (10)	N1—C12—H12A	110.1
N1—Zn1—O2	178.54 (10)	C13—C12—H12A	110.1
N2—Zn1—O2	93.16 (10)	N1—C12—H12B	110.1
O1—Zn1—O2	86.52 (9)	C13—C12—H12B	110.1
C2—O1—Zn1	128.25 (19)	H12A—C12—H12B	108.5
C16—O2—Zn1	127.71 (19)	N2—C13—C12	106.7 (2)
C11—N1—C12	118.1 (3)	N2—C13—H13A	110.4
C11—N1—Zn1	127.7 (2)	C12—C13—H13A	110.4
C12—N1—Zn1	114.2 (2)	N2—C13—H13B	110.4
C14—N2—C13	118.3 (3)	C12—C13—H13B	110.4
C14—N2—Zn1	128.0 (2)	H13A—C13—H13B	108.6
C13—N2—Zn1	113.44 (19)	N2—C14—C15	125.7 (3)
C2—C1—C11	119.8 (3)	N2—C14—H14	117.1
C2—C1—C10	120.0 (3)	C15—C14—H14	117.1
C11—C1—C10	120.2 (3)	C16—C15—C14	118.8 (3)
O1—C2—C1	124.8 (3)	C16—C15—C24	120.4 (3)
O1—C2—C3	116.5 (3)	C14—C15—C24	120.6 (3)
C1—C2—C3	118.7 (3)	O2—C16—C15	125.6 (3)
C4—C3—C2	121.4 (3)	O2—C16—C17	116.5 (3)
C4—C3—H3	119.3	C15—C16—C17	117.8 (3)
C2—C3—H3	119.3	C18—C17—C16	121.7 (3)
C3—C4—C5	121.9 (3)	C18—C17—H17	119.1
C3—C4—H4	119.0	C16—C17—H17	119.1
C5—C4—H4	119.0	C17—C18—C19	121.9 (3)
C10—C5—C6	119.0 (4)	C17—C18—H18	119.0
C10—C5—C4	118.9 (3)	C19—C18—H18	119.0
C6—C5—C4	122.1 (3)	C20—C19—C24	119.7 (4)
C7—C6—C5	121.8 (4)	C20—C19—C18	121.6 (3)
C7—C6—H6	119.1	C24—C19—C18	118.7 (3)
C5—C6—H6	119.1	C21—C20—C19	121.5 (4)
C6—C7—C8	119.3 (4)	C21—C20—H20	119.2
C6—C7—H7	120.3	C19—C20—H20	119.2
C8—C7—H7	120.3	C20—C21—C22	119.2 (4)
C9—C8—C7	121.0 (4)	C20—C21—H21	120.4
C9—C8—H8	119.5	C22—C21—H21	120.4
C7—C8—H8	119.5	C23—C22—C21	121.6 (4)
C8—C9—C10	121.6 (4)	C23—C22—H22	119.2
C8—C9—H9	119.2	C21—C22—H22	119.2
C10—C9—H9	119.2	C22—C23—C24	120.5 (4)
C9—C10—C5	117.2 (3)	C22—C23—H23	119.7
C9—C10—C1	123.8 (3)	C24—C23—H23	119.7
C5—C10—C1	119.0 (3)	C19—C24—C23	117.3 (3)
N1—C11—C1	125.8 (3)	C19—C24—C15	119.4 (3)
N1—C11—H11	117.1	C23—C24—C15	123.3 (3)
N1—Zn1—O1—C2	3.3 (3)	Zn1—N1—C11—C1	−0.5 (5)
O2—Zn1—O1—C2	−178.1 (3)	C2—C1—C11—N1	−0.4 (5)
N2—Zn1—O2—C16	7.9 (2)	C10—C1—C11—N1	179.6 (3)
O1—Zn1—O2—C16	−175.2 (2)	C11—N1—C12—C13	−157.4 (3)
N2—Zn1—N1—C11	176.3 (3)	Zn1—N1—C12—C13	23.7 (3)
O1—Zn1—N1—C11	−0.6 (3)	C14—N2—C13—C12	−153.9 (3)
N2—Zn1—N1—C12	−4.8 (2)	Zn1—N2—C13—C12	32.2 (3)
O1—Zn1—N1—C12	178.2 (2)	N1—C12—C13—N2	−34.0 (3)
N1—Zn1—N2—C14	170.6 (3)	C13—N2—C14—C15	−171.5 (3)
O2—Zn1—N2—C14	−7.9 (3)	Zn1—N2—C14—C15	1.5 (5)
N1—Zn1—N2—C13	−16.2 (2)	N2—C14—C15—C16	7.8 (5)
O2—Zn1—N2—C13	165.3 (2)	N2—C14—C15—C24	−178.5 (3)
Zn1—O1—C2—C1	−5.1 (4)	Zn1—O2—C16—C15	−1.5 (4)
Zn1—O1—C2—C3	174.4 (2)	Zn1—O2—C16—C17	−179.86 (19)
C11—C1—C2—O1	3.3 (5)	C14—C15—C16—O2	−7.8 (4)
C10—C1—C2—O1	−176.7 (3)	C24—C15—C16—O2	178.5 (3)
C11—C1—C2—C3	−176.2 (3)	C14—C15—C16—C17	170.6 (3)
C10—C1—C2—C3	3.8 (4)	C24—C15—C16—C17	−3.1 (4)
O1—C2—C3—C4	176.7 (3)	O2—C16—C17—C18	179.4 (3)
C1—C2—C3—C4	−3.8 (5)	C15—C16—C17—C18	0.9 (4)
C2—C3—C4—C5	0.5 (5)	C16—C17—C18—C19	1.4 (5)
C3—C4—C5—C10	2.8 (5)	C17—C18—C19—C20	180.0 (3)
C3—C4—C5—C6	−177.5 (4)	C17—C18—C19—C24	−1.3 (5)
C10—C5—C6—C7	0.3 (6)	C24—C19—C20—C21	1.3 (6)
C4—C5—C6—C7	−179.3 (4)	C18—C19—C20—C21	180.0 (4)
C5—C6—C7—C8	0.6 (7)	C19—C20—C21—C22	−0.2 (7)
C6—C7—C8—C9	−0.3 (7)	C20—C21—C22—C23	0.1 (7)
C7—C8—C9—C10	−0.9 (7)	C21—C22—C23—C24	−1.1 (6)
C8—C9—C10—C5	1.7 (5)	C20—C19—C24—C23	−2.2 (5)
C8—C9—C10—C1	−177.3 (4)	C18—C19—C24—C23	179.1 (3)
C6—C5—C10—C9	−1.4 (5)	C20—C19—C24—C15	177.8 (3)
C4—C5—C10—C9	178.2 (3)	C18—C19—C24—C15	−1.0 (5)
C6—C5—C10—C1	177.6 (3)	C22—C23—C24—C19	2.1 (5)
C4—C5—C10—C1	−2.7 (5)	C22—C23—C24—C15	−177.8 (3)
C2—C1—C10—C9	178.4 (3)	C16—C15—C24—C19	3.2 (4)
C11—C1—C10—C9	−1.6 (5)	C14—C15—C24—C19	−170.4 (3)
C2—C1—C10—C5	−0.6 (4)	C16—C15—C24—C23	−176.9 (3)
C11—C1—C10—C5	179.4 (3)	C14—C15—C24—C23	9.5 (5)
C12—N1—C11—C1	−179.3 (3)