{1,1'-[1,3-Propane­diyl­bis­(nitrilo­methyl­idyne)]di-2-naphtholato}zinc(II), containing a square-planar ZnO₂N₂ group

The title compound, [Zn(C₂₄H₁₈N₂O₂)], is a mononuclear zinc(II) complex. The Zn atom is located on a mirror plane and is coordinated by two N atoms and two O atoms from a Schiff base ligand in a slightly distorted square-planar geometry.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.041
• wR factor = 0.124
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13     ..       5.17 su

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.48
           From the CIF: _reflns_number_total               1983
           Count of symmetry unique reflns         1139
           Completeness (_total/calc)            174.10%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       844
           Fraction of Friedel pairs measured     0.741
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 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.

{1,1'-[1,3-Propanediylbis(nitrilomethylidyne)]di-2-naphtholato}zinc(II)

Crystal data

[Zn(C25H20N2O2)]	F(000) = 920
Mr = 445.80	Dx = 1.478 Mg m^−3
Orthorhombic, Cmc21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2	Cell parameters from 3565 reflections
a = 30.601 (4) Å	θ = 2.5–27.2°
b = 8.4526 (11) Å	µ = 1.25 mm^−1
c = 7.7465 (10) Å	T = 273 K
V = 2003.7 (5) Å^3	Block, colourless
Z = 4	0.27 × 0.22 × 0.19 mm

Data collection

Bruker SMART1000 CCD diffractometer	1983 independent reflections
Radiation source: fine-focus sealed tube	1908 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 26.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −37→37
Tmin = 0.729, Tmax = 0.797	k = −7→10
5623 measured reflections	l = −9→9

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0924P)^2 + 0.1608P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.124	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.57 e Å^−3
1983 reflections	Δρmin = −0.35 e Å^−3
140 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0049 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 844 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.09 (2)

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	0.5000	0.07324 (5)	0.38651 (8)	0.0529 (2)
O1	0.46015 (8)	0.2317 (3)	0.4355 (3)	0.0556 (6)
N1	0.45487 (11)	−0.0697 (3)	0.3394 (4)	0.0526 (8)
C1	0.40010 (10)	0.1321 (4)	0.2722 (4)	0.0512 (7)
C2	0.42126 (10)	0.2482 (3)	0.3706 (5)	0.0498 (7)
C3	0.39833 (12)	0.3918 (4)	0.4094 (6)	0.0580 (8)
H3	0.4112	0.4667	0.4813	0.070*
C4	0.35824 (15)	0.4195 (4)	0.3423 (6)	0.0671 (13)
H4	0.3439	0.5131	0.3698	0.081*
C5	0.33754 (11)	0.3091 (5)	0.2309 (5)	0.0604 (8)
C6	0.29611 (13)	0.3414 (6)	0.1577 (6)	0.0745 (11)
H6	0.2820	0.4360	0.1831	0.089*
C7	0.27672 (13)	0.2349 (7)	0.0504 (7)	0.0828 (13)
H7	0.2496	0.2576	0.0021	0.099*
C8	0.29713 (16)	0.0932 (5)	0.0130 (8)	0.0766 (12)
H8	0.2837	0.0218	−0.0613	0.092*
C9	0.33675 (14)	0.0567 (5)	0.0835 (6)	0.0666 (10)
H9	0.3498	−0.0398	0.0575	0.080*
C10	0.35819 (10)	0.1634 (4)	0.1956 (4)	0.0540 (7)
C11	0.41737 (11)	−0.0268 (5)	0.2789 (5)	0.0564 (8)
H11	0.3996	−0.1066	0.2350	0.068*
C12	0.45942 (14)	−0.2424 (4)	0.3686 (8)	0.0746 (12)
H12A	0.4348	−0.2790	0.4364	0.090*
H12B	0.4584	−0.2961	0.2580	0.090*
C13	0.5000	−0.2867 (7)	0.4575 (10)	0.0813 (19)
H13A	0.5000	−0.4004	0.4744	0.098*
H13B	0.5000	−0.2378	0.5708	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0610 (3)	0.0465 (3)	0.0513 (3)	0.000	0.000	−0.0016 (2)
O1	0.0554 (12)	0.0471 (10)	0.0643 (17)	−0.0008 (8)	0.0016 (10)	−0.0096 (10)
N1	0.0603 (16)	0.0408 (13)	0.057 (2)	−0.0040 (9)	0.0071 (12)	−0.0018 (10)
C1	0.0497 (16)	0.0564 (18)	0.0475 (16)	−0.0020 (14)	0.0136 (13)	−0.0023 (13)
C2	0.0540 (14)	0.0485 (13)	0.0469 (16)	−0.0025 (10)	0.0139 (16)	0.0018 (15)
C3	0.0615 (17)	0.0494 (14)	0.063 (2)	−0.0031 (12)	0.0083 (17)	−0.0021 (17)
C4	0.065 (2)	0.0573 (19)	0.079 (4)	0.0045 (13)	0.0170 (19)	−0.0033 (15)
C5	0.0524 (17)	0.071 (2)	0.058 (2)	−0.0022 (15)	0.0143 (15)	0.0056 (16)
C6	0.0549 (19)	0.089 (3)	0.080 (3)	0.008 (2)	0.0125 (19)	0.005 (2)
C7	0.053 (2)	0.114 (4)	0.082 (3)	−0.003 (2)	−0.001 (2)	0.000 (3)
C8	0.056 (2)	0.099 (3)	0.075 (3)	−0.0074 (19)	−0.001 (2)	−0.010 (2)
C9	0.054 (2)	0.082 (3)	0.064 (3)	−0.0052 (16)	0.0115 (18)	−0.0134 (17)
C10	0.0471 (15)	0.0691 (19)	0.0458 (16)	−0.0051 (15)	0.0163 (14)	0.0010 (14)
C11	0.0575 (18)	0.0532 (18)	0.058 (2)	−0.0069 (15)	0.0087 (16)	−0.0082 (15)
C12	0.084 (2)	0.0400 (14)	0.100 (3)	−0.0043 (13)	−0.005 (3)	−0.001 (2)
C13	0.124 (6)	0.049 (3)	0.071 (3)	0.000	0.000	0.006 (2)

Geometric parameters (Å, º)

Zn1—O1	1.851 (2)	C5—C6	1.415 (6)
Zn1—O1^i	1.851 (2)	C6—C7	1.361 (7)
Zn1—N1	1.871 (3)	C6—H6	0.9300
Zn1—N1^i	1.871 (3)	C7—C8	1.381 (7)
O1—C2	1.299 (4)	C7—H7	0.9300
N1—C11	1.291 (5)	C8—C9	1.365 (7)
N1—C12	1.484 (4)	C8—H8	0.9300
C1—C2	1.401 (5)	C9—C10	1.413 (6)
C1—C10	1.438 (5)	C9—H9	0.9300
C1—C11	1.444 (5)	C11—H11	0.9300
C2—C3	1.434 (4)	C12—C13	1.469 (6)
C3—C4	1.352 (6)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.420 (6)	C13—C12^i	1.469 (6)
C4—H4	0.9300	C13—H13A	0.9700
C5—C10	1.411 (5)	C13—H13B	0.9700
O1—Zn1—O1^i	82.42 (14)	C6—C7—C8	120.3 (4)
O1—Zn1—N1	91.20 (12)	C6—C7—H7	119.9
O1^i—Zn1—N1	173.59 (11)	C8—C7—H7	119.9
O1—Zn1—N1^i	173.59 (11)	C9—C8—C7	120.9 (4)
O1^i—Zn1—N1^i	91.20 (12)	C9—C8—H8	119.5
N1—Zn1—N1^i	95.17 (18)	C7—C8—H8	119.5
C2—O1—Zn1	127.0 (2)	C8—C9—C10	120.9 (4)
C11—N1—C12	114.5 (3)	C8—C9—H9	119.5
C11—N1—Zn1	123.1 (2)	C10—C9—H9	119.5
C12—N1—Zn1	122.4 (3)	C5—C10—C9	117.9 (3)
C2—C1—C10	120.5 (3)	C5—C10—C1	118.7 (3)
C2—C1—C11	117.6 (3)	C9—C10—C1	123.4 (4)
C10—C1—C11	120.8 (3)	N1—C11—C1	126.8 (3)
O1—C2—C1	124.0 (3)	N1—C11—H11	116.6
O1—C2—C3	117.3 (3)	C1—C11—H11	116.6
C1—C2—C3	118.7 (3)	C13—C12—N1	113.7 (4)
C4—C3—C2	120.6 (4)	C13—C12—H12A	108.8
C4—C3—H3	119.7	N1—C12—H12A	108.8
C2—C3—H3	119.7	C13—C12—H12B	108.8
C3—C4—C5	121.6 (3)	N1—C12—H12B	108.8
C3—C4—H4	119.2	H12A—C12—H12B	107.7
C5—C4—H4	119.2	C12—C13—C12^i	115.4 (6)
C10—C5—C6	119.5 (4)	C12—C13—H13A	108.4
C10—C5—C4	119.4 (3)	C12^i—C13—H13A	108.4
C6—C5—C4	121.1 (4)	C12—C13—H13B	108.4
C7—C6—C5	120.5 (4)	C12^i—C13—H13B	108.4
C7—C6—H6	119.8	H13A—C13—H13B	107.5
C5—C6—H6	119.8

Symmetry code: (i) −x+1, y, z.