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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023177/hb6099sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023177/hb6099Isup2.hkl
Contains datablock I

CCDC reference: 255406

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

Computing details top

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) top
Crystal data top
[Zn(C25H20N2O2)]F(000) = 920
Mr = 445.80Dx = 1.478 Mg m3
Orthorhombic, Cmc21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2Cell parameters from 3565 reflections
a = 30.601 (4) Åθ = 2.5–27.2°
b = 8.4526 (11) ŵ = 1.25 mm1
c = 7.7465 (10) ÅT = 273 K
V = 2003.7 (5) Å3Block, colourless
Z = 40.27 × 0.22 × 0.19 mm
Data collection top
Bruker SMART1000 CCD
diffractometer
1983 independent reflections
Radiation source: fine-focus sealed tube1908 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 26.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3737
Tmin = 0.729, Tmax = 0.797k = 710
5623 measured reflectionsl = 99
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0924P)2 + 0.1608P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.124(Δ/σ)max < 0.001
S = 1.11Δρmax = 0.57 e Å3
1983 reflectionsΔρmin = 0.35 e Å3
140 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0049 (10)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 844 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.09 (2)
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
xyzUiso*/Ueq
Zn10.50000.07324 (5)0.38651 (8)0.0529 (2)
O10.46015 (8)0.2317 (3)0.4355 (3)0.0556 (6)
N10.45487 (11)0.0697 (3)0.3394 (4)0.0526 (8)
C10.40010 (10)0.1321 (4)0.2722 (4)0.0512 (7)
C20.42126 (10)0.2482 (3)0.3706 (5)0.0498 (7)
C30.39833 (12)0.3918 (4)0.4094 (6)0.0580 (8)
H30.41120.46670.48130.070*
C40.35824 (15)0.4195 (4)0.3423 (6)0.0671 (13)
H40.34390.51310.36980.081*
C50.33754 (11)0.3091 (5)0.2309 (5)0.0604 (8)
C60.29611 (13)0.3414 (6)0.1577 (6)0.0745 (11)
H60.28200.43600.18310.089*
C70.27672 (13)0.2349 (7)0.0504 (7)0.0828 (13)
H70.24960.25760.00210.099*
C80.29713 (16)0.0932 (5)0.0130 (8)0.0766 (12)
H80.28370.02180.06130.092*
C90.33675 (14)0.0567 (5)0.0835 (6)0.0666 (10)
H90.34980.03980.05750.080*
C100.35819 (10)0.1634 (4)0.1956 (4)0.0540 (7)
C110.41737 (11)0.0268 (5)0.2789 (5)0.0564 (8)
H110.39960.10660.23500.068*
C120.45942 (14)0.2424 (4)0.3686 (8)0.0746 (12)
H12A0.43480.27900.43640.090*
H12B0.45840.29610.25800.090*
C130.50000.2867 (7)0.4575 (10)0.0813 (19)
H13A0.50000.40040.47440.098*
H13B0.50000.23780.57080.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0610 (3)0.0465 (3)0.0513 (3)0.0000.0000.0016 (2)
O10.0554 (12)0.0471 (10)0.0643 (17)0.0008 (8)0.0016 (10)0.0096 (10)
N10.0603 (16)0.0408 (13)0.057 (2)0.0040 (9)0.0071 (12)0.0018 (10)
C10.0497 (16)0.0564 (18)0.0475 (16)0.0020 (14)0.0136 (13)0.0023 (13)
C20.0540 (14)0.0485 (13)0.0469 (16)0.0025 (10)0.0139 (16)0.0018 (15)
C30.0615 (17)0.0494 (14)0.063 (2)0.0031 (12)0.0083 (17)0.0021 (17)
C40.065 (2)0.0573 (19)0.079 (4)0.0045 (13)0.0170 (19)0.0033 (15)
C50.0524 (17)0.071 (2)0.058 (2)0.0022 (15)0.0143 (15)0.0056 (16)
C60.0549 (19)0.089 (3)0.080 (3)0.008 (2)0.0125 (19)0.005 (2)
C70.053 (2)0.114 (4)0.082 (3)0.003 (2)0.001 (2)0.000 (3)
C80.056 (2)0.099 (3)0.075 (3)0.0074 (19)0.001 (2)0.010 (2)
C90.054 (2)0.082 (3)0.064 (3)0.0052 (16)0.0115 (18)0.0134 (17)
C100.0471 (15)0.0691 (19)0.0458 (16)0.0051 (15)0.0163 (14)0.0010 (14)
C110.0575 (18)0.0532 (18)0.058 (2)0.0069 (15)0.0087 (16)0.0082 (15)
C120.084 (2)0.0400 (14)0.100 (3)0.0043 (13)0.005 (3)0.001 (2)
C130.124 (6)0.049 (3)0.071 (3)0.0000.0000.006 (2)
Geometric parameters (Å, º) top
Zn1—O11.851 (2)C5—C61.415 (6)
Zn1—O1i1.851 (2)C6—C71.361 (7)
Zn1—N11.871 (3)C6—H60.9300
Zn1—N1i1.871 (3)C7—C81.381 (7)
O1—C21.299 (4)C7—H70.9300
N1—C111.291 (5)C8—C91.365 (7)
N1—C121.484 (4)C8—H80.9300
C1—C21.401 (5)C9—C101.413 (6)
C1—C101.438 (5)C9—H90.9300
C1—C111.444 (5)C11—H110.9300
C2—C31.434 (4)C12—C131.469 (6)
C3—C41.352 (6)C12—H12A0.9700
C3—H30.9300C12—H12B0.9700
C4—C51.420 (6)C13—C12i1.469 (6)
C4—H40.9300C13—H13A0.9700
C5—C101.411 (5)C13—H13B0.9700
O1—Zn1—O1i82.42 (14)C6—C7—C8120.3 (4)
O1—Zn1—N191.20 (12)C6—C7—H7119.9
O1i—Zn1—N1173.59 (11)C8—C7—H7119.9
O1—Zn1—N1i173.59 (11)C9—C8—C7120.9 (4)
O1i—Zn1—N1i91.20 (12)C9—C8—H8119.5
N1—Zn1—N1i95.17 (18)C7—C8—H8119.5
C2—O1—Zn1127.0 (2)C8—C9—C10120.9 (4)
C11—N1—C12114.5 (3)C8—C9—H9119.5
C11—N1—Zn1123.1 (2)C10—C9—H9119.5
C12—N1—Zn1122.4 (3)C5—C10—C9117.9 (3)
C2—C1—C10120.5 (3)C5—C10—C1118.7 (3)
C2—C1—C11117.6 (3)C9—C10—C1123.4 (4)
C10—C1—C11120.8 (3)N1—C11—C1126.8 (3)
O1—C2—C1124.0 (3)N1—C11—H11116.6
O1—C2—C3117.3 (3)C1—C11—H11116.6
C1—C2—C3118.7 (3)C13—C12—N1113.7 (4)
C4—C3—C2120.6 (4)C13—C12—H12A108.8
C4—C3—H3119.7N1—C12—H12A108.8
C2—C3—H3119.7C13—C12—H12B108.8
C3—C4—C5121.6 (3)N1—C12—H12B108.8
C3—C4—H4119.2H12A—C12—H12B107.7
C5—C4—H4119.2C12—C13—C12i115.4 (6)
C10—C5—C6119.5 (4)C12—C13—H13A108.4
C10—C5—C4119.4 (3)C12i—C13—H13A108.4
C6—C5—C4121.1 (4)C12—C13—H13B108.4
C7—C6—C5120.5 (4)C12i—C13—H13B108.4
C7—C6—H6119.8H13A—C13—H13B107.5
C5—C6—H6119.8
Symmetry code: (i) x+1, y, z.
 

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