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The crystal structure of the title compound, {[Zn(C52H36N4O8)]·2C4H9NO}n, consists of two-dimensional coordination polymers of the six-coordinate zinc–porphyrin unit [Zn—N = 2.039 (2) and 2.061 (2) Å, and Zn—O = 2.540 (2) Å], which inter­calate between the mol­ecules of N,N-dimethyl­acetamide solvent. The Zn atom lies on an inversion centre.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106035840/ga3024sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106035840/ga3024Isup2.hkl
Contains datablock I

CCDC reference: 625682

Comment top

The formulation of porphyrin network and framework solids has received increasing attention in recent years (Goldberg, 2005; Kosal et al., 2002; Diskin-Posner et al., 2000; Krupitsky et al., 1994; Abrahams et al., 1994), due to their potential application to problems of materials storage and separation as well as heterogeneous catalysis. Most of the supramolecular architectures reported to date involve external auxiliaries (metal ions or organic ligands) as linkers between the porphyrin units. Only a few examples of direct networking between suitably functionalized metalloporphyrins have been observed thus far, including our first robust porous solid consisting of a three-dimensional coordination polymer of the zinc–tetra(4-pyridyl)porphyrin (Krupitsky et al., 1994; Shmilovits et al., 2004a; George et al., 2006). As part of our systematic investigation of porphyrin-based solids, we report here the direct coordination polymerization of the title porphyrin derivative and the intercalate-type crystal structure it forms with N,N'-dimethylacetamide solvent, (I) (Fig. 1).

The carbomethoxy function has not been utilized before in the supramolecular assembly of porphyrin arrays. The bond lengths and angles in (I) (Table 1) show standard values [Cambridge Structural Database, Version 5.27; Mercury (Macrae et al., 2006); Allen, 2002], in particular for the Zn—N(pyrrole) distances (Shmilovits et al., 2004b).

The inter-porphyrin coordination pattern in (I) is illustrated in Fig. 2. It represents a unique two-dimensional coordination polymer obtained by direct coordination of two trans-related peripheral carbomethoxy groups of one porphyrin to the metal core of neighbouring moieties. Thus, formation of the polymeric array is effected by axial coordination of the Zn centres from above and below to the carbomethoxy groups of two perching unitsacross inversion at Zn—O(C) of 2.540 (2) Å. Two trans-related carbomethoxyphenyl arms along a roughly perpendicular direction of the central molecule associate with the metal centres of two other neighbouring entities. Each porphyrin unit (located on an inversion centre) is thus involved in a four-point connection to the surrounding species, affording a condensed two-dimensional coordination polymer assembly. The supramolecular Zn—O coordinative interactions operate between molecular units related to each other by the screw/glide symmetry (thus forming a herringbone pattern). There are fortuitous C—H···π interactions [PLATON (Spek, 2003)] between the adjacent carbomethoxy methyl atom H32A and the Zn-pyrrole ring (Zn/N11/C4–C6/N12) at (x, 1/2 − y, z − 1/2) of 2.45 Å (C—H···π angle 167°). The resulting polymeric arrays have corrugated surfaces.

Similar polymer constructions have been reported previously only for the Mn–tetrakis(4'-carboxyphenyl)porphyrin, with the embedded Mn ions having a distinct preference for a six-coordinate environment and exhibiting considerably shorter Mn—O axial interactions (2.2–2.3 Å; Shmilovits et al., 2004a; George et al., 2006). Octahedral coordination is less common for the d10 Zn ions, with lower affinity for oxo ligands than Mn, thus representing somewhat weaker though still significant interactions at Zn—O near 2.5 Å (Krishna Kumar et al., 1998). The crystal structure of (I) consists of a stacked arrangement of the polymeric layers along the a axis, which do not interact directly (except by dispersion). The corresponding shortest non-bonding distance involves the terminal carbomethoxy substituents, with C32···O20(2 − x, y − 3/2, 1/2 − z) = 3.351 (3) Å.

Overall, this represents an intercalated pattern, with the N,N'-dimethylacetamide solvent species incorporated into the interface regions parallel to the layered arrays (Fig. 3). Thus, the structure of (I) consists of uniquely assembled two-dimensional multi-porphyrin arrays via direct coordination polymerization, which is rarely observed.

Experimental top

The title porphyrin moiety was synthesized by standard literature procedures (Lindsey et al., 1987; Adler et al., 1970). The initially obtained free base porphyrin derivative was fully characterized by 1H NMR, UV–vis and MS techniques. Crystals of (I) were obtained by dissolving the metallated product in N,N'-dimethylacetamide, followed by slow evaporation.

Refinement top

The H atoms were located in calculated positions and were constrained to ride on their parent atoms, with C—H distances in the range 0.95–0.98 Å and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C).

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of compound (I), showing the atom-labelling scheme of the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level at ca 110 K. H atoms have been omitted for clarity. The metalloporphyrin molecule is located on a centre of inversion at (1/2, 1/2, 1/2).
[Figure 2] Fig. 2. A stereoview, approximately down the a axis, of the crystal structure of (I), illustrating the coordination polymerization scheme. Each porphyrin unit is coordinated to four neighbouring species via two Zn—O(C) and two (C)O—Zn bonds of 2.540 (2) Å. The Zn, N and O atoms are indicated by darkened spheres, and the C atoms by open circles. H atoms have been omitted for clarity.
[Figure 3] Fig. 3. The crystalline architecture of (I), projected down the b axis of the unit cell (c is horizontal and a is vertical). The porphyrin coordination polymers (three successive corrugated layers) are shown in space-filling mode. The N,N'-dimethylacetamide solvent mlecules intercalated between the porphyrin layers are illustrated in stick mode.
Poly[[[µ-5,10,15,20-tetrakis(4-carbomethoxyphenyl)porphyrinato(2-)]zinc(II)] N,N'-dimethylacetamide disolvate] top
Crystal data top
[Zn(C52H36N4O8)]·2C4H9NOF(000) = 1132
Mr = 1084.46Dx = 1.387 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.8014 (4) ÅCell parameters from 5531 reflections
b = 8.9030 (4) Åθ = 1.4–27.9°
c = 21.1399 (9) ŵ = 0.54 mm1
β = 91.675 (3)°T = 110 K
V = 2596.43 (18) Å3Needle, red
Z = 20.45 × 0.10 × 0.10 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
4518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.081
Graphite monochromatorθmax = 27.9°, θmin = 2.4°
Detector resolution: 12.8 pixels mm-1h = 1818
ϕ scansk = 1111
19518 measured reflectionsl = 2727
6135 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0204P)2 + 3.6188P]
where P = (Fo2 + 2Fc2)/3
6135 reflections(Δ/σ)max = 0.002
354 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.54 e Å3
Crystal data top
[Zn(C52H36N4O8)]·2C4H9NOV = 2596.43 (18) Å3
Mr = 1084.46Z = 2
Monoclinic, P21/cMo Kα radiation
a = 13.8014 (4) ŵ = 0.54 mm1
b = 8.9030 (4) ÅT = 110 K
c = 21.1399 (9) Å0.45 × 0.10 × 0.10 mm
β = 91.675 (3)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
4518 reflections with I > 2σ(I)
19518 measured reflectionsRint = 0.081
6135 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.08Δρmax = 0.63 e Å3
6135 reflectionsΔρmin = 0.54 e Å3
354 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
xyzUiso*/Ueq
Zn0.50000.50000.50000.01652 (12)
C10.50651 (18)0.7233 (3)0.61000 (12)0.0178 (6)
C20.55096 (19)0.8623 (3)0.63019 (13)0.0223 (6)
H20.54210.91160.66950.027*
C30.60761 (19)0.9098 (3)0.58306 (13)0.0221 (6)
H30.64580.99860.58290.027*
C40.59897 (18)0.8000 (3)0.53307 (12)0.0181 (6)
C50.64958 (18)0.8049 (3)0.47596 (12)0.0174 (5)
C60.64447 (18)0.6959 (3)0.42805 (12)0.0170 (5)
C70.69243 (19)0.7061 (3)0.36823 (13)0.0215 (6)
H70.73340.78510.35500.026*
C80.66763 (19)0.5813 (3)0.33466 (13)0.0207 (6)
H80.68850.55610.29360.025*
C90.60354 (17)0.4940 (3)0.37303 (11)0.0168 (5)
C100.55909 (18)0.3588 (3)0.35461 (12)0.0176 (5)
N110.53677 (14)0.6880 (2)0.55030 (10)0.0167 (5)
N120.59107 (15)0.5663 (2)0.42966 (10)0.0157 (5)
C130.71720 (18)0.9338 (3)0.46742 (12)0.0167 (5)
C140.81698 (19)0.9071 (3)0.46342 (13)0.0203 (6)
H140.84120.80750.46730.024*
C150.88033 (18)1.0248 (3)0.45392 (12)0.0209 (6)
H150.94781.00550.45140.025*
C160.84606 (18)1.1710 (3)0.44803 (12)0.0184 (6)
C170.74705 (18)1.1991 (3)0.45322 (12)0.0182 (6)
H170.72311.29890.44990.022*
C180.68365 (19)1.0811 (3)0.46330 (12)0.0189 (6)
H180.61651.10110.46740.023*
C190.91657 (19)1.2924 (3)0.43530 (13)0.0217 (6)
O201.00352 (14)1.2801 (2)0.44232 (11)0.0351 (5)
O210.87361 (13)1.4178 (2)0.41391 (10)0.0277 (5)
C220.9374 (2)1.5408 (3)0.39855 (17)0.0342 (8)
H22A0.96911.57880.43740.051*
H22B0.89951.62150.37820.051*
H22C0.98661.50520.36960.051*
C230.58595 (18)0.2923 (3)0.29207 (12)0.0173 (5)
C240.6668 (2)0.1985 (4)0.28915 (13)0.0337 (8)
H240.70420.17790.32660.040*
C250.6928 (2)0.1353 (4)0.23242 (13)0.0324 (8)
H250.74730.07030.23110.039*
C260.63931 (18)0.1666 (3)0.17711 (12)0.0188 (6)
C270.55851 (19)0.2590 (3)0.17987 (12)0.0197 (6)
H270.52160.28090.14240.024*
C280.53155 (19)0.3195 (3)0.23715 (12)0.0206 (6)
H280.47510.38030.23880.025*
C290.66900 (18)0.1086 (3)0.11456 (12)0.0177 (6)
O300.62883 (13)0.1405 (2)0.06465 (8)0.0213 (4)
O310.74769 (13)0.0207 (2)0.11978 (8)0.0246 (5)
C320.7877 (2)0.0283 (4)0.06075 (13)0.0279 (7)
H32A0.73560.06760.03290.042*
H32B0.83580.10730.06920.042*
H32C0.81880.05690.04010.042*
O331.0124 (2)0.3466 (3)0.16201 (13)0.0611 (8)
C340.9438 (3)0.4405 (5)0.16349 (16)0.0443 (9)
C350.8486 (3)0.4059 (5)0.1322 (2)0.0632 (12)
H35A0.85170.30740.11170.095*
H35B0.83310.48290.10040.095*
H35C0.79830.40460.16390.095*
N360.9567 (2)0.5682 (4)0.19365 (15)0.0463 (8)
C371.0521 (2)0.6100 (5)0.22035 (19)0.0535 (11)
H37A1.09890.53040.21160.080*
H37B1.04790.62340.26620.080*
H37C1.07330.70410.20110.080*
C380.8806 (3)0.6828 (5)0.1978 (2)0.0608 (12)
H38A0.89510.76660.16960.091*
H38B0.87820.71950.24150.091*
H38C0.81790.63880.18530.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0173 (2)0.0173 (2)0.0151 (2)0.0031 (2)0.00324 (15)0.00225 (19)
C10.0176 (12)0.0192 (14)0.0165 (13)0.0012 (11)0.0008 (10)0.0018 (11)
C20.0241 (14)0.0232 (15)0.0198 (14)0.0026 (12)0.0026 (11)0.0060 (12)
C30.0230 (14)0.0209 (15)0.0226 (14)0.0056 (12)0.0012 (11)0.0043 (12)
C40.0159 (12)0.0196 (14)0.0187 (13)0.0014 (11)0.0004 (10)0.0015 (11)
C50.0153 (12)0.0173 (14)0.0195 (13)0.0002 (11)0.0011 (10)0.0017 (11)
C60.0151 (12)0.0185 (14)0.0175 (13)0.0015 (11)0.0009 (10)0.0028 (11)
C70.0195 (13)0.0243 (15)0.0210 (14)0.0047 (12)0.0039 (11)0.0023 (12)
C80.0214 (13)0.0244 (15)0.0166 (13)0.0014 (12)0.0040 (11)0.0011 (11)
C90.0157 (11)0.0176 (13)0.0171 (12)0.0021 (12)0.0008 (9)0.0011 (12)
C100.0160 (12)0.0214 (14)0.0155 (13)0.0027 (11)0.0000 (10)0.0016 (11)
N110.0155 (10)0.0174 (12)0.0173 (11)0.0010 (9)0.0012 (9)0.0000 (9)
N120.0165 (10)0.0169 (11)0.0137 (11)0.0005 (9)0.0003 (8)0.0017 (9)
C130.0172 (12)0.0203 (14)0.0124 (12)0.0025 (11)0.0006 (10)0.0003 (11)
C140.0203 (13)0.0168 (14)0.0238 (14)0.0014 (11)0.0018 (11)0.0006 (11)
C150.0158 (12)0.0255 (17)0.0217 (13)0.0013 (11)0.0034 (10)0.0007 (11)
C160.0189 (13)0.0206 (14)0.0158 (13)0.0050 (11)0.0012 (10)0.0011 (11)
C170.0197 (13)0.0165 (14)0.0183 (13)0.0003 (11)0.0010 (10)0.0005 (11)
C180.0170 (13)0.0221 (15)0.0175 (13)0.0019 (12)0.0001 (10)0.0006 (11)
C190.0205 (14)0.0231 (15)0.0217 (14)0.0046 (12)0.0013 (11)0.0019 (12)
O200.0191 (10)0.0311 (13)0.0550 (15)0.0070 (9)0.0003 (10)0.0092 (11)
O210.0231 (10)0.0225 (11)0.0378 (12)0.0048 (9)0.0035 (9)0.0076 (9)
C220.0314 (16)0.0241 (17)0.048 (2)0.0083 (13)0.0091 (15)0.0060 (14)
C230.0157 (12)0.0188 (14)0.0177 (13)0.0027 (11)0.0034 (10)0.0020 (11)
C240.0286 (15)0.057 (2)0.0156 (14)0.0174 (16)0.0051 (12)0.0049 (14)
C250.0271 (15)0.049 (2)0.0212 (15)0.0183 (15)0.0042 (12)0.0067 (14)
C260.0186 (13)0.0204 (14)0.0175 (13)0.0018 (11)0.0019 (10)0.0017 (11)
C270.0210 (13)0.0213 (14)0.0166 (13)0.0015 (11)0.0022 (11)0.0013 (11)
C280.0188 (13)0.0225 (15)0.0204 (14)0.0037 (12)0.0016 (11)0.0004 (11)
C290.0165 (12)0.0173 (14)0.0195 (14)0.0023 (11)0.0018 (11)0.0017 (11)
O300.0205 (9)0.0270 (11)0.0163 (9)0.0017 (8)0.0000 (8)0.0015 (8)
O310.0226 (9)0.0321 (12)0.0191 (9)0.0110 (9)0.0004 (8)0.0044 (9)
C320.0234 (14)0.037 (2)0.0235 (14)0.0082 (13)0.0044 (11)0.0095 (13)
O330.083 (2)0.0431 (16)0.0587 (18)0.0222 (16)0.0258 (15)0.0088 (14)
C340.060 (2)0.046 (2)0.0272 (18)0.016 (2)0.0064 (17)0.0057 (16)
C350.064 (3)0.076 (3)0.048 (2)0.032 (2)0.002 (2)0.003 (2)
N360.0447 (17)0.0466 (19)0.0476 (19)0.0016 (15)0.0013 (14)0.0045 (16)
C370.039 (2)0.073 (3)0.047 (2)0.008 (2)0.0070 (17)0.011 (2)
C380.059 (2)0.052 (3)0.072 (3)0.022 (2)0.019 (2)0.010 (2)
Geometric parameters (Å, º) top
Zn—N112.039 (2)C19—O201.210 (3)
Zn—N11i2.039 (2)C19—O211.336 (3)
Zn—N12i2.061 (2)O21—C221.447 (3)
Zn—N122.061 (2)C22—H22A0.9800
Zn—O30ii2.540 (2)C22—H22B0.9800
Zn—O30iii2.540 (2)C22—H22C0.9800
C1—N111.377 (3)C23—C281.385 (4)
C1—C10i1.398 (4)C23—C241.396 (4)
C1—C21.440 (4)C24—C251.382 (4)
C2—C31.352 (4)C24—H240.9500
C2—H20.9500C25—C261.393 (4)
C3—C41.442 (4)C25—H250.9500
C3—H30.9500C26—C271.389 (4)
C4—N111.372 (3)C26—C291.488 (4)
C4—C51.413 (3)C27—C281.386 (4)
C5—C61.403 (4)C27—H270.9500
C5—C131.493 (4)C28—H280.9500
C6—N121.370 (3)C29—O301.211 (3)
C6—C71.447 (3)C29—O311.340 (3)
C7—C81.357 (4)O31—C321.447 (3)
C7—H70.9500C32—H32A0.9800
C8—C91.445 (4)C32—H32B0.9800
C8—H80.9500C32—H32C0.9800
C9—N121.374 (3)O33—C341.264 (5)
C9—C101.401 (4)C34—N361.313 (5)
C10—C1i1.398 (4)C34—C351.486 (5)
C10—C231.505 (3)C35—H35A0.9800
C13—C181.393 (4)C35—H35B0.9800
C13—C141.403 (4)C35—H35C0.9800
C14—C151.383 (4)N36—C371.466 (4)
C14—H140.9500N36—C381.468 (5)
C15—C161.389 (4)C37—H37A0.9800
C15—H150.9500C37—H37B0.9800
C16—C171.397 (4)C37—H37C0.9800
C16—C191.484 (4)C38—H38A0.9800
C17—C181.387 (4)C38—H38B0.9800
C17—H170.9500C38—H38C0.9800
C18—H180.9500
N11—Zn—N11i180.0O20—C19—C16124.4 (3)
N11—Zn—N12i90.37 (8)O21—C19—C16112.5 (2)
N11i—Zn—N12i89.63 (8)C19—O21—C22116.2 (2)
N11—Zn—N1289.63 (8)O21—C22—H22A109.5
N11i—Zn—N1290.37 (8)O21—C22—H22B109.5
N12i—Zn—N12180.0H22A—C22—H22B109.5
N11—C1—C10i126.1 (2)O21—C22—H22C109.5
N11—C1—C2109.3 (2)H22A—C22—H22C109.5
C10i—C1—C2124.6 (2)H22B—C22—H22C109.5
C3—C2—C1107.5 (2)C28—C23—C24118.8 (2)
C3—C2—H2126.2C28—C23—C10121.8 (2)
C1—C2—H2126.2C24—C23—C10119.4 (2)
C2—C3—C4106.9 (2)C25—C24—C23120.7 (3)
C2—C3—H3126.6C25—C24—H24119.7
C4—C3—H3126.6C23—C24—H24119.7
N11—C4—C5125.3 (2)C24—C25—C26120.2 (3)
N11—C4—C3109.7 (2)C24—C25—H25119.9
C5—C4—C3124.9 (2)C26—C25—H25119.9
C6—C5—C4125.4 (2)C27—C26—C25119.3 (2)
C6—C5—C13117.6 (2)C27—C26—C29119.0 (2)
C4—C5—C13117.0 (2)C25—C26—C29121.6 (2)
N12—C6—C5125.5 (2)C28—C27—C26120.2 (2)
N12—C6—C7109.6 (2)C28—C27—H27119.9
C5—C6—C7124.9 (2)C26—C27—H27119.9
C8—C7—C6106.9 (2)C23—C28—C27120.8 (2)
C8—C7—H7126.6C23—C28—H28119.6
C6—C7—H7126.6C27—C28—H28119.6
C7—C8—C9107.2 (2)O30—C29—O31123.9 (2)
C7—C8—H8126.4O30—C29—C26124.2 (2)
C9—C8—H8126.4O31—C29—C26111.9 (2)
N12—C9—C10125.4 (2)C29—O31—C32115.7 (2)
N12—C9—C8109.4 (2)O31—C32—H32A109.5
C10—C9—C8125.2 (2)O31—C32—H32B109.5
C1i—C10—C9125.9 (2)H32A—C32—H32B109.5
C1i—C10—C23116.4 (2)O31—C32—H32C109.5
C9—C10—C23117.7 (2)H32A—C32—H32C109.5
C4—N11—C1106.6 (2)H32B—C32—H32C109.5
C4—N11—Zn127.32 (17)O33—C34—N36119.6 (4)
C1—N11—Zn126.01 (17)O33—C34—C35120.4 (4)
C6—N12—C9106.9 (2)N36—C34—C35120.0 (4)
C6—N12—Zn126.79 (17)C34—C35—H35A109.5
C9—N12—Zn126.08 (18)C34—C35—H35B109.5
C18—C13—C14118.8 (2)H35A—C35—H35B109.5
C18—C13—C5121.6 (2)C34—C35—H35C109.5
C14—C13—C5119.7 (2)H35A—C35—H35C109.5
C15—C14—C13120.4 (3)H35B—C35—H35C109.5
C15—C14—H14119.8C34—N36—C37120.9 (3)
C13—C14—H14119.8C34—N36—C38123.0 (3)
C14—C15—C16120.5 (2)C37—N36—C38115.9 (3)
C14—C15—H15119.7N36—C37—H37A109.5
C16—C15—H15119.7N36—C37—H37B109.5
C15—C16—C17119.5 (2)H37A—C37—H37B109.5
C15—C16—C19118.4 (2)N36—C37—H37C109.5
C17—C16—C19122.1 (3)H37A—C37—H37C109.5
C18—C17—C16120.0 (3)H37B—C37—H37C109.5
C18—C17—H17120.0N36—C38—H38A109.5
C16—C17—H17120.0N36—C38—H38B109.5
C17—C18—C13120.8 (2)H38A—C38—H38B109.5
C17—C18—H18119.6N36—C38—H38C109.5
C13—C18—H18119.6H38A—C38—H38C109.5
O20—C19—O21123.1 (3)H38B—C38—H38C109.5
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Zn(C52H36N4O8)]·2C4H9NO
Mr1084.46
Crystal system, space groupMonoclinic, P21/c
Temperature (K)110
a, b, c (Å)13.8014 (4), 8.9030 (4), 21.1399 (9)
β (°) 91.675 (3)
V3)2596.43 (18)
Z2
Radiation typeMo Kα
µ (mm1)0.54
Crystal size (mm)0.45 × 0.10 × 0.10
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
19518, 6135, 4518
Rint0.081
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.116, 1.08
No. of reflections6135
No. of parameters354
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.63, 0.54

Computer programs: COLLECT (Nonius, 1999), DENZO (Otwinowski & Minor, 1997), DENZO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97.

Selected geometric parameters (Å, º) top
Zn—N112.039 (2)Zn—O30i2.540 (2)
Zn—N122.061 (2)
N11—Zn—N1289.63 (8)N11ii—Zn—N1290.37 (8)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y+1, z+1.
 

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