meso-[5,10,15,20-Tetra­kis(4-cyano­phen­yl)porphyrinato]zinc

Dong, S.; Jiang, J.

doi:10.1107/S160053681100849X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page m431

doi:10.1107/S160053681100849X

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meso-[5,10,15,20-Tetrakis(4-cyanophenyl)porphyrinato]zinc

Shuai Dong ^a and Jianzhuang Jiang ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
^*Correspondence e-mail: jianzhuang@ustb.edu.cn

(Received 2 March 2011; accepted 6 March 2011; online 12 March 2011)

In the title compound, [Zn(C₄₈H₂₄N₈)], the coordination environment of the Zn²⁺ ion (site symmetry $[\overline1]$ ) is octahedral, with four indole N atoms forming the equatorial plane and the axial positions being occupied by N atoms from the cyanide groups of neighbouring molecules. In the crystal, adjacent molecules are assembled into a two-dimensional supramolecular framework parallel to ( $[\overline1]$ 01) via the coodination bonding. Topology analysis reveals this compound to be a (4,4)-connected network.

Related literature

For background to the use of porphyrins and derivatives, see: Jiang & Ng (2009 ). For the use of their metal complexes as catalysts, see: Chen et al. (2004 ). For Zn—N bond lengths in other Zn(II) porphyrin species, see: Muniappan et al. (2006 ). For the synthesis of the ligand, see: Kumar et al. (1998 ).

Experimental

Crystal data

[Zn(C₄₈H₂₄N₈)]
M_r = 778.12
Monoclinic, P 2₁ /n
a = 9.7373 (10) Å
b = 9.4468 (10) Å
c = 21.280 (2) Å
β = 101.229 (2)°
V = 1920.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.69 mm⁻¹
T = 295 K
0.30 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1995 ) T_min = 0.726, T_max = 0.967
9272 measured reflections
3376 independent reflections
2610 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.05
3376 reflections
259 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 1998 ); software used to prepare material for publication: XP.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100849X/jh2269sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100849X/jh2269Isup2.hkl

checkCIF report

Comment top

Porphyrins and derivatives have been an important class of dyes and pigments with extensive applications in the paints, printing, and textile industries ever since last century (Jiang & Ng, 2009). Their metal complexes are well known catalysts for numerous chemical reactions (Chen et al., 2004). Therefore, it is worthy to prepare corresponding metal complex.

As shown in Fig.1, compound I is a mononuclear neutral complex with a two-dimensional supramolecular configuration. Each Zn(II) atom is octa-coordinated completed by four indole nitrogen atoms and two nitrogen atoms of cyanogen groups. The bond length is in line with the distances of Zn—N in other Zn(II) porphyrin species (Muniappan et al., 2006). The neighboring Zn(TCPP) molecules are connected via the coodination bonding, forming a two-dimensional supramolecular network. The Zn(II) ion is treated as a node, this compound is a (4,4)-connected network, Figure 2.

Related literature top

For background to the use of porphyrins and derivatives, see: Jiang & Ng (2009). For the use of their metal complexes as catalysts, see: Chen et al. (2004). For Zn—N bond lengths in other Zn(II) porphyrin species, see: Muniappan et al. (2006). For the synthesis of the ligand, see: Kumar et al. (1998).

Experimental top

The H₂TCPP ligand was synthesized according to the previous literature(Kumar et al., 1998). The synthesis method of the compound I was obtained by allowing the mixure of Zn(OAc)₂ (0.02 g, 0.1 mmol) and H₂TCPP (0.072 g, 0.1 mmol), and 15 mL DMF was sealed in 25 ml Teflon-lined stainless steel reactor, which was heated to 110°C. Purple block-shaped crystals suitable for X-ray diffraction analysis were separated by filtration with the yield of 35%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: XP (Sheldrick, 1998).

Figures top

	Fig. 1. A view of (I) with the unique atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level, hydrogen atoms are omited for clarity.
	Fig. 2. A view of two-dimensional supramolecular configuration of (I).

meso-[5,10,15,20-Tetrakis(4-cyanophenyl)porphyrinato]zinc top

Crystal data top

[Zn(C₄₈H₂₄N₈)]	F(000) = 796
M_r = 778.12	D_x = 1.346 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2737 reflections
a = 9.7373 (10) Å	θ = 2.4–25.3°
b = 9.4468 (10) Å	µ = 0.69 mm⁻¹
c = 21.280 (2) Å	T = 295 K
β = 101.229 (2)°	Needle, purple
V = 1920.0 (3) Å³	0.30 × 0.05 × 0.05 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3376 independent reflections
Radiation source: fine-focus sealed tube	2610 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 0 pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1995)	k = −11→11
T_min = 0.726, T_max = 0.967	l = −22→25
9272 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0599P)² + 0.3654P] where P = (F_o² + 2F_c²)/3
3376 reflections	(Δ/σ)_max = 0.001
259 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Zn(C₄₈H₂₄N₈)]	V = 1920.0 (3) Å³
M_r = 778.12	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7373 (10) Å	µ = 0.69 mm⁻¹
b = 9.4468 (10) Å	T = 295 K
c = 21.280 (2) Å	0.30 × 0.05 × 0.05 mm
β = 101.229 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3376 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1995)	2610 reflections with I > 2σ(I)
T_min = 0.726, T_max = 0.967	R_int = 0.028
9272 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	Δρ_max = 0.34 e Å⁻³
3376 reflections	Δρ_min = −0.24 e Å⁻³
259 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	1.0000	0.0000	1.0000	0.03997 (16)
N2	0.9529 (2)	0.0662 (2)	1.08533 (8)	0.0377 (5)
C5	1.0664 (3)	−0.1265 (3)	1.15417 (10)	0.0382 (6)
C10	0.8349 (2)	0.2917 (3)	1.04962 (11)	0.0379 (6)
N1	1.0918 (2)	−0.1781 (2)	1.04326 (8)	0.0370 (5)
C4	1.1139 (3)	−0.2084 (3)	1.10731 (11)	0.0388 (6)
C16	1.0114 (3)	−0.2648 (3)	1.24674 (12)	0.0565 (7)
H16	0.9250	−0.2874	1.2216	0.068*
C13	1.2649 (3)	−0.1964 (3)	1.32212 (13)	0.0590 (8)
H13	1.3505	−0.1722	1.3475	0.071*
C9	0.8856 (3)	0.1885 (3)	1.09594 (11)	0.0399 (6)
C14	1.1741 (3)	−0.2811 (3)	1.34609 (11)	0.0487 (7)
C18	0.6411 (3)	0.3997 (3)	1.09533 (13)	0.0508 (7)
H18	0.6022	0.3099	1.0958	0.061*
C11	1.1027 (3)	−0.1798 (3)	1.22180 (10)	0.0390 (6)
N3	1.2522 (4)	−0.3731 (3)	1.46169 (12)	0.0859 (9)
C20	0.6318 (3)	0.6457 (3)	1.11635 (13)	0.0542 (7)
C8	0.8808 (3)	0.1975 (3)	1.16333 (12)	0.0516 (7)
H8	0.8407	0.2701	1.1832	0.062*
C12	1.2296 (3)	−0.1464 (3)	1.26005 (12)	0.0535 (7)
H12	1.2924	−0.0895	1.2439	0.064*
C23	0.7632 (3)	0.4171 (3)	1.07089 (11)	0.0397 (6)
C21	0.7496 (3)	0.6674 (3)	1.09048 (12)	0.0539 (7)
H21	0.7846	0.7584	1.0880	0.065*
C6	0.9912 (3)	−0.0002 (2)	1.14336 (11)	0.0386 (6)
C17	1.2141 (4)	−0.3342 (3)	1.41096 (13)	0.0638 (8)
C22	0.8154 (3)	0.5528 (3)	1.06823 (12)	0.0474 (6)
H22	0.8955	0.5673	1.0514	0.057*
C24	0.5695 (4)	0.7637 (4)	1.14423 (19)	0.0853 (11)
C19	0.5774 (3)	0.5122 (3)	1.11873 (15)	0.0558 (7)
H19	0.4980	0.4981	1.1361	0.067*
C7	0.9447 (3)	0.0823 (3)	1.19189 (11)	0.0503 (7)
H7	0.9568	0.0599	1.2352	0.060*
C15	1.0462 (3)	−0.3172 (3)	1.30882 (13)	0.0585 (8)
H15	0.9844	−0.3756	1.3250	0.070*
C1	1.1545 (3)	−0.2842 (3)	1.01528 (11)	0.0390 (6)
C2	1.2155 (3)	−0.3853 (3)	1.06340 (12)	0.0498 (7)
H2	1.2628	−0.4678	1.0567	0.060*
C3	1.1911 (3)	−0.3379 (3)	1.11993 (12)	0.0500 (7)
H3	1.2191	−0.3810	1.1597	0.060*
N4	0.5198 (5)	0.8532 (4)	1.1673 (2)	0.1405 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0588 (3)	0.0366 (3)	0.0254 (2)	0.01046 (19)	0.01037 (17)	0.00220 (16)
N2	0.0477 (12)	0.0378 (11)	0.0285 (10)	0.0083 (10)	0.0098 (9)	0.0020 (9)
C5	0.0476 (14)	0.0389 (14)	0.0275 (12)	0.0001 (11)	0.0061 (10)	0.0028 (10)
C10	0.0418 (13)	0.0395 (14)	0.0324 (12)	0.0046 (11)	0.0075 (10)	−0.0015 (10)
N1	0.0479 (12)	0.0367 (11)	0.0263 (9)	0.0073 (9)	0.0070 (8)	−0.0001 (8)
C4	0.0497 (14)	0.0358 (13)	0.0297 (12)	0.0037 (11)	0.0048 (10)	0.0021 (10)
C16	0.0678 (19)	0.0610 (18)	0.0364 (14)	−0.0128 (15)	−0.0002 (13)	0.0056 (13)
C13	0.0562 (17)	0.076 (2)	0.0393 (15)	0.0041 (16)	−0.0047 (13)	0.0030 (14)
C9	0.0471 (14)	0.0415 (14)	0.0319 (12)	0.0050 (11)	0.0097 (10)	−0.0008 (10)
C14	0.0720 (19)	0.0447 (15)	0.0280 (12)	0.0195 (14)	0.0063 (13)	0.0003 (11)
C18	0.0547 (16)	0.0402 (15)	0.0610 (17)	0.0013 (13)	0.0195 (13)	−0.0009 (13)
C11	0.0523 (15)	0.0365 (13)	0.0277 (12)	0.0063 (11)	0.0068 (11)	0.0001 (10)
N3	0.129 (3)	0.088 (2)	0.0374 (14)	0.0310 (19)	0.0062 (15)	0.0121 (14)
C20	0.0636 (18)	0.0475 (17)	0.0531 (17)	0.0133 (14)	0.0152 (14)	−0.0054 (13)
C8	0.0727 (18)	0.0519 (17)	0.0327 (13)	0.0172 (14)	0.0168 (13)	−0.0011 (12)
C12	0.0564 (17)	0.0639 (19)	0.0394 (14)	−0.0039 (14)	0.0075 (13)	0.0074 (13)
C23	0.0472 (14)	0.0391 (15)	0.0315 (12)	0.0068 (11)	0.0049 (10)	−0.0009 (11)
C21	0.075 (2)	0.0362 (15)	0.0485 (16)	−0.0011 (14)	0.0061 (14)	−0.0061 (12)
C6	0.0490 (14)	0.0399 (14)	0.0270 (11)	0.0027 (11)	0.0076 (10)	0.0011 (10)
C17	0.092 (2)	0.0591 (19)	0.0392 (16)	0.0252 (17)	0.0088 (15)	0.0042 (14)
C22	0.0531 (16)	0.0479 (15)	0.0417 (14)	0.0013 (13)	0.0102 (12)	−0.0025 (12)
C24	0.105 (3)	0.050 (2)	0.111 (3)	0.0098 (19)	0.047 (2)	−0.013 (2)
C19	0.0550 (17)	0.0512 (18)	0.0669 (19)	0.0081 (14)	0.0254 (14)	−0.0049 (14)
C7	0.0736 (19)	0.0507 (17)	0.0288 (13)	0.0152 (14)	0.0149 (12)	0.0045 (12)
C15	0.085 (2)	0.0498 (17)	0.0425 (15)	−0.0079 (16)	0.0159 (15)	0.0093 (13)
C1	0.0441 (14)	0.0393 (14)	0.0330 (12)	0.0067 (11)	0.0061 (11)	0.0006 (10)
C2	0.0650 (18)	0.0457 (15)	0.0378 (14)	0.0208 (13)	0.0077 (12)	0.0026 (12)
C3	0.0685 (18)	0.0485 (16)	0.0310 (13)	0.0172 (14)	0.0049 (12)	0.0081 (11)
N4	0.181 (4)	0.070 (2)	0.197 (4)	0.024 (3)	0.101 (3)	−0.036 (3)

Geometric parameters (Å, º) top

Zn1—N1ⁱ	2.0391 (19)	C18—C19	1.372 (4)
Zn1—N1	2.0391 (19)	C18—C23	1.396 (4)
Zn1—N2	2.0546 (18)	C18—H18	0.9300
Zn1—N2ⁱ	2.0546 (18)	C11—C12	1.377 (4)
Zn1—N3ⁱⁱ	2.675 (2)	N3—C17	1.132 (3)
Zn1—N3ⁱⁱⁱ	2.675 (2)	C20—C19	1.372 (4)
N2—C9	1.369 (3)	C20—C21	1.381 (4)
N2—C6	1.370 (3)	C20—C24	1.450 (4)
C5—C6	1.396 (3)	C8—C7	1.339 (4)
C5—C4	1.409 (3)	C8—H8	0.9300
C5—C11	1.501 (3)	C12—H12	0.9300
C10—C9	1.406 (3)	C23—C22	1.384 (4)
C10—C1ⁱ	1.406 (3)	C21—C22	1.387 (4)
C10—C23	1.490 (3)	C21—H21	0.9300
N1—C4	1.368 (3)	C6—C7	1.435 (3)
N1—C1	1.368 (3)	C22—H22	0.9300
C4—C3	1.434 (3)	C24—N4	1.134 (4)
C16—C11	1.379 (4)	C19—H19	0.9300
C16—C15	1.390 (4)	C7—H7	0.9300
C16—H16	0.9300	C15—H15	0.9300
C13—C14	1.363 (4)	C1—C10ⁱ	1.406 (3)
C13—C12	1.382 (4)	C1—C2	1.441 (3)
C13—H13	0.9300	C2—C3	1.348 (3)
C9—C8	1.446 (3)	C2—H2	0.9300
C14—C15	1.383 (4)	C3—H3	0.9300
C14—C17	1.449 (4)

N1ⁱ—Zn1—N1	180.000 (1)	C19—C20—C24	119.7 (3)
N1ⁱ—Zn1—N2	89.67 (7)	C21—C20—C24	119.7 (3)
N1—Zn1—N2	90.33 (7)	C7—C8—C9	107.5 (2)
N1ⁱ—Zn1—N2ⁱ	90.33 (7)	C7—C8—H8	126.3
N1—Zn1—N2ⁱ	89.67 (7)	C9—C8—H8	126.3
N2—Zn1—N2ⁱ	180.000 (1)	C11—C12—C13	121.0 (3)
C9—N2—C6	106.99 (18)	C11—C12—H12	119.5
C9—N2—Zn1	126.80 (15)	C13—C12—H12	119.5
C6—N2—Zn1	126.09 (16)	C22—C23—C18	118.1 (2)
C6—C5—C4	125.9 (2)	C22—C23—C10	121.7 (2)
C6—C5—C11	117.6 (2)	C18—C23—C10	120.2 (2)
C4—C5—C11	116.5 (2)	C20—C21—C22	119.6 (3)
C9—C10—C1ⁱ	124.8 (2)	C20—C21—H21	120.2
C9—C10—C23	117.4 (2)	C22—C21—H21	120.2
C1ⁱ—C10—C23	117.8 (2)	N2—C6—C5	125.5 (2)
C4—N1—C1	106.49 (18)	N2—C6—C7	109.4 (2)
C4—N1—Zn1	126.31 (16)	C5—C6—C7	125.1 (2)
C1—N1—Zn1	126.96 (15)	N3—C17—C14	176.4 (4)
N1—C4—C5	125.5 (2)	C23—C22—C21	120.7 (3)
N1—C4—C3	109.9 (2)	C23—C22—H22	119.6
C5—C4—C3	124.6 (2)	C21—C22—H22	119.6
C11—C16—C15	121.2 (3)	N4—C24—C20	177.9 (4)
C11—C16—H16	119.4	C20—C19—C18	119.6 (3)
C15—C16—H16	119.4	C20—C19—H19	120.2
C14—C13—C12	120.0 (3)	C18—C19—H19	120.2
C14—C13—H13	120.0	C8—C7—C6	107.4 (2)
C12—C13—H13	120.0	C8—C7—H7	126.3
N2—C9—C10	125.7 (2)	C6—C7—H7	126.3
N2—C9—C8	108.8 (2)	C14—C15—C16	118.9 (3)
C10—C9—C8	125.4 (2)	C14—C15—H15	120.6
C13—C14—C15	120.5 (2)	C16—C15—H15	120.6
C13—C14—C17	119.1 (3)	N1—C1—C10ⁱ	126.1 (2)
C15—C14—C17	120.4 (3)	N1—C1—C2	109.5 (2)
C19—C18—C23	121.4 (3)	C10ⁱ—C1—C2	124.4 (2)
C19—C18—H18	119.3	C3—C2—C1	107.1 (2)
C23—C18—H18	119.3	C3—C2—H2	126.5
C12—C11—C16	118.5 (2)	C1—C2—H2	126.5
C12—C11—C5	120.5 (2)	C2—C3—C4	107.1 (2)
C16—C11—C5	121.0 (2)	C2—C3—H3	126.5
C19—C20—C21	120.5 (3)	C4—C3—H3	126.5

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+5/2, y+1/2, −z+5/2; (iii) x−1/2, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₄₈H₂₄N₈)]
M_r	778.12
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	9.7373 (10), 9.4468 (10), 21.280 (2)
β (°)	101.229 (2)
V (Å³)	1920.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.30 × 0.05 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1995)
T_min, T_max	0.726, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	9272, 3376, 2610
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.05
No. of reflections	3376
No. of parameters	259
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.24

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 1998).

Acknowledgements

This work was supported by the Natural Science Foundation of China.

References

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