Substitutional disorder in bis­[(cyanato-κO)/hydroxido(0.5/0.5)](5,10,15,20-tetra­phenyl­porphyrinato-κ4N)tin(IV)

Ben Moussa, I.; Belkhiria, M.S.; Najmudin, S.; Bonifacio, C.; Nasri, H.

doi:10.1107/S1600536811021544

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages m903-m904

doi:10.1107/S1600536811021544

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Substitutional disorder in bis[(cyanato-κO)/hydroxido(0.5/0.5)](5,10,15,20-tetraphenylporphyrinato-κ⁴N)tin(IV)

Imen Ben Moussa,^a Mohamed Salah Belkhiria,^a Shabir Najmudin,^b Cecilia Bonifacio ^c and Habib Nasri ^a ^*

^aDépartement de Chimie, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l'Environnement, 5019 Monastir, Tunisia, ^bFaculdade de Medicina Veterinária, Universidade Técnica de Lisboa, Avenida da Universidade Técnica, 1300-477 Lisboa, Portugal, and ^cDepartamento de Química, FCT-UNL, 2829-516 Caparica, Portugal
^*Correspondence e-mail: hnasri1@gmail.com

(Received 1 June 2011; accepted 3 June 2011; online 11 June 2011)

The title complex, [Sn^IV(C₄₄H₂₈N₄)(CNO)(OH)], exhibits substitutional disorder of the OH⁻ and OCN⁻ axial ligands. Thus, the cyanato-O ligand and the hydroxyl group bonded to the central Sn^IV atom share statistically the axial position. The Sn^IV ion is hexacoordinated by the four N atoms of the pyrrole rings of the tetraphenylporphyrin (TPP) and the O atoms of the two disordered OCN⁻ and OH⁻ axial ligands. The equatorial tin–pyrrole N atom distance (Sn—N_p) is 2.100 (2) Å and the axial Sn—O(OCN) or Sn—O(OH) bond length is 2.074 (2) Å.

Related literature

For a review of porphyrin complexes, see: Scheidt (2000 ). For the synthesis of tin(IV) porphyrin species, see: Fallon et al. (2002 ); Martelli et al. (2009 ). For comparative bond lengths, see: Allen et al. (1987 ); Smith et al. (1991 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

[Sn(C₄₄H₂₈N₄)(CNO)(OH)]
M_r = 790.42
Monoclinic, P 2₁ /c
a = 11.2943 (6) Å
b = 12.6972 (7) Å
c = 13.0711 (7) Å
β = 114.251 (2)°
V = 1709.06 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.870, T_max = 0.954
27811 measured reflections
5968 independent reflections
5241 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.097
S = 1.13
5968 reflections
250 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −1.34 e Å⁻³

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021544/dn2696sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021544/dn2696Isup2.hkl

checkCIF report

Comment top

The search in the Cambridge Crystallographic Database (version 5.32 with addenda up to November 26, 2010; Allen, 2002) shows that the majority of the reported X-ray molecular structures of porphyrin tin(IV) complexes are hexa-coordinated type [Sn^IV(Porph)(X)₂] for which X is an anionic unidentate ligand bonded to the tin(IV) ion through the oxygen atom. To the best of our knowledge, there is no X-ray molecular structure of a tin(IV) cyanato-O porphyrin species reported in the literature.

The bis{(cyanato-O)/(hydroxo)(0.5/0.5) }(5,10,15,20-tetraphenylporphyrin)tin(IV) complex [Sn^IV(C₄₄H₂₈N₄)(OCN)(OH)] exhibits substitutional disorder of both thiocyanato-O and hydroxo ligands with equal occupancy factor of 0.5. The tin atom which is octahedrally coordinated lies on an inversion center (Fig. 1).

The equatorial tin–pyrrole N atom distance (Sn—N_p) is 2.100 (2) Å which is normal for tin(IV) porphyrin species. The Sn—O(OH) distance is 2.088 (6) Å which is longer than the one of the related species [Sn^IV(TPP)(OH)₂] (2.023 (4) Å) (Smith et al., 1991). The Sn—O(OCN) bond lengh value is 2.059 (8) Å which is close to those of related porphyrin species, i.e, for [Sn^IV(TTP)(OC₆H₅)₂] (TTP is the meso-tetrakis(p-tolyl)porphyrin) (Fallon et al., 2002) the Sn—O(OPh) distance is 2.055 (2) Å.

There are no intermolecular or intramolecular hydrogen bonds in the structure of (I). The packing diagram for (I) (Fig.2) is simple; there is no evidence for intermolecular π -π bonding between the faces of the porphyrin cores in compound (I). The absence of the π-π interactions results mainly in the steric restrictions requirements of the phenyl groups that determine the packing environment.

Related literature top

For a review of porphyrin complexes, see: Scheidt (2000). For the synthesis of tin(IV) porphyrin species, see: Fallon et al. (2002); Martelli et al. (2009). For comparative bond lengths, see: Allen et al. (1987); Smith et al. (1991). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The reaction of the [Sn^IV(TPP)(OH)₂] complex (30 mg, 0.037 mmol) (Martelli et al., 2009) with an excess of sodium cyanate, NaOCN (85 mg, 1.31 mmol) and 18-crown-6 (90 mg, 0.34 mmol) in dichloromethane (4 ml) give a pink-violet solution. Crystals of the title complex were obtained by diffusion of ether through the dichloromethane solution.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip 2010).

Figures top

	Fig. 1. A view of the structure of the complex [Sn^IV(C₄₄H₂₈N₄)(OCN)(OH)] showing the atom numbering scheme. Displacement ellipsoids are drawn at 30%. The O atoms of the hydroxo axial ligands and the H atoms have been omitted for clarity. [Symmetry code: (i) -x + 1,-y, -z + 1]
	Fig. 2. A unit cell packing of the title complex viewed down the b axis. H atoms have been omitted for clarity.

bis[(cyanato-κO)/hydroxido(0.5/0.5)](5,10,15,20- tetraphenylporphyrinato-κ⁴N)tin(IV) top

Crystal data top

[Sn(C₄₄H₂₈N₄)(CNO)(OH)]	F(000) = 800
M_r = 790.42	D_x = 1.536 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 27811 reflections
a = 11.2943 (6) Å	θ = 2.6–32.2°
b = 12.6972 (7) Å	µ = 0.80 mm⁻¹
c = 13.0711 (7) Å	T = 293 K
β = 114.251 (2)°	Prism, purple
V = 1709.06 (16) Å³	0.20 × 0.18 × 0.12 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	5968 independent reflections
Radiation source: fine-focus sealed tube	5241 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 32.2°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −16→15
T_min = 0.870, T_max = 0.954	k = 0→18
27811 measured reflections	l = 0→19

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) = 0.097	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0357P)² + 1.5751P] where P = (F_o² + 2F_c²)/3
5968 reflections	(Δ/σ)_max < 0.001
250 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −1.34 e Å⁻³

Crystal data top

[Sn(C₄₄H₂₈N₄)(CNO)(OH)]	V = 1709.06 (16) Å³
M_r = 790.42	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2943 (6) Å	µ = 0.80 mm⁻¹
b = 12.6972 (7) Å	T = 293 K
c = 13.0711 (7) Å	0.20 × 0.18 × 0.12 mm
β = 114.251 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5968 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	5241 reflections with I > 2σ(I)
T_min = 0.870, T_max = 0.954	R_int = 0.028
27811 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.13	Δρ_max = 0.73 e Å⁻³
5968 reflections	Δρ_min = −1.34 e Å⁻³
250 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	Occ. (<1)
Sn1	0.5000	0.0000	0.5000	0.02969 (7)
N2	0.50052 (16)	0.15106 (14)	0.43522 (13)	0.0276 (3)
N1	0.63300 (16)	0.04991 (14)	0.65913 (13)	0.0269 (3)
O1	0.65060 (16)	−0.03859 (15)	0.45502 (15)	0.0389 (4)	0.50
N3	0.8546 (4)	0.0655 (5)	0.5244 (4)	0.0513 (12)	0.50
C23	0.7509 (6)	0.0155 (5)	0.4921 (5)	0.0479 (13)	0.50
O2	0.65060 (16)	−0.03859 (15)	0.45502 (15)	0.0389 (4)	0.50
H2A	0.6917	−0.0883	0.4933	0.058*	0.50
C1	0.68716 (18)	−0.01306 (15)	0.75191 (15)	0.0245 (3)
C2	0.78155 (19)	0.04888 (16)	0.84031 (15)	0.0259 (4)
H2	0.8319	0.0262	0.9130	0.031*
C3	0.78367 (19)	0.14687 (17)	0.79813 (16)	0.0274 (4)
H3	0.8360	0.2030	0.8365	0.033*
C4	0.68969 (18)	0.14729 (16)	0.68298 (16)	0.0262 (4)
C5	0.66400 (19)	0.23239 (16)	0.60800 (16)	0.0266 (4)
C6	0.57669 (19)	0.23375 (16)	0.49389 (16)	0.0268 (4)
C7	0.55237 (19)	0.32147 (16)	0.41809 (17)	0.0284 (4)
H7	0.5903	0.3878	0.4360	0.034*
C8	0.46382 (19)	0.29004 (16)	0.31546 (16)	0.0279 (4)
H8	0.4310	0.3306	0.2505	0.033*
C9	0.43046 (18)	0.18217 (16)	0.32611 (15)	0.0253 (4)
C10	0.65856 (18)	−0.11936 (16)	0.75997 (15)	0.0247 (3)
C11	0.73248 (19)	−0.17185 (16)	0.87048 (15)	0.0251 (3)
C12	0.8373 (2)	−0.23659 (18)	0.88507 (17)	0.0314 (4)
H12	0.8602	−0.2483	0.8253	0.038*
C13	0.9080 (2)	−0.2840 (2)	0.98771 (19)	0.0376 (5)
H13	0.9778	−0.3274	0.9964	0.045*
C14	0.8756 (2)	−0.2673 (2)	1.07638 (18)	0.0387 (5)
H14	0.9238	−0.2986	1.1454	0.046*
C15	0.7702 (3)	−0.2033 (2)	1.06295 (18)	0.0393 (5)
H15	0.7475	−0.1924	1.1229	0.047*
C16	0.6988 (2)	−0.15561 (19)	0.96030 (17)	0.0334 (4)
H16	0.6285	−0.1128	0.9516	0.040*
C17	0.74361 (19)	0.32920 (16)	0.65294 (17)	0.0280 (4)
C18	0.8459 (2)	0.35026 (19)	0.62357 (18)	0.0341 (4)
H18	0.8621	0.3061	0.5740	0.041*
C19	0.9245 (2)	0.4378 (2)	0.6684 (2)	0.0448 (6)
H19	0.9926	0.4522	0.6481	0.054*
C20	0.9024 (3)	0.5030 (2)	0.7422 (3)	0.0563 (8)
H20	0.9560	0.5608	0.7725	0.068*
C21	0.8015 (4)	0.4829 (2)	0.7712 (3)	0.0622 (9)
H21	0.7861	0.5275	0.8208	0.075*
C22	0.7216 (3)	0.3962 (2)	0.7270 (3)	0.0490 (6)
H22	0.6530	0.3831	0.7472	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03022 (10)	0.02873 (10)	0.02008 (9)	−0.01209 (8)	0.00016 (7)	0.00446 (7)
N2	0.0283 (8)	0.0275 (8)	0.0206 (7)	−0.0088 (6)	0.0037 (6)	0.0030 (6)
N1	0.0266 (7)	0.0268 (8)	0.0208 (7)	−0.0068 (6)	0.0031 (6)	0.0026 (6)
O1	0.0350 (8)	0.0416 (9)	0.0396 (9)	0.0014 (7)	0.0149 (7)	0.0072 (7)
N3	0.037 (2)	0.076 (4)	0.044 (2)	−0.013 (2)	0.0184 (19)	−0.005 (2)
C23	0.048 (3)	0.055 (3)	0.040 (3)	0.001 (2)	0.017 (2)	0.005 (2)
O2	0.0350 (8)	0.0416 (9)	0.0396 (9)	0.0014 (7)	0.0149 (7)	0.0072 (7)
C1	0.0231 (8)	0.0279 (9)	0.0195 (7)	−0.0017 (7)	0.0057 (6)	0.0009 (6)
C2	0.0249 (8)	0.0288 (9)	0.0202 (7)	−0.0008 (7)	0.0055 (6)	−0.0021 (7)
C3	0.0247 (8)	0.0305 (10)	0.0224 (8)	−0.0054 (7)	0.0049 (7)	−0.0033 (7)
C4	0.0240 (8)	0.0283 (9)	0.0221 (8)	−0.0063 (7)	0.0054 (6)	−0.0011 (7)
C5	0.0257 (8)	0.0256 (9)	0.0248 (8)	−0.0073 (7)	0.0066 (7)	−0.0009 (7)
C6	0.0257 (8)	0.0264 (9)	0.0241 (8)	−0.0074 (7)	0.0060 (7)	0.0018 (7)
C7	0.0287 (9)	0.0254 (9)	0.0280 (9)	−0.0068 (7)	0.0085 (7)	0.0032 (7)
C8	0.0283 (9)	0.0278 (9)	0.0254 (8)	−0.0035 (7)	0.0088 (7)	0.0053 (7)
C9	0.0247 (8)	0.0268 (9)	0.0217 (7)	−0.0038 (7)	0.0068 (6)	0.0031 (6)
C10	0.0237 (8)	0.0288 (9)	0.0196 (7)	−0.0027 (7)	0.0070 (6)	0.0020 (6)
C11	0.0268 (8)	0.0247 (8)	0.0199 (7)	−0.0035 (7)	0.0056 (6)	0.0005 (6)
C12	0.0309 (9)	0.0356 (11)	0.0238 (8)	0.0024 (8)	0.0072 (7)	−0.0005 (7)
C13	0.0311 (10)	0.0377 (12)	0.0327 (10)	0.0004 (9)	0.0017 (8)	0.0033 (9)
C14	0.0376 (11)	0.0405 (12)	0.0259 (9)	−0.0074 (10)	0.0008 (8)	0.0086 (8)
C15	0.0485 (13)	0.0441 (13)	0.0249 (9)	−0.0062 (11)	0.0148 (9)	0.0042 (9)
C16	0.0388 (11)	0.0375 (11)	0.0264 (9)	0.0011 (9)	0.0159 (8)	0.0033 (8)
C17	0.0271 (8)	0.0241 (9)	0.0266 (8)	−0.0052 (7)	0.0049 (7)	0.0009 (7)
C18	0.0323 (10)	0.0344 (11)	0.0311 (10)	−0.0076 (8)	0.0084 (8)	0.0010 (8)
C19	0.0340 (11)	0.0420 (13)	0.0462 (13)	−0.0153 (10)	0.0042 (10)	0.0105 (11)
C20	0.0528 (16)	0.0293 (12)	0.0615 (18)	−0.0169 (11)	−0.0019 (13)	−0.0039 (12)
C21	0.067 (2)	0.0404 (16)	0.075 (2)	−0.0133 (14)	0.0255 (18)	−0.0291 (15)
C22	0.0483 (14)	0.0454 (15)	0.0580 (16)	−0.0131 (12)	0.0265 (13)	−0.0187 (12)

Geometric parameters (Å, º) top

Sn1—O2ⁱ	2.0737 (18)	C8—C9	1.442 (3)
Sn1—O1ⁱ	2.0737 (18)	C8—H8	0.9300
Sn1—O1	2.0737 (18)	C9—C10ⁱ	1.408 (3)
Sn1—N2ⁱ	2.0976 (17)	C10—C9ⁱ	1.408 (3)
Sn1—N2	2.0976 (17)	C10—C11	1.496 (3)
Sn1—N1	2.1018 (16)	C11—C12	1.388 (3)
Sn1—N1ⁱ	2.1018 (16)	C11—C16	1.390 (3)
N2—C6	1.374 (2)	C12—C13	1.386 (3)
N2—C9	1.375 (2)	C12—H12	0.9300
N1—C4	1.368 (3)	C13—C14	1.368 (4)
N1—C1	1.369 (2)	C13—H13	0.9300
O1—C23	1.241 (6)	C14—C15	1.391 (4)
O1—H2A	0.8202	C14—H14	0.9300
N3—C23	1.244 (7)	C15—C16	1.389 (3)
C23—H2A	1.4810	C15—H15	0.9300
C1—C10	1.402 (3)	C16—H16	0.9300
C1—C2	1.442 (3)	C17—C18	1.385 (3)
C2—C3	1.365 (3)	C17—C22	1.386 (3)
C2—H2	0.9300	C18—C19	1.393 (3)
C3—C4	1.442 (3)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.370 (5)
C4—C5	1.407 (3)	C19—H19	0.9300
C5—C6	1.410 (3)	C20—C21	1.364 (5)
C5—C17	1.494 (3)	C20—H20	0.9300
C6—C7	1.440 (3)	C21—C22	1.390 (4)
C7—C8	1.363 (3)	C21—H21	0.9300
C7—H7	0.9300	C22—H22	0.9300

O2ⁱ—Sn1—O1ⁱ	0.00 (4)	C5—C6—C7	126.15 (18)
O2ⁱ—Sn1—O1	180.0	C8—C7—C6	107.83 (17)
O1ⁱ—Sn1—O1	180.0	C8—C7—H7	126.1
O2ⁱ—Sn1—N2ⁱ	87.88 (7)	C6—C7—H7	126.1
O1ⁱ—Sn1—N2ⁱ	87.88 (7)	C7—C8—C9	107.36 (17)
O1—Sn1—N2ⁱ	92.12 (7)	C7—C8—H8	126.3
O2ⁱ—Sn1—N2	92.12 (7)	C9—C8—H8	126.3
O1ⁱ—Sn1—N2	92.12 (7)	N2—C9—C10ⁱ	125.74 (18)
O1—Sn1—N2	87.88 (7)	N2—C9—C8	108.13 (16)
N2ⁱ—Sn1—N2	180.0	C10ⁱ—C9—C8	126.13 (17)
O2ⁱ—Sn1—N1	89.10 (7)	C1—C10—C9ⁱ	126.59 (17)
O1ⁱ—Sn1—N1	89.10 (7)	C1—C10—C11	116.56 (16)
O1—Sn1—N1	90.90 (7)	C9ⁱ—C10—C11	116.83 (17)
N2ⁱ—Sn1—N1	89.75 (6)	C12—C11—C16	119.03 (18)
N2—Sn1—N1	90.25 (6)	C12—C11—C10	120.18 (18)
O2ⁱ—Sn1—N1ⁱ	90.90 (7)	C16—C11—C10	120.79 (19)
O1ⁱ—Sn1—N1ⁱ	90.90 (7)	C13—C12—C11	120.7 (2)
O1—Sn1—N1ⁱ	89.10 (7)	C13—C12—H12	119.7
N2ⁱ—Sn1—N1ⁱ	90.25 (6)	C11—C12—H12	119.7
N2—Sn1—N1ⁱ	89.75 (6)	C14—C13—C12	120.3 (2)
N1—Sn1—N1ⁱ	180.0	C14—C13—H13	119.9
C6—N2—C9	108.73 (16)	C12—C13—H13	119.9
C6—N2—Sn1	125.33 (13)	C13—C14—C15	119.8 (2)
C9—N2—Sn1	125.86 (13)	C13—C14—H14	120.1
C4—N1—C1	109.20 (15)	C15—C14—H14	120.1
C4—N1—Sn1	125.12 (13)	C16—C15—C14	120.2 (2)
C1—N1—Sn1	125.33 (13)	C16—C15—H15	119.9
C23—O1—Sn1	118.8 (3)	C14—C15—H15	119.9
C23—O1—H2A	89.5	C15—C16—C11	120.0 (2)
Sn1—O1—H2A	109.4	C15—C16—H16	120.0
O1—C23—N3	175.3 (6)	C11—C16—H16	120.0
O1—C23—H2A	33.6	C18—C17—C22	119.0 (2)
N3—C23—H2A	144.8	C18—C17—C5	119.1 (2)
N1—C1—C10	126.57 (17)	C22—C17—C5	121.9 (2)
N1—C1—C2	107.80 (17)	C17—C18—C19	119.8 (2)
C10—C1—C2	125.62 (17)	C17—C18—H18	120.1
C3—C2—C1	107.66 (16)	C19—C18—H18	120.1
C3—C2—H2	126.2	C20—C19—C18	120.7 (3)
C1—C2—H2	126.2	C20—C19—H19	119.7
C2—C3—C4	107.30 (17)	C18—C19—H19	119.7
C2—C3—H3	126.3	C21—C20—C19	119.8 (2)
C4—C3—H3	126.3	C21—C20—H20	120.1
N1—C4—C5	126.31 (17)	C19—C20—H20	120.1
N1—C4—C3	108.03 (17)	C20—C21—C22	120.5 (3)
C5—C4—C3	125.64 (18)	C20—C21—H21	119.8
C4—C5—C6	126.92 (18)	C22—C21—H21	119.8
C4—C5—C17	116.08 (16)	C17—C22—C21	120.3 (3)
C6—C5—C17	116.89 (17)	C17—C22—H22	119.9
N2—C6—C5	125.89 (18)	C21—C22—H22	119.9
N2—C6—C7	107.95 (16)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn(C₄₄H₂₈N₄)(CNO)(OH)]
M_r	790.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.2943 (6), 12.6972 (7), 13.0711 (7)
β (°)	114.251 (2)
V (Å³)	1709.06 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.870, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	27811, 5968, 5241
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.749

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.097, 1.13
No. of reflections	5968
No. of parameters	250
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −1.34

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), publCIF (Westrip 2010).

Acknowledgements

We are grateful to the Fundacão para a Ciência e Tecnologia (FCT, Portugal) for support through projects SFRH/BPD/24889/2005 and PTDC/BIA-PRO/103980/2008 and for funding the purchase of the single-crystal diffractometer. We thank Paula Brandão from the Universidade de Aveiro for the crystal mounting and data collection.

References

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