5,15-Bis(4-pentyl­oxyphen­yl)porphyrin

Senge, M.O.

doi:10.1107/S160053681301550X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1048

https://doi.org/10.1107/S160053681301550X

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5,15-Bis(4-pentyloxyphenyl)porphyrin

Mathias O. Senge ^a ^*

^aSchool of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Sciences Institute, 152-160 Pearse Street, Trinity College Dublin, Dublin 2, Ireland
^*Correspondence e-mail: sengem@tcd.ie

(Received 26 May 2013; accepted 4 June 2013; online 8 June 2013)

In the title compound, C₄₂H₄₂N₄O₂, the complete molecule is generated by a crystallographic inversion centre. The porphyrin system exhibits a near planar macrocycle conformation with an average deviation from the least-squares plane of the 24 macrocycle atoms of 0.037 (5) Å. The phenyl ipso C atoms are positioned above and below the porphyrin plane by 0.35 (1) Å and the macrocycle shows evidence of in-plane rectangular elongation with N⋯N separations of 3.032 (5) and 2.803 (5) Å. Two intramolecular N—H⋯N hydrogen bonds occur.

Related literature

For the conformation of porphyrins, see: Scheidt & Lee (1987 ); Senge et al. (1997 ); Senge (2006 ). For the synthesis of such compounds, see: Wiehe et al. (2005 ).

Experimental

Crystal data

C₄₂H₄₂N₄O₂
M_r = 634.80
Triclinic, $[P \overline 1]$
a = 9.5222 (6) Å
b = 9.5799 (6) Å
c = 10.2195 (6) Å
α = 67.777 (1)°
β = 88.063 (1)°
γ = 72.464 (1)°
V = 819.49 (9) Å³
Z = 1
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 90 K
0.30 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.97, T_max = 0.99
9093 measured reflections
3606 independent reflections
2489 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.109
S = 1.04
3606 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21—H21⋯N24	0.88	2.50	3.033 (2)	119
N21—H21⋯N24ⁱ	0.88	2.22	2.804 (2)	123
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL.

Supporting information

Crystal structure: contains datablocks I, 2R. DOI: https://doi.org/10.1107/S160053681301550X/zl2552sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681301550X/zl2552Isup2.hkl

checkCIF report

Comment top

Many porphyrin structures with four meso substituents have been reported (Scheidt & Lee, 1987). The available number of structures for systems with only two meso residues is much smaller. In the context of an ongoing program on the conformational flexibilty of porphyrins (Senge, 2006) we are interested in a comparative analysis of 5,10-A₂– and 5,15-A₂-disubstituted porphyrins. The title compound is an example for the latter and exhibits a planar macrocycle with an average deviation from the least-squares-plane of the 24 macrocycle atoms of Δ24 = 0.037 (5) Å. The phenyl ipso carbon atoms are positioned above and below the porphyrin plane by 0.35 Å and the macrocycle shows evidence for in-plane distortion with N···N separations of 3.032 (5) and 2.803 (5) Å. This is similar to the situation found in 2,3,5,7,8,12,13,15, 17,18- decasubstituted porphyrins (Senge et al., 1997) where peri interaction between the meso and beta substituents occur. The molecules pack in parallel layers with the alkyl chains separating the macrocycles and only minimal π-aggregation.

Related literature top

For the conformation of porphyrins, see: Scheidt & Lee (1987); Senge et al. (1997); Senge (2006). For the synthesis of such compounds, see: Wiehe et al. (2005).

Experimental top

The compound was prepared as described by Wiehe et al. (2005) and crystallized from CH₂Cl₂/CH₃OH.

Structure description top

For the conformation of porphyrins, see: Scheidt & Lee (1987); Senge et al. (1997); Senge (2006). For the synthesis of such compounds, see: Wiehe et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. : Molecular structure of the title compound. Thermal ellipsoids are drawn at 50% probability level; hydrogen atoms have been omitted for clarity.

5,15-Bis(4-pentyloxyphenyl)porphyrin top

Crystal data top

C₄₂H₄₂N₄O₂	Z = 1
M_r = 634.80	F(000) = 338
Triclinic, P1	D_x = 1.286 Mg m⁻³ D_m = n/d Mg m⁻³ D_m measured by not measured
Hall symbol: -P 1	Melting point: n/d K
a = 9.5222 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5799 (6) Å	Cell parameters from 1771 reflections
c = 10.2195 (6) Å	θ = 4.5–60.7°
α = 67.777 (1)°	µ = 0.08 mm⁻¹
β = 88.063 (1)°	T = 90 K
γ = 72.464 (1)°	Parallelpiped, red
V = 819.49 (9) Å³	0.30 × 0.10 × 0.08 mm

Data collection top

Bruker SMART APEXII diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2489 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 8.3 pixels mm^-1	θ_max = 27.1°, θ_min = 2.2°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
T_min = 0.97, T_max = 0.99	l = −13→13
9093 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0433P)² + 0.1316P] where P = (F_o² + 2F_c²)/3
3606 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₄₂H₄₂N₄O₂	γ = 72.464 (1)°
M_r = 634.80	V = 819.49 (9) Å³
Triclinic, P1	Z = 1
a = 9.5222 (6) Å	Mo Kα radiation
b = 9.5799 (6) Å	µ = 0.08 mm⁻¹
c = 10.2195 (6) Å	T = 90 K
α = 67.777 (1)°	0.30 × 0.10 × 0.08 mm
β = 88.063 (1)°

Data collection top

Bruker SMART APEXII diffractometer	3606 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2489 reflections with I > 2σ(I)
T_min = 0.97, T_max = 0.99	R_int = 0.039
9093 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	Δρ_max = 0.27 e Å⁻³
3606 reflections	Δρ_min = −0.23 e Å⁻³
219 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
N21	0.64309 (14)	−0.19503 (16)	0.46008 (14)	0.0171 (3)
H21	0.5815	−0.1069	0.4627	0.047 (6)*
N24	0.36841 (13)	−0.12143 (15)	0.61217 (14)	0.0160 (3)
C1	0.62390 (16)	−0.34160 (19)	0.52069 (17)	0.0179 (4)
C2	0.74472 (17)	−0.4492 (2)	0.48647 (18)	0.0190 (4)
H2A	0.7600	−0.5592	0.5123	0.023*
C3	0.83431 (17)	−0.36651 (19)	0.41037 (17)	0.0185 (4)
H3A	0.9229	−0.4090	0.3740	0.022*
C4	0.77200 (16)	−0.20511 (19)	0.39479 (17)	0.0169 (4)
C5	0.83034 (16)	−0.07952 (19)	0.33369 (17)	0.0169 (4)
C16	0.24129 (16)	−0.07563 (19)	0.67302 (16)	0.0164 (3)
C17	0.18961 (17)	−0.2107 (2)	0.74985 (18)	0.0195 (4)
H17A	0.1041	−0.2097	0.8006	0.023*
C18	0.28721 (17)	−0.3376 (2)	0.73457 (18)	0.0198 (4)
H18A	0.2843	−0.4437	0.7732	0.024*
C19	0.39727 (16)	−0.28065 (19)	0.64781 (17)	0.0172 (4)
C20	0.51314 (16)	−0.37959 (19)	0.60556 (17)	0.0185 (4)
H20A	0.5167	−0.4877	0.6396	0.022*
C51	0.98127 (17)	−0.11283 (19)	0.28262 (17)	0.0177 (4)
C52	1.01657 (17)	−0.1671 (2)	0.17315 (18)	0.0206 (4)
H52A	0.9421	−0.1859	0.1286	0.025*
C53	1.15769 (17)	−0.1945 (2)	0.12745 (18)	0.0207 (4)
H53A	1.1792	−0.2316	0.0527	0.025*
C54	1.26742 (16)	−0.16720 (19)	0.19238 (18)	0.0188 (4)
C55	1.23542 (17)	−0.11454 (19)	0.30202 (17)	0.0192 (4)
H55A	1.3103	−0.0965	0.3467	0.023*
C56	1.09475 (17)	−0.08822 (19)	0.34664 (18)	0.0192 (4)
H56A	1.0744	−0.0526	0.4224	0.023*
O1	1.41004 (11)	−0.18754 (14)	0.15628 (12)	0.0226 (3)
C57	1.45008 (17)	−0.2298 (2)	0.03660 (18)	0.0227 (4)
H57A	1.3832	−0.1524	−0.0488	0.027*
H57B	1.4430	−0.3366	0.0554	0.027*
C58	1.60744 (17)	−0.2284 (2)	0.01421 (18)	0.0211 (4)
H58A	1.6702	−0.2943	0.1048	0.025*
H58B	1.6106	−0.1185	−0.0147	0.025*
C59	1.66924 (17)	−0.2919 (2)	−0.09922 (19)	0.0249 (4)
H59A	1.6492	−0.3934	−0.0788	0.030*
H59B	1.6167	−0.2157	−0.1927	0.030*
C510	1.83383 (17)	−0.3191 (2)	−0.10777 (18)	0.0217 (4)
H51A	1.8868	−0.3995	−0.0159	0.026*
H51B	1.8546	−0.2190	−0.1236	0.026*
C511	1.89275 (18)	−0.3744 (2)	−0.22522 (19)	0.0277 (4)
H51C	2.0009	−0.4029	−0.2182	0.042*
H51D	1.8518	−0.2889	−0.3175	0.042*
H51E	1.8637	−0.4673	−0.2159	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N21	0.0139 (7)	0.0134 (7)	0.0229 (8)	−0.0023 (5)	0.0014 (5)	−0.0075 (6)
N24	0.0136 (6)	0.0145 (7)	0.0195 (7)	−0.0030 (5)	−0.0003 (5)	−0.0071 (6)
C1	0.0159 (8)	0.0165 (8)	0.0220 (9)	−0.0040 (6)	−0.0007 (6)	−0.0088 (7)
C2	0.0184 (8)	0.0141 (8)	0.0241 (9)	−0.0023 (6)	0.0006 (7)	−0.0090 (7)
C3	0.0148 (8)	0.0197 (9)	0.0206 (9)	−0.0017 (6)	0.0021 (6)	−0.0103 (7)
C4	0.0119 (7)	0.0192 (9)	0.0184 (9)	−0.0012 (6)	0.0004 (6)	−0.0087 (7)
C5	0.0151 (8)	0.0190 (9)	0.0171 (8)	−0.0047 (6)	0.0008 (6)	−0.0078 (7)
C16	0.0156 (8)	0.0186 (9)	0.0146 (8)	−0.0046 (6)	0.0001 (6)	−0.0065 (7)
C17	0.0179 (8)	0.0206 (9)	0.0199 (9)	−0.0071 (7)	0.0040 (6)	−0.0071 (7)
C18	0.0193 (8)	0.0156 (9)	0.0237 (9)	−0.0066 (7)	0.0022 (7)	−0.0059 (7)
C19	0.0153 (8)	0.0159 (8)	0.0201 (9)	−0.0046 (6)	−0.0004 (6)	−0.0066 (7)
C20	0.0180 (8)	0.0136 (8)	0.0236 (9)	−0.0054 (6)	−0.0001 (6)	−0.0063 (7)
C51	0.0171 (8)	0.0144 (8)	0.0191 (9)	−0.0031 (6)	0.0028 (6)	−0.0052 (7)
C52	0.0183 (8)	0.0214 (9)	0.0221 (9)	−0.0066 (7)	0.0012 (7)	−0.0080 (8)
C53	0.0232 (9)	0.0212 (9)	0.0189 (9)	−0.0060 (7)	0.0045 (7)	−0.0100 (7)
C54	0.0146 (8)	0.0146 (8)	0.0222 (9)	−0.0026 (6)	0.0047 (6)	−0.0036 (7)
C55	0.0193 (8)	0.0165 (9)	0.0204 (9)	−0.0057 (7)	−0.0015 (7)	−0.0053 (7)
C56	0.0197 (8)	0.0182 (9)	0.0184 (9)	−0.0034 (7)	0.0021 (6)	−0.0078 (7)
O1	0.0168 (6)	0.0286 (7)	0.0251 (7)	−0.0071 (5)	0.0065 (5)	−0.0135 (6)
C57	0.0202 (8)	0.0268 (10)	0.0229 (9)	−0.0062 (7)	0.0069 (7)	−0.0127 (8)
C58	0.0180 (8)	0.0183 (9)	0.0233 (9)	−0.0047 (7)	0.0060 (7)	−0.0050 (7)
C59	0.0204 (9)	0.0312 (11)	0.0260 (10)	−0.0096 (8)	0.0071 (7)	−0.0135 (8)
C510	0.0185 (8)	0.0216 (9)	0.0237 (9)	−0.0046 (7)	0.0049 (7)	−0.0088 (8)
C511	0.0209 (9)	0.0360 (11)	0.0324 (11)	−0.0105 (8)	0.0071 (8)	−0.0190 (9)

Geometric parameters (Å, º) top

N21—C1	1.370 (2)	C52—H52A	0.9500
N21—C4	1.3722 (19)	C53—C54	1.394 (2)
N21—H21	0.8800	C53—H53A	0.9500
N24—C19	1.367 (2)	C54—O1	1.3710 (18)
N24—C16	1.3711 (19)	C54—C55	1.384 (2)
C1—C20	1.388 (2)	C55—C56	1.381 (2)
C1—C2	1.428 (2)	C55—H55A	0.9500
C2—C3	1.362 (2)	C56—H56A	0.9500
C2—H2A	0.9500	O1—C57	1.4335 (19)
C3—C4	1.427 (2)	C57—C58	1.511 (2)
C3—H3A	0.9500	C57—H57A	0.9900
C4—C5	1.399 (2)	C57—H57B	0.9900
C5—C16ⁱ	1.412 (2)	C58—C59	1.527 (2)
C5—C51	1.496 (2)	C58—H58A	0.9900
C16—C5ⁱ	1.412 (2)	C58—H58B	0.9900
C16—C17	1.457 (2)	C59—C510	1.515 (2)
C17—C18	1.348 (2)	C59—H59A	0.9900
C17—H17A	0.9500	C59—H59B	0.9900
C18—C19	1.448 (2)	C510—C511	1.514 (2)
C18—H18A	0.9500	C510—H51A	0.9900
C19—C20	1.396 (2)	C510—H51B	0.9900
C20—H20A	0.9500	C511—H51C	0.9800
C51—C52	1.394 (2)	C511—H51D	0.9800
C51—C56	1.403 (2)	C511—H51E	0.9800
C52—C53	1.389 (2)

C1—N21—C4	110.37 (13)	C54—C53—H53A	120.3
C1—N21—H21	124.8	O1—C54—C55	114.91 (14)
C4—N21—H21	124.8	O1—C54—C53	125.17 (15)
C19—N24—C16	105.16 (13)	C55—C54—C53	119.92 (14)
N21—C1—C20	126.59 (15)	C56—C55—C54	120.09 (15)
N21—C1—C2	106.65 (13)	C56—C55—H55A	120.0
C20—C1—C2	126.68 (15)	C54—C55—H55A	120.0
C3—C2—C1	108.13 (15)	C55—C56—C51	121.49 (16)
C3—C2—H2A	125.9	C55—C56—H56A	119.3
C1—C2—H2A	125.9	C51—C56—H56A	119.3
C2—C3—C4	108.17 (14)	C54—O1—C57	118.76 (12)
C2—C3—H3A	125.9	O1—C57—C58	106.88 (13)
C4—C3—H3A	125.9	O1—C57—H57A	110.3
N21—C4—C5	124.67 (14)	C58—C57—H57A	110.3
N21—C4—C3	106.62 (14)	O1—C57—H57B	110.3
C5—C4—C3	128.61 (14)	C58—C57—H57B	110.3
C4—C5—C16ⁱ	123.29 (14)	H57A—C57—H57B	108.6
C4—C5—C51	118.72 (14)	C57—C58—C59	111.63 (14)
C16ⁱ—C5—C51	117.82 (14)	C57—C58—H58A	109.3
N24—C16—C5ⁱ	125.69 (15)	C59—C58—H58A	109.3
N24—C16—C17	110.71 (14)	C57—C58—H58B	109.3
C5ⁱ—C16—C17	123.59 (14)	C59—C58—H58B	109.3
C18—C17—C16	106.36 (14)	H58A—C58—H58B	108.0
C18—C17—H17A	126.8	C510—C59—C58	113.42 (14)
C16—C17—H17A	126.8	C510—C59—H59A	108.9
C17—C18—C19	106.69 (15)	C58—C59—H59A	108.9
C17—C18—H18A	126.7	C510—C59—H59B	108.9
C19—C18—H18A	126.7	C58—C59—H59B	108.9
N24—C19—C20	126.46 (14)	H59A—C59—H59B	107.7
N24—C19—C18	111.07 (13)	C59—C510—C511	113.04 (14)
C20—C19—C18	122.44 (15)	C59—C510—H51A	109.0
C1—C20—C19	128.88 (15)	C511—C510—H51A	109.0
C1—C20—H20A	115.6	C59—C510—H51B	109.0
C19—C20—H20A	115.6	C511—C510—H51B	109.0
C52—C51—C56	117.34 (14)	H51A—C510—H51B	107.8
C52—C51—C5	123.54 (14)	C510—C511—H51C	109.5
C56—C51—C5	119.12 (15)	C510—C511—H51D	109.5
C53—C52—C51	121.78 (15)	H51C—C511—H51D	109.5
C53—C52—H52A	119.1	C510—C511—H51E	109.5
C51—C52—H52A	119.1	H51C—C511—H51E	109.5
C52—C53—C54	119.38 (16)	H51D—C511—H51E	109.5
C52—C53—H53A	120.3

C4—N21—C1—C20	174.18 (15)	C2—C1—C20—C19	176.51 (16)
C4—N21—C1—C2	−2.51 (18)	N24—C19—C20—C1	0.4 (3)
N21—C1—C2—C3	1.54 (18)	C18—C19—C20—C1	178.43 (16)
C20—C1—C2—C3	−175.14 (16)	C4—C5—C51—C52	63.4 (2)
C1—C2—C3—C4	−0.05 (19)	C16ⁱ—C5—C51—C52	−121.15 (18)
C1—N21—C4—C5	−174.17 (15)	C4—C5—C51—C56	−116.84 (18)
C1—N21—C4—C3	2.48 (18)	C16ⁱ—C5—C51—C56	58.6 (2)
C2—C3—C4—N21	−1.45 (18)	C56—C51—C52—C53	−0.7 (2)
C2—C3—C4—C5	175.01 (16)	C5—C51—C52—C53	179.07 (15)
N21—C4—C5—C16ⁱ	−2.8 (3)	C51—C52—C53—C54	0.0 (2)
C3—C4—C5—C16ⁱ	−178.73 (16)	C52—C53—C54—O1	−179.13 (15)
N21—C4—C5—C51	172.32 (14)	C52—C53—C54—C55	0.5 (2)
C3—C4—C5—C51	−3.6 (3)	O1—C54—C55—C56	179.34 (14)
C19—N24—C16—C5ⁱ	179.15 (15)	C53—C54—C55—C56	−0.4 (2)
C19—N24—C16—C17	0.37 (17)	C54—C55—C56—C51	−0.4 (2)
N24—C16—C17—C18	0.14 (18)	C52—C51—C56—C55	0.9 (2)
C5ⁱ—C16—C17—C18	−178.68 (15)	C5—C51—C56—C55	−178.90 (15)
C16—C17—C18—C19	−0.56 (18)	C55—C54—O1—C57	−175.16 (14)
C16—N24—C19—C20	177.47 (16)	C53—C54—O1—C57	4.5 (2)
C16—N24—C19—C18	−0.72 (17)	C54—O1—C57—C58	174.70 (13)
C17—C18—C19—N24	0.84 (19)	O1—C57—C58—C59	172.84 (13)
C17—C18—C19—C20	−177.45 (15)	C57—C58—C59—C510	−170.19 (15)
N21—C1—C20—C19	0.5 (3)	C58—C59—C510—C511	−177.21 (15)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···N24	0.88	2.50	3.033 (2)	119
N21—H21···N24ⁱ	0.88	2.22	2.804 (2)	123

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₄₂H₄₂N₄O₂
M_r	634.80
Crystal system, space group	Triclinic, P1
Temperature (K)	90
a, b, c (Å)	9.5222 (6), 9.5799 (6), 10.2195 (6)
α, β, γ (°)	67.777 (1), 88.063 (1), 72.464 (1)
V (Å³)	819.49 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.97, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	9093, 3606, 2489
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.109, 1.04
No. of reflections	3606
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···N24	0.88	2.50	3.033 (2)	119
N21—H21···N24ⁱ	0.88	2.22	2.804 (2)	123

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

This work was supported by a grant from Science Foundation Ireland (SFI P.I. 09/IN.1/B2650).

References

Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Scheidt, W. R. & Lee, Y. J. (1987). Struct. Bond. 64, 1–70. CrossRef CAS Google Scholar
Senge, M. O. (2006). Chem. Commun. pp. 243–256. Web of Science CrossRef Google Scholar
Senge, M. O., Medforth, C. J., Forsyth, T. P., Lee, D. A., Olmstead, M. M., Jentzen, W., Pandey, R. K., Shelnutt, J. A. & Smith, K. M. (1997). Inorg. Chem. 36, 1149–1163. CSD CrossRef PubMed CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wiehe, A., Shaker, Y. M., Brandt, J. C., Mebs, S. & Senge, M. O. (2005). Tetrahedron, 61, 5535–5564. Web of Science CrossRef CAS Google Scholar

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