Bis[1-(2-eth­oxy­phen­yl)-3-(4-nitro­phen­yl)triazenido]mercury(II)

Rofouei, M.K.; Fereyduni, E.; Attar Gharamaleki, J.; Bruno, G.; Amiri Rudbari, H.

doi:10.1107/S1600536810031326

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1082

https://doi.org/10.1107/S1600536810031326

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Bis[1-(2-ethoxyphenyl)-3-(4-nitrophenyl)triazenido]mercury(II)

Mohammad Kazem Rofouei,^a ^* Ehsan Fereyduni,^a Jafar Attar Gharamaleki,^b Giuseppe Bruno ^c and Hadi Amiri Rudbari ^c

^aFaculty of Chemistry, Tarbiat Moallem University, Tehran, Iran, ^bYoung Researchers Club, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^cDipartimento di Chimica Inorganica, Vill. S. Agata, Salita Sperone 31, Universita di Messina 98166 Messina, Italy
^*Correspondence e-mail: rofouei_mk@yahoo.com

(Received 27 July 2010; accepted 4 August 2010; online 11 August 2010)

In the title compound, [Hg(C₁₄H₁₃N₄O₃)₂], the central Hg atom (site symmetry 2) is six-coordinated by two tridentate 1-(2-ethoxyphenyl)-3-(4-nitrophenyl)triazenide ligands through two N and one O atoms. The mononuclear complex molecules are connected into two parallel chains by intermolecular C—H⋯O hydrogen-bonding interactions. These chains are connected to each other by face-to-edge C—H⋯π interactions between the CH of the ethoxy groups and the aromatic rings, resulting in a two-dimensional architecture in the ac plane.

Related literature

For related structures, see: Melardi et al. (2007 , 2009 ); Rofouei et al. (2009 ). For a similar complex with the same ligand, see: Melardi et al. (2010 ).

Experimental

Crystal data

[Hg(C₁₄H₁₃N₄O₃)₂]
M_r = 771.1
Orthorhombic, A b a 2
a = 15.4637 (3) Å
b = 18.6594 (4) Å
c = 9.8008 (2) Å
V = 2827.96 (10) Å³
Z = 4
Mo Kα radiation
μ = 5.50 mm⁻¹
T = 296 K
0.50 × 0.45 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: integration (SADABS; Bruker, 2005 ) T_min = 0.129, T_max = 0.280
51881 measured reflections
3358 independent reflections
2629 reflections with I > 2σ(I)
R_int = 0.122

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.110
S = 1.15
3358 reflections
196 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 2.28 e Å⁻³
Δρ_min = −2.52 e Å⁻³
Absolute structure: Flack (1983 ), 1575 Friedel pairs
Flack parameter: −0.08 (2)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.93	2.52	3.446 (9)	177
C13—H13A⋯Cg1ⁱⁱ	0.97	2.86	3.764 (8)	155
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-1]$ ; (ii) $[-x+2, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810031326/pv2312sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031326/pv2312Isup2.hkl

checkCIF report

Comment top

The study of transition-metal complexes containing 1,3-diaryltriazene ligands has greatly increased in the past few years because of the versatility of their coordination forms, yielding a variety of coordination compounds with large structural diversity. The crystal structures of a few complexes related to the title compound have been reported recently from our laboratory (Melardi et al., 2007, 2009, 2010; Rofouei et al., 2009).

In the title complex (Fig. 1), two [1-(2-ethoxyphenyl)3-(4-nitrophenyl)triazenido] ligands are coordinated to the central atom Hg(II), each through two N atoms [Hg1—N1 = 2.7873 (1) Å and Hg1—N3 = 2.0836 (1) Å] and one O atom [Hg1—O1 = 2.6562 (1) Å]. The Hg1—N1 is significantly longer than the Hg1—N3 bond. In the lattice of the title compound, the monomeric Hg(C₁₄H₁₃N₄O₃)₂ moieties are linked into chains through non-classical C8—H8···O1 hydrogen bonds, as well as C—H···π stacking interactions. Moreover, the mono-nuclear complexe molceules are connected to form two parallel chains by distinct intermolecular non-classical C—H···O hydrogen bonds. Consequently, 1-D chains are connected with one another by C—H···π stacking interactions, resulting in a 2-D architecture. These C—H···π edge-to-face interactions are present between CH group of ethoxy with aromatic rings with H···π distance of 2.86 Å for C13—H12A···Cg1 (2 - x,3/2 - y, z-1/2) [Cg1= C1—C6 (Tab. 1, Figs. 2 and 3). Also, the sum of the weak non-covalent interactions seems to play an important role in the crystal packing and the formation of a formed framework. The unit cell packing diagram of the title compound is shown in Fig. 4.

Related literature top

For related structures, see: Melardi et al. (2007, 2009); Rofouei et al. (2009). For a similar complex with the same ligand, see: Melardi et al. (2010).

Experimental top

The title complex was prepared by dissolving [1-(2-ethoxyphenyl)3- (4-nitrophenyl)]triazene (0.58 g, 2 mmol) in 20 ml anhydrous methanol. A solution of mercury acetate (0.32 g, 1 mmol) in 20 ml anhydrous methanol was added to the ligand solution. After 1 h, a red-orange solid was readily precipitated out. After two weeks beautiful red-orange and air-stable crystals of the title complex were obtained by slow evaporation of the solvent.

Structure description top

For related structures, see: Melardi et al. (2007, 2009); Rofouei et al. (2009). For a similar complex with the same ligand, see: Melardi et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2005); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, with ellipsoids drawn at 50% probability level.
	Fig. 2. C8—H8···O1 Non-classical hydrogen bonds between Hg(C₁₄H₁₃N₄O₃)₂ moieties.
	Fig. 3. C—H···π stacking interactions between two Hg(C₁₄H₁₃N₄O₃)₂ moieties.
	Fig. 4. The unit cell packing diagram of the title compound along the c axis. Hydrogen atoms not involving in the hydrogen bonds are omitted for clarity.

Bis[1-(2-ethoxyphenyl)-3-(4-nitrophenyl)triazenido]mercury(II) top

Crystal data top

[Hg(C₁₄H₁₃N₄O₃)₂]	F(000) = 1512
M_r = 771.1	D_x = 1.811 Mg m⁻³ D_m = 1.8 Mg m⁻³ D_m measured by not measured
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 9751 reflections
a = 15.4637 (3) Å	θ = 2.6–27.8°
b = 18.6594 (4) Å	µ = 5.50 mm⁻¹
c = 9.8008 (2) Å	T = 296 K
V = 2827.96 (10) Å³	Irregular, red
Z = 4	0.50 × 0.45 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	3358 independent reflections
Radiation source: fine-focus sealed tube	2629 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.122
φ and ω scans	θ_max = 27.9°, θ_min = 2.6°
Absorption correction: integration (SADABS; Bruker, 2005)	h = −20→20
T_min = 0.129, T_max = 0.280	k = −24→24
51881 measured reflections	l = −12→12

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.0655P)² + 3.2492P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.110	(Δ/σ)_max < 0.001
S = 1.15	Δρ_max = 2.28 e Å⁻³
3358 reflections	Δρ_min = −2.52 e Å⁻³
196 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00070 (17)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1575 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.08 (2)

Crystal data top

[Hg(C₁₄H₁₃N₄O₃)₂]	V = 2827.96 (10) Å³
M_r = 771.1	Z = 4
Orthorhombic, Aba2	Mo Kα radiation
a = 15.4637 (3) Å	µ = 5.50 mm⁻¹
b = 18.6594 (4) Å	T = 296 K
c = 9.8008 (2) Å	0.50 × 0.45 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	3358 independent reflections
Absorption correction: integration (SADABS; Bruker, 2005)	2629 reflections with I > 2σ(I)
T_min = 0.129, T_max = 0.280	R_int = 0.122
51881 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.110	Δρ_max = 2.28 e Å⁻³
S = 1.15	Δρ_min = −2.52 e Å⁻³
3358 reflections	Absolute structure: Flack (1983), 1575 Friedel pairs
196 parameters	Absolute structure parameter: −0.08 (2)
1 restraint

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Hg1	1.0000	1.0000	0.7679 (3)	0.03974 (13)
C7	1.1773 (4)	0.9517 (3)	0.5961 (6)	0.0546 (14)
C2	0.9670 (4)	0.8059 (3)	1.0850 (7)	0.0545 (14)
H2	1.0236	0.8178	1.0624	0.065*
O1	0.7000 (3)	0.7116 (3)	1.2795 (6)	0.0925 (17)
O3	1.0915 (3)	0.9353 (2)	0.5744 (5)	0.0615 (11)
N1	0.9199 (3)	0.8912 (2)	0.9162 (5)	0.0554 (11)
C3	0.9533 (5)	0.7573 (3)	1.1860 (7)	0.0627 (16)
H3	0.9999	0.7371	1.2319	0.075*
C14	0.9689 (8)	0.8927 (5)	0.4560 (11)	0.080 (3)
H14A	0.9497	0.8639	0.3806	0.120*
H14B	0.9488	0.9410	0.4444	0.120*
H14C	0.9462	0.8734	0.5394	0.120*
C8	1.2429 (5)	0.9181 (3)	0.5204 (8)	0.0659 (15)
H8	1.2297	0.8841	0.4543	0.079*
N3	0.8716 (3)	0.9660 (2)	0.7669 (6)	0.0492 (9)
N2	0.8539 (3)	0.9140 (3)	0.8513 (5)	0.0536 (11)
C1	0.8989 (3)	0.8390 (3)	1.0133 (6)	0.0505 (12)
C4	0.8678 (5)	0.7375 (3)	1.2210 (7)	0.0586 (15)
H4	0.8568	0.7048	1.2905	0.070*
C5	0.8026 (5)	0.7683 (4)	1.1489 (8)	0.0528 (16)
N4	0.7125 (5)	0.7478 (4)	1.1825 (7)	0.0661 (18)
O2	0.6572 (3)	0.7650 (4)	1.1014 (9)	0.116 (3)
C6	0.8148 (3)	0.8168 (3)	1.0484 (7)	0.0526 (13)
H6	0.7675	0.8357	1.0022	0.063*
C13	1.0658 (5)	0.8922 (4)	0.4614 (8)	0.0605 (18)
H13A	1.0869	0.8436	0.4728	0.073*
H13B	1.0895	0.9115	0.3774	0.073*
C9	1.3285 (5)	0.9371 (4)	0.5470 (9)	0.080 (2)
H9	1.3728	0.9154	0.4979	0.096*
C12	1.1960 (5)	1.0019 (2)	0.6943 (9)	0.0420 (15)
C11	1.2818 (5)	1.0216 (5)	0.7181 (9)	0.0652 (17)
H11	1.2950	1.0569	0.7818	0.078*
C10	1.3485 (7)	0.9873 (5)	0.6443 (13)	0.075 (3)
H10	1.4060	0.9988	0.6616	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.03350 (17)	0.04451 (17)	0.04121 (18)	−0.00398 (7)	0.000	0.000
C7	0.047 (3)	0.053 (3)	0.064 (4)	−0.002 (2)	0.000 (3)	0.013 (3)
C2	0.033 (3)	0.063 (3)	0.068 (4)	−0.002 (2)	−0.001 (3)	−0.005 (3)
O1	0.080 (3)	0.101 (4)	0.097 (4)	−0.019 (3)	0.029 (3)	0.012 (3)
O3	0.045 (2)	0.068 (2)	0.071 (3)	−0.0021 (18)	0.0040 (18)	−0.016 (2)
N1	0.047 (2)	0.059 (3)	0.061 (3)	−0.006 (2)	0.009 (2)	0.000 (3)
C3	0.052 (4)	0.069 (4)	0.067 (4)	0.003 (3)	0.000 (3)	−0.001 (3)
C14	0.081 (6)	0.073 (5)	0.086 (6)	−0.008 (5)	−0.014 (6)	−0.029 (4)
C8	0.061 (4)	0.065 (3)	0.071 (3)	0.008 (3)	0.009 (3)	0.017 (4)
N3	0.037 (2)	0.053 (2)	0.058 (3)	−0.0038 (17)	0.002 (2)	−0.006 (3)
N2	0.048 (3)	0.057 (3)	0.056 (3)	−0.008 (2)	0.008 (2)	−0.004 (2)
C1	0.042 (3)	0.053 (3)	0.057 (3)	−0.010 (2)	0.007 (2)	−0.009 (3)
C4	0.061 (4)	0.058 (3)	0.057 (4)	−0.009 (3)	0.005 (3)	−0.002 (3)
C5	0.042 (3)	0.054 (3)	0.062 (4)	−0.004 (2)	0.013 (3)	−0.012 (3)
N4	0.047 (4)	0.070 (4)	0.081 (5)	−0.011 (2)	0.020 (3)	0.012 (3)
O2	0.040 (3)	0.148 (5)	0.159 (6)	−0.005 (3)	0.012 (4)	0.066 (5)
C6	0.035 (2)	0.056 (3)	0.067 (4)	−0.006 (2)	0.007 (2)	−0.004 (3)
C13	0.075 (5)	0.044 (3)	0.062 (4)	−0.001 (3)	0.009 (4)	−0.009 (3)
C9	0.061 (4)	0.082 (5)	0.096 (6)	0.020 (4)	0.023 (4)	0.036 (5)
C12	0.039 (4)	0.046 (3)	0.041 (4)	−0.0032 (18)	0.000 (3)	0.0117 (19)
C11	0.043 (4)	0.081 (4)	0.071 (5)	−0.008 (4)	0.000 (3)	0.012 (4)
C10	0.040 (4)	0.103 (6)	0.082 (7)	−0.005 (4)	0.002 (4)	0.032 (5)

Geometric parameters (Å, º) top

Hg1—N3ⁱ	2.084 (4)	C8—C9	1.394 (11)
Hg1—N3	2.084 (4)	C8—H8	0.9300
Hg1—O3	2.656 (5)	N3—N2	1.304 (6)
Hg1—O3ⁱ	2.656 (5)	N3—C12ⁱ	1.400 (9)
C7—C12	1.374 (9)	C1—C6	1.407 (6)
C7—O3	1.378 (7)	C4—C5	1.359 (11)
C7—C8	1.406 (9)	C4—H4	0.9300
C2—C3	1.359 (9)	C5—C6	1.351 (10)
C2—C1	1.409 (8)	C5—N4	1.481 (10)
C2—H2	0.9300	N4—O2	1.211 (10)
O1—N4	1.182 (9)	C6—H6	0.9300
O3—C13	1.425 (8)	C13—H13A	0.9700
N1—N2	1.275 (6)	C13—H13B	0.9700
N1—C1	1.400 (7)	C9—C10	1.372 (14)
C3—C4	1.414 (9)	C9—H9	0.9300
C3—H3	0.9300	C12—C11	1.396 (11)
C14—C13	1.500 (13)	C12—N3ⁱ	1.400 (9)
C14—H14A	0.9600	C11—C10	1.412 (15)
C14—H14B	0.9600	C11—H11	0.9300
C14—H14C	0.9600	C10—H10	0.9300

N3ⁱ—Hg1—N3	179.4 (4)	N1—C1—C2	118.1 (5)
N3ⁱ—Hg1—O3	68.12 (18)	C6—C1—C2	116.1 (6)
N3—Hg1—O3	111.46 (18)	C5—C4—C3	117.2 (6)
N3ⁱ—Hg1—O3ⁱ	111.46 (18)	C5—C4—H4	121.4
N3—Hg1—O3ⁱ	68.12 (18)	C3—C4—H4	121.4
O3—Hg1—O3ⁱ	88.9 (2)	C6—C5—C4	123.9 (6)
C12—C7—O3	117.6 (6)	C6—C5—N4	117.8 (7)
C12—C7—C8	121.5 (6)	C4—C5—N4	118.2 (7)
O3—C7—C8	121.0 (6)	O1—N4—O2	124.3 (7)
C3—C2—C1	122.6 (6)	O1—N4—C5	118.7 (7)
C3—C2—H2	118.7	O2—N4—C5	116.8 (6)
C1—C2—H2	118.7	C5—C6—C1	120.3 (6)
C7—O3—C13	120.9 (5)	C5—C6—H6	119.8
C7—O3—Hg1	107.5 (4)	C1—C6—H6	119.8
C13—O3—Hg1	131.5 (4)	O3—C13—C14	107.6 (5)
N2—N1—C1	112.7 (4)	O3—C13—H13A	110.2
C2—C3—C4	119.8 (6)	C14—C13—H13A	110.2
C2—C3—H3	120.1	O3—C13—H13B	110.2
C4—C3—H3	120.1	C14—C13—H13B	110.2
C13—C14—H14A	109.5	H13A—C13—H13B	108.5
C13—C14—H14B	109.5	C10—C9—C8	121.2 (8)
H14A—C14—H14B	109.5	C10—C9—H9	119.4
C13—C14—H14C	109.5	C8—C9—H9	119.4
H14A—C14—H14C	109.5	C7—C12—C11	119.8 (8)
H14B—C14—H14C	109.5	C7—C12—N3ⁱ	119.3 (6)
C9—C8—C7	118.2 (7)	C11—C12—N3ⁱ	120.9 (7)
C9—C8—H8	120.9	C12—C11—C10	119.2 (9)
C7—C8—H8	120.9	C12—C11—H11	120.4
N2—N3—C12ⁱ	118.9 (5)	C10—C11—H11	120.4
N2—N3—Hg1	115.1 (4)	C9—C10—C11	120.1 (9)
C12ⁱ—N3—Hg1	125.8 (4)	C9—C10—H10	120.0
N1—N2—N3	113.4 (4)	C11—C10—H10	120.0
N1—C1—C6	125.8 (5)

C12—C7—O3—C13	170.6 (6)	C3—C2—C1—C6	−2.4 (9)
C8—C7—O3—C13	−9.5 (8)	C2—C3—C4—C5	0.8 (10)
C12—C7—O3—Hg1	−8.0 (6)	C3—C4—C5—C6	−1.0 (11)
C8—C7—O3—Hg1	172.0 (4)	C3—C4—C5—N4	179.2 (6)
N3ⁱ—Hg1—O3—C7	10.0 (3)	C6—C5—N4—O1	−171.7 (7)
N3—Hg1—O3—C7	−170.4 (3)	C4—C5—N4—O1	8.0 (10)
O3ⁱ—Hg1—O3—C7	123.7 (4)	C6—C5—N4—O2	13.8 (11)
N3ⁱ—Hg1—O3—C13	−168.4 (6)	C4—C5—N4—O2	−166.5 (7)
N3—Hg1—O3—C13	11.3 (6)	C4—C5—C6—C1	−0.5 (10)
O3ⁱ—Hg1—O3—C13	−54.6 (5)	N4—C5—C6—C1	179.2 (6)
C1—C2—C3—C4	0.9 (9)	N1—C1—C6—C5	−176.8 (6)
C12—C7—C8—C9	−0.2 (9)	C2—C1—C6—C5	2.2 (8)
O3—C7—C8—C9	179.8 (5)	C7—O3—C13—C14	−172.6 (6)
O3—Hg1—N3—N2	94.9 (4)	Hg1—O3—C13—C14	5.6 (8)
O3ⁱ—Hg1—N3—N2	174.5 (4)	C7—C8—C9—C10	−0.1 (10)
O3—Hg1—N3—C12ⁱ	−91.2 (5)	O3—C7—C12—C11	−178.5 (6)
O3ⁱ—Hg1—N3—C12ⁱ	−11.6 (5)	C8—C7—C12—C11	1.5 (9)
C1—N1—N2—N3	175.7 (4)	O3—C7—C12—N3ⁱ	−0.1 (8)
C12ⁱ—N3—N2—N1	−177.0 (5)	C8—C7—C12—N3ⁱ	179.9 (6)
Hg1—N3—N2—N1	−2.6 (6)	C7—C12—C11—C10	−2.5 (11)
N2—N1—C1—C6	−5.5 (7)	N3ⁱ—C12—C11—C10	179.1 (7)
N2—N1—C1—C2	175.6 (5)	C8—C9—C10—C11	−1.0 (12)
C3—C2—C1—N1	176.6 (5)	C12—C11—C10—C9	2.3 (13)

Symmetry code: (i) −x+2, −y+2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱⁱ	0.93	2.52	3.446 (9)	177
C13—H13A···Cg1ⁱⁱⁱ	0.97	2.86	3.764 (8)	155

Symmetry codes: (ii) x+1/2, −y+3/2, z−1; (iii) −x+2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Hg(C₁₄H₁₃N₄O₃)₂]
M_r	771.1
Crystal system, space group	Orthorhombic, Aba2
Temperature (K)	296
a, b, c (Å)	15.4637 (3), 18.6594 (4), 9.8008 (2)
V (Å³)	2827.96 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.50
Crystal size (mm)	0.50 × 0.45 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Integration (SADABS; Bruker, 2005)
T_min, T_max	0.129, 0.280
No. of measured, independent and observed [I > 2σ(I)] reflections	51881, 3358, 2629
R_int	0.122
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.110, 1.15
No. of reflections	3358
No. of parameters	196
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.28, −2.52
Absolute structure	Flack (1983), 1575 Friedel pairs
Absolute structure parameter	−0.08 (2)

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.52	3.446 (9)	177
C13—H13A···Cg1ⁱⁱ	0.97	2.86	3.764 (8)	155

Symmetry codes: (i) x+1/2, −y+3/2, z−1; (ii) −x+2, −y+3/2, z+1/2.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Melardi, M. R., Roohi, Z., Heidari, N. & Rofouei, M. K. (2010). Acta Cryst. E66, m975. Web of Science CSD CrossRef IUCr Journals Google Scholar
Melardi, M. R., Rofouei, M. K. & Massomi, J. (2007). Anal. Sci. 23, x67–x68. CAS Google Scholar
Melardi, M. R., Salemi, Y., Razi Kazemi, S. & Rofouei, M. K. (2009). Acta Cryst. E65, m302. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rofouei, M. K., Hematyar, M., Ghoulipour, V. & Attar Gharamaleki, J. (2009). Inorg. Chim. Acta. 362, 3777–3784. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 9| September 2010| Page m1082

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