[1,3-Bis(2-ethoxy­phen­yl)triazenido]chloridomercury(II)

Melardi, M.R.; Salemi, Y.; Razi Kazemi, S.; Rofouei, M.K.

doi:10.1107/S160053680900539X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m302

doi:10.1107/S160053680900539X

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[1,3-Bis(2-ethoxyphenyl)triazenido]chloridomercury(II)

Mohammad Reza Melardi,^a Yasaman Salemi,^a Saba Razi Kazemi ^a and Mohammad Kazem Rofouei ^b ^*

^aDepartment of Chemistry, Islamic Azad University, Karaj Branch, Karaj, Iran, and ^bFaculty of Chemistry, Tarbiat Moallem University, Tehran, Iran
^*Correspondence e-mail: rofouei_mk@yahoo.com

(Received 7 February 2009; accepted 15 February 2009; online 21 February 2009)

In the title compound, [Hg(C₁₆H₁₈N₃O₂)Cl], the Hg^II atom is four-coordinated in a tetrahedral geometry by two N atoms from the 1,3-chelating and one O atom of a 1,3-bis(2-ethoxyphenyl)triazenido ligand and one terminal chloride ion. The dihedral angle between the aromatic rings is 1.72 (14)°. In the crystal C—H⋯π stacking interactions occur.

Related literature

For related structures, see: Rofouei et al. 2008 ; Melardi et al. 2007 .

Experimental

Crystal data

[Hg(C₁₆H₁₈N₃O₂)Cl]
M_r = 520.37
Monoclinic, P 2₁ /n
a = 10.1600 (5) Å
b = 7.3802 (4) Å
c = 22.5655 (11) Å
β = 97.817 (1)°
V = 1676.30 (15) Å³
Z = 4
Mo Kα radiation
μ = 9.35 mm⁻¹
T = 100 K
0.15 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (APEX2; Bruker, 2005 ) T_min = 0.280, T_max = 0.479
19713 measured reflections
4451 independent reflections
4009 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.049
S = 1.01
4451 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −1.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cg1ⁱ	0.95	2.87	3.598 (3)	134
C15—H15B⋯Cg1ⁱⁱ	0.99	2.68	3.511 (3)	142
Symmetry codes: (i) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z. Cg1 is the centroid of the C1–C6 ring.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900539X/pv2138sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900539X/pv2138Isup2.hkl

checkCIF report

Comment top

Recently we have reported the synthesis and crystal structure of [1,3-bis(2-methoxyphenyl)triazene with Hg^II as ML₂ structure [Rofouei et al., 2008] and [1,3-bis(2-methoxybenzene)triazene with Hg^II as ML structure [Melardi et al., 2007]. In this article we report the synthesis and crystal structure of the title compound, (I).

In the title compound, the Hg^II atom is four-coordinated in a tetrahedral configuration by two N atoms from the chelating (1,3) and one O atom of ethoxyphenyl triazenido ligand and one terminal Cl atom leading to an asymmetric molecule (Fig. 1). There are interesting C—H···π stacking interactions between CH groups and aromatic phenyl rings with C—H···π distances of 2.869 Å for C3—H3A···Cg1 (5/2 - x, 1/2 + y, 1/2 - z) and 2.681 Å for C15—H15B···Cg1 (2 - x, 1 - y, -z) (Cg1 is centroid of C1—C6 ring) as presented in Fig. 2. The unit cell packing of the title compound showing stacking of molecules is presented at Fig. 3.

Related literature top

For related structures, see: Rofouei et al. 2008; Melardi et al. 2007.

Experimental top

A solution of [1,3-bis(2-ethoxyphenyl)triazene] (1 mmol, 0.285 g) in acetonitril (10 ml) and triethylamin (0.3 ml) was added to a solution of HgCl₂ (1 mmol, 0.271 g) in methanol (10 ml) yielded the title compound. The suitable crystals for X-ray analysis were obtained from a solution of ethyl acetate after one week. m.p. = 449-451 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); 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 complex. Thermal ellipsoids are drawn at 50% probability level.
	Fig. 2. C—H···π Stacking interactions between CH groups and aromatic phenyl rings centroid.
	Fig. 3. Unit cell packing diagram of the title complex.

[1,3-Bis(2-ethoxyphenyl)triazenido]chloridomercury(II) top

Crystal data top

[Hg(C₁₆H₁₈N₃O₂)Cl]	F(000) = 992
M_r = 520.37	D_x = 2.062 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8520 reflections
a = 10.1600 (5) Å	θ = 3–29°
b = 7.3802 (4) Å	µ = 9.35 mm⁻¹
c = 22.5655 (11) Å	T = 100 K
β = 97.817 (1)°	Prism, colorless
V = 1676.30 (15) Å³	0.15 × 0.12 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4451 independent reflections
Radiation source: fine-focus sealed tube	4009 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 29.0°, θ_min = 1.8°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −13→13
T_min = 0.280, T_max = 0.479	k = −10→10
19713 measured reflections	l = −30→30

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.02P)² + 2P] where P = (F_o² + 2F_c²)/3
4451 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.98 e Å⁻³
0 restraints	Δρ_min = −1.19 e Å⁻³

Crystal data top

[Hg(C₁₆H₁₈N₃O₂)Cl]	V = 1676.30 (15) Å³
M_r = 520.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1600 (5) Å	µ = 9.35 mm⁻¹
b = 7.3802 (4) Å	T = 100 K
c = 22.5655 (11) Å	0.15 × 0.12 × 0.08 mm
β = 97.817 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4451 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2005)	4009 reflections with I > 2σ(I)
T_min = 0.280, T_max = 0.479	R_int = 0.036
19713 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.049	H-atom parameters constrained
S = 1.01	Δρ_max = 0.98 e Å⁻³
4451 reflections	Δρ_min = −1.19 e Å⁻³
210 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
Hg1	0.849438 (10)	0.312052 (15)	0.054958 (5)	0.01838 (4)
Cl1	0.65126 (8)	0.35249 (12)	0.09032 (4)	0.03193 (18)
O1	1.0251 (2)	0.5538 (3)	0.20153 (9)	0.0187 (4)
O2	0.82363 (19)	0.1411 (3)	−0.05286 (9)	0.0174 (4)
N1	1.0926 (2)	0.4172 (3)	0.10284 (10)	0.0159 (4)
N2	1.1288 (2)	0.3584 (3)	0.05434 (11)	0.0160 (5)
N3	1.0261 (2)	0.2874 (3)	0.01919 (11)	0.0158 (5)
C1	1.1957 (3)	0.4946 (4)	0.14348 (12)	0.0154 (5)
C2	1.1558 (3)	0.5710 (4)	0.19570 (12)	0.0162 (5)
C3	1.2500 (3)	0.6550 (4)	0.23737 (13)	0.0195 (6)
H3A	1.2236	0.7097	0.2720	0.023*
C4	1.3828 (3)	0.6591 (4)	0.22844 (13)	0.0198 (6)
H4A	1.4464	0.7174	0.2569	0.024*
C5	1.4232 (3)	0.5785 (4)	0.17820 (13)	0.0197 (6)
H5A	1.5143	0.5790	0.1728	0.024*
C6	1.3297 (3)	0.4974 (4)	0.13598 (13)	0.0175 (5)
H6A	1.3572	0.4432	0.1015	0.021*
C7	0.9817 (3)	0.6273 (4)	0.25429 (14)	0.0237 (6)
H7A	0.9954	0.7601	0.2559	0.028*
H7B	1.0324	0.5727	0.2905	0.028*
C8	0.8362 (3)	0.5833 (5)	0.25128 (16)	0.0304 (7)
H8A	0.8021	0.6340	0.2864	0.046*
H8B	0.8242	0.4515	0.2507	0.046*
H8C	0.7874	0.6359	0.2148	0.046*
C9	1.0519 (3)	0.2108 (4)	−0.03482 (12)	0.0153 (5)
C10	0.9451 (3)	0.1305 (4)	−0.07242 (12)	0.0148 (5)
C11	0.9671 (3)	0.0489 (4)	−0.12541 (12)	0.0183 (5)
H11A	0.8950	−0.0038	−0.1508	0.022*
C12	1.0944 (3)	0.0436 (4)	−0.14161 (13)	0.0204 (6)
H12A	1.1091	−0.0147	−0.1777	0.024*
C13	1.1995 (3)	0.1227 (4)	−0.10547 (13)	0.0210 (6)
H13A	1.2860	0.1197	−0.1170	0.025*
C14	1.1789 (3)	0.2072 (4)	−0.05198 (13)	0.0183 (6)
H14A	1.2512	0.2621	−0.0274	0.022*
C15	0.7136 (3)	0.0536 (4)	−0.08871 (13)	0.0190 (5)
H15A	0.7319	−0.0773	−0.0925	0.023*
H15B	0.6993	0.1072	−0.1293	0.023*
C16	0.5924 (3)	0.0808 (5)	−0.05819 (15)	0.0258 (6)
H16A	0.5188	0.0086	−0.0785	0.039*
H16B	0.5677	0.2092	−0.0598	0.039*
H16C	0.6117	0.0423	−0.0163	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.01754 (6)	0.02133 (6)	0.01728 (6)	0.00076 (4)	0.00604 (4)	−0.00146 (4)
Cl1	0.0241 (4)	0.0361 (4)	0.0390 (5)	−0.0002 (3)	0.0165 (3)	−0.0071 (3)
O1	0.0217 (10)	0.0216 (10)	0.0140 (9)	−0.0016 (8)	0.0065 (8)	−0.0038 (8)
O2	0.0142 (9)	0.0238 (10)	0.0144 (9)	−0.0025 (7)	0.0026 (8)	−0.0018 (8)
N1	0.0206 (11)	0.0148 (11)	0.0119 (10)	0.0023 (9)	0.0014 (9)	−0.0006 (9)
N2	0.0193 (11)	0.0152 (11)	0.0130 (11)	0.0024 (9)	0.0007 (9)	0.0007 (8)
N3	0.0156 (11)	0.0189 (12)	0.0127 (11)	−0.0012 (9)	0.0016 (9)	0.0002 (9)
C1	0.0193 (13)	0.0121 (12)	0.0142 (12)	0.0003 (10)	0.0000 (10)	0.0001 (10)
C2	0.0207 (13)	0.0132 (12)	0.0146 (12)	0.0013 (10)	0.0020 (10)	0.0011 (10)
C3	0.0268 (15)	0.0160 (14)	0.0150 (13)	0.0007 (11)	0.0010 (11)	−0.0007 (10)
C4	0.0259 (14)	0.0145 (13)	0.0171 (13)	−0.0006 (11)	−0.0046 (11)	0.0019 (10)
C5	0.0171 (13)	0.0196 (14)	0.0212 (14)	0.0009 (11)	−0.0017 (11)	0.0021 (11)
C6	0.0208 (13)	0.0164 (13)	0.0151 (13)	0.0027 (10)	0.0017 (11)	0.0013 (10)
C7	0.0329 (17)	0.0215 (14)	0.0182 (14)	−0.0011 (12)	0.0095 (13)	−0.0021 (11)
C8	0.0306 (17)	0.0317 (18)	0.0326 (18)	−0.0023 (14)	0.0175 (14)	−0.0018 (14)
C9	0.0179 (13)	0.0167 (13)	0.0115 (12)	0.0016 (10)	0.0023 (10)	0.0017 (10)
C10	0.0160 (12)	0.0141 (12)	0.0146 (12)	−0.0005 (10)	0.0028 (10)	0.0031 (10)
C11	0.0224 (13)	0.0196 (13)	0.0128 (12)	−0.0014 (11)	0.0016 (10)	−0.0001 (11)
C12	0.0226 (14)	0.0243 (15)	0.0150 (13)	0.0047 (11)	0.0050 (11)	0.0011 (11)
C13	0.0182 (13)	0.0262 (15)	0.0191 (14)	0.0052 (11)	0.0043 (11)	0.0004 (12)
C14	0.0161 (12)	0.0239 (15)	0.0148 (13)	−0.0010 (10)	0.0016 (10)	0.0004 (11)
C15	0.0166 (12)	0.0210 (14)	0.0186 (13)	−0.0030 (11)	−0.0006 (10)	0.0012 (11)
C16	0.0169 (13)	0.0344 (17)	0.0268 (16)	−0.0021 (12)	0.0053 (12)	0.0041 (13)

Geometric parameters (Å, º) top

Hg1—N3	2.074 (2)	C7—C8	1.507 (5)
Hg1—Cl1	2.2840 (8)	C7—H7A	0.9900
Hg1—N1	2.674 (2)	C7—H7B	0.9900
Hg1—O2	2.721 (2)	C8—H8A	0.9800
O1—C2	1.358 (3)	C8—H8B	0.9800
O1—C7	1.431 (3)	C8—H8C	0.9800
O2—C10	1.368 (3)	C9—C14	1.397 (4)
O2—C15	1.441 (3)	C9—C10	1.413 (4)
N1—N2	1.277 (3)	C10—C11	1.384 (4)
N1—C1	1.415 (3)	C11—C12	1.391 (4)
N2—N3	1.329 (3)	C11—H11A	0.9500
N3—C9	1.400 (4)	C12—C13	1.382 (4)
C1—C6	1.395 (4)	C12—H12A	0.9500
C1—C2	1.415 (4)	C13—C14	1.399 (4)
C2—C3	1.393 (4)	C13—H13A	0.9500
C3—C4	1.391 (4)	C14—H14A	0.9500
C3—H3A	0.9500	C15—C16	1.503 (4)
C4—C5	1.391 (4)	C15—H15A	0.9900
C4—H4A	0.9500	C15—H15B	0.9900
C5—C6	1.386 (4)	C16—H16A	0.9800
C5—H5A	0.9500	C16—H16B	0.9800
C6—H6A	0.9500	C16—H16C	0.9800

N3—Hg1—Cl1	176.60 (7)	C8—C7—H7B	110.3
N3—Hg1—N1	51.80 (8)	H7A—C7—H7B	108.6
Cl1—Hg1—N1	129.12 (5)	C7—C8—H8A	109.5
N3—Hg1—O2	66.09 (8)	C7—C8—H8B	109.5
Cl1—Hg1—O2	112.99 (5)	H8A—C8—H8B	109.5
N1—Hg1—O2	117.86 (6)	C7—C8—H8C	109.5
Hg1—O2—C10	109.48 (8)	H8A—C8—H8C	109.5
Hg1—O2—C15	133.07 (16)	H8B—C8—H8C	109.5
C2—O1—C7	117.4 (2)	C14—C9—N3	122.6 (3)
C10—O2—C15	117.3 (2)	C14—C9—C10	119.2 (3)
N2—N1—C1	114.7 (2)	N3—C9—C10	118.2 (2)
N2—N1—Hg1	85.01 (16)	O2—C10—C11	124.2 (2)
C1—N1—Hg1	160.18 (18)	O2—C10—C9	115.8 (2)
N1—N2—N3	110.6 (2)	C11—C10—C9	120.0 (3)
N2—N3—C9	117.0 (2)	C10—C11—C12	120.3 (3)
N2—N3—Hg1	112.58 (18)	C10—C11—H11A	119.9
C9—N3—Hg1	130.44 (19)	C12—C11—H11A	119.9
C6—C1—C2	119.4 (3)	C13—C12—C11	120.3 (3)
C6—C1—N1	125.2 (3)	C13—C12—H12A	119.9
C2—C1—N1	115.5 (2)	C11—C12—H12A	119.9
O1—C2—C3	124.6 (3)	C12—C13—C14	120.2 (3)
O1—C2—C1	116.0 (2)	C12—C13—H13A	119.9
C3—C2—C1	119.4 (3)	C14—C13—H13A	119.9
C4—C3—C2	120.2 (3)	C9—C14—C13	120.0 (3)
C4—C3—H3A	119.9	C9—C14—H14A	120.0
C2—C3—H3A	119.9	C13—C14—H14A	120.0
C3—C4—C5	120.6 (3)	O2—C15—C16	107.7 (2)
C3—C4—H4A	119.7	O2—C15—H15A	110.2
C5—C4—H4A	119.7	C16—C15—H15A	110.2
C6—C5—C4	119.6 (3)	O2—C15—H15B	110.2
C6—C5—H5A	120.2	C16—C15—H15B	110.2
C4—C5—H5A	120.2	H15A—C15—H15B	108.5
C5—C6—C1	120.8 (3)	C15—C16—H16A	109.5
C5—C6—H6A	119.6	C15—C16—H16B	109.5
C1—C6—H6A	119.6	H16A—C16—H16B	109.5
O1—C7—C8	107.0 (3)	C15—C16—H16C	109.5
O1—C7—H7A	110.3	H16A—C16—H16C	109.5
C8—C7—H7A	110.3	H16B—C16—H16C	109.5
O1—C7—H7B	110.3

N3—Hg1—O2—C10	0.40 (16)	N1—C1—C2—C3	−178.1 (2)
Cl1—Hg1—O2—C10	176.84 (15)	O1—C2—C3—C4	177.3 (3)
N1—Hg1—O2—C10	−1.31 (18)	C1—C2—C3—C4	−1.8 (4)
N3—Hg1—O2—C15	175.4 (2)	C2—C3—C4—C5	−0.5 (4)
Cl1—Hg1—O2—C15	−8.2 (2)	C3—C4—C5—C6	1.6 (4)
N1—Hg1—O2—C15	173.7 (2)	C4—C5—C6—C1	−0.5 (4)
N3—Hg1—N1—N2	1.55 (15)	C2—C1—C6—C5	−1.8 (4)
Cl1—Hg1—N1—N2	−174.26 (12)	N1—C1—C6—C5	179.3 (3)
O2—Hg1—N1—N2	3.54 (17)	C2—O1—C7—C8	−177.5 (2)
N3—Hg1—N1—C1	177.1 (6)	N2—N3—C9—C14	0.1 (4)
Cl1—Hg1—N1—C1	1.3 (6)	Hg1—N3—C9—C14	179.6 (2)
O2—Hg1—N1—C1	179.1 (5)	N2—N3—C9—C10	178.6 (2)
C1—N1—N2—N3	179.6 (2)	Hg1—N3—C9—C10	−2.0 (4)
Hg1—N1—N2—N3	−2.03 (19)	C15—O2—C10—C11	3.1 (4)
N1—N2—N3—C9	−177.6 (2)	C15—O2—C10—C9	−177.3 (2)
N1—N2—N3—Hg1	2.8 (3)	C14—C9—C10—O2	−179.4 (2)
N1—Hg1—N3—N2	−1.61 (15)	N3—C9—C10—O2	2.1 (4)
N1—Hg1—N3—C9	178.9 (3)	C14—C9—C10—C11	0.3 (4)
N2—N1—C1—C6	−5.0 (4)	N3—C9—C10—C11	−178.2 (2)
Hg1—N1—C1—C6	179.8 (4)	O2—C10—C11—C12	−179.6 (3)
N2—N1—C1—C2	176.1 (2)	C9—C10—C11—C12	0.7 (4)
Hg1—N1—C1—C2	0.9 (7)	C10—C11—C12—C13	−1.2 (4)
C7—O1—C2—C3	0.0 (4)	C11—C12—C13—C14	0.6 (5)
C7—O1—C2—C1	179.1 (2)	N3—C9—C14—C13	177.6 (3)
C6—C1—C2—O1	−176.3 (2)	C10—C9—C14—C13	−0.9 (4)
N1—C1—C2—O1	2.7 (4)	C12—C13—C14—C9	0.4 (4)
C6—C1—C2—C3	2.9 (4)	C10—O2—C15—C16	179.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg1ⁱ	0.95	2.87	3.598 (3)	134
C15—H15B···Cg1ⁱⁱ	0.99	2.68	3.511 (3)	142

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

Experimental details

Crystal data
Chemical formula	[Hg(C₁₆H₁₈N₃O₂)Cl]
M_r	520.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.1600 (5), 7.3802 (4), 22.5655 (11)
β (°)	97.817 (1)
V (Å³)	1676.30 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	9.35
Crystal size (mm)	0.15 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (APEX2; Bruker, 2005)
T_min, T_max	0.280, 0.479
No. of measured, independent and observed [I > 2σ(I)] reflections	19713, 4451, 4009
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.049, 1.01
No. of reflections	4451
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −1.19

Computer programs: APEX2 (Bruker, 2005), 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
C3—H3A···Cg1ⁱ	0.95	2.87	3.598 (3)	134
C15—H15B···Cg1ⁱⁱ	0.99	2.68	3.511 (3)	142

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

References

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Melardi, M. R., Rofouei, M. K. & Massomi, J. (2007). Anal. Sci. 23, x67–x68. CAS Google Scholar
Rofouei, M. K., Melardi, M. R., Barkhi, M. & Khalili Ghaydar, H. R. (2008). Anal. Sci. 24, x81–x82. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m302

doi:10.1107/S160053680900539X

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