[(4-Dimethyl­amino-2-methyl-5-phenyl­furan-3-yl)meth­yl]diethyl­methyl­aza­nium iodide

Ayvazyan, A.

doi:10.1107/S1600536811037743

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2693

https://doi.org/10.1107/S1600536811037743

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[(4-Dimethylamino-2-methyl-5-phenylfuran-3-yl)methyl]diethylmethylazanium iodide

Armen Ayvazyan ^a ^*

^aMolecule Structure Research Center, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences, Republic of Armenia, Azatutyan Ave. 26, Yerevan 0014, Armenia
^*Correspondence e-mail: armen@msrc.am

(Received 7 September 2011; accepted 15 September 2011; online 20 September 2011)

In the title compound, C₁₉H₂₉N₂O⁺·I⁻, the dihedral angle between the mean planes of the essentially planar furan (r.m.s. deviation = 0.007 Å) and phenyl rings is 48.4 (1)°. In the crystal, cations and anions are arranged in layers lying parallel to (100).

Related literature

For the biological activities of furan derivatives, see: Chen et al. (2006 ); Meotti et al. (2003 ); Kazuo et al. (2001 ). For details of the synthesis, see: Manukyan et al. (2007 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₂₉N₂O⁺·I⁻
M_r = 428.34
Monoclinic, P 2₁ /c
a = 17.905 (4) Å
b = 7.2458 (14) Å
c = 15.732 (3) Å
β = 94.84 (3)°
V = 2033.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.58 mm⁻¹
T = 293 K
0.4 × 0.36 × 0.3 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (PLATON; Spek, 2009 ) T_min = 0.395, T_max = 0.430
6119 measured reflections
5911 independent reflections
4370 reflections with I > 2σ(I)
R_int = 0.013
3 standard reflections every 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.081
S = 0.99
5911 reflections
258 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1988 ); cell refinement: SETANG in CAD-4 Software (Enraf–Nonius, 1988); data reduction: HELENA (Spek, 1997 ); 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: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811037743/lh5334sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037743/lh5334Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037743/lh5334Isup3.cml

checkCIF report

Comment top

Compounds containing furan rings are distinguished by a number of interesting biological properties. In particular, the certain representatives of this family show antibacterial, antioxidant and anti-inflammatory activities (Chen et al., 2006, Meotti et al., 2003, Kazuo et al., 2001). Such a diversity of biological properties of these materials stimulates the interest in their structural studies. The asymmetric unit of title compound is shown in Fig.1. The molecule contains one quaternary N⁺ cation, the positive charge on which is balanced by an iodide anion. All bond lengths (Allen et al., 1987) and angles in good agreement with their standard values. In the crystal, cations and anions are arranged in layers parallel to (100) with N⁺···I^- distances in the range 4.429 (1) Å–5.332 (1) Å (see Fig. 2).

Related literature top

For the biological activities of furan derivatives, see: Chen et al. (2006); Meotti et al. (2003); Kazuo et al. (2001). For details of the synthesis, see: Manukyan et al. (2007). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was synthesized via Stevens rearrangement by the interaction of methyl iodide and 2-phenyl-3-dimethylamino-4-diethylamino-5-methylfuran (Manukyan et al., 2007). Single crystals were grown by slow evaporation of a solution of the title compound in ethanol at room temperature.

Structure description top

For the biological activities of furan derivatives, see: Chen et al. (2006); Meotti et al. (2003); Kazuo et al. (2001). For details of the synthesis, see: Manukyan et al. (2007). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1988); cell refinement: SETANG in CAD-4 Software (Enraf–Nonius, 1988); data reduction: HELENA (Spek, 1997); 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: enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. The molecular structure with displacement displacement ellipsoids drawn at the 50% probability level (H atoms are omitted for clarity).
	Fig. 2. Part of the crystal structure emphasizing arrangement of cations and anions with dashed lines.

[(4-Dimethylamino-2-methyl-5-phenylfuran-3-yl)methyl]diethylmethylazanium iodide top

Crystal data top

C₁₉H₂₉N₂O⁺·I⁻	F(000) = 872
M_r = 428.34	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 353 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.905 (4) Å	Cell parameters from 25 reflections
b = 7.2458 (14) Å	θ = 13.9–16.3°
c = 15.732 (3) Å	µ = 1.58 mm⁻¹
β = 94.84 (3)°	T = 293 K
V = 2033.7 (7) Å³	Prism, red
Z = 4	0.4 × 0.36 × 0.3 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	4370 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.013
Graphite monochromator	θ_max = 30.0°, θ_min = 1.1°
θ/2θ scans	h = −25→25
Absorption correction: ψ scan (PLATON; Spek, 2009)	k = −10→0
T_min = 0.395, T_max = 0.430	l = 0→22
6119 measured reflections	3 standard reflections every 60 min
5911 independent reflections	intensity decay: none

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)] = 0.032	Hydrogen site location: mixed
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0331P)² + 0.9333P] where P = (F_o² + 2F_c²)/3
5911 reflections	(Δ/σ)_max = 0.002
258 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₁₉H₂₉N₂O⁺·I⁻	V = 2033.7 (7) Å³
M_r = 428.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.905 (4) Å	µ = 1.58 mm⁻¹
b = 7.2458 (14) Å	T = 293 K
c = 15.732 (3) Å	0.4 × 0.36 × 0.3 mm
β = 94.84 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	4370 reflections with I > 2σ(I)
Absorption correction: ψ scan (PLATON; Spek, 2009)	R_int = 0.013
T_min = 0.395, T_max = 0.430	3 standard reflections every 60 min
6119 measured reflections	intensity decay: none
5911 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.67 e Å⁻³
5911 reflections	Δρ_min = −0.55 e Å⁻³
258 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
I	0.360258 (9)	0.60153 (2)	0.329552 (12)	0.05986 (7)
O1	0.17460 (9)	0.8773 (2)	0.27018 (10)	0.0496 (4)
C2	0.22386 (12)	1.0199 (3)	0.26901 (15)	0.0467 (5)
C3	0.23667 (11)	1.0608 (3)	0.18794 (14)	0.0440 (5)
C4	0.19021 (11)	0.9379 (3)	0.13392 (14)	0.0444 (5)
C5	0.15362 (12)	0.8279 (4)	0.18675 (14)	0.0465 (5)
C6	0.10368 (12)	0.6681 (4)	0.17655 (15)	0.0497 (5)
C7	0.03983 (15)	0.6718 (5)	0.1197 (2)	0.0673 (7)
H7	0.0271 (19)	0.788 (5)	0.089 (2)	0.092 (11)*
C8	−0.00691 (18)	0.5198 (6)	0.1117 (2)	0.0806 (10)
H8	−0.046 (2)	0.519 (5)	0.073 (2)	0.094 (11)*
C9	0.0084 (2)	0.3651 (5)	0.1599 (3)	0.0834 (11)
H9	−0.020 (2)	0.259 (5)	0.154 (2)	0.091 (11)*
C10	0.0716 (2)	0.3597 (5)	0.2157 (3)	0.0831 (10)
H10	0.0835 (19)	0.267 (5)	0.249 (2)	0.083 (11)*
C11	0.11910 (17)	0.5108 (4)	0.2253 (2)	0.0659 (7)
H11	0.1584 (17)	0.506 (5)	0.2656 (19)	0.070 (9)*
N12	0.18903 (11)	0.9401 (3)	0.04386 (13)	0.0568 (5)
C13	0.19220 (18)	0.7624 (5)	0.00155 (19)	0.0816 (10)
H13A	0.2260	0.6824	0.0348	0.122*
H13B	0.2096	0.7792	−0.0540	0.122*
H13C	0.1431	0.7083	−0.0041	0.122*
C14	0.1351 (2)	1.0677 (6)	0.0018 (2)	0.0916 (11)
H14A	0.0855	1.0187	0.0034	0.137*
H14B	0.1459	1.0839	−0.0565	0.137*
H14C	0.1384	1.1845	0.0306	0.137*
C15	0.28935 (12)	1.2003 (3)	0.15767 (16)	0.0465 (5)
H15A	0.2958 (15)	1.312 (4)	0.1934 (17)	0.061 (7)*
H15B	0.2725 (13)	1.242 (3)	0.0983 (16)	0.049 (7)*
N16	0.36958 (10)	1.1291 (2)	0.15215 (12)	0.0445 (4)
C17	0.41598 (14)	1.2812 (4)	0.11586 (18)	0.0551 (6)
H17A	0.4678 (15)	1.232 (4)	0.1215 (16)	0.058 (7)*
H17B	0.4089 (17)	1.395 (4)	0.154 (2)	0.072 (9)*
C18	0.39221 (18)	1.3347 (5)	0.02513 (19)	0.0740 (8)
H18A	0.3949	1.2288	−0.0111	0.111*
H18B	0.4249	1.4294	0.0071	0.111*
H18C	0.3417	1.3800	0.0215	0.111*
C19	0.36726 (14)	0.9537 (4)	0.09966 (19)	0.0543 (6)
H19A	0.3403 (15)	0.988 (4)	0.0445 (18)	0.059 (7)*
H19B	0.3352 (17)	0.867 (4)	0.1319 (18)	0.065 (8)*
C20	0.44255 (16)	0.8662 (4)	0.0897 (2)	0.0725 (8)
H20A	0.4770	0.9588	0.0736	0.109*
H20B	0.4372	0.7728	0.0464	0.109*
H20C	0.4613	0.8114	0.1428	0.109*
C21	0.40518 (14)	1.0903 (4)	0.24027 (16)	0.0552 (6)
H21A	0.3786	0.9921	0.2655	0.083*
H21B	0.4032	1.1993	0.2747	0.083*
H21C	0.4565	1.0545	0.2369	0.083*
C22	0.25056 (17)	1.0946 (4)	0.35412 (16)	0.0636 (7)
H22A	0.2853	1.0094	0.3826	0.095*
H22B	0.2086	1.1118	0.3875	0.095*
H22C	0.2750	1.2109	0.3472	0.095*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I	0.05869 (10)	0.04681 (9)	0.07390 (12)	0.00165 (7)	0.00458 (8)	0.00206 (8)
O1	0.0473 (8)	0.0588 (10)	0.0431 (8)	−0.0070 (7)	0.0066 (6)	−0.0025 (7)
C2	0.0431 (11)	0.0487 (12)	0.0484 (12)	−0.0015 (9)	0.0054 (9)	−0.0034 (10)
C3	0.0374 (10)	0.0457 (11)	0.0484 (12)	0.0002 (8)	0.0015 (8)	−0.0017 (9)
C4	0.0362 (9)	0.0547 (13)	0.0422 (11)	−0.0021 (9)	0.0022 (8)	−0.0031 (9)
C5	0.0379 (10)	0.0556 (13)	0.0463 (12)	−0.0044 (9)	0.0044 (8)	−0.0045 (10)
C6	0.0397 (11)	0.0609 (14)	0.0496 (12)	−0.0104 (10)	0.0109 (9)	−0.0038 (11)
C7	0.0503 (14)	0.082 (2)	0.0690 (17)	−0.0184 (14)	0.0016 (12)	−0.0006 (16)
C8	0.0576 (16)	0.105 (3)	0.078 (2)	−0.0328 (18)	0.0029 (15)	−0.012 (2)
C9	0.073 (2)	0.084 (2)	0.097 (2)	−0.0362 (18)	0.0300 (18)	−0.020 (2)
C10	0.081 (2)	0.069 (2)	0.103 (3)	−0.0127 (17)	0.026 (2)	0.0092 (19)
C11	0.0575 (15)	0.0672 (18)	0.0736 (19)	−0.0084 (14)	0.0094 (14)	0.0031 (15)
N12	0.0507 (11)	0.0776 (15)	0.0419 (10)	−0.0121 (10)	0.0028 (8)	−0.0029 (10)
C13	0.082 (2)	0.106 (3)	0.0587 (16)	−0.0292 (19)	0.0181 (14)	−0.0309 (17)
C14	0.090 (2)	0.119 (3)	0.0623 (18)	−0.009 (2)	−0.0130 (16)	0.0278 (19)
C15	0.0423 (11)	0.0432 (12)	0.0536 (13)	−0.0004 (9)	0.0014 (9)	0.0028 (10)
N16	0.0387 (8)	0.0426 (10)	0.0517 (10)	−0.0046 (7)	0.0017 (7)	0.0016 (8)
C17	0.0491 (13)	0.0508 (13)	0.0653 (15)	−0.0121 (11)	0.0036 (11)	0.0034 (12)
C18	0.0786 (19)	0.077 (2)	0.0674 (18)	−0.0070 (16)	0.0140 (15)	0.0166 (16)
C19	0.0459 (12)	0.0503 (13)	0.0667 (16)	−0.0031 (10)	0.0048 (11)	−0.0124 (12)
C20	0.0537 (14)	0.0706 (19)	0.095 (2)	0.0021 (13)	0.0139 (14)	−0.0185 (16)
C21	0.0529 (12)	0.0562 (14)	0.0546 (13)	0.0000 (11)	−0.0075 (10)	0.0025 (11)
C22	0.0742 (17)	0.0670 (17)	0.0497 (13)	−0.0135 (14)	0.0061 (12)	−0.0102 (13)

Geometric parameters (Å, º) top

O1—C2	1.360 (3)	C14—H14B	0.9600
O1—C5	1.382 (3)	C14—H14C	0.9600
C2—C3	1.348 (3)	C15—N16	1.536 (3)
C2—C22	1.485 (3)	C15—H15A	0.99 (3)
C3—C4	1.445 (3)	C15—H15B	1.00 (2)
C3—C15	1.488 (3)	N16—C21	1.503 (3)
C4—C5	1.359 (3)	N16—C19	1.514 (3)
C4—N12	1.415 (3)	N16—C17	1.520 (3)
C5—C6	1.463 (3)	C17—C18	1.505 (4)
C6—C11	1.388 (4)	C17—H17A	0.99 (3)
C6—C7	1.391 (4)	C17—H17B	1.04 (3)
C7—C8	1.383 (4)	C18—H18A	0.9600
C7—H7	0.99 (4)	C18—H18B	0.9600
C8—C9	1.369 (6)	C18—H18C	0.9600
C8—H8	0.88 (4)	C19—C20	1.510 (4)
C9—C10	1.371 (6)	C19—H19A	0.99 (3)
C9—H9	0.92 (4)	C19—H19B	1.02 (3)
C10—C11	1.387 (5)	C20—H20A	0.9600
C10—H10	0.86 (3)	C20—H20B	0.9600
C11—H11	0.91 (3)	C20—H20C	0.9600
N12—C13	1.452 (4)	C21—H21A	0.9600
N12—C14	1.455 (4)	C21—H21B	0.9600
C13—H13A	0.9600	C21—H21C	0.9600
C13—H13B	0.9600	C22—H22A	0.9600
C13—H13C	0.9600	C22—H22B	0.9600
C14—H14A	0.9600	C22—H22C	0.9600

C2—O1—C5	107.99 (17)	C3—C15—H15A	114.9 (16)
C3—C2—O1	110.01 (19)	N16—C15—H15A	104.0 (16)
C3—C2—C22	134.9 (2)	C3—C15—H15B	110.6 (14)
O1—C2—C22	115.1 (2)	N16—C15—H15B	105.0 (14)
C2—C3—C4	106.6 (2)	H15A—C15—H15B	107 (2)
C2—C3—C15	128.0 (2)	C21—N16—C19	109.63 (19)
C4—C3—C15	125.4 (2)	C21—N16—C17	106.23 (18)
C5—C4—N12	130.6 (2)	C19—N16—C17	113.2 (2)
C5—C4—C3	106.6 (2)	C21—N16—C15	109.68 (19)
N12—C4—C3	122.8 (2)	C19—N16—C15	109.27 (17)
C4—C5—O1	108.81 (19)	C17—N16—C15	108.73 (18)
C4—C5—C6	135.9 (2)	C18—C17—N16	115.0 (2)
O1—C5—C6	115.1 (2)	C18—C17—H17A	111.4 (15)
C11—C6—C7	119.0 (3)	N16—C17—H17A	104.1 (16)
C11—C6—C5	119.9 (2)	C18—C17—H17B	107.9 (17)
C7—C6—C5	121.1 (3)	N16—C17—H17B	105.2 (17)
C8—C7—C6	120.1 (3)	H17A—C17—H17B	113 (2)
C8—C7—H7	121 (2)	C17—C18—H18A	109.5
C6—C7—H7	118 (2)	C17—C18—H18B	109.5
C9—C8—C7	120.7 (3)	H18A—C18—H18B	109.5
C9—C8—H8	119 (3)	C17—C18—H18C	109.5
C7—C8—H8	120 (3)	H18A—C18—H18C	109.5
C10—C9—C8	119.6 (3)	H18B—C18—H18C	109.5
C10—C9—H9	118 (2)	C20—C19—N16	115.2 (2)
C8—C9—H9	123 (2)	C20—C19—H19A	112.9 (16)
C9—C10—C11	120.8 (4)	N16—C19—H19A	104.9 (17)
C9—C10—H10	124 (2)	C20—C19—H19B	109.8 (16)
C11—C10—H10	115 (2)	N16—C19—H19B	103.7 (16)
C10—C11—C6	119.8 (3)	H19A—C19—H19B	110 (2)
C10—C11—H11	119 (2)	C19—C20—H20A	109.5
C6—C11—H11	121 (2)	C19—C20—H20B	109.5
C4—N12—C13	116.8 (2)	H20A—C20—H20B	109.5
C4—N12—C14	114.6 (2)	C19—C20—H20C	109.5
C13—N12—C14	113.9 (3)	H20A—C20—H20C	109.5
N12—C13—H13A	109.5	H20B—C20—H20C	109.5
N12—C13—H13B	109.5	N16—C21—H21A	109.5
H13A—C13—H13B	109.5	N16—C21—H21B	109.5
N12—C13—H13C	109.5	H21A—C21—H21B	109.5
H13A—C13—H13C	109.5	N16—C21—H21C	109.5
H13B—C13—H13C	109.5	H21A—C21—H21C	109.5
N12—C14—H14A	109.5	H21B—C21—H21C	109.5
N12—C14—H14B	109.5	C2—C22—H22A	109.5
H14A—C14—H14B	109.5	C2—C22—H22B	109.5
N12—C14—H14C	109.5	H22A—C22—H22B	109.5
H14A—C14—H14C	109.5	C2—C22—H22C	109.5
H14B—C14—H14C	109.5	H22A—C22—H22C	109.5
C3—C15—N16	114.28 (18)	H22B—C22—H22C	109.5

C5—O1—C2—C3	−1.5 (3)	C6—C7—C8—C9	0.7 (5)
C5—O1—C2—C22	178.2 (2)	C7—C8—C9—C10	−1.2 (6)
O1—C2—C3—C4	1.8 (3)	C8—C9—C10—C11	1.6 (6)
C22—C2—C3—C4	−177.9 (3)	C9—C10—C11—C6	−1.5 (5)
O1—C2—C3—C15	−176.7 (2)	C7—C6—C11—C10	1.0 (4)
C22—C2—C3—C15	3.7 (4)	C5—C6—C11—C10	179.8 (3)
C2—C3—C4—C5	−1.4 (3)	C5—C4—N12—C13	−43.1 (4)
C15—C3—C4—C5	177.2 (2)	C3—C4—N12—C13	134.8 (2)
C2—C3—C4—N12	−179.7 (2)	C5—C4—N12—C14	93.7 (3)
C15—C3—C4—N12	−1.2 (4)	C3—C4—N12—C14	−88.3 (3)
N12—C4—C5—O1	178.6 (2)	C2—C3—C15—N16	86.9 (3)
C3—C4—C5—O1	0.5 (3)	C4—C3—C15—N16	−91.3 (3)
N12—C4—C5—C6	3.9 (5)	C3—C15—N16—C21	−67.4 (2)
C3—C4—C5—C6	−174.3 (3)	C3—C15—N16—C19	52.8 (3)
C2—O1—C5—C4	0.6 (3)	C3—C15—N16—C17	176.8 (2)
C2—O1—C5—C6	176.6 (2)	C21—N16—C17—C18	176.8 (2)
C4—C5—C6—C11	128.8 (3)	C19—N16—C17—C18	56.4 (3)
O1—C5—C6—C11	−45.7 (3)	C15—N16—C17—C18	−65.2 (3)
C4—C5—C6—C7	−52.4 (4)	C21—N16—C19—C20	−59.0 (3)
O1—C5—C6—C7	133.1 (3)	C17—N16—C19—C20	59.4 (3)
C11—C6—C7—C8	−0.5 (4)	C15—N16—C19—C20	−179.2 (2)
C5—C6—C7—C8	−179.4 (3)

Experimental details

Crystal data
Chemical formula	C₁₉H₂₉N₂O⁺·I⁻
M_r	428.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.905 (4), 7.2458 (14), 15.732 (3)
β (°)	94.84 (3)
V (Å³)	2033.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.58
Crystal size (mm)	0.4 × 0.36 × 0.3

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (PLATON; Spek, 2009)
T_min, T_max	0.395, 0.430
No. of measured, independent and observed [I > 2σ(I)] reflections	6119, 5911, 4370
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.081, 0.99
No. of reflections	5911
No. of parameters	258
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.55

Computer programs: SETANG in CAD-4 Software (Enraf–Nonius, 1988), HELENA (Spek, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), enCIFer (Allen et al., 2004).

Acknowledgements

The title compound was provided by M. O. Manukyan, synthesized within the framework of State Committee of Science of Armenia (grant No. 11B-1d024).

References

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