(5E)-Dimethyl 2-bromo­methyl-5-cyclo­hexyl­imino-2-phenyl-2,5-dihydro­furan-3,4-dicarboxyl­ate

Zonouzi, A.; Biniaz, M.; Rahmani, H.; Ng, S.W.

doi:10.1107/S1600536809008496

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o751

doi:10.1107/S1600536809008496

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(5E)-Dimethyl 2-bromomethyl-5-cyclohexylimino-2-phenyl-2,5-dihydrofuran-3,4-dicarboxylate

Afsaneh Zonouzi,^a Mojtaba Biniaz,^a Hossein Rahmani ^b and Seik Weng Ng ^c ^*

^aDepartment of Chemistry, College of Science, University of Tehran, PO Box 13145-143, Tehran, Iran, ^bInstitute of Chemical Industries, Iranian Research Organization for Science and Technology, PO Box 15815-358, Tehran, Iran, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 March 2009; accepted 9 March 2009; online 14 March 2009)

The molecule of the title compound, C₂₁H₂₄BrNO₅, has a planar furan ring [maximum deviation = 0.025 (3) Å]. The carboxymethyl group in the 3-position is nearly coplanar with this ring [dihedral angle = 7.9 (1)°], whereas that in the 4-position is nearly perpendicular to it [dihedral angle = 78.9 (1) Å].

Related literature

The iminolactone was synthesized by the one-pot, solvent-free reaction of dimethyl acetylenedicarboxylate, cyclohexyl isocyanide and α-bromoacetophenone under microwave irradiation; for other synthetic methods, see: Ma & Xie (2002 , 2005 ); Nair et al. (2000 ); Villemin & Liao (2003 ).

Experimental

Crystal data

C₂₁H₂₄BrNO₅
M_r = 450.32
Monoclinic, P 2₁ /c
a = 16.8599 (3) Å
b = 7.2871 (1) Å
c = 17.4145 (3) Å
β = 97.330 (1)°
V = 2122.06 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.97 mm⁻¹
T = 123 K
0.30 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.590, T_max = 0.828
19142 measured reflections
4873 independent reflections
4034 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.156
S = 1.08
4873 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 2.31 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008496/tk2389sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008496/tk2389Isup2.hkl

checkCIF report

Related literature top

The iminolactone was synthesized by the one-pot, solvent-free reaction of dimethyl acetylenedicarboxylate, cyclohexyl isocyanide and α-bromoacetophenone under microwave irradiation; for other synthetic methods, see: Ma & Xie (2002, 2005); Nair et al. (2000); Villemin & Liao (2003).

Experimental top

To a mixture of 2-bromo-1-phenyl ethanone (α-bromo acetophenone, 0.398 g, 2 mmol) and dimethyl acetylenedicarboxylate (0.25 ml, 2 mmol), cyclohexyl isocyanide (0.25 ml, 2 mmol) was added. Irradiation of the mixture with microwave radiation (180 W) for 5 min produced the title iminolactone. The reaction was monitored by TLC (ethyl acetate n-hexane 4:1) until no α-bromoacetophenone was detectable. The product was recrystalized from methanol; yield 90%, m.p. 351 K.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellisoid plot (Barbour, 2001) of C₂₁H₂₄BrNO₅; probability levels are set at 70% and H-atoms are drawn as spheres of arbitrary radius.

(5E)-Dimethyl 2-bromomethyl-5-cyclohexylimino-2-phenyl-2,5-dihydrofuran-3,4-dicarboxylate top

Crystal data top

C₂₁H₂₄BrNO₅	F(000) = 928
M_r = 450.32	D_x = 1.410 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3661 reflections
a = 16.8599 (3) Å	θ = 2.7–28.3°
b = 7.2871 (1) Å	µ = 1.97 mm⁻¹
c = 17.4145 (3) Å	T = 123 K
β = 97.330 (1)°	Prism, colorless
V = 2122.06 (6) Å³	0.30 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4873 independent reflections
Radiation source: fine-focus sealed tube	4034 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scans	θ_max = 27.5°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
T_min = 0.590, T_max = 0.828	k = −9→9
19142 measured reflections	l = −22→22

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0837P)² + 3.6326P] where P = (F_o² + 2F_c²)/3
4873 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 2.31 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

C₂₁H₂₄BrNO₅	V = 2122.06 (6) Å³
M_r = 450.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.8599 (3) Å	µ = 1.97 mm⁻¹
b = 7.2871 (1) Å	T = 123 K
c = 17.4145 (3) Å	0.30 × 0.15 × 0.10 mm
β = 97.330 (1)°

Data collection top

Bruker SMART APEX diffractometer	4873 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4034 reflections with I > 2σ(I)
T_min = 0.590, T_max = 0.828	R_int = 0.046
19142 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.08	Δρ_max = 2.31 e Å⁻³
4873 reflections	Δρ_min = −0.67 e Å⁻³
255 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.25611 (3)	1.02341 (5)	0.45239 (2)	0.03930 (16)
O1	0.29800 (12)	0.6088 (3)	0.49013 (12)	0.0216 (4)
O2	0.09230 (13)	0.3244 (3)	0.36320 (12)	0.0240 (5)
O3	0.11434 (15)	0.5554 (4)	0.28251 (13)	0.0297 (5)
O4	0.06942 (14)	0.8094 (3)	0.54175 (13)	0.0289 (5)
O5	0.02390 (13)	0.6629 (3)	0.43103 (13)	0.0259 (5)
N1	0.30562 (15)	0.4537 (4)	0.37308 (15)	0.0207 (5)
C1	0.23476 (17)	0.6816 (4)	0.53027 (16)	0.0186 (6)
C2	0.16009 (17)	0.6470 (4)	0.47364 (16)	0.0185 (6)
C3	0.17954 (17)	0.5531 (4)	0.41267 (16)	0.0183 (6)
C4	0.26637 (18)	0.5307 (4)	0.42102 (16)	0.0185 (6)
C5	0.25368 (19)	0.8840 (4)	0.54633 (17)	0.0240 (6)
H5A	0.3062	0.8943	0.5787	0.029*
H5B	0.2128	0.9369	0.5759	0.029*
C6	0.23270 (17)	0.5743 (4)	0.60559 (16)	0.0190 (6)
C7	0.25969 (18)	0.3940 (4)	0.61047 (17)	0.0219 (6)
H7	0.2790	0.3382	0.5672	0.026*
C8	0.25852 (19)	0.2952 (4)	0.67858 (19)	0.0251 (6)
H8	0.2771	0.1720	0.6815	0.030*
C9	0.2307 (2)	0.3741 (5)	0.74210 (19)	0.0281 (7)
H9	0.2305	0.3060	0.7886	0.034*
C10	0.2030 (2)	0.5530 (5)	0.73749 (19)	0.0308 (7)
H10	0.1836	0.6080	0.7809	0.037*
C11	0.20363 (19)	0.6531 (5)	0.66923 (18)	0.0252 (6)
H11	0.1841	0.7755	0.6662	0.030*
C12	0.08049 (18)	0.7155 (4)	0.48724 (17)	0.0212 (6)
C13	−0.05632 (18)	0.7330 (5)	0.4356 (2)	0.0291 (7)
H13A	−0.0942	0.6741	0.3957	0.044*
H13B	−0.0571	0.8660	0.4273	0.044*
H13C	−0.0717	0.7059	0.4868	0.044*
C14	0.12496 (18)	0.4812 (4)	0.34460 (17)	0.0194 (6)
C15	0.0330 (2)	0.2459 (5)	0.3044 (2)	0.0329 (8)
H15A	0.0136	0.1294	0.3232	0.049*
H15B	0.0572	0.2240	0.2570	0.049*
H15C	−0.0120	0.3312	0.2934	0.049*
C16	0.39323 (18)	0.4490 (5)	0.38899 (18)	0.0236 (6)
H16	0.4097	0.4544	0.4462	0.028*
C17	0.4273 (2)	0.6150 (5)	0.3507 (2)	0.0330 (8)
H17A	0.4051	0.6189	0.2953	0.040*
H17B	0.4109	0.7288	0.3755	0.040*
C18	0.5186 (2)	0.6070 (6)	0.3579 (2)	0.0382 (9)
H18A	0.5385	0.7119	0.3297	0.046*
H18B	0.5410	0.6176	0.4130	0.046*
C19	0.5467 (2)	0.4285 (7)	0.3250 (2)	0.0402 (9)
H19A	0.5280	0.4226	0.2688	0.048*
H19B	0.6059	0.4249	0.3321	0.048*
C20	0.5149 (2)	0.2658 (6)	0.3648 (2)	0.0405 (9)
H20A	0.5370	0.2663	0.4202	0.049*
H20B	0.5323	0.1512	0.3414	0.049*
C21	0.4232 (2)	0.2705 (5)	0.3573 (2)	0.0338 (8)
H21A	0.4010	0.2575	0.3022	0.041*
H21B	0.4040	0.1656	0.3860	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0740 (3)	0.0243 (2)	0.0196 (2)	−0.01265 (16)	0.00615 (16)	0.00297 (13)
O1	0.0240 (10)	0.0273 (12)	0.0134 (10)	−0.0023 (8)	0.0023 (8)	−0.0049 (8)
O2	0.0316 (11)	0.0228 (11)	0.0167 (10)	−0.0060 (9)	−0.0010 (8)	−0.0029 (8)
O3	0.0384 (13)	0.0344 (13)	0.0146 (11)	−0.0051 (10)	−0.0029 (9)	0.0058 (9)
O4	0.0321 (12)	0.0330 (13)	0.0214 (11)	0.0071 (10)	0.0022 (9)	−0.0057 (10)
O5	0.0228 (10)	0.0296 (12)	0.0245 (11)	0.0021 (9)	0.0007 (8)	−0.0072 (9)
N1	0.0246 (13)	0.0224 (13)	0.0157 (12)	−0.0007 (10)	0.0047 (9)	−0.0015 (10)
C1	0.0241 (14)	0.0189 (14)	0.0129 (13)	−0.0010 (10)	0.0033 (10)	−0.0019 (10)
C2	0.0261 (14)	0.0156 (13)	0.0132 (12)	−0.0013 (11)	0.0006 (10)	0.0021 (10)
C3	0.0244 (14)	0.0189 (14)	0.0115 (13)	−0.0008 (11)	0.0015 (10)	0.0005 (10)
C4	0.0260 (14)	0.0190 (14)	0.0100 (13)	−0.0037 (11)	0.0007 (10)	−0.0002 (10)
C5	0.0340 (16)	0.0218 (15)	0.0161 (14)	−0.0043 (12)	0.0027 (12)	−0.0008 (11)
C6	0.0209 (13)	0.0217 (14)	0.0139 (13)	−0.0006 (11)	0.0004 (10)	−0.0009 (11)
C7	0.0258 (14)	0.0210 (15)	0.0184 (14)	−0.0001 (11)	0.0007 (11)	−0.0031 (11)
C8	0.0304 (16)	0.0195 (14)	0.0241 (15)	0.0003 (12)	−0.0013 (12)	0.0023 (12)
C9	0.0359 (17)	0.0299 (17)	0.0178 (14)	−0.0010 (13)	0.0009 (12)	0.0061 (13)
C10	0.045 (2)	0.0323 (18)	0.0158 (15)	0.0074 (15)	0.0073 (13)	0.0037 (13)
C11	0.0366 (17)	0.0228 (15)	0.0167 (14)	0.0068 (13)	0.0046 (12)	0.0001 (12)
C12	0.0279 (15)	0.0191 (14)	0.0164 (13)	0.0015 (11)	0.0025 (11)	0.0027 (11)
C13	0.0236 (15)	0.0311 (17)	0.0322 (17)	0.0024 (13)	0.0016 (12)	0.0002 (14)
C14	0.0225 (14)	0.0216 (14)	0.0141 (13)	0.0012 (11)	0.0026 (10)	−0.0018 (11)
C15	0.0348 (18)	0.0362 (19)	0.0265 (17)	−0.0122 (15)	−0.0015 (13)	−0.0112 (14)
C16	0.0241 (15)	0.0324 (17)	0.0141 (14)	−0.0019 (12)	0.0021 (11)	−0.0023 (12)
C17	0.0313 (17)	0.036 (2)	0.0314 (18)	−0.0065 (14)	0.0037 (13)	0.0027 (15)
C18	0.0310 (18)	0.048 (2)	0.036 (2)	−0.0099 (16)	0.0038 (14)	0.0017 (17)
C19	0.0253 (16)	0.063 (3)	0.0332 (19)	−0.0053 (17)	0.0070 (14)	−0.0088 (19)
C20	0.0305 (18)	0.046 (2)	0.044 (2)	0.0075 (16)	0.0026 (15)	−0.0067 (18)
C21	0.0279 (17)	0.0329 (19)	0.041 (2)	0.0002 (14)	0.0073 (14)	−0.0066 (16)

Geometric parameters (Å, º) top

Br1—C5	1.930 (3)	C9—H9	0.9500
O1—C4	1.376 (3)	C10—C11	1.396 (4)
O1—C1	1.448 (3)	C10—H10	0.9500
O2—C14	1.326 (4)	C11—H11	0.9500
O2—C15	1.454 (4)	C13—H13A	0.9800
O3—C14	1.202 (4)	C13—H13B	0.9800
O4—C12	1.204 (4)	C13—H13C	0.9800
O5—C12	1.333 (4)	C15—H15A	0.9800
O5—C13	1.457 (4)	C15—H15B	0.9800
N1—C4	1.261 (4)	C15—H15C	0.9800
N1—C16	1.468 (4)	C16—C21	1.524 (5)
C1—C2	1.518 (4)	C16—C17	1.528 (5)
C1—C5	1.528 (4)	C16—H16	1.0000
C1—C6	1.531 (4)	C17—C18	1.529 (5)
C2—C3	1.339 (4)	C17—H17A	0.9900
C2—C12	1.479 (4)	C17—H17B	0.9900
C3—C4	1.462 (4)	C18—C19	1.521 (6)
C3—C14	1.499 (4)	C18—H18A	0.9900
C5—H5A	0.9900	C18—H18B	0.9900
C5—H5B	0.9900	C19—C20	1.506 (6)
C6—C11	1.392 (4)	C19—H19A	0.9900
C6—C7	1.389 (4)	C19—H19B	0.9900
C7—C8	1.390 (4)	C20—C21	1.535 (5)
C7—H7	0.9500	C20—H20A	0.9900
C8—C9	1.381 (5)	C20—H20B	0.9900
C8—H8	0.9500	C21—H21A	0.9900
C9—C10	1.384 (5)	C21—H21B	0.9900

C4—O1—C1	110.3 (2)	O5—C13—H13C	109.5
C14—O2—C15	115.9 (3)	H13A—C13—H13C	109.5
C12—O5—C13	116.2 (2)	H13B—C13—H13C	109.5
C4—N1—C16	119.1 (3)	O3—C14—O2	126.0 (3)
O1—C1—C2	103.1 (2)	O3—C14—C3	124.1 (3)
O1—C1—C5	107.0 (2)	O2—C14—C3	109.9 (2)
C2—C1—C5	114.6 (2)	O2—C15—H15A	109.5
O1—C1—C6	109.0 (2)	O2—C15—H15B	109.5
C2—C1—C6	111.4 (2)	H15A—C15—H15B	109.5
C5—C1—C6	111.3 (2)	O2—C15—H15C	109.5
C3—C2—C12	128.2 (3)	H15A—C15—H15C	109.5
C3—C2—C1	109.5 (3)	H15B—C15—H15C	109.5
C12—C2—C1	122.3 (3)	N1—C16—C21	108.9 (3)
C2—C3—C4	108.8 (2)	N1—C16—C17	108.9 (3)
C2—C3—C14	128.2 (3)	C21—C16—C17	111.0 (3)
C4—C3—C14	123.1 (3)	N1—C16—H16	109.3
N1—C4—O1	125.8 (3)	C21—C16—H16	109.3
N1—C4—C3	126.0 (3)	C17—C16—H16	109.3
O1—C4—C3	108.2 (2)	C18—C17—C16	111.4 (3)
C1—C5—Br1	112.3 (2)	C18—C17—H17A	109.3
C1—C5—H5A	109.1	C16—C17—H17A	109.3
Br1—C5—H5A	109.1	C18—C17—H17B	109.3
C1—C5—H5B	109.1	C16—C17—H17B	109.3
Br1—C5—H5B	109.1	H17A—C17—H17B	108.0
H5A—C5—H5B	107.9	C19—C18—C17	111.2 (3)
C11—C6—C7	119.2 (3)	C19—C18—H18A	109.4
C11—C6—C1	121.3 (3)	C17—C18—H18A	109.4
C7—C6—C1	119.5 (3)	C19—C18—H18B	109.4
C6—C7—C8	120.1 (3)	C17—C18—H18B	109.4
C6—C7—H7	119.9	H18A—C18—H18B	108.0
C8—C7—H7	119.9	C20—C19—C18	110.8 (3)
C9—C8—C7	120.7 (3)	C20—C19—H19A	109.5
C9—C8—H8	119.6	C18—C19—H19A	109.5
C7—C8—H8	119.6	C20—C19—H19B	109.5
C8—C9—C10	119.5 (3)	C18—C19—H19B	109.5
C8—C9—H9	120.3	H19A—C19—H19B	108.1
C10—C9—H9	120.3	C19—C20—C21	110.9 (3)
C9—C10—C11	120.2 (3)	C19—C20—H20A	109.5
C9—C10—H10	119.9	C21—C20—H20A	109.5
C11—C10—H10	119.9	C19—C20—H20B	109.5
C6—C11—C10	120.3 (3)	C21—C20—H20B	109.5
C6—C11—H11	119.9	H20A—C20—H20B	108.0
C10—C11—H11	119.9	C16—C21—C20	111.4 (3)
O4—C12—O5	125.0 (3)	C16—C21—H21A	109.3
O4—C12—C2	123.6 (3)	C20—C21—H21A	109.3
O5—C12—C2	111.4 (3)	C16—C21—H21B	109.3
O5—C13—H13A	109.5	C20—C21—H21B	109.3
O5—C13—H13B	109.5	H21A—C21—H21B	108.0
H13A—C13—H13B	109.5

C4—O1—C1—C2	−3.2 (3)	C11—C6—C7—C8	−0.8 (4)
C4—O1—C1—C5	−124.4 (2)	C1—C6—C7—C8	179.7 (3)
C4—O1—C1—C6	115.1 (2)	C6—C7—C8—C9	0.0 (5)
O1—C1—C2—C3	4.5 (3)	C7—C8—C9—C10	0.6 (5)
C5—C1—C2—C3	120.4 (3)	C8—C9—C10—C11	−0.3 (5)
C6—C1—C2—C3	−112.2 (3)	C7—C6—C11—C10	1.1 (5)
O1—C1—C2—C12	−174.1 (2)	C1—C6—C11—C10	−179.4 (3)
C5—C1—C2—C12	−58.2 (4)	C9—C10—C11—C6	−0.6 (5)
C6—C1—C2—C12	69.2 (3)	C13—O5—C12—O4	2.8 (5)
C12—C2—C3—C4	174.5 (3)	C13—O5—C12—C2	−176.0 (3)
C1—C2—C3—C4	−4.0 (3)	C3—C2—C12—O4	−175.0 (3)
C12—C2—C3—C14	−4.6 (5)	C1—C2—C12—O4	3.3 (5)
C1—C2—C3—C14	176.9 (3)	C3—C2—C12—O5	3.8 (4)
C16—N1—C4—O1	−2.1 (5)	C1—C2—C12—O5	−177.9 (3)
C16—N1—C4—C3	177.6 (3)	C15—O2—C14—O3	−5.8 (4)
C1—O1—C4—N1	−179.2 (3)	C15—O2—C14—C3	175.4 (3)
C1—O1—C4—C3	1.1 (3)	C2—C3—C14—O3	100.1 (4)
C2—C3—C4—N1	−177.8 (3)	C4—C3—C14—O3	−78.9 (4)
C14—C3—C4—N1	1.4 (5)	C2—C3—C14—O2	−81.1 (4)
C2—C3—C4—O1	2.0 (3)	C4—C3—C14—O2	99.9 (3)
C14—C3—C4—O1	−178.9 (3)	C4—N1—C16—C21	146.3 (3)
O1—C1—C5—Br1	61.4 (3)	C4—N1—C16—C17	−92.6 (3)
C2—C1—C5—Br1	−52.2 (3)	N1—C16—C17—C18	−173.9 (3)
C6—C1—C5—Br1	−179.67 (19)	C21—C16—C17—C18	−54.1 (4)
O1—C1—C6—C11	153.4 (3)	C16—C17—C18—C19	55.4 (4)
C2—C1—C6—C11	−93.6 (3)	C17—C18—C19—C20	−57.0 (4)
C5—C1—C6—C11	35.6 (4)	C18—C19—C20—C21	57.2 (4)
O1—C1—C6—C7	−27.2 (3)	N1—C16—C21—C20	174.2 (3)
C2—C1—C6—C7	85.9 (3)	C17—C16—C21—C20	54.4 (4)
C5—C1—C6—C7	−145.0 (3)	C19—C20—C21—C16	−56.3 (4)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄BrNO₅
M_r	450.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	16.8599 (3), 7.2871 (1), 17.4145 (3)
β (°)	97.330 (1)
V (Å³)	2122.06 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.97
Crystal size (mm)	0.30 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.590, 0.828
No. of measured, independent and observed [I > 2σ(I)] reflections	19142, 4873, 4034
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.156, 1.08
No. of reflections	4873
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.31, −0.67

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the Research Council of Tehran University and the University of Malaya for supporting this study.

References

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