(5-Benzoyl-2-methyl-4-{[1-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl]meth­oxy}-1-benzofuran-7-yl)(phen­yl)methanone

Zhang, X.; Zhang, H.-L.; Dong, Z.-Y.; Qian, Q.; Wang, Y.-G.

doi:10.1107/S1600536812023720

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1916

doi:10.1107/S1600536812023720

Open

access

(5-Benzoyl-2-methyl-4-{[1-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl]methoxy}-1-benzofuran-7-yl)(phenyl)methanone

Xiao-qin Zhang,^a Hai-Liang Zhang,^b Zhu-Yong Dong,^b Qiang Qian ^b and Yu-Guang Wang ^a ^*

^aCollege of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and ^bZhejiang SiXian Pharmaceutical Co. Ltd, ShaoXing 312065, People's Republic of China
^*Correspondence e-mail: yuguangw@zjut.edu.cn

(Received 13 April 2012; accepted 24 May 2012; online 31 May 2012)

The crystal structure of the title compound, C₃₁H₂₂N₄O₄, features weak C—H⋯O interactions. The dihedral angle between the fused benzene and furan rings is 2.49 (15)°, while that between the triazole and pyridine rings is 10.23(18)°.

Related literature

For bioactive nnitrogen-linked heterocyclic compounds, see: Anderson et al. (2004 ); Ha et al. (2009 ); Liu et al. (2011 ); Tan et al. (2012 ); Venkatesan et al. (2010 ); Yim et al. (2010 ). For the bioactivity of benzofuran analogues substituted by heterocyclic moieties, see: El-Shehry et al. (2010 ); Kaldrikyan et al. (2009 ); Saberi et al. (2006 ). For a related structure, see: Liu et al. (2012 ).

Experimental

Crystal data

C₃₁H₂₂N₄O₄
M_r = 514.53
Triclinic, $[P \overline 1]$
a = 10.11 (2) Å
b = 10.87 (3) Å
c = 11.64 (3) Å
α = 94.73 (4)°
β = 92.07 (3)°
γ = 92.05 (4)°
V = 1273 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.38 × 0.22 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.966, T_max = 0.988
9629 measured reflections
4699 independent reflections
2743 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.200
S = 0.85
4699 reflections
353 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O3ⁱ	0.93	2.33	3.225 (10)	161
C16—H16⋯O3ⁱ	0.93	2.55	3.473 (10)	171
Symmetry code: (i) x, y, z-1.

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812023720/ds2193sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023720/ds2193Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023720/ds2193Isup3.cml

checkCIF report

Related literature top

For bioactive nnitrogen-linked heterocyclic compounds, see: Anderson et al. (2004); Ha et al. (2009); Liu et al. (2011); Tan et al. (2012); Venkatesan et al. (2010); Yim et al. (2010). For the bioactivity of benzofuran analogues substituted by heterocyclic moieties, see: El-Shehry et al. (2010); Kaldrikyan et al. (2009); Saberi et al. (2006). For a related structure, see: Liu et al. (2012).

Experimental top

General procedure to synthesize the title compound: Under a positive pressure of nitrogen, to a suspension of the swollen 2-polystyrene supported selanylmethyl-4-(prop-2-ynyloxy)-5,7-dibenzoyl- 2,3-dihydro-benzofuran in DMSO (30 mL) was added the mixed solution of 0.2 g (4.0 mmol) Cu₂SO₄ 5H₂O and 0.8 g(4.5 mmol) ascorbic acid in 10 mL water, 5.0 mmol 4-Azido-pyridine. After stirring for 15 h at 60°C, the resin was collected by filtration, washed with H₂O (30 mL×2), THF (20 mL×1), hot DMF (15 mL×1), H2O (30 mL×1), THF (20 mL×1), THF/H₂O (2:1) (20 mL×2), hot DMF (15 mL×1), THF (20 mL×1), THF/H₂O (2:1) (20 mL×2), THF (20 mL×2). The washed resin was suspended in THF (15 mL), 30% H₂O₂ (20.0 equiv) was added, and the mixture was stirred for 10 h at room temperature. The resin was collected by filtration, washed with H₂O (20 mL×2), THF (10 mL×2), THF/H₂O (2:1) (10 mL×2), THF (10 mL×2) , CH₂Cl₂ (10 mL×2), toluene (10 mL×2). The washed resin was suspended in 15 mL toluene, DBU (0.4 equiv) was added, and the mixture was stirred for 5.0 h at 80°C. The mixture was filtered, and the resin was washed with CH₂Cl₂ (15 mL ×2). The filtrate was washed with 0.25M HCl (30 mL×2), saturated sodium bicarbonate solution(35 mL×2), dried with anhydrous magnesium sulfate, and evaporated to dryness under vacuum to obtain the title compound. Further purification was via flash chromatography with n-hexanes-EtOAc (3:1, V/V) as the eluent for microanalyses. ¹H-NMR(CDCl₃, 400MHz, Bruker Avance spectrometer): δ 8.78-8.76 (d, 2H, J=5.6Hz), 7.85-7.81 (m, 4H), 7.64-7.40 (m, 10H), 6.77 (d, 1H, J=0.8Hz), 5.52 (s, 2H), 2.47 (s, 3H); 13C-NMR(CDCl3): δ 195.6, 192,8, 157.7, 156.2, 152.5, 151.9, 145.4, 143.1, 138.4, 137.9, 133.4, 133.2, 130.3, 130.2, 128.7, 128.6, 128.1, 125.0, 122.1, 120.5, 118.3, 113.9, 101.2, 67.1, 14.3; MS(ESI) m/z 515 (M+H)⁺. The title compound was recrystallized from CHCl₂ at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound showing the atom numbering scheme and the ellipsoids at the 50% probability level.

(5-Benzoyl-2-methyl-4-{[1-(pyridin-4-yl)-1H-1,2,3-triazol-4- yl]methoxy}-1-benzofuran-7-yl)(phenyl)methanone top

Crystal data top

C₃₁H₂₂N₄O₄	Z = 2
M_r = 514.53	F(000) = 536
Triclinic, P1	D_x = 1.343 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.11 (2) Å	Cell parameters from 1346 reflections
b = 10.87 (3) Å	θ = 2.5–21.0°
c = 11.64 (3) Å	µ = 0.09 mm⁻¹
α = 94.73 (4)°	T = 296 K
β = 92.07 (3)°	Block, colourless
γ = 92.05 (4)°	0.38 × 0.22 × 0.13 mm
V = 1273 (5) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4699 independent reflections
Radiation source: fine-focus sealed tube	2743 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
phi and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.966, T_max = 0.988	k = −12→13
9629 measured reflections	l = −14→14

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) = 0.200	H-atom parameters constrained
S = 0.85	w = 1/[σ²(F_o²) + (0.1P)² + 0.4387P] where P = (F_o² + 2F_c²)/3
4699 reflections	(Δ/σ)_max < 0.001
353 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₃₁H₂₂N₄O₄	γ = 92.05 (4)°
M_r = 514.53	V = 1273 (5) Å³
Triclinic, P1	Z = 2
a = 10.11 (2) Å	Mo Kα radiation
b = 10.87 (3) Å	µ = 0.09 mm⁻¹
c = 11.64 (3) Å	T = 296 K
α = 94.73 (4)°	0.38 × 0.22 × 0.13 mm
β = 92.07 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4699 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2743 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.988	R_int = 0.044
9629 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.200	H-atom parameters constrained
S = 0.85	Δρ_max = 0.26 e Å⁻³
4699 reflections	Δρ_min = −0.17 e Å⁻³
353 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	0.4387 (2)	−0.1220 (2)	−0.3567 (2)	0.0473 (6)
N2	0.5280 (3)	−0.1333 (3)	−0.2672 (2)	0.0622 (8)
N3	0.4837 (3)	−0.0696 (3)	−0.1759 (2)	0.0614 (8)
N4	0.5183 (3)	−0.2859 (3)	−0.6907 (3)	0.0806 (10)
O1	0.20278 (18)	−0.01035 (18)	−0.05837 (16)	0.0467 (5)
O2	−0.0057 (2)	−0.2440 (2)	0.12502 (19)	0.0610 (6)
O3	0.1408 (2)	0.0551 (2)	0.48995 (19)	0.0654 (7)
O4	0.19574 (18)	0.30077 (17)	0.25525 (16)	0.0464 (5)
C1	0.1656 (3)	0.1786 (3)	0.2199 (2)	0.0406 (7)
C2	0.1172 (3)	0.0928 (3)	0.2923 (2)	0.0425 (7)
C3	0.0985 (3)	−0.0274 (3)	0.2403 (2)	0.0448 (7)
H3	0.0657	−0.0882	0.2846	0.054*
C4	0.1268 (2)	−0.0616 (3)	0.1240 (2)	0.0405 (7)
C5	0.1774 (3)	0.0282 (3)	0.0540 (2)	0.0398 (7)
C6	0.1954 (2)	0.1526 (3)	0.1030 (2)	0.0401 (7)
C7	0.2451 (3)	0.2700 (3)	0.0659 (2)	0.0448 (7)
H7	0.2711	0.2844	−0.0078	0.054*
C8	0.2462 (3)	0.3540 (3)	0.1584 (2)	0.0452 (7)
C9	0.2956 (3)	0.0639 (3)	−0.1195 (3)	0.0516 (8)
H9A	0.3597	0.1067	−0.0648	0.062*
H9B	0.2482	0.1253	−0.1586	0.062*
C10	0.3658 (3)	−0.0175 (3)	−0.2056 (2)	0.0465 (7)
C11	0.3382 (3)	−0.0494 (3)	−0.3205 (3)	0.0474 (7)
H11	0.2660	−0.0265	−0.3646	0.057*
C12	0.4637 (3)	−0.1773 (3)	−0.4698 (3)	0.0491 (7)
C13	0.5661 (4)	−0.2603 (4)	−0.4842 (3)	0.0738 (11)
H13	0.6175	−0.2813	−0.4214	0.089*
C14	0.5883 (4)	−0.3104 (4)	−0.5955 (4)	0.0874 (13)
H14	0.6567	−0.3648	−0.6046	0.105*
C15	0.4212 (4)	−0.2071 (4)	−0.6724 (3)	0.0698 (10)
H15	0.3701	−0.1886	−0.7363	0.084*
C16	0.3902 (3)	−0.1506 (3)	−0.5659 (3)	0.0567 (8)
H16	0.3216	−0.0960	−0.5596	0.068*
C17	0.0912 (3)	−0.1942 (3)	0.0833 (3)	0.0468 (7)
C18	0.1739 (3)	−0.2720 (3)	0.0022 (2)	0.0448 (7)
C19	0.1132 (3)	−0.3795 (3)	−0.0558 (3)	0.0547 (8)
H19	0.0227	−0.3952	−0.0504	0.066*
C20	0.1884 (4)	−0.4627 (3)	−0.1214 (3)	0.0639 (9)
H20	0.1477	−0.5333	−0.1595	0.077*
C21	0.3240 (4)	−0.4402 (3)	−0.1299 (3)	0.0683 (10)
H21	0.3739	−0.4959	−0.1733	0.082*
C22	0.3846 (3)	−0.3340 (3)	−0.0732 (3)	0.0627 (9)
H22	0.4752	−0.3188	−0.0788	0.075*
C23	0.3098 (3)	−0.2500 (3)	−0.0078 (3)	0.0520 (8)
H23	0.3510	−0.1789	0.0293	0.062*
C24	0.0941 (3)	0.1209 (3)	0.4186 (2)	0.0456 (7)
C25	0.0118 (3)	0.2283 (3)	0.4561 (2)	0.0447 (7)
C26	−0.0814 (3)	0.2755 (3)	0.3805 (3)	0.0522 (8)
H26	−0.0883	0.2445	0.3035	0.063*
C27	−0.1641 (4)	0.3690 (3)	0.4208 (3)	0.0676 (10)
H27	−0.2274	0.3984	0.3710	0.081*
C28	−0.1517 (4)	0.4178 (3)	0.5349 (3)	0.0737 (11)
H28	−0.2062	0.4803	0.5614	0.088*
C29	−0.0573 (4)	0.3730 (3)	0.6102 (3)	0.0698 (10)
H29	−0.0478	0.4067	0.6863	0.084*
C30	0.0217 (3)	0.2784 (3)	0.5712 (3)	0.0571 (8)
H30	0.0825	0.2474	0.6221	0.068*
C31	0.2916 (4)	0.4852 (3)	0.1780 (3)	0.0660 (10)
H31A	0.3324	0.5105	0.1101	0.099*
H31B	0.3547	0.4950	0.2421	0.099*
H31C	0.2171	0.5351	0.1946	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0469 (13)	0.0519 (15)	0.0426 (14)	0.0057 (11)	0.0023 (11)	−0.0015 (12)
N2	0.0580 (16)	0.087 (2)	0.0416 (15)	0.0196 (15)	−0.0011 (12)	−0.0016 (14)
N3	0.0566 (16)	0.083 (2)	0.0443 (16)	0.0135 (14)	0.0016 (12)	−0.0016 (14)
N4	0.080 (2)	0.090 (2)	0.066 (2)	0.0052 (18)	0.0064 (17)	−0.0285 (18)
O1	0.0542 (12)	0.0487 (12)	0.0367 (11)	−0.0012 (9)	0.0065 (9)	0.0000 (9)
O2	0.0587 (13)	0.0587 (14)	0.0641 (15)	−0.0120 (11)	0.0105 (11)	−0.0002 (11)
O3	0.0742 (15)	0.0765 (16)	0.0481 (14)	0.0220 (12)	0.0009 (11)	0.0133 (12)
O4	0.0534 (12)	0.0416 (12)	0.0440 (12)	0.0014 (9)	0.0062 (9)	0.0006 (9)
C1	0.0412 (15)	0.0398 (16)	0.0409 (16)	0.0028 (12)	0.0037 (12)	0.0013 (13)
C2	0.0448 (15)	0.0470 (17)	0.0362 (16)	0.0024 (13)	0.0034 (12)	0.0048 (13)
C3	0.0465 (16)	0.0443 (17)	0.0449 (17)	0.0009 (13)	0.0060 (13)	0.0093 (13)
C4	0.0378 (14)	0.0431 (16)	0.0410 (16)	0.0015 (12)	0.0025 (12)	0.0055 (13)
C5	0.0368 (14)	0.0465 (17)	0.0357 (16)	0.0038 (12)	0.0005 (11)	0.0016 (12)
C6	0.0366 (14)	0.0433 (17)	0.0407 (16)	0.0020 (12)	0.0002 (12)	0.0054 (13)
C7	0.0474 (16)	0.0479 (18)	0.0393 (16)	0.0001 (13)	0.0063 (12)	0.0037 (13)
C8	0.0488 (16)	0.0446 (17)	0.0432 (17)	0.0023 (13)	0.0078 (13)	0.0068 (14)
C9	0.0605 (19)	0.0501 (18)	0.0438 (18)	−0.0023 (15)	0.0129 (14)	−0.0003 (14)
C10	0.0493 (17)	0.0476 (17)	0.0427 (17)	0.0017 (13)	0.0057 (13)	0.0022 (14)
C11	0.0465 (16)	0.0529 (18)	0.0430 (17)	0.0071 (14)	0.0022 (13)	0.0035 (14)
C12	0.0529 (17)	0.0502 (18)	0.0427 (17)	0.0005 (14)	0.0035 (13)	−0.0057 (14)
C13	0.072 (2)	0.080 (3)	0.066 (2)	0.026 (2)	−0.0107 (18)	−0.019 (2)
C14	0.081 (3)	0.094 (3)	0.081 (3)	0.027 (2)	−0.007 (2)	−0.038 (2)
C15	0.080 (2)	0.081 (3)	0.045 (2)	0.003 (2)	0.0019 (17)	−0.0092 (18)
C16	0.062 (2)	0.061 (2)	0.0470 (19)	0.0081 (16)	0.0018 (15)	−0.0014 (15)
C17	0.0452 (16)	0.0491 (18)	0.0457 (17)	−0.0031 (14)	−0.0022 (13)	0.0055 (14)
C18	0.0489 (16)	0.0412 (17)	0.0443 (17)	0.0021 (13)	−0.0028 (13)	0.0046 (13)
C19	0.0511 (18)	0.0520 (19)	0.059 (2)	−0.0061 (15)	−0.0065 (15)	−0.0002 (16)
C20	0.080 (2)	0.051 (2)	0.057 (2)	−0.0020 (18)	−0.0036 (18)	−0.0091 (16)
C21	0.080 (2)	0.067 (2)	0.057 (2)	0.0141 (19)	0.0093 (18)	−0.0092 (18)
C22	0.0550 (19)	0.061 (2)	0.073 (2)	0.0063 (16)	0.0108 (16)	0.0037 (18)
C23	0.0523 (17)	0.0480 (18)	0.0551 (19)	0.0005 (14)	0.0007 (14)	0.0027 (15)
C24	0.0467 (16)	0.0507 (18)	0.0398 (17)	−0.0002 (13)	0.0014 (13)	0.0068 (14)
C25	0.0482 (16)	0.0480 (17)	0.0388 (16)	−0.0016 (13)	0.0094 (13)	0.0067 (13)
C26	0.0605 (19)	0.0560 (19)	0.0406 (17)	0.0045 (15)	0.0101 (14)	0.0016 (14)
C27	0.074 (2)	0.070 (2)	0.062 (2)	0.0198 (19)	0.0130 (17)	0.0144 (19)
C28	0.092 (3)	0.062 (2)	0.068 (3)	0.010 (2)	0.030 (2)	−0.0012 (19)
C29	0.082 (3)	0.076 (3)	0.050 (2)	0.005 (2)	0.0135 (19)	−0.0058 (19)
C30	0.064 (2)	0.066 (2)	0.0414 (18)	0.0011 (17)	0.0065 (15)	0.0019 (15)
C31	0.085 (2)	0.050 (2)	0.062 (2)	−0.0033 (17)	0.0115 (18)	−0.0044 (17)

Geometric parameters (Å, º) top

N1—C11	1.366 (4)	C13—C14	1.391 (6)
N1—N2	1.369 (4)	C13—H13	0.9300
N1—C12	1.437 (5)	C14—H14	0.9300
N2—N3	1.320 (4)	C15—C16	1.388 (5)
N3—C10	1.383 (4)	C15—H15	0.9300
N4—C15	1.337 (5)	C16—H16	0.9300
N4—C14	1.343 (6)	C17—C18	1.509 (5)
O1—C5	1.376 (4)	C18—C23	1.397 (5)
O1—C9	1.458 (4)	C18—C19	1.410 (5)
O2—C17	1.236 (4)	C19—C20	1.398 (5)
O3—C24	1.232 (4)	C19—H19	0.9300
O4—C1	1.378 (4)	C20—C21	1.392 (6)
O4—C8	1.412 (4)	C20—H20	0.9300
C1—C2	1.395 (4)	C21—C22	1.393 (5)
C1—C6	1.412 (5)	C21—H21	0.9300
C2—C3	1.398 (5)	C22—C23	1.401 (5)
C2—C24	1.505 (5)	C22—H22	0.9300
C3—C4	1.416 (5)	C23—H23	0.9300
C3—H3	0.9300	C24—C25	1.503 (5)
C4—C5	1.416 (4)	C25—C30	1.402 (5)
C4—C17	1.507 (5)	C25—C26	1.405 (5)
C5—C6	1.426 (5)	C26—C27	1.401 (5)
C6—C7	1.459 (5)	C26—H26	0.9300
C7—C8	1.352 (4)	C27—C28	1.389 (6)
C7—H7	0.9300	C27—H27	0.9300
C8—C31	1.480 (5)	C28—C29	1.399 (6)
C9—C10	1.497 (4)	C28—H28	0.9300
C9—H9A	0.9700	C29—C30	1.382 (5)
C9—H9B	0.9700	C29—H29	0.9300
C10—C11	1.369 (5)	C30—H30	0.9300
C11—H11	0.9300	C31—H31A	0.9600
C12—C16	1.376 (5)	C31—H31B	0.9600
C12—C13	1.402 (5)	C31—H31C	0.9600

C11—N1—N2	110.2 (3)	N4—C15—H15	117.3
C11—N1—C12	130.0 (3)	C16—C15—H15	117.3
N2—N1—C12	119.7 (3)	C12—C16—C15	118.3 (3)
N3—N2—N1	106.9 (3)	C12—C16—H16	120.8
N2—N3—C10	109.4 (3)	C15—C16—H16	120.8
C15—N4—C14	115.0 (3)	O2—C17—C4	117.9 (3)
C5—O1—C9	118.3 (2)	O2—C17—C18	118.5 (3)
C1—O4—C8	106.1 (2)	C4—C17—C18	123.5 (3)
O4—C1—C2	123.9 (3)	C23—C18—C19	118.8 (3)
O4—C1—C6	110.6 (2)	C23—C18—C17	123.1 (3)
C2—C1—C6	125.5 (3)	C19—C18—C17	117.8 (3)
C1—C2—C3	114.7 (3)	C20—C19—C18	120.4 (3)
C1—C2—C24	124.6 (3)	C20—C19—H19	119.8
C3—C2—C24	120.7 (3)	C18—C19—H19	119.8
C2—C3—C4	123.5 (3)	C21—C20—C19	120.3 (3)
C2—C3—H3	118.2	C21—C20—H20	119.8
C4—C3—H3	118.2	C19—C20—H20	119.8
C5—C4—C3	119.9 (3)	C22—C21—C20	119.7 (3)
C5—C4—C17	125.1 (3)	C22—C21—H21	120.2
C3—C4—C17	114.9 (2)	C20—C21—H21	120.2
O1—C5—C4	117.3 (3)	C21—C22—C23	120.3 (3)
O1—C5—C6	124.3 (3)	C21—C22—H22	119.8
C4—C5—C6	118.3 (3)	C23—C22—H22	119.8
C1—C6—C5	118.1 (3)	C18—C23—C22	120.5 (3)
C1—C6—C7	104.9 (3)	C18—C23—H23	119.7
C5—C6—C7	136.9 (3)	C22—C23—H23	119.7
C8—C7—C6	107.4 (3)	O3—C24—C25	120.7 (3)
C8—C7—H7	126.3	O3—C24—C2	120.1 (3)
C6—C7—H7	126.3	C25—C24—C2	119.3 (3)
C7—C8—O4	110.9 (3)	C30—C25—C26	118.7 (3)
C7—C8—C31	133.4 (3)	C30—C25—C24	119.5 (3)
O4—C8—C31	115.6 (3)	C26—C25—C24	121.7 (3)
O1—C9—C10	109.8 (3)	C27—C26—C25	120.2 (3)
O1—C9—H9A	109.7	C27—C26—H26	119.9
C10—C9—H9A	109.7	C25—C26—H26	119.9
O1—C9—H9B	109.7	C28—C27—C26	120.1 (3)
C10—C9—H9B	109.7	C28—C27—H27	120.0
H9A—C9—H9B	108.2	C26—C27—H27	120.0
C11—C10—N3	107.9 (3)	C27—C28—C29	120.1 (4)
C11—C10—C9	131.1 (3)	C27—C28—H28	120.0
N3—C10—C9	121.0 (3)	C29—C28—H28	120.0
N1—C11—C10	105.6 (3)	C30—C29—C28	119.8 (3)
N1—C11—H11	127.2	C30—C29—H29	120.1
C10—C11—H11	127.2	C28—C29—H29	120.1
C16—C12—C13	118.5 (3)	C29—C30—C25	121.2 (3)
C16—C12—N1	121.7 (3)	C29—C30—H30	119.4
C13—C12—N1	119.8 (3)	C25—C30—H30	119.4
C14—C13—C12	117.9 (3)	C8—C31—H31A	109.5
C14—C13—H13	121.0	C8—C31—H31B	109.5
C12—C13—H13	121.0	H31A—C31—H31B	109.5
N4—C14—C13	124.9 (4)	C8—C31—H31C	109.5
N4—C14—H14	117.6	H31A—C31—H31C	109.5
C13—C14—H14	117.6	H31B—C31—H31C	109.5
N4—C15—C16	125.4 (4)

C11—N1—N2—N3	0.5 (3)	N2—N1—C12—C16	−168.3 (3)
C12—N1—N2—N3	177.1 (3)	C11—N1—C12—C13	−172.8 (3)
N1—N2—N3—C10	0.3 (4)	N2—N1—C12—C13	11.3 (4)
C8—O4—C1—C2	177.6 (2)	C16—C12—C13—C14	0.5 (5)
C8—O4—C1—C6	−0.1 (3)	N1—C12—C13—C14	−179.0 (3)
O4—C1—C2—C3	−177.4 (2)	C15—N4—C14—C13	0.0 (6)
C6—C1—C2—C3	0.0 (4)	C12—C13—C14—N4	−0.5 (7)
O4—C1—C2—C24	−1.4 (4)	C14—N4—C15—C16	0.6 (6)
C6—C1—C2—C24	176.0 (3)	C13—C12—C16—C15	−0.1 (5)
C1—C2—C3—C4	0.5 (4)	N1—C12—C16—C15	179.5 (3)
C24—C2—C3—C4	−175.7 (2)	N4—C15—C16—C12	−0.5 (6)
C2—C3—C4—C5	0.3 (4)	C5—C4—C17—O2	−144.0 (3)
C2—C3—C4—C17	−176.2 (2)	C3—C4—C17—O2	32.3 (4)
C9—O1—C5—C4	−158.5 (2)	C5—C4—C17—C18	41.3 (4)
C9—O1—C5—C6	23.3 (4)	C3—C4—C17—C18	−142.4 (3)
C3—C4—C5—O1	−179.9 (2)	O2—C17—C18—C23	−149.1 (3)
C17—C4—C5—O1	−3.7 (4)	C4—C17—C18—C23	25.6 (4)
C3—C4—C5—C6	−1.6 (4)	O2—C17—C18—C19	23.6 (4)
C17—C4—C5—C6	174.6 (2)	C4—C17—C18—C19	−161.7 (3)
O4—C1—C6—C5	176.4 (2)	C23—C18—C19—C20	0.4 (5)
C2—C1—C6—C5	−1.3 (4)	C17—C18—C19—C20	−172.6 (3)
O4—C1—C6—C7	−1.1 (3)	C18—C19—C20—C21	0.1 (5)
C2—C1—C6—C7	−178.7 (3)	C19—C20—C21—C22	−0.3 (5)
O1—C5—C6—C1	−179.8 (2)	C20—C21—C22—C23	0.0 (5)
C4—C5—C6—C1	2.0 (4)	C19—C18—C23—C22	−0.7 (5)
O1—C5—C6—C7	−3.4 (5)	C17—C18—C23—C22	171.9 (3)
C4—C5—C6—C7	178.4 (3)	C21—C22—C23—C18	0.5 (5)
C1—C6—C7—C8	1.9 (3)	C1—C2—C24—O3	−128.6 (3)
C5—C6—C7—C8	−174.9 (3)	C3—C2—C24—O3	47.1 (4)
C6—C7—C8—O4	−2.0 (3)	C1—C2—C24—C25	52.4 (4)
C6—C7—C8—C31	176.2 (3)	C3—C2—C24—C25	−131.8 (3)
C1—O4—C8—C7	1.3 (3)	O3—C24—C25—C30	20.2 (4)
C1—O4—C8—C31	−177.2 (2)	C2—C24—C25—C30	−160.8 (3)
C5—O1—C9—C10	149.1 (2)	O3—C24—C25—C26	−155.7 (3)
N2—N3—C10—C11	−0.9 (4)	C2—C24—C25—C26	23.2 (4)
N2—N3—C10—C9	−177.8 (3)	C30—C25—C26—C27	−1.2 (4)
O1—C9—C10—C11	93.6 (4)	C24—C25—C26—C27	174.8 (3)
O1—C9—C10—N3	−90.4 (4)	C25—C26—C27—C28	1.8 (5)
N2—N1—C11—C10	−1.0 (3)	C26—C27—C28—C29	−0.5 (5)
C12—N1—C11—C10	−177.2 (3)	C27—C28—C29—C30	−1.2 (6)
N3—C10—C11—N1	1.2 (3)	C28—C29—C30—C25	1.8 (5)
C9—C10—C11—N1	177.6 (3)	C26—C25—C30—C29	−0.5 (5)
C11—N1—C12—C16	7.6 (5)	C24—C25—C30—C29	−176.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O3ⁱ	0.93	2.33	3.225 (10)	161
C16—H16···O3ⁱ	0.93	2.55	3.473 (10)	171

Symmetry code: (i) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₃₁H₂₂N₄O₄
M_r	514.53
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.11 (2), 10.87 (3), 11.64 (3)
α, β, γ (°)	94.73 (4), 92.07 (3), 92.05 (4)
V (Å³)	1273 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.38 × 0.22 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.966, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	9629, 4699, 2743
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.200, 0.85
No. of reflections	4699
No. of parameters	353
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.17

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O3ⁱ	0.93	2.33	3.225 (10)	161
C16—H16···O3ⁱ	0.93	2.55	3.473 (10)	171

Symmetry code: (i) x, y, z−1.

Acknowledgements

The authors are grateful for financial support by the Science and Technology Department of Zhejiang Province Foundation of China (project No. 2010 C32022) and the Zhejiang Province Natural Science Foundation of China (project No. Y4090410.)

References

Anderson, S., Taylor, P. N. & Verschoor, G. L. B. (2004). Chem. Eur. J. 10, 518–527. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
El-Shehry, M. F., Swellema, R. H., Abu-Bakr, Sh. M. & El-Telbani, E. M. (2010). Eur. J. Med. Chem. 45, 4783–4787. Web of Science CAS PubMed Google Scholar
Ha, D. T., Kim, H. J., Thuong, P. T., Ngoc, T. M., Lee, I., Nguyen, D. H. & Bae, K. H. (2009). J. Ethnopharmacol. 125, 304–309. Web of Science CrossRef PubMed CAS Google Scholar
Kaldrikyan, M. A., Grigoryan, L. A., Melik-Ogandzhanyan, R. G. & Arsenyan, F. G. (2009). Pharm. Chem. J. 43, 242–244. Web of Science CrossRef CAS Google Scholar
Liu, X. H., Tan, C. X. & Jian, Q. W. (2011). Phosphorus Sulfur Silicon Relat. Elem. 186, 552–557. Web of Science CrossRef CAS Google Scholar
Liu, X.-H., Tan, C.-X., Weng, J.-Q. & Liu, H.-J. (2012). Acta Cryst. E68, o493. Web of Science CSD CrossRef IUCr Journals Google Scholar
Saberi, M. R., Vinh, T. K., Yee, S. W., Griffiths, B. J. N., Evans, P. J. & Simons, C. (2006). J. Med. Chem. 49, 1016–1022. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tan, C. X., Shi, Y. X., Jian, Q. W., Liu, X. H., Zhao, W. G. & Li, B. J. (2012). Lett. Drug. Des. Discov. 9, 431–435. CrossRef CAS Google Scholar
Venkatesan, A. M., Santos, O. D., Ellingboe, J., Evrard, D. A., Harrison, B., Smith, D. L., Scerni, R., Hornby, G. A., Schechter, L. E. & Andree, T. H. (2010). Bioorg. Med. Chem. Lett. 20, 824–827. Web of Science CrossRef CAS PubMed Google Scholar
Yim, N. H., Ha, D. T., Trung, T. N., Kim, J. P., Lee, S. M., Na, M. K., Jung, H. J., Kim, H. S., Kim, Y. H. & Bae, K. H. (2010). Bioorg. Med. Chem. Lett. 20, 1165–1168. Web of Science CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1916

doi:10.1107/S1600536812023720

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(5-Benzoyl-2-methyl-4-{[1-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl]meth­­oxy}-1-benzo­furan-7-yl)(phen­yl)methanone

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(5-Benzoyl-2-methyl-4-{[1-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl]methoxy}-1-benzofuran-7-yl)(phenyl)methanone