(E)-3-(9-Anthr-yl)-1-(4-chloro-phen-yl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one.

In the title compound, C(25)H(16)ClN(3)O, the anthryl and chloro-phenyl substituents are on opposite sides of the triazole ring. The anthryl and benzene mean planes are aligned at 83.35 (2) and 89.09 (2)°, respectively, with respect to the triazole ring.

Related literature

For general background to the biological properties of chalcones, see: Corréa et al. (2001 ▶). For the synthesis, see: Erhardt et al. (1985 ▶); Kranz et al. (1980 ▶). For similar crystal structures, see: Lu et al. (2009 ▶); Wang et al. (2009 ▶); Yan et al. (2009 ▶).

Experimental

Crystal data

C25H16ClN3O

M = 409.86

Orthorhombic,

a = 13.1464 (11) Å

b = 13.5485 (12) Å

c = 22.0974 (19) Å

V = 3935.9 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 298 K

0.26 × 0.12 × 0.10 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.946, T max = 0.979

19759 measured reflections

3859 independent reflections

3430 reflections with I > 2σ(I)

R int = 0.119

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.162

S = 1.12

3859 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 2001 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038628/ng2650sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038628/ng2650Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H16ClN3O	F(000) = 1696
Mr = 409.86	Dx = 1.383 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6265 reflections
a = 13.1464 (11) Å	θ = 2.4–27.5°
b = 13.5485 (12) Å	µ = 0.22 mm−1
c = 22.0974 (19) Å	T = 298 K
V = 3935.9 (6) Å3	Block, yellow
Z = 8	0.26 × 0.12 × 0.10 mm

Bruker SMART diffractometer	3859 independent reflections
Radiation source: fine-focus sealed tube	3430 reflections with I > 2σ(I)
graphite	Rint = 0.119
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.946, Tmax = 0.979	k = −16→16
19759 measured reflections	l = −17→27

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0638P)2 + 1.7945P] where P = (Fo2 + 2Fc2)/3
3859 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.30643 (17)	1.1607 (2)	0.39287 (11)	0.0426 (6)
C2	0.27174 (18)	1.0658 (2)	0.40129 (11)	0.0447 (6)
H2	0.2393	1.0481	0.4371	0.054*
C3	0.28585 (17)	0.99743 (18)	0.35589 (11)	0.0391 (5)
H3	0.2607	0.9337	0.3604	0.047*
C4	0.33774 (15)	1.02351 (17)	0.30331 (9)	0.0330 (5)
C5	0.37216 (18)	1.11961 (18)	0.29626 (11)	0.0421 (6)
H5	0.4068	1.1373	0.2612	0.051*
C6	0.35564 (19)	1.18896 (19)	0.34055 (12)	0.0474 (6)
H6	0.3772	1.2538	0.3353	0.057*
C7	0.35073 (16)	0.95057 (16)	0.25405 (10)	0.0346 (5)
C8	0.45084 (15)	0.95049 (15)	0.22047 (9)	0.0303 (5)
C9	0.3687 (2)	0.9653 (2)	0.11838 (12)	0.0535 (7)
H9	0.3044	0.9863	0.1304	0.064*
C10	0.4936 (2)	0.9244 (2)	0.06792 (11)	0.0484 (6)
H10	0.5345	0.9105	0.0347	0.058*
C11	0.54031 (16)	0.94857 (17)	0.24822 (9)	0.0340 (5)
H11	0.5985	0.9497	0.2243	0.041*
C12	0.55381 (15)	0.94475 (17)	0.31479 (9)	0.0327 (5)
C13	0.52315 (15)	0.86077 (17)	0.34745 (9)	0.0332 (5)
C14	0.48195 (18)	0.77419 (18)	0.32006 (11)	0.0406 (5)
H14	0.4733	0.7724	0.2783	0.049*
C15	0.4552 (2)	0.6945 (2)	0.35349 (13)	0.0506 (6)
H15	0.4292	0.6389	0.3343	0.061*
C16	0.4662 (2)	0.6944 (2)	0.41698 (12)	0.0517 (7)
H16	0.4470	0.6393	0.4394	0.062*
C17	0.5045 (2)	0.7742 (2)	0.44502 (11)	0.0464 (6)
H17	0.5110	0.7735	0.4869	0.056*
C18	0.53536 (16)	0.85998 (18)	0.41238 (10)	0.0376 (5)
C19	0.57685 (18)	0.94139 (19)	0.44096 (10)	0.0423 (6)
H19	0.5826	0.9411	0.4829	0.051*
C20	0.61025 (17)	1.02352 (18)	0.40905 (10)	0.0386 (5)
C21	0.6548 (2)	1.1069 (2)	0.43795 (12)	0.0534 (7)
H21	0.6603	1.1075	0.4799	0.064*
C22	0.6890 (3)	1.1848 (2)	0.40624 (14)	0.0653 (8)
H22	0.7177	1.2383	0.4263	0.078*
C23	0.6813 (2)	1.1853 (2)	0.34226 (13)	0.0590 (7)
H23	0.7065	1.2386	0.3204	0.071*
C24	0.63764 (19)	1.10861 (19)	0.31269 (11)	0.0450 (6)
H24	0.6321	1.1108	0.2708	0.054*
C25	0.60008 (16)	1.02502 (17)	0.34426 (9)	0.0345 (5)
Cl1	0.28705 (6)	1.24841 (6)	0.44918 (4)	0.0647 (3)
N4	0.39691 (19)	0.95338 (19)	0.06181 (9)	0.0571 (6)
N5	0.52736 (15)	0.91671 (17)	0.12348 (9)	0.0449 (5)
N6	0.44473 (13)	0.94308 (14)	0.15650 (8)	0.0334 (4)
O1	0.28455 (12)	0.89224 (14)	0.24077 (9)	0.0505 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0445 (12)	0.0499 (15)	0.0335 (12)	0.0064 (11)	0.0001 (9)	−0.0160 (11)
C2	0.0506 (14)	0.0532 (16)	0.0303 (12)	0.0020 (11)	0.0086 (10)	−0.0021 (11)
C3	0.0449 (12)	0.0371 (13)	0.0354 (12)	−0.0013 (10)	0.0042 (9)	0.0017 (10)
C4	0.0348 (11)	0.0350 (12)	0.0293 (11)	0.0028 (9)	0.0000 (8)	−0.0028 (9)
C5	0.0513 (13)	0.0387 (13)	0.0364 (13)	−0.0036 (10)	0.0105 (10)	−0.0026 (10)
C6	0.0573 (15)	0.0347 (13)	0.0503 (15)	−0.0030 (11)	0.0081 (11)	−0.0093 (11)
C7	0.0378 (11)	0.0346 (12)	0.0313 (11)	0.0009 (9)	−0.0031 (8)	−0.0021 (9)
C8	0.0418 (11)	0.0280 (11)	0.0211 (10)	0.0010 (8)	0.0003 (8)	−0.0030 (8)
C9	0.0489 (14)	0.078 (2)	0.0332 (13)	0.0122 (13)	−0.0078 (10)	−0.0027 (13)
C10	0.0687 (16)	0.0541 (16)	0.0225 (11)	0.0060 (13)	0.0009 (11)	−0.0051 (11)
C11	0.0397 (11)	0.0380 (12)	0.0244 (11)	0.0011 (9)	0.0025 (8)	−0.0015 (9)
C12	0.0365 (11)	0.0386 (12)	0.0230 (11)	0.0049 (9)	−0.0012 (8)	−0.0014 (9)
C13	0.0358 (11)	0.0377 (12)	0.0260 (11)	0.0070 (9)	0.0000 (8)	−0.0019 (9)
C14	0.0520 (13)	0.0389 (13)	0.0309 (12)	0.0042 (10)	−0.0024 (10)	−0.0025 (10)
C15	0.0654 (16)	0.0412 (15)	0.0454 (15)	−0.0044 (12)	−0.0060 (12)	0.0003 (12)
C16	0.0632 (16)	0.0476 (16)	0.0444 (15)	−0.0039 (12)	−0.0039 (12)	0.0151 (12)
C17	0.0566 (15)	0.0524 (16)	0.0303 (12)	0.0013 (12)	−0.0055 (10)	0.0108 (11)
C18	0.0423 (12)	0.0432 (13)	0.0272 (11)	0.0060 (10)	−0.0009 (9)	0.0012 (10)
C19	0.0568 (14)	0.0494 (15)	0.0208 (11)	0.0048 (11)	−0.0032 (9)	−0.0036 (10)
C20	0.0487 (13)	0.0406 (13)	0.0264 (11)	0.0074 (10)	−0.0045 (9)	−0.0051 (10)
C21	0.0813 (19)	0.0464 (15)	0.0324 (13)	−0.0027 (13)	−0.0121 (12)	−0.0104 (11)
C22	0.102 (2)	0.0429 (16)	0.0509 (17)	−0.0114 (15)	−0.0188 (16)	−0.0087 (13)
C23	0.087 (2)	0.0419 (15)	0.0486 (16)	−0.0120 (14)	−0.0113 (14)	0.0063 (12)
C24	0.0604 (15)	0.0420 (14)	0.0325 (12)	−0.0027 (11)	−0.0076 (10)	0.0040 (10)
C25	0.0397 (11)	0.0376 (12)	0.0261 (11)	0.0057 (9)	−0.0041 (8)	−0.0021 (9)
Cl1	0.0712 (5)	0.0703 (5)	0.0526 (5)	0.0044 (4)	0.0062 (3)	−0.0339 (4)
N4	0.0731 (15)	0.0724 (17)	0.0258 (11)	0.0103 (13)	−0.0114 (10)	−0.0013 (10)
N5	0.0533 (11)	0.0574 (13)	0.0240 (10)	0.0118 (10)	0.0013 (8)	−0.0069 (9)
N6	0.0422 (10)	0.0347 (10)	0.0234 (9)	0.0036 (8)	−0.0032 (7)	−0.0042 (7)
O1	0.0446 (9)	0.0519 (11)	0.0550 (11)	−0.0086 (8)	0.0035 (8)	−0.0199 (9)

C1—C2	1.377 (4)	C12—C13	1.406 (3)
C1—C6	1.379 (4)	C13—C14	1.427 (3)
C1—Cl1	1.740 (2)	C13—C18	1.444 (3)
C2—C3	1.378 (3)	C14—C15	1.355 (4)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.393 (3)	C15—C16	1.411 (4)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.387 (3)	C16—C17	1.344 (4)
C4—C7	1.480 (3)	C16—H16	0.9300
C5—C6	1.374 (3)	C17—C18	1.427 (4)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.383 (3)
C7—O1	1.211 (3)	C19—C20	1.388 (4)
C7—C8	1.511 (3)	C19—H19	0.9300
C8—C11	1.327 (3)	C20—C21	1.424 (3)
C8—N6	1.419 (3)	C20—C25	1.438 (3)
C9—N4	1.314 (3)	C21—C22	1.344 (4)
C9—N6	1.342 (3)	C21—H21	0.9300
C9—H9	0.9300	C22—C23	1.417 (4)
C10—N5	1.310 (3)	C22—H22	0.9300
C10—N4	1.337 (4)	C23—C24	1.355 (4)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.483 (3)	C24—C25	1.419 (3)
C11—H11	0.9300	C24—H24	0.9300
C12—C25	1.406 (3)	N5—N6	1.356 (3)
C2—C1—C6	121.9 (2)	C15—C14—H14	119.2
C2—C1—Cl1	119.53 (19)	C13—C14—H14	119.2
C6—C1—Cl1	118.6 (2)	C14—C15—C16	121.1 (2)
C1—C2—C3	119.0 (2)	C14—C15—H15	119.5
C1—C2—H2	120.5	C16—C15—H15	119.5
C3—C2—H2	120.5	C17—C16—C15	119.8 (2)
C2—C3—C4	120.2 (2)	C17—C16—H16	120.1
C2—C3—H3	119.9	C15—C16—H16	120.1
C4—C3—H3	119.9	C16—C17—C18	121.9 (2)
C5—C4—C3	119.4 (2)	C16—C17—H17	119.0
C5—C4—C7	120.4 (2)	C18—C17—H17	119.0
C3—C4—C7	120.0 (2)	C19—C18—C17	122.1 (2)
C6—C5—C4	120.7 (2)	C19—C18—C13	119.5 (2)
C6—C5—H5	119.7	C17—C18—C13	118.5 (2)
C4—C5—H5	119.7	C18—C19—C20	122.1 (2)
C5—C6—C1	118.8 (2)	C18—C19—H19	118.9
C5—C6—H6	120.6	C20—C19—H19	118.9
C1—C6—H6	120.6	C19—C20—C21	122.6 (2)
O1—C7—C4	122.1 (2)	C19—C20—C25	119.2 (2)
O1—C7—C8	120.4 (2)	C21—C20—C25	118.3 (2)
C4—C7—C8	117.53 (18)	C22—C21—C20	121.8 (2)
C11—C8—N6	120.60 (18)	C22—C21—H21	119.1
C11—C8—C7	123.04 (19)	C20—C21—H21	119.1
N6—C8—C7	116.10 (17)	C21—C22—C23	120.0 (3)
N4—C9—N6	111.1 (2)	C21—C22—H22	120.0
N4—C9—H9	124.5	C23—C22—H22	120.0
N6—C9—H9	124.5	C24—C23—C22	120.5 (3)
N5—C10—N4	116.1 (2)	C24—C23—H23	119.8
N5—C10—H10	121.9	C22—C23—H23	119.8
N4—C10—H10	121.9	C23—C24—C25	121.5 (2)
C8—C11—C12	124.43 (19)	C23—C24—H24	119.3
C8—C11—H11	117.8	C25—C24—H24	119.3
C12—C11—H11	117.8	C12—C25—C24	122.7 (2)
C25—C12—C13	120.81 (19)	C12—C25—C20	119.4 (2)
C25—C12—C11	119.0 (2)	C24—C25—C20	117.9 (2)
C13—C12—C11	120.2 (2)	C9—N4—C10	102.0 (2)
C12—C13—C14	123.8 (2)	C10—N5—N6	102.22 (19)
C12—C13—C18	118.9 (2)	C9—N6—N5	108.56 (19)
C14—C13—C18	117.2 (2)	C9—N6—C8	130.66 (19)
C15—C14—C13	121.5 (2)	N5—N6—C8	120.59 (17)
C6—C1—C2—C3	−0.6 (4)	C14—C13—C18—C19	178.7 (2)
Cl1—C1—C2—C3	178.79 (19)	C12—C13—C18—C17	−179.7 (2)
C1—C2—C3—C4	2.3 (4)	C14—C13—C18—C17	−0.9 (3)
C2—C3—C4—C5	−2.0 (3)	C17—C18—C19—C20	177.7 (2)
C2—C3—C4—C7	−178.6 (2)	C13—C18—C19—C20	−1.9 (3)
C3—C4—C5—C6	0.1 (4)	C18—C19—C20—C21	−178.8 (2)
C7—C4—C5—C6	176.6 (2)	C18—C19—C20—C25	1.0 (3)
C4—C5—C6—C1	1.6 (4)	C19—C20—C21—C22	178.3 (3)
C2—C1—C6—C5	−1.4 (4)	C25—C20—C21—C22	−1.5 (4)
Cl1—C1—C6—C5	179.2 (2)	C20—C21—C22—C23	−0.1 (5)
C5—C4—C7—O1	−138.9 (2)	C21—C22—C23—C24	1.5 (5)
C3—C4—C7—O1	37.7 (3)	C22—C23—C24—C25	−1.2 (5)
C5—C4—C7—C8	41.5 (3)	C13—C12—C25—C24	176.2 (2)
C3—C4—C7—C8	−142.0 (2)	C11—C12—C25—C24	−2.1 (3)
O1—C7—C8—C11	−129.5 (2)	C13—C12—C25—C20	−3.9 (3)
C4—C7—C8—C11	50.1 (3)	C11—C12—C25—C20	177.82 (19)
O1—C7—C8—N6	44.7 (3)	C23—C24—C25—C12	179.6 (2)
C4—C7—C8—N6	−135.7 (2)	C23—C24—C25—C20	−0.4 (4)
N6—C8—C11—C12	−173.0 (2)	C19—C20—C25—C12	1.9 (3)
C7—C8—C11—C12	1.0 (4)	C21—C20—C25—C12	−178.2 (2)
C8—C11—C12—C25	−115.3 (3)	C19—C20—C25—C24	−178.1 (2)
C8—C11—C12—C13	66.4 (3)	C21—C20—C25—C24	1.7 (3)
C25—C12—C13—C14	−175.7 (2)	N6—C9—N4—C10	−0.8 (3)
C11—C12—C13—C14	2.5 (3)	N5—C10—N4—C9	0.4 (4)
C25—C12—C13—C18	3.0 (3)	N4—C10—N5—N6	0.1 (3)
C11—C12—C13—C18	−178.76 (19)	N4—C9—N6—N5	0.9 (3)
C12—C13—C14—C15	178.8 (2)	N4—C9—N6—C8	175.9 (2)
C18—C13—C14—C15	0.1 (3)	C10—N5—N6—C9	−0.6 (3)
C13—C14—C15—C16	0.6 (4)	C10—N5—N6—C8	−176.1 (2)
C14—C15—C16—C17	−0.5 (4)	C11—C8—N6—C9	−162.8 (3)
C15—C16—C17—C18	−0.4 (4)	C7—C8—N6—C9	22.9 (4)
C16—C17—C18—C19	−178.6 (2)	C11—C8—N6—N5	11.6 (3)
C16—C17—C18—C13	1.1 (4)	C7—C8—N6—N5	−162.7 (2)
C12—C13—C18—C19	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O1i	0.93	2.48	3.381 (3)	162