(E)-3-{4-[(7-Chloro­quinolin-4-yl)­oxy]-3-meth­oxy­phenyl}-1-(4-methyl­phenyl)prop-2-en-1-one: a ladder-like structure resulting solely from π–π stacking inter­actions

In the title compound, C₂₆H₂₀ClNO₃, the quinoline fragment is nearly orthogonal to the adjacent aryl ring, while the rest of the mol­ecular skeleton is close to being planar. The crystal structure contains no hydrogen bonds of any sort, but there are two π–π stacking inter­actions present. One, involving the quinoline ring, links mol­ecules related by inversion, while the other, involving the two nonfused aryl rings, links mol­ecules related by translation, so together forming a ladder-type arrangement

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

(E)-3-{4-[(7-Chloroquinolin-4-yl)oxy]-3-methoxyphenyl}-1-(4-methylphenyl)prop-2-en-1-one

Crystal data

C26H20ClNO3	F(000) = 896
Mr = 429.88	Dx = 1.376 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4753 reflections
a = 7.9521 (9) Å	θ = 2.8–27.5°
b = 32.170 (3) Å	µ = 0.21 mm^−1
c = 8.5382 (10) Å	T = 120 K
β = 108.240 (16)°	Block, yellow
V = 2074.5 (4) Å^3	0.39 × 0.32 × 0.19 mm
Z = 4

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	4747 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2666 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.3°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −41→41
Tmin = 0.882, Tmax = 0.960	l = −11→11
24962 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0661P)^2 + 0.7161P] where P = (Fo^2 + 2Fc^2)/3
4747 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.7614 (4)	0.19510 (8)	1.0948 (3)	0.0322 (6)
C2	0.6259 (4)	0.16948 (8)	0.9750 (3)	0.0321 (6)
H2	0.5737	0.1467	1.0132	0.039*
C3	0.5766 (3)	0.17803 (8)	0.8148 (3)	0.0301 (6)
H3	0.6298	0.2019	0.7848	0.036*
O1	0.8280 (3)	0.22494 (6)	1.0457 (2)	0.0408 (5)
C11	0.8162 (3)	0.18483 (8)	1.2727 (3)	0.0285 (6)
C12	0.7683 (4)	0.14875 (9)	1.3371 (3)	0.0348 (7)
H12	0.6924	0.1293	1.2650	0.042*
C13	0.8295 (4)	0.14070 (9)	1.5046 (3)	0.0365 (7)
H13	0.7952	0.1157	1.5458	0.044*
C14	0.9406 (4)	0.16864 (9)	1.6139 (3)	0.0331 (7)
C15	0.9879 (4)	0.20457 (9)	1.5499 (3)	0.0380 (7)
H15	1.0635	0.2241	1.6219	0.046*
C16	0.9268 (4)	0.21254 (9)	1.3829 (3)	0.0372 (7)
H16	0.9611	0.2376	1.3421	0.045*
C17	1.0095 (4)	0.16017 (10)	1.7960 (3)	0.0424 (7)
H17A	1.1387	0.1576	1.8303	0.064*
H17B	0.9580	0.1342	1.8204	0.064*
H17C	0.9767	0.1832	1.8559	0.064*
C31	0.4519 (3)	0.15576 (8)	0.6787 (3)	0.0286 (6)
C32	0.4087 (3)	0.17295 (8)	0.5205 (3)	0.0297 (6)
H32	0.4567	0.1992	0.5060	0.036*
C33	0.2974 (4)	0.15249 (8)	0.3847 (3)	0.0309 (6)
C34	0.2289 (3)	0.11402 (8)	0.4094 (3)	0.0307 (6)
C35	0.2670 (3)	0.09714 (9)	0.5638 (3)	0.0326 (6)
H35	0.2167	0.0712	0.5781	0.039*
C36	0.3782 (3)	0.11762 (8)	0.6986 (3)	0.0316 (6)
H36	0.4044	0.1057	0.8054	0.038*
O33	0.2479 (3)	0.16673 (5)	0.2266 (2)	0.0381 (5)
C37	0.3059 (4)	0.20758 (9)	0.2013 (3)	0.0419 (7)
H37A	0.2695	0.2274	0.2717	0.063*
H37B	0.2528	0.2155	0.0854	0.063*
H37C	0.4352	0.2078	0.2295	0.063*
O34	0.1135 (2)	0.09325 (6)	0.2747 (2)	0.0335 (5)
N41	0.3189 (3)	0.03318 (7)	−0.0597 (3)	0.0303 (5)
C42	0.4223 (3)	0.04635 (8)	0.0840 (3)	0.0301 (6)
H42	0.5456	0.0412	0.1101	0.036*
C43	0.3650 (3)	0.06740 (8)	0.2018 (3)	0.0288 (6)
H43	0.4474	0.0769	0.3019	0.035*
C44	0.1879 (3)	0.07392 (7)	0.1690 (3)	0.0265 (6)
C44a	0.0673 (3)	0.05947 (7)	0.0199 (3)	0.0265 (6)
C45	−0.1180 (3)	0.06409 (8)	−0.0232 (3)	0.0303 (6)
H45	−0.1680	0.0767	0.0526	0.036*
C46	−0.2264 (4)	0.05072 (8)	−0.1722 (3)	0.0324 (6)
H46	−0.3511	0.0539	−0.2000	0.039*
C47	−0.1522 (3)	0.03234 (8)	−0.2837 (3)	0.0291 (6)
Cl47	−0.29032 (9)	0.01742 (2)	−0.47598 (9)	0.0412 (2)
C48	0.0261 (3)	0.02615 (8)	−0.2449 (3)	0.0295 (6)
H48	0.0726	0.0126	−0.3213	0.035*
C48a	0.1414 (3)	0.03969 (7)	−0.0921 (3)	0.0254 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0351 (16)	0.0311 (15)	0.0310 (16)	0.0059 (13)	0.0113 (13)	0.0008 (12)
C2	0.0370 (16)	0.0298 (15)	0.0304 (16)	0.0021 (12)	0.0119 (13)	0.0016 (12)
C3	0.0323 (16)	0.0270 (14)	0.0314 (16)	0.0054 (12)	0.0107 (13)	−0.0010 (12)
O1	0.0522 (13)	0.0331 (11)	0.0363 (12)	−0.0056 (10)	0.0129 (10)	0.0032 (9)
C11	0.0276 (15)	0.0297 (14)	0.0280 (15)	0.0049 (11)	0.0084 (12)	0.0003 (11)
C12	0.0353 (16)	0.0358 (16)	0.0314 (16)	−0.0033 (13)	0.0078 (13)	0.0015 (12)
C13	0.0409 (17)	0.0357 (16)	0.0334 (17)	0.0011 (13)	0.0125 (14)	0.0073 (13)
C14	0.0300 (16)	0.0413 (17)	0.0294 (15)	0.0068 (13)	0.0114 (12)	−0.0004 (13)
C15	0.0410 (17)	0.0398 (17)	0.0314 (17)	−0.0060 (14)	0.0089 (13)	−0.0068 (13)
C16	0.0415 (17)	0.0362 (16)	0.0338 (17)	−0.0048 (13)	0.0117 (14)	−0.0021 (13)
C17	0.0426 (18)	0.054 (2)	0.0294 (16)	0.0034 (15)	0.0098 (14)	0.0034 (14)
C31	0.0285 (15)	0.0295 (14)	0.0279 (15)	0.0058 (12)	0.0091 (12)	−0.0017 (11)
C32	0.0322 (16)	0.0266 (14)	0.0294 (15)	0.0014 (12)	0.0085 (12)	−0.0017 (11)
C33	0.0363 (16)	0.0311 (15)	0.0268 (15)	0.0076 (12)	0.0120 (13)	0.0024 (11)
C34	0.0279 (15)	0.0323 (15)	0.0319 (16)	0.0019 (12)	0.0093 (12)	−0.0083 (12)
C35	0.0329 (16)	0.0327 (15)	0.0345 (16)	−0.0009 (12)	0.0139 (13)	−0.0032 (12)
C36	0.0357 (16)	0.0318 (15)	0.0293 (15)	0.0058 (12)	0.0130 (13)	0.0031 (12)
O33	0.0508 (12)	0.0336 (11)	0.0262 (11)	−0.0004 (9)	0.0066 (9)	0.0003 (8)
C37	0.055 (2)	0.0376 (17)	0.0304 (17)	0.0059 (15)	0.0086 (14)	0.0036 (13)
O34	0.0294 (10)	0.0393 (11)	0.0332 (11)	−0.0021 (8)	0.0118 (9)	−0.0110 (9)
N41	0.0257 (13)	0.0328 (12)	0.0327 (13)	0.0017 (10)	0.0095 (10)	−0.0012 (10)
C42	0.0214 (14)	0.0346 (15)	0.0331 (16)	0.0018 (12)	0.0066 (12)	−0.0001 (12)
C43	0.0258 (15)	0.0311 (15)	0.0272 (15)	−0.0013 (11)	0.0050 (12)	−0.0015 (11)
C44	0.0298 (15)	0.0236 (13)	0.0285 (15)	0.0005 (11)	0.0127 (12)	0.0003 (11)
C44a	0.0280 (15)	0.0252 (14)	0.0275 (14)	0.0020 (11)	0.0103 (12)	0.0021 (11)
C45	0.0273 (15)	0.0301 (15)	0.0355 (16)	0.0007 (12)	0.0126 (12)	−0.0005 (12)
C46	0.0243 (15)	0.0335 (15)	0.0368 (17)	0.0034 (12)	0.0057 (13)	0.0020 (12)
C47	0.0264 (15)	0.0292 (14)	0.0268 (15)	−0.0025 (11)	0.0014 (12)	0.0023 (11)
Cl47	0.0353 (4)	0.0456 (4)	0.0351 (4)	−0.0030 (3)	0.0000 (3)	−0.0028 (3)
C48	0.0305 (16)	0.0309 (15)	0.0291 (15)	0.0011 (12)	0.0124 (12)	0.0018 (11)
C48a	0.0245 (14)	0.0236 (13)	0.0295 (15)	−0.0003 (11)	0.0106 (12)	0.0051 (11)

Geometric parameters (Å, º)

C1—O1	1.231 (3)	C34—C35	1.369 (4)
C1—C11	1.481 (4)	C34—O34	1.397 (3)
C1—C2	1.482 (4)	C35—C36	1.380 (4)
C2—C3	1.328 (3)	C35—H35	0.9500
C2—H2	0.9500	C36—H36	0.9500
C3—C31	1.458 (4)	O33—C37	1.431 (3)
C3—H3	0.9500	C37—H37A	0.9800
C11—C12	1.387 (4)	C37—H37B	0.9800
C11—C16	1.391 (4)	C37—H37C	0.9800
C12—C13	1.383 (4)	O34—C44	1.373 (3)
C12—H12	0.9500	N41—C42	1.315 (3)
C13—C14	1.394 (4)	N41—C48a	1.367 (3)
C13—H13	0.9500	C42—C43	1.402 (4)
C14—C15	1.380 (4)	C42—H42	0.9500
C14—C17	1.503 (4)	C43—C44	1.363 (3)
C15—C16	1.379 (4)	C43—H43	0.9500
C15—H15	0.9500	C44—C44a	1.412 (3)
C16—H16	0.9500	C44a—C45	1.411 (4)
C17—H17A	0.9800	C44a—C48a	1.420 (3)
C17—H17B	0.9800	C45—C46	1.364 (4)
C17—H17C	0.9800	C45—H45	0.9500
C31—C36	1.393 (4)	C46—C47	1.398 (4)
C31—C32	1.399 (3)	C46—H46	0.9500
C32—C33	1.385 (4)	C47—C48	1.366 (4)
C32—H32	0.9500	C47—Cl47	1.733 (3)
C33—O33	1.362 (3)	C48—C48a	1.408 (4)
C33—C34	1.395 (4)	C48—H48	0.9500
O1—C1—C11	120.2 (2)	O34—C34—C33	119.2 (2)
O1—C1—C2	119.7 (2)	C34—C35—C36	120.3 (3)
C11—C1—C2	120.1 (2)	C34—C35—H35	119.8
C3—C2—C1	120.8 (3)	C36—C35—H35	119.8
C3—C2—H2	119.6	C35—C36—C31	120.2 (3)
C1—C2—H2	119.6	C35—C36—H36	119.9
C2—C3—C31	128.8 (3)	C31—C36—H36	119.9
C2—C3—H3	115.6	O33—C37—H37A	109.5
C31—C3—H3	115.6	O33—C37—H37B	109.5
C12—C11—C16	117.5 (2)	H37A—C37—H37B	109.5
C12—C11—C1	124.3 (2)	O33—C37—H37C	109.5
C16—C11—C1	118.1 (2)	H37A—C37—H37C	109.5
C13—C12—C11	121.0 (3)	H37B—C37—H37C	109.5
C13—C12—H12	119.5	C42—N41—C48a	116.3 (2)
C11—C12—H12	119.5	N41—C42—C43	125.2 (2)
C12—C13—C14	121.0 (3)	N41—C42—H42	117.4
C12—C13—H13	119.5	C43—C42—H42	117.4
C14—C13—H13	119.5	C44—C43—C42	118.3 (2)
C15—C14—C13	118.0 (3)	C44—C43—H43	120.9
C15—C14—C17	120.3 (3)	C42—C43—H43	120.9
C13—C14—C17	121.7 (3)	O34—C44—C43	124.4 (2)
C16—C15—C14	120.9 (3)	C43—C44—C44a	120.1 (2)
C16—C15—H15	119.5	O34—C44—C44a	115.5 (2)
C14—C15—H15	119.5	C33—O33—C37	116.8 (2)
C15—C16—C11	121.6 (3)	C34—O34—C44	116.79 (19)
C15—C16—H16	119.2	C45—C44a—C44	124.0 (2)
C11—C16—H16	119.2	C45—C44a—C48a	119.4 (2)
C14—C17—H17A	109.5	C44—C44a—C48a	116.5 (2)
C14—C17—H17B	109.5	C46—C45—C44a	120.9 (2)
H17A—C17—H17B	109.5	C46—C45—H45	119.5
C14—C17—H17C	109.5	C44a—C45—H45	119.5
H17A—C17—H17C	109.5	C45—C46—C47	119.4 (2)
H17B—C17—H17C	109.5	C45—C46—H46	120.3
C36—C31—C32	118.7 (2)	C47—C46—H46	120.3
C36—C31—C3	122.8 (2)	C48—C47—C46	121.6 (2)
C32—C31—C3	118.4 (2)	C48—C47—Cl47	119.5 (2)
C33—C32—C31	121.3 (3)	C46—C47—Cl47	119.0 (2)
C33—C32—H32	119.3	C47—C48—C48a	120.3 (2)
C31—C32—H32	119.3	C47—C48—H48	119.8
O33—C33—C32	125.5 (2)	C48a—C48—H48	119.8
O33—C33—C34	116.3 (2)	N41—C48a—C48	118.1 (2)
C32—C33—C34	118.2 (2)	N41—C48a—C44a	123.5 (2)
C35—C34—C33	121.2 (2)	C48—C48a—C44a	118.4 (2)
O34—C34—C35	119.6 (2)
O1—C1—C2—C3	0.7 (4)	C3—C31—C36—C35	−177.1 (2)
C12—C11—C1—C2	9.7 (4)	C32—C33—O33—C37	−4.8 (4)
C11—C1—C2—C3	−179.3 (2)	C34—C33—O33—C37	175.2 (2)
C1—C2—C3—C31	177.4 (2)	C35—C34—O34—C44	−106.4 (3)
O1—C1—C11—C12	−170.4 (3)	C33—C34—O34—C44	76.2 (3)
O1—C1—C11—C16	7.8 (4)	C48a—N41—C42—C43	−2.2 (4)
C2—C1—C11—C16	−172.1 (2)	N41—C42—C43—C44	2.1 (4)
C16—C11—C12—C13	−0.3 (4)	C42—C43—C44—O34	178.5 (2)
C1—C11—C12—C13	177.9 (2)	C42—C43—C44—C44a	0.3 (4)
C11—C12—C13—C14	0.2 (4)	C34—O34—C44—C43	12.3 (4)
C12—C13—C14—C15	0.0 (4)	C34—O34—C44—C44a	−169.4 (2)
C12—C13—C14—C17	−179.4 (3)	C43—C44—C44a—C45	178.7 (2)
C13—C14—C15—C16	0.0 (4)	O34—C44—C44a—C45	0.3 (4)
C17—C14—C15—C16	179.4 (2)	C43—C44—C44a—C48a	−2.1 (4)
C14—C15—C16—C11	−0.2 (4)	O34—C44—C44a—C48a	179.5 (2)
C12—C11—C16—C15	0.3 (4)	C44—C44a—C45—C46	177.6 (2)
C1—C11—C16—C15	−178.0 (2)	C48a—C44a—C45—C46	−1.6 (4)
C2—C3—C31—C36	−7.7 (4)	C44a—C45—C46—C47	−0.3 (4)
C2—C3—C31—C32	174.2 (3)	C45—C46—C47—C48	2.3 (4)
C36—C31—C32—C33	−1.1 (4)	C45—C46—C47—Cl47	−177.4 (2)
C3—C31—C32—C33	177.1 (2)	C46—C47—C48—C48a	−2.4 (4)
C31—C32—C33—O33	180.0 (2)	Cl47—C47—C48—C48a	177.23 (19)
C31—C32—C33—C34	0.0 (4)	C42—N41—C48a—C48	179.8 (2)
O33—C33—C34—C35	−178.7 (2)	C42—N41—C48a—C44a	0.1 (4)
C32—C33—C34—C35	1.3 (4)	C47—C48—C48a—N41	−179.3 (2)
O33—C33—C34—O34	−1.3 (3)	C47—C48—C48a—C44a	0.5 (4)
C32—C33—C34—O34	178.7 (2)	C45—C44a—C48a—N41	−178.8 (2)
C33—C34—C35—C36	−1.4 (4)	C44—C44a—C48a—N41	2.0 (4)
O34—C34—C35—C36	−178.8 (2)	C45—C44a—C48a—C48	1.4 (4)
C34—C35—C36—C31	0.2 (4)	C44—C44a—C48a—C48	−177.8 (2)
C32—C31—C36—C35	1.0 (4)