1,3-Bis(4-chloro-phen-yl)-1-methyl-1H-benzo[f]chromene.

The title compound, C(26)H(18)Cl(2)O, is a heterocyclic structure consisting of a benzo[f]chromene ring and two aromatic rings. The non-H atoms of the benzo[f]chromene ring are almost coplanar (rms deviation = 0.107 Å), and the methyl C atom lies 1.340 (4) Å from the mean plane of the benzo[f]chromene ring. The chromene ring forms dihedral angles of 88.45 (2)° with the benzene ring linked to the quaternary C atom and 50.74 (3)° with the benzene ring linked to the 3-position, while the dihedral angle between the two benzene rings is 67.58 (3)°.

Related literature

For the construction of a 4H-chromene scaffold, see: Shi & Shi (2007 ▶); Zeni & Larrock (2004 ▶). For the biological and pharmacological activity of 4H-chromene derivatives, see: Kidwai et al. (2005 ▶). For 4H-chromene derivatives possessing a tertiary carbon in the scaffold, see: Liu et al. (2010 ▶); Wang & Zhu (2010 ▶). For iron trichloride-catalysed synthesis of 4H-chromenes, see: Kozlikovskii et al. (1986 ▶).

Experimental

Crystal data

C26H18Cl2O

M = 417.33

Triclinic,

a = 8.9554 (6) Å

b = 9.4439 (6) Å

c = 12.3206 (7) Å

α = 93.511 (2)°

β = 102.0453 (15)°

γ = 94.287 (2)°

V = 1013.05 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 296 K

0.42 × 0.37 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.874, T max = 0.910

10050 measured reflections

4596 independent reflections

2783 reflections with F 2 > 2σ(F 2)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.095

S = 1.00

4596 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.33 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022610/zq2041sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022610/zq2041Isup2.hkl

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

C26H18Cl2O	Z = 2
Mr = 417.33	F(000) = 432.00
Triclinic, P1	Dx = 1.368 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 8.9554 (6) Å	Cell parameters from 6736 reflections
b = 9.4439 (6) Å	θ = 3.0–27.4°
c = 12.3206 (7) Å	µ = 0.34 mm−1
α = 93.511 (2)°	T = 296 K
β = 102.0453 (15)°	Chunk, colorless
γ = 94.287 (2)°	0.42 × 0.37 × 0.28 mm
V = 1013.05 (11) Å3

Rigaku R-AXIS RAPID diffractometer	2783 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.021
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.874, Tmax = 0.910	k = −12→12
10050 measured reflections	l = −15→14
4596 independent reflections

Refinement on F2	w = 1/[σ2(Fo2) + (0.001P)2 + 0.920P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.042	(Δ/σ)max < 0.001
wR(F2) = 0.095	Δρmax = 0.28 e Å−3
S = 1.00	Δρmin = −0.33 e Å−3
4596 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008)
264 parameters	Extinction coefficient: 0.0188 (6)
H-atom parameters constrained

Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
Cl1	0.25919 (11)	−0.05748 (9)	0.82025 (6)	0.0899 (3)
Cl2	0.54898 (11)	0.29006 (9)	−0.01095 (6)	0.0875 (2)
O1	0.27277 (19)	0.50754 (14)	0.53308 (12)	0.0492 (4)
C1	0.1329 (2)	0.4692 (2)	0.29332 (18)	0.0405 (5)
C2	0.2049 (2)	0.6121 (2)	0.35548 (17)	0.0380 (4)
C3	0.2145 (2)	0.7416 (2)	0.29947 (18)	0.0406 (5)
C4	0.1688 (2)	0.7468 (2)	0.1828 (2)	0.0521 (6)
C5	0.1790 (3)	0.8718 (2)	0.1324 (2)	0.0614 (7)
C6	0.2364 (3)	0.9992 (2)	0.1961 (2)	0.0635 (7)
C7	0.2840 (2)	0.9991 (2)	0.3080 (2)	0.0543 (6)
C8	0.2758 (2)	0.8720 (2)	0.3627 (2)	0.0430 (5)
C9	0.3277 (2)	0.8730 (2)	0.4787 (2)	0.0473 (5)
C10	0.3245 (2)	0.7510 (2)	0.53063 (19)	0.0465 (5)
C11	0.2644 (2)	0.6220 (2)	0.46756 (18)	0.0403 (4)
C12	0.2041 (2)	0.3771 (2)	0.48333 (18)	0.0406 (5)
C13	0.1397 (2)	0.3577 (2)	0.37734 (19)	0.0431 (5)
C14	0.2173 (2)	0.2685 (2)	0.56609 (18)	0.0401 (4)
C15	0.0923 (2)	0.1769 (2)	0.5723 (2)	0.0542 (6)
C16	0.1045 (2)	0.0765 (2)	0.6511 (2)	0.0609 (7)
C17	0.2428 (3)	0.0687 (2)	0.7219 (2)	0.0532 (6)
C18	0.3693 (2)	0.1574 (2)	0.7168 (2)	0.0538 (6)
C19	0.3551 (2)	0.2575 (2)	0.63937 (19)	0.0483 (5)
C20	0.2310 (2)	0.4205 (2)	0.21085 (17)	0.0419 (5)
C21	0.1736 (3)	0.3746 (2)	0.09965 (19)	0.0542 (6)
C22	0.2691 (3)	0.3322 (2)	0.0309 (2)	0.0618 (7)
C23	0.4242 (3)	0.3367 (2)	0.0735 (2)	0.0571 (6)
C24	0.4842 (2)	0.3788 (2)	0.1839 (2)	0.0547 (6)
C25	0.3879 (2)	0.4192 (2)	0.25085 (19)	0.0475 (5)
C26	−0.0378 (2)	0.4756 (2)	0.2390 (2)	0.0551 (6)
H4	0.1309	0.6630	0.1389	0.063*
H5	0.1474	0.8717	0.0556	0.074*
H6	0.2420	1.0839	0.1619	0.076*
H7	0.3229	1.0842	0.3498	0.065*
H9	0.3648	0.9586	0.5202	0.057*
H10	0.3615	0.7523	0.6071	0.056*
H13	0.0939	0.2670	0.3510	0.052*
H15	−0.0010	0.1823	0.5234	0.065*
H16	0.0198	0.0156	0.6555	0.073*
H18	0.4629	0.1501	0.7649	0.065*
H19	0.4400	0.3190	0.6363	0.058*
H21	0.0688	0.3724	0.0707	0.065*
H22	0.2287	0.3010	−0.0432	0.074*
H24	0.5889	0.3798	0.2127	0.066*
H25	0.4289	0.4468	0.3256	0.057*
H261	−0.0469	0.5428	0.1831	0.066*
H262	−0.0806	0.3831	0.2052	0.066*
H263	−0.0921	0.5047	0.2948	0.066*

	U11	U22	U33	U12	U13	U23
Cl1	0.1224 (7)	0.0753 (5)	0.0833 (5)	0.0203 (4)	0.0317 (5)	0.0476 (4)
Cl2	0.1234 (7)	0.0946 (6)	0.0600 (4)	0.0380 (5)	0.0429 (4)	0.0140 (4)
O1	0.0640 (10)	0.0346 (8)	0.0440 (8)	−0.0043 (7)	0.0019 (7)	0.0087 (6)
C1	0.0442 (12)	0.0305 (10)	0.0439 (11)	0.0003 (9)	0.0033 (9)	0.0046 (8)
C2	0.0383 (11)	0.0323 (11)	0.0446 (11)	0.0043 (9)	0.0101 (9)	0.0065 (9)
C3	0.0414 (11)	0.0340 (11)	0.0490 (12)	0.0066 (9)	0.0127 (10)	0.0096 (9)
C4	0.0627 (15)	0.0421 (13)	0.0529 (14)	0.0086 (11)	0.0117 (12)	0.0126 (10)
C5	0.0797 (19)	0.0519 (15)	0.0579 (15)	0.0144 (13)	0.0186 (14)	0.0216 (12)
C6	0.0733 (18)	0.0409 (14)	0.085 (2)	0.0116 (13)	0.0274 (15)	0.0283 (13)
C7	0.0544 (14)	0.0338 (12)	0.0771 (18)	0.0028 (10)	0.0179 (13)	0.0117 (11)
C8	0.0401 (11)	0.0315 (11)	0.0598 (14)	0.0037 (9)	0.0150 (10)	0.0062 (9)
C9	0.0452 (13)	0.0346 (11)	0.0615 (14)	−0.0016 (9)	0.0131 (11)	−0.0011 (10)
C10	0.0487 (13)	0.0407 (12)	0.0469 (12)	−0.0022 (10)	0.0058 (10)	−0.0006 (10)
C11	0.0410 (11)	0.0336 (11)	0.0466 (12)	0.0017 (9)	0.0095 (10)	0.0083 (9)
C12	0.0391 (11)	0.0332 (11)	0.0493 (12)	0.0003 (9)	0.0083 (10)	0.0086 (9)
C13	0.0465 (12)	0.0311 (11)	0.0502 (13)	−0.0014 (9)	0.0075 (10)	0.0070 (9)
C14	0.0425 (12)	0.0356 (11)	0.0448 (11)	0.0046 (9)	0.0135 (10)	0.0080 (9)
C15	0.0407 (13)	0.0519 (14)	0.0718 (16)	0.0053 (11)	0.0108 (12)	0.0225 (12)
C16	0.0542 (15)	0.0499 (15)	0.0861 (19)	0.0028 (11)	0.0262 (14)	0.0271 (13)
C17	0.0697 (17)	0.0452 (13)	0.0521 (14)	0.0150 (12)	0.0220 (13)	0.0196 (11)
C18	0.0573 (15)	0.0542 (15)	0.0485 (13)	0.0079 (12)	0.0046 (11)	0.0126 (11)
C19	0.0467 (13)	0.0471 (13)	0.0496 (13)	−0.0023 (10)	0.0076 (11)	0.0084 (10)
C20	0.0541 (13)	0.0300 (10)	0.0390 (11)	0.0037 (9)	0.0031 (10)	0.0066 (8)
C21	0.0660 (16)	0.0473 (14)	0.0425 (12)	0.0097 (12)	−0.0054 (11)	0.0039 (10)
C22	0.093 (2)	0.0555 (16)	0.0343 (12)	0.0178 (14)	0.0038 (13)	0.0045 (10)
C23	0.087 (2)	0.0459 (14)	0.0441 (13)	0.0187 (13)	0.0209 (13)	0.0105 (10)
C24	0.0596 (15)	0.0562 (15)	0.0498 (14)	0.0118 (12)	0.0125 (12)	0.0057 (11)
C25	0.0542 (14)	0.0457 (13)	0.0403 (11)	0.0046 (11)	0.0058 (10)	0.0004 (9)
C26	0.0474 (14)	0.0512 (14)	0.0624 (15)	0.0012 (11)	0.0015 (11)	0.0098 (11)

Cl1—C17	1.743 (2)	C18—C19	1.378 (3)
Cl2—C23	1.740 (3)	C20—C21	1.389 (2)
O1—C11	1.385 (2)	C20—C25	1.389 (3)
O1—C12	1.381 (2)	C21—C22	1.386 (4)
C1—C2	1.536 (2)	C22—C23	1.375 (4)
C1—C13	1.517 (3)	C23—C24	1.375 (3)
C1—C20	1.547 (3)	C24—C25	1.371 (3)
C1—C26	1.542 (3)	C4—H4	0.930
C2—C3	1.446 (3)	C5—H5	0.930
C2—C11	1.367 (2)	C6—H6	0.930
C3—C4	1.415 (3)	C7—H7	0.930
C3—C8	1.424 (2)	C9—H9	0.930
C4—C5	1.373 (3)	C10—H10	0.930
C5—C6	1.397 (3)	C13—H13	0.930
C6—C7	1.356 (4)	C15—H15	0.930
C7—C8	1.416 (3)	C16—H16	0.930
C8—C9	1.407 (3)	C18—H18	0.930
C9—C10	1.353 (3)	C19—H19	0.930
C10—C11	1.411 (2)	C21—H21	0.930
C12—C13	1.308 (2)	C22—H22	0.930
C12—C14	1.484 (3)	C24—H24	0.930
C14—C15	1.381 (3)	C25—H25	0.930
C14—C19	1.383 (2)	C26—H261	0.960
C15—C16	1.391 (3)	C26—H262	0.960
C16—C17	1.368 (3)	C26—H263	0.960
C17—C18	1.372 (3)
C11—O1—C12	117.40 (15)	C21—C22—C23	119.3 (2)
C2—C1—C13	108.24 (16)	Cl2—C23—C22	120.80 (18)
C2—C1—C20	109.59 (17)	Cl2—C23—C24	118.6 (2)
C2—C1—C26	111.80 (18)	C22—C23—C24	120.6 (2)
C13—C1—C20	106.20 (17)	C23—C24—C25	119.3 (2)
C13—C1—C26	106.86 (18)	C20—C25—C24	122.2 (2)
C20—C1—C26	113.82 (17)	C3—C4—H4	119.0
C1—C2—C3	122.33 (17)	C5—C4—H4	119.0
C1—C2—C11	120.91 (18)	C4—C5—H5	119.8
C3—C2—C11	116.76 (17)	C6—C5—H5	119.8
C2—C3—C4	123.51 (18)	C5—C6—H6	120.1
C2—C3—C8	119.56 (19)	C7—C6—H6	120.1
C4—C3—C8	116.9 (2)	C6—C7—H7	119.3
C3—C4—C5	121.9 (2)	C8—C7—H7	119.3
C4—C5—C6	120.3 (2)	C8—C9—H9	119.5
C5—C6—C7	119.8 (2)	C10—C9—H9	119.5
C6—C7—C8	121.4 (2)	C9—C10—H10	120.4
C3—C8—C7	119.6 (2)	C11—C10—H10	120.4
C3—C8—C9	119.6 (2)	C1—C13—H13	116.9
C7—C8—C9	120.82 (19)	C12—C13—H13	116.9
C8—C9—C10	120.91 (19)	C14—C15—H15	119.6
C9—C10—C11	119.3 (2)	C16—C15—H15	119.6
O1—C11—C2	124.47 (17)	C15—C16—H16	120.5
O1—C11—C10	111.76 (17)	C17—C16—H16	120.5
C2—C11—C10	123.8 (2)	C17—C18—H18	120.6
O1—C12—C13	122.56 (19)	C19—C18—H18	120.6
O1—C12—C14	110.38 (16)	C14—C19—H19	119.3
C13—C12—C14	127.05 (18)	C18—C19—H19	119.3
C1—C13—C12	126.12 (19)	C20—C21—H21	119.3
C12—C14—C15	120.82 (19)	C22—C21—H21	119.3
C12—C14—C19	120.67 (19)	C21—C22—H22	120.4
C15—C14—C19	118.5 (2)	C23—C22—H22	120.4
C14—C15—C16	120.7 (2)	C23—C24—H24	120.4
C15—C16—C17	119.1 (2)	C25—C24—H24	120.4
Cl1—C17—C16	119.3 (2)	C20—C25—H25	118.9
Cl1—C17—C18	119.22 (18)	C24—C25—H25	118.9
C16—C17—C18	121.5 (2)	C1—C26—H261	109.5
C17—C18—C19	118.9 (2)	C1—C26—H262	109.5
C14—C19—C18	121.4 (2)	C1—C26—H263	109.5
C1—C20—C21	124.8 (2)	H261—C26—H262	109.5
C1—C20—C25	118.00 (17)	H261—C26—H263	109.5
C21—C20—C25	117.2 (2)	H262—C26—H263	109.5
C20—C21—C22	121.4 (2)
C11—O1—C12—C13	3.5 (3)	C5—C6—C7—C8	−0.5 (4)
C11—O1—C12—C14	−177.32 (19)	C6—C7—C8—C3	−0.9 (3)
C12—O1—C11—C2	−6.0 (3)	C6—C7—C8—C9	179.0 (2)
C12—O1—C11—C10	173.84 (19)	C3—C8—C9—C10	2.0 (3)
C2—C1—C13—C12	−3.8 (3)	C7—C8—C9—C10	−177.9 (2)
C13—C1—C2—C3	−179.1 (2)	C8—C9—C10—C11	−1.7 (3)
C13—C1—C2—C11	1.3 (2)	C9—C10—C11—O1	178.7 (2)
C2—C1—C20—C21	−131.0 (2)	C9—C10—C11—C2	−1.5 (3)
C2—C1—C20—C25	50.4 (2)	O1—C12—C13—C1	1.6 (3)
C20—C1—C2—C3	65.5 (2)	O1—C12—C14—C15	133.8 (2)
C20—C1—C2—C11	−114.1 (2)	O1—C12—C14—C19	−45.6 (2)
C26—C1—C2—C3	−61.6 (2)	C13—C12—C14—C15	−47.0 (3)
C26—C1—C2—C11	118.8 (2)	C13—C12—C14—C19	133.5 (2)
C13—C1—C20—C21	112.3 (2)	C14—C12—C13—C1	−177.5 (2)
C13—C1—C20—C25	−66.3 (2)	C12—C14—C15—C16	−179.0 (2)
C20—C1—C13—C12	113.8 (2)	C12—C14—C19—C18	179.9 (2)
C26—C1—C13—C12	−124.4 (2)	C15—C14—C19—C18	0.4 (3)
C26—C1—C20—C21	−5.0 (3)	C19—C14—C15—C16	0.4 (3)
C26—C1—C20—C25	176.4 (2)	C14—C15—C16—C17	−0.6 (4)
C1—C2—C3—C4	−4.6 (3)	C15—C16—C17—Cl1	−179.6 (2)
C1—C2—C3—C8	176.9 (2)	C15—C16—C17—C18	−0.0 (3)
C1—C2—C11—O1	3.4 (3)	Cl1—C17—C18—C19	−179.58 (19)
C1—C2—C11—C10	−176.4 (2)	C16—C17—C18—C19	0.8 (3)
C3—C2—C11—O1	−176.2 (2)	C17—C18—C19—C14	−1.0 (3)
C3—C2—C11—C10	4.0 (3)	C1—C20—C21—C22	−179.8 (2)
C11—C2—C3—C4	175.1 (2)	C1—C20—C25—C24	−179.5 (2)
C11—C2—C3—C8	−3.4 (3)	C21—C20—C25—C24	1.8 (3)
C2—C3—C4—C5	179.8 (2)	C25—C20—C21—C22	−1.2 (3)
C2—C3—C8—C7	−179.5 (2)	C20—C21—C22—C23	−0.6 (3)
C2—C3—C8—C9	0.6 (3)	C21—C22—C23—Cl2	−177.82 (19)
C4—C3—C8—C7	1.9 (3)	C21—C22—C23—C24	1.9 (3)
C4—C3—C8—C9	−178.0 (2)	Cl2—C23—C24—C25	178.40 (19)
C8—C3—C4—C5	−1.7 (3)	C22—C23—C24—C25	−1.3 (3)
C3—C4—C5—C6	0.4 (4)	C23—C24—C25—C20	−0.6 (3)
C4—C5—C6—C7	0.7 (4)