2,3-Bis(2-chloro-benz-yl)naphthalene-1,4-dione.

The title disubstituted naphthalene-1,4-dione, C(24)H(16)Cl(2)O(2), has the two chloro-benzyl substituents related by a non-crystallographic twofold rotation axis, generating a chiral conformation; both enantiomers are present. The two chlorobenzene rings are nearly perpendicular to the fused ring system, making angles of 88.8 (1) and 77.5 (1)° with it.

Related literature

2,3-Bis(2-chloro­benz­yl)naphthalene-1,4-dione was the unexpected product in the attempted synthesis of 2-(2-chloro­benz­yl)naphthalene-1,4-dione by a free-radical alkyl­ation (see Boehm et al., 1981 ▶; Chen et al., 2005 ▶; Tsai et al., 2001 ▶). Although the title dichloro compound has not been reported, 2,3-dibenzyl­naphthalene-1,4-dione has been known for a long time (Baxter & Sanders, 1974 ▶; Chen et al., 2005 ▶; Oettmeier et al., 1986 ▶; Sharma & Torssell, 1978 ▶; Yamago et al., 2002 ▶). This class of compounds exhibits anti­tumour activity (Driscoll, 1974 ▶; Driscoll et al., 1974 ▶).

Experimental

Crystal data

C24H16Cl2O2

M = 407.27

Monoclinic,

a = 9.998 (1) Å

b = 10.272 (1) Å

c = 18.804 (2) Å

β = 99.071 (1)°

V = 1907.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 295 (2) K

0.5 × 0.5 × 0.5 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: none

12440 measured reflections

4366 independent reflections

2921 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.131

S = 1.02

4366 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068006/ob2105sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068006/ob2105Isup2.hkl

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

C24H16Cl2O2	F000 = 840
Mr = 407.27	Dx = 1.418 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6278 reflections
a = 9.998 (1) Å	θ = 2.2–27.5º
b = 10.272 (1) Å	µ = 0.36 mm−1
c = 18.804 (2) Å	T = 295 (2) K
β = 99.071 (1)º	Block, yellow
V = 1907.1 (3) Å3	0.5 × 0.5 × 0.5 mm
Z = 4

Bruker SMART area-detector diffractometer	2921 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	Rint = 0.035
Monochromator: graphite	θmax = 27.5º
T = 295(2) K	θmin = 2.2º
φ and ω scans	h = −12→12
Absorption correction: none	k = −13→13
12440 measured reflections	l = −24→11
4366 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0628P)2 + 0.3578P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4366 reflections	Δρmax = 0.18 e Å−3
253 parameters	Δρmin = −0.42 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
Cl1	0.53007 (6)	0.55702 (6)	0.66580 (4)	0.0779 (2)
Cl2	−0.07641 (7)	0.55387 (6)	0.39047 (4)	0.0856 (2)
O1	0.48173 (15)	1.00324 (15)	0.60292 (8)	0.0693 (4)
O2	0.03492 (16)	1.00716 (16)	0.40921 (9)	0.0763 (5)
C1	0.39509 (19)	0.64277 (17)	0.69086 (10)	0.0508 (5)
C2	0.3610 (3)	0.6185 (2)	0.75798 (11)	0.0707 (7)
H2	0.4108	0.5589	0.7887	0.085*
C3	0.2548 (3)	0.6819 (2)	0.77899 (13)	0.0821 (8)
H3	0.2317	0.6658	0.8242	0.099*
C4	0.1817 (3)	0.7694 (2)	0.73391 (13)	0.0743 (7)
H4	0.1081	0.8118	0.7481	0.089*
C5	0.2169 (2)	0.79478 (19)	0.66737 (10)	0.0550 (5)
H5	0.1667	0.8550	0.6373	0.066*
C6	0.32481 (18)	0.73306 (16)	0.64433 (9)	0.0438 (4)
C7	0.3679 (2)	0.76083 (18)	0.57207 (10)	0.0524 (5)
H7A	0.4658	0.7688	0.5789	0.063*
H7B	0.3431	0.6871	0.5405	0.063*
C8	0.30674 (17)	0.88202 (17)	0.53547 (9)	0.0426 (4)
C9	0.37930 (17)	1.00544 (18)	0.55815 (9)	0.0438 (4)
C10	0.32835 (17)	1.12940 (16)	0.52474 (9)	0.0422 (4)
C11	0.39225 (19)	1.24608 (19)	0.54606 (11)	0.0555 (5)
H11	0.4650	1.2469	0.5836	0.067*
C12	0.3487 (2)	1.3603 (2)	0.51213 (14)	0.0698 (6)
H12	0.3920	1.4382	0.5266	0.084*
C13	0.2408 (2)	1.3596 (2)	0.45657 (15)	0.0745 (7)
H13	0.2131	1.4368	0.4330	0.089*
C14	0.1739 (2)	1.2458 (2)	0.43582 (12)	0.0618 (5)
H14	0.1002	1.2465	0.3988	0.074*
C15	0.21608 (18)	1.12966 (17)	0.47002 (9)	0.0447 (4)
C16	0.14175 (18)	1.00724 (18)	0.45086 (9)	0.0476 (4)
C17	0.19512 (18)	0.88289 (17)	0.48466 (9)	0.0443 (4)
C18	0.1139 (2)	0.76407 (19)	0.45892 (11)	0.0566 (5)
H18A	0.0185	0.7835	0.4574	0.068*
H18B	0.1372	0.6946	0.4936	0.068*
C19	0.13550 (17)	0.71606 (17)	0.38532 (10)	0.0466 (4)
C20	0.23605 (19)	0.76496 (19)	0.35008 (10)	0.0542 (5)
H20	0.2938	0.8290	0.3724	0.065*
C21	0.2529 (2)	0.7209 (2)	0.28236 (12)	0.0675 (6)
H21	0.3211	0.7555	0.2597	0.081*
C22	0.1689 (3)	0.6263 (3)	0.24877 (13)	0.0762 (7)
H22	0.1804	0.5965	0.2034	0.091*
C23	0.0682 (2)	0.5759 (2)	0.28197 (13)	0.0694 (6)
H23	0.0108	0.5121	0.2592	0.083*
C24	0.05248 (19)	0.62039 (18)	0.34967 (11)	0.0553 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0746 (4)	0.0631 (4)	0.0901 (5)	0.0227 (3)	−0.0056 (3)	0.0124 (3)
Cl2	0.0785 (4)	0.0736 (4)	0.1006 (5)	−0.0274 (3)	0.0012 (3)	0.0022 (3)
O1	0.0628 (9)	0.0722 (10)	0.0629 (9)	0.0011 (7)	−0.0211 (7)	0.0104 (7)
O2	0.0696 (9)	0.0745 (10)	0.0715 (10)	0.0136 (8)	−0.0305 (8)	−0.0104 (8)
C1	0.0583 (11)	0.0404 (9)	0.0490 (10)	−0.0050 (8)	−0.0064 (9)	0.0029 (8)
C2	0.1079 (19)	0.0510 (12)	0.0466 (12)	−0.0113 (12)	−0.0080 (12)	0.0110 (10)
C3	0.134 (2)	0.0653 (15)	0.0519 (13)	−0.0148 (16)	0.0309 (14)	0.0074 (11)
C4	0.0997 (18)	0.0636 (14)	0.0682 (14)	−0.0003 (13)	0.0402 (13)	0.0038 (11)
C5	0.0640 (12)	0.0510 (11)	0.0520 (11)	0.0054 (9)	0.0157 (9)	0.0062 (9)
C6	0.0519 (10)	0.0376 (8)	0.0399 (9)	−0.0032 (7)	0.0012 (7)	0.0009 (7)
C7	0.0638 (11)	0.0465 (10)	0.0479 (10)	0.0142 (9)	0.0118 (9)	0.0056 (8)
C8	0.0507 (10)	0.0447 (10)	0.0333 (8)	0.0093 (8)	0.0100 (7)	0.0031 (7)
C9	0.0442 (9)	0.0532 (10)	0.0332 (8)	0.0052 (8)	0.0037 (7)	0.0011 (7)
C10	0.0453 (9)	0.0439 (9)	0.0385 (9)	0.0045 (7)	0.0102 (7)	−0.0013 (7)
C11	0.0516 (10)	0.0549 (11)	0.0603 (12)	−0.0011 (9)	0.0097 (9)	−0.0046 (9)
C12	0.0709 (14)	0.0443 (11)	0.0967 (18)	−0.0021 (10)	0.0214 (13)	−0.0018 (11)
C13	0.0813 (15)	0.0472 (12)	0.0973 (18)	0.0131 (11)	0.0211 (14)	0.0212 (12)
C14	0.0621 (12)	0.0606 (13)	0.0610 (12)	0.0173 (10)	0.0050 (10)	0.0161 (10)
C15	0.0478 (9)	0.0467 (10)	0.0397 (9)	0.0097 (8)	0.0073 (7)	0.0034 (7)
C16	0.0505 (10)	0.0539 (11)	0.0359 (9)	0.0089 (8)	−0.0009 (8)	−0.0028 (8)
C17	0.0509 (10)	0.0465 (10)	0.0365 (9)	0.0017 (8)	0.0097 (7)	−0.0027 (7)
C18	0.0641 (12)	0.0530 (11)	0.0531 (11)	−0.0076 (9)	0.0101 (9)	−0.0038 (9)
C19	0.0468 (9)	0.0418 (9)	0.0476 (10)	0.0059 (8)	−0.0036 (8)	−0.0018 (8)
C20	0.0497 (10)	0.0586 (11)	0.0514 (11)	0.0030 (9)	−0.0007 (9)	−0.0095 (9)
C21	0.0657 (13)	0.0817 (16)	0.0549 (12)	0.0107 (12)	0.0092 (10)	−0.0092 (11)
C22	0.0836 (16)	0.0850 (17)	0.0555 (13)	0.0203 (14)	−0.0027 (12)	−0.0212 (12)
C23	0.0766 (15)	0.0565 (12)	0.0658 (14)	0.0061 (11)	−0.0176 (12)	−0.0163 (11)
C24	0.0538 (11)	0.0436 (10)	0.0626 (12)	0.0045 (8)	−0.0089 (9)	−0.0003 (9)

Cl1—C1	1.738 (2)	C11—H11	0.9300
Cl2—C24	1.740 (2)	C12—C13	1.379 (3)
O1—C9	1.219 (2)	C12—H12	0.9300
O2—C16	1.221 (2)	C13—C14	1.372 (3)
C1—C2	1.381 (3)	C13—H13	0.9300
C1—C6	1.388 (2)	C14—C15	1.389 (3)
C2—C3	1.357 (3)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.476 (3)
C3—C4	1.365 (3)	C16—C17	1.488 (2)
C3—H3	0.9300	C17—C18	1.503 (3)
C4—C5	1.377 (3)	C18—C19	1.516 (3)
C4—H4	0.9300	C18—H18A	0.9700
C5—C6	1.379 (3)	C18—H18B	0.9700
C5—H5	0.9300	C19—C20	1.383 (3)
C6—C7	1.516 (2)	C19—C24	1.389 (2)
C7—C8	1.505 (2)	C20—C21	1.386 (3)
C7—H7A	0.9700	C20—H20	0.9300
C7—H7B	0.9700	C21—C22	1.371 (3)
C8—C17	1.350 (2)	C21—H21	0.9300
C8—C9	1.489 (3)	C22—C23	1.367 (3)
C9—C10	1.475 (2)	C22—H22	0.9300
C10—C11	1.387 (3)	C23—C24	1.385 (3)
C10—C15	1.398 (2)	C23—H23	0.9300
C11—C12	1.373 (3)
C2—C1—C6	121.6 (2)	C14—C13—C12	120.6 (2)
C2—C1—Cl1	118.05 (16)	C14—C13—H13	119.7
C6—C1—Cl1	120.36 (15)	C12—C13—H13	119.7
C3—C2—C1	119.8 (2)	C13—C14—C15	120.1 (2)
C3—C2—H2	120.1	C13—C14—H14	120.0
C1—C2—H2	120.1	C15—C14—H14	120.0
C2—C3—C4	120.1 (2)	C14—C15—C10	119.49 (18)
C2—C3—H3	119.9	C14—C15—C16	120.95 (17)
C4—C3—H3	119.9	C10—C15—C16	119.53 (15)
C3—C4—C5	120.0 (2)	O2—C16—C15	120.86 (17)
C3—C4—H4	120.0	O2—C16—C17	119.48 (18)
C5—C4—H4	120.0	C15—C16—C17	119.62 (15)
C4—C5—C6	121.55 (19)	C8—C17—C16	120.59 (16)
C4—C5—H5	119.2	C8—C17—C18	124.53 (16)
C6—C5—H5	119.2	C16—C17—C18	114.86 (16)
C5—C6—C1	116.92 (17)	C17—C18—C19	114.23 (16)
C5—C6—C7	122.83 (16)	C17—C18—H18A	108.7
C1—C6—C7	120.25 (16)	C19—C18—H18A	108.7
C8—C7—C6	114.41 (15)	C17—C18—H18B	108.7
C8—C7—H7A	108.7	C19—C18—H18B	108.7
C6—C7—H7A	108.7	H18A—C18—H18B	107.6
C8—C7—H7B	108.7	C20—C19—C24	116.75 (18)
C6—C7—H7B	108.7	C20—C19—C18	122.56 (16)
H7A—C7—H7B	107.6	C24—C19—C18	120.68 (18)
C17—C8—C9	120.54 (15)	C19—C20—C21	121.61 (19)
C17—C8—C7	124.07 (17)	C19—C20—H20	119.2
C9—C8—C7	115.39 (15)	C21—C20—H20	119.2
O1—C9—C10	120.42 (17)	C22—C21—C20	120.0 (2)
O1—C9—C8	120.02 (17)	C22—C21—H21	120.0
C10—C9—C8	119.54 (15)	C20—C21—H21	120.0
C11—C10—C15	119.39 (16)	C23—C22—C21	120.0 (2)
C11—C10—C9	120.69 (16)	C23—C22—H22	120.0
C15—C10—C9	119.90 (15)	C21—C22—H22	120.0
C12—C11—C10	120.40 (19)	C22—C23—C24	119.5 (2)
C12—C11—H11	119.8	C22—C23—H23	120.2
C10—C11—H11	119.8	C24—C23—H23	120.2
C11—C12—C13	120.0 (2)	C19—C24—C23	122.1 (2)
C11—C12—H12	120.0	C19—C24—Cl2	119.53 (16)
C13—C12—H12	120.0	C23—C24—Cl2	118.37 (16)
C6—C1—C2—C3	1.4 (3)	C9—C10—C15—C14	−176.07 (17)
Cl1—C1—C2—C3	−178.88 (18)	C11—C10—C15—C16	−175.53 (16)
C1—C2—C3—C4	0.0 (4)	C9—C10—C15—C16	5.7 (2)
C2—C3—C4—C5	−0.9 (4)	C14—C15—C16—O2	−6.5 (3)
C3—C4—C5—C6	0.4 (4)	C10—C15—C16—O2	171.68 (18)
C4—C5—C6—C1	0.9 (3)	C14—C15—C16—C17	175.61 (17)
C4—C5—C6—C7	−178.7 (2)	C10—C15—C16—C17	−6.2 (3)
C2—C1—C6—C5	−1.8 (3)	C9—C8—C17—C16	−0.6 (2)
Cl1—C1—C6—C5	178.44 (14)	C7—C8—C17—C16	−179.65 (16)
C2—C1—C6—C7	177.85 (18)	C9—C8—C17—C18	−179.10 (16)
Cl1—C1—C6—C7	−1.9 (2)	C7—C8—C17—C18	1.8 (3)
C5—C6—C7—C8	14.0 (3)	O2—C16—C17—C8	−174.32 (18)
C1—C6—C7—C8	−165.61 (16)	C15—C16—C17—C8	3.6 (3)
C6—C7—C8—C17	−96.4 (2)	O2—C16—C17—C18	4.4 (3)
C6—C7—C8—C9	84.5 (2)	C15—C16—C17—C18	−177.76 (16)
C17—C8—C9—O1	−178.37 (17)	C8—C17—C18—C19	−104.7 (2)
C7—C8—C9—O1	0.8 (2)	C16—C17—C18—C19	76.7 (2)
C17—C8—C9—C10	0.1 (2)	C17—C18—C19—C20	9.4 (3)
C7—C8—C9—C10	179.22 (15)	C17—C18—C19—C24	−169.87 (16)
O1—C9—C10—C11	−3.0 (3)	C24—C19—C20—C21	0.2 (3)
C8—C9—C10—C11	178.54 (16)	C18—C19—C20—C21	−179.10 (18)
O1—C9—C10—C15	175.71 (17)	C19—C20—C21—C22	−0.2 (3)
C8—C9—C10—C15	−2.7 (2)	C20—C21—C22—C23	0.3 (3)
C15—C10—C11—C12	−2.2 (3)	C21—C22—C23—C24	−0.4 (3)
C9—C10—C11—C12	176.55 (18)	C20—C19—C24—C23	−0.3 (3)
C10—C11—C12—C13	0.1 (3)	C18—C19—C24—C23	179.01 (18)
C11—C12—C13—C14	1.6 (4)	C20—C19—C24—Cl2	179.97 (14)
C12—C13—C14—C15	−1.1 (3)	C18—C19—C24—Cl2	−0.7 (2)
C13—C14—C15—C10	−1.1 (3)	C22—C23—C24—C19	0.4 (3)
C13—C14—C15—C16	177.1 (2)	C22—C23—C24—Cl2	−179.87 (17)
C11—C10—C15—C14	2.7 (3)