3-(3,4-Dichloro-benzyl-idene)chroman-4-one.

The distinctive feature of the structure of the title compound, C(16)H(10)Cl(2)O(2), is the formation of a zigzag chain along [100] via Cl⋯Cl inter-actions [3.591 (1) and 3.631 (1) Å]. The chroman-one moiety is fused with the benzene ring and adopts a half-chair conformation. The dihedral angle between the benzene ring of the chromanone moiety and the dichlorobenzene plane is 56.14 (8)°.

Related literature

For background to homoisoflavonoids, see: Kirkiacharian et al. (1984 ▶). For a related structure, see: Gopaul et al. (2012 ▶).

Experimental

Crystal data

C16H10Cl2O2

M = 305.14

Monoclinic,

a = 3.9224 (3) Å

b = 11.5175 (10) Å

c = 28.957 (3) Å

β = 92.270 (2)°

V = 1307.12 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 173 K

0.16 × 0.12 × 0.11 mm

Data collection

Bruker Kappa Duo APEXII Diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.925, T max = 0.948

15291 measured reflections

3258 independent reflections

2611 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.089

S = 1.03

3258 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040561/hg5252sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040561/hg5252Isup2.hkl

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

C16H10Cl2O2	F(000) = 624
Mr = 305.14	Dx = 1.551 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15291 reflections
a = 3.9224 (3) Å	θ = 1.9–28.3°
b = 11.5175 (10) Å	µ = 0.49 mm−1
c = 28.957 (3) Å	T = 173 K
β = 92.270 (2)°	Block, colourless
V = 1307.12 (19) Å3	0.16 × 0.12 × 0.11 mm
Z = 4

Bruker Kappa Duo APEXII Diffractometer	3258 independent reflections
Radiation source: fine-focus sealed tube	2611 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
0.5° φ scans and ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −5→5
Tmin = 0.925, Tmax = 0.948	k = −15→15
15291 measured reflections	l = −38→38

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.370P] where P = (Fo2 + 2Fc2)/3
3258 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.21 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
Cl1	0.42734 (11)	0.87066 (4)	0.446666 (14)	0.03559 (12)
Cl2	0.24634 (12)	0.61056 (4)	0.471571 (14)	0.04001 (13)
O1	0.1216 (3)	0.60873 (9)	0.19421 (4)	0.0295 (3)
O2	−0.4016 (3)	0.91508 (10)	0.20528 (4)	0.0370 (3)
C1	0.0018 (4)	0.66516 (13)	0.15546 (5)	0.0257 (3)
C2	−0.0674 (4)	0.62604 (13)	0.23556 (5)	0.0264 (3)
H2A	0.0689	0.5962	0.2625	0.032*
H2B	−0.2815	0.5806	0.2330	0.032*
C3	−0.1530 (4)	0.75127 (12)	0.24381 (5)	0.0246 (3)
C4	−0.2625 (4)	0.82037 (13)	0.20229 (6)	0.0263 (3)
C5	−0.1875 (4)	0.76778 (13)	0.15740 (5)	0.0253 (3)
C6	−0.2890 (4)	0.82258 (14)	0.11584 (6)	0.0316 (4)
H6	−0.4186	0.8922	0.1166	0.038*
C7	−0.2037 (5)	0.77697 (16)	0.07401 (6)	0.0374 (4)
H7	−0.2737	0.8148	0.0461	0.045*
C8	−0.0143 (5)	0.67520 (16)	0.07285 (6)	0.0365 (4)
H8	0.0453	0.6437	0.0439	0.044*
C9	0.0882 (4)	0.61927 (14)	0.11313 (6)	0.0315 (3)
H9	0.2174	0.5496	0.1120	0.038*
C10	−0.1366 (4)	0.80455 (13)	0.28501 (5)	0.0269 (3)
H10	−0.1923	0.8848	0.2848	0.032*
C11	−0.0434 (4)	0.75431 (13)	0.33026 (5)	0.0253 (3)
C12	0.1296 (4)	0.82387 (13)	0.36316 (5)	0.0258 (3)
H12	0.1865	0.9015	0.3555	0.031*
C13	0.2187 (4)	0.78142 (13)	0.40650 (5)	0.0256 (3)
C14	0.1346 (4)	0.66795 (14)	0.41804 (5)	0.0263 (3)
C15	−0.0449 (4)	0.59937 (13)	0.38621 (6)	0.0275 (3)
H15	−0.1075	0.5226	0.3944	0.033*
C16	−0.1336 (4)	0.64150 (13)	0.34272 (5)	0.0261 (3)
H16	−0.2565	0.5936	0.3212	0.031*

	U11	U22	U33	U12	U13	U23
Cl1	0.0386 (2)	0.0369 (2)	0.0310 (2)	−0.00723 (17)	−0.00110 (17)	−0.00681 (16)
Cl2	0.0470 (3)	0.0436 (3)	0.0291 (2)	−0.00285 (19)	−0.00218 (18)	0.00968 (17)
O1	0.0354 (6)	0.0268 (6)	0.0265 (6)	0.0085 (4)	0.0024 (5)	0.0026 (4)
O2	0.0447 (7)	0.0258 (6)	0.0400 (7)	0.0113 (5)	−0.0050 (6)	0.0018 (5)
C1	0.0265 (7)	0.0234 (7)	0.0269 (8)	−0.0051 (6)	−0.0014 (6)	0.0021 (6)
C2	0.0314 (8)	0.0232 (7)	0.0245 (7)	0.0025 (6)	0.0013 (6)	0.0011 (6)
C3	0.0226 (7)	0.0227 (7)	0.0283 (8)	0.0016 (5)	−0.0007 (6)	0.0020 (6)
C4	0.0247 (7)	0.0217 (7)	0.0321 (8)	0.0006 (6)	−0.0032 (6)	0.0020 (6)
C5	0.0236 (7)	0.0240 (7)	0.0279 (8)	−0.0047 (6)	−0.0030 (6)	0.0034 (6)
C6	0.0283 (8)	0.0314 (8)	0.0348 (9)	−0.0041 (6)	−0.0046 (7)	0.0082 (7)
C7	0.0363 (9)	0.0467 (10)	0.0286 (9)	−0.0110 (8)	−0.0049 (7)	0.0108 (7)
C8	0.0387 (9)	0.0440 (10)	0.0271 (8)	−0.0118 (8)	0.0044 (7)	−0.0016 (7)
C9	0.0332 (8)	0.0298 (8)	0.0317 (9)	−0.0066 (7)	0.0052 (7)	−0.0013 (6)
C10	0.0262 (7)	0.0224 (7)	0.0322 (8)	0.0013 (6)	0.0014 (6)	0.0013 (6)
C11	0.0264 (7)	0.0232 (7)	0.0265 (8)	0.0030 (6)	0.0044 (6)	−0.0008 (6)
C12	0.0282 (8)	0.0207 (7)	0.0287 (8)	0.0000 (6)	0.0052 (6)	−0.0021 (6)
C13	0.0242 (7)	0.0266 (7)	0.0261 (8)	−0.0008 (6)	0.0030 (6)	−0.0038 (6)
C14	0.0258 (7)	0.0299 (8)	0.0233 (7)	0.0020 (6)	0.0036 (6)	0.0039 (6)
C15	0.0274 (8)	0.0224 (7)	0.0330 (8)	−0.0016 (6)	0.0058 (6)	0.0021 (6)
C16	0.0257 (7)	0.0239 (7)	0.0287 (8)	−0.0010 (6)	0.0020 (6)	−0.0032 (6)

Cl1—C13	1.7330 (15)	C7—C8	1.389 (3)
Cl2—C14	1.7256 (15)	C7—H7	0.9500
O1—C1	1.3641 (18)	C8—C9	1.378 (2)
O1—C2	1.4470 (19)	C8—H8	0.9500
O2—C4	1.2243 (19)	C9—H9	0.9500
C1—C9	1.389 (2)	C10—C11	1.465 (2)
C1—C5	1.398 (2)	C10—H10	0.9500
C2—C3	1.502 (2)	C11—C16	1.398 (2)
C2—H2A	0.9900	C11—C12	1.400 (2)
C2—H2B	0.9900	C12—C13	1.379 (2)
C3—C10	1.341 (2)	C12—H12	0.9500
C3—C4	1.491 (2)	C13—C14	1.392 (2)
C4—C5	1.474 (2)	C14—C15	1.385 (2)
C5—C6	1.402 (2)	C15—C16	1.381 (2)
C6—C7	1.374 (3)	C15—H15	0.9500
C6—H6	0.9500	C16—H16	0.9500
C1—O1—C2	116.35 (12)	C9—C8—H8	119.6
O1—C1—C9	117.15 (14)	C7—C8—H8	119.6
O1—C1—C5	122.42 (14)	C8—C9—C1	119.71 (16)
C9—C1—C5	120.37 (15)	C8—C9—H9	120.1
O1—C2—C3	112.89 (12)	C1—C9—H9	120.1
O1—C2—H2A	109.0	C3—C10—C11	128.05 (14)
C3—C2—H2A	109.0	C3—C10—H10	116.0
O1—C2—H2B	109.0	C11—C10—H10	116.0
C3—C2—H2B	109.0	C16—C11—C12	118.51 (14)
H2A—C2—H2B	107.8	C16—C11—C10	122.76 (14)
C10—C3—C4	118.39 (13)	C12—C11—C10	118.66 (13)
C10—C3—C2	125.29 (14)	C13—C12—C11	121.01 (14)
C4—C3—C2	116.32 (13)	C13—C12—H12	119.5
O2—C4—C5	122.25 (14)	C11—C12—H12	119.5
O2—C4—C3	122.24 (15)	C12—C13—C14	119.84 (14)
C5—C4—C3	115.51 (13)	C12—C13—Cl1	119.77 (12)
C1—C5—C6	118.63 (15)	C14—C13—Cl1	120.38 (12)
C1—C5—C4	120.50 (13)	C15—C14—C13	119.66 (14)
C6—C5—C4	120.79 (14)	C15—C14—Cl2	118.93 (12)
C7—C6—C5	120.90 (16)	C13—C14—Cl2	121.41 (12)
C7—C6—H6	119.5	C16—C15—C14	120.64 (14)
C5—C6—H6	119.5	C16—C15—H15	119.7
C6—C7—C8	119.56 (16)	C14—C15—H15	119.7
C6—C7—H7	120.2	C15—C16—C11	120.31 (14)
C8—C7—H7	120.2	C15—C16—H16	119.8
C9—C8—C7	120.82 (16)	C11—C16—H16	119.8
C2—O1—C1—C9	−156.47 (14)	C7—C8—C9—C1	−0.1 (2)
C2—O1—C1—C5	26.3 (2)	O1—C1—C9—C8	−177.45 (14)
C1—O1—C2—C3	−46.21 (17)	C5—C1—C9—C8	−0.2 (2)
O1—C2—C3—C10	−138.89 (16)	C4—C3—C10—C11	178.67 (15)
O1—C2—C3—C4	40.74 (18)	C2—C3—C10—C11	−1.7 (3)
C10—C3—C4—O2	−15.1 (2)	C3—C10—C11—C16	−36.4 (2)
C2—C3—C4—O2	165.28 (15)	C3—C10—C11—C12	146.59 (17)
C10—C3—C4—C5	164.10 (14)	C16—C11—C12—C13	1.9 (2)
C2—C3—C4—C5	−15.56 (19)	C10—C11—C12—C13	179.04 (14)
O1—C1—C5—C6	177.47 (13)	C11—C12—C13—C14	−0.4 (2)
C9—C1—C5—C6	0.3 (2)	C11—C12—C13—Cl1	−179.05 (12)
O1—C1—C5—C4	0.7 (2)	C12—C13—C14—C15	−1.4 (2)
C9—C1—C5—C4	−176.41 (14)	Cl1—C13—C14—C15	177.26 (12)
O2—C4—C5—C1	173.56 (15)	C12—C13—C14—Cl2	179.08 (12)
C3—C4—C5—C1	−5.6 (2)	Cl1—C13—C14—Cl2	−2.23 (19)
O2—C4—C5—C6	−3.1 (2)	C13—C14—C15—C16	1.6 (2)
C3—C4—C5—C6	177.72 (14)	Cl2—C14—C15—C16	−178.85 (12)
C1—C5—C6—C7	−0.3 (2)	C14—C15—C16—C11	−0.1 (2)
C4—C5—C6—C7	176.48 (15)	C12—C11—C16—C15	−1.7 (2)
C5—C6—C7—C8	0.0 (2)	C10—C11—C16—C15	−178.69 (15)
C6—C7—C8—C9	0.2 (3)