Molecules of the title compound, C
34H
24Cl
2O
6, lie across crystallographic inversion centres. The flavone moiety is slightly folded, with the benzene and dihydropyrone rings making a dihedral angle of 2.5 (2)°. In the crystal, the molecules exist as cyclic intermolecular C—H
Cl hydrogen-bonded dimers. The structure is further stabilized by van der Waals interactions.
Supporting information
CCDC reference: 202358
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.011 Å
- R factor = 0.056
- wR factor = 0.159
- Data-to-parameter ratio = 10.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
THETM_01 Alert B The value of sine(theta_max)/wavelength is less than 0.575
Calculated sin(theta_max)/wavelength = 0.5651
| Author response: see _publ_section_exptl_refinement
|
Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10
Rint given 0.122
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check
A suspension of 6-chloro-3-hydroxy-2-(2-furyl)-4-oxo-4H-1-benzopyran (1 g, 0.0038 mol), 1,4-dibromobutane (0.0019 mol), tetra-n-butylammonium iodide (1 g) and freshly ignited K2Co3 (1 g) were refluxed in dry acetone (30 ml) for 4 h. The colour of the reaction mixture changed from yellow to colourless. The reaction mixture, after filtration and distillation of acetone, was poured into cold water to obtain a mixture of the monochromone and bischromone. This was then crystallized from acetone to obtain pure bischromone.
All H atoms were fixed geometrically and allowed to ride on the corresponding non-H atoms, with C—H distances of 0.93 or 0.97 Å, and Uiso(H) = 1.2Ueq(C). The large Rint value (0.122) and low ratio of observed to unique reflections (1/3), are a result of the poor diffraction quality of the crystal. The intensity data collection was restricted to θmax of 23.68°, as the reflections were found to be rather weak at higher angles.
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
6,6'-Dichloro-3,3'-(butane-1,4-diyldioxy)diflavone
top
Crystal data top
C34H24Cl2O6 | Z = 1 |
Mr = 599.43 | F(000) = 310 |
Triclinic, P1 | Dx = 1.460 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.335 (9) Å | Cell parameters from 25 reflections |
b = 9.242 (8) Å | θ = 2–22° |
c = 13.969 (9) Å | µ = 0.29 mm−1 |
α = 89.27 (1)° | T = 293 K |
β = 82.68 (1)° | Block, colourless |
γ = 86.47 (1)° | 0.30 × 0.29 × 0.27 mm |
V = 681.8 (14) Å3 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.122 |
Radiation source: fine-focus sealed tube | θmax = 23.7°, θmin = 2.7° |
Graphite monochromator | h = −6→0 |
Non–profiled w/2θ scans | k = −10→10 |
2312 measured reflections | l = −15→15 |
2056 independent reflections | 3 standard reflections every 100 reflections |
685 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.159 | w = 1/[σ2(Fo2) + (0.0553P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max < 0.001 |
2056 reflections | Δρmax = 0.29 e Å−3 |
191 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.018 (4) |
Crystal data top
C34H24Cl2O6 | γ = 86.47 (1)° |
Mr = 599.43 | V = 681.8 (14) Å3 |
Triclinic, P1 | Z = 1 |
a = 5.335 (9) Å | Mo Kα radiation |
b = 9.242 (8) Å | µ = 0.29 mm−1 |
c = 13.969 (9) Å | T = 293 K |
α = 89.27 (1)° | 0.30 × 0.29 × 0.27 mm |
β = 82.68 (1)° | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.122 |
2312 measured reflections | θmax = 23.7° |
2056 independent reflections | 3 standard reflections every 100 reflections |
685 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 0.91 | Δρmax = 0.29 e Å−3 |
2056 reflections | Δρmin = −0.27 e Å−3 |
191 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.1694 (4) | 0.3740 (2) | −0.13199 (14) | 0.0600 (8) | |
O1 | 0.2970 (10) | 0.4448 (6) | 0.2383 (3) | 0.0561 (17) | |
O2 | 0.8111 (10) | 0.1188 (5) | 0.1416 (3) | 0.0483 (14) | |
O3 | 0.6268 (9) | 0.3219 (5) | 0.3616 (3) | 0.0426 (14) | |
C1 | 0.6415 (15) | 0.2821 (8) | 0.2677 (5) | 0.041 (2) | |
C2 | 0.4600 (14) | 0.3528 (8) | 0.2076 (5) | 0.041 (2) | |
C3 | 0.4871 (14) | 0.2954 (7) | 0.1094 (5) | 0.035 (2) | |
C4 | 0.3335 (15) | 0.3517 (8) | 0.0416 (5) | 0.049 (2) | |
H4 | 0.2096 | 0.4247 | 0.0599 | 0.059* | |
C5 | 0.3626 (14) | 0.3015 (8) | −0.0498 (5) | 0.042 (2) | |
C6 | 0.5444 (14) | 0.1923 (8) | −0.0786 (5) | 0.047 (2) | |
H6 | 0.5648 | 0.1596 | −0.1420 | 0.057* | |
C7 | 0.6934 (14) | 0.1326 (8) | −0.0147 (5) | 0.048 (2) | |
H7 | 0.8134 | 0.0575 | −0.0331 | 0.058* | |
C8 | 0.6621 (15) | 0.1862 (8) | 0.0785 (5) | 0.045 (2) | |
C9 | 0.8047 (14) | 0.1687 (8) | 0.2353 (5) | 0.039 (2) | |
C10 | 0.9624 (13) | 0.0765 (8) | 0.2910 (4) | 0.035 (2) | |
C11 | 0.9814 (16) | −0.0723 (8) | 0.2778 (5) | 0.060 (3) | |
H11 | 0.8893 | −0.1111 | 0.2332 | 0.072* | |
C12 | 1.1281 (16) | −0.1643 (9) | 0.3270 (6) | 0.066 (3) | |
H12 | 1.1337 | −0.2639 | 0.3175 | 0.079* | |
C13 | 1.2698 (16) | −0.1045 (9) | 0.3920 (6) | 0.060 (2) | |
H13 | 1.3748 | −0.1645 | 0.4257 | 0.072* | |
C14 | 1.2551 (16) | 0.0400 (10) | 0.4064 (6) | 0.065 (3) | |
H14 | 1.3487 | 0.0786 | 0.4507 | 0.078* | |
C15 | 1.1043 (14) | 0.1310 (8) | 0.3566 (5) | 0.048 (2) | |
H15 | 1.0976 | 0.2304 | 0.3672 | 0.058* | |
C16 | 0.7018 (15) | 0.4696 (8) | 0.3761 (4) | 0.049 (2) | |
H16A | 0.6097 | 0.5384 | 0.3385 | 0.058* | |
H16B | 0.8816 | 0.4759 | 0.3558 | 0.058* | |
C17 | 0.6415 (12) | 0.5022 (8) | 0.4805 (4) | 0.042 (2) | |
H17A | 0.6967 | 0.5977 | 0.4921 | 0.051* | |
H17B | 0.7372 | 0.4328 | 0.5164 | 0.051* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0686 (18) | 0.0651 (16) | 0.0508 (14) | −0.0001 (13) | −0.0262 (12) | −0.0019 (11) |
O1 | 0.058 (4) | 0.063 (4) | 0.044 (3) | 0.024 (3) | −0.005 (3) | −0.018 (3) |
O2 | 0.054 (4) | 0.056 (3) | 0.033 (3) | 0.021 (3) | −0.007 (3) | −0.015 (3) |
O3 | 0.058 (4) | 0.038 (3) | 0.031 (3) | 0.004 (3) | −0.004 (3) | −0.011 (2) |
C1 | 0.057 (6) | 0.044 (5) | 0.023 (4) | −0.005 (5) | −0.007 (4) | −0.005 (4) |
C2 | 0.041 (6) | 0.041 (5) | 0.041 (5) | 0.000 (5) | −0.002 (4) | −0.009 (4) |
C3 | 0.047 (6) | 0.028 (5) | 0.030 (4) | 0.003 (4) | −0.006 (4) | −0.005 (4) |
C4 | 0.058 (6) | 0.038 (5) | 0.051 (5) | 0.003 (5) | −0.005 (5) | 0.001 (4) |
C5 | 0.056 (7) | 0.046 (5) | 0.026 (5) | −0.002 (5) | −0.015 (4) | 0.001 (4) |
C6 | 0.051 (6) | 0.056 (6) | 0.033 (4) | 0.005 (5) | −0.003 (5) | −0.012 (4) |
C7 | 0.043 (6) | 0.063 (6) | 0.039 (5) | 0.012 (5) | −0.010 (4) | −0.018 (4) |
C8 | 0.047 (6) | 0.051 (6) | 0.038 (5) | 0.011 (5) | −0.011 (4) | −0.005 (4) |
C9 | 0.049 (6) | 0.038 (5) | 0.031 (4) | 0.010 (4) | −0.010 (4) | −0.021 (4) |
C10 | 0.031 (5) | 0.048 (5) | 0.025 (4) | 0.008 (4) | −0.005 (4) | −0.002 (4) |
C11 | 0.088 (7) | 0.050 (6) | 0.043 (5) | 0.021 (5) | −0.025 (5) | −0.021 (4) |
C12 | 0.080 (7) | 0.049 (6) | 0.073 (6) | 0.009 (5) | −0.037 (6) | −0.005 (5) |
C13 | 0.064 (7) | 0.055 (6) | 0.063 (6) | 0.007 (5) | −0.019 (5) | 0.016 (5) |
C14 | 0.083 (7) | 0.058 (6) | 0.061 (6) | 0.010 (6) | −0.045 (5) | 0.007 (5) |
C15 | 0.062 (6) | 0.037 (5) | 0.047 (5) | −0.004 (5) | −0.013 (5) | −0.004 (4) |
C16 | 0.058 (6) | 0.047 (6) | 0.038 (5) | −0.011 (5) | 0.006 (4) | −0.009 (4) |
C17 | 0.063 (6) | 0.038 (5) | 0.025 (4) | 0.012 (5) | −0.007 (4) | −0.007 (3) |
Geometric parameters (Å, º) top
Cl1—C5 | 1.740 (7) | C9—C10 | 1.450 (9) |
O1—C2 | 1.220 (7) | C10—C15 | 1.379 (8) |
O2—C8 | 1.378 (7) | C10—C11 | 1.385 (9) |
O2—C9 | 1.388 (7) | C11—C12 | 1.359 (9) |
O3—C1 | 1.358 (7) | C11—H11 | 0.93 |
O3—C16 | 1.470 (7) | C12—C13 | 1.393 (9) |
C1—C9 | 1.365 (8) | C12—H12 | 0.93 |
C1—C2 | 1.478 (9) | C13—C14 | 1.350 (9) |
C2—C3 | 1.464 (8) | C13—H13 | 0.93 |
C3—C8 | 1.367 (9) | C14—C15 | 1.372 (9) |
C3—C4 | 1.405 (8) | C14—H14 | 0.93 |
C4—C5 | 1.351 (9) | C15—H15 | 0.93 |
C4—H4 | 0.93 | C16—C17 | 1.484 (8) |
C5—C6 | 1.382 (9) | C16—H16A | 0.97 |
C6—C7 | 1.359 (8) | C16—H16B | 0.97 |
C6—H6 | 0.93 | C17—C17i | 1.541 (13) |
C7—C8 | 1.386 (8) | C17—H17A | 0.97 |
C7—H7 | 0.93 | C17—H17B | 0.97 |
| | | |
C8—O2—C9 | 121.0 (6) | C15—C10—C9 | 122.6 (7) |
C1—O3—C16 | 114.4 (5) | C11—C10—C9 | 120.3 (7) |
O3—C1—C9 | 118.8 (6) | C12—C11—C10 | 123.2 (7) |
O3—C1—C2 | 118.5 (7) | C12—C11—H11 | 118.4 |
C9—C1—C2 | 122.4 (6) | C10—C11—H11 | 118.4 |
O1—C2—C3 | 123.6 (7) | C11—C12—C13 | 117.9 (8) |
O1—C2—C1 | 123.2 (7) | C11—C12—H12 | 121.1 |
C3—C2—C1 | 113.1 (7) | C13—C12—H12 | 121.1 |
C8—C3—C4 | 116.6 (7) | C14—C13—C12 | 120.3 (8) |
C8—C3—C2 | 122.4 (7) | C14—C13—H13 | 119.9 |
C4—C3—C2 | 121.0 (7) | C12—C13—H13 | 119.9 |
C5—C4—C3 | 121.1 (7) | C13—C14—C15 | 121.0 (8) |
C5—C4—H4 | 119.4 | C13—C14—H14 | 119.5 |
C3—C4—H4 | 119.4 | C15—C14—H14 | 119.5 |
C4—C5—C6 | 120.5 (7) | C14—C15—C10 | 120.7 (7) |
C4—C5—Cl1 | 119.9 (6) | C14—C15—H15 | 119.7 |
C6—C5—Cl1 | 119.6 (6) | C10—C15—H15 | 119.7 |
C7—C6—C5 | 120.3 (7) | O3—C16—C17 | 107.3 (5) |
C7—C6—H6 | 119.9 | O3—C16—H16A | 110.2 |
C5—C6—H6 | 119.9 | C17—C16—H16A | 110.2 |
C6—C7—C8 | 118.4 (8) | O3—C16—H16B | 110.2 |
C6—C7—H7 | 120.8 | C17—C16—H16B | 110.2 |
C8—C7—H7 | 120.8 | H16A—C16—H16B | 108.5 |
C3—C8—O2 | 120.6 (7) | C16—C17—C17i | 114.3 (7) |
C3—C8—C7 | 123.1 (7) | C16—C17—H17A | 108.7 |
O2—C8—C7 | 116.3 (7) | C17i—C17—H17A | 108.7 |
C1—C9—O2 | 120.2 (6) | C16—C17—H17B | 108.7 |
C1—C9—C10 | 127.5 (6) | C17i—C17—H17B | 108.7 |
O2—C9—C10 | 111.9 (6) | H17A—C17—H17B | 107.6 |
C15—C10—C11 | 117.0 (7) | | |
| | | |
C16—O3—C1—C9 | 117.5 (7) | C6—C7—C8—C3 | 0.6 (12) |
C16—O3—C1—C2 | −69.2 (8) | C6—C7—C8—O2 | 177.8 (7) |
O3—C1—C2—O1 | −0.2 (11) | O3—C1—C9—O2 | 175.4 (6) |
C9—C1—C2—O1 | 172.8 (8) | C2—C1—C9—O2 | 2.4 (11) |
O3—C1—C2—C3 | −177.1 (6) | O3—C1—C9—C10 | 3.3 (12) |
C9—C1—C2—C3 | −4.1 (10) | C2—C1—C9—C10 | −169.7 (7) |
O1—C2—C3—C8 | −176.1 (8) | C8—O2—C9—C1 | 2.8 (10) |
C1—C2—C3—C8 | 0.8 (10) | C8—O2—C9—C10 | 176.1 (7) |
O1—C2—C3—C4 | 4.4 (12) | C1—C9—C10—C15 | −45.6 (12) |
C1—C2—C3—C4 | −178.7 (7) | O2—C9—C10—C15 | 141.8 (7) |
C8—C3—C4—C5 | −1.3 (11) | C1—C9—C10—C11 | 136.3 (8) |
C2—C3—C4—C5 | 178.3 (7) | O2—C9—C10—C11 | −36.3 (10) |
C3—C4—C5—C6 | 0.4 (11) | C15—C10—C11—C12 | 1.0 (12) |
C3—C4—C5—Cl1 | −179.9 (6) | C9—C10—C11—C12 | 179.2 (8) |
C4—C5—C6—C7 | 1.1 (12) | C10—C11—C12—C13 | −1.5 (13) |
Cl1—C5—C6—C7 | −178.7 (6) | C11—C12—C13—C14 | 1.4 (13) |
C5—C6—C7—C8 | −1.5 (12) | C12—C13—C14—C15 | −0.9 (14) |
C4—C3—C8—O2 | −176.3 (7) | C13—C14—C15—C10 | 0.4 (13) |
C2—C3—C8—O2 | 4.2 (11) | C11—C10—C15—C14 | −0.4 (11) |
C4—C3—C8—C7 | 0.8 (11) | C9—C10—C15—C14 | −178.6 (8) |
C2—C3—C8—C7 | −178.7 (7) | C1—O3—C16—C17 | 172.4 (6) |
C9—O2—C8—C3 | −6.1 (11) | O3—C16—C17—C17i | −61.0 (10) |
C9—O2—C8—C7 | 176.6 (6) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O1 | 0.97 | 2.51 | 3.091 (10) | 118 |
C4—H4···Cl1ii | 0.93 | 2.76 | 3.688 (10) | 174 |
Symmetry code: (ii) −x, −y+1, −z. |
Experimental details
Crystal data |
Chemical formula | C34H24Cl2O6 |
Mr | 599.43 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 5.335 (9), 9.242 (8), 13.969 (9) |
α, β, γ (°) | 89.27 (1), 82.68 (1), 86.47 (1) |
V (Å3) | 681.8 (14) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.30 × 0.29 × 0.27 |
|
Data collection |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2312, 2056, 685 |
Rint | 0.122 |
θmax (°) | 23.7 |
(sin θ/λ)max (Å−1) | 0.565 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.159, 0.91 |
No. of reflections | 2056 |
No. of parameters | 191 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.27 |
Selected geometric parameters (Å, º) topO1—C2 | 1.220 (7) | O3—C16 | 1.470 (7) |
O2—C8 | 1.378 (7) | C16—C17 | 1.484 (8) |
O2—C9 | 1.388 (7) | C17—C17i | 1.541 (13) |
O3—C1 | 1.358 (7) | | |
| | | |
O1—C2—C3 | 123.6 (7) | O2—C8—C7 | 116.3 (7) |
O1—C2—C1 | 123.2 (7) | C1—C9—C10 | 127.5 (6) |
C3—C2—C1 | 113.1 (7) | O2—C9—C10 | 111.9 (6) |
C8—C3—C4 | 116.6 (7) | C15—C10—C11 | 117.0 (7) |
C8—C3—C2 | 122.4 (7) | C15—C10—C9 | 122.6 (7) |
C3—C8—C7 | 123.1 (7) | | |
| | | |
C16—O3—C1—C2 | −69.2 (8) | C1—O3—C16—C17 | 172.4 (6) |
C1—C9—C10—C15 | −45.6 (12) | O3—C16—C17—C17i | −61.0 (10) |
O2—C9—C10—C11 | −36.3 (10) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O1 | 0.97 | 2.51 | 3.091 (10) | 118 |
C4—H4···Cl1ii | 0.93 | 2.76 | 3.688 (10) | 174 |
Symmetry code: (ii) −x, −y+1, −z. |
Benzopyran derivatives are anti-inflammatory and anti-allergic, and are used to treat elephantiasis. These compounds are capable of inducing alteration in DNA structure and replication. Flavonoids exhibit antidiabetic (Hii & Howell, 1985; Basnet et al., 1993; Ragunathan & Sulochana, 1994) and aldose reductase inhibitory activities (Varma & Kinoshita, 1976; Okuda et al., 1984; Aida et al., 1990). Chromanone compounds are used to treat angina pectoris (Hasegaida, 1967) and these compounds show vasodilating activity on the coronary vascular bed (Nagao et al., 1972). Diethyl 2,6-dimethyl-4-(2-phenyl-4-oxo-4H-1-benzopyran-6-yl)-1,4-dihydropyridine- 3,5-dicarboxylate, containing a 2-phenyl-4H-benzopyran-4-one (flavone) is known to have a coronary dilatory effect (Itz & Potzsch, 1963) and capillary resistance activity (Gabor, 1981).
The asymmetric unit of the title compound, (I), consists of one-half of the molecule, with the other half generated by a crystallographic inversion centre at (1 − x, 1 − y, 1 − z). The geometry of the benzopyran moiety is comparable with those observed in related structures (Thinagar et al., 2000; Bruno et al., 2001; Ozbey et al., 1999). The bond angles around C2 of the heterocyclic ring vary from 113.1 (7) to 123.6 (7)°, indicating significant deviation from the ideal value. The O2—C9—C10—C15 torsion angle [141.8 (7)°] shows a +anticlinal conformation of the phenyl ring with respect to the flavone moiety. The O3—C16 bond is in a trans orientation with respect to the flavone moiety, which is evidenced by the C1—O3—C16—C17 torsion angle of 172.4 (6)°. The pyran ring is planar within ±0.032 (8) Å, compared to the usual half-chair conformation (Alex et al. 1993). However, the flavone moiety is not strictly planar, as the benzene and dihydropyrone rings form a dihedral angle of 2.2 (3)°. The O atom of the keto group deviates from the flavone moiety by −0.084 (5). The dihedral angle between the planes of the flavone moiety and the phenyl ring is 42.5 (3)°.
The molecular structure of (I) is stabilized by intramolecular C—H···O hydrogen bonds and the crystal packing is stabilized by C—H···Cl intermolecular hydrogen bonds (Table 2). The intramolecular C16—H16A···O1 hydrogen bond is involved in R11(5) ring formation. In the crystal, an intermolecular C4—H4···Cl(-x, 1 − y, −z) hydrogen bond is involved in cyclic dimer formation, with an R22(8) ring descriptor (Bernstein et al., 1995).