Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053810/tk2208sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053810/tk2208Isup2.hkl |
CCDC reference: 672785
The title compound was prepared by reacting 3-bromo-β-lapachone (De Simone et al., 2002) with phenylhydrazone in refluxing methanol for 24 h. Recrystallization from an ethanol solution of (I) afforded red blocks.
The N-bound H atom was located in a difference map, relocated to an idealized position (N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(N). The remaining hydrogen atoms were geometrically placed (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate, but not to tip, to best fit the electron density.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C21H19BrN2O2 | F(000) = 840 |
Mr = 411.29 | Dx = 1.487 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8040 reflections |
a = 6.3799 (3) Å | θ = 2.0–27.2° |
b = 20.3789 (11) Å | µ = 2.25 mm−1 |
c = 14.4125 (8) Å | T = 293 K |
β = 101.269 (1)° | Block, red |
V = 1837.72 (17) Å3 | 0.39 × 0.34 × 0.11 mm |
Z = 4 |
Bruker SMART1000 CCD diffractometer | 4225 independent reflections |
Radiation source: fine-focus sealed tube | 2488 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −8→7 |
Tmin = 0.473, Tmax = 0.790 | k = −26→26 |
13653 measured reflections | l = −18→18 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.85 | w = 1/[σ2(Fo2) + (0.0398P)2] where P = (Fo2 + 2Fc2)/3 |
4225 reflections | (Δ/σ)max < 0.001 |
237 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
C21H19BrN2O2 | V = 1837.72 (17) Å3 |
Mr = 411.29 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.3799 (3) Å | µ = 2.25 mm−1 |
b = 20.3789 (11) Å | T = 293 K |
c = 14.4125 (8) Å | 0.39 × 0.34 × 0.11 mm |
β = 101.269 (1)° |
Bruker SMART1000 CCD diffractometer | 4225 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 2488 reflections with I > 2σ(I) |
Tmin = 0.473, Tmax = 0.790 | Rint = 0.036 |
13653 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.85 | Δρmax = 0.38 e Å−3 |
4225 reflections | Δρmin = −0.46 e Å−3 |
237 parameters |
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 | ||
C1 | 0.2158 (3) | 0.41562 (10) | 0.36365 (17) | 0.0432 (6) | |
H1 | 0.1327 | 0.3875 | 0.3982 | 0.052* | |
C2 | 0.4456 (3) | 0.39307 (10) | 0.38700 (18) | 0.0460 (6) | |
H2A | 0.5372 | 0.4260 | 0.3670 | 0.055* | |
H2B | 0.4894 | 0.3872 | 0.4548 | 0.055* | |
C3 | 0.4676 (3) | 0.32921 (10) | 0.33710 (16) | 0.0390 (5) | |
C4 | 0.3083 (3) | 0.30539 (10) | 0.26907 (16) | 0.0384 (5) | |
C5 | 0.1201 (3) | 0.40928 (10) | 0.25768 (17) | 0.0434 (6) | |
C6 | 0.2454 (4) | 0.44491 (12) | 0.19404 (18) | 0.0604 (7) | |
H6A | 0.3913 | 0.4303 | 0.2076 | 0.091* | |
H6B | 0.2407 | 0.4913 | 0.2051 | 0.091* | |
H6C | 0.1838 | 0.4358 | 0.1291 | 0.091* | |
C7 | −0.1144 (4) | 0.42674 (12) | 0.2355 (2) | 0.0606 (7) | |
H7A | −0.1885 | 0.4021 | 0.2759 | 0.091* | |
H7B | −0.1727 | 0.4164 | 0.1706 | 0.091* | |
H7C | −0.1312 | 0.4728 | 0.2460 | 0.091* | |
C8 | 0.3172 (3) | 0.24149 (10) | 0.22508 (16) | 0.0391 (5) | |
C9 | 0.1427 (4) | 0.21550 (11) | 0.16214 (17) | 0.0455 (6) | |
H9 | 0.0165 | 0.2394 | 0.1474 | 0.055* | |
C10 | 0.1553 (4) | 0.15525 (12) | 0.12204 (18) | 0.0544 (7) | |
H10 | 0.0373 | 0.1382 | 0.0808 | 0.065* | |
C11 | 0.3429 (4) | 0.11943 (12) | 0.14250 (18) | 0.0545 (7) | |
H11 | 0.3510 | 0.0786 | 0.1146 | 0.065* | |
C12 | 0.5170 (4) | 0.14396 (11) | 0.20380 (18) | 0.0506 (6) | |
H12 | 0.6431 | 0.1198 | 0.2161 | 0.061* | |
C13 | 0.5081 (3) | 0.20479 (10) | 0.24819 (16) | 0.0396 (5) | |
C14 | 0.6863 (3) | 0.23012 (10) | 0.31862 (16) | 0.0397 (5) | |
C15 | 0.6641 (3) | 0.29275 (10) | 0.36498 (17) | 0.0411 (6) | |
C16 | 1.2036 (3) | 0.17164 (11) | 0.42902 (17) | 0.0440 (6) | |
C17 | 1.3754 (4) | 0.19699 (11) | 0.49211 (18) | 0.0496 (6) | |
H17 | 1.3666 | 0.2384 | 0.5182 | 0.060* | |
C18 | 1.5606 (4) | 0.16053 (13) | 0.51634 (19) | 0.0584 (7) | |
H18 | 1.6767 | 0.1774 | 0.5589 | 0.070* | |
C19 | 1.5736 (4) | 0.09970 (14) | 0.4779 (2) | 0.0638 (7) | |
H19 | 1.6989 | 0.0754 | 0.4939 | 0.077* | |
C20 | 1.4013 (4) | 0.07436 (12) | 0.4156 (2) | 0.0646 (8) | |
H20 | 1.4106 | 0.0328 | 0.3900 | 0.078* | |
C21 | 1.2151 (4) | 0.11001 (12) | 0.39096 (19) | 0.0565 (7) | |
H21 | 1.0986 | 0.0927 | 0.3492 | 0.068* | |
N1 | 0.8577 (3) | 0.19224 (9) | 0.33927 (14) | 0.0430 (5) | |
N2 | 1.0202 (3) | 0.21120 (9) | 0.40449 (14) | 0.0469 (5) | |
H2 | 1.0145 | 0.2482 | 0.4325 | 0.056* | |
O1 | 0.1235 (2) | 0.33873 (7) | 0.23736 (11) | 0.0465 (4) | |
O2 | 0.8114 (2) | 0.31524 (7) | 0.42808 (12) | 0.0537 (4) | |
Br1 | 0.19534 (4) | 0.505529 (12) | 0.40785 (2) | 0.06343 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0428 (13) | 0.0301 (12) | 0.0565 (16) | 0.0019 (9) | 0.0091 (12) | 0.0015 (11) |
C2 | 0.0436 (13) | 0.0377 (13) | 0.0539 (16) | 0.0045 (10) | 0.0025 (12) | −0.0059 (11) |
C3 | 0.0375 (13) | 0.0320 (12) | 0.0459 (15) | 0.0015 (9) | 0.0038 (11) | −0.0001 (10) |
C4 | 0.0351 (12) | 0.0364 (12) | 0.0425 (14) | 0.0014 (10) | 0.0044 (11) | 0.0027 (11) |
C5 | 0.0409 (13) | 0.0334 (12) | 0.0537 (16) | 0.0054 (9) | 0.0043 (12) | 0.0034 (11) |
C6 | 0.0657 (17) | 0.0534 (16) | 0.0636 (19) | 0.0021 (12) | 0.0163 (15) | 0.0107 (13) |
C7 | 0.0440 (15) | 0.0535 (16) | 0.078 (2) | 0.0097 (12) | −0.0025 (14) | 0.0031 (14) |
C8 | 0.0421 (13) | 0.0349 (12) | 0.0390 (13) | −0.0025 (10) | 0.0050 (11) | 0.0021 (10) |
C9 | 0.0441 (14) | 0.0423 (14) | 0.0457 (15) | −0.0026 (10) | −0.0015 (12) | 0.0017 (11) |
C10 | 0.0638 (17) | 0.0459 (15) | 0.0474 (16) | −0.0141 (12) | −0.0038 (13) | −0.0026 (12) |
C11 | 0.0672 (17) | 0.0395 (14) | 0.0526 (17) | −0.0024 (12) | 0.0014 (14) | −0.0086 (12) |
C12 | 0.0541 (15) | 0.0419 (14) | 0.0542 (17) | 0.0061 (11) | 0.0069 (13) | −0.0052 (12) |
C13 | 0.0427 (13) | 0.0365 (13) | 0.0388 (14) | −0.0009 (10) | 0.0059 (11) | 0.0011 (10) |
C14 | 0.0385 (13) | 0.0352 (12) | 0.0448 (15) | 0.0042 (10) | 0.0067 (11) | 0.0024 (11) |
C15 | 0.0399 (13) | 0.0351 (12) | 0.0457 (15) | −0.0005 (10) | 0.0017 (12) | 0.0027 (11) |
C16 | 0.0410 (13) | 0.0420 (13) | 0.0489 (16) | 0.0087 (10) | 0.0084 (12) | 0.0078 (11) |
C17 | 0.0468 (15) | 0.0475 (15) | 0.0526 (17) | 0.0045 (11) | 0.0044 (13) | 0.0020 (12) |
C18 | 0.0486 (16) | 0.0621 (18) | 0.0590 (19) | 0.0054 (12) | −0.0027 (13) | 0.0083 (14) |
C19 | 0.0527 (16) | 0.0649 (19) | 0.071 (2) | 0.0235 (14) | 0.0045 (15) | 0.0107 (15) |
C20 | 0.0654 (18) | 0.0479 (16) | 0.075 (2) | 0.0192 (13) | 0.0014 (16) | 0.0000 (14) |
C21 | 0.0549 (16) | 0.0465 (15) | 0.0637 (18) | 0.0063 (12) | 0.0004 (13) | −0.0021 (13) |
N1 | 0.0405 (11) | 0.0409 (11) | 0.0461 (13) | 0.0033 (9) | 0.0050 (10) | 0.0014 (9) |
N2 | 0.0427 (11) | 0.0420 (11) | 0.0534 (14) | 0.0056 (9) | 0.0032 (10) | −0.0027 (10) |
O1 | 0.0378 (9) | 0.0378 (9) | 0.0585 (11) | 0.0037 (7) | −0.0042 (8) | −0.0031 (8) |
O2 | 0.0422 (9) | 0.0459 (10) | 0.0640 (12) | 0.0045 (7) | −0.0121 (9) | −0.0130 (9) |
Br1 | 0.06445 (19) | 0.04274 (16) | 0.0824 (2) | 0.00948 (12) | 0.01259 (15) | −0.01133 (14) |
C1—C2 | 1.511 (3) | C10—C11 | 1.384 (3) |
C1—C5 | 1.535 (3) | C10—H10 | 0.9300 |
C1—Br1 | 1.952 (2) | C11—C12 | 1.371 (3) |
C1—H1 | 0.9800 | C11—H11 | 0.9300 |
C2—C3 | 1.507 (3) | C12—C13 | 1.401 (3) |
C2—H2A | 0.9700 | C12—H12 | 0.9300 |
C2—H2B | 0.9700 | C13—C14 | 1.462 (3) |
C3—C4 | 1.357 (3) | C14—N1 | 1.324 (3) |
C3—C15 | 1.445 (3) | C14—C15 | 1.460 (3) |
C4—O1 | 1.360 (2) | C15—O2 | 1.260 (2) |
C4—C8 | 1.454 (3) | C16—C21 | 1.378 (3) |
C5—O1 | 1.468 (2) | C16—C17 | 1.380 (3) |
C5—C7 | 1.510 (3) | C16—N2 | 1.408 (3) |
C5—C6 | 1.515 (3) | C17—C18 | 1.382 (3) |
C6—H6A | 0.9600 | C17—H17 | 0.9300 |
C6—H6B | 0.9600 | C18—C19 | 1.367 (3) |
C6—H6C | 0.9600 | C18—H18 | 0.9300 |
C7—H7A | 0.9600 | C19—C20 | 1.377 (4) |
C7—H7B | 0.9600 | C19—H19 | 0.9300 |
C7—H7C | 0.9600 | C20—C21 | 1.379 (3) |
C8—C9 | 1.396 (3) | C20—H20 | 0.9300 |
C8—C13 | 1.412 (3) | C21—H21 | 0.9300 |
C9—C10 | 1.366 (3) | N1—N2 | 1.314 (2) |
C9—H9 | 0.9300 | N2—H2 | 0.8600 |
C2—C1—C5 | 112.08 (19) | C9—C10—C11 | 120.3 (2) |
C2—C1—Br1 | 109.67 (14) | C9—C10—H10 | 119.9 |
C5—C1—Br1 | 111.39 (14) | C11—C10—H10 | 119.9 |
C2—C1—H1 | 107.8 | C12—C11—C10 | 120.2 (2) |
C5—C1—H1 | 107.8 | C12—C11—H11 | 119.9 |
Br1—C1—H1 | 107.8 | C10—C11—H11 | 119.9 |
C3—C2—C1 | 109.48 (18) | C11—C12—C13 | 121.1 (2) |
C3—C2—H2A | 109.8 | C11—C12—H12 | 119.5 |
C1—C2—H2A | 109.8 | C13—C12—H12 | 119.5 |
C3—C2—H2B | 109.8 | C12—C13—C8 | 118.1 (2) |
C1—C2—H2B | 109.8 | C12—C13—C14 | 122.3 (2) |
H2A—C2—H2B | 108.2 | C8—C13—C14 | 119.62 (19) |
C4—C3—C15 | 120.2 (2) | N1—C14—C15 | 123.8 (2) |
C4—C3—C2 | 121.83 (19) | N1—C14—C13 | 116.5 (2) |
C15—C3—C2 | 117.92 (19) | C15—C14—C13 | 119.64 (18) |
C3—C4—O1 | 122.82 (19) | O2—C15—C3 | 119.9 (2) |
C3—C4—C8 | 123.22 (19) | O2—C15—C14 | 121.54 (19) |
O1—C4—C8 | 113.95 (18) | C3—C15—C14 | 118.6 (2) |
O1—C5—C7 | 103.95 (17) | C21—C16—C17 | 120.4 (2) |
O1—C5—C6 | 108.58 (19) | C21—C16—N2 | 121.9 (2) |
C7—C5—C6 | 112.2 (2) | C17—C16—N2 | 117.7 (2) |
O1—C5—C1 | 105.21 (16) | C16—C17—C18 | 119.7 (2) |
C7—C5—C1 | 112.05 (19) | C16—C17—H17 | 120.2 |
C6—C5—C1 | 114.06 (19) | C18—C17—H17 | 120.2 |
C5—C6—H6A | 109.5 | C19—C18—C17 | 120.1 (2) |
C5—C6—H6B | 109.5 | C19—C18—H18 | 119.9 |
H6A—C6—H6B | 109.5 | C17—C18—H18 | 119.9 |
C5—C6—H6C | 109.5 | C18—C19—C20 | 120.0 (2) |
H6A—C6—H6C | 109.5 | C18—C19—H19 | 120.0 |
H6B—C6—H6C | 109.5 | C20—C19—H19 | 120.0 |
C5—C7—H7A | 109.5 | C19—C20—C21 | 120.6 (3) |
C5—C7—H7B | 109.5 | C19—C20—H20 | 119.7 |
H7A—C7—H7B | 109.5 | C21—C20—H20 | 119.7 |
C5—C7—H7C | 109.5 | C16—C21—C20 | 119.2 (2) |
H7A—C7—H7C | 109.5 | C16—C21—H21 | 120.4 |
H7B—C7—H7C | 109.5 | C20—C21—H21 | 120.4 |
C9—C8—C13 | 119.6 (2) | N2—N1—C14 | 119.41 (19) |
C9—C8—C4 | 121.9 (2) | N1—N2—C16 | 120.81 (19) |
C13—C8—C4 | 118.47 (19) | N1—N2—H2 | 119.6 |
C10—C9—C8 | 120.7 (2) | C16—N2—H2 | 119.6 |
C10—C9—H9 | 119.7 | C4—O1—C5 | 117.88 (16) |
C8—C9—H9 | 119.7 | ||
C5—C1—C2—C3 | −45.1 (2) | C8—C13—C14—N1 | 177.8 (2) |
Br1—C1—C2—C3 | −169.34 (16) | C12—C13—C14—C15 | −177.7 (2) |
C1—C2—C3—C4 | 11.2 (3) | C8—C13—C14—C15 | 0.6 (3) |
C1—C2—C3—C15 | −167.68 (19) | C4—C3—C15—O2 | 179.9 (2) |
C15—C3—C4—O1 | −177.3 (2) | C2—C3—C15—O2 | −1.2 (3) |
C2—C3—C4—O1 | 3.8 (3) | C4—C3—C15—C14 | −0.2 (3) |
C15—C3—C4—C8 | 4.1 (3) | C2—C3—C15—C14 | 178.8 (2) |
C2—C3—C4—C8 | −174.8 (2) | N1—C14—C15—O2 | 0.8 (4) |
C2—C1—C5—O1 | 63.2 (2) | C13—C14—C15—O2 | 177.8 (2) |
Br1—C1—C5—O1 | −173.54 (13) | N1—C14—C15—C3 | −179.1 (2) |
C2—C1—C5—C7 | 175.48 (18) | C13—C14—C15—C3 | −2.2 (3) |
Br1—C1—C5—C7 | −61.2 (2) | C21—C16—C17—C18 | 0.7 (4) |
C2—C1—C5—C6 | −55.7 (2) | N2—C16—C17—C18 | −178.4 (2) |
Br1—C1—C5—C6 | 67.6 (2) | C16—C17—C18—C19 | 0.1 (4) |
C3—C4—C8—C9 | 173.5 (2) | C17—C18—C19—C20 | −0.6 (4) |
O1—C4—C8—C9 | −5.1 (3) | C18—C19—C20—C21 | 0.4 (4) |
C3—C4—C8—C13 | −5.7 (3) | C17—C16—C21—C20 | −0.9 (4) |
O1—C4—C8—C13 | 175.69 (19) | N2—C16—C21—C20 | 178.1 (2) |
C13—C8—C9—C10 | −0.6 (3) | C19—C20—C21—C16 | 0.4 (4) |
C4—C8—C9—C10 | −179.8 (2) | C15—C14—N1—N2 | −0.5 (3) |
C8—C9—C10—C11 | −0.8 (4) | C13—C14—N1—N2 | −177.58 (19) |
C9—C10—C11—C12 | 0.5 (4) | C14—N1—N2—C16 | 179.1 (2) |
C10—C11—C12—C13 | 1.2 (4) | C21—C16—N2—N1 | −4.5 (3) |
C11—C12—C13—C8 | −2.6 (4) | C17—C16—N2—N1 | 174.6 (2) |
C11—C12—C13—C14 | 175.8 (2) | C3—C4—O1—C5 | 17.2 (3) |
C9—C8—C13—C12 | 2.3 (3) | C8—C4—O1—C5 | −164.19 (18) |
C4—C8—C13—C12 | −178.5 (2) | C7—C5—O1—C4 | −166.46 (19) |
C9—C8—C13—C14 | −176.1 (2) | C6—C5—O1—C4 | 74.0 (2) |
C4—C8—C13—C14 | 3.1 (3) | C1—C5—O1—C4 | −48.5 (2) |
C12—C13—C14—N1 | −0.5 (3) |
Experimental details
Crystal data | |
Chemical formula | C21H19BrN2O2 |
Mr | 411.29 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 6.3799 (3), 20.3789 (11), 14.4125 (8) |
β (°) | 101.269 (1) |
V (Å3) | 1837.72 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.25 |
Crystal size (mm) | 0.39 × 0.34 × 0.11 |
Data collection | |
Diffractometer | Bruker SMART1000 CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.473, 0.790 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13653, 4225, 2488 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.079, 0.85 |
No. of reflections | 4225 |
No. of parameters | 237 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.46 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).
The title compound, (I), is a derivative of 3-bromo-β-lapachone (De Simone et al., 2002). It was prepared as part of our on-going studies of azo dyes with possible medical applications (Carvalho et al., 2002).
Compound (I) exists in its hydrazo tautomeric form in the solid-state (Fig. 1), in which the mobile H atom is attached to the N2 atom. NMR spectroscopic measurements indicate that the azo tautomer [with the H atom attached to O2 and the B (C3/C4/C8/C13–C15) ring aromatic; see Scheme] also occurs in solution. The hydrazo conformation in (I) is stabilized by an intramolecular N—H···O hydrogen bond (Table 1).
In the solid-state structure of (I), the carbon-carbon bond lengths in the B ring (see Scheme) indicate its weak aromatic character, with four of the six C—C bonds longer than 1.44 Å and one shorter than 1.36 Å. Even so, it is almost flat (r.m.s. deviation = 0.008 Å). The A ring and B ring planes are slightly twisted [dihedral angle = 3.71 (13)°]. The D ring plane makes an angle of 4.01 (13)° with the B ring mean plane. The heterocyclic C ring adopts a half-chair conformation with C2/C3/C4/O1 approximately co-planar (r.m.s. deviation = 0.012 Å) and C1 and C5 deviating from the plane by -0.341 (4) Å and 0.449 (4) Å, respectively. Such a conformation was also seen in 3-bromo-β-lapachone (De Simone et al., 2002). The title molecule is chiral: in the arbitrarily chosen asymmetric molecule C1 has R configuration, but crystal symmetry generates a racemic mixture. Otherwise, the geometric parameters of (I) may be regarded as normal (Allen et al., 1987).
In the crystal, aromatic π–π stacking involving the B and D rings helps to consolidate the packing [B···Di centroid-centroid separation = 3.6804 (14) Å, i = x - 1, y, z].