3-(2,4-Dibromo-anilino)-2,2-dimethyl-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione: a new substituted aryl-amino nor-β-lapachone derivative.

The title compound, C(20)H(15)Br(2)NO(3), shows the furan ring to adopt a half-chair conformation and the two ring systems to be approximately perpendicular [dihedral angle = 71.0 (2)°]. In the crystal structure, inter-molecular C-H⋯O contacts link the mol-ecules.

Related literature

For general background, see: Hillard et al. (2008 ▶); Pinto et al., (1997 ▶); Dos Santos et al. (2001 ▶); Lima et al. (2004 ▶). For related structures and biological activity, see: da Silva Júnior et al. (2007 ▶, 2008 ▶); Lima et al. (2002 ▶). For the synthesis, see: da Silva Júnior et al. (2007 ▶, 2008 ▶). For geometric analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C20H15Br2NO3

M = 477.15

Triclinic,

a = 8.1430 (3) Å

b = 11.2584 (4) Å

c = 11.4742 (5) Å

α = 112.073 (2)°

β = 95.546 (2)°

γ = 108.696 (2)°

V = 894.70 (6) Å3

Z = 2

Mo Kα radiation

μ = 4.55 mm−1

T = 293 (2) K

0.31 × 0.28 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.272, T max = 0.490

9784 measured reflections

4099 independent reflections

3610 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.139

S = 1.09

4070 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −1.49 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034545/tk2311sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034545/tk2311Isup2.hkl

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

C20H15Br2NO3	Z = 2
Mr = 477.15	F000 = 472
Triclinic, P1	Dx = 1.771 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.1430 (3) Å	Cell parameters from 7882 reflections
b = 11.2584 (4) Å	θ = 1.0–27.5º
c = 11.4742 (5) Å	µ = 4.55 mm−1
α = 112.073 (2)º	T = 293 (2) K
β = 95.546 (2)º	Plate, colorless
γ = 108.696 (2)º	0.31 × 0.28 × 0.16 mm
V = 894.70 (6) Å3

Nonius KappaCCD diffractometer	4099 independent reflections
Radiation source: Enraf Nonius FR590	3610 reflections with I > 2σ(I)
Monochromator: horizonally mounted graphite crystal	Rint = 0.032
Detector resolution: 9 pixels mm-1	θmax = 27.5º
CCD rotation images, thick slices scans	θmin = 2.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.272, Tmax = 0.490	k = −14→14
9784 measured reflections	l = −14→14

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0642P)2 + 1.7472P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
4070 reflections	Δρmax = 0.59 e Å−3
235 parameters	Δρmin = −1.49 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Br1	0.13493 (6)	0.15969 (6)	0.15092 (5)	0.06302 (18)
Br2	0.61904 (6)	0.13670 (4)	−0.16856 (4)	0.04728 (15)
O1	0.5871 (4)	0.4358 (3)	0.6646 (3)	0.0405 (6)
O2	0.2827 (4)	−0.0404 (3)	0.4343 (3)	0.0475 (7)
O3	0.0912 (5)	−0.0405 (3)	0.6162 (4)	0.0647 (10)
N1	0.4572 (4)	0.2348 (4)	0.3578 (3)	0.0388 (7)
H1	0.3585	0.2460	0.3654	0.047*
C2	0.6940 (5)	0.3902 (4)	0.5704 (4)	0.0376 (8)
C3	0.5652 (5)	0.2412 (4)	0.4710 (4)	0.0343 (7)
H3	0.6291	0.1787	0.4452	0.041*
C3A	0.4399 (5)	0.2026 (4)	0.5504 (3)	0.0335 (7)
C4	0.3082 (5)	0.0695 (4)	0.5251 (4)	0.0355 (7)
C5	0.1911 (5)	0.0697 (4)	0.6241 (4)	0.0396 (8)
C5A	0.2076 (5)	0.2057 (4)	0.7271 (4)	0.0356 (7)
C6	0.0916 (5)	0.2100 (4)	0.8081 (4)	0.0430 (9)
H6	0.0005	0.1284	0.7967	0.052*
C7	0.1114 (6)	0.3356 (5)	0.9059 (4)	0.0487 (10)
H7	0.0348	0.3379	0.9610	0.058*
C8	0.2437 (7)	0.4573 (5)	0.9222 (5)	0.0503 (10)
H8	0.2560	0.5413	0.9882	0.060*
C9	0.3589 (6)	0.4550 (4)	0.8403 (4)	0.0449 (9)
H9	0.4480	0.5374	0.8514	0.054*
C9A	0.3410 (5)	0.3304 (4)	0.7427 (4)	0.0347 (7)
C9B	0.4547 (5)	0.3204 (4)	0.6524 (4)	0.0339 (7)
C1'	0.4990 (5)	0.2127 (4)	0.2403 (4)	0.0336 (7)
C2'	0.3688 (5)	0.1795 (4)	0.1324 (4)	0.0349 (7)
C3'	0.4010 (5)	0.1562 (4)	0.0115 (4)	0.0384 (8)
H3'	0.3101	0.1327	−0.0586	0.046*
C4'	0.5725 (5)	0.1686 (4)	−0.0031 (4)	0.0370 (8)
C5'	0.7048 (6)	0.2006 (5)	0.1004 (4)	0.0428 (9)
H5'	0.8189	0.2081	0.0898	0.051*
C6'	0.6691 (5)	0.2220 (4)	0.2212 (4)	0.0406 (8)
H6'	0.7597	0.2429	0.2904	0.049*
C1''	0.8530 (6)	0.3854 (5)	0.6478 (5)	0.0509 (10)
H1A	0.8108	0.3159	0.6791	0.076*
H1B	0.9175	0.4744	0.7201	0.076*
H1C	0.9308	0.3628	0.5930	0.076*
C2''	0.7497 (6)	0.4983 (4)	0.5182 (5)	0.0466 (9)
H2A	0.6454	0.4971	0.4703	0.070*
H2B	0.8268	0.4777	0.4621	0.070*
H2C	0.8124	0.5886	0.5891	0.070*

	U11	U22	U33	U12	U13	U23
Br1	0.0428 (3)	0.0937 (4)	0.0536 (3)	0.0282 (3)	0.0146 (2)	0.0306 (3)
Br2	0.0576 (3)	0.0534 (3)	0.0380 (2)	0.0228 (2)	0.02256 (19)	0.02340 (19)
O1	0.0463 (15)	0.0328 (12)	0.0396 (14)	0.0101 (11)	0.0189 (12)	0.0153 (11)
O2	0.0541 (17)	0.0357 (14)	0.0432 (16)	0.0129 (12)	0.0138 (13)	0.0105 (12)
O3	0.075 (2)	0.0385 (16)	0.074 (2)	0.0084 (15)	0.0367 (19)	0.0246 (16)
N1	0.0419 (17)	0.0533 (19)	0.0326 (16)	0.0262 (15)	0.0153 (13)	0.0222 (14)
C2	0.0393 (19)	0.0401 (19)	0.0381 (19)	0.0139 (15)	0.0151 (16)	0.0217 (16)
C3	0.0386 (18)	0.0405 (18)	0.0338 (18)	0.0199 (15)	0.0151 (15)	0.0209 (15)
C3A	0.0394 (18)	0.0368 (17)	0.0285 (16)	0.0143 (15)	0.0105 (14)	0.0184 (14)
C4	0.0398 (19)	0.0353 (17)	0.0323 (18)	0.0144 (15)	0.0083 (14)	0.0157 (14)
C5	0.0404 (19)	0.0386 (19)	0.041 (2)	0.0121 (15)	0.0120 (16)	0.0207 (16)
C5A	0.0364 (18)	0.0389 (18)	0.0357 (18)	0.0140 (15)	0.0106 (15)	0.0204 (15)
C6	0.0378 (19)	0.050 (2)	0.048 (2)	0.0166 (17)	0.0189 (17)	0.0268 (18)
C7	0.051 (2)	0.062 (3)	0.045 (2)	0.028 (2)	0.0240 (19)	0.027 (2)
C8	0.061 (3)	0.049 (2)	0.042 (2)	0.025 (2)	0.022 (2)	0.0159 (18)
C9	0.054 (2)	0.0382 (19)	0.041 (2)	0.0149 (17)	0.0172 (18)	0.0162 (17)
C9A	0.0393 (18)	0.0355 (17)	0.0302 (17)	0.0124 (14)	0.0101 (14)	0.0165 (14)
C9B	0.0392 (18)	0.0356 (17)	0.0329 (17)	0.0141 (14)	0.0123 (14)	0.0203 (14)
C1'	0.0389 (18)	0.0373 (17)	0.0314 (17)	0.0177 (15)	0.0121 (14)	0.0185 (14)
C2'	0.0329 (17)	0.0388 (18)	0.0382 (19)	0.0162 (14)	0.0122 (14)	0.0192 (15)
C3'	0.043 (2)	0.043 (2)	0.0331 (18)	0.0185 (16)	0.0097 (15)	0.0195 (16)
C4'	0.046 (2)	0.0383 (18)	0.0341 (18)	0.0186 (16)	0.0189 (16)	0.0199 (15)
C5'	0.041 (2)	0.055 (2)	0.044 (2)	0.0241 (18)	0.0193 (17)	0.0271 (19)
C6'	0.0374 (19)	0.055 (2)	0.0371 (19)	0.0220 (17)	0.0111 (15)	0.0235 (17)
C1''	0.042 (2)	0.054 (2)	0.055 (3)	0.0127 (18)	0.0059 (19)	0.029 (2)
C2''	0.052 (2)	0.044 (2)	0.056 (3)	0.0180 (18)	0.027 (2)	0.0305 (19)

Br1—C2'	1.887 (4)	C7—C8	1.377 (7)
Br2—C4'	1.895 (4)	C7—H7	0.9300
O1—C9B	1.344 (4)	C8—C9	1.389 (6)
O1—C2	1.497 (5)	C8—H8	0.9300
O2—C4	1.219 (5)	C9—C9A	1.379 (6)
O3—C5	1.210 (5)	C9—H9	0.9300
N1—C1'	1.374 (5)	C9A—C9B	1.451 (5)
N1—C3	1.461 (5)	C1'—C2'	1.394 (5)
N1—H1	0.8600	C1'—C6'	1.400 (5)
C2—C2''	1.514 (5)	C2'—C3'	1.379 (5)
C2—C1''	1.525 (6)	C3'—C4'	1.392 (5)
C2—C3	1.556 (5)	C3'—H3'	0.9300
C3—C3A	1.501 (5)	C4'—C5'	1.372 (6)
C3—H3	0.9800	C5'—C6'	1.391 (6)
C3A—C9B	1.360 (5)	C5'—H5'	0.9300
C3A—C4	1.436 (5)	C6'—H6'	0.9300
C4—C5	1.552 (5)	C1''—H1A	0.9600
C5—C5A	1.496 (5)	C1''—H1B	0.9600
C5A—C6	1.387 (5)	C1''—H1C	0.9600
C5A—C9A	1.406 (5)	C2''—H2A	0.9600
C6—C7	1.382 (6)	C2''—H2B	0.9600
C6—H6	0.9300	C2''—H2C	0.9600
C9B—O1—C2	107.1 (3)	C9A—C9—H9	120.0
C1'—N1—C3	125.9 (3)	C8—C9—H9	120.0
C1'—N1—H1	117.0	C9—C9A—C5A	119.9 (4)
C3—N1—H1	117.0	C9—C9A—C9B	122.9 (3)
O1—C2—C2''	106.1 (3)	C5A—C9A—C9B	117.2 (3)
O1—C2—C1''	106.1 (3)	O1—C9B—C3A	114.0 (3)
C2''—C2—C1''	112.7 (3)	O1—C9B—C9A	119.7 (3)
O1—C2—C3	104.0 (3)	C3A—C9B—C9A	126.2 (3)
C2''—C2—C3	116.4 (3)	N1—C1'—C2'	119.9 (3)
C1''—C2—C3	110.5 (3)	N1—C1'—C6'	123.5 (3)
N1—C3—C3A	106.9 (3)	C2'—C1'—C6'	116.6 (3)
N1—C3—C2	114.7 (3)	C3'—C2'—C1'	123.2 (3)
C3A—C3—C2	100.7 (3)	C3'—C2'—Br1	118.3 (3)
N1—C3—H3	111.3	C1'—C2'—Br1	118.5 (3)
C3A—C3—H3	111.3	C2'—C3'—C4'	118.5 (3)
C2—C3—H3	111.3	C2'—C3'—H3'	120.8
C9B—C3A—C4	121.3 (3)	C4'—C3'—H3'	120.8
C9B—C3A—C3	108.9 (3)	C5'—C4'—C3'	120.3 (3)
C4—C3A—C3	129.6 (3)	C5'—C4'—Br2	120.6 (3)
O2—C4—C3A	125.6 (4)	C3'—C4'—Br2	119.0 (3)
O2—C4—C5	118.8 (3)	C4'—C5'—C6'	120.3 (4)
C3A—C4—C5	115.6 (3)	C4'—C5'—H5'	119.8
O3—C5—C5A	122.3 (4)	C6'—C5'—H5'	119.8
O3—C5—C4	118.7 (4)	C5'—C6'—C1'	121.0 (4)
C5A—C5—C4	119.0 (3)	C5'—C6'—H6'	119.5
C6—C5A—C9A	119.5 (4)	C1'—C6'—H6'	119.5
C6—C5A—C5	120.3 (3)	C2—C1''—H1A	109.5
C9A—C5A—C5	120.3 (3)	C2—C1''—H1B	109.5
C7—C6—C5A	119.9 (4)	H1A—C1''—H1B	109.5
C7—C6—H6	120.0	C2—C1''—H1C	109.5
C5A—C6—H6	120.0	H1A—C1''—H1C	109.5
C8—C7—C6	120.5 (4)	H1B—C1''—H1C	109.5
C8—C7—H7	119.7	C2—C2''—H2A	109.5
C6—C7—H7	119.7	C2—C2''—H2B	109.5
C7—C8—C9	120.2 (4)	H2A—C2''—H2B	109.5
C7—C8—H8	119.9	C2—C2''—H2C	109.5
C9—C8—H8	119.9	H2A—C2''—H2C	109.5
C9A—C9—C8	119.9 (4)	H2B—C2''—H2C	109.5
C9B—O1—C2—C2''	143.2 (3)	C8—C9—C9A—C5A	−0.8 (6)
C9B—O1—C2—C1''	−96.7 (3)	C8—C9—C9A—C9B	179.1 (4)
C9B—O1—C2—C3	19.9 (4)	C6—C5A—C9A—C9	2.0 (6)
C1'—N1—C3—C3A	−154.9 (4)	C5—C5A—C9A—C9	−178.1 (4)
C1'—N1—C3—C2	94.4 (4)	C6—C5A—C9A—C9B	−177.9 (4)
O1—C2—C3—N1	92.0 (3)	C5—C5A—C9A—C9B	2.1 (5)
C2''—C2—C3—N1	−24.3 (5)	C2—O1—C9B—C3A	−8.8 (4)
C1''—C2—C3—N1	−154.5 (3)	C2—O1—C9B—C9A	172.6 (3)
O1—C2—C3—C3A	−22.4 (3)	C4—C3A—C9B—O1	178.5 (3)
C2''—C2—C3—C3A	−138.7 (3)	C3—C3A—C9B—O1	−6.9 (4)
C1''—C2—C3—C3A	91.1 (4)	C4—C3A—C9B—C9A	−3.0 (6)
N1—C3—C3A—C9B	−101.7 (4)	C3—C3A—C9B—C9A	171.6 (3)
C2—C3—C3A—C9B	18.4 (4)	C9—C9A—C9B—O1	1.7 (6)
N1—C3—C3A—C4	72.3 (5)	C5A—C9A—C9B—O1	−178.5 (3)
C2—C3—C3A—C4	−167.6 (4)	C9—C9A—C9B—C3A	−176.7 (4)
C9B—C3A—C4—O2	178.0 (4)	C5A—C9A—C9B—C3A	3.1 (6)
C3—C3A—C4—O2	4.7 (7)	C3—N1—C1'—C2'	166.3 (3)
C9B—C3A—C4—C5	−2.1 (5)	C3—N1—C1'—C6'	−14.0 (6)
C3—C3A—C4—C5	−175.4 (3)	N1—C1'—C2'—C3'	179.8 (3)
O2—C4—C5—O3	7.7 (6)	C6'—C1'—C2'—C3'	0.1 (5)
C3A—C4—C5—O3	−172.1 (4)	N1—C1'—C2'—Br1	−2.3 (5)
O2—C4—C5—C5A	−173.3 (4)	C6'—C1'—C2'—Br1	178.0 (3)
C3A—C4—C5—C5A	6.8 (5)	C1'—C2'—C3'—C4'	−1.1 (6)
O3—C5—C5A—C6	−8.0 (6)	Br1—C2'—C3'—C4'	−179.0 (3)
C4—C5—C5A—C6	173.1 (4)	C2'—C3'—C4'—C5'	1.3 (6)
O3—C5—C5A—C9A	172.0 (4)	C2'—C3'—C4'—Br2	179.9 (3)
C4—C5—C5A—C9A	−6.9 (5)	C3'—C4'—C5'—C6'	−0.4 (6)
C9A—C5A—C6—C7	−2.1 (6)	Br2—C4'—C5'—C6'	−179.1 (3)
C5—C5A—C6—C7	177.9 (4)	C4'—C5'—C6'—C1'	−0.6 (6)
C5A—C6—C7—C8	1.2 (7)	N1—C1'—C6'—C5'	−179.0 (4)
C6—C7—C8—C9	0.0 (7)	C2'—C1'—C6'—C5'	0.7 (6)
C7—C8—C9—C9A	−0.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.98	2.64	3.347 (6)	129
C1''—H1A···O2i	0.96	2.67	3.389 (6)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.98	2.64	3.347 (6)	129
C1′′—H1A⋯O2i	0.96	2.67	3.389 (6)	132

Symmetry code: (i) .