N-(3-Bromo-1,4-dioxo-1,4-dihydro-2-naphth-yl)-4-fluoro-N-(4-fluoro-benzo-yl)benzamide.

In the title compound, C(24)H(12)BrF(2)NO(4), synthesized from 2-amino-3-bromo-1,4-naphthoquinone and 4-fluoro-benzoyl chloride, the two p-fluoro-phenyl rings are inclined at 73.9 (1) and 73.6 (1)° to the naphthoquinone ring system. The two imido carbonyl O atoms are anti to each other, while the fluoro-phenyl rings are located opposite each other, connected to the imide group in a funnel-like arrangement. This conformation allows the fluorine groups be oriented slightly away from each other. An examination of the packing shows a close inter-molecular F⋯O contact of 2.982 (5) Å and a Br⋯O contact of 2.977 (4) Å. In addition, the mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯F inter-actions.

Related literature

For similar structures, see: Lien et al. (1997 ▶); Huang et al. (2005 ▶); Bakare et al. (2003 ▶); Akinboye et al. (2009 ▶); Win et al. (2005 ▶); Rubin-Preminger et al. (2004 ▶). For general background, see: Berhe et al. (2008 ▶).

Experimental

Crystal data

C24H12BrF2NO4

M = 496.26

Monoclinic,

a = 14.5931 (3) Å

b = 6.6471 (1) Å

c = 20.6324 (4) Å

β = 98.407 (2)°

V = 1979.88 (6) Å3

Z = 4

Cu Kα radiation

μ = 3.30 mm−1

T = 200 (2) K

0.53 × 0.48 × 0.32 mm

Data collection

Oxford Diffraction Gemini R diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.230, T max = 0.348

7835 measured reflections

3802 independent reflections

3362 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.158

S = 1.14

3802 reflections

289 parameters

H-atom parameters constrained

Δρmax = 1.29 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000117/bq2117sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000117/bq2117Isup2.hkl

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

C24H12BrF2NO4	F(000) = 992
Mr = 496.26	Dx = 1.665 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 5844 reflections
a = 14.5931 (3) Å	θ = 4.0–73.4°
b = 6.6471 (1) Å	µ = 3.30 mm−1
c = 20.6324 (4) Å	T = 200 K
β = 98.407 (2)°	Prism, pale yellow
V = 1979.88 (6) Å3	0.53 × 0.48 × 0.32 mm
Z = 4

Oxford Diffraction Gemini R diffractometer	3802 independent reflections
Radiation source: fine-focus sealed tube	3362 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 10.5081 pixels mm-1	θmax = 73.6°, θmin = 4.0°
φ and ω scans	h = −17→18
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −8→5
Tmin = 0.230, Tmax = 0.348	l = −25→25
7835 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0639P)2 + 6.5199P] where P = (Fo2 + 2Fc2)/3
3802 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 1.29 e Å−3
0 restraints	Δρmin = −0.51 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
Br	0.22095 (3)	0.70099 (8)	0.19146 (2)	0.0444 (2)
F1A	−0.2690 (2)	0.9709 (5)	0.41727 (16)	0.0599 (8)
F1B	0.1251 (3)	0.7110 (6)	0.52944 (16)	0.0752 (11)
O1	0.1976 (2)	0.7543 (6)	0.04619 (17)	0.0448 (8)
O2	−0.1290 (2)	0.8464 (5)	0.12723 (16)	0.0439 (8)
O1A	−0.0683 (2)	0.4826 (5)	0.21656 (17)	0.0479 (8)
O1B	0.0933 (2)	1.0688 (5)	0.24341 (15)	0.0424 (7)
N	0.0163 (2)	0.7707 (6)	0.22161 (18)	0.0358 (8)
C1	0.1109 (3)	0.7445 (7)	0.1341 (2)	0.0330 (9)
C2	0.1213 (3)	0.7515 (6)	0.0634 (2)	0.0335 (9)
C3	0.0344 (3)	0.7515 (6)	0.0152 (2)	0.0336 (9)
C4	0.0391 (3)	0.7337 (7)	−0.0509 (2)	0.0386 (10)
H4A	0.0976	0.7218	−0.0656	0.046*
C5	−0.0414 (4)	0.7333 (6)	−0.0961 (2)	0.0404 (10)
H5A	−0.0380	0.7208	−0.1415	0.048*
C6	−0.1272 (3)	0.7512 (7)	−0.0744 (2)	0.0395 (10)
H6A	−0.1824	0.7503	−0.1051	0.047*
C7	−0.1317 (3)	0.7702 (7)	−0.0086 (2)	0.0375 (10)
H7A	−0.1903	0.7830	0.0059	0.045*
C8	−0.0513 (3)	0.7706 (6)	0.0370 (2)	0.0333 (9)
C9	−0.0579 (3)	0.7970 (6)	0.1070 (2)	0.0343 (9)
C10	0.0287 (3)	0.7658 (6)	0.1550 (2)	0.0324 (9)
C1A	−0.0557 (3)	0.6469 (7)	0.2405 (2)	0.0372 (10)
C2A	−0.1127 (3)	0.7365 (7)	0.2871 (2)	0.0363 (9)
C3A	−0.1389 (3)	0.9372 (7)	0.2822 (2)	0.0389 (10)
H3AA	−0.1194	1.0199	0.2493	0.047*
C4A	−0.1936 (3)	1.0168 (8)	0.3254 (2)	0.0424 (10)
H4AA	−0.2131	1.1532	0.3222	0.051*
C5A	−0.2187 (3)	0.8922 (9)	0.3732 (2)	0.0457 (11)
C6A	−0.1944 (4)	0.6934 (8)	0.3788 (3)	0.0492 (12)
H6AA	−0.2135	0.6120	0.4122	0.059*
C7A	−0.1415 (3)	0.6137 (8)	0.3348 (2)	0.0444 (11)
H7AA	−0.1248	0.4754	0.3371	0.053*
C1B	0.0646 (3)	0.9152 (7)	0.2643 (2)	0.0354 (9)
C2B	0.0816 (3)	0.8578 (8)	0.3349 (2)	0.0382 (10)
C3B	0.0772 (3)	1.0046 (8)	0.3817 (2)	0.0452 (11)
H3BA	0.0641	1.1397	0.3685	0.054*
C4B	0.0918 (4)	0.9575 (10)	0.4476 (3)	0.0529 (13)
H4BA	0.0880	1.0576	0.4799	0.063*
C5B	0.1121 (4)	0.7597 (10)	0.4649 (3)	0.0544 (14)
C6B	0.1210 (3)	0.6130 (9)	0.4200 (3)	0.0517 (13)
H6BA	0.1377	0.4798	0.4337	0.062*
C7B	0.1051 (3)	0.6619 (8)	0.3541 (2)	0.0430 (11)
H7BA	0.1103	0.5616	0.3220	0.052*

	U11	U22	U33	U12	U13	U23
Br	0.0270 (3)	0.0572 (4)	0.0469 (3)	0.0056 (2)	−0.00134 (19)	0.0002 (2)
F1A	0.0519 (17)	0.068 (2)	0.0664 (19)	0.0020 (15)	0.0300 (15)	−0.0024 (16)
F1B	0.084 (3)	0.098 (3)	0.0405 (17)	−0.006 (2)	−0.0033 (16)	0.0140 (17)
O1	0.0291 (15)	0.057 (2)	0.0496 (19)	0.0045 (14)	0.0103 (13)	−0.0014 (16)
O2	0.0304 (15)	0.058 (2)	0.0429 (17)	0.0055 (15)	0.0043 (13)	−0.0034 (15)
O1A	0.0466 (19)	0.0395 (19)	0.059 (2)	−0.0065 (15)	0.0130 (16)	−0.0070 (16)
O1B	0.0404 (17)	0.0418 (18)	0.0429 (17)	−0.0065 (14)	−0.0012 (13)	−0.0001 (14)
N	0.0286 (17)	0.042 (2)	0.0366 (19)	−0.0023 (15)	0.0036 (14)	−0.0002 (15)
C1	0.0211 (18)	0.033 (2)	0.043 (2)	0.0010 (16)	−0.0030 (16)	−0.0005 (17)
C2	0.032 (2)	0.025 (2)	0.043 (2)	0.0023 (16)	0.0040 (17)	−0.0023 (17)
C3	0.033 (2)	0.026 (2)	0.041 (2)	0.0018 (17)	0.0048 (17)	0.0015 (17)
C4	0.044 (3)	0.029 (2)	0.043 (2)	0.0020 (19)	0.0075 (19)	0.0007 (18)
C5	0.056 (3)	0.023 (2)	0.041 (2)	0.0026 (19)	0.006 (2)	−0.0002 (17)
C6	0.045 (3)	0.027 (2)	0.043 (2)	−0.0013 (19)	−0.006 (2)	0.0010 (18)
C7	0.031 (2)	0.034 (2)	0.046 (2)	0.0018 (18)	0.0000 (18)	0.0016 (18)
C8	0.030 (2)	0.027 (2)	0.042 (2)	−0.0008 (16)	0.0012 (17)	0.0009 (17)
C9	0.027 (2)	0.033 (2)	0.042 (2)	−0.0026 (17)	0.0021 (17)	0.0000 (17)
C10	0.031 (2)	0.026 (2)	0.040 (2)	−0.0008 (16)	0.0012 (17)	0.0000 (16)
C1A	0.030 (2)	0.042 (3)	0.039 (2)	−0.0005 (19)	0.0017 (17)	0.0016 (19)
C2A	0.027 (2)	0.042 (2)	0.039 (2)	−0.0057 (18)	0.0015 (17)	0.0000 (18)
C3A	0.030 (2)	0.046 (3)	0.040 (2)	−0.0022 (19)	0.0029 (17)	0.0060 (19)
C4A	0.030 (2)	0.046 (3)	0.051 (3)	0.0027 (19)	0.0042 (19)	0.003 (2)
C5A	0.030 (2)	0.062 (3)	0.046 (3)	−0.003 (2)	0.0092 (19)	−0.002 (2)
C6A	0.045 (3)	0.051 (3)	0.055 (3)	−0.005 (2)	0.015 (2)	0.009 (2)
C7A	0.039 (2)	0.041 (3)	0.054 (3)	−0.004 (2)	0.009 (2)	0.004 (2)
C1B	0.0225 (18)	0.042 (3)	0.041 (2)	−0.0030 (17)	0.0015 (16)	−0.0013 (19)
C2B	0.0250 (19)	0.049 (3)	0.040 (2)	−0.0066 (19)	0.0008 (16)	0.000 (2)
C3B	0.036 (2)	0.050 (3)	0.049 (3)	−0.004 (2)	0.003 (2)	−0.002 (2)
C4B	0.046 (3)	0.069 (4)	0.043 (3)	−0.008 (3)	0.004 (2)	−0.007 (2)
C5B	0.040 (3)	0.083 (4)	0.039 (3)	−0.012 (3)	−0.001 (2)	0.010 (3)
C6B	0.035 (2)	0.062 (3)	0.056 (3)	0.002 (2)	−0.002 (2)	0.011 (3)
C7B	0.029 (2)	0.051 (3)	0.048 (3)	0.003 (2)	−0.0004 (18)	0.002 (2)

Br—C1	1.873 (4)	C9—C10	1.503 (6)
F1A—C5A	1.353 (6)	C1A—C2A	1.486 (6)
F1B—C5B	1.356 (6)	C2A—C3A	1.387 (7)
O1—C2	1.217 (5)	C2A—C7A	1.390 (7)
O2—C9	1.218 (5)	C3A—C4A	1.385 (7)
O1A—C1A	1.201 (6)	C3A—H3AA	0.9500
O1B—C1B	1.207 (6)	C4A—C5A	1.378 (7)
N—C10	1.412 (6)	C4A—H4AA	0.9500
N—C1B	1.419 (6)	C5A—C6A	1.369 (8)
N—C1A	1.433 (6)	C6A—C7A	1.381 (7)
C1—C10	1.340 (6)	C6A—H6AA	0.9500
C1—C2	1.489 (6)	C7A—H7AA	0.9500
C2—C3	1.493 (6)	C1B—C2B	1.492 (6)
C3—C4	1.382 (6)	C2B—C3B	1.381 (7)
C3—C8	1.395 (6)	C2B—C7B	1.390 (7)
C4—C5	1.388 (7)	C3B—C4B	1.380 (7)
C4—H4A	0.9500	C3B—H3BA	0.9500
C5—C6	1.395 (7)	C4B—C5B	1.383 (9)
C5—H5A	0.9500	C4B—H4BA	0.9500
C6—C7	1.374 (7)	C5B—C6B	1.365 (9)
C6—H6A	0.9500	C6B—C7B	1.384 (7)
C7—C8	1.393 (6)	C6B—H6BA	0.9500
C7—H7A	0.9500	C7B—H7BA	0.9500
C8—C9	1.473 (6)
C10—N—C1B	119.8 (4)	C7A—C2A—C1A	118.6 (4)
C10—N—C1A	117.0 (4)	C4A—C3A—C2A	119.9 (4)
C1B—N—C1A	122.5 (4)	C4A—C3A—H3AA	120.0
C10—C1—C2	122.5 (4)	C2A—C3A—H3AA	120.0
C10—C1—Br	122.5 (3)	C5A—C4A—C3A	118.0 (5)
C2—C1—Br	115.0 (3)	C5A—C4A—H4AA	121.0
O1—C2—C1	121.0 (4)	C3A—C4A—H4AA	121.0
O1—C2—C3	122.0 (4)	F1A—C5A—C6A	118.4 (5)
C1—C2—C3	117.0 (4)	F1A—C5A—C4A	118.4 (5)
C4—C3—C8	120.1 (4)	C6A—C5A—C4A	123.2 (5)
C4—C3—C2	119.9 (4)	C5A—C6A—C7A	118.6 (5)
C8—C3—C2	120.0 (4)	C5A—C6A—H6AA	120.7
C3—C4—C5	120.3 (4)	C7A—C6A—H6AA	120.7
C3—C4—H4A	119.8	C6A—C7A—C2A	119.7 (5)
C5—C4—H4A	119.8	C6A—C7A—H7AA	120.1
C4—C5—C6	119.7 (4)	C2A—C7A—H7AA	120.1
C4—C5—H5A	120.2	O1B—C1B—N	121.2 (4)
C6—C5—H5A	120.2	O1B—C1B—C2B	123.3 (4)
C7—C6—C5	120.0 (4)	N—C1B—C2B	115.4 (4)
C7—C6—H6A	120.0	C3B—C2B—C7B	119.9 (4)
C5—C6—H6A	120.0	C3B—C2B—C1B	119.0 (4)
C6—C7—C8	120.7 (4)	C7B—C2B—C1B	121.1 (4)
C6—C7—H7A	119.7	C4B—C3B—C2B	120.8 (5)
C8—C7—H7A	119.7	C4B—C3B—H3BA	119.6
C7—C8—C3	119.3 (4)	C2B—C3B—H3BA	119.6
C7—C8—C9	119.6 (4)	C3B—C4B—C5B	117.8 (5)
C3—C8—C9	121.1 (4)	C3B—C4B—H4BA	121.1
O2—C9—C8	123.4 (4)	C5B—C4B—H4BA	121.1
O2—C9—C10	119.2 (4)	F1B—C5B—C6B	118.9 (6)
C8—C9—C10	117.4 (4)	F1B—C5B—C4B	118.3 (5)
C1—C10—N	124.3 (4)	C6B—C5B—C4B	122.8 (5)
C1—C10—C9	120.6 (4)	C5B—C6B—C7B	118.7 (5)
N—C10—C9	115.0 (4)	C5B—C6B—H6BA	120.6
O1A—C1A—N	119.0 (4)	C7B—C6B—H6BA	120.6
O1A—C1A—C2A	124.3 (4)	C6B—C7B—C2B	119.9 (5)
N—C1A—C2A	116.6 (4)	C6B—C7B—H7BA	120.1
C3A—C2A—C7A	120.6 (4)	C2B—C7B—H7BA	120.1
C3A—C2A—C1A	120.8 (4)
C10—C1—C2—O1	171.7 (4)	C1B—N—C1A—O1A	−150.5 (4)
Br—C1—C2—O1	−8.9 (6)	C10—N—C1A—C2A	−138.8 (4)
C10—C1—C2—C3	−9.3 (6)	C1B—N—C1A—C2A	31.9 (6)
Br—C1—C2—C3	170.1 (3)	O1A—C1A—C2A—C3A	−138.5 (5)
O1—C2—C3—C4	6.7 (7)	N—C1A—C2A—C3A	39.0 (6)
C1—C2—C3—C4	−172.3 (4)	O1A—C1A—C2A—C7A	39.8 (7)
O1—C2—C3—C8	−172.9 (4)	N—C1A—C2A—C7A	−142.8 (4)
C1—C2—C3—C8	8.1 (6)	C7A—C2A—C3A—C4A	0.5 (7)
C8—C3—C4—C5	−0.5 (6)	C1A—C2A—C3A—C4A	178.8 (4)
C2—C3—C4—C5	179.9 (4)	C2A—C3A—C4A—C5A	1.2 (7)
C3—C4—C5—C6	0.1 (7)	C3A—C4A—C5A—F1A	177.4 (4)
C4—C5—C6—C7	0.3 (7)	C3A—C4A—C5A—C6A	−1.8 (7)
C5—C6—C7—C8	−0.3 (7)	F1A—C5A—C6A—C7A	−178.6 (5)
C6—C7—C8—C3	−0.1 (7)	C4A—C5A—C6A—C7A	0.5 (8)
C6—C7—C8—C9	178.3 (4)	C5A—C6A—C7A—C2A	1.3 (8)
C4—C3—C8—C7	0.5 (6)	C3A—C2A—C7A—C6A	−1.8 (7)
C2—C3—C8—C7	−179.9 (4)	C1A—C2A—C7A—C6A	179.9 (4)
C4—C3—C8—C9	−177.8 (4)	C10—N—C1B—O1B	22.6 (6)
C2—C3—C8—C9	1.8 (6)	C1A—N—C1B—O1B	−147.9 (4)
C7—C8—C9—O2	−10.5 (7)	C10—N—C1B—C2B	−154.1 (4)
C3—C8—C9—O2	167.7 (4)	C1A—N—C1B—C2B	35.4 (6)
C7—C8—C9—C10	171.1 (4)	O1B—C1B—C2B—C3B	40.0 (6)
C3—C8—C9—C10	−10.6 (6)	N—C1B—C2B—C3B	−143.5 (4)
C2—C1—C10—N	−176.5 (4)	O1B—C1B—C2B—C7B	−137.4 (5)
Br—C1—C10—N	4.1 (6)	N—C1B—C2B—C7B	39.1 (6)
C2—C1—C10—C9	0.4 (6)	C7B—C2B—C3B—C4B	−3.1 (7)
Br—C1—C10—C9	−179.0 (3)	C1B—C2B—C3B—C4B	179.5 (4)
C1B—N—C10—C1	56.5 (6)	C2B—C3B—C4B—C5B	0.9 (7)
C1A—N—C10—C1	−132.5 (5)	C3B—C4B—C5B—F1B	−179.0 (5)
C1B—N—C10—C9	−120.6 (4)	C3B—C4B—C5B—C6B	2.1 (8)
C1A—N—C10—C9	50.5 (5)	F1B—C5B—C6B—C7B	178.2 (5)
O2—C9—C10—C1	−168.8 (4)	C4B—C5B—C6B—C7B	−2.9 (8)
C8—C9—C10—C1	9.6 (6)	C5B—C6B—C7B—C2B	0.7 (7)
O2—C9—C10—N	8.3 (6)	C3B—C2B—C7B—C6B	2.2 (7)
C8—C9—C10—N	−173.2 (4)	C1B—C2B—C7B—C6B	179.6 (4)
C10—N—C1A—O1A	38.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1Bi	0.95	2.56	3.297 (6)	135
C4—H4A···F1Aii	0.95	2.40	3.266 (6)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1Bi	0.95	2.56	3.297 (6)	135
C4—H4A⋯F1Aii	0.95	2.40	3.266 (6)	151

Symmetry codes: (i) ; (ii) .