N-(3-Bromo-1,4-dioxo-1,4-dihydro-2-naphth­yl)-4-fluoro-N-(4-fluoro­benzo­yl)benzamide

Akinboye, E.S.; Butcher, R.J.; Wright, D.A.; Brandy, Y.; Bakare, O.

doi:10.1107/S1600536809000117

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o277

doi:10.1107/S1600536809000117

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N-(3-Bromo-1,4-dioxo-1,4-dihydro-2-naphthyl)-4-fluoro-N-(4-fluorobenzoyl)benzamide

Emmanuel S. Akinboye,^a Ray J. Butcher,^a ^* Dwayne A. Wright,^a Yakini Brandy ^a and Oladapo Bakare ^a

^aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 30 December 2008; accepted 2 January 2009; online 10 January 2009)

In the title compound, C₂₄H₁₂BrF₂NO₄, synthesized from 2-amino-3-bromo-1,4-naphthoquinone and 4-fluorobenzoyl chloride, the two p-fluorophenyl 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 fluorophenyl 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 intermolecular F⋯O contact of 2.982 (5) Å and a Br⋯O contact of 2.977 (4) Å. In addition, the molecules are linked by weak intermolecular C—H⋯O and C—H⋯F interactions.

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_r = 496.26
Monoclinic, P 2₁ /n
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 $[Oxford Diffraction (2007). CrysAlisPro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) 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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.158
S = 1.14
3802 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 1.29 e Å⁻³
Δρ_min = −0.51 e Å⁻³

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) -x, -y+2, -z; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlisPro (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlisPro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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.

Supporting information

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

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

checkCIF report

Comment top

We have developed some imido-substituted 2-chloro-1,4-naphthoquinones with cytotoxic activities on some cancer cell lines (Bakare et al., 2003; Berhe et al., 2008); and have recently reported on the crystal structure of N-(3-bromo-1,4-dioxo- 1,4-dihydro-naphthalen-2-yl)-2-chloro-N-(2-chloro-benzoyl)-benzamide (Akinboye et al., 2009). In continuation of our work, the title compound C₂₄H₁₂BrF₂NO₄, (I), was synthesized as a potential anticancer agent.

The crystal structure shows that the two p-fluorophenyl rings are inclined at 73.9 (1) and 73.6 (1)° to the naphthoquinone ring. The two imido carbonyl oxygen atoms are anti-to each other, while fluorophenyl rings are placed facing each other and connected to the imide moiety in a funnel-like arrangement. This conformation allowed the fluorine groups in the para position of each fluorophenyl ring to be oriented slightly away from each other. An examination of the packing shows a close contact between F1A and O2 at (1/2 - x, 1/2 + y, 1/2 - z) (2.982 (5)Å) and between C2 and O1B at (1/2 - x, -1/2 + y, 1/2 - z) (2.977 (4)Å). In addition, the molecules are linked by weak intermolecular C—H···O and C—H···F interactions (Table 1).

Related literature top

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 top

To a solution 2-amino-3-bromo-1,4-naphthoquinone (300 mg, 1.19 mmol) in dry THF was added NaH (68.64 mg 2.86 mmol) and the mixture was stirred for 15 minutes. 4-Fluoro-benzoylchloride (0.35 ml, 2.86 mmol) was added thereafter and this mixture was stirred at room temperature for 16–24 hr under argon. The solvent was removed in vacuo and the solid residue was dissolved in dichloromethane (40 ml). The resultant solution was washed with water (3 x 15 ml), saturated NaCl solution (2 x 15 ml) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo and the residue recrystallized from ethyl acetate to obtain a yellow solid (391.0 g m). Further recrystallization was carried out in ethanol to furnish the title imide (340.2 mg, 57%).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 20% probability level.
	Fig. 2. View of the packing viewed down the a axis. Dashed bonds show weak C—H···F interactions as well as the close Br···O intermolecular contact.

N-(3-Bromo-1,4-dioxo-1,4-dihydro-2-naphthyl)-4-fluoro-N- (4-fluorobenzoyl)benzamide top

Crystal data top

C₂₄H₁₂BrF₂NO₄	F(000) = 992
M_r = 496.26	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0639P)² + 6.5199P] where P = (F_o² + 2F_c²)/3
3802 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 1.29 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₂₄H₁₂BrF₂NO₄	V = 1979.88 (6) Å³
M_r = 496.26	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 14.5931 (3) Å	µ = 3.30 mm⁻¹
b = 6.6471 (1) Å	T = 200 K
c = 20.6324 (4) Å	0.53 × 0.48 × 0.32 mm
β = 98.407 (2)°

Data collection top

Oxford Diffraction Gemini R diffractometer	3802 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	3362 reflections with I > 2σ(I)
T_min = 0.230, T_max = 0.348	R_int = 0.023
7835 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.14	Δρ_max = 1.29 e Å⁻³
3802 reflections	Δρ_min = −0.51 e Å⁻³
289 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	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+2, −z; (ii) x+1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₂BrF₂NO₄
M_r	496.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	14.5931 (3), 6.6471 (1), 20.6324 (4)
β (°)	98.407 (2)
V (Å³)	1979.88 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.30
Crystal size (mm)	0.53 × 0.48 × 0.32

Data collection
Diffractometer	Oxford Diffraction Gemini R diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.230, 0.348
No. of measured, independent and observed [I > 2σ(I)] reflections	7835, 3802, 3362
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.158, 1.14
No. of reflections	3802
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.29, −0.51

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1Bⁱ	0.95	2.56	3.297 (6)	135.1
C4—H4A···F1Aⁱⁱ	0.95	2.40	3.266 (6)	151.4

Symmetry codes: (i) −x, −y+2, −z; (ii) x+1/2, −y+3/2, z−1/2.

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Akinboye, E. S., Butcher, R. J., Brandy, Y., Adesiyun, T. A. & Bakare, O. (2009). Acta Cryst. E65, o24. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bakare, O., Ashendel, C. L., Peng, H., Zalkow, L. H. & Burgess, E. M. (2003). Bioorg. Med. Chem. 11, 3165–3170. Web of Science CrossRef PubMed CAS Google Scholar
Berhe, S., Kanaan, Y., Copeland, R. L., Wright, D. A., Zalkow, L. H. & Bakare, O. (2008). Lett. Drug Des. Disc. 5, 485–488. CrossRef CAS Google Scholar
Huang, L., Chang, F., Lee, K., Wang, J., Teng, C. & Kuo, S. (2005). Bioorg. Med. Chem. 6, 2261–2269. Web of Science CrossRef Google Scholar
Lien, J., Huang, L., Wang, J., Teng, C., Lee, K. & Kuo, S. (1997). Bioorg. Med. Chem. 5, 2111–2120. Web of Science CrossRef CAS PubMed Google Scholar
Oxford Diffraction (2007). CrysAlisPro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Rubin-Preminger, J. M., Win, T., Granot, Y. & Bittner, S. (2004). Z. Kristallogr. New Cryst. Struct. 219, o323. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Win, T., Yerushalmi, S. & Bittner, S. (2005). Synthesis, p. 1631. Google Scholar

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Volume 65| Part 2| February 2009| Page o277

doi:10.1107/S1600536809000117

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-(3-Bromo-1,4-dioxo-1,4-di­hydro-2-naphth­yl)-4-fluoro-N-(4-fluoro­benzo­yl)benzamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(3-Bromo-1,4-dioxo-1,4-dihydro-2-naphthyl)-4-fluoro-N-(4-fluorobenzoyl)benzamide