N-(3-Bromo-1,4-dioxo-1,4-dihydro-2-naphth­yl)-2-chloro-N-(2-chloro­benzoyl)benzamide

Akinboye, E.S.; Butcher, R.J.; Brandy, Y.; Adesiyun, T.A.; Bakare, O.

doi:10.1107/S1600536808039214

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o24

doi:10.1107/S1600536808039214

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N-(3-Bromo-1,4-dioxo-1,4-dihydro-2-naphthyl)-2-chloro-N-(2-chlorobenzoyl)benzamide

Emmanuel S. Akinboye,^a Ray J. Butcher,^a ^* Yakini Brandy,^a Tolulope A. Adesiyun ^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 9 October 2008; accepted 21 November 2008; online 6 December 2008)

The title compound, C₂₄H₁₂BrCl₂NO₄, was synthesized from 2-amino-3-bromo-1,4-naphthoquinone and 2-chlorobenzoyl chloride. The crystal structure shows that each of the chlorophenyl rings is inclined at about 60° to the naphthoquinone ring system. The two chlorophenyl rings adopt a conformation that ensures that chlorine substituents are anti so as to reduce electronic repulsion. An examination of the packing shows close O⋯Br and Cl⋯Cl contacts of 2.947 (2) and 3.346 (1) Å, respectively. In addition, the molecules are linked by weak intermolecular C—H⋯O and C—H⋯Cl interactions.

Related literature

For similar structures, see: Lien et al. (1997 ); Huang et al. (1998 ); Bakare et al. (2003 ); Copeland et al. (2007 ); Win et al. (2005 ); Rubin-Preminger et al. (2004 ). For the properties of compounds with the chloro-1,4-naphthoquinone skeleton, see: Chang et al. (1999 ); Ertl et al. (1999 ).

Experimental

Crystal data

C₂₄H₁₂BrCl₂NO₄
M_r = 529.16
Monoclinic, P 2₁ /n
a = 12.8590 (3) Å
b = 7.81260 (10) Å
c = 21.9574 (4) Å
β = 106.272 (2)°
V = 2117.53 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.23 mm⁻¹
T = 200 (2) K
0.46 × 0.18 × 0.15 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.945, T_max = 1.000 (expected range = 0.676–0.716)
27164 measured reflections
8407 independent reflections
4388 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.123
S = 0.92
8407 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 2.03 e Å⁻³
Δρ_min = −0.70 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	2.51	3.209 (3)	131
C4B—H4BA⋯O1ⁱⁱ	0.95	2.67	3.335 (3)	128
C6B—H6BA⋯O2ⁱⁱⁱ	0.95	2.65	3.296 (3)	126
Symmetry codes: (i) -x, -y, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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/S1600536808039214/bq2099sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039214/bq2099Isup2.hkl

checkCIF report

Comment top

Certain compounds with the chloro-1,4-naphthoquinone skeleton were reported to exhibit antineoplastic property and some have inhibitory effects on human cytomegalovirus (HCMV) protease (Chang et al., 1999; Ertl et al., 1999). The amido and imido derivatives of 3-chloro-1,4-naphthoquinone have been reported to exhibit appreciable anti-inflammatory, antiplatelet, antiallergic and anticancer activities (Lien et al., 1997; Huang et al., 1998; Bakare et al., 2003; Copeland et al.,2007) We have developed some imido-substituted 2-chloro-1,4-naphthoquinones with cytotoxic activities on some prostate cancer cell lines. In continuation of our work, the title compound (I) was synthesized as a potential anticancer agent.

Each of the phenyl groups is inclined at about 60° to the naphthoquinone ring of the titled compound C₂₄H₁₂BrCl₂NO₄. The two chlorophenyl rings adopt a conformation that ensures that chlorine substituents are anti to each other so as to reduce electronic repulsion. An examination of the packing shows close contacts between O1A and Br at (1/2 - x, 1/2 + y, 3/2 - z) (2.947 (2) Å) and Cl1A and Cl1B at (x, 1 + y, z) (3.346 (1) Å). The explanation of these close contacts lies in a balance between the torsion angles subtended at the N which balances short intramolecular contacts against short intermolecular contacts and comes up with the best compromise.

Related literature top

For similar structures, see: Lien et al. (1997); Huang et al. (1998); Bakare et al. (2003); Copeland et al. (2007); Win et al. (2005); Rubin-Preminger et al. (2004). For the properties of compounds with the chloro-1,4-naphthoquinone skeleton, see: Chang et al. (1999); Ertl et al. (1999).

Experimental top

To a solution of 2-amino-3-bromo-1,4-naphthoquinone (300 mg, 1.21 mmol) in dry THF was added NaH (72.6 mg 3.025 mmol) and the mixture was stirred for 15 minutes. 2-Chloro-benzoylchloride (0.37 ml) 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 triturated in ethyl acetate to give a yellow solid (280.0 g m). This was recrystallized in ethyl acetate to furnish the title imide (214.2 mg, 34%).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (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···O interactions and close Cl···Cl contacts.

N-(3-Bromo-1,4-dioxo-1,4-dihydro-2-naphthyl)-2-chloro-N-(2- chlorobenzoyl)benzamide top

Crystal data top

C₂₄H₁₂BrCl₂NO₄	F(000) = 1056
M_r = 529.16	D_x = 1.660 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.8590 (3) Å	Cell parameters from 6385 reflections
b = 7.8126 (1) Å	θ = 4.5–34.8°
c = 21.9574 (4) Å	µ = 2.23 mm⁻¹
β = 106.272 (2)°	T = 200 K
V = 2117.53 (7) Å³	Needle, pale yellow
Z = 4	0.46 × 0.18 × 0.15 mm

Data collection top

Oxford Diffraction Gemini R diffractometer	8407 independent reflections
Radiation source: fine-focus sealed tube	4388 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 10.5081 pixels mm^-1	θ_max = 34.8°, θ_min = 4.5°
ϕ and ω scans	h = −19→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −12→12
T_min = 0.945, T_max = 1.000	l = −34→28
27164 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 0.92	w = 1/[σ²(F_o²) + (0.0618P)²] where P = (F_o² + 2F_c²)/3
8407 reflections	(Δ/σ)_max = 0.003
289 parameters	Δρ_max = 2.03 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

C₂₄H₁₂BrCl₂NO₄	V = 2117.53 (7) Å³
M_r = 529.16	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.8590 (3) Å	µ = 2.23 mm⁻¹
b = 7.8126 (1) Å	T = 200 K
c = 21.9574 (4) Å	0.46 × 0.18 × 0.15 mm
β = 106.272 (2)°

Data collection top

Oxford Diffraction Gemini R diffractometer	8407 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	4388 reflections with I > 2σ(I)
T_min = 0.945, T_max = 1.000	R_int = 0.041
27164 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 0.92	Δρ_max = 2.03 e Å⁻³
8407 reflections	Δρ_min = −0.70 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	0.16560 (2)	0.07777 (4)	0.693146 (11)	0.03453 (9)
Cl1A	0.54339 (7)	0.57382 (8)	0.71533 (4)	0.04354 (18)
Cl1B	0.56864 (7)	−0.14656 (8)	0.60493 (4)	0.04445 (19)
O1	−0.05313 (17)	0.1335 (4)	0.60398 (10)	0.0601 (7)
O2	0.24523 (15)	0.3427 (3)	0.49462 (8)	0.0406 (5)
O1A	0.31064 (15)	0.4218 (2)	0.68149 (8)	0.0325 (4)
O1B	0.33990 (16)	−0.0028 (2)	0.54700 (9)	0.0389 (5)
N	0.32004 (15)	0.2100 (2)	0.61270 (8)	0.0207 (4)
C1	0.20724 (18)	0.2157 (3)	0.58269 (10)	0.0207 (4)
C2	0.1317 (2)	0.1653 (3)	0.61071 (10)	0.0251 (5)
C3	0.0139 (2)	0.1748 (3)	0.57732 (11)	0.0298 (5)
C4	−0.01873 (19)	0.2343 (3)	0.51068 (10)	0.0239 (5)
C5	−0.1271 (2)	0.2365 (3)	0.47668 (11)	0.0290 (5)
H5A	−0.1803	0.1963	0.4957	0.035*
C6	−0.1578 (2)	0.2969 (3)	0.41533 (12)	0.0342 (6)
H6A	−0.2323	0.2996	0.3925	0.041*
C7	−0.0814 (2)	0.3536 (4)	0.38673 (12)	0.0367 (6)
H7A	−0.1037	0.3955	0.3444	0.044*
C8	0.0275 (2)	0.3495 (3)	0.41937 (11)	0.0333 (6)
H8A	0.0800	0.3873	0.3994	0.040*
C9	0.0601 (2)	0.2897 (3)	0.48187 (10)	0.0237 (5)
C10	0.1758 (2)	0.2874 (3)	0.51699 (10)	0.0252 (5)
C1A	0.36326 (19)	0.3069 (3)	0.66818 (10)	0.0211 (4)
C2A	0.47008 (19)	0.2488 (3)	0.71062 (10)	0.0235 (5)
C3A	0.5541 (2)	0.3614 (3)	0.73579 (11)	0.0292 (5)
C4A	0.6516 (2)	0.3043 (4)	0.77548 (12)	0.0405 (7)
H4AA	0.7095	0.3823	0.7914	0.049*
C5A	0.6642 (3)	0.1328 (4)	0.79186 (13)	0.0454 (7)
H5AA	0.7309	0.0933	0.8192	0.054*
C6A	0.5810 (3)	0.0197 (4)	0.76886 (12)	0.0404 (7)
H6AA	0.5896	−0.0974	0.7809	0.048*
C7A	0.4848 (2)	0.0758 (3)	0.72825 (11)	0.0298 (5)
H7AA	0.4277	−0.0035	0.7120	0.036*
C1B	0.38232 (19)	0.1143 (3)	0.57957 (11)	0.0235 (5)
C2B	0.49383 (19)	0.1791 (3)	0.58353 (10)	0.0228 (5)
C3B	0.5818 (2)	0.0694 (3)	0.59230 (11)	0.0260 (5)
C4B	0.6829 (2)	0.1307 (3)	0.59320 (12)	0.0319 (6)
H4BA	0.7432	0.0552	0.6007	0.038*
C5B	0.6956 (2)	0.3040 (3)	0.58300 (12)	0.0323 (6)
H5BA	0.7648	0.3470	0.5832	0.039*
C6B	0.6095 (2)	0.4132 (3)	0.57274 (12)	0.0307 (5)
H6BA	0.6186	0.5308	0.5646	0.037*
C7B	0.5094 (2)	0.3529 (3)	0.57424 (10)	0.0252 (5)
H7BA	0.4505	0.4304	0.5689	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.02744 (14)	0.05392 (17)	0.02277 (12)	−0.00532 (12)	0.00791 (9)	0.01052 (11)
Cl1A	0.0473 (5)	0.0356 (3)	0.0481 (4)	−0.0096 (3)	0.0140 (3)	−0.0032 (3)
Cl1B	0.0482 (5)	0.0279 (3)	0.0601 (5)	0.0041 (3)	0.0198 (4)	0.0029 (3)
O1	0.0209 (11)	0.120 (2)	0.0407 (12)	−0.0055 (12)	0.0117 (9)	0.0258 (13)
O2	0.0219 (10)	0.0688 (12)	0.0316 (10)	−0.0072 (9)	0.0084 (8)	0.0174 (9)
O1A	0.0269 (10)	0.0382 (9)	0.0299 (9)	0.0062 (8)	0.0040 (7)	−0.0080 (8)
O1B	0.0308 (11)	0.0415 (10)	0.0461 (11)	−0.0133 (9)	0.0134 (8)	−0.0235 (9)
N	0.0144 (9)	0.0301 (9)	0.0175 (8)	−0.0022 (8)	0.0044 (7)	−0.0041 (7)
C1	0.0158 (11)	0.0288 (11)	0.0170 (10)	−0.0020 (9)	0.0040 (8)	−0.0006 (9)
C2	0.0196 (12)	0.0373 (13)	0.0190 (10)	−0.0022 (10)	0.0061 (9)	0.0007 (9)
C3	0.0178 (12)	0.0454 (14)	0.0279 (12)	−0.0019 (11)	0.0090 (10)	0.0050 (11)
C4	0.0178 (12)	0.0308 (12)	0.0222 (11)	−0.0022 (10)	0.0043 (8)	−0.0022 (9)
C5	0.0175 (12)	0.0344 (13)	0.0341 (13)	−0.0033 (10)	0.0056 (10)	−0.0015 (11)
C6	0.0199 (13)	0.0412 (14)	0.0349 (13)	0.0011 (11)	−0.0033 (10)	−0.0042 (12)
C7	0.0324 (16)	0.0460 (15)	0.0258 (12)	0.0015 (13)	−0.0016 (11)	0.0050 (11)
C8	0.0289 (15)	0.0462 (14)	0.0242 (12)	−0.0028 (12)	0.0065 (10)	0.0057 (11)
C9	0.0216 (12)	0.0282 (11)	0.0195 (10)	−0.0017 (10)	0.0028 (8)	0.0004 (9)
C10	0.0209 (12)	0.0329 (12)	0.0217 (10)	−0.0036 (10)	0.0062 (9)	0.0003 (9)
C1A	0.0212 (12)	0.0238 (10)	0.0179 (10)	−0.0029 (9)	0.0047 (8)	0.0008 (8)
C2A	0.0197 (12)	0.0345 (12)	0.0163 (9)	−0.0008 (10)	0.0051 (8)	−0.0021 (9)
C3A	0.0252 (13)	0.0389 (13)	0.0235 (11)	−0.0071 (11)	0.0068 (10)	−0.0034 (10)
C4A	0.0286 (15)	0.0624 (18)	0.0266 (13)	−0.0115 (14)	0.0009 (11)	−0.0042 (13)
C5A	0.0344 (17)	0.0663 (19)	0.0318 (14)	0.0121 (15)	0.0031 (12)	0.0050 (14)
C6A	0.049 (2)	0.0436 (15)	0.0270 (13)	0.0128 (14)	0.0079 (12)	0.0035 (12)
C7A	0.0329 (14)	0.0333 (12)	0.0222 (11)	0.0048 (11)	0.0058 (9)	−0.0010 (10)
C1B	0.0189 (12)	0.0303 (12)	0.0221 (10)	0.0003 (9)	0.0070 (9)	−0.0014 (9)
C2B	0.0200 (12)	0.0318 (12)	0.0165 (9)	0.0000 (10)	0.0051 (8)	−0.0029 (9)
C3B	0.0265 (13)	0.0287 (11)	0.0251 (11)	0.0048 (11)	0.0111 (9)	0.0001 (10)
C4B	0.0249 (14)	0.0430 (14)	0.0290 (12)	0.0044 (11)	0.0094 (10)	0.0000 (11)
C5B	0.0241 (14)	0.0441 (14)	0.0313 (13)	−0.0098 (12)	0.0119 (10)	−0.0066 (11)
C6B	0.0326 (14)	0.0322 (12)	0.0309 (12)	−0.0063 (12)	0.0148 (10)	−0.0015 (11)
C7B	0.0201 (12)	0.0349 (12)	0.0221 (11)	−0.0026 (10)	0.0083 (9)	−0.0004 (10)

Geometric parameters (Å, º) top

Br—C2	1.869 (2)	C1A—C2A	1.498 (3)
Cl1A—C3A	1.715 (3)	C2A—C3A	1.383 (3)
Cl1B—C3B	1.726 (2)	C2A—C7A	1.404 (3)
O1—C3	1.214 (3)	C3A—C4A	1.384 (4)
O2—C10	1.213 (3)	C4A—C5A	1.385 (4)
O1A—C1A	1.209 (3)	C4A—H4AA	0.9500
O1B—C1B	1.195 (3)	C5A—C6A	1.370 (5)
N—C1A	1.410 (3)	C5A—H5AA	0.9500
N—C1	1.416 (3)	C6A—C7A	1.378 (4)
N—C1B	1.434 (3)	C6A—H6AA	0.9500
C1—C2	1.346 (3)	C7A—H7AA	0.9500
C1—C10	1.494 (3)	C1B—C2B	1.500 (3)
C2—C3	1.489 (3)	C2B—C3B	1.389 (3)
C3—C4	1.479 (3)	C2B—C7B	1.396 (3)
C4—C5	1.384 (3)	C3B—C4B	1.381 (4)
C4—C9	1.405 (3)	C4B—C5B	1.390 (4)
C5—C6	1.377 (3)	C4B—H4BA	0.9500
C5—H5A	0.9500	C5B—C6B	1.365 (4)
C6—C7	1.378 (4)	C5B—H5BA	0.9500
C6—H6A	0.9500	C6B—C7B	1.380 (4)
C7—C8	1.383 (4)	C6B—H6BA	0.9500
C7—H7A	0.9500	C7B—H7BA	0.9500
C8—C9	1.398 (3)	H6AA—Cl1Aⁱ	2.923
C8—H8A	0.9500	H6BA—Cl1Bⁱⁱ	2.805
C9—C10	1.471 (3)

C1A—N—C1	119.32 (18)	C7A—C2A—C1A	119.5 (2)
C1A—N—C1B	125.28 (19)	C2A—C3A—C4A	121.0 (3)
C1—N—C1B	115.17 (17)	C2A—C3A—Cl1A	120.9 (2)
C2—C1—N	123.7 (2)	C4A—C3A—Cl1A	118.0 (2)
C2—C1—C10	121.1 (2)	C3A—C4A—C5A	119.6 (3)
N—C1—C10	115.22 (18)	C3A—C4A—H4AA	120.2
C1—C2—C3	121.7 (2)	C5A—C4A—H4AA	120.2
C1—C2—Br	123.22 (18)	C6A—C5A—C4A	120.4 (3)
C3—C2—Br	115.11 (16)	C6A—C5A—H5AA	119.8
O1—C3—C4	121.2 (2)	C4A—C5A—H5AA	119.8
O1—C3—C2	120.8 (2)	C5A—C6A—C7A	120.0 (3)
C4—C3—C2	118.1 (2)	C5A—C6A—H6AA	120.0
C5—C4—C9	119.8 (2)	C7A—C6A—H6AA	120.0
C5—C4—C3	120.1 (2)	C6A—C7A—C2A	120.8 (3)
C9—C4—C3	120.1 (2)	C6A—C7A—H7AA	119.6
C6—C5—C4	120.1 (2)	C2A—C7A—H7AA	119.6
C6—C5—H5A	120.0	O1B—C1B—N	118.5 (2)
C4—C5—H5A	120.0	O1B—C1B—C2B	124.2 (2)
C5—C6—C7	120.7 (2)	N—C1B—C2B	117.08 (19)
C5—C6—H6A	119.7	C3B—C2B—C7B	118.4 (2)
C7—C6—H6A	119.7	C3B—C2B—C1B	121.8 (2)
C6—C7—C8	120.2 (2)	C7B—C2B—C1B	119.6 (2)
C6—C7—H7A	119.9	C4B—C3B—C2B	121.0 (2)
C8—C7—H7A	119.9	C4B—C3B—Cl1B	118.11 (19)
C7—C8—C9	119.9 (2)	C2B—C3B—Cl1B	120.86 (19)
C7—C8—H8A	120.1	C3B—C4B—C5B	119.2 (2)
C9—C8—H8A	120.1	C3B—C4B—H4BA	120.4
C8—C9—C4	119.3 (2)	C5B—C4B—H4BA	120.4
C8—C9—C10	120.0 (2)	C6B—C5B—C4B	120.6 (2)
C4—C9—C10	120.7 (2)	C6B—C5B—H5BA	119.7
O2—C10—C9	122.3 (2)	C4B—C5B—H5BA	119.7
O2—C10—C1	119.6 (2)	C5B—C6B—C7B	120.1 (2)
C9—C10—C1	118.1 (2)	C5B—C6B—H6BA	119.9
O1A—C1A—N	119.8 (2)	C7B—C6B—H6BA	119.9
O1A—C1A—C2A	123.5 (2)	C6B—C7B—C2B	120.5 (2)
N—C1A—C2A	116.47 (19)	C6B—C7B—H7BA	119.7
C3A—C2A—C7A	118.2 (2)	C2B—C7B—H7BA	119.7
C3A—C2A—C1A	122.3 (2)

C1A—N—C1—C2	−61.2 (3)	C1—N—C1A—C2A	157.69 (19)
C1B—N—C1—C2	124.0 (2)	C1B—N—C1A—C2A	−28.1 (3)
C1A—N—C1—C10	117.1 (2)	O1A—C1A—C2A—C3A	−51.8 (3)
C1B—N—C1—C10	−57.7 (3)	N—C1A—C2A—C3A	133.8 (2)
N—C1—C2—C3	179.6 (2)	O1A—C1A—C2A—C7A	125.2 (2)
C10—C1—C2—C3	1.4 (4)	N—C1A—C2A—C7A	−49.3 (3)
N—C1—C2—Br	−0.8 (3)	C7A—C2A—C3A—C4A	2.3 (4)
C10—C1—C2—Br	−179.02 (17)	C1A—C2A—C3A—C4A	179.3 (2)
C1—C2—C3—O1	−177.8 (3)	C7A—C2A—C3A—Cl1A	178.70 (18)
Br—C2—C3—O1	2.5 (4)	C1A—C2A—C3A—Cl1A	−4.3 (3)
C1—C2—C3—C4	2.8 (4)	C2A—C3A—C4A—C5A	−2.0 (4)
Br—C2—C3—C4	−176.85 (17)	Cl1A—C3A—C4A—C5A	−178.5 (2)
O1—C3—C4—C5	−2.9 (4)	C3A—C4A—C5A—C6A	0.2 (4)
C2—C3—C4—C5	176.5 (2)	C4A—C5A—C6A—C7A	1.2 (4)
O1—C3—C4—C9	176.8 (3)	C5A—C6A—C7A—C2A	−0.9 (4)
C2—C3—C4—C9	−3.9 (4)	C3A—C2A—C7A—C6A	−0.9 (4)
C9—C4—C5—C6	−1.7 (4)	C1A—C2A—C7A—C6A	−177.9 (2)
C3—C4—C5—C6	177.9 (2)	C1A—N—C1B—O1B	156.2 (2)
C4—C5—C6—C7	0.9 (4)	C1—N—C1B—O1B	−29.3 (3)
C5—C6—C7—C8	0.3 (4)	C1A—N—C1B—C2B	−29.4 (3)
C6—C7—C8—C9	−0.8 (4)	C1—N—C1B—C2B	145.08 (19)
C7—C8—C9—C4	0.0 (4)	O1B—C1B—C2B—C3B	−48.2 (3)
C7—C8—C9—C10	−179.2 (2)	N—C1B—C2B—C3B	137.8 (2)
C5—C4—C9—C8	1.2 (4)	O1B—C1B—C2B—C7B	127.7 (3)
C3—C4—C9—C8	−178.4 (2)	N—C1B—C2B—C7B	−46.3 (3)
C5—C4—C9—C10	−179.6 (2)	C7B—C2B—C3B—C4B	1.4 (3)
C3—C4—C9—C10	0.8 (3)	C1B—C2B—C3B—C4B	177.3 (2)
C8—C9—C10—O2	3.2 (4)	C7B—C2B—C3B—Cl1B	179.26 (17)
C4—C9—C10—O2	−176.0 (2)	C1B—C2B—C3B—Cl1B	−4.8 (3)
C8—C9—C10—C1	−177.5 (2)	C2B—C3B—C4B—C5B	−2.2 (3)
C4—C9—C10—C1	3.3 (3)	Cl1B—C3B—C4B—C5B	179.85 (19)
C2—C1—C10—O2	174.9 (2)	C3B—C4B—C5B—C6B	0.6 (4)
N—C1—C10—O2	−3.4 (3)	C4B—C5B—C6B—C7B	1.9 (4)
C2—C1—C10—C9	−4.4 (3)	C5B—C6B—C7B—C2B	−2.7 (4)
N—C1—C10—C9	177.21 (19)	C3B—C2B—C7B—C6B	1.1 (3)
C1—N—C1A—O1A	−17.0 (3)	C1B—C2B—C7B—C6B	−174.9 (2)
C1B—N—C1A—O1A	157.3 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1Bⁱⁱⁱ	0.95	2.51	3.209 (3)	131
C4B—H4BA···O1^iv	0.95	2.67	3.335 (3)	128
C6B—H6BA···O2^v	0.95	2.65	3.296 (3)	126

Symmetry codes: (iii) −x, −y, −z+1; (iv) x+1, y, z; (v) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₂BrCl₂NO₄
M_r	529.16
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	12.8590 (3), 7.8126 (1), 21.9574 (4)
β (°)	106.272 (2)
V (Å³)	2117.53 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.23
Crystal size (mm)	0.46 × 0.18 × 0.15

Data collection
Diffractometer	Oxford Diffraction Gemini R diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.945, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	27164, 8407, 4388
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.804

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.123, 0.92
No. of reflections	8407
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.03, −0.70

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (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	2.51	3.209 (3)	130.5
C4B—H4BA···O1ⁱⁱ	0.95	2.67	3.335 (3)	127.5
C6B—H6BA···O2ⁱⁱⁱ	0.95	2.65	3.296 (3)	126.0

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

Acknowledgements

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

References

Bakare, O., Ashendel, C. L., Peng, H., Zalkow, L. H. & Burgess, E. M. (2003). Bioorg. Med. Chem. E11, o3165–o3170. Web of Science CrossRef Google Scholar
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Ertl, P., Cooper, D., Allen, G. & Slater, M. J. (1999). Bioorg. Med. Chem. Lett. E9, o2863–o2866. Web of Science CrossRef Google Scholar
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Oxford Diffraction (2007). CrysAlis CCD 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, 323–324. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 65| Part 1| January 2009| Page o24

doi:10.1107/S1600536808039214

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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)-2-chloro-N-(2-chloro­benzoyl)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)-2-chloro-N-(2-chlorobenzoyl)benzamide