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

The title compound, C(24)H(12)BrCl(2)NO(4), was synthesized from 2-amino-3-bromo-1,4-naphthoquinone and 2-chloro-benzoyl chloride. The crystal structure shows that each of the chloro-phenyl rings is inclined at about 60° to the naphthoquinone ring system. The two chloro-phenyl 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 = 529.16

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 0.92

8407 reflections

289 parameters

H-atom parameters constrained

Δρmax = 2.03 e Å−3

Δρmin = −0.70 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039214/bq2099sup1.cif

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

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

C24H12BrCl2NO4	F(000) = 1056
Mr = 529.16	Dx = 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

Oxford Diffraction Gemini R diffractometer	8407 independent reflections
Radiation source: fine-focus sealed tube	4388 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 10.5081 pixels mm-1	θmax = 34.8°, θmin = 4.5°
φ and ω scans	h = −19→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −12→12
Tmin = 0.945, Tmax = 1.000	l = −34→28
27164 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.0618P)2] where P = (Fo2 + 2Fc2)/3
8407 reflections	(Δ/σ)max = 0.003
289 parameters	Δρmax = 2.03 e Å−3
0 restraints	Δρmin = −0.70 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	0.16560 (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*

	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)

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)

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···O1iv	0.95	2.67	3.335 (3)	128
C6B—H6BA···O2v	0.95	2.65	3.296 (3)	126

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) ; (ii) ; (iii) .