2-Chloro-N-(2-chloro-benzo-yl)-N-(2-ethyl-4-oxo-3,4-di-hydro-quinazolin-3-yl)benzamide.

In the title compound, C24H17Cl2N3O3, the quinazolinone ring system is close to planar (r.m.s. deviation = 0.0132 Å), with the imide unit almost perpendicular to it, subtending a dihedral angle of 89.1 (1)°. However, the imide unit itself is not planar, the dihedral angle between the two O=C-N components being 34.6 (1)°. The dihedral angle between the two chlorobenzene rings is 40.50 (7)°, while the angles between these rings and the imide moiety are 54.6 (1) and 58.2 (1)°, respectively. The dihedral angles between the 2-chloro-phenyl rings and the quinazolinone ring system are 48.77 (5) and 32.92 (7)° for rings A and B, respectively. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into a three-dimensional array.

Related literature

For the synthesis and biological evaluation of some imido-substituted 1,4-naphtho­quinone derivatives, see: Bakare et al. (2003 ▶); Berhe et al. (2008 ▶); Brandy et al. (2013 ▶); Khraiwesh et al. (2012 ▶). For similar X-ray structures, see: Akinboye et al. (2009a ▶,b ▶); Brandy et al. (2012 ▶).

Experimental

Crystal data

C24H17Cl2N3O3

M = 466.31

Orthorhombic,

a = 17.2597 (6) Å

b = 13.5463 (4) Å

c = 18.9683 (7) Å

V = 4434.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 200 K

0.52 × 0.18 × 0.15 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012 ▶) T min = 0.935, T max = 1.000

32371 measured reflections

7466 independent reflections

2351 reflections with I > 2σ(I)

R int = 0.123

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.079

S = 0.77

7466 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis CCD (Agilent, 2012 ▶); cell refinement: CrysAlis RED (Agilent, 2012 ▶); 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 datablock(s) I. DOI: 10.1107/S1600536814006035/bt6969sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006035/bt6969Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006035/bt6969Isup3.cml

CCDC reference: 992424

Additional supporting information: crystallographic information; 3D view; checkCIF report

C24H17Cl2N3O3	F(000) = 1920
Mr = 466.31	Dx = 1.397 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4113 reflections
a = 17.2597 (6) Å	θ = 4.6–32.5°
b = 13.5463 (4) Å	µ = 0.33 mm−1
c = 18.9683 (7) Å	T = 200 K
V = 4434.9 (3) Å3	Needle, colourless
Z = 8	0.52 × 0.18 × 0.15 mm

Oxford Diffraction Gemini diffractometer	7466 independent reflections
Radiation source: fine-focus sealed tube	2351 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.123
Detector resolution: 10.5081 pixels mm-1	θmax = 32.6°, θmin = 4.6°
φ and ω scans	h = −26→25
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	k = −19→20
Tmin = 0.935, Tmax = 1.000	l = −25→28
32371 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 0.77	w = 1/[σ2(Fo2) + (0.0239P)2] where P = (Fo2 + 2Fc2)/3
7466 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.24 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
Cl1A	0.17309 (3)	0.55900 (4)	0.16919 (3)	0.04342 (14)
Cl1B	0.46697 (3)	0.43992 (4)	0.37319 (3)	0.05512 (17)
O	0.18853 (8)	0.70694 (9)	0.40899 (7)	0.0423 (4)
O1A	0.12604 (7)	0.51488 (9)	0.32178 (7)	0.0417 (4)
O1B	0.33657 (7)	0.55297 (10)	0.46096 (7)	0.0433 (3)
N	0.23311 (8)	0.52344 (9)	0.39013 (7)	0.0249 (4)
N1	0.18318 (8)	0.54745 (10)	0.44570 (7)	0.0265 (3)
N2	0.10350 (9)	0.49031 (11)	0.53679 (8)	0.0328 (4)
C1	0.15976 (11)	0.64646 (14)	0.44890 (10)	0.0297 (5)
C2	0.10246 (10)	0.66490 (14)	0.50310 (10)	0.0315 (5)
C3	0.07421 (12)	0.76030 (15)	0.51353 (11)	0.0447 (6)
H3A	0.0929	0.8133	0.4854	0.054*
C4	0.01927 (13)	0.77749 (17)	0.56451 (12)	0.0550 (7)
H4A	0.0000	0.8424	0.5719	0.066*
C5	−0.00805 (12)	0.69966 (18)	0.60521 (12)	0.0516 (6)
H5A	−0.0460	0.7118	0.6404	0.062*
C6	0.01906 (11)	0.60552 (16)	0.59530 (10)	0.0415 (5)
H6A	−0.0004	0.5531	0.6234	0.050*
C7	0.07533 (10)	0.58646 (14)	0.54378 (10)	0.0311 (5)
C8	0.15506 (10)	0.47290 (12)	0.48974 (10)	0.0283 (5)
C9	0.18893 (12)	0.37229 (12)	0.47998 (10)	0.0376 (5)
H9A	0.2461	0.3775	0.4800	0.045*
H9B	0.1729	0.3463	0.4334	0.045*
C10	0.16416 (13)	0.29949 (14)	0.53710 (10)	0.0543 (6)
H10A	0.1871	0.2347	0.5275	0.081*
H10B	0.1076	0.2938	0.5374	0.081*
H10C	0.1819	0.3232	0.5831	0.081*
C1A	0.19483 (11)	0.49986 (12)	0.32637 (10)	0.0269 (4)
C2A	0.24009 (10)	0.44610 (13)	0.27213 (9)	0.0248 (4)
C3A	0.22865 (10)	0.46128 (13)	0.20026 (10)	0.0295 (4)
C4A	0.26354 (11)	0.40133 (13)	0.15073 (10)	0.0359 (5)
H4AA	0.2551	0.4123	0.1019	0.043*
C5A	0.31076 (12)	0.32527 (13)	0.17292 (11)	0.0401 (5)
H5AA	0.3342	0.2831	0.1391	0.048*
C6A	0.32422 (11)	0.30990 (13)	0.24376 (11)	0.0372 (5)
H6AA	0.3577	0.2583	0.2586	0.045*
C7A	0.28880 (10)	0.36974 (13)	0.29274 (10)	0.0304 (5)
H7AA	0.2978	0.3586	0.3415	0.037*
C1B	0.31255 (10)	0.54950 (13)	0.40145 (10)	0.0292 (4)
C2B	0.35792 (10)	0.57646 (12)	0.33781 (9)	0.0258 (4)
C3B	0.42944 (10)	0.53492 (13)	0.32191 (10)	0.0334 (5)
C4B	0.47126 (11)	0.56635 (16)	0.26462 (11)	0.0447 (5)
H4BA	0.5197	0.5365	0.2539	0.054*
C5B	0.44293 (12)	0.64119 (16)	0.22275 (11)	0.0481 (6)
H5BA	0.4719	0.6628	0.1830	0.058*
C6B	0.37257 (12)	0.68506 (14)	0.23818 (11)	0.0412 (5)
H6BA	0.3535	0.7375	0.2098	0.049*
C7B	0.33058 (11)	0.65183 (12)	0.29506 (10)	0.0329 (5)
H7BA	0.2818	0.6811	0.3053	0.040*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0517 (3)	0.0467 (3)	0.0319 (3)	0.0063 (3)	−0.0019 (3)	0.0055 (2)
Cl1B	0.0382 (3)	0.0594 (4)	0.0677 (4)	0.0131 (3)	0.0015 (3)	0.0122 (3)
O	0.0556 (9)	0.0345 (8)	0.0369 (9)	0.0039 (7)	0.0148 (8)	0.0053 (6)
O1A	0.0225 (7)	0.0719 (10)	0.0307 (9)	0.0020 (7)	−0.0006 (7)	−0.0031 (7)
O1B	0.0359 (8)	0.0682 (9)	0.0259 (8)	−0.0045 (7)	−0.0048 (7)	−0.0015 (7)
N	0.0235 (8)	0.0331 (9)	0.0181 (9)	0.0008 (7)	0.0038 (8)	−0.0038 (6)
N1	0.0281 (8)	0.0300 (9)	0.0212 (9)	0.0017 (8)	0.0064 (8)	−0.0011 (7)
N2	0.0319 (9)	0.0397 (11)	0.0267 (10)	−0.0036 (8)	0.0064 (9)	−0.0023 (7)
C1	0.0317 (11)	0.0318 (12)	0.0256 (12)	0.0047 (10)	0.0003 (10)	−0.0012 (9)
C2	0.0313 (11)	0.0389 (12)	0.0245 (12)	0.0057 (10)	0.0014 (10)	−0.0037 (9)
C3	0.0487 (13)	0.0504 (15)	0.0348 (14)	0.0140 (12)	0.0050 (12)	0.0018 (10)
C4	0.0586 (16)	0.0568 (16)	0.0495 (17)	0.0246 (13)	0.0052 (14)	−0.0088 (12)
C5	0.0374 (13)	0.0756 (18)	0.0417 (15)	0.0153 (13)	0.0119 (12)	−0.0125 (13)
C6	0.0328 (12)	0.0632 (15)	0.0286 (13)	−0.0028 (11)	0.0113 (11)	−0.0032 (10)
C7	0.0254 (10)	0.0432 (13)	0.0247 (12)	−0.0008 (10)	−0.0017 (10)	−0.0032 (9)
C8	0.0280 (11)	0.0349 (12)	0.0221 (11)	−0.0034 (9)	−0.0043 (10)	−0.0001 (8)
C9	0.0480 (13)	0.0309 (12)	0.0339 (13)	0.0026 (10)	0.0028 (11)	−0.0007 (9)
C10	0.0830 (17)	0.0398 (13)	0.0401 (14)	0.0017 (13)	0.0111 (14)	0.0063 (10)
C1A	0.0277 (10)	0.0312 (10)	0.0219 (11)	−0.0047 (9)	−0.0003 (10)	0.0020 (8)
C2A	0.0234 (9)	0.0266 (10)	0.0244 (11)	−0.0064 (9)	0.0018 (9)	−0.0043 (8)
C3A	0.0286 (10)	0.0283 (11)	0.0315 (12)	−0.0050 (9)	0.0016 (10)	−0.0017 (8)
C4A	0.0502 (13)	0.0324 (12)	0.0252 (12)	−0.0064 (11)	0.0074 (11)	−0.0006 (9)
C5A	0.0513 (13)	0.0322 (12)	0.0368 (14)	−0.0057 (11)	0.0184 (12)	−0.0101 (9)
C6A	0.0400 (12)	0.0281 (11)	0.0434 (14)	0.0032 (10)	0.0061 (12)	−0.0030 (10)
C7A	0.0319 (11)	0.0320 (12)	0.0273 (12)	−0.0056 (10)	0.0032 (10)	−0.0012 (9)
C1B	0.0260 (10)	0.0317 (11)	0.0298 (12)	0.0034 (9)	−0.0023 (10)	−0.0033 (9)
C2B	0.0219 (9)	0.0336 (11)	0.0219 (11)	−0.0045 (9)	0.0013 (9)	−0.0040 (8)
C3B	0.0257 (10)	0.0394 (12)	0.0351 (13)	−0.0002 (9)	−0.0009 (10)	−0.0004 (9)
C4B	0.0265 (11)	0.0655 (15)	0.0421 (14)	0.0007 (12)	0.0049 (11)	−0.0075 (12)
C5B	0.0379 (13)	0.0743 (17)	0.0321 (14)	−0.0111 (13)	0.0111 (12)	0.0042 (12)
C6B	0.0411 (12)	0.0477 (13)	0.0346 (14)	−0.0070 (11)	0.0010 (12)	0.0054 (10)
C7B	0.0282 (10)	0.0385 (12)	0.0321 (12)	−0.0023 (10)	−0.0009 (10)	−0.0059 (9)

Cl1A—C3A	1.7376 (18)	C9—H9B	0.9900
Cl1B—C3B	1.7385 (19)	C10—H10A	0.9800
O—C1	1.2211 (19)	C10—H10B	0.9800
O1A—C1A	1.208 (2)	C10—H10C	0.9800
O1B—C1B	1.2034 (19)	C1A—C2A	1.483 (2)
N—N1	1.3999 (17)	C2A—C7A	1.389 (2)
N—C1A	1.415 (2)	C2A—C3A	1.393 (2)
N—C1B	1.432 (2)	C3A—C4A	1.380 (2)
N1—C8	1.398 (2)	C4A—C5A	1.379 (2)
N1—C1	1.402 (2)	C4A—H4AA	0.9500
N2—C8	1.282 (2)	C5A—C6A	1.379 (3)
N2—C7	1.397 (2)	C5A—H5AA	0.9500
C1—C2	1.448 (2)	C6A—C7A	1.376 (2)
C2—C7	1.394 (2)	C6A—H6AA	0.9500
C2—C3	1.395 (2)	C7A—H7AA	0.9500
C3—C4	1.374 (3)	C1B—C2B	1.485 (2)
C3—H3A	0.9500	C2B—C7B	1.387 (2)
C4—C5	1.389 (3)	C2B—C3B	1.390 (2)
C4—H4A	0.9500	C3B—C4B	1.372 (2)
C5—C6	1.371 (3)	C4B—C5B	1.378 (3)
C5—H5A	0.9500	C4B—H4BA	0.9500
C6—C7	1.402 (2)	C5B—C6B	1.383 (3)
C6—H6A	0.9500	C5B—H5BA	0.9500
C8—C9	1.494 (2)	C6B—C7B	1.376 (2)
C9—C10	1.526 (2)	C6B—H6BA	0.9500
C9—H9A	0.9900	C7B—H7BA	0.9500
N1—N—C1A	114.12 (13)	O1A—C1A—N	118.87 (17)
N1—N—C1B	114.78 (13)	O1A—C1A—C2A	123.41 (18)
C1A—N—C1B	129.13 (15)	N—C1A—C2A	117.25 (15)
C8—N1—N	119.73 (14)	C7A—C2A—C3A	118.12 (16)
C8—N1—C1	124.42 (15)	C7A—C2A—C1A	119.29 (16)
N—N1—C1	115.61 (13)	C3A—C2A—C1A	122.13 (17)
C8—N2—C7	118.64 (16)	C4A—C3A—C2A	121.17 (17)
O—C1—N1	119.86 (17)	C4A—C3A—Cl1A	117.27 (15)
O—C1—C2	127.02 (17)	C2A—C3A—Cl1A	121.51 (14)
N1—C1—C2	113.11 (16)	C5A—C4A—C3A	119.31 (18)
C7—C2—C3	120.68 (18)	C5A—C4A—H4AA	120.3
C7—C2—C1	119.39 (17)	C3A—C4A—H4AA	120.3
C3—C2—C1	119.93 (18)	C6A—C5A—C4A	120.63 (18)
C4—C3—C2	119.8 (2)	C6A—C5A—H5AA	119.7
C4—C3—H3A	120.1	C4A—C5A—H5AA	119.7
C2—C3—H3A	120.1	C7A—C6A—C5A	119.60 (18)
C3—C4—C5	119.8 (2)	C7A—C6A—H6AA	120.2
C3—C4—H4A	120.1	C5A—C6A—H6AA	120.2
C5—C4—H4A	120.1	C6A—C7A—C2A	121.16 (18)
C6—C5—C4	120.9 (2)	C6A—C7A—H7AA	119.4
C6—C5—H5A	119.5	C2A—C7A—H7AA	119.4
C4—C5—H5A	119.5	O1B—C1B—N	118.70 (17)
C5—C6—C7	120.2 (2)	O1B—C1B—C2B	124.85 (16)
C5—C6—H6A	119.9	N—C1B—C2B	116.34 (16)
C7—C6—H6A	119.9	C7B—C2B—C3B	118.26 (17)
C2—C7—N2	122.77 (17)	C7B—C2B—C1B	118.50 (16)
C2—C7—C6	118.56 (18)	C3B—C2B—C1B	123.05 (17)
N2—C7—C6	118.64 (18)	C4B—C3B—C2B	120.90 (18)
N2—C8—N1	121.61 (16)	C4B—C3B—Cl1B	118.48 (15)
N2—C8—C9	121.70 (17)	C2B—C3B—Cl1B	120.61 (15)
N1—C8—C9	116.69 (16)	C3B—C4B—C5B	119.87 (19)
C8—C9—C10	113.07 (16)	C3B—C4B—H4BA	120.1
C8—C9—H9A	109.0	C5B—C4B—H4BA	120.1
C10—C9—H9A	109.0	C4B—C5B—C6B	120.4 (2)
C8—C9—H9B	109.0	C4B—C5B—H5BA	119.8
C10—C9—H9B	109.0	C6B—C5B—H5BA	119.8
H9A—C9—H9B	107.8	C7B—C6B—C5B	119.20 (19)
C9—C10—H10A	109.5	C7B—C6B—H6BA	120.4
C9—C10—H10B	109.5	C5B—C6B—H6BA	120.4
H10A—C10—H10B	109.5	C6B—C7B—C2B	121.35 (18)
C9—C10—H10C	109.5	C6B—C7B—H7BA	119.3
H10A—C10—H10C	109.5	C2B—C7B—H7BA	119.3
H10B—C10—H10C	109.5
C1A—N—N1—C8	88.76 (18)	C1B—N—C1A—C2A	34.5 (2)
C1B—N—N1—C8	−105.67 (17)	O1A—C1A—C2A—C7A	−130.35 (19)
C1A—N—N1—C1	−85.93 (17)	N—C1A—C2A—C7A	41.7 (2)
C1B—N—N1—C1	79.63 (18)	O1A—C1A—C2A—C3A	41.7 (3)
C8—N1—C1—O	178.75 (16)	N—C1A—C2A—C3A	−146.27 (16)
N—N1—C1—O	−6.8 (2)	C7A—C2A—C3A—C4A	1.1 (2)
C8—N1—C1—C2	−0.1 (2)	C1A—C2A—C3A—C4A	−171.08 (16)
N—N1—C1—C2	174.35 (14)	C7A—C2A—C3A—Cl1A	−176.41 (12)
O—C1—C2—C7	179.50 (19)	C1A—C2A—C3A—Cl1A	11.4 (2)
N1—C1—C2—C7	−1.8 (2)	C2A—C3A—C4A—C5A	−0.2 (3)
O—C1—C2—C3	0.3 (3)	Cl1A—C3A—C4A—C5A	177.38 (14)
N1—C1—C2—C3	179.05 (17)	C3A—C4A—C5A—C6A	−1.1 (3)
C7—C2—C3—C4	0.2 (3)	C4A—C5A—C6A—C7A	1.4 (3)
C1—C2—C3—C4	179.35 (18)	C5A—C6A—C7A—C2A	−0.5 (3)
C2—C3—C4—C5	−0.2 (3)	C3A—C2A—C7A—C6A	−0.7 (2)
C3—C4—C5—C6	0.0 (3)	C1A—C2A—C7A—C6A	171.68 (16)
C4—C5—C6—C7	0.2 (3)	N1—N—C1B—O1B	27.8 (2)
C3—C2—C7—N2	−177.99 (17)	C1A—N—C1B—O1B	−169.29 (16)
C1—C2—C7—N2	2.9 (3)	N1—N—C1B—C2B	−148.52 (14)
C3—C2—C7—C6	0.0 (3)	C1A—N—C1B—C2B	14.4 (2)
C1—C2—C7—C6	−179.09 (16)	O1B—C1B—C2B—C7B	−120.3 (2)
C8—N2—C7—C2	−1.9 (3)	N—C1B—C2B—C7B	55.7 (2)
C8—N2—C7—C6	−179.90 (16)	O1B—C1B—C2B—C3B	54.6 (3)
C5—C6—C7—C2	−0.3 (3)	N—C1B—C2B—C3B	−129.34 (18)
C5—C6—C7—N2	177.84 (18)	C7B—C2B—C3B—C4B	−1.2 (3)
C7—N2—C8—N1	−0.1 (2)	C1B—C2B—C3B—C4B	−176.20 (17)
C7—N2—C8—C9	178.94 (16)	C7B—C2B—C3B—Cl1B	−179.81 (13)
N—N1—C8—N2	−173.11 (15)	C1B—C2B—C3B—Cl1B	5.2 (2)
C1—N1—C8—N2	1.1 (3)	C2B—C3B—C4B—C5B	1.1 (3)
N—N1—C8—C9	7.8 (2)	Cl1B—C3B—C4B—C5B	179.71 (15)
C1—N1—C8—C9	−178.03 (16)	C3B—C4B—C5B—C6B	0.1 (3)
N2—C8—C9—C10	−7.8 (3)	C4B—C5B—C6B—C7B	−1.2 (3)
N1—C8—C9—C10	171.29 (16)	C5B—C6B—C7B—C2B	1.0 (3)
N1—N—C1A—O1A	9.9 (2)	C3B—C2B—C7B—C6B	0.1 (3)
C1B—N—C1A—O1A	−153.11 (17)	C1B—C2B—C7B—C6B	175.35 (16)
N1—N—C1A—C2A	−162.47 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AA···Oi	0.95	2.43	3.143 (2)	132
C4B—H4BA···O1Aii	0.95	2.35	3.211 (2)	151
C6—H6A···O1Aiii	0.95	2.58	3.377 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7A—H7AA⋯Oi	0.95	2.43	3.143 (2)	132
C4B—H4BA⋯O1A ii	0.95	2.35	3.211 (2)	151
C6—H6A⋯O1A iii	0.95	2.58	3.377 (2)	142

Symmetry codes: (i) ; (ii) ; (iii) .