N,N-Di­benzoyl-4-chloro­aniline

In the title compound, C₂₀H₁₄ClNO₂, the three aromatic rings are almost orthogonal to one another. The molecular packing is stabilized by weak C—H...π interactions and van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.131
• Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

N,N-(dibenzoyl)-4-chloroaniline

Crystal data

C20H14ClNO2	Dx = 1.337 Mg m^−3
Mr = 335.77	Melting point: 418K K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2697 (2) Å	Cell parameters from 3800 reflections
b = 9.0419 (2) Å	θ = 2.2–29.6°
c = 17.9903 (4) Å	µ = 0.24 mm^−1
β = 92.877 (1)°	T = 183 K
V = 1668.4 (1) Å^3	Block, colorless
Z = 4	0.46 × 0.20 × 0.12 mm
F(000) = 696

Data collection

Siemens SMART CCD area-detector diffractometer	2911 independent reflections
Radiation source: fine-focus sealed tube	1684 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.087
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 2.2°
ω scans	h = −12→12
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.898, Tmax = 0.972	l = −21→17
8993 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	Riding
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0499P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.89	(Δ/σ)max < 0.001
2911 reflections	Δρmax = 0.32 e Å^−3
218 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (3)

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.66392 (9)	0.90583 (9)	0.52576 (5)	0.0723 (4)
O1	0.59382 (18)	0.1458 (2)	0.32021 (11)	0.0492 (6)
O2	0.35486 (19)	0.4500 (2)	0.31169 (12)	0.0596 (6)
N1	0.57269 (19)	0.3970 (2)	0.32059 (11)	0.0339 (6)
C1	0.5815 (3)	0.6630 (3)	0.34445 (15)	0.0402 (7)
H1	0.5577	0.6790	0.2945	0.048*
C2	0.6004 (3)	0.7821 (3)	0.39191 (17)	0.0433 (7)
H2	0.5879	0.8782	0.3746	0.052*
C3	0.6381 (3)	0.7556 (3)	0.46548 (16)	0.0402 (7)
C4	0.6556 (3)	0.6142 (3)	0.49236 (16)	0.0423 (7)
H4	0.6815	0.5984	0.5420	0.051*
C5	0.6343 (2)	0.4960 (3)	0.44469 (14)	0.0361 (7)
H5	0.6445	0.3999	0.4625	0.043*
C6	0.5979 (2)	0.5196 (3)	0.37080 (14)	0.0315 (6)
C7	0.6473 (3)	0.2659 (3)	0.32712 (14)	0.0351 (7)
C8	0.7906 (2)	0.2806 (3)	0.33938 (14)	0.0321 (6)
C9	0.8604 (3)	0.3986 (3)	0.31098 (16)	0.0404 (7)
H9	0.8159	0.4769	0.2878	0.049*
C10	0.9943 (3)	0.3998 (3)	0.31711 (17)	0.0477 (8)
H10	1.0401	0.4777	0.2970	0.057*
C11	1.0610 (3)	0.2862 (4)	0.35287 (17)	0.0514 (8)
H11	1.1516	0.2881	0.3572	0.062*
C12	0.9934 (3)	0.1686 (3)	0.38265 (17)	0.0492 (8)
H12	1.0385	0.0927	0.4076	0.059*
C13	0.8594 (3)	0.1653 (3)	0.37499 (15)	0.0421 (7)
H13	0.8142	0.0855	0.3937	0.051*
C14	0.4458 (3)	0.3898 (3)	0.28422 (15)	0.0367 (7)
C15	0.4335 (2)	0.3185 (3)	0.20957 (14)	0.0331 (6)
C16	0.5397 (3)	0.2986 (3)	0.16446 (15)	0.0406 (7)
H16	0.6234	0.3230	0.1825	0.049*
C17	0.5202 (3)	0.2431 (3)	0.09388 (16)	0.0493 (8)
H17	0.5907	0.2307	0.0640	0.059*
C18	0.3961 (3)	0.2055 (3)	0.06679 (16)	0.0522 (8)
H18	0.3834	0.1673	0.0190	0.063*
C19	0.2913 (3)	0.2248 (3)	0.11077 (16)	0.0517 (8)
H19	0.2079	0.1993	0.0927	0.062*
C20	0.3100 (3)	0.2818 (3)	0.18159 (16)	0.0448 (7)
H20	0.2388	0.2957	0.2108	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0767 (7)	0.0616 (6)	0.0767 (7)	0.0103 (4)	−0.0143 (5)	−0.0356 (5)
O1	0.0518 (13)	0.0341 (11)	0.0609 (14)	−0.0091 (10)	−0.0053 (10)	0.0042 (10)
O2	0.0392 (12)	0.0772 (15)	0.0624 (15)	0.0090 (11)	0.0035 (11)	−0.0273 (12)
N1	0.0337 (13)	0.0330 (12)	0.0346 (13)	0.0020 (10)	−0.0022 (10)	−0.0046 (11)
C1	0.0476 (18)	0.0386 (16)	0.0341 (16)	0.0003 (13)	−0.0001 (13)	0.0023 (14)
C2	0.0446 (17)	0.0316 (15)	0.054 (2)	0.0016 (13)	0.0000 (15)	0.0026 (15)
C3	0.0343 (16)	0.0420 (17)	0.0445 (18)	0.0004 (13)	0.0047 (13)	−0.0140 (14)
C4	0.0437 (17)	0.0551 (18)	0.0279 (15)	0.0027 (15)	0.0003 (12)	−0.0033 (15)
C5	0.0371 (16)	0.0385 (16)	0.0328 (16)	0.0002 (13)	0.0026 (12)	0.0042 (13)
C6	0.0320 (15)	0.0312 (14)	0.0316 (15)	−0.0004 (12)	0.0044 (12)	−0.0002 (13)
C7	0.0417 (16)	0.0364 (16)	0.0270 (15)	0.0005 (13)	0.0004 (12)	−0.0006 (13)
C8	0.0358 (15)	0.0295 (14)	0.0308 (15)	0.0004 (12)	−0.0007 (12)	−0.0047 (12)
C9	0.0425 (17)	0.0342 (15)	0.0445 (18)	0.0023 (13)	0.0017 (13)	−0.0039 (13)
C10	0.0449 (18)	0.0427 (17)	0.056 (2)	−0.0056 (15)	0.0083 (15)	−0.0128 (16)
C11	0.0388 (17)	0.058 (2)	0.057 (2)	0.0009 (16)	−0.0019 (15)	−0.0207 (18)
C12	0.0473 (19)	0.0485 (19)	0.050 (2)	0.0135 (16)	−0.0121 (15)	−0.0047 (16)
C13	0.0475 (18)	0.0388 (16)	0.0396 (17)	0.0024 (14)	−0.0023 (14)	−0.0008 (14)
C14	0.0340 (16)	0.0366 (15)	0.0397 (17)	−0.0028 (13)	0.0017 (13)	−0.0055 (13)
C15	0.0349 (16)	0.0326 (15)	0.0317 (15)	−0.0026 (12)	−0.0003 (12)	0.0023 (12)
C16	0.0371 (16)	0.0459 (17)	0.0389 (17)	−0.0037 (13)	0.0022 (13)	0.0023 (14)
C17	0.054 (2)	0.0590 (19)	0.0362 (18)	−0.0078 (16)	0.0122 (15)	−0.0007 (15)
C18	0.065 (2)	0.061 (2)	0.0305 (17)	−0.0131 (17)	−0.0012 (16)	−0.0045 (15)
C19	0.0413 (18)	0.073 (2)	0.0402 (18)	−0.0107 (16)	−0.0044 (15)	−0.0032 (17)
C20	0.0370 (16)	0.0573 (18)	0.0403 (18)	−0.0063 (14)	0.0051 (14)	−0.0026 (15)

Geometric parameters (Å, º)

Cl1—C3	1.750 (3)	C9—H9	0.93
O1—C7	1.221 (3)	C10—C11	1.376 (4)
O2—C14	1.207 (3)	C10—H10	0.93
N1—C7	1.413 (3)	C11—C12	1.392 (4)
N1—C14	1.430 (3)	C11—H11	0.93
N1—C6	1.445 (3)	C12—C13	1.376 (4)
C1—C2	1.382 (4)	C12—H12	0.93
C1—C6	1.387 (3)	C13—H13	0.93
C1—H1	0.93	C14—C15	1.490 (4)
C2—C3	1.381 (4)	C15—C20	1.382 (4)
C2—H2	0.93	C15—C16	1.403 (3)
C3—C4	1.375 (4)	C16—C17	1.371 (4)
C4—C5	1.381 (3)	C16—H16	0.93
C4—H4	0.93	C17—C18	1.384 (4)
C5—C6	1.379 (4)	C17—H17	0.93
C5—H5	0.93	C18—C19	1.378 (4)
C7—C8	1.483 (4)	C18—H18	0.93
C8—C9	1.396 (3)	C19—C20	1.379 (4)
C8—C13	1.397 (3)	C19—H19	0.93
C9—C10	1.374 (4)	C20—H20	0.93
C7—N1—C14	118.6 (2)	C11—C10—H10	119.9
C7—N1—C6	120.8 (2)	C10—C11—C12	120.3 (3)
C14—N1—C6	116.8 (2)	C10—C11—H11	119.9
C2—C1—C6	120.4 (3)	C12—C11—H11	119.9
C2—C1—H1	119.8	C13—C12—C11	119.6 (3)
C6—C1—H1	119.8	C13—C12—H12	120.2
C3—C2—C1	118.7 (3)	C11—C12—H12	120.2
C3—C2—H2	120.6	C12—C13—C8	120.7 (3)
C1—C2—H2	120.6	C12—C13—H13	119.7
C4—C3—C2	121.6 (3)	C8—C13—H13	119.7
C4—C3—Cl1	119.4 (2)	O2—C14—N1	119.9 (2)
C2—C3—Cl1	119.1 (2)	O2—C14—C15	122.2 (3)
C3—C4—C5	119.2 (3)	N1—C14—C15	117.7 (2)
C3—C4—H4	120.4	C20—C15—C16	119.0 (2)
C5—C4—H4	120.4	C20—C15—C14	117.8 (2)
C6—C5—C4	120.4 (2)	C16—C15—C14	123.0 (2)
C6—C5—H5	119.8	C17—C16—C15	120.1 (3)
C4—C5—H5	119.8	C17—C16—H16	120.0
C5—C6—C1	119.8 (2)	C15—C16—H16	120.0
C5—C6—N1	121.0 (2)	C16—C17—C18	120.4 (3)
C1—C6—N1	119.2 (2)	C16—C17—H17	119.8
O1—C7—N1	119.9 (2)	C18—C17—H17	119.8
O1—C7—C8	122.2 (2)	C19—C18—C17	119.9 (3)
N1—C7—C8	117.9 (2)	C19—C18—H18	120.1
C9—C8—C13	118.8 (3)	C17—C18—H18	120.1
C9—C8—C7	122.5 (2)	C18—C19—C20	120.1 (3)
C13—C8—C7	118.5 (2)	C18—C19—H19	119.9
C10—C9—C8	120.4 (3)	C20—C19—H19	119.9
C10—C9—H9	119.8	C19—C20—C15	120.6 (3)
C8—C9—H9	119.8	C19—C20—H20	119.7
C9—C10—C11	120.3 (3)	C15—C20—H20	119.7
C9—C10—H10	119.9
C6—C1—C2—C3	1.2 (4)	C7—C8—C9—C10	−173.2 (2)
C1—C2—C3—C4	−0.8 (4)	C8—C9—C10—C11	−1.5 (4)
C1—C2—C3—Cl1	179.35 (19)	C9—C10—C11—C12	0.5 (4)
C2—C3—C4—C5	−0.3 (4)	C10—C11—C12—C13	1.1 (4)
Cl1—C3—C4—C5	179.55 (19)	C11—C12—C13—C8	−1.7 (4)
C3—C4—C5—C6	1.0 (4)	C9—C8—C13—C12	0.7 (4)
C4—C5—C6—C1	−0.6 (4)	C7—C8—C13—C12	175.1 (2)
C4—C5—C6—N1	−178.8 (2)	C7—N1—C14—O2	134.4 (3)
C2—C1—C6—C5	−0.5 (4)	C6—N1—C14—O2	−23.8 (3)
C2—C1—C6—N1	177.7 (2)	C7—N1—C14—C15	−50.9 (3)
C7—N1—C6—C5	−36.3 (3)	C6—N1—C14—C15	150.9 (2)
C14—N1—C6—C5	121.3 (3)	O2—C14—C15—C20	−19.5 (4)
C7—N1—C6—C1	145.5 (2)	N1—C14—C15—C20	166.0 (2)
C14—N1—C6—C1	−56.8 (3)	O2—C14—C15—C16	155.1 (3)
C14—N1—C7—O1	−18.9 (3)	N1—C14—C15—C16	−19.5 (4)
C6—N1—C7—O1	138.4 (2)	C20—C15—C16—C17	−0.2 (4)
C14—N1—C7—C8	158.7 (2)	C14—C15—C16—C17	−174.7 (2)
C6—N1—C7—C8	−44.0 (3)	C15—C16—C17—C18	−0.4 (4)
O1—C7—C8—C9	146.2 (3)	C16—C17—C18—C19	0.5 (5)
N1—C7—C8—C9	−31.4 (4)	C17—C18—C19—C20	0.2 (5)
O1—C7—C8—C13	−28.0 (4)	C18—C19—C20—C15	−0.8 (5)
N1—C7—C8—C13	154.4 (2)	C16—C15—C20—C19	0.8 (4)
C13—C8—C9—C10	0.9 (4)	C14—C15—C20—C19	175.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg(B)^i	0.93	2.72	3.597 (2)	158
C10—H10···Cg(C)^i	0.93	2.85	3.489 (2)	127

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