2-[(4-Bromo­phenyl)­amino]-1-phenyl­ethano­ne

The crystal structure of the title compound, C₁₄H₁₂BrNO, has been determined in the triclinic space group P at room temperature. The molecules pack in an all-trans conformation in the crystal structure which precludes the formation of any hydrogen bond. The shortest intermolecular contact between N and O in a neighbouring molecule is 3.411 Å.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.054
• wR factor = 0.100
• Data-to-parameter ratio = 13.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of Tmax/Tmin expected RT(exp) is > 1.10
          Absorption corrections should be applied.
          Tmin and Tmax expected:      0.789     0.935
          RT(exp) =      1.184


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

The title compound, (I), provides the required starting material for the synthesis of 2,5-diphenyl-3,4-bis(p-bromoanilino)furan in good yield (Bryce et al., 1965). It is interesting to note that the atoms C4—N1—C7—C8—C9 (Fig. 1) possess an all trans conformation and the N1—H1···O1 intermolecular hydrogen bond which could be expected to form dimers across the centre of symmetry is absent (Fig. 2). The bond lengths and angles are as expected.

S2. Experimental

To a solution of acetophenone in acetic acid, bromine in acetic acid was added and the contents were shaken for 10–15 min and allowed to stand for half an hour. Crushed ice was added to the mixture and the resulting solid was washed with absolute alcohol to yield phenacyl bromide. The latter was dissolved in ethanol and slowly added to an ethanol solution of p-bromoaniline. The reaction mixture was heated for 15–20 min until the colour changed to dark brown. The contents were cooled to room temperature. The solid obtained by filtration was crystallized from dry ethanol.

S3. Refinement

The H atoms were positioned geometrically and allowed to ride on their parent atoms, with U_iso(H) equal to U_eq of the parent atom.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1996) in the suite WinGX (Farrugia, 1999); software used to prepare material for publication: PLATON (Spek, 1990).

Figures

	Fig. 1. View of the title compound, showing the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radii.
	Fig. 2. Packing diagram of the title compound, viewed down the a axis.

2-[(4-bromophenyl)amino]-1-phenylethanone

Crystal data

C14H12BrNO	Z = 2
Mr = 290.15	F(000) = 292
Triclinic, P1	Dx = 1.587 Mg m^−3
Hall symbol: -P 1	Melting point: 439 K
a = 5.7609 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5689 (11) Å	Cell parameters from 903 reflections
c = 14.227 (2) Å	θ = 2.8–25.0°
α = 99.374 (2)°	µ = 3.37 mm^−1
β = 91.216 (2)°	T = 293 K
γ = 96.778 (2)°	Rod, pale yellow
V = 607.27 (16) Å^3	0.40 × 0.06 × 0.02 × 0.04 (radius) mm

Data collection

Bruker SMART CCD area-detector diffractometer	1748 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Graphite monochromator	θmax = 25.1°, θmin = 1.5°
ϕ and ω scans	h = −6→6
5884 measured reflections	k = −9→9
2133 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0397P)^2] where P = (Fo^2 + 2Fc^2)/3
2133 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

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
Br1	0.43743 (9)	0.85277 (7)	0.16251 (3)	0.0558 (2)
C4	−0.0071 (7)	0.7351 (5)	0.4223 (3)	0.0376 (10)
C9	−0.1970 (7)	0.7097 (5)	0.7617 (3)	0.0366 (10)
N1	−0.1440 (6)	0.6989 (5)	0.4956 (2)	0.0486 (10)
H1	−0.2859	0.6503	0.4823	0.058*
O1	−0.4484 (6)	0.6275 (5)	0.6248 (2)	0.0618 (9)
C1	0.2574 (7)	0.8076 (5)	0.2686 (3)	0.0392 (10)
C6	0.0314 (8)	0.7235 (6)	0.2534 (3)	0.0445 (11)
H6	−0.0323	0.6894	0.1916	0.053*
C7	−0.0631 (7)	0.7378 (6)	0.5940 (3)	0.0405 (10)
H7A	−0.0091	0.8656	0.6111	0.049*
H7B	0.0679	0.6717	0.6027	0.049*
C2	0.3534 (8)	0.8543 (6)	0.3592 (3)	0.0454 (11)
H2	0.5066	0.9099	0.3695	0.054*
C3	0.2221 (7)	0.8186 (6)	0.4356 (3)	0.0441 (11)
H3	0.2883	0.8512	0.4971	0.053*
C8	−0.2535 (8)	0.6866 (5)	0.6579 (3)	0.0408 (10)
C5	−0.0992 (7)	0.6899 (6)	0.3288 (3)	0.0422 (11)
H5	−0.2529	0.6357	0.3177	0.051*
C14	−0.3667 (8)	0.6519 (6)	0.8206 (3)	0.0503 (12)
H14	−0.5136	0.6004	0.7947	0.060*
C13	−0.3209 (10)	0.6695 (7)	0.9168 (4)	0.0628 (14)
H13	−0.4373	0.6306	0.9557	0.075*
C10	0.0199 (8)	0.7858 (6)	0.8022 (3)	0.0515 (12)
H10	0.1363	0.8260	0.7636	0.062*
C11	0.0652 (9)	0.8025 (7)	0.8986 (4)	0.0672 (15)
H11	0.2116	0.8537	0.9251	0.081*
C12	−0.1064 (11)	0.7434 (7)	0.9561 (3)	0.0680 (15)
H12	−0.0761	0.7538	1.0214	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0572 (3)	0.0634 (3)	0.0492 (3)	0.0032 (2)	0.0180 (2)	0.0171 (2)
C4	0.041 (3)	0.039 (2)	0.034 (2)	0.006 (2)	0.004 (2)	0.0058 (19)
C9	0.044 (3)	0.031 (2)	0.034 (2)	0.0040 (19)	0.006 (2)	0.0045 (18)
N1	0.038 (2)	0.073 (3)	0.031 (2)	−0.0104 (19)	0.0017 (17)	0.0060 (18)
O1	0.045 (2)	0.089 (3)	0.045 (2)	−0.0127 (18)	−0.0014 (16)	0.0090 (17)
C1	0.041 (3)	0.043 (2)	0.036 (3)	0.009 (2)	0.010 (2)	0.010 (2)
C6	0.043 (3)	0.054 (3)	0.034 (2)	0.004 (2)	−0.003 (2)	0.004 (2)
C7	0.043 (3)	0.047 (3)	0.030 (2)	0.003 (2)	0.003 (2)	0.0037 (19)
C2	0.039 (3)	0.050 (3)	0.043 (3)	−0.004 (2)	0.001 (2)	0.001 (2)
C3	0.043 (3)	0.055 (3)	0.030 (2)	0.000 (2)	−0.001 (2)	0.000 (2)
C8	0.046 (3)	0.038 (2)	0.039 (3)	0.005 (2)	0.006 (2)	0.0065 (19)
C5	0.032 (2)	0.052 (3)	0.039 (3)	−0.003 (2)	0.000 (2)	0.003 (2)
C14	0.054 (3)	0.049 (3)	0.044 (3)	−0.007 (2)	0.007 (2)	0.005 (2)
C13	0.073 (4)	0.067 (3)	0.047 (3)	−0.005 (3)	0.018 (3)	0.014 (3)
C10	0.046 (3)	0.068 (3)	0.038 (3)	−0.002 (2)	0.005 (2)	0.008 (2)
C11	0.059 (3)	0.093 (4)	0.046 (3)	0.001 (3)	−0.010 (3)	0.008 (3)
C12	0.095 (5)	0.079 (4)	0.031 (3)	0.008 (3)	−0.001 (3)	0.013 (3)

Geometric parameters (Å, º)

Br1—C1	1.903 (4)	C7—H7A	0.9700
C4—N1	1.365 (5)	C7—H7B	0.9700
C4—C3	1.390 (6)	C2—C3	1.381 (6)
C4—C5	1.395 (6)	C2—H2	0.9300
C9—C14	1.379 (6)	C3—H3	0.9300
C9—C10	1.384 (6)	C5—H5	0.9300
C9—C8	1.483 (6)	C14—C13	1.371 (6)
N1—C7	1.438 (5)	C14—H14	0.9300
N1—H1	0.8600	C13—C12	1.363 (7)
O1—C8	1.214 (5)	C13—H13	0.9300
C1—C2	1.367 (6)	C10—C11	1.374 (6)
C1—C6	1.376 (6)	C10—H10	0.9300
C6—C5	1.364 (6)	C11—C12	1.377 (7)
C6—H6	0.9300	C11—H11	0.9300
C7—C8	1.496 (6)	C12—H12	0.9300
N1—C4—C3	123.3 (4)	C2—C3—C4	121.2 (4)
N1—C4—C5	119.4 (4)	C2—C3—H3	119.4
C3—C4—C5	117.3 (4)	C4—C3—H3	119.4
C14—C9—C10	118.4 (4)	O1—C8—C9	121.5 (4)
C14—C9—C8	118.8 (4)	O1—C8—C7	120.2 (4)
C10—C9—C8	122.8 (4)	C9—C8—C7	118.3 (4)
C4—N1—C7	123.4 (3)	C6—C5—C4	121.4 (4)
C4—N1—H1	118.3	C6—C5—H5	119.3
C7—N1—H1	118.3	C4—C5—H5	119.3
C2—C1—C6	120.1 (4)	C13—C14—C9	120.6 (4)
C2—C1—Br1	120.3 (3)	C13—C14—H14	119.7
C6—C1—Br1	119.6 (3)	C9—C14—H14	119.7
C5—C6—C1	120.1 (4)	C12—C13—C14	120.7 (5)
C5—C6—H6	119.9	C12—C13—H13	119.7
C1—C6—H6	119.9	C14—C13—H13	119.7
N1—C7—C8	111.1 (3)	C11—C10—C9	120.7 (4)
N1—C7—H7A	109.4	C11—C10—H10	119.6
C8—C7—H7A	109.4	C9—C10—H10	119.6
N1—C7—H7B	109.4	C10—C11—C12	119.9 (5)
C8—C7—H7B	109.4	C10—C11—H11	120.0
H7A—C7—H7B	108.0	C12—C11—H11	120.0
C1—C2—C3	119.8 (4)	C13—C12—C11	119.6 (5)
C1—C2—H2	120.1	C13—C12—H12	120.2
C3—C2—H2	120.1	C11—C12—H12	120.2