N-(4,4'-Dibromo-[1,1'-biphen-yl]-2-yl)benzamide.

In the title compound, C(19)H(13)Br(2)NO, the dihedral angle between the rings of the biphenyl group is 53.59 (14)°. The ring of the benzamide group is inclined to the phenyl rings of the biphenyl group by 23.87 (15) and 75.89 (15)°. There are no significant inter-molecular inter-actions in the crystal structure.

Related literature

For applications of the title compound, see: Libman & Slack (1951 ▶); Mandadapu et al. (2009 ▶); Youn & Bihn (2009 ▶); Yulan et al. (2010 ▶). For pharmacological properties of biphenyl aniline, see: Zhu et al. (2008 ▶). For related structures, see: Li & Cui (2011 ▶); Kuś et al. (2009 ▶); Hammond et al. (2009 ▶); Gowda et al. (2010 ▶); Novina et al. (2012 ▶).

Experimental

Crystal data

C19H13Br2NO

M = 431.12

Monoclinic,

a = 9.0188 (5) Å

b = 11.6415 (9) Å

c = 16.0068 (12) Å

β = 100.737 (2)°

V = 1651.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 4.91 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.238, T max = 0.374

16420 measured reflections

3453 independent reflections

2302 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.075

S = 1.01

3453 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000597/su2551sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000597/su2551Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000597/su2551Isup3.cml

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

C19H13Br2NO	F(000) = 848
Mr = 431.12	Dx = 1.734 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3453 reflections
a = 9.0188 (5) Å	θ = 2.2–26.6°
b = 11.6415 (9) Å	µ = 4.91 mm−1
c = 16.0068 (12) Å	T = 293 K
β = 100.737 (2)°	Block, colourless
V = 1651.2 (2) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3453 independent reflections
Radiation source: fine-focus sealed tube	2302 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scan	θmax = 26.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.238, Tmax = 0.374	k = −14→14
16420 measured reflections	l = −19→20

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0267P)2 + 1.1775P] where P = (Fo2 + 2Fc2)/3
3453 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

Experimental. Spectroscopic data for the title compound: IR (νN—H) 3399 cm-1, 1567 cm-1, (νC═O) 1666 cm-1, 1H NMR (CDCl3, 500 MHz) δ: 8.74 (d, J = 1.5 Hz, 1 H), 7.85 (s, 1H), 7.60 (dd, J = 6.5, 2.0 Hz, 2 H), 7.59–7.61 (m, 2 H), 7.52–7.55 (m, 1 H), 7.42–7.45 (m, 2 H), 7.35 (d, J = 1.5 Hz, 1 H), 7.30 (dd, J = 6.5, 2.0 Hz, 2 H), 7.11 (d, J = 8.0 Hz, 1 H); 13C NMR (CDCl3, 125 MHz) δ 165.1, 136.0, 135.8, 134.1, 133.7, 32.6, 131.1, 130.8, 130.2, 130.1, 129.0, 128.5, 127.7, 126.8, 124.6, 122.9, 122.7.

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
Br1	0.63621 (4)	0.21302 (3)	0.15668 (2)	0.06302 (13)
Br2	0.22124 (4)	1.08134 (3)	0.04697 (3)	0.07108 (15)
O1	0.1733 (2)	0.33800 (17)	−0.05842 (14)	0.0542 (6)
C1	0.3653 (3)	0.4886 (2)	0.06373 (17)	0.0342 (6)
C8	0.4769 (3)	0.7869 (2)	0.09646 (18)	0.0414 (7)
H8	0.5785	0.7681	0.1022	0.050*
C19	0.0269 (3)	0.4448 (3)	−0.2115 (2)	0.0496 (8)
H19	0.0688	0.3731	−0.2180	0.060*
N1	0.2512 (2)	0.51464 (19)	−0.00712 (14)	0.0380 (6)
H1	0.2333	0.5866	−0.0160	0.046*
C11	0.1763 (3)	0.8444 (3)	0.07935 (19)	0.0480 (8)
H11	0.0750	0.8640	0.0737	0.058*
C2	0.4251 (3)	0.3787 (2)	0.07720 (18)	0.0397 (7)
H2	0.3859	0.3185	0.0417	0.048*
C4	0.6025 (3)	0.4467 (3)	0.19891 (18)	0.0455 (8)
H4	0.6806	0.4320	0.2444	0.055*
C3	0.5430 (3)	0.3604 (3)	0.14369 (18)	0.0410 (7)
C7	0.3728 (3)	0.7005 (2)	0.10278 (17)	0.0361 (6)
C12	0.2218 (3)	0.7322 (3)	0.09524 (19)	0.0440 (7)
H12	0.1504	0.6766	0.1010	0.053*
C14	0.0602 (3)	0.5010 (2)	−0.13340 (18)	0.0372 (7)
C9	0.4329 (3)	0.8994 (2)	0.08194 (19)	0.0439 (7)
H9	0.5043	0.9562	0.0789	0.053*
C10	0.2825 (3)	0.9271 (2)	0.07198 (19)	0.0437 (7)
C5	0.5431 (3)	0.5548 (3)	0.18479 (19)	0.0455 (7)
H5	0.5831	0.6139	0.2213	0.055*
C6	0.4249 (3)	0.5796 (2)	0.11777 (17)	0.0367 (6)
C13	0.1656 (3)	0.4425 (2)	−0.06326 (18)	0.0373 (7)
C18	−0.0677 (4)	0.4950 (3)	−0.2791 (2)	0.0626 (10)
H18	−0.0875	0.4581	−0.3315	0.075*
C17	−0.1326 (4)	0.5993 (4)	−0.2690 (3)	0.0746 (11)
H17	−0.1956	0.6334	−0.3149	0.089*
C15	−0.0075 (3)	0.6061 (3)	−0.1242 (2)	0.0493 (8)
H15	0.0130	0.6446	−0.0725	0.059*
C16	−0.1055 (4)	0.6535 (3)	−0.1922 (3)	0.0664 (10)
H16	−0.1532	0.7228	−0.1855	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0675 (2)	0.0512 (2)	0.0659 (2)	0.01286 (17)	0.00079 (18)	0.01402 (17)
Br2	0.0641 (2)	0.0444 (2)	0.0985 (3)	0.00851 (17)	−0.0009 (2)	0.0004 (2)
O1	0.0578 (13)	0.0335 (12)	0.0629 (14)	−0.0026 (10)	−0.0104 (11)	−0.0010 (10)
C1	0.0326 (15)	0.0391 (16)	0.0314 (15)	−0.0046 (12)	0.0071 (12)	0.0051 (13)
C8	0.0324 (15)	0.0438 (18)	0.0471 (18)	−0.0032 (13)	0.0048 (13)	−0.0074 (15)
C19	0.0484 (18)	0.0491 (19)	0.0467 (19)	−0.0067 (15)	−0.0033 (15)	−0.0017 (16)
N1	0.0417 (13)	0.0296 (13)	0.0390 (14)	−0.0036 (10)	−0.0018 (11)	0.0029 (11)
C11	0.0359 (16)	0.054 (2)	0.052 (2)	0.0038 (15)	0.0044 (14)	−0.0088 (16)
C2	0.0421 (16)	0.0373 (16)	0.0389 (17)	−0.0044 (13)	0.0055 (14)	0.0031 (13)
C4	0.0430 (17)	0.060 (2)	0.0311 (16)	0.0009 (15)	0.0000 (14)	0.0086 (15)
C3	0.0417 (16)	0.0442 (17)	0.0382 (17)	0.0009 (14)	0.0104 (14)	0.0127 (14)
C7	0.0369 (15)	0.0385 (16)	0.0316 (15)	−0.0024 (13)	0.0035 (12)	−0.0055 (13)
C12	0.0369 (16)	0.0481 (19)	0.0473 (18)	−0.0097 (14)	0.0082 (14)	−0.0066 (15)
C14	0.0324 (14)	0.0391 (16)	0.0394 (17)	−0.0069 (12)	0.0050 (13)	0.0024 (13)
C9	0.0408 (17)	0.0397 (17)	0.0498 (19)	−0.0085 (13)	0.0052 (14)	−0.0060 (14)
C10	0.0478 (18)	0.0375 (17)	0.0428 (18)	0.0015 (14)	0.0003 (14)	−0.0059 (14)
C5	0.0442 (17)	0.0528 (19)	0.0368 (17)	−0.0030 (15)	0.0004 (14)	−0.0036 (15)
C6	0.0349 (15)	0.0421 (17)	0.0337 (16)	−0.0037 (13)	0.0083 (13)	0.0013 (13)
C13	0.0348 (15)	0.0381 (17)	0.0393 (17)	−0.0065 (12)	0.0072 (13)	0.0005 (13)
C18	0.063 (2)	0.073 (3)	0.045 (2)	−0.019 (2)	−0.0081 (18)	0.0018 (18)
C17	0.060 (2)	0.086 (3)	0.068 (3)	0.001 (2)	−0.015 (2)	0.026 (2)
C15	0.0505 (18)	0.0472 (19)	0.0496 (19)	0.0029 (15)	0.0079 (16)	0.0050 (15)
C16	0.062 (2)	0.060 (2)	0.074 (3)	0.0151 (18)	0.005 (2)	0.016 (2)

Br1—C3	1.904 (3)	C4—C5	1.370 (4)
Br2—C10	1.899 (3)	C4—C3	1.379 (4)
O1—C13	1.221 (3)	C4—H4	0.9300
C1—C2	1.390 (4)	C7—C12	1.394 (4)
C1—C6	1.409 (4)	C7—C6	1.489 (4)
C1—N1	1.415 (3)	C12—H12	0.9300
C8—C9	1.376 (4)	C14—C15	1.388 (4)
C8—C7	1.393 (4)	C14—C13	1.493 (4)
C8—H8	0.9300	C9—C10	1.374 (4)
C19—C18	1.377 (4)	C9—H9	0.9300
C19—C14	1.393 (4)	C5—C6	1.395 (4)
C19—H19	0.9300	C5—H5	0.9300
N1—C13	1.360 (3)	C18—C17	1.371 (5)
N1—H1	0.8600	C18—H18	0.9300
C11—C12	1.378 (4)	C17—C16	1.362 (5)
C11—C10	1.379 (4)	C17—H17	0.9300
C11—H11	0.9300	C15—C16	1.382 (4)
C2—C3	1.374 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—H16	0.9300
C2—C1—C6	120.3 (2)	C15—C14—C19	118.9 (3)
C2—C1—N1	121.7 (2)	C15—C14—C13	123.6 (3)
C6—C1—N1	117.9 (2)	C19—C14—C13	117.5 (3)
C9—C8—C7	121.5 (3)	C10—C9—C8	119.4 (3)
C9—C8—H8	119.2	C10—C9—H9	120.3
C7—C8—H8	119.2	C8—C9—H9	120.3
C18—C19—C14	120.3 (3)	C9—C10—C11	120.8 (3)
C18—C19—H19	119.8	C9—C10—Br2	119.2 (2)
C14—C19—H19	119.8	C11—C10—Br2	119.9 (2)
C13—N1—C1	129.5 (2)	C4—C5—C6	122.4 (3)
C13—N1—H1	115.3	C4—C5—H5	118.8
C1—N1—H1	115.3	C6—C5—H5	118.8
C12—C11—C10	119.3 (3)	C5—C6—C1	117.8 (3)
C12—C11—H11	120.3	C5—C6—C7	119.5 (3)
C10—C11—H11	120.3	C1—C6—C7	122.6 (2)
C3—C2—C1	119.0 (3)	O1—C13—N1	123.7 (3)
C3—C2—H2	120.5	O1—C13—C14	121.5 (3)
C1—C2—H2	120.5	N1—C13—C14	114.8 (2)
C5—C4—C3	118.1 (3)	C17—C18—C19	119.9 (3)
C5—C4—H4	121.0	C17—C18—H18	120.1
C3—C4—H4	121.0	C19—C18—H18	120.1
C2—C3—C4	122.4 (3)	C16—C17—C18	120.5 (3)
C2—C3—Br1	119.1 (2)	C16—C17—H17	119.7
C4—C3—Br1	118.4 (2)	C18—C17—H17	119.7
C8—C7—C12	117.6 (3)	C16—C15—C14	119.9 (3)
C8—C7—C6	119.9 (2)	C16—C15—H15	120.1
C12—C7—C6	122.5 (2)	C14—C15—H15	120.1
C11—C12—C7	121.3 (3)	C17—C16—C15	120.4 (3)
C11—C12—H12	119.4	C17—C16—H16	119.8
C7—C12—H12	119.4	C15—C16—H16	119.8
C2—C1—N1—C13	11.6 (4)	C4—C5—C6—C7	−175.9 (3)
C6—C1—N1—C13	−172.7 (3)	C2—C1—C6—C5	−0.8 (4)
C6—C1—C2—C3	−0.1 (4)	N1—C1—C6—C5	−176.5 (2)
N1—C1—C2—C3	175.5 (2)	C2—C1—C6—C7	175.5 (2)
C1—C2—C3—C4	1.4 (4)	N1—C1—C6—C7	−0.2 (4)
C1—C2—C3—Br1	−174.8 (2)	C8—C7—C6—C5	51.6 (4)
C5—C4—C3—C2	−1.7 (4)	C12—C7—C6—C5	−127.9 (3)
C5—C4—C3—Br1	174.6 (2)	C8—C7—C6—C1	−124.6 (3)
C9—C8—C7—C12	−1.0 (4)	C12—C7—C6—C1	55.9 (4)
C9—C8—C7—C6	179.5 (3)	C1—N1—C13—O1	2.2 (5)
C10—C11—C12—C7	−0.9 (5)	C1—N1—C13—C14	−177.1 (2)
C8—C7—C12—C11	2.1 (4)	C15—C14—C13—O1	148.3 (3)
C6—C7—C12—C11	−178.4 (3)	C19—C14—C13—O1	−30.4 (4)
C18—C19—C14—C15	2.2 (4)	C15—C14—C13—N1	−32.3 (4)
C18—C19—C14—C13	−179.0 (3)	C19—C14—C13—N1	149.0 (3)
C7—C8—C9—C10	−1.1 (5)	C14—C19—C18—C17	−1.7 (5)
C8—C9—C10—C11	2.3 (5)	C19—C18—C17—C16	−0.7 (6)
C8—C9—C10—Br2	−177.2 (2)	C19—C14—C15—C16	−0.4 (4)
C12—C11—C10—C9	−1.3 (5)	C13—C14—C15—C16	−179.1 (3)
C12—C11—C10—Br2	178.3 (2)	C18—C17—C16—C15	2.5 (6)
C3—C4—C5—C6	0.7 (4)	C14—C15—C16—C17	−2.0 (5)
C4—C5—C6—C1	0.5 (4)