2-(2-{2-[2-(Dibromo-meth-yl)phen-oxy]eth-oxy}benz-yloxy)benzaldehyde.

The mol-ecule of the title compound, C(23)H(20)Br(2)O(4), adopts a Z conformation as a result of inter-molecular C-H⋯Br bonding. One benzene ring, with the structure R-CHBr(2), makes a dihedral angle of 63.0 (2)° with the other benzene ring attached to the aldehyde group. Inter-molecular π-π stacking inter-actions [centroid-centroid distance = 3.698 (4) Å] and a weak C-H⋯Br contact is present in the crystal structure.

Related literature

For general background to the biological activity of salicyl­aldehydes and their derivatives, see: Jahnke et al. (1993 ▶); Pelttari et al. (2007 ▶); Fillebeen & Pantopoulos (2010 ▶); Fan et al. (2010 ▶). For related structures, see: Mori et al. (2010 ▶); Potapov et al. (2009 ▶); Purushothaman & Raghunathan (2009 ▶). For the preparation of the title compound, see: Purushothaman & Raghunathan (2009 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

C23H20Br2O4

M = 520.19

Monoclinic,

a = 12.867 (7) Å

b = 18.07 (1) Å

c = 9.649 (5) Å

β = 108.955 (6)°

V = 2122 (2) Å3

Z = 4

Mo Kα radiation

μ = 3.85 mm−1

T = 296 K

0.34 × 0.32 × 0.28 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.281, T max = 0.341

15392 measured reflections

3944 independent reflections

1905 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.207

S = 1.02

3944 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.75 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S160053681100643X/rk2257sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100643X/rk2257Isup2.hkl

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

C23H20Br2O4	F(000) = 1040
Mr = 520.19	Dx = 1.628 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1808 reflections
a = 12.867 (7) Å	θ = 2.3–17.5°
b = 18.07 (1) Å	µ = 3.85 mm−1
c = 9.649 (5) Å	T = 296 K
β = 108.955 (6)°	Block, colourless
V = 2122 (2) Å3	0.34 × 0.32 × 0.28 mm
Z = 4

Bruker APEXII CCD diffractometer	3944 independent reflections
Radiation source: fine-focus sealed tube	1905 reflections with I > 2σ(I)
graphite	Rint = 0.063
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.281, Tmax = 0.341	k = −21→21
15392 measured reflections	l = −11→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062	H-atom parameters constrained
wR(F2) = 0.207	w = 1/[σ2(Fo2) + (0.1049P)2 + 0.4797P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3944 reflections	Δρmax = 0.79 e Å−3
263 parameters	Δρmin = −0.75 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0020 (3)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.56817 (7)	0.30130 (6)	0.29797 (13)	0.1092 (5)
Br2	0.37069 (9)	0.31794 (5)	−0.00106 (10)	0.0986 (5)
C1	−0.1269 (7)	0.7137 (4)	−0.1294 (8)	0.069 (2)
H1	−0.1621	0.6777	−0.0919	0.083*
C2	−0.0059 (6)	0.7075 (3)	−0.0932 (6)	0.0509 (16)
C3	0.0495 (7)	0.7556 (4)	−0.1572 (7)	0.0658 (19)
H3	0.0096	0.7922	−0.2199	0.079*
C4	0.1583 (7)	0.7514 (4)	−0.1323 (8)	0.073 (2)
H4	0.1932	0.7846	−0.1761	0.088*
C5	0.2176 (6)	0.6962 (4)	−0.0397 (8)	0.070 (2)
H5	0.2930	0.6929	−0.0213	0.084*
C6	0.1660 (6)	0.6458 (4)	0.0260 (7)	0.0551 (16)
H6	0.2062	0.6085	0.0865	0.066*
C7	0.0548 (6)	0.6522 (3)	−0.0001 (6)	0.0511 (16)
C8	0.0522 (5)	0.5531 (3)	0.1655 (7)	0.0487 (15)
H8A	0.1057	0.5775	0.2474	0.058*
H8B	0.0905	0.5182	0.1229	0.058*
C9	−0.0317 (5)	0.5130 (3)	0.2169 (6)	0.0470 (15)
C10	−0.1419 (6)	0.5287 (4)	0.1643 (7)	0.0617 (18)
H10	−0.1676	0.5664	0.0961	0.074*
C11	−0.2162 (6)	0.4878 (5)	0.2135 (8)	0.070 (2)
H11	−0.2910	0.4979	0.1766	0.084*
C12	−0.1791 (7)	0.4340 (4)	0.3138 (8)	0.071 (2)
H12	−0.2284	0.4073	0.3465	0.085*
C13	−0.0685 (6)	0.4184 (4)	0.3684 (7)	0.0602 (17)
H13	−0.0436	0.3811	0.4378	0.072*
C14	0.0057 (5)	0.4576 (3)	0.3211 (7)	0.0487 (16)
C15	0.1611 (5)	0.3890 (3)	0.4722 (6)	0.0536 (16)
H15A	0.1381	0.3412	0.4268	0.064*
H15B	0.1347	0.3939	0.5552	0.064*
C16	0.2849 (6)	0.3950 (4)	0.5223 (7)	0.0670 (19)
H16A	0.3066	0.4437	0.5639	0.080*
H16B	0.3163	0.3586	0.5984	0.080*
C17	0.3652 (5)	0.4407 (4)	0.3435 (7)	0.0556 (17)
C18	0.3584 (6)	0.5154 (4)	0.3772 (8)	0.0675 (19)
H18	0.3226	0.5295	0.4426	0.081*
C19	0.4055 (6)	0.5681 (4)	0.3121 (9)	0.077 (2)
H19	0.4046	0.6176	0.3381	0.092*
C20	0.4531 (6)	0.5485 (5)	0.2106 (9)	0.076 (2)
H20	0.4825	0.5846	0.1656	0.091*
C21	0.4579 (6)	0.4750 (5)	0.1743 (8)	0.071 (2)
H21	0.4906	0.4622	0.1047	0.086*
C22	0.4145 (5)	0.4197 (4)	0.2401 (7)	0.0536 (16)
C23	0.4210 (6)	0.3400 (4)	0.2060 (8)	0.0657 (19)
H23	0.3725	0.3135	0.2490	0.079*
O1	−0.1819 (4)	0.7608 (3)	−0.2023 (5)	0.0824 (16)
O2	−0.0053 (3)	0.6067 (2)	0.0578 (4)	0.0549 (11)
O3	0.1171 (4)	0.4474 (2)	0.3681 (4)	0.0560 (11)
O4	0.3266 (4)	0.3834 (2)	0.4054 (5)	0.0737 (14)

	U11	U22	U33	U12	U13	U23
Br1	0.0693 (7)	0.0994 (8)	0.1485 (10)	0.0213 (5)	0.0212 (6)	0.0112 (6)
Br2	0.1243 (9)	0.0954 (7)	0.0791 (7)	0.0014 (5)	0.0372 (6)	−0.0179 (5)
C1	0.084 (6)	0.059 (4)	0.059 (5)	0.000 (4)	0.015 (4)	0.000 (4)
C2	0.070 (5)	0.037 (3)	0.042 (4)	−0.006 (3)	0.013 (3)	−0.004 (3)
C3	0.087 (6)	0.052 (4)	0.054 (4)	−0.005 (4)	0.017 (4)	−0.002 (3)
C4	0.096 (6)	0.059 (5)	0.065 (5)	−0.022 (4)	0.027 (5)	0.010 (4)
C5	0.063 (5)	0.082 (5)	0.064 (5)	−0.015 (4)	0.019 (4)	−0.008 (4)
C6	0.058 (5)	0.051 (4)	0.049 (4)	−0.005 (3)	0.008 (3)	−0.001 (3)
C7	0.062 (5)	0.046 (4)	0.041 (4)	−0.004 (3)	0.011 (3)	−0.007 (3)
C8	0.056 (4)	0.040 (3)	0.051 (4)	0.001 (3)	0.019 (3)	0.004 (3)
C9	0.056 (4)	0.044 (4)	0.042 (4)	0.000 (3)	0.016 (3)	−0.010 (3)
C10	0.073 (5)	0.055 (4)	0.060 (4)	0.005 (4)	0.026 (4)	−0.005 (3)
C11	0.051 (4)	0.087 (5)	0.077 (5)	−0.013 (4)	0.030 (4)	−0.016 (5)
C12	0.083 (6)	0.078 (5)	0.071 (5)	−0.028 (4)	0.049 (5)	−0.019 (4)
C13	0.069 (5)	0.062 (4)	0.051 (4)	−0.008 (4)	0.021 (4)	0.002 (3)
C14	0.058 (5)	0.045 (4)	0.049 (4)	−0.005 (3)	0.025 (3)	−0.001 (3)
C15	0.071 (5)	0.056 (4)	0.034 (3)	0.001 (3)	0.017 (3)	0.006 (3)
C16	0.082 (5)	0.069 (5)	0.053 (4)	0.004 (4)	0.025 (4)	0.006 (4)
C17	0.047 (4)	0.060 (4)	0.056 (4)	0.000 (3)	0.012 (3)	0.003 (3)
C18	0.064 (5)	0.065 (5)	0.075 (5)	0.008 (4)	0.024 (4)	0.011 (4)
C19	0.064 (5)	0.057 (4)	0.086 (6)	0.004 (4)	−0.006 (5)	0.003 (4)
C20	0.063 (5)	0.082 (6)	0.079 (6)	−0.023 (4)	0.020 (4)	0.013 (4)
C21	0.061 (5)	0.088 (6)	0.064 (5)	−0.019 (4)	0.018 (4)	−0.002 (4)
C22	0.038 (4)	0.069 (4)	0.052 (4)	−0.005 (3)	0.011 (3)	−0.003 (3)
C23	0.061 (5)	0.064 (4)	0.081 (5)	0.007 (3)	0.035 (4)	0.001 (4)
O1	0.089 (4)	0.072 (3)	0.068 (3)	0.029 (3)	0.000 (3)	0.008 (3)
O2	0.058 (3)	0.050 (3)	0.057 (3)	0.002 (2)	0.019 (2)	0.014 (2)
O3	0.061 (3)	0.058 (3)	0.051 (3)	−0.002 (2)	0.021 (2)	0.011 (2)
O4	0.097 (4)	0.059 (3)	0.084 (3)	0.006 (3)	0.056 (3)	0.007 (3)

Br1—C23	1.941 (7)	C12—C13	1.377 (10)
Br2—C23	1.931 (7)	C12—H12	0.9300
C1—O1	1.182 (8)	C13—C14	1.380 (8)
C1—C2	1.485 (10)	C13—H13	0.9300
C1—H1	0.9300	C14—O3	1.368 (7)
C2—C3	1.389 (9)	C15—O3	1.441 (7)
C2—C7	1.400 (8)	C15—C16	1.510 (9)
C3—C4	1.344 (10)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.389 (10)	C16—O4	1.414 (7)
C4—H4	0.9300	C16—H16A	0.9700
C5—C6	1.395 (9)	C16—H16B	0.9700
C5—H5	0.9300	C17—O4	1.367 (7)
C6—C7	1.376 (9)	C17—C18	1.397 (9)
C6—H6	0.9300	C17—C22	1.397 (9)
C7—O2	1.366 (7)	C18—C19	1.385 (10)
C8—O2	1.437 (7)	C18—H18	0.9300
C8—C9	1.510 (8)	C19—C20	1.361 (11)
C8—H8A	0.9700	C19—H19	0.9300
C8—H8B	0.9700	C20—C21	1.379 (11)
C9—C10	1.372 (9)	C20—H20	0.9300
C9—C14	1.390 (8)	C21—C22	1.394 (9)
C10—C11	1.408 (9)	C21—H21	0.9300
C10—H10	0.9300	C22—C23	1.486 (9)
C11—C12	1.344 (10)	C23—H23	0.9800
C11—H11	0.9300
O1—C1—C2	124.9 (7)	O3—C14—C13	125.8 (6)
O1—C1—H1	117.5	O3—C14—C9	114.6 (5)
C2—C1—H1	117.5	C13—C14—C9	119.7 (6)
C3—C2—C7	118.2 (7)	O3—C15—C16	107.8 (5)
C3—C2—C1	119.9 (6)	O3—C15—H15A	110.1
C7—C2—C1	121.9 (6)	C16—C15—H15A	110.1
C4—C3—C2	122.7 (7)	O3—C15—H15B	110.1
C4—C3—H3	118.7	C16—C15—H15B	110.1
C2—C3—H3	118.7	H15A—C15—H15B	108.5
C3—C4—C5	118.6 (7)	O4—C16—C15	111.6 (5)
C3—C4—H4	120.7	O4—C16—H16A	109.3
C5—C4—H4	120.7	C15—C16—H16A	109.3
C4—C5—C6	121.2 (7)	O4—C16—H16B	109.3
C4—C5—H5	119.4	C15—C16—H16B	109.3
C6—C5—H5	119.4	H16A—C16—H16B	108.0
C7—C6—C5	118.8 (6)	O4—C17—C18	124.7 (6)
C7—C6—H6	120.6	O4—C17—C22	114.9 (6)
C5—C6—H6	120.6	C18—C17—C22	120.4 (6)
O2—C7—C6	124.6 (6)	C19—C18—C17	119.3 (7)
O2—C7—C2	114.9 (6)	C19—C18—H18	120.4
C6—C7—C2	120.5 (6)	C17—C18—H18	120.4
O2—C8—C9	107.8 (5)	C20—C19—C18	120.8 (7)
O2—C8—H8A	110.1	C20—C19—H19	119.6
C9—C8—H8A	110.1	C18—C19—H19	119.6
O2—C8—H8B	110.1	C19—C20—C21	120.1 (7)
C9—C8—H8B	110.1	C19—C20—H20	119.9
H8A—C8—H8B	108.5	C21—C20—H20	119.9
C10—C9—C14	119.3 (6)	C20—C21—C22	121.1 (7)
C10—C9—C8	122.8 (6)	C20—C21—H21	119.5
C14—C9—C8	117.8 (5)	C22—C21—H21	119.5
C9—C10—C11	120.0 (7)	C17—C22—C21	118.2 (7)
C9—C10—H10	120.0	C17—C22—C23	119.5 (6)
C11—C10—H10	120.0	C21—C22—C23	122.3 (6)
C12—C11—C10	120.1 (7)	C22—C23—Br2	113.9 (5)
C12—C11—H11	120.0	C22—C23—Br1	111.4 (5)
C10—C11—H11	120.0	Br2—C23—Br1	110.4 (3)
C11—C12—C13	120.3 (6)	C22—C23—H23	106.9
C11—C12—H12	119.8	Br2—C23—H23	106.9
C13—C12—H12	119.8	Br1—C23—H23	106.9
C14—C13—C12	120.6 (7)	C7—O2—C8	118.4 (5)
C14—C13—H13	119.7	C14—O3—C15	117.5 (5)
C12—C13—H13	119.7	C17—O4—C16	121.6 (5)
O1—C1—C2—C3	−6.0 (10)	O3—C15—C16—O4	−63.5 (7)
O1—C1—C2—C7	176.8 (6)	O4—C17—C18—C19	176.8 (6)
C7—C2—C3—C4	−0.6 (10)	C22—C17—C18—C19	−3.0 (10)
C1—C2—C3—C4	−178.0 (6)	C17—C18—C19—C20	3.4 (11)
C2—C3—C4—C5	0.6 (10)	C18—C19—C20—C21	−1.9 (11)
C3—C4—C5—C6	0.3 (10)	C19—C20—C21—C22	0.0 (11)
C4—C5—C6—C7	−1.1 (10)	O4—C17—C22—C21	−178.7 (6)
C5—C6—C7—O2	−179.8 (5)	C18—C17—C22—C21	1.1 (9)
C5—C6—C7—C2	1.1 (9)	O4—C17—C22—C23	0.1 (9)
C3—C2—C7—O2	−179.5 (5)	C18—C17—C22—C23	179.9 (6)
C1—C2—C7—O2	−2.2 (8)	C20—C21—C22—C17	0.4 (10)
C3—C2—C7—C6	−0.3 (9)	C20—C21—C22—C23	−178.3 (7)
C1—C2—C7—C6	177.0 (6)	C17—C22—C23—Br2	130.6 (5)
O2—C8—C9—C10	0.0 (8)	C21—C22—C23—Br2	−50.7 (8)
O2—C8—C9—C14	179.3 (5)	C17—C22—C23—Br1	−103.8 (6)
C14—C9—C10—C11	−1.3 (9)	C21—C22—C23—Br1	75.0 (7)
C8—C9—C10—C11	178.0 (5)	C6—C7—O2—C8	6.8 (8)
C9—C10—C11—C12	1.0 (10)	C2—C7—O2—C8	−174.1 (5)
C10—C11—C12—C13	−0.4 (10)	C9—C8—O2—C7	177.1 (4)
C11—C12—C13—C14	0.0 (10)	C13—C14—O3—C15	2.5 (8)
C12—C13—C14—O3	179.5 (6)	C9—C14—O3—C15	−177.8 (5)
C12—C13—C14—C9	−0.3 (9)	C16—C15—O3—C14	−172.6 (5)
C10—C9—C14—O3	−178.8 (5)	C18—C17—O4—C16	−6.4 (10)
C8—C9—C14—O3	1.8 (7)	C22—C17—O4—C16	173.5 (5)
C10—C9—C14—C13	1.0 (9)	C15—C16—O4—C17	105.9 (7)
C8—C9—C14—C13	−178.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2	0.93	2.42	2.753 (9)	101
C10—H10···O2	0.93	2.35	2.710 (8)	102
C23—H23···O4	0.98	2.19	2.700 (8)	111
C5—H5···Br1i	0.93	3.03	3.529 (7)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Br1i	0.93	3.03	3.529 (7)	116

Symmetry code: (i) .