2,4-Dibromo-6-[(E)-({3-[(E)-(3,5-dibromo-2-oxidobenzyl-idene)aza-nium-yl]-2,2-dimethyl-prop-yl}iminium-yl)meth-yl]phenolate.

In the title mol-ecule, C(19)H(18)Br(4)N(2)O(2), the dihedral angle between the benzene rings is 73.9 (2)°. Two intra-molecular N-H⋯O hydrogen bonds make S(6) ring motifs. In the crystal, mol-ecules are linked via C-H⋯O inter-actions, forming chains propagating along the a-axis directon. A short C⋯Br [3.401 (5) Å] contact is present in the crystal structure, which is further stabilized by a π-π inter-action [centroid-centroid distance = 3.739 (3) Å].

Related literature

For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Kargar et al. (2011 ▶); Kia et al. (2010 ▶).

Experimental

Crystal data

C19H18Br4N2O

M = 625.99

Orthorhombic,

a = 11.6861 (3) Å

b = 11.4616 (3) Å

c = 31.3782 (9) Å

V = 4202.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 7.68 mm−1

T = 291 K

0.25 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.250, T max = 0.459

38547 measured reflections

5242 independent reflections

2756 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.138

S = 1.04

5242 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.64 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055899/su2354sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055899/su2354Isup2.hkl

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

C19H18Br4N2O	F(000) = 2416
Mr = 625.99	Dx = 1.979 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2370 reflections
a = 11.6861 (3) Å	θ = 2.5–27.5°
b = 11.4616 (3) Å	µ = 7.68 mm−1
c = 31.3782 (9) Å	T = 291 K
V = 4202.8 (2) Å3	Block, yellow
Z = 8	0.25 × 0.16 × 0.12 mm

Bruker SMART APEXII CCD area-detector diffractometer	5242 independent reflections
Radiation source: fine-focus sealed tube	2756 reflections with I > 2σ(I)
graphite	Rint = 0.090
φ and ω scans	θmax = 28.4°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→15
Tmin = 0.250, Tmax = 0.459	k = −15→15
38547 measured reflections	l = −41→41

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0616P)2] where P = (Fo2 + 2Fc2)/3
5242 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.64 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.34182 (5)	−0.30064 (6)	0.37158 (2)	0.0653 (2)
Br2	0.17302 (6)	0.00225 (6)	0.49759 (2)	0.0695 (2)
Br3	0.32582 (5)	0.27233 (8)	0.11028 (2)	0.0748 (3)
Br4	−0.02936 (5)	0.17726 (6)	−0.006978 (18)	0.0531 (2)
O1	0.1272 (3)	−0.2212 (3)	0.32548 (12)	0.0456 (9)
O2	0.1731 (3)	0.1290 (3)	0.16822 (12)	0.0493 (10)
N1	−0.0616 (3)	−0.1131 (4)	0.31559 (14)	0.0399 (11)
H1	−0.0092	−0.1601	0.3081	0.048*
N2	0.0054 (3)	−0.0002 (3)	0.18846 (14)	0.0401 (11)
H2	0.0681	0.0364	0.1930	0.048*
C1	0.0493 (4)	−0.0982 (4)	0.37894 (16)	0.0339 (11)
C2	0.1341 (4)	−0.1743 (4)	0.36298 (16)	0.0348 (12)
C3	0.2273 (4)	−0.1966 (4)	0.39035 (17)	0.0399 (13)
C4	0.2376 (4)	−0.1472 (5)	0.42992 (17)	0.0430 (13)
H4	0.3002	−0.1645	0.4471	0.052*
C5	0.1525 (4)	−0.0701 (5)	0.44416 (17)	0.0417 (13)
C6	0.0597 (4)	−0.0475 (4)	0.41923 (17)	0.0398 (13)
H6	0.0026	0.0022	0.4291	0.048*
C7	−0.0502 (4)	−0.0723 (5)	0.35284 (17)	0.0396 (13)
H7	−0.1072	−0.0243	0.3638	0.047*
C8	−0.1584 (4)	−0.0846 (5)	0.28844 (17)	0.0422 (13)
H8A	−0.2174	−0.0478	0.3055	0.051*
H8B	−0.1899	−0.1560	0.2767	0.051*
C9	−0.1256 (4)	−0.0031 (4)	0.25192 (16)	0.0351 (12)
C10	−0.0651 (4)	0.1058 (4)	0.26898 (17)	0.0438 (13)
H10A	−0.1097	0.1392	0.2916	0.066*
H10B	−0.0568	0.1618	0.2464	0.066*
H10C	0.0090	0.0848	0.2796	0.066*
C11	−0.2360 (4)	0.0326 (5)	0.22920 (19)	0.0528 (16)
H11A	−0.2745	−0.0359	0.2189	0.079*
H11B	−0.2180	0.0827	0.2056	0.079*
H11C	−0.2849	0.0732	0.2488	0.079*
C12	−0.0487 (4)	−0.0721 (5)	0.22116 (17)	0.0444 (13)
H12A	0.0105	−0.1111	0.2375	0.053*
H12B	−0.0943	−0.1318	0.2073	0.053*
C13	−0.0332 (4)	0.0110 (4)	0.15044 (17)	0.0379 (12)
H13	−0.1005	−0.0271	0.1429	0.045*
C14	0.0254 (4)	0.0815 (4)	0.11903 (15)	0.0338 (11)
C15	0.1304 (4)	0.1368 (4)	0.13050 (17)	0.0365 (12)
C16	0.1851 (4)	0.2010 (5)	0.09768 (18)	0.0407 (13)
C17	0.1389 (4)	0.2107 (4)	0.05729 (17)	0.0412 (13)
H17	0.1776	0.2522	0.0363	0.049*
C18	0.0336 (4)	0.1579 (4)	0.04800 (15)	0.0354 (11)
C19	−0.0218 (4)	0.0939 (4)	0.07783 (16)	0.0365 (12)
H19	−0.0909	0.0580	0.0712	0.044*

	U11	U22	U33	U12	U13	U23
Br1	0.0620 (4)	0.0651 (4)	0.0688 (5)	0.0276 (3)	−0.0133 (3)	−0.0081 (4)
Br2	0.0780 (5)	0.0835 (5)	0.0470 (4)	−0.0080 (4)	−0.0106 (3)	−0.0238 (3)
Br3	0.0533 (4)	0.1174 (6)	0.0537 (4)	−0.0359 (4)	0.0020 (3)	0.0015 (4)
Br4	0.0591 (4)	0.0723 (4)	0.0279 (3)	0.0027 (3)	−0.0031 (3)	0.0027 (3)
O1	0.056 (2)	0.048 (2)	0.033 (2)	0.0070 (18)	−0.0035 (18)	−0.0054 (18)
O2	0.043 (2)	0.071 (3)	0.034 (2)	−0.0015 (18)	−0.0082 (18)	0.008 (2)
N1	0.037 (2)	0.051 (3)	0.032 (3)	0.0050 (19)	0.001 (2)	0.005 (2)
N2	0.040 (2)	0.046 (3)	0.035 (3)	0.0020 (19)	0.007 (2)	0.008 (2)
C1	0.039 (3)	0.034 (3)	0.029 (3)	−0.001 (2)	0.002 (2)	0.007 (2)
C2	0.044 (3)	0.030 (3)	0.031 (3)	−0.004 (2)	−0.002 (2)	0.008 (2)
C3	0.042 (3)	0.033 (3)	0.044 (4)	−0.001 (2)	−0.005 (3)	0.007 (3)
C4	0.043 (3)	0.048 (3)	0.038 (3)	−0.004 (3)	−0.008 (3)	0.002 (3)
C5	0.053 (3)	0.043 (3)	0.029 (3)	−0.010 (3)	−0.004 (3)	−0.001 (2)
C6	0.046 (3)	0.040 (3)	0.033 (3)	−0.001 (2)	0.004 (3)	0.001 (3)
C7	0.046 (3)	0.040 (3)	0.033 (3)	0.003 (2)	0.008 (3)	0.007 (2)
C8	0.035 (3)	0.060 (4)	0.032 (3)	−0.003 (3)	−0.005 (2)	0.010 (3)
C9	0.030 (2)	0.048 (3)	0.028 (3)	0.002 (2)	0.003 (2)	0.010 (2)
C10	0.046 (3)	0.049 (3)	0.037 (3)	−0.001 (3)	0.003 (3)	0.006 (3)
C11	0.036 (3)	0.077 (4)	0.045 (4)	−0.001 (3)	−0.005 (3)	0.021 (3)
C12	0.052 (3)	0.048 (3)	0.033 (3)	0.001 (3)	0.004 (3)	0.011 (3)
C13	0.041 (3)	0.037 (3)	0.036 (3)	−0.005 (2)	0.000 (3)	−0.001 (2)
C14	0.040 (3)	0.037 (3)	0.024 (3)	0.005 (2)	0.003 (2)	−0.005 (2)
C15	0.033 (3)	0.038 (3)	0.039 (3)	0.002 (2)	0.001 (2)	−0.004 (3)
C16	0.036 (3)	0.050 (3)	0.036 (3)	−0.006 (2)	0.005 (2)	−0.002 (3)
C17	0.046 (3)	0.044 (3)	0.033 (3)	0.003 (3)	0.012 (3)	0.005 (3)
C18	0.046 (3)	0.039 (3)	0.022 (3)	0.005 (2)	0.000 (2)	−0.005 (2)
C19	0.035 (3)	0.043 (3)	0.031 (3)	−0.001 (2)	0.000 (2)	−0.006 (2)

Br1—C3	1.887 (5)	C8—H8A	0.9700
Br2—C5	1.886 (5)	C8—H8B	0.9700
Br3—C16	1.879 (5)	C9—C11	1.530 (7)
Br4—C18	1.889 (5)	C9—C10	1.531 (7)
O1—C2	1.296 (6)	C9—C12	1.538 (7)
O2—C15	1.287 (6)	C10—H10A	0.9600
N1—C7	1.266 (6)	C10—H10B	0.9600
N1—C8	1.453 (6)	C10—H10C	0.9600
N1—H1	0.8479	C11—H11A	0.9600
N2—C13	1.282 (6)	C11—H11B	0.9600
N2—C12	1.460 (6)	C11—H11C	0.9600
N2—H2	0.8557	C12—H12A	0.9700
C1—C6	1.397 (7)	C12—H12B	0.9700
C1—C2	1.412 (7)	C13—C14	1.447 (7)
C1—C7	1.454 (7)	C13—H13	0.9300
C2—C3	1.410 (7)	C14—C19	1.412 (7)
C3—C4	1.370 (7)	C14—C15	1.427 (7)
C4—C5	1.403 (7)	C15—C16	1.418 (7)
C4—H4	0.9300	C16—C17	1.382 (7)
C5—C6	1.363 (7)	C17—C18	1.402 (7)
C6—H6	0.9300	C17—H17	0.9300
C7—H7	0.9300	C18—C19	1.354 (7)
C8—C9	1.527 (7)	C19—H19	0.9300
C7—N1—C8	122.6 (5)	C9—C10—H10A	109.5
C7—N1—H1	114.5	C9—C10—H10B	109.5
C8—N1—H1	122.9	H10A—C10—H10B	109.5
C13—N2—C12	123.9 (5)	C9—C10—H10C	109.5
C13—N2—H2	114.0	H10A—C10—H10C	109.5
C12—N2—H2	122.1	H10B—C10—H10C	109.5
C6—C1—C2	121.2 (5)	C9—C11—H11A	109.5
C6—C1—C7	119.6 (5)	C9—C11—H11B	109.5
C2—C1—C7	119.2 (5)	H11A—C11—H11B	109.5
O1—C2—C3	121.8 (5)	C9—C11—H11C	109.5
O1—C2—C1	122.3 (5)	H11A—C11—H11C	109.5
C3—C2—C1	115.9 (5)	H11B—C11—H11C	109.5
C4—C3—C2	123.1 (5)	N2—C12—C9	113.8 (4)
C4—C3—Br1	118.8 (4)	N2—C12—H12A	108.8
C2—C3—Br1	118.1 (4)	C9—C12—H12A	108.8
C3—C4—C5	119.1 (5)	N2—C12—H12B	108.8
C3—C4—H4	120.4	C9—C12—H12B	108.8
C5—C4—H4	120.4	H12A—C12—H12B	107.7
C6—C5—C4	120.1 (5)	N2—C13—C14	121.5 (5)
C6—C5—Br2	121.9 (4)	N2—C13—H13	119.2
C4—C5—Br2	118.0 (4)	C14—C13—H13	119.2
C5—C6—C1	120.6 (5)	C19—C14—C15	121.5 (5)
C5—C6—H6	119.7	C19—C14—C13	119.6 (5)
C1—C6—H6	119.7	C15—C14—C13	118.9 (5)
N1—C7—C1	121.9 (5)	O2—C15—C16	121.9 (5)
N1—C7—H7	119.1	O2—C15—C14	122.3 (5)
C1—C7—H7	119.1	C16—C15—C14	115.8 (5)
N1—C8—C9	112.5 (4)	C17—C16—C15	122.1 (5)
N1—C8—H8A	109.1	C17—C16—Br3	120.0 (4)
C9—C8—H8A	109.1	C15—C16—Br3	117.9 (4)
N1—C8—H8B	109.1	C16—C17—C18	119.9 (5)
C9—C8—H8B	109.1	C16—C17—H17	120.0
H8A—C8—H8B	107.8	C18—C17—H17	120.0
C8—C9—C11	107.5 (4)	C19—C18—C17	120.7 (5)
C8—C9—C10	110.6 (4)	C19—C18—Br4	120.6 (4)
C11—C9—C10	109.6 (4)	C17—C18—Br4	118.8 (4)
C8—C9—C12	107.6 (4)	C18—C19—C14	120.0 (5)
C11—C9—C12	109.7 (4)	C18—C19—H19	120.0
C10—C9—C12	111.7 (4)	C14—C19—H19	120.0
C6—C1—C2—O1	−179.0 (4)	C13—N2—C12—C9	−97.7 (6)
C7—C1—C2—O1	0.9 (7)	C8—C9—C12—N2	−170.1 (4)
C6—C1—C2—C3	1.0 (7)	C11—C9—C12—N2	73.2 (5)
C7—C1—C2—C3	−179.1 (4)	C10—C9—C12—N2	−48.5 (6)
O1—C2—C3—C4	179.1 (5)	C12—N2—C13—C14	−178.6 (4)
C1—C2—C3—C4	−0.9 (7)	N2—C13—C14—C19	−178.4 (5)
O1—C2—C3—Br1	−1.6 (6)	N2—C13—C14—C15	1.9 (7)
C1—C2—C3—Br1	178.4 (3)	C19—C14—C15—O2	178.1 (5)
C2—C3—C4—C5	−0.4 (8)	C13—C14—C15—O2	−2.2 (7)
Br1—C3—C4—C5	−179.7 (4)	C19—C14—C15—C16	−1.9 (7)
C3—C4—C5—C6	1.7 (8)	C13—C14—C15—C16	177.8 (4)
C3—C4—C5—Br2	−177.0 (4)	O2—C15—C16—C17	−179.2 (5)
C4—C5—C6—C1	−1.5 (8)	C14—C15—C16—C17	0.8 (7)
Br2—C5—C6—C1	177.0 (4)	O2—C15—C16—Br3	1.7 (7)
C2—C1—C6—C5	0.2 (8)	C14—C15—C16—Br3	−178.3 (3)
C7—C1—C6—C5	−179.7 (5)	C15—C16—C17—C18	1.2 (8)
C8—N1—C7—C1	−177.6 (4)	Br3—C16—C17—C18	−179.7 (4)
C6—C1—C7—N1	177.6 (5)	C16—C17—C18—C19	−2.3 (8)
C2—C1—C7—N1	−2.2 (7)	C16—C17—C18—Br4	177.9 (4)
C7—N1—C8—C9	107.5 (6)	C17—C18—C19—C14	1.2 (7)
N1—C8—C9—C11	−173.0 (5)	Br4—C18—C19—C14	−179.0 (4)
N1—C8—C9—C10	−53.4 (6)	C15—C14—C19—C18	1.0 (7)
N1—C8—C9—C12	68.8 (6)	C13—C14—C19—C18	−178.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.85	1.82	2.549 (5)	142
N2—H2···O2	0.86	1.80	2.537 (5)	143
C8—H8A···O2i	0.97	2.53	3.424 (7)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.85	1.82	2.549 (5)	142
N2—H2⋯O2	0.86	1.80	2.537 (5)	143
C8—H8A⋯O2i	0.97	2.53	3.424 (7)	152

Symmetry code: (i) .