2-(4-{3-[1-(3-Bromo-prop-yl)-3,3-dimethyl-2,3-dihydro-1H-indol-2-yl-idene]prop-1-en-yl}-3-cyano-5,5-dimethyl-2,5-dihydro-furan-2-yl-idene)malononitrile.

The backbone of the title mol-ecule, C(26)H(25)BrN(4)O, is approximately planar: the dihedral angle between the planes of the indoline ring system and the furan ring is 7.68 (14)°. In the crystal, layers lying parallel to (10) occur, with the mol-ecules inter-acting via weak C-H⋯N(cyano) and C-H⋯Br bonds and short N(cyano)⋯Br contacts [3.345 (4) Å].

Related literature

For general background to zwitterionic dyes and their applications, see: Dalton (2002 ▶); Gainsford et al. (2007 ▶, 2008 ▶); Kay et al. (2004 ▶). For related structures, see: Li et al. (2005 ▶); Marder et al. (1993 ▶); Mushkalo & Sogulayaev (1986 ▶); Wang et al. (2007 ▶). For a description of the Cambridge Stuctural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C26H25BrN4O

M = 489.41

Monoclinic,

a = 10.2349 (4) Å

b = 9.4017 (4) Å

c = 24.4524 (10) Å

β = 96.175 (2)°

V = 2339.29 (17) Å3

Z = 4

Mo Kα radiation

μ = 1.78 mm−1

T = 122 K

0.85 × 0.36 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.549, T max = 0.746 (expected range = 0.616–0.837)

56895 measured reflections

6791 independent reflections

5482 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.156

S = 1.19

6791 reflections

293 parameters

H-atom parameters constrained

Δρmax = 3.08 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT and SADABS (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017747/hb2973sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017747/hb2973Isup2.hkl

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

C26H25BrN4O	F(000) = 1008
Mr = 489.41	Dx = 1.390 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9973 reflections
a = 10.2349 (4) Å	θ = 2.3–29.3°
b = 9.4017 (4) Å	µ = 1.78 mm−1
c = 24.4524 (10) Å	T = 122 K
β = 96.175 (2)°	Block, red
V = 2339.29 (17) Å3	0.85 × 0.36 × 0.10 mm
Z = 4

Bruker APEXII CCD diffractometer	6791 independent reflections
Radiation source: fine-focus sealed tube	5482 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 8.333 pixels mm-1	θmax = 30.0°, θmin = 2.5°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (Blessing, 1995)	k = −13→13
Tmin = 0.549, Tmax = 0.746	l = −34→34
56895 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0596P)2 + 4.5665P] where P = (Fo2 + 2Fc2)/3
6791 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 3.08 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

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	1.04264 (4)	−0.19667 (4)	0.464951 (13)	0.03123 (11)
O1	0.4789 (2)	0.4651 (2)	0.11618 (9)	0.0259 (5)
N1	0.5733 (4)	0.9332 (3)	0.18253 (17)	0.0487 (9)
N2	0.3317 (4)	0.7471 (5)	0.04014 (15)	0.0487 (9)
N3	0.7924 (3)	0.6919 (3)	0.24466 (12)	0.0302 (6)
N4	1.0399 (2)	0.1410 (3)	0.36430 (10)	0.0183 (4)
C1	0.5374 (4)	0.8345 (4)	0.15816 (16)	0.0330 (7)
C2	0.4909 (3)	0.7121 (3)	0.12784 (14)	0.0258 (6)
C3	0.4020 (3)	0.7300 (4)	0.07938 (15)	0.0317 (7)
C4	0.6310 (3)	0.3831 (3)	0.18773 (11)	0.0186 (5)
C5	0.5308 (3)	0.3319 (3)	0.14217 (12)	0.0210 (6)
C6	0.5325 (3)	0.5769 (3)	0.14380 (12)	0.0210 (5)
C7	0.6286 (3)	0.5313 (3)	0.18679 (12)	0.0195 (5)
C8	0.5913 (3)	0.2449 (4)	0.09903 (13)	0.0263 (6)
H8A	0.5238	0.2225	0.0688	0.040*
H8B	0.6274	0.1564	0.1156	0.040*
H8C	0.6619	0.2997	0.0849	0.040*
C9	0.4168 (3)	0.2573 (4)	0.16424 (16)	0.0308 (7)
H9A	0.3757	0.3215	0.1890	0.046*
H9B	0.4486	0.1720	0.1845	0.046*
H9C	0.3520	0.2300	0.1336	0.046*
C10	0.7165 (3)	0.6235 (3)	0.21904 (12)	0.0213 (5)
C11	0.7057 (3)	0.2857 (3)	0.22079 (12)	0.0208 (5)
H11	0.6935	0.1877	0.2123	0.025*
C12	0.7964 (3)	0.3200 (3)	0.26505 (12)	0.0213 (6)
H12	0.8067	0.4170	0.2755	0.026*
C13	0.8724 (3)	0.2188 (3)	0.29458 (12)	0.0209 (5)
H13	0.8588	0.1224	0.2838	0.025*
C14	0.9674 (3)	0.2454 (3)	0.33870 (11)	0.0182 (5)
C15	1.1325 (3)	0.1961 (3)	0.40603 (11)	0.0201 (5)
C16	1.2270 (3)	0.1236 (3)	0.43992 (12)	0.0214 (5)
H16	1.2363	0.0233	0.4377	0.026*
C17	1.3078 (3)	0.2043 (4)	0.47734 (13)	0.0280 (6)
H17	1.3740	0.1583	0.5012	0.034*
C18	1.2933 (3)	0.3511 (4)	0.48045 (14)	0.0293 (7)
H18	1.3500	0.4040	0.5063	0.035*
C19	1.1968 (3)	0.4214 (4)	0.44613 (13)	0.0267 (6)
H19	1.1860	0.5215	0.4485	0.032*
C20	1.1171 (3)	0.3418 (3)	0.40854 (12)	0.0203 (5)
C21	1.0071 (3)	0.3868 (3)	0.36571 (11)	0.0193 (5)
C22	1.0602 (3)	0.4925 (3)	0.32554 (14)	0.0272 (6)
H22A	1.1278	0.4459	0.3064	0.041*
H22B	1.0984	0.5748	0.3460	0.041*
H22C	0.9882	0.5241	0.2986	0.041*
C23	0.8931 (3)	0.4525 (4)	0.39357 (13)	0.0263 (6)
H23A	0.8224	0.4806	0.3654	0.039*
H23B	0.9248	0.5363	0.4148	0.039*
H23C	0.8596	0.3823	0.4182	0.039*
C24	1.0321 (3)	−0.0092 (3)	0.34754 (12)	0.0206 (5)
H24A	1.1117	−0.0592	0.3643	0.025*
H24B	1.0317	−0.0147	0.3071	0.025*
C25	0.9108 (3)	−0.0860 (3)	0.36403 (12)	0.0237 (6)
H25A	0.8316	−0.0389	0.3455	0.028*
H25B	0.9116	−0.1849	0.3502	0.028*
C26	0.8990 (3)	−0.0903 (4)	0.42482 (13)	0.0281 (6)
H26A	0.8143	−0.1349	0.4311	0.034*
H26B	0.8990	0.0082	0.4392	0.034*

	U11	U22	U33	U12	U13	U23
Br1	0.0428 (2)	0.02650 (17)	0.02325 (16)	−0.00417 (14)	−0.00169 (12)	0.00277 (13)
O1	0.0256 (10)	0.0217 (10)	0.0283 (11)	0.0037 (8)	−0.0076 (8)	0.0013 (9)
N1	0.061 (2)	0.0208 (15)	0.061 (2)	0.0085 (15)	−0.0063 (18)	−0.0004 (15)
N2	0.0389 (18)	0.065 (2)	0.0400 (19)	0.0197 (17)	−0.0053 (15)	0.0059 (17)
N3	0.0309 (14)	0.0266 (14)	0.0326 (14)	0.0013 (11)	0.0015 (11)	−0.0061 (12)
N4	0.0171 (10)	0.0198 (11)	0.0173 (11)	−0.0004 (9)	−0.0010 (8)	0.0007 (9)
C1	0.0345 (17)	0.0250 (16)	0.0390 (19)	0.0095 (13)	0.0019 (14)	0.0068 (14)
C2	0.0247 (14)	0.0243 (15)	0.0280 (15)	0.0087 (12)	0.0012 (11)	0.0049 (12)
C3	0.0285 (16)	0.0319 (18)	0.0348 (18)	0.0122 (13)	0.0032 (13)	0.0056 (14)
C4	0.0176 (12)	0.0212 (13)	0.0169 (12)	0.0015 (10)	0.0013 (9)	−0.0016 (10)
C5	0.0188 (12)	0.0187 (13)	0.0242 (14)	0.0030 (10)	−0.0044 (10)	0.0021 (10)
C6	0.0196 (12)	0.0221 (14)	0.0210 (13)	0.0046 (10)	0.0017 (10)	0.0015 (11)
C7	0.0198 (12)	0.0193 (13)	0.0193 (13)	0.0032 (10)	0.0012 (10)	−0.0007 (10)
C8	0.0299 (16)	0.0261 (15)	0.0221 (14)	0.0014 (12)	−0.0016 (12)	−0.0022 (12)
C9	0.0172 (13)	0.0291 (16)	0.046 (2)	0.0003 (12)	0.0014 (13)	0.0062 (14)
C10	0.0228 (13)	0.0179 (13)	0.0232 (14)	0.0042 (10)	0.0034 (10)	−0.0013 (11)
C11	0.0215 (13)	0.0190 (13)	0.0212 (13)	0.0018 (10)	−0.0016 (10)	0.0005 (10)
C12	0.0209 (13)	0.0216 (14)	0.0210 (13)	0.0000 (10)	0.0004 (10)	−0.0001 (10)
C13	0.0226 (13)	0.0192 (13)	0.0200 (13)	−0.0012 (10)	−0.0021 (10)	0.0001 (10)
C14	0.0178 (12)	0.0204 (13)	0.0165 (12)	0.0000 (10)	0.0018 (10)	0.0025 (10)
C15	0.0159 (11)	0.0288 (14)	0.0155 (12)	−0.0019 (11)	0.0017 (9)	0.0028 (11)
C16	0.0188 (12)	0.0238 (14)	0.0212 (13)	−0.0010 (10)	0.0002 (10)	0.0026 (11)
C17	0.0198 (13)	0.0391 (18)	0.0237 (14)	−0.0021 (13)	−0.0043 (11)	0.0043 (13)
C18	0.0241 (14)	0.0344 (17)	0.0271 (15)	−0.0080 (13)	−0.0074 (12)	−0.0015 (13)
C19	0.0272 (14)	0.0232 (15)	0.0283 (15)	−0.0074 (12)	−0.0040 (12)	0.0001 (12)
C20	0.0194 (12)	0.0221 (13)	0.0188 (13)	−0.0042 (10)	−0.0008 (10)	0.0024 (10)
C21	0.0201 (12)	0.0191 (13)	0.0179 (12)	−0.0038 (10)	−0.0011 (10)	0.0024 (10)
C22	0.0296 (15)	0.0215 (14)	0.0296 (15)	−0.0067 (12)	−0.0014 (12)	0.0065 (12)
C23	0.0253 (14)	0.0252 (15)	0.0278 (15)	−0.0004 (12)	0.0009 (11)	−0.0057 (12)
C24	0.0237 (13)	0.0194 (13)	0.0184 (13)	0.0011 (10)	0.0012 (10)	−0.0014 (10)
C25	0.0253 (14)	0.0222 (14)	0.0227 (14)	−0.0060 (11)	−0.0021 (11)	−0.0002 (11)
C26	0.0278 (15)	0.0312 (17)	0.0261 (15)	−0.0029 (13)	0.0061 (12)	0.0006 (13)

Br1—C26	1.953 (3)	C13—H13	0.9500
O1—C6	1.336 (4)	C14—C21	1.520 (4)
O1—C5	1.476 (3)	C15—C20	1.382 (4)
N1—C1	1.142 (5)	C15—C16	1.383 (4)
N2—C3	1.147 (5)	C16—C17	1.390 (4)
N3—C10	1.142 (4)	C16—H16	0.9500
N4—C14	1.344 (4)	C17—C18	1.392 (5)
N4—C15	1.414 (4)	C17—H17	0.9500
N4—C24	1.470 (4)	C18—C19	1.393 (4)
C1—C2	1.423 (5)	C18—H18	0.9500
C2—C6	1.383 (4)	C19—C20	1.382 (4)
C2—C3	1.424 (5)	C19—H19	0.9500
C4—C7	1.394 (4)	C20—C21	1.513 (4)
C4—C11	1.395 (4)	C21—C22	1.537 (4)
C4—C5	1.510 (4)	C21—C23	1.542 (4)
C5—C9	1.510 (4)	C22—H22A	0.9800
C5—C8	1.519 (4)	C22—H22B	0.9800
C6—C7	1.426 (4)	C22—H22C	0.9800
C7—C10	1.424 (4)	C23—H23A	0.9800
C8—H8A	0.9800	C23—H23B	0.9800
C8—H8B	0.9800	C23—H23C	0.9800
C8—H8C	0.9800	C24—C25	1.528 (4)
C9—H9A	0.9800	C24—H24A	0.9900
C9—H9B	0.9800	C24—H24B	0.9900
C9—H9C	0.9800	C25—C26	1.505 (4)
C11—C12	1.386 (4)	C25—H25A	0.9900
C11—H11	0.9500	C25—H25B	0.9900
C12—C13	1.383 (4)	C26—H26A	0.9900
C12—H12	0.9500	C26—H26B	0.9900
C13—C14	1.395 (4)
C6—O1—C5	109.9 (2)	C15—C16—C17	117.0 (3)
C14—N4—C15	111.2 (2)	C15—C16—H16	121.5
C14—N4—C24	124.2 (2)	C17—C16—H16	121.5
C15—N4—C24	124.4 (2)	C16—C17—C18	121.2 (3)
N1—C1—C2	179.2 (4)	C16—C17—H17	119.4
C6—C2—C1	121.4 (3)	C18—C17—H17	119.4
C6—C2—C3	119.5 (3)	C17—C18—C19	120.7 (3)
C1—C2—C3	119.1 (3)	C17—C18—H18	119.7
N2—C3—C2	178.6 (4)	C19—C18—H18	119.7
C7—C4—C11	132.4 (3)	C20—C19—C18	118.3 (3)
C7—C4—C5	107.3 (2)	C20—C19—H19	120.9
C11—C4—C5	120.3 (3)	C18—C19—H19	120.9
O1—C5—C4	103.4 (2)	C15—C20—C19	120.3 (3)
O1—C5—C9	107.0 (2)	C15—C20—C21	109.1 (2)
C4—C5—C9	112.0 (3)	C19—C20—C21	130.6 (3)
O1—C5—C8	108.2 (2)	C20—C21—C14	101.6 (2)
C4—C5—C8	112.9 (2)	C20—C21—C22	109.6 (2)
C9—C5—C8	112.7 (3)	C14—C21—C22	112.6 (2)
O1—C6—C2	118.9 (3)	C20—C21—C23	110.4 (2)
O1—C6—C7	110.4 (2)	C14—C21—C23	111.2 (2)
C2—C6—C7	130.6 (3)	C22—C21—C23	111.1 (3)
C4—C7—C10	126.2 (3)	C21—C22—H22A	109.5
C4—C7—C6	108.8 (3)	C21—C22—H22B	109.5
C10—C7—C6	124.7 (3)	H22A—C22—H22B	109.5
C5—C8—H8A	109.5	C21—C22—H22C	109.5
C5—C8—H8B	109.5	H22A—C22—H22C	109.5
H8A—C8—H8B	109.5	H22B—C22—H22C	109.5
C5—C8—H8C	109.5	C21—C23—H23A	109.5
H8A—C8—H8C	109.5	C21—C23—H23B	109.5
H8B—C8—H8C	109.5	H23A—C23—H23B	109.5
C5—C9—H9A	109.5	C21—C23—H23C	109.5
C5—C9—H9B	109.5	H23A—C23—H23C	109.5
H9A—C9—H9B	109.5	H23B—C23—H23C	109.5
C5—C9—H9C	109.5	N4—C24—C25	113.6 (2)
H9A—C9—H9C	109.5	N4—C24—H24A	108.8
H9B—C9—H9C	109.5	C25—C24—H24A	108.8
N3—C10—C7	176.1 (3)	N4—C24—H24B	108.8
C12—C11—C4	125.4 (3)	C25—C24—H24B	108.8
C12—C11—H11	117.3	H24A—C24—H24B	107.7
C4—C11—H11	117.3	C26—C25—C24	115.3 (2)
C13—C12—C11	122.7 (3)	C26—C25—H25A	108.5
C13—C12—H12	118.7	C24—C25—H25A	108.5
C11—C12—H12	118.7	C26—C25—H25B	108.5
C12—C13—C14	125.9 (3)	C24—C25—H25B	108.5
C12—C13—H13	117.0	H25A—C25—H25B	107.5
C14—C13—H13	117.0	C25—C26—Br1	112.0 (2)
N4—C14—C13	122.2 (3)	C25—C26—H26A	109.2
N4—C14—C21	109.2 (2)	Br1—C26—H26A	109.2
C13—C14—C21	128.6 (3)	C25—C26—H26B	109.2
C20—C15—C16	122.5 (3)	Br1—C26—H26B	109.2
C20—C15—N4	108.9 (2)	H26A—C26—H26B	107.9
C16—C15—N4	128.5 (3)
C6—O1—C5—C4	−3.6 (3)	C12—C13—C14—C21	2.0 (5)
C6—O1—C5—C9	114.8 (3)	C14—N4—C15—C20	1.6 (3)
C6—O1—C5—C8	−123.5 (3)	C24—N4—C15—C20	176.2 (2)
C7—C4—C5—O1	1.8 (3)	C14—N4—C15—C16	−177.6 (3)
C11—C4—C5—O1	−177.6 (3)	C24—N4—C15—C16	−3.0 (4)
C7—C4—C5—C9	−113.0 (3)	C20—C15—C16—C17	−0.1 (4)
C11—C4—C5—C9	67.6 (3)	N4—C15—C16—C17	179.0 (3)
C7—C4—C5—C8	118.5 (3)	C15—C16—C17—C18	0.2 (5)
C11—C4—C5—C8	−60.9 (4)	C16—C17—C18—C19	0.3 (5)
C5—O1—C6—C2	−176.3 (3)	C17—C18—C19—C20	−0.8 (5)
C5—O1—C6—C7	4.1 (3)	C16—C15—C20—C19	−0.5 (4)
C1—C2—C6—O1	175.3 (3)	N4—C15—C20—C19	−179.7 (3)
C3—C2—C6—O1	−6.1 (5)	C16—C15—C20—C21	179.2 (3)
C1—C2—C6—C7	−5.1 (5)	N4—C15—C20—C21	0.0 (3)
C3—C2—C6—C7	173.4 (3)	C18—C19—C20—C15	0.9 (5)
C11—C4—C7—C10	6.0 (5)	C18—C19—C20—C21	−178.7 (3)
C5—C4—C7—C10	−173.3 (3)	C15—C20—C21—C14	−1.4 (3)
C11—C4—C7—C6	179.7 (3)	C19—C20—C21—C14	178.3 (3)
C5—C4—C7—C6	0.5 (3)	C15—C20—C21—C22	−120.6 (3)
O1—C6—C7—C4	−2.9 (3)	C19—C20—C21—C22	59.1 (4)
C2—C6—C7—C4	177.6 (3)	C15—C20—C21—C23	116.7 (3)
O1—C6—C7—C10	171.0 (3)	C19—C20—C21—C23	−63.6 (4)
C2—C6—C7—C10	−8.6 (5)	N4—C14—C21—C20	2.3 (3)
C7—C4—C11—C12	3.6 (5)	C13—C14—C21—C20	−177.8 (3)
C5—C4—C11—C12	−177.2 (3)	N4—C14—C21—C22	119.4 (3)
C4—C11—C12—C13	−176.6 (3)	C13—C14—C21—C22	−60.7 (4)
C11—C12—C13—C14	178.5 (3)	N4—C14—C21—C23	−115.1 (3)
C15—N4—C14—C13	177.6 (3)	C13—C14—C21—C23	64.8 (4)
C24—N4—C14—C13	2.9 (4)	C14—N4—C24—C25	−76.2 (3)
C15—N4—C14—C21	−2.5 (3)	C15—N4—C24—C25	109.9 (3)
C24—N4—C14—C21	−177.1 (2)	N4—C24—C25—C26	−60.1 (4)
C12—C13—C14—N4	−178.1 (3)	C24—C25—C26—Br1	−63.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···N1i	0.98	2.59	3.449 (5)	147
C23—H23B···Br1ii	0.98	2.99	3.962 (4)	171
C26—H26B···Br1iii	0.99	2.95	3.815 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯N1i	0.98	2.59	3.449 (5)	147
C23—H23B⋯Br1ii	0.98	2.99	3.962 (4)	171
C26—H26B⋯Br1iii	0.99	2.95	3.815 (4)	147

Symmetry codes: (i) ; (ii) ; (iii) .