(E)-1,1'-Dibutyl-3,3'-biindolinyl-idene-2,2'-dione.

In the title mol-ecule, C(24)H(26)N(2)O(2), the two indol-2-one units, which are connected by a C=C double bond, are almost coplanar with an inter-planar angle of 6.8 (1)°. On cooling from 293 to 120 K, the space group changes from P2(1)/n to P2(1). Two intra-molecular C-H⋯O hydrogen bonds occur.

Related literature

For uses of isoindigo derivatives as medicines, see: Sassatelli et al. (2004 ▶). For the room temperature (293 K) structure, see: Yuan et al. (2007 ▶).

Experimental

Crystal data

C24H26N2O2

M = 374.47

Monoclinic,

a = 8.9224 (3) Å

b = 11.9605 (5) Å

c = 9.6827 (4) Å

β = 110.782 (1)°

V = 966.07 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.20 × 0.11 × 0.09 mm

Data collection

Bruker SMART 6K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.984, T max = 0.993

13014 measured reflections

2926 independent reflections

2477 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.121

S = 1.04

2926 reflections

257 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681005066X/jh2237sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005066X/jh2237Isup2.hkl

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

C24H26N2O2	F(000) = 400
Mr = 374.47	Dx = 1.287 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3669 reflections
a = 8.9224 (3) Å	θ = 2.7–30.0°
b = 11.9605 (5) Å	µ = 0.08 mm−1
c = 9.6827 (4) Å	T = 120 K
β = 110.782 (1)°	Plank, purple
V = 966.07 (7) Å3	0.20 × 0.11 × 0.09 mm
Z = 2

Bruker SMART 6K CCD area-detector diffractometer	2926 independent reflections
Radiation source: fine-focus sealed tube	2477 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: ω pixels mm-1	θmax = 30.0°, θmin = 2.3°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −16→16
Tmin = 0.984, Tmax = 0.993	l = −13→13
13014 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0708P)2 + 0.1553P] where P = (Fo2 + 2Fc2)/3
2926 reflections	(Δ/σ)max = 0.003
257 parameters	Δρmax = 0.38 e Å−3
1 restraint	Δρmin = −0.22 e Å−3

Experimental. The data collection nominally covered full sphere of reciprocal space, by a combination of 3 runs of narrow-frame ω-scans (scan width 0.3° ω, 20 s exposure), every run at a different φ angle. Crystal to detector distance 4.83 cm.

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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. Methyl groups were refined as rigid bodies rotating around C—C bonds, with a common refined U for three H atoms. Other H atoms: riding model.

	x	y	z	Uiso*/Ueq
O1	0.5183 (2)	0.40482 (16)	0.3409 (2)	0.0316 (4)
O2	0.9572 (2)	0.57182 (16)	0.1333 (2)	0.0298 (4)
N1	0.7459 (2)	0.30308 (16)	0.4455 (2)	0.0223 (4)
N2	0.7454 (2)	0.69090 (16)	0.0617 (2)	0.0212 (4)
C1	0.6589 (3)	0.3867 (2)	0.3584 (2)	0.0219 (4)
C2	0.7669 (2)	0.44723 (18)	0.2919 (2)	0.0192 (4)
C3	0.9220 (2)	0.38775 (19)	0.3518 (2)	0.0195 (4)
C4	1.0726 (3)	0.3982 (2)	0.3403 (3)	0.0227 (4)
H4	1.0912	0.4548	0.2795	0.027*
C5	1.1959 (3)	0.3257 (2)	0.4182 (3)	0.0266 (5)
H5	1.2985	0.3338	0.4103	0.032*
C6	1.1715 (3)	0.2420 (2)	0.5069 (3)	0.0265 (5)
H6A	1.2570	0.1932	0.5587	0.032*
C7	1.0227 (3)	0.2291 (2)	0.5203 (3)	0.0257 (5)
H7	1.0049	0.1719	0.5809	0.031*
C8	0.9016 (3)	0.30130 (19)	0.4437 (2)	0.0210 (4)
C9	0.6854 (3)	0.2281 (2)	0.5331 (2)	0.0259 (5)
H9A	0.5909	0.2631	0.5466	0.031*
H9B	0.7690	0.2188	0.6321	0.031*
C10	0.6377 (3)	0.1131 (2)	0.4634 (3)	0.0289 (5)
H10A	0.7291	0.0810	0.4414	0.035*
H10B	0.6157	0.0633	0.5356	0.035*
C11	0.4915 (3)	0.1152 (2)	0.3223 (3)	0.0330 (5)
H11A	0.4000	0.1472	0.3440	0.040*
H11B	0.5135	0.1646	0.2496	0.040*
C12	0.4457 (4)	0.0003 (2)	0.2548 (3)	0.0424 (7)
H12A	0.3545	0.0068	0.1617	0.049 (6)*
H12B	0.4161	−0.0474	0.3233	0.049 (6)*
H12C	0.5370	−0.0328	0.2358	0.049 (6)*
C21	0.8248 (2)	0.59781 (19)	0.1318 (2)	0.0205 (4)
C22	0.7168 (2)	0.53754 (18)	0.1994 (2)	0.0193 (4)
C23	0.5658 (2)	0.60189 (19)	0.1468 (2)	0.0186 (4)
C24	0.4134 (2)	0.5911 (2)	0.1555 (2)	0.0230 (4)
H24	0.3907	0.5296	0.2070	0.028*
C25	0.2947 (3)	0.6699 (2)	0.0894 (3)	0.0243 (5)
H25	0.1908	0.6605	0.0940	0.029*
C26	0.3261 (3)	0.7618 (2)	0.0169 (2)	0.0253 (5)
H26	0.2445	0.8158	−0.0254	0.030*
C27	0.4764 (3)	0.7760 (2)	0.0054 (3)	0.0245 (5)
H27	0.4993	0.8391	−0.0432	0.029*
C28	0.5909 (2)	0.69476 (18)	0.0674 (2)	0.0199 (4)
C29	0.8118 (3)	0.7658 (2)	−0.0215 (2)	0.0240 (4)
H29A	0.7229	0.8062	−0.0964	0.029*
H29B	0.8676	0.7207	−0.0742	0.029*
C30	0.9289 (3)	0.8506 (2)	0.0767 (3)	0.0287 (5)
H30A	1.0197	0.8098	0.1487	0.034*
H30B	0.9724	0.8966	0.0146	0.034*
C31	0.8570 (3)	0.9279 (2)	0.1606 (3)	0.0321 (5)
H31A	0.8193	0.8831	0.2279	0.039*
H31B	0.7631	0.9667	0.0898	0.039*
C32	0.9782 (4)	1.0145 (3)	0.2504 (3)	0.0479 (8)
H32A	1.0220	1.0551	0.1853	0.054 (6)*
H32B	0.9249	1.0674	0.2953	0.054 (6)*
H32C	1.0654	0.9769	0.3283	0.054 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0265 (8)	0.0276 (9)	0.0468 (11)	0.0064 (7)	0.0204 (8)	0.0120 (8)
O2	0.0262 (8)	0.0267 (9)	0.0415 (9)	0.0058 (7)	0.0183 (7)	0.0102 (7)
N1	0.0218 (8)	0.0200 (9)	0.0262 (9)	−0.0022 (7)	0.0100 (7)	0.0037 (7)
N2	0.0202 (8)	0.0200 (9)	0.0245 (9)	0.0009 (7)	0.0093 (7)	0.0034 (7)
C1	0.0236 (10)	0.0197 (10)	0.0245 (10)	−0.0014 (9)	0.0112 (8)	−0.0011 (8)
C2	0.0201 (9)	0.0160 (9)	0.0226 (10)	−0.0010 (8)	0.0091 (7)	−0.0018 (7)
C3	0.0207 (9)	0.0173 (10)	0.0195 (9)	−0.0012 (8)	0.0060 (7)	−0.0011 (8)
C4	0.0226 (9)	0.0181 (10)	0.0269 (10)	0.0000 (9)	0.0083 (8)	0.0018 (8)
C5	0.0216 (10)	0.0267 (12)	0.0308 (12)	−0.0002 (9)	0.0084 (9)	0.0022 (10)
C6	0.0222 (10)	0.0251 (11)	0.0284 (11)	0.0016 (9)	0.0042 (8)	0.0046 (9)
C7	0.0252 (11)	0.0226 (11)	0.0263 (11)	−0.0017 (9)	0.0054 (9)	0.0036 (9)
C8	0.0212 (9)	0.0190 (10)	0.0223 (10)	−0.0014 (8)	0.0071 (7)	−0.0003 (8)
C9	0.0282 (11)	0.0263 (11)	0.0243 (10)	−0.0022 (10)	0.0107 (9)	0.0059 (9)
C10	0.0314 (11)	0.0224 (11)	0.0345 (12)	0.0002 (10)	0.0138 (9)	0.0070 (9)
C11	0.0379 (13)	0.0232 (11)	0.0337 (12)	−0.0016 (10)	0.0077 (10)	0.0016 (10)
C12	0.0505 (17)	0.0257 (13)	0.0462 (16)	−0.0037 (12)	0.0113 (13)	−0.0035 (11)
C21	0.0221 (9)	0.0174 (10)	0.0228 (10)	−0.0009 (8)	0.0091 (8)	0.0011 (8)
C22	0.0207 (9)	0.0164 (9)	0.0215 (10)	−0.0019 (8)	0.0083 (7)	−0.0020 (7)
C23	0.0180 (8)	0.0163 (9)	0.0200 (9)	0.0012 (8)	0.0051 (7)	−0.0016 (7)
C24	0.0214 (10)	0.0237 (11)	0.0251 (10)	−0.0021 (9)	0.0097 (8)	0.0000 (8)
C25	0.0208 (10)	0.0249 (12)	0.0276 (11)	−0.0008 (9)	0.0091 (8)	−0.0003 (9)
C26	0.0232 (10)	0.0257 (11)	0.0261 (10)	0.0054 (9)	0.0076 (8)	0.0030 (9)
C27	0.0232 (10)	0.0225 (11)	0.0274 (10)	0.0025 (9)	0.0083 (8)	0.0047 (9)
C28	0.0198 (9)	0.0191 (10)	0.0205 (9)	−0.0008 (8)	0.0067 (7)	−0.0017 (8)
C29	0.0255 (10)	0.0215 (10)	0.0269 (11)	−0.0010 (9)	0.0117 (9)	0.0048 (9)
C30	0.0281 (11)	0.0249 (11)	0.0347 (12)	−0.0038 (9)	0.0129 (9)	0.0052 (9)
C31	0.0365 (12)	0.0227 (11)	0.0361 (13)	−0.0028 (10)	0.0114 (10)	0.0009 (9)
C32	0.064 (2)	0.0330 (15)	0.0429 (16)	−0.0158 (15)	0.0146 (14)	−0.0077 (12)

O1—C1	1.224 (3)	C11—H11B	0.9900
O2—C21	1.217 (3)	C12—H12A	0.9801
N1—C1	1.360 (3)	C12—H12B	0.9801
N1—C8	1.396 (3)	C12—H12C	0.9801
N1—C9	1.463 (3)	C21—C22	1.524 (3)
N2—C21	1.364 (3)	C22—C23	1.477 (3)
N2—C28	1.399 (3)	C23—C24	1.398 (3)
N2—C29	1.464 (3)	C23—C28	1.413 (3)
C1—C2	1.519 (3)	C24—C25	1.392 (3)
C2—C22	1.373 (3)	C24—H24	0.9500
C2—C3	1.479 (3)	C25—C26	1.386 (3)
C3—C4	1.393 (3)	C25—H25	0.9500
C3—C8	1.417 (3)	C26—C27	1.394 (3)
C4—C5	1.394 (3)	C26—H26	0.9500
C4—H4	0.9500	C27—C28	1.383 (3)
C5—C6	1.386 (3)	C27—H27	0.9500
C5—H5	0.9500	C29—C30	1.523 (3)
C6—C7	1.388 (3)	C29—H29A	0.9900
C6—H6A	0.9500	C29—H29B	0.9900
C7—C8	1.376 (3)	C30—C31	1.514 (4)
C7—H7	0.9500	C30—H30A	0.9900
C9—C10	1.525 (3)	C30—H30B	0.9900
C9—H9A	0.9900	C31—C32	1.528 (4)
C9—H9B	0.9900	C31—H31A	0.9900
C10—C11	1.518 (3)	C31—H31B	0.9900
C10—H10A	0.9900	C32—H32A	0.9802
C10—H10B	0.9900	C32—H32B	0.9802
C11—C12	1.513 (4)	C32—H32C	0.9802
C11—H11A	0.9900
C1—N1—C8	110.82 (18)	C11—C12—H12C	109.4
C1—N1—C9	124.27 (18)	H12A—C12—H12C	109.5
C8—N1—C9	124.88 (19)	H12B—C12—H12C	109.5
C21—N2—C28	110.65 (17)	O2—C21—N2	123.0 (2)
C21—N2—C29	122.21 (18)	O2—C21—C22	129.3 (2)
C28—N2—C29	126.74 (18)	N2—C21—C22	107.66 (17)
O1—C1—N1	123.2 (2)	C2—C22—C23	132.94 (19)
O1—C1—C2	129.1 (2)	C2—C22—C21	122.89 (18)
N1—C1—C2	107.73 (17)	C23—C22—C21	104.12 (18)
C22—C2—C3	132.62 (18)	C24—C23—C28	116.8 (2)
C22—C2—C1	122.87 (17)	C24—C23—C22	136.0 (2)
C3—C2—C1	104.50 (18)	C28—C23—C22	107.22 (18)
C4—C3—C8	117.3 (2)	C25—C24—C23	120.5 (2)
C4—C3—C2	136.1 (2)	C25—C24—H24	119.7
C8—C3—C2	106.67 (18)	C23—C24—H24	119.7
C3—C4—C5	120.0 (2)	C26—C25—C24	120.8 (2)
C3—C4—H4	120.0	C26—C25—H25	119.6
C5—C4—H4	120.0	C24—C25—H25	119.6
C6—C5—C4	121.2 (2)	C25—C26—C27	120.7 (2)
C6—C5—H5	119.4	C25—C26—H26	119.7
C4—C5—H5	119.4	C27—C26—H26	119.7
C5—C6—C7	120.3 (2)	C28—C27—C26	117.6 (2)
C5—C6—H6A	119.9	C28—C27—H27	121.2
C7—C6—H6A	119.9	C26—C27—H27	121.2
C8—C7—C6	118.3 (2)	C27—C28—N2	126.3 (2)
C8—C7—H7	120.9	C27—C28—C23	123.57 (19)
C6—C7—H7	120.9	N2—C28—C23	110.10 (18)
C7—C8—N1	126.7 (2)	N2—C29—C30	112.71 (18)
C7—C8—C3	123.1 (2)	N2—C29—H29A	109.0
N1—C8—C3	110.28 (19)	C30—C29—H29A	109.0
N1—C9—C10	113.50 (19)	N2—C29—H29B	109.0
N1—C9—H9A	108.9	C30—C29—H29B	109.0
C10—C9—H9A	108.9	H29A—C29—H29B	107.8
N1—C9—H9B	108.9	C31—C30—C29	114.5 (2)
C10—C9—H9B	108.9	C31—C30—H30A	108.6
H9A—C9—H9B	107.7	C29—C30—H30A	108.6
C11—C10—C9	113.5 (2)	C31—C30—H30B	108.6
C11—C10—H10A	108.9	C29—C30—H30B	108.6
C9—C10—H10A	108.9	H30A—C30—H30B	107.6
C11—C10—H10B	108.9	C30—C31—C32	111.7 (2)
C9—C10—H10B	108.9	C30—C31—H31A	109.3
H10A—C10—H10B	107.7	C32—C31—H31A	109.3
C12—C11—C10	112.8 (2)	C30—C31—H31B	109.3
C12—C11—H11A	109.0	C32—C31—H31B	109.3
C10—C11—H11A	109.0	H31A—C31—H31B	107.9
C12—C11—H11B	109.0	C31—C32—H32A	109.5
C10—C11—H11B	109.0	C31—C32—H32B	109.5
H11A—C11—H11B	107.8	H32A—C32—H32B	109.5
C11—C12—H12A	109.5	C31—C32—H32C	109.5
C11—C12—H12B	109.5	H32A—C32—H32C	109.5
H12A—C12—H12B	109.5	H32B—C32—H32C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2	0.95	2.05	2.815 (3)	137
C24—H24···O1	0.95	2.04	2.805 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2	0.95	2.05	2.815 (3)	137
C24—H24⋯O1	0.95	2.04	2.805 (3)	136