N,N'-(Oxydi-p-phenyl-ene)diphthalimide.

The title compound, C(28)H(16)N(2)O(5), is a bis-imide derivative in which two phthalimide units are linked by an oxydi-p-phenyl-ene bridge. The dihedral angle between the planes of the two central benzene rings is 86.1 (4)°. The isoindole groups make dihedral angles of 46.0 (14) and 77.5 (13)° with the attached benzene rings. Inter-molecular C-H⋯O hydrogen bonds contribute to the stability of the structure.

Related literature

For details of the biological activity and uses of bis-imide derivatives, see: Rich et al. (1975 ▶); Degenhardt et al. (2002 ▶); Mallakpour & Kowsari (2004 ▶); Zhang et al. (1999 ▶); Langhals & Kirner (2000 ▶); Yakimov & Forrest (2002 ▶). For a related structure, see: Li et al. (2007 ▶).

Experimental

Crystal data

C28H16N2O5

M = 460.43

Orthorhombic,

a = 7.5059 (11) Å

b = 16.480 (3) Å

c = 17.551 (3) Å

V = 2171.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 292 (2) K

0.30 × 0.30 × 0.30 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: none

13091 measured reflections

2925 independent reflections

2644 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.118

S = 1.23

2925 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807057455/wn2220sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807057455/wn2220Isup2.hkl

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

C28H16N2O5	F000 = 952
Mr = 460.43	Dx = 1.409 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5562 reflections
a = 7.5059 (11) Å	θ = 2.3–25.9º
b = 16.480 (3) Å	µ = 0.10 mm−1
c = 17.551 (3) Å	T = 292 (2) K
V = 2171.0 (6) Å3	Block, colourless
Z = 4	0.30 × 0.30 × 0.30 mm

Bruker SMART 4K CCD area-detector diffractometer	2644 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Monochromator: graphite	θmax = 28.0º
T = 292(2) K	θmin = 2.3º
φ and ω scans	h = −8→9
Absorption correction: none	k = −21→17
13091 measured reflections	l = −22→22
2925 independent reflections

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.06P)2 + 0.1294P] where P = (Fo2 + 2Fc2)/3
S = 1.23	(Δ/σ)max = 0.017
2925 reflections	Δρmax = 0.16 e Å−3
316 parameters	Δρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.8558 (3)	0.62700 (13)	1.04648 (13)	0.0449 (5)
C2	0.9322 (4)	0.70185 (14)	1.05712 (13)	0.0492 (5)
H2	0.9588	0.7202	1.1059	0.059*
C3	0.9691 (4)	0.74958 (14)	0.99444 (15)	0.0492 (6)
H3	1.0231	0.7999	1.0009	0.059*
C4	0.9259 (3)	0.72283 (12)	0.92192 (12)	0.0432 (5)
C5	0.8447 (4)	0.64854 (13)	0.91224 (12)	0.0474 (5)
H5	0.8124	0.6313	0.8637	0.057*
C6	0.8115 (4)	0.59984 (13)	0.97454 (13)	0.0485 (5)
H6	0.7595	0.5491	0.9681	0.058*
C7	0.9251 (4)	0.85440 (13)	0.84975 (13)	0.0474 (5)
C8	1.0414 (4)	0.74006 (15)	0.78915 (14)	0.0506 (6)
C9	0.9801 (3)	0.87704 (15)	0.77128 (14)	0.0491 (5)
C10	1.0480 (3)	0.80952 (15)	0.73544 (13)	0.0494 (5)
C11	1.1046 (4)	0.81216 (19)	0.66035 (15)	0.0616 (7)
H11	1.1511	0.7665	0.6363	0.074*
C12	1.0891 (5)	0.8850 (2)	0.62283 (15)	0.0712 (9)
H12	1.1250	0.8886	0.5722	0.085*
C13	1.0219 (4)	0.9526 (2)	0.65846 (17)	0.0706 (9)
H13	1.0131	1.0009	0.6313	0.085*
C14	0.9667 (4)	0.95066 (17)	0.73407 (16)	0.0598 (7)
H14	0.9228	0.9966	0.7584	0.072*
C15	0.8345 (4)	0.49870 (14)	1.10677 (13)	0.0493 (6)
C16	0.6860 (4)	0.45102 (17)	1.11019 (18)	0.0634 (7)
H16	0.5730	0.4742	1.1105	0.076*
C17	0.7065 (4)	0.36759 (17)	1.11325 (19)	0.0649 (7)
H17	0.6066	0.3343	1.1156	0.078*
C18	0.8727 (4)	0.33395 (13)	1.11278 (13)	0.0484 (6)
C19	1.0208 (4)	0.38264 (17)	1.1071 (2)	0.0687 (8)
H19	1.1340	0.3598	1.1052	0.082*
C20	0.9999 (4)	0.46591 (17)	1.1043 (2)	0.0693 (8)
H20	1.0993	0.4994	1.1006	0.083*
C21	0.9359 (4)	0.20766 (15)	1.18659 (14)	0.0559 (6)
C22	0.8648 (4)	0.19351 (15)	1.05848 (15)	0.0577 (7)
C23	0.9404 (4)	0.12045 (15)	1.16640 (15)	0.0556 (6)
C24	0.8952 (4)	0.11189 (15)	1.09096 (15)	0.0563 (6)
C25	0.8777 (5)	0.03623 (17)	1.0583 (2)	0.0741 (9)
H25	0.8460	0.0300	1.0074	0.089*
C26	0.9095 (6)	−0.03000 (18)	1.1046 (3)	0.0897 (12)
H26	0.8972	−0.0819	1.0844	0.108*
C27	0.9587 (6)	−0.0216 (2)	1.1793 (3)	0.0890 (12)
H27	0.9808	−0.0676	1.2085	0.107*
C28	0.9758 (5)	0.05402 (19)	1.2116 (2)	0.0757 (9)
H28	1.0101	0.0601	1.2622	0.091*
N1	0.9654 (3)	0.77149 (11)	0.85670 (10)	0.0471 (5)
N2	0.8933 (3)	0.24810 (11)	1.11843 (11)	0.0533 (5)
O1	0.8144 (3)	0.58251 (10)	1.11128 (10)	0.0597 (5)
O2	0.8594 (3)	0.89603 (10)	0.89869 (11)	0.0626 (5)
O3	1.0881 (3)	0.67169 (11)	0.77944 (11)	0.0703 (6)
O4	0.9586 (4)	0.24056 (13)	1.24656 (11)	0.0848 (8)
O5	0.8234 (4)	0.21334 (12)	0.99506 (11)	0.0835 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0544 (13)	0.0353 (10)	0.0449 (11)	0.0030 (10)	0.0066 (10)	0.0026 (9)
C2	0.0603 (14)	0.0456 (12)	0.0416 (10)	−0.0062 (11)	−0.0017 (11)	−0.0034 (9)
C3	0.0631 (15)	0.0353 (9)	0.0491 (11)	−0.0105 (10)	−0.0011 (11)	−0.0034 (9)
C4	0.0522 (12)	0.0335 (9)	0.0437 (10)	0.0012 (9)	0.0038 (10)	0.0009 (9)
C5	0.0631 (14)	0.0363 (11)	0.0427 (11)	0.0000 (10)	−0.0001 (11)	−0.0062 (9)
C6	0.0644 (14)	0.0298 (9)	0.0515 (12)	−0.0061 (10)	0.0062 (11)	−0.0041 (9)
C7	0.0549 (13)	0.0344 (10)	0.0528 (13)	−0.0017 (10)	0.0010 (11)	0.0026 (9)
C8	0.0596 (15)	0.0459 (13)	0.0464 (12)	−0.0013 (11)	0.0034 (11)	−0.0033 (10)
C9	0.0511 (13)	0.0459 (12)	0.0502 (12)	−0.0065 (10)	−0.0071 (11)	0.0058 (10)
C10	0.0522 (13)	0.0511 (13)	0.0449 (12)	−0.0085 (11)	−0.0035 (10)	0.0019 (10)
C11	0.0655 (17)	0.0728 (17)	0.0467 (12)	−0.0166 (14)	−0.0006 (12)	−0.0007 (12)
C12	0.0768 (19)	0.090 (2)	0.0469 (13)	−0.0275 (18)	−0.0038 (13)	0.0141 (15)
C13	0.0731 (19)	0.0712 (18)	0.0674 (17)	−0.0239 (16)	−0.0144 (15)	0.0306 (16)
C14	0.0633 (16)	0.0489 (13)	0.0673 (16)	−0.0089 (12)	−0.0110 (14)	0.0154 (12)
C15	0.0711 (16)	0.0379 (11)	0.0387 (10)	−0.0051 (11)	0.0079 (11)	0.0024 (9)
C16	0.0620 (16)	0.0486 (13)	0.0797 (18)	0.0008 (12)	−0.0009 (15)	0.0064 (13)
C17	0.0617 (16)	0.0456 (13)	0.087 (2)	−0.0137 (12)	0.0021 (15)	0.0080 (14)
C18	0.0660 (15)	0.0370 (10)	0.0423 (11)	−0.0051 (11)	0.0033 (11)	0.0042 (9)
C19	0.0567 (15)	0.0478 (14)	0.102 (2)	−0.0010 (12)	0.0124 (16)	−0.0028 (15)
C20	0.0626 (17)	0.0446 (13)	0.101 (2)	−0.0120 (13)	0.0191 (16)	−0.0048 (15)
C21	0.0687 (17)	0.0492 (14)	0.0496 (13)	−0.0032 (13)	0.0003 (12)	0.0084 (11)
C22	0.0773 (18)	0.0470 (13)	0.0489 (13)	−0.0085 (13)	0.0083 (13)	−0.0022 (10)
C23	0.0586 (14)	0.0461 (12)	0.0622 (14)	0.0027 (12)	0.0086 (12)	0.0093 (11)
C24	0.0628 (15)	0.0429 (12)	0.0633 (14)	−0.0016 (11)	0.0173 (13)	−0.0003 (11)
C25	0.088 (2)	0.0525 (15)	0.0818 (19)	−0.0029 (16)	0.0251 (18)	−0.0115 (15)
C26	0.099 (3)	0.0418 (14)	0.128 (3)	0.0071 (16)	0.044 (3)	−0.0095 (18)
C27	0.094 (3)	0.0545 (17)	0.118 (3)	0.0193 (18)	0.030 (2)	0.0254 (19)
C28	0.083 (2)	0.0565 (17)	0.088 (2)	0.0114 (15)	0.0092 (18)	0.0242 (16)
N1	0.0628 (12)	0.0349 (9)	0.0436 (9)	−0.0002 (9)	0.0033 (9)	0.0016 (8)
N2	0.0771 (14)	0.0392 (9)	0.0437 (10)	−0.0040 (10)	−0.0006 (10)	0.0045 (8)
O1	0.0951 (14)	0.0372 (8)	0.0470 (9)	−0.0010 (9)	0.0187 (10)	0.0013 (7)
O2	0.0824 (13)	0.0389 (9)	0.0666 (11)	0.0050 (9)	0.0175 (10)	−0.0008 (8)
O3	0.1010 (15)	0.0449 (9)	0.0649 (10)	0.0095 (10)	0.0192 (12)	−0.0044 (8)
O4	0.138 (2)	0.0649 (12)	0.0520 (11)	−0.0018 (14)	−0.0199 (13)	0.0008 (9)
O5	0.142 (2)	0.0636 (12)	0.0452 (10)	−0.0148 (14)	−0.0081 (12)	0.0031 (9)

C1—C2	1.373 (3)	C15—C20	1.354 (4)
C1—C6	1.380 (3)	C15—C16	1.365 (4)
C1—O1	1.388 (3)	C15—O1	1.392 (3)
C2—C3	1.380 (3)	C16—C17	1.385 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.385 (3)	C17—C18	1.365 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.378 (3)	C18—C19	1.374 (4)
C4—N1	1.429 (3)	C18—N2	1.427 (3)
C5—C6	1.379 (3)	C19—C20	1.382 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—O2	1.205 (3)	C21—O4	1.196 (3)
C7—N1	1.405 (3)	C21—N2	1.406 (3)
C7—C9	1.485 (3)	C21—C23	1.481 (4)
C8—O3	1.192 (3)	C22—O5	1.201 (3)
C8—N1	1.414 (3)	C22—N2	1.401 (3)
C8—C10	1.484 (3)	C22—C24	1.478 (4)
C9—C10	1.376 (4)	C23—C24	1.374 (4)
C9—C14	1.382 (3)	C23—C28	1.378 (4)
C10—C11	1.385 (4)	C24—C25	1.378 (4)
C11—C12	1.374 (4)	C25—C26	1.381 (5)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.374 (5)	C26—C27	1.368 (6)
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.391 (4)	C27—C28	1.375 (5)
C13—H13	0.9300	C27—H27	0.9300
C14—H14	0.9300	C28—H28	0.9300
C2—C1—C6	121.1 (2)	C15—C16—H16	120.6
C2—C1—O1	117.2 (2)	C17—C16—H16	120.6
C6—C1—O1	121.6 (2)	C18—C17—C16	120.3 (3)
C1—C2—C3	119.2 (2)	C18—C17—H17	119.8
C1—C2—H2	120.4	C16—C17—H17	119.8
C3—C2—H2	120.4	C17—C18—C19	120.2 (2)
C2—C3—C4	120.3 (2)	C17—C18—N2	120.1 (2)
C2—C3—H3	119.9	C19—C18—N2	119.8 (3)
C4—C3—H3	119.9	C18—C19—C20	119.4 (3)
C5—C4—C3	120.0 (2)	C18—C19—H19	120.3
C5—C4—N1	119.44 (19)	C20—C19—H19	120.3
C3—C4—N1	120.60 (19)	C15—C20—C19	119.9 (3)
C4—C5—C6	119.9 (2)	C15—C20—H20	120.0
C4—C5—H5	120.0	C19—C20—H20	120.0
C6—C5—H5	120.0	O4—C21—N2	124.5 (2)
C1—C6—C5	119.5 (2)	O4—C21—C23	130.3 (2)
C1—C6—H6	120.2	N2—C21—C23	105.2 (2)
C5—C6—H6	120.2	O5—C22—N2	124.1 (2)
O2—C7—N1	125.5 (2)	O5—C22—C24	130.1 (2)
O2—C7—C9	129.2 (2)	N2—C22—C24	105.7 (2)
N1—C7—C9	105.4 (2)	C24—C23—C28	121.4 (3)
O3—C8—N1	125.8 (2)	C24—C23—C21	108.9 (2)
O3—C8—C10	128.9 (2)	C28—C23—C21	129.6 (3)
N1—C8—C10	105.29 (19)	C23—C24—C25	121.1 (3)
C10—C9—C14	121.4 (2)	C23—C24—C22	108.4 (2)
C10—C9—C7	108.9 (2)	C25—C24—C22	130.4 (3)
C14—C9—C7	129.7 (3)	C24—C25—C26	117.0 (3)
C9—C10—C11	121.5 (2)	C24—C25—H25	121.5
C9—C10—C8	108.7 (2)	C26—C25—H25	121.5
C11—C10—C8	129.7 (2)	C27—C26—C25	122.0 (3)
C12—C11—C10	117.2 (3)	C27—C26—H26	119.0
C12—C11—H11	121.4	C25—C26—H26	119.0
C10—C11—H11	121.4	C26—C27—C28	120.8 (3)
C11—C12—C13	121.4 (3)	C26—C27—H27	119.6
C11—C12—H12	119.3	C28—C27—H27	119.6
C13—C12—H12	119.3	C27—C28—C23	117.6 (3)
C12—C13—C14	121.6 (3)	C27—C28—H28	121.2
C12—C13—H13	119.2	C23—C28—H28	121.2
C14—C13—H13	119.2	C7—N1—C8	111.74 (19)
C9—C14—C13	116.7 (3)	C7—N1—C4	124.81 (19)
C9—C14—H14	121.6	C8—N1—C4	123.36 (18)
C13—C14—H14	121.6	C22—N2—C21	111.7 (2)
C20—C15—C16	121.3 (2)	C22—N2—C18	124.6 (2)
C20—C15—O1	119.8 (2)	C21—N2—C18	123.6 (2)
C16—C15—O1	118.7 (3)	C1—O1—C15	116.95 (18)
C15—C16—C17	118.8 (3)
C6—C1—C2—C3	−1.7 (4)	C28—C23—C24—C25	2.2 (5)
O1—C1—C2—C3	−177.4 (2)	C21—C23—C24—C25	−175.8 (3)
C1—C2—C3—C4	1.4 (4)	C28—C23—C24—C22	179.7 (3)
C2—C3—C4—C5	0.5 (4)	C21—C23—C24—C22	1.7 (3)
C2—C3—C4—N1	−179.3 (2)	O5—C22—C24—C23	−180.0 (3)
C3—C4—C5—C6	−2.0 (4)	N2—C22—C24—C23	−0.4 (3)
N1—C4—C5—C6	177.8 (2)	O5—C22—C24—C25	−2.8 (6)
C2—C1—C6—C5	0.2 (4)	N2—C22—C24—C25	176.8 (3)
O1—C1—C6—C5	175.7 (2)	C23—C24—C25—C26	−0.7 (5)
C4—C5—C6—C1	1.7 (4)	C22—C24—C25—C26	−177.6 (4)
O2—C7—C9—C10	−179.7 (3)	C24—C25—C26—C27	−0.9 (6)
N1—C7—C9—C10	0.2 (3)	C25—C26—C27—C28	1.0 (6)
O2—C7—C9—C14	−1.5 (5)	C26—C27—C28—C23	0.5 (6)
N1—C7—C9—C14	178.4 (3)	C24—C23—C28—C27	−2.1 (5)
C14—C9—C10—C11	−0.5 (4)	C21—C23—C28—C27	175.5 (3)
C7—C9—C10—C11	177.8 (2)	O2—C7—N1—C8	179.9 (3)
C14—C9—C10—C8	−178.7 (2)	C9—C7—N1—C8	0.1 (3)
C7—C9—C10—C8	−0.4 (3)	O2—C7—N1—C4	3.4 (4)
O3—C8—C10—C9	−179.8 (3)	C9—C7—N1—C4	−176.5 (2)
N1—C8—C10—C9	0.4 (3)	O3—C8—N1—C7	179.9 (3)
O3—C8—C10—C11	2.2 (5)	C10—C8—N1—C7	−0.3 (3)
N1—C8—C10—C11	−177.6 (3)	O3—C8—N1—C4	−3.4 (4)
C9—C10—C11—C12	−0.4 (4)	C10—C8—N1—C4	176.4 (2)
C8—C10—C11—C12	177.4 (3)	C5—C4—N1—C7	131.9 (3)
C10—C11—C12—C13	0.6 (5)	C3—C4—N1—C7	−48.3 (4)
C11—C12—C13—C14	0.1 (5)	C5—C4—N1—C8	−44.3 (3)
C10—C9—C14—C13	1.2 (4)	C3—C4—N1—C8	135.5 (3)
C7—C9—C14—C13	−176.8 (3)	O5—C22—N2—C21	178.5 (3)
C12—C13—C14—C9	−1.0 (4)	C24—C22—N2—C21	−1.1 (3)
C20—C15—C16—C17	1.8 (4)	O5—C22—N2—C18	1.6 (5)
O1—C15—C16—C17	−173.8 (3)	C24—C22—N2—C18	−178.0 (3)
C15—C16—C17—C18	0.0 (5)	O4—C21—N2—C22	−176.6 (3)
C16—C17—C18—C19	−1.8 (4)	C23—C21—N2—C22	2.1 (3)
C16—C17—C18—N2	178.0 (3)	O4—C21—N2—C18	0.3 (5)
C17—C18—C19—C20	2.0 (5)	C23—C21—N2—C18	179.0 (3)
N2—C18—C19—C20	−177.8 (3)	C17—C18—N2—C22	77.1 (4)
C16—C15—C20—C19	−1.7 (5)	C19—C18—N2—C22	−103.1 (3)
O1—C15—C20—C19	173.8 (3)	C17—C18—N2—C21	−99.4 (3)
C18—C19—C20—C15	−0.2 (5)	C19—C18—N2—C21	80.4 (4)
O4—C21—C23—C24	176.3 (4)	C2—C1—O1—C15	−144.7 (3)
N2—C21—C23—C24	−2.3 (3)	C6—C1—O1—C15	39.6 (4)
O4—C21—C23—C28	−1.5 (6)	C20—C15—O1—C1	71.4 (3)
N2—C21—C23—C28	179.9 (3)	C16—C15—O1—C1	−113.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O5i	0.93	2.47	3.222 (4)	138
C19—H19···O5ii	0.93	2.56	3.298 (4)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O5i	0.93	2.47	3.222 (4)	138
C19—H19⋯O5ii	0.93	2.56	3.298 (4)	136

Symmetry codes: (i) ; (ii) .