N,N′-(Oxydi-p-phenyl­ene)diphthalimide

Li, Y.-T.; Wang, Z.

doi:10.1107/S1600536807057455

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o77

https://doi.org/10.1107/S1600536807057455

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N,N′-(Oxydi-p-phenylene)diphthalimide

Yi-Tao Li ^a ^* and Zhiguo Wang ^b

^aKey Laboratory of Pesticides and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China, and ^bSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
^*Correspondence e-mail: lytm1234@yahoo.com.cn

(Received 5 November 2007; accepted 9 November 2007; online 6 December 2007)

The title compound, C₂₈H₁₆N₂O₅, is a bis-imide derivative in which two phthalimide units are linked by an oxydi-p-phenylene 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. Intermolecular 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_r = 460.43
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.118
S = 1.23
2925 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807057455/wn2220Isup2.hkl

checkCIF report

Comment top

Bisimides are heterocyclic compounds, some of which have biological activity (Rich et al., 1975). Moreover, they are synthetic precursors with applications in organic synthesis (Degenhardt et al., 2002), polymer synthesis (Mallakpour & Kowsari, 2004), supramolecular chemistry (Zhang et al., 1999), and for the development of new materials (Langhals & Kirner, 2000) and molecular electronic devices (Yakimov & Forrest, 2002).

Following our studies on the synthesis of bisimide derivatives (Li et al., 2007), we report here the structure of the title compound (Fig. 1). The two phthalimide units are linked by a (phenoxy)phenylene 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. Compared to a similar structure, N,N'-(methylenedi-p-phenylene)diphthalimide (Li et al., 2007), the packing pattern is different; this may be due to the bridging methylene group being replaced by the bridging O atom. Intermolecular C—H···O hydrogen bonds contribute to the stability of the structure (Table 1).

Related literature top

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 top

A solution of phthaloyl dichoride (420 mg, 2 mmol) was added slowly over a period of 10 min to a solution of 4-aminophenyl ether (400 mg, 2 mmol) in dichloromethane (25 ml) at 273 K to yield a light yellow precipitate. Triethylamine (5 ml) was then added to dissolve the precipitate which became a yellow suspension after stirring for 12 h. The compound was filtered and dried (yield 510 mg, 70%). Single crystals of the title compound were obtained by recrystallization from dimethylformamide at room temperature.

Structure description top

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).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Bruker, 1997).

Figures top

Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids. H atoms have been omitted.

N,N'-(Oxydi-p-phenylene)diphthalimide top

Crystal data top

C₂₈H₁₆N₂O₅	F(000) = 952
M_r = 460.43	D_x = 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 = 2.3–25.9°
b = 16.480 (3) Å	µ = 0.10 mm⁻¹
c = 17.551 (3) Å	T = 292 K
V = 2171.0 (6) Å³	Block, colourless
Z = 4	0.30 × 0.30 × 0.30 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2644 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 28.0°, θ_min = 2.3°
φ and ω scans	h = −8→9
13091 measured reflections	k = −21→17
2925 independent reflections	l = −22→22

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.23	w = 1/[σ²(F_o²) + (0.06P)² + 0.1294P] where P = (F_o² + 2F_c²)/3
2925 reflections	(Δ/σ)_max = 0.017
316 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₈H₁₆N₂O₅	V = 2171.0 (6) Å³
M_r = 460.43	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.5059 (11) Å	µ = 0.10 mm⁻¹
b = 16.480 (3) Å	T = 292 K
c = 17.551 (3) Å	0.30 × 0.30 × 0.30 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2644 reflections with I > 2σ(I)
13091 measured reflections	R_int = 0.027
2925 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.23	Δρ_max = 0.16 e Å⁻³
2925 reflections	Δρ_min = −0.26 e Å⁻³
316 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₈H₁₆N₂O₅
M_r	460.43
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	292
a, b, c (Å)	7.5059 (11), 16.480 (3), 17.551 (3)
V (Å³)	2171.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13091, 2925, 2644
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.118, 1.23
No. of reflections	2925
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O5ⁱ	0.93	2.47	3.222 (4)	137.5
C19—H19···O5ⁱⁱ	0.93	2.56	3.298 (4)	136.2

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, −z+2.

Acknowledgements

The authors thank Dr Xiang-Gao Meng for the data collection.

References

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