The β-form of di-tert-butyl 1,4-dioxo-3,6-di­phenyl-1,2,4,5-tetra­hydro­pyrrolo­[3,4-c]­pyrrole-2,5-di­carboxyl­ate

Mizuguchi, J.

doi:10.1107/S1600536803005300

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The β-form of di-tert-butyl 1,4-dioxo-3,6-diphenyl-1,2,4,5-tetrahydropyrrolo[3,4-c]pyrrole-2,5-dicarboxylate

J. Mizuguchi

The title compound, C₂₈H₂₈N₂O₆, is a soluble precursor (`latent pigment') of diketopyrrolopyrrole pigments. The molecules are stacked along the a axis in a parallel arrangement. The present structure of the β-form is quite different from that of the previously reported α-form [MacLean et al. (2000). J. Chem. Soc. Perkin Trans. 2, pp. 1513–1519].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803005300/ob6220sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803005300/ob6220Isup2.hkl Contains datablock I

CCDC reference: 209951

checkCIF report

Key indicators

Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.005 Å
R factor = 0.058
wR factor = 0.125
Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

The title compound, (I), is a soluble yellow precursor (`latent pigment') (Zambounis et al., 1994, 1997) of diketopyrrolopyrrole pigments (DPP) (Herbst & Hunger, 1997) that is known as an industrially important red pigment. The soluble precursor is prepared by replacing the H atom of the NH group with a tert-butoxycarbonyl (t-BOC) group, hereafter called t-BOC DPP. The insoluble parent DPP can then be regenerated by thermochemical treatment of the precursor. The present `latent pigment technology' is a versatile and promising technique for the preparation of nano pigment particles, as well as transparent pigmented thin films, etc. The crystal structure of the parent DPP has previously been reported by us (Mizuguchi et al., 1992). In regard to the structure of t-BOC DPP, MacLean et al. (2000) reported that there exist two crystal modifications (α and β) and presented the structure of the α form, as obtained by Rietveld refinement from powder X-ray diffraction data, as well as the β form solved directly from powder X-ray diffraction data using their Monte Carlo technique and Rietveld refinement. We have reported previously the structure of the α-form based on single crystals (Mizuguchi, 2003). Our report here deals with the full structure analysis of the β form, (I).

The title compound crystallizes in space group P2₁/c with four non-centrosymmetric molecules (C₁ symmetry). An ORTEPIII (Burnett & Johnson, 1996) plot is shown in Fig. 1. The phenyl rings are asymmetrically deviated, in opposite directions, from the heterocyclic system by 34.3 (1)° (N1/C1/C2/C5/C6 and C7–C12}) and 29.3 (1)° (N2/C2–C5 and C15–C20). The t-BOC groups attached to the N atom of the heterocyclic ring are also twisted in opposite directions with respect to the heterocyclic system by 45.3 (1)° (N1/C14/O5/O6 and N1/C1/C2/C5/C6) and 41.5 (1)° (N2/C13/O3/O4 and N2/C2–C5). Furthermore, the heterocyclic ring system is not entirely planar, but is folded in the middle with a dihedral angle of 169.5 (1)°. The molecules are stacked along the a axis in a parallel arrangement (Fig. 2). The present result is similar but still different from the studies of MacLean et al. (2000) based on powder diffraction analysis, because they assumed that the molecule has an inversion center, leading to the space group of P2₁/c with Z = 2. Therefore, the a axis [6.2280 (5) Å] is half of our value [a = 12.798 (2) Å; P2₁/c with Z = 4 in our case].

Experimental top

The title compound was prepared according to the method described in the literature (Zambounis et al., 1994). The product was then dissolved in acetonitrile and the single crystals [(I), β-form] were grown by slowly and completely evaporating the solvent over a period of a week. This slow solvent evaporation was the key to the successful growth of the β-form; whereas the crystals of the α-form were easily obtained by recrystallization from an acetonitrile solution in a closed system (Mizuguchi, 2003).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.

Figures top

	Fig. 1. A view of the molecular structure of (I), showing ellipsoids at the 50% probability level for non-H atoms.
	Fig. 2. Packing structure of the β-form of (I).

(I) top

Crystal data top

C₂₈H₂₈N₂O₆	F(000) = 1032
M_r = 488.54	D_x = 1.326 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
a = 12.798 (2) Å	Cell parameters from 16150 reflections
b = 10.466 (1) Å	θ = 3.6–68.2°
c = 19.215 (3) Å	µ = 0.77 mm⁻¹
β = 108.10 (1)°	T = 93 K
V = 2446.5 (6) Å³	Prism, yellow-green
Z = 4	0.30 × 0.20 × 0.06 mm

Data collection top

Rigaku R-AXIS RAPID Imaging Plate diffractometer	2190 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.060
48 frames, delta ω = 15 deg scans	θ_max = 67.8°
Absorption correction: multi-scan (Higashi, 1995)	h = −15→15
T_min = 0.783, T_max = 0.955	k = −11→12
21098 measured reflections	l = −23→23
4408 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.058	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.126	(Δ/σ)_max = 0.0003
S = 0.88	Δρ_max = 0.34 e Å⁻³
4401 reflections	Δρ_min = −0.47 e Å⁻³
325 parameters

Crystal data top

C₂₈H₂₈N₂O₆	V = 2446.5 (6) Å³
M_r = 488.54	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.798 (2) Å	µ = 0.77 mm⁻¹
b = 10.466 (1) Å	T = 93 K
c = 19.215 (3) Å	0.30 × 0.20 × 0.06 mm
β = 108.10 (1)°

Data collection top

Rigaku R-AXIS RAPID Imaging Plate diffractometer	4408 independent reflections
Absorption correction: multi-scan (Higashi, 1995)	2190 reflections with F² > 2σ(F²)
T_min = 0.783, T_max = 0.955	R_int = 0.060
21098 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	325 parameters
wR(F²) = 0.126	H-atom parameters constrained
S = 0.88	Δρ_max = 0.34 e Å⁻³
4401 reflections	Δρ_min = −0.47 e Å⁻³

Special details top

Refinement. Refinement using reflections with F² > −10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
O1	0.6688 (2)	−0.0640 (2)	0.0585 (1)	0.0379 (7)
O2	0.7958 (2)	0.3998 (2)	−0.0714 (1)	0.0346 (7)
O3	0.8421 (2)	0.1088 (2)	−0.1926 (1)	0.0341 (7)
O4	0.9380 (2)	0.2800 (2)	−0.1325 (1)	0.0335 (7)
O5	0.6344 (2)	0.0634 (2)	0.1762 (1)	0.0314 (7)
O6	0.5092 (2)	0.2123 (2)	0.1163 (1)	0.0351 (7)
N1	0.6573 (2)	0.1566 (2)	0.0779 (1)	0.0291 (8)
N2	0.8246 (2)	0.1790 (2)	−0.0830 (1)	0.0288 (8)
C1	0.6779 (3)	0.2701 (3)	0.0430 (2)	0.031 (1)
C2	0.7221 (3)	0.2345 (3)	−0.0093 (2)	0.0285 (10)
C3	0.7828 (3)	0.2904 (3)	−0.0546 (2)	0.0294 (10)
C4	0.7948 (3)	0.0642 (3)	−0.0545 (2)	0.0292 (10)
C5	0.7315 (3)	0.0984 (3)	−0.0113 (2)	0.0294 (10)
C6	0.6868 (3)	0.0446 (3)	0.0430 (2)	0.032 (1)
C7	0.6630 (3)	0.3980 (3)	0.0695 (2)	0.0281 (10)
C8	0.6788 (3)	0.4249 (3)	0.1432 (2)	0.033 (1)
C9	0.6702 (3)	0.5496 (3)	0.1655 (2)	0.0315 (10)
C10	0.6428 (3)	0.6475 (3)	0.1150 (2)	0.034 (1)
C11	0.6257 (3)	0.6213 (3)	0.0417 (2)	0.033 (1)
C12	0.6365 (3)	0.4984 (3)	0.0186 (2)	0.0306 (10)
C13	0.8678 (3)	0.1838 (3)	−0.1428 (2)	0.0301 (10)
C14	0.5903 (3)	0.1489 (3)	0.1245 (2)	0.030 (1)
C15	0.8375 (3)	−0.0624 (3)	−0.0634 (2)	0.0307 (10)
C16	0.9387 (3)	−0.0819 (3)	−0.0753 (2)	0.033 (1)
C17	0.9784 (3)	−0.2045 (3)	−0.0758 (2)	0.033 (1)
C18	0.9195 (3)	−0.3095 (3)	−0.0657 (2)	0.035 (1)
C19	0.8179 (3)	−0.2914 (3)	−0.0554 (2)	0.034 (1)
C20	0.7762 (3)	−0.1687 (3)	−0.0548 (2)	0.033 (1)
C21	0.9954 (3)	0.3107 (3)	−0.1875 (2)	0.033 (1)
C22	1.0522 (3)	0.4355 (3)	−0.1582 (2)	0.041 (1)
C23	0.9129 (3)	0.3298 (3)	−0.2622 (2)	0.040 (1)
C24	1.0770 (3)	0.2047 (3)	−0.1858 (2)	0.044 (1)
C25	0.5760 (3)	0.0245 (3)	0.2287 (2)	0.031 (1)
C26	0.5667 (3)	0.1392 (3)	0.2742 (2)	0.035 (1)
C27	0.4665 (3)	−0.0328 (3)	0.1871 (2)	0.038 (1)
C28	0.6536 (3)	−0.0746 (3)	0.2749 (2)	0.036 (1)
H1	0.6956	0.3578	0.1782	0.0389*
H2	0.6837	0.5676	0.2161	0.0389*
H3	0.6353	0.7326	0.1305	0.0414*
H4	0.6061	0.6884	0.0066	0.0405*
H5	0.6264	0.4822	−0.0319	0.0370*
H6	0.9802	−0.0108	−0.0830	0.0397*
H7	1.0479	−0.2169	−0.0834	0.0395*
H8	0.9481	−0.3933	−0.0659	0.0425*
H9	0.7765	−0.3634	−0.0485	0.0412*
H10	0.7059	−0.1572	−0.0487	0.0401*
H11	1.1008	0.4227	−0.1098	0.0492*
H12	1.0925	0.4650	−0.1887	0.0492*
H13	0.9985	0.4977	−0.1565	0.0492*
H14	0.8640	0.3969	−0.2604	0.0473*
H15	0.9496	0.3492	−0.2966	0.0473*
H16	0.8714	0.2526	−0.2768	0.0473*
H17	1.0386	0.1254	−0.1971	0.0518*
H18	1.1143	0.2215	−0.2199	0.0518*
H19	1.1285	0.1991	−0.1377	0.0518*
H20	0.6380	0.1698	0.3003	0.0411*
H21	0.5265	0.2052	0.2430	0.0411*
H22	0.5292	0.1160	0.3080	0.0411*
H23	0.4235	0.0276	0.1536	0.0442*
H24	0.4779	−0.1063	0.1607	0.0442*
H25	0.4286	−0.0585	0.2203	0.0442*
H26	0.6246	−0.1067	0.3115	0.0426*
H27	0.6622	−0.1430	0.2447	0.0426*
H28	0.7234	−0.0365	0.2980	0.0426*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.054 (2)	0.022 (1)	0.043 (1)	−0.002 (1)	0.024 (1)	0.002 (1)
O2	0.046 (2)	0.020 (1)	0.040 (1)	0.001 (1)	0.016 (1)	0.004 (1)
O3	0.045 (2)	0.026 (1)	0.031 (1)	−0.003 (1)	0.012 (1)	−0.004 (1)
O4	0.040 (2)	0.024 (1)	0.038 (1)	−0.007 (1)	0.015 (1)	−0.003 (1)
O5	0.039 (1)	0.023 (1)	0.031 (1)	0.002 (1)	0.009 (1)	0.006 (1)
O6	0.036 (2)	0.027 (1)	0.044 (2)	0.003 (1)	0.014 (1)	0.006 (1)
N1	0.044 (2)	0.018 (1)	0.030 (2)	0.003 (1)	0.018 (1)	−0.002 (1)
N2	0.040 (2)	0.019 (1)	0.030 (2)	−0.001 (1)	0.015 (1)	−0.002 (1)
C1	0.035 (2)	0.023 (2)	0.035 (2)	−0.001 (2)	0.009 (2)	0.003 (2)
C2	0.035 (2)	0.021 (2)	0.030 (2)	0.000 (2)	0.012 (2)	0.000 (2)
C3	0.039 (2)	0.023 (2)	0.023 (2)	0.003 (2)	0.007 (2)	−0.006 (2)
C4	0.037 (2)	0.021 (2)	0.027 (2)	−0.003 (2)	0.007 (2)	0.005 (1)
C5	0.039 (2)	0.022 (2)	0.027 (2)	−0.001 (2)	0.009 (2)	0.000 (1)
C6	0.040 (2)	0.024 (2)	0.033 (2)	0.002 (2)	0.012 (2)	0.001 (2)
C7	0.031 (2)	0.021 (2)	0.032 (2)	0.001 (2)	0.009 (2)	−0.001 (1)
C8	0.034 (2)	0.024 (2)	0.039 (2)	−0.002 (2)	0.010 (2)	0.002 (2)
C9	0.036 (2)	0.028 (2)	0.032 (2)	−0.003 (2)	0.012 (2)	−0.003 (2)
C10	0.039 (2)	0.024 (2)	0.042 (2)	0.003 (2)	0.016 (2)	0.000 (2)
C11	0.039 (2)	0.023 (2)	0.038 (2)	0.001 (2)	0.012 (2)	0.002 (2)
C12	0.035 (2)	0.028 (2)	0.027 (2)	0.001 (2)	0.006 (2)	0.002 (2)
C13	0.033 (2)	0.021 (2)	0.032 (2)	0.004 (2)	0.004 (2)	0.001 (2)
C14	0.040 (2)	0.022 (2)	0.025 (2)	−0.006 (2)	0.006 (2)	−0.003 (2)
C15	0.038 (2)	0.020 (2)	0.030 (2)	−0.002 (2)	0.006 (2)	0.000 (2)
C16	0.041 (2)	0.025 (2)	0.031 (2)	−0.005 (2)	0.009 (2)	−0.001 (2)
C17	0.038 (2)	0.029 (2)	0.032 (2)	0.003 (2)	0.013 (2)	0.002 (2)
C18	0.047 (2)	0.022 (2)	0.036 (2)	0.003 (2)	0.013 (2)	−0.003 (2)
C19	0.052 (2)	0.024 (2)	0.031 (2)	−0.005 (2)	0.018 (2)	0.000 (2)
C20	0.036 (2)	0.025 (2)	0.041 (2)	−0.002 (2)	0.015 (2)	−0.004 (2)
C21	0.039 (2)	0.026 (2)	0.037 (2)	0.000 (2)	0.015 (2)	0.000 (2)
C22	0.047 (2)	0.029 (2)	0.047 (2)	−0.005 (2)	0.015 (2)	0.001 (2)
C23	0.048 (2)	0.034 (2)	0.041 (2)	−0.006 (2)	0.018 (2)	0.001 (2)
C24	0.045 (2)	0.034 (2)	0.058 (3)	−0.003 (2)	0.021 (2)	0.003 (2)
C25	0.039 (2)	0.024 (2)	0.031 (2)	−0.005 (2)	0.013 (2)	0.003 (2)
C26	0.047 (2)	0.028 (2)	0.033 (2)	−0.002 (2)	0.014 (2)	0.001 (2)
C27	0.052 (3)	0.024 (2)	0.038 (2)	−0.003 (2)	0.015 (2)	0.001 (2)
C28	0.047 (2)	0.024 (2)	0.037 (2)	−0.001 (2)	0.013 (2)	0.001 (2)

Geometric parameters (Å, º) top

O1—C6	1.215 (4)	C16—C17	1.382 (5)
O2—C3	1.215 (4)	C16—H6	0.952
O3—C13	1.202 (4)	C17—C18	1.379 (5)
O4—C13	1.324 (4)	C17—H7	0.954
O4—C21	1.497 (5)	C18—C19	1.387 (6)
O5—C14	1.326 (4)	C18—H8	0.951
O5—C25	1.487 (5)	C19—C20	1.392 (5)
O6—C14	1.200 (4)	C19—H9	0.954
N1—C1	1.429 (4)	C20—H10	0.951
N1—C6	1.457 (4)	C21—C22	1.515 (4)
N1—C14	1.422 (5)	C21—C23	1.509 (4)
N2—C3	1.458 (4)	C21—C24	1.516 (5)
N2—C4	1.421 (4)	C22—H11	0.954
N2—C13	1.422 (5)	C22—H12	0.944
C1—C2	1.349 (5)	C22—H13	0.955
C1—C7	1.466 (5)	C23—H14	0.949
C2—C3	1.457 (5)	C23—H15	0.944
C2—C5	1.430 (4)	C23—H16	0.959
C4—C5	1.375 (5)	C24—H17	0.955
C4—C15	1.463 (5)	C24—H18	0.940
C5—C6	1.452 (5)	C24—H19	0.956
C7—C8	1.397 (5)	C25—C26	1.511 (5)
C7—C12	1.403 (4)	C25—C27	1.505 (4)
C8—C9	1.389 (4)	C25—C28	1.518 (4)
C8—H1	0.950	C26—H20	0.950
C9—C10	1.380 (4)	C26—H21	0.953
C9—H2	0.951	C26—H22	0.951
C10—C11	1.384 (5)	C27—H23	0.947
C10—H3	0.954	C27—H24	0.957
C11—C12	1.382 (5)	C27—H25	0.952
C11—H4	0.951	C28—H26	0.953
C12—H5	0.953	C28—H27	0.948
C15—C16	1.399 (6)	C28—H28	0.952
C15—C20	1.399 (5)

O1···C10ⁱ	3.260 (4)	N2···C17^vii	3.310 (4)
O1···C11ⁱ	3.339 (4)	C3···C17^vii	3.416 (4)
O2···C19ⁱⁱ	3.251 (4)	C4···C17^vii	3.512 (4)
O2···C18ⁱⁱ	3.416 (4)	C4···C27^vi	3.534 (4)
O2···C28ⁱⁱⁱ	3.470 (4)	C4···C16^vii	3.550 (4)
O2···C26ⁱⁱⁱ	3.487 (4)	C11···C12^v	3.429 (5)
O3···C8ⁱⁱⁱ	3.217 (4)	C12···C12^v	3.343 (7)
O3···C9ⁱⁱⁱ	3.361 (4)	C15···C16^vii	3.584 (4)
O5···C23^iv	3.568 (4)	C16···C16^vii	3.309 (6)
O6···C11^v	3.460 (4)	C19···C28^viii	3.573 (4)
O6···C20^vi	3.503 (4)	C26···C27^ix	3.566 (4)

C13—O4—C21	121.2 (3)	C18—C17—H7	119.4
C14—O5—C25	120.4 (3)	C17—C18—C19	119.3 (3)
C1—N1—C6	109.9 (3)	C17—C18—H8	120.4
C1—N1—C14	125.4 (3)	C19—C18—H8	120.4
C6—N1—C14	122.5 (3)	C18—C19—C20	120.4 (3)
C3—N2—C4	111.0 (3)	C18—C19—H9	119.9
C3—N2—C13	123.7 (3)	C20—C19—H9	119.8
C4—N2—C13	124.0 (3)	C15—C20—C19	120.1 (3)
N1—C1—C2	107.5 (3)	C15—C20—H10	120.1
N1—C1—C7	122.2 (3)	C19—C20—H10	119.8
C2—C1—C7	129.9 (3)	O4—C21—C22	102.0 (3)
C1—C2—C3	139.3 (3)	O4—C21—C23	110.4 (3)
C1—C2—C5	110.7 (3)	O4—C21—C24	108.2 (3)
C3—C2—C5	108.6 (3)	C22—C21—C23	110.7 (3)
O2—C3—N2	123.9 (3)	C22—C21—C24	112.0 (3)
O2—C3—C2	132.8 (3)	C23—C21—C24	113.0 (3)
N2—C3—C2	103.2 (3)	C21—C22—H11	109.5
N2—C4—C5	106.9 (3)	C21—C22—H12	110.0
N2—C4—C15	124.5 (3)	C21—C22—H13	109.4
C5—C4—C15	128.1 (3)	H11—C22—H12	109.6
C2—C5—C4	110.3 (3)	H11—C22—H13	108.7
C2—C5—C6	108.1 (3)	H12—C22—H13	109.6
C4—C5—C6	140.4 (3)	C21—C23—H14	109.7
O1—C6—N1	122.9 (3)	C21—C23—H15	110.0
O1—C6—C5	133.4 (3)	C21—C23—H16	109.1
N1—C6—C5	103.6 (3)	H14—C23—H15	110.1
C1—C7—C8	122.9 (3)	H14—C23—H16	108.8
C1—C7—C12	118.1 (3)	H15—C23—H16	109.2
C8—C7—C12	119.0 (3)	C21—C24—H17	109.2
C7—C8—C9	120.1 (3)	C21—C24—H18	110.1
C7—C8—H1	120.0	C21—C24—H19	109.2
C9—C8—H1	119.9	H17—C24—H18	109.9
C8—C9—C10	120.5 (3)	H17—C24—H19	108.6
C8—C9—H2	119.7	H18—C24—H19	109.8
C10—C9—H2	119.8	O5—C25—C26	108.8 (3)
C9—C10—C11	119.6 (3)	O5—C25—C27	109.3 (3)
C9—C10—H3	120.1	O5—C25—C28	102.0 (3)
C11—C10—H3	120.3	C26—C25—C27	113.3 (3)
C10—C11—C12	120.8 (3)	C26—C25—C28	111.1 (3)
C10—C11—H4	119.8	C27—C25—C28	111.7 (3)
C12—C11—H4	119.4	C25—C26—H20	109.7
C7—C12—C11	120.0 (3)	C25—C26—H21	109.6
C7—C12—H5	120.2	C25—C26—H22	109.9
C11—C12—H5	119.8	H20—C26—H21	109.2
O3—C13—O4	128.3 (4)	H20—C26—H22	109.4
O3—C13—N2	122.8 (3)	H21—C26—H22	109.1
O4—C13—N2	108.8 (3)	C25—C27—H23	110.1
O5—C14—O6	128.4 (4)	C25—C27—H24	109.4
O5—C14—N1	108.0 (3)	C25—C27—H25	109.9
O6—C14—N1	123.5 (3)	H23—C27—H24	109.2
C4—C15—C16	123.3 (3)	H23—C27—H25	109.5
C4—C15—C20	117.6 (3)	H24—C27—H25	108.7
C16—C15—C20	119.0 (3)	C25—C28—H26	109.7
C15—C16—C17	119.8 (3)	C25—C28—H27	109.8
C15—C16—H6	120.1	C25—C28—H28	109.6
C17—C16—H6	120.0	H26—C28—H27	109.3
C16—C17—C18	121.4 (4)	H26—C28—H28	109.0
C16—C17—H7	119.3	H27—C28—H28	109.4

O1—C6—N1—C1	−173.9 (3)	C2—C1—C7—C8	−141.0 (4)
O1—C6—N1—C14	−10.1 (4)	C2—C1—C7—C12	36.1 (5)
O1—C6—C5—C2	173.7 (3)	C2—C3—N2—C4	−2.1 (3)
O1—C6—C5—C4	−20.7 (7)	C2—C3—N2—C13	165.1 (2)
O2—C3—N2—C4	−178.9 (3)	C2—C5—C4—C15	170.8 (3)
O2—C3—N2—C13	−11.6 (4)	C3—N2—C4—C5	2.5 (3)
O2—C3—C2—C1	−18.4 (6)	C3—N2—C4—C15	−170.4 (3)
O2—C3—C2—C5	177.3 (3)	C3—C2—C1—C7	9.2 (6)
O3—C13—O4—C21	2.0 (5)	C3—C2—C5—C4	0.4 (3)
O3—C13—N2—C3	−133.2 (3)	C3—C2—C5—C6	170.7 (2)
O3—C13—N2—C4	32.4 (4)	C4—C15—C16—C17	173.5 (3)
O4—C13—N2—C3	47.6 (3)	C4—C15—C20—C19	−173.6 (3)
O4—C13—N2—C4	−146.8 (3)	C5—C2—C1—C7	173.3 (3)
O5—C14—N1—C1	−145.1 (3)	C5—C4—N2—C13	−164.7 (3)
O5—C14—N1—C6	53.7 (3)	C5—C4—C15—C16	−146.3 (3)
O6—C14—O5—C25	7.3 (5)	C5—C4—C15—C20	29.6 (4)
O6—C14—N1—C1	34.1 (4)	C5—C6—N1—C14	167.0 (2)
O6—C14—N1—C6	−127.2 (3)	C6—N1—C1—C7	−175.8 (3)
N1—C1—C2—C3	−163.6 (3)	C6—C5—C4—C15	5.4 (6)
N1—C1—C2—C5	0.5 (3)	C7—C1—N1—C14	20.9 (4)
N1—C1—C7—C8	30.9 (5)	C7—C8—C9—C10	1.9 (5)
N1—C1—C7—C12	−152.0 (3)	C7—C12—C11—C10	1.3 (5)
N1—C6—C5—C2	−2.8 (3)	C8—C7—C12—C11	−0.5 (5)
N1—C6—C5—C4	162.8 (4)	C8—C9—C10—C11	−1.1 (5)
N1—C14—O5—C25	−173.6 (2)	C9—C8—C7—C12	−1.1 (5)
N2—C3—C2—C1	165.3 (4)	C9—C10—C11—C12	−0.5 (5)
N2—C3—C2—C5	1.0 (3)	C13—O4—C21—C22	172.2 (2)
N2—C4—C5—C2	−1.7 (3)	C13—O4—C21—C23	54.6 (3)
N2—C4—C5—C6	−167.1 (4)	C13—O4—C21—C24	−69.6 (3)
N2—C4—C15—C16	25.0 (4)	C13—N2—C4—C15	22.4 (4)
N2—C4—C15—C20	−159.1 (3)	C14—O5—C25—C26	−64.1 (3)
N2—C13—O4—C21	−178.8 (2)	C14—O5—C25—C27	60.1 (3)
C1—N1—C6—C5	3.2 (3)	C14—O5—C25—C28	178.5 (2)
C1—C2—C5—C4	−168.7 (3)	C15—C16—C17—C18	0.8 (5)
C1—C2—C5—C6	1.6 (3)	C15—C20—C19—C18	−1.0 (5)
C1—C7—C8—C9	175.9 (3)	C16—C15—C20—C19	2.4 (4)
C1—C7—C12—C11	−177.7 (3)	C16—C17—C18—C19	0.6 (5)
C2—C1—N1—C6	−2.3 (3)	C17—C16—C15—C20	−2.3 (4)
C2—C1—N1—C14	−165.6 (3)	C17—C18—C19—C20	−0.5 (5)

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) x, −y+1/2, z−1/2; (iv) x, −y+1/2, z+1/2; (v) −x+1, −y+1, −z; (vi) −x+1, −y, −z; (vii) −x+2, −y, −z; (viii) x, −y−1/2, z−1/2; (ix) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₈N₂O₆
M_r	488.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	93
a, b, c (Å)	12.798 (2), 10.466 (1), 19.215 (3)
β (°)	108.10 (1)
V (Å³)	2446.5 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.30 × 0.20 × 0.06

Data collection
Diffractometer	Rigaku R-AXIS RAPID Imaging Plate diffractometer
Absorption correction	Multi-scan (Higashi, 1995)
T_min, T_max	0.783, 0.955
No. of measured, independent and observed [F² > 2σ(F²)] reflections	21098, 4408, 2190
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.126, 0.88
No. of reflections	4401
No. of parameters	325
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.47

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, TEXSAN (Molecular Structure Corporation, 2001), SHELXS86 (Sheldrick, 1985), TEXSAN, ORTEPIII (Burnett & Johnson, 1996).

Selected geometric parameters (Å, º) top

O1—C6	1.215 (4)	N2—C3	1.458 (4)
O2—C3	1.215 (4)	N2—C4	1.421 (4)
O3—C13	1.202 (4)	N2—C13	1.422 (5)
O4—C13	1.324 (4)	C1—C2	1.349 (5)
O4—C21	1.497 (5)	C1—C7	1.466 (5)
O5—C14	1.326 (4)	C2—C3	1.457 (5)
O5—C25	1.487 (5)	C2—C5	1.430 (4)
O6—C14	1.200 (4)	C4—C5	1.375 (5)
N1—C1	1.429 (4)	C4—C15	1.463 (5)
N1—C6	1.457 (4)	C5—C6	1.452 (5)
N1—C14	1.422 (5)

O3—C13—N2—C3	−133.2 (3)	N1—C1—C7—C8	30.9 (5)
O3—C13—N2—C4	32.4 (4)	N1—C1—C7—C12	−152.0 (3)
O4—C13—N2—C3	47.6 (3)	N2—C4—C15—C16	25.0 (4)
O4—C13—N2—C4	−146.8 (3)	N2—C4—C15—C20	−159.1 (3)
O5—C14—N1—C1	−145.1 (3)	C2—C1—N1—C14	−165.6 (3)
O5—C14—N1—C6	53.7 (3)	C2—C1—C7—C8	−141.0 (4)
O6—C14—N1—C1	34.1 (4)	C5—C4—C15—C16	−146.3 (3)
O6—C14—N1—C6	−127.2 (3)	C5—C4—C15—C20	29.6 (4)

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