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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].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803005300/ob6220sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803005300/ob6220Isup2.hkl
Contains datablock I

CCDC reference: 209951

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](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).

Refinement top

All H atoms were positioned by calculation but not refined.

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
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing ellipsoids at the 50% probability level for non-H atoms.
[Figure 2] Fig. 2. Packing structure of the β-form of (I).
(I) top
Crystal data top
C28H28N2O6F(000) = 1032
Mr = 488.54Dx = 1.326 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
a = 12.798 (2) ÅCell parameters from 16150 reflections
b = 10.466 (1) Åθ = 3.6–68.2°
c = 19.215 (3) ŵ = 0.77 mm1
β = 108.10 (1)°T = 93 K
V = 2446.5 (6) Å3Prism, yellow-green
Z = 40.30 × 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-1Rint = 0.060
48 frames, delta ω = 15 deg scansθmax = 67.8°
Absorption correction: multi-scan
(Higashi, 1995)
h = 1515
Tmin = 0.783, Tmax = 0.955k = 1112
21098 measured reflectionsl = 2323
4408 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.058 w = 1/[σ2(Fo2) + (0.05P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.126(Δ/σ)max = 0.0003
S = 0.88Δρmax = 0.34 e Å3
4401 reflectionsΔρmin = 0.47 e Å3
325 parameters
Crystal data top
C28H28N2O6V = 2446.5 (6) Å3
Mr = 488.54Z = 4
Monoclinic, P21/cCu Kα radiation
a = 12.798 (2) ŵ = 0.77 mm1
b = 10.466 (1) ÅT = 93 K
c = 19.215 (3) Å0.30 × 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)
Tmin = 0.783, Tmax = 0.955Rint = 0.060
21098 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.058325 parameters
wR(F2) = 0.126H-atom parameters constrained
S = 0.88Δρmax = 0.34 e Å3
4401 reflectionsΔρmin = 0.47 e Å3
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
xyzUiso*/Ueq
O10.6688 (2)0.0640 (2)0.0585 (1)0.0379 (7)
O20.7958 (2)0.3998 (2)0.0714 (1)0.0346 (7)
O30.8421 (2)0.1088 (2)0.1926 (1)0.0341 (7)
O40.9380 (2)0.2800 (2)0.1325 (1)0.0335 (7)
O50.6344 (2)0.0634 (2)0.1762 (1)0.0314 (7)
O60.5092 (2)0.2123 (2)0.1163 (1)0.0351 (7)
N10.6573 (2)0.1566 (2)0.0779 (1)0.0291 (8)
N20.8246 (2)0.1790 (2)0.0830 (1)0.0288 (8)
C10.6779 (3)0.2701 (3)0.0430 (2)0.031 (1)
C20.7221 (3)0.2345 (3)0.0093 (2)0.0285 (10)
C30.7828 (3)0.2904 (3)0.0546 (2)0.0294 (10)
C40.7948 (3)0.0642 (3)0.0545 (2)0.0292 (10)
C50.7315 (3)0.0984 (3)0.0113 (2)0.0294 (10)
C60.6868 (3)0.0446 (3)0.0430 (2)0.032 (1)
C70.6630 (3)0.3980 (3)0.0695 (2)0.0281 (10)
C80.6788 (3)0.4249 (3)0.1432 (2)0.033 (1)
C90.6702 (3)0.5496 (3)0.1655 (2)0.0315 (10)
C100.6428 (3)0.6475 (3)0.1150 (2)0.034 (1)
C110.6257 (3)0.6213 (3)0.0417 (2)0.033 (1)
C120.6365 (3)0.4984 (3)0.0186 (2)0.0306 (10)
C130.8678 (3)0.1838 (3)0.1428 (2)0.0301 (10)
C140.5903 (3)0.1489 (3)0.1245 (2)0.030 (1)
C150.8375 (3)0.0624 (3)0.0634 (2)0.0307 (10)
C160.9387 (3)0.0819 (3)0.0753 (2)0.033 (1)
C170.9784 (3)0.2045 (3)0.0758 (2)0.033 (1)
C180.9195 (3)0.3095 (3)0.0657 (2)0.035 (1)
C190.8179 (3)0.2914 (3)0.0554 (2)0.034 (1)
C200.7762 (3)0.1687 (3)0.0548 (2)0.033 (1)
C210.9954 (3)0.3107 (3)0.1875 (2)0.033 (1)
C221.0522 (3)0.4355 (3)0.1582 (2)0.041 (1)
C230.9129 (3)0.3298 (3)0.2622 (2)0.040 (1)
C241.0770 (3)0.2047 (3)0.1858 (2)0.044 (1)
C250.5760 (3)0.0245 (3)0.2287 (2)0.031 (1)
C260.5667 (3)0.1392 (3)0.2742 (2)0.035 (1)
C270.4665 (3)0.0328 (3)0.1871 (2)0.038 (1)
C280.6536 (3)0.0746 (3)0.2749 (2)0.036 (1)
H10.69560.35780.17820.0389*
H20.68370.56760.21610.0389*
H30.63530.73260.13050.0414*
H40.60610.68840.00660.0405*
H50.62640.48220.03190.0370*
H60.98020.01080.08300.0397*
H71.04790.21690.08340.0395*
H80.94810.39330.06590.0425*
H90.77650.36340.04850.0412*
H100.70590.15720.04870.0401*
H111.10080.42270.10980.0492*
H121.09250.46500.18870.0492*
H130.99850.49770.15650.0492*
H140.86400.39690.26040.0473*
H150.94960.34920.29660.0473*
H160.87140.25260.27680.0473*
H171.03860.12540.19710.0518*
H181.11430.22150.21990.0518*
H191.12850.19910.13770.0518*
H200.63800.16980.30030.0411*
H210.52650.20520.24300.0411*
H220.52920.11600.30800.0411*
H230.42350.02760.15360.0442*
H240.47790.10630.16070.0442*
H250.42860.05850.22030.0442*
H260.62460.10670.31150.0426*
H270.66220.14300.24470.0426*
H280.72340.03650.29800.0426*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.054 (2)0.022 (1)0.043 (1)0.002 (1)0.024 (1)0.002 (1)
O20.046 (2)0.020 (1)0.040 (1)0.001 (1)0.016 (1)0.004 (1)
O30.045 (2)0.026 (1)0.031 (1)0.003 (1)0.012 (1)0.004 (1)
O40.040 (2)0.024 (1)0.038 (1)0.007 (1)0.015 (1)0.003 (1)
O50.039 (1)0.023 (1)0.031 (1)0.002 (1)0.009 (1)0.006 (1)
O60.036 (2)0.027 (1)0.044 (2)0.003 (1)0.014 (1)0.006 (1)
N10.044 (2)0.018 (1)0.030 (2)0.003 (1)0.018 (1)0.002 (1)
N20.040 (2)0.019 (1)0.030 (2)0.001 (1)0.015 (1)0.002 (1)
C10.035 (2)0.023 (2)0.035 (2)0.001 (2)0.009 (2)0.003 (2)
C20.035 (2)0.021 (2)0.030 (2)0.000 (2)0.012 (2)0.000 (2)
C30.039 (2)0.023 (2)0.023 (2)0.003 (2)0.007 (2)0.006 (2)
C40.037 (2)0.021 (2)0.027 (2)0.003 (2)0.007 (2)0.005 (1)
C50.039 (2)0.022 (2)0.027 (2)0.001 (2)0.009 (2)0.000 (1)
C60.040 (2)0.024 (2)0.033 (2)0.002 (2)0.012 (2)0.001 (2)
C70.031 (2)0.021 (2)0.032 (2)0.001 (2)0.009 (2)0.001 (1)
C80.034 (2)0.024 (2)0.039 (2)0.002 (2)0.010 (2)0.002 (2)
C90.036 (2)0.028 (2)0.032 (2)0.003 (2)0.012 (2)0.003 (2)
C100.039 (2)0.024 (2)0.042 (2)0.003 (2)0.016 (2)0.000 (2)
C110.039 (2)0.023 (2)0.038 (2)0.001 (2)0.012 (2)0.002 (2)
C120.035 (2)0.028 (2)0.027 (2)0.001 (2)0.006 (2)0.002 (2)
C130.033 (2)0.021 (2)0.032 (2)0.004 (2)0.004 (2)0.001 (2)
C140.040 (2)0.022 (2)0.025 (2)0.006 (2)0.006 (2)0.003 (2)
C150.038 (2)0.020 (2)0.030 (2)0.002 (2)0.006 (2)0.000 (2)
C160.041 (2)0.025 (2)0.031 (2)0.005 (2)0.009 (2)0.001 (2)
C170.038 (2)0.029 (2)0.032 (2)0.003 (2)0.013 (2)0.002 (2)
C180.047 (2)0.022 (2)0.036 (2)0.003 (2)0.013 (2)0.003 (2)
C190.052 (2)0.024 (2)0.031 (2)0.005 (2)0.018 (2)0.000 (2)
C200.036 (2)0.025 (2)0.041 (2)0.002 (2)0.015 (2)0.004 (2)
C210.039 (2)0.026 (2)0.037 (2)0.000 (2)0.015 (2)0.000 (2)
C220.047 (2)0.029 (2)0.047 (2)0.005 (2)0.015 (2)0.001 (2)
C230.048 (2)0.034 (2)0.041 (2)0.006 (2)0.018 (2)0.001 (2)
C240.045 (2)0.034 (2)0.058 (3)0.003 (2)0.021 (2)0.003 (2)
C250.039 (2)0.024 (2)0.031 (2)0.005 (2)0.013 (2)0.003 (2)
C260.047 (2)0.028 (2)0.033 (2)0.002 (2)0.014 (2)0.001 (2)
C270.052 (3)0.024 (2)0.038 (2)0.003 (2)0.015 (2)0.001 (2)
C280.047 (2)0.024 (2)0.037 (2)0.001 (2)0.013 (2)0.001 (2)
Geometric parameters (Å, º) top
O1—C61.215 (4)C16—C171.382 (5)
O2—C31.215 (4)C16—H60.952
O3—C131.202 (4)C17—C181.379 (5)
O4—C131.324 (4)C17—H70.954
O4—C211.497 (5)C18—C191.387 (6)
O5—C141.326 (4)C18—H80.951
O5—C251.487 (5)C19—C201.392 (5)
O6—C141.200 (4)C19—H90.954
N1—C11.429 (4)C20—H100.951
N1—C61.457 (4)C21—C221.515 (4)
N1—C141.422 (5)C21—C231.509 (4)
N2—C31.458 (4)C21—C241.516 (5)
N2—C41.421 (4)C22—H110.954
N2—C131.422 (5)C22—H120.944
C1—C21.349 (5)C22—H130.955
C1—C71.466 (5)C23—H140.949
C2—C31.457 (5)C23—H150.944
C2—C51.430 (4)C23—H160.959
C4—C51.375 (5)C24—H170.955
C4—C151.463 (5)C24—H180.940
C5—C61.452 (5)C24—H190.956
C7—C81.397 (5)C25—C261.511 (5)
C7—C121.403 (4)C25—C271.505 (4)
C8—C91.389 (4)C25—C281.518 (4)
C8—H10.950C26—H200.950
C9—C101.380 (4)C26—H210.953
C9—H20.951C26—H220.951
C10—C111.384 (5)C27—H230.947
C10—H30.954C27—H240.957
C11—C121.382 (5)C27—H250.952
C11—H40.951C28—H260.953
C12—H50.953C28—H270.948
C15—C161.399 (6)C28—H280.952
C15—C201.399 (5)
O1···C10i3.260 (4)N2···C17vii3.310 (4)
O1···C11i3.339 (4)C3···C17vii3.416 (4)
O2···C19ii3.251 (4)C4···C17vii3.512 (4)
O2···C18ii3.416 (4)C4···C27vi3.534 (4)
O2···C28iii3.470 (4)C4···C16vii3.550 (4)
O2···C26iii3.487 (4)C11···C12v3.429 (5)
O3···C8iii3.217 (4)C12···C12v3.343 (7)
O3···C9iii3.361 (4)C15···C16vii3.584 (4)
O5···C23iv3.568 (4)C16···C16vii3.309 (6)
O6···C11v3.460 (4)C19···C28viii3.573 (4)
O6···C20vi3.503 (4)C26···C27ix3.566 (4)
C13—O4—C21121.2 (3)C18—C17—H7119.4
C14—O5—C25120.4 (3)C17—C18—C19119.3 (3)
C1—N1—C6109.9 (3)C17—C18—H8120.4
C1—N1—C14125.4 (3)C19—C18—H8120.4
C6—N1—C14122.5 (3)C18—C19—C20120.4 (3)
C3—N2—C4111.0 (3)C18—C19—H9119.9
C3—N2—C13123.7 (3)C20—C19—H9119.8
C4—N2—C13124.0 (3)C15—C20—C19120.1 (3)
N1—C1—C2107.5 (3)C15—C20—H10120.1
N1—C1—C7122.2 (3)C19—C20—H10119.8
C2—C1—C7129.9 (3)O4—C21—C22102.0 (3)
C1—C2—C3139.3 (3)O4—C21—C23110.4 (3)
C1—C2—C5110.7 (3)O4—C21—C24108.2 (3)
C3—C2—C5108.6 (3)C22—C21—C23110.7 (3)
O2—C3—N2123.9 (3)C22—C21—C24112.0 (3)
O2—C3—C2132.8 (3)C23—C21—C24113.0 (3)
N2—C3—C2103.2 (3)C21—C22—H11109.5
N2—C4—C5106.9 (3)C21—C22—H12110.0
N2—C4—C15124.5 (3)C21—C22—H13109.4
C5—C4—C15128.1 (3)H11—C22—H12109.6
C2—C5—C4110.3 (3)H11—C22—H13108.7
C2—C5—C6108.1 (3)H12—C22—H13109.6
C4—C5—C6140.4 (3)C21—C23—H14109.7
O1—C6—N1122.9 (3)C21—C23—H15110.0
O1—C6—C5133.4 (3)C21—C23—H16109.1
N1—C6—C5103.6 (3)H14—C23—H15110.1
C1—C7—C8122.9 (3)H14—C23—H16108.8
C1—C7—C12118.1 (3)H15—C23—H16109.2
C8—C7—C12119.0 (3)C21—C24—H17109.2
C7—C8—C9120.1 (3)C21—C24—H18110.1
C7—C8—H1120.0C21—C24—H19109.2
C9—C8—H1119.9H17—C24—H18109.9
C8—C9—C10120.5 (3)H17—C24—H19108.6
C8—C9—H2119.7H18—C24—H19109.8
C10—C9—H2119.8O5—C25—C26108.8 (3)
C9—C10—C11119.6 (3)O5—C25—C27109.3 (3)
C9—C10—H3120.1O5—C25—C28102.0 (3)
C11—C10—H3120.3C26—C25—C27113.3 (3)
C10—C11—C12120.8 (3)C26—C25—C28111.1 (3)
C10—C11—H4119.8C27—C25—C28111.7 (3)
C12—C11—H4119.4C25—C26—H20109.7
C7—C12—C11120.0 (3)C25—C26—H21109.6
C7—C12—H5120.2C25—C26—H22109.9
C11—C12—H5119.8H20—C26—H21109.2
O3—C13—O4128.3 (4)H20—C26—H22109.4
O3—C13—N2122.8 (3)H21—C26—H22109.1
O4—C13—N2108.8 (3)C25—C27—H23110.1
O5—C14—O6128.4 (4)C25—C27—H24109.4
O5—C14—N1108.0 (3)C25—C27—H25109.9
O6—C14—N1123.5 (3)H23—C27—H24109.2
C4—C15—C16123.3 (3)H23—C27—H25109.5
C4—C15—C20117.6 (3)H24—C27—H25108.7
C16—C15—C20119.0 (3)C25—C28—H26109.7
C15—C16—C17119.8 (3)C25—C28—H27109.8
C15—C16—H6120.1C25—C28—H28109.6
C17—C16—H6120.0H26—C28—H27109.3
C16—C17—C18121.4 (4)H26—C28—H28109.0
C16—C17—H7119.3H27—C28—H28109.4
O1—C6—N1—C1173.9 (3)C2—C1—C7—C8141.0 (4)
O1—C6—N1—C1410.1 (4)C2—C1—C7—C1236.1 (5)
O1—C6—C5—C2173.7 (3)C2—C3—N2—C42.1 (3)
O1—C6—C5—C420.7 (7)C2—C3—N2—C13165.1 (2)
O2—C3—N2—C4178.9 (3)C2—C5—C4—C15170.8 (3)
O2—C3—N2—C1311.6 (4)C3—N2—C4—C52.5 (3)
O2—C3—C2—C118.4 (6)C3—N2—C4—C15170.4 (3)
O2—C3—C2—C5177.3 (3)C3—C2—C1—C79.2 (6)
O3—C13—O4—C212.0 (5)C3—C2—C5—C40.4 (3)
O3—C13—N2—C3133.2 (3)C3—C2—C5—C6170.7 (2)
O3—C13—N2—C432.4 (4)C4—C15—C16—C17173.5 (3)
O4—C13—N2—C347.6 (3)C4—C15—C20—C19173.6 (3)
O4—C13—N2—C4146.8 (3)C5—C2—C1—C7173.3 (3)
O5—C14—N1—C1145.1 (3)C5—C4—N2—C13164.7 (3)
O5—C14—N1—C653.7 (3)C5—C4—C15—C16146.3 (3)
O6—C14—O5—C257.3 (5)C5—C4—C15—C2029.6 (4)
O6—C14—N1—C134.1 (4)C5—C6—N1—C14167.0 (2)
O6—C14—N1—C6127.2 (3)C6—N1—C1—C7175.8 (3)
N1—C1—C2—C3163.6 (3)C6—C5—C4—C155.4 (6)
N1—C1—C2—C50.5 (3)C7—C1—N1—C1420.9 (4)
N1—C1—C7—C830.9 (5)C7—C8—C9—C101.9 (5)
N1—C1—C7—C12152.0 (3)C7—C12—C11—C101.3 (5)
N1—C6—C5—C22.8 (3)C8—C7—C12—C110.5 (5)
N1—C6—C5—C4162.8 (4)C8—C9—C10—C111.1 (5)
N1—C14—O5—C25173.6 (2)C9—C8—C7—C121.1 (5)
N2—C3—C2—C1165.3 (4)C9—C10—C11—C120.5 (5)
N2—C3—C2—C51.0 (3)C13—O4—C21—C22172.2 (2)
N2—C4—C5—C21.7 (3)C13—O4—C21—C2354.6 (3)
N2—C4—C5—C6167.1 (4)C13—O4—C21—C2469.6 (3)
N2—C4—C15—C1625.0 (4)C13—N2—C4—C1522.4 (4)
N2—C4—C15—C20159.1 (3)C14—O5—C25—C2664.1 (3)
N2—C13—O4—C21178.8 (2)C14—O5—C25—C2760.1 (3)
C1—N1—C6—C53.2 (3)C14—O5—C25—C28178.5 (2)
C1—C2—C5—C4168.7 (3)C15—C16—C17—C180.8 (5)
C1—C2—C5—C61.6 (3)C15—C20—C19—C181.0 (5)
C1—C7—C8—C9175.9 (3)C16—C15—C20—C192.4 (4)
C1—C7—C12—C11177.7 (3)C16—C17—C18—C190.6 (5)
C2—C1—N1—C62.3 (3)C17—C16—C15—C202.3 (4)
C2—C1—N1—C14165.6 (3)C17—C18—C19—C200.5 (5)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z; (iii) x, y+1/2, z1/2; (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, y1/2, z1/2; (ix) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC28H28N2O6
Mr488.54
Crystal system, space groupMonoclinic, P21/c
Temperature (K)93
a, b, c (Å)12.798 (2), 10.466 (1), 19.215 (3)
β (°) 108.10 (1)
V3)2446.5 (6)
Z4
Radiation typeCu Kα
µ (mm1)0.77
Crystal size (mm)0.30 × 0.20 × 0.06
Data collection
DiffractometerRigaku R-AXIS RAPID Imaging Plate
diffractometer
Absorption correctionMulti-scan
(Higashi, 1995)
Tmin, Tmax0.783, 0.955
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
21098, 4408, 2190
Rint0.060
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.126, 0.88
No. of reflections4401
No. of parameters325
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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—C61.215 (4)N2—C31.458 (4)
O2—C31.215 (4)N2—C41.421 (4)
O3—C131.202 (4)N2—C131.422 (5)
O4—C131.324 (4)C1—C21.349 (5)
O4—C211.497 (5)C1—C71.466 (5)
O5—C141.326 (4)C2—C31.457 (5)
O5—C251.487 (5)C2—C51.430 (4)
O6—C141.200 (4)C4—C51.375 (5)
N1—C11.429 (4)C4—C151.463 (5)
N1—C61.457 (4)C5—C61.452 (5)
N1—C141.422 (5)
O3—C13—N2—C3133.2 (3)N1—C1—C7—C830.9 (5)
O3—C13—N2—C432.4 (4)N1—C1—C7—C12152.0 (3)
O4—C13—N2—C347.6 (3)N2—C4—C15—C1625.0 (4)
O4—C13—N2—C4146.8 (3)N2—C4—C15—C20159.1 (3)
O5—C14—N1—C1145.1 (3)C2—C1—N1—C14165.6 (3)
O5—C14—N1—C653.7 (3)C2—C1—C7—C8141.0 (4)
O6—C14—N1—C134.1 (4)C5—C4—C15—C16146.3 (3)
O6—C14—N1—C6127.2 (3)C5—C4—C15—C2029.6 (4)
 

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