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ISSN: 2056-9890

(E)-3,3,6,6-Tetra­methyl-9-(2-nitro­styr­yl)-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione

aCenter for Neuro-Medicine, Korea Institute of Science and Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and bAdvanced Analysis Center, Korea Institute of Science and Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea
*Correspondence e-mail: jhcha@kist.re.kr

(Received 3 May 2012; accepted 23 May 2012; online 31 May 2012)

In the title compound, C25H27NO5, each of the cyclo­hexenone rings adopts a half-chair conformation, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating from the plane of the other four atoms. In the crystal, weak C—H⋯O hydrogen bonds link mol­ecules into chains parallel to the c axis.

Related literature

For the crystal structures of xanthene derivatives studied recently by our group, see: Cha et al. (2012[Cha, J. H., Pae, A. N., Lee, J. K. & Cho, Y. S. (2012). Acta Cryst. E68, o454.]); Lee et al. (2012[Lee, J. K., Pae, A. N., Cho, Y. S. & Cha, J. H. (2012). Acta Cryst. E68, o501.]).

[Scheme 1]

Experimental

Crystal data
  • C25H27NO5

  • Mr = 421.49

  • Monoclinic, C 2/c

  • a = 33.312 (3) Å

  • b = 9.4144 (6) Å

  • c = 14.4581 (10) Å

  • β = 102.3931 (19)°

  • V = 4428.6 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.30 × 0.30 × 0.30 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.753, Tmax = 0.974

  • 20666 measured reflections

  • 5066 independent reflections

  • 3965 reflections with F2 > 2.0σ(F2)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.153

  • S = 1.05

  • 5066 reflections

  • 288 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C17—H17⋯O5i 0.93 2.49 3.420 (3) 176
Symmetry code: (i) [x, -y, z-{\script{1\over 2}}].

Data collection: RAPID-AUTO (Rigaku, 2006[Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR2008 in Il Milione (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

As part of our ongoing study of the substituent effect on the solid state structures of xanthene derivatives (Cha et al., (2012). We present here the crystal structure of the title compound (I) (Fig. 1).

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related structures (Cha et al., 2012). All two cyclohexenone rings in (I) display half-chair conformation, whereas the pyran ring adopts a boat conformation.

In the crystal, weak intermolecular C17—H17···O5 hydrogen bonds into chains parallel to the c axis.

Related literature top

For the crystal structures of xanthene derivatives studied recently by our group, see: Cha et al. (2012); Lee et al. (2012).

Experimental top

To solution of (E)-2.2-(3-(2-Nitrophenyl)prop-2-ene-1,1-diyl)bis (3-hydroxy-5,5-δimethylcyclohex-2-enone) (1.25 mmol) in methanol (12.5 ml) was added catalytic amount of sulfuric acid under nitrogen atmosphere. After stirring for 3 h, the solvent was evaporated and the remaining residue dissolved in ethyl acetate. The mixture was neutralized with saturated sodium bicarbonate and the solution was extracted with ethyl acetate. The resulting residue solid was purified by recrystallization from a mixture of ethanol and methylene chloride (1:1) to afford colorless block type crystals suitable for X-ray analysis.

Refinement top

All hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–1.00 Å and Uiso(H) = 1.2 or 1.5 Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 1995); data reduction: RAPID-AUTO (Rigaku, 1995); program(s) used to solve structure: SIR2008 in Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoid.
(E)-3,3,6,6-Tetramethyl-9-(2-nitrostyryl)-3,4,5,6,7,9-hexahydro- 1H-xanthene-1,8(2H)-dione top
Crystal data top
C25H27NO5F(000) = 1792.00
Mr = 421.49Dx = 1.264 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2ycCell parameters from 15305 reflections
a = 33.312 (3) Åθ = 3.0–27.5°
b = 9.4144 (6) ŵ = 0.09 mm1
c = 14.4581 (10) ÅT = 296 K
β = 102.3931 (19)°Block, colourless
V = 4428.6 (6) Å30.30 × 0.30 × 0.30 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3965 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.022
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 4343
Tmin = 0.753, Tmax = 0.974k = 1112
20666 measured reflectionsl = 1815
5066 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.085P)2 + 1.6883P]
where P = (Fo2 + 2Fc2)/3
5066 reflections(Δ/σ)max < 0.001
288 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.27 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H27NO5V = 4428.6 (6) Å3
Mr = 421.49Z = 8
Monoclinic, C2/cMo Kα radiation
a = 33.312 (3) ŵ = 0.09 mm1
b = 9.4144 (6) ÅT = 296 K
c = 14.4581 (10) Å0.30 × 0.30 × 0.30 mm
β = 102.3931 (19)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5066 independent reflections
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
3965 reflections with F2 > 2.0σ(F2)
Tmin = 0.753, Tmax = 0.974Rint = 0.022
20666 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.32 e Å3
5066 reflectionsΔρmin = 0.27 e Å3
288 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 was performed using all reflections. 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
O10.17679 (3)0.29705 (11)0.33160 (7)0.0425 (3)
O20.10180 (4)0.41560 (15)0.56326 (9)0.0605 (4)
O30.20630 (5)0.00886 (16)0.59592 (9)0.0732 (5)
O40.10890 (7)0.1543 (3)0.70033 (15)0.1349 (10)
O50.05219 (8)0.1355 (3)0.74228 (13)0.1202 (8)
N10.07269 (6)0.14573 (18)0.68205 (12)0.0698 (5)
C10.14994 (4)0.19968 (16)0.49809 (10)0.0386 (3)
C20.11356 (4)0.44403 (17)0.49075 (10)0.0434 (4)
C30.10484 (5)0.58616 (18)0.44234 (12)0.0513 (4)
C40.10020 (5)0.58137 (17)0.33439 (11)0.0447 (4)
C50.13839 (5)0.50909 (17)0.31324 (11)0.0457 (4)
C60.23027 (5)0.12986 (15)0.34094 (11)0.0426 (4)
C70.24393 (5)0.01947 (16)0.37621 (11)0.0428 (4)
C80.24960 (5)0.01955 (18)0.48454 (11)0.0489 (4)
C90.21302 (5)0.03331 (17)0.52095 (11)0.0453 (4)
C100.13847 (4)0.34177 (15)0.45014 (10)0.0376 (3)
C110.15034 (4)0.37823 (15)0.37052 (10)0.0378 (3)
C120.19683 (4)0.18691 (15)0.38454 (10)0.0372 (3)
C130.18697 (4)0.14200 (15)0.46483 (10)0.0374 (3)
C140.11429 (5)0.09666 (17)0.47453 (11)0.0415 (4)
C150.09654 (5)0.03555 (16)0.53714 (10)0.0410 (4)
C160.06166 (4)0.06426 (15)0.51520 (10)0.0389 (3)
C170.03628 (5)0.07231 (17)0.42507 (11)0.0458 (4)
C180.00380 (5)0.1662 (2)0.40412 (13)0.0561 (5)
C190.00562 (6)0.2543 (2)0.47284 (15)0.0599 (5)
C200.01737 (6)0.24595 (18)0.56348 (14)0.0565 (5)
C210.05035 (5)0.15289 (16)0.58291 (11)0.0454 (4)
C220.21140 (6)0.12792 (19)0.33232 (14)0.0595 (5)
C230.28438 (6)0.0549 (2)0.34786 (15)0.0626 (5)
C240.09700 (6)0.73118 (19)0.29204 (14)0.0602 (5)
C250.06161 (5)0.4985 (3)0.28947 (14)0.0641 (5)
H10.15730.21380.56680.0463*
H3A0.12700.65090.46870.0616*
H3B0.07980.62430.45640.0616*
H5A0.13320.48460.24660.0548*
H5B0.16110.57560.32580.0548*
H6A0.25370.19340.35540.0511*
H6B0.22070.12750.27270.0511*
H8A0.25580.11570.50730.0587*
H8B0.27320.03920.51130.0587*
H170.04140.01260.37770.0549*
H180.01200.17010.34280.0673*
H190.02730.31850.45780.0718*
H200.01090.30190.61130.0678*
H22A0.18750.11620.35870.0714*
H22B0.22220.22210.34560.0714*
H22C0.20400.11380.26510.0714*
H23A0.29180.15150.36460.0751*
H23B0.30560.00740.38040.0751*
H23C0.28120.04280.28070.0751*
H24A0.12140.78390.31900.0723*
H24B0.07350.77850.30590.0723*
H24C0.09420.72500.22470.0723*
H25A0.03790.54490.30350.0769*
H25B0.06350.40380.31450.0769*
H25C0.05910.49480.22210.0769*
H140.1051 (7)0.077 (3)0.4067 (15)0.067 (6)*
H150.1074 (6)0.060 (2)0.6052 (14)0.060 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0439 (6)0.0459 (6)0.0424 (6)0.0097 (5)0.0198 (5)0.0088 (5)
O20.0655 (8)0.0719 (8)0.0529 (7)0.0029 (7)0.0325 (6)0.0044 (6)
O30.0850 (10)0.0879 (10)0.0501 (7)0.0225 (8)0.0219 (7)0.0266 (7)
O40.0867 (14)0.203 (3)0.0983 (14)0.0202 (15)0.0178 (11)0.0736 (16)
O50.170 (2)0.1387 (19)0.0595 (10)0.0029 (16)0.0417 (12)0.0070 (11)
N10.0843 (13)0.0648 (10)0.0570 (10)0.0125 (9)0.0078 (9)0.0220 (8)
C10.0382 (8)0.0456 (8)0.0339 (7)0.0040 (6)0.0123 (6)0.0003 (6)
C20.0364 (8)0.0538 (9)0.0417 (8)0.0022 (7)0.0121 (6)0.0079 (7)
C30.0501 (9)0.0510 (9)0.0545 (9)0.0070 (7)0.0149 (7)0.0080 (8)
C40.0376 (8)0.0464 (8)0.0502 (9)0.0059 (6)0.0095 (7)0.0004 (7)
C50.0421 (8)0.0472 (9)0.0507 (9)0.0062 (7)0.0163 (7)0.0078 (7)
C60.0411 (8)0.0415 (8)0.0495 (9)0.0003 (6)0.0194 (7)0.0004 (7)
C70.0412 (8)0.0401 (8)0.0472 (8)0.0013 (6)0.0095 (6)0.0038 (7)
C80.0456 (9)0.0484 (9)0.0496 (9)0.0083 (7)0.0032 (7)0.0012 (7)
C90.0484 (9)0.0474 (9)0.0384 (8)0.0001 (7)0.0057 (7)0.0020 (7)
C100.0319 (7)0.0438 (8)0.0384 (7)0.0020 (6)0.0104 (6)0.0014 (6)
C110.0315 (7)0.0424 (8)0.0410 (7)0.0005 (6)0.0113 (6)0.0001 (6)
C120.0340 (7)0.0380 (7)0.0404 (7)0.0002 (6)0.0100 (6)0.0010 (6)
C130.0356 (7)0.0401 (7)0.0373 (7)0.0025 (6)0.0096 (6)0.0012 (6)
C140.0407 (8)0.0486 (8)0.0365 (7)0.0052 (6)0.0112 (6)0.0005 (7)
C150.0428 (8)0.0438 (8)0.0378 (8)0.0026 (6)0.0120 (6)0.0013 (7)
C160.0379 (7)0.0385 (7)0.0436 (8)0.0024 (6)0.0163 (6)0.0002 (6)
C170.0449 (8)0.0509 (9)0.0438 (8)0.0005 (7)0.0146 (7)0.0001 (7)
C180.0441 (9)0.0627 (11)0.0600 (10)0.0021 (8)0.0083 (8)0.0075 (9)
C190.0433 (9)0.0537 (10)0.0849 (14)0.0093 (8)0.0191 (9)0.0069 (10)
C200.0571 (11)0.0459 (9)0.0727 (12)0.0059 (8)0.0279 (9)0.0075 (9)
C210.0481 (9)0.0421 (8)0.0487 (9)0.0012 (7)0.0163 (7)0.0052 (7)
C220.0687 (12)0.0489 (9)0.0596 (11)0.0118 (8)0.0108 (9)0.0091 (8)
C230.0537 (11)0.0621 (11)0.0747 (12)0.0149 (9)0.0201 (9)0.0056 (10)
C240.0599 (11)0.0530 (10)0.0688 (12)0.0158 (8)0.0160 (9)0.0065 (9)
C250.0437 (10)0.0749 (13)0.0682 (12)0.0002 (9)0.0001 (8)0.0048 (10)
Geometric parameters (Å, º) top
O1—C111.3747 (19)C18—C191.381 (3)
O1—C121.3738 (17)C19—C201.371 (3)
O2—C21.225 (2)C20—C211.386 (3)
O3—C91.219 (3)C1—H10.980
O4—N11.181 (3)C3—H3A0.970
O5—N11.220 (4)C3—H3B0.970
N1—C211.468 (3)C5—H5A0.970
C1—C101.517 (2)C5—H5B0.970
C1—C131.517 (2)C6—H6A0.970
C1—C141.514 (3)C6—H6B0.970
C2—C31.509 (3)C8—H8A0.970
C2—C101.473 (3)C8—H8B0.970
C3—C41.536 (3)C14—H140.98 (2)
C4—C51.530 (3)C15—H151.001 (19)
C4—C241.532 (3)C17—H170.930
C4—C251.525 (3)C18—H180.930
C5—C111.490 (2)C19—H190.930
C6—C71.531 (2)C20—H200.930
C6—C121.493 (3)C22—H22A0.960
C7—C81.537 (3)C22—H22B0.960
C7—C221.525 (3)C22—H22C0.960
C7—C231.527 (3)C23—H23A0.960
C8—C91.512 (3)C23—H23B0.960
C9—C131.468 (2)C23—H23C0.960
C10—C111.340 (3)C24—H24A0.960
C12—C131.341 (3)C24—H24B0.960
C14—C151.315 (3)C24—H24C0.960
C15—C161.475 (2)C25—H25A0.960
C16—C171.395 (2)C25—H25B0.960
C16—C211.398 (3)C25—H25C0.960
C17—C181.379 (3)
O1···C12.8912 (19)O3···H6Biv2.7353
O2···C12.871 (2)O3···H22Bxi3.4562
O2···C113.527 (3)O3···H22Civ2.7199
O2···C143.326 (3)O3···H23Axi3.2460
O2···C153.598 (2)O3···H23Civ3.2773
O3···C12.871 (2)O4···H5Aiv3.2458
O3···C123.525 (2)O4···H25Biv3.4054
O3···C143.340 (3)O4···H14iv3.10 (3)
O3···C153.596 (3)O5···H17iii3.5151
O4···C152.918 (3)O5···H17iv2.4916
O4···C162.924 (3)O5···H18iii3.2981
O4···C203.371 (3)O5···H24Bx3.5167
O5···C163.431 (3)O5···H25Biv2.7278
O5···C202.797 (3)O5···H25Civ3.4071
N1···C152.941 (3)O5···H14iv2.69 (2)
C2···C52.925 (3)N1···H17iv3.5458
C2···C143.279 (3)N1···H18iii3.5702
C2···C253.093 (3)N1···H25Biv3.1486
C3···C112.808 (3)N1···H25Civ3.3845
C4···C102.932 (2)N1···H14iv3.26 (2)
C6···C92.928 (3)C1···H6Aix3.5897
C7···C132.932 (3)C1···H8Bix3.5738
C8···C122.805 (2)C1···H23Bix3.4306
C9···C143.267 (3)C2···H19iii3.3364
C9···C223.112 (3)C2···H23Bix2.9634
C10···C122.756 (2)C5···H8Bix3.4808
C10···C153.549 (3)C5···H23Cii3.2897
C10···C253.402 (3)C6···H23Aii3.5589
C11···C132.753 (2)C6···H23Cii3.5284
C11···C143.392 (3)C8···H8Axi3.4423
C11···C253.147 (2)C8···H22Bxi3.4415
C12···C143.393 (3)C9···H6Aix3.1931
C12···C223.122 (3)C10···H8Bix3.0866
C13···C153.539 (3)C10···H23Bix3.0874
C13···C223.385 (3)C11···H8Bix2.8547
C14···C173.000 (3)C11···H23Cii3.5605
C16···C192.830 (3)C12···H8Bix3.0450
C17···C202.759 (3)C13···H6Aix3.2954
C18···C212.717 (3)C13···H8Bix3.2704
O1···O4i2.946 (3)C15···H19iii3.5356
O1···C23ii3.434 (3)C15···H24Cx3.5397
O2···C19iii3.482 (3)C16···H3Bvi3.1469
O4···O1iv2.946 (3)C16···H24Bvi3.4656
O4···C11iv3.308 (3)C17···H3Bvi3.1904
O4···C12iv3.524 (3)C17···H24Bvi2.7183
O5···O5v3.532 (4)C18···H3Bvi3.1692
O5···C14iv3.565 (3)C18···H24Bvi3.0142
O5···C17iv3.420 (3)C18···H24Bxii3.5727
O5···C25iv3.486 (4)C18···H24Cxii3.5436
C11···O4i3.308 (3)C18···H25Avi3.3944
C12···O4i3.524 (3)C19···H3Bvi3.1212
C14···O5i3.565 (3)C20···H3Bvi3.0969
C16···C18iii3.452 (3)C20···H17iii3.3465
C16···C19iii3.557 (3)C20···H25Civ3.3632
C17···O5i3.420 (3)C21···H3Bvi3.0783
C17···C20iii3.511 (3)C21···H17iii3.5840
C17···C21iii3.563 (3)C21···H18iii3.5529
C17···C24vi3.589 (3)C22···H5Bvi3.2455
C18···C16iii3.452 (3)C22···H6Avii3.5913
C18···C21iii3.529 (3)C22···H8Axi3.3626
C19···O2iii3.482 (3)C22···H24Avi3.0775
C19···C16iii3.557 (3)C23···H5Avii3.3396
C20···C17iii3.511 (3)C23···H6Bvii3.4470
C21···C17iii3.563 (3)C24···H17viii3.4298
C21···C18iii3.529 (3)C24···H18xiii3.2108
C23···O1vii3.434 (3)C24···H22Aviii3.2921
C24···C17viii3.589 (3)C24···H15xiv3.42 (2)
C25···O5i3.486 (4)C25···H20iii3.5796
O1···H5A2.4439C25···H20i3.3237
O1···H5B2.6718C25···H25Axv3.3288
O1···H6A2.6941H1···H6Aix3.0646
O1···H6B2.4398H1···H22Civ3.1000
O1···H143.50 (3)H1···H23Bix2.9325
O2···H12.6432H1···H24Cx3.4669
O2···H3A2.8236H3A···H22Aviii3.5743
O2···H3B2.5103H3A···H23Aix3.2141
O2···H25B3.5502H3A···H23Bix3.1495
O2···H153.40 (2)H3B···C16viii3.1469
O3···H12.6349H3B···C17viii3.1904
O3···H8A2.5055H3B···C18viii3.1692
O3···H8B2.7992H3B···C19viii3.1212
O3···H22A3.5002H3B···C20viii3.0969
O3···H153.39 (2)H3B···C21viii3.0783
O4···H203.5265H3B···H20viii3.5998
O4···H152.44 (2)H5A···O2xiv2.7946
O5···H202.6105H5A···O4i3.2458
O5···H153.50 (3)H5A···C23ii3.3396
N1···H202.5572H5A···H23Aii3.4923
N1···H152.63 (2)H5A···H23Bii3.0312
C1···H152.66 (3)H5A···H23Cii2.9733
C2···H12.7095H5B···C22viii3.2455
C2···H5B3.3702H5B···H8Aix3.2789
C2···H25A3.4131H5B···H8Bix3.0487
C2···H25B2.7554H5B···H22Aviii3.0393
C3···H5A3.3114H5B···H22Bviii2.7555
C3···H5B2.7791H5B···H22Cviii3.4496
C3···H24A2.7150H5B···H23Bii3.4571
C3···H24B2.7158H5B···H23Cii2.9283
C3···H24C3.3556H6A···O3ix3.2694
C3···H25A2.6884H6A···C1ix3.5897
C3···H25B2.6773H6A···C9ix3.1931
C3···H25C3.3346H6A···C13ix3.2954
C5···H3A2.7099H6A···C22ii3.5913
C5···H3B3.3179H6A···H1ix3.0646
C5···H24A2.6534H6A···H8Bix3.4060
C5···H24B3.3203H6A···H22Bii3.2741
C5···H24C2.6711H6A···H22Cii3.0596
C5···H25A3.3359H6A···H23Aii3.5312
C5···H25B2.6881H6A···H23Cii3.2265
C5···H25C2.6911H6B···O3i2.7353
C6···H8A3.3131H6B···C23ii3.4470
C6···H8B2.7064H6B···H22Bii3.1533
C6···H22A2.7600H6B···H23Aii2.8434
C6···H22B3.3260H6B···H23Cii3.1963
C6···H22C2.6111H8A···C8xi3.4423
C6···H23A3.3216H8A···C22xi3.3626
C6···H23B2.7079H8A···H5Bix3.2789
C6···H23C2.6291H8A···H8Axi2.5608
C8···H6A2.7633H8A···H22Axi3.4811
C8···H6B3.3104H8A···H22Bxi2.5932
C8···H22A2.6076H8A···H23Axi3.4651
C8···H22B2.7784H8B···O1ix2.9483
C8···H22C3.3309H8B···C1ix3.5738
C8···H23A2.7521H8B···C5ix3.4808
C8···H23B2.6478H8B···C10ix3.0866
C8···H23C3.3421H8B···C11ix2.8547
C9···H12.7026H8B···C12ix3.0450
C9···H6A3.3516H8B···C13ix3.2704
C9···H22A2.7108H8B···H5Bix3.0487
C9···H22B3.5546H8B···H6Aix3.4060
C10···H3A2.9546H17···O5iii3.5151
C10···H3B3.3143H17···O5i2.4916
C10···H5A3.2062H17···N1i3.5458
C10···H5B3.0385H17···C20iii3.3465
C10···H25B2.8843H17···C21iii3.5840
C10···H142.74 (2)H17···C24vi3.4298
C11···H13.1975H17···H18xv3.4610
C11···H3A3.1115H17···H20iii3.4577
C11···H25B2.8416H17···H24Avi3.5294
C11···H25C3.5005H17···H24Bvi2.5609
C11···H143.30 (2)H18···O5iii3.2981
C12···H13.1995H18···N1iii3.5702
C12···H8B3.1239H18···C21iii3.5529
C12···H22A2.8858H18···C24xii3.2108
C12···H22C3.3516H18···H17xv3.4610
C12···H143.30 (3)H18···H18xv2.9593
C13···H6A3.0319H18···H24Bvi3.0455
C13···H6B3.2160H18···H24Bxii2.6754
C13···H8A3.3039H18···H24Cxii2.8754
C13···H8B2.9675H18···H25Avi3.2705
C13···H22A2.8763H18···H25Axii3.4107
C13···H142.74 (2)H18···H25Cxii3.5574
C14···H172.7299H18···H15iii3.5711
C15···H12.5922H19···O2iii2.6018
C15···H172.6598H19···C2iii3.3364
C16···H183.2566H19···C15iii3.5356
C16···H203.2862H19···H24Cxii3.0939
C16···H142.70 (3)H19···H25Cxii3.1296
C17···H193.2415H19···H15iii3.5795
C17···H142.75 (3)H20···C25iii3.5796
C17···H153.363 (18)H20···C25iv3.3237
C18···H203.2178H20···H3Bvi3.5998
C19···H173.2330H20···H17iii3.4577
C20···H183.2108H20···H25Aiii3.2033
C21···H173.2027H20···H25Aiv3.5624
C21···H193.2217H20···H25Biii3.0597
C21···H152.74 (2)H20···H25Biv3.2270
C22···H6A3.3236H20···H25Civ2.7081
C22···H6B2.5953H22A···C24vi3.2921
C22···H8A2.6456H22A···H3Avi3.5743
C22···H8B3.3342H22A···H5Bvi3.0393
C22···H23A2.6269H22A···H8Axi3.4811
C22···H23B3.3183H22A···H24Avi2.3506
C22···H23C2.7109H22B···O3xi3.4562
C23···H6A2.5625H22B···C8xi3.4415
C23···H6B2.7632H22B···H5Bvi2.7555
C23···H8A2.7372H22B···H6Avii3.2741
C23···H8B2.6236H22B···H6Bvii3.1533
C23···H22A3.3149H22B···H8Axi2.5932
C23···H22B2.5968H22B···H23Cvii3.5180
C23···H22C2.7443H22B···H24Avi3.2970
C24···H3A2.6457H22C···O3i2.7199
C24···H3B2.7518H22C···H1i3.1000
C24···H5A2.7594H22C···H5Bvi3.4496
C24···H5B2.5496H22C···H6Avii3.0596
C24···H25A2.6674H22C···H24Avi3.1680
C24···H25B3.3178H22C···H15i3.5723
C24···H25C2.6499H23A···O1vii3.2632
C25···H3A3.3310H23A···O3xi3.2460
C25···H3B2.6391H23A···C6vii3.5589
C25···H5A2.5925H23A···H3Aix3.2141
C25···H5B3.3239H23A···H5Avii3.4923
C25···H24A3.3164H23A···H6Avii3.5312
C25···H24B2.6681H23A···H6Bvii2.8434
C25···H24C2.6528H23A···H8Axi3.4651
H1···H142.8809H23B···O2ix3.1035
H1···H152.3552H23B···C1ix3.4306
H3A···H5B2.6594H23B···C2ix2.9634
H3A···H24A2.4729H23B···C10ix3.0874
H3A···H24B2.8917H23B···H1ix2.9325
H3A···H24C3.5323H23B···H3Aix3.1495
H3A···H25A3.5304H23B···H5Avii3.0312
H3A···H25B3.5823H23B···H5Bvii3.4571
H3B···H24A3.0507H23C···O1vii2.8010
H3B···H24B2.5856H23C···O3i3.2773
H3B···H25A2.4626H23C···C5vii3.2897
H3B···H25B2.8870H23C···C6vii3.5284
H3B···H25C3.5259H23C···C11vii3.5605
H5A···H24A3.0605H23C···H5Avii2.9733
H5A···H24C2.5958H23C···H5Bvii2.9283
H5A···H25A3.4909H23C···H6Avii3.2265
H5A···H25B2.8125H23C···H6Bvii3.1963
H5A···H25C2.4196H23C···H22Bii3.5180
H5B···H24A2.3562H24A···C22viii3.0775
H5B···H24B3.4498H24A···H17viii3.5294
H5B···H24C2.7739H24A···H22Aviii2.3506
H5B···H25C3.4928H24A···H22Bviii3.2970
H6A···H8B2.6423H24A···H22Cviii3.1680
H6A···H22C3.4467H24A···H14viii3.1352
H6A···H23A3.4783H24A···H15xiv3.3614
H6A···H23B2.4317H24B···O5xiv3.5167
H6A···H23C2.7150H24B···C16viii3.4656
H6B···H22A2.9368H24B···C17viii2.7183
H6B···H22B3.4524H24B···C18viii3.0142
H6B···H22C2.3353H24B···C18xiii3.5727
H6B···H23A3.5939H24B···H17viii2.5609
H6B···H23B3.1308H24B···H18viii3.0455
H6B···H23C2.5573H24B···H18xiii2.6754
H8A···H22A2.7741H24B···H14viii3.2391
H8A···H22B2.5702H24C···O2xiv2.7421
H8A···H22C3.5574H24C···C15xiv3.5397
H8A···H23A2.6218H24C···C18xiii3.5436
H8A···H23B2.9602H24C···H1xiv3.4669
H8B···H22A3.5276H24C···H18xiii2.8754
H8B···H22B3.5955H24C···H19xiii3.0939
H8B···H23A2.9446H24C···H15xiv2.7534
H8B···H23B2.3893H25A···C18viii3.3944
H8B···H23C3.4868H25A···C25xv3.3288
H17···H182.2884H25A···H18viii3.2705
H17···H142.2395H25A···H18xiii3.4107
H18···H192.3106H25A···H20iii3.2033
H19···H202.3136H25A···H20i3.5624
H22A···H23A3.4724H25A···H25Axv2.6653
H22A···H143.4855H25A···H25Cxv3.2077
H22B···H23A2.3707H25B···O4i3.4054
H22B···H23B3.4697H25B···O5i2.7278
H22B···H23C2.8956H25B···N1i3.1486
H22C···H23A2.9896H25B···H20iii3.0597
H22C···H23C2.6188H25B···H20i3.2270
H24A···H25A3.5458H25C···O2xiv3.0683
H24A···H25C3.5254H25C···O5i3.4071
H24B···H25A2.4942H25C···N1i3.3845
H24B···H25B3.5482H25C···C20i3.3632
H24B···H25C2.9295H25C···H18xiii3.5574
H24C···H25A2.9326H25C···H19xiii3.1296
H24C···H25B3.5283H25C···H20i2.7081
H24C···H25C2.4591H25C···H25Axv3.2077
H25B···H143.5141H14···O4i3.10 (3)
H14···H152.86 (3)H14···O5i2.69 (2)
O1···H8Bix2.9483H14···N1i3.26 (2)
O1···H23Aii3.2632H14···H24Avi3.1352
O1···H23Cii2.8010H14···H24Bvi3.2391
O2···H5Ax2.7946H15···C24x3.42 (2)
O2···H19iii2.6018H15···H18iii3.5711
O2···H23Bix3.1035H15···H19iii3.5795
O2···H24Cx2.7421H15···H22Civ3.5723
O2···H25Cx3.0683H15···H24Ax3.3614
O3···H6Aix3.2694H15···H24Cx2.7534
C11—O1—C12117.97 (12)C2—C3—H3A108.664
O4—N1—O5123.2 (2)C2—C3—H3B108.668
O4—N1—C21119.7 (2)C4—C3—H3A108.660
O5—N1—C21117.15 (19)C4—C3—H3B108.666
C10—C1—C13108.23 (13)H3A—C3—H3B107.605
C10—C1—C14110.70 (11)C4—C5—H5A108.979
C13—C1—C14110.56 (13)C4—C5—H5B108.973
O2—C2—C3121.71 (15)C11—C5—H5A108.980
O2—C2—C10120.62 (15)C11—C5—H5B108.977
C3—C2—C10117.61 (14)H5A—C5—H5B107.787
C2—C3—C4114.37 (14)C7—C6—H6A109.061
C3—C4—C5108.03 (13)C7—C6—H6B109.060
C3—C4—C24111.24 (14)C12—C6—H6A109.064
C3—C4—C25109.86 (15)C12—C6—H6B109.075
C5—C4—C24108.60 (15)H6A—C6—H6B107.811
C5—C4—C25110.40 (14)C7—C8—H8A108.514
C24—C4—C25108.70 (14)C7—C8—H8B108.512
C4—C5—C11113.01 (14)C9—C8—H8A108.525
C7—C6—C12112.65 (14)C9—C8—H8B108.528
C6—C7—C8107.62 (13)H8A—C8—H8B107.507
C6—C7—C22110.02 (13)C1—C14—H14113.9 (13)
C6—C7—C23109.11 (15)C15—C14—H14121.2 (13)
C8—C7—C22110.17 (15)C14—C15—H15117.0 (12)
C8—C7—C23110.54 (14)C16—C15—H15117.6 (12)
C22—C7—C23109.35 (15)C16—C17—H17119.000
C7—C8—C9115.01 (13)C18—C17—H17119.023
O3—C9—C8121.19 (15)C17—C18—H18119.485
O3—C9—C13121.24 (17)C19—C18—H18119.482
C8—C9—C13117.51 (14)C18—C19—H19120.454
C1—C10—C2120.15 (14)C20—C19—H19120.441
C1—C10—C11121.78 (14)C19—C20—H20120.458
C2—C10—C11118.07 (13)C21—C20—H20120.461
O1—C11—C5110.51 (13)C7—C22—H22A109.462
O1—C11—C10122.86 (13)C7—C22—H22B109.482
C5—C11—C10126.62 (14)C7—C22—H22C109.478
O1—C12—C6110.72 (13)H22A—C22—H22B109.463
O1—C12—C13122.70 (14)H22A—C22—H22C109.456
C6—C12—C13126.57 (13)H22B—C22—H22C109.486
C1—C13—C9119.90 (14)C7—C23—H23A109.465
C1—C13—C12121.90 (13)C7—C23—H23B109.469
C9—C13—C12118.20 (14)C7—C23—H23C109.458
C1—C14—C15124.89 (14)H23A—C23—H23B109.488
C14—C15—C16125.48 (14)H23A—C23—H23C109.468
C15—C16—C17121.81 (14)H23B—C23—H23C109.479
C15—C16—C21123.22 (13)C4—C24—H24A109.472
C17—C16—C21114.92 (13)C4—C24—H24B109.473
C16—C17—C18121.98 (16)C4—C24—H24C109.477
C17—C18—C19121.03 (16)H24A—C24—H24B109.466
C18—C19—C20119.10 (18)H24A—C24—H24C109.470
C19—C20—C21119.08 (18)H24B—C24—H24C109.470
N1—C21—C16120.00 (14)C4—C25—H25A109.470
N1—C21—C20116.14 (16)C4—C25—H25B109.480
C16—C21—C20123.80 (15)C4—C25—H25C109.479
C10—C1—H1109.114H25A—C25—H25B109.468
C13—C1—H1109.098H25A—C25—H25C109.463
C14—C1—H1109.114H25B—C25—H25C109.467
C11—O1—C12—C6168.31 (10)C12—C6—C7—C846.35 (15)
C11—O1—C12—C1310.75 (17)C12—C6—C7—C2273.70 (15)
C12—O1—C11—C5168.03 (10)C12—C6—C7—C23166.33 (10)
C12—O1—C11—C1010.74 (17)C6—C7—C8—C953.11 (17)
O4—N1—C21—C1651.8 (3)C22—C7—C8—C966.85 (17)
O4—N1—C21—C20130.9 (3)C23—C7—C8—C9172.18 (13)
O5—N1—C21—C16130.5 (2)C7—C8—C9—O3151.50 (14)
O5—N1—C21—C2046.8 (3)C7—C8—C9—C1331.18 (19)
C10—C1—C13—C9159.62 (10)O3—C9—C13—C12.4 (2)
C10—C1—C13—C1220.69 (16)O3—C9—C13—C12177.92 (14)
C13—C1—C10—C2159.45 (10)C8—C9—C13—C1179.69 (11)
C13—C1—C10—C1120.69 (16)C8—C9—C13—C120.61 (19)
C10—C1—C14—C15120.69 (15)C1—C10—C11—O16.46 (19)
C14—C1—C10—C279.24 (15)C1—C10—C11—C5174.98 (11)
C14—C1—C10—C11100.62 (15)C2—C10—C11—O1173.67 (11)
C13—C1—C14—C15119.39 (16)C2—C10—C11—C54.89 (19)
C14—C1—C13—C978.98 (14)O1—C12—C13—C16.4 (2)
C14—C1—C13—C12100.70 (15)O1—C12—C13—C9173.88 (10)
O2—C2—C3—C4149.19 (13)C6—C12—C13—C1174.67 (11)
O2—C2—C10—C10.14 (19)C6—C12—C13—C95.0 (2)
O2—C2—C10—C11179.73 (12)C1—C14—C15—C16179.61 (13)
C3—C2—C10—C1177.22 (11)C14—C15—C16—C1719.3 (3)
C3—C2—C10—C112.92 (17)C14—C15—C16—C21163.59 (15)
C10—C2—C3—C433.48 (17)C15—C16—C17—C18179.56 (13)
C2—C3—C4—C553.53 (17)C15—C16—C21—N12.2 (3)
C2—C3—C4—C24172.64 (12)C15—C16—C21—C20179.23 (13)
C2—C3—C4—C2566.95 (16)C17—C16—C21—N1175.15 (13)
C3—C4—C5—C1145.07 (16)C17—C16—C21—C201.9 (3)
C24—C4—C5—C11165.84 (12)C21—C16—C17—C183.1 (3)
C25—C4—C5—C1175.08 (16)C16—C17—C18—C191.7 (3)
C4—C5—C11—O1163.21 (11)C17—C18—C19—C201.2 (3)
C4—C5—C11—C1018.08 (19)C18—C19—C20—C212.3 (3)
C7—C6—C12—O1161.08 (11)C19—C20—C21—N1177.90 (16)
C7—C6—C12—C1319.91 (19)C19—C20—C21—C160.7 (3)
Symmetry codes: (i) x, y, z1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x, y, z+1; (iv) x, y, z+1/2; (v) x, y, z+3/2; (vi) x, y1, z; (vii) x+1/2, y1/2, z+1/2; (viii) x, y+1, z; (ix) x+1/2, y+1/2, z+1; (x) x, y+1, z+1/2; (xi) x+1/2, y1/2, z+1; (xii) x, y1, z+1/2; (xiii) x, y+1, z+1/2; (xiv) x, y+1, z1/2; (xv) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O5i0.932.493.420 (3)176
Symmetry code: (i) x, y, z1/2.

Experimental details

Crystal data
Chemical formulaC25H27NO5
Mr421.49
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)33.312 (3), 9.4144 (6), 14.4581 (10)
β (°) 102.3931 (19)
V3)4428.6 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.30 × 0.30
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Rigaku, 1995)
Tmin, Tmax0.753, 0.974
No. of measured, independent and
observed [F2 > 2.0σ(F2)] reflections
20666, 5066, 3965
Rint0.022
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.153, 1.05
No. of reflections5066
No. of parameters288
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.27

Computer programs: RAPID-AUTO (Rigaku, 2006), RAPID-AUTO (Rigaku, 1995), SIR2008 in Il Milione (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···O5i0.9302.49163.420 (3)176.0
Symmetry code: (i) x, y, z1/2.
 

Acknowledgements

Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

References

First citationBurla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609–613.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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