organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(E)-2,2′-[3-(2-Nitro­phen­yl)prop-2-ene-1,1-di­yl]bis­­(3-hy­dr­oxy­cyclo­hex-2-en-1-one)

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

(Received 8 December 2011; accepted 19 December 2011; online 23 December 2011)

In the title compound, C21H21NO6, each of the cyclo­hexenone rings adopts a half-chair conformation. Each of the pairs of hy­droxy and carbonyl O atoms are oriented to allow for the formation of intra­molecular O—H⋯O hydrogen bonds, which are typical of xanthene derivatives.

Related literature

For the biological activity xanthenes and their derivatives and for related structures, see: Lee et al. (2011[Lee, J. K., Min, S.-J., Cho, Y. S., Cha, J. H. & Sato, H. (2011). Acta Cryst. E67, o3407.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21NO6

  • Mr = 383.40

  • Monoclinic, P 21 /n

  • a = 8.0785 (7) Å

  • b = 8.7261 (6) Å

  • c = 26.2616 (17) Å

  • β = 90.829 (3)°

  • V = 1851.1 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.739, Tmax = 0.990

  • 14705 measured reflections

  • 3387 independent reflections

  • 2335 reflections with F2 > 2σ(F2)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.156

  • S = 1.14

  • 3387 reflections

  • 263 parameters

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

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O3 0.82 1.83 2.627 (2) 164
O4—H4⋯O1 0.82 1.78 2.579 (2) 165

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: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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 (Lee et al., 2011). 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 Lee et al., 2011). In the title compound, both cyclohexenone rings in (Fig.1) display half-chair conformation. The nitro group is not co-planar with the benzene ring to which it is attached as seen in the O5—N28—C27—C26 torsion angle of 141.7 (2)°. The hydroxy and carbonyl O atoms face each other and are orientated to allow for the formation of two intramolecular O—H···O hydrogen bonds (Table 1) which are typical of xanthene derivatives.

Related literature top

For the biological activity xanthenes and their derivatives and for related structures, see: Lee et al. (2011).

Experimental top

To solution of 1,3-cyclohexanedione (4.61 mmol), 2-nitrocinnamaldehyde (1.84 mmol) and 4Å MS was added catalytic amounts of L-proline (0.47 mmol) in under nitrogen atmosphere. After stirring for 2 h, The anhydrous ethyl acetate (0.5 ml) was added to a reaction mixture and the solution was stirred for 12 h. The reaction mixture was filtered through pad of celite to remove MS and concentrated. The residue oil was purified by flash column chromatography to afford product which was recrystallized from ethanol to give yellow crystals suitable for X-ray analysis.

Refinement top

All hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.91–0.98 Å and Uiso(H) = 1.2 Ueq(C,O). A rotating model was used for OH groups.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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)-2,2'-[3-(2-Nitrophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxycyclohex-2- en-1-one) top
Crystal data top
C21H21NO6F(000) = 808.00
Mr = 383.40Dx = 1.376 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ynCell parameters from 11386 reflections
a = 8.0785 (7) Åθ = 3.1–27.5°
b = 8.7261 (6) ŵ = 0.10 mm1
c = 26.2616 (17) ÅT = 296 K
β = 90.829 (3)°Block, colourless
V = 1851.1 (3) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2335 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.028
ω scansθmax = 25.4°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 99
Tmin = 0.739, Tmax = 0.990k = 109
14705 measured reflectionsl = 3131
3387 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.0927P)2]
where P = (Fo2 + 2Fc2)/3
3387 reflections(Δ/σ)max = 0.026
263 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.24 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C21H21NO6V = 1851.1 (3) Å3
Mr = 383.40Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.0785 (7) ŵ = 0.10 mm1
b = 8.7261 (6) ÅT = 296 K
c = 26.2616 (17) Å0.30 × 0.20 × 0.10 mm
β = 90.829 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3387 independent reflections
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
2335 reflections with F2 > 2σ(F2)
Tmin = 0.739, Tmax = 0.990Rint = 0.028
14705 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.156H atoms treated by a mixture of independent and constrained refinement
S = 1.14Δρmax = 0.31 e Å3
3387 reflectionsΔρmin = 0.24 e Å3
263 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
O10.45785 (19)0.22041 (16)0.07963 (5)0.0513 (4)
O20.3744 (3)0.49657 (15)0.22975 (5)0.0564 (5)
O30.4192 (2)0.24905 (17)0.28520 (5)0.0529 (5)
O40.5653 (3)0.00381 (17)0.13489 (6)0.0624 (5)
O50.1568 (3)0.3544 (2)0.09158 (9)0.0951 (8)
O60.1984 (3)0.3325 (3)0.01141 (8)0.0992 (8)
N280.1634 (3)0.2779 (3)0.05255 (8)0.0639 (6)
C70.4594 (3)0.1130 (2)0.20880 (7)0.0379 (5)
C80.5667 (3)0.0171 (2)0.18386 (8)0.0453 (5)
C90.6980 (3)0.0716 (3)0.21168 (10)0.0634 (7)
C100.6446 (4)0.1116 (3)0.26478 (10)0.0688 (8)
C110.5914 (4)0.0305 (3)0.29310 (9)0.0646 (8)
C120.4847 (3)0.1371 (3)0.26209 (8)0.0446 (5)
C130.3883 (3)0.4839 (3)0.18035 (8)0.0425 (5)
C140.4224 (4)0.6324 (3)0.15382 (8)0.0550 (6)
C150.3716 (4)0.6286 (3)0.09916 (9)0.0633 (7)
C160.4457 (4)0.4907 (3)0.07317 (9)0.0582 (7)
C170.4256 (3)0.3441 (3)0.10290 (8)0.0430 (5)
C180.3761 (3)0.3469 (2)0.15437 (7)0.0361 (5)
C190.3217 (3)0.2019 (2)0.18202 (7)0.0356 (5)
C200.2077 (3)0.0996 (3)0.15054 (8)0.0429 (5)
C210.0903 (3)0.1434 (3)0.12109 (10)0.0617 (7)
C220.0262 (3)0.0497 (3)0.09109 (7)0.0446 (5)
C230.0204 (3)0.1105 (3)0.09304 (8)0.0524 (6)
C240.1205 (4)0.2002 (3)0.06219 (9)0.0623 (7)
C250.2285 (4)0.1343 (3)0.02791 (9)0.0644 (7)
C260.2383 (3)0.0213 (3)0.02454 (8)0.0585 (7)
C270.1403 (3)0.1105 (3)0.05629 (7)0.0460 (5)
H20.37810.41120.24280.0677*
H40.51660.06750.12090.0748*
H9A0.79880.01120.21350.0760*
H9B0.72170.16490.19310.0760*
H10A0.55320.18370.26300.0825*
H10B0.73560.16030.28310.0825*
H11A0.53120.00030.32310.0775*
H11B0.68950.08560.30450.0775*
H14A0.36320.71420.17080.0660*
H14B0.53980.65480.15640.0660*
H15A0.40830.72150.08250.0759*
H15B0.25180.62410.09640.0759*
H16A0.39360.47850.03990.0699*
H16B0.56270.50910.06800.0699*
H190.25230.23920.20970.0427*
H200.221 (6)0.001 (4)0.1592 (14)0.134 (14)*
H210.083 (5)0.251 (5)0.1152 (14)0.134 (14)*
H230.05290.15770.11570.0629*
H240.11450.30640.06470.0747*
H250.29490.19560.00700.0773*
H260.31020.06700.00110.0701*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0567 (10)0.0544 (9)0.0427 (8)0.0037 (7)0.0023 (7)0.0073 (7)
O20.0823 (13)0.0447 (8)0.0421 (8)0.0114 (8)0.0029 (8)0.0048 (7)
O30.0658 (11)0.0523 (9)0.0403 (8)0.0022 (8)0.0093 (7)0.0046 (7)
O40.0779 (13)0.0533 (10)0.0561 (10)0.0166 (8)0.0095 (9)0.0027 (8)
O50.1043 (18)0.0674 (12)0.1119 (17)0.0224 (11)0.0542 (14)0.0214 (12)
O60.1102 (18)0.1062 (16)0.0808 (13)0.0340 (14)0.0112 (13)0.0364 (12)
N280.0511 (13)0.0701 (13)0.0699 (13)0.0104 (10)0.0181 (10)0.0060 (11)
C70.0336 (11)0.0372 (10)0.0425 (11)0.0030 (8)0.0069 (9)0.0000 (8)
C80.0402 (12)0.0375 (10)0.0581 (13)0.0008 (9)0.0023 (10)0.0005 (10)
C90.0483 (15)0.0515 (13)0.0900 (18)0.0082 (11)0.0104 (13)0.0025 (13)
C100.0639 (18)0.0549 (14)0.0867 (18)0.0059 (12)0.0259 (14)0.0135 (13)
C110.0783 (19)0.0516 (13)0.0629 (15)0.0011 (12)0.0363 (14)0.0062 (11)
C120.0450 (13)0.0394 (11)0.0490 (12)0.0074 (9)0.0129 (10)0.0012 (9)
C130.0407 (12)0.0432 (11)0.0435 (11)0.0072 (9)0.0064 (9)0.0015 (9)
C140.0628 (16)0.0409 (11)0.0612 (14)0.0018 (10)0.0029 (12)0.0036 (10)
C150.0778 (19)0.0517 (13)0.0602 (14)0.0097 (12)0.0019 (13)0.0142 (11)
C160.0691 (17)0.0585 (14)0.0473 (12)0.0079 (12)0.0064 (11)0.0138 (11)
C170.0387 (12)0.0479 (11)0.0422 (11)0.0014 (9)0.0057 (9)0.0026 (9)
C180.0312 (11)0.0406 (10)0.0365 (10)0.0015 (8)0.0053 (8)0.0014 (8)
C190.0315 (11)0.0392 (10)0.0360 (9)0.0003 (8)0.0034 (8)0.0012 (8)
C200.0363 (12)0.0446 (11)0.0474 (11)0.0035 (9)0.0084 (9)0.0029 (10)
C210.0515 (16)0.0474 (13)0.0852 (18)0.0090 (11)0.0331 (13)0.0134 (12)
C220.0351 (12)0.0516 (12)0.0468 (11)0.0007 (9)0.0072 (9)0.0051 (10)
C230.0493 (14)0.0511 (12)0.0564 (13)0.0025 (10)0.0149 (11)0.0054 (10)
C240.0629 (17)0.0584 (14)0.0655 (15)0.0078 (12)0.0021 (12)0.0161 (12)
C250.0573 (17)0.0815 (18)0.0543 (14)0.0151 (13)0.0092 (12)0.0254 (13)
C260.0436 (14)0.0909 (18)0.0406 (12)0.0009 (12)0.0105 (10)0.0045 (12)
C270.0378 (12)0.0574 (13)0.0424 (11)0.0030 (9)0.0059 (9)0.0007 (10)
Geometric parameters (Å, º) top
O1—C171.269 (3)C23—C241.380 (4)
O2—C131.308 (3)C24—C251.371 (4)
O3—C121.270 (3)C25—C261.363 (4)
O4—C81.299 (3)C26—C271.381 (4)
O5—N281.224 (3)O2—H20.820
O6—N281.210 (3)O4—H40.820
N28—C271.476 (3)C9—H9A0.970
C7—C81.377 (3)C9—H9B0.970
C7—C121.427 (3)C10—H10A0.970
C7—C191.520 (3)C10—H10B0.970
C8—C91.495 (4)C11—H11A0.970
C9—C101.507 (4)C11—H11B0.970
C10—C111.512 (4)C14—H14A0.970
C11—C121.500 (4)C14—H14B0.970
C13—C141.499 (3)C15—H15A0.970
C13—C181.379 (3)C15—H15B0.970
C14—C151.488 (4)C16—H16A0.970
C15—C161.511 (4)C16—H16B0.970
C16—C171.509 (3)C19—H190.980
C17—C181.415 (3)C20—H200.91 (4)
C18—C191.527 (3)C21—H210.96 (4)
C19—C201.519 (3)C23—H230.930
C20—C211.273 (4)C24—H240.930
C21—C221.468 (4)C25—H250.930
C22—C231.400 (3)C26—H260.930
C22—C271.393 (3)
O1···O42.579 (2)O2···H20iii3.03 (4)
O1···C73.519 (3)O3···H9Av3.0932
O1···C83.368 (3)O3···H9Bv3.0427
O1···C133.555 (3)O3···H10Bv3.4297
O1···C192.924 (3)O3···H14Aiv2.5908
O1···C202.962 (3)O3···H15Biv3.5910
O1···C213.247 (3)O3···H20iii2.87 (4)
O2···O32.627 (2)O3···H23iii2.7324
O2···C73.462 (3)O4···H14Avi3.1070
O2···C123.367 (3)O4···H14Bvi3.0395
O2···C192.889 (3)O4···H15Avi3.0330
O3···C83.563 (3)O5···H10Biii3.3645
O3···C133.439 (3)O5···H11Aiii2.7557
O3···C183.553 (3)O5···H11Biii3.4070
O3···C192.841 (3)O5···H16Bvii2.7012
O4···C103.587 (3)O5···H24x3.0638
O4···C173.342 (3)O6···H15Aviii3.0095
O4···C183.462 (3)O6···H15Bviii2.8817
O4···C192.949 (3)O6···H16Aviii2.6382
O4···C203.060 (3)O6···H16Bvii2.8973
O5···C212.816 (4)O6···H24x3.5097
O5···C222.860 (3)O6···H24ii3.2529
O5···C263.456 (4)N28···H16Bvii3.0259
O6···C223.510 (3)C7···H2iv3.5002
O6···C262.757 (4)C7···H10Bv3.1650
N28···C212.952 (4)C8···H10Bv3.3457
C7···C102.860 (4)C8···H14Avi3.1288
C7···C133.369 (3)C8···H14Bvi3.2486
C7···C173.443 (3)C9···H11Bix3.1575
C8···C112.875 (4)C9···H14Avi3.4471
C8···C183.349 (3)C9···H14Bvi3.0638
C8···C203.102 (3)C10···H9Aix3.5614
C9···C122.847 (4)C10···H11Bix3.4871
C12···C183.472 (3)C10···H14Bvi3.5913
C13···C162.860 (4)C10···H19iv3.5334
C14···C172.849 (3)C11···H9Bv3.0754
C15···C182.854 (3)C11···H14Bix3.4199
C17···C203.047 (3)C12···H2iv3.5325
C17···C213.266 (4)C12···H9Av3.5861
C18···C213.032 (3)C12···H9Bv3.1492
C20···C232.992 (3)C12···H10Bv3.1173
C22···C252.815 (4)C12···H14Aiv3.4067
C23···C262.751 (4)C13···H10Bv3.4141
C24···C272.720 (4)C13···H11Aiii3.3914
O1···O5i3.335 (3)C13···H11Bv3.5415
O1···O6i3.467 (3)C14···H9Bx3.1573
O1···N28i3.191 (3)C14···H10Ax3.4394
O1···C25ii3.438 (3)C14···H11Bv3.3315
O1···C26i3.353 (3)C14···H20x3.60 (4)
O1···C27i3.449 (3)C15···H23x3.2135
O2···O3iii3.256 (3)C16···H16Axi3.2693
O2···C7iii3.321 (3)C16···H25ii3.5326
O2···C12iii3.159 (3)C17···H25ii3.3230
O2···C19iii3.346 (3)C18···H10Bv3.5206
O2···C20iii3.345 (3)C19···H10Aiii3.5190
O3···O2iv3.256 (3)C20···H2iv3.3300
O3···C9v3.466 (3)C21···H11Aiii3.5807
O3···C13iv3.522 (3)C22···H9Avii3.5700
O3···C14iv3.368 (3)C23···H9Bvii3.4100
O3···C23iii3.510 (3)C23···H15Bvi3.1937
O4···C14vi3.417 (3)C24···H15Bvi3.4815
O4···C22i3.541 (3)C25···H15Axii3.5163
O4···C25i3.478 (3)C26···H4vii3.2613
O4···C26i3.331 (3)C27···H4vii3.2928
O4···C27i3.325 (3)H2···C7iii3.5002
O5···O1vii3.335 (3)H2···C12iii3.5325
O5···C11iii3.430 (4)H2···C20iii3.3300
O5···C16vii3.452 (4)H2···H9Av2.9166
O5···C17vii3.392 (4)H2···H10Aiii3.5826
O6···O1vii3.467 (3)H2···H10Bv3.2636
O6···C15viii3.223 (4)H2···H14Aiv3.4703
O6···C16vii3.597 (4)H2···H19iii3.3010
O6···C16viii3.343 (4)H2···H20iii2.8135
O6···C24ii3.442 (4)H4···C26i3.2613
N28···O1vii3.191 (3)H4···C27i3.2928
C7···O2iv3.321 (3)H4···H14Avi3.5776
C9···O3ix3.466 (3)H4···H15Avi3.2979
C11···O5iv3.430 (4)H4···H26i3.4624
C12···O2iv3.159 (3)H9A···O2ix3.0144
C13···O3iii3.522 (3)H9A···O3ix3.0932
C14···O3iii3.368 (3)H9A···C10v3.5614
C14···O4x3.417 (3)H9A···C12ix3.5861
C15···O6viii3.223 (4)H9A···C22i3.5700
C16···O5i3.452 (4)H9A···H2ix2.9166
C16···O6i3.597 (4)H9A···H10Av3.1552
C16···O6viii3.343 (4)H9A···H10Bv3.0761
C17···O5i3.392 (4)H9A···H11Bix3.5519
C19···O2iv3.346 (3)H9A···H23i3.5489
C20···O2iv3.345 (3)H9B···O3ix3.0427
C22···O4vii3.541 (3)H9B···C11ix3.0754
C23···O3iv3.510 (3)H9B···C12ix3.1492
C24···O6ii3.442 (4)H9B···C14vi3.1573
C25···O1ii3.438 (3)H9B···C23i3.4100
C25···O4vii3.478 (3)H9B···H11Aix3.5713
C26···O1vii3.353 (3)H9B···H11Bix2.2934
C26···O4vii3.331 (3)H9B···H14Avi3.1297
C27···O1vii3.449 (3)H9B···H14Bvi2.3497
C27···O4vii3.325 (3)H9B···H23i3.3834
O1···H41.7797H10A···O2vi3.2557
O1···H16A2.5328H10A···C14vi3.4394
O1···H16B2.6764H10A···C19iv3.5190
O1···H203.45 (4)H10A···H2iv3.5826
O1···H213.20 (4)H10A···H9Aix3.1552
O2···H14A2.4515H10A···H11Bix3.4095
O2···H14B2.7342H10A···H14Avi2.9857
O2···H192.5059H10A···H14Bvi3.1345
O3···H21.8284H10A···H19iv2.6664
O3···H11A2.5527H10A···H21iv3.4421
O3···H11B2.6512H10B···O2ix3.4565
O3···H192.3833H10B···O3ix3.4297
O4···H9A2.7765H10B···O5iv3.3645
O4···H9B2.4191H10B···C7ix3.1650
O4···H202.86 (5)H10B···C8ix3.3457
O5···H212.21 (4)H10B···C12ix3.1173
O6···H213.59 (4)H10B···C13ix3.4141
O6···H262.4996H10B···C18ix3.5206
N28···H212.57 (4)H10B···H2ix3.2636
N28···H262.5635H10B···H9Aix3.0761
C7···H22.8310H10B···H11Bix3.2578
C7···H42.3932H11A···O2iv3.5398
C7···H9A2.9491H11A···O5iv2.7557
C7···H9B3.2507H11A···C13iv3.3914
C7···H10A3.0455H11A···C21iv3.5807
C7···H11A3.2052H11A···H9Bv3.5713
C7···H11B3.1136H11A···H15Biv3.3195
C7···H202.51 (4)H11A···H19iv3.3316
C8···H10A2.7220H11A···H21iv2.8645
C8···H10B3.3077H11A···H23iii3.4653
C8···H11B3.3598H11A···H24iii3.4561
C8···H193.2735H11B···O5iv3.4070
C8···H202.86 (5)H11B···C9v3.1575
C9···H43.0330H11B···C10v3.4871
C9···H11A3.2983H11B···C13ix3.5415
C9···H11B2.7984H11B···C14ix3.3315
C11···H9A2.7222H11B···H9Av3.5519
C11···H9B3.3157H11B···H9Bv2.2934
C12···H22.5899H11B···H10Av3.4095
C12···H9A3.1361H11B···H10Bv3.2578
C12···H10A2.8535H11B···H14Bix2.4774
C12···H10B3.3335H14A···O3iii2.5908
C12···H192.4772H14A···O4x3.1070
C13···H15A3.3079H14A···C8x3.1288
C13···H15B2.7399H14A···C9x3.4471
C13···H16B3.2943H14A···C12iii3.4067
C13···H192.5268H14A···H2iii3.4703
C14···H23.0552H14A···H4x3.5776
C14···H16A3.2842H14A···H9Bx3.1297
C14···H16B2.7552H14A···H10Ax2.9857
C16···H14A3.2958H14A···H19iii3.2957
C16···H14B2.7130H14A···H20x2.7563
C17···H42.5654H14A···H23x3.0853
C17···H14B3.1843H14B···O4x3.0395
C17···H15A3.3387H14B···C8x3.2486
C17···H15B2.8219H14B···C9x3.0638
C17···H193.2829H14B···C10x3.5913
C17···H212.91 (4)H14B···C11v3.4199
C18···H22.3882H14B···H9Bx2.3497
C18···H42.8343H14B···H10Ax3.1345
C18···H14A3.2352H14B···H11Bv2.4774
C18···H14B2.9946H15A···O4x3.0330
C18···H15B3.0226H15A···O6viii3.0095
C18···H16A3.2228H15A···C25xiii3.5163
C18···H16B3.0842H15A···H4x3.2979
C18···H203.28 (4)H15A···H20x3.5105
C18···H212.70 (4)H15A···H23x3.1925
C19···H22.4632H15A···H25xiii3.2146
C19···H42.5495H15A···H26viii2.9669
C19···H212.63 (4)H15B···O3iii3.5910
C20···H42.6397H15B···O6viii2.8817
C20···H232.7218H15B···C23x3.1937
C21···H43.5068H15B···C24x3.4815
C21···H192.7814H15B···H11Aiii3.3195
C21···H232.6486H15B···H23x2.5472
C22···H202.70 (4)H15B···H24x3.1222
C22···H243.2604H16A···O6viii2.6382
C22···H263.2731H16A···C16xi3.2693
C23···H202.76 (4)H16A···H16Axi2.7561
C23···H213.32 (4)H16A···H16Bxi2.8642
C23···H253.2288H16A···H25ii2.8676
C24···H263.2078H16B···O5i2.7012
C25···H233.2212H16B···O6i2.8973
C26···H243.2027H16B···N28i3.0259
C27···H212.66 (4)H16B···H16Axi2.8642
C27···H233.2058H16B···H24xiii3.0668
C27···H253.2123H16B···H25xiii3.2534
H2···H14A3.2518H19···O2iv2.8468
H2···H14B3.3843H19···C10iii3.5334
H2···H192.0038H19···H2iv3.3010
H4···H9A3.3788H19···H10Aiii2.6664
H4···H9B3.2183H19···H11Aiii3.3316
H4···H193.5186H19···H14Aiv3.2957
H4···H202.6720H20···O2iv3.03 (4)
H9A···H10A2.8225H20···O3iv2.87 (4)
H9A···H10B2.3061H20···C14vi3.60 (4)
H9A···H11B2.6954H20···H2iv2.8135
H9B···H10A2.3074H20···H14Avi2.7563
H9B···H10B2.3641H20···H15Avi3.5105
H10A···H11A2.2564H21···H10Aiii3.4421
H10A···H11B2.8078H21···H11Aiii2.8645
H10B···H11A2.4148H23···O3iv2.7324
H10B···H11B2.2502H23···C15vi3.2135
H14A···H15A2.3527H23···H9Avii3.5489
H14A···H15B2.2789H23···H9Bvii3.3834
H14B···H15A2.2751H23···H11Aiv3.4653
H14B···H15B2.8045H23···H14Avi3.0853
H14B···H16B2.6552H23···H15Avi3.1925
H15A···H16A2.3988H23···H15Bvi2.5472
H15A···H16B2.2686H24···O5vi3.0638
H15B···H16A2.2743H24···O6vi3.5097
H15B···H16B2.8148H24···O6ii3.2529
H15B···H213.5649H24···H11Aiv3.4561
H19···H202.4879H24···H15Bvi3.1222
H19···H212.8185H24···H16Bxii3.0668
H20···H212.72 (6)H25···O1ii2.6218
H20···H232.2321H25···C16ii3.5326
H21···H233.5786H25···C17ii3.3230
H23···H242.2928H25···H15Axii3.2146
H24···H252.2988H25···H16Aii2.8676
H25···H262.3001H25···H16Bxii3.2534
O1···H25ii2.6218H25···H26xiv3.3855
O1···H26i3.1092H26···O1vii3.1092
O1···H26ii3.4836H26···O1ii3.4836
O2···H9Av3.0144H26···H4vii3.4624
O2···H10Ax3.2557H26···H15Aviii2.9669
O2···H10Bv3.4565H26···H25xiv3.3855
O2···H11Aiii3.5398H26···H26xiv3.2819
O2···H19iii2.8468
O5—N28—O6122.7 (3)C8—C9—H9B109.396
O5—N28—C27118.7 (2)C10—C9—H9A109.398
O6—N28—C27118.5 (2)C10—C9—H9B109.398
C8—C7—C12118.27 (18)H9A—C9—H9B108.010
C8—C7—C19123.45 (17)C9—C10—H10A109.530
C12—C7—C19118.18 (17)C9—C10—H10B109.527
O4—C8—C7124.04 (19)C11—C10—H10A109.524
O4—C8—C9114.01 (19)C11—C10—H10B109.522
C7—C8—C9121.9 (2)H10A—C10—H10B108.089
C8—C9—C10111.2 (2)C10—C11—H11A108.754
C9—C10—C11110.6 (2)C10—C11—H11B108.754
C10—C11—C12114.0 (2)C12—C11—H11A108.752
O3—C12—C7121.82 (18)C12—C11—H11B108.748
O3—C12—C11117.23 (19)H11A—C11—H11B107.664
C7—C12—C11120.94 (18)C13—C14—H14A109.140
O2—C13—C14114.00 (17)C13—C14—H14B109.137
O2—C13—C18123.87 (18)C15—C14—H14A109.150
C14—C13—C18122.12 (19)C15—C14—H14B109.159
C13—C14—C15112.29 (19)H14A—C14—H14B107.867
C14—C15—C16110.4 (2)C14—C15—H15A109.576
C15—C16—C17113.3 (2)C14—C15—H15B109.565
O1—C17—C16116.59 (19)C16—C15—H15A109.587
O1—C17—C18122.50 (18)C16—C15—H15B109.585
C16—C17—C18120.91 (18)H15A—C15—H15B108.120
C13—C18—C17117.93 (18)C15—C16—H16A108.917
C13—C18—C19120.13 (17)C15—C16—H16B108.926
C17—C18—C19121.81 (16)C17—C16—H16A108.930
C7—C19—C18115.44 (16)C17—C16—H16B108.927
C7—C19—C20112.70 (15)H16A—C16—H16B107.735
C18—C19—C20113.87 (16)C7—C19—H19104.427
C19—C20—C21126.5 (2)C18—C19—H19104.434
C20—C21—C22128.7 (2)C20—C19—H19104.428
C21—C22—C23121.05 (19)C19—C20—H20111 (3)
C21—C22—C27123.57 (19)C21—C20—H20122 (3)
C23—C22—C27115.21 (19)C20—C21—H21116 (3)
C22—C23—C24121.7 (2)C22—C21—H21115 (3)
C23—C24—C25120.6 (3)C22—C23—H23119.134
C24—C25—C26119.7 (3)C24—C23—H23119.136
C25—C26—C27119.3 (3)C23—C24—H24119.669
N28—C27—C22120.16 (19)C25—C24—H24119.681
N28—C27—C26116.5 (2)C24—C25—H25120.135
C22—C27—C26123.3 (2)C26—C25—H25120.133
C13—O2—H2109.476C25—C26—H26120.338
C8—O4—H4109.473C27—C26—H26120.342
C8—C9—H9A109.394
O5—N28—C27—C2237.3 (3)C13—C14—C15—C1652.0 (3)
O5—N28—C27—C26141.7 (2)C14—C15—C16—C1747.0 (3)
O6—N28—C27—C22147.3 (2)C15—C16—C17—O1167.85 (19)
O6—N28—C27—C2633.7 (3)C15—C16—C17—C1813.3 (3)
C8—C7—C12—O3162.73 (18)O1—C17—C18—C13162.33 (17)
C8—C7—C12—C1116.9 (3)O1—C17—C18—C1913.6 (3)
C12—C7—C8—O4173.91 (17)C16—C17—C18—C1316.5 (3)
C12—C7—C8—C95.3 (3)C16—C17—C18—C19167.59 (18)
C8—C7—C19—C1878.8 (3)C13—C18—C19—C786.4 (2)
C8—C7—C19—C2054.4 (3)C13—C18—C19—C20140.88 (17)
C19—C7—C8—O42.3 (3)C17—C18—C19—C789.4 (2)
C19—C7—C8—C9178.46 (15)C17—C18—C19—C2043.3 (3)
C12—C7—C19—C1897.47 (19)C7—C19—C20—C21174.18 (18)
C12—C7—C19—C20129.31 (17)C18—C19—C20—C2140.2 (3)
C19—C7—C12—O313.7 (3)C19—C20—C21—C22178.03 (19)
C19—C7—C12—C11166.64 (15)C20—C21—C22—C231.3 (4)
O4—C8—C9—C10150.09 (17)C20—C21—C22—C27173.7 (3)
C7—C8—C9—C1030.6 (3)C21—C22—C23—C24174.94 (19)
C8—C9—C10—C1153.8 (3)C21—C22—C27—N287.7 (3)
C9—C10—C11—C1243.6 (3)C21—C22—C27—C26173.38 (18)
C10—C11—C12—O3171.66 (19)C23—C22—C27—N28177.06 (17)
C10—C11—C12—C78.7 (3)C23—C22—C27—C261.9 (3)
O2—C13—C14—C15156.97 (18)C27—C22—C23—C240.4 (3)
O2—C13—C18—C17167.73 (18)C22—C23—C24—C250.7 (4)
O2—C13—C18—C198.3 (3)C23—C24—C25—C260.5 (4)
C14—C13—C18—C1711.0 (3)C24—C25—C26—C270.8 (4)
C14—C13—C18—C19172.96 (18)C25—C26—C27—N28176.85 (19)
C18—C13—C14—C1524.2 (3)C25—C26—C27—C222.1 (4)
Symmetry codes: (i) x+1, y, z; (ii) x, y, z; (iii) x+1/2, y+1/2, z+1/2; (iv) x+1/2, y1/2, z+1/2; (v) x+3/2, y+1/2, z+1/2; (vi) x, y1, z; (vii) x1, y, z; (viii) x, y+1, z; (ix) x+3/2, y1/2, z+1/2; (x) x, y+1, z; (xi) x+1, y+1, z; (xii) x1, y1, z; (xiii) x+1, y+1, z; (xiv) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.821.832.627 (2)164
O4—H4···O10.821.782.579 (2)165

Experimental details

Crystal data
Chemical formulaC21H21NO6
Mr383.40
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)8.0785 (7), 8.7261 (6), 26.2616 (17)
β (°) 90.829 (3)
V3)1851.1 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Rigaku, 1995)
Tmin, Tmax0.739, 0.990
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
14705, 3387, 2335
Rint0.028
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.156, 1.14
No. of reflections3387
No. of parameters263
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.31, 0.24

Computer programs: RAPID-AUTO (Rigaku, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.8201.8282.627 (2)164.2
O4—H4···O10.8201.7802.579 (2)164.5
 

Acknowledgements

This work was supported financially by a grant from the Korea Institute of Science and Technology (KIST).

References

First citationLee, J. K., Min, S.-J., Cho, Y. S., Cha, J. H. & Sato, H. (2011). Acta Cryst. E67, o3407.  Web of Science CSD CrossRef IUCr Journals
First citationRigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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