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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

9-[(E)-2-(4-Chloro­phen­yl)ethen­yl]-3,3,6,6-tetra­methyl-2,3,4,5,6,7,8,9-octa­hydro-1H-xanthene-1,8-dione

aAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul, 136-791, South Korea, bCenter for Neuro-Medicine, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul, 136-791, South Korea, and cDrug Discovery Platform Technology Team, Korea Research Institute, of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, South Korea
*Correspondence e-mail: j9601@kist.re.kr

(Received 2 September 2013; accepted 9 September 2013; online 18 September 2013)

In the title compound, C25H27ClO3, each of the cyclo­hexenone rings adopts an envelope 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. The C=C double bond is in the trans conformation. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into chains running parallel to the b axis.

Related literature

For the synthesis and the crystal structures of xanthene derivatives studied recently by our group, see: Cha et al. (2013[Cha, J. H., Lee, J. K., Min, S.-J., Cho, Y. S. & Park, J. (2013). Acta Cryst. E69, o1347.]); Lee et al. (2012[Lee, J. K., Min, S.-J., Cho, Y. S., Lee, K. S. & Cha, J. H. (2012). Acta Cryst. E68, o1947.], 2013[Lee, J. K., Min, S.-J., Cho, Y. S., Cha, J. H. & Won, S. O. (2013). Acta Cryst. E69, o985.]).

[Scheme 1]

Experimental

Crystal data
  • C25H27ClO3

  • Mr = 410.94

  • Monoclinic, P 21 /n

  • a = 5.9686 (4) Å

  • b = 18.7567 (13) Å

  • c = 20.1089 (13) Å

  • β = 100.9322 (18)°

  • V = 2210.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 296 K

  • 0.40 × 0.10 × 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 = 0.629, Tmax = 0.981

  • 21185 measured reflections

  • 5042 independent reflections

  • 2842 reflections with F2 > 2.0σ(F2)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.194

  • S = 1.11

  • 5042 reflections

  • 274 parameters

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

  • Δρmax = 0.49 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C23—H23B⋯O2i 0.96 2.53 3.461 (4) 163
Symmetry code: (i) [-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\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: 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., 2013; Lee et al., 2012, 2013). We present here the crystal structure of the title compound (I) (Fig. 1).

The starting material, (E)-2.2-(3-(4-chlorophenyl)prop-2-ene-1,1-diyl) bis(3-hydroxy-5,5-δimethylcyclohex-2-enone) was prepared according to the reported method (Cha et al., 2013). In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related structures (Lee et al., 2013).

The torsion angle C2—C1—C14—C15 between the benzene ring (C16 - C21) system and the pyran ring (C1—C2—C7—O3—C8—C13) is 41.74 (2)°. The double bond [C14=C15] is in the trans conformation. All two cyclohexenone rings in (Fig.1) display envelope conformation, whereas the pyran ring adopts a boat conformation.

In the crystal, weak intermolecular C—H···O hydrogen bonds link molecules into chains running parallel to the b-axis.

Related literature top

For the synthesis and the crystal structures of xanthene derivatives studied recently by our group, see: Cha et al. (2013); Lee et al. (2012, 2013).

Experimental top

To solution of (E)-2.2-(3-(4-Chlorophenyl)prop-2-ene-1,1-diyl)bis (3-hydroxy-5,5-dimethylcyclohex-2-enone) (1.25 mmol) was added methanol and catalytic amounts of sulfuric acid in under nitrogen atmosphere. After stirring for 4 h, the progress of reaction was monitored by TLC. 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 solid residue was purified by recrystallization from ethanol and methylene chloride (1:7 v/v) to afford (yield 95%) 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 = 0.86–0.98 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: 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 ellipsoids.
9-[(E)-2-(4-Chlorophenyl)ethenyl]-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione top
Crystal data top
C25H27ClO3F(000) = 872.00
Mr = 410.94Dx = 1.235 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ynCell parameters from 12401 reflections
a = 5.9686 (4) Åθ = 3.0–27.5°
b = 18.7567 (13) ŵ = 0.20 mm1
c = 20.1089 (13) ÅT = 296 K
β = 100.9322 (18)°Block, colorless
V = 2210.4 (3) Å30.40 × 0.10 × 0.10 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2842 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.042
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR, Rigaku, 1995)
h = 77
Tmin = 0.629, Tmax = 0.981k = 2424
21185 measured reflectionsl = 2626
5042 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0909P)2 + 0.3774P]
where P = (Fo2 + 2Fc2)/3
5042 reflections(Δ/σ)max < 0.001
274 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.37 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H27ClO3V = 2210.4 (3) Å3
Mr = 410.94Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.9686 (4) ŵ = 0.20 mm1
b = 18.7567 (13) ÅT = 296 K
c = 20.1089 (13) Å0.40 × 0.10 × 0.10 mm
β = 100.9322 (18)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5042 independent reflections
Absorption correction: multi-scan
(ABSCOR, Rigaku, 1995)
2842 reflections with F2 > 2.0σ(F2)
Tmin = 0.629, Tmax = 0.981Rint = 0.042
21185 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.49 e Å3
5042 reflectionsΔρmin = 0.37 e Å3
274 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
Cl10.69966 (17)0.07641 (5)1.05177 (4)0.0940 (4)
O10.7005 (3)0.30837 (9)0.63125 (9)0.0555 (5)
O21.1309 (4)0.09617 (11)0.64406 (11)0.0807 (7)
O31.4226 (3)0.33059 (11)0.77323 (11)0.0772 (7)
C11.0997 (4)0.23354 (12)0.70199 (12)0.0475 (6)
C21.0643 (4)0.31308 (12)0.70432 (11)0.0445 (6)
C31.2468 (4)0.35734 (14)0.74179 (14)0.0553 (7)
C41.2148 (5)0.43693 (14)0.73819 (14)0.0574 (7)
C50.9668 (4)0.46069 (12)0.73584 (12)0.0465 (6)
C60.8129 (4)0.42116 (12)0.67791 (12)0.0476 (6)
C70.8714 (4)0.34484 (12)0.67331 (11)0.0433 (5)
C80.7416 (4)0.23900 (13)0.61490 (12)0.0502 (6)
C90.5527 (5)0.21123 (15)0.56166 (13)0.0594 (7)
C100.6217 (5)0.14590 (12)0.52433 (12)0.0497 (6)
C110.7561 (5)0.09527 (13)0.57644 (14)0.0623 (7)
C120.9542 (5)0.12910 (13)0.62313 (13)0.0560 (7)
C130.9267 (4)0.20277 (13)0.64482 (11)0.0478 (6)
C141.0738 (5)0.19832 (13)0.76848 (12)0.0502 (6)
C150.9167 (5)0.21453 (14)0.80290 (14)0.0540 (7)
C160.8714 (4)0.18080 (12)0.86494 (12)0.0477 (6)
C170.6773 (5)0.20050 (14)0.88966 (13)0.0563 (7)
C180.6241 (5)0.16827 (14)0.94691 (14)0.0607 (7)
C190.7662 (5)0.11714 (15)0.98006 (13)0.0587 (7)
C200.9630 (5)0.09732 (14)0.95799 (14)0.0605 (7)
C211.0122 (4)0.12912 (13)0.90070 (13)0.0539 (6)
C220.9015 (5)0.44069 (16)0.80400 (14)0.0677 (8)
C230.9392 (6)0.54004 (15)0.72602 (18)0.0790 (9)
C240.4088 (5)0.10911 (16)0.48605 (15)0.0692 (8)
C250.7708 (5)0.16842 (16)0.47402 (14)0.0694 (8)
H11.25330.22400.69360.0570*
H4A1.26500.45460.69810.0689*
H4B1.31100.45840.77740.0689*
H6A0.65600.42490.68400.0572*
H6B0.82340.44430.63550.0572*
H9A0.50290.24880.52900.0713*
H9B0.42440.19860.58260.0713*
H11A0.65320.07530.60350.0747*
H11B0.81290.05620.55270.0747*
H170.58190.23580.86750.0676*
H180.49300.18140.96250.0728*
H201.06030.06320.98140.0726*
H211.14370.11560.88550.0647*
H22A0.74820.45600.80420.0813*
H22B1.00410.46370.84020.0813*
H22C0.91160.38990.81000.0813*
H23A0.97510.55310.68310.0948*
H23B1.04040.56430.76160.0948*
H23C0.78450.55320.72710.0948*
H24A0.45210.06800.46310.0831*
H24B0.32530.14150.45350.0831*
H24C0.31460.09460.51740.0831*
H25A0.90610.19140.49790.0833*
H25B0.68730.20090.44160.0833*
H25C0.81260.12710.45100.0833*
H141.170 (5)0.1623 (16)0.7859 (15)0.073 (9)*
H150.820 (5)0.2468 (16)0.7866 (15)0.069 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1078 (7)0.1136 (8)0.0698 (6)0.0045 (6)0.0402 (5)0.0178 (5)
O10.0479 (9)0.0512 (11)0.0609 (11)0.0086 (8)0.0067 (8)0.0155 (8)
O20.0945 (16)0.0552 (12)0.0814 (15)0.0261 (11)0.0114 (12)0.0069 (10)
O30.0510 (11)0.0622 (13)0.1048 (17)0.0042 (9)0.0200 (11)0.0069 (11)
C10.0466 (13)0.0483 (14)0.0452 (13)0.0060 (11)0.0026 (10)0.0004 (10)
C20.0430 (12)0.0453 (13)0.0438 (12)0.0024 (10)0.0042 (10)0.0012 (10)
C30.0445 (13)0.0549 (15)0.0628 (16)0.0012 (12)0.0011 (12)0.0043 (12)
C40.0513 (14)0.0562 (16)0.0638 (16)0.0055 (12)0.0085 (13)0.0025 (13)
C50.0452 (12)0.0452 (13)0.0476 (13)0.0006 (10)0.0046 (10)0.0022 (10)
C60.0459 (13)0.0447 (13)0.0508 (13)0.0036 (10)0.0053 (11)0.0010 (10)
C70.0391 (11)0.0488 (13)0.0411 (12)0.0004 (10)0.0048 (10)0.0012 (10)
C80.0560 (14)0.0462 (14)0.0476 (13)0.0030 (11)0.0076 (11)0.0064 (11)
C90.0561 (15)0.0594 (16)0.0573 (15)0.0022 (13)0.0029 (13)0.0121 (13)
C100.0570 (14)0.0444 (13)0.0465 (13)0.0044 (11)0.0069 (11)0.0026 (11)
C110.0803 (19)0.0438 (14)0.0594 (16)0.0041 (13)0.0049 (15)0.0004 (12)
C120.0721 (17)0.0468 (14)0.0474 (14)0.0072 (13)0.0065 (13)0.0039 (11)
C130.0533 (14)0.0469 (13)0.0419 (12)0.0055 (11)0.0057 (11)0.0002 (10)
C140.0568 (14)0.0438 (14)0.0465 (13)0.0101 (12)0.0008 (12)0.0034 (11)
C150.0509 (14)0.0466 (15)0.0622 (16)0.0073 (12)0.0050 (13)0.0095 (12)
C160.0491 (13)0.0408 (13)0.0517 (13)0.0001 (10)0.0061 (11)0.0020 (10)
C170.0530 (14)0.0498 (14)0.0639 (16)0.0049 (12)0.0054 (13)0.0021 (12)
C180.0549 (15)0.0623 (17)0.0669 (17)0.0020 (13)0.0167 (14)0.0144 (14)
C190.0643 (16)0.0610 (16)0.0529 (15)0.0059 (13)0.0165 (13)0.0062 (13)
C200.0640 (16)0.0597 (17)0.0574 (16)0.0091 (13)0.0104 (14)0.0086 (13)
C210.0518 (14)0.0550 (15)0.0566 (15)0.0062 (12)0.0142 (12)0.0048 (12)
C220.0724 (18)0.0711 (19)0.0613 (17)0.0038 (15)0.0167 (15)0.0112 (14)
C230.081 (2)0.0485 (17)0.097 (3)0.0016 (15)0.0104 (18)0.0047 (16)
C240.0748 (19)0.0643 (18)0.0657 (18)0.0121 (15)0.0059 (15)0.0137 (14)
C250.0766 (19)0.075 (2)0.0565 (16)0.0090 (16)0.0124 (15)0.0023 (14)
Geometric parameters (Å, º) top
Cl1—C191.743 (3)C19—C201.383 (5)
O1—C71.377 (3)C20—C211.377 (4)
O1—C81.375 (3)C1—H10.980
O2—C121.226 (4)C4—H4A0.970
O3—C31.225 (3)C4—H4B0.970
C1—C21.509 (4)C6—H6A0.970
C1—C131.507 (3)C6—H6B0.970
C1—C141.525 (4)C9—H9A0.970
C2—C31.460 (4)C9—H9B0.970
C2—C71.341 (3)C11—H11A0.970
C3—C41.505 (4)C11—H11B0.970
C4—C51.538 (4)C14—H140.91 (3)
C5—C61.531 (3)C15—H150.86 (3)
C5—C221.541 (4)C17—H170.930
C5—C231.506 (4)C18—H180.930
C6—C71.481 (4)C20—H200.930
C8—C91.494 (4)C21—H210.930
C8—C131.339 (4)C22—H22A0.960
C9—C101.534 (4)C22—H22B0.960
C10—C111.525 (4)C22—H22C0.960
C10—C241.521 (4)C23—H23A0.960
C10—C251.528 (5)C23—H23B0.960
C11—C121.504 (4)C23—H23C0.960
C12—C131.468 (4)C24—H24A0.960
C14—C151.303 (4)C24—H24B0.960
C15—C161.469 (4)C24—H24C0.960
C16—C171.395 (4)C25—H25A0.960
C16—C211.390 (4)C25—H25B0.960
C17—C181.389 (4)C25—H25C0.960
C18—C191.367 (4)
O1···C12.896 (3)O3···H17iii2.6407
O2···C12.848 (4)O3···H22Aiii3.0396
O2···C83.522 (4)O3···H22Ciii3.0799
O2···C143.220 (4)O3···H15iii2.82 (3)
O3···C12.834 (3)C1···H9Biii3.4232
O3···C73.525 (3)C3···H6Aiii3.1619
O3···C143.228 (4)C3···H22Aiii3.5402
C2···C52.923 (4)C4···H6Aiii3.0432
C2···C82.750 (3)C4···H22Aiii3.2287
C2···C152.964 (4)C6···H4Ai3.4288
C2···C223.381 (4)C8···H1i3.5812
C3···C62.920 (4)C9···H1i3.4761
C3···C143.234 (4)C11···H22Aiv3.5505
C3···C223.039 (5)C11···H22Biv3.5075
C4···C72.806 (4)C11···H24Ax3.3429
C7···C132.759 (4)C12···H9Biii3.3330
C7···C143.435 (4)C12···H24Ciii3.3615
C7···C153.546 (4)C13···H9Biii3.4364
C7···C223.161 (4)C14···H17iii3.3706
C8···C112.811 (4)C14···H23Bii3.5372
C8···C143.425 (4)C14···H23Civ3.4729
C8···C253.162 (4)C15···H23Civ3.2686
C9···C122.919 (4)C15···H25Bviii3.3457
C10···C132.941 (3)C16···H9Aviii3.5021
C12···C143.154 (4)C16···H23Aiv3.1917
C12···C253.080 (4)C16···H23Civ3.0596
C13···C153.198 (4)C16···H25Bviii3.1228
C13···C253.445 (4)C17···H9Aviii3.2356
C14···C213.043 (4)C17···H21i3.5474
C16···C192.780 (4)C17···H23Aiv3.1784
C17···C202.767 (4)C17···H24Bviii3.2834
C18···C212.754 (4)C17···H25Avii3.5780
O1···O3i3.588 (3)C17···H25Bviii3.5459
O2···C23ii3.461 (4)C17···H14i3.41 (3)
O3···O1iii3.588 (3)C18···H9Aviii2.9736
O3···C17iii3.521 (4)C18···H21i3.0630
O3···C22iii3.485 (4)C18···H23Aiv3.3557
C16···C23iv3.531 (4)C18···H25Avii3.1900
C17···O3i3.521 (4)C18···H25Bvii3.5671
C22···O3i3.485 (4)C19···H9Aviii2.9604
C23···O2v3.461 (4)C19···H20ix3.5788
C23···C16vi3.531 (4)C19···H23Aiv3.5336
Cl1···H182.7888C20···H9Aviii3.2097
Cl1···H202.8027C20···H18iii3.5198
O1···H6A2.4660C20···H20ix3.2609
O1···H6B2.6503C20···H23Aiv3.5721
O1···H9A2.4389C21···H9Aviii3.4585
O1···H9B2.7017C21···H18iii3.0641
O1···H153.28 (3)C21···H23Aiv3.3869
O2···H12.6456C21···H23Civ3.1681
O2···H11A2.8399C21···H25Bviii3.4071
O2···H11B2.4933C22···H4Bi3.4792
O2···H25A3.4838C22···H11Avi3.1893
O2···H143.08 (3)C22···H24Aviii3.1594
O3···H12.6400C22···H24Bviii3.4848
O3···H4A2.8353C23···H14v3.31 (3)
O3···H4B2.4940C24···H11Bx3.4035
O3···H22C3.4562C24···H22Bxi3.3790
O3···H143.53 (3)C24···H22Cxi3.5428
C1···H152.61 (4)C24···H24Ax3.5277
C2···H4A2.9246C24···H25Ai3.4227
C2···H4B3.3067C24···H25Ci3.5105
C2···H6A3.1828C25···H17xii3.5745
C2···H6B3.0478C25···H18xii3.1411
C2···H22C2.8571C25···H24Biii3.4493
C2···H143.27 (3)C25···H24Ciii3.4838
C2···H152.71 (3)H1···O1iii3.5308
C3···H12.6851H1···C8iii3.5812
C3···H6B3.4013H1···C9iii3.4761
C3···H22B3.3286H1···H9Biii2.6676
C3···H22C2.7018H1···H23Bii3.2982
C3···H153.53 (3)H1···H15iii3.5668
C4···H6A3.3141H4A···Cl1xii2.9523
C4···H6B2.8128H4A···C6iii3.4288
C4···H22A3.3239H4A···H6Aiii2.4673
C4···H22B2.6496H4A···H21v3.5481
C4···H22C2.6700H4A···H22Aiii3.2460
C4···H23A2.7246H4A···H23Ciii3.5624
C4···H23B2.6835H4B···O2v3.0143
C4···H23C3.3444H4B···C22iii3.4792
C6···H4A2.7247H4B···H6Aiii3.1024
C6···H4B3.3272H4B···H22Aiii2.5631
C6···H22A2.7202H6A···Cl1xi3.4267
C6···H22B3.3433H6A···O3i3.0391
C6···H22C2.6749H6A···C3i3.1619
C6···H23A2.6530H6A···C4i3.0432
C6···H23B3.3202H6A···H4Ai2.4673
C6···H23C2.6843H6A···H4Bi3.1024
C7···H13.1850H6B···Cl1xii3.0761
C7···H4A3.0922H6B···H20xi3.2003
C7···H22A3.5430H9A···C16xi3.5021
C7···H22C2.8428H9A···C17xi3.2356
C7···H152.99 (3)H9A···C18xi2.9736
C8···H13.1742H9A···C19xi2.9604
C8···H11A3.1166H9A···C20xi3.2097
C8···H25A2.8589H9A···C21xi3.4585
C8···H25B3.5123H9A···H18xi3.3500
C8···H153.40 (3)H9B···O2i3.0186
C9···H11A2.7160H9B···C1i3.4232
C9···H11B3.3174H9B···C12i3.3330
C9···H24A3.3259H9B···C13i3.4364
C9···H24B2.6757H9B···H1i2.6676
C9···H24C2.6673H9B···H25Ai3.2393
C9···H25A2.6941H11A···O2i3.3915
C9···H25B2.6929H11A···C22iv3.1893
C9···H25C3.3406H11A···H22Aiv2.8952
C11···H9A3.3070H11A···H22Biv2.6364
C11···H9B2.7901H11A···H23Biv3.1498
C11···H24A2.6805H11A···H23Civ3.3821
C11···H24B3.3260H11A···H24Ax3.0146
C11···H24C2.6775H11B···C24x3.4035
C11···H25A2.6618H11B···H22Aiv3.5133
C11···H25B3.3206H11B···H22Biv3.5745
C11···H25C2.6749H11B···H24Ax2.7995
C12···H12.7208H11B···H24Ciii3.2856
C12···H9B3.3743H11B···H24Cx3.1883
C12···H25A2.7419H17···O3i2.6407
C12···H25C3.4042H17···C14i3.3706
C12···H143.34 (3)H17···C25vii3.5745
C13···H9A3.2143H17···H21i3.5230
C13···H9B3.0225H17···H23Aiv3.5712
C13···H11A2.9252H17···H24Bviii3.0741
C13···H11B3.3124H17···H25Avii3.2996
C13···H25A2.9417H17···H25Bvii3.2416
C13···H143.03 (3)H17···H14i3.0182
C13···H153.15 (3)H18···C20i3.5198
C14···H212.7825H18···C21i3.0641
C15···H13.2524H18···C25vii3.1411
C15···H172.6117H18···H9Aviii3.3500
C15···H212.6798H18···H20i3.4782
C15···H22C3.2936H18···H21i2.6544
C16···H183.2612H18···H25Avii2.5705
C16···H203.2588H18···H25Bvii2.8446
C16···H142.62 (4)H20···Cl1ix3.1167
C17···H213.2218H20···C19ix3.5788
C17···H152.54 (3)H20···C20ix3.2609
C18···H203.2342H20···H6Bviii3.2003
C19···H173.2162H20···H18iii3.4782
C19···H213.2126H20···H20ix2.6271
C20···H183.2345H21···C17iii3.5474
C21···H173.2241H21···C18iii3.0630
C21···H142.72 (4)H21···H4Aii3.5481
C21···H153.23 (3)H21···H17iii3.5230
C22···H4A3.3256H21···H18iii2.6544
C22···H4B2.6204H21···H23Aii3.1049
C22···H6A2.5916H21···H23Civ3.2903
C22···H6B3.3326H22A···O3i3.0396
C22···H23A3.3103H22A···C3i3.5402
C22···H23B2.6569H22A···C4i3.2287
C22···H23C2.6320H22A···C11vi3.5505
C23···H4A2.6603H22A···H4Ai3.2460
C23···H4B2.7322H22A···H4Bi2.5631
C23···H6A2.7737H22A···H11Avi2.8952
C23···H6B2.5571H22A···H11Bvi3.5133
C23···H22A2.6338H22A···H24Aviii3.2266
C23···H22B2.6719H22A···H24Bviii3.4712
C23···H22C3.3035H22B···O2v3.2809
C24···H9A2.7818H22B···C11vi3.5075
C24···H9B2.5546H22B···C24viii3.3790
C24···H11A2.6079H22B···H11Avi2.6364
C24···H11B2.7150H22B···H11Bvi3.5745
C24···H25A3.3138H22B···H24Aviii2.6154
C24···H25B2.6629H22B···H24Bviii3.3381
C24···H25C2.6575H22B···H25Cviii3.1132
C25···H9A2.5925H22C···O3i3.0799
C25···H9B3.3273H22C···C24viii3.5428
C25···H11A3.3190H22C···H24Aviii3.1416
C25···H11B2.6161H22C···H24Bviii3.0828
C25···H24A2.6568H22C···H25Bviii3.3101
C25···H24B2.6603H22C···H25Cviii3.3602
C25···H24C3.3152H23A···C16vi3.1917
H1···H142.3218H23A···C17vi3.1784
H1···H153.4931H23A···C18vi3.3557
H4A···H6B2.7040H23A···C19vi3.5336
H4A···H22B3.5081H23A···C20vi3.5721
H4A···H22C3.5755H23A···C21vi3.3869
H4A···H23A2.5103H23A···H17vi3.5712
H4A···H23B2.8831H23A···H21v3.1049
H4A···H23C3.5521H23A···H14v2.9290
H4B···H22A3.5021H23B···O2v2.5279
H4B···H22B2.4168H23B···C14v3.5372
H4B···H22C2.8907H23B···H1v3.2982
H4B···H23A3.0541H23B···H11Avi3.1498
H4B···H23B2.5417H23B···H14v2.8139
H4B···H23C3.5853H23C···C14vi3.4729
H6A···H22A2.4458H23C···C15vi3.2686
H6A···H22B3.4981H23C···C16vi3.0596
H6A···H22C2.7774H23C···C21vi3.1681
H6A···H23A3.0704H23C···H4Ai3.5624
H6A···H23C2.6228H23C···H11Avi3.3821
H6B···H22A3.5129H23C···H21vi3.2903
H6B···H22C3.5968H23C···H14vi3.3666
H6B···H23A2.3609H24A···C11x3.3429
H6B···H23B3.4547H24A···C22xi3.1594
H6B···H23C2.7893H24A···C24x3.5277
H9A···H24B2.6196H24A···H11Ax3.0146
H9A···H24C3.0943H24A···H11Bx2.7995
H9A···H25A2.8127H24A···H22Axi3.2266
H9A···H25B2.4175H24A···H22Bxi2.6154
H9A···H25C3.4909H24A···H22Cxi3.1416
H9B···H11A2.6782H24A···H24Ax2.9515
H9B···H24A3.4582H24A···H24Cx3.3448
H9B···H24B2.7656H24B···C17xi3.2834
H9B···H24C2.3718H24B···C22xi3.4848
H9B···H25B3.4917H24B···C25i3.4493
H11A···H24A2.8548H24B···H17xi3.0741
H11A···H24B3.4969H24B···H22Axi3.4712
H11A···H24C2.4264H24B···H22Bxi3.3381
H11A···H25A3.5705H24B···H22Cxi3.0828
H11A···H25C3.5156H24B···H25Ai2.9632
H11B···H24A2.5422H24B···H25Ci3.0634
H11B···H24B3.5782H24C···O2i2.9582
H11B···H24C3.0115H24C···C12i3.3615
H11B···H25A2.8613H24C···C25i3.4838
H11B···H25B3.5047H24C···H11Bi3.2856
H11B···H25C2.4387H24C···H11Bx3.1883
H17···H182.3158H24C···H24Ax3.3448
H17···H152.3633H24C···H25Ai3.0052
H20···H212.3019H24C···H25Ci3.1006
H21···H142.2169H25A···C17xii3.5780
H21···H153.5043H25A···C18xii3.1900
H22A···H23A3.5125H25A···C24iii3.4227
H22A···H23B2.9104H25A···H9Biii3.2393
H22A···H23C2.4305H25A···H17xii3.2996
H22B···H23A3.5530H25A···H18xii2.5705
H22B···H23B2.4981H25A···H24Biii2.9632
H22B···H23C2.9305H25A···H24Ciii3.0052
H22C···H23B3.5385H25B···C15xi3.3457
H22C···H23C3.5014H25B···C16xi3.1228
H22C···H152.7633H25B···C17xi3.5459
H24A···H25A3.5321H25B···C18xii3.5671
H24A···H25B2.9335H25B···C21xi3.4071
H24A···H25C2.4730H25B···H17xii3.2416
H24B···H25A3.5373H25B···H18xii2.8446
H24B···H25B2.4825H25B···H22Cxi3.3101
H24B···H25C2.9306H25B···H15xi3.5908
H24C···H25B3.5402H25C···C24iii3.5105
H24C···H25C3.5345H25C···H22Bxi3.1132
H14···H152.62 (5)H25C···H22Cxi3.3602
Cl1···H4Avii2.9523H25C···H24Biii3.0634
Cl1···H6Aviii3.4267H25C···H24Ciii3.1006
Cl1···H6Bvii3.0761H14···C17iii3.41 (3)
Cl1···H20ix3.1167H14···C23ii3.31 (3)
O1···H1i3.5308H14···H17iii3.0182
O2···H4Bii3.0143H14···H23Aii2.9290
O2···H9Biii3.0186H14···H23Bii2.8139
O2···H11Aiii3.3915H14···H23Civ3.3666
O2···H22Bii3.2809H15···O3i2.82 (3)
O2···H23Bii2.5279H15···H1i3.5668
O2···H24Ciii2.9582H15···H25Bviii3.5908
O3···H6Aiii3.0391
C7—O1—C8118.15 (17)C5—C4—H4A108.827
C2—C1—C13108.84 (18)C5—C4—H4B108.825
C2—C1—C14111.3 (2)H4A—C4—H4B107.694
C13—C1—C14109.5 (2)C5—C6—H6A108.843
C1—C2—C3118.91 (19)C5—C6—H6B108.834
C1—C2—C7122.5 (2)C7—C6—H6A108.840
C3—C2—C7118.6 (2)C7—C6—H6B108.826
O3—C3—C2121.0 (3)H6A—C6—H6B107.685
O3—C3—C4121.3 (3)C8—C9—H9A108.954
C2—C3—C4117.6 (2)C8—C9—H9B108.952
C3—C4—C5113.7 (2)C10—C9—H9A108.954
C4—C5—C6108.5 (2)C10—C9—H9B108.949
C4—C5—C22107.8 (2)H9A—C9—H9B107.758
C4—C5—C23111.8 (3)C10—C11—H11A108.624
C6—C5—C22110.0 (2)C10—C11—H11B108.623
C6—C5—C23110.1 (2)C12—C11—H11A108.627
C22—C5—C23108.5 (3)C12—C11—H11B108.630
C5—C6—C7113.65 (18)H11A—C11—H11B107.591
O1—C7—C2122.4 (2)C1—C14—H14120 (2)
O1—C7—C6111.26 (18)C15—C14—H14116 (2)
C2—C7—C6126.3 (2)C14—C15—H15117 (2)
O1—C8—C9110.9 (2)C16—C15—H15114 (2)
O1—C8—C13122.8 (2)C16—C17—H17119.465
C9—C8—C13126.3 (3)C18—C17—H17119.480
C8—C9—C10113.1 (2)C17—C18—H18120.276
C9—C10—C11108.5 (2)C19—C18—H18120.295
C9—C10—C24109.5 (3)C19—C20—H20120.642
C9—C10—C25110.3 (2)C21—C20—H20120.636
C11—C10—C24110.2 (2)C16—C21—H21118.966
C11—C10—C25109.3 (3)C20—C21—H21118.975
C24—C10—C25109.0 (3)C5—C22—H22A109.468
C10—C11—C12114.5 (2)C5—C22—H22B109.471
O2—C12—C11121.7 (3)C5—C22—H22C109.474
O2—C12—C13120.7 (3)H22A—C22—H22B109.480
C11—C12—C13117.6 (3)H22A—C22—H22C109.469
C1—C13—C8122.4 (3)H22B—C22—H22C109.466
C1—C13—C12119.2 (2)C5—C23—H23A109.469
C8—C13—C12118.3 (2)C5—C23—H23B109.479
C1—C14—C15124.6 (3)C5—C23—H23C109.476
C14—C15—C16128.1 (3)H23A—C23—H23B109.462
C15—C16—C17119.2 (2)H23A—C23—H23C109.469
C15—C16—C21123.3 (3)H23B—C23—H23C109.473
C17—C16—C21117.5 (3)C10—C24—H24A109.468
C16—C17—C18121.1 (3)C10—C24—H24B109.469
C17—C18—C19119.4 (3)C10—C24—H24C109.475
Cl1—C19—C18119.6 (3)H24A—C24—H24B109.469
Cl1—C19—C20119.2 (2)H24A—C24—H24C109.479
C18—C19—C20121.2 (3)H24B—C24—H24C109.467
C19—C20—C21118.7 (3)C10—C25—H25A109.481
C16—C21—C20122.1 (3)C10—C25—H25B109.472
C2—C1—H1109.048C10—C25—H25C109.464
C13—C1—H1109.049H25A—C25—H25B109.478
C14—C1—H1109.033H25A—C25—H25C109.467
C3—C4—H4A108.824H25B—C25—H25C109.466
C3—C4—H4B108.827
C7—O1—C8—C9172.00 (18)O1—C8—C9—C10160.40 (19)
C7—O1—C8—C139.1 (4)O1—C8—C13—C13.6 (4)
C8—O1—C7—C27.4 (4)O1—C8—C13—C12179.6 (2)
C8—O1—C7—C6171.84 (18)C9—C8—C13—C1175.1 (3)
C2—C1—C13—C815.6 (3)C9—C8—C13—C121.6 (4)
C2—C1—C13—C12167.64 (19)C13—C8—C9—C1020.7 (4)
C13—C1—C2—C3162.82 (19)C8—C9—C10—C1144.0 (3)
C13—C1—C2—C717.3 (3)C8—C9—C10—C24164.34 (19)
C2—C1—C14—C1541.8 (3)C8—C9—C10—C2575.7 (3)
C14—C1—C2—C376.4 (3)C9—C10—C11—C1252.8 (3)
C14—C1—C2—C7103.6 (3)C24—C10—C11—C12172.7 (3)
C13—C1—C14—C1578.6 (3)C25—C10—C11—C1267.5 (3)
C14—C1—C13—C8106.3 (3)C10—C11—C12—O2145.5 (3)
C14—C1—C13—C1270.5 (3)C10—C11—C12—C1336.4 (4)
C1—C2—C3—O32.9 (4)O2—C12—C13—C110.4 (4)
C1—C2—C3—C4174.8 (2)O2—C12—C13—C8172.7 (3)
C1—C2—C7—O16.9 (4)C11—C12—C13—C1167.7 (2)
C1—C2—C7—C6174.0 (2)C11—C12—C13—C89.2 (4)
C3—C2—C7—O1173.2 (2)C1—C14—C15—C16176.2 (2)
C3—C2—C7—C65.9 (4)C14—C15—C16—C17172.4 (3)
C7—C2—C3—O3177.0 (3)C14—C15—C16—C217.1 (4)
C7—C2—C3—C45.2 (4)C15—C16—C17—C18177.9 (2)
O3—C3—C4—C5146.3 (3)C15—C16—C21—C20178.6 (2)
C2—C3—C4—C536.0 (4)C17—C16—C21—C200.8 (4)
C3—C4—C5—C653.3 (3)C21—C16—C17—C181.6 (4)
C3—C4—C5—C2265.9 (3)C16—C17—C18—C190.9 (4)
C3—C4—C5—C23174.92 (19)C17—C18—C19—Cl1179.8 (2)
C4—C5—C6—C742.2 (3)C17—C18—C19—C200.6 (4)
C22—C5—C6—C775.5 (3)Cl1—C19—C20—C21179.07 (16)
C23—C5—C6—C7164.9 (3)C18—C19—C20—C211.3 (4)
C5—C6—C7—O1166.44 (19)C19—C20—C21—C160.6 (4)
C5—C6—C7—C214.4 (4)
Symmetry codes: (i) x1, y, z; (ii) x+5/2, y1/2, z+3/2; (iii) x+1, y, z; (iv) x+3/2, y1/2, z+3/2; (v) x+5/2, y+1/2, z+3/2; (vi) x+3/2, y+1/2, z+3/2; (vii) x1/2, y+1/2, z+1/2; (viii) x+1/2, y+1/2, z+1/2; (ix) x+2, y, z+2; (x) x+1, y, z+1; (xi) x1/2, y+1/2, z1/2; (xii) x+1/2, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23B···O2v0.962.533.461 (4)163
Symmetry code: (v) x+5/2, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23B···O2i0.9602.52793.461 (4)163.0
Symmetry code: (i) x+5/2, y+1/2, z+3/2.
 

Acknowledgements

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

References

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