supplementary materials


ff2113 scheme

Acta Cryst. (2013). E69, o1347    [ doi:10.1107/S1600536813020357 ]

(E)-2,2'-[3-(4-Chlorophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

J. H. Cha, J. K. Lee, S.-J. Min, Y. S. Cho and J. Park

Abstract top

The title compound, C25H29ClO4, adopts a trans conformation about the C=C double bond and the dimethylcyclohexenone rings both show an envelope conformation with the dimethyl-substituted C atom as the flap. In the molecule, the hydroxy and carbonyl groups form two intramolecular O-H...O hydrogen bonds typical for xanthene derivatives. In the crystal, weak C-H...O hydrogen bonds link the molecules into chains running parallel to the a-axis direction.

Comment top

As part of our ongoing study of the substituent effect on the solid state structures of dimethyl cyclohexenone ring derivatives (Cha et al., 2011, 2012, 2013) we present here the crystal structure of the title compound, C25H29ClO4. In the title compound (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related structures. Both dimethyl cyclohexenone rings (C2—C7), (C8—C13) show an envelope conformation. The hydroxy and carbonyl O atoms face each other and are oriented to allow for the formation of two intramolecular O—H···O hydrogen bonds. In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into chains running parallel to the a-axis.

Related literature top

For the crystal structures of xanthene derivatives studied recently our group, see: Cha et al. (2011, 2012, 2013).

Experimental top

To solution of 5,5-Dimethyl-1,3-cyclohexanedione (4.61 mmol), 4-chlorocinnamaldehyde(1.84 mmol) and 4 Å molecular sieve (M.S.) was added catalytic amounts of L-proline under nitrogen atmosphere. The anhydrous ethyl acetate (2 ml) was added to a reaction mixture and the solution was stirred at room temperature for 6 h. The progress of reaction was monitored by TLC. After completion of reaction, the reaction mixture was filtered through aa pad of celite to remove M.S. and evaporation of the solvent afforded a mixture. The mixture was purified by flash column chromatography (E.A.: Hexane = 1:3) to afford the title compound as a colorless solid in yield 91%. Recrystallization from ethanol gave crystals suitable for X-ray analysis.

Refinement top

All hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.82–1.03 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, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); 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 ellipsoid.
(E)-2,2'-[3-(4-Chlorophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) top
Crystal data top
C25H29ClO4F(000) = 1824.00
Mr = 428.95Dx = 1.255 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2ycCell parameters from 15174 reflections
a = 25.8781 (16) Åθ = 3.2–27.5°
b = 9.7820 (6) ŵ = 0.20 mm1
c = 20.9904 (11) ÅT = 296 K
β = 121.2919 (15)°Block, colourless
V = 4540.5 (5) Å30.20 × 0.20 × 0.20 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3926 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.028
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 3333
Tmin = 0.692, Tmax = 0.962k = 1212
21331 measured reflectionsl = 2724
5175 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) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0716P)2 + 1.3045P]
where P = (Fo2 + 2Fc2)/3
5175 reflections(Δ/σ)max < 0.001
281 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.28 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H29ClO4V = 4540.5 (5) Å3
Mr = 428.95Z = 8
Monoclinic, C2/cMo Kα radiation
a = 25.8781 (16) ŵ = 0.20 mm1
b = 9.7820 (6) ÅT = 296 K
c = 20.9904 (11) Å0.20 × 0.20 × 0.20 mm
β = 121.2919 (15)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5175 independent reflections
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
3926 reflections with F2 > 2σ(F2)
Tmin = 0.692, Tmax = 0.962Rint = 0.028
21331 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.135Δρmax = 0.31 e Å3
S = 1.08Δρmin = 0.28 e Å3
5175 reflectionsAbsolute structure: ?
281 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
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
Cl10.60735 (3)0.86965 (6)1.00738 (3)0.0801 (2)
O10.53057 (5)0.38582 (12)0.63842 (7)0.0500 (3)
O20.56169 (5)0.60824 (13)0.59936 (7)0.0537 (3)
O30.73761 (5)0.38291 (13)0.64466 (7)0.0527 (3)
O40.71474 (5)0.17267 (13)0.70741 (7)0.0538 (3)
C10.66126 (6)0.43105 (16)0.70337 (8)0.0374 (3)
C20.62898 (6)0.29467 (15)0.68798 (8)0.0374 (3)
C30.56690 (7)0.28289 (16)0.66028 (8)0.0414 (4)
C40.53791 (8)0.14617 (18)0.65355 (11)0.0536 (5)
C50.58134 (8)0.03632 (17)0.70514 (9)0.0489 (4)
C60.63474 (8)0.03533 (17)0.69324 (10)0.0513 (4)
C70.66125 (7)0.17326 (17)0.69678 (8)0.0427 (4)
C80.65497 (6)0.50368 (16)0.63540 (8)0.0372 (3)
C90.60755 (7)0.59492 (16)0.59183 (8)0.0416 (4)
C100.60661 (7)0.68081 (18)0.53225 (9)0.0474 (4)
C110.66824 (8)0.69941 (17)0.53963 (8)0.0453 (4)
C120.69780 (8)0.55825 (18)0.55360 (9)0.0474 (4)
C130.69722 (7)0.47803 (16)0.61431 (8)0.0407 (4)
C140.65213 (7)0.52792 (17)0.75347 (8)0.0403 (4)
C150.62794 (7)0.49923 (17)0.79349 (9)0.0441 (4)
C160.62435 (7)0.59311 (15)0.84652 (8)0.0399 (4)
C170.57709 (7)0.57897 (17)0.85930 (9)0.0447 (4)
C180.57174 (8)0.66411 (18)0.90809 (10)0.0489 (4)
C190.61431 (8)0.76360 (16)0.94535 (8)0.0460 (4)
C200.66228 (8)0.78006 (18)0.93498 (10)0.0539 (5)
C210.66711 (8)0.69360 (19)0.88557 (9)0.0505 (4)
C220.65859 (10)0.7597 (3)0.46664 (10)0.0627 (5)
C230.70827 (9)0.7961 (2)0.60417 (10)0.0576 (5)
C240.60344 (11)0.0684 (3)0.78706 (11)0.0652 (5)
C250.55002 (11)0.1028 (2)0.68548 (14)0.0720 (6)
H10.70420.40700.73310.0449*
H20.55480.53530.61280.0645*
H4A0.51950.11480.60240.0643*
H4B0.50590.15760.66420.0643*
H40.72090.24510.69280.0646*
H6A0.66620.02290.73080.0616*
H6B0.62160.00490.64490.0616*
H10A0.59070.77030.53280.0569*
H10B0.57910.63940.48420.0569*
H12A0.67700.50590.50770.0569*
H12B0.73940.56970.56660.0569*
H140.6705 (9)0.616 (2)0.7603 (11)0.057 (6)*
H150.6082 (9)0.405 (3)0.7873 (11)0.060 (6)*
H170.54840.51080.83450.0537*
H180.53950.65400.91560.0587*
H200.69100.84780.96060.0647*
H210.69960.70350.87870.0606*
H22A0.69700.77010.47040.0753*
H22B0.63930.84730.45780.0753*
H22C0.63350.69940.42610.0753*
H23A0.71280.76080.64950.0691*
H23B0.68980.88480.59410.0691*
H23C0.74730.80320.60930.0691*
H24A0.56940.07260.79360.0783*
H24B0.62410.15470.80040.0783*
H24C0.63060.00210.81830.0783*
H25A0.53720.12530.63490.0864*
H25B0.51540.09940.69100.0864*
H25C0.57770.17110.71830.0864*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1143 (5)0.0719 (4)0.0670 (4)0.0022 (3)0.0562 (4)0.0239 (3)
O10.0344 (6)0.0510 (7)0.0608 (7)0.0095 (5)0.0220 (6)0.0033 (6)
O20.0445 (7)0.0595 (8)0.0684 (8)0.0160 (6)0.0371 (6)0.0161 (6)
O30.0411 (7)0.0610 (8)0.0635 (7)0.0144 (6)0.0323 (6)0.0061 (6)
O40.0441 (7)0.0592 (8)0.0618 (7)0.0185 (6)0.0301 (6)0.0112 (6)
C10.0318 (7)0.0474 (8)0.0338 (7)0.0066 (6)0.0175 (6)0.0018 (6)
C20.0360 (8)0.0434 (8)0.0335 (7)0.0063 (6)0.0185 (6)0.0021 (6)
C30.0376 (8)0.0474 (8)0.0382 (7)0.0049 (7)0.0191 (7)0.0008 (7)
C40.0434 (10)0.0510 (10)0.0597 (10)0.0014 (8)0.0221 (8)0.0032 (8)
C50.0546 (10)0.0429 (9)0.0504 (9)0.0005 (7)0.0281 (8)0.0027 (7)
C60.0593 (11)0.0446 (9)0.0505 (9)0.0115 (8)0.0289 (9)0.0012 (7)
C70.0418 (8)0.0515 (9)0.0338 (7)0.0101 (7)0.0188 (7)0.0024 (7)
C80.0328 (7)0.0458 (8)0.0355 (7)0.0031 (6)0.0195 (6)0.0009 (6)
C90.0367 (8)0.0497 (9)0.0390 (8)0.0027 (7)0.0202 (7)0.0007 (7)
C100.0432 (9)0.0570 (10)0.0393 (8)0.0050 (8)0.0195 (7)0.0072 (7)
C110.0491 (9)0.0522 (9)0.0382 (8)0.0021 (8)0.0253 (7)0.0001 (7)
C120.0500 (10)0.0572 (10)0.0471 (9)0.0022 (8)0.0337 (8)0.0047 (8)
C130.0360 (8)0.0484 (9)0.0412 (8)0.0001 (7)0.0225 (7)0.0048 (7)
C140.0410 (8)0.0444 (8)0.0379 (8)0.0011 (7)0.0221 (7)0.0011 (7)
C150.0481 (9)0.0453 (9)0.0453 (8)0.0020 (7)0.0288 (8)0.0028 (7)
C160.0443 (9)0.0419 (8)0.0371 (7)0.0007 (7)0.0237 (7)0.0024 (6)
C170.0418 (9)0.0490 (9)0.0470 (8)0.0074 (7)0.0255 (7)0.0081 (7)
C180.0475 (10)0.0537 (9)0.0554 (10)0.0005 (8)0.0336 (8)0.0053 (8)
C190.0597 (10)0.0433 (8)0.0389 (8)0.0020 (8)0.0284 (8)0.0032 (7)
C200.0606 (11)0.0494 (9)0.0495 (9)0.0182 (8)0.0270 (9)0.0071 (8)
C210.0517 (10)0.0588 (10)0.0527 (9)0.0102 (8)0.0353 (8)0.0005 (8)
C220.0753 (13)0.0712 (13)0.0517 (10)0.0018 (10)0.0400 (10)0.0076 (9)
C230.0613 (11)0.0572 (11)0.0523 (10)0.0086 (9)0.0281 (9)0.0064 (8)
C240.0855 (15)0.0636 (12)0.0579 (11)0.0058 (11)0.0452 (11)0.0004 (9)
C250.0824 (16)0.0480 (10)0.0873 (15)0.0073 (10)0.0452 (13)0.0059 (10)
Geometric parameters (Å, º) top
Cl1—C191.746 (2)C20—C211.393 (3)
O1—C31.288 (2)O2—H20.820
O2—C91.283 (3)O4—H40.820
O3—C131.2932 (19)C1—H10.980
O4—C71.283 (3)C4—H4A0.970
C1—C21.517 (3)C4—H4B0.970
C1—C81.525 (3)C6—H6A0.970
C1—C141.522 (3)C6—H6B0.970
C2—C31.401 (3)C10—H10A0.970
C2—C71.408 (3)C10—H10B0.970
C3—C41.504 (3)C12—H12A0.970
C4—C51.525 (3)C12—H12B0.970
C5—C61.527 (4)C14—H140.96 (2)
C5—C241.537 (3)C15—H151.03 (3)
C5—C251.527 (3)C17—H170.930
C6—C71.498 (3)C18—H180.930
C8—C91.405 (2)C20—H200.930
C8—C131.399 (3)C21—H210.930
C9—C101.496 (3)C22—H22A0.960
C10—C111.531 (3)C22—H22B0.960
C11—C121.531 (3)C22—H22C0.960
C11—C221.536 (3)C23—H23A0.960
C11—C231.531 (3)C23—H23B0.960
C12—C131.503 (3)C23—H23C0.960
C14—C151.312 (3)C24—H24A0.960
C15—C161.483 (3)C24—H24B0.960
C16—C171.388 (3)C24—H24C0.960
C16—C211.386 (3)C25—H25A0.960
C17—C181.382 (3)C25—H25B0.960
C18—C191.370 (3)C25—H25C0.960
C19—C201.377 (4)
O1···O22.596 (2)H22B···H23C2.9787
O1···C12.9500 (19)H22C···H23B3.5386
O1···C73.600 (2)H22C···H23C3.5689
O1···C83.451 (3)H24A···H25A3.5586
O1···C93.337 (3)H24A···H25B2.5096
O1···C143.1254 (18)H24A···H25C2.9303
O1···C153.1072 (18)H24B···H25B3.5566
O2···C12.9268 (17)H24B···H25C3.5249
O2···C23.5406 (19)H24C···H25A3.5295
O2···C33.406 (2)H24C···H25B2.9424
O2···C133.589 (3)H24C···H25C2.4564
O2···C142.9486 (17)Cl1···H6Bi3.0186
O3···O42.669 (2)Cl1···H22Bxi3.2133
O3···C12.859 (3)Cl1···H23Bxi3.0987
O3···C23.483 (3)Cl1···H25Aviii3.3630
O3···C73.399 (3)O1···H10Bii2.6745
O4···C12.862 (2)O1···H17iii2.6842
O4···C33.584 (3)O1···H18iii3.0529
O4···C83.568 (2)O2···H18iii2.5113
O4···C133.468 (2)O2···H25Aiv2.8705
C2···C52.915 (3)O2···H25Civ3.1597
C2···C93.442 (3)O3···H6Avii2.6688
C2···C133.401 (3)O3···H14v3.395 (18)
C2···C152.995 (3)O3···H20v3.5562
C2···C243.330 (4)O3···H21v2.6046
C3···C62.857 (3)O3···H24Cvii3.2782
C3···C83.372 (3)O4···H1v3.1608
C3···C143.155 (2)O4···H14v2.74 (3)
C3···C153.194 (3)O4···H21v3.5252
C3···C243.125 (3)O4···H23Av2.7257
C4···C72.841 (3)O4···H23Bix3.5219
C7···C83.452 (3)C1···H23Av3.5318
C7···C243.135 (4)C1···H23Cv3.5995
C8···C112.923 (3)C3···H10Bii3.4852
C8···C233.384 (3)C4···H10Bii3.5823
C9···C122.859 (4)C4···H24Aiii3.5584
C9···C143.034 (3)C6···H23Bix3.4066
C9···C233.167 (3)C7···H23Av3.2924
C10···C132.864 (3)C12···H22Axii3.4517
C13···C233.142 (3)C13···H6Avii3.3361
C14···C213.058 (3)C14···H4vii3.5679
C16···C192.777 (3)C14···H23Cv3.4805
C17···C202.760 (3)C14···H25Civ3.3828
C18···C212.759 (4)C15···H22Ci3.3353
Cl1···C7i3.4881 (18)C15···H23Cv3.3798
O1···C10ii3.5567 (17)C15···H25Civ3.5282
O1···C17iii3.387 (3)C16···H12Ai3.0750
O1···C18iii3.562 (3)C16···H22Ci3.2586
O2···C18iii3.418 (3)C16···H25Civ3.2630
O2···C25iv3.452 (3)C17···H10Bi3.3620
O3···C21v3.397 (3)C17···H12Ai2.9514
O4···C14v3.407 (3)C17···H22Ci3.0627
O4···C23v3.589 (3)C18···H2iii3.3192
C7···Cl1vi3.4881 (18)C18···H10Bi3.3305
C10···O1ii3.5567 (17)C18···H12Ai2.9391
C14···O4vii3.407 (3)C18···H25Aviii3.2196
C17···O1iii3.387 (3)C18···H25Bviii3.1455
C18···O1iii3.562 (3)C19···H12Ai3.0146
C18···O2iii3.418 (3)C19···H25Aviii3.5403
C18···C25viii3.544 (3)C19···H25Bviii3.3584
C21···O3vii3.397 (3)C20···H12Ai3.1142
C23···O4vii3.589 (3)C20···H20xiii3.4842
C25···O2ix3.452 (3)C20···H24Civ3.0203
C25···C18x3.544 (3)C21···H12Ai3.1255
Cl1···H182.7805C21···H20xiii3.4292
Cl1···H202.8122C21···H24Civ3.2186
O1···H21.7810C21···H25Civ3.3161
O1···H4A2.7306C22···H12Bxii3.4859
O1···H4B2.4584C22···H22Axii3.2667
O1···H152.704 (19)C22···H23Cxii3.5905
O2···H10A2.4728C22···H24Avi3.5355
O2···H10B2.6956C22···H24Bvi3.2308
O2···H143.076 (16)C23···H1vii3.1526
O3···H12.4318C23···H6Biv3.3975
O3···H41.8652C23···H22Axii3.5874
O3···H12A2.7362C24···H4Biii3.5806
O3···H12B2.4712C24···H22Bi3.3070
O4···H12.4024C24···H22Ci3.4528
O4···H6A2.4738C25···H18x3.2287
O4···H6B2.6942H1···O4vii3.1608
C1···H22.6080H1···C23v3.1526
C1···H42.4692H1···H6Avii3.1070
C1···H152.75 (3)H1···H23Av2.6890
C2···H22.9270H1···H23Bv3.2230
C2···H4A3.0110H1···H23Cv3.0387
C2···H4B3.2466H2···C18iii3.3192
C2···H42.3780H2···H10Bii3.4272
C2···H6A3.2378H2···H17iii3.3905
C2···H6B3.0428H2···H18iii2.4809
C2···H143.411 (19)H2···H25Aiv3.4155
C2···H152.64 (3)H2···H25Civ3.4842
C2···H24B2.7872H4A···H10Aii3.0071
C3···H13.2857H4A···H10Bii3.2823
C3···H22.6198H4B···C24iii3.5806
C3···H6B3.2414H4B···H10Bii3.3716
C3···H152.59 (3)H4B···H22Bii3.2691
C3···H24A3.4462H4B···H22Cii3.3845
C3···H24B2.8090H4B···H24Aiii2.6583
C4···H6A3.2847H4···C14v3.5679
C4···H6B2.7049H4···H6Avii3.3756
C4···H153.51 (2)H4···H14v2.7543
C4···H24A2.7083H4···H21v3.1385
C4···H24B2.7094H4···H23Av2.8328
C4···H24C3.3471H6A···O3v2.6688
C4···H25A2.6831H6A···C13v3.3361
C4···H25B2.6826H6A···H1v3.1070
C4···H25C3.3297H6A···H4v3.3756
C6···H4A2.6888H6A···H14ix3.5791
C6···H4B3.2874H6A···H23Aix3.3147
C6···H43.0338H6A···H23Bix3.3524
C6···H24A3.3360H6B···Cl1vi3.0186
C6···H24B2.6727H6B···C23ix3.3975
C6···H24C2.7078H6B···H10Aix3.0101
C6···H25A2.6697H6B···H23Aix3.2557
C6···H25B3.3338H6B···H23Bix2.7143
C6···H25C2.7091H10A···H4Aii3.0071
C7···H12.4829H10A···H6Biv3.0101
C7···H4A3.1881H10A···H25Aiv3.2595
C7···H24B2.8038H10B···O1ii2.6745
C7···H24C3.4905H10B···C3ii3.4852
C8···H22.3998H10B···C4ii3.5823
C8···H42.9370H10B···C17vi3.3620
C8···H10A3.2378H10B···C18vi3.3305
C8···H10B3.0358H10B···H2ii3.4272
C8···H12A3.0152H10B···H4Aii3.2823
C8···H12B3.2493H10B···H4Bii3.3716
C8···H142.67 (3)H10B···H17vi3.1744
C8···H23A2.8629H10B···H18vi3.1355
C9···H13.2747H12A···C16vi3.0750
C9···H12A3.2242H12A···C17vi2.9514
C9···H143.04 (2)H12A···C18vi2.9391
C9···H23A2.8454H12A···C19vi3.0146
C9···H23B3.5311H12A···C20vi3.1142
C10···H23.0054H12A···C21vi3.1255
C10···H12A2.7350H12A···H17vi3.4273
C10···H12B3.3071H12A···H18vi3.4190
C10···H22A3.3271H12A···H20v3.4853
C10···H22B2.6797H12B···C22xii3.4859
C10···H22C2.6633H12B···H20v3.0569
C10···H23A2.6830H12B···H22Axii2.6641
C10···H23B2.7203H12B···H22Bxii3.5275
C10···H23C3.3442H12B···H24Bvii3.2747
C12···H10A3.3044H12B···H24Cvii3.0340
C12···H10B2.7462H14···O3vii3.395 (18)
C12···H22A2.7028H14···O4vii2.74 (3)
C12···H22B3.3414H14···H4vii2.7543
C12···H22C2.6861H14···H6Aiv3.5791
C12···H23A2.7048H14···H25Civ2.9474
C12···H23B3.3398H15···H22Ci2.8245
C12···H23C2.6821H15···H23Cv3.3563
C13···H12.5025H17···O1iii2.6842
C13···H42.6894H17···H2iii3.3905
C13···H10B3.2593H17···H10Bi3.1744
C13···H23A2.8373H17···H12Ai3.4273
C13···H23C3.4566H17···H17iii3.1033
C14···H22.7098H17···H22Ci2.8924
C14···H212.8306H18···O1iii3.0529
C15···H12.9862H18···O2iii2.5113
C15···H23.2616H18···C25viii3.2287
C15···H172.6127H18···H2iii2.4809
C15···H212.6806H18···H10Bi3.1355
C15···H24B3.3767H18···H12Ai3.4190
C16···H142.65 (3)H18···H25Aviii2.7464
C16···H183.2524H18···H25Bviii3.0890
C16···H203.2591H18···H25Cviii3.3419
C17···H152.66 (3)H20···O3vii3.5562
C17···H213.2194H20···C20xiii3.4842
C18···H203.2304H20···C21xiii3.4292
C19···H173.2119H20···H12Avii3.4853
C19···H213.2230H20···H12Bvii3.0569
C20···H183.2300H20···H20xiii3.2364
C21···H142.78 (3)H20···H21xiii3.1193
C21···H153.36 (2)H20···H22Bxi3.2572
C21···H173.2185H20···H24Civ2.9433
C22···H10A2.7502H21···O3vii2.6046
C22···H10B2.5576H21···O4vii3.5252
C22···H12A2.5897H21···H4vii3.1385
C22···H12B2.7693H21···H20xiii3.1193
C22···H23A3.3326H21···H24Civ3.2766
C22···H23B2.6584H21···H25Civ3.4292
C22···H23C2.6978H22A···C12xii3.4517
C23···H10A2.6139H22A···C22xii3.2667
C23···H10B3.3344H22A···C23xii3.5874
C23···H12A3.3328H22A···H12Bxii2.6641
C23···H12B2.6147H22A···H22Axii2.3851
C23···H22A2.6798H22A···H23Cxii2.8117
C23···H22B2.6786H22A···H24Bvi3.1369
C23···H22C3.3321H22A···H24Cvi3.5488
C24···H4A3.3461H22B···Cl1xiv3.2133
C24···H4B2.6497H22B···C24vi3.3070
C24···H6A2.6115H22B···H4Bii3.2691
C24···H6B3.3310H22B···H12Bxii3.5275
C24···H153.30 (2)H22B···H20xiv3.2572
C24···H25A3.3237H22B···H24Avi3.0483
C24···H25B2.6787H22B···H24Bvi3.1185
C24···H25C2.6497H22B···H24Cvi3.1990
C25···H4A2.6001H22C···C15vi3.3353
C25···H4B2.7312H22C···C16vi3.2586
C25···H6A2.7533H22C···C17vi3.0627
C25···H6B2.5914H22C···C24vi3.4528
C25···H24A2.6767H22C···H4Bii3.3845
C25···H24B3.3219H22C···H15vi2.8245
C25···H24C2.6561H22C···H17vi2.8924
H1···H23.5717H22C···H23Cxii3.5301
H1···H41.9467H22C···H24Avi3.2653
H1···H142.4037H22C···H24Bvi2.8963
H1···H153.2263H23A···O4vii2.7257
H2···H10A3.2527H23A···C1vii3.5318
H2···H10B3.2362H23A···C7vii3.2924
H2···H143.0890H23A···H1vii2.6890
H2···H153.4192H23A···H4vii2.8328
H4A···H6A3.5860H23A···H6Aiv3.3147
H4A···H6B2.5897H23A···H6Biv3.2557
H4A···H24A3.5430H23B···Cl1xiv3.0987
H4A···H25A2.4219H23B···O4iv3.5219
H4A···H25B2.8373H23B···C6iv3.4066
H4A···H25C3.4925H23B···H1vii3.2230
H4B···H6B3.5940H23B···H6Aiv3.3524
H4B···H153.5270H23B···H6Biv2.7143
H4B···H24A2.4764H23C···C1vii3.5995
H4B···H24B2.9061H23C···C14vii3.4805
H4B···H24C3.5322H23C···C15vii3.3798
H4B···H25A3.0352H23C···C22xii3.5905
H4B···H25B2.5591H23C···H1vii3.0387
H4B···H25C3.5902H23C···H15vii3.3563
H4···H6A3.2689H23C···H22Axii2.8117
H4···H6B3.3024H23C···H22Cxii3.5301
H6A···H24A3.5087H23C···H24Bvii3.1984
H6A···H24B2.8271H24A···C4iii3.5584
H6A···H24C2.4542H24A···C22i3.5355
H6A···H25A3.0355H24A···H4Biii2.6583
H6A···H25C2.6056H24A···H22Bi3.0483
H6B···H24B3.5883H24A···H22Ci3.2653
H6B···H24C3.5251H24A···H24Aiii3.0705
H6B···H25A2.3928H24A···H25Biii2.9152
H6B···H25B3.4781H24B···C22i3.2308
H6B···H25C2.8506H24B···H12Bv3.2747
H10A···H22B2.5856H24B···H22Ai3.1369
H10A···H22C3.0503H24B···H22Bi3.1185
H10A···H23A2.8210H24B···H22Ci2.8963
H10A···H23B2.4624H24B···H23Cv3.1984
H10A···H23C3.5133H24C···O3v3.2782
H10B···H12A2.6583H24C···C20ix3.0203
H10B···H22A3.4558H24C···C21ix3.2186
H10B···H22B2.7868H24C···H12Bv3.0340
H10B···H22C2.3661H24C···H20ix2.9433
H10B···H23A3.5987H24C···H21ix3.2766
H10B···H23B3.5251H24C···H22Ai3.5488
H12A···H22A2.8250H24C···H22Bi3.1990
H12A···H22B3.4839H25A···Cl1x3.3630
H12A···H22C2.4046H25A···O2ix2.8705
H12A···H23C3.5052H25A···C18x3.2196
H12B···H22A2.6114H25A···C19x3.5403
H12B···H22C3.0698H25A···H2ix3.4155
H12B···H23A2.8708H25A···H10Aix3.2595
H12B···H23B3.5008H25A···H18x2.7464
H12B···H23C2.4241H25B···C18x3.1455
H14···H152.85 (4)H25B···C19x3.3584
H14···H212.3527H25B···H18x3.0890
H14···H23A3.3554H25B···H24Aiii2.9152
H15···H172.4558H25B···H25Biii2.9735
H15···H24A3.4262H25C···O2ix3.1597
H15···H24B2.4753H25C···C14ix3.3828
H17···H182.3063H25C···C15ix3.5282
H20···H212.3224H25C···C16ix3.2630
H22A···H23A3.5645H25C···C21ix3.3161
H22A···H23B2.9224H25C···H2ix3.4842
H22A···H23C2.5220H25C···H14ix2.9474
H22B···H23A3.5451H25C···H18x3.3419
H22B···H23B2.4785H25C···H21ix3.4292
C2—C1—C8115.54 (12)C3—C4—H4B108.669
C2—C1—C14115.38 (17)C5—C4—H4A108.673
C8—C1—C14112.14 (14)C5—C4—H4B108.662
C1—C2—C3123.14 (14)H4A—C4—H4B107.607
C1—C2—C7119.37 (14)C5—C6—H6A108.612
C3—C2—C7117.35 (14)C5—C6—H6B108.599
O1—C3—C2123.43 (15)C7—C6—H6A108.615
O1—C3—C4115.18 (15)C7—C6—H6B108.621
C2—C3—C4121.39 (15)H6A—C6—H6B107.574
C3—C4—C5114.34 (14)C9—C10—H10A108.598
C4—C5—C6106.51 (18)C9—C10—H10B108.584
C4—C5—C24111.06 (18)C11—C10—H10A108.574
C4—C5—C25110.12 (14)C11—C10—H10B108.582
C6—C5—C24110.00 (16)H10A—C10—H10B107.551
C6—C5—C25110.41 (19)C11—C12—H12A108.724
C24—C5—C25108.7 (2)C11—C12—H12B108.715
C5—C6—C7114.60 (16)C13—C12—H12A108.717
O4—C7—C2122.66 (16)C13—C12—H12B108.714
O4—C7—C6115.45 (16)H12A—C12—H12B107.633
C2—C7—C6121.89 (17)C1—C14—H14114.8 (17)
C1—C8—C9122.53 (17)C15—C14—H14117.5 (16)
C1—C8—C13119.43 (13)C14—C15—H15118.8 (16)
C9—C8—C13118.03 (17)C16—C15—H15115.4 (16)
O2—C9—C8122.39 (17)C16—C17—H17119.307
O2—C9—C10115.56 (14)C18—C17—H17119.318
C8—C9—C10122.03 (18)C17—C18—H18120.298
C9—C10—C11114.73 (13)C19—C18—H18120.306
C10—C11—C12107.62 (16)C19—C20—H20120.532
C10—C11—C22108.88 (14)C21—C20—H20120.546
C10—C11—C23110.69 (18)C16—C21—H21119.403
C12—C11—C22110.08 (18)C20—C21—H21119.393
C12—C11—C23110.26 (13)C11—C22—H22A109.471
C22—C11—C23109.28 (16)C11—C22—H22B109.480
C11—C12—C13114.15 (19)C11—C22—H22C109.472
O3—C13—C8122.53 (17)H22A—C22—H22B109.466
O3—C13—C12115.58 (19)H22A—C22—H22C109.470
C8—C13—C12121.88 (15)H22B—C22—H22C109.468
C1—C14—C15127.28 (16)C11—C23—H23A109.477
C14—C15—C16125.79 (16)C11—C23—H23B109.479
C15—C16—C17119.23 (14)C11—C23—H23C109.464
C15—C16—C21122.77 (19)H23A—C23—H23B109.479
C17—C16—C21117.99 (18)H23A—C23—H23C109.466
C16—C17—C18121.37 (16)H23B—C23—H23C109.462
C17—C18—C19119.4 (3)C5—C24—H24A109.461
Cl1—C19—C18118.95 (19)C5—C24—H24B109.474
Cl1—C19—C20119.95 (13)C5—C24—H24C109.468
C18—C19—C20121.10 (19)H24A—C24—H24B109.465
C19—C20—C21118.92 (16)H24A—C24—H24C109.480
C16—C21—C20121.2 (2)H24B—C24—H24C109.479
C9—O2—H2109.471C5—C25—H25A109.468
C7—O4—H4109.468C5—C25—H25B109.474
C2—C1—H1103.982C5—C25—H25C109.469
C8—C1—H1104.004H25A—C25—H25B109.471
C14—C1—H1103.975H25A—C25—H25C109.476
C3—C4—H4A108.685H25B—C25—H25C109.469
C2—C1—C8—C989.25 (18)C1—C8—C13—O38.4 (2)
C2—C1—C8—C1389.82 (15)C1—C8—C13—C12172.70 (11)
C8—C1—C2—C380.3 (2)C9—C8—C13—O3170.70 (12)
C8—C1—C2—C795.27 (15)C9—C8—C13—C128.2 (2)
C2—C1—C14—C1511.56 (18)C13—C8—C9—O2168.60 (13)
C14—C1—C2—C353.27 (18)C13—C8—C9—C1010.0 (2)
C14—C1—C2—C7131.20 (14)O2—C9—C10—C11161.45 (13)
C8—C1—C14—C15146.64 (12)C8—C9—C10—C1119.9 (2)
C14—C1—C8—C945.75 (17)C9—C10—C11—C1247.70 (18)
C14—C1—C8—C13135.18 (13)C9—C10—C11—C22167.00 (13)
C1—C2—C3—O17.1 (3)C9—C10—C11—C2372.86 (17)
C1—C2—C3—C4173.35 (14)C10—C11—C12—C1349.17 (15)
C1—C2—C7—O49.8 (3)C22—C11—C12—C13167.69 (13)
C1—C2—C7—C6171.04 (13)C23—C11—C12—C1371.7 (2)
C3—C2—C7—O4165.96 (15)C11—C12—C13—O3157.80 (12)
C3—C2—C7—C613.2 (3)C11—C12—C13—C823.23 (19)
C7—C2—C3—O1168.47 (15)C1—C14—C15—C16174.60 (11)
C7—C2—C3—C411.0 (3)C14—C15—C16—C17151.19 (14)
O1—C3—C4—C5157.25 (16)C14—C15—C16—C2130.2 (2)
C2—C3—C4—C523.2 (3)C15—C16—C17—C18179.88 (12)
C3—C4—C5—C651.3 (3)C15—C16—C21—C20180.00 (13)
C3—C4—C5—C2468.4 (3)C17—C16—C21—C201.4 (3)
C3—C4—C5—C25171.05 (17)C21—C16—C17—C181.5 (2)
C4—C5—C6—C749.33 (17)C16—C17—C18—C190.8 (3)
C24—C5—C6—C771.11 (17)C17—C18—C19—Cl1179.51 (12)
C25—C5—C6—C7168.87 (14)C17—C18—C19—C200.0 (3)
C5—C6—C7—O4161.70 (13)Cl1—C19—C20—C21179.56 (10)
C5—C6—C7—C219.1 (2)C18—C19—C20—C210.1 (3)
C1—C8—C9—O210.5 (2)C19—C20—C21—C160.7 (3)
C1—C8—C9—C10170.94 (11)
Symmetry codes: (i) x, y+1, z+1/2; (ii) x+1, y+1, z+1; (iii) x+1, y, z+3/2; (iv) x, y+1, z; (v) x+3/2, y1/2, z+3/2; (vi) x, y+1, z1/2; (vii) x+3/2, y+1/2, z+3/2; (viii) x+1, y+1, z+3/2; (ix) x, y1, z; (x) x+1, y1, z+3/2; (xi) x, y+2, z+1/2; (xii) x+3/2, y+3/2, z+1; (xiii) x+3/2, y+3/2, z+2; (xiv) x, y+2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.821.782.596 (2)173
O4—H4···O30.821.872.669 (2)166
C18—H18···O2iii0.932.513.418 (3)165
C21—H21···O3vii0.932.613.397 (3)143
Symmetry codes: (iii) x+1, y, z+3/2; (vii) x+3/2, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.8201.7812.596 (2)172.6
O4—H4···O30.8201.8652.669 (2)166.4
C18—H18···O2i0.9302.5113.418 (3)165.00
C21—H21···O3ii0.9302.6053.397 (3)143.00
Symmetry codes: (i) x+1, y, z+3/2; (ii) x+3/2, y+1/2, z+3/2.
Acknowledgements top

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

references
References top

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Cha, J. H., Cho, Y. S., Lee, J. K., Park, J. & Sato, H. (2012). Acta Cryst. E68, o2510.

Cha, J. H., Kim, Y. H., Min, S.-J., Cho, Y. S. & Lee, J. K. (2011). Acta Cryst. E67, o3153.

Cha, J. H., Min, S.-J., Cho, Y. S., Lee, J. K. & Park, J. (2013). Acta Cryst. E69, o397.

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Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.