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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1456.
Published online 2008 July 12. doi:  10.1107/S1600536808020801
PMCID: PMC2962086

2-(4-Isopropyl­benzylidene)propanoic acid

Abstract

The two mol­ecules in the asymmetric unit of the title compound, C13H16O2, form dimers through O—H(...)O hydrogen bonding, resulting in R 2 2(8) rings. Each carboxyl­ O atom is involved in inter­amolecular C—H(...)O hydrogen bonds, forming five-membered rings. There exist dissimilar dihedral angles within the two mol­ecules, for example the carboxylate and isopropyl groups make dihedral angles of 59.6 (4) and 71.7 (3)° in the two molecules. There are no intermolecular π inter­actions.

Related literature

For related literature, see: Burt (2004 [triangle]); Hertog et al. (1995 [triangle]); Ma & Hayes (2004 [triangle]); Muhammad et al. (2007 [triangle]).

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Object name is e-64-o1456-scheme1.jpg

Experimental

Crystal data

  • C13H16O2
  • M r = 204.26
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1456-efi1.jpg
  • a = 9.8406 (4) Å
  • b = 10.5739 (4) Å
  • c = 11.9142 (5) Å
  • α = 96.330 (2)°
  • β = 98.486 (3)°
  • γ = 104.497 (2)°
  • V = 1172.99 (8) Å3
  • Z = 4
  • Mo Kα radiation radiation
  • μ = 0.08 mm−1
  • T = 296 (2) K
  • 0.30 × 0.18 × 0.12 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.977, T max = 0.986
  • 23066 measured reflections
  • 6000 independent reflections
  • 2803 reflections with I > 3σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.157
  • S = 1.04
  • 6000 reflections
  • 290 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020801/jh2064sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020801/jh2064Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer and for financial support to NM for PhD studies under the Indigenous Scholarship Scheme.

supplementary crystallographic information

Comment

Cinnamic acids and their derivatives are widely used chemicals in a variety of fields (Ma & Hayes, 2004). They posses antibacterial, antifungal and parasite fighting abilities (Burt, 2004). A derivative of cinnamic acid is an important pharmaceutical for high blood pressure and stroke prevention and possess antitumour activity (Hertog et al., 1995).

The crystal structure of 3-(4-Bromophenyl)-2-methylacrylic acid (Muhammad et al., 2007) has been reported. The title compound (I) have a replacement of Br-atom with isopropyl at the same position. The ligand has been prepared to synthesize various organotin complexes.

The crystallographic asymmetric unit consists of two ligands. These two ligands form dimers through O—H···O hydrogen bonding with each other by completing a R22(8) rings (Table 1, Fig 2). Each O-atom of carboxylate ligands is involved in interamolecular H-bonds of C—H···O type forming five-membered rings. The bond distances in the benzene ring (C4—C9) have values in the range 1.372 (4)–1.390 (4) Å, whereas in (C17—C22) its range is 1.374 (4)–1.384 (4) Å. The bond angle (C11—C10—C12) of isopropyl moiety is 111.2 (3)°, whereas the same for (C24—C23—C25) is 109.8 (3)°. There exist a dissimilar dihedral angles within the two moieties. The dihedral angles of the isopropyl moieties (C10/C11/C12) and (C23/C24/C25) with their adjacent benzene rings (C4—C9) and (C17—C22) have values of 86.80 (13)° and 85.06 (13)°, respectively. The dihedral angles of the moieties (C2/C3/C13) and (C15/C16/C26) with their adjacent carboxylate moities (C1/O1/O2) and (C14/O3/O4) have values of 7.65 (51)° and 7.06 (43)°, respectively, whereas with benzene rings (C4—C9) and (C17—C22), the values of their dihedral angles is 32.18 (23)° and 34.49 (20)°, respectively. The dihedral angle between the benzene rings of two ligands is 83.34 (9)°. There does not exist any kind of π-interaction.

Experimental

Compound (I) was prepared according to the reported procedure in literature (Muhammad et al., 2007). A mixture of 4-isopropylbenzaldehyde (10 mmol, 1.51 ml), methylmalonic acid (2.36 g, 20 mmol) and piperidine (20 mmol, 1.98 ml) in pyridine (12.5 ml) solution was heated on a steam-bath for 24 h. The reaction mixture was cooled and added to a mixture of 25 ml of concentrated HCl and 50 g of ice. The precipitate formed in the acidified mixture was filtered off and washed with ice-cold water. The product was recrystallized from ethanol. The yield was 80%.

Refinement

H atoms were positioned geometrically, with C—H = 0.93, and 0.96 Å for aromatic and methyl H, and constrained to ride on their parent atoms, while the coordinates of all other H-atoms were refined. The H-atoms were treated as isotropic with Uiso(H) = xUeq(C,O), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Figures

Fig. 1.
ORTEP drawing of the title compound, (C13H16O2)2 with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. The intramolecular H-bonds are shown by doted lines. ...
Fig. 2.
The partial packing figure (PLATON: Spek, 2003) which shows the dimeric nature of the compound.

Crystal data

C13H16O2Z = 4
Mr = 204.26F000 = 440
Triclinic, P1Dx = 1.157 Mg m3
Hall symbol: -P 1Mo Kα radiation radiation λ = 0.71073 Å
a = 9.8406 (4) ÅCell parameters from 2803 reflections
b = 10.5739 (4) Åθ = 2.2–28.8º
c = 11.9142 (5) ŵ = 0.08 mm1
α = 96.330 (2)ºT = 296 (2) K
β = 98.486 (3)ºPrismatic, colourless
γ = 104.497 (2)º0.30 × 0.18 × 0.12 mm
V = 1172.99 (8) Å3

Data collection

Bruker Kappa APEXII CCD diffractometer6000 independent reflections
Radiation source: fine-focus sealed tube2803 reflections with I > 3σ(I)
Monochromator: graphiteRint = 0.033
Detector resolution: 7.4 pixels mm-1θmax = 28.8º
T = 296(2) Kθmin = 2.2º
ω scansh = −13→13
Absorption correction: multi-scan(SADABS; Bruker, 2005)k = −13→14
Tmin = 0.977, Tmax = 0.986l = −15→16
23066 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.053  w = 1/[σ2(Fo2) + (0.0998P)2 + 0.3929P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.157(Δ/σ)max = 0.002
S = 1.04Δρmax = 0.28 e Å3
6000 reflectionsΔρmin = −0.23 e Å3
290 parametersExtinction correction: empirical, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (3)
Secondary atom site location: difference Fourier map

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.4946 (3)0.6966 (3)0.41038 (19)0.0929 (11)
O20.3929 (3)0.8025 (3)0.52698 (18)0.0859 (10)
C10.4167 (3)0.7736 (3)0.4302 (3)0.0604 (10)
C20.3538 (3)0.8277 (3)0.3319 (2)0.0558 (10)
C30.3665 (3)0.7807 (3)0.2271 (2)0.0572 (10)
C40.3150 (3)0.8149 (3)0.1158 (2)0.0529 (9)
C50.2805 (3)0.7198 (3)0.0194 (2)0.0567 (10)
C60.2312 (3)0.7457 (3)−0.0873 (2)0.0575 (9)
C70.2160 (3)0.8681 (3)−0.1039 (2)0.0536 (9)
C80.2534 (4)0.9643 (3)−0.0083 (3)0.0816 (13)
C90.3021 (4)0.9397 (3)0.0992 (3)0.0802 (13)
C100.1631 (3)0.8967 (3)−0.2215 (3)0.0652 (11)
C110.2802 (4)0.9901 (4)−0.2652 (3)0.0981 (16)
C120.0319 (4)0.9478 (4)−0.2243 (3)0.0919 (17)
C130.2769 (4)0.9280 (3)0.3617 (3)0.0818 (12)
O30.5215 (3)0.7354 (3)−0.28826 (18)0.0829 (9)
O40.6264 (3)0.6312 (3)−0.40400 (18)0.0887 (10)
C140.6113 (3)0.6697 (3)−0.3062 (2)0.0559 (10)
C150.6987 (3)0.6413 (3)−0.2046 (2)0.0531 (9)
C160.6664 (3)0.6713 (3)−0.1024 (2)0.0538 (9)
C170.7335 (3)0.6564 (2)0.0123 (2)0.0490 (9)
C180.6479 (3)0.6330 (3)0.0942 (2)0.0640 (10)
C190.7024 (3)0.6191 (3)0.2041 (2)0.0697 (13)
C200.8461 (3)0.6321 (3)0.2382 (2)0.0548 (9)
C210.9313 (3)0.6562 (3)0.1571 (2)0.0561 (9)
C220.8773 (3)0.6688 (3)0.0464 (2)0.0562 (9)
C230.9076 (4)0.6231 (3)0.3602 (3)0.0708 (11)
C240.8264 (4)0.5008 (4)0.4022 (3)0.0926 (16)
C250.9114 (4)0.7468 (4)0.4414 (3)0.0945 (16)
C260.8123 (3)0.5764 (3)−0.2296 (3)0.0682 (11)
H10.537 (4)0.669 (4)0.476 (3)0.1113*
H30.410 (3)0.709 (3)0.218 (2)0.0686*
H50.290820.635930.026930.0680*
H60.207480.67847−0.149880.0690*
H80.245471.04865−0.016760.0975*
H90.326711.007360.161520.0961*
H100.140 (3)0.809 (3)−0.279 (3)0.0784*
H11A0.243201.00662−0.339650.1470*
H11B0.357490.95085−0.270470.1470*
H11C0.313991.07189−0.213010.1470*
H12A0.002140.96492−0.300280.1381*
H12B0.054221.02807−0.170770.1381*
H12C−0.043760.88278−0.203770.1381*
H13A0.284650.945090.443530.1227*
H13B0.178040.895130.326310.1227*
H13C0.318341.008400.334370.1227*
H3A0.470 (4)0.748 (3)−0.356 (3)0.0995*
H160.587 (3)0.701 (3)−0.102 (2)0.0645*
H180.551080.626370.074610.0768*
H190.641290.600650.256320.0836*
H211.028410.664230.177400.0674*
H220.938530.68585−0.005980.0674*
H231.009 (4)0.624 (3)0.362 (3)0.0851*
H24A0.869760.499230.479530.1391*
H24B0.829170.423210.353470.1391*
H24C0.729070.502590.400180.1391*
H25A0.950960.739540.518300.1420*
H25B0.816210.755380.438880.1420*
H25C0.969450.823220.418100.1420*
H26A0.813760.56746−0.310440.1023*
H26B0.792480.49055−0.206330.1023*
H26C0.903490.62961−0.188000.1023*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.124 (2)0.133 (2)0.0530 (14)0.0852 (18)0.0161 (13)0.0295 (13)
O20.1026 (17)0.129 (2)0.0474 (13)0.0638 (15)0.0173 (12)0.0229 (12)
C10.0587 (17)0.0766 (19)0.0484 (18)0.0235 (14)0.0068 (13)0.0122 (14)
C20.0520 (16)0.0657 (17)0.0501 (17)0.0173 (13)0.0042 (12)0.0140 (13)
C30.0579 (17)0.0641 (17)0.0521 (18)0.0204 (14)0.0070 (13)0.0150 (13)
C40.0521 (15)0.0582 (16)0.0479 (16)0.0154 (12)0.0041 (12)0.0113 (12)
C50.0657 (17)0.0561 (16)0.0539 (18)0.0277 (13)0.0077 (13)0.0108 (13)
C60.0669 (17)0.0578 (16)0.0485 (16)0.0256 (13)0.0022 (13)0.0015 (12)
C70.0585 (16)0.0545 (15)0.0463 (16)0.0175 (12)0.0013 (12)0.0073 (12)
C80.132 (3)0.0526 (17)0.059 (2)0.0344 (18)−0.0045 (19)0.0109 (14)
C90.127 (3)0.0553 (17)0.0504 (19)0.0250 (17)−0.0045 (18)0.0022 (13)
C100.082 (2)0.0626 (18)0.0511 (18)0.0279 (16)−0.0016 (15)0.0081 (14)
C110.119 (3)0.114 (3)0.070 (2)0.033 (2)0.028 (2)0.033 (2)
C120.096 (3)0.101 (3)0.086 (3)0.050 (2)−0.006 (2)0.021 (2)
C130.096 (2)0.100 (2)0.060 (2)0.051 (2)0.0051 (17)0.0127 (17)
O30.0924 (16)0.1221 (19)0.0495 (13)0.0610 (15)0.0026 (11)0.0178 (12)
O40.121 (2)0.1225 (19)0.0434 (13)0.0694 (16)0.0134 (12)0.0186 (12)
C140.0642 (17)0.0628 (16)0.0431 (17)0.0216 (14)0.0066 (13)0.0128 (12)
C150.0584 (16)0.0521 (14)0.0479 (16)0.0146 (12)0.0059 (12)0.0105 (12)
C160.0567 (16)0.0578 (16)0.0483 (17)0.0213 (13)0.0034 (13)0.0093 (12)
C170.0559 (16)0.0495 (14)0.0431 (15)0.0198 (11)0.0046 (12)0.0069 (11)
C180.0521 (16)0.098 (2)0.0483 (17)0.0340 (15)0.0073 (13)0.0095 (15)
C190.0619 (19)0.113 (3)0.0445 (17)0.0346 (17)0.0169 (14)0.0206 (16)
C200.0565 (17)0.0635 (16)0.0466 (16)0.0220 (13)0.0048 (13)0.0109 (12)
C210.0468 (15)0.0680 (17)0.0530 (17)0.0167 (12)0.0035 (13)0.0116 (13)
C220.0537 (16)0.0681 (17)0.0469 (16)0.0138 (13)0.0112 (12)0.0131 (13)
C230.0678 (19)0.100 (2)0.0496 (18)0.0323 (18)0.0030 (15)0.0207 (16)
C240.132 (3)0.093 (3)0.057 (2)0.038 (2)0.008 (2)0.0242 (18)
C250.110 (3)0.099 (3)0.057 (2)0.010 (2)−0.0022 (19)0.0044 (18)
C260.080 (2)0.077 (2)0.0547 (19)0.0349 (16)0.0105 (15)0.0105 (14)

Geometric parameters (Å, °)

O1—C11.277 (4)C13—H13A0.9600
O2—C11.231 (4)C13—H13B0.9600
O1—H10.94 (4)C13—H13C0.9600
O3—C141.281 (4)C14—C151.482 (4)
O4—C141.234 (3)C15—C161.328 (4)
O3—H3A0.93 (4)C15—C261.499 (4)
C1—C21.481 (4)C16—C171.470 (3)
C2—C131.491 (5)C17—C181.384 (4)
C2—C31.327 (3)C17—C221.382 (4)
C3—C41.465 (4)C18—C191.378 (3)
C4—C51.380 (4)C19—C201.380 (4)
C4—C91.390 (4)C20—C211.374 (4)
C5—C61.374 (4)C20—C231.513 (4)
C6—C71.372 (4)C21—C221.381 (3)
C7—C101.511 (4)C23—C241.518 (5)
C7—C81.379 (4)C23—C251.528 (5)
C8—C91.376 (5)C16—H160.91 (3)
C10—C111.515 (5)C18—H180.9300
C10—C121.517 (5)C19—H190.9300
C3—H30.96 (3)C21—H210.9300
C5—H50.9300C22—H220.9300
C6—H60.9300C23—H230.99 (4)
C8—H80.9300C24—H24A0.9600
C9—H90.9300C24—H24B0.9600
C10—H101.04 (3)C24—H24C0.9600
C11—H11A0.9600C25—H25A0.9600
C11—H11B0.9600C25—H25B0.9600
C11—H11C0.9600C25—H25C0.9600
C12—H12C0.9600C26—H26A0.9600
C12—H12B0.9600C26—H26B0.9600
C12—H12A0.9600C26—H26C0.9600
O1···O4i2.644 (4)H5···C17iv3.0200
O2···O3i2.631 (3)H6···H102.3100
O2···C14i3.377 (4)H6···H24Biv2.4800
O3···O2ii2.631 (3)H8···H11C2.5500
O4···C1ii3.382 (4)H8···H12B2.3800
O4···O1ii2.644 (4)H8···C16iii2.9900
O1···H192.7500H8···C17iii3.0700
O1···H3Ai2.83 (4)H8···C122.9000
O1···H32.35 (2)H8···C113.0400
O2···H11Bi2.8400H9···C132.6900
O2···H13A2.2800H9···C22.9600
O2···H3Ai1.71 (4)H9···O3iii2.8800
O3···H9iii2.8800H9···H13C2.0700
O3···H162.31 (2)H10···H62.3100
O3···H1ii2.86 (4)H11A···H12A2.4300
O4···H1ii1.71 (4)H11B···O2ii2.8400
O4···H26A2.3000H11C···C82.8800
C1···O4i3.382 (4)H11C···H82.5500
C9···C133.187 (5)H12A···H13Bv2.5900
C13···C93.187 (5)H12A···H11A2.4300
C14···O2ii3.377 (4)H12B···C82.8100
C22···C263.246 (4)H12B···H82.3800
C26···C223.246 (4)H13A···O22.2800
C1···H3Ai2.58 (3)H13B···H25Cvi2.4600
C2···H92.9600H13B···H12Av2.5900
C3···H26Biv2.8700H13C···C92.7900
C5···H183.0700H13C···H92.0700
C8···H11C2.8800H16···O32.31 (2)
C8···H12B2.8100H16···H182.3700
C9···H13C2.7900H18···C53.0700
C11···H83.0400H18···H32.5700
C12···H82.9000H18···H52.5700
C13···H92.6900H18···H162.3700
C14···H1ii2.59 (4)H19···O12.7500
C15···H222.9900H19···C242.8100
C16···H8iii2.9900H19···H24C2.2700
C17···H5iv3.0200H21···H232.3100
C17···H8iii3.0700H22···C152.9900
C19···H24C2.7700H22···C262.7600
C19···H25B2.9200H22···H26C2.1400
C22···H26C2.8400H23···H212.3100
C24···H192.8100H24A···H25A2.4300
C26···H222.7600H24A···H24Avii2.5300
H1···O4i1.71 (4)H24B···H6iv2.4800
H1···O3i2.86 (4)H24C···C192.7700
H1···C14i2.59 (4)H24C···H192.2700
H1···H3Ai2.33 (5)H24C···H25B2.5600
H3···H52.3500H25A···H24A2.4300
H3···O12.35 (2)H25B···C192.9200
H3···H182.5700H25B···H24C2.5600
H3···H26Biv2.4900H25C···H13Bviii2.4600
H3A···C1ii2.58 (3)H26A···O42.3000
H3A···O1ii2.83 (4)H26B···C3iv2.8700
H3A···O2ii1.71 (4)H26B···H3iv2.4900
H3A···H1ii2.33 (5)H26C···C222.8400
H5···H32.3500H26C···H222.1400
H5···H182.5700
C1—O1—H1115 (2)H13A—C13—H13C109.00
C14—O3—H3A113 (2)O3—C14—O4122.0 (3)
O1—C1—O2122.1 (3)O3—C14—C15117.7 (2)
O1—C1—C2117.7 (3)O4—C14—C15120.4 (3)
O2—C1—C2120.2 (3)C14—C15—C16117.6 (3)
C1—C2—C13115.4 (2)C14—C15—C26115.6 (2)
C1—C2—C3118.2 (3)C16—C15—C26126.8 (3)
C3—C2—C13126.4 (3)C15—C16—C17130.1 (3)
C2—C3—C4129.9 (3)C16—C17—C22125.0 (2)
C3—C4—C9124.2 (3)C18—C17—C22117.0 (2)
C3—C4—C5119.0 (3)C16—C17—C18117.9 (3)
C5—C4—C9116.7 (3)C17—C18—C19121.7 (3)
C4—C5—C6121.8 (3)C18—C19—C20121.2 (3)
C5—C6—C7121.7 (3)C19—C20—C21117.1 (2)
C8—C7—C10121.6 (3)C21—C20—C23121.5 (3)
C6—C7—C8116.7 (2)C19—C20—C23121.4 (3)
C6—C7—C10121.6 (2)C20—C21—C22122.1 (3)
C7—C8—C9122.2 (3)C17—C22—C21120.9 (3)
C4—C9—C8120.8 (3)C20—C23—C25110.6 (3)
C7—C10—C12112.2 (3)C24—C23—C25109.8 (3)
C7—C10—C11111.5 (3)C20—C23—C24112.6 (3)
C11—C10—C12111.2 (3)C15—C16—H16116.4 (15)
C2—C3—H3118.7 (14)C17—C16—H16113.4 (15)
C4—C3—H3111.3 (14)C17—C18—H18119.00
C6—C5—H5119.00C19—C18—H18119.00
C4—C5—H5119.00C18—C19—H19119.00
C5—C6—H6119.00C20—C19—H19119.00
C7—C6—H6119.00C20—C21—H21119.00
C9—C8—H8119.00C22—C21—H21119.00
C7—C8—H8119.00C17—C22—H22120.00
C4—C9—H9120.00C21—C22—H22120.00
C8—C9—H9120.00C20—C23—H23107 (2)
C11—C10—H10103.8 (18)C24—C23—H23111.1 (19)
C12—C10—H10110.3 (17)C25—C23—H23105.4 (19)
C7—C10—H10107.5 (19)C23—C24—H24A109.00
C10—C11—H11B109.00C23—C24—H24B109.00
C10—C11—H11C109.00C23—C24—H24C109.00
H11A—C11—H11B110.00H24A—C24—H24B109.00
H11A—C11—H11C110.00H24A—C24—H24C109.00
H11B—C11—H11C109.00H24B—C24—H24C109.00
C10—C11—H11A109.00C23—C25—H25A109.00
C10—C12—H12A109.00C23—C25—H25B109.00
C10—C12—H12C109.00C23—C25—H25C109.00
H12A—C12—H12B109.00H25A—C25—H25B109.00
H12A—C12—H12C109.00H25A—C25—H25C109.00
H12B—C12—H12C109.00H25B—C25—H25C109.00
C10—C12—H12B110.00C15—C26—H26A109.00
C2—C13—H13A110.00C15—C26—H26B109.00
C2—C13—H13C109.00C15—C26—H26C109.00
H13A—C13—H13B109.00H26A—C26—H26B109.00
C2—C13—H13B109.00H26A—C26—H26C109.00
H13B—C13—H13C109.00H26B—C26—H26C109.00
O1—C1—C2—C38.4 (5)O3—C14—C15—C168.1 (4)
O1—C1—C2—C13−173.7 (3)O3—C14—C15—C26−174.0 (3)
O2—C1—C2—C3−171.3 (3)O4—C14—C15—C16−172.2 (3)
O2—C1—C2—C136.6 (5)O4—C14—C15—C265.7 (4)
C1—C2—C3—C4179.7 (3)C14—C15—C16—C17−179.3 (3)
C13—C2—C3—C42.0 (6)C26—C15—C16—C173.1 (5)
C2—C3—C4—C5−150.3 (3)C15—C16—C17—C18−149.2 (3)
C2—C3—C4—C931.8 (5)C15—C16—C17—C2233.4 (5)
C3—C4—C5—C6179.8 (3)C16—C17—C18—C19−179.4 (3)
C9—C4—C5—C6−2.1 (5)C22—C17—C18—C19−1.7 (4)
C3—C4—C9—C8179.7 (3)C16—C17—C22—C21178.4 (3)
C5—C4—C9—C81.7 (5)C18—C17—C22—C210.9 (4)
C4—C5—C6—C71.1 (5)C17—C18—C19—C202.1 (5)
C5—C6—C7—C80.4 (5)C18—C19—C20—C21−1.6 (5)
C5—C6—C7—C10179.4 (3)C18—C19—C20—C23177.2 (3)
C6—C7—C8—C9−0.8 (5)C19—C20—C21—C220.8 (5)
C10—C7—C8—C9−179.8 (3)C23—C20—C21—C22−177.9 (3)
C6—C7—C10—C11−111.1 (3)C19—C20—C23—C2450.7 (4)
C6—C7—C10—C12123.4 (3)C19—C20—C23—C25−72.6 (4)
C8—C7—C10—C1168.0 (4)C21—C20—C23—C24−130.6 (3)
C8—C7—C10—C12−57.6 (4)C21—C20—C23—C25106.1 (4)
C7—C8—C9—C4−0.3 (6)C20—C21—C22—C17−0.6 (5)

Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (iii) −x+1, −y+2, −z; (iv) −x+1, −y+1, −z; (v) −x, −y+2, −z; (vi) x−1, y, z; (vii) −x+2, −y+1, −z+1; (viii) x+1, y, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.94 (4)1.71 (4)2.644 (4)175 (3)
O3—H3A···O2ii0.93 (4)1.71 (4)2.631 (3)169 (3)
C3—H3···O10.96 (3)2.35 (2)2.707 (4)101.2 (16)
C13—H13A···O20.96002.28002.759 (4)110.00
C16—H16···O30.91 (3)2.31 (2)2.698 (4)105.1 (18)
C26—H26A···O40.96002.30002.770 (4)110.00

Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2064).

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