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ISSN: 2056-9890

2-(2,5-Di­methyl­phen­­oxy)ethanol

aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan
*Correspondence e-mail: okuno@center.wakayama-u.ac.jp

(Received 31 January 2013; accepted 22 February 2013; online 28 February 2013)

There are two independent mol­ecules in the asymmetric unit of the title phen­oxy­ethanol derivative, C10H14O2, Each molecule has an approximately planar structure except for the hy­droxy groups (r.m.s. deviations = 0.0281 and 0.0144 Å). The ethyl­enedi­oxy groups have a gauche conformation. In the crystal, the mol­ecules form O—H⋯O hydrogen-bonded chains along the a axis.

Related literature

For related structures of phen­oxy­ethanol derivatives, see: Sanyal & Lahti (2006[Sanyal, N. & Lahti, P. M. (2006). Cryst. Growth Des. 6, 1253-1255.]); Sierra & Lahti (2004[Sierra, C. A. & Lahti, P. M. (2004). Chem. Mater. 16, 55-61.]).

[Scheme 1]

Experimental

Crystal data
  • C10H14O2

  • Mr = 166.22

  • Orthorhombic, P n a 21

  • a = 8.274 (3) Å

  • b = 13.745 (4) Å

  • c = 17.113 (5) Å

  • V = 1946.2 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 93 K

  • 0.10 × 0.09 × 0.09 mm

Data collection
  • Rigaku Saturn724+ diffractometer

  • Absorption correction: numerical (NUMABS; Rigaku, 1999[Rigaku (1999). NUMABS Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.989, Tmax = 0.993

  • 16794 measured reflections

  • 2661 independent reflections

  • 2440 reflections with F2 > 2σ(F2)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.121

  • S = 1.09

  • 2660 reflections

  • 223 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O4i 0.84 1.82 2.623 (3) 159
O4—H4⋯O2ii 0.84 1.80 2.626 (3) 167
Symmetry codes: (i) [-x+1, -y+1, z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare, et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information


Comment top

The title compound, C10H14O2, is a phenoxyethanol derivative whose structures are often observed in phenyleneethynylene derivatives (Sanyal & Lahti, 2006) or phynylenevinylene derivatives (Sierra & Lahti, 2004). Introduction of ethylenedioxy groups was aiming for control of intermolecular interacrions and/or for improvement of solubility to common organic solvents.

The molecular structure of the title compound is shown in Fig. 1. There are two crystallographically independent molecules (A and B) in the unit cell. Both molecules have a planar structure (the C1—C10/O1 plane: r.m.s. deviation = 0.0281 Å, the C11—C20/O3 plane: r.m.s. deviation = 0.0144 Å) except for the hydroxyl groups. The significant difference between A and B is recognized at the torsion angles of ethylenedioxy groups which have a gauche conformation.

In the crystal, the molecules form one-dimensional O—H···O hydrogen-bonds (Fig. 2), where the intermolecular distances of O2···O4i and O2···O4ii are 2.623 (3) Å and 2.626 (3) Å, respectively [Symmetry codes: (i) -x + 1, -y + 1, z + 1/2; (ii) -x + 1/2, y + 1/2, z + 1/2.].

Related literature top

For related structures of phenoxyethanol derivatives, see: Sanyal & Lahti (2006); Sierra & Lahti (2004).

Experimental top

The title compound was commercially purchased. Single crystals with sufficient quality were prepared by sublimation at room temperature.

Refinement top

Although CheckCIF suggested the spacegroup Pbcn, there existed many reflections which broke systematic absence under Pbcn on (0kl) reflections. In this reason, the space group Pna21 was selected after the lattice transformation. Friedel pairs were merged because the molecule itself was achiral and because there were not any anomalous scattering effects. All H atoms were placed at ideal positions and were refined as riding on their parent atoms. Uiso(H) values of the H atoms were set at 1.2Ueq(parent atom).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SIR92 (Altomare, et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres.
[Figure 2] Fig. 2. A view of the intermolecular interactions in the title compound. [Symmetry codes: (i) -x + 1, -y + 1, z + 1/2; (ii) -x + 1/2, y + 1/2, z + 1/2.]
2-(2,5-Dimethylphenoxy)ethanol top
Crystal data top
C10H14O2F(000) = 720.00
Mr = 166.22Dx = 1.134 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2c -2nCell parameters from 6921 reflections
a = 8.274 (3) Åθ = 2.5–31.2°
b = 13.745 (4) ŵ = 0.08 mm1
c = 17.113 (5) ÅT = 93 K
V = 1946.2 (11) Å3Block, colourless
Z = 80.10 × 0.09 × 0.09 mm
Data collection top
Rigaku Saturn724+
diffractometer
2440 reflections with F2 > 2σ(F2)
Detector resolution: 28.445 pixels mm-1Rint = 0.027
ω scansθmax = 29.0°
Absorption correction: numerical
(NUMABS; Rigaku, 1999)
h = 1111
Tmin = 0.989, Tmax = 0.993k = 1814
16794 measured reflectionsl = 2321
2661 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0655P)2 + 0.3857P]
where P = (Fo2 + 2Fc2)/3
2660 reflections(Δ/σ)max < 0.001
223 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.18 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C10H14O2V = 1946.2 (11) Å3
Mr = 166.22Z = 8
Orthorhombic, Pna21Mo Kα radiation
a = 8.274 (3) ŵ = 0.08 mm1
b = 13.745 (4) ÅT = 93 K
c = 17.113 (5) Å0.10 × 0.09 × 0.09 mm
Data collection top
Rigaku Saturn724+
diffractometer
2661 independent reflections
Absorption correction: numerical
(NUMABS; Rigaku, 1999)
2440 reflections with F2 > 2σ(F2)
Tmin = 0.989, Tmax = 0.993Rint = 0.027
16794 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0461 restraint
wR(F2) = 0.121H-atom parameters constrained
S = 1.09Δρmax = 0.23 e Å3
2660 reflectionsΔρmin = 0.18 e Å3
223 parameters
Special details top

Refinement. Refinement was performed using all reflections except for one with very negative F2. 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
O10.83268 (18)0.62210 (11)0.70220 (11)0.0250 (4)
O20.60617 (19)0.72154 (12)0.80422 (13)0.0318 (4)
O30.34067 (18)0.38176 (11)0.49535 (10)0.0250 (4)
O40.13226 (17)0.28761 (13)0.39046 (13)0.0328 (4)
C10.9552 (3)0.61937 (15)0.64824 (15)0.0225 (5)
C21.0979 (3)0.57326 (15)0.67334 (17)0.0257 (5)
C31.2248 (3)0.5683 (2)0.62073 (18)0.0311 (6)
C41.2134 (3)0.6070 (2)0.54556 (19)0.0356 (7)
C51.0719 (3)0.65250 (17)0.52115 (19)0.0328 (6)
C60.9431 (3)0.65832 (17)0.57361 (17)0.0272 (6)
C71.1107 (3)0.53209 (18)0.7542 (2)0.0321 (6)
C81.0567 (4)0.6947 (3)0.4399 (2)0.0479 (8)
C90.6793 (3)0.65794 (17)0.67692 (18)0.0262 (5)
C100.5661 (3)0.65268 (19)0.74576 (17)0.0279 (6)
C110.4644 (3)0.38227 (16)0.54812 (16)0.0241 (5)
C120.6078 (3)0.42751 (15)0.52298 (18)0.0267 (6)
C130.7366 (3)0.4303 (2)0.57477 (19)0.0319 (6)
C140.7263 (3)0.3917 (2)0.64977 (18)0.0345 (7)
C150.5848 (3)0.34733 (18)0.67431 (19)0.0322 (6)
C160.4525 (3)0.34246 (17)0.62299 (17)0.0279 (6)
C170.6194 (3)0.46858 (18)0.4415 (2)0.0321 (6)
C180.5700 (4)0.3044 (3)0.7549 (2)0.0481 (8)
C190.1892 (3)0.34104 (16)0.51982 (16)0.0236 (5)
C200.0756 (3)0.34828 (17)0.45185 (17)0.0264 (5)
H20.69220.70460.82650.0382*
H31.32250.53770.63630.0374*
H40.05570.27490.35990.0393*
H4A1.30280.60220.51090.0428*
H60.84570.68940.55800.0327*
H7A1.10320.58490.79250.0385*
H7B1.21460.49870.76010.0385*
H7C1.02250.48570.76290.0385*
H8A1.12730.65880.40410.0575*
H8B1.08860.76330.44080.0575*
H8C0.94440.68920.42230.0575*
H9A0.63750.61780.63330.0314*
H9B0.68940.72600.65860.0314*
H10A0.45420.66460.72770.0335*
H10B0.57030.58650.76850.0335*
H130.83510.45950.55850.0383*
H140.81630.39580.68410.0413*
H160.35500.31210.63920.0335*
H17A0.61890.41530.40350.0385*
H17B0.71990.50570.43630.0385*
H17C0.52700.51150.43170.0385*
H18A0.67790.29620.77750.0577*
H18B0.51630.24100.75160.0577*
H18C0.50610.34810.78790.0577*
H19A0.14590.37760.56510.0284*
H19B0.20350.27220.53530.0284*
H20A0.03410.32760.46800.0317*
H20B0.06950.41650.43360.0317*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0203 (7)0.0299 (9)0.0248 (10)0.0023 (6)0.0004 (7)0.0004 (7)
O20.0259 (7)0.0418 (9)0.0278 (10)0.0065 (6)0.0010 (7)0.0035 (8)
O30.0197 (7)0.0298 (9)0.0255 (10)0.0032 (6)0.0002 (7)0.0008 (7)
O40.0231 (7)0.0476 (9)0.0276 (10)0.0026 (7)0.0004 (7)0.0118 (9)
C10.0204 (9)0.0213 (10)0.0258 (13)0.0014 (7)0.0004 (9)0.0039 (10)
C20.0240 (9)0.0219 (10)0.0312 (15)0.0004 (8)0.0018 (9)0.0068 (10)
C30.0251 (10)0.0263 (13)0.0420 (17)0.0029 (8)0.0022 (11)0.0107 (11)
C40.0323 (11)0.0323 (13)0.0423 (18)0.0009 (10)0.0110 (12)0.0112 (13)
C50.0366 (12)0.0295 (12)0.0323 (16)0.0020 (9)0.0082 (12)0.0057 (11)
C60.0288 (10)0.0267 (12)0.0262 (14)0.0014 (8)0.0005 (10)0.0039 (10)
C70.0285 (11)0.0309 (12)0.0369 (18)0.0037 (9)0.0062 (10)0.0037 (12)
C80.0570 (17)0.0544 (17)0.0323 (18)0.0001 (14)0.0147 (14)0.0006 (16)
C90.0222 (9)0.0287 (11)0.0276 (14)0.0041 (8)0.0029 (9)0.0007 (11)
C100.0207 (10)0.0351 (13)0.0280 (15)0.0009 (8)0.0021 (9)0.0022 (11)
C110.0219 (9)0.0235 (11)0.0269 (13)0.0012 (8)0.0015 (9)0.0065 (10)
C120.0239 (9)0.0215 (10)0.0347 (16)0.0006 (8)0.0022 (9)0.0066 (10)
C130.0223 (10)0.0278 (13)0.0456 (18)0.0028 (8)0.0017 (11)0.0117 (12)
C140.0300 (11)0.0321 (13)0.0413 (18)0.0014 (9)0.0131 (11)0.0105 (12)
C150.0343 (12)0.0325 (12)0.0297 (16)0.0036 (9)0.0060 (12)0.0043 (12)
C160.0260 (10)0.0281 (12)0.0295 (15)0.0016 (8)0.0010 (10)0.0032 (10)
C170.0292 (11)0.0315 (12)0.0355 (17)0.0056 (9)0.0072 (10)0.0009 (12)
C180.0497 (16)0.0611 (19)0.0335 (19)0.0021 (14)0.0109 (14)0.0048 (16)
C190.0200 (9)0.0276 (11)0.0233 (13)0.0028 (8)0.0001 (8)0.0010 (10)
C200.0207 (9)0.0280 (12)0.0305 (15)0.0001 (8)0.0009 (9)0.0029 (11)
Geometric parameters (Å, º) top
O1—C11.372 (3)C3—H30.950
O1—C91.429 (3)C4—H4A0.950
O2—C101.417 (4)C6—H60.950
O3—C111.365 (3)C7—H7A0.980
O3—C191.435 (3)C7—H7B0.980
O4—C201.421 (4)C7—H7C0.980
C1—C21.407 (3)C8—H8A0.980
C1—C61.388 (4)C8—H8B0.980
C2—C31.384 (4)C8—H8C0.980
C2—C71.499 (5)C9—H9A0.990
C3—C41.395 (5)C9—H9B0.990
C4—C51.392 (4)C10—H10A0.990
C5—C61.396 (4)C10—H10B0.990
C5—C81.511 (5)C13—H130.950
C9—C101.506 (4)C14—H140.950
C11—C121.407 (4)C16—H160.950
C11—C161.397 (4)C17—H17A0.980
C12—C131.387 (4)C17—H17B0.980
C12—C171.507 (5)C17—H17C0.980
C13—C141.391 (5)C18—H18A0.980
C14—C151.385 (4)C18—H18B0.980
C15—C161.405 (4)C18—H18C0.980
C15—C181.504 (5)C19—H19A0.990
C19—C201.499 (4)C19—H19B0.990
O2—H20.840C20—H20A0.990
O4—H40.840C20—H20B0.990
O1···O22.903 (3)H2···H20Aiv3.2293
O1···C72.759 (3)H2···H20Bii3.1657
O3···O42.805 (3)H3···O3viii3.2303
O3···C172.755 (3)H3···C9viii3.4535
C1···C42.772 (4)H3···C10viii3.1731
C2···C52.831 (5)H3···C11viii2.8669
C3···C62.759 (4)H3···C12viii3.4095
C6···C92.809 (4)H3···C15viii3.4613
C11···C142.782 (4)H3···C16viii2.9000
C12···C152.821 (5)H3···C19viii3.5351
C13···C162.769 (4)H3···H9Aviii2.8298
C16···C192.804 (4)H3···H9Bi3.4509
O1···O2i3.576 (3)H3···H10Aviii2.5836
O1···O4ii3.465 (3)H3···H10Bviii3.1252
O1···C133.512 (4)H3···H16viii3.1130
O1···C143.407 (4)H3···H19Aviii2.9097
O2···O1iii3.576 (3)H4···O1v3.1850
O2···O3ii3.593 (3)H4···O2vii1.7996
O2···O4iv2.626 (3)H4···O2v2.9563
O2···O4ii2.623 (3)H4···C7v3.4937
O2···C7iii3.493 (4)H4···C10vii2.7662
O2···C20iv3.417 (4)H4···H2vii2.3376
O3···O2v3.593 (3)H4···H2v2.1820
O3···C3vi3.479 (4)H4···H7Av2.6022
O3···C4vi3.381 (4)H4···H10Avii2.7247
O4···O1v3.465 (3)H4···H10Bvii3.2001
O4···O2vii2.626 (3)H4···H17Ax2.7674
O4···O2v2.623 (3)H4A···O3viii3.0584
O4···C10vii3.502 (4)H4A···C11viii3.3670
C1···C133.406 (4)H4A···C12viii3.4901
C3···O3viii3.479 (4)H4A···C17viii3.4133
C3···C11viii3.466 (4)H4A···H6i2.9966
C3···C19viii3.582 (4)H4A···H8Bi3.2319
C4···O3viii3.381 (4)H4A···H8Ci3.4481
C6···C133.569 (4)H4A···H9Aviii3.4798
C7···O2i3.493 (4)H4A···H9Bi3.5838
C10···O4iv3.502 (4)H4A···H17Cviii2.6142
C11···C3vi3.466 (4)H4A···H19Aviii3.4762
C13···O13.512 (4)H4A···H20Bviii3.4628
C13···C13.406 (4)H6···C4iii3.0126
C13···C63.569 (4)H6···C5iii3.2023
C14···O13.407 (4)H6···C8iii3.5130
C19···C3vi3.582 (4)H6···H4Aiii2.9966
C20···O2vii3.417 (4)H6···H8Biii2.9956
O1···H22.6761H6···H9Bi3.5218
O1···H62.6371H6···H133.1605
O1···H7A2.7675H6···H17B3.4341
O1···H7C2.6573H7A···O2i2.6680
O1···H10A3.2155H7A···O4ii3.1101
O1···H10B2.4978H7A···C17xi3.5084
O2···H9A3.2640H7A···C20ii3.2347
O2···H9B2.5862H7A···H2i3.0416
O3···H162.6444H7A···H4ii2.6022
O3···H17A2.8254H7A···H9Bi3.5382
O3···H17C2.5963H7A···H10Aviii3.2964
O3···H20A3.2233H7A···H17Axi2.9824
O3···H20B2.5260H7A···H17Bxi3.1225
O4···H19A3.2360H7A···H20Aii3.2843
O4···H19B2.5572H7A···H20Bii2.8050
C1···H33.2463H7B···C17xi3.4235
C1···H7A2.7964H7B···H10Aviii3.0714
C1···H7B3.3202H7B···H10Bviii3.1834
C1···H7C2.7453H7B···H16viii3.4946
C1···H9A2.6409H7B···H17Axi3.0518
C1···H9B2.6484H7B···H17Bxi3.0638
C2···H4A3.2802H7B···H18Cviii3.2140
C2···H63.2858H7C···C143.3800
C3···H7A3.1158H7C···H8Axi3.3643
C3···H7B2.5718H7C···H142.5017
C3···H7C3.1640H7C···H18Bix3.1223
C4···H63.2535H7C···H20Bii3.3040
C4···H8A2.6225H8A···H7Cxii3.3643
C4···H8B2.9832H8A···H8Ci3.3680
C4···H8C3.2688H8A···H18Axii2.7695
C5···H33.2670H8A···H18Bxiii3.0820
C6···H4A3.2561H8A···H18Cxiii3.4546
C6···H8A3.2772H8A···H20Bviii3.4022
C6···H8B2.9495H8B···C18xiii3.4879
C6···H8C2.6249H8B···H4Aiii3.2319
C6···H9A2.7832H8B···H6i2.9956
C6···H9B2.7175H8B···H8Ci3.0322
C7···H32.6742H8B···H17Bi3.3558
C8···H4A2.6893H8B···H17Ci3.1407
C8···H62.6717H8B···H18Axiii3.5878
C9···H22.6408H8B···H18Axii3.4942
C9···H62.4947H8B···H18Bxiii3.3665
C11···H133.2509H8B···H18Cxiii2.9685
C11···H17A2.8222H8C···C8iii3.5956
C11···H17B3.3184H8C···C18xiii3.2752
C11···H17C2.7183H8C···H4Aiii3.4481
C11···H19A2.6519H8C···H8Aiii3.3680
C11···H19B2.6451H8C···H8Biii3.0322
C12···H143.2820H8C···H17B3.1414
C12···H163.2937H8C···H18Axiii3.0530
C13···H17A3.0953H8C···H18Bxiii3.0237
C13···H17B2.5899H8C···H18Cxiii3.1964
C13···H17C3.2007H9A···C3vi3.4888
C14···H163.2666H9A···C123.2353
C14···H18A2.5812H9A···C132.8840
C14···H18B3.2167H9A···C143.2058
C14···H18C3.0450H9A···H3vi2.8298
C15···H133.2548H9A···H4Avi3.4798
C16···H143.2697H9A···H133.0072
C16···H18A3.2977H9A···H143.5011
C16···H18B2.6582H9B···C1iii2.8820
C16···H18C2.8584H9B···C2iii2.8725
C16···H19A2.7659H9B···C3iii2.9151
C16···H19B2.7254H9B···C4iii3.0086
C17···H132.6849H9B···C5iii3.0444
C18···H142.6823H9B···C6iii2.9663
C18···H162.6629H9B···H3iii3.4509
C19···H43.0880H9B···H4Aiii3.5838
C19···H162.4931H9B···H6iii3.5218
H2···H9A3.5433H9B···H7Aiii3.5382
H2···H9B2.8882H9B···H10Ai2.9082
H2···H10A2.6529H10A···O1iii3.1299
H2···H10B2.1538H10A···O2iii3.5292
H3···H4A2.3282H10A···O4iv3.3360
H3···H7A3.2960H10A···C1iii3.2658
H3···H7B2.3611H10A···C2vi3.3360
H3···H7C3.3715H10A···C3vi2.9502
H4···H19B3.2418H10A···C6iii3.5896
H4···H20A2.1200H10A···C7vi3.4061
H4···H20B2.3226H10A···C9iii3.4465
H4A···H8A2.4601H10A···H2iii3.2850
H4A···H8B3.0791H10A···H3vi2.5836
H4A···H8C3.5383H10A···H4iv2.7247
H6···H8A3.5420H10A···H7Avi3.2964
H6···H8B3.0161H10A···H7Bvi3.0714
H6···H8C2.4630H10A···H9Biii2.9082
H6···H9A2.3655H10A···H17Aii3.2593
H6···H9B2.2106H10B···C143.5999
H9A···H10A2.3073H10B···C17ii3.4361
H9A···H10B2.4173H10B···H3vi3.1252
H9B···H10A2.4288H10B···H4iv3.2001
H9B···H10B2.8607H10B···H7Bvi3.1834
H13···H142.3267H10B···H17Aii2.7916
H13···H17A3.2566H10B···H17Cii3.2042
H13···H17B2.3840H10B···H18C3.3363
H13···H17C3.4227H13···O13.3226
H14···H18A2.3954H13···C12.8586
H14···H18B3.4669H13···C23.3218
H14···H18C3.1897H13···C53.3588
H16···H18A3.5759H13···C62.8862
H16···H18B2.5364H13···C19viii3.4168
H16···H18C2.8783H13···C20viii3.1030
H16···H19A2.3263H13···H63.1605
H16···H19B2.2432H13···H9A3.0072
H19A···H20A2.3351H13···H19Aviii2.8099
H19A···H20B2.3980H13···H19Bix3.3894
H19B···H20A2.4028H13···H20Aviii2.6198
H19B···H20B2.8631H13···H20Bviii2.9460
O1···H4ii3.1850H14···O13.1293
O1···H10Ai3.1299H14···C13.3383
O1···H133.3226H14···C23.3789
O1···H143.1293H14···C73.2990
O2···H2iii3.5932H14···H7C2.5017
O2···H4iv1.7996H14···H9A3.5011
O2···H4ii2.9563H14···H16ix2.9757
O2···H7Aiii2.6680H14···H18Bix2.7574
O2···H10Ai3.5292H14···H19Aviii3.4131
O2···H17Aii3.1450H14···H19Bix3.5612
O2···H20Aiv3.2142H16···C14x3.0020
O3···H2v3.1357H16···C15x3.1872
O3···H3vi3.2303H16···C18x3.4700
O3···H4Avi3.0584H16···H3vi3.1130
O3···H20Aix3.0937H16···H7Bvi3.4946
O4···H2vii3.1153H16···H14x2.9757
O4···H2v1.8223H16···H18Ax3.1566
O4···H7Av3.1101H16···H18Bx3.4759
O4···H10Avii3.3360H16···H19Bix3.5801
O4···H17Ax2.7994H17A···O2v3.1450
O4···H20Aix3.4476H17A···O4ix2.7994
C1···H9Bi2.8820H17A···C7xii3.4722
C1···H10Ai3.2658H17A···C10v3.2409
C1···H132.8586H17A···H2xvi3.5447
C1···H143.3383H17A···H2v3.3280
C2···H9Bi2.8725H17A···H4ix2.7674
C2···H10Aviii3.3360H17A···H7Axii2.9824
C2···H133.3218H17A···H7Bxii3.0518
C2···H143.3789H17A···H10Av3.2593
C2···H19Aviii3.2902H17A···H10Bv2.7916
C3···H9Aviii3.4888H17A···H19Bix3.4953
C3···H9Bi2.9151H17A···H20Aviii3.3032
C3···H10Aviii2.9502H17B···C7xii3.4561
C3···H19Aviii2.8652H17B···H63.4341
C4···H6i3.0126H17B···H7Axii3.1225
C4···H9Bi3.0086H17B···H7Bxii3.0638
C4···H17Cviii3.4999H17B···H8Biii3.3558
C4···H19Aviii3.2203H17B···H8C3.1414
C4···H20Bviii3.4561H17B···H20Aviii3.2300
C5···H6i3.2023H17B···H20Bviii3.1414
C5···H9Bi3.0444H17C···C4vi3.4999
C5···H133.3588H17C···H4Avi2.6142
C5···H20Bviii3.5728H17C···H8Biii3.1407
C6···H9Bi2.9663H17C···H10Bv3.2042
C6···H10Ai3.5896H17C···H18Cv3.1396
C6···H132.8862H18A···C8xi3.5442
C7···H4ii3.4937H18A···C18ix3.5479
C7···H10Aviii3.4061H18A···H8Axi2.7695
C7···H143.2990H18A···H8Bxiv3.5878
C7···H17Axi3.4722H18A···H8Bxi3.4942
C7···H17Bxi3.4561H18A···H8Cxiv3.0530
C7···H20Bii3.4845H18A···H16ix3.1566
C8···H6i3.5130H18A···H18Bix2.8806
C8···H8Ci3.5956H18A···H18Cix3.3671
C8···H18Axii3.5442H18B···C8xiv3.3407
C8···H18Bxiii3.3407H18B···C14x3.4809
C8···H18Cxiii3.3883H18B···H7Cx3.1223
C9···H3vi3.4535H18B···H8Axiv3.0820
C9···H10Ai3.4465H18B···H8Bxiv3.3665
C10···H3vi3.1731H18B···H8Cxiv3.0237
C10···H4iv2.7662H18B···H14x2.7574
C10···H17Aii3.2409H18B···H16ix3.4759
C11···H3vi2.8669H18B···H18Ax2.8806
C11···H4Avi3.3670H18C···C8xiv3.3883
C11···H19Bix2.9103H18C···H7Bvi3.2140
C11···H20Aix3.1938H18C···H8Axiv3.4546
C12···H3vi3.4095H18C···H8Bxiv2.9685
C12···H4Avi3.4901H18C···H8Cxiv3.1964
C12···H9A3.2353H18C···H10B3.3363
C12···H19Bix2.8647H18C···H17Cii3.1396
C12···H20Aviii3.3992H18C···H18Ax3.3671
C13···H9A2.8840H19A···C2vi3.2902
C13···H19Aviii3.4670H19A···C3vi2.8652
C13···H19Bix2.8771H19A···C4vi3.2203
C13···H20Aviii2.9891H19A···C13vi3.4670
C14···H7C3.3800H19A···C16x3.5619
C14···H9A3.2058H19A···H3vi2.9097
C14···H10B3.5999H19A···H4Avi3.4762
C14···H16ix3.0020H19A···H13vi2.8099
C14···H18Bix3.4809H19A···H14vi3.4131
C14···H19Bix2.9908H19B···C11x2.9103
C15···H3vi3.4613H19B···C12x2.8647
C15···H16ix3.1872H19B···C13x2.8771
C15···H19Bix3.0526H19B···C14x2.9908
C16···H3vi2.9000H19B···C15x3.0526
C16···H19Aix3.5619H19B···C16x3.0076
C16···H19Bix3.0076H19B···H13x3.3894
C16···H20Aix3.5372H19B···H14x3.5612
C17···H4Avi3.4133H19B···H16x3.5801
C17···H7Axii3.5084H19B···H17Ax3.4953
C17···H7Bxii3.4235H19B···H20Aix2.8149
C17···H10Bv3.4361H20A···O2vii3.2142
C17···H20Aviii3.4900H20A···O3x3.0937
C18···H8Bxiv3.4879H20A···O4x3.4476
C18···H8Cxiv3.2752H20A···C11x3.1938
C18···H16ix3.4700H20A···C12vi3.3992
C18···H18Ax3.5479H20A···C13vi2.9891
C19···H2v3.5076H20A···C16x3.5372
C19···H3vi3.5351H20A···C17vi3.4900
C19···H13vi3.4168H20A···C19x3.3764
C19···H20Aix3.3764H20A···H2vii3.2293
C20···H2v2.9706H20A···H7Av3.2843
C20···H7Av3.2347H20A···H13vi2.6198
C20···H13vi3.1030H20A···H17Avi3.3032
H2···O2i3.5932H20A···H17Bvi3.2300
H2···O3ii3.1357H20A···H19Bx2.8149
H2···O4iv3.1153H20B···C4vi3.4561
H2···O4ii1.8223H20B···C5vi3.5728
H2···C19ii3.5076H20B···C7v3.4845
H2···C20ii2.9706H20B···H2v3.1657
H2···H4iv2.3376H20B···H4Avi3.4628
H2···H4ii2.1820H20B···H7Av2.8050
H2···H7Aiii3.0416H20B···H7Cv3.3040
H2···H10Ai3.2850H20B···H8Avi3.4022
H2···H17Axv3.5447H20B···H13vi2.9460
H2···H17Aii3.3280H20B···H17Bvi3.1414
C1—O1—C9117.5 (2)C5—C8—H8A109.470
C11—O3—C19117.64 (19)C5—C8—H8B109.468
O1—C1—C2115.3 (3)C5—C8—H8C109.474
O1—C1—C6123.7 (2)H8A—C8—H8B109.474
C2—C1—C6121.0 (3)H8A—C8—H8C109.469
C1—C2—C3117.4 (3)H8B—C8—H8C109.472
C1—C2—C7120.7 (3)O1—C9—H9A110.232
C3—C2—C7121.9 (3)O1—C9—H9B110.239
C2—C3—C4122.0 (3)C10—C9—H9A110.237
C3—C4—C5120.3 (3)C10—C9—H9B110.237
C4—C5—C6118.4 (3)H9A—C9—H9B108.510
C4—C5—C8121.2 (3)O2—C10—H10A109.205
C6—C5—C8120.4 (3)O2—C10—H10B109.199
C1—C6—C5121.0 (3)C9—C10—H10A109.216
O1—C9—C10107.4 (3)C9—C10—H10B109.218
O2—C10—C9112.0 (2)H10A—C10—H10B107.903
O3—C11—C12115.6 (3)C12—C13—H13118.933
O3—C11—C16123.5 (2)C14—C13—H13118.940
C12—C11—C16120.9 (3)C13—C14—H14120.026
C11—C12—C13117.7 (3)C15—C14—H14120.024
C11—C12—C17120.2 (3)C11—C16—H16120.006
C13—C12—C17122.1 (3)C15—C16—H16120.001
C12—C13—C14122.1 (3)C12—C17—H17A109.476
C13—C14—C15119.9 (3)C12—C17—H17B109.472
C14—C15—C16119.3 (3)C12—C17—H17C109.470
C14—C15—C18121.3 (3)H17A—C17—H17B109.469
C16—C15—C18119.4 (3)H17A—C17—H17C109.473
C11—C16—C15120.0 (3)H17B—C17—H17C109.467
O3—C19—C20107.2 (2)C15—C18—H18A109.471
O4—C20—C19109.13 (19)C15—C18—H18B109.477
C10—O2—H2109.470C15—C18—H18C109.474
C20—O4—H4109.472H18A—C18—H18B109.467
C2—C3—H3118.987H18A—C18—H18C109.469
C4—C3—H3118.991H18B—C18—H18C109.469
C3—C4—H4A119.849O3—C19—H19A110.279
C5—C4—H4A119.860O3—C19—H19B110.282
C1—C6—H6119.517C20—C19—H19A110.281
C5—C6—H6119.522C20—C19—H19B110.283
C2—C7—H7A109.477H19A—C19—H19B108.533
C2—C7—H7B109.480O4—C20—H20A109.852
C2—C7—H7C109.477O4—C20—H20B109.858
H7A—C7—H7B109.459C19—C20—H20A109.852
H7A—C7—H7C109.465C19—C20—H20B109.858
H7B—C7—H7C109.469H20A—C20—H20B108.282
C1—O1—C9—C10179.42 (15)C4—C5—C6—C10.3 (4)
C9—O1—C1—C2172.98 (16)C8—C5—C6—C1179.6 (3)
C9—O1—C1—C66.8 (3)O1—C9—C10—O269.9 (3)
C11—O3—C19—C20179.47 (16)O3—C11—C12—C13179.65 (17)
C19—O3—C11—C12176.76 (16)O3—C11—C12—C172.0 (3)
C19—O3—C11—C162.3 (3)O3—C11—C16—C15178.99 (18)
O1—C1—C2—C3179.72 (16)C12—C11—C16—C150.0 (4)
O1—C1—C2—C70.7 (3)C16—C11—C12—C130.6 (4)
O1—C1—C6—C5179.49 (18)C16—C11—C12—C17178.96 (19)
C2—C1—C6—C50.3 (4)C11—C12—C13—C141.1 (4)
C6—C1—C2—C30.1 (3)C17—C12—C13—C14179.5 (2)
C6—C1—C2—C7179.49 (19)C12—C13—C14—C151.0 (4)
C1—C2—C3—C40.1 (4)C13—C14—C15—C160.4 (4)
C7—C2—C3—C4179.7 (2)C13—C14—C15—C18179.7 (3)
C2—C3—C4—C50.1 (4)C14—C15—C16—C110.1 (4)
C3—C4—C5—C60.1 (4)C18—C15—C16—C11179.8 (3)
C3—C4—C5—C8179.8 (3)O3—C19—C20—O465.7 (2)
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x+1, y+1, z+1/2; (iii) x1/2, y+3/2, z; (iv) x+1/2, y+1/2, z+1/2; (v) x+1, y+1, z1/2; (vi) x1, y, z; (vii) x+1/2, y1/2, z1/2; (viii) x+1, y, z; (ix) x+1/2, y+1/2, z; (x) x1/2, y+1/2, z; (xi) x+2, y+1, z+1/2; (xii) x+2, y+1, z1/2; (xiii) x+3/2, y+1/2, z1/2; (xiv) x+3/2, y1/2, z+1/2; (xv) x+3/2, y+1/2, z+1/2; (xvi) x+3/2, y1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O4ii0.841.822.623 (3)159
O4—H4···O2vii0.841.802.626 (3)167
Symmetry codes: (ii) x+1, y+1, z+1/2; (vii) x+1/2, y1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC10H14O2
Mr166.22
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)93
a, b, c (Å)8.274 (3), 13.745 (4), 17.113 (5)
V3)1946.2 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.10 × 0.09 × 0.09
Data collection
DiffractometerRigaku Saturn724+
diffractometer
Absorption correctionNumerical
(NUMABS; Rigaku, 1999)
Tmin, Tmax0.989, 0.993
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
16794, 2661, 2440
Rint0.027
(sin θ/λ)max1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.121, 1.09
No. of reflections2660
No. of parameters223
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.18

Computer programs: CrystalClear (Rigaku, 2008), SIR92 (Altomare, et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O4i0.8401.8222.623 (3)158.7
O4—H4···O2ii0.8401.8002.626 (3)167.4
Symmetry codes: (i) x+1, y+1, z+1/2; (ii) x+1/2, y1/2, z1/2.
 

Acknowledgements

This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).

References

First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationRigaku (1999). NUMABS Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
First citationRigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
First citationSanyal, N. & Lahti, P. M. (2006). Cryst. Growth Des. 6, 1253–1255.  Web of Science CSD CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSierra, C. A. & Lahti, P. M. (2004). Chem. Mater. 16, 55–61.  Web of Science CSD CrossRef CAS

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