organic compounds
2-(Naphthalen-1-yl)ethanol
aChemistry Department, SUNY Buffalo State, 1300 Elmwood Ave, Buffalo, NY 14222, USA
*Correspondence e-mail: nazareay@buffalostate.edu
The title compound, C12H11OH, crystallizes with two molecules, A and B, in the with different conformations of the ethanol side chain; one is gauche [torsion angle = 59.58 (17)°] and the other is anti [176.20 (13)°]. In the crystal, [100] chains of alternating A and B molecules are linked by O—H⋯O hydrogen bonds.
Keywords: crystal structure; aromatic; hydrogen bond.
CCDC reference: 1465147
Structure description
The title compound was synthesized by selective hydrogenation of the corresponding ester C10H7CH2CH2CO2Et (Adkins & Burgoyne, 1949) and has some applications as a synthetic block (Huang et al., 2014) and as a labeling agent. One of applications is detection of low concentrations of oxygen-containing functional groups through fluorescent labeling (Feng et al., 2006).
The title compound crystallizes with two molecules in the asymmetric uint: both molecules exhibit standard bond lengths and angles and almost planar naphthalene rings (Fig. 1). They differ in the conformations of the ethanol side-chains; the C1—C11—C12—O1 torsion angle of 176.20 (13)° indicates an anti orientation, whereas the equivalent angle in the second molecule [C21—C31—C32—O2 = 59.58 (17)°] corresponds to a gauche conformation. In the crystal, chains of alternating C1- and C21-molecules are linked by O—H⋯O hydrogen bonds (Table 1, Fig. 2), generating C(2) [100] chains.
Synthesis and crystallization
The title compound is commercially available from Aldrich as 1-napthaleneethanol. The bulk material is suitable for X-ray ); re-crystallization from acetonitrile yields better quality crystals which were used in current study.
(Fig. 3Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1465147
10.1107/S2414314616004235/hb4026sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616004235/hb4026Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616004235/hb4026Isup3.cdx
Supporting information file. DOI: 10.1107/S2414314616004235/hb4026Isup4.cml
The title compound is commercially available from Aldrich as 1-napthaleneethanol. The bulk material is suitable for X-ray
(Fig. 3); re-crystallization from acetonitrile yields better quality crystals which were used in current study.The title compound was synthesized by selective hydrogenation of the corresponding ester C10H7CH2CH2CO2Et (Adkins & Burgoyne, 1949) and has some applications as a synthetic block (Huang et al., 2014) and as a labeling agent. One of applications is detection of low concentrations of oxygen-containing functional groups through fluorescent labeling (Feng et al., 2006).
The title compound crystallizes with two molecules in the asymmetric uint: both molecules exhibit standard bond lengths and angles and almost planar naphthalene rings (Fig. 1). They differ in the conformations of the ethanol side-chains; the C1—C11—C12—O1 torsion angle of 176.20 (13)° indicates an anti orientation, whereas the equivalent angle in the second molecule [C21—C31—C32—O2 = 59.58 (17)°] corresponds to a
conformation. In the crystal, chains of alternating C1- and C21-molecules are linked by O—H···O hydrogen bonds (Table 1), generating C(2) [100] chains.Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. An infinitive chain of 2-(naphthalen-1-yl)ethanol molecules connected via hydrogen bonds. The view is along the c axis. | |
Fig. 3. X-ray powder diffraction diagram of polycrystalline 2-(naphthalen-1-yl)ethanol. Blue line: experimental data after baseline correction. Red line: Simulation from single-crystal data (this structure). |
C12H12O | Dx = 1.239 Mg m−3 |
Mr = 172.22 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, Pca21 | Cell parameters from 9816 reflections |
a = 9.8022 (6) Å | θ = 3.5–78.7° |
b = 14.9047 (9) Å | µ = 0.60 mm−1 |
c = 12.6430 (7) Å | T = 173 K |
V = 1847.13 (19) Å3 | Prism, colourless |
Z = 8 | 0.59 × 0.44 × 0.22 mm |
F(000) = 736 |
Bruker PHOTON 100 CMOS diffractometer | 3893 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.024 |
φ and ω scans | θmax = 78.9°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −12→12 |
Tmin = 0.776, Tmax = 0.931 | k = −18→18 |
60021 measured reflections | l = −16→15 |
3937 independent reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.028 | w = 1/[σ2(Fo2) + (0.0419P)2 + 0.2448P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.074 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.14 e Å−3 |
3937 reflections | Δρmin = −0.16 e Å−3 |
261 parameters | Absolute structure: Flack x determined using 1786 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.04 (3) |
C12H12O | V = 1847.13 (19) Å3 |
Mr = 172.22 | Z = 8 |
Orthorhombic, Pca21 | Cu Kα radiation |
a = 9.8022 (6) Å | µ = 0.60 mm−1 |
b = 14.9047 (9) Å | T = 173 K |
c = 12.6430 (7) Å | 0.59 × 0.44 × 0.22 mm |
Bruker PHOTON 100 CMOS diffractometer | 3937 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | 3893 reflections with I > 2σ(I) |
Tmin = 0.776, Tmax = 0.931 | Rint = 0.024 |
60021 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.074 | Δρmax = 0.14 e Å−3 |
S = 1.04 | Δρmin = −0.16 e Å−3 |
3937 reflections | Absolute structure: Flack x determined using 1786 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
261 parameters | Absolute structure parameter: 0.04 (3) |
1 restraint |
Experimental. SADABS2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0570 before and 0.0501 after correction. The Ratio of minimum to maximum transmission is 0.8328. The λ/2 correction factor is 0.00150. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.49885 (12) | 0.45896 (7) | 0.36984 (11) | 0.0337 (3) | |
H1 | 0.580 (3) | 0.4703 (14) | 0.3905 (19) | 0.045 (6)* | |
C1 | 0.54796 (17) | 0.21367 (11) | 0.30591 (12) | 0.0309 (3) | |
C2 | 0.45133 (19) | 0.16711 (14) | 0.25009 (14) | 0.0406 (4) | |
H2 | 0.3956 (14) | 0.2000 (8) | 0.1943 (14) | 0.049* | |
C3 | 0.4267 (3) | 0.07555 (15) | 0.26726 (17) | 0.0538 (5) | |
H3 | 0.360 (2) | 0.0452 (9) | 0.2269 (12) | 0.065* | |
C4 | 0.4994 (3) | 0.03039 (13) | 0.34271 (19) | 0.0533 (5) | |
H4 | 0.4828 (5) | −0.0293 (17) | 0.3542 (4) | 0.064* | |
C5 | 0.5996 (2) | 0.07497 (11) | 0.40304 (15) | 0.0397 (4) | |
C6 | 0.6740 (2) | 0.03077 (14) | 0.48406 (19) | 0.0536 (5) | |
H6 | 0.6538 (6) | −0.0342 (17) | 0.4997 (5) | 0.064* | |
C7 | 0.7716 (2) | 0.07348 (17) | 0.54095 (18) | 0.0575 (6) | |
H7 | 0.8239 (16) | 0.0399 (10) | 0.5981 (17) | 0.069* | |
C8 | 0.8006 (2) | 0.16422 (15) | 0.52095 (16) | 0.0482 (5) | |
H8 | 0.8739 (19) | 0.1952 (8) | 0.5620 (11) | 0.058* | |
C9 | 0.72891 (17) | 0.21065 (12) | 0.44539 (13) | 0.0346 (3) | |
H9 | 0.7492 (5) | 0.2748 (14) | 0.4332 (3) | 0.042* | |
C10 | 0.62625 (17) | 0.16800 (11) | 0.38452 (12) | 0.0312 (3) | |
C11 | 0.56252 (17) | 0.31391 (11) | 0.29043 (13) | 0.0318 (3) | |
H11A | 0.5286 (5) | 0.3305 (3) | 0.2212 (11) | 0.038* | |
H11B | 0.6580 (15) | 0.3305 (3) | 0.29433 (14) | 0.038* | |
C12 | 0.48255 (17) | 0.36354 (10) | 0.37543 (14) | 0.0334 (3) | |
H12A | 0.3873 (16) | 0.3491 (3) | 0.36835 (17) | 0.040* | |
H12B | 0.5122 (5) | 0.3431 (3) | 0.4438 (11) | 0.040* | |
O2 | 0.26483 (13) | 0.54063 (8) | 0.44908 (10) | 0.0355 (3) | |
H2A | 0.333 (3) | 0.5135 (17) | 0.424 (2) | 0.051 (6)* | |
C21 | 0.21629 (15) | 0.37666 (10) | 0.58262 (12) | 0.0281 (3) | |
C22 | 0.14186 (16) | 0.33293 (11) | 0.50662 (14) | 0.0325 (3) | |
H22 | 0.0633 (18) | 0.3629 (7) | 0.4757 (7) | 0.039* | |
C23 | 0.17591 (18) | 0.24575 (11) | 0.47191 (13) | 0.0350 (4) | |
H23 | 0.1248 (13) | 0.2184 (7) | 0.4197 (13) | 0.042* | |
C24 | 0.28412 (17) | 0.20191 (10) | 0.51537 (14) | 0.0317 (3) | |
H24 | 0.3075 (5) | 0.1431 (13) | 0.4909 (6) | 0.038* | |
C25 | 0.36234 (15) | 0.24240 (10) | 0.59631 (12) | 0.0269 (3) | |
C26 | 0.47452 (17) | 0.19757 (11) | 0.64316 (13) | 0.0325 (3) | |
H26 | 0.4950 (5) | 0.1380 (14) | 0.6223 (5) | 0.039* | |
C27 | 0.55353 (18) | 0.23832 (13) | 0.71755 (13) | 0.0367 (4) | |
H27 | 0.6345 (18) | 0.2052 (8) | 0.7494 (7) | 0.044* | |
C28 | 0.52301 (17) | 0.32634 (12) | 0.75026 (13) | 0.0341 (4) | |
H28 | 0.5807 (14) | 0.3558 (7) | 0.8037 (13) | 0.041* | |
C29 | 0.41387 (16) | 0.37134 (11) | 0.70841 (12) | 0.0297 (3) | |
H29 | 0.3933 (5) | 0.4323 (13) | 0.7331 (6) | 0.036* | |
C30 | 0.33003 (15) | 0.33137 (10) | 0.63004 (11) | 0.0255 (3) | |
C31 | 0.18036 (16) | 0.47189 (11) | 0.61290 (13) | 0.0316 (3) | |
H31A | 0.18674 (18) | 0.47767 (14) | 0.6894 (12) | 0.038* | |
H31B | 0.0860 (15) | 0.4833 (2) | 0.5930 (3) | 0.038* | |
C32 | 0.27051 (17) | 0.54330 (11) | 0.56206 (14) | 0.0332 (4) | |
H32A | 0.2407 (5) | 0.6039 (9) | 0.5870 (4) | 0.040* | |
H32B | 0.3670 (15) | 0.53414 (16) | 0.5854 (4) | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0312 (6) | 0.0279 (5) | 0.0422 (6) | 0.0007 (4) | 0.0011 (5) | 0.0058 (5) |
C1 | 0.0316 (8) | 0.0341 (8) | 0.0269 (7) | 0.0009 (6) | 0.0062 (6) | −0.0008 (6) |
C2 | 0.0405 (9) | 0.0497 (10) | 0.0316 (8) | −0.0042 (8) | −0.0002 (7) | −0.0046 (8) |
C3 | 0.0626 (13) | 0.0508 (11) | 0.0481 (12) | −0.0178 (10) | 0.0068 (10) | −0.0190 (9) |
C4 | 0.0698 (13) | 0.0313 (9) | 0.0588 (13) | −0.0084 (9) | 0.0208 (11) | −0.0102 (8) |
C5 | 0.0457 (10) | 0.0296 (8) | 0.0439 (9) | 0.0089 (7) | 0.0158 (8) | 0.0006 (7) |
C6 | 0.0608 (13) | 0.0387 (10) | 0.0611 (13) | 0.0213 (9) | 0.0209 (11) | 0.0127 (9) |
C7 | 0.0501 (12) | 0.0701 (14) | 0.0523 (12) | 0.0306 (11) | 0.0102 (9) | 0.0245 (11) |
C8 | 0.0333 (9) | 0.0717 (13) | 0.0397 (10) | 0.0109 (9) | 0.0026 (8) | 0.0093 (9) |
C9 | 0.0306 (7) | 0.0420 (9) | 0.0312 (8) | 0.0043 (7) | 0.0051 (6) | 0.0040 (7) |
C10 | 0.0322 (7) | 0.0322 (8) | 0.0290 (8) | 0.0043 (6) | 0.0090 (6) | 0.0002 (6) |
C11 | 0.0308 (7) | 0.0347 (8) | 0.0298 (7) | 0.0013 (6) | 0.0025 (6) | 0.0070 (6) |
C12 | 0.0308 (8) | 0.0292 (7) | 0.0402 (8) | 0.0000 (6) | 0.0085 (7) | 0.0060 (7) |
O2 | 0.0316 (6) | 0.0351 (6) | 0.0396 (6) | 0.0069 (5) | 0.0010 (5) | 0.0029 (5) |
C21 | 0.0249 (7) | 0.0311 (7) | 0.0283 (7) | −0.0033 (6) | 0.0054 (6) | 0.0001 (6) |
C22 | 0.0266 (7) | 0.0375 (8) | 0.0334 (8) | −0.0037 (6) | −0.0014 (6) | 0.0023 (7) |
C23 | 0.0360 (8) | 0.0370 (8) | 0.0320 (8) | −0.0125 (7) | −0.0024 (7) | −0.0040 (6) |
C24 | 0.0361 (8) | 0.0261 (7) | 0.0330 (8) | −0.0077 (6) | 0.0049 (7) | −0.0034 (6) |
C25 | 0.0276 (7) | 0.0277 (7) | 0.0255 (7) | −0.0043 (6) | 0.0055 (6) | 0.0009 (5) |
C26 | 0.0351 (8) | 0.0301 (8) | 0.0324 (8) | 0.0029 (6) | 0.0055 (6) | 0.0010 (6) |
C27 | 0.0308 (8) | 0.0457 (9) | 0.0337 (9) | 0.0045 (7) | −0.0006 (7) | 0.0061 (7) |
C28 | 0.0304 (8) | 0.0444 (9) | 0.0274 (8) | −0.0026 (7) | −0.0014 (6) | −0.0020 (7) |
C29 | 0.0308 (8) | 0.0327 (8) | 0.0256 (7) | −0.0035 (6) | 0.0029 (6) | −0.0031 (6) |
C30 | 0.0244 (6) | 0.0276 (7) | 0.0244 (7) | −0.0040 (5) | 0.0046 (5) | 0.0009 (5) |
C31 | 0.0260 (7) | 0.0340 (8) | 0.0349 (8) | 0.0041 (6) | 0.0023 (6) | −0.0031 (6) |
C32 | 0.0298 (8) | 0.0304 (8) | 0.0393 (9) | 0.0026 (6) | −0.0014 (7) | −0.0023 (6) |
O1—H1 | 0.86 (3) | O2—H2A | 0.84 (3) |
O1—C12 | 1.4330 (18) | O2—C32 | 1.430 (2) |
C1—C2 | 1.370 (2) | C21—C22 | 1.371 (2) |
C1—C10 | 1.428 (2) | C21—C30 | 1.435 (2) |
C1—C11 | 1.514 (2) | C21—C31 | 1.512 (2) |
C2—H2 | 1.02 (2) | C22—H22 | 0.97 (2) |
C2—C3 | 1.403 (3) | C22—C23 | 1.411 (2) |
C3—H3 | 0.94 (3) | C23—H23 | 0.92 (2) |
C3—C4 | 1.367 (4) | C23—C24 | 1.362 (3) |
C4—H4 | 0.92 (3) | C24—H24 | 0.96 (2) |
C4—C5 | 1.410 (3) | C24—C25 | 1.414 (2) |
C5—C6 | 1.420 (3) | C25—C26 | 1.417 (2) |
C5—C10 | 1.430 (2) | C25—C30 | 1.428 (2) |
C6—H6 | 1.01 (3) | C26—H26 | 0.95 (2) |
C6—C7 | 1.356 (4) | C26—C27 | 1.361 (3) |
C7—H7 | 1.02 (3) | C27—H27 | 1.02 (2) |
C7—C8 | 1.405 (3) | C27—C28 | 1.408 (3) |
C8—H8 | 1.00 (3) | C28—H28 | 0.98 (2) |
C8—C9 | 1.373 (3) | C28—C29 | 1.369 (2) |
C9—H9 | 0.99 (2) | C29—H29 | 0.98 (2) |
C9—C10 | 1.417 (2) | C29—C30 | 1.418 (2) |
C11—H11A | 0.969 (15) | C31—H31A | 0.973 (16) |
C11—H11B | 0.969 (15) | C31—H31B | 0.973 (16) |
C11—C12 | 1.522 (2) | C31—C32 | 1.525 (2) |
C12—H12A | 0.962 (15) | C32—H32A | 1.001 (15) |
C12—H12B | 0.962 (15) | C32—H32B | 1.001 (15) |
C12—O1—H1 | 106.5 (15) | C32—O2—H2A | 110.5 (17) |
C2—C1—C10 | 119.24 (16) | C22—C21—C30 | 118.85 (14) |
C2—C1—C11 | 119.91 (16) | C22—C21—C31 | 119.99 (14) |
C10—C1—C11 | 120.65 (15) | C30—C21—C31 | 121.13 (14) |
C1—C2—H2 | 118.9 | C21—C22—H22 | 119.0 |
C1—C2—C3 | 122.13 (19) | C21—C22—C23 | 121.98 (15) |
C3—C2—H2 | 118.9 | C23—C22—H22 | 119.0 |
C2—C3—H3 | 120.1 | C22—C23—H23 | 120.0 |
C4—C3—C2 | 119.8 (2) | C24—C23—C22 | 120.04 (15) |
C4—C3—H3 | 120.1 | C24—C23—H23 | 120.0 |
C3—C4—H4 | 119.7 | C23—C24—H24 | 119.7 |
C3—C4—C5 | 120.54 (18) | C23—C24—C25 | 120.64 (14) |
C5—C4—H4 | 119.7 | C25—C24—H24 | 119.7 |
C4—C5—C6 | 121.98 (19) | C24—C25—C26 | 121.48 (15) |
C4—C5—C10 | 119.70 (18) | C24—C25—C30 | 119.47 (14) |
C6—C5—C10 | 118.30 (18) | C26—C25—C30 | 119.03 (14) |
C5—C6—H6 | 119.1 | C25—C26—H26 | 119.3 |
C7—C6—C5 | 121.84 (19) | C27—C26—C25 | 121.33 (15) |
C7—C6—H6 | 119.1 | C27—C26—H26 | 119.3 |
C6—C7—H7 | 120.0 | C26—C27—H27 | 120.1 |
C6—C7—C8 | 119.94 (19) | C26—C27—C28 | 119.86 (16) |
C8—C7—H7 | 120.0 | C28—C27—H27 | 120.1 |
C7—C8—H8 | 119.8 | C27—C28—H28 | 119.7 |
C9—C8—C7 | 120.5 (2) | C29—C28—C27 | 120.60 (16) |
C9—C8—H8 | 119.8 | C29—C28—H28 | 119.7 |
C8—C9—H9 | 119.5 | C28—C29—H29 | 119.4 |
C8—C9—C10 | 120.99 (18) | C28—C29—C30 | 121.13 (15) |
C10—C9—H9 | 119.5 | C30—C29—H29 | 119.4 |
C1—C10—C5 | 118.54 (16) | C25—C30—C21 | 118.97 (14) |
C9—C10—C1 | 123.06 (15) | C29—C30—C21 | 122.99 (14) |
C9—C10—C5 | 118.40 (16) | C29—C30—C25 | 118.03 (14) |
C1—C11—H11A | 109.7 | C21—C31—H31A | 108.7 |
C1—C11—H11B | 109.7 | C21—C31—H31B | 108.7 |
C1—C11—C12 | 109.87 (13) | C21—C31—C32 | 114.43 (13) |
H11A—C11—H11B | 108.2 | H31A—C31—H31B | 107.6 |
C12—C11—H11A | 109.7 | C32—C31—H31A | 108.7 |
C12—C11—H11B | 109.7 | C32—C31—H31B | 108.7 |
O1—C12—C11 | 112.96 (13) | O2—C32—C31 | 112.26 (14) |
O1—C12—H12A | 109.0 | O2—C32—H32A | 109.2 |
O1—C12—H12B | 109.0 | O2—C32—H32B | 109.2 |
C11—C12—H12A | 109.0 | C31—C32—H32A | 109.2 |
C11—C12—H12B | 109.0 | C31—C32—H32B | 109.2 |
H12A—C12—H12B | 107.8 | H32A—C32—H32B | 107.9 |
C1—C2—C3—C4 | 0.8 (3) | C21—C22—C23—C24 | 1.1 (2) |
C1—C11—C12—O1 | 176.20 (13) | C21—C31—C32—O2 | 59.58 (17) |
C2—C1—C10—C5 | −0.7 (2) | C22—C21—C30—C25 | 0.2 (2) |
C2—C1—C10—C9 | 179.51 (15) | C22—C21—C30—C29 | 179.33 (14) |
C2—C1—C11—C12 | 95.94 (18) | C22—C21—C31—C32 | −100.07 (17) |
C2—C3—C4—C5 | −0.4 (3) | C22—C23—C24—C25 | 0.8 (2) |
C3—C4—C5—C6 | 178.1 (2) | C23—C24—C25—C26 | 179.43 (15) |
C3—C4—C5—C10 | −0.5 (3) | C23—C24—C25—C30 | −2.2 (2) |
C4—C5—C6—C7 | 179.09 (19) | C24—C25—C26—C27 | 176.88 (15) |
C4—C5—C10—C1 | 1.1 (2) | C24—C25—C30—C21 | 1.6 (2) |
C4—C5—C10—C9 | −179.13 (16) | C24—C25—C30—C29 | −177.53 (14) |
C5—C6—C7—C8 | 0.6 (3) | C25—C26—C27—C28 | 0.9 (3) |
C6—C5—C10—C1 | −177.61 (16) | C26—C25—C30—C21 | −179.92 (14) |
C6—C5—C10—C9 | 2.2 (2) | C26—C25—C30—C29 | 0.9 (2) |
C6—C7—C8—C9 | 1.2 (3) | C26—C27—C28—C29 | 0.4 (3) |
C7—C8—C9—C10 | −1.2 (3) | C27—C28—C29—C30 | −1.0 (2) |
C8—C9—C10—C1 | 179.27 (16) | C28—C29—C30—C21 | −178.79 (14) |
C8—C9—C10—C5 | −0.5 (2) | C28—C29—C30—C25 | 0.3 (2) |
C10—C1—C2—C3 | −0.2 (3) | C30—C21—C22—C23 | −1.6 (2) |
C10—C1—C11—C12 | −78.87 (18) | C30—C21—C31—C32 | 78.18 (18) |
C10—C5—C6—C7 | −2.2 (3) | C30—C25—C26—C27 | −1.5 (2) |
C11—C1—C2—C3 | −175.10 (17) | C31—C21—C22—C23 | 176.68 (15) |
C11—C1—C10—C5 | 174.12 (14) | C31—C21—C30—C25 | −178.05 (13) |
C11—C1—C10—C9 | −5.6 (2) | C31—C21—C30—C29 | 1.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.86 (3) | 1.96 (3) | 2.7931 (17) | 163 (2) |
O2—H2A···O1 | 0.84 (3) | 1.94 (3) | 2.7834 (17) | 176 (2) |
Symmetry code: (i) x+1/2, −y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.86 (3) | 1.96 (3) | 2.7931 (17) | 163 (2) |
O2—H2A···O1 | 0.84 (3) | 1.94 (3) | 2.7834 (17) | 176 (2) |
Symmetry code: (i) x+1/2, −y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C12H12O |
Mr | 172.22 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 173 |
a, b, c (Å) | 9.8022 (6), 14.9047 (9), 12.6430 (7) |
V (Å3) | 1847.13 (19) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.60 |
Crystal size (mm) | 0.59 × 0.44 × 0.22 |
Data collection | |
Diffractometer | Bruker PHOTON 100 CMOS |
Absorption correction | Multi-scan (SADABS; Bruker, 2014) |
Tmin, Tmax | 0.776, 0.931 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 60021, 3937, 3893 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.636 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.074, 1.04 |
No. of reflections | 3937 |
No. of parameters | 261 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.16 |
Absolute structure | Flack x determined using 1786 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Absolute structure parameter | 0.04 (3) |
Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2013), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009).
Acknowledgements
Financial support from the State University of New York for acquisition and maintenance of the X-ray diffractometer is gratefully acknowledged.
References
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