organic compounds
Orthorhombic polymorph of (2E)-2-(2,3-dihydro-1H-inden-1-ylidene)-2,3-dihydro-1H-inden-1-one†
aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
*Correspondence e-mail: ffroncz@lsu.edu
The title compound, C18H14O, is polymorphic at 123 K. The orthorhombic form reported herein has two independent molecules in the with molecular volume 313.5 Å3. The previously reported triclinic (P-1) form [Raston & Scott (2000). Green Chem., 2, 49–52] has molecular volume 309.6 Å3 at the same temperature. All three molecules deviate significantly and systematically from the putative Cs symmetry (δr.m.s. = 0.0265, 0.0256, 0.0497 Å). Comparison of the two molecules in the orthorhombic polymorph shows that 16 of the 19 equivalent pairs of framework atoms have a mirror-image pattern of deviations (above/below plane), suggesting that the two are quasi-enantiomorphs. The pattern of deviations in the triclinic form is nearly the same (13 of 19 atom pairs) as the orthorhombic form.
Related literature
For the title compound co-crystallized with 2,4-di-tert-butylphenol, see: Turner et al. (2003; CSD refcode IQAZAB). For the Cambridge Structural Database (CSD), see: Allen (2002). For the determination of an from Bijvoet pairs, see: Hooft et al. (2008). For the synthesis of the title compound, see: Bell & Spanswick (1966). For cis-trans in the title compound, see: Williams (1967).
Experimental
Crystal data
|
Data collection: COLLECT (Nonius, 2000); cell DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: IDEAL (Gould et al., 1988) and WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536812035994/jj2149sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035994/jj2149Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035994/jj2149Isup3.cml
The synthesis is detailed by Bell & Spanswick (1966): benzyl cyanide (1.8 g.) was added to a solution of sodium (0.35 g) in ethanol (20 ml). Indan-1-one (2 g) was then added, and the mixture warmed on a steam-bath for 20 min. The product was cooled, diluted, and acidified with acetic acid. The sticky precipitate was crystallized from ethanol to yield yellow needles, m.p. 141–143°C.
The
could not be determined by analysis of 1665 Bijvoet pairs (Flack (1983) x = 0(2), Hooft et al. (2008) y = 0.4 (12). All H atoms were placed in calculated positions, with C—H distances of 0.95–0.99 Å, Uiso = 1.2 of the attached carbon atom, and thereafter treated as riding.Data collection: COLLECT (Nonius, 2000); cell
DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: IDEAL (Gould et al., 1988) and WinGX (Farrugia, 1999).C18H14O | Dx = 1.304 Mg m−3 |
Mr = 246.29 | Melting point = 414–416 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2407 reflections |
a = 5.291 (2) Å | θ = 2.5–25° |
b = 17.809 (5) Å | µ = 0.08 mm−1 |
c = 26.622 (9) Å | T = 123 K |
V = 2508.5 (15) Å3 | Needle, yellow |
Z = 8 | 0.35 × 0.12 × 0.05 mm |
F(000) = 1040 |
Nonius KappaCCD diffractometer | 4236 independent reflections |
Radiation source: sealed tube | 3145 reflections with I > 2σ(I) |
Horizonally mounted graphite crystal monochromator | Rint = 0.074 |
Detector resolution: 9 pixels mm-1 | θmax = 25.0°, θmin = 2.6° |
ω and ϕ scans | h = −6→6 |
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor 1997) | k = −20→21 |
Tmin = 0.973, Tmax = 0.996 | l = −31→31 |
11743 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.057 | w = 1/[σ2(Fo2) + (0.0283P)2 + 1.1913P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.110 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.21 e Å−3 |
4236 reflections | Δρmin = −0.18 e Å−3 |
344 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0049 (8) |
0 constraints | Absolute structure: Flack (1983), with 1665 Bijvoet pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (2) |
Secondary atom site location: difference Fourier map |
C18H14O | V = 2508.5 (15) Å3 |
Mr = 246.29 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.291 (2) Å | µ = 0.08 mm−1 |
b = 17.809 (5) Å | T = 123 K |
c = 26.622 (9) Å | 0.35 × 0.12 × 0.05 mm |
Nonius KappaCCD diffractometer | 4236 independent reflections |
Absorption correction: multi-scan HKL SCALEPACK (Otwinowski & Minor 1997) | 3145 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.996 | Rint = 0.074 |
11743 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.110 | Δρmax = 0.21 e Å−3 |
S = 1.05 | Δρmin = −0.18 e Å−3 |
4236 reflections | Absolute structure: Flack (1983), with 1665 Bijvoet pairs |
344 parameters | Absolute structure parameter: 0 (2) |
0 restraints |
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 | ||
C1 | 0.3862 (6) | 0.10668 (16) | 0.32450 (12) | 0.0256 (7) | |
C2 | 0.5813 (5) | 0.05703 (16) | 0.30273 (11) | 0.0244 (7) | |
C3 | 0.7531 (6) | 0.01103 (17) | 0.32733 (12) | 0.0300 (8) | |
H3 | 0.7526 | 0.0072 | 0.3629 | 0.036* | |
C4 | 0.9248 (6) | −0.02910 (17) | 0.29896 (12) | 0.0309 (8) | |
H4 | 1.0456 | −0.0603 | 0.3151 | 0.037* | |
C5 | 0.9216 (6) | −0.02405 (17) | 0.24675 (13) | 0.0310 (8) | |
H5 | 1.0391 | −0.0526 | 0.2277 | 0.037* | |
C6 | 0.7499 (6) | 0.02196 (16) | 0.22196 (12) | 0.0269 (7) | |
H6 | 0.7488 | 0.0252 | 0.1863 | 0.032* | |
C7 | 0.5794 (6) | 0.06329 (16) | 0.25077 (11) | 0.0239 (8) | |
C8 | 0.3800 (5) | 0.11835 (16) | 0.23340 (11) | 0.0238 (7) | |
H8A | 0.2542 | 0.0934 | 0.2115 | 0.029* | |
H8B | 0.4574 | 0.1607 | 0.2148 | 0.029* | |
C9 | 0.2586 (5) | 0.14540 (16) | 0.28197 (11) | 0.0221 (7) | |
C10 | 0.0721 (5) | 0.19601 (16) | 0.28771 (11) | 0.0230 (7) | |
C11 | −0.0697 (5) | 0.23669 (15) | 0.24841 (11) | 0.0225 (7) | |
C12 | −0.0489 (6) | 0.23430 (16) | 0.19628 (11) | 0.0257 (7) | |
H12 | 0.0758 | 0.2038 | 0.1807 | 0.031* | |
C13 | −0.2134 (6) | 0.27720 (17) | 0.16749 (12) | 0.0296 (8) | |
H13 | −0.1998 | 0.2763 | 0.1319 | 0.036* | |
C14 | −0.3968 (6) | 0.32121 (17) | 0.18995 (13) | 0.0345 (9) | |
H14 | −0.5096 | 0.3494 | 0.1696 | 0.041* | |
C15 | −0.4178 (6) | 0.32469 (17) | 0.24150 (14) | 0.0331 (8) | |
H15 | −0.5428 | 0.3555 | 0.2567 | 0.04* | |
C16 | −0.2536 (6) | 0.28247 (16) | 0.27084 (11) | 0.0271 (8) | |
C17 | −0.2433 (6) | 0.27776 (17) | 0.32697 (12) | 0.0313 (8) | |
H17A | −0.4076 | 0.2609 | 0.3407 | 0.038* | |
H17B | −0.2005 | 0.3272 | 0.3417 | 0.038* | |
C18 | −0.0346 (6) | 0.21981 (18) | 0.33823 (11) | 0.0299 (8) | |
H18A | 0.0994 | 0.2425 | 0.3593 | 0.036* | |
H18B | −0.1057 | 0.176 | 0.3562 | 0.036* | |
O1 | 0.3417 (4) | 0.11400 (12) | 0.36966 (8) | 0.0380 (6) | |
C19 | 0.0040 (5) | −0.05063 (16) | 0.07403 (12) | 0.0248 (7) | |
C20 | −0.1891 (5) | −0.09719 (15) | 0.04914 (11) | 0.0236 (7) | |
C21 | −0.3649 (6) | −0.14487 (17) | 0.07113 (12) | 0.0293 (8) | |
H21 | −0.3691 | −0.1517 | 0.1065 | 0.035* | |
C22 | −0.5337 (6) | −0.18215 (16) | 0.04030 (13) | 0.0343 (8) | |
H22 | −0.6548 | −0.2153 | 0.0545 | 0.041* | |
C23 | −0.5264 (6) | −0.17121 (17) | −0.01129 (13) | 0.0328 (8) | |
H23 | −0.6433 | −0.1973 | −0.032 | 0.039* | |
C24 | −0.3526 (6) | −0.12311 (16) | −0.03339 (12) | 0.0301 (8) | |
H24 | −0.3498 | −0.1159 | −0.0687 | 0.036* | |
C25 | −0.1821 (6) | −0.08560 (16) | −0.00228 (11) | 0.0237 (8) | |
C26 | 0.0229 (5) | −0.03001 (16) | −0.01635 (11) | 0.0249 (7) | |
H26A | 0.1504 | −0.0535 | −0.0386 | 0.03* | |
H26B | −0.0494 | 0.0144 | −0.0335 | 0.03* | |
C27 | 0.1375 (5) | −0.00859 (15) | 0.03373 (11) | 0.0227 (7) | |
C28 | 0.3261 (5) | 0.04062 (16) | 0.04303 (11) | 0.0224 (7) | |
C29 | 0.4744 (6) | 0.08474 (16) | 0.00679 (11) | 0.0223 (7) | |
C30 | 0.4644 (6) | 0.08748 (16) | −0.04551 (11) | 0.0266 (7) | |
H30 | 0.3434 | 0.0585 | −0.0634 | 0.032* | |
C31 | 0.6341 (6) | 0.13329 (17) | −0.07129 (12) | 0.0307 (8) | |
H31 | 0.6296 | 0.1352 | −0.1069 | 0.037* | |
C32 | 0.8107 (6) | 0.17629 (16) | −0.04507 (13) | 0.0323 (8) | |
H32 | 0.9255 | 0.2072 | −0.0631 | 0.039* | |
C33 | 0.8205 (6) | 0.17441 (17) | 0.00674 (13) | 0.0309 (9) | |
H33 | 0.9406 | 0.204 | 0.0244 | 0.037* | |
C34 | 0.6521 (6) | 0.12866 (16) | 0.03270 (11) | 0.0265 (8) | |
C35 | 0.6346 (6) | 0.11740 (17) | 0.08845 (11) | 0.0335 (8) | |
H35A | 0.5896 | 0.1649 | 0.1056 | 0.04* | |
H35B | 0.797 | 0.0989 | 0.1022 | 0.04* | |
C36 | 0.4246 (6) | 0.05840 (17) | 0.09514 (11) | 0.0284 (8) | |
H36A | 0.4931 | 0.0126 | 0.1112 | 0.034* | |
H36B | 0.2873 | 0.0785 | 0.1165 | 0.034* | |
O2 | 0.0410 (4) | −0.04698 (12) | 0.11985 (8) | 0.0332 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0271 (18) | 0.0229 (17) | 0.027 (2) | −0.0017 (15) | −0.0014 (14) | 0.0003 (14) |
C2 | 0.0230 (17) | 0.0179 (16) | 0.032 (2) | −0.0054 (15) | −0.0018 (14) | 0.0011 (14) |
C3 | 0.0305 (18) | 0.0240 (18) | 0.035 (2) | 0.0015 (16) | −0.0022 (16) | 0.0078 (15) |
C4 | 0.0235 (17) | 0.0214 (17) | 0.048 (2) | 0.0034 (16) | −0.0030 (16) | 0.0088 (15) |
C5 | 0.0241 (18) | 0.0195 (17) | 0.049 (2) | 0.0000 (16) | 0.0031 (16) | 0.0010 (15) |
C6 | 0.0246 (16) | 0.0242 (17) | 0.0318 (19) | −0.0042 (15) | 0.0016 (15) | −0.0020 (15) |
C7 | 0.0224 (17) | 0.0158 (16) | 0.033 (2) | −0.0026 (15) | 0.0001 (15) | 0.0020 (14) |
C8 | 0.0238 (16) | 0.0206 (16) | 0.0269 (17) | −0.0014 (14) | 0.0028 (13) | −0.0004 (13) |
C9 | 0.0232 (16) | 0.0210 (17) | 0.0221 (18) | −0.0033 (15) | 0.0001 (14) | −0.0006 (13) |
C10 | 0.0237 (16) | 0.0164 (16) | 0.0290 (19) | −0.0032 (14) | 0.0016 (14) | −0.0019 (13) |
C11 | 0.0188 (17) | 0.0147 (15) | 0.034 (2) | −0.0014 (14) | −0.0013 (14) | −0.0006 (14) |
C12 | 0.0248 (17) | 0.0223 (16) | 0.030 (2) | −0.0030 (15) | −0.0027 (14) | 0.0000 (14) |
C13 | 0.0284 (19) | 0.0222 (17) | 0.038 (2) | −0.0068 (16) | −0.0041 (15) | 0.0059 (15) |
C14 | 0.030 (2) | 0.0236 (18) | 0.050 (2) | −0.0043 (17) | −0.0148 (17) | 0.0068 (16) |
C15 | 0.0239 (18) | 0.0188 (17) | 0.057 (3) | 0.0040 (15) | −0.0060 (17) | −0.0035 (16) |
C16 | 0.0216 (16) | 0.0212 (17) | 0.039 (2) | −0.0073 (15) | −0.0018 (15) | −0.0019 (15) |
C17 | 0.0240 (18) | 0.0239 (18) | 0.046 (2) | 0.0019 (15) | 0.0042 (16) | −0.0073 (15) |
C18 | 0.0306 (18) | 0.0306 (18) | 0.0286 (19) | 0.0003 (16) | 0.0035 (14) | −0.0065 (14) |
O1 | 0.0468 (15) | 0.0413 (14) | 0.0259 (14) | 0.0089 (12) | 0.0002 (11) | 0.0016 (11) |
C19 | 0.0214 (17) | 0.0203 (17) | 0.033 (2) | 0.0077 (14) | −0.0001 (15) | 0.0031 (14) |
C20 | 0.0206 (17) | 0.0151 (16) | 0.035 (2) | 0.0042 (14) | 0.0008 (14) | 0.0011 (14) |
C21 | 0.0242 (17) | 0.0272 (18) | 0.037 (2) | 0.0025 (16) | 0.0068 (15) | 0.0077 (15) |
C22 | 0.0290 (19) | 0.0192 (17) | 0.055 (2) | −0.0037 (15) | 0.0060 (17) | 0.0014 (16) |
C23 | 0.0254 (19) | 0.0219 (18) | 0.051 (2) | −0.0032 (16) | −0.0032 (17) | −0.0083 (16) |
C24 | 0.033 (2) | 0.0221 (17) | 0.035 (2) | 0.0000 (17) | −0.0015 (15) | −0.0077 (15) |
C25 | 0.0198 (18) | 0.0173 (16) | 0.034 (2) | 0.0037 (14) | 0.0020 (13) | 0.0000 (14) |
C26 | 0.0261 (17) | 0.0217 (16) | 0.0268 (18) | 0.0027 (15) | 0.0031 (14) | −0.0007 (14) |
C27 | 0.0230 (17) | 0.0183 (16) | 0.0267 (19) | 0.0041 (15) | 0.0018 (13) | −0.0023 (13) |
C28 | 0.0182 (16) | 0.0205 (16) | 0.0286 (18) | 0.0074 (15) | 0.0004 (13) | −0.0011 (14) |
C29 | 0.0178 (17) | 0.0165 (16) | 0.033 (2) | 0.0044 (14) | 0.0011 (14) | −0.0009 (14) |
C30 | 0.0228 (17) | 0.0242 (17) | 0.033 (2) | 0.0012 (15) | −0.0012 (14) | 0.0008 (14) |
C31 | 0.0285 (18) | 0.0272 (18) | 0.036 (2) | 0.0068 (16) | 0.0029 (15) | 0.0061 (15) |
C32 | 0.0263 (19) | 0.0189 (17) | 0.052 (2) | 0.0001 (15) | 0.0062 (16) | 0.0080 (15) |
C33 | 0.029 (2) | 0.0200 (18) | 0.044 (2) | 0.0003 (16) | 0.0005 (16) | −0.0002 (15) |
C34 | 0.0280 (18) | 0.0170 (16) | 0.035 (2) | 0.0039 (16) | −0.0004 (14) | −0.0005 (14) |
C35 | 0.0361 (19) | 0.0253 (18) | 0.039 (2) | −0.0027 (17) | −0.0050 (16) | 0.0001 (15) |
C36 | 0.0246 (18) | 0.0306 (19) | 0.0300 (19) | −0.0039 (15) | 0.0002 (15) | −0.0012 (14) |
O2 | 0.0327 (13) | 0.0400 (14) | 0.0268 (14) | −0.0005 (11) | 0.0007 (10) | 0.0030 (10) |
C1—O1 | 1.232 (3) | C19—O2 | 1.237 (3) |
C1—C2 | 1.478 (4) | C19—C20 | 1.473 (4) |
C1—C9 | 1.488 (4) | C19—C27 | 1.487 (4) |
C2—C3 | 1.388 (4) | C20—C25 | 1.385 (4) |
C2—C7 | 1.388 (4) | C20—C21 | 1.389 (4) |
C3—C4 | 1.381 (4) | C21—C22 | 1.383 (4) |
C3—H3 | 0.95 | C21—H21 | 0.95 |
C4—C5 | 1.393 (4) | C22—C23 | 1.388 (4) |
C4—H4 | 0.95 | C22—H22 | 0.95 |
C5—C6 | 1.390 (4) | C23—C24 | 1.388 (4) |
C5—H5 | 0.95 | C23—H23 | 0.95 |
C6—C7 | 1.394 (4) | C24—C25 | 1.395 (4) |
C6—H6 | 0.95 | C24—H24 | 0.95 |
C7—C8 | 1.513 (4) | C25—C26 | 1.516 (4) |
C8—C9 | 1.522 (4) | C26—C27 | 1.514 (4) |
C8—H8A | 0.99 | C26—H26A | 0.99 |
C8—H8B | 0.99 | C26—H26B | 0.99 |
C9—C10 | 1.345 (4) | C27—C28 | 1.351 (4) |
C10—C11 | 1.477 (4) | C28—C29 | 1.471 (4) |
C10—C18 | 1.519 (4) | C28—C36 | 1.515 (4) |
C11—C12 | 1.393 (4) | C29—C30 | 1.394 (4) |
C11—C16 | 1.403 (4) | C29—C34 | 1.404 (4) |
C12—C13 | 1.389 (4) | C30—C31 | 1.394 (4) |
C12—H12 | 0.95 | C30—H30 | 0.95 |
C13—C14 | 1.383 (4) | C31—C32 | 1.395 (4) |
C13—H13 | 0.95 | C31—H31 | 0.95 |
C14—C15 | 1.378 (5) | C32—C33 | 1.381 (4) |
C14—H14 | 0.95 | C32—H32 | 0.95 |
C15—C16 | 1.389 (4) | C33—C34 | 1.391 (4) |
C15—H15 | 0.95 | C33—H33 | 0.95 |
C16—C17 | 1.498 (4) | C34—C35 | 1.501 (4) |
C17—C18 | 1.541 (4) | C35—C36 | 1.540 (4) |
C17—H17A | 0.99 | C35—H35A | 0.99 |
C17—H17B | 0.99 | C35—H35B | 0.99 |
C18—H18A | 0.99 | C36—H36A | 0.99 |
C18—H18B | 0.99 | C36—H36B | 0.99 |
O1—C1—C2 | 125.4 (3) | O2—C19—C20 | 125.7 (3) |
O1—C1—C9 | 127.4 (3) | O2—C19—C27 | 127.6 (3) |
C2—C1—C9 | 107.2 (2) | C20—C19—C27 | 106.8 (3) |
C3—C2—C7 | 121.5 (3) | C25—C20—C21 | 121.7 (3) |
C3—C2—C1 | 128.7 (3) | C25—C20—C19 | 110.0 (3) |
C7—C2—C1 | 109.7 (3) | C21—C20—C19 | 128.2 (3) |
C4—C3—C2 | 118.6 (3) | C22—C21—C20 | 118.4 (3) |
C4—C3—H3 | 120.7 | C22—C21—H21 | 120.8 |
C2—C3—H3 | 120.7 | C20—C21—H21 | 120.8 |
C3—C4—C5 | 120.3 (3) | C21—C22—C23 | 120.2 (3) |
C3—C4—H4 | 119.9 | C21—C22—H22 | 119.9 |
C5—C4—H4 | 119.9 | C23—C22—H22 | 119.9 |
C6—C5—C4 | 121.3 (3) | C22—C23—C24 | 121.6 (3) |
C6—C5—H5 | 119.3 | C22—C23—H23 | 119.2 |
C4—C5—H5 | 119.3 | C24—C23—H23 | 119.2 |
C5—C6—C7 | 118.2 (3) | C23—C24—C25 | 118.2 (3) |
C5—C6—H6 | 120.9 | C23—C24—H24 | 120.9 |
C7—C6—H6 | 120.9 | C25—C24—H24 | 120.9 |
C2—C7—C6 | 120.1 (3) | C20—C25—C24 | 119.9 (3) |
C2—C7—C8 | 111.2 (3) | C20—C25—C26 | 111.1 (3) |
C6—C7—C8 | 128.7 (3) | C24—C25—C26 | 129.0 (3) |
C7—C8—C9 | 103.9 (2) | C27—C26—C25 | 103.5 (2) |
C7—C8—H8A | 111 | C27—C26—H26A | 111.1 |
C9—C8—H8A | 111 | C25—C26—H26A | 111.1 |
C7—C8—H8B | 111 | C27—C26—H26B | 111.1 |
C9—C8—H8B | 111 | C25—C26—H26B | 111.1 |
H8A—C8—H8B | 109 | H26A—C26—H26B | 109 |
C10—C9—C1 | 123.9 (3) | C28—C27—C19 | 123.0 (3) |
C10—C9—C8 | 128.2 (3) | C28—C27—C26 | 128.4 (3) |
C1—C9—C8 | 107.9 (2) | C19—C27—C26 | 108.6 (2) |
C9—C10—C11 | 128.4 (3) | C27—C28—C29 | 128.3 (3) |
C9—C10—C18 | 124.1 (3) | C27—C28—C36 | 123.9 (3) |
C11—C10—C18 | 107.6 (2) | C29—C28—C36 | 107.8 (2) |
C12—C11—C16 | 119.8 (3) | C30—C29—C34 | 119.8 (3) |
C12—C11—C10 | 130.6 (3) | C30—C29—C28 | 130.8 (3) |
C16—C11—C10 | 109.6 (3) | C34—C29—C28 | 109.4 (3) |
C13—C12—C11 | 118.9 (3) | C31—C30—C29 | 119.2 (3) |
C13—C12—H12 | 120.5 | C31—C30—H30 | 120.4 |
C11—C12—H12 | 120.5 | C29—C30—H30 | 120.4 |
C14—C13—C12 | 120.8 (3) | C30—C31—C32 | 120.4 (3) |
C14—C13—H13 | 119.6 | C30—C31—H31 | 119.8 |
C12—C13—H13 | 119.6 | C32—C31—H31 | 119.8 |
C15—C14—C13 | 120.8 (3) | C33—C32—C31 | 120.8 (3) |
C15—C14—H14 | 119.6 | C33—C32—H32 | 119.6 |
C13—C14—H14 | 119.6 | C31—C32—H32 | 119.6 |
C14—C15—C16 | 119.0 (3) | C32—C33—C34 | 119.1 (3) |
C14—C15—H15 | 120.5 | C32—C33—H33 | 120.5 |
C16—C15—H15 | 120.5 | C34—C33—H33 | 120.5 |
C15—C16—C11 | 120.6 (3) | C33—C34—C29 | 120.7 (3) |
C15—C16—C17 | 127.9 (3) | C33—C34—C35 | 127.5 (3) |
C11—C16—C17 | 111.5 (3) | C29—C34—C35 | 111.7 (3) |
C16—C17—C18 | 104.9 (2) | C34—C35—C36 | 104.5 (2) |
C16—C17—H17A | 110.8 | C34—C35—H35A | 110.9 |
C18—C17—H17A | 110.8 | C36—C35—H35A | 110.9 |
C16—C17—H17B | 110.8 | C34—C35—H35B | 110.9 |
C18—C17—H17B | 110.8 | C36—C35—H35B | 110.9 |
H17A—C17—H17B | 108.8 | H35A—C35—H35B | 108.9 |
C10—C18—C17 | 106.3 (2) | C28—C36—C35 | 106.6 (2) |
C10—C18—H18A | 110.5 | C28—C36—H36A | 110.4 |
C17—C18—H18A | 110.5 | C35—C36—H36A | 110.4 |
C10—C18—H18B | 110.5 | C28—C36—H36B | 110.4 |
C17—C18—H18B | 110.5 | C35—C36—H36B | 110.4 |
H18A—C18—H18B | 108.7 | H36A—C36—H36B | 108.6 |
O1—C1—C2—C3 | −1.5 (5) | O2—C19—C20—C25 | 178.1 (3) |
C9—C1—C2—C3 | 178.2 (3) | C27—C19—C20—C25 | −0.6 (3) |
O1—C1—C2—C7 | −179.7 (3) | O2—C19—C20—C21 | 0.3 (5) |
C9—C1—C2—C7 | 0.0 (3) | C27—C19—C20—C21 | −178.3 (3) |
C7—C2—C3—C4 | 0.0 (5) | C25—C20—C21—C22 | 1.0 (4) |
C1—C2—C3—C4 | −178.0 (3) | C19—C20—C21—C22 | 178.5 (3) |
C2—C3—C4—C5 | −1.0 (5) | C20—C21—C22—C23 | −0.5 (4) |
C3—C4—C5—C6 | 1.0 (5) | C21—C22—C23—C24 | −0.1 (5) |
C4—C5—C6—C7 | 0.0 (4) | C22—C23—C24—C25 | 0.2 (5) |
C3—C2—C7—C6 | 1.0 (4) | C21—C20—C25—C24 | −0.9 (4) |
C1—C2—C7—C6 | 179.4 (2) | C19—C20—C25—C24 | −178.8 (2) |
C3—C2—C7—C8 | −178.4 (3) | C21—C20—C25—C26 | 178.8 (3) |
C1—C2—C7—C8 | 0.0 (3) | C19—C20—C25—C26 | 0.8 (3) |
C5—C6—C7—C2 | −1.0 (4) | C23—C24—C25—C20 | 0.3 (4) |
C5—C6—C7—C8 | 178.3 (3) | C23—C24—C25—C26 | −179.3 (3) |
C2—C7—C8—C9 | 0.0 (3) | C20—C25—C26—C27 | −0.7 (3) |
C6—C7—C8—C9 | −179.3 (3) | C24—C25—C26—C27 | 178.9 (3) |
O1—C1—C9—C10 | 0.7 (5) | O2—C19—C27—C28 | 0.6 (5) |
C2—C1—C9—C10 | −179.0 (3) | C20—C19—C27—C28 | 179.2 (3) |
O1—C1—C9—C8 | 179.7 (3) | O2—C19—C27—C26 | −178.5 (3) |
C2—C1—C9—C8 | 0.0 (3) | C20—C19—C27—C26 | 0.1 (3) |
C7—C8—C9—C10 | 178.9 (3) | C25—C26—C27—C28 | −178.7 (3) |
C7—C8—C9—C1 | 0.0 (3) | C25—C26—C27—C19 | 0.4 (3) |
C1—C9—C10—C11 | −179.0 (3) | C19—C27—C28—C29 | 179.2 (3) |
C8—C9—C10—C11 | 2.3 (5) | C26—C27—C28—C29 | −1.9 (5) |
C1—C9—C10—C18 | −0.6 (4) | C19—C27—C28—C36 | 0.4 (4) |
C8—C9—C10—C18 | −179.4 (3) | C26—C27—C28—C36 | 179.4 (3) |
C9—C10—C11—C12 | −0.5 (5) | C27—C28—C29—C30 | −0.8 (5) |
C18—C10—C11—C12 | −179.0 (3) | C36—C28—C29—C30 | 178.1 (3) |
C9—C10—C11—C16 | 178.1 (3) | C27—C28—C29—C34 | −179.8 (3) |
C18—C10—C11—C16 | −0.4 (3) | C36—C28—C29—C34 | −0.9 (3) |
C16—C11—C12—C13 | −0.5 (4) | C34—C29—C30—C31 | 0.8 (4) |
C10—C11—C12—C13 | 178.0 (3) | C28—C29—C30—C31 | −178.1 (3) |
C11—C12—C13—C14 | −0.5 (4) | C29—C30—C31—C32 | −0.5 (4) |
C12—C13—C14—C15 | 1.2 (5) | C30—C31—C32—C33 | −0.1 (5) |
C13—C14—C15—C16 | −0.8 (5) | C31—C32—C33—C34 | 0.3 (5) |
C14—C15—C16—C11 | −0.3 (5) | C32—C33—C34—C29 | 0.1 (4) |
C14—C15—C16—C17 | −179.9 (3) | C32—C33—C34—C35 | 178.7 (3) |
C12—C11—C16—C15 | 0.9 (4) | C30—C29—C34—C33 | −0.7 (4) |
C10—C11—C16—C15 | −177.9 (3) | C28—C29—C34—C33 | 178.5 (3) |
C12—C11—C16—C17 | −179.4 (3) | C30—C29—C34—C35 | −179.5 (3) |
C10—C11—C16—C17 | 1.8 (3) | C28—C29—C34—C35 | −0.3 (3) |
C15—C16—C17—C18 | 177.2 (3) | C33—C34—C35—C36 | −177.3 (3) |
C11—C16—C17—C18 | −2.4 (3) | C29—C34—C35—C36 | 1.4 (3) |
C9—C10—C18—C17 | −179.7 (3) | C27—C28—C36—C35 | −179.3 (3) |
C11—C10—C18—C17 | −1.0 (3) | C29—C28—C36—C35 | 1.7 (3) |
C16—C17—C18—C10 | 2.0 (3) | C34—C35—C36—C28 | −1.8 (3) |
Experimental details
Crystal data | |
Chemical formula | C18H14O |
Mr | 246.29 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 123 |
a, b, c (Å) | 5.291 (2), 17.809 (5), 26.622 (9) |
V (Å3) | 2508.5 (15) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.12 × 0.05 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan HKL SCALEPACK (Otwinowski & Minor 1997) |
Tmin, Tmax | 0.973, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11743, 4236, 3145 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.110, 1.05 |
No. of reflections | 4236 |
No. of parameters | 344 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.18 |
Absolute structure | Flack (1983), with 1665 Bijvoet pairs |
Absolute structure parameter | 0 (2) |
Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), IDEAL (Gould et al., 1988) and WinGX (Farrugia, 1999).
Footnotes
†CAS 17563-12-1.
Acknowledgements
The purchase of the diffractometer was made possible by grant No. LEQSF(1999–2000)-ESH-TR-13, administered by the Louisiana Board of Regents. We thank Dr Raj Dhar for providing the sample.
References
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bell, F. & Spanswick, J. (1966). J. Chem. Soc. C, pp. 1887–1888. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gould, R. O., Moulden, N. & Taylor, P. (1988). IDEAL. Department of Chemistry, University of Edinburgh, Scotland. Google Scholar
Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96–103. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Raston, C. L. & Scott, J. L. (2000). Green Chem. 2, 49–52. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Turner, L. E., Thorn, M. G., Swartz, R. D., Chesnut, R. W., Fanwick, P. E. & Rothwell, I. P. (2003). Dalton Trans. pp. 4580–4589. Web of Science CSD CrossRef Google Scholar
Williams, P. (1967). Chem. Commun. 14, 719–20. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Four pairs (Ia, Ib) of independent molecules of the title compound occupy an orthorhombic unit cell at 123 K. Thirteen non-H framework atoms of Ia, and sixteen atoms of Ib, deviate significantly from their mean planes: δmax = 0.053 (3) and δr.m.s. = 0.027 Å, δmax = 0.052 (3) and δr.m.s. = 0.026 Å respectively. A least-squares fit of chemically equivalent pairs of non-H atomic positions (IDEAL, Gould et al., 1988) shows an average mis-match δr.m.s. = 0.051 Å, and also reveals a mirror-image pattern of deviations (above/below plane) for sixteen of the nineteen pairs. This suggests that Ia and Ib are quasi-enantiomorphs. Indeed, a least-squares fit of the relative atomic coordinates of Ia to those of Ib inverted through the origin give an average mis-match δr.m.s. = 0.022 Å.
The triclinic form of I at 123 K has been reported (Raston & Scott, 2000; CCDC refcode LOLYUG; Allen, 2002). It is also significantly non-planar with δ/σ > 3 for sixteen framework atoms. The relative atomic positions match closely those of Ia (δr.m.s. = 0.051 Å) and Ib (δr.m.s. = 0.050 Å), and the pattern of deviations for thirteen non-H atoms is identical to equivalent atoms in Ia.