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The simplest alkyl aryl ether, anisole (methoxybenzene), C
7H
8O, is a feedstock chemical and is widely used in the pharmaceutical industry. The structure of anisole at 100 K, as determined by single-crystal X-ray analysis, is reported. A crystal (m.p. 236 K) suitable for X-ray diffraction was obtained from the melt. The title compound crystallizes in the centrosymmetric space group
P2
1/
c with two molecules in the asymmetric unit (
Z' = 2). Both crystallographically distinct molecules adopt a virtually flat (
Cs-symmetric) conformation. The arrangement of the molecules in the solid state appears to be governed by close packing. No face-to-face
-
stacking of the molecules is observed, but rather edge-to-face interactions result in a herringbone packing motif.
Supporting information
CCDC reference: 1409620
Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2014); software used to prepare material for publication: enCIFer (Allen et al., 2004).
Crystal data top
C7H8O | Dx = 1.199 Mg m−3 |
Mr = 108.13 | Melting point: 236 K |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 13.4809 (6) Å | Cell parameters from 9877 reflections |
b = 14.3767 (7) Å | θ = 6.6–67.3° |
c = 6.2095 (3) Å | µ = 0.63 mm−1 |
β = 95.570 (1)° | T = 100 K |
V = 1197.79 (10) Å3 | Cylinder, colourless |
Z = 8 | 1.00 × 0.50 × 0.50 mm |
F(000) = 464 | |
Data collection top
Bruker X8 Proteum diffractometer | 2105 independent reflections |
Radiation source: 0.2 x 2mm2 focus rotating anode | 2004 reflections with I > 2σ(I) |
MONTEL graded multilayer optic monochromator | Rint = 0.038 |
Detector resolution: 16.67 pixels mm-1 | θmax = 67.4°, θmin = 3.3° |
φ– and ω scans | h = −16→16 |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | k = −15→13 |
Tmin = 0.387, Tmax = 1.000 | l = −7→7 |
40069 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0577P)2 + 0.3031P] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max < 0.001 |
2105 reflections | Δρmax = 0.24 e Å−3 |
148 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0127 (11) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.14035 (6) | 0.62419 (5) | 0.64955 (12) | 0.0233 (2) | |
O2 | 0.35693 (6) | 0.36283 (6) | 0.36620 (12) | 0.0225 (2) | |
C1 | 0.23901 (8) | 0.62538 (7) | 0.72931 (16) | 0.0184 (3) | |
C2 | 0.31286 (8) | 0.67430 (8) | 0.63526 (17) | 0.0209 (3) | |
H2 | 0.2968 | 0.7103 | 0.5083 | 0.025* | |
C3 | 0.41069 (8) | 0.66959 (8) | 0.73071 (18) | 0.0221 (3) | |
H3 | 0.4615 | 0.7031 | 0.6683 | 0.027* | |
C4 | 0.43501 (9) | 0.61702 (8) | 0.91443 (18) | 0.0233 (3) | |
H4 | 0.5021 | 0.6135 | 0.9765 | 0.028* | |
C5 | 0.36030 (9) | 0.56921 (8) | 1.00777 (17) | 0.0241 (3) | |
H5 | 0.3764 | 0.5336 | 1.1353 | 0.029* | |
C6 | 0.26252 (8) | 0.57318 (7) | 0.91574 (17) | 0.0214 (3) | |
H6 | 0.2117 | 0.5403 | 0.9798 | 0.026* | |
C7 | 0.11322 (9) | 0.67593 (9) | 0.45767 (18) | 0.0281 (3) | |
H7A | 0.1306 | 0.7415 | 0.4825 | 0.042* | |
H7B | 0.0413 | 0.6703 | 0.4184 | 0.042* | |
H7C | 0.1491 | 0.6516 | 0.3399 | 0.042* | |
C8 | 0.26025 (8) | 0.37312 (7) | 0.27805 (17) | 0.0181 (3) | |
C9 | 0.18780 (8) | 0.42311 (7) | 0.37448 (17) | 0.0215 (3) | |
H9 | 0.2035 | 0.4532 | 0.5098 | 0.026* | |
C10 | 0.09204 (8) | 0.42819 (8) | 0.26886 (19) | 0.0239 (3) | |
H10 | 0.0423 | 0.4624 | 0.3329 | 0.029* | |
C11 | 0.06800 (9) | 0.38443 (8) | 0.07286 (19) | 0.0248 (3) | |
H11 | 0.0022 | 0.3883 | 0.0031 | 0.030* | |
C12 | 0.14099 (9) | 0.33451 (8) | −0.02174 (17) | 0.0235 (3) | |
H12 | 0.1251 | 0.3043 | −0.1568 | 0.028* | |
C13 | 0.23676 (8) | 0.32882 (7) | 0.08087 (17) | 0.0203 (3) | |
H13 | 0.2864 | 0.2946 | 0.0163 | 0.024* | |
C14 | 0.38442 (9) | 0.40747 (9) | 0.56823 (18) | 0.0281 (3) | |
H14A | 0.3739 | 0.4747 | 0.5525 | 0.042* | |
H14B | 0.4549 | 0.3951 | 0.6136 | 0.042* | |
H14C | 0.3434 | 0.3833 | 0.6775 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0196 (4) | 0.0269 (5) | 0.0233 (4) | −0.0003 (3) | 0.0017 (3) | 0.0035 (3) |
O2 | 0.0212 (4) | 0.0275 (5) | 0.0187 (4) | 0.0011 (3) | 0.0013 (3) | −0.0031 (3) |
C1 | 0.0203 (6) | 0.0170 (6) | 0.0185 (5) | 0.0011 (4) | 0.0046 (4) | −0.0029 (4) |
C2 | 0.0247 (6) | 0.0199 (6) | 0.0187 (5) | 0.0023 (4) | 0.0046 (4) | 0.0016 (4) |
C3 | 0.0220 (6) | 0.0206 (6) | 0.0247 (6) | −0.0011 (4) | 0.0072 (4) | −0.0010 (4) |
C4 | 0.0217 (6) | 0.0240 (6) | 0.0239 (6) | 0.0021 (4) | 0.0001 (4) | −0.0032 (4) |
C5 | 0.0321 (6) | 0.0216 (6) | 0.0187 (5) | 0.0030 (5) | 0.0026 (5) | 0.0029 (4) |
C6 | 0.0260 (6) | 0.0191 (6) | 0.0200 (5) | −0.0010 (4) | 0.0066 (4) | −0.0002 (4) |
C7 | 0.0243 (6) | 0.0327 (7) | 0.0267 (6) | 0.0016 (5) | −0.0014 (5) | 0.0056 (5) |
C8 | 0.0204 (6) | 0.0164 (6) | 0.0180 (5) | −0.0021 (4) | 0.0053 (4) | 0.0028 (4) |
C9 | 0.0268 (6) | 0.0196 (6) | 0.0190 (5) | −0.0022 (4) | 0.0063 (4) | −0.0020 (4) |
C10 | 0.0232 (6) | 0.0216 (6) | 0.0283 (6) | 0.0011 (4) | 0.0096 (5) | 0.0001 (4) |
C11 | 0.0212 (6) | 0.0247 (6) | 0.0282 (6) | −0.0015 (4) | 0.0006 (5) | 0.0017 (4) |
C12 | 0.0296 (6) | 0.0215 (6) | 0.0194 (5) | −0.0030 (4) | 0.0025 (4) | −0.0024 (4) |
C13 | 0.0247 (6) | 0.0183 (6) | 0.0186 (5) | 0.0001 (4) | 0.0060 (4) | −0.0003 (4) |
C14 | 0.0271 (6) | 0.0368 (7) | 0.0201 (6) | −0.0016 (5) | 0.0004 (5) | −0.0049 (5) |
Geometric parameters (Å, º) top
O1—C1 | 1.3736 (13) | C7—H7B | 0.9800 |
O1—C7 | 1.4220 (13) | C7—H7C | 0.9800 |
O2—C8 | 1.3718 (13) | C8—C13 | 1.3891 (15) |
O2—C14 | 1.4257 (13) | C8—C9 | 1.3938 (15) |
C1—C6 | 1.3902 (15) | C9—C10 | 1.3920 (16) |
C1—C2 | 1.3927 (15) | C9—H9 | 0.9500 |
C2—C3 | 1.3941 (16) | C10—C11 | 1.3804 (16) |
C2—H2 | 0.9500 | C10—H10 | 0.9500 |
C3—C4 | 1.3811 (16) | C11—C12 | 1.3930 (16) |
C3—H3 | 0.9500 | C11—H11 | 0.9500 |
C4—C5 | 1.3914 (16) | C12—C13 | 1.3856 (16) |
C4—H4 | 0.9500 | C12—H12 | 0.9500 |
C5—C6 | 1.3861 (16) | C13—H13 | 0.9500 |
C5—H5 | 0.9500 | C14—H14A | 0.9800 |
C6—H6 | 0.9500 | C14—H14B | 0.9800 |
C7—H7A | 0.9800 | C14—H14C | 0.9800 |
| | | |
C1—O1—C7 | 117.18 (8) | H7B—C7—H7C | 109.5 |
C8—O2—C14 | 117.28 (8) | O2—C8—C13 | 115.39 (9) |
O1—C1—C6 | 115.34 (9) | O2—C8—C9 | 124.22 (10) |
O1—C1—C2 | 124.17 (10) | C13—C8—C9 | 120.39 (10) |
C6—C1—C2 | 120.49 (10) | C10—C9—C8 | 118.76 (10) |
C1—C2—C3 | 118.84 (10) | C10—C9—H9 | 120.6 |
C1—C2—H2 | 120.6 | C8—C9—H9 | 120.6 |
C3—C2—H2 | 120.6 | C11—C10—C9 | 121.27 (10) |
C4—C3—C2 | 121.12 (10) | C11—C10—H10 | 119.4 |
C4—C3—H3 | 119.4 | C9—C10—H10 | 119.4 |
C2—C3—H3 | 119.4 | C10—C11—C12 | 119.45 (11) |
C3—C4—C5 | 119.40 (10) | C10—C11—H11 | 120.3 |
C3—C4—H4 | 120.3 | C12—C11—H11 | 120.3 |
C5—C4—H4 | 120.3 | C13—C12—C11 | 120.08 (10) |
C6—C5—C4 | 120.39 (10) | C13—C12—H12 | 120.0 |
C6—C5—H5 | 119.8 | C11—C12—H12 | 120.0 |
C4—C5—H5 | 119.8 | C12—C13—C8 | 120.05 (10) |
C5—C6—C1 | 119.75 (10) | C12—C13—H13 | 120.0 |
C5—C6—H6 | 120.1 | C8—C13—H13 | 120.0 |
C1—C6—H6 | 120.1 | O2—C14—H14A | 109.5 |
O1—C7—H7A | 109.5 | O2—C14—H14B | 109.5 |
O1—C7—H7B | 109.5 | H14A—C14—H14B | 109.5 |
H7A—C7—H7B | 109.5 | O2—C14—H14C | 109.5 |
O1—C7—H7C | 109.5 | H14A—C14—H14C | 109.5 |
H7A—C7—H7C | 109.5 | H14B—C14—H14C | 109.5 |
| | | |
C2—C1—O1—C7 | 0.53 (15) | C9—C8—O2—C14 | −0.81 (15) |
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