Anisole at 100 K: the first crystal structure determination

The simplest alkyl aryl ether, anisole (meth­oxy­benzene), C₇H₈O, 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 P2₁/c with two mol­ecules in the asymmetric unit (Z' = 2). Both crystallographically distinct mol­ecules adopt a virtually flat (C_s-symmetric) conformation. The arrangement of the mol­ecules in the solid state appears to be governed by close packing. No face-to-face [pi]-[pi] stacking of the mol­ecules is observed, but rather edge-to-face inter­actions result in a herringbone packing motif.

Computing details

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).

Methoxybenzene

Crystal data

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) Å^3	Cylinder, colourless
Z = 8	1.00 × 0.50 × 0.50 mm
F(000) = 464

Data collection

Bruker X8 Proteum diffractometer	2105 independent reflections
Radiation source: 0.2 x 2mm^2 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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0577P)^2 + 0.3031P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0127 (11)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)