Conformational transformation coupled with the order-disorder phase transition in 2-methyl-1,3-cyclohexanedione crystals

The half-chair conformation of the dynamically disordered molecular ring of 2-methyl-1,3-cyclohexanedione, CHO, transforms to a sofa below = 244 K, when the crystal undergoes a continuous phase transition induced by the onset of halting large-amplitude vibrations of methylene groups C(4)H and C(5)H. The temperature dependence of the crystal structure has been investigated by X-ray diffraction. The Ibam symmetry of the crystal reduces below to space group Pccn. The mechanism of the phase transition and of the conversion of the ring conformation is discussed.

Computing details

For all compounds, program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993).

Figures

(123)

Crystal data

C7H10O2	Z = 8
Mr = 126.15	F(000) = 544
Orthorhombic, Pccn	Dx = 1.313 Mg m^−3
Hall symbol: -P 2ab 2ac	Mo Kα radiation, λ = 0.71073 Å
a = 13.427 (3) Å	µ = 0.10 mm^−1
b = 13.689 (3) Å	T = 123 K
c = 6.946 (2) Å	Plate, colourless
V = 1276.7 (5) Å^3	0.3 × 0.3 × 0.2 mm

Data collection

KUMA-4-CCD diffractometer	Rint = 0.055
Radiation source: fine-focus sealed tube	θmax = 29.7°, θmin = 3.0°
Graphite monochromator	h = −17→16
6596 measured reflections	k = −18→18
1616 independent reflections	l = −7→9
1322 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.157	Calculated w = 1/[σ^2(Fo^2) + (0.1052P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = −0.014
1616 reflections	Δρmax = 0.44 e Å^−3
117 parameters	Δρmin = −0.31 e Å^−3
0 restraints

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.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.56748 (7)	0.45070 (6)	0.23059 (14)	0.0204 (3)
H1	0.5274 (18)	0.3894 (17)	0.229 (3)	0.046 (7)*
O2	0.52702 (8)	0.78702 (7)	0.2790 (2)	0.0248 (3)
C1	0.50884 (10)	0.52910 (9)	0.2458 (2)	0.0155 (3)
C2	0.55143 (10)	0.61931 (9)	0.2478 (2)	0.0165 (3)
C7	0.66143 (10)	0.63485 (10)	0.2226 (2)	0.0253 (4)
H7A	0.67266 (10)	0.6811 (6)	0.1210 (10)	0.033*
H7B	0.69266 (15)	0.5739 (2)	0.1905 (15)	0.033*
H7C	0.6893 (2)	0.6595 (7)	0.3403 (5)	0.033*
C3	0.48991 (10)	0.70373 (9)	0.2796 (2)	0.0175 (3)
C4	0.37998 (9)	0.68976 (9)	0.3210 (2)	0.0205 (3)
H4A	0.3435 (13)	0.7508 (13)	0.289 (2)	0.025*
H4B	0.3761 (11)	0.6800 (10)	0.459 (3)	0.025*
C5	0.33758 (9)	0.60178 (9)	0.2154 (2)	0.0195 (3)
H5A	0.2630 (15)	0.5867 (13)	0.254 (2)	0.023*
H5B	0.3401 (11)	0.6117 (11)	0.079 (2)	0.023*
C6	0.39853 (10)	0.51077 (9)	0.2618 (2)	0.0181 (3)
H6A	0.3857 (11)	0.4891 (11)	0.397 (2)	0.022*
H6B	0.3817 (12)	0.4569 (12)	0.179 (3)	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0196 (5)	0.0104 (5)	0.0313 (7)	0.0016 (3)	0.0001 (4)	−0.0018 (3)
O2	0.0272 (5)	0.0104 (5)	0.0367 (7)	−0.0005 (3)	−0.0032 (4)	−0.0010 (4)
C1	0.0189 (6)	0.0118 (6)	0.0156 (7)	0.0010 (4)	−0.0012 (4)	0.0006 (4)
C2	0.0171 (6)	0.0112 (6)	0.0212 (7)	0.0003 (4)	−0.0021 (4)	0.0005 (4)
C7	0.0179 (6)	0.0170 (7)	0.0411 (9)	−0.0027 (4)	−0.0009 (5)	−0.0008 (5)
C3	0.0211 (6)	0.0117 (6)	0.0196 (8)	0.0002 (4)	−0.0028 (5)	−0.0003 (4)
C4	0.0211 (6)	0.0153 (6)	0.0250 (8)	0.0034 (4)	0.0030 (5)	−0.0017 (5)
C5	0.0169 (6)	0.0166 (6)	0.0249 (8)	0.0018 (4)	−0.0005 (5)	−0.0002 (5)
C6	0.0164 (6)	0.0129 (6)	0.0249 (8)	−0.0019 (4)	−0.0004 (4)	0.0009 (5)

Geometric parameters (Å, º)

O1—C1	1.3353 (15)	C3—C4	1.516 (2)
O1—H1	1.00 (2)	C4—C5	1.521 (2)
O2—C3	1.2443 (15)	C4—H4A	0.99 (2)
C1—C2	1.361 (2)	C4—H4B	0.97 (2)
C1—C6	1.506 (2)	C5—C6	1.525 (2)
C2—C3	1.438 (2)	C5—H5A	1.06 (2)
C2—C7	1.502 (2)	C5—H5B	0.96 (2)
C7—H7A	0.96	C6—H6A	1.00 (2)
C7—H7B	0.96	C6—H6B	0.96 (2)
C7—H7C	0.96
C1—O1—H1	111.1 (13)	C3—C4—H4A	109.4 (10)
O1—C1—C2	118.84 (12)	C5—C4—H4A	112.0 (10)
O1—C1—C6	116.85 (11)	C3—C4—H4B	104.9 (9)
C2—C1—C6	124.30 (12)	C5—C4—H4B	110.3 (9)
C1—C2—C3	119.31 (12)	H4A—C4—H4B	108.0 (13)
C1—C2—C7	122.71 (12)	C4—C5—C6	110.11 (11)
C3—C2—C7	117.96 (11)	C4—C5—H5A	112.8 (9)
C2—C7—H7A	109.47 (7)	C6—C5—H5A	107.2 (10)
C2—C7—H7B	109.47 (7)	C4—C5—H5B	110.6 (9)
H7A—C7—H7B	109.5	C6—C5—H5B	107.8 (9)
C2—C7—H7C	109.47 (7)	H5A—C5—H5B	108.1 (12)
H7A—C7—H7C	109.5	C1—C6—C5	112.08 (10)
H7B—C7—H7C	109.5	C1—C6—H6A	106.7 (9)
O2—C3—C2	120.40 (12)	C5—C6—H6A	110.4 (9)
O2—C3—C4	120.41 (11)	C1—C6—H6B	108.3 (10)
C2—C3—C4	119.16 (10)	C5—C6—H6B	111.9 (10)
C3—C4—C5	111.90 (11)	H6A—C6—H6B	107.2 (13)
O1—C1—C2—C3	−175.04 (11)	C7—C2—C3—C4	−175.28 (12)
C6—C1—C2—C3	4.3 (2)	O2—C3—C4—C5	148.88 (13)
O1—C1—C2—C7	3.5 (2)	C2—C3—C4—C5	−33.3 (2)
C6—C1—C2—C7	−177.20 (11)	C3—C4—C5—C6	54.4 (2)
C1—C2—C3—O2	−178.86 (11)	O1—C1—C6—C5	−162.03 (12)
C7—C2—C3—O2	2.6 (2)	C2—C1—C6—C5	18.6 (2)
C1—C2—C3—C4	3.3 (2)	C4—C5—C6—C1	−47.0 (2)

(170)

Crystal data

C7H10O2	Z = 8
Mr = 126.15	F(000) = 544
Orthorhombic, Pccn	Dx = 1.305 Mg m^−3
Hall symbol: -P 2ab 2ac	Mo Kα radiation, λ = 0.71069 Å
a = 13.426 (4) Å	µ = 0.10 mm^−1
b = 13.690 (4) Å	T = 170 K
c = 6.987 (2) Å	Plate, colourless
V = 1284.2 (6) Å^3	0.3 × 0.3 × 0.2 mm

Data collection

KUMA-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 28.1°, θmin = 2.1°
Graphite monochromator	h = 0→17
846 measured reflections	k = 0→18
846 independent reflections	l = 0→9
742 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	Calculated w = 1/[σ^2(Fo^2) + (0.0807P)^2 + 0.3895P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.014
846 reflections	Δρmax = 0.38 e Å^−3
91 parameters	Δρmin = −0.14 e Å^−3
0 restraints

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.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.56773 (9)	0.45101 (8)	0.238 (11)	0.028 (5)
H1	0.528 (2)	0.3913 (18)	0.212 (6)	0.049 (9)*
O2	0.52638 (10)	0.78717 (9)	0.2790 (8)	0.0303 (12)
C1	0.50905 (12)	0.52962 (11)	0.2370 (6)	0.0150 (4)
C2	0.55142 (12)	0.61959 (11)	0.233 (3)	0.014 (2)
C7	0.66109 (14)	0.63493 (13)	0.2239 (12)	0.0282 (15)
H7A	0.6857 (2)	0.6505 (14)	0.3492 (13)	0.055 (6)*
H7B	0.6756 (2)	0.6878 (10)	0.138 (3)	0.055 (6)*
H7C	0.6927 (2)	0.5764 (5)	0.179 (3)	0.055 (6)*
C3	0.48967 (13)	0.70385 (11)	0.2793 (6)	0.0195 (10)
C4	0.38005 (13)	0.68972 (14)	0.3192 (3)	0.0245 (4)
H4A	0.34392 (13)	0.74761 (14)	0.2793 (3)	0.036 (4)*
H4B	0.37017 (13)	0.68158 (14)	0.4558 (3)	0.036 (4)*
C5	0.33843 (13)	0.60127 (13)	0.2150 (4)	0.0254 (8)
H5A	0.26956 (13)	0.59127 (13)	0.2520 (4)	0.039 (4)*
H5B	0.34029 (13)	0.61268 (13)	0.0780 (4)	0.039 (4)*
C6	0.39884 (12)	0.51075 (12)	0.263 (3)	0.0205 (12)
H6A	0.38597 (12)	0.49167 (12)	0.394 (3)	0.032 (5)*
H6B	0.37849 (12)	0.45738 (12)	0.180 (3)	0.032 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0201 (5)	0.0117 (5)	0.052 (14)	0.0022 (3)	0.000 (2)	−0.001 (2)
O2	0.0315 (7)	0.0109 (5)	0.049 (4)	0.0000 (4)	−0.0042 (8)	−0.0007 (7)
C1	0.0183 (6)	0.0134 (6)	0.0134 (6)	0.0021 (4)	−0.0013 (13)	−0.0036 (12)
C2	0.0169 (6)	0.0140 (6)	0.012 (6)	0.0004 (5)	−0.0007 (10)	−0.0005 (9)
C7	0.0174 (7)	0.0213 (8)	0.046 (5)	−0.0038 (5)	0.0000 (11)	−0.0007 (11)
C3	0.0222 (7)	0.0128 (7)	0.024 (3)	0.0013 (5)	−0.0029 (7)	−0.0001 (7)
C4	0.0209 (9)	0.0183 (8)	0.0341 (9)	0.0054 (6)	0.0026 (7)	−0.0015 (7)
C5	0.0164 (7)	0.0212 (8)	0.038 (3)	0.0021 (5)	−0.0012 (7)	0.0001 (7)
C6	0.0175 (6)	0.0156 (6)	0.029 (3)	−0.0018 (5)	−0.0012 (15)	0.000 (2)

Geometric parameters (Å, º)

O1—C1	1.334 (2)	C3—C4	1.510 (3)
O1—H1	0.99 (3)	C4—C5	1.519 (3)
O2—C3	1.243 (2)	C4—H4A	0.97
C1—C2	1.357 (2)	C4—H4B	0.97
C1—C6	1.513 (3)	C5—C6	1.518 (4)
C2—C3	1.457 (5)	C5—H5A	0.97
C2—C7	1.489 (2)	C5—H5B	0.97
C7—H7A	0.96	C6—H6A	0.97
C7—H7B	0.96	C6—H6B	0.97
C7—H7C	0.96
C1—O1—H1	110.4 (18)	C3—C4—H4A	109.25 (10)
O1—C1—C2	119.0 (2)	C5—C4—H4A	109.25 (10)
O1—C1—C6	116.1 (4)	C3—C4—H4B	109.2 (2)
C2—C1—C6	124.6 (2)	C5—C4—H4B	109.25 (12)
C1—C2—C3	118.4 (4)	H4A—C4—H4B	107.9
C1—C2—C7	122.92 (15)	C6—C5—C4	110.4 (4)
C3—C2—C7	117.4 (3)	C6—C5—H5A	109.6 (2)
C2—C7—H7A	109.5 (8)	C4—C5—H5A	109.58 (10)
C2—C7—H7B	109.5 (6)	C6—C5—H5B	109.6 (6)
H7A—C7—H7B	109.5	C4—C5—H5B	109.58 (12)
C2—C7—H7C	109.5 (3)	H5A—C5—H5B	108.1
H7A—C7—H7C	109.5	C1—C6—C5	110.9 (4)
H7B—C7—H7C	109.5	C1—C6—H6A	109.5 (6)
O2—C3—C2	120.0 (2)	C5—C6—H6A	109.5 (6)
O2—C3—C4	120.3 (2)	C1—C6—H6B	109.5 (5)
C2—C3—C4	119.6 (2)	C5—C6—H6B	109.5 (5)
C3—C4—C5	111.8 (2)	H6A—C6—H6B	108.0
O1—C1—C2—C3	−165 (4)	C7—C2—C3—C4	−170.9 (9)
C6—C1—C2—C3	8 (2)	O2—C3—C4—C5	149.3 (4)
O1—C1—C2—C7	2 (4)	C2—C3—C4—C5	−28.1 (10)
C6—C1—C2—C7	174.6 (13)	C3—C4—C5—C6	54.5 (6)
C1—C2—C3—O2	179.1 (11)	O1—C1—C6—C5	−167 (4)
C7—C2—C3—O2	11.7 (18)	C2—C1—C6—C5	19.7 (17)
C1—C2—C3—C4	−3.5 (19)	C4—C5—C6—C1	−50.0 (11)

(180)

Crystal data

C7H10O2	Z = 8
Mr = 126.15	F(000) = 544
Orthorhombic, Pccn	Dx = 1.289 Mg m^−3
Hall symbol: -P 2ab 2ac	Mo Kα radiation, λ = 0.71073 Å
a = 13.466 (4) Å	µ = 0.09 mm^−1
b = 13.691 (4) Å	T = 180 K
c = 7.053 (2) Å	Plate, colourless
V = 1300.3 (7) Å^3	0.4 × 0.3 × 0.2 mm

Data collection

KUMA-4-CCD diffractometer	Rint = 0.077
Radiation source: fine-focus sealed tube	θmax = 29.7°, θmin = 2.1°
Graphite monochromator	h = −18→15
7637 measured reflections	k = −17→18
1712 independent reflections	l = −7→9
1088 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.092	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.278	Calculated w = 1/[σ^2(Fo^2) + (0.1519P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.007
1712 reflections	Δρmax = 0.66 e Å^−3
117 parameters	Δρmin = −0.30 e Å^−3
0 restraints

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.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.56745 (13)	0.45111 (14)	0.2322 (3)	0.0418 (6)
H1	0.528 (3)	0.378 (3)	0.232 (5)	0.075 (14)*
O2	0.52617 (15)	0.78690 (15)	0.2775 (3)	0.0489 (7)
C1	0.5088 (2)	0.5297 (2)	0.2461 (3)	0.0341 (6)
C2	0.5514 (2)	0.6194 (2)	0.2484 (4)	0.0349 (7)
C7	0.6615 (2)	0.6352 (3)	0.2258 (6)	0.0503 (9)
H7A	0.678 (3)	0.683 (3)	0.109 (6)	0.090 (8)*
H7B	0.686 (3)	0.583 (4)	0.195 (6)	0.090 (8)*
H7C	0.684 (3)	0.665 (3)	0.330 (6)	0.090 (8)*
C3	0.4900 (2)	0.7042 (2)	0.2776 (4)	0.0362 (7)
C4	0.3796 (2)	0.6895 (2)	0.3176 (5)	0.0443 (8)
H4A	0.347 (2)	0.754 (3)	0.283 (4)	0.056 (6)*
H4B	0.377 (2)	0.679 (2)	0.463 (5)	0.056 (6)*
C5	0.3383 (2)	0.6008 (2)	0.2154 (4)	0.0405 (7)
H5A	0.339 (2)	0.612 (2)	0.070 (4)	0.047 (6)*
H5B	0.265 (3)	0.586 (3)	0.258 (4)	0.047 (6)*
C6	0.3984 (2)	0.5109 (2)	0.2609 (4)	0.0383 (7)
H6A	0.385 (3)	0.486 (3)	0.404 (5)	0.063 (7)*
H6B	0.381 (3)	0.456 (3)	0.173 (5)	0.063 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0263 (10)	0.0326 (11)	0.0665 (14)	0.0017 (7)	−0.0011 (8)	−0.0016 (8)
O2	0.0361 (11)	0.0329 (11)	0.078 (2)	−0.0010 (8)	−0.0051 (9)	0.0006 (9)
C1	0.0236 (11)	0.0334 (14)	0.0453 (14)	0.0022 (9)	−0.0023 (10)	0.0010 (10)
C2	0.0252 (12)	0.0315 (14)	0.048 (2)	0.0025 (9)	−0.0051 (10)	−0.0024 (10)
C7	0.0238 (13)	0.042 (2)	0.085 (3)	−0.0038 (11)	0.0018 (14)	−0.002 (2)
C3	0.0292 (13)	0.0337 (14)	0.046 (2)	0.0017 (10)	−0.0035 (10)	−0.0021 (10)
C4	0.0292 (14)	0.0381 (15)	0.066 (2)	0.0066 (10)	0.0021 (13)	−0.0010 (14)
C5	0.0203 (12)	0.043 (2)	0.058 (2)	0.0020 (10)	0.0025 (11)	0.0003 (13)
C6	0.0233 (12)	0.0362 (14)	0.055 (2)	−0.0022 (10)	−0.0026 (11)	0.0013 (12)

Geometric parameters (Å, º)

O1—C1	1.338 (3)	C3—C4	1.525 (4)
O1—H1	1.13 (4)	C4—C5	1.518 (4)
O2—C3	1.233 (3)	C4—H4A	1.02 (4)
C1—C2	1.355 (4)	C4—H4B	1.03 (3)
C1—C6	1.513 (4)	C5—C6	1.508 (4)
C2—C3	1.440 (3)	C5—H5A	1.04 (3)
C2—C7	1.507 (4)	C5—H5B	1.05 (4)
C7—H7A	1.07 (4)	C6—H6A	1.08 (3)
C7—H7B	0.82 (5)	C6—H6B	1.00 (4)
C7—H7C	0.89 (4)
C1—O1—H1	116 (2)	C5—C4—H4A	115.1 (19)
O1—C1—C2	118.7 (2)	C3—C4—H4A	105.3 (19)
O1—C1—C6	116.6 (2)	C5—C4—H4B	109.9 (17)
C2—C1—C6	124.7 (2)	C3—C4—H4B	103.9 (17)
C1—C2—C3	119.3 (2)	H4A—C4—H4B	110 (2)
C1—C2—C7	123.0 (3)	C6—C5—C4	110.8 (2)
C3—C2—C7	117.7 (2)	C6—C5—H5A	109.3 (15)
C2—C7—H7A	112 (2)	C4—C5—H5A	110.4 (15)
C2—C7—H7B	108 (3)	C6—C5—H5B	106.3 (19)
H7A—C7—H7B	104 (4)	C4—C5—H5B	111.6 (17)
C2—C7—H7C	108 (3)	H5A—C5—H5B	108 (2)
H7A—C7—H7C	107 (4)	C5—C6—C1	111.9 (2)
H7B—C7—H7C	119 (4)	C5—C6—H6A	111.4 (18)
O2—C3—C2	120.9 (2)	C1—C6—H6A	106.7 (18)
O2—C3—C4	120.4 (2)	C5—C6—H6B	111 (2)
C2—C3—C4	118.7 (2)	C1—C6—H6B	108 (2)
C5—C4—C3	112.0 (2)	H6A—C6—H6B	108 (3)
O1—C1—C2—C3	−175.4 (2)	C7—C2—C3—C4	−174.9 (3)
C6—C1—C2—C3	3.7 (4)	O2—C3—C4—C5	149.6 (3)
O1—C1—C2—C7	3.3 (4)	C2—C3—C4—C5	−33.1 (4)
C6—C1—C2—C7	−177.6 (3)	C3—C4—C5—C6	54.0 (3)
C1—C2—C3—O2	−178.8 (2)	C4—C5—C6—C1	−46.5 (3)
C7—C2—C3—O2	2.4 (4)	O1—C1—C6—C5	−162.3 (2)
C1—C2—C3—C4	3.9 (4)	C2—C1—C6—C5	18.5 (4)

(220)

Crystal data

C7H10O2	Z = 8
Mr = 126.15	F(000) = 544
Orthorhombic, Pccn	Dx = 1.289 Mg m^−3
Hall symbol: -P 2ab 2ac	Mo Kα radiation, λ = 0.71073 Å
a = 13.466 (4) Å	µ = 0.09 mm^−1
b = 13.691 (4) Å	T = 220 K
c = 7.053 (2) Å	Plate, colourless
V = 1300.3 (7) Å^3	0.3 × 0.3 × 0.2 mm

Data collection

KUMA-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 28.1°, θmin = 2.1°
Graphite monochromator	h = 0→17
856 measured reflections	k = 0→18
856 independent reflections	l = 0→9
723 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	Calculated w = 1/[σ^2(Fo^2) + (0.099P)^2 + 0.2039P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.047
856 reflections	Δρmax = 0.18 e Å^−3
91 parameters	Δρmin = −0.39 e Å^−3
0 restraints

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.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.56810 (9)	0.45141 (8)	0.234 (6)	0.034 (4)
H1	0.529 (2)	0.390 (2)	0.213 (6)	0.057 (10)*
O2	0.52514 (11)	0.78711 (10)	0.2783 (11)	0.040 (2)
C1	0.50914 (12)	0.52959 (12)	0.234 (5)	0.020 (3)
C2	0.55107 (12)	0.61977 (12)	0.233 (4)	0.021 (3)
C7	0.66039 (14)	0.63522 (14)	0.2249 (18)	0.038 (2)
H7A	0.6748 (2)	0.6904 (8)	0.146 (3)	0.063 (6)*
H7B	0.6917 (2)	0.5781 (5)	0.174 (3)	0.063 (6)*
H7C	0.6852 (2)	0.6471 (13)	0.3504 (18)	0.063 (6)*
C3	0.48909 (14)	0.70370 (12)	0.2771 (10)	0.0274 (14)
C4	0.37972 (14)	0.68935 (15)	0.3143 (3)	0.0343 (5)
H4A	0.34373 (14)	0.74685 (15)	0.2726 (3)	0.051 (5)*
H4B	0.36904 (14)	0.68208 (15)	0.4496 (3)	0.051 (5)*
C5	0.33917 (13)	0.60035 (14)	0.2127 (5)	0.0376 (12)
H5A	0.34148 (13)	0.61099 (14)	0.0768 (5)	0.055 (5)*
H5B	0.27041 (13)	0.59024 (14)	0.2487 (5)	0.055 (5)*
C6	0.39953 (13)	0.51045 (13)	0.263 (3)	0.0290 (13)
H6A	0.38755 (13)	0.49286 (13)	0.394 (3)	0.044 (6)*
H6B	0.37889 (13)	0.45615 (13)	0.184 (3)	0.044 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0265 (6)	0.0147 (5)	0.061 (11)	0.0032 (4)	0.0013 (15)	−0.002 (2)
O2	0.0406 (7)	0.0142 (6)	0.066 (5)	0.0000 (4)	−0.0048 (10)	−0.0004 (8)
C1	0.0223 (6)	0.0159 (6)	0.022 (9)	0.0020 (5)	0.0013 (12)	−0.0003 (11)
C2	0.0212 (6)	0.0158 (7)	0.027 (8)	−0.0001 (5)	−0.0006 (11)	−0.0008 (11)
C7	0.0209 (7)	0.0268 (9)	0.066 (6)	−0.0046 (5)	0.0006 (14)	−0.0009 (14)
C3	0.0291 (8)	0.0155 (8)	0.038 (4)	0.0016 (5)	−0.0023 (9)	0.0008 (8)
C4	0.0273 (9)	0.0228 (9)	0.0528 (12)	0.0067 (7)	0.0051 (8)	0.0002 (8)
C5	0.0218 (8)	0.0282 (10)	0.063 (4)	0.0025 (6)	−0.0020 (9)	0.0027 (10)
C6	0.0217 (7)	0.0205 (7)	0.045 (4)	−0.0035 (5)	−0.003 (2)	0.001 (2)

Geometric parameters (Å, º)

O1—C1	1.333 (2)	C3—C4	1.509 (3)
O1—H1	1.00 (3)	C4—C5	1.515 (3)
O2—C3	1.241 (2)	C4—H4A	0.97
C1—C2	1.358 (2)	C4—H4B	0.97
C1—C6	1.513 (5)	C5—C6	1.517 (5)
C2—C3	1.454 (6)	C5—H5A	0.97
C2—C7	1.488 (3)	C5—H5B	0.97
C7—H7A	0.96	C6—H6A	0.97
C7—H7B	0.96	C6—H6B	0.97
C7—H7C	0.96
C1—O1—H1	111.2 (16)	C3—C4—H4A	109.22 (14)
O1—C1—C2	118.9 (2)	C5—C4—H4A	109.22 (12)
O1—C1—C6	116.2 (4)	C3—C4—H4B	109.2 (3)
C2—C1—C6	124.3 (4)	C5—C4—H4B	109.22 (15)
C1—C2—C3	118.6 (6)	H4A—C4—H4B	107.9
C1—C2—C7	122.7 (2)	C4—C5—C6	110.4 (5)
C3—C2—C7	117.6 (4)	C4—C5—H5A	109.56 (15)
C2—C7—H7A	109.5 (7)	C6—C5—H5A	109.6 (7)
C2—C7—H7B	109.5 (5)	C4—C5—H5B	109.56 (11)
H7A—C7—H7B	109.5	C6—C5—H5B	109.6 (3)
C2—C7—H7C	109.5 (12)	H5A—C5—H5B	108.1
H7A—C7—H7C	109.5	C1—C6—C5	110.5 (5)
H7B—C7—H7C	109.5	C1—C6—H6A	109.5 (13)
O2—C3—C2	120.3 (2)	C5—C6—H6A	109.6 (7)
O2—C3—C4	120.0 (2)	C1—C6—H6B	109.5 (9)
C2—C3—C4	119.7 (2)	C5—C6—H6B	109.5 (5)
C3—C4—C5	112.0 (2)	H6A—C6—H6B	108.1
O1—C1—C2—C3	−166 (3)	C7—C2—C3—C4	−171.3 (13)
C6—C1—C2—C3	5 (4)	O2—C3—C4—C5	150.2 (6)
O1—C1—C2—C7	2 (5)	C2—C3—C4—C5	−27.5 (13)
C6—C1—C2—C7	173 (2)	C3—C4—C5—C6	54.3 (7)
C1—C2—C3—O2	180 (2)	O1—C1—C6—C5	−166 (3)
C7—C2—C3—O2	11 (3)	C2—C1—C6—C5	23 (3)
C1—C2—C3—C4	−3 (3)	C4—C5—C6—C1	−51.2 (17)

(225)

Crystal data

C7H10O2	Z = 8
Mr = 126.15	F(000) = 544
Orthorhombic, Pccn	Dx = 1.286 Mg m^−3
Hall symbol: -P 2ab 2ac	Mo Kα radiation, λ = 0.71073 Å
a = 13.472 (4) Å	µ = 0.09 mm^−1
b = 13.692 (4) Å	T = 225 K
c = 7.062 (2) Å	Plate, colourless
V = 1302.6 (7) Å^3	0.4 × 0.3 × 0.2 mm

Data collection

KUMA-4-CCD diffractometer	Rint = 0.044
Radiation source: fine-focus sealed tube	θmax = 29.7°, θmin = 3.0°
Graphite monochromator	h = −18→15
8309 measured reflections	k = −18→18
1756 independent reflections	l = −7→9
1097 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.091	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.272	Calculated w = 1/[σ^2(Fo^2) + (0.1436P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.17	(Δ/σ)max = 0.017
1756 reflections	Δρmax = 0.51 e Å^−3
117 parameters	Δρmin = −0.24 e Å^−3
0 restraints

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.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.56807 (13)	0.45129 (14)	0.2343 (3)	0.0455 (6)
H1	0.533 (3)	0.383 (3)	0.233 (4)	0.085 (14)*
O2	0.5250 (2)	0.78678 (14)	0.2741 (3)	0.0565 (7)
C1	0.5090 (2)	0.5297 (2)	0.2475 (3)	0.0348 (6)
C2	0.5510 (2)	0.6196 (2)	0.2492 (3)	0.0382 (6)
C7	0.6604 (2)	0.6356 (3)	0.2296 (6)	0.0562 (9)
H7A	0.673 (3)	0.677 (4)	0.104 (6)	0.128 (11)*
H7B	0.689 (4)	0.579 (5)	0.213 (6)	0.128 (11)*
H7C	0.681 (4)	0.667 (4)	0.325 (7)	0.128 (11)*
C3	0.4891 (2)	0.7036 (2)	0.2747 (4)	0.0394 (7)
C4	0.3794 (2)	0.6891 (2)	0.3108 (5)	0.0531 (8)
H4A	0.342 (3)	0.748 (4)	0.279 (5)	0.095 (9)*
H4B	0.373 (3)	0.671 (3)	0.457 (6)	0.095 (9)*
C5	0.3391 (2)	0.6000 (2)	0.2153 (5)	0.0525 (9)
H5A	0.343 (2)	0.619 (2)	0.063 (5)	0.075 (7)*
H5B	0.261 (4)	0.582 (3)	0.253 (4)	0.075 (7)*
C6	0.3993 (2)	0.5106 (2)	0.2601 (4)	0.0417 (7)
H6A	0.386 (3)	0.483 (3)	0.391 (5)	0.078 (8)*
H6B	0.384 (3)	0.458 (3)	0.186 (5)	0.078 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0333 (10)	0.0295 (11)	0.0738 (14)	0.0022 (7)	0.0007 (8)	−0.0019 (8)
O2	0.0492 (13)	0.0288 (11)	0.092 (2)	−0.0004 (8)	−0.0037 (10)	−0.0014 (8)
C1	0.0294 (11)	0.0313 (13)	0.0437 (13)	0.0014 (9)	−0.0018 (9)	0.0000 (9)
C2	0.0274 (12)	0.0319 (13)	0.055 (2)	0.0003 (9)	−0.0039 (10)	−0.0022 (10)
C7	0.0278 (13)	0.043 (2)	0.098 (3)	−0.0045 (11)	−0.0012 (14)	−0.002 (2)
C3	0.0352 (13)	0.0308 (13)	0.0522 (15)	0.0019 (9)	−0.0039 (10)	−0.0012 (10)
C4	0.0354 (14)	0.041 (2)	0.083 (2)	0.0089 (11)	0.0055 (14)	−0.0006 (15)
C5	0.0288 (13)	0.042 (2)	0.087 (2)	0.0045 (10)	0.0026 (13)	0.0015 (14)
C6	0.0286 (12)	0.0355 (13)	0.061 (2)	−0.0033 (10)	−0.0013 (11)	−0.0006 (12)

Geometric parameters (Å, º)

O1—C1	1.339 (3)	C3—C4	1.512 (4)
O1—H1	1.05 (5)	C4—C5	1.496 (4)
O2—C3	1.238 (3)	C4—H4A	0.97 (5)
C1—C2	1.355 (3)	C4—H4B	1.06 (4)
C1—C6	1.504 (4)	C5—C6	1.502 (4)
C2—C3	1.432 (3)	C5—H5A	1.11 (3)
C2—C7	1.497 (4)	C5—H5B	1.11 (5)
C7—H7A	1.06 (5)	C6—H6A	1.02 (3)
C7—H7B	0.87 (6)	C6—H6B	0.92 (4)
C7—H7C	0.84 (5)
C1—O1—H1	117 (2)	C5—C4—H4A	113 (3)
O1—C1—C2	118.8 (2)	C3—C4—H4A	111 (3)
O1—C1—C6	116.7 (2)	C5—C4—H4B	102 (2)
C2—C1—C6	124.6 (2)	C3—C4—H4B	106.1 (18)
C1—C2—C3	119.2 (2)	H4A—C4—H4B	112 (3)
C1—C2—C7	122.9 (3)	C4—C5—C6	111.9 (3)
C3—C2—C7	117.9 (2)	C4—C5—H5A	103.1 (16)
C2—C7—H7A	108 (2)	C6—C5—H5A	111.6 (16)
C2—C7—H7B	108 (4)	C4—C5—H5B	115 (2)
H7A—C7—H7B	106 (4)	C6—C5—H5B	106 (2)
C2—C7—H7C	109 (3)	H5A—C5—H5B	110 (2)
H7A—C7—H7C	110 (4)	C5—C6—C1	112.1 (2)
H7B—C7—H7C	114 (5)	C5—C6—H6A	113 (2)
O2—C3—C2	120.7 (2)	C1—C6—H6A	107 (2)
O2—C3—C4	120.3 (2)	C5—C6—H6B	114 (3)
C2—C3—C4	119.0 (2)	C1—C6—H6B	109 (3)
C5—C4—C3	112.7 (2)	H6A—C6—H6B	101 (3)
O1—C1—C2—C3	−176.3 (2)	C7—C2—C3—C4	−175.1 (3)
C6—C1—C2—C3	3.6 (4)	O2—C3—C4—C5	150.9 (3)
O1—C1—C2—C7	2.3 (4)	C2—C3—C4—C5	−31.6 (4)
C6—C1—C2—C7	−177.8 (3)	C3—C4—C5—C6	51.8 (4)
C1—C2—C3—O2	−178.9 (2)	C4—C5—C6—C1	−44.5 (4)
C7—C2—C3—O2	2.4 (4)	O1—C1—C6—C5	−162.7 (2)
C1—C2—C3—C4	3.6 (4)	C2—C1—C6—C5	17.5 (4)

(239)

Crystal data

C7H10O2	Z = 8
Mr = 126.15	F(000) = 544
Orthorhombic, Pccn	Dx = 1.281 Mg m^−3
Hall symbol: -P 2ab 2ac	Mo Kα radiation, λ = 0.71073 Å
a = 13.472 (4) Å	µ = 0.09 mm^−1
b = 13.692 (4) Å	T = 239.K K
c = 7.090 (2) Å	Plate, colourless
V = 1307.8 (7) Å^3	0.4 × 0.3 × 0.2 mm

Data collection

KUMA-4-CCD diffractometer	Rint = 0.035
Radiation source: fine-focus sealed tube	θmax = 29.6°, θmin = 3.0°
Graphite monochromator	h = −18→16
8221 measured reflections	k = −18→18
1758 independent reflections	l = −7→9
1073 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.107	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.329	Calculated w = 1/[σ^2(Fo^2) + (0.1617P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.26	(Δ/σ)max = 0.045
1758 reflections	Δρmax = 0.50 e Å^−3
117 parameters	Δρmin = −0.21 e Å^−3
0 restraints

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.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5686 (2)	0.4513 (2)	0.2380 (3)	0.0479 (8)
H1	0.533 (4)	0.390 (4)	0.241 (4)	0.072 (14)*
O2	0.5241 (2)	0.7868 (2)	0.2690 (4)	0.0610 (9)
C1	0.5091 (2)	0.5294 (2)	0.2478 (4)	0.0353 (7)
C2	0.5510 (2)	0.6196 (2)	0.2494 (4)	0.0383 (8)
C7	0.6600 (2)	0.6358 (3)	0.2352 (7)	0.0579 (12)
H7A	0.674 (4)	0.681 (5)	0.109 (8)	0.148 (16)*
H7B	0.685 (6)	0.588 (6)	0.224 (8)	0.148 (16)*
H7C	0.685 (5)	0.676 (5)	0.349 (8)	0.148 (16)*
C3	0.4884 (2)	0.7033 (2)	0.2692 (4)	0.0433 (9)
C4	0.3787 (3)	0.6888 (3)	0.3012 (7)	0.0650 (13)
H4A	0.337 (4)	0.749 (5)	0.276 (6)	0.101 (11)*
H4B	0.371 (3)	0.663 (3)	0.466 (6)	0.101 (11)*
C5	0.3400 (3)	0.5993 (3)	0.2186 (7)	0.0692 (14)
H5A	0.355 (3)	0.632 (3)	0.054 (7)	0.103 (11)*
H5B	0.266 (5)	0.582 (5)	0.253 (5)	0.103 (11)*
C6	0.3998 (2)	0.5100 (2)	0.2588 (5)	0.0423 (8)
H6A	0.395 (4)	0.477 (3)	0.382 (6)	0.088 (11)*
H6B	0.390 (4)	0.464 (4)	0.176 (6)	0.088 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0353 (12)	0.0262 (12)	0.082 (2)	0.0019 (8)	0.0007 (10)	−0.0010 (9)
O2	0.053 (2)	0.0261 (12)	0.104 (2)	−0.0004 (10)	−0.0012 (12)	−0.0007 (10)
C1	0.0316 (14)	0.0275 (15)	0.047 (2)	0.0018 (10)	−0.0015 (11)	−0.0010 (11)
C2	0.0293 (14)	0.0287 (15)	0.057 (2)	0.0019 (11)	−0.0031 (12)	0.0004 (12)
C7	0.028 (2)	0.038 (2)	0.108 (3)	−0.0045 (12)	−0.002 (2)	0.003 (2)
C3	0.037 (2)	0.028 (2)	0.065 (2)	0.0018 (11)	0.0001 (13)	−0.0006 (12)
C4	0.035 (2)	0.037 (2)	0.123 (4)	0.0083 (14)	0.005 (2)	−0.003 (2)
C5	0.030 (2)	0.039 (2)	0.139 (4)	0.0022 (13)	0.001 (2)	0.005 (2)
C6	0.0309 (15)	0.033 (2)	0.063 (2)	−0.0046 (11)	0.0006 (14)	0.0012 (14)

Geometric parameters (Å, º)

O1—C1	1.337 (3)	C3—C4	1.508 (5)
O1—H1	0.98 (5)	C4—C5	1.454 (6)
O2—C3	1.240 (4)	C4—H4A	1.01 (6)
C1—C2	1.357 (4)	C4—H4B	1.22 (4)
C1—C6	1.499 (4)	C5—C6	1.493 (5)
C2—C3	1.430 (4)	C5—H5A	1.27 (5)
C2—C7	1.489 (4)	C5—H5B	1.05 (7)
C7—H7A	1.10 (6)	C6—H6A	0.98 (4)
C7—H7B	0.74 (8)	C6—H6B	0.87 (5)
C7—H7C	1.03 (6)
C1—O1—H1	113 (3)	C5—C4—H4A	114 (3)
O1—C1—C2	118.6 (3)	C3—C4—H4A	114 (3)
O1—C1—C6	116.7 (2)	C5—C4—H4B	96 (2)
C2—C1—C6	124.7 (3)	C3—C4—H4B	105 (2)
C1—C2—C3	119.1 (3)	H4A—C4—H4B	111 (3)
C1—C2—C7	123.0 (3)	C4—C5—C6	114.8 (3)
C3—C2—C7	117.9 (3)	C4—C5—H5A	91 (2)
C2—C7—H7A	108 (3)	C6—C5—H5A	112 (2)
C2—C7—H7B	109 (6)	C4—C5—H5B	116 (3)
H7A—C7—H7B	109 (6)	C6—C5—H5B	107 (4)
C2—C7—H7C	111 (3)	H5A—C5—H5B	116 (3)
H7A—C7—H7C	106 (5)	C5—C6—C1	112.0 (3)
H7B—C7—H7C	114 (6)	C5—C6—H6A	120 (3)
O2—C3—C2	120.7 (3)	C1—C6—H6A	101 (3)
O2—C3—C4	120.1 (3)	C5—C6—H6B	112 (3)
C2—C3—C4	119.1 (3)	C1—C6—H6B	104 (4)
C5—C4—C3	113.7 (3)	H6A—C6—H6B	105 (4)
O1—C1—C2—C3	−176.9 (2)	C7—C2—C3—C4	−174.6 (4)
C6—C1—C2—C3	2.2 (4)	O2—C3—C4—C5	154.2 (4)
O1—C1—C2—C7	1.9 (5)	C2—C3—C4—C5	−29.1 (5)
C6—C1—C2—C7	−179.0 (3)	C3—C4—C5—C6	47.5 (6)
C1—C2—C3—O2	−179.1 (3)	C4—C5—C6—C1	−40.6 (5)
C7—C2—C3—O2	2.0 (5)	O1—C1—C6—C5	−165.1 (3)
C1—C2—C3—C4	4.2 (4)	C2—C1—C6—C5	15.8 (5)

(240)

Crystal data

C7H10O2	Z = 8
Mr = 126.15	F(000) = 544
Orthorhombic, Pccn	Dx = 1.279 Mg m^−3
Hall symbol: -P 2ab 2ac	Mo Kα radiation, λ = 0.71073 Å
a = 13.492 (4) Å	µ = 0.09 mm^−1
b = 13.692 (4) Å	T = 240 K
c = 7.091 (2) Å	Plate, colourless
V = 1309.9 (7) Å^3	0.4 × 0.3 × 0.2 mm

Data collection

KUMA-4-CCD diffractometer	Rint = 0.066
Radiation source: fine-focus sealed tube	θmax = 29.9°, θmin = 2.1°
Graphite monochromator	h = −18→16
8148 measured reflections	k = −18→18
1777 independent reflections	l = −7→9
948 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.196	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.490	Calculated w = 1/[σ^2(Fo^2) + (0.1986P)^2 + 0.544P] where P = (Fo^2 + 2Fc^2)/3
S = 1.31	(Δ/σ)max = 0.114
1777 reflections	Δρmax = 0.57 e Å^−3
91 parameters	Δρmin = −0.32 e Å^−3
0 restraints

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.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5690 (3)	0.4522 (3)	0.2386 (6)	0.0530 (14)
H1	0.531 (7)	0.406 (8)	0.231 (10)	0.09 (3)*
O2	0.5252 (4)	0.7866 (3)	0.2697 (7)	0.063 (2)
C1	0.5088 (4)	0.5290 (4)	0.2471 (7)	0.0372 (14)
C2	0.5512 (4)	0.6192 (4)	0.2481 (7)	0.0411 (15)
C7	0.6606 (4)	0.6355 (5)	0.2365 (9)	0.061 (2)
H7A	0.6770 (7)	0.663 (4)	0.116 (3)	0.17 (3)*
H7B	0.6945 (5)	0.5744 (8)	0.253 (8)	0.17 (3)*
H7C	0.6807 (8)	0.680 (3)	0.334 (5)	0.17 (3)*
C3	0.4886 (4)	0.7030 (4)	0.2694 (8)	0.045 (2)
C4	0.3790 (5)	0.6887 (5)	0.2986 (13)	0.074 (3)
H4A	0.3651 (5)	0.6899 (5)	0.4328 (13)	0.14 (3)*
H4B	0.3439 (5)	0.7431 (5)	0.2415 (13)	0.14 (3)*
C5	0.3415 (5)	0.5994 (5)	0.2210 (12)	0.072 (3)
H5A	0.3363 (5)	0.6071 (5)	0.0853 (12)	0.086 (19)*
H5B	0.2750 (5)	0.5892 (5)	0.2692 (12)	0.086 (19)*
C6	0.4006 (4)	0.5101 (4)	0.2599 (7)	0.047 (2)
H6A	0.3826 (4)	0.4596 (4)	0.1701 (7)	0.17 (4)*
H6B	0.3849 (4)	0.4862 (4)	0.3852 (7)	0.17 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.039 (2)	0.026 (2)	0.094 (4)	0.004 (2)	−0.006 (2)	0.002 (2)
O2	0.060 (3)	0.030 (2)	0.100 (4)	0.001 (2)	0.001 (2)	0.001 (2)
C1	0.037 (3)	0.030 (3)	0.045 (3)	−0.001 (2)	−0.009 (2)	0.005 (2)
C2	0.030 (3)	0.036 (3)	0.057 (4)	0.001 (2)	0.006 (2)	−0.002 (3)
C7	0.030 (3)	0.054 (4)	0.100 (6)	−0.002 (3)	−0.007 (3)	0.013 (4)
C3	0.032 (3)	0.034 (3)	0.070 (4)	0.002 (2)	−0.006 (3)	−0.006 (3)
C4	0.036 (4)	0.050 (4)	0.137 (7)	0.010 (3)	0.004 (4)	−0.003 (4)
C5	0.035 (3)	0.038 (4)	0.143 (8)	0.000 (3)	−0.006 (4)	0.014 (4)
C6	0.031 (3)	0.041 (3)	0.068 (4)	−0.003 (2)	0.021 (3)	0.005 (3)

Geometric parameters (Å, º)

O1—C1	1.330 (6)	C3—C4	1.506 (9)
O1—H1	0.82 (10)	C4—C5	1.434 (10)
O2—C3	1.247 (7)	C4—H4A	0.97
C1—C2	1.361 (7)	C4—H4B	0.97
C1—C6	1.485 (8)	C5—C6	1.486 (8)
C2—C3	1.433 (7)	C5—H5A	0.97
C2—C7	1.496 (8)	C5—H5B	0.97
C7—H7A	0.96	C6—H6A	0.97
C7—H7B	0.96	C6—H6B	0.97
C7—H7C	0.96
C1—O1—H1	103 (7)	C5—C4—H4A	108.8 (5)
O1—C1—C2	117.4 (5)	C3—C4—H4A	108.8 (4)
O1—C1—C6	117.8 (5)	C5—C4—H4B	108.8 (4)
C2—C1—C6	124.8 (5)	C3—C4—H4B	108.8 (4)
C1—C2—C3	118.7 (5)	H4A—C4—H4B	107.7
C1—C2—C7	123.4 (5)	C4—C5—C6	116.2 (6)
C3—C2—C7	117.9 (5)	C4—C5—H5A	108.3 (5)
C2—C7—H7A	109.5 (3)	C6—C5—H5A	108.2 (4)
C2—C7—H7B	109.5 (4)	C4—C5—H5B	108.2 (4)
H7A—C7—H7B	109.5	C6—C5—H5B	108.2 (3)
C2—C7—H7C	109.5 (3)	H5A—C5—H5B	107.4
H7A—C7—H7C	109.5	C5—C6—C1	111.9 (5)
H7B—C7—H7C	109.5	C5—C6—H6A	109.2 (4)
O2—C3—C2	120.1 (5)	C1—C6—H6A	109.2 (3)
O2—C3—C4	120.6 (5)	C5—C6—H6B	109.2 (4)
C2—C3—C4	119.3 (5)	C1—C6—H6B	109.2 (3)
C5—C4—C3	113.8 (6)	H6A—C6—H6B	107.9
O1—C1—C2—C3	−176.0 (5)	C7—C2—C3—C4	−174.7 (6)
C6—C1—C2—C3	2.3 (8)	O2—C3—C4—C5	155.8 (7)
O1—C1—C2—C7	1.2 (8)	C2—C3—C4—C5	−26.5 (10)
C6—C1—C2—C7	179.5 (5)	C3—C4—C5—C6	45.7 (10)
C1—C2—C3—O2	−179.6 (5)	C4—C5—C6—C1	−40.1 (9)
C7—C2—C3—O2	3.1 (8)	O1—C1—C6—C5	−165.9 (5)
C1—C2—C3—C4	2.7 (8)	C2—C1—C6—C5	15.8 (8)

(242)

Crystal data

C7H10O2	Z = 8
Mr = 126.15	F(000) = 544
Orthorhombic, Pccn	Dx = 1.278 Mg m^−3
Hall symbol: -P 2ab 2ac	Mo Kα radiation, λ = 0.71073 Å
a = 13.498 (4) Å	µ = 0.09 mm^−1
b = 13.691 (4) Å	T = 242 K
c = 7.095 (2) Å	Plate, colourless
V = 1311.2 (7) Å^3	0.4 × 0.3 × 0.2 mm

Data collection

KUMA-4-CCD diffractometer	889 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
Graphite monochromator	θmax = 29.8°, θmin = 2.1°
rotation scans	h = −18→16
8192 measured reflections	k = −18→18
1778 independent reflections	l = −7→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.186	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.510	Calculated w = 1/[σ^2(Fo^2) + (0.1975P)^2 + 1.2779P] where P = (Fo^2 + 2Fc^2)/3
S = 1.29	(Δ/σ)max = 0.017
1778 reflections	Δρmax = 0.50 e Å^−3
91 parameters	Δρmin = −0.35 e Å^−3
0 restraints

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.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5684 (3)	0.4522 (3)	0.2412 (6)	0.0547 (15)
H1	0.524 (8)	0.396 (8)	0.239 (10)	0.11 (4)*
O2	0.5249 (4)	0.7869 (3)	0.2676 (7)	0.068 (2)
C1	0.5093 (4)	0.5291 (4)	0.2469 (8)	0.0413 (15)
C2	0.5512 (4)	0.6187 (4)	0.2467 (8)	0.046 (2)
C7	0.6607 (5)	0.6361 (5)	0.2393 (10)	0.064 (2)
H7A	0.6773 (8)	0.668 (4)	0.123 (4)	0.18 (3)*
H7B	0.6949 (5)	0.5748 (6)	0.247 (9)	0.18 (3)*
H7C	0.6800 (9)	0.677 (4)	0.344 (5)	0.18 (3)*
C3	0.4883 (5)	0.7030 (5)	0.2676 (9)	0.051 (2)
C4	0.3788 (5)	0.6881 (6)	0.2895 (15)	0.090 (3)
H4A	0.3624 (5)	0.6939 (6)	0.4222 (15)	0.18 (4)*
H4B	0.3449 (5)	0.7404 (6)	0.2237 (15)	0.18 (4)*
C5	0.3416 (5)	0.5996 (5)	0.2242 (14)	0.085 (3)
H5A	0.3317 (5)	0.6055 (5)	0.0893 (14)	0.15 (3)*
H5B	0.2769 (5)	0.5899 (5)	0.2807 (14)	0.15 (3)*
C6	0.4003 (5)	0.5108 (5)	0.2582 (8)	0.053 (2)
H6A	0.3823 (5)	0.4617 (5)	0.1658 (8)	0.17 (4)*
H6B	0.3844 (5)	0.4852 (5)	0.3821 (8)	0.17 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.042 (3)	0.029 (2)	0.093 (4)	0.004 (2)	−0.013 (2)	0.003 (2)
O2	0.068 (3)	0.028 (2)	0.108 (4)	−0.001 (2)	0.002 (3)	−0.004 (2)
C1	0.034 (3)	0.035 (3)	0.055 (3)	0.004 (2)	−0.013 (3)	0.011 (3)
C2	0.034 (3)	0.037 (3)	0.068 (4)	−0.002 (2)	0.014 (3)	0.003 (3)
C7	0.033 (3)	0.051 (4)	0.108 (6)	−0.005 (3)	−0.010 (3)	−0.004 (4)
C3	0.038 (3)	0.040 (3)	0.075 (5)	0.008 (2)	−0.009 (3)	−0.013 (3)
C4	0.038 (4)	0.053 (5)	0.180 (10)	0.012 (3)	0.007 (5)	−0.003 (5)
C5	0.039 (4)	0.031 (3)	0.185 (10)	0.002 (3)	−0.016 (4)	0.023 (4)
C6	0.036 (3)	0.044 (3)	0.078 (5)	−0.003 (3)	0.026 (3)	0.010 (3)

Geometric parameters (Å, º)

O1—C1	1.322 (7)	C3—C4	1.500 (10)
O1—H1	0.97 (11)	C4—C5	1.391 (11)
O2—C3	1.250 (7)	C4—H4A	0.97
C1—C2	1.351 (8)	C4—H4B	0.97
C1—C6	1.494 (9)	C5—C6	1.471 (9)
C2—C3	1.442 (8)	C5—H5A	0.97
C2—C7	1.497 (9)	C5—H5B	0.97
C7—H7A	0.96	C6—H6A	0.97
C7—H7B	0.96	C6—H6B	0.97
C7—H7C	0.96
C1—O1—H1	105 (6)	C5—C4—H4A	108.3 (6)
O1—C1—C2	118.1 (5)	C3—C4—H4A	108.3 (5)
O1—C1—C6	117.5 (5)	C5—C4—H4B	108.3 (5)
C2—C1—C6	124.4 (5)	C3—C4—H4B	108.3 (4)
C1—C2—C3	118.7 (5)	H4A—C4—H4B	107.4
C1—C2—C7	123.9 (6)	C4—C5—C6	118.1 (7)
C3—C2—C7	117.2 (5)	C4—C5—H5A	107.8 (6)
C2—C7—H7A	109.5 (3)	C6—C5—H5A	107.8 (5)
C2—C7—H7B	109.5 (4)	C4—C5—H5B	107.8 (5)
H7A—C7—H7B	109.5	C6—C5—H5B	107.8 (4)
C2—C7—H7C	109.5 (4)	H5A—C5—H5B	107.1
H7A—C7—H7C	109.5	C5—C6—C1	112.5 (5)
H7B—C7—H7C	109.5	C5—C6—H6A	109.1 (4)
O2—C3—C2	120.1 (6)	C1—C6—H6A	109.1 (3)
O2—C3—C4	121.0 (6)	C5—C6—H6B	109.1 (4)
C2—C3—C4	118.8 (6)	C1—C6—H6B	109.1 (3)
C5—C4—C3	116.1 (7)	H6A—C6—H6B	107.8
O1—C1—C2—C3	−175.2 (5)	C7—C2—C3—C4	−175.7 (7)
C6—C1—C2—C3	3.1 (9)	O2—C3—C4—C5	158.5 (8)
O1—C1—C2—C7	0.3 (9)	C2—C3—C4—C5	−21.6 (12)
C6—C1—C2—C7	178.7 (5)	C3—C4—C5—C6	39.9 (13)
C1—C2—C3—O2	−179.9 (6)	C4—C5—C6—C1	−35.5 (11)
C7—C2—C3—O2	4.2 (9)	O1—C1—C6—C5	−168.1 (6)
C1—C2—C3—C4	0.2 (9)	C2—C1—C6—C5	13.5 (9)

(250)

Crystal data

C7H10O2	Z = 8
Mr = 126.15	F(000) = 544
Orthorhombic, Ibam	Dx = 1.274 Mg m^−3
Hall symbol: -I 2 2c	Mo Kα radiation, λ = 0.71069 Å
a = 13.510 (3) Å	µ = 0.09 mm^−1
b = 13.690 (3) Å	T = 250 K
c = 7.111 (1) Å	Plate, colourless
V = 1315.2 (5) Å^3	0.3 × 0.3 × 0.2 mm

Data collection

KUMA-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 28.1°, θmin = 2.1°
Graphite monochromator	h = 0→17
θ–2θ scans	k = 0→18
866 measured reflections	l = 0→9
866 independent reflections	2 standard reflections every 100 reflections
655 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	Calculated w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.0891P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.013
866 reflections	Δρmax = 0.25 e Å^−3
104 parameters	Δρmin = −0.18 e Å^−3
0 restraints

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.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.31902 (8)	0.20153 (8)	0.0000	0.0524 (4)
O2	0.27336 (11)	0.53660 (9)	0.0000	0.0710 (6)
C1	0.25946 (11)	0.27924 (10)	0.0000	0.0380 (4)
C2	0.30069 (10)	0.36961 (10)	0.0000	0.0396 (4)
C7	0.40993 (13)	0.38555 (14)	0.0000	0.0595 (7)
H71	0.425 (5)	0.447 (5)	0.0000	0.09 (3)*	0.47 (6)
H72	0.438 (3)	0.341 (4)	0.121 (7)	0.082 (19)*	0.47 (6)
H73	0.426 (2)	0.423 (2)	0.126 (4)	0.046 (12)*	0.53 (6)
H74	0.444 (4)	0.330 (5)	0.0000	0.080 (18)*	0.53 (6)
C3	0.23808 (13)	0.45325 (11)	0.0000	0.0522 (5)
C4	0.1283 (2)	0.4382 (2)	−0.0525 (4)	0.0523 (11)	0.50
H41	0.0928 (18)	0.501 (2)	−0.041 (4)	0.053 (8)*	0.50
H42	0.119 (3)	0.434 (3)	−0.175 (5)	0.061 (10)*	0.50
C5	0.0904 (2)	0.3484 (2)	0.0489 (5)	0.056 (2)	0.50
H51	0.103 (2)	0.361 (2)	0.188 (5)	0.056 (9)*	0.50
H52	0.0187 (18)	0.3351 (17)	0.042 (4)	0.043 (8)*	0.50
C6	0.15042 (12)	0.25947 (12)	0.0000	0.0465 (5)
H61	0.139 (2)	0.202 (2)	0.065 (4)	0.046 (8)*	0.50
H62	0.137 (2)	0.237 (2)	−0.149 (4)	0.053 (8)*	0.50
H1	0.283 (2)	0.140 (2)	0.0000	0.086 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0343 (6)	0.0210 (6)	0.1018 (11)	0.0024 (4)	0.000	0.000
O2	0.0523 (8)	0.0204 (6)	0.1403 (15)	0.0013 (5)	0.000	0.000
C1	0.0295 (7)	0.0229 (7)	0.0618 (9)	0.0018 (5)	0.000	0.000
C2	0.0274 (7)	0.0225 (7)	0.0691 (10)	−0.0003 (5)	0.000	0.000
C7	0.0280 (8)	0.0329 (9)	0.118 (2)	−0.0056 (5)	0.000	0.000
C3	0.0362 (9)	0.0226 (8)	0.0980 (14)	0.0031 (5)	0.000	0.000
C4	0.0350 (11)	0.0346 (11)	0.087 (3)	0.0096 (7)	−0.0055 (10)	0.0005 (10)
C5	0.0280 (9)	0.0387 (12)	0.103 (5)	0.0028 (7)	0.0042 (11)	−0.0051 (12)
C6	0.0292 (8)	0.0293 (8)	0.0808 (12)	−0.0046 (6)	0.000	0.000

Geometric parameters (Å, º)

O1—C1	1.334 (2)	C4—C4^i	0.747 (6)
O1—H1	0.97 (3)	C4—C5^i	1.332 (3)
O2—C3	1.237 (2)	C4—C5	1.514 (4)
C1—C2	1.357 (2)	C4—H41	0.99 (3)
C1—C6	1.498 (2)	C4—H42	0.88 (3)
C2—C3	1.424 (2)	C5—C5^i	0.696 (7)
C2—C7	1.492 (2)	C5—C4^i	1.332 (3)
C7—H71	0.86 (7)	C5—C6	1.504 (3)
C7—H72	1.12 (5)	C5—H51	1.02 (3)
C7—H73	1.05 (3)	C5—H52	0.99 (2)
C7—H74	0.89 (7)	C6—C5^i	1.504 (3)
C3—C4	1.544 (3)	C6—H61	0.93 (3)
C3—C4^i	1.544 (3)	C6—H62	1.12 (3)
C1—O1—H1	112.7 (18)	C3—C4—H41	109.3 (15)
O1—C1—C2	118.66 (14)	C4^i—C4—H42	171 (2)
O1—C1—C6	116.69 (13)	C5^i—C4—H42	84 (2)
C2—C1—C6	124.65 (13)	C5—C4—H42	112 (2)
C1—C2—C3	119.30 (13)	C3—C4—H42	112 (2)
C1—C2—C7	122.65 (14)	H41—C4—H42	94 (3)
C3—C2—C7	118.05 (14)	C5^i—C5—C4^i	91.1 (2)
C2—C7—H71	112 (5)	C5^i—C5—C6	76.62 (12)
C2—C7—H72	105 (2)	C4^i—C5—C6	123.0 (2)
H71—C7—H72	117 (3)	C5^i—C5—C4	61.5 (2)
C2—C7—H73	106.0 (15)	C4^i—C5—C4	29.6 (2)
H71—C7—H73	58.7 (14)	C6—C5—C4	111.4 (2)
H72—C7—H73	63 (2)	C5^i—C5—H51	166.7 (18)
C2—C7—H74	113 (4)	C4^i—C5—H51	76.6 (18)
H71—C7—H74	136 (6)	C6—C5—H51	105.6 (18)
H72—C7—H74	50 (2)	C4—C5—H51	106.1 (18)
H73—C7—H74	108 (2)	C5^i—C5—H52	86.9 (15)
O2—C3—C2	120.87 (15)	C4^i—C5—H52	123.3 (14)
O2—C3—C4	119.57 (15)	C6—C5—H52	111.6 (14)
C2—C3—C4	117.64 (14)	C4—C5—H52	117.1 (14)
O2—C3—C4^i	119.57 (15)	H51—C5—H52	104 (2)
C2—C3—C4^i	117.64 (14)	C1—C6—C5	112.58 (14)
C4—C3—C4^i	28.0 (2)	C1—C6—C5^i	112.58 (14)
C4^i—C4—C5^i	88.9 (2)	C5—C6—C5^i	26.8 (3)
C4^i—C4—C5	61.5 (2)	C1—C6—H61	108.7 (19)
C5^i—C4—C5	27.3 (3)	C5—C6—H61	118.9 (18)
C4^i—C4—C3	75.99 (11)	C5^i—C6—H61	135.5 (19)
C5^i—C4—C3	119.2 (2)	C1—C6—H62	102.1 (17)
C5—C4—C3	108.5 (2)	C5—C6—H62	110.6 (17)
C4^i—C4—H41	85.4 (17)	C5^i—C6—H62	85.0 (17)
C5^i—C4—H41	128.0 (15)	H61—C6—H62	102 (3)
C5—C4—H41	120.3 (16)
O1—C1—C2—C3	180.0	C4^i—C4—C5—C5^i	180.000 (1)
C6—C1—C2—C3	0.0	C5^i—C4—C5—C5^i	0.0
O1—C1—C2—C7	0.0	C3—C4—C5—C5^i	−118.1 (2)
C6—C1—C2—C7	180.0	C4^i—C4—C5—C4^i	0.000 (1)
C1—C2—C3—O2	180.0	C5^i—C4—C5—C4^i	180.000 (1)
C7—C2—C3—O2	0.0	C3—C4—C5—C4^i	61.9 (2)
C1—C2—C3—C4	−15.85 (12)	C4^i—C4—C5—C6	−119.7 (2)
C7—C2—C3—C4	164.15 (12)	C5^i—C4—C5—C6	60.3 (2)
C1—C2—C3—C4^i	15.85 (12)	C3—C4—C5—C6	−57.8 (3)
C7—C2—C3—C4^i	−164.15 (12)	O1—C1—C6—C5	165.49 (14)
O2—C3—C4—C4^i	−98.13 (8)	C2—C1—C6—C5	−14.51 (14)
C2—C3—C4—C4^i	97.50 (7)	O1—C1—C6—C5^i	−165.49 (14)
C4^i—C3—C4—C4^i	0.0	C2—C1—C6—C5^i	14.51 (14)
O2—C3—C4—C5^i	−178.8 (2)	C5^i—C5—C6—C1	95.67 (7)
C2—C3—C4—C5^i	16.8 (3)	C4^i—C5—C6—C1	13.2 (3)
C4^i—C3—C4—C5^i	−80.7 (3)	C4—C5—C6—C1	43.9 (2)
O2—C3—C4—C5	−151.17 (15)	C5^i—C5—C6—C5^i	0.0
C2—C3—C4—C5	44.5 (2)	C4^i—C5—C6—C5^i	−82.5 (3)
C4^i—C3—C4—C5	−53.0 (2)	C4—C5—C6—C5^i	−51.7 (2)

Symmetry code: (i) x, y, −z.

(293)

Crystal data

C7H10O2	Z = 8
Mr = 126.15	F(000) = 544
Orthorhombic, Ibam	Dx = 1.258 Mg m^−3
Hall symbol: -I 2 2c	Mo Kα radiation, λ = 0.71069 Å
a = 13.558 (3) Å	µ = 0.09 mm^−1
b = 13.696 (3) Å	T = 293 K
c = 7.174 (1) Å	Plate, colourless
V = 1332.1 (5) Å^3	0.5 × 0.4 × 0.2 mm

Data collection

KUMA-4 diffractometer	Rint = 0.019
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.1°
Graphite monochromator	h = −12→−1
θ–2θ scans	k = −16→0
568 measured reflections	l = 0→8
566 independent reflections	2 standard reflections every 100 reflections
526 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.044	Calculated w = 1/[σ^2(Fo^2) + (0.0993P)^2 + 0.0875P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.116	(Δ/σ)max = 3.670
S = 1.03	Δρmax = 0.22 e Å^−3
566 reflections	Δρmin = −0.18 e Å^−3
105 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0649 (72)
Primary atom site location: structure-invariant direct methods

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.

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.31952 (9)	0.20214 (8)	0.0000	0.0654 (5)
O2	0.27230 (12)	0.53650 (9)	0.0000	0.0856 (6)
C1	0.25952 (14)	0.27921 (10)	0.0000	0.0492 (5)
C2	0.30043 (12)	0.36966 (12)	0.0000	0.0528 (6)
C7	0.4090 (2)	0.38588 (14)	0.0000	0.0778 (8)
H71	0.417 (6)	0.448 (8)	0.0000	0.11 (3)*	0.37 (6)
H72	0.444 (3)	0.338 (3)	0.117 (6)	0.062 (18)*	0.37 (6)
H73	0.428 (2)	0.425 (3)	0.122 (4)	0.087 (13)*	0.63 (6)
H74	0.444 (3)	0.329 (4)	0.0000	0.077 (13)*	0.63 (6)
C3	0.2374 (2)	0.45319 (12)	0.0000	0.0630 (6)
C4	0.1281 (2)	0.4377 (2)	−0.0472 (6)	0.071 (2)	0.50
H41	0.0934 (17)	0.496 (2)	−0.041 (4)	0.056 (7)*	0.50
H42	0.122 (3)	0.432 (4)	−0.192 (6)	0.109 (15)*	0.50
C5	0.0915 (2)	0.3476 (2)	0.0530 (4)	0.0684 (14)	0.50
H51	0.103 (2)	0.360 (3)	0.196 (5)	0.079 (9)*	0.50
H52	0.019 (2)	0.3348 (19)	0.040 (4)	0.063 (9)*	0.50
C6	0.15149 (15)	0.25900 (13)	0.0000	0.0591 (6)
H61	0.136 (2)	0.199 (3)	0.065 (4)	0.068 (10)*	0.50
H62	0.137 (2)	0.238 (3)	−0.141 (5)	0.069 (9)*	0.50
H1	0.283 (3)	0.145 (3)	0.0000	0.110 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0452 (10)	0.0298 (7)	0.1213 (12)	0.0026 (4)	0.000	0.000
O2	0.0692 (11)	0.0286 (7)	0.159 (2)	0.0008 (5)	0.000	0.000
C1	0.0431 (12)	0.0322 (8)	0.0723 (10)	0.0017 (5)	0.000	0.000
C2	0.0400 (12)	0.0332 (9)	0.0853 (13)	−0.0006 (6)	0.000	0.000
C7	0.0435 (14)	0.0422 (11)	0.148 (2)	−0.0054 (7)	0.000	0.000
C3	0.0494 (13)	0.0332 (9)	0.1064 (14)	0.0027 (6)	0.000	0.000
C4	0.049 (2)	0.0445 (12)	0.121 (7)	0.0119 (9)	−0.0044 (12)	0.0022 (12)
C5	0.040 (2)	0.0539 (14)	0.111 (4)	0.0017 (9)	0.0050 (10)	−0.0047 (11)
C6	0.0445 (13)	0.0376 (9)	0.0951 (15)	−0.0067 (7)	0.000	0.000

Geometric parameters (Å, º)

O1—C1	1.333 (2)	C4—C4^i	0.678 (8)
O1—H1	0.93 (4)	C4—C5^i	1.331 (4)
O2—C3	1.235 (2)	C4—C5	1.513 (4)
C1—C2	1.357 (2)	C4—H41	0.93 (3)
C1—C6	1.491 (3)	C4—H42	1.04 (4)
C2—C3	1.428 (2)	C5—C5^i	0.761 (6)
C2—C7	1.489 (3)	C5—C4^i	1.331 (4)
C7—H71	0.85 (11)	C5—C6	1.509 (3)
C7—H72	1.17 (5)	C5—H51	1.05 (4)
C7—H73	1.06 (3)	C5—H52	1.01 (3)
C7—H74	0.91 (5)	C6—C5^i	1.509 (3)
C3—C4	1.536 (4)	C6—H61	0.97 (3)
C3—C4^i	1.536 (4)	C6—H62	1.07 (3)
C1—O1—H1	110 (2)	C3—C4—H41	111.0 (14)
O1—C1—C2	118.3 (2)	C4^i—C4—H42	174 (2)
O1—C1—C6	116.92 (14)	C5^i—C4—H42	83 (3)
C2—C1—C6	124.81 (15)	C5—C4—H42	113 (3)
C1—C2—C3	119.1 (2)	C3—C4—H42	108 (2)
C1—C2—C7	122.7 (2)	H41—C4—H42	94 (3)
C3—C2—C7	118.15 (15)	C5^i—C5—C4^i	88.2 (2)
C2—C7—H71	106 (6)	C5^i—C5—C6	75.40 (11)
C2—C7—H72	108.8 (19)	C4^i—C5—C6	122.4 (2)
H71—C7—H72	121 (4)	C5^i—C5—C4	61.6 (2)
C2—C7—H73	108.4 (15)	C4^i—C5—C4	26.6 (3)
H71—C7—H73	58.1 (19)	C6—C5—C4	111.1 (2)
H72—C7—H73	66 (2)	C5^i—C5—H51	167.2 (18)
C2—C7—H74	113 (3)	C4^i—C5—H51	80 (2)
H71—C7—H74	142 (6)	C6—C5—H51	106.9 (19)
H72—C7—H74	46 (2)	C4—C5—H51	107 (2)
H73—C7—H74	108 (2)	C5^i—C5—H52	84.8 (16)
O2—C3—C2	120.8 (2)	C4^i—C5—H52	121.6 (15)
O2—C3—C4	119.8 (2)	C6—C5—H52	111.5 (16)
C2—C3—C4	117.83 (15)	C4—C5—H52	114.9 (15)
O2—C3—C4^i	119.8 (2)	H51—C5—H52	106 (2)
C2—C3—C4^i	117.83 (15)	C1—C6—C5	112.4 (2)
C4—C3—C4^i	25.5 (3)	C1—C6—C5^i	112.4 (2)
C4^i—C4—C5^i	91.8 (2)	C5—C6—C5^i	29.2 (2)
C4^i—C4—C5	61.6 (2)	C1—C6—H61	112.0 (19)
C5^i—C4—C5	30.2 (2)	C5—C6—H61	116 (2)
C4^i—C4—C3	77.3 (2)	C5^i—C6—H61	133.1 (19)
C5^i—C4—C3	119.6 (2)	C1—C6—H62	103.1 (17)
C5—C4—C3	108.9 (2)	C5—C6—H62	111.1 (19)
C4^i—C4—H41	87.3 (16)	C5^i—C6—H62	83.3 (19)
C5^i—C4—H41	127.7 (15)	H61—C6—H62	101 (3)
C5—C4—H41	121.0 (15)
O1—C1—C2—C3	180.0	C4^i—C4—C5—C5^i	180.000 (1)
C6—C1—C2—C3	0.0	C5^i—C4—C5—C5^i	0.000 (1)
O1—C1—C2—C7	0.0	C3—C4—C5—C5^i	−116.8 (2)
C6—C1—C2—C7	180.0	C4^i—C4—C5—C4^i	0.000 (1)
C1—C2—C3—O2	180.0	C5^i—C4—C5—C4^i	180.000 (2)
C7—C2—C3—O2	0.0	C3—C4—C5—C4^i	63.2 (2)
C1—C2—C3—C4	−14.4 (2)	C4^i—C4—C5—C6	−121.0 (2)
C7—C2—C3—C4	165.6 (2)	C5^i—C4—C5—C6	59.0 (2)
C1—C2—C3—C4^i	14.4 (2)	C3—C4—C5—C6	−57.8 (3)
C7—C2—C3—C4^i	−165.6 (2)	O1—C1—C6—C5	164.18 (12)
O2—C3—C4—C4^i	−97.44 (10)	C2—C1—C6—C5	−15.82 (12)
C2—C3—C4—C4^i	96.86 (9)	O1—C1—C6—C5^i	−164.18 (12)
C4^i—C3—C4—C4^i	0.0	C2—C1—C6—C5^i	15.82 (12)
O2—C3—C4—C5^i	177.8 (2)	C5^i—C5—C6—C1	96.16 (7)
C2—C3—C4—C5^i	12.1 (4)	C4^i—C5—C6—C1	17.9 (3)
C4^i—C3—C4—C5^i	−84.7 (3)	C4—C5—C6—C1	45.0 (2)
O2—C3—C4—C5	−151.1 (2)	C5^i—C5—C6—C5^i	0.0
C2—C3—C4—C5	43.2 (3)	C4^i—C5—C6—C5^i	−78.2 (3)
C4^i—C3—C4—C5	−53.6 (2)	C4—C5—C6—C5^i	−51.2 (2)

Symmetry code: (i) x, y, −z.