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

Katrusiak, A.

doi:10.1107/S0108768100005905

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

A. Katrusiak

The half-chair conformation of the dynamically disordered molecular ring of 2-methyl-1,3-cyclohexanedione, C

H $_{10}$ O

, 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.

Keywords: Conformation; Order-disorder; Phase transitions; Temperature dependence.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100005905/hr0044sup1.cif Contains datablocks 123, 170, 180, 220, 225, 239, 240, 242, 250, 293, global
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100005905/hr0044123sup2.hkl Contains datablock 123
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100005905/hr0044170sup3.hkl Contains datablock 170
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100005905/hr0044180sup4.hkl Contains datablock 180
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100005905/hr0044220sup5.hkl Contains datablock 220
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100005905/hr0044225sup6.hkl Contains datablock 225
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100005905/hr0044239sup7.hkl Contains datablock 239
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100005905/hr0044240sup8.hkl Contains datablock 240
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100005905/hr0044242sup9.hkl Contains datablock 242
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100005905/hr0044250sup10.hkl Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768100005905/hr0044293sup11.hkl Supplementary material

CCDC references: 153328; 153329; 153330; 153331; 153332; 153333; 153334; 153335; 153336; 153337

Computing details top

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

Figures top

(123) top

Crystal data top

C₇H₁₀O₂	Z = 8
M_r = 126.15	F(000) = 544
Orthorhombic, Pccn	D_x = 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) Å³	0.3 × 0.3 × 0.2 mm

Data collection top

KUMA-4-CCD diffractometer	R_int = 0.055
Radiation source: fine-focus sealed tube	θ_max = 29.7°, θ_min = 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 top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	Calculated w = 1/[σ²(F_o²) + (0.1052P)²] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = −0.014
1616 reflections	Δρ_max = 0.44 e Å⁻³
117 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints

Crystal data top

C₇H₁₀O₂	V = 1276.7 (5) Å³
M_r = 126.15	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 13.427 (3) Å	µ = 0.10 mm⁻¹
b = 13.689 (3) Å	T = 123 K
c = 6.946 (2) Å	0.3 × 0.3 × 0.2 mm

Data collection top

KUMA-4-CCD diffractometer	1322 reflections with I > 2σ(I)
6596 measured reflections	R_int = 0.055
1616 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	117 parameters
wR(F²) = 0.157	0 restraints
S = 1.10	Δρ_max = 0.44 e Å⁻³
1616 reflections	Δρ_min = −0.31 e Å⁻³

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.

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

Crystal data top

C₇H₁₀O₂	Z = 8
M_r = 126.15	F(000) = 544
Orthorhombic, Pccn	D_x = 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) Å³	0.3 × 0.3 × 0.2 mm

Data collection top

KUMA-4 diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 28.1°, θ_min = 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 top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	Calculated w = 1/[σ²(F_o²) + (0.0807P)² + 0.3895P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.014
846 reflections	Δρ_max = 0.38 e Å⁻³
91 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints

Crystal data top

C₇H₁₀O₂	V = 1284.2 (6) Å³
M_r = 126.15	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 13.426 (4) Å	µ = 0.10 mm⁻¹
b = 13.690 (4) Å	T = 170 K
c = 6.987 (2) Å	0.3 × 0.3 × 0.2 mm

Data collection top

KUMA-4 diffractometer	742 reflections with I > 2σ(I)
846 measured reflections	R_int = 0.000
846 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	91 parameters
wR(F²) = 0.118	0 restraints
S = 1.04	Δρ_max = 0.38 e Å⁻³
846 reflections	Δρ_min = −0.14 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

Crystal data top

C₇H₁₀O₂	Z = 8
M_r = 126.15	F(000) = 544
Orthorhombic, Pccn	D_x = 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) Å³	0.4 × 0.3 × 0.2 mm

Data collection top

KUMA-4-CCD diffractometer	R_int = 0.077
Radiation source: fine-focus sealed tube	θ_max = 29.7°, θ_min = 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 top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.092	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.278	Calculated w = 1/[σ²(F_o²) + (0.1519P)²] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.007
1712 reflections	Δρ_max = 0.66 e Å⁻³
117 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints

Crystal data top

C₇H₁₀O₂	V = 1300.3 (7) Å³
M_r = 126.15	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 13.466 (4) Å	µ = 0.09 mm⁻¹
b = 13.691 (4) Å	T = 180 K
c = 7.053 (2) Å	0.4 × 0.3 × 0.2 mm

Data collection top

KUMA-4-CCD diffractometer	1088 reflections with I > 2σ(I)
7637 measured reflections	R_int = 0.077
1712 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.092	117 parameters
wR(F²) = 0.278	0 restraints
S = 1.15	Δρ_max = 0.66 e Å⁻³
1712 reflections	Δρ_min = −0.30 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

Crystal data top

C₇H₁₀O₂	Z = 8
M_r = 126.15	F(000) = 544
Orthorhombic, Pccn	D_x = 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) Å³	0.3 × 0.3 × 0.2 mm

Data collection top

KUMA-4 diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 28.1°, θ_min = 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 top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	Calculated w = 1/[σ²(F_o²) + (0.099P)² + 0.2039P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.047
856 reflections	Δρ_max = 0.18 e Å⁻³
91 parameters	Δρ_min = −0.39 e Å⁻³
0 restraints

Crystal data top

C₇H₁₀O₂	V = 1300.3 (7) Å³
M_r = 126.15	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 13.466 (4) Å	µ = 0.09 mm⁻¹
b = 13.691 (4) Å	T = 220 K
c = 7.053 (2) Å	0.3 × 0.3 × 0.2 mm

Data collection top

KUMA-4 diffractometer	723 reflections with I > 2σ(I)
856 measured reflections	R_int = 0.000
856 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	91 parameters
wR(F²) = 0.135	0 restraints
S = 1.04	Δρ_max = 0.18 e Å⁻³
856 reflections	Δρ_min = −0.39 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

Crystal data top

C₇H₁₀O₂	Z = 8
M_r = 126.15	F(000) = 544
Orthorhombic, Pccn	D_x = 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) Å³	0.4 × 0.3 × 0.2 mm

Data collection top

KUMA-4-CCD diffractometer	R_int = 0.044
Radiation source: fine-focus sealed tube	θ_max = 29.7°, θ_min = 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 top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.091	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.272	Calculated w = 1/[σ²(F_o²) + (0.1436P)²] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max = 0.017
1756 reflections	Δρ_max = 0.51 e Å⁻³
117 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints

Crystal data top

C₇H₁₀O₂	V = 1302.6 (7) Å³
M_r = 126.15	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 13.472 (4) Å	µ = 0.09 mm⁻¹
b = 13.692 (4) Å	T = 225 K
c = 7.062 (2) Å	0.4 × 0.3 × 0.2 mm

Data collection top

KUMA-4-CCD diffractometer	1097 reflections with I > 2σ(I)
8309 measured reflections	R_int = 0.044
1756 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.091	117 parameters
wR(F²) = 0.272	0 restraints
S = 1.17	Δρ_max = 0.51 e Å⁻³
1756 reflections	Δρ_min = −0.24 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

Crystal data top

C₇H₁₀O₂	Z = 8
M_r = 126.15	F(000) = 544
Orthorhombic, Pccn	D_x = 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) Å³	0.4 × 0.3 × 0.2 mm

Data collection top

KUMA-4-CCD diffractometer	R_int = 0.035
Radiation source: fine-focus sealed tube	θ_max = 29.6°, θ_min = 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 top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.107	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.329	Calculated w = 1/[σ²(F_o²) + (0.1617P)²] where P = (F_o² + 2F_c²)/3
S = 1.26	(Δ/σ)_max = 0.045
1758 reflections	Δρ_max = 0.50 e Å⁻³
117 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

Crystal data top

C₇H₁₀O₂	V = 1307.8 (7) Å³
M_r = 126.15	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 13.472 (4) Å	µ = 0.09 mm⁻¹
b = 13.692 (4) Å	T = 239.K K
c = 7.090 (2) Å	0.4 × 0.3 × 0.2 mm

Data collection top

KUMA-4-CCD diffractometer	1073 reflections with I > 2σ(I)
8221 measured reflections	R_int = 0.035
1758 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.107	117 parameters
wR(F²) = 0.329	0 restraints
S = 1.26	Δρ_max = 0.50 e Å⁻³
1758 reflections	Δρ_min = −0.21 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

Crystal data top

C₇H₁₀O₂	Z = 8
M_r = 126.15	F(000) = 544
Orthorhombic, Pccn	D_x = 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) Å³	0.4 × 0.3 × 0.2 mm

Data collection top

KUMA-4-CCD diffractometer	R_int = 0.066
Radiation source: fine-focus sealed tube	θ_max = 29.9°, θ_min = 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 top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.196	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.490	Calculated w = 1/[σ²(F_o²) + (0.1986P)² + 0.544P] where P = (F_o² + 2F_c²)/3
S = 1.31	(Δ/σ)_max = 0.114
1777 reflections	Δρ_max = 0.57 e Å⁻³
91 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints

Crystal data top

C₇H₁₀O₂	V = 1309.9 (7) Å³
M_r = 126.15	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 13.492 (4) Å	µ = 0.09 mm⁻¹
b = 13.692 (4) Å	T = 240 K
c = 7.091 (2) Å	0.4 × 0.3 × 0.2 mm

Data collection top

KUMA-4-CCD diffractometer	948 reflections with I > 2σ(I)
8148 measured reflections	R_int = 0.066
1777 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.196	0 restraints
wR(F²) = 0.490	(Δ/σ)_max = 0.114
S = 1.31	Δρ_max = 0.57 e Å⁻³
1777 reflections	Δρ_min = −0.32 e Å⁻³
91 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

Crystal data top

C₇H₁₀O₂	Z = 8
M_r = 126.15	F(000) = 544
Orthorhombic, Pccn	D_x = 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) Å³	0.4 × 0.3 × 0.2 mm

Data collection top

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

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.186	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.510	Calculated w = 1/[σ²(F_o²) + (0.1975P)² + 1.2779P] where P = (F_o² + 2F_c²)/3
S = 1.29	(Δ/σ)_max = 0.017
1778 reflections	Δρ_max = 0.50 e Å⁻³
91 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints

Crystal data top

C₇H₁₀O₂	V = 1311.2 (7) Å³
M_r = 126.15	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 13.498 (4) Å	µ = 0.09 mm⁻¹
b = 13.691 (4) Å	T = 242 K
c = 7.095 (2) Å	0.4 × 0.3 × 0.2 mm

Data collection top

KUMA-4-CCD diffractometer	889 reflections with I > 2σ(I)
8192 measured reflections	R_int = 0.066
1778 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.186	91 parameters
wR(F²) = 0.510	0 restraints
S = 1.29	Δρ_max = 0.50 e Å⁻³
1778 reflections	Δρ_min = −0.35 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

Crystal data top

C₇H₁₀O₂	Z = 8
M_r = 126.15	F(000) = 544
Orthorhombic, Ibam	D_x = 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) Å³	0.3 × 0.3 × 0.2 mm

Data collection top

KUMA-4 diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 28.1°, θ_min = 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 top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	Calculated w = 1/[σ²(F_o²) + (0.1P)² + 0.0891P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.013
866 reflections	Δρ_max = 0.25 e Å⁻³
104 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints

Crystal data top

C₇H₁₀O₂	V = 1315.2 (5) Å³
M_r = 126.15	Z = 8
Orthorhombic, Ibam	Mo Kα radiation
a = 13.510 (3) Å	µ = 0.09 mm⁻¹
b = 13.690 (3) Å	T = 250 K
c = 7.111 (1) Å	0.3 × 0.3 × 0.2 mm

Data collection top

KUMA-4 diffractometer	R_int = 0.000
866 measured reflections	2 standard reflections every 100 reflections
866 independent reflections	intensity decay: none
655 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.045	104 parameters
wR(F²) = 0.138	0 restraints
S = 1.03	Δρ_max = 0.25 e Å⁻³
866 reflections	Δρ_min = −0.18 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

O1—C1	1.334 (2)	C4—C4ⁱ	0.747 (6)
O1—H1	0.97 (3)	C4—C5ⁱ	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—C5ⁱ	0.696 (7)
C2—C7	1.492 (2)	C5—C4ⁱ	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—C5ⁱ	1.504 (3)
C3—C4	1.544 (3)	C6—H61	0.93 (3)
C3—C4ⁱ	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)	C4ⁱ—C4—H42	171 (2)
O1—C1—C6	116.69 (13)	C5ⁱ—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)	C5ⁱ—C5—C4ⁱ	91.1 (2)
C2—C7—H71	112 (5)	C5ⁱ—C5—C6	76.62 (12)
C2—C7—H72	105 (2)	C4ⁱ—C5—C6	123.0 (2)
H71—C7—H72	117 (3)	C5ⁱ—C5—C4	61.5 (2)
C2—C7—H73	106.0 (15)	C4ⁱ—C5—C4	29.6 (2)
H71—C7—H73	58.7 (14)	C6—C5—C4	111.4 (2)
H72—C7—H73	63 (2)	C5ⁱ—C5—H51	166.7 (18)
C2—C7—H74	113 (4)	C4ⁱ—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)	C5ⁱ—C5—H52	86.9 (15)
O2—C3—C2	120.87 (15)	C4ⁱ—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—C4ⁱ	119.57 (15)	H51—C5—H52	104 (2)
C2—C3—C4ⁱ	117.64 (14)	C1—C6—C5	112.58 (14)
C4—C3—C4ⁱ	28.0 (2)	C1—C6—C5ⁱ	112.58 (14)
C4ⁱ—C4—C5ⁱ	88.9 (2)	C5—C6—C5ⁱ	26.8 (3)
C4ⁱ—C4—C5	61.5 (2)	C1—C6—H61	108.7 (19)
C5ⁱ—C4—C5	27.3 (3)	C5—C6—H61	118.9 (18)
C4ⁱ—C4—C3	75.99 (11)	C5ⁱ—C6—H61	135.5 (19)
C5ⁱ—C4—C3	119.2 (2)	C1—C6—H62	102.1 (17)
C5—C4—C3	108.5 (2)	C5—C6—H62	110.6 (17)
C4ⁱ—C4—H41	85.4 (17)	C5ⁱ—C6—H62	85.0 (17)
C5ⁱ—C4—H41	128.0 (15)	H61—C6—H62	102 (3)
C5—C4—H41	120.3 (16)

O1—C1—C2—C3	180.0	C4ⁱ—C4—C5—C5ⁱ	180.000 (1)
C6—C1—C2—C3	0.0	C5ⁱ—C4—C5—C5ⁱ	0.0
O1—C1—C2—C7	0.0	C3—C4—C5—C5ⁱ	−118.1 (2)
C6—C1—C2—C7	180.0	C4ⁱ—C4—C5—C4ⁱ	0.000 (1)
C1—C2—C3—O2	180.0	C5ⁱ—C4—C5—C4ⁱ	180.000 (1)
C7—C2—C3—O2	0.0	C3—C4—C5—C4ⁱ	61.9 (2)
C1—C2—C3—C4	−15.85 (12)	C4ⁱ—C4—C5—C6	−119.7 (2)
C7—C2—C3—C4	164.15 (12)	C5ⁱ—C4—C5—C6	60.3 (2)
C1—C2—C3—C4ⁱ	15.85 (12)	C3—C4—C5—C6	−57.8 (3)
C7—C2—C3—C4ⁱ	−164.15 (12)	O1—C1—C6—C5	165.49 (14)
O2—C3—C4—C4ⁱ	−98.13 (8)	C2—C1—C6—C5	−14.51 (14)
C2—C3—C4—C4ⁱ	97.50 (7)	O1—C1—C6—C5ⁱ	−165.49 (14)
C4ⁱ—C3—C4—C4ⁱ	0.0	C2—C1—C6—C5ⁱ	14.51 (14)
O2—C3—C4—C5ⁱ	−178.8 (2)	C5ⁱ—C5—C6—C1	95.67 (7)
C2—C3—C4—C5ⁱ	16.8 (3)	C4ⁱ—C5—C6—C1	13.2 (3)
C4ⁱ—C3—C4—C5ⁱ	−80.7 (3)	C4—C5—C6—C1	43.9 (2)
O2—C3—C4—C5	−151.17 (15)	C5ⁱ—C5—C6—C5ⁱ	0.0
C2—C3—C4—C5	44.5 (2)	C4ⁱ—C5—C6—C5ⁱ	−82.5 (3)
C4ⁱ—C3—C4—C5	−53.0 (2)	C4—C5—C6—C5ⁱ	−51.7 (2)

Symmetry code: (i) x, y, −z.

(293) top

Crystal data top

C₇H₁₀O₂	Z = 8
M_r = 126.15	F(000) = 544
Orthorhombic, Ibam	D_x = 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) Å³	0.5 × 0.4 × 0.2 mm

Data collection top

KUMA-4 diffractometer	R_int = 0.019
Radiation source: fine-focus sealed tube	θ_max = 26.0°, θ_min = 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 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)] = 0.044	Calculated w = 1/[σ²(F_o²) + (0.0993P)² + 0.0875P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.116	(Δ/σ)_max = 3.670
S = 1.03	Δρ_max = 0.22 e Å⁻³
566 reflections	Δρ_min = −0.18 e Å⁻³
105 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0649 (72)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₇H₁₀O₂	V = 1332.1 (5) Å³
M_r = 126.15	Z = 8
Orthorhombic, Ibam	Mo Kα radiation
a = 13.558 (3) Å	µ = 0.09 mm⁻¹
b = 13.696 (3) Å	T = 293 K
c = 7.174 (1) Å	0.5 × 0.4 × 0.2 mm

Data collection top

KUMA-4 diffractometer	R_int = 0.019
568 measured reflections	2 standard reflections every 100 reflections
566 independent reflections	intensity decay: none
526 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.116	(Δ/σ)_max = 3.670
S = 1.03	Δρ_max = 0.22 e Å⁻³
566 reflections	Δρ_min = −0.18 e Å⁻³
105 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

O1—C1	1.333 (2)	C4—C4ⁱ	0.678 (8)
O1—H1	0.93 (4)	C4—C5ⁱ	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—C5ⁱ	0.761 (6)
C2—C7	1.489 (3)	C5—C4ⁱ	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—C5ⁱ	1.509 (3)
C3—C4	1.536 (4)	C6—H61	0.97 (3)
C3—C4ⁱ	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)	C4ⁱ—C4—H42	174 (2)
O1—C1—C6	116.92 (14)	C5ⁱ—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)	C5ⁱ—C5—C4ⁱ	88.2 (2)
C2—C7—H71	106 (6)	C5ⁱ—C5—C6	75.40 (11)
C2—C7—H72	108.8 (19)	C4ⁱ—C5—C6	122.4 (2)
H71—C7—H72	121 (4)	C5ⁱ—C5—C4	61.6 (2)
C2—C7—H73	108.4 (15)	C4ⁱ—C5—C4	26.6 (3)
H71—C7—H73	58.1 (19)	C6—C5—C4	111.1 (2)
H72—C7—H73	66 (2)	C5ⁱ—C5—H51	167.2 (18)
C2—C7—H74	113 (3)	C4ⁱ—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)	C5ⁱ—C5—H52	84.8 (16)
O2—C3—C2	120.8 (2)	C4ⁱ—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—C4ⁱ	119.8 (2)	H51—C5—H52	106 (2)
C2—C3—C4ⁱ	117.83 (15)	C1—C6—C5	112.4 (2)
C4—C3—C4ⁱ	25.5 (3)	C1—C6—C5ⁱ	112.4 (2)
C4ⁱ—C4—C5ⁱ	91.8 (2)	C5—C6—C5ⁱ	29.2 (2)
C4ⁱ—C4—C5	61.6 (2)	C1—C6—H61	112.0 (19)
C5ⁱ—C4—C5	30.2 (2)	C5—C6—H61	116 (2)
C4ⁱ—C4—C3	77.3 (2)	C5ⁱ—C6—H61	133.1 (19)
C5ⁱ—C4—C3	119.6 (2)	C1—C6—H62	103.1 (17)
C5—C4—C3	108.9 (2)	C5—C6—H62	111.1 (19)
C4ⁱ—C4—H41	87.3 (16)	C5ⁱ—C6—H62	83.3 (19)
C5ⁱ—C4—H41	127.7 (15)	H61—C6—H62	101 (3)
C5—C4—H41	121.0 (15)

O1—C1—C2—C3	180.0	C4ⁱ—C4—C5—C5ⁱ	180.000 (1)
C6—C1—C2—C3	0.0	C5ⁱ—C4—C5—C5ⁱ	0.000 (1)
O1—C1—C2—C7	0.0	C3—C4—C5—C5ⁱ	−116.8 (2)
C6—C1—C2—C7	180.0	C4ⁱ—C4—C5—C4ⁱ	0.000 (1)
C1—C2—C3—O2	180.0	C5ⁱ—C4—C5—C4ⁱ	180.000 (2)
C7—C2—C3—O2	0.0	C3—C4—C5—C4ⁱ	63.2 (2)
C1—C2—C3—C4	−14.4 (2)	C4ⁱ—C4—C5—C6	−121.0 (2)
C7—C2—C3—C4	165.6 (2)	C5ⁱ—C4—C5—C6	59.0 (2)
C1—C2—C3—C4ⁱ	14.4 (2)	C3—C4—C5—C6	−57.8 (3)
C7—C2—C3—C4ⁱ	−165.6 (2)	O1—C1—C6—C5	164.18 (12)
O2—C3—C4—C4ⁱ	−97.44 (10)	C2—C1—C6—C5	−15.82 (12)
C2—C3—C4—C4ⁱ	96.86 (9)	O1—C1—C6—C5ⁱ	−164.18 (12)
C4ⁱ—C3—C4—C4ⁱ	0.0	C2—C1—C6—C5ⁱ	15.82 (12)
O2—C3—C4—C5ⁱ	177.8 (2)	C5ⁱ—C5—C6—C1	96.16 (7)
C2—C3—C4—C5ⁱ	12.1 (4)	C4ⁱ—C5—C6—C1	17.9 (3)
C4ⁱ—C3—C4—C5ⁱ	−84.7 (3)	C4—C5—C6—C1	45.0 (2)
O2—C3—C4—C5	−151.1 (2)	C5ⁱ—C5—C6—C5ⁱ	0.0
C2—C3—C4—C5	43.2 (3)	C4ⁱ—C5—C6—C5ⁱ	−78.2 (3)
C4ⁱ—C3—C4—C5	−53.6 (2)	C4—C5—C6—C5ⁱ	−51.2 (2)

Symmetry code: (i) x, y, −z.

Experimental details

	(123)	(170)	(180)	(220)
Crystal data
Chemical formula	C₇H₁₀O₂	C₇H₁₀O₂	C₇H₁₀O₂	C₇H₁₀O₂
M_r	126.15	126.15	126.15	126.15
Crystal system, space group	Orthorhombic, Pccn	Orthorhombic, Pccn	Orthorhombic, Pccn	Orthorhombic, Pccn
Temperature (K)	123	170	180	220
a, b, c (Å)	13.427 (3), 13.689 (3), 6.946 (2)	13.426 (4), 13.690 (4), 6.987 (2)	13.466 (4), 13.691 (4), 7.053 (2)	13.466 (4), 13.691 (4), 7.053 (2)
V (Å³)	1276.7 (5)	1284.2 (6)	1300.3 (7)	1300.3 (7)
Z	8	8	8	8
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.10	0.10	0.09	0.09
Crystal size (mm)	0.3 × 0.3 × 0.2	0.3 × 0.3 × 0.2	0.4 × 0.3 × 0.2	0.3 × 0.3 × 0.2

Data collection
Diffractometer	KUMA-4-CCD diffractometer	KUMA-4 diffractometer	KUMA-4-CCD diffractometer	KUMA-4 diffractometer
Absorption correction	–	–	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6596, 1616, 1322	846, 846, 742	7637, 1712, 1088	856, 856, 723
R_int	0.055	0.000	0.077	0.000
(sin θ/λ)_max (Å⁻¹)	0.698	0.662	0.698	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.157, 1.10	0.040, 0.118, 1.04	0.092, 0.278, 1.15	0.044, 0.135, 1.04
No. of reflections	1616	846	1712	856
No. of parameters	117	91	117	91
(Δ/σ)_max	−0.014	0.014	0.007	0.047
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.31	0.38, −0.14	0.66, −0.30	0.18, −0.39

	(225)	(239)	(240)	(242)
Crystal data
Chemical formula	C₇H₁₀O₂	C₇H₁₀O₂	C₇H₁₀O₂	C₇H₁₀O₂
M_r	126.15	126.15	126.15	126.15
Crystal system, space group	Orthorhombic, Pccn	Orthorhombic, Pccn	Orthorhombic, Pccn	Orthorhombic, Pccn
Temperature (K)	225	239.K	240	242
a, b, c (Å)	13.472 (4), 13.692 (4), 7.062 (2)	13.472 (4), 13.692 (4), 7.090 (2)	13.492 (4), 13.692 (4), 7.091 (2)	13.498 (4), 13.691 (4), 7.095 (2)
V (Å³)	1302.6 (7)	1307.8 (7)	1309.9 (7)	1311.2 (7)
Z	8	8	8	8
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.09	0.09	0.09	0.09
Crystal size (mm)	0.4 × 0.3 × 0.2	0.4 × 0.3 × 0.2	0.4 × 0.3 × 0.2	0.4 × 0.3 × 0.2

Data collection
Diffractometer	KUMA-4-CCD diffractometer	KUMA-4-CCD diffractometer	KUMA-4-CCD diffractometer	KUMA-4-CCD diffractometer
Absorption correction	–	–	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8309, 1756, 1097	8221, 1758, 1073	8148, 1777, 948	8192, 1778, 889
R_int	0.044	0.035	0.066	0.066
(sin θ/λ)_max (Å⁻¹)	0.696	0.696	0.701	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.091, 0.272, 1.17	0.107, 0.329, 1.26	0.196, 0.490, 1.31	0.186, 0.510, 1.29
No. of reflections	1756	1758	1777	1778
No. of parameters	117	117	91	91
(Δ/σ)_max	0.017	0.045	0.114	0.017
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.24	0.50, −0.21	0.57, −0.32	0.50, −0.35

	(250)	(293)
Crystal data
Chemical formula	C₇H₁₀O₂	C₇H₁₀O₂
M_r	126.15	126.15
Crystal system, space group	Orthorhombic, Ibam	Orthorhombic, Ibam
Temperature (K)	250	293
a, b, c (Å)	13.510 (3), 13.690 (3), 7.111 (1)	13.558 (3), 13.696 (3), 7.174 (1)
V (Å³)	1315.2 (5)	1332.1 (5)
Z	8	8
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.09	0.09
Crystal size (mm)	0.3 × 0.3 × 0.2	0.5 × 0.4 × 0.2

Data collection
Diffractometer	KUMA-4 diffractometer	KUMA-4 diffractometer
Absorption correction	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	866, 866, 655	568, 566, 526
R_int	0.000	0.019
(sin θ/λ)_max (Å⁻¹)	0.662	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.138, 1.03	0.044, 0.116, 1.03
No. of reflections	866	566
No. of parameters	104	105
(Δ/σ)_max	0.013	3.670
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.18	0.22, −0.18

Computer programs: SHELXS86 (Sheldrick, 1990), SHELXL93 (Sheldrick, 1993).

Hydrogen-bond dimensions in 2-methyl-1,3-cyclohexanedione at varied temperatures. Angle $ρho$ between the line passing through O(1) and O(2) of one molecule and the [010] direction describes the inclination of the molecules to the direction of the chains. Also the deviations of methylene atoms C(4) and C(5) from the least-squares plane fitted to the remaining non-H atoms of the molecule, denoted d[C(4)] and d[C(5)] respectively, have been given. The negative sign of d[C(5)] indicate the location of C(5) on the opposite site of the plane than C(4). top

	123K	170K	180K	220K	225K	239K	250K	293K
O(1)···O(2ⁱ)	2.576 (1)	2.577 (4)	2.578 (3)	2.578 (2)	2.579 (3)	2.576 (3)	2.580 (2)	2.588 (2)
O(1)–H(1)	1.00 (2)	0.99 (3)	1.13 (4)	1.00 (3)	1.05 (5)	0.98 (5)	0.97 (3)	0.93 (3)
H(1)···O(2ⁱ)	1.58 (2)	1.60 (3)	1.45 (4)	1.59 (3)	1.53 (5)	1.60 (5)	1.61 (3)	1.66 (3)
O(1)–H(1)···O(2ⁱ)	175 (2)	166 (5)	177 (3)	168 (4)	175 (4)	176 (3)	178 (3)	175 (3)
C(1)–O(1)–H(1)(η_d)	111.1 (13)	110.4 (18)	115 (2)	111.2 (16)	117 (3)	113 (3)	112.7 (18)	110.3 (19)
H(1)···O(2ⁱ)=C(3ⁱ)(η_a)	128.8 (8)	129.4 (9)	126 (2)	129.3 (10)	126 (2)	128.6 (18)	129.2 (11)	130.6 (12)
C(1)–O(1)···O(2ⁱ)(η'_d)	114.25 (8)	114.4 (2)	114.49 (16)	114.25 (14)	114.37 (15)	114.2 (2)	113.97 (10)	113.63 (11)
O(1)···O(2ⁱ)=C(3ⁱ)(η'_a)	126.86 (9)	127.20 (13)	127.42 (17)	127.76 (13)	127.82	128.2 (2)	128.40 (12)	128.75 (14)
$ρho$	7.90 (2)	7.7 (4)	7.94 (4)	8.1 (3)	7.98 (4)	7.90 (4)	7.66 (9)	7.96 (3)
$d$[C(4)][{AA}]	0.114 (2)	0.159 (9)	0.125 (5)	0.160 (21)	0.118 (5)	0.126 (7)	0.373 (3)	0.339 (4)
$d$[C(5)]	-0.614 (2)	-0.556 (8)	-0.586 (6)	-0.529 (30)	-0.547 (7)	-0.449 (8)	-0.348 (3)	-0.381 (3)

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