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The low-temperature crystal stuctures of D- and DL-camphoric anhydride, C10H14O3, have been determined by X-ray diffraction methods. Although the two enantiomers crystallize in different space groups, the cell volumes and densities are essentially the same. The six-membered rings deviate significantly from planarity, both exhibiting half-boat conformations. The dihedral angle between the six- and five-membered rings is 80.3 (1)° in both cases. The main difference in the molecular stuctures can be described by two torsion angles associated with the H atoms of the methyl substituents. The packing of the racemic and chiral structures are essentially the same.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100001840/qb0154sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001840/qb0154Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001840/qb0154IIsup3.hkl
Contains datablock II

Comment top

The physical properties of several camphor derivatives have been extensively studied, especially in relation to their chiroptical features which is affected by the nature of the substituent attached to the bicyclic ring in the bridgehead position (Yager & Morgan, 1935; Williams & Symth, 1962; Mjojo & Welsh, 1992; Mora & Fitch, 1997). We report hete the low-temperature structural data for D-camphoric anhydride, (I), and DL-camphoric anhydride, (II). The former was reinvestigated for comparison.

The corresponding internuclear distances and angles of the two molecules are statistically equal and all geometrical parameters of the low-temperature structure of (I) compare well with those obtained earlier based on room-temperature data (Wichmann et al., 1987). The conformation of the six-membered rings were determined in terms of their ring-puckering parameters (Cremer & Pople, 1975); (I): Q = 0.637 (1) Å, θ = 45.6 (1)° and ϕ = -3.1 (1)°; (II): Q = 0.628 (1) Å, θ = 45.1° and ϕ = -5.1 (1)°. These values indicate that the rings adopt half-boat conformations. The groups of atoms C7/C3/C2/C1 and C1/C6/C5/C4 lie in the least-squares planes of their respective six- and five-membered rings. In both structures, the planes form an angle of 80.3 (1)°.

Weak C—H···O type hydrogen bonds connect molecules of the same chirality, forming linear chains. These columns of D—L, (I), and D—D, (II), isomers are held together by even weaker contacts giving rise to a remarkable similarity in the packing. This observation does not support the conclusion by Brock et al. (1991) that the racemic crystal tend to be denser than its chiral counterpart.

Experimental top

Commercially available (I) and (II) were purchased and crystallized from benzene and toluene, respectively, by slow evaporation at room temperature.

Refinement top

H atoms were located from difference Fourier maps and refined isotropically. The C—H distances range from 0.91 (2) to 1.02 (2) Å. Due to the absence of suitable anomolous scatteres within (I), the determination of the absolute configuration was not possible from our X-ray data. Friedel opposites were therefore merged before the refinement.

Computing details top

For both compounds, data collection: SMART (Bruker, 1997); cell refinement: SAINT-Plus (Bruker, 1997); data reduction: SAINT-Plus (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Shelsrick, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

(I) (1R)-1,8,8-Trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione top
Crystal data top
C10H14O3Dx = 1.316 Mg m3
Mr = 182.21Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 8192 reflections
a = 6.4262 (3) Åθ = 2.4–29.9°
b = 11.0841 (4) ŵ = 0.10 mm1
c = 12.9142 (5) ÅT = 110 K
V = 919.86 (6) Å3Rectangular block, colourless
Z = 40.45 × 0.4 × 0.3 mm
F(000) = 392
Data collection top
Brukers SMART CCD area-detector
diffractometer
Rint = 0.021
Detector resolution: 0.75 pixels mm-1θmax = 26.4°, θmin = 2.4°
ω scansh = 08
11128 measured reflectionsk = 013
1103 independent reflectionsl = 016
1090 reflections with I > 2σ(I)
Refinement top
Refinement on F2174 parameters
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.029Cal w = 1/[σ2(Fo2) + (0.0548P)2 + 0.088P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.072(Δ/σ)max = 0.001
S = 1.11Δρmax = 0.20 e Å3
1103 reflectionsΔρmin = 0.20 e Å3
Crystal data top
C10H14O3V = 919.86 (6) Å3
Mr = 182.21Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.4262 (3) ŵ = 0.10 mm1
b = 11.0841 (4) ÅT = 110 K
c = 12.9142 (5) Å0.45 × 0.4 × 0.3 mm
Data collection top
Brukers SMART CCD area-detector
diffractometer
1090 reflections with I > 2σ(I)
11128 measured reflectionsRint = 0.021
1103 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.029174 parameters
wR(F2) = 0.072All H-atom parameters refined
S = 1.11Δρmax = 0.20 e Å3
1103 reflectionsΔρmin = 0.20 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.41254 (15)0.42254 (9)0.05444 (7)0.0212 (2)
O20.40437 (18)0.55783 (11)0.07026 (8)0.0304 (3)
O30.44800 (17)0.31127 (9)0.19501 (8)0.0278 (3)
C10.0790 (2)0.53040 (11)0.02361 (9)0.0180 (3)
C20.3068 (2)0.51016 (12)0.00295 (10)0.0203 (3)
C30.3326 (2)0.37385 (11)0.14613 (10)0.0188 (3)
C40.1093 (2)0.40161 (11)0.16907 (10)0.0182 (3)
C50.0244 (2)0.32934 (12)0.09029 (11)0.0222 (3)
C60.0370 (2)0.41185 (13)0.00581 (10)0.0220 (3)
C70.0623 (2)0.53546 (11)0.14420 (10)0.0169 (3)
C80.2144 (2)0.62333 (12)0.19523 (11)0.0215 (3)
C90.1590 (2)0.56685 (13)0.17943 (11)0.0234 (3)
C100.0023 (3)0.64059 (14)0.03417 (12)0.0277 (3)
H40.085 (3)0.3795 (14)0.2394 (12)0.018 (4)*
H5A0.037 (3)0.2486 (16)0.0755 (12)0.024 (4)*
H5B0.163 (3)0.3184 (16)0.1179 (15)0.030 (5)*
H6A0.176 (3)0.4320 (17)0.0221 (15)0.029 (4)*
H6B0.027 (3)0.3731 (15)0.0682 (13)0.025 (4)*
H8A0.204 (3)0.6164 (16)0.2674 (14)0.030 (5)*
H8B0.359 (3)0.6087 (18)0.1756 (16)0.032 (5)*
H8C0.181 (3)0.7091 (16)0.1742 (13)0.026 (4)*
H9A0.254 (3)0.5216 (18)0.1463 (15)0.029 (5)*
H9B0.166 (3)0.5510 (16)0.2549 (15)0.032 (5)*
H9C0.188 (3)0.6552 (18)0.1664 (14)0.033 (5)*
H10A0.160 (3)0.6431 (16)0.0231 (14)0.028 (4)*
H10B0.061 (3)0.7154 (16)0.0084 (15)0.031 (5)*
H10C0.021 (3)0.6309 (17)0.1076 (16)0.037 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0169 (4)0.0252 (5)0.0216 (4)0.0034 (4)0.0019 (4)0.0026 (4)
O20.0257 (5)0.0421 (6)0.0236 (5)0.0038 (4)0.0059 (4)0.0046 (5)
O30.0266 (5)0.0247 (5)0.0320 (5)0.0012 (4)0.0039 (4)0.0062 (4)
C10.0162 (6)0.0197 (6)0.0181 (6)0.0011 (5)0.0004 (5)0.0013 (5)
C20.0196 (7)0.0242 (6)0.0171 (6)0.0044 (5)0.0003 (5)0.0019 (5)
C30.0205 (6)0.0164 (6)0.0196 (6)0.0033 (5)0.0007 (5)0.0006 (5)
C40.0184 (6)0.0174 (6)0.0186 (6)0.0004 (5)0.0023 (5)0.0006 (5)
C50.0199 (6)0.0189 (6)0.0277 (7)0.0036 (5)0.0000 (6)0.0032 (6)
C60.0183 (7)0.0256 (6)0.0221 (6)0.0059 (5)0.0012 (5)0.0034 (6)
C70.0150 (6)0.0165 (6)0.0192 (6)0.0024 (4)0.0012 (5)0.0002 (5)
C80.0219 (7)0.0198 (6)0.0227 (6)0.0052 (5)0.0005 (5)0.0019 (6)
C90.0182 (6)0.0247 (6)0.0273 (7)0.0054 (6)0.0032 (6)0.0019 (6)
C100.0273 (7)0.0288 (7)0.0271 (7)0.0067 (6)0.0021 (6)0.0030 (6)
Geometric parameters (Å, º) top
O1—C21.3980 (17)C5—H5B0.97 (2)
O1—C31.3989 (16)C6—H6A0.94 (2)
O2—C21.1950 (17)C6—H6B1.001 (18)
O3—C31.1954 (17)C7—C81.5293 (19)
C1—C21.5201 (19)C7—C91.5327 (18)
C1—C101.5236 (18)C8—H8A0.938 (18)
C1—C61.5578 (18)C8—H8B0.98 (2)
C1—C71.5620 (17)C8—H8C1.012 (18)
C3—C41.4975 (19)C9—H9A0.90 (2)
C4—C71.5478 (17)C9—H9B0.992 (19)
C4—C51.5541 (18)C9—H9C1.01 (2)
C4—H40.954 (16)C10—H10A1.03 (2)
C5—C61.544 (2)C10—H10B0.981 (18)
C5—H5A0.995 (18)C10—H10C0.97 (2)
C2—O1—C3122.57 (10)C5—C6—H6B111.8 (10)
C2—C1—C10109.75 (12)C1—C6—H6B111.3 (10)
C2—C1—C6106.34 (10)H6A—C6—H6B108.0 (16)
C10—C1—C6113.12 (11)C8—C7—C9108.70 (11)
C2—C1—C7107.25 (10)C8—C7—C4113.34 (11)
C10—C1—C7115.84 (11)C9—C7—C4109.70 (11)
C6—C1—C7103.91 (10)C8—C7—C1114.11 (11)
O2—C2—O1115.95 (13)C9—C7—C1111.59 (11)
O2—C2—C1127.18 (13)C4—C7—C199.15 (10)
O1—C2—C1116.81 (11)C7—C8—H8A109.3 (12)
O3—C3—O1116.31 (13)C7—C8—H8B113.0 (12)
O3—C3—C4127.52 (13)H8A—C8—H8B108.3 (17)
O1—C3—C4116.10 (11)C7—C8—H8C110.3 (11)
C3—C4—C7110.07 (11)H8A—C8—H8C109.1 (15)
C3—C4—C5107.13 (10)H8B—C8—H8C106.8 (16)
C7—C4—C5104.49 (10)C7—C9—H9A111.2 (13)
C3—C4—H4107.1 (11)C7—C9—H9B107.2 (12)
C7—C4—H4114.3 (10)H9A—C9—H9B109.7 (17)
C5—C4—H4113.5 (10)C7—C9—H9C110.0 (12)
C6—C5—C4104.47 (10)H9A—C9—H9C109.7 (18)
C6—C5—H5A113.5 (9)H9B—C9—H9C109.1 (16)
C4—C5—H5A111.8 (10)C1—C10—H10A107.0 (10)
C6—C5—H5B108.8 (11)C1—C10—H10B111.6 (11)
C4—C5—H5B109.4 (12)H10A—C10—H10B109.9 (16)
H5A—C5—H5B108.7 (15)C1—C10—H10C109.8 (12)
C5—C6—C1106.17 (10)H10A—C10—H10C106.9 (17)
C5—C6—H6A111.7 (12)H10B—C10—H10C111.4 (17)
C1—C6—H6A107.9 (12)
C3—O1—C2—O2168.79 (11)C6—C1—C10—H10C62.92 (1.30)
C3—O1—C2—C113.84 (16)C7—C1—C10—H10A67.07 (1.14)
C10—C1—C2—O211.46 (18)C7—C1—C10—H10B53.20 (1.21)
C6—C1—C2—O2111.22 (15)C7—C1—C10—H10C177.26 (1.29)
C7—C1—C2—O2138.08 (14)C3—C4—C5—H5A36.94 (1.10)
C10—C1—C2—O1171.50 (12)C3—C4—C5—H5B157.36 (1.23)
C6—C1—C2—O165.82 (13)C7—C4—C5—H5A153.71 (1.09)
C7—C1—C2—O144.88 (14)C7—C4—C5—H5B85.87 (1.23)
C2—O1—C3—O3170.88 (12)H4—C4—C5—C6155.76 (1.08)
C2—O1—C3—C411.85 (16)H4—C4—C5—H5A81.06 (1.54)
O3—C3—C4—C7140.87 (13)H4—C4—C5—H5B39.36 (1.64)
O1—C3—C4—C742.21 (14)H4—C4—C7—C1169.98 (1.09)
O3—C3—C4—C5106.09 (14)H4—C4—C7—C868.68 (1.09)
O1—C3—C4—C570.82 (13)H4—C4—C7—C953.01 (1.09)
C3—C4—C5—C686.25 (13)C4—C5—C6—H6A120.33 (1.31)
C7—C4—C5—C630.53 (14)C4—C5—C6—H6B118.51 (1.10)
C4—C5—C6—C12.99 (14)H5A—C5—C6—C1125.02 (1.11)
C2—C1—C6—C587.82 (12)H5A—C5—C6—H6A117.64 (1.72)
C10—C1—C6—C5151.64 (12)H5A—C5—C6—H6B3.53 (1.57)
C7—C1—C6—C525.19 (13)H5B—C5—C6—C1113.79 (1.23)
C3—C4—C7—C851.86 (14)H5B—C5—C6—H6B124.72 (1.65)
C5—C4—C7—C8166.59 (11)H5B—C5—C6—H6A3.55 (1.80)
C3—C4—C7—C9173.55 (10)C1—C7—C8—H8A174.94 (1.24)
C5—C4—C7—C971.72 (12)C1—C7—C8—H8B54.35 (1.35)
C3—C4—C7—C169.48 (12)C1—C7—C8—H8C65.09 (1.11)
C5—C4—C7—C145.25 (13)C4—C7—C8—H8A62.43 (1.24)
C2—C1—C7—C851.26 (14)C4—C7—C8—H8B58.15 (1.35)
C10—C1—C7—C871.67 (16)C4—C7—C8—H8C177.59 (1.10)
C6—C1—C7—C8163.62 (11)C9—C7—C8—H8A59.82 (1.24)
C2—C1—C7—C9174.95 (11)C9—C7—C8—H8B179.59 (1.34)
C10—C1—C7—C952.02 (16)C9—C7—C8—H8C60.15 (1.11)
C6—C1—C7—C972.69 (13)C1—C7—C9—H9A47.90 (1.37)
C2—C1—C7—C469.52 (12)C1—C7—C9—H9B167.79 (1.18)
C10—C1—C7—C4167.55 (11)C1—C7—C9—H9C73.76 (1.22)
C6—C1—C7—C442.84 (12)C4—C7—C9—H9A60.97 (1.37)
C2—C1—C10—H10A171.33 (1.13)C4—C7—C9—H9B58.93 (1.18)
C2—C1—C10—H10B68.40 (1.21)C4—C7—C9—H9C177.37 (1.22)
C2—C1—C10—H10C55.66 (1.30)C8—C7—C9—H9A174.60 (1.37)
C6—C1—C10—H10A52.75 (1.14)C8—C7—C9—H9B65.50 (1.18)
C6—C1—C10—H10B173.02 (1.21)C8—C7—C9—H9C52.94 (1.23)
(II) (R/S)-1,8,8-Trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione top
Crystal data top
C10H14O3F(000) = 392
Mr = 182.21Dx = 1.313 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.4152 (4) ÅCell parameters from 8192 reflections
b = 11.4413 (8) Åθ = 2.2–30.1°
c = 12.5623 (8) ŵ = 0.10 mm1
β = 91.9680°T = 110 K
V = 921.51 (10) Å3Rectangular block, colourless
Z = 40.5 × 0.45 × 0.3 mm
Data collection top
Bruckers SMART CCD area-detector
diffractometer
Rint = 0.012
Detector resolution: 0.75 pixels mm-1θmax = 26.4°
ω scansh = 77
11276 measured reflectionsk = 014
1875 independent reflectionsl = 015
1825 reflections with I > 2σ(I)
Refinement top
Refinement on F2174 parameters
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0403P)2 + 0.3112P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.081(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.35 e Å3
1875 reflectionsΔρmin = 0.17 e Å3
Crystal data top
C10H14O3V = 921.51 (10) Å3
Mr = 182.21Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.4152 (4) ŵ = 0.10 mm1
b = 11.4413 (8) ÅT = 110 K
c = 12.5623 (8) Å0.5 × 0.45 × 0.3 mm
β = 91.9680°
Data collection top
Bruckers SMART CCD area-detector
diffractometer
1825 reflections with I > 2σ(I)
11276 measured reflectionsRint = 0.012
1875 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032174 parameters
wR(F2) = 0.081All H-atom parameters refined
S = 1.06Δρmax = 0.35 e Å3
1875 reflectionsΔρmin = 0.17 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.11225 (11)0.67221 (6)0.45800 (6)0.02161 (18)
O20.13006 (12)0.81147 (7)0.57870 (6)0.0289 (2)
O30.12307 (12)0.55693 (7)0.31747 (6)0.0295 (2)
C10.20971 (15)0.78513 (8)0.48998 (7)0.0188 (2)
C20.01948 (15)0.76254 (9)0.51441 (7)0.0199 (2)
C30.01820 (16)0.62310 (8)0.36619 (8)0.0205 (2)
C40.20542 (15)0.65516 (8)0.34346 (8)0.0196 (2)
C50.33578 (16)0.59093 (9)0.42730 (8)0.0231 (2)
C60.33062 (16)0.67362 (9)0.52465 (8)0.0219 (2)
C70.24227 (15)0.78614 (8)0.36642 (7)0.0181 (2)
C80.09264 (17)0.86681 (9)0.30874 (8)0.0239 (2)
C90.46702 (17)0.81945 (10)0.33370 (9)0.0246 (2)
C100.27696 (18)0.89523 (10)0.54756 (9)0.0265 (2)
H40.2417 (19)0.6336 (11)0.2703 (10)0.021 (3)*
H5A0.278 (2)0.5114 (12)0.4436 (10)0.029 (3)*
H5B0.478 (2)0.5795 (12)0.3983 (11)0.030 (3)*
H6A0.473 (2)0.6973 (12)0.5428 (10)0.027 (3)*
H6B0.264 (2)0.6367 (12)0.5877 (10)0.026 (3)*
H8A0.120 (2)0.8619 (12)0.2330 (12)0.034 (3)*
H8B0.054 (2)0.8466 (13)0.3228 (11)0.034 (3)*
H8C0.112 (2)0.9488 (13)0.3333 (11)0.035 (4)*
H9A0.570 (2)0.7780 (12)0.3751 (11)0.032 (3)*
H9B0.493 (2)0.8008 (12)0.2585 (12)0.035 (4)*
H9C0.485 (2)0.9038 (13)0.3433 (10)0.031 (3)*
H10A0.431 (2)0.9027 (12)0.5386 (11)0.034 (4)*
H10B0.210 (2)0.9661 (13)0.5179 (11)0.036 (4)*
H10C0.243 (2)0.8890 (13)0.6235 (12)0.035 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0182 (3)0.0232 (4)0.0233 (4)0.0005 (3)0.0017 (3)0.0033 (3)
O20.0272 (4)0.0346 (4)0.0245 (4)0.0049 (3)0.0048 (3)0.0022 (3)
O30.0303 (4)0.0269 (4)0.0314 (4)0.0050 (3)0.0029 (3)0.0081 (3)
C10.0195 (5)0.0186 (5)0.0183 (5)0.0005 (4)0.0009 (3)0.0010 (4)
C20.0226 (5)0.0204 (5)0.0168 (4)0.0022 (4)0.0013 (4)0.0001 (4)
C30.0237 (5)0.0170 (5)0.0208 (5)0.0013 (4)0.0009 (4)0.0007 (4)
C40.0215 (5)0.0178 (5)0.0192 (5)0.0009 (4)0.0023 (4)0.0005 (4)
C50.0216 (5)0.0188 (5)0.0288 (5)0.0028 (4)0.0011 (4)0.0023 (4)
C60.0208 (5)0.0226 (5)0.0224 (5)0.0050 (4)0.0025 (4)0.0006 (4)
C70.0191 (5)0.0173 (5)0.0180 (4)0.0014 (3)0.0004 (3)0.0017 (4)
C80.0263 (6)0.0222 (5)0.0232 (5)0.0050 (4)0.0022 (4)0.0003 (4)
C90.0226 (5)0.0258 (5)0.0250 (5)0.0033 (4)0.0028 (4)0.0050 (4)
C100.0303 (6)0.0245 (5)0.0248 (5)0.0048 (4)0.0025 (4)0.0049 (4)
Geometric parameters (Å, º) top
O1—C21.3976 (12)C5—H5B0.981 (14)
O1—C31.4008 (12)C6—H6A0.985 (14)
O2—C21.1956 (13)C6—H6B0.983 (13)
O3—C31.1952 (12)C7—C81.5317 (13)
C1—C21.5139 (13)C7—C91.5337 (13)
C1—C101.5224 (13)C8—H8A0.963 (14)
C1—C71.5591 (13)C8—H8B0.982 (15)
C1—C61.5628 (13)C8—H8C0.997 (15)
C3—C41.4986 (13)C9—H9A0.976 (14)
C4—C71.5457 (13)C9—H9B0.978 (15)
C4—C51.5522 (14)C9—H9C0.981 (14)
C4—H40.972 (12)C10—H10A0.993 (14)
C5—C61.5456 (15)C10—H10B0.997 (15)
C5—H5A1.001 (14)C10—H10C0.974 (15)
C2—O1—C3122.36 (8)C5—C6—H6B111.8 (8)
C2—C1—C10109.51 (8)C1—C6—H6B111.6 (8)
C2—C1—C7107.40 (7)H6A—C6—H6B108.2 (10)
C10—C1—C7115.88 (8)C8—C7—C9108.79 (8)
C2—C1—C6106.98 (8)C8—C7—C4113.18 (8)
C10—C1—C6113.05 (8)C9—C7—C4109.84 (8)
C7—C1—C6103.46 (8)C8—C7—C1114.25 (8)
O2—C2—O1115.83 (9)C9—C7—C1111.17 (8)
O2—C2—C1127.34 (9)C4—C7—C199.35 (7)
O1—C2—C1116.80 (8)C7—C8—H8A109.6 (8)
O3—C3—O1116.20 (9)C7—C8—H8B112.8 (8)
O3—C3—C4127.55 (9)H8A—C8—H8B107.8 (11)
O1—C3—C4116.17 (8)C7—C8—H8C109.4 (8)
C3—C4—C7110.69 (8)H8A—C8—H8C109.9 (12)
C3—C4—C5106.82 (8)H8B—C8—H8C107.3 (12)
C7—C4—C5104.07 (8)C7—C9—H9A112.4 (8)
C3—C4—H4108.3 (7)C7—C9—H9B109.5 (8)
C7—C4—H4112.9 (7)H9A—C9—H9B108.2 (11)
C5—C4—H4113.8 (7)C7—C9—H9C109.2 (8)
C6—C5—C4104.46 (8)H9A—C9—H9C109.0 (11)
C6—C5—H5A113.4 (7)H9B—C9—H9C108.5 (11)
C4—C5—H5A111.4 (7)C1—C10—H10A108.3 (8)
C6—C5—H5B111.7 (8)C1—C10—H10B111.3 (8)
C4—C5—H5B109.1 (8)H10A—C10—H10B109.2 (11)
H5A—C5—H5B106.7 (11)C1—C10—H10C110.3 (8)
C5—C6—C1106.05 (8)H10A—C10—H10C107.8 (11)
C5—C6—H6A110.9 (8)H10B—C10—H10C109.9 (12)
C1—C6—H6A108.2 (8)
C3—O1—C2—O2166.59 (9)C6—C1—C10—H10A53.3 (9)
C3—O1—C2—C115.18 (13)C6—C1—C10—H10B173.4 (9)
C10—C1—C2—O29.17 (14)C6—C1—C10—H10C64.5 (9)
C7—C1—C2—O2135.78 (10)C7—C1—C10—H10A65.9 (9)
C6—C1—C2—O2113.69 (11)C7—C1—C10—H10B54.2 (9)
C10—C1—C2—O1172.82 (8)C7—C1—C10—H10C176.4 (9)
C7—C1—C2—O146.21 (11)O1—C3—C4—H4165.4 (7)
C6—C1—C2—O164.32 (10)O3—C3—C4—H418.0 (8)
C2—O1—C3—O3171.02 (9)C3—C4—C5—H5A37.0 (8)
C2—O1—C3—C411.84 (13)C3—C4—C5—H5B154.6 (8)
O3—C3—C4—C7142.28 (10)C7—C4—C5—H5A154.1 (8)
O1—C3—C4—C740.97 (11)C7—C4—C5—H5B88.3 (9)
O3—C3—C4—C5105.04 (12)H4—C4—C5—C6154.7 (8)
O1—C3—C4—C571.71 (10)H4—C4—C5—H5A82.5 (10)
C3—C4—C5—C685.83 (9)H4—C4—C5—H5B35.1 (10)
C7—C4—C5—C631.32 (10)H4—C4—C7—C1170.2 (8)
C4—C5—C6—C13.50 (10)H4—C4—C7—C868.2 (8)
C2—C1—C6—C588.09 (9)H4—C4—C7—C953.6 (8)
C10—C1—C6—C5151.28 (9)C4—C5—C6—H6A120.7 (8)
C7—C1—C6—C525.15 (10)C4—C5—C6—H6B118.3 (8)
C3—C4—C7—C853.40 (11)H5A—C5—C6—C1125.0 (8)
C5—C4—C7—C8167.82 (8)H5A—C5—C6—H6A117.8 (10)
C3—C4—C7—C9175.20 (8)H5A—C5—C6—H6B3.1 (10)
C5—C4—C7—C970.38 (9)H5B—C5—C6—C1114.4 (9)
C3—C4—C7—C168.16 (9)H5B—C5—C6—H6A2.9 (10)
C5—C4—C7—C146.27 (9)H5B—C5—C6—H6B123.81
C2—C1—C7—C851.29 (10)C1—C7—C8—H8A179.01
C10—C1—C7—C871.47 (11)C1—C7—C8—H8B58.87
C6—C1—C7—C8164.22 (8)C1—C7—C8—H8C60.49
C2—C1—C7—C9174.88 (8)C4—C7—C8—H8A66.3 (9)
C10—C1—C7—C952.13 (11)C4—C7—C8—H8B53.9 (9)
C6—C1—C7—C972.18 (10)C4—C7—C8—H8C173.2 (9)
C2—C1—C7—C469.49 (9)C9—C7—C8—H8A56.1 (9)
C10—C1—C7—C4167.76 (9)C9—C7—C8—H8B176.3 (9)
C6—C1—C7—C443.45 (9)C9—C7—C8—H8C64.4 (9)
C2—C1—C6—H6A152.9 (8)C1—C7—C9—H9A45.7 (9)
C2—C1—C6—H6B33.9 (8)C1—C7—C9—H9B166.0 (9)
C7—C1—C6—H6A93.9 (8)C1—C7—C9—H9C75.5 (9)
C7—C1—C6—H6B147.1 (8)C4—C7—C9—H9A63.3 (9)
C10—C1—C6—H6A32.2 (8)C4—C7—C9—H9B57.0 (9)
C10—C1—C6—H6B86.73C4—C7—C9—H9C175.6 (9)
C2—C1—C10—H10A172.5 (9)C8—C7—C9—H9A172.3 (9)
C2—C1—C10—H10B67.5 (9)C8—C7—C9—H9B67.4 (9)
C2—C1—C10—H10C54.7 (9)C8—C7—C9—H9C51.2 (9)

Experimental details

(I)(II)
Crystal data
Chemical formulaC10H14O3C10H14O3
Mr182.21182.21
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21/n
Temperature (K)110110
a, b, c (Å)6.4262 (3), 11.0841 (4), 12.9142 (5)6.4152 (4), 11.4413 (8), 12.5623 (8)
α, β, γ (°)90, 90, 9090, 91.9680, 90
V3)919.86 (6)921.51 (10)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.100.10
Crystal size (mm)0.45 × 0.4 × 0.30.5 × 0.45 × 0.3
Data collection
DiffractometerBrukers SMART CCD area-detector
diffractometer
Bruckers SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11128, 1103, 1090 11276, 1875, 1825
Rint0.0210.012
(sin θ/λ)max1)0.6250.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.072, 1.11 0.032, 0.081, 1.06
No. of reflections11031875
No. of parameters174174
No. of restraints??
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.20, 0.200.35, 0.17

Computer programs: SMART (Bruker, 1997), SAINT-Plus (Bruker, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Shelsrick, 1997), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) for (I) top
O1—C21.3980 (17)C1—C71.5620 (17)
O1—C31.3989 (16)C3—C41.4975 (19)
O2—C21.1950 (17)C4—C71.5478 (17)
O3—C31.1954 (17)C4—C51.5541 (18)
C1—C21.5201 (19)C5—C61.544 (2)
C1—C101.5236 (18)C7—C81.5293 (19)
C1—C61.5578 (18)C7—C91.5327 (18)
C2—O1—C3122.57 (10)O1—C3—C4116.10 (11)
C2—C1—C10109.75 (12)C3—C4—C7110.07 (11)
C2—C1—C6106.34 (10)C3—C4—C5107.13 (10)
C10—C1—C6113.12 (11)C7—C4—C5104.49 (10)
C2—C1—C7107.25 (10)C6—C5—C4104.47 (10)
C10—C1—C7115.84 (11)C5—C6—C1106.17 (10)
C6—C1—C7103.91 (10)C8—C7—C9108.70 (11)
O2—C2—O1115.95 (13)C8—C7—C4113.34 (11)
O2—C2—C1127.18 (13)C9—C7—C4109.70 (11)
O1—C2—C1116.81 (11)C8—C7—C1114.11 (11)
O3—C3—O1116.31 (13)C9—C7—C1111.59 (11)
O3—C3—C4127.52 (13)C4—C7—C199.15 (10)
C3—O1—C2—C113.84 (16)O1—C3—C4—C742.21 (14)
C7—C1—C2—O144.88 (14)C3—C4—C7—C169.48 (12)
C2—O1—C3—C411.85 (16)C2—C1—C7—C469.52 (12)
Selected geometric parameters (Å, º) for (II) top
O1—C21.3976 (12)C1—C61.5628 (13)
O1—C31.4008 (12)C3—C41.4986 (13)
O2—C21.1956 (13)C4—C71.5457 (13)
O3—C31.1952 (12)C4—C51.5522 (14)
C1—C21.5139 (13)C5—C61.5456 (15)
C1—C101.5224 (13)C7—C81.5317 (13)
C1—C71.5591 (13)C7—C91.5337 (13)
C2—O1—C3122.36 (8)O1—C3—C4116.17 (8)
C2—C1—C10109.51 (8)C3—C4—C7110.69 (8)
C2—C1—C7107.40 (7)C3—C4—C5106.82 (8)
C10—C1—C7115.88 (8)C7—C4—C5104.07 (8)
C2—C1—C6106.98 (8)C6—C5—C4104.46 (8)
C10—C1—C6113.05 (8)C5—C6—C1106.05 (8)
C7—C1—C6103.46 (8)C8—C7—C9108.79 (8)
O2—C2—O1115.83 (9)C8—C7—C4113.18 (8)
O2—C2—C1127.34 (9)C9—C7—C4109.84 (8)
O1—C2—C1116.80 (8)C8—C7—C1114.25 (8)
O3—C3—O1116.20 (9)C9—C7—C1111.17 (8)
O3—C3—C4127.55 (9)C4—C7—C199.35 (7)
C3—O1—C2—C115.18 (13)O1—C3—C4—C740.97 (11)
C7—C1—C2—O146.21 (11)C3—C4—C7—C168.16 (9)
C2—O1—C3—C411.84 (13)C2—C1—C7—C469.49 (9)
 

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