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Two polytypic modifications of (1R,3S)-dimethyl 2-oxocyclohexane-1,3-dicarboxylate intergrow to form allotwins. One phase shows monoclinic symmetry, Cc, while the other is orthorhombic Pmc21. The structures may be considered as two different modes of superstructure ordering of an underlying, disordered structure. Considered in the same metrically orthorhombic unit cell a = 37.8883, b = 4.7233, c = 11.6835 Å, the two can be conveniently distinguished by their non-standard centering, Cc being represented as Xc with the centering vectors (0 0 0); (½ 0 ½); (¼ ½ ¾); (¾ ½ ¼); and Pmc21 as Xmc21 with the centering vectors (0 0 0); (½ 0 0). The difference between the allotwin domains lies only in the relationship between next-nearest neighbors along the stacking direction 100 and hence the conformations and packing efficiencies are identical for both phases and all three domains. The stacking sequences for the two phases correspond to ABAB for the orthorhombic stacking and ABA'B'/AB'A'B for the two (equivalent) monoclinic stackings. The monoclinic phase dominates comprising ca 80% of the total volume. Within the monoclinic phase, the ratio between the two possible orientations is highly unbalanced (6:1) indicating relatively large domains. The allotwinning detected in this sample may appear exotic in molecular compounds, but we suggest that the rarity of such examples in the literature is a reflection of the paucity of software that can identify and handle such cases. It is easy to overlook the possibility that a complex diffraction pattern originates from allotwinning and assume that normal mono-component twinning is the cause. The underlying mechanism in this case is the formation of two-dimensional layers of molecules that allow for two equivalent, but in terms of absolute geometry, different, ways of stacking.
Supporting information
CCDC references: 971735; 971736
For both compounds, data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET) (compiled Jan 27 2011,13:34:29); cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET) (compiled Jan 27 2011,13:34:29); data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET) (compiled Jan 27 2011,13:34:29); program(s) used to solve structure: Palatinus L., Chapuis G. (2007). J. Appl. Cryst. 40, 786-790; program(s) used to refine structure: Petricek, V., Dusek, M. & Palatinus, L. (2006). Jana2006. Structure Determination Software Programs. Institute of Physics, Praha, Czech Republic.
Crystal data top
C10H14O5 | F(000) = 912 |
Mr = 214.2 | Dx = 1.361 Mg m−3 |
Monoclinic, Xc | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: Xc | Cell parameters from 5939 reflections |
a = 37.8883 (18) Å | θ = 2.7–29.2° |
b = 4.7233 (2) Å | µ = 0.11 mm−1 |
c = 11.6835 (12) Å | T = 293 K |
β = 90.000 (7)° | Cube, colourless |
V = 2090.9 (3) Å3 | 0.5 × 0.5 × 0.5 mm |
Z = 8 | |
Data collection top
Xcalibur, Sapphire3 diffractometer | 7281 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3986 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.068 |
Detector resolution: 16.1829 pixels mm-1 | θmax = 29.2°, θmin = 3.2° |
ω scans | h = −50→50 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −6→6 |
Tmin = 0.806, Tmax = 1 | l = −15→15 |
31649 measured reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.050 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
wR(F2) = 0.145 | (Δ/σ)max = 0.042 |
S = 1.34 | Δρmax = 0.16 e Å−3 |
7281 reflections | Δρmin = −0.12 e Å−3 |
281 parameters | Extinction correction: B-C type 1 Gaussian isotropic (Becker & Coppens, 1974) |
0 restraints | Extinction coefficient: 81E2 (7) |
120 constraints | Absolute structure: 2977 of Friedel pairs used in the refinement |
Crystal data top
C10H14O5 | V = 2090.9 (3) Å3 |
Mr = 214.2 | Z = 8 |
Monoclinic, Xc | Mo Kα radiation |
a = 37.8883 (18) Å | µ = 0.11 mm−1 |
b = 4.7233 (2) Å | T = 293 K |
c = 11.6835 (12) Å | 0.5 × 0.5 × 0.5 mm |
β = 90.000 (7)° | |
Data collection top
Xcalibur, Sapphire3 diffractometer | 7281 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | 3986 reflections with I > 3σ(I) |
Tmin = 0.806, Tmax = 1 | Rint = 0.068 |
31649 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.34 | Δρmax = 0.16 e Å−3 |
7281 reflections | Δρmin = −0.12 e Å−3 |
281 parameters | Absolute structure: 2977 of Friedel pairs used in the refinement |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | −0.10367 (15) | −0.0154 (6) | 0.8197 (4) | 0.0567 (13) | |
O1 | −0.07594 (7) | 0.1638 (4) | 0.7744 (2) | 0.0497 (6) | |
C2 | −0.06522 (8) | 0.1069 (5) | 0.6683 (3) | 0.0376 (8) | |
O2 | −0.07840 (8) | −0.0738 (5) | 0.6100 (3) | 0.0571 (7) | |
C3 | −0.03430 (8) | 0.2873 (4) | 0.6316 (2) | 0.0343 (6) | |
C4 | −0.00031 (8) | 0.1487 (4) | 0.6705 (3) | 0.0304 (6) | |
O3 | 0 | −0.0690 (4) | 0.725879 | 0.0411 (6) | |
C5 | −0.03366 (9) | 0.3401 (5) | 0.5021 (3) | 0.0415 (7) | |
C6 | −0.00072 (12) | 0.4995 (5) | 0.4657 (4) | 0.0464 (15) | |
C7 | 0.03277 (9) | 0.3467 (5) | 0.5023 (3) | 0.0431 (8) | |
C8 | 0.03338 (8) | 0.2961 (4) | 0.6318 (3) | 0.0348 (6) | |
C9 | 0.06482 (8) | 0.1219 (5) | 0.6689 (3) | 0.0381 (8) | |
O4 | 0.07888 (9) | −0.0531 (6) | 0.6110 (3) | 0.0637 (8) | |
O5 | 0.07476 (8) | 0.1816 (4) | 0.7755 (2) | 0.0511 (6) | |
C10 | 0.10277 (14) | 0.0094 (6) | 0.8205 (4) | 0.0569 (14) | |
H1c1 | −0.104733 | 0.005411 | 0.901378 | 0.068* | |
H2c1 | −0.125885 | 0.038902 | 0.786854 | 0.068* | |
H3c1 | −0.098766 | −0.209349 | 0.800921 | 0.068* | |
H1c3 | −0.036779 | 0.469512 | 0.667119 | 0.0411* | |
H1c5 | −0.03473 | 0.162345 | 0.462386 | 0.0498* | |
H2c5 | −0.0542 | 0.446334 | 0.480297 | 0.0498* | |
H1c6 | −0.001022 | 0.68588 | 0.498482 | 0.0557* | |
H2c6 | −0.000736 | 0.522515 | 0.384087 | 0.0557* | |
H1c7 | 0.034318 | 0.168453 | 0.463092 | 0.0517* | |
H2c7 | 0.052969 | 0.456982 | 0.480586 | 0.0517* | |
H1c8 | 0.035135 | 0.479039 | 0.667127 | 0.0417* | |
H1c10 | 0.105549 | 0.04709 | 0.900771 | 0.0683* | |
H2c10 | 0.097114 | −0.186899 | 0.809626 | 0.0683* | |
H3c10 | 0.124358 | 0.052857 | 0.781281 | 0.0683* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.047 (2) | 0.071 (2) | 0.053 (2) | −0.0032 (12) | 0.0055 (17) | 0.0122 (12) |
O1 | 0.0483 (10) | 0.0564 (11) | 0.0444 (10) | −0.0021 (8) | 0.0103 (8) | −0.0074 (8) |
C2 | 0.0319 (12) | 0.0404 (14) | 0.0404 (13) | 0.0079 (10) | −0.0017 (10) | −0.0011 (10) |
O2 | 0.0544 (14) | 0.0631 (11) | 0.0539 (13) | −0.0193 (12) | −0.0024 (10) | −0.0099 (12) |
C3 | 0.0399 (12) | 0.0281 (10) | 0.0349 (11) | 0.0036 (9) | −0.0023 (9) | −0.0039 (8) |
C4 | 0.0388 (11) | 0.0260 (10) | 0.0265 (10) | 0.0008 (9) | 0.0011 (8) | −0.0055 (8) |
O3 | 0.0425 (10) | 0.0366 (8) | 0.0443 (11) | 0.0007 (8) | −0.0008 (8) | 0.0112 (10) |
C5 | 0.0439 (13) | 0.0434 (14) | 0.0372 (12) | 0.0069 (10) | −0.0063 (10) | 0.0024 (10) |
C6 | 0.066 (3) | 0.033 (2) | 0.041 (2) | 0.0001 (9) | −0.0014 (16) | 0.0060 (8) |
C7 | 0.0476 (14) | 0.0465 (14) | 0.0352 (12) | −0.0041 (11) | 0.0073 (11) | 0.0033 (10) |
C8 | 0.0380 (11) | 0.0300 (11) | 0.0363 (11) | −0.0011 (9) | 0.0003 (9) | −0.0036 (8) |
C9 | 0.0320 (12) | 0.0419 (14) | 0.0405 (13) | −0.0059 (10) | 0.0030 (10) | −0.0024 (10) |
O4 | 0.0653 (16) | 0.0764 (14) | 0.0495 (13) | 0.0317 (13) | −0.0007 (11) | −0.0133 (12) |
O5 | 0.0483 (10) | 0.0596 (11) | 0.0453 (10) | 0.0041 (8) | −0.0092 (7) | −0.0054 (8) |
C10 | 0.044 (2) | 0.079 (3) | 0.048 (2) | 0.0042 (12) | −0.0053 (16) | 0.0075 (12) |
Geometric parameters (Å, º) top
C1—O1 | 1.450 (5) | C6—C7 | 1.521 (5) |
C1—H1c1 | 0.96 | C6—H1c6 | 0.96 |
C1—H2c1 | 0.96 | C6—H2c6 | 0.96 |
C1—H3c1 | 0.96 | C7—C8 | 1.532 (4) |
O1—C2 | 1.331 (4) | C7—H1c7 | 0.96 |
C2—O2 | 1.201 (4) | C7—H2c7 | 0.96 |
C2—C3 | 1.511 (4) | C8—C9 | 1.511 (4) |
C3—C4 | 1.515 (4) | C8—H1c8 | 0.96 |
C3—C5 | 1.534 (4) | C9—O4 | 1.193 (4) |
C3—H1c3 | 0.96 | C9—O5 | 1.332 (4) |
C4—O3 | 1.215 (3) | O5—C10 | 1.437 (5) |
C4—C8 | 1.523 (4) | C10—H1c10 | 0.96 |
C5—C6 | 1.518 (5) | C10—H2c10 | 0.96 |
C5—H1c5 | 0.96 | C10—H3c10 | 0.96 |
C5—H2c5 | 0.96 | | |
| | | |
O1—C1—H1c1 | 109.47 | C5—C6—H2c6 | 109.47 |
O1—C1—H2c1 | 109.47 | C7—C6—H1c6 | 109.47 |
O1—C1—H3c1 | 109.47 | C7—C6—H2c6 | 109.47 |
H1c1—C1—H2c1 | 109.47 | H1c6—C6—H2c6 | 106.99 |
H1c1—C1—H3c1 | 109.47 | C6—C7—C8 | 111.3 (3) |
H2c1—C1—H3c1 | 109.47 | C6—C7—H1c7 | 109.47 |
C1—O1—C2 | 116.3 (3) | C6—C7—H2c7 | 109.47 |
O1—C2—O2 | 123.0 (3) | C8—C7—H1c7 | 109.47 |
O1—C2—C3 | 112.8 (2) | C8—C7—H2c7 | 109.47 |
O2—C2—C3 | 124.2 (3) | H1c7—C7—H2c7 | 107.53 |
C2—C3—C4 | 109.3 (2) | C4—C8—C7 | 110.6 (2) |
C2—C3—C5 | 112.6 (2) | C4—C8—C9 | 109.1 (2) |
C2—C3—H1c3 | 107.88 | C4—C8—H1c8 | 110 |
C4—C3—C5 | 110.7 (2) | C7—C8—C9 | 112.3 (2) |
C4—C3—H1c3 | 109.91 | C7—C8—H1c8 | 106.57 |
C5—C3—H1c3 | 106.4 | C9—C8—H1c8 | 108.19 |
C3—C4—O3 | 122.3 (2) | C8—C9—O4 | 124.5 (3) |
C3—C4—C8 | 115.2 (2) | C8—C9—O5 | 112.1 (2) |
O3—C4—C8 | 122.5 (2) | O4—C9—O5 | 123.4 (3) |
C3—C5—C6 | 111.7 (3) | C9—O5—C10 | 115.6 (3) |
C3—C5—H1c5 | 109.47 | O5—C10—H1c10 | 109.47 |
C3—C5—H2c5 | 109.47 | O5—C10—H2c10 | 109.47 |
C6—C5—H1c5 | 109.47 | O5—C10—H3c10 | 109.47 |
C6—C5—H2c5 | 109.47 | H1c10—C10—H2c10 | 109.47 |
H1c5—C5—H2c5 | 107.17 | H1c10—C10—H3c10 | 109.47 |
C5—C6—C7 | 111.8 (2) | H2c10—C10—H3c10 | 109.47 |
C5—C6—H1c6 | 109.47 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H3c1···O2 | 0.96 | 2.45 | 2.645 (6) | 91.15 |
Crystal data top
C10H14O5 | F(000) = 912 |
Mr = 214.2 | Dx = 1.361 Mg m−3 |
Orthorhombic, Xmc21 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: Xmc21 | Cell parameters from 5939 reflections |
a = 37.8883 Å | θ = 2.7–29.2° |
b = 4.7233 Å | µ = 0.11 mm−1 |
c = 11.6835 Å | T = 293 K |
V = 2090.85 Å3 | Cube, colourless |
Z = 8 | 0.5 × 0.5 × 0.5 mm |
Data collection top
Xcalibur, Sapphire3 diffractometer | 7281 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3986 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.068 |
Detector resolution: 16.1829 pixels mm-1 | θmax = 29.2°, θmin = 3.2° |
ω scans | h = −50→50 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −6→6 |
Tmin = 0.806, Tmax = 1 | l = −15→15 |
31649 measured reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.050 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2) |
wR(F2) = 0.145 | (Δ/σ)max = 0.042 |
S = 1.34 | Δρmax = 0.16 e Å−3 |
7281 reflections | Δρmin = −0.12 e Å−3 |
281 parameters | Extinction correction: B-C type 1 Gaussian isotropic (Becker & Coppens, 1974) |
0 restraints | Extinction coefficient: 81E2 (7) |
120 constraints | Absolute structure: 3002 of Friedel pairs used in the refinement |
Crystal data top
C10H14O5 | V = 2090.85 Å3 |
Mr = 214.2 | Z = 8 |
Orthorhombic, Xmc21 | Mo Kα radiation |
a = 37.8883 Å | µ = 0.11 mm−1 |
b = 4.7233 Å | T = 293 K |
c = 11.6835 Å | 0.5 × 0.5 × 0.5 mm |
Data collection top
Xcalibur, Sapphire3 diffractometer | 7281 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | 3986 reflections with I > 3σ(I) |
Tmin = 0.806, Tmax = 1 | Rint = 0.068 |
31649 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.34 | Δρmax = 0.16 e Å−3 |
7281 reflections | Δρmin = −0.12 e Å−3 |
281 parameters | Absolute structure: 3002 of Friedel pairs used in the refinement |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1-2_1 | −0.1033 (3) | −0.0196 (13) | 0.818 (3) | 0.070 (4) | |
C1-2_2 | 0.1451 (3) | 0.4871 (12) | 1.562 (3) | 0.078 (4) | |
O1-2_1 | −0.07522 (6) | 0.1618 (6) | 0.774 (3) | 0.0363 (11) | |
O1-2_2 | 0.17446 (8) | 0.3180 (6) | 1.523 (3) | 0.0432 (11) | |
C2-2_1 | −0.06536 (10) | 0.1036 (10) | 0.668 (3) | 0.0256 (13) | |
C2-2_2 | 0.18476 (11) | 0.3747 (10) | 1.414 (3) | 0.0306 (15) | |
O2-2_1 | −0.07768 (12) | −0.0813 (10) | 0.611 (3) | 0.0491 (15) | |
O2-2_2 | 0.17179 (16) | 0.5564 (11) | 1.357 (3) | 0.0578 (17) | |
C3-2_1 | −0.03404 (8) | 0.2859 (7) | 0.631 (3) | 0.0226 (11) | |
C3-2_2 | 0.21646 (9) | 0.1961 (7) | 1.379 (3) | 0.0251 (12) | |
C4-2_1 | 0 | 0.1331 (13) | 0.671 (3) | 0.0180 (16) | |
C4-2_2 | 0.25 | 0.3457 (12) | 1.417 (3) | 0.0232 (17) | |
O3-2_1 | 0 | −0.0778 (11) | 0.726 (3) | 0.0291 (15) | |
O3-2_2 | 0.25 | 0.5617 (11) | 1.470 (3) | 0.0331 (16) | |
C5-2_1 | −0.03323 (10) | 0.3396 (8) | 0.502 (3) | 0.0267 (12) | |
C5-2_2 | 0.21710 (10) | 0.1505 (8) | 1.249 (3) | 0.0325 (13) | |
C6-2_1 | 0 | 0.4923 (10) | 0.464 (3) | 0.027 (3) | |
C6-2_2 | 0.25 | −0.0079 (12) | 1.212 (3) | 0.038 (4) | |
H1c1-2_1 | −0.095366 | −0.212697 | 0.818709 | 0.0838* | |
H2c1-2_1 | −0.109257 | 0.037768 | 0.894352 | 0.0838* | |
H3c1-2_1 | −0.123696 | −0.003354 | 0.769713 | 0.0838* | |
H1c1-2_2 | 0.129257 | 0.370329 | 1.605571 | 0.094* | |
H2c1-2_2 | 0.153743 | 0.637664 | 1.609787 | 0.094* | |
H3c1-2_2 | 0.132863 | 0.565514 | 1.497679 | 0.094* | |
H1c3-2_1 | −0.036051 | 0.469391 | 0.665924 | 0.0271* | |
H1c3-2_2 | 0.214823 | 0.013452 | 1.414308 | 0.0301* | |
H1c5-2_1 | −0.035114 | 0.162647 | 0.461877 | 0.0321* | |
H2c5-2_1 | −0.053547 | 0.44848 | 0.480065 | 0.0321* | |
H1c5-2_2 | 0.19657 | 0.045406 | 1.226384 | 0.039* | |
H2c5-2_2 | 0.216275 | 0.330476 | 1.211001 | 0.039* | |
H1c6-2_1 | 0 | 0.681188 | 0.494109 | 0.0326* | |
H2c6-2_1 | 0 | 0.510037 | 0.381888 | 0.0326* | |
H1c6-2_2 | 0.25 | −0.029698 | 1.130796 | 0.0461* | |
H2c6-2_2 | 0.25 | −0.193055 | 1.246399 | 0.0461* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1-2_1 | 0.033 (5) | 0.097 (7) | 0.079 (6) | −0.010 (3) | 0.025 (5) | 0.015 (3) |
C1-2_2 | 0.039 (6) | 0.095 (7) | 0.101 (8) | 0.008 (3) | 0.034 (5) | −0.022 (3) |
O1-2_1 | 0.0190 (14) | 0.051 (2) | 0.039 (2) | −0.0044 (13) | 0.0063 (13) | −0.0039 (14) |
O1-2_2 | 0.0375 (17) | 0.052 (2) | 0.0397 (19) | 0.0045 (14) | 0.0084 (14) | 0.0106 (15) |
C2-2_1 | 0.0145 (19) | 0.034 (3) | 0.028 (2) | −0.0027 (16) | −0.0039 (17) | 0.001 (2) |
C2-2_2 | 0.033 (2) | 0.032 (3) | 0.027 (2) | −0.0019 (18) | −0.0052 (18) | 0.0000 (19) |
O2-2_1 | 0.035 (2) | 0.054 (2) | 0.059 (3) | −0.014 (2) | 0.005 (2) | −0.011 (3) |
O2-2_2 | 0.060 (3) | 0.059 (2) | 0.054 (3) | 0.019 (3) | 0.002 (2) | 0.022 (3) |
C3-2_1 | 0.0126 (16) | 0.0245 (19) | 0.031 (2) | 0.0063 (13) | 0.0005 (16) | 0.0022 (15) |
C3-2_2 | 0.030 (2) | 0.021 (2) | 0.024 (2) | −0.0017 (15) | −0.0016 (16) | −0.0020 (14) |
C4-2_1 | 0.012 (2) | 0.031 (3) | 0.011 (3) | 0 | 0 | −0.008 (2) |
C4-2_2 | 0.035 (3) | 0.020 (3) | 0.014 (3) | 0 | 0 | 0.005 (2) |
O3-2_1 | 0.028 (2) | 0.022 (2) | 0.037 (3) | 0 | 0 | 0.010 (3) |
O3-2_2 | 0.050 (3) | 0.018 (2) | 0.032 (3) | 0 | 0 | 0.001 (3) |
C5-2_1 | 0.0177 (18) | 0.034 (2) | 0.028 (2) | 0.0063 (15) | −0.0058 (15) | 0.0018 (16) |
C5-2_2 | 0.039 (2) | 0.031 (2) | 0.027 (2) | −0.0067 (17) | −0.0066 (19) | −0.0025 (16) |
C6-2_1 | 0.025 (6) | 0.038 (6) | 0.019 (5) | 0 | 0 | 0.0054 (19) |
C6-2_2 | 0.059 (9) | 0.038 (7) | 0.017 (5) | 0 | 0 | −0.008 (2) |
Bond lengths (Å) top
C1-2_1—O1-2_1 | 1.46 (2) | C3-2_1—H1c3-2_1 | 0.96 |
C1-2_1—H1c1-2_1 | 0.96 | C3-2_2—C4-2_2 | 1.522 (17) |
C1-2_1—H2c1-2_1 | 0.96 | C3-2_2—C5-2_2 | 1.53 (6) |
C1-2_1—H3c1-2_1 | 0.96 | C3-2_2—H1c3-2_2 | 0.96 |
C1-2_2—O1-2_2 | 1.45 (2) | C4-2_1—O3-2_1 | 1.18 (3) |
C1-2_2—H1c1-2_2 | 0.96 | C4-2_2—O3-2_2 | 1.19 (3) |
C1-2_2—H2c1-2_2 | 0.96 | C5-2_1—C6-2_1 | 1.517 (17) |
C1-2_2—H3c1-2_2 | 0.96 | C5-2_1—H1c5-2_1 | 0.96 |
O1-2_1—C2-2_1 | 1.32 (5) | C5-2_1—H2c5-2_1 | 0.96 |
O1-2_2—C2-2_2 | 1.35 (5) | C5-2_2—C6-2_2 | 1.515 (17) |
C2-2_1—O2-2_1 | 1.19 (3) | C5-2_2—H1c5-2_2 | 0.96 |
C2-2_1—C3-2_1 | 1.527 (17) | C5-2_2—H2c5-2_2 | 0.96 |
C2-2_2—O2-2_2 | 1.20 (3) | C6-2_1—H1c6-2_1 | 0.96 |
C2-2_2—C3-2_2 | 1.524 (16) | C6-2_1—H2c6-2_1 | 0.96 |
C3-2_1—C4-2_1 | 1.550 (17) | C6-2_2—H1c6-2_2 | 0.96 |
C3-2_1—C5-2_1 | 1.53 (6) | C6-2_2—H2c6-2_2 | 0.96 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1-2_2—H3c1-2_2···O2-2_2 | 0.96 | 2.21 | 2.63 (5) | 104.81 |
Experimental details
| (Phase_I) | (Phase_II) |
Crystal data |
Chemical formula | C10H14O5 | C10H14O5 |
Mr | 214.2 | 214.2 |
Crystal system, space group | Monoclinic, Xc | Orthorhombic, Xmc21 |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 37.8883 (18), 4.7233 (2), 11.6835 (12) | 37.8883, 4.7233, 11.6835 |
α, β, γ (°) | 90, 90.000 (7), 90 | 90, 90, 90 |
V (Å3) | 2090.9 (3) | 2090.85 |
Z | 8 | 8 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.11 |
Crystal size (mm) | 0.5 × 0.5 × 0.5 | 0.5 × 0.5 × 0.5 |
|
Data collection |
Diffractometer | Xcalibur, Sapphire3 diffractometer | Xcalibur, Sapphire3 diffractometer |
Absorption correction | Multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | Multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET)
(compiled Jan 27 2011,13:34:29)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. |
Tmin, Tmax | 0.806, 1 | 0.806, 1 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 31649, 7281, 3986 | 31649, 7281, 3986 |
Rint | 0.068 | 0.068 |
(sin θ/λ)max (Å−1) | 0.687 | 0.687 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.145, 1.34 | 0.050, 0.145, 1.34 |
No. of reflections | 7281 | 7281 |
No. of parameters | 281 | 281 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.12 | 0.16, −0.12 |
Absolute structure | 2977 of Friedel pairs used in the refinement | 3002 of Friedel pairs used in the refinement |

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