Allotwinning in a molecular crystal: (1R,3S)-dimethyl 2-oxocyclohexane-1,3-dicarboxylate

Jahangiri, A.; Fleckhaus, A.; Lidin, S.; Strand, D.

doi:10.1107/S2052519213018605

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Allotwinning in a molecular crystal: (1R,3S)-dimethyl 2-oxocyclohexane-1,3-dicarboxylate

A. Jahangiri, A. Fleckhaus, S. Lidin and D. Strand

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.

Keywords: allotwinning; organic meso structure; superstructure ordering; disorder.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519213018605/dk5017sup1.cif Contains datablocks global1, Phase_I, Phase_II
	Text file https://doi.org/10.1107/S2052519213018605/dk5017sup1.txt JANA2006. m40 file. This file contains the atomic parameters for the two structures
	Text file https://doi.org/10.1107/S2052519213018605/dk5017sup2.txt JANA2006. m50 file. This file contains symmetry information, the twin laws, constraints, scattering factor tables etc.
	Text file https://doi.org/10.1107/S2052519213018605/dk5017sup3.txt JANA2006. m91 file. This file contains the symmetry averaged hkl, Fo, sig information
	Text file https://doi.org/10.1107/S2052519213018605/dk5017sup4.txt JANA2006. m95 file. This file contains the unaveraged, raw data.

CCDC references: 971735; 971736

Computing details top

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.

Figures top

(Phase_I) top

Crystal data top

C₁₀H₁₄O₅	F(000) = 912
M_r = 214.2	D_x = 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	R_int = 0.068
Detector resolution: 16.1829 pixels mm^-1	θ_max = 29.2°, θ_min = 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
T_min = 0.806, T_max = 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	Δρ_max = 0.16 e Å⁻³
7281 reflections	Δρ_min = −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
M_r = 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)
T_min = 0.806, T_max = 1	R_int = 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	Δρ_max = 0.16 e Å⁻³
7281 reflections	Δρ_min = −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	U_iso*/U_eq
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

(Phase_II) top

Crystal data top

C₁₀H₁₄O₅	F(000) = 912
M_r = 214.2	D_x = 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	R_int = 0.068
Detector resolution: 16.1829 pixels mm^-1	θ_max = 29.2°, θ_min = 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
T_min = 0.806, T_max = 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	Δρ_max = 0.16 e Å⁻³
7281 reflections	Δρ_min = −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
M_r = 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)
T_min = 0.806, T_max = 1	R_int = 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	Δρ_max = 0.16 e Å⁻³
7281 reflections	Δρ_min = −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	U_iso*/U_eq
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
M_r	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.
T_min, T_max	0.806, 1	0.806, 1
No. of measured, independent and observed [I > 3σ(I)] reflections	31649, 7281, 3986	31649, 7281, 3986
R_int	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
Δρ_max, Δρ_min (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

Computer programs: CrysAlis PRO, Agilent Technologies, Version 1.171.35.6 (release 27-01-2011 CrysAlis171 .NET) (compiled Jan 27 2011,13:34:29), Palatinus L., Chapuis G. (2007). J. Appl. Cryst. 40, 786-790, Petricek, V., Dusek, M. & Palatinus, L. (2006). Jana2006. Structure Determination Software Programs. Institute of Physics, Praha, Czech Republic..

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