Novel, predicted patterns of supramolecular self-assembly, afforded by tetrameric rings of C₂ symmetry in the crystal structures of 2-hydroxy-1-cyclopentanecarboxylic acid, 2-hydroxy-1-cyclohexanecarboxylic acid and 2-hydroxy-1-cycloheptanecarboxylic acid

Determination of the crystal structures of the homologous (1R*,2R*)-trans-2-hydroxy-1-cyclopentanecarboxylic acid (5T), (1R*,2S*)-cis-2-hydroxy-1-cyclohexanecarboxylic acid (6C) and (1R*,2S*)-cis-2-hydroxy-1-cycloheptanecarboxylic acid (7C) proved a predicted pattern of supramolecular close packing. The prediction was based on the common features observed in the crystal structures of six related 2-hydroxy-1-cyclopentanecarboxylic acids and analogous carboxamides [Kálmán et al. (2001). Acta Cryst. B57, 539–550]. This pattern is characterized by tetrameric rings of C₂ symmetry formed from dimeric rings. The C₂ symmetry of such tetramers is not common in the literature, usually they have C_i symmetry. Both types of tetramers are formed from dimers with similar or opposite orientation. The dimers differ in their hydrogen bonds. In 5T the monomers are joined by a pair of O1—H...O2=C bonds, whereas in 7C they are joined by a pair of O3—H...O1-H bonds. In 6C 60% of the disordered dimers are similar to those in 7C, while 40% resemble those in 5T. Apart from these hydrogen-bonding differences and the ring-size differences, the three crystals exhibit isostructurality.

Computing details

For all compounds, data collection: CAD-4 EXPRESS; cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms 1996); program(s) used to solve structure: SHELXS97 (Sheldrick 1997); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: PLATON (Spek 1998).

(5ts) trans-2-hydroxy-1-cyclopentane carboxylic acid

Crystal data

C6H10O3	F(000) = 560
Mr = 130.14	Dx = 1.325 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
a = 17.383 (2) Å	Cell parameters from 25 reflections
b = 6.188 (1) Å	θ = 13.1–14.3°
c = 12.361 (1) Å	µ = 0.11 mm^−1
β = 101.16 (1)°	T = 293 K
V = 1304.5 (3) Å^3	Block, colourless
Z = 8	0.40 × 0.25 × 0.15 mm

Data collection

Enraf-Nonius CAD4 diffractometer	838 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 28.0°, θmin = 3.4°
ω–2θ scans	h = −22→22
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24 350-359	k = −8→8
Tmin = 0.959, Tmax = 0.984	l = −16→16
3396 measured reflections	3 standard reflections every 60 min
1575 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 0.82	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
1575 reflections	(Δ/σ)max < 0.001
84 parameters	Δρmax = 0.18 e Å^−3
21 restraints	Δρmin = −0.16 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.08144 (9)	0.4250 (3)	0.21183 (10)	0.0579 (5)
H1	0.0490	0.5042	0.1743	0.075*
O2	0.02571 (8)	0.3088 (2)	−0.07966 (11)	0.0546 (4)
O3	0.14061 (9)	0.4528 (3)	−0.08640 (12)	0.0707 (5)
H3	0.1164	0.4997	−0.1452	0.092*
C1	0.13442 (10)	0.2386 (3)	0.06747 (13)	0.0377 (4)
H1A	0.1823	0.3203	0.0960	0.049*
C2	0.08541 (11)	0.2263 (3)	0.15561 (13)	0.0419 (5)
H2	0.0323	0.1789	0.1225	0.054*
C3	0.12508 (14)	0.0535 (4)	0.23511 (17)	0.0576 (6)
H3A	0.1566	0.1198	0.2999	0.075*
H3B	0.0861	−0.0387	0.2584	0.075*
C4	0.17620 (14)	−0.0766 (4)	0.17334 (17)	0.0585 (6)
H4A	0.1652	−0.2298	0.1776	0.076*
H4B	0.2312	−0.0520	0.2039	0.076*
C5	0.15589 (13)	0.0017 (4)	0.05415 (16)	0.0501 (5)
H5A	0.1120	−0.0783	0.0124	0.065*
H5B	0.2005	−0.0114	0.0179	0.065*
C6	0.09401 (11)	0.3382 (3)	−0.03940 (13)	0.0386 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0760 (10)	0.0679 (10)	0.0260 (6)	0.0230 (7)	0.0003 (7)	−0.0076 (6)
O2	0.0520 (8)	0.0710 (11)	0.0384 (7)	0.0009 (7)	0.0026 (6)	0.0138 (7)
O3	0.0698 (10)	0.0993 (13)	0.0376 (8)	−0.0248 (9)	−0.0029 (7)	0.0256 (8)
C1	0.0428 (9)	0.0445 (11)	0.0246 (8)	−0.0027 (8)	0.0035 (7)	0.0014 (7)
C2	0.0521 (10)	0.0490 (11)	0.0240 (7)	−0.0008 (8)	0.0057 (7)	0.0011 (7)
C3	0.0799 (15)	0.0599 (14)	0.0326 (9)	0.0006 (11)	0.0096 (10)	0.0146 (9)
C4	0.0706 (14)	0.0508 (13)	0.0504 (12)	0.0069 (10)	0.0024 (10)	0.0145 (10)
C5	0.0598 (11)	0.0514 (11)	0.0379 (10)	0.0103 (10)	0.0064 (9)	−0.0010 (9)
C6	0.0507 (10)	0.0411 (10)	0.0232 (7)	0.0010 (8)	0.0051 (7)	−0.0015 (7)

Geometric parameters (Å, º)

O1—C2	1.421 (2)	C2—H2	0.9800
O1—H1	0.8200	C3—C4	1.511 (3)
O2—C6	1.209 (2)	C3—H3A	0.9700
O3—C6	1.296 (2)	C3—H3B	0.9700
O3—H3	0.8200	C4—C5	1.526 (3)
C1—C6	1.503 (2)	C4—H4A	0.9700
C1—C2	1.509 (3)	C4—H4B	0.9700
C1—C5	1.530 (3)	C5—H5A	0.9700
C1—H1A	0.9800	C5—H5B	0.9700
C2—C3	1.524 (3)
C2—O1—H1	109.5	C2—C3—H3B	110.4
C6—O3—H3	109.5	H3A—C3—H3B	108.6
C6—C1—C2	114.96 (15)	C3—C4—C5	105.66 (16)
C6—C1—C5	112.37 (15)	C3—C4—H4A	110.6
C2—C1—C5	102.29 (16)	C5—C4—H4A	110.6
C6—C1—H1A	109.0	C3—C4—H4B	110.6
C2—C1—H1A	109.0	C5—C4—H4B	110.6
C5—C1—H1A	109.0	H4A—C4—H4B	108.7
O1—C2—C1	113.39 (16)	C4—C5—C1	102.48 (16)
O1—C2—C3	110.53 (15)	C4—C5—H5A	111.3
C1—C2—C3	104.64 (16)	C1—C5—H5A	111.3
O1—C2—H2	109.4	C4—C5—H5B	111.3
C1—C2—H2	109.4	C1—C5—H5B	111.3
C3—C2—H2	109.4	H5A—C5—H5B	109.2
C4—C3—C2	106.56 (16)	O2—C6—O3	123.17 (16)
C4—C3—H3A	110.4	O2—C6—C1	123.71 (17)
C2—C3—H3A	110.4	O3—C6—C1	113.08 (16)
C4—C3—H3B	110.4
C6—C1—C2—O1	−79.5 (2)	C3—C4—C5—C1	31.3 (2)
C5—C1—C2—O1	158.39 (15)	C6—C1—C5—C4	−166.49 (16)
C6—C1—C2—C3	159.94 (17)	C2—C1—C5—C4	−42.66 (19)
C5—C1—C2—C3	37.87 (18)	C2—C1—C6—O2	−38.4 (3)
O1—C2—C3—C4	−140.97 (18)	C5—C1—C6—O2	78.1 (2)
C1—C2—C3—C4	−18.6 (2)	C2—C1—C6—O3	144.04 (18)
C2—C3—C4—C5	−8.2 (2)	C5—C1—C6—O3	−99.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	1.95	2.7701 (19)	178
O3—H3···O1^ii	0.82	1.81	2.6187 (19)	167

Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+1, z−1/2.

(6cs) (1R*,2S*)-2-hydroxy-1-cyclohexanecarboxylic acid

Crystal data

C7H12O3	F(000) = 624
Mr = 144.17	Dx = 1.248 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
a = 21.436 (8) Å	Cell parameters from 25 reflections
b = 5.974 (1) Å	θ = 30.1–34.5°
c = 12.095 (3) Å	µ = 0.81 mm^−1
β = 97.70 (3)°	T = 293 K
V = 1534.9 (7) Å^3	Block, colourless
Z = 8	0.40 × 0.25 × 0.03 mm

Data collection

Enraf-Nonius CAD4 diffractometer	1287 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.010
Graphite monochromator	θmax = 75.6°, θmin = 4.2°
ω–2θ scans	h = −26→26
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24, 350-359	k = 0→7
Tmin = 0.738, Tmax = 0.976	l = 0→15
1794 measured reflections	3 standard reflections every 60 min
1597 independent reflections	intensity decay: 16%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
1597 reflections	(Δ/σ)max = 0.001
122 parameters	Δρmax = 0.19 e Å^−3
40 restraints	Δρmin = −0.16 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.06910 (4)	0.07106 (14)	0.18797 (6)	0.0511 (3)
H1X	0.0753	0.0656	0.2563	0.066*	0.604 (12)
H1Y	0.0385	0.0066	0.1544	0.066*	0.396 (12)
O2A	0.0897 (3)	0.0166 (8)	−0.0891 (4)	0.0667 (9)	0.604 (12)
O3A	0.0056 (3)	0.2159 (15)	−0.0642 (6)	0.0504 (12)	0.604 (12)
H3X	−0.0115	0.1223	−0.1077	0.066*	0.604 (12)
O2B	0.0174 (4)	0.202 (3)	−0.0774 (11)	0.0556 (17)	0.396 (12)
O3B	0.1107 (4)	0.0603 (13)	−0.0999 (5)	0.0624 (15)	0.396 (12)
H3Y	0.0915	0.0148	−0.1588	0.081*	0.396 (12)
C1	0.10260 (5)	0.31317 (18)	0.04841 (8)	0.0395 (3)
H1A	0.1005	0.4708	0.0258	0.051*	0.604 (12)
H1B	0.0980	0.4653	0.0180	0.051*	0.396 (12)
C2	0.06923 (5)	0.30032 (16)	0.15243 (8)	0.0375 (3)
H2	0.0257	0.3518	0.1336	0.049*
C3	0.10238 (6)	0.4462 (2)	0.24469 (10)	0.0508 (3)
H3A	0.0965	0.6021	0.2233	0.066*
H3B	0.0831	0.4232	0.3119	0.066*
C4	0.17203 (6)	0.3984 (2)	0.27000 (11)	0.0580 (4)
H4A	0.1782	0.2491	0.3011	0.075*
H4B	0.1912	0.5043	0.3251	0.075*
C5	0.20362 (6)	0.4158 (3)	0.16539 (13)	0.0670 (4)
H5A	0.2478	0.3770	0.1829	0.087*
H5B	0.2009	0.5688	0.1383	0.087*
C6	0.17235 (6)	0.2601 (3)	0.07521 (11)	0.0593 (4)
H6A	0.1776	0.1062	0.1003	0.077*
H6B	0.1924	0.2764	0.0084	0.077*
C7A	0.0700 (3)	0.1837 (13)	−0.0512 (6)	0.0381 (12)	0.604 (12)
C7B	0.0683 (5)	0.154 (2)	−0.0350 (8)	0.040 (2)	0.396 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0646 (5)	0.0517 (5)	0.0351 (4)	−0.0160 (4)	−0.0003 (3)	0.0076 (3)
O2A	0.076 (2)	0.0853 (19)	0.0387 (11)	0.0076 (15)	0.0088 (13)	−0.0234 (12)
O3A	0.056 (2)	0.0437 (11)	0.046 (2)	−0.0028 (16)	−0.0124 (16)	0.0014 (14)
O2B	0.056 (3)	0.063 (4)	0.046 (2)	−0.015 (2)	−0.003 (2)	−0.001 (2)
O3B	0.078 (3)	0.076 (3)	0.0316 (16)	0.018 (2)	−0.0002 (19)	−0.0143 (16)
C1	0.0488 (6)	0.0422 (6)	0.0274 (5)	−0.0026 (4)	0.0046 (4)	0.0018 (4)
C2	0.0401 (5)	0.0415 (6)	0.0308 (5)	0.0024 (4)	0.0042 (4)	−0.0028 (4)
C3	0.0625 (7)	0.0504 (6)	0.0392 (6)	0.0000 (5)	0.0052 (5)	−0.0136 (5)
C4	0.0602 (7)	0.0631 (8)	0.0460 (7)	−0.0109 (6)	−0.0103 (5)	−0.0082 (6)
C5	0.0453 (6)	0.0846 (10)	0.0697 (9)	−0.0165 (6)	0.0023 (6)	−0.0025 (7)
C6	0.0464 (7)	0.0844 (9)	0.0493 (7)	−0.0023 (6)	0.0152 (5)	−0.0089 (7)
C7A	0.0610 (18)	0.0359 (17)	0.0153 (19)	−0.0005 (11)	−0.0020 (14)	0.0092 (19)
C7B	0.063 (3)	0.043 (4)	0.015 (3)	0.005 (2)	0.0080 (16)	0.015 (2)

Geometric parameters (Å, º)

O1—C2	1.4356 (13)	C1—H1B	0.9800
O1—H1X	0.8200	C2—C3	1.5158 (15)
O1—H1Y	0.8200	C2—H2	0.9800
O2A—C7A	1.198 (8)	C3—C4	1.5105 (19)
O3A—C7A	1.380 (10)	C3—H3A	0.9700
O3A—H3X	0.8200	C3—H3B	0.9700
O2B—C7B	1.178 (12)	C4—C5	1.516 (2)
O3B—C7B	1.393 (11)	C4—H4A	0.9700
O3B—H3Y	0.8200	C4—H4B	0.9700
C1—C7B	1.505 (6)	C5—C6	1.519 (2)
C1—C6	1.5204 (18)	C5—H5A	0.9700
C1—C2	1.5302 (14)	C5—H5B	0.9700
C1—C7A	1.521 (4)	C6—H6A	0.9700
C1—H1A	0.9800	C6—H6B	0.9700
C2—O1—H1X	109.5	H3A—C3—H3B	107.8
C2—O1—H1Y	109.5	C3—C4—C5	110.95 (10)
C7B—O3B—H3Y	109.5	C3—C4—H4A	109.4
C7B—C1—C6	112.9 (5)	C5—C4—H4A	109.4
C7B—C1—C2	106.2 (5)	C3—C4—H4B	109.4
C6—C1—C2	111.64 (9)	C5—C4—H4B	109.4
C6—C1—C7A	113.4 (3)	H4A—C4—H4B	108.0
C2—C1—C7A	114.2 (4)	C4—C5—C6	110.72 (11)
C6—C1—H1A	105.6	C4—C5—H5A	109.5
C2—C1—H1A	105.6	C6—C5—H5A	109.5
C7A—C1—H1A	105.6	C4—C5—H5B	109.5
C7B—C1—H1B	108.7	C6—C5—H5B	109.5
C6—C1—H1B	108.7	H5A—C5—H5B	108.1
C2—C1—H1B	108.7	C5—C6—C1	110.60 (11)
O1—C2—C3	110.35 (9)	C5—C6—H6A	109.5
O1—C2—C1	108.29 (8)	C1—C6—H6A	109.5
C3—C2—C1	110.60 (9)	C5—C6—H6B	109.5
O1—C2—H2	109.2	C1—C6—H6B	109.5
C3—C2—H2	109.2	H6A—C6—H6B	108.1
C1—C2—H2	109.2	O2A—C7A—O3A	118.1 (6)
C4—C3—C2	113.18 (10)	O2A—C7A—C1	125.3 (6)
C4—C3—H3A	108.9	O3A—C7A—C1	111.4 (6)
C2—C3—H3A	108.9	O2B—C7B—O3B	119.2 (9)
C4—C3—H3B	108.9	O2B—C7B—C1	118.6 (10)
C2—C3—H3B	108.9	O3B—C7B—C1	109.6 (7)
C7B—C1—C2—O1	55.9 (5)	C7B—C1—C6—C5	−176.1 (6)
C6—C1—C2—O1	−67.52 (12)	C2—C1—C6—C5	−56.56 (14)
C7A—C1—C2—O1	62.8 (4)	C7A—C1—C6—C5	172.7 (4)
C7B—C1—C2—C3	176.9 (5)	C6—C1—C7A—O2A	18.7 (12)
C6—C1—C2—C3	53.51 (13)	C2—C1—C7A—O2A	−110.7 (10)
C7A—C1—C2—C3	−176.2 (4)	C6—C1—C7A—O3A	172.6 (6)
O1—C2—C3—C4	67.02 (13)	C2—C1—C7A—O3A	43.2 (8)
C1—C2—C3—C4	−52.78 (13)	C6—C1—C7B—O2B	−166.1 (12)
C2—C3—C4—C5	54.55 (16)	C2—C1—C7B—O2B	71.2 (14)
C3—C4—C5—C6	−56.27 (17)	C6—C1—C7B—O3B	−24.6 (10)
C4—C5—C6—C1	57.65 (16)	C2—C1—C7B—O3B	−147.2 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1X···O2A^i	0.82	1.92	2.724 (4)	167
O1—H1Y···O2B^ii	0.82	1.89	2.687 (14)	166
O3A—H3X···O1^ii	0.82	1.87	2.665 (9)	165
O3B—H3Y···O1^iii	0.82	1.92	2.717 (6)	163

Symmetry codes: (i) x, −y, z+1/2; (ii) −x, −y, −z; (iii) x, −y, z−1/2.

(7cs) (1R*,2S*)-2-hydroxy-1-cycloheptane carboxylic acid

Crystal data

C8H14O3	F(000) = 688
Mr = 158.19	Dx = 1.257 Mg m^−3
Monoclinic, I2/c	Cu Kα radiation, λ = 1.54180 Å
a = 22.876 (5) Å	Cell parameters from 25 reflections
b = 6.224 (1) Å	θ = 37.1–39.9°
c = 11.793 (2) Å	µ = 0.79 mm^−1
β = 95.56 (3)°	T = 293 K
V = 1671.2 (5) Å^3	Block, colourless
Z = 8	0.35 × 0.25 × 0.20 mm

Data collection

Enraf-Nonius CAD4 diffractometer	1574 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 76.0°, θmin = 3.9°
ω–2θ scans	h = −28→28
Absorption correction: ψ scan North A.C., Philips, D.C. & Mathews, F. (1968) Acta Cryst. A24, 350-359	k = −7→7
Tmin = 0.771, Tmax = 0.859	l = −14→14
6926 measured reflections	3 standard reflections every 60 min
1720 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.38	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
1720 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.15 e Å^−3
245 restraints	Δρmin = −0.15 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.05831 (4)	−0.11228 (13)	0.17608 (5)	0.0565 (3)
H1	0.0642	−0.1176	0.2457	0.073*
O2	0.08762 (4)	0.03752 (15)	−0.09191 (7)	0.0663 (3)
O3	0.01314 (3)	−0.18594 (12)	−0.08259 (6)	0.0536 (3)
H3	−0.0054	−0.0868	−0.1145	0.070*
C1	0.10206 (4)	−0.28259 (14)	0.02337 (7)	0.0420 (3)
H1A	0.1028	−0.4202	−0.0168	0.055*	0.851 (5)
H1B	0.0957	−0.4189	−0.0175	0.055*	0.149 (5)
C2	0.06954 (4)	−0.31900 (15)	0.12895 (7)	0.0409 (3)
H2A	0.0319	−0.3887	0.1056	0.053*	0.851 (5)
H2B	0.0307	−0.3720	0.0990	0.053*	0.149 (5)
C3A	0.10321 (11)	−0.4563 (5)	0.22091 (19)	0.0577 (6)	0.851 (5)
H3A	0.0748	−0.5242	0.2653	0.075*	0.851 (5)
H3B	0.1268	−0.3609	0.2717	0.075*	0.851 (5)
C3B	0.0935 (5)	−0.491 (3)	0.2101 (14)	0.076 (5)	0.149 (5)
H3C	0.0733	−0.4825	0.2785	0.099*	0.149 (5)
H3D	0.0844	−0.6300	0.1754	0.099*	0.149 (5)
C4A	0.14359 (7)	−0.6321 (2)	0.18140 (13)	0.0642 (5)	0.851 (5)
H4A	0.1479	−0.7445	0.2386	0.084*	0.851 (5)
H4B	0.1255	−0.6951	0.1114	0.084*	0.851 (5)
C4B	0.1583 (3)	−0.4808 (19)	0.2436 (7)	0.076 (3)	0.149 (5)
H4C	0.1661	−0.5505	0.3171	0.099*	0.149 (5)
H4D	0.1691	−0.3309	0.2538	0.099*	0.149 (5)
C5A	0.20469 (12)	−0.5463 (6)	0.1610 (3)	0.0757 (10)	0.851 (5)
H5A	0.2205	−0.4718	0.2294	0.098*	0.851 (5)
H5B	0.2300	−0.6688	0.1513	0.098*	0.851 (5)
C5B	0.1984 (8)	−0.581 (3)	0.1626 (13)	0.072 (4)	0.149 (5)
H5C	0.2380	−0.5846	0.2006	0.094*	0.149 (5)
H5D	0.1861	−0.7282	0.1484	0.094*	0.149 (5)
C6A	0.20894 (12)	−0.3976 (5)	0.0615 (3)	0.0712 (8)	0.851 (5)
H6A	0.2032	−0.4819	−0.0079	0.093*	0.851 (5)
H6B	0.2485	−0.3403	0.0663	0.093*	0.851 (5)
C6B	0.2005 (6)	−0.470 (2)	0.0491 (12)	0.064 (4)	0.149 (5)
H6C	0.1856	−0.5689	−0.0105	0.083*	0.149 (5)
H6D	0.2413	−0.4408	0.0384	0.083*	0.149 (5)
C7A	0.16627 (8)	−0.2101 (5)	0.0507 (3)	0.0570 (7)	0.851 (5)
H7A	0.1768	−0.1148	−0.0091	0.074*	0.851 (5)
H7B	0.1697	−0.1297	0.1216	0.074*	0.851 (5)
C7B	0.1666 (4)	−0.264 (2)	0.0341 (17)	0.058 (4)	0.149 (5)
H7C	0.1783	−0.1716	0.0987	0.076*	0.149 (5)
H7D	0.1780	−0.1921	−0.0334	0.076*	0.149 (5)
C8	0.06781 (4)	−0.12552 (15)	−0.05584 (7)	0.0442 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0779 (6)	0.0603 (5)	0.0308 (4)	0.0234 (4)	0.0021 (3)	−0.0044 (3)
O2	0.0744 (6)	0.0700 (6)	0.0534 (5)	−0.0034 (4)	0.0012 (4)	0.0278 (4)
O3	0.0593 (5)	0.0507 (5)	0.0491 (5)	0.0084 (3)	−0.0032 (3)	0.0002 (3)
C1	0.0528 (5)	0.0411 (5)	0.0331 (5)	0.0070 (3)	0.0094 (4)	0.0029 (3)
C2	0.0467 (5)	0.0436 (5)	0.0330 (5)	−0.0023 (3)	0.0062 (3)	0.0027 (3)
C3A	0.0777 (10)	0.0584 (12)	0.0386 (7)	0.0136 (10)	0.0132 (8)	0.0161 (7)
C3B	0.090 (6)	0.055 (6)	0.082 (10)	−0.027 (4)	−0.008 (6)	0.031 (6)
C4A	0.0905 (11)	0.0408 (7)	0.0606 (8)	0.0106 (6)	0.0034 (7)	0.0105 (6)
C4B	0.063 (4)	0.099 (8)	0.064 (5)	0.011 (4)	−0.001 (4)	0.034 (5)
C5A	0.0693 (11)	0.073 (2)	0.0847 (19)	0.0286 (12)	0.0052 (10)	0.0195 (13)
C5B	0.127 (11)	0.033 (4)	0.057 (7)	0.005 (5)	0.009 (6)	0.004 (4)
C6A	0.0563 (9)	0.0718 (17)	0.0878 (14)	0.0193 (10)	0.0182 (9)	0.0182 (12)
C6B	0.061 (6)	0.049 (7)	0.083 (7)	0.030 (5)	0.015 (5)	0.008 (5)
C7A	0.0448 (8)	0.0537 (13)	0.0739 (14)	0.0065 (6)	0.0132 (7)	0.0181 (11)
C7B	0.068 (5)	0.047 (7)	0.063 (6)	0.010 (4)	0.027 (4)	0.016 (6)
C8	0.0571 (5)	0.0483 (5)	0.0280 (4)	0.0081 (4)	0.0084 (3)	0.0011 (3)

Geometric parameters (Å, º)

O1—C2	1.4346 (11)	C4A—H4A	0.9700
O1—H1	0.8200	C4A—H4B	0.9700
O2—C8	1.2055 (13)	C4B—C5B	1.520 (10)
O3—C8	1.3147 (13)	C4B—H4C	0.9700
O3—H3	0.8200	C4B—H4D	0.9700
C1—C7B	1.474 (10)	C5A—C6A	1.505 (3)
C1—C8	1.5167 (13)	C5A—H5A	0.9700
C1—C2	1.5278 (11)	C5A—H5B	0.9700
C1—C7A	1.541 (2)	C5B—C6B	1.510 (11)
C1—H1A	0.9800	C5B—H5C	0.9700
C1—H1B	0.9800	C5B—H5D	0.9700
C2—C3B	1.504 (9)	C6A—C7A	1.519 (3)
C2—C3A	1.5289 (19)	C6A—H6A	0.9700
C2—H2A	0.9800	C6A—H6B	0.9700
C2—H2B	0.9800	C6B—C7B	1.504 (10)
C3A—C4A	1.533 (3)	C6B—H6C	0.9700
C3A—H3A	0.9700	C6B—H6D	0.9700
C3A—H3B	0.9700	C7A—H7A	0.9700
C3B—C4B	1.498 (10)	C7A—H7B	0.9700
C3B—H3C	0.9700	C7B—H7C	0.9700
C3B—H3D	0.9700	C7B—H7D	0.9700
C4A—C5A	1.537 (4)
C2—O1—H1	109.5	C5B—C4B—H4C	108.0
C8—O3—H3	109.5	C3B—C4B—H4D	108.0
C7B—C1—C8	117.0 (6)	C5B—C4B—H4D	108.0
C7B—C1—C2	120.3 (7)	H4C—C4B—H4D	107.2
C8—C1—C2	109.53 (7)	C6A—C5A—C4A	117.7 (2)
C8—C1—C7A	111.43 (13)	C6A—C5A—H5A	107.9
C2—C1—C7A	113.72 (16)	C4A—C5A—H5A	107.9
C8—C1—H1A	107.3	C6A—C5A—H5B	107.9
C2—C1—H1A	107.3	C4A—C5A—H5B	107.9
C7A—C1—H1A	107.3	H5A—C5A—H5B	107.2
C7B—C1—H1B	102.2	C6B—C5B—C4B	116.3 (9)
C8—C1—H1B	102.2	C6B—C5B—H5C	108.2
C2—C1—H1B	102.2	C4B—C5B—H5C	108.2
O1—C2—C3B	117.4 (8)	C6B—C5B—H5D	108.2
O1—C2—C3A	108.86 (13)	C4B—C5B—H5D	108.2
O1—C2—C1	107.60 (7)	H5C—C5B—H5D	107.4
C3B—C2—C1	116.6 (6)	C5A—C6A—C7A	116.6 (2)
C3A—C2—C1	114.16 (9)	C5A—C6A—H6A	108.1
O1—C2—H2A	108.7	C7A—C6A—H6A	108.1
C3A—C2—H2A	108.7	C5A—C6A—H6B	108.1
C1—C2—H2A	108.7	C7A—C6A—H6B	108.1
O1—C2—H2B	104.6	H6A—C6A—H6B	107.3
C3B—C2—H2B	104.6	C5B—C6B—C7B	115.7 (10)
C1—C2—H2B	104.6	C5B—C6B—H6C	108.4
C2—C3A—C4A	117.40 (16)	C7B—C6B—H6C	108.4
C2—C3A—H3A	108.0	C5B—C6B—H6D	108.4
C4A—C3A—H3A	108.0	C7B—C6B—H6D	108.4
C2—C3A—H3B	108.0	H6C—C6B—H6D	107.4
C4A—C3A—H3B	108.0	C6A—C7A—C1	112.6 (2)
H3A—C3A—H3B	107.2	C6A—C7A—H7A	109.1
C4B—C3B—C2	115.3 (8)	C1—C7A—H7A	109.1
C4B—C3B—H3C	108.4	C6A—C7A—H7B	109.1
C2—C3B—H3C	108.4	C1—C7A—H7B	109.1
C4B—C3B—H3D	108.4	H7A—C7A—H7B	107.8
C2—C3B—H3D	108.4	C1—C7B—C6B	116.3 (11)
H3C—C3B—H3D	107.5	C1—C7B—H7C	108.2
C5A—C4A—C3A	112.6 (2)	C6B—C7B—H7C	108.2
C5A—C4A—H4A	109.1	C1—C7B—H7D	108.2
C3A—C4A—H4A	109.1	C6B—C7B—H7D	108.2
C5A—C4A—H4B	109.1	H7C—C7B—H7D	107.4
C3A—C4A—H4B	109.1	O2—C8—O3	122.52 (9)
H4A—C4A—H4B	107.8	O2—C8—C1	124.78 (9)
C3B—C4B—C5B	117.3 (11)	O3—C8—C1	112.71 (8)
C3B—C4B—H4C	108.0
C7B—C1—C2—O1	87.1 (7)	C4A—C5A—C6A—C7A	49.4 (4)
C8—C1—C2—O1	−52.91 (10)	C4B—C5B—C6B—C7B	5 (2)
C7A—C1—C2—O1	72.49 (15)	C5A—C6A—C7A—C1	−67.1 (4)
C7B—C1—C2—C3B	−47.3 (10)	C8—C1—C7A—C6A	−144.1 (2)
C8—C1—C2—C3B	172.7 (8)	C2—C1—C7A—C6A	91.6 (2)
C8—C1—C2—C3A	−173.84 (16)	C8—C1—C7B—C6B	−144.8 (10)
C7A—C1—C2—C3A	−48.4 (2)	C2—C1—C7B—C6B	78.1 (15)
O1—C2—C3A—C4A	−152.4 (2)	C5B—C6B—C7B—C1	−70 (2)
C1—C2—C3A—C4A	−32.2 (3)	C7B—C1—C8—O2	−15.8 (9)
O1—C2—C3B—C4B	−80.8 (14)	C2—C1—C8—O2	125.63 (10)
C1—C2—C3B—C4B	49.0 (17)	C7A—C1—C8—O2	−1.08 (19)
C2—C3A—C4A—C5A	84.5 (3)	C7B—C1—C8—O3	163.9 (8)
C2—C3B—C4B—C5B	−82.9 (17)	C2—C1—C8—O3	−54.66 (10)
C3A—C4A—C5A—C6A	−68.9 (3)	C7A—C1—C8—O3	178.62 (16)
C3B—C4B—C5B—C6B	67.7 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	2.00	2.7923 (12)	162
O3—H3···O1^ii	0.82	1.83	2.6425 (11)	170

Symmetry codes: (i) x, −y, z+1/2; (ii) −x, −y, −z.