Hexakis(hydroxy­meth­yl)benzene

The centrosymmetric title compound, C₁₂H₁₈O₆, exhibits a three-dimensional network structure. The structure displays extensive O—H...O hydrogen bonding. In each molecule, two sets of three neighboring hydr­oxy groups are located above and below the plane defined by the central benzene ring.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.166
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  O3      ..       2.71 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Hexakis(hydroxymethyl)benzene

Crystal data

C12H18O6	F(000) = 276
Mr = 258.26	Dx = 1.561 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3072 reflections
a = 4.5946 (9) Å	θ = 5.4–54°
b = 8.9294 (18) Å	µ = 0.13 mm^−1
c = 13.452 (3) Å	T = 120 K
β = 95.50 (3)°	Block, yellow
V = 549.35 (19) Å^3	0.50 × 0.30 × 0.10 mm
Z = 2

Data collection

Stoe IPDSII diffractometer	868 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.088
Graphite monochromator	θmax = 27.3°, θmin = 2.7°
Detector resolution: 6.67 pixels mm^-1	h = −5→5
rotation scans	k = −11→11
4212 measured reflections	l = −15→17
1143 independent reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.166	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.1181P)^2 + 0.1727P] where P = (Fo^2 + 2Fc^2)/3
1143 reflections	(Δ/σ)max < 0.001
85 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.33 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	0.3475 (4)	0.96923 (17)	0.25965 (12)	0.0276 (4)
H1	0.2286	1.0296	0.2814	0.041*
O2	0.0001 (4)	0.70314 (17)	0.19362 (13)	0.0284 (5)
H2	0.0194	0.7692	0.2382	0.043*
O3	−0.1603 (4)	0.64146 (18)	−0.12987 (13)	0.0305 (5)
H3	−0.2914	0.5906	−0.1620	0.046*
C1	0.2175 (5)	1.0143 (2)	0.08068 (17)	0.0231 (5)
C2	0.0901 (5)	0.8736 (2)	0.05699 (17)	0.0234 (5)
C3	−0.1297 (5)	0.8597 (2)	−0.02302 (17)	0.0234 (5)
C4	0.4467 (5)	1.0273 (2)	0.16896 (17)	0.0264 (5)
H4A	0.6243	0.9722	0.1540	0.032*
H4B	0.5006	1.1340	0.1790	0.032*
C5	0.1890 (5)	0.7362 (2)	0.11797 (17)	0.0260 (5)
H5A	0.1947	0.6490	0.0728	0.031*
H5B	0.3896	0.7531	0.1498	0.031*
C6	−0.2763 (5)	0.7098 (2)	−0.04582 (18)	0.0271 (5)
H6A	−0.2432	0.6433	0.0131	0.033*
H6B	−0.4897	0.7244	−0.0604	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0332 (9)	0.0233 (8)	0.0265 (9)	0.0026 (6)	0.0042 (7)	−0.0002 (6)
O2	0.0368 (9)	0.0219 (8)	0.0270 (9)	−0.0014 (6)	0.0055 (7)	0.0008 (6)
O3	0.0362 (9)	0.0222 (8)	0.0337 (10)	−0.0032 (6)	0.0063 (7)	−0.0068 (6)
C1	0.0258 (10)	0.0194 (10)	0.0246 (11)	0.0004 (8)	0.0056 (8)	−0.0011 (8)
C2	0.0270 (10)	0.0187 (10)	0.0250 (12)	0.0014 (8)	0.0058 (9)	0.0001 (8)
C3	0.0268 (11)	0.0184 (10)	0.0257 (12)	−0.0007 (8)	0.0062 (9)	−0.0024 (8)
C4	0.0294 (12)	0.0215 (10)	0.0283 (13)	0.0002 (8)	0.0028 (9)	0.0004 (8)
C5	0.0330 (12)	0.0179 (10)	0.0277 (12)	0.0014 (8)	0.0063 (10)	0.0009 (8)
C6	0.0350 (12)	0.0181 (10)	0.0288 (12)	−0.0022 (8)	0.0062 (10)	−0.0006 (8)

Geometric parameters (Å, º)

O1—C4	1.439 (3)	C2—C5	1.520 (3)
O1—H1	0.8400	C3—C1^i	1.404 (3)
O2—C5	1.430 (3)	C3—C6	1.517 (3)
O2—H2	0.8400	C4—H4A	0.9900
O3—C6	1.432 (3)	C4—H4B	0.9900
O3—H3	0.8400	C5—H5A	0.9900
C1—C3^i	1.404 (3)	C5—H5B	0.9900
C1—C2	1.410 (3)	C6—H6A	0.9900
C1—C4	1.514 (3)	C6—H6B	0.9900
C2—C3	1.409 (3)
C4—O1—H1	109.5	O1—C4—H4B	109.1
C5—O2—H2	109.5	C1—C4—H4B	109.1
C6—O3—H3	109.5	H4A—C4—H4B	107.8
C3^i—C1—C2	119.9 (2)	O2—C5—C2	112.35 (18)
C3^i—C1—C4	120.85 (19)	O2—C5—H5A	109.1
C2—C1—C4	119.25 (19)	C2—C5—H5A	109.1
C3—C2—C1	120.18 (19)	O2—C5—H5B	109.1
C3—C2—C5	119.77 (18)	C2—C5—H5B	109.1
C1—C2—C5	120.05 (19)	H5A—C5—H5B	107.9
C1^i—C3—C2	119.90 (19)	O3—C6—C3	110.11 (18)
C1^i—C3—C6	119.8 (2)	O3—C6—H6A	109.6
C2—C3—C6	120.26 (19)	C3—C6—H6A	109.6
O1—C4—C1	112.57 (18)	O3—C6—H6B	109.6
O1—C4—H4A	109.1	C3—C6—H6B	109.6
C1—C4—H4A	109.1	H6A—C6—H6B	108.2

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.84	2.34	2.951 (2)	130
O1—H1···O2^ii	0.84	1.92	2.739 (2)	165
O1—H1···O3^iii	0.84	2.71	3.049 (3)	106
O2—H2···O3^iii	0.84	2.18	2.906 (3)	145
O3—H3···O1^iv	0.84	1.95	2.767 (2)	163

Symmetry codes: (ii) −x, y+1/2, −z+1/2; (iii) x, −y+3/2, z+1/2; (iv) x−1, −y+3/2, z−1/2.