Benzene-1,2,4,5-tetra­carboxyl­ic acid di­methyl sulfoxide disolvate: a redetermination at 150 K

The title compound, C₁₀H₆O₈.2C₂H₆OS, one of the few known examples of the cocrystallization of pyromellitic acid with common organic solvents, has been previously analysed by single-crystal X-ray diffraction at 296 K [Jin, Pan, Shen, Li & Hu (2003). Acta Cryst. C59, o205–o206]. We present here a redetermination at low temperature (150 K). The centrosymmetric compound crystallizes in space group P and exhibits co-operative strong (acid)O—H...O(solvent) and weaker (solvent)C—H...O(acid) hydrogen-bonding interactions, giving rise to a one-dimensional ribbon structure along the bc diagonal of the unit cell.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.028
• wR factor = 0.075
• Data-to-parameter ratio = 16.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           29.05
         From the CIF: _reflns_number_total               2112
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         2425
         Completeness (_total/calc)             87.09%
          Alert B: < 90% complete (theta max?)


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

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Computing details

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

(I)

Crystal data

C10H6O8·2C2H6OS	Z = 1
Mr = 410.40	F(000) = 214
Triclinic, P1	Dx = 1.495 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3283 (6) Å	Cell parameters from 3039 reflections
b = 7.3331 (6) Å	θ = 2.3–29.0°
c = 8.9456 (8) Å	µ = 0.34 mm^−1
α = 80.510 (2)°	T = 150 K
β = 81.124 (2)°	Block, colourless
γ = 75.474 (2)°	0.47 × 0.23 × 0.21 mm
V = 455.77 (7) Å^3

Data collection

Bruker SMART 1000 CCD diffractometer	2112 independent reflections
Radiation source: sealed tube	1918 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
ω rotation with narrow frames scans	θmax = 29.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→9
Tmin = 0.849, Tmax = 0.931	k = −9→9
4046 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: All non-H atoms found by direct methods
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: Geom except OH coords freely refined
wR(F^2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0387P)^2 + 0.1844P] where P = (Fo^2 + 2Fc^2)/3
2112 reflections	(Δ/σ)max = 0.001
126 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.26 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
C1	0.56940 (17)	0.94904 (17)	0.14218 (13)	0.0162 (2)
C2	0.58863 (17)	1.11937 (17)	0.05261 (14)	0.0168 (2)
H2	0.6497	1.2009	0.0885	0.020*
C3	0.51965 (17)	1.17155 (17)	−0.08860 (14)	0.0160 (2)
C4	0.64701 (18)	0.90580 (17)	0.29329 (14)	0.0178 (2)
O1	0.54595 (14)	0.81614 (14)	0.40204 (10)	0.0229 (2)
H1	0.604 (3)	0.793 (3)	0.484 (2)	0.034*
O2	0.78731 (15)	0.95498 (16)	0.31123 (11)	0.0295 (2)
C5	0.52586 (18)	1.36689 (17)	−0.17080 (14)	0.0174 (2)
O3	0.69967 (14)	1.39404 (14)	−0.19728 (12)	0.0268 (2)
H3	0.704 (3)	1.496 (3)	−0.238 (2)	0.040*
O4	0.38433 (14)	1.48471 (14)	−0.20067 (13)	0.0290 (2)
S1	0.88455 (4)	0.82189 (4)	0.65791 (4)	0.01906 (10)
O5	0.72689 (13)	0.72202 (13)	0.64578 (10)	0.0217 (2)
C6	1.09286 (19)	0.6984 (2)	0.55329 (16)	0.0257 (3)
H6A	1.1141	0.5620	0.5895	0.039*
H6B	1.2022	0.7447	0.5683	0.039*
H6C	1.0769	0.7206	0.4445	0.039*
C7	0.9472 (2)	0.7387 (2)	0.84614 (16)	0.0291 (3)
H7A	0.8374	0.7794	0.9206	0.044*
H7B	1.0522	0.7912	0.8617	0.044*
H7C	0.9863	0.5996	0.8595	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0158 (5)	0.0178 (6)	0.0150 (5)	−0.0041 (4)	−0.0023 (4)	−0.0016 (4)
C2	0.0177 (6)	0.0165 (6)	0.0173 (6)	−0.0055 (4)	−0.0032 (4)	−0.0021 (4)
C3	0.0160 (5)	0.0158 (5)	0.0164 (5)	−0.0046 (4)	−0.0017 (4)	−0.0011 (4)
C4	0.0206 (6)	0.0166 (6)	0.0170 (6)	−0.0052 (4)	−0.0047 (4)	−0.0007 (4)
O1	0.0253 (5)	0.0295 (5)	0.0160 (4)	−0.0125 (4)	−0.0064 (4)	0.0043 (4)
O2	0.0303 (5)	0.0405 (6)	0.0235 (5)	−0.0204 (5)	−0.0117 (4)	0.0066 (4)
C5	0.0220 (6)	0.0173 (6)	0.0143 (5)	−0.0066 (5)	−0.0037 (4)	−0.0013 (4)
O3	0.0230 (5)	0.0219 (5)	0.0344 (6)	−0.0107 (4)	−0.0051 (4)	0.0101 (4)
O4	0.0244 (5)	0.0184 (5)	0.0426 (6)	−0.0036 (4)	−0.0098 (4)	0.0036 (4)
S1	0.01852 (16)	0.01855 (16)	0.02112 (17)	−0.00685 (11)	−0.00345 (11)	−0.00049 (11)
O5	0.0227 (5)	0.0241 (5)	0.0209 (4)	−0.0126 (4)	−0.0072 (4)	0.0048 (4)
C6	0.0228 (7)	0.0299 (7)	0.0235 (7)	−0.0054 (5)	0.0004 (5)	−0.0049 (5)
C7	0.0227 (7)	0.0480 (9)	0.0187 (6)	−0.0111 (6)	−0.0037 (5)	−0.0040 (6)

Geometric parameters (Å, º)

C1—C2	1.3947 (17)	C5—O3	1.3178 (15)
C1—C3^i	1.4013 (16)	O3—H3	0.78 (2)
C1—C4	1.5022 (16)	S1—O5	1.5403 (9)
C2—C3	1.3922 (17)	S1—C6	1.7808 (14)
C2—H2	0.9500	S1—C7	1.7825 (14)
C3—C5	1.5066 (16)	C6—H6A	0.9800
C4—O2	1.2120 (15)	C6—H6B	0.9800
C4—O1	1.3184 (15)	C6—H6C	0.9800
O1—H1	0.87 (2)	C7—H7A	0.9800
O2—S1	3.2270 (10)	C7—H7B	0.9800
C5—O4	1.2056 (16)	C7—H7C	0.9800
C2—C1—C3^i	119.41 (11)	C4—O1—H1	107.3 (12)
C2—C1—C4	117.05 (11)	O4—C5—O3	125.33 (12)
C3^i—C1—C4	123.54 (11)	O4—C5—C3	122.35 (11)
C3—C2—C1	120.94 (11)	O3—C5—C3	112.22 (10)
C3—C2—H2	119.5	C5—O3—H3	112.9 (15)
C1—C2—H2	119.5	H6A—C6—H6B	109.5
C2—C3—C1^i	119.64 (11)	H6A—C6—H6C	109.5
C2—C3—C5	117.87 (11)	H6B—C6—H6C	109.5
C1^i—C3—C5	122.17 (11)	H7A—C7—H7B	109.5
O2—C4—O1	124.39 (11)	H7A—C7—H7C	109.5
O2—C4—C1	121.73 (11)	H7B—C7—H7C	109.5
O1—C4—C1	113.86 (10)
C3^i—C1—C2—C3	0.38 (19)	C3^i—C1—C4—O1	−35.24 (16)
C4—C1—C2—C3	−179.55 (11)	O1—C4—O2—S1	2.03 (16)
C1—C2—C3—C1^i	−0.39 (19)	C1—C4—O2—S1	−179.96 (9)
C1—C2—C3—C5	173.29 (11)	C2—C3—C5—O4	−118.06 (14)
C2—C1—C4—O2	−33.53 (17)	C1^i—C3—C5—O4	55.45 (18)
C3^i—C1—C4—O2	146.55 (13)	C2—C3—C5—O3	58.60 (15)
C2—C1—C4—O1	144.69 (11)	C1^i—C3—C5—O3	−127.89 (13)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	0.87 (2)	1.76 (2)	2.6317 (13)	173.9 (18)
O3—H3···O5^ii	0.78 (2)	1.84 (2)	2.6146 (13)	173 (2)
C6—H6C···O2	0.98	2.67	3.3595 (18)	127

Symmetry code: (ii) x, y+1, z−1.