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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\overline 1 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016295/fl6049sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016295/fl6049Isup2.hkl
Contains datablock I

CCDC reference: 221712

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


Amber Alert 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

Computing details top

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) top
Crystal data top
C10H6O8·2C2H6OSZ = 1
Mr = 410.40F(000) = 214
Triclinic, P1Dx = 1.495 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3283 (6) ÅCell parameters from 3039 reflections
b = 7.3331 (6) Åθ = 2.3–29.0°
c = 8.9456 (8) ŵ = 0.34 mm1
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) Å3
Data collection top
Bruker SMART 1000 CCD
diffractometer
2112 independent reflections
Radiation source: sealed tube1918 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.010
ω rotation with narrow frames scansθmax = 29.1°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 99
Tmin = 0.849, Tmax = 0.931k = 99
4046 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: All non-H atoms found by direct methods
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: Geom except OH coords freely refined
wR(F2) = 0.075H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0387P)2 + 0.1844P]
where P = (Fo2 + 2Fc2)/3
2112 reflections(Δ/σ)max = 0.001
126 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.56940 (17)0.94904 (17)0.14218 (13)0.0162 (2)
C20.58863 (17)1.11937 (17)0.05261 (14)0.0168 (2)
H20.64971.20090.08850.020*
C30.51965 (17)1.17155 (17)0.08860 (14)0.0160 (2)
C40.64701 (18)0.90580 (17)0.29329 (14)0.0178 (2)
O10.54595 (14)0.81614 (14)0.40204 (10)0.0229 (2)
H10.604 (3)0.793 (3)0.484 (2)0.034*
O20.78731 (15)0.95498 (16)0.31123 (11)0.0295 (2)
C50.52586 (18)1.36689 (17)0.17080 (14)0.0174 (2)
O30.69967 (14)1.39404 (14)0.19728 (12)0.0268 (2)
H30.704 (3)1.496 (3)0.238 (2)0.040*
O40.38433 (14)1.48471 (14)0.20067 (13)0.0290 (2)
S10.88455 (4)0.82189 (4)0.65791 (4)0.01906 (10)
O50.72689 (13)0.72202 (13)0.64578 (10)0.0217 (2)
C61.09286 (19)0.6984 (2)0.55329 (16)0.0257 (3)
H6A1.11410.56200.58950.039*
H6B1.20220.74470.56830.039*
H6C1.07690.72060.44450.039*
C70.9472 (2)0.7387 (2)0.84614 (16)0.0291 (3)
H7A0.83740.77940.92060.044*
H7B1.05220.79120.86170.044*
H7C0.98630.59960.85950.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0158 (5)0.0178 (6)0.0150 (5)0.0041 (4)0.0023 (4)0.0016 (4)
C20.0177 (6)0.0165 (6)0.0173 (6)0.0055 (4)0.0032 (4)0.0021 (4)
C30.0160 (5)0.0158 (5)0.0164 (5)0.0046 (4)0.0017 (4)0.0011 (4)
C40.0206 (6)0.0166 (6)0.0170 (6)0.0052 (4)0.0047 (4)0.0007 (4)
O10.0253 (5)0.0295 (5)0.0160 (4)0.0125 (4)0.0064 (4)0.0043 (4)
O20.0303 (5)0.0405 (6)0.0235 (5)0.0204 (5)0.0117 (4)0.0066 (4)
C50.0220 (6)0.0173 (6)0.0143 (5)0.0066 (5)0.0037 (4)0.0013 (4)
O30.0230 (5)0.0219 (5)0.0344 (6)0.0107 (4)0.0051 (4)0.0101 (4)
O40.0244 (5)0.0184 (5)0.0426 (6)0.0036 (4)0.0098 (4)0.0036 (4)
S10.01852 (16)0.01855 (16)0.02112 (17)0.00685 (11)0.00345 (11)0.00049 (11)
O50.0227 (5)0.0241 (5)0.0209 (4)0.0126 (4)0.0072 (4)0.0048 (4)
C60.0228 (7)0.0299 (7)0.0235 (7)0.0054 (5)0.0004 (5)0.0049 (5)
C70.0227 (7)0.0480 (9)0.0187 (6)0.0111 (6)0.0037 (5)0.0040 (6)
Geometric parameters (Å, º) top
C1—C21.3947 (17)C5—O31.3178 (15)
C1—C3i1.4013 (16)O3—H30.78 (2)
C1—C41.5022 (16)S1—O51.5403 (9)
C2—C31.3922 (17)S1—C61.7808 (14)
C2—H20.9500S1—C71.7825 (14)
C3—C51.5066 (16)C6—H6A0.9800
C4—O21.2120 (15)C6—H6B0.9800
C4—O11.3184 (15)C6—H6C0.9800
O1—H10.87 (2)C7—H7A0.9800
O2—S13.2270 (10)C7—H7B0.9800
C5—O41.2056 (16)C7—H7C0.9800
C2—C1—C3i119.41 (11)C4—O1—H1107.3 (12)
C2—C1—C4117.05 (11)O4—C5—O3125.33 (12)
C3i—C1—C4123.54 (11)O4—C5—C3122.35 (11)
C3—C2—C1120.94 (11)O3—C5—C3112.22 (10)
C3—C2—H2119.5C5—O3—H3112.9 (15)
C1—C2—H2119.5H6A—C6—H6B109.5
C2—C3—C1i119.64 (11)H6A—C6—H6C109.5
C2—C3—C5117.87 (11)H6B—C6—H6C109.5
C1i—C3—C5122.17 (11)H7A—C7—H7B109.5
O2—C4—O1124.39 (11)H7A—C7—H7C109.5
O2—C4—C1121.73 (11)H7B—C7—H7C109.5
O1—C4—C1113.86 (10)
C3i—C1—C2—C30.38 (19)C3i—C1—C4—O135.24 (16)
C4—C1—C2—C3179.55 (11)O1—C4—O2—S12.03 (16)
C1—C2—C3—C1i0.39 (19)C1—C4—O2—S1179.96 (9)
C1—C2—C3—C5173.29 (11)C2—C3—C5—O4118.06 (14)
C2—C1—C4—O233.53 (17)C1i—C3—C5—O455.45 (18)
C3i—C1—C4—O2146.55 (13)C2—C3—C5—O358.60 (15)
C2—C1—C4—O1144.69 (11)C1i—C3—C5—O3127.89 (13)
Symmetry code: (i) x+1, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O50.87 (2)1.76 (2)2.6317 (13)173.9 (18)
O3—H3···O5ii0.78 (2)1.84 (2)2.6146 (13)173 (2)
C6—H6C···O20.982.673.3595 (18)127
Symmetry code: (ii) x, y+1, z1.
 

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