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The title solvate, C7H6O4·C2H3N, comprises two mol­ecules, one acid and one solvent. The main mol­ecules are arranged in layers by a two-dimensional hydrogen-bond network. In this way, channels are formed along the [100] axis, which are occupied by tail-to-tail solvent mol­ecules in a manner similar to that observed previously in related structures. However, the hydrogen bond between an acetonitrile N atom and one of the hydroxyl groups is relatively normal, with an N...O separation of 2.8189 (10) Å. The placement of the solvent mol­ecules makes the whole structure unstable under ambient conditions. Several minutes after removing the crystal from the mother solution it became milky, which probably indicates release of the solvent from the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702987X/bh2117sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680702987X/bh2117Isup2.hkl
Contains datablock I

CCDC reference: 655014

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.045
  • wR factor = 0.131
  • Data-to-parameter ratio = 26.0

checkCIF/PLATON results

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Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.17 Ratio PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.42
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Related literature top

Related structures have been described, in which solvent molecules fill channels generated by a supramolecular arrangement (Aitipamula & Nangia, 2005; Gerkensmeier et al., 1999).

Experimental top

An amount of 3,4-dihydroxybenzoic acid monohydrate (0.2 g) were diluted in 6 ml of acetonitrile. The resulting mixture was warmed to 333 K and then slowly cooled to 293 K. After several hours, colourless crystals were formed.

Refinement top

All H atoms for the 3,4-dihydroxybenzoic acid molecule were found in a difference map and refined isotropically. H atoms of the methyl group in acetonitrile were placed in idealized positions, with C—H bond lengths constrained to 0.98 Å and Uiso(H) = 1.5Ueq(C14). This group was considered as a rigid group but allowed to rotate about C13—C14 σ bond.

Structure description top

Related structures have been described, in which solvent molecules fill channels generated by a supramolecular arrangement (Aitipamula & Nangia, 2005; Gerkensmeier et al., 1999).

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: HKL (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEPII view of the title solvate. The dashed bond shows the hydrogen bond connecting main molecule and solvent in the asymmetric unit.
3,4-Dihydroxybenozic acid acetonitile solvate top
Crystal data top
C7H6O4·C2H3NF(000) = 408
Mr = 195.17Dx = 1.427 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2242 reflections
a = 6.3792 (6) Åθ = 1.0–35.0°
b = 10.4941 (8) ŵ = 0.11 mm1
c = 13.7634 (12) ÅT = 120 K
β = 99.4790 (14)°Parallelepiped, colourless
V = 908.80 (14) Å30.4 × 0.2 × 0.2 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
3466 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 35.0°, θmin = 3.6°
CCD scansh = 1010
9774 measured reflectionsk = 1216
3948 independent reflectionsl = 2218
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0745P)2 + 0.1499P]
where P = (Fo2 + 2Fc2)/3
3948 reflections(Δ/σ)max = 0.025
152 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C7H6O4·C2H3NV = 908.80 (14) Å3
Mr = 195.17Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.3792 (6) ŵ = 0.11 mm1
b = 10.4941 (8) ÅT = 120 K
c = 13.7634 (12) Å0.4 × 0.2 × 0.2 mm
β = 99.4790 (14)°
Data collection top
Nonius KappaCCD
diffractometer
3466 reflections with I > 2σ(I)
9774 measured reflectionsRint = 0.026
3948 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.49 e Å3
3948 reflectionsΔρmin = 0.37 e Å3
152 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.25161 (9)1.05508 (6)0.06328 (5)0.02453 (13)
H10.381 (4)1.080 (2)0.0265 (17)0.073 (6)*
C20.24757 (11)0.93132 (7)0.07528 (5)0.01851 (13)
O30.39826 (10)0.86069 (6)0.04151 (5)0.02659 (14)
C40.04961 (10)0.87984 (7)0.13234 (5)0.01694 (13)
C50.12150 (11)0.96085 (7)0.16568 (5)0.01803 (13)
H50.113 (2)1.0546 (14)0.1515 (10)0.030 (3)*
C60.30668 (11)0.91081 (7)0.21885 (5)0.01761 (13)
O70.48099 (9)0.98127 (6)0.25608 (5)0.02552 (14)
H70.464 (3)1.059 (2)0.2347 (13)0.052 (5)*
C80.32202 (10)0.77978 (7)0.23852 (5)0.01706 (13)
O90.50348 (9)0.72937 (5)0.29073 (5)0.02233 (13)
H90.596 (3)0.7824 (19)0.3070 (14)0.056 (5)*
C100.15149 (11)0.69939 (7)0.20561 (6)0.01884 (13)
H100.1655 (19)0.6080 (12)0.2212 (9)0.023 (3)*
C110.03439 (11)0.74969 (7)0.15260 (5)0.01867 (13)
H110.155 (2)0.6970 (14)0.1283 (10)0.030 (3)*
N120.88052 (13)0.84338 (8)0.38793 (6)0.02975 (16)
C131.05256 (13)0.86299 (8)0.42443 (6)0.02431 (15)
C141.26991 (13)0.89099 (10)0.47069 (7)0.02865 (18)
H14A1.34320.93650.42390.043*
H14B1.34480.81110.49020.043*
H14C1.26800.94420.52910.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0197 (2)0.0181 (3)0.0325 (3)0.00133 (19)0.0057 (2)0.0037 (2)
C20.0154 (3)0.0175 (3)0.0212 (3)0.0009 (2)0.0013 (2)0.0003 (2)
O30.0183 (3)0.0207 (3)0.0363 (3)0.00038 (19)0.0086 (2)0.0010 (2)
C40.0134 (3)0.0165 (3)0.0196 (3)0.0007 (2)0.0014 (2)0.0001 (2)
C50.0147 (3)0.0148 (3)0.0232 (3)0.0003 (2)0.0010 (2)0.0014 (2)
C60.0135 (3)0.0138 (3)0.0241 (3)0.00094 (19)0.0012 (2)0.0004 (2)
O70.0162 (2)0.0147 (2)0.0414 (3)0.00371 (18)0.0077 (2)0.0035 (2)
C80.0130 (2)0.0140 (3)0.0227 (3)0.00081 (19)0.0012 (2)0.0000 (2)
O90.0148 (2)0.0150 (2)0.0338 (3)0.00113 (17)0.00611 (19)0.00066 (19)
C100.0158 (3)0.0135 (3)0.0257 (3)0.0006 (2)0.0012 (2)0.0003 (2)
C110.0151 (3)0.0157 (3)0.0237 (3)0.0012 (2)0.0014 (2)0.0011 (2)
N120.0237 (3)0.0309 (4)0.0329 (4)0.0007 (3)0.0004 (3)0.0005 (3)
C130.0226 (3)0.0236 (3)0.0258 (3)0.0024 (3)0.0012 (3)0.0013 (3)
C140.0204 (3)0.0325 (4)0.0312 (4)0.0012 (3)0.0013 (3)0.0052 (3)
Geometric parameters (Å, º) top
O1—C21.3089 (9)C8—O91.3646 (8)
O1—H10.93 (2)C8—C101.3922 (10)
C2—O31.2419 (9)O9—H90.82 (2)
C2—C41.4753 (10)C10—C111.3900 (10)
C4—C111.3942 (10)C10—H100.983 (13)
C4—C51.3999 (10)C11—H110.960 (14)
C5—C61.3864 (10)N12—C131.1478 (12)
C5—H51.003 (14)C13—C141.4572 (12)
C6—O71.3631 (9)C14—H14A0.9800
C6—C81.4017 (10)C14—H14B0.9800
O7—H70.87 (2)C14—H14C0.9800
C2—O1—H1110.1 (14)C10—C8—C6120.37 (6)
O3—C2—O1123.16 (7)C8—O9—H9113.2 (13)
O3—C2—C4121.51 (7)C11—C10—C8119.60 (6)
O1—C2—C4115.33 (6)C11—C10—H10121.6 (7)
C11—C4—C5120.30 (6)C8—C10—H10118.8 (7)
C11—C4—C2119.37 (6)C10—C11—C4120.16 (6)
C5—C4—C2120.33 (6)C10—C11—H11121.9 (9)
C6—C5—C4119.58 (6)C4—C11—H11118.0 (9)
C6—C5—H5119.2 (8)N12—C13—C14178.69 (10)
C4—C5—H5121.2 (8)C13—C14—H14A109.5
O7—C6—C5124.35 (6)C13—C14—H14B109.5
O7—C6—C8115.65 (6)H14A—C14—H14B109.5
C5—C6—C8119.99 (6)C13—C14—H14C109.5
C6—O7—H7109.3 (12)H14A—C14—H14C109.5
O9—C8—C10119.08 (6)H14B—C14—H14C109.5
O9—C8—C6120.54 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.93 (2)1.68 (2)2.6056 (9)174 (2)
O7—H7···O9ii0.87 (2)1.84 (2)2.6878 (8)164.8 (17)
O9—H9···N120.82 (2)2.07 (2)2.8189 (10)153.0 (18)
Symmetry codes: (i) x1, y+2, z; (ii) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC7H6O4·C2H3N
Mr195.17
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)6.3792 (6), 10.4941 (8), 13.7634 (12)
β (°) 99.4790 (14)
V3)908.80 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.4 × 0.2 × 0.2
Data collection
DiffractometerNonius KappaCCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9774, 3948, 3466
Rint0.026
(sin θ/λ)max1)0.806
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.131, 1.05
No. of reflections3948
No. of parameters152
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.49, 0.37

Computer programs: KappaCCD Server Software (Nonius, 1997), HKL (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.93 (2)1.68 (2)2.6056 (9)174 (2)
O7—H7···O9ii0.87 (2)1.84 (2)2.6878 (8)164.8 (17)
O9—H9···N120.82 (2)2.07 (2)2.8189 (10)153.0 (18)
Symmetry codes: (i) x1, y+2, z; (ii) x+1, y+1/2, z+1/2.
 

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