In the title salt adduct, 2H3O+·C10H6O6S22-·2C3H7NO, the 1,5-naphthalenedisulfonate dianion lies on an inversion center. Intermolecular interactions link two hydroxonium cations, one 1,5-naphthalenedisulfonate dianion and two N,N-dimethylformamide molecules into a short hydrogen-bonded chain. A supramolecular hydrogen-bonding network structure is formed via further intermolecular hydrogen bonds.
Supporting information
CCDC reference: 293814
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.111
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N1
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O1W
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Dihydroxonium 1,5-naphthalenedisulfonate
N,
N-dimethylformamide
disolvate
top
Crystal data top
2H3O+·C10H6O6S2−·2C3H7NO | F(000) = 496 |
Mr = 470.51 | Dx = 1.424 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9318 reflections |
a = 9.1614 (18) Å | θ = 3.3–27.5° |
b = 12.101 (2) Å | µ = 0.30 mm−1 |
c = 10.053 (2) Å | T = 295 K |
β = 100.10 (3)° | Prism, colorless |
V = 1097.2 (4) Å3 | 0.32 × 0.27 × 0.20 mm |
Z = 2 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2507 independent reflections |
Radiation source: fine-focus sealed tube | 2193 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.3° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −15→15 |
Tmin = 0.911, Tmax = 0.943 | l = −13→13 |
10588 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0663P)2 + 0.3282P] where P = (Fo2 + 2Fc2)/3 |
2507 reflections | (Δ/σ)max < 0.001 |
147 parameters | Δρmax = 0.52 e Å−3 |
6 restraints | Δρmin = −0.27 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.14585 (4) | 0.37380 (3) | 0.24652 (4) | 0.03585 (15) | |
O1W | 0.48829 (16) | 0.24214 (14) | 0.42229 (15) | 0.0632 (4) | |
O1 | 0.25032 (16) | 0.42020 (12) | 0.17018 (14) | 0.0554 (4) | |
O2 | 0.20371 (15) | 0.27821 (10) | 0.32684 (14) | 0.0499 (3) | |
O3 | 0.00218 (15) | 0.34940 (13) | 0.16396 (14) | 0.0569 (4) | |
O4 | 0.66802 (15) | 0.15210 (12) | 0.30644 (15) | 0.0531 (3) | |
N1 | 0.81967 (18) | 0.00553 (15) | 0.31535 (18) | 0.0524 (4) | |
C1 | 0.15364 (19) | 0.66179 (14) | 0.44739 (18) | 0.0412 (4) | |
C2 | 0.17900 (17) | 0.57714 (13) | 0.35873 (17) | 0.0372 (3) | |
C3 | 0.11041 (16) | 0.47705 (12) | 0.36244 (15) | 0.0303 (3) | |
C4 | 0.01221 (15) | 0.45644 (11) | 0.45502 (14) | 0.0281 (3) | |
C5 | −0.06208 (18) | 0.35437 (13) | 0.46205 (17) | 0.0370 (3) | |
C6 | 0.8891 (3) | 0.0471 (3) | 0.2058 (3) | 0.0823 (8) | |
C7 | 0.8689 (3) | −0.1014 (2) | 0.3770 (4) | 0.0849 (9) | |
C8 | 0.71438 (19) | 0.05935 (16) | 0.35600 (19) | 0.0449 (4) | |
H1W1 | 0.541 (2) | 0.1976 (19) | 0.382 (2) | 0.095* | |
H1W2 | 0.3976 (13) | 0.240 (2) | 0.381 (2) | 0.095* | |
H1W3 | 0.488 (3) | 0.217 (2) | 0.5029 (12) | 0.095* | |
H1 | 0.2002 | 0.7298 | 0.4440 | 0.049* | |
H2 | 0.2425 | 0.5891 | 0.2974 | 0.045* | |
H5 | −0.0477 | 0.2975 | 0.4035 | 0.044* | |
H6A | 0.8338 | 0.1092 | 0.1642 | 0.124* | |
H6B | 0.8904 | −0.0101 | 0.1398 | 0.124* | |
H6C | 0.9889 | 0.0697 | 0.2410 | 0.124* | |
H7A | 0.8227 | −0.1140 | 0.4542 | 0.127* | |
H7B | 0.9747 | −0.1007 | 0.4046 | 0.127* | |
H7C | 0.8416 | −0.1594 | 0.3122 | 0.127* | |
H8 | 0.6705 | 0.0291 | 0.4244 | 0.054* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0351 (2) | 0.0426 (2) | 0.0311 (2) | 0.00923 (15) | 0.00916 (15) | −0.00635 (14) |
O1 | 0.0612 (8) | 0.0647 (9) | 0.0484 (8) | 0.0068 (7) | 0.0323 (7) | −0.0054 (6) |
O2 | 0.0529 (7) | 0.0447 (7) | 0.0542 (8) | 0.0184 (6) | 0.0152 (6) | −0.0013 (6) |
O3 | 0.0469 (7) | 0.0770 (10) | 0.0439 (7) | 0.0083 (6) | −0.0001 (6) | −0.0233 (7) |
O4 | 0.0497 (7) | 0.0587 (8) | 0.0514 (8) | 0.0014 (6) | 0.0103 (6) | 0.0054 (6) |
O1W | 0.0504 (8) | 0.0906 (12) | 0.0490 (8) | 0.0208 (8) | 0.0098 (7) | 0.0155 (8) |
N1 | 0.0415 (8) | 0.0559 (9) | 0.0592 (10) | −0.0036 (7) | 0.0070 (7) | −0.0140 (7) |
C1 | 0.0445 (9) | 0.0331 (8) | 0.0490 (10) | −0.0095 (6) | 0.0163 (7) | −0.0006 (7) |
C2 | 0.0359 (8) | 0.0410 (8) | 0.0378 (8) | −0.0016 (6) | 0.0146 (6) | 0.0028 (6) |
C3 | 0.0307 (7) | 0.0328 (7) | 0.0282 (7) | 0.0051 (5) | 0.0078 (5) | −0.0014 (5) |
C4 | 0.0285 (7) | 0.0289 (7) | 0.0271 (7) | 0.0028 (5) | 0.0058 (5) | −0.0010 (5) |
C5 | 0.0425 (8) | 0.0306 (7) | 0.0396 (8) | −0.0032 (6) | 0.0120 (7) | −0.0056 (6) |
C6 | 0.0629 (15) | 0.111 (2) | 0.0812 (18) | 0.0022 (14) | 0.0341 (13) | −0.0110 (16) |
C7 | 0.0726 (16) | 0.0561 (14) | 0.124 (3) | 0.0080 (12) | 0.0114 (16) | −0.0077 (15) |
C8 | 0.0390 (8) | 0.0525 (10) | 0.0422 (9) | −0.0097 (7) | 0.0043 (7) | −0.0069 (7) |
Geometric parameters (Å, º) top
S1—O1 | 1.4415 (14) | C5—C1i | 1.356 (2) |
S1—O2 | 1.4564 (13) | O1W—H1W1 | 0.87 (2) |
S1—O3 | 1.4579 (14) | O1W—H1W2 | 0.87 (2) |
S1—C3 | 1.7769 (15) | O1W—H1W3 | 0.87 (2) |
O4—C8 | 1.270 (2) | C1—H1 | 0.9300 |
N1—C8 | 1.288 (2) | C2—H2 | 0.9300 |
N1—C6 | 1.455 (3) | C5—H5 | 0.9300 |
N1—C7 | 1.471 (3) | C6—H6A | 0.9600 |
C1—C5i | 1.356 (2) | C6—H6B | 0.9600 |
C1—C2 | 1.404 (2) | C6—H6C | 0.9600 |
C2—C3 | 1.368 (2) | C7—H7A | 0.9600 |
C3—C4 | 1.425 (2) | C7—H7B | 0.9600 |
C4—C5 | 1.418 (2) | C7—H7C | 0.9600 |
C4—C4i | 1.432 (3) | C8—H8 | 0.9300 |
| | | |
O1—S1—C3 | 106.86 (8) | N1—C6—H6B | 109.5 |
O1—S1—O2 | 113.17 (8) | N1—C6—H6C | 109.5 |
O1—S1—O3 | 113.16 (9) | N1—C7—H7A | 109.5 |
O2—S1—C3 | 106.59 (7) | N1—C7—H7B | 109.5 |
O2—S1—O3 | 111.05 (9) | N1—C7—H7C | 109.5 |
O3—S1—C3 | 105.39 (7) | N1—C8—H8 | 118.7 |
O4—C8—N1 | 122.66 (19) | C1—C2—H2 | 120.0 |
C1i—C5—C4 | 121.19 (14) | C1i—C5—H5 | 119.4 |
C2—C3—C4 | 121.22 (13) | C2—C1—H1 | 119.6 |
C2—C3—S1 | 117.84 (11) | C3—C2—H2 | 120.0 |
C3—C2—C1 | 120.06 (14) | C4—C5—H5 | 119.4 |
C3—C4—C4i | 118.04 (16) | C5i—C1—H1 | 119.6 |
C4—C3—S1 | 120.94 (11) | H1W1—O1W—H1W2 | 109.1 (14) |
C5i—C1—C2 | 120.79 (15) | H1W1—O1W—H1W3 | 107.8 (14) |
C5—C4—C3 | 123.25 (13) | H1W2—O1W—H1W3 | 106.1 (13) |
C5—C4—C4i | 118.71 (16) | H6A—C6—H6B | 109.5 |
C6—N1—C7 | 118.7 (2) | H6A—C6—H6C | 109.5 |
C8—N1—C6 | 121.1 (2) | H6B—C6—H6C | 109.5 |
C8—N1—C7 | 120.2 (2) | H7A—C7—H7B | 109.5 |
O4—C8—H8 | 118.7 | H7A—C7—H7C | 109.5 |
N1—C6—H6A | 109.5 | H7B—C7—H7C | 109.5 |
| | | |
S1—C3—C4—C4i | −179.54 (13) | C1—C2—C3—S1 | 179.43 (13) |
S1—C3—C4—C5 | 0.4 (2) | C2—C3—C4—C4i | −0.3 (2) |
O1—S1—C3—C2 | 1.65 (15) | C2—C3—C4—C5 | 179.60 (15) |
O1—S1—C3—C4 | −179.11 (12) | C3—C4—C5—C1i | 179.45 (15) |
O2—S1—C3—C2 | 122.94 (13) | C4i—C4—C5—C1i | −0.6 (3) |
O2—S1—C3—C4 | −57.83 (14) | C5i—C1—C2—C3 | 0.4 (3) |
O3—S1—C3—C2 | −118.98 (14) | C6—N1—C8—O4 | −2.0 (3) |
O3—S1—C3—C4 | 60.25 (14) | C7—N1—C8—O4 | 179.8 (2) |
C1—C2—C3—C4 | 0.2 (2) | | |
Symmetry code: (i) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O4 | 0.87 (2) | 1.60 (1) | 2.435 (2) | 161 (3) |
O1W—H1W2···O2 | 0.87 (2) | 1.82 (1) | 2.652 (2) | 161 (3) |
O1W—H1W3···O3ii | 0.87 (2) | 1.79 (1) | 2.653 (2) | 173 (2) |
Symmetry code: (ii) x+1/2, −y+1/2, z+1/2. |