Dihydroxonium 1,5-naphthalene­disulfonate N,N-dimethyl­formamide disolvate

Deng, Z.-P.; Gao, S.; Huo, L.-H.; Zhao, H.

doi:10.1107/S1600536805037347

Dihydroxonium 1,5-naphthalenedisulfonate N,N-dimethylformamide disolvate

Z.-P. Deng, S. Gao, L.-H. Huo and H. Zhao

In the title salt adduct, 2H₃O⁺·C₁₀H₆O₆S₂^2-·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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805037347/at6050sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805037347/at6050Isup2.hkl Contains datablock I

CCDC reference: 293814

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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

Computing details top

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
M_r = 470.51	D_x = 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	R_int = 0.015
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
T_min = 0.911, T_max = 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(F_o²) + (0.0663P)² + 0.3282P] where P = (F_o² + 2F_c²)/3
2507 reflections	(Δ/σ)_max < 0.001
147 parameters	Δρ_max = 0.52 e Å⁻³
6 restraints	Δρ_min = −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	U_iso*/U_eq
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.

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Dihydroxonium 1,5-naphthalene­disulfonate N,N-dimethyl­formamide disolvate

Supporting information

Key indicators

checkCIF/PLATON results

Dihydroxonium 1,5-naphthalenedisulfonate N,N-dimethylformamide disolvate