In the title compound, CH
6N
3S
+·C
7H
5O
6S
−, the crystal packing is stabilized by an extensive three-dimensional hydrogen-bonded network, formed by intermolecular N—H
O and O—H
O hydrogen bonds, and π–π interactions between aromatic rings of neighbouring anions.
Supporting information
CCDC reference: 642955
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.033
- wR factor = 0.087
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ?
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
1 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
(Aminocarbonothioyl)hydrazinium 3-carboxy-4-hydroxybenzenesulfonate
top
Crystal data top
CH6N3S+·C7H5O6S− | F(000) = 640 |
Mr = 309.32 | Dx = 1.608 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5107 reflections |
a = 10.479 (7) Å | θ = 2.6–28.3° |
b = 7.625 (5) Å | µ = 0.44 mm−1 |
c = 16.357 (11) Å | T = 298 K |
β = 102.119 (11)° | Block, colourless |
V = 1277.8 (15) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2753 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 2546 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
0.3° wide ω exposures scans | θmax = 27.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −13→7 |
Tmin = 0.879, Tmax = 0.917 | k = −9→9 |
7850 measured reflections | l = −20→20 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.039P)2 + 0.4215P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
2753 reflections | Δρmax = 0.29 e Å−3 |
197 parameters | Δρmin = −0.39 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0172 (17) |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.56833 (14) | 0.84889 (19) | 0.10417 (9) | 0.0256 (3) | |
C2 | 0.61929 (14) | 0.8167 (2) | 0.03067 (10) | 0.0274 (3) | |
C3 | 0.53816 (16) | 0.7370 (2) | −0.04070 (10) | 0.0309 (3) | |
H3 | 0.5706 | 0.7179 | −0.0887 | 0.037* | |
C4 | 0.40923 (15) | 0.6869 (2) | −0.03899 (9) | 0.0273 (3) | |
H4 | 0.3572 | 0.6342 | −0.0855 | 0.033* | |
C5 | 0.35867 (13) | 0.71735 (19) | 0.03421 (9) | 0.0227 (3) | |
C6 | 0.43736 (14) | 0.7984 (2) | 0.10499 (9) | 0.0249 (3) | |
H6 | 0.4036 | 0.8190 | 0.1523 | 0.030* | |
C7 | 0.65308 (15) | 0.9391 (2) | 0.17811 (10) | 0.0318 (4) | |
C8 | 0.08614 (15) | 0.1228 (2) | 0.23987 (9) | 0.0268 (3) | |
N1 | 0.02271 (16) | 0.1511 (2) | 0.30249 (10) | 0.0405 (4) | |
H1A | −0.052 (2) | 0.199 (3) | 0.2929 (13) | 0.049* | |
H1B | 0.059 (2) | 0.111 (3) | 0.3544 (15) | 0.049* | |
N2 | 0.02342 (14) | 0.1857 (2) | 0.16191 (9) | 0.0353 (3) | |
H2 | −0.034 (2) | 0.259 (3) | 0.1550 (13) | 0.042* | |
N3 | 0.09222 (14) | 0.1840 (2) | 0.09460 (8) | 0.0283 (3) | |
H3A | 0.1435 (19) | 0.286 (3) | 0.0960 (12) | 0.034* | |
H3B | 0.143 (2) | 0.088 (3) | 0.1017 (12) | 0.034* | |
H3C | 0.030 (2) | 0.179 (3) | 0.0463 (13) | 0.034* | |
O1 | 0.59773 (13) | 0.9587 (2) | 0.24474 (8) | 0.0456 (4) | |
H1 | 0.650 (3) | 1.002 (3) | 0.2827 (18) | 0.068* | |
O2 | 0.76570 (12) | 0.99294 (19) | 0.17773 (9) | 0.0467 (3) | |
O3 | 0.74555 (12) | 0.86069 (17) | 0.02604 (9) | 0.0401 (3) | |
H3D | 0.777 (2) | 0.917 (3) | 0.0705 (16) | 0.060* | |
O4 | 0.11736 (10) | 0.80793 (15) | 0.04875 (7) | 0.0306 (3) | |
O5 | 0.21034 (11) | 0.52940 (15) | 0.11242 (7) | 0.0327 (3) | |
O6 | 0.14066 (11) | 0.55637 (15) | −0.04141 (7) | 0.0323 (3) | |
S1 | 0.19548 (3) | 0.64794 (4) | 0.03805 (2) | 0.02111 (13) | |
S2 | 0.23143 (5) | 0.01322 (7) | 0.25237 (3) | 0.04475 (16) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0207 (7) | 0.0268 (7) | 0.0279 (7) | −0.0008 (6) | 0.0020 (6) | 0.0006 (6) |
C2 | 0.0226 (7) | 0.0248 (7) | 0.0366 (8) | 0.0011 (6) | 0.0105 (6) | 0.0054 (6) |
C3 | 0.0342 (8) | 0.0334 (8) | 0.0285 (7) | 0.0013 (7) | 0.0145 (6) | 0.0009 (6) |
C4 | 0.0300 (8) | 0.0288 (7) | 0.0224 (7) | −0.0003 (6) | 0.0041 (6) | −0.0013 (6) |
C5 | 0.0195 (7) | 0.0247 (7) | 0.0236 (7) | −0.0007 (5) | 0.0037 (5) | 0.0014 (5) |
C6 | 0.0220 (7) | 0.0308 (7) | 0.0221 (7) | −0.0010 (6) | 0.0049 (5) | −0.0008 (6) |
C7 | 0.0226 (7) | 0.0332 (8) | 0.0364 (8) | −0.0018 (6) | −0.0009 (6) | −0.0012 (7) |
C8 | 0.0262 (7) | 0.0268 (7) | 0.0260 (7) | −0.0040 (6) | 0.0022 (6) | 0.0019 (6) |
N1 | 0.0334 (8) | 0.0572 (10) | 0.0323 (8) | 0.0028 (7) | 0.0098 (7) | 0.0079 (7) |
N2 | 0.0256 (7) | 0.0488 (8) | 0.0326 (7) | 0.0107 (6) | 0.0086 (6) | 0.0143 (6) |
N3 | 0.0265 (7) | 0.0329 (7) | 0.0241 (6) | 0.0003 (6) | 0.0024 (5) | 0.0045 (5) |
O1 | 0.0319 (7) | 0.0673 (9) | 0.0349 (7) | −0.0100 (6) | 0.0011 (5) | −0.0187 (6) |
O2 | 0.0281 (6) | 0.0566 (8) | 0.0524 (8) | −0.0148 (6) | 0.0014 (6) | −0.0057 (6) |
O3 | 0.0269 (6) | 0.0463 (7) | 0.0509 (8) | −0.0060 (5) | 0.0166 (6) | −0.0008 (6) |
O4 | 0.0240 (5) | 0.0308 (6) | 0.0354 (6) | 0.0023 (4) | 0.0025 (4) | −0.0054 (5) |
O5 | 0.0277 (6) | 0.0397 (6) | 0.0290 (6) | −0.0050 (5) | 0.0022 (4) | 0.0102 (5) |
O6 | 0.0284 (6) | 0.0386 (6) | 0.0274 (6) | −0.0040 (5) | 0.0002 (4) | −0.0087 (5) |
S1 | 0.01857 (19) | 0.0244 (2) | 0.01903 (19) | −0.00152 (13) | 0.00088 (13) | −0.00022 (12) |
S2 | 0.0443 (3) | 0.0596 (3) | 0.0263 (2) | 0.0258 (2) | −0.00185 (19) | 0.00031 (19) |
Geometric parameters (Å, º) top
C1—C6 | 1.428 (2) | C8—N2 | 1.391 (2) |
C1—C2 | 1.436 (2) | C8—S2 | 1.7111 (19) |
C1—C7 | 1.508 (2) | N1—H1A | 0.85 (2) |
C2—O3 | 1.382 (2) | N1—H1B | 0.91 (2) |
C2—C3 | 1.428 (2) | N2—N3 | 1.437 (2) |
C3—C4 | 1.410 (2) | N2—H2 | 0.81 (2) |
C3—H3 | 0.9300 | N3—H3A | 0.94 (2) |
C4—C5 | 1.426 (2) | N3—H3B | 0.90 (2) |
C4—H4 | 0.9300 | N3—H3C | 0.91 (2) |
C5—C6 | 1.415 (2) | O1—H1 | 0.81 (3) |
C5—S1 | 1.8038 (18) | O3—H3D | 0.85 (3) |
C6—H6 | 0.9300 | O4—S1 | 1.4997 (14) |
C7—O2 | 1.251 (2) | O5—S1 | 1.4972 (13) |
C7—O1 | 1.346 (2) | O6—S1 | 1.4810 (13) |
C8—N1 | 1.350 (2) | | |
| | | |
C6—C1—C2 | 119.27 (14) | N1—C8—S2 | 123.68 (13) |
C6—C1—C7 | 121.38 (14) | N2—C8—S2 | 121.01 (12) |
C2—C1—C7 | 119.33 (14) | C8—N1—H1A | 120.7 (15) |
O3—C2—C3 | 118.11 (14) | C8—N1—H1B | 118.4 (14) |
O3—C2—C1 | 122.20 (14) | H1A—N1—H1B | 121 (2) |
C3—C2—C1 | 119.69 (14) | C8—N2—N3 | 118.85 (14) |
C4—C3—C2 | 120.51 (14) | C8—N2—H2 | 124.0 (15) |
C4—C3—H3 | 119.7 | N3—N2—H2 | 112.1 (15) |
C2—C3—H3 | 119.7 | N2—N3—H3A | 110.4 (11) |
C3—C4—C5 | 119.94 (14) | N2—N3—H3B | 106.7 (12) |
C3—C4—H4 | 120.0 | H3A—N3—H3B | 110.5 (16) |
C5—C4—H4 | 120.0 | N2—N3—H3C | 106.4 (12) |
C6—C5—C4 | 120.17 (13) | H3A—N3—H3C | 110.7 (17) |
C6—C5—S1 | 119.58 (11) | H3B—N3—H3C | 112.0 (17) |
C4—C5—S1 | 120.23 (11) | C7—O1—H1 | 109.3 (19) |
C5—C6—C1 | 120.41 (13) | C2—O3—H3D | 106.5 (17) |
C5—C6—H6 | 119.8 | O6—S1—O5 | 112.55 (8) |
C1—C6—H6 | 119.8 | O6—S1—O4 | 111.43 (7) |
O2—C7—O1 | 122.35 (15) | O5—S1—O4 | 111.25 (7) |
O2—C7—C1 | 122.89 (15) | O6—S1—C5 | 107.67 (7) |
O1—C7—C1 | 114.76 (14) | O5—S1—C5 | 105.53 (7) |
N1—C8—N2 | 115.29 (15) | O4—S1—C5 | 108.07 (8) |
| | | |
C6—C1—C2—O3 | −179.36 (14) | C6—C1—C7—O2 | −176.24 (16) |
C7—C1—C2—O3 | 2.1 (2) | C2—C1—C7—O2 | 2.3 (2) |
C6—C1—C2—C3 | 0.8 (2) | C6—C1—C7—O1 | 3.3 (2) |
C7—C1—C2—C3 | −177.77 (14) | C2—C1—C7—O1 | −178.18 (14) |
O3—C2—C3—C4 | 179.03 (14) | N1—C8—N2—N3 | 171.15 (15) |
C1—C2—C3—C4 | −1.1 (2) | S2—C8—N2—N3 | −10.4 (2) |
C2—C3—C4—C5 | 0.6 (2) | C6—C5—S1—O6 | −175.75 (11) |
C3—C4—C5—C6 | 0.3 (2) | C4—C5—S1—O6 | 2.76 (14) |
C3—C4—C5—S1 | −178.18 (11) | C6—C5—S1—O5 | −55.33 (14) |
C4—C5—C6—C1 | −0.6 (2) | C4—C5—S1—O5 | 123.17 (13) |
S1—C5—C6—C1 | 177.87 (11) | C6—C5—S1—O4 | 63.77 (13) |
C2—C1—C6—C5 | 0.1 (2) | C4—C5—S1—O4 | −117.72 (12) |
C7—C1—C6—C5 | 178.61 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O5 | 0.94 (2) | 1.98 (2) | 2.899 (2) | 163.5 (17) |
N3—H3B···O4i | 0.90 (2) | 2.30 (2) | 2.989 (3) | 133.7 (16) |
N3—H3C···O4ii | 0.91 (2) | 1.95 (2) | 2.857 (2) | 171.7 (17) |
N2—H2···O6ii | 0.81 (2) | 2.41 (2) | 3.047 (2) | 136.0 (18) |
N1—H1B···O6iii | 0.91 (2) | 2.16 (2) | 3.037 (2) | 163.3 (19) |
O1—H1···O5iv | 0.81 (3) | 2.02 (3) | 2.797 (2) | 162 (3) |
O3—H3D···O2 | 0.85 (3) | 1.87 (3) | 2.645 (3) | 150 (2) |
Symmetry codes: (i) x, y−1, z; (ii) −x, −y+1, −z; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2. |