Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023124/lh2389sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023124/lh2389Isup2.hkl |
CCDC reference: 651475
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.003 Å
- R factor = 0.057
- wR factor = 0.130
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 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
The author has recently determined the crystal structures of two closely related compounds (Xie 2007a,b).
All reagents and solvents were used as obtained without further purification. Equivalent molar amounts of isonicid and sulfosalicylic acid were dissolved in 95% methanol (10 ml). The mixture was stirred for ten minutes at ambient temperature and then filtered. The resulting colourless solution was kept in air for two days. colourless crystals of (I) suitable for single-crystal X-ray diffraction analysis were grown by slow evaporation of the solution at the bottom of the vessel.
H atoms bonded to C atoms were placed in calculated positions with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). All the other H atoms were located from the difference maps with the constraints of N—H = 0.86 (1) Å, Uiso(H) = 1.2Ueq(N); O—H = 0.82 (1) Å, H—H = 1.39 (1) Å and Uiso(H) = 1.5Ueq(O).
As part of our continuing studies on the inter-ion and intra-associative H-bonding interactions of organic superstructures (Xie, 2007a, b)), we report herein the crystal structure of (I) formed by isonicid and sulfosalicylic acid.
In (I) (Fig.1), like the earlier reported structure (Xie, 2007a), the acid H atom is released from the sulfonic group to pyridine N atom forming the stechiometrical 1:1 organic salt with one water solvent molecule incorporated into the selected asymmetric unit.
In the supramolecular structure, the molecules are linked by a combination of C (or N, O)–H···O and N–H···N hydrogen bonds into a three-dimensional network whose formation is readily analysed in terms of three substructures. In the first of these substructures, by a combination of the first five hydrognen bonds listed in table 1 the 4-(Hydrazinecarbonyl)pyridinium cations and water molecules are linked into a two-dimensional network running parallel to the (101) direction (Fig.2). The second substructure is formed by linking of the sulphonate anions via three O–H···O hydrogen bonds, i.e. O3–H3B···O7iii, O4–H4A···O2 and O4–H4A···O5iv, [symmetry codes as in Table 1] so forming another two-dimensional framework running parallel to the (101) direction (Fig.3). The third substructure is the combination of the last four hydrogen bonds in Tabel 1 which link the adjacent (101) planes into a three-dimensional network (Fig.4).
There are two aromatic π–π stacking interactions in the structure of (I), which serve to reinforce the adjacent (101) sheets. The phenyl ring in the molecule at (x,y,z) and the pyridine ring in the molecule at (1/2 - x,1 - y,-1/2 + z), which lie in the different (101) sheets, are almost parallel, with a dihedral angle between the two rings of only 3.53 (1)°, an interplanar spacing of 3.243 (1) Å, and ring-centroid separation of 3.615 (1) Å PLATON (Spek,2003).
The author has recently determined the crystal structures of two closely related compounds (Xie 2007a,b).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.
C6H8N3O+·C7H5O6S−·H2O | F(000) = 1552 |
Mr = 373.34 | Dx = 1.625 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2943 reflections |
a = 13.7628 (8) Å | θ = 2.8–21.4° |
b = 13.0656 (8) Å | µ = 0.27 mm−1 |
c = 16.9752 (10) Å | T = 299 K |
V = 3052.5 (3) Å3 | Plate, colourless |
Z = 8 | 0.30 × 0.20 × 0.04 mm |
Bruker SMART APEX CCD area-detector diffractometer | 3747 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 2727 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
0.3° wide ω exposures scans | θmax = 28.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −18→18 |
Tmin = 0.927, Tmax = 0.990 | k = −17→17 |
33729 measured reflections | l = −22→21 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0503P)2 + 1.8424P] where P = (Fo2 + 2Fc2)/3 |
3747 reflections | (Δ/σ)max < 0.001 |
250 parameters | Δρmax = 0.31 e Å−3 |
9 restraints | Δρmin = −0.34 e Å−3 |
C6H8N3O+·C7H5O6S−·H2O | V = 3052.5 (3) Å3 |
Mr = 373.34 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 13.7628 (8) Å | µ = 0.27 mm−1 |
b = 13.0656 (8) Å | T = 299 K |
c = 16.9752 (10) Å | 0.30 × 0.20 × 0.04 mm |
Bruker SMART APEX CCD area-detector diffractometer | 3747 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 2727 reflections with I > 2σ(I) |
Tmin = 0.927, Tmax = 0.990 | Rint = 0.075 |
33729 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 9 restraints |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.31 e Å−3 |
3747 reflections | Δρmin = −0.34 e Å−3 |
250 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.17378 (17) | 0.51847 (17) | 0.82574 (12) | 0.0254 (5) | |
C2 | 0.27410 (17) | 0.52771 (19) | 0.83228 (13) | 0.0312 (5) | |
H2 | 0.3121 | 0.5368 | 0.7875 | 0.037* | |
C3 | 0.31671 (19) | 0.52328 (19) | 0.90534 (14) | 0.0354 (6) | |
H3 | 0.3838 | 0.5285 | 0.9101 | 0.042* | |
C4 | 0.16537 (19) | 0.5029 (2) | 0.96546 (14) | 0.0392 (6) | |
H4 | 0.1292 | 0.4949 | 1.0113 | 0.047* | |
C5 | 0.11965 (18) | 0.5060 (2) | 0.89398 (14) | 0.0339 (6) | |
H5 | 0.0524 | 0.4997 | 0.8911 | 0.041* | |
C6 | 0.11982 (17) | 0.51932 (17) | 0.74783 (13) | 0.0266 (5) | |
C7 | 0.15251 (16) | 0.71604 (18) | 0.26384 (13) | 0.0267 (5) | |
C8 | 0.24789 (16) | 0.72193 (17) | 0.29228 (13) | 0.0271 (5) | |
C9 | 0.26353 (16) | 0.73103 (18) | 0.37378 (14) | 0.0287 (5) | |
H9 | 0.3267 | 0.7349 | 0.3931 | 0.034* | |
C10 | 0.18697 (17) | 0.73430 (17) | 0.42491 (13) | 0.0279 (5) | |
H10 | 0.1981 | 0.7406 | 0.4787 | 0.033* | |
C11 | 0.09111 (16) | 0.72820 (17) | 0.39610 (12) | 0.0243 (5) | |
C12 | 0.07484 (16) | 0.71956 (18) | 0.31632 (13) | 0.0269 (5) | |
H12 | 0.0115 | 0.7161 | 0.2974 | 0.032* | |
C13 | 0.13520 (18) | 0.7073 (2) | 0.17783 (13) | 0.0329 (6) | |
N1 | 0.13200 (16) | 0.51270 (19) | 0.60756 (12) | 0.0363 (5) | |
H1A | 0.0923 (16) | 0.5630 (15) | 0.6003 (17) | 0.044* | |
H1B | 0.0998 (18) | 0.4563 (13) | 0.6098 (17) | 0.044* | |
N2 | 0.17413 (14) | 0.52155 (17) | 0.68322 (11) | 0.0312 (5) | |
H2A | 0.2359 (8) | 0.528 (2) | 0.6823 (15) | 0.037* | |
N3 | 0.26167 (17) | 0.51140 (17) | 0.96953 (11) | 0.0358 (5) | |
H3A | 0.2938 (18) | 0.509 (2) | 1.0131 (10) | 0.043* | |
O1 | 0.03087 (13) | 0.51570 (15) | 0.74565 (10) | 0.0406 (5) | |
O2 | 0.20020 (14) | 0.70257 (19) | 0.12983 (10) | 0.0564 (6) | |
O3 | 0.04337 (14) | 0.7035 (2) | 0.15867 (10) | 0.0533 (6) | |
H3B | 0.036 (3) | 0.695 (3) | 0.1110 (7) | 0.080* | |
O4 | 0.32670 (13) | 0.71925 (15) | 0.24516 (10) | 0.0408 (5) | |
H4A | 0.306 (2) | 0.715 (3) | 0.2000 (9) | 0.061* | |
O5 | −0.09471 (12) | 0.73591 (16) | 0.41419 (10) | 0.0439 (5) | |
O6 | −0.00170 (13) | 0.63684 (15) | 0.50742 (11) | 0.0458 (5) | |
O7 | 0.00528 (12) | 0.82175 (14) | 0.51056 (9) | 0.0366 (4) | |
O8 | 0.37530 (13) | 0.56058 (16) | 0.65203 (11) | 0.0428 (5) | |
H8A | 0.381 (2) | 0.6196 (12) | 0.6353 (18) | 0.064* | |
H8B | 0.4214 (16) | 0.543 (2) | 0.6807 (16) | 0.064* | |
S1 | −0.00779 (4) | 0.73054 (5) | 0.46210 (3) | 0.02779 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0319 (12) | 0.0238 (11) | 0.0204 (11) | 0.0015 (9) | −0.0018 (9) | −0.0019 (9) |
C2 | 0.0328 (13) | 0.0360 (14) | 0.0246 (11) | −0.0057 (11) | 0.0009 (10) | 0.0011 (10) |
C3 | 0.0353 (14) | 0.0395 (15) | 0.0313 (13) | −0.0032 (11) | −0.0056 (11) | 0.0002 (11) |
C4 | 0.0418 (16) | 0.0542 (17) | 0.0216 (12) | 0.0109 (13) | 0.0049 (11) | 0.0042 (11) |
C5 | 0.0298 (13) | 0.0473 (16) | 0.0247 (12) | 0.0072 (11) | 0.0025 (10) | 0.0034 (11) |
C6 | 0.0281 (13) | 0.0297 (12) | 0.0219 (11) | −0.0009 (9) | −0.0009 (9) | 0.0006 (9) |
C7 | 0.0267 (12) | 0.0320 (13) | 0.0215 (11) | 0.0002 (9) | −0.0001 (9) | 0.0032 (9) |
C8 | 0.0258 (11) | 0.0261 (12) | 0.0293 (12) | −0.0010 (9) | 0.0013 (10) | 0.0031 (10) |
C9 | 0.0232 (11) | 0.0293 (12) | 0.0336 (12) | 0.0002 (10) | −0.0057 (9) | 0.0003 (10) |
C10 | 0.0332 (12) | 0.0288 (12) | 0.0216 (11) | −0.0012 (10) | −0.0043 (9) | −0.0005 (9) |
C11 | 0.0271 (11) | 0.0258 (12) | 0.0200 (10) | 0.0007 (9) | 0.0000 (9) | 0.0032 (9) |
C12 | 0.0252 (11) | 0.0332 (13) | 0.0225 (11) | 0.0005 (9) | −0.0030 (9) | 0.0033 (10) |
C13 | 0.0316 (13) | 0.0459 (15) | 0.0211 (11) | 0.0023 (11) | 0.0004 (10) | 0.0036 (10) |
N1 | 0.0335 (12) | 0.0554 (15) | 0.0201 (10) | −0.0043 (10) | −0.0038 (9) | −0.0007 (10) |
N2 | 0.0255 (10) | 0.0505 (13) | 0.0177 (9) | −0.0053 (9) | −0.0023 (8) | 0.0015 (9) |
N3 | 0.0487 (14) | 0.0391 (12) | 0.0197 (10) | 0.0066 (10) | −0.0087 (9) | −0.0008 (9) |
O1 | 0.0267 (9) | 0.0676 (13) | 0.0275 (9) | −0.0010 (8) | −0.0006 (7) | −0.0022 (9) |
O2 | 0.0362 (11) | 0.1076 (18) | 0.0252 (9) | −0.0048 (11) | 0.0060 (8) | −0.0027 (11) |
O3 | 0.0332 (10) | 0.1089 (18) | 0.0178 (9) | 0.0039 (11) | −0.0022 (8) | 0.0001 (10) |
O4 | 0.0276 (9) | 0.0624 (13) | 0.0323 (9) | −0.0007 (8) | 0.0049 (8) | −0.0030 (9) |
O5 | 0.0254 (9) | 0.0791 (14) | 0.0274 (9) | −0.0032 (9) | −0.0039 (7) | −0.0009 (9) |
O6 | 0.0473 (11) | 0.0475 (12) | 0.0425 (11) | −0.0055 (9) | 0.0058 (9) | 0.0184 (9) |
O7 | 0.0392 (10) | 0.0483 (11) | 0.0224 (8) | 0.0025 (8) | −0.0005 (7) | −0.0048 (8) |
O8 | 0.0297 (10) | 0.0618 (14) | 0.0369 (11) | −0.0034 (9) | −0.0004 (8) | 0.0022 (9) |
S1 | 0.0253 (3) | 0.0402 (4) | 0.0178 (3) | −0.0019 (2) | −0.0011 (2) | 0.0033 (2) |
C1—C5 | 1.387 (3) | C10—C11 | 1.409 (3) |
C1—C2 | 1.390 (3) | C10—H10 | 0.9300 |
C1—C6 | 1.517 (3) | C11—C12 | 1.377 (3) |
C2—C3 | 1.373 (3) | C11—S1 | 1.763 (2) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C3—N3 | 1.336 (3) | C13—O2 | 1.212 (3) |
C3—H3 | 0.9300 | C13—O3 | 1.306 (3) |
C4—N3 | 1.332 (3) | N1—N2 | 1.414 (3) |
C4—C5 | 1.367 (3) | N1—H1A | 0.864 (10) |
C4—H4 | 0.9300 | N1—H1B | 0.861 (10) |
C5—H5 | 0.9300 | N2—H2A | 0.855 (10) |
C6—O1 | 1.226 (3) | N3—H3A | 0.862 (10) |
C6—N2 | 1.328 (3) | O3—H3B | 0.823 (10) |
C7—C12 | 1.392 (3) | O4—H4A | 0.821 (10) |
C7—C8 | 1.401 (3) | O5—S1 | 1.4482 (17) |
C7—C13 | 1.484 (3) | O6—S1 | 1.4484 (18) |
C8—O4 | 1.348 (3) | O7—S1 | 1.4593 (18) |
C8—C9 | 1.405 (3) | O8—H8A | 0.826 (10) |
C9—C10 | 1.366 (3) | O8—H8B | 0.832 (10) |
C9—H9 | 0.9300 | ||
C5—C1—C2 | 118.5 (2) | C12—C11—C10 | 119.9 (2) |
C5—C1—C6 | 117.8 (2) | C12—C11—S1 | 120.04 (17) |
C2—C1—C6 | 123.7 (2) | C10—C11—S1 | 120.09 (17) |
C3—C2—C1 | 119.5 (2) | C11—C12—C7 | 120.5 (2) |
C3—C2—H2 | 120.2 | C11—C12—H12 | 119.8 |
C1—C2—H2 | 120.2 | C7—C12—H12 | 119.8 |
N3—C3—C2 | 120.0 (2) | O2—C13—O3 | 123.0 (2) |
N3—C3—H3 | 120.0 | O2—C13—C7 | 123.2 (2) |
C2—C3—H3 | 120.0 | O3—C13—C7 | 113.8 (2) |
N3—C4—C5 | 120.1 (2) | N2—N1—H1A | 109.1 (19) |
N3—C4—H4 | 119.9 | N2—N1—H1B | 103.9 (19) |
C5—C4—H4 | 119.9 | H1A—N1—H1B | 109 (3) |
C4—C5—C1 | 119.8 (2) | C6—N2—N1 | 121.2 (2) |
C4—C5—H5 | 120.1 | C6—N2—H2A | 125.3 (18) |
C1—C5—H5 | 120.1 | N1—N2—H2A | 113.5 (18) |
O1—C6—N2 | 122.6 (2) | C4—N3—C3 | 122.1 (2) |
O1—C6—C1 | 121.0 (2) | C4—N3—H3A | 123.5 (19) |
N2—C6—C1 | 116.4 (2) | C3—N3—H3A | 114.4 (19) |
C12—C7—C8 | 119.8 (2) | C13—O3—H3B | 112 (3) |
C12—C7—C13 | 120.6 (2) | C8—O4—H4A | 106 (2) |
C8—C7—C13 | 119.6 (2) | S1—O6—H1A | 140.0 (7) |
O4—C8—C7 | 123.2 (2) | H2A—O8—H8A | 112 (2) |
O4—C8—C9 | 117.6 (2) | H2A—O8—H8B | 121 (2) |
C7—C8—C9 | 119.2 (2) | H8A—O8—H8B | 112.5 (17) |
C10—C9—C8 | 120.7 (2) | O5—S1—O6 | 112.77 (12) |
C10—C9—H9 | 119.7 | O5—S1—O7 | 112.27 (11) |
C8—C9—H9 | 119.7 | O6—S1—O7 | 112.56 (11) |
C9—C10—C11 | 120.0 (2) | O5—S1—C11 | 106.37 (10) |
C9—C10—H10 | 120.0 | O6—S1—C11 | 106.15 (11) |
C11—C10—H10 | 120.0 | O7—S1—C11 | 106.09 (10) |
C5—C1—C2—C3 | 0.6 (4) | S1—C11—C12—C7 | −178.99 (18) |
C6—C1—C2—C3 | −178.2 (2) | C8—C7—C12—C11 | −0.4 (3) |
C1—C2—C3—N3 | −0.8 (4) | C13—C7—C12—C11 | −179.6 (2) |
N3—C4—C5—C1 | −0.3 (4) | C12—C7—C13—O2 | −179.0 (3) |
C2—C1—C5—C4 | 0.0 (4) | C8—C7—C13—O2 | 1.8 (4) |
C6—C1—C5—C4 | 178.8 (2) | C12—C7—C13—O3 | −0.1 (3) |
C5—C1—C6—O1 | 4.6 (3) | C8—C7—C13—O3 | −179.3 (2) |
C2—C1—C6—O1 | −176.6 (2) | O1—C6—N2—N1 | −4.4 (4) |
C5—C1—C6—N2 | −173.8 (2) | C1—C6—N2—N1 | 173.9 (2) |
C2—C1—C6—N2 | 5.1 (3) | C5—C4—N3—C3 | 0.1 (4) |
C12—C7—C8—O4 | −179.9 (2) | C2—C3—N3—C4 | 0.4 (4) |
C13—C7—C8—O4 | −0.6 (4) | H1A—O6—S1—O5 | −174.7 (10) |
C12—C7—C8—C9 | 0.2 (3) | H1A—O6—S1—O7 | −46.4 (10) |
C13—C7—C8—C9 | 179.5 (2) | H1A—O6—S1—C11 | 69.2 (10) |
O4—C8—C9—C10 | 179.9 (2) | C12—C11—S1—O5 | −7.5 (2) |
C7—C8—C9—C10 | −0.1 (3) | C10—C11—S1—O5 | 173.08 (19) |
C8—C9—C10—C11 | 0.2 (3) | C12—C11—S1—O6 | 112.9 (2) |
C9—C10—C11—C12 | −0.4 (3) | C10—C11—S1—O6 | −66.6 (2) |
C9—C10—C11—S1 | 179.08 (18) | C12—C11—S1—O7 | −127.18 (19) |
C10—C11—C12—C7 | 0.5 (3) | C10—C11—S1—O7 | 53.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O8 | 0.93 | 2.48 | 3.389 (3) | 166 |
C4—H4···O8i | 0.93 | 2.50 | 3.321 (3) | 148 |
N2—H2A···O8 | 0.86 (1) | 2.03 (1) | 2.865 (3) | 165 (2) |
N3—H3A···N1i | 0.86 (1) | 1.92 (1) | 2.780 (3) | 173 (3) |
O8—H8B···O1ii | 0.83 (1) | 1.99 (1) | 2.819 (3) | 174 (3) |
O3—H3B···O7iii | 0.82 (1) | 1.77 (1) | 2.589 (2) | 174 (4) |
O4—H4A···O2 | 0.82 (1) | 1.89 (2) | 2.629 (3) | 150 (3) |
O4—H4A···O5iv | 0.82 (1) | 2.39 (3) | 2.921 (2) | 123 (3) |
C3—H3···O6ii | 0.93 | 2.54 | 3.262 (3) | 135 |
N1—H1A···O6 | 0.86 (1) | 2.26 (2) | 2.984 (3) | 142 (2) |
N1—H1B···O5v | 0.86 (1) | 2.55 (2) | 3.309 (3) | 148 (2) |
O8—H8A···O5vi | 0.83 (1) | 2.09 (1) | 2.916 (3) | 175 (3) |
Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) x+1/2, y, −z+3/2; (iii) x, −y+3/2, z−1/2; (iv) x+1/2, y, −z+1/2; (v) −x, −y+1, −z+1; (vi) x+1/2, −y+3/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C6H8N3O+·C7H5O6S−·H2O |
Mr | 373.34 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 299 |
a, b, c (Å) | 13.7628 (8), 13.0656 (8), 16.9752 (10) |
V (Å3) | 3052.5 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.30 × 0.20 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.927, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33729, 3747, 2727 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.130, 1.06 |
No. of reflections | 3747 |
No. of parameters | 250 |
No. of restraints | 9 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.34 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O8 | 0.93 | 2.48 | 3.389 (3) | 166.3 |
C4—H4···O8i | 0.93 | 2.50 | 3.321 (3) | 147.8 |
N2—H2A···O8 | 0.855 (10) | 2.030 (12) | 2.865 (3) | 165 (2) |
N3—H3A···N1i | 0.862 (10) | 1.923 (11) | 2.780 (3) | 173 (3) |
O8—H8B···O1ii | 0.832 (10) | 1.990 (11) | 2.819 (3) | 174 (3) |
O3—H3B···O7iii | 0.823 (10) | 1.769 (11) | 2.589 (2) | 174 (4) |
O4—H4A···O2 | 0.821 (10) | 1.886 (18) | 2.629 (3) | 150 (3) |
O4—H4A···O5iv | 0.821 (10) | 2.39 (3) | 2.921 (2) | 123 (3) |
C3—H3···O6ii | 0.93 | 2.54 | 3.262 (3) | 134.9 |
N1—H1A···O6 | 0.864 (10) | 2.256 (19) | 2.984 (3) | 142 (2) |
N1—H1B···O5v | 0.861 (10) | 2.545 (17) | 3.309 (3) | 148 (2) |
O8—H8A···O5vi | 0.826 (10) | 2.093 (11) | 2.916 (3) | 175 (3) |
Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) x+1/2, y, −z+3/2; (iii) x, −y+3/2, z−1/2; (iv) x+1/2, y, −z+1/2; (v) −x, −y+1, −z+1; (vi) x+1/2, −y+3/2, −z+1. |
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As part of our continuing studies on the inter-ion and intra-associative H-bonding interactions of organic superstructures (Xie, 2007a, b)), we report herein the crystal structure of (I) formed by isonicid and sulfosalicylic acid.
In (I) (Fig.1), like the earlier reported structure (Xie, 2007a), the acid H atom is released from the sulfonic group to pyridine N atom forming the stechiometrical 1:1 organic salt with one water solvent molecule incorporated into the selected asymmetric unit.
In the supramolecular structure, the molecules are linked by a combination of C (or N, O)–H···O and N–H···N hydrogen bonds into a three-dimensional network whose formation is readily analysed in terms of three substructures. In the first of these substructures, by a combination of the first five hydrognen bonds listed in table 1 the 4-(Hydrazinecarbonyl)pyridinium cations and water molecules are linked into a two-dimensional network running parallel to the (101) direction (Fig.2). The second substructure is formed by linking of the sulphonate anions via three O–H···O hydrogen bonds, i.e. O3–H3B···O7iii, O4–H4A···O2 and O4–H4A···O5iv, [symmetry codes as in Table 1] so forming another two-dimensional framework running parallel to the (101) direction (Fig.3). The third substructure is the combination of the last four hydrogen bonds in Tabel 1 which link the adjacent (101) planes into a three-dimensional network (Fig.4).
There are two aromatic π–π stacking interactions in the structure of (I), which serve to reinforce the adjacent (101) sheets. The phenyl ring in the molecule at (x,y,z) and the pyridine ring in the molecule at (1/2 - x,1 - y,-1/2 + z), which lie in the different (101) sheets, are almost parallel, with a dihedral angle between the two rings of only 3.53 (1)°, an interplanar spacing of 3.243 (1) Å, and ring-centroid separation of 3.615 (1) Å PLATON (Spek,2003).