In the structure of the title compound, 2C
5H
7N
2+·SO
42−, the S atom of the sulfate anion lies on a twofold axis. The structure is stabilized by an extensive network of N—H
O hydrogen bonds.
Supporting information
CCDC reference: 613816
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.031
- wR factor = 0.086
- Data-to-parameter ratio = 8.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.98
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
Alert level G
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 74.62
From the CIF: _reflns_number_total 702
Count of symmetry unique reflns 702
Completeness (_total/calc) 100.00%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXL97.
Bis(2-aminopyridinium) sulfate
top
Crystal data top
2C5H7N2+·SO42− | F(000) = 1200 |
Mr = 286.31 | Dx = 1.458 Mg m−3 |
Orthorhombic, Fdd2 | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: F 2 -2d | Cell parameters from 23 reflections |
a = 12.873 (7) Å | θ = 40.3–42.9° |
b = 16.835 (8) Å | µ = 2.39 mm−1 |
c = 12.035 (8) Å | T = 293 K |
V = 2608 (3) Å3 | Block, colourless |
Z = 8 | 0.5 × 0.25 × 0.25 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.000 |
ω/2θ scans | θmax = 74.6°, θmin = 5.7° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→16 |
Tmin = 0.513, Tmax = 0.550 | k = 0→21 |
702 measured reflections | l = 0→15 |
702 independent reflections | 2 standard reflections every 60 min |
698 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.077P)2 + 0.5871P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.031 | (Δ/σ)max < 0.001 |
wR(F2) = 0.086 | Δρmax = 0.27 e Å−3 |
S = 1.08 | Δρmin = −0.66 e Å−3 |
702 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
88 parameters | Extinction coefficient: 0.0017 (2) |
1 restraint | |
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 | 0.25 | 0.25 | 0.72078 (5) | 0.0180 (3) | |
N1 | 0.25620 (13) | 0.04579 (14) | 0.37291 (19) | 0.0282 (5) | |
H1 | 0.2065 | 0.0138 | 0.3895 | 0.034* | |
N7 | 0.30648 (17) | −0.04142 (13) | 0.2343 (2) | 0.0394 (6) | |
H7A | 0.2558 | −0.0723 | 0.2517 | 0.047* | |
H7B | 0.3478 | −0.0542 | 0.181 | 0.047* | |
O2 | 0.19969 (12) | 0.31087 (9) | 0.79111 (14) | 0.0266 (4) | |
O1 | 0.17051 (13) | 0.21146 (10) | 0.64998 (16) | 0.0323 (4) | |
C3 | 0.40158 (19) | 0.07981 (15) | 0.2628 (2) | 0.0335 (6) | |
H3 | 0.447 | 0.0687 | 0.2048 | 0.04* | |
C6 | 0.26608 (19) | 0.11458 (17) | 0.4322 (2) | 0.0336 (6) | |
H6 | 0.219 | 0.126 | 0.4886 | 0.04* | |
C5 | 0.3432 (2) | 0.16582 (16) | 0.4096 (3) | 0.0396 (7) | |
H5 | 0.3507 | 0.2122 | 0.4508 | 0.047* | |
C4 | 0.4122 (2) | 0.14824 (15) | 0.3229 (2) | 0.0396 (7) | |
H4 | 0.4656 | 0.1834 | 0.306 | 0.048* | |
C2 | 0.32100 (17) | 0.02608 (13) | 0.2897 (2) | 0.0256 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0202 (3) | 0.0128 (3) | 0.0210 (4) | 0.0023 (2) | 0 | 0 |
N1 | 0.0261 (9) | 0.0260 (10) | 0.0324 (11) | −0.0057 (7) | 0.0066 (7) | −0.0012 (8) |
N7 | 0.0450 (11) | 0.0216 (9) | 0.0515 (14) | −0.0045 (9) | 0.0077 (11) | −0.0120 (10) |
O2 | 0.0297 (8) | 0.0211 (8) | 0.0291 (9) | 0.0056 (5) | 0.0033 (6) | −0.0060 (6) |
O1 | 0.0351 (8) | 0.0217 (7) | 0.0402 (9) | 0.0065 (6) | −0.0142 (8) | −0.0086 (8) |
C3 | 0.0333 (11) | 0.0314 (11) | 0.0357 (11) | −0.0067 (10) | 0.0133 (10) | −0.0058 (10) |
C6 | 0.0340 (11) | 0.0356 (14) | 0.0312 (12) | 0.0014 (10) | 0.0070 (10) | −0.0084 (11) |
C5 | 0.0428 (14) | 0.0309 (11) | 0.0450 (16) | −0.0060 (11) | 0.0032 (12) | −0.0136 (12) |
C4 | 0.0424 (14) | 0.0310 (13) | 0.0455 (15) | −0.0153 (10) | 0.0089 (12) | −0.0030 (12) |
C2 | 0.0279 (10) | 0.0191 (10) | 0.0298 (12) | −0.0005 (8) | 0.0027 (9) | −0.0023 (8) |
Geometric parameters (Å, º) top
S1—O2i | 1.4785 (16) | N7—H7B | 0.86 |
S1—O2 | 1.4785 (16) | C3—C4 | 1.367 (4) |
S1—O1 | 1.4812 (18) | C3—C2 | 1.414 (3) |
S1—O1i | 1.4812 (18) | C3—H3 | 0.93 |
N1—C2 | 1.345 (3) | C6—C5 | 1.343 (4) |
N1—C6 | 1.366 (4) | C6—H6 | 0.93 |
N1—H1 | 0.86 | C5—C4 | 1.402 (4) |
N7—C2 | 1.331 (3) | C5—H5 | 0.93 |
N7—H7A | 0.86 | C4—H4 | 0.93 |
| | | |
O2i—S1—O2 | 110.15 (14) | C2—C3—H3 | 120.3 |
O2i—S1—O1 | 109.17 (10) | C5—C6—N1 | 120.5 (2) |
O2—S1—O1 | 109.28 (10) | C5—C6—H6 | 119.7 |
O2i—S1—O1i | 109.28 (10) | N1—C6—H6 | 119.7 |
O2—S1—O1i | 109.17 (10) | C6—C5—C4 | 118.9 (2) |
O1—S1—O1i | 109.77 (17) | C6—C5—H5 | 120.6 |
C2—N1—C6 | 122.7 (2) | C4—C5—H5 | 120.6 |
C2—N1—H1 | 118.7 | C3—C4—C5 | 120.6 (2) |
C6—N1—H1 | 118.7 | C3—C4—H4 | 119.7 |
C2—N7—H7A | 120 | C5—C4—H4 | 119.7 |
C2—N7—H7B | 120 | N7—C2—N1 | 119.8 (2) |
H7A—N7—H7B | 120 | N7—C2—C3 | 122.3 (2) |
C4—C3—C2 | 119.4 (2) | N1—C2—C3 | 117.9 (2) |
C4—C3—H3 | 120.3 | | |
Symmetry code: (i) −x+1/2, −y+1/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1ii | 0.86 | 1.86 | 2.701 (3) | 165 |
N7—H7A···O2iii | 0.86 | 2.15 | 2.923 (3) | 150 |
N7—H7B···O2iv | 0.86 | 2.14 | 2.985 (3) | 168 |
Symmetry codes: (ii) −x+1/4, y−1/4, z−1/4; (iii) x, y−1/2, z−1/2; (iv) x+1/4, −y+1/4, z−3/4. |