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In the structure of the title compound, 2C5H7N2+·SO42−, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019593/sj2069sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019593/sj2069Isup2.hkl
Contains datablock I

CCDC reference: 613816

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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+·SO42F(000) = 1200
Mr = 286.31Dx = 1.458 Mg m3
Orthorhombic, Fdd2Cu Kα radiation, λ = 1.5418 Å
Hall symbol: F 2 -2dCell parameters from 23 reflections
a = 12.873 (7) Åθ = 40.3–42.9°
b = 16.835 (8) ŵ = 2.39 mm1
c = 12.035 (8) ÅT = 293 K
V = 2608 (3) Å3Block, colourless
Z = 80.5 × 0.25 × 0.25 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.000
ω/2θ scansθmax = 74.6°, θmin = 5.7°
Absorption correction: ψ scan
(North et al., 1968)
h = 016
Tmin = 0.513, Tmax = 0.550k = 021
702 measured reflectionsl = 015
702 independent reflections2 standard reflections every 60 min
698 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2H-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) = 0.086Δρmax = 0.27 e Å3
S = 1.08Δρmin = 0.66 e Å3
702 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
88 parametersExtinction 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
xyzUiso*/Ueq
S10.250.250.72078 (5)0.0180 (3)
N10.25620 (13)0.04579 (14)0.37291 (19)0.0282 (5)
H10.20650.01380.38950.034*
N70.30648 (17)0.04142 (13)0.2343 (2)0.0394 (6)
H7A0.25580.07230.25170.047*
H7B0.34780.05420.1810.047*
O20.19969 (12)0.31087 (9)0.79111 (14)0.0266 (4)
O10.17051 (13)0.21146 (10)0.64998 (16)0.0323 (4)
C30.40158 (19)0.07981 (15)0.2628 (2)0.0335 (6)
H30.4470.06870.20480.04*
C60.26608 (19)0.11458 (17)0.4322 (2)0.0336 (6)
H60.2190.1260.48860.04*
C50.3432 (2)0.16582 (16)0.4096 (3)0.0396 (7)
H50.35070.21220.45080.047*
C40.4122 (2)0.14824 (15)0.3229 (2)0.0396 (7)
H40.46560.18340.3060.048*
C20.32100 (17)0.02608 (13)0.2897 (2)0.0256 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0202 (3)0.0128 (3)0.0210 (4)0.0023 (2)00
N10.0261 (9)0.0260 (10)0.0324 (11)0.0057 (7)0.0066 (7)0.0012 (8)
N70.0450 (11)0.0216 (9)0.0515 (14)0.0045 (9)0.0077 (11)0.0120 (10)
O20.0297 (8)0.0211 (8)0.0291 (9)0.0056 (5)0.0033 (6)0.0060 (6)
O10.0351 (8)0.0217 (7)0.0402 (9)0.0065 (6)0.0142 (8)0.0086 (8)
C30.0333 (11)0.0314 (11)0.0357 (11)0.0067 (10)0.0133 (10)0.0058 (10)
C60.0340 (11)0.0356 (14)0.0312 (12)0.0014 (10)0.0070 (10)0.0084 (11)
C50.0428 (14)0.0309 (11)0.0450 (16)0.0060 (11)0.0032 (12)0.0136 (12)
C40.0424 (14)0.0310 (13)0.0455 (15)0.0153 (10)0.0089 (12)0.0030 (12)
C20.0279 (10)0.0191 (10)0.0298 (12)0.0005 (8)0.0027 (9)0.0023 (8)
Geometric parameters (Å, º) top
S1—O2i1.4785 (16)N7—H7B0.86
S1—O21.4785 (16)C3—C41.367 (4)
S1—O11.4812 (18)C3—C21.414 (3)
S1—O1i1.4812 (18)C3—H30.93
N1—C21.345 (3)C6—C51.343 (4)
N1—C61.366 (4)C6—H60.93
N1—H10.86C5—C41.402 (4)
N7—C21.331 (3)C5—H50.93
N7—H7A0.86C4—H40.93
O2i—S1—O2110.15 (14)C2—C3—H3120.3
O2i—S1—O1109.17 (10)C5—C6—N1120.5 (2)
O2—S1—O1109.28 (10)C5—C6—H6119.7
O2i—S1—O1i109.28 (10)N1—C6—H6119.7
O2—S1—O1i109.17 (10)C6—C5—C4118.9 (2)
O1—S1—O1i109.77 (17)C6—C5—H5120.6
C2—N1—C6122.7 (2)C4—C5—H5120.6
C2—N1—H1118.7C3—C4—C5120.6 (2)
C6—N1—H1118.7C3—C4—H4119.7
C2—N7—H7A120C5—C4—H4119.7
C2—N7—H7B120N7—C2—N1119.8 (2)
H7A—N7—H7B120N7—C2—C3122.3 (2)
C4—C3—C2119.4 (2)N1—C2—C3117.9 (2)
C4—C3—H3120.3
Symmetry code: (i) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1ii0.861.862.701 (3)165
N7—H7A···O2iii0.862.152.923 (3)150
N7—H7B···O2iv0.862.142.985 (3)168
Symmetry codes: (ii) x+1/4, y1/4, z1/4; (iii) x, y1/2, z1/2; (iv) x+1/4, y+1/4, z3/4.
 

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