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In the title compound, C7H8NO2+·HSO4, there is an intricate cation–cation, cation–anion and anion–anion three-dimensional hydrogen-bond network. Cations are linked two-dimensionally by C—H...O hydrogen bonds, and anions are linked two-dimensionally by O—H...O hydrogen bonds; however, interactions between cations and anions involve a three-dimensional network of N—H...O and O—H...O hydrogen bonds. The strongest hydrogen bond is observed between anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023134/dn6102sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023134/dn6102Isup2.hkl
Contains datablock I

CCDC reference: 227012

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.035
  • wR factor = 0.115
  • Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
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 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KappaCCD Reference Manual (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C7H8NO2+·HSO4F(000) = 488
Mr = 235.21Dx = 1.697 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12041 reflections
a = 11.4160 (3) Åθ = 1.8–30.0°
b = 10.5090 (3) ŵ = 0.36 mm1
c = 7.6810 (2) ÅT = 293 K
β = 92.562 (2)°Prism, brown
V = 920.57 (4) Å30.4 × 0.3 × 0.25 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2331 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 30.0°, θmin = 1.8°
φ scansh = 016
12041 measured reflectionsk = 140
2694 independent reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.17 w = 1/[σ2(Fo2) + (0.0573P)2 + 0.3395P]
where P = (Fo2 + 2Fc2)/3
2654 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.48 e Å3
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
xyzUiso*/Ueq
S1.08057 (3)0.41668 (3)0.81551 (4)0.02310 (13)
O61.03192 (11)0.54457 (11)0.79674 (16)0.0321 (3)
C20.55502 (12)0.37274 (14)0.65857 (19)0.0238 (3)
O31.18335 (10)0.41531 (13)0.93462 (16)0.0351 (3)
N0.79902 (11)0.60929 (12)0.66838 (17)0.0251 (3)
H110.75590.66450.72570.038*
H120.81740.64280.56670.038*
H130.86440.59200.73140.038*
C40.73202 (12)0.49166 (14)0.63767 (18)0.0221 (3)
O20.36894 (10)0.27236 (12)0.6651 (2)0.0408 (3)
O50.98590 (11)0.33295 (12)0.89992 (16)0.0340 (3)
H50.97110.36240.99530.051*
O41.09769 (13)0.35504 (14)0.65199 (16)0.0414 (3)
C50.78403 (13)0.39216 (16)0.5513 (2)0.0285 (3)
H510.86060.39920.51570.034*
C60.71984 (14)0.28176 (16)0.5188 (2)0.0330 (3)
H60.75370.21390.46170.040*
O10.40013 (10)0.44931 (13)0.82109 (19)0.0395 (3)
H10.33220.43700.84720.059*
C70.60533 (14)0.27223 (15)0.5710 (2)0.0291 (3)
H70.56230.19860.54750.035*
C30.61902 (12)0.48396 (14)0.69359 (19)0.0232 (3)
H30.58620.55120.75320.028*
C10.43239 (13)0.35927 (14)0.7140 (2)0.0266 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.02055 (19)0.0274 (2)0.02172 (19)0.00378 (12)0.00483 (12)0.00036 (12)
O60.0343 (6)0.0289 (6)0.0335 (6)0.0066 (5)0.0055 (5)0.0050 (5)
C20.0179 (6)0.0261 (7)0.0275 (7)0.0009 (5)0.0029 (5)0.0019 (5)
O30.0196 (5)0.0535 (8)0.0322 (6)0.0049 (5)0.0016 (4)0.0019 (5)
N0.0199 (5)0.0275 (6)0.0281 (6)0.0027 (4)0.0031 (4)0.0004 (5)
C40.0183 (6)0.0244 (6)0.0236 (6)0.0009 (5)0.0010 (5)0.0016 (5)
O20.0274 (6)0.0327 (6)0.0635 (9)0.0095 (5)0.0128 (6)0.0083 (6)
O50.0341 (6)0.0346 (6)0.0338 (6)0.0090 (5)0.0064 (5)0.0001 (5)
O40.0483 (8)0.0485 (7)0.0282 (6)0.0056 (6)0.0110 (5)0.0099 (5)
C50.0206 (6)0.0341 (8)0.0313 (7)0.0010 (6)0.0066 (5)0.0032 (6)
C60.0278 (7)0.0315 (8)0.0402 (8)0.0026 (6)0.0072 (6)0.0097 (7)
O10.0226 (5)0.0421 (7)0.0549 (8)0.0059 (5)0.0141 (5)0.0155 (6)
C70.0267 (7)0.0259 (7)0.0349 (8)0.0019 (5)0.0025 (6)0.0044 (6)
C30.0204 (6)0.0230 (6)0.0264 (7)0.0006 (5)0.0035 (5)0.0006 (5)
C10.0209 (6)0.0251 (7)0.0340 (7)0.0004 (5)0.0046 (5)0.0030 (6)
Geometric parameters (Å, º) top
S—O41.4343 (12)C4—C51.386 (2)
S—O31.4554 (12)O2—C11.2149 (19)
S—O61.4589 (12)O5—H50.8200
S—O51.5574 (12)C5—C61.389 (2)
C2—C71.390 (2)C5—H510.9300
C2—C31.398 (2)C6—C71.388 (2)
C2—C11.4881 (19)C6—H60.9300
N—C41.4672 (18)O1—C11.317 (2)
N—H110.8900O1—H10.8200
N—H120.8900C7—H70.9300
N—H130.8900C3—H30.9300
C4—C31.3801 (19)
O4—S—O3114.11 (8)S—O5—H5109.5
O4—S—O6113.31 (8)C4—C5—C6118.84 (14)
O3—S—O6111.34 (8)C4—C5—H51120.6
O4—S—O5103.51 (8)C6—C5—H51120.6
O3—S—O5106.72 (7)C7—C6—C5120.29 (14)
O6—S—O5107.06 (7)C7—C6—H6119.9
C7—C2—C3120.31 (13)C5—C6—H6119.9
C7—C2—C1118.71 (14)C1—O1—H1109.5
C3—C2—C1120.98 (13)C6—C7—C2119.99 (14)
C4—N—H11109.5C6—C7—H7120.0
C4—N—H12109.5C2—C7—H7120.0
H11—N—H12109.5C4—C3—C2118.48 (13)
C4—N—H13109.5C4—C3—H3120.8
H11—N—H13109.5C2—C3—H3120.8
H12—N—H13109.5O2—C1—O1123.63 (14)
C3—C4—C5122.08 (13)O2—C1—C2122.59 (14)
C3—C4—N119.15 (13)O1—C1—C2113.78 (13)
C5—C4—N118.76 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H11···O2i0.892.032.9101 (18)169
N—H12···O4ii0.891.982.8010 (18)153
N—H13···O60.892.022.8757 (18)162
O5—H5···O6iii0.821.872.6776 (17)166
O1—H1···O3iv0.821.872.6843 (16)173
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x+2, y+1, z+1; (iii) x+2, y+1, z+2; (iv) x1, y, z.
 

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