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The title compound, 2C6H5NO2·H+·ClO4, consists of [(nicotinic acid)2H]+ cations and ClO4 anions. Two nicotinic acid zwitterions are linked by a strong symmetric O—H...O hydrogen bond, with the H atom on an inversion center and an O...·O distance of 2.464 (4) Å, forming a cation. The nicotinic acid cation forms hydrogen bonds to adjacent cations, giving two-dimensional layers. The Cl atom of the perchlorate anion lies on a twofold axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022877/sj6119sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022877/sj6119Isup2.hkl
Contains datablock I

CCDC reference: 282638

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.127
  • Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT355_ALERT_3_A Long O-H Bond (0.82A) O1B - H1B ... 1.23 Ang.
Author Response: The H atom lies on the inversion center and links the two nicotinic
 acid residue through strong symmetric O-H...O hydrogen bond.


Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.93 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.04 PLAT751_ALERT_4_C Bond Calc 1.23000, Rep 1.2320(18) ...... Senseless su O1B -H1B 1.555 1.555 PLAT752_ALERT_4_C Angle Calc 112.00, Rep 112.11(18) ...... Senseless su C31 -O1B -H1B 1.555 1.555 1.555
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 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 2 ALERT type 3 Indicator that the structure quality may be low 4 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: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

Bis(nicotinic acid) hydrogen perchlorate top
Crystal data top
2C6H5NO2·H+·ClO4F(000) = 712
Mr = 346.68Dx = 1.597 Mg m3
Dm = 1.583 Mg m3
Dm measured by flotation technique; xylene & CHBr3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 11.824 (3) ÅCell parameters from 25 reflections
b = 9.6214 (11) Åθ = 9.7–14.2°
c = 13.669 (2) ŵ = 0.31 mm1
β = 111.990 (18)°T = 293 K
V = 1441.9 (4) Å3Block, colorless
Z = 40.19 × 0.15 × 0.12 mm
Data collection top
Nonius MACH3 four-circle
diffractometer
1030 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 25.0°, θmin = 2.8°
ω–2θ scansh = 014
Absorption correction: ψ scan
(North et al., 1968)
k = 111
Tmin = 0.970, Tmax = 0.999l = 1615
1490 measured reflections3 standard reflections every 60 min
1261 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043All H-atom parameters refined
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0634P)2 + 2.6398P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1261 reflectionsΔρmax = 0.45 e Å3
127 parametersΔρmin = 0.35 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=3DkFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0039 (11)
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
N10.3582 (2)0.1368 (2)0.77018 (16)0.0354 (5)
H10.348 (3)0.114 (3)0.706 (3)0.053 (9)*
C20.3400 (2)0.0332 (3)0.82685 (19)0.0339 (6)
H20.322 (3)0.050 (3)0.795 (2)0.048 (8)*
C30.3486 (2)0.0576 (3)0.92873 (18)0.0317 (6)
C40.3802 (3)0.1895 (3)0.9705 (2)0.0403 (7)
H40.390 (3)0.208 (3)1.041 (2)0.048 (8)*
C50.3997 (3)0.2945 (3)0.9098 (2)0.0440 (7)
H50.427 (3)0.389 (4)0.936 (3)0.067 (10)*
C60.3867 (2)0.2662 (3)0.8078 (2)0.0389 (6)
H60.396 (3)0.340 (3)0.761 (2)0.045 (8)*
C310.3221 (2)0.0556 (3)0.99283 (19)0.0375 (6)
O1A0.3476 (2)0.0342 (2)1.08684 (15)0.0633 (7)
O1B0.2752 (2)0.1657 (2)0.94342 (15)0.0502 (6)
H1B0.25000.25001.00000.091 (18)*
Cl10.00000.14087 (9)0.75000.0413 (3)
O10.0416 (3)0.0541 (3)0.8395 (2)0.0981 (11)
O20.0970 (3)0.2270 (4)0.7554 (3)0.1139 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0436 (13)0.0410 (13)0.0250 (11)0.0020 (10)0.0168 (9)0.0006 (9)
C20.0408 (14)0.0341 (14)0.0278 (12)0.0023 (11)0.0140 (10)0.0031 (11)
C30.0352 (13)0.0356 (14)0.0251 (11)0.0016 (10)0.0120 (9)0.0003 (10)
C40.0527 (16)0.0420 (15)0.0272 (13)0.0053 (13)0.0161 (11)0.0059 (11)
C50.0570 (17)0.0336 (15)0.0425 (15)0.0087 (13)0.0198 (13)0.0047 (12)
C60.0428 (15)0.0387 (15)0.0374 (14)0.0028 (12)0.0175 (12)0.0063 (12)
C310.0457 (15)0.0392 (15)0.0302 (13)0.0003 (12)0.0173 (11)0.0024 (11)
O1A0.1080 (19)0.0565 (14)0.0298 (11)0.0244 (13)0.0309 (11)0.0021 (9)
O1B0.0811 (15)0.0355 (11)0.0366 (10)0.0127 (10)0.0252 (10)0.0012 (8)
Cl10.0448 (6)0.0333 (5)0.0427 (5)0.0000.0127 (4)0.000
O10.147 (3)0.0704 (18)0.0585 (16)0.0255 (18)0.0169 (16)0.0201 (14)
O20.0694 (18)0.100 (2)0.170 (3)0.0213 (17)0.042 (2)0.047 (2)
Geometric parameters (Å, º) top
N1—C21.328 (3)C5—H50.99 (4)
N1—C61.341 (4)C6—H60.99 (3)
N1—H10.87 (3)C31—O1A1.222 (3)
C2—C31.378 (3)C31—O1B1.267 (3)
C2—H20.90 (3)O1B—H1B1.2320 (18)
C3—C41.384 (4)Cl1—O21.395 (3)
C3—C311.503 (3)Cl1—O2i1.395 (3)
C4—C51.380 (4)Cl1—O1i1.409 (3)
C4—H40.94 (3)Cl1—O11.409 (3)
C5—C61.371 (4)
C2—N1—C6123.0 (2)C4—C5—H5124 (2)
C2—N1—H1114 (2)N1—C6—C5119.4 (2)
C6—N1—H1123 (2)N1—C6—H6119.1 (17)
N1—C2—C3119.7 (2)C5—C6—H6121.5 (17)
N1—C2—H2116.7 (19)O1A—C31—O1B126.0 (2)
C3—C2—H2124 (2)O1A—C31—C3117.9 (2)
C2—C3—C4118.6 (2)O1B—C31—C3116.1 (2)
C2—C3—C31120.9 (2)C31—O1B—H1B112.11 (18)
C4—C3—C31120.5 (2)O2—Cl1—O2i107.1 (3)
C5—C4—C3120.2 (2)O2—Cl1—O1i114.3 (2)
C5—C4—H4119.4 (19)O2i—Cl1—O1i107.06 (19)
C3—C4—H4120.4 (19)O2—Cl1—O1107.06 (19)
C6—C5—C4119.1 (3)O2i—Cl1—O1114.3 (2)
C6—C5—H5117 (2)O1i—Cl1—O1107.3 (3)
C6—N1—C2—C31.0 (4)C2—N1—C6—C50.9 (4)
N1—C2—C3—C42.1 (4)C4—C5—C6—N11.5 (4)
N1—C2—C3—C31176.7 (2)C2—C3—C31—O1A169.9 (3)
C2—C3—C4—C51.4 (4)C4—C3—C31—O1A11.3 (4)
C31—C3—C4—C5177.4 (3)C2—C3—C31—O1B9.8 (4)
C3—C4—C5—C60.4 (4)C4—C3—C31—O1B169.0 (3)
Symmetry code: (i) x, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H1B···O1Bii1.231.232.464 (4)180
N1—H1···O1Aiii0.87 (3)1.80 (3)2.652 (3)168 (3)
Symmetry codes: (ii) x+1/2, y1/2, z+2; (iii) x, y, z1/2.
 

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