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The title compound, 2C
6H
5NO
2·H
+·ClO
4−, consists of [(nicotinic acid)
2H]
+ cations and ClO
4− 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
CCDC reference: 282638
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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+·ClO4− | F(000) = 712 |
Mr = 346.68 | Dx = 1.597 Mg m−3 Dm = 1.583 Mg m−3 Dm measured by flotation technique; xylene & CHBr3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.824 (3) Å | Cell parameters from 25 reflections |
b = 9.6214 (11) Å | θ = 9.7–14.2° |
c = 13.669 (2) Å | µ = 0.31 mm−1 |
β = 111.990 (18)° | T = 293 K |
V = 1441.9 (4) Å3 | Block, colorless |
Z = 4 | 0.19 × 0.15 × 0.12 mm |
Data collection top
Nonius MACH3 four-circle diffractometer | 1030 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 25.0°, θmin = 2.8° |
ω–2θ scans | h = 0→14 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→11 |
Tmin = 0.970, Tmax = 0.999 | l = −16→15 |
1490 measured reflections | 3 standard reflections every 60 min |
1261 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | All 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 reflections | Δρmax = 0.45 e Å−3 |
127 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=3DkFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
N1 | 0.3582 (2) | 0.1368 (2) | 0.77018 (16) | 0.0354 (5) | |
H1 | 0.348 (3) | 0.114 (3) | 0.706 (3) | 0.053 (9)* | |
C2 | 0.3400 (2) | 0.0332 (3) | 0.82685 (19) | 0.0339 (6) | |
H2 | 0.322 (3) | −0.050 (3) | 0.795 (2) | 0.048 (8)* | |
C3 | 0.3486 (2) | 0.0576 (3) | 0.92873 (18) | 0.0317 (6) | |
C4 | 0.3802 (3) | 0.1895 (3) | 0.9705 (2) | 0.0403 (7) | |
H4 | 0.390 (3) | 0.208 (3) | 1.041 (2) | 0.048 (8)* | |
C5 | 0.3997 (3) | 0.2945 (3) | 0.9098 (2) | 0.0440 (7) | |
H5 | 0.427 (3) | 0.389 (4) | 0.936 (3) | 0.067 (10)* | |
C6 | 0.3867 (2) | 0.2662 (3) | 0.8078 (2) | 0.0389 (6) | |
H6 | 0.396 (3) | 0.340 (3) | 0.761 (2) | 0.045 (8)* | |
C31 | 0.3221 (2) | −0.0556 (3) | 0.99283 (19) | 0.0375 (6) | |
O1A | 0.3476 (2) | −0.0342 (2) | 1.08684 (15) | 0.0633 (7) | |
O1B | 0.2752 (2) | −0.1657 (2) | 0.94342 (15) | 0.0502 (6) | |
H1B | 0.2500 | −0.2500 | 1.0000 | 0.091 (18)* | |
Cl1 | 0.0000 | 0.14087 (9) | 0.7500 | 0.0413 (3) | |
O1 | 0.0416 (3) | 0.0541 (3) | 0.8395 (2) | 0.0981 (11) | |
O2 | 0.0970 (3) | 0.2270 (4) | 0.7554 (3) | 0.1139 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0436 (13) | 0.0410 (13) | 0.0250 (11) | −0.0020 (10) | 0.0168 (9) | 0.0006 (9) |
C2 | 0.0408 (14) | 0.0341 (14) | 0.0278 (12) | −0.0023 (11) | 0.0140 (10) | −0.0031 (11) |
C3 | 0.0352 (13) | 0.0356 (14) | 0.0251 (11) | −0.0016 (10) | 0.0120 (9) | −0.0003 (10) |
C4 | 0.0527 (16) | 0.0420 (15) | 0.0272 (13) | −0.0053 (13) | 0.0161 (11) | −0.0059 (11) |
C5 | 0.0570 (17) | 0.0336 (15) | 0.0425 (15) | −0.0087 (13) | 0.0198 (13) | −0.0047 (12) |
C6 | 0.0428 (15) | 0.0387 (15) | 0.0374 (14) | −0.0028 (12) | 0.0175 (12) | 0.0063 (12) |
C31 | 0.0457 (15) | 0.0392 (15) | 0.0302 (13) | 0.0003 (12) | 0.0173 (11) | 0.0024 (11) |
O1A | 0.1080 (19) | 0.0565 (14) | 0.0298 (11) | −0.0244 (13) | 0.0309 (11) | −0.0021 (9) |
O1B | 0.0811 (15) | 0.0355 (11) | 0.0366 (10) | −0.0127 (10) | 0.0252 (10) | −0.0012 (8) |
Cl1 | 0.0448 (6) | 0.0333 (5) | 0.0427 (5) | 0.000 | 0.0127 (4) | 0.000 |
O1 | 0.147 (3) | 0.0704 (18) | 0.0585 (16) | −0.0255 (18) | 0.0169 (16) | 0.0201 (14) |
O2 | 0.0694 (18) | 0.100 (2) | 0.170 (3) | −0.0213 (17) | 0.042 (2) | 0.047 (2) |
Geometric parameters (Å, º) top
N1—C2 | 1.328 (3) | C5—H5 | 0.99 (4) |
N1—C6 | 1.341 (4) | C6—H6 | 0.99 (3) |
N1—H1 | 0.87 (3) | C31—O1A | 1.222 (3) |
C2—C3 | 1.378 (3) | C31—O1B | 1.267 (3) |
C2—H2 | 0.90 (3) | O1B—H1B | 1.2320 (18) |
C3—C4 | 1.384 (4) | Cl1—O2 | 1.395 (3) |
C3—C31 | 1.503 (3) | Cl1—O2i | 1.395 (3) |
C4—C5 | 1.380 (4) | Cl1—O1i | 1.409 (3) |
C4—H4 | 0.94 (3) | Cl1—O1 | 1.409 (3) |
C5—C6 | 1.371 (4) | | |
| | | |
C2—N1—C6 | 123.0 (2) | C4—C5—H5 | 124 (2) |
C2—N1—H1 | 114 (2) | N1—C6—C5 | 119.4 (2) |
C6—N1—H1 | 123 (2) | N1—C6—H6 | 119.1 (17) |
N1—C2—C3 | 119.7 (2) | C5—C6—H6 | 121.5 (17) |
N1—C2—H2 | 116.7 (19) | O1A—C31—O1B | 126.0 (2) |
C3—C2—H2 | 124 (2) | O1A—C31—C3 | 117.9 (2) |
C2—C3—C4 | 118.6 (2) | O1B—C31—C3 | 116.1 (2) |
C2—C3—C31 | 120.9 (2) | C31—O1B—H1B | 112.11 (18) |
C4—C3—C31 | 120.5 (2) | O2—Cl1—O2i | 107.1 (3) |
C5—C4—C3 | 120.2 (2) | O2—Cl1—O1i | 114.3 (2) |
C5—C4—H4 | 119.4 (19) | O2i—Cl1—O1i | 107.06 (19) |
C3—C4—H4 | 120.4 (19) | O2—Cl1—O1 | 107.06 (19) |
C6—C5—C4 | 119.1 (3) | O2i—Cl1—O1 | 114.3 (2) |
C6—C5—H5 | 117 (2) | O1i—Cl1—O1 | 107.3 (3) |
| | | |
C6—N1—C2—C3 | 1.0 (4) | C2—N1—C6—C5 | 0.9 (4) |
N1—C2—C3—C4 | −2.1 (4) | C4—C5—C6—N1 | −1.5 (4) |
N1—C2—C3—C31 | 176.7 (2) | C2—C3—C31—O1A | 169.9 (3) |
C2—C3—C4—C5 | 1.4 (4) | C4—C3—C31—O1A | −11.3 (4) |
C31—C3—C4—C5 | −177.4 (3) | C2—C3—C31—O1B | −9.8 (4) |
C3—C4—C5—C6 | 0.4 (4) | C4—C3—C31—O1B | 169.0 (3) |
Symmetry code: (i) −x, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···O1Bii | 1.23 | 1.23 | 2.464 (4) | 180 |
N1—H1···O1Aiii | 0.87 (3) | 1.80 (3) | 2.652 (3) | 168 (3) |
Symmetry codes: (ii) −x+1/2, −y−1/2, −z+2; (iii) x, −y, z−1/2. |
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