



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810047872/su2230sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810047872/su2230Isup2.hkl |
CCDC reference: 803250
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.105
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) ..... 11
Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.43 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 5 PLAT041_ALERT_1_C Calc. and Reported SumFormula Strings Differ ? PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C8 H7 O2 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 2
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was synthesized by heating together under reflux for 10 mins, 1 mmol quantities of piperidine-4-carboxamide (isonipecotamide) and phenylacetic acid in 50 ml of 50% methanol–water. After concentration to ca 30 ml, partial room temperature evaporation of the hot-filtered solution gave colourless plates of (I) from which a specimen was cleaved for the X-ray diffraction analysis.
Hydrogen atoms involved in hydrogen-bonding interactions were located in difference Fourier maps and were freely refined. Other H-atoms were included in calculated positions using a riding-model approximation [C–H = 0.93–0.98 Å] and with Uiso(H) = 1.2Ueq(C)].
The amide piperidine-4-carboxamide (isonipecotamide, INIPA) has proved to be a particularly useful synthon for the construction of hydrogen-bonded crystalline salts with a range of aromatic carboxylic acids, enabling their structure determination (Smith & Wermuth, 2010a, 2010b, 2010c; Smith et al., 2010). The title compound from the 1:1 stoichiometric reaction of phenylacetic acid with INIPA, the hemihydrate C6H13N2O+ C8H7O2-. 0.5H2O, (I) was obtained and the structure is reported on herein.
In (I) the asymmetric unit contains two phenylacetate anions (A and B), two INIPA cations (C and D) and a water molecule of solvation (O1W) (Fig. 1). The hydrogen-bonding environments for both sets of ion pairs are essentially identical with the piperidinium and amide 'ends' of each cation involved in lateral heteromolecular cyclic hydrogen-bonded associations [graph set R22(11) (Etter et al., 1990)] (Table 1) which incorporate a single carboxyl O-atom acceptor (Fig. 2). The rings involve (a): cation C pyrimidinium and cation D amide N—H donors and cation C amide and anion B carboxyl O-atom acceptors and (b): cation D pyrimidinium and cation C amide N—H donors and cation D amide and anion A carboxyl O-atom acceptors. These ring motifs enclose larger cyclic systems [graph set R55(21)] forming sheet substructures which lie parallel to (101) and are linked across b by the single water molecule via water O—H···Ocarboxyl associations to give the two-dimensional duplex-sheet structure (Fig. 3).
In the two independent phenylacetate anions, the conformation of the acetate side chains are significantly different [comparative torsion angles (maximum) for C2/C6–C1–C11–C12, 95.07 (17)° (A) and 124.84 (17)° (B); C1–C11–C12–O12/O13, 90.43 (16)° (A) and 127.76 (16)° (B)].
For structural data on isonipecotamide salts, see: Smith et al. (2010); Smith & Wermuth (2010a,b,c). For graph-set analysis, see Etter et al. (1990).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).
C6H13N2O+·C8H7O2−·0.5H2O | F(000) = 1176 |
Mr = 273.33 | Dx = 1.226 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5553 reflections |
a = 12.3107 (9) Å | θ = 3.2–28.9° |
b = 25.214 (2) Å | µ = 0.09 mm−1 |
c = 9.5402 (10) Å | T = 200 K |
β = 90.469 (9)° | Prism, colourless |
V = 2961.2 (4) Å3 | 0.50 × 0.22 × 0.20 mm |
Z = 8 |
Oxford Diffraction Gemini-S CCD-detector diffractometer | 5802 independent reflections |
Radiation source: Enhance (Mo) X-ray source | 4258 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 16.066 pixels mm-1 | θmax = 26.0°, θmin = 3.2° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = −31→30 |
Tmin = 0.959, Tmax = 0.979 | l = −11→11 |
21326 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.056P)2] where P = (Fo2 + 2Fc2)/3 |
5802 reflections | (Δ/σ)max = 0.002 |
392 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C6H13N2O+·C8H7O2−·0.5H2O | V = 2961.2 (4) Å3 |
Mr = 273.33 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.3107 (9) Å | µ = 0.09 mm−1 |
b = 25.214 (2) Å | T = 200 K |
c = 9.5402 (10) Å | 0.50 × 0.22 × 0.20 mm |
β = 90.469 (9)° |
Oxford Diffraction Gemini-S CCD-detector diffractometer | 5802 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 4258 reflections with I > 2σ(I) |
Tmin = 0.959, Tmax = 0.979 | Rint = 0.041 |
21326 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.17 e Å−3 |
5802 reflections | Δρmin = −0.20 e Å−3 |
392 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | ||
O41C | 0.64163 (9) | 0.15818 (5) | 0.16896 (11) | 0.0435 (4) | |
N1C | 1.02344 (12) | 0.17322 (6) | 0.12820 (14) | 0.0270 (4) | |
N41C | 0.61664 (12) | 0.16239 (6) | −0.06342 (14) | 0.0281 (4) | |
C2C | 0.96731 (14) | 0.22255 (7) | 0.08191 (18) | 0.0350 (6) | |
C3C | 0.84553 (13) | 0.21748 (7) | 0.10209 (18) | 0.0328 (5) | |
C4C | 0.80024 (12) | 0.16875 (6) | 0.02592 (15) | 0.0263 (5) | |
C5C | 0.86040 (13) | 0.11923 (6) | 0.07541 (17) | 0.0296 (5) | |
C6C | 0.98170 (13) | 0.12504 (7) | 0.05565 (17) | 0.0350 (6) | |
C41C | 0.67876 (13) | 0.16266 (6) | 0.04932 (15) | 0.0263 (5) | |
O41D | 0.71839 (9) | 0.15906 (5) | 0.66969 (11) | 0.0340 (4) | |
N1D | 0.33442 (11) | 0.16040 (5) | 0.62431 (14) | 0.0239 (4) | |
N41D | 0.74212 (12) | 0.15583 (6) | 0.43668 (14) | 0.0275 (4) | |
C2D | 0.38272 (13) | 0.11238 (6) | 0.55692 (16) | 0.0268 (5) | |
C3D | 0.50450 (12) | 0.11097 (6) | 0.57817 (16) | 0.0257 (5) | |
C4D | 0.55825 (12) | 0.16182 (6) | 0.52381 (15) | 0.0229 (5) | |
C5D | 0.50677 (12) | 0.21026 (6) | 0.59475 (16) | 0.0265 (5) | |
C6D | 0.38455 (13) | 0.21083 (6) | 0.57385 (17) | 0.0281 (5) | |
C41D | 0.68013 (13) | 0.15910 (6) | 0.54975 (15) | 0.0225 (5) | |
O12A | 0.38376 (9) | 0.15741 (4) | 0.90984 (10) | 0.0303 (3) | |
O13A | 0.21718 (9) | 0.17101 (4) | 0.99066 (10) | 0.0269 (3) | |
C1A | 0.34155 (14) | 0.08390 (6) | 1.17288 (14) | 0.0267 (5) | |
C2A | 0.42802 (16) | 0.04963 (7) | 1.14988 (17) | 0.0409 (6) | |
C3A | 0.41423 (19) | −0.00506 (8) | 1.1602 (2) | 0.0515 (8) | |
C4A | 0.31547 (19) | −0.02627 (7) | 1.19230 (18) | 0.0477 (7) | |
C5A | 0.22827 (17) | 0.00717 (7) | 1.21644 (18) | 0.0421 (6) | |
C6A | 0.24171 (14) | 0.06180 (7) | 1.20799 (16) | 0.0330 (6) | |
C11A | 0.35341 (13) | 0.14331 (6) | 1.15417 (15) | 0.0262 (5) | |
C12A | 0.31531 (12) | 0.15890 (6) | 1.00715 (15) | 0.0212 (5) | |
O12B | 0.14841 (9) | 0.16112 (4) | 0.47053 (11) | 0.0337 (4) | |
O13B | −0.02269 (9) | 0.15006 (5) | 0.40455 (11) | 0.0344 (4) | |
C1B | 0.10892 (13) | 0.06973 (7) | 0.65695 (16) | 0.0291 (5) | |
C2B | 0.12468 (16) | 0.02946 (7) | 0.55923 (18) | 0.0422 (7) | |
C3B | 0.19546 (18) | −0.01206 (7) | 0.5849 (2) | 0.0488 (7) | |
C4B | 0.25265 (17) | −0.01453 (7) | 0.70955 (19) | 0.0432 (7) | |
C5B | 0.23861 (15) | 0.02523 (7) | 0.80669 (17) | 0.0387 (6) | |
C6B | 0.16796 (14) | 0.06710 (7) | 0.78084 (16) | 0.0329 (6) | |
C11B | 0.03138 (15) | 0.11508 (8) | 0.62690 (17) | 0.0408 (6) | |
C12B | 0.05390 (13) | 0.14407 (6) | 0.48988 (15) | 0.0247 (5) | |
O1W | 0.16998 (12) | 0.24940 (7) | 0.79325 (14) | 0.0469 (5) | |
H4C | 0.81260 | 0.17310 | −0.07480 | 0.0320* | |
H11C | 1.0116 (15) | 0.1664 (6) | 0.2238 (19) | 0.038 (5)* | |
H12C | 1.0962 (19) | 0.1748 (7) | 0.104 (2) | 0.051 (6)* | |
H21C | 0.98250 | 0.22910 | −0.01620 | 0.0420* | |
H22C | 0.99450 | 0.25240 | 0.13570 | 0.0420* | |
H31C | 0.80980 | 0.24910 | 0.06660 | 0.0390* | |
H32C | 0.83010 | 0.21470 | 0.20140 | 0.0390* | |
H41C | 0.5472 (17) | 0.1585 (6) | −0.0576 (18) | 0.035 (5)* | |
H42C | 0.6465 (16) | 0.1648 (6) | −0.1533 (19) | 0.040 (5)* | |
H51C | 0.84530 | 0.11320 | 0.17370 | 0.0360* | |
H52C | 0.83450 | 0.08870 | 0.02290 | 0.0360* | |
H61C | 1.01830 | 0.09390 | 0.09270 | 0.0420* | |
H62C | 0.99740 | 0.12740 | −0.04360 | 0.0420* | |
H4D | 0.54510 | 0.16430 | 0.42260 | 0.0270* | |
H11D | 0.3410 (14) | 0.1582 (6) | 0.7207 (18) | 0.031 (5)* | |
H12D | 0.2590 (17) | 0.1610 (7) | 0.5982 (19) | 0.043 (5)* | |
H21D | 0.36610 | 0.11270 | 0.45740 | 0.0320* | |
H22D | 0.35080 | 0.08070 | 0.59700 | 0.0320* | |
H31D | 0.53420 | 0.08060 | 0.52920 | 0.0310* | |
H32D | 0.52090 | 0.10690 | 0.67720 | 0.0310* | |
H41D | 0.8121 (17) | 0.1539 (7) | 0.4489 (18) | 0.036 (5)* | |
H42D | 0.7104 (16) | 0.1581 (7) | 0.350 (2) | 0.046 (6)* | |
H51D | 0.52350 | 0.20960 | 0.69430 | 0.0320* | |
H52D | 0.53750 | 0.24240 | 0.55580 | 0.0320* | |
H61D | 0.35380 | 0.24050 | 0.62460 | 0.0340* | |
H62D | 0.36780 | 0.21560 | 0.47510 | 0.0340* | |
H2A | 0.49580 | 0.06340 | 1.12740 | 0.0490* | |
H3A | 0.47310 | −0.02740 | 1.14510 | 0.0620* | |
H4A | 0.30680 | −0.06280 | 1.19790 | 0.0570* | |
H5A | 0.16070 | −0.00700 | 1.23830 | 0.0510* | |
H6A | 0.18310 | 0.08400 | 1.22610 | 0.0400* | |
H11A | 0.42880 | 0.15350 | 1.16740 | 0.0320* | |
H12A | 0.31030 | 0.16170 | 1.22360 | 0.0320* | |
H2B | 0.08670 | 0.03050 | 0.47460 | 0.0510* | |
H3B | 0.20450 | −0.03840 | 0.51780 | 0.0590* | |
H4B | 0.29990 | −0.04250 | 0.72770 | 0.0520* | |
H5B | 0.27710 | 0.02400 | 0.89100 | 0.0460* | |
H6B | 0.16020 | 0.09370 | 0.84760 | 0.0400* | |
H11B | 0.03570 | 0.14030 | 0.70350 | 0.0490* | |
H12B | −0.04220 | 0.10130 | 0.62380 | 0.0490* | |
H11W | 0.1841 (19) | 0.2232 (9) | 0.846 (2) | 0.065 (7)* | |
H12W | 0.163 (2) | 0.2760 (11) | 0.846 (3) | 0.086 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O41C | 0.0191 (6) | 0.0934 (10) | 0.0181 (6) | −0.0034 (6) | 0.0012 (5) | 0.0025 (6) |
N1C | 0.0149 (7) | 0.0434 (9) | 0.0226 (7) | −0.0017 (6) | 0.0017 (6) | 0.0040 (6) |
N41C | 0.0144 (7) | 0.0510 (9) | 0.0189 (7) | 0.0010 (7) | 0.0001 (6) | −0.0011 (6) |
C2C | 0.0265 (10) | 0.0390 (10) | 0.0395 (10) | −0.0072 (8) | −0.0041 (8) | 0.0141 (8) |
C3C | 0.0237 (9) | 0.0306 (9) | 0.0442 (10) | 0.0037 (7) | −0.0016 (8) | 0.0081 (8) |
C4C | 0.0160 (8) | 0.0466 (10) | 0.0163 (7) | 0.0002 (7) | −0.0002 (6) | 0.0043 (7) |
C5C | 0.0229 (9) | 0.0359 (10) | 0.0301 (8) | −0.0013 (7) | −0.0014 (7) | −0.0096 (7) |
C6C | 0.0215 (9) | 0.0496 (11) | 0.0338 (9) | 0.0079 (8) | 0.0002 (7) | −0.0102 (8) |
C41C | 0.0188 (8) | 0.0401 (10) | 0.0200 (8) | 0.0012 (7) | 0.0001 (6) | 0.0004 (7) |
O41D | 0.0217 (6) | 0.0623 (8) | 0.0181 (5) | −0.0019 (6) | −0.0009 (5) | 0.0038 (5) |
N1D | 0.0143 (7) | 0.0379 (8) | 0.0195 (7) | −0.0006 (6) | −0.0009 (5) | 0.0042 (6) |
N41D | 0.0155 (7) | 0.0484 (9) | 0.0185 (7) | 0.0002 (7) | 0.0013 (6) | −0.0012 (6) |
C2D | 0.0230 (9) | 0.0317 (9) | 0.0258 (8) | −0.0058 (7) | 0.0010 (7) | −0.0035 (7) |
C3D | 0.0203 (9) | 0.0261 (8) | 0.0307 (8) | 0.0001 (7) | 0.0021 (7) | −0.0016 (7) |
C4D | 0.0172 (8) | 0.0339 (9) | 0.0175 (7) | −0.0010 (7) | 0.0013 (6) | 0.0038 (6) |
C5D | 0.0221 (9) | 0.0248 (8) | 0.0326 (8) | −0.0023 (7) | −0.0001 (7) | 0.0062 (7) |
C6D | 0.0220 (9) | 0.0297 (9) | 0.0327 (8) | 0.0031 (7) | −0.0004 (7) | 0.0077 (7) |
C41D | 0.0221 (8) | 0.0268 (8) | 0.0187 (8) | −0.0020 (7) | 0.0018 (6) | 0.0028 (6) |
O12A | 0.0181 (6) | 0.0532 (7) | 0.0197 (5) | 0.0004 (5) | 0.0027 (5) | 0.0023 (5) |
O13A | 0.0175 (6) | 0.0357 (6) | 0.0274 (6) | 0.0027 (5) | 0.0030 (5) | 0.0035 (5) |
C1A | 0.0293 (9) | 0.0371 (9) | 0.0138 (7) | 0.0067 (8) | −0.0014 (6) | 0.0020 (7) |
C2A | 0.0361 (11) | 0.0503 (12) | 0.0363 (10) | 0.0116 (9) | 0.0064 (8) | 0.0089 (9) |
C3A | 0.0600 (15) | 0.0461 (12) | 0.0486 (12) | 0.0266 (11) | 0.0090 (10) | 0.0079 (9) |
C4A | 0.0755 (16) | 0.0314 (11) | 0.0361 (10) | 0.0096 (10) | −0.0034 (10) | 0.0064 (8) |
C5A | 0.0494 (12) | 0.0411 (11) | 0.0358 (10) | −0.0062 (10) | −0.0026 (9) | 0.0088 (8) |
C6A | 0.0324 (10) | 0.0367 (10) | 0.0298 (9) | 0.0061 (8) | 0.0001 (7) | 0.0036 (7) |
C11A | 0.0236 (9) | 0.0359 (9) | 0.0192 (8) | −0.0002 (7) | −0.0005 (6) | −0.0017 (7) |
C12A | 0.0193 (8) | 0.0223 (8) | 0.0220 (8) | −0.0036 (6) | 0.0007 (6) | −0.0012 (6) |
O12B | 0.0200 (6) | 0.0432 (7) | 0.0377 (6) | −0.0031 (5) | −0.0059 (5) | 0.0081 (5) |
O13B | 0.0167 (6) | 0.0597 (8) | 0.0268 (6) | −0.0025 (5) | −0.0036 (5) | 0.0070 (5) |
C1B | 0.0238 (9) | 0.0388 (10) | 0.0248 (8) | −0.0061 (7) | 0.0030 (7) | 0.0071 (7) |
C2B | 0.0518 (13) | 0.0444 (12) | 0.0303 (9) | −0.0107 (10) | −0.0115 (9) | 0.0002 (8) |
C3B | 0.0715 (15) | 0.0283 (10) | 0.0465 (11) | −0.0041 (10) | −0.0065 (11) | −0.0039 (9) |
C4B | 0.0502 (13) | 0.0329 (10) | 0.0466 (11) | 0.0020 (9) | 0.0024 (9) | 0.0140 (9) |
C5B | 0.0357 (11) | 0.0533 (12) | 0.0270 (9) | −0.0009 (9) | −0.0037 (8) | 0.0107 (8) |
C6B | 0.0304 (10) | 0.0465 (11) | 0.0219 (8) | −0.0027 (8) | 0.0025 (7) | −0.0002 (7) |
C11B | 0.0275 (10) | 0.0645 (13) | 0.0306 (9) | 0.0098 (9) | 0.0064 (8) | 0.0111 (9) |
C12B | 0.0168 (8) | 0.0322 (9) | 0.0251 (8) | 0.0042 (7) | 0.0004 (7) | −0.0016 (7) |
O1W | 0.0625 (10) | 0.0482 (9) | 0.0300 (7) | 0.0147 (8) | −0.0042 (7) | 0.0048 (7) |
O41C—C41C | 1.2382 (18) | C5D—C6D | 1.516 (2) |
O41D—C41D | 1.2338 (18) | C2D—H21D | 0.9700 |
O12A—C12A | 1.2594 (18) | C2D—H22D | 0.9700 |
O13A—C12A | 1.2547 (18) | C3D—H31D | 0.9700 |
O12B—C12B | 1.2554 (19) | C3D—H32D | 0.9700 |
O13B—C12B | 1.2498 (19) | C4D—H4D | 0.9800 |
O1W—H11W | 0.85 (2) | C5D—H52D | 0.9700 |
O1W—H12W | 0.84 (3) | C5D—H51D | 0.9700 |
N1C—C6C | 1.488 (2) | C6D—H61D | 0.9700 |
N1C—C2C | 1.488 (2) | C6D—H62D | 0.9700 |
N41C—C41C | 1.315 (2) | C1A—C6A | 1.393 (2) |
N1C—H12C | 0.93 (2) | C1A—C2A | 1.390 (3) |
N1C—H11C | 0.941 (18) | C1A—C11A | 1.516 (2) |
N41C—H41C | 0.86 (2) | C2A—C3A | 1.393 (3) |
N41C—H42C | 0.938 (18) | C3A—C4A | 1.365 (3) |
N1D—C2D | 1.496 (2) | C4A—C5A | 1.386 (3) |
N1D—C6D | 1.495 (2) | C5A—C6A | 1.390 (3) |
N41D—C41D | 1.329 (2) | C11A—C12A | 1.527 (2) |
N1D—H12D | 0.96 (2) | C2A—H2A | 0.9300 |
N1D—H11D | 0.924 (17) | C3A—H3A | 0.9300 |
N41D—H42D | 0.913 (19) | C4A—H4A | 0.9300 |
N41D—H41D | 0.87 (2) | C5A—H5A | 0.9300 |
C2C—C3C | 1.519 (2) | C6A—H6A | 0.9300 |
C3C—C4C | 1.530 (2) | C11A—H11A | 0.9700 |
C4C—C5C | 1.525 (2) | C11A—H12A | 0.9700 |
C4C—C41C | 1.522 (2) | C1B—C11B | 1.515 (3) |
C5C—C6C | 1.514 (2) | C1B—C6B | 1.384 (2) |
C2C—H21C | 0.9700 | C1B—C2B | 1.393 (2) |
C2C—H22C | 0.9700 | C2B—C3B | 1.383 (3) |
C3C—H31C | 0.9700 | C3B—C4B | 1.378 (3) |
C3C—H32C | 0.9700 | C4B—C5B | 1.377 (2) |
C4C—H4C | 0.9800 | C5B—C6B | 1.389 (3) |
C5C—H52C | 0.9700 | C11B—C12B | 1.525 (2) |
C5C—H51C | 0.9700 | C2B—H2B | 0.9300 |
C6C—H62C | 0.9700 | C3B—H3B | 0.9300 |
C6C—H61C | 0.9700 | C4B—H4B | 0.9300 |
C2D—C3D | 1.512 (2) | C5B—H5B | 0.9300 |
C3D—C4D | 1.535 (2) | C6B—H6B | 0.9300 |
C4D—C5D | 1.536 (2) | C11B—H12B | 0.9700 |
C4D—C41D | 1.520 (2) | C11B—H11B | 0.9700 |
O1W···O13A | 2.7881 (19) | C12B···H2B | 2.9000 |
O1W···C2Ci | 3.272 (2) | C12B···H22Ci | 3.0500 |
O1W···O12Bii | 2.8335 (19) | C12B···H11Cvi | 2.648 (18) |
O1W···N1Ci | 3.081 (2) | C41C···H42D | 2.894 (19) |
O12A···N1D | 2.7871 (17) | C41C···H52Div | 2.9600 |
O12A···N41Ciii | 2.8789 (19) | C41D···H31Cii | 2.8200 |
O12B···N1D | 2.7095 (18) | C41D···H42Ciii | 2.870 (18) |
O12B···O1Wiv | 2.8335 (19) | H2A···H11A | 2.4500 |
O12B···C6D | 3.309 (2) | H2B···C5Avii | 3.0900 |
O12B···C2D | 3.236 (2) | H2B···C2Bxii | 3.0200 |
O13A···C6B | 3.349 (2) | H2B···C12B | 2.9000 |
O13A···C6Cv | 3.188 (2) | H4A···O41Dviii | 2.7500 |
O13A···O1W | 2.7881 (19) | H4C···O41Dvii | 2.7100 |
O13A···N1Cv | 2.7322 (18) | H4C···H62C | 2.5700 |
O13B···N41Dvi | 2.9177 (19) | H4C···H42C | 2.1800 |
O13B···N1Cvi | 2.7638 (17) | H4C···H21C | 2.5800 |
O13B···C6Cvi | 3.389 (2) | H4D···H42D | 2.1600 |
O41C···N41D | 2.8294 (18) | H4D···O41C | 2.7100 |
O41D···N41Ciii | 2.8480 (18) | H4D···H62D | 2.5900 |
O1W···H61D | 2.8000 | H4D···H21D | 2.5800 |
O1W···H12Aiv | 2.9100 | H6A···H12A | 2.5100 |
O1W···H12Ci | 2.777 (19) | H6A···H61Cv | 2.4000 |
O1W···H22Ci | 2.6200 | H6B···H11B | 2.3600 |
O12A···H41Ciii | 2.03 (2) | H6B···O13A | 2.4800 |
O12A···H11D | 1.876 (17) | H6B···C12A | 2.9400 |
O12B···H12Wiv | 1.99 (3) | H6B···C6Cv | 3.0800 |
O12B···H12D | 1.82 (2) | H6B···H62Cv | 2.4200 |
O12B···H11Cvi | 2.886 (18) | H11A···H2A | 2.4500 |
O13A···H11W | 1.95 (2) | H11A···O41Ciii | 2.6200 |
O13A···H6B | 2.4800 | H11B···H62Cv | 2.4800 |
O13A···H12Cv | 1.85 (2) | H11B···H6B | 2.3600 |
O13B···H41Dvi | 2.08 (2) | H11C···O13Bix | 1.826 (18) |
O13B···H11Cvi | 1.826 (18) | H11C···O12Bix | 2.886 (18) |
O13B···H51Cvi | 2.8800 | H11C···H32C | 2.5500 |
O41C···H32C | 2.7400 | H11C···H51C | 2.4900 |
O41C···H51C | 2.7500 | H11C···C12Bix | 2.648 (18) |
O41C···H4D | 2.7100 | H11D···C12A | 2.754 (17) |
O41C···H42D | 1.917 (19) | H11D···O12A | 1.876 (17) |
O41C···H11Avii | 2.6200 | H11W···C12A | 2.75 (2) |
O41D···H51D | 2.7300 | H11W···O13A | 1.95 (2) |
O41D···H4Aviii | 2.7500 | H12A···H6A | 2.5100 |
O41D···H42Ciii | 1.918 (18) | H12A···O1Wii | 2.9100 |
O41D···H31Cii | 2.7600 | H12C···C12Axi | 2.89 (2) |
O41D···H4Ciii | 2.7100 | H12C···O1Wx | 2.777 (19) |
O41D···H32D | 2.7700 | H12C···O13Axi | 1.85 (2) |
N1C···O13Bix | 2.7638 (17) | H12D···C12B | 2.75 (2) |
N1C···O1Wx | 3.081 (2) | H12D···O12B | 1.82 (2) |
N1C···O13Axi | 2.7322 (18) | H12D···C1B | 3.007 (19) |
N1D···O12A | 2.7871 (17) | H12D···C11B | 3.05 (2) |
N1D···O12B | 2.7095 (18) | H12W···C12Bii | 2.79 (3) |
N41C···O12Avii | 2.8789 (19) | H12W···O12Bii | 1.99 (3) |
N41C···O41Dvii | 2.8480 (18) | H21C···H4C | 2.5800 |
N41D···O41C | 2.8294 (18) | H21C···H62C | 2.5800 |
N41D···O13Bix | 2.9177 (19) | H21D···C6Avii | 3.1000 |
N41C···H52Div | 2.8300 | H21D···C1Avii | 2.8200 |
N41C···H51Dvii | 2.8300 | H21D···C11Avii | 3.0000 |
N41D···H32C | 2.9100 | H21D···H4D | 2.5800 |
N41D···H31Cii | 2.8200 | H22C···C12Bx | 3.0500 |
C2B···C5Avii | 3.564 (3) | H22C···O1Wx | 2.6200 |
C2B···C2Bxii | 3.585 (3) | H22D···C4B | 2.9000 |
C2C···O1Wx | 3.272 (2) | H22D···C5B | 2.8100 |
C2D···C6B | 3.599 (2) | H22D···C6B | 2.8900 |
C2D···O12B | 3.236 (2) | H22D···C3B | 3.0200 |
C3B···C5Avii | 3.575 (3) | H22D···C1B | 3.0500 |
C5A···C2Biii | 3.564 (3) | H22D···C2B | 3.0900 |
C5A···C3Biii | 3.575 (3) | H31C···C41Div | 2.8200 |
C6B···O13A | 3.349 (2) | H31C···O41Div | 2.7600 |
C6B···C2D | 3.599 (2) | H31C···N41Div | 2.8200 |
C6C···O13Axi | 3.188 (2) | H32C···O41C | 2.7400 |
C6C···O13Bix | 3.389 (2) | H32C···N41D | 2.9100 |
C6D···C12Aiv | 3.451 (2) | H32C···H11C | 2.5500 |
C6D···O12B | 3.309 (2) | H32C···H42D | 2.5000 |
C12A···C6Dii | 3.451 (2) | H32C···H51C | 2.5800 |
C1A···H21Diii | 2.8200 | H32D···H51D | 2.5900 |
C1B···H22D | 3.0500 | H32D···O41D | 2.7700 |
C1B···H12D | 3.007 (19) | H41C···C12Avii | 2.93 (2) |
C2B···H22D | 3.0900 | H41C···O12Avii | 2.03 (2) |
C2B···H2Bxii | 3.0200 | H41D···O13Bix | 2.08 (2) |
C3B···H22D | 3.0200 | H41D···C12Bix | 3.01 (2) |
C4B···H22D | 2.9000 | H42C···O41Dvii | 1.918 (18) |
C4B···H51Cxiii | 2.9800 | H42C···H51Dvii | 2.3800 |
C5A···H2Biii | 3.0900 | H42C···C41Dvii | 2.870 (18) |
C5B···H22D | 2.8100 | H42C···H4C | 2.1800 |
C6A···H21Diii | 3.1000 | H42D···H4D | 2.1600 |
C6A···H61Cv | 3.0600 | H42D···C41C | 2.894 (19) |
C6B···H22D | 2.8900 | H42D···O41C | 1.917 (19) |
C6B···H62Cv | 3.1000 | H42D···H32C | 2.5000 |
C6C···H6Bxi | 3.0800 | H51C···H32C | 2.5800 |
C11A···H61Dii | 2.9400 | H51C···O13Bix | 2.8800 |
C11A···H21Diii | 3.0000 | H51C···C4Bxiii | 2.9800 |
C11B···H12D | 3.05 (2) | H51C···O41C | 2.7500 |
C12A···H12Cv | 2.89 (2) | H51C···H11C | 2.4900 |
C12A···H11W | 2.75 (2) | H51D···O41D | 2.7300 |
C12A···H11D | 2.754 (17) | H51D···N41Ciii | 2.8300 |
C12A···H41Ciii | 2.93 (2) | H51D···H32D | 2.5900 |
C12A···H61Dii | 2.8100 | H51D···H42Ciii | 2.3800 |
C12A···H6B | 2.9400 | H52D···C41Cii | 2.9600 |
C12B···H41Dvi | 3.01 (2) | H52D···N41Cii | 2.8300 |
C12B···H12D | 2.75 (2) | H61C···C6Axi | 3.0600 |
C12B···H12Wiv | 2.79 (3) | H61C···H6Axi | 2.4000 |
H11W—O1W—H12W | 107 (2) | H31D—C3D—H32D | 108.00 |
C2C—N1C—C6C | 112.75 (13) | C4D—C3D—H31D | 109.00 |
C2C—N1C—H12C | 109.7 (11) | C3D—C4D—H4D | 109.00 |
C6C—N1C—H11C | 104.3 (10) | C41D—C4D—H4D | 109.00 |
H11C—N1C—H12C | 114.0 (17) | C5D—C4D—H4D | 109.00 |
C2C—N1C—H11C | 111.4 (10) | C4D—C5D—H51D | 109.00 |
C6C—N1C—H12C | 104.5 (11) | C6D—C5D—H51D | 109.00 |
H41C—N41C—H42C | 117.5 (16) | C6D—C5D—H52D | 109.00 |
C41C—N41C—H42C | 121.2 (12) | H51D—C5D—H52D | 108.00 |
C41C—N41C—H41C | 121.2 (11) | C4D—C5D—H52D | 109.00 |
C2D—N1D—C6D | 112.54 (12) | N1D—C6D—H62D | 109.00 |
C2D—N1D—H11D | 110.3 (10) | C5D—C6D—H61D | 109.00 |
C6D—N1D—H11D | 109.8 (10) | N1D—C6D—H61D | 109.00 |
C6D—N1D—H12D | 107.7 (11) | H61D—C6D—H62D | 108.00 |
H11D—N1D—H12D | 109.6 (15) | C5D—C6D—H62D | 109.00 |
C2D—N1D—H12D | 106.8 (11) | C2A—C1A—C6A | 117.89 (15) |
C41D—N41D—H42D | 119.1 (13) | C6A—C1A—C11A | 120.65 (15) |
H41D—N41D—H42D | 122.7 (17) | C2A—C1A—C11A | 121.41 (15) |
C41D—N41D—H41D | 118.0 (11) | C1A—C2A—C3A | 120.69 (18) |
N1C—C2C—C3C | 110.40 (14) | C2A—C3A—C4A | 120.9 (2) |
C2C—C3C—C4C | 111.32 (14) | C3A—C4A—C5A | 119.43 (17) |
C3C—C4C—C41C | 111.47 (12) | C4A—C5A—C6A | 120.04 (18) |
C3C—C4C—C5C | 109.65 (12) | C1A—C6A—C5A | 121.08 (16) |
C5C—C4C—C41C | 110.33 (12) | C1A—C11A—C12A | 109.48 (12) |
C4C—C5C—C6C | 111.06 (13) | O12A—C12A—C11A | 117.85 (13) |
N1C—C6C—C5C | 111.00 (13) | O13A—C12A—C11A | 117.78 (13) |
O41C—C41C—C4C | 121.01 (13) | O12A—C12A—O13A | 124.35 (13) |
O41C—C41C—N41C | 122.48 (15) | C1A—C2A—H2A | 120.00 |
N41C—C41C—C4C | 116.51 (13) | C3A—C2A—H2A | 120.00 |
N1C—C2C—H21C | 110.00 | C2A—C3A—H3A | 120.00 |
N1C—C2C—H22C | 110.00 | C4A—C3A—H3A | 120.00 |
C3C—C2C—H22C | 110.00 | C5A—C4A—H4A | 120.00 |
H21C—C2C—H22C | 108.00 | C3A—C4A—H4A | 120.00 |
C3C—C2C—H21C | 110.00 | C4A—C5A—H5A | 120.00 |
C2C—C3C—H31C | 109.00 | C6A—C5A—H5A | 120.00 |
C2C—C3C—H32C | 109.00 | C5A—C6A—H6A | 120.00 |
C4C—C3C—H32C | 109.00 | C1A—C6A—H6A | 119.00 |
C4C—C3C—H31C | 109.00 | C1A—C11A—H11A | 110.00 |
H31C—C3C—H32C | 108.00 | C12A—C11A—H11A | 110.00 |
C41C—C4C—H4C | 108.00 | C12A—C11A—H12A | 110.00 |
C5C—C4C—H4C | 108.00 | H11A—C11A—H12A | 108.00 |
C3C—C4C—H4C | 108.00 | C1A—C11A—H12A | 110.00 |
C6C—C5C—H51C | 109.00 | C2B—C1B—C6B | 117.49 (16) |
C4C—C5C—H51C | 109.00 | C2B—C1B—C11B | 120.95 (15) |
H51C—C5C—H52C | 108.00 | C6B—C1B—C11B | 121.55 (15) |
C6C—C5C—H52C | 109.00 | C1B—C2B—C3B | 121.63 (16) |
C4C—C5C—H52C | 109.00 | C2B—C3B—C4B | 120.25 (17) |
N1C—C6C—H61C | 109.00 | C3B—C4B—C5B | 118.79 (17) |
C5C—C6C—H62C | 109.00 | C4B—C5B—C6B | 121.05 (16) |
N1C—C6C—H62C | 109.00 | C1B—C6B—C5B | 120.79 (15) |
C5C—C6C—H61C | 109.00 | C1B—C11B—C12B | 113.90 (14) |
H61C—C6C—H62C | 108.00 | O12B—C12B—C11B | 117.73 (14) |
N1D—C2D—C3D | 111.01 (12) | O13B—C12B—C11B | 118.34 (14) |
C2D—C3D—C4D | 111.40 (12) | O12B—C12B—O13B | 123.92 (14) |
C5D—C4D—C41D | 111.99 (12) | C3B—C2B—H2B | 119.00 |
C3D—C4D—C5D | 109.56 (12) | C1B—C2B—H2B | 119.00 |
C3D—C4D—C41D | 109.57 (12) | C4B—C3B—H3B | 120.00 |
C4D—C5D—C6D | 111.24 (12) | C2B—C3B—H3B | 120.00 |
N1D—C6D—C5D | 111.19 (12) | C3B—C4B—H4B | 121.00 |
N41D—C41D—C4D | 116.31 (13) | C5B—C4B—H4B | 121.00 |
O41D—C41D—N41D | 122.36 (15) | C4B—C5B—H5B | 119.00 |
O41D—C41D—C4D | 121.32 (13) | C6B—C5B—H5B | 120.00 |
N1D—C2D—H22D | 109.00 | C5B—C6B—H6B | 120.00 |
C3D—C2D—H21D | 109.00 | C1B—C6B—H6B | 120.00 |
C3D—C2D—H22D | 109.00 | C1B—C11B—H11B | 109.00 |
H21D—C2D—H22D | 108.00 | C1B—C11B—H12B | 109.00 |
N1D—C2D—H21D | 109.00 | C12B—C11B—H12B | 109.00 |
C2D—C3D—H31D | 109.00 | H11B—C11B—H12B | 108.00 |
C2D—C3D—H32D | 109.00 | C12B—C11B—H11B | 109.00 |
C4D—C3D—H32D | 109.00 | ||
C6C—N1C—C2C—C3C | 56.10 (17) | C6A—C1A—C2A—C3A | 0.8 (2) |
C2C—N1C—C6C—C5C | −56.36 (17) | C11A—C1A—C2A—C3A | −176.53 (15) |
C6D—N1D—C2D—C3D | 55.70 (16) | C2A—C1A—C6A—C5A | −1.5 (2) |
C2D—N1D—C6D—C5D | −55.55 (17) | C11A—C1A—C6A—C5A | 175.77 (14) |
N1C—C2C—C3C—C4C | −55.83 (18) | C2A—C1A—C11A—C12A | 95.07 (17) |
C2C—C3C—C4C—C41C | 178.39 (13) | C6A—C1A—C11A—C12A | −82.13 (16) |
C2C—C3C—C4C—C5C | 55.91 (17) | C1A—C2A—C3A—C4A | 0.4 (3) |
C3C—C4C—C41C—O41C | −58.46 (19) | C2A—C3A—C4A—C5A | −0.7 (3) |
C3C—C4C—C41C—N41C | 121.61 (15) | C3A—C4A—C5A—C6A | 0.0 (3) |
C5C—C4C—C41C—O41C | 63.62 (19) | C4A—C5A—C6A—C1A | 1.2 (2) |
C5C—C4C—C41C—N41C | −116.31 (15) | C1A—C11A—C12A—O12A | −87.75 (17) |
C3C—C4C—C5C—C6C | −55.69 (17) | C1A—C11A—C12A—O13A | 90.43 (16) |
C41C—C4C—C5C—C6C | −178.84 (12) | C6B—C1B—C2B—C3B | 0.8 (3) |
C4C—C5C—C6C—N1C | 55.90 (17) | C11B—C1B—C2B—C3B | 179.74 (17) |
N1D—C2D—C3D—C4D | −55.88 (16) | C2B—C1B—C6B—C5B | −1.1 (3) |
C2D—C3D—C4D—C5D | 55.72 (16) | C11B—C1B—C6B—C5B | 179.96 (17) |
C2D—C3D—C4D—C41D | 178.95 (12) | C2B—C1B—C11B—C12B | −54.1 (2) |
C3D—C4D—C5D—C6D | −55.38 (16) | C6B—C1B—C11B—C12B | 124.84 (17) |
C41D—C4D—C5D—C6D | −177.17 (12) | C1B—C2B—C3B—C4B | 0.1 (3) |
C3D—C4D—C41D—O41D | −66.13 (18) | C2B—C3B—C4B—C5B | −0.6 (3) |
C3D—C4D—C41D—N41D | 112.70 (15) | C3B—C4B—C5B—C6B | 0.3 (3) |
C5D—C4D—C41D—O41D | 55.66 (19) | C4B—C5B—C6B—C1B | 0.6 (3) |
C5D—C4D—C41D—N41D | −125.52 (15) | C1B—C11B—C12B—O12B | −53.1 (2) |
C4D—C5D—C6D—N1D | 55.47 (16) | C1B—C11B—C12B—O13B | 127.76 (16) |
Symmetry codes: (i) x−1, −y+1/2, z+1/2; (ii) x, −y+1/2, z+1/2; (iii) x, y, z+1; (iv) x, −y+1/2, z−1/2; (v) x−1, y, z+1; (vi) x−1, y, z; (vii) x, y, z−1; (viii) −x+1, −y, −z+2; (ix) x+1, y, z; (x) x+1, −y+1/2, z−1/2; (xi) x+1, y, z−1; (xii) −x, −y, −z+1; (xiii) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1C—H11C···O13Bix | 0.941 (18) | 1.826 (18) | 2.7638 (17) | 174.8 (17) |
N1C—H12C···O13Axi | 0.93 (2) | 1.85 (2) | 2.7322 (18) | 157.9 (18) |
N1D—H11D···O12A | 0.924 (17) | 1.876 (17) | 2.7871 (17) | 168.4 (16) |
N1D—H12D···O12B | 0.96 (2) | 1.82 (2) | 2.7095 (18) | 153.0 (17) |
N41C—H41C···O12Avii | 0.86 (2) | 2.03 (2) | 2.8789 (19) | 166.3 (16) |
N41C—H42C···O41Dvii | 0.938 (18) | 1.918 (18) | 2.8480 (18) | 170.8 (14) |
N41D—H41D···O13Bix | 0.87 (2) | 2.08 (2) | 2.9177 (19) | 160.6 (16) |
N41D—H42D···O41C | 0.913 (19) | 1.917 (19) | 2.8294 (18) | 176.4 (18) |
O1W—H11W···O13A | 0.85 (2) | 1.95 (2) | 2.7881 (19) | 171 (2) |
O1W—H12W···O12Bii | 0.84 (3) | 1.99 (3) | 2.8335 (19) | 179 (3) |
C6B—H6B···O13A | 0.93 | 2.48 | 3.349 (2) | 156 |
Symmetry codes: (ii) x, −y+1/2, z+1/2; (vii) x, y, z−1; (ix) x+1, y, z; (xi) x+1, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C6H13N2O+·C8H7O2−·0.5H2O |
Mr | 273.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 12.3107 (9), 25.214 (2), 9.5402 (10) |
β (°) | 90.469 (9) |
V (Å3) | 2961.2 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini-S CCD-detector |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.959, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21326, 5802, 4258 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.105, 1.05 |
No. of reflections | 5802 |
No. of parameters | 392 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.20 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1C—H11C···O13Bi | 0.941 (18) | 1.826 (18) | 2.7638 (17) | 174.8 (17) |
N1C—H12C···O13Aii | 0.93 (2) | 1.85 (2) | 2.7322 (18) | 157.9 (18) |
N1D—H11D···O12A | 0.924 (17) | 1.876 (17) | 2.7871 (17) | 168.4 (16) |
N1D—H12D···O12B | 0.96 (2) | 1.82 (2) | 2.7095 (18) | 153.0 (17) |
N41C—H41C···O12Aiii | 0.86 (2) | 2.03 (2) | 2.8789 (19) | 166.3 (16) |
N41C—H42C···O41Diii | 0.938 (18) | 1.918 (18) | 2.8480 (18) | 170.8 (14) |
N41D—H41D···O13Bi | 0.87 (2) | 2.08 (2) | 2.9177 (19) | 160.6 (16) |
N41D—H42D···O41C | 0.913 (19) | 1.917 (19) | 2.8294 (18) | 176.4 (18) |
O1W—H11W···O13A | 0.85 (2) | 1.95 (2) | 2.7881 (19) | 171 (2) |
O1W—H12W···O12Biv | 0.84 (3) | 1.99 (3) | 2.8335 (19) | 179 (3) |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z−1; (iii) x, y, z−1; (iv) x, −y+1/2, z+1/2. |
The amide piperidine-4-carboxamide (isonipecotamide, INIPA) has proved to be a particularly useful synthon for the construction of hydrogen-bonded crystalline salts with a range of aromatic carboxylic acids, enabling their structure determination (Smith & Wermuth, 2010a, 2010b, 2010c; Smith et al., 2010). The title compound from the 1:1 stoichiometric reaction of phenylacetic acid with INIPA, the hemihydrate C6H13N2O+ C8H7O2-. 0.5H2O, (I) was obtained and the structure is reported on herein.
In (I) the asymmetric unit contains two phenylacetate anions (A and B), two INIPA cations (C and D) and a water molecule of solvation (O1W) (Fig. 1). The hydrogen-bonding environments for both sets of ion pairs are essentially identical with the piperidinium and amide 'ends' of each cation involved in lateral heteromolecular cyclic hydrogen-bonded associations [graph set R22(11) (Etter et al., 1990)] (Table 1) which incorporate a single carboxyl O-atom acceptor (Fig. 2). The rings involve (a): cation C pyrimidinium and cation D amide N—H donors and cation C amide and anion B carboxyl O-atom acceptors and (b): cation D pyrimidinium and cation C amide N—H donors and cation D amide and anion A carboxyl O-atom acceptors. These ring motifs enclose larger cyclic systems [graph set R55(21)] forming sheet substructures which lie parallel to (101) and are linked across b by the single water molecule via water O—H···Ocarboxyl associations to give the two-dimensional duplex-sheet structure (Fig. 3).
In the two independent phenylacetate anions, the conformation of the acetate side chains are significantly different [comparative torsion angles (maximum) for C2/C6–C1–C11–C12, 95.07 (17)° (A) and 124.84 (17)° (B); C1–C11–C12–O12/O13, 90.43 (16)° (A) and 127.76 (16)° (B)].