Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046867/hb2553sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046867/hb2553Isup2.hkl |
CCDC reference: 663844
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.057
- wR factor = 0.156
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 1000 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT230_ALERT_2_C Hirshfeld Test Diff for C29 - C30 .. 5.23 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C35 - C36 .. 5.41 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C37 - C38 .. 6.27 su PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C14 H11 O3
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
10 ml 2-methylpyridine was added to a 20-ml hot aqueous solution of benzylic acid (1.0 mmol, 0.23 g) and the mixture was stirred for 10 minutes under the temperature of 373 K. Then, the solution was filtered, and the filtrate was kept at room temperature. After 5 d, colorless crystals of (I) were obtained.
The N– and O-bound H atoms were located in a difference map and refined with distance restraints N—H = 0.86 (1) Å and O—H = 0.82 (1) Å; their Uiso values were freely refined.
The C-bound H atoms were placed in calculated positions (C—H = 0.93–0.96 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Supramolecular hydrogen-bonded molecular networks are of great current interest (Zhang & Chen, 2005). In this paper, we report the title supramolecular salt, (I), in which the component ions are connected by hydrogen bonds.
Compound (I) contains two pairs of 2-methylpyridinium anions and benzylate anions, in which each 2-methylpyridinium anion interacts with its adjacent benzylate anion through an intermolecular N—H···O hydrogen bond (Fig. 1 and Table 1). In addition, an intramolecular O—H···O hydrogen bond also exists in each benzylate anion and forms an S(6) ring. These O—H···O bonds are bifurcated to nearby O atoms, thus forming inversion dimers.
For related literature, see: Zhang & Chen (2005).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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: PLATON (Spek, 2003).
Fig. 1. The molecular structure of (I). Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. |
C6H8N+·C14H11O3− | Z = 4 |
Mr = 321.36 | F(000) = 680 |
Triclinic, P1 | Dx = 1.269 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.411 (6) Å | Cell parameters from 3910 reflections |
b = 12.342 (8) Å | θ = 2.5–28.2° |
c = 16.291 (11) Å | µ = 0.09 mm−1 |
α = 91.93 (1)° | T = 298 K |
β = 90.10 (1)° | Block, colourless |
γ = 95.77 (1)° | 0.45 × 0.21 × 0.12 mm |
V = 1682 (2) Å3 |
Bruker SMART APEX CCD diffractometer | 6472 independent reflections |
Radiation source: fine-focus sealed tube | 4128 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 26.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −10→9 |
Tmin = 0.963, Tmax = 0.990 | k = −15→14 |
9222 measured reflections | l = −20→13 |
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)] = 0.057 | Hydrogen site location: difmap and geom |
wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0823P)2] where P = (Fo2 + 2Fc2)/3 |
6472 reflections | (Δ/σ)max = 0.005 |
451 parameters | Δρmax = 0.20 e Å−3 |
4 restraints | Δρmin = −0.19 e Å−3 |
C6H8N+·C14H11O3− | γ = 95.77 (1)° |
Mr = 321.36 | V = 1682 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.411 (6) Å | Mo Kα radiation |
b = 12.342 (8) Å | µ = 0.09 mm−1 |
c = 16.291 (11) Å | T = 298 K |
α = 91.93 (1)° | 0.45 × 0.21 × 0.12 mm |
β = 90.10 (1)° |
Bruker SMART APEX CCD diffractometer | 6472 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 4128 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.990 | Rint = 0.021 |
9222 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 4 restraints |
wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.20 e Å−3 |
6472 reflections | Δρmin = −0.19 e Å−3 |
451 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.55457 (15) | 0.82749 (9) | 0.75636 (7) | 0.0485 (3) | |
H1A | 0.5007 (14) | 0.8084 (11) | 0.7996 (6) | 0.078 (5)* | |
N2 | 0.89574 (15) | 0.81387 (10) | 0.26014 (7) | 0.0502 (3) | |
H2A | 0.9425 (15) | 0.7909 (11) | 0.3023 (6) | 0.091 (6)* | |
O1 | 1.04816 (13) | 0.74676 (8) | 0.38526 (6) | 0.0570 (3) | |
O2 | 0.98770 (13) | 0.90310 (8) | 0.43913 (6) | 0.0596 (3) | |
O3 | 1.21228 (13) | 0.91798 (7) | 0.54884 (6) | 0.0521 (3) | |
H3 | 1.1438 (11) | 0.9577 (9) | 0.5379 (9) | 0.082 (6)* | |
O4 | 0.38038 (14) | 0.75371 (8) | 0.87914 (6) | 0.0632 (3) | |
O5 | 0.47755 (13) | 0.91188 (8) | 0.93295 (6) | 0.0621 (3) | |
O6 | 0.25502 (13) | 0.92267 (7) | 1.04037 (6) | 0.0494 (3) | |
H6 | 0.3435 (10) | 0.9560 (12) | 1.0315 (11) | 0.113 (7)* | |
C1 | 0.57741 (19) | 0.75707 (11) | 0.69531 (8) | 0.0497 (4) | |
C2 | 0.6699 (2) | 0.79273 (13) | 0.63023 (9) | 0.0661 (5) | |
H2 | 0.6880 | 0.7448 | 0.5868 | 0.079* | |
C3 | 0.7350 (2) | 0.89825 (14) | 0.62927 (10) | 0.0703 (5) | |
H3A | 0.7974 | 0.9224 | 0.5851 | 0.084* | |
C4 | 0.7087 (2) | 0.96873 (14) | 0.69324 (10) | 0.0691 (5) | |
H4 | 0.7526 | 1.0410 | 0.6932 | 0.083* | |
C5 | 0.6171 (2) | 0.93118 (13) | 0.75678 (9) | 0.0599 (5) | |
H5 | 0.5979 | 0.9780 | 0.8008 | 0.072* | |
C6 | 0.5010 (2) | 0.64462 (12) | 0.70150 (10) | 0.0716 (6) | |
H6A | 0.4730 | 0.6313 | 0.7576 | 0.107* | |
H6B | 0.5740 | 0.5941 | 0.6829 | 0.107* | |
H6C | 0.4063 | 0.6353 | 0.6680 | 0.107* | |
C7 | 1.05986 (17) | 0.82215 (11) | 0.43985 (8) | 0.0400 (4) | |
C8 | 1.17637 (17) | 0.81246 (10) | 0.51333 (8) | 0.0403 (4) | |
C9 | 1.33132 (17) | 0.77351 (10) | 0.48098 (8) | 0.0407 (4) | |
C10 | 1.35768 (19) | 0.66546 (11) | 0.47539 (9) | 0.0500 (4) | |
H10 | 1.2806 | 0.6130 | 0.4943 | 0.060* | |
C11 | 1.4980 (2) | 0.63371 (13) | 0.44183 (9) | 0.0606 (5) | |
H11 | 1.5139 | 0.5602 | 0.4385 | 0.073* | |
C12 | 1.6127 (2) | 0.70919 (14) | 0.41370 (9) | 0.0655 (5) | |
H12 | 1.7066 | 0.6878 | 0.3911 | 0.079* | |
C13 | 1.5875 (2) | 0.81688 (14) | 0.41924 (10) | 0.0651 (5) | |
H13 | 1.6651 | 0.8692 | 0.4005 | 0.078* | |
C14 | 1.4494 (2) | 0.84836 (12) | 0.45196 (9) | 0.0535 (4) | |
H14 | 1.4344 | 0.9220 | 0.4548 | 0.064* | |
C15 | 1.09641 (17) | 0.73823 (10) | 0.57771 (8) | 0.0416 (4) | |
C16 | 0.9994 (2) | 0.64452 (12) | 0.55794 (9) | 0.0556 (5) | |
H16 | 0.9780 | 0.6247 | 0.5031 | 0.067* | |
C17 | 0.9334 (2) | 0.57936 (13) | 0.61955 (10) | 0.0674 (5) | |
H17 | 0.8690 | 0.5157 | 0.6057 | 0.081* | |
C18 | 0.9622 (2) | 0.60797 (13) | 0.70014 (10) | 0.0677 (5) | |
H18 | 0.9160 | 0.5645 | 0.7410 | 0.081* | |
C19 | 1.0583 (2) | 0.69983 (14) | 0.72092 (10) | 0.0681 (5) | |
H19 | 1.0784 | 0.7191 | 0.7759 | 0.082* | |
C20 | 1.1260 (2) | 0.76461 (12) | 0.66033 (9) | 0.0553 (5) | |
H20 | 1.1926 | 0.8270 | 0.6750 | 0.066* | |
C21 | 0.85741 (19) | 0.74396 (12) | 0.19715 (9) | 0.0508 (4) | |
C22 | 0.7842 (2) | 0.78106 (13) | 0.12961 (9) | 0.0632 (5) | |
H22 | 0.7579 | 0.7339 | 0.0849 | 0.076* | |
C23 | 0.7499 (2) | 0.88649 (14) | 0.12772 (10) | 0.0720 (6) | |
H23 | 0.6987 | 0.9110 | 0.0822 | 0.086* | |
C24 | 0.7913 (2) | 0.95657 (14) | 0.19350 (10) | 0.0689 (5) | |
H24 | 0.7699 | 1.0290 | 0.1930 | 0.083* | |
C25 | 0.8642 (2) | 0.91750 (12) | 0.25919 (9) | 0.0584 (5) | |
H25 | 0.8925 | 0.9638 | 0.3042 | 0.070* | |
C26 | 0.8965 (2) | 0.63068 (13) | 0.20524 (11) | 0.0757 (6) | |
H26A | 0.9899 | 0.6196 | 0.1735 | 0.114* | |
H26B | 0.8083 | 0.5811 | 0.1855 | 0.114* | |
H26C | 0.9166 | 0.6177 | 0.2619 | 0.114* | |
C27 | 0.38621 (17) | 0.82880 (11) | 0.93368 (8) | 0.0417 (4) | |
C28 | 0.26647 (17) | 0.81715 (10) | 1.00538 (8) | 0.0396 (4) | |
C29 | 0.10108 (17) | 0.77338 (10) | 0.97282 (8) | 0.0385 (4) | |
C30 | 0.05481 (19) | 0.66345 (11) | 0.96260 (9) | 0.0498 (4) | |
H30 | 0.1252 | 0.6136 | 0.9768 | 0.060* | |
C31 | −0.0947 (2) | 0.62605 (12) | 0.93151 (9) | 0.0577 (5) | |
H31 | −0.1241 | 0.5515 | 0.9256 | 0.069* | |
C32 | −0.1989 (2) | 0.69766 (13) | 0.90959 (9) | 0.0600 (5) | |
H32 | −0.2998 | 0.6724 | 0.8893 | 0.072* | |
C33 | −0.1539 (2) | 0.80724 (13) | 0.91777 (9) | 0.0590 (5) | |
H33 | −0.2238 | 0.8567 | 0.9022 | 0.071* | |
C34 | −0.00477 (19) | 0.84452 (12) | 0.94907 (8) | 0.0496 (4) | |
H34 | 0.0246 | 0.9191 | 0.9542 | 0.060* | |
C35 | 0.32473 (17) | 0.74434 (11) | 1.07113 (8) | 0.0432 (4) | |
C36 | 0.2938 (2) | 0.76866 (13) | 1.15287 (9) | 0.0605 (5) | |
H36 | 0.2389 | 0.8285 | 1.1662 | 0.073* | |
C37 | 0.3424 (3) | 0.70632 (14) | 1.21463 (10) | 0.0775 (6) | |
H37 | 0.3202 | 0.7241 | 1.2691 | 0.093* | |
C38 | 0.4231 (3) | 0.61854 (14) | 1.19611 (11) | 0.0818 (6) | |
H38 | 0.4566 | 0.5765 | 1.2379 | 0.098* | |
C39 | 0.4550 (2) | 0.59202 (13) | 1.11579 (11) | 0.0749 (6) | |
H39 | 0.5091 | 0.5315 | 1.1031 | 0.090* | |
C40 | 0.4066 (2) | 0.65565 (12) | 1.05309 (10) | 0.0580 (5) | |
H40 | 0.4298 | 0.6380 | 0.9988 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0511 (8) | 0.0545 (7) | 0.0395 (6) | 0.0025 (6) | 0.0054 (6) | 0.0026 (5) |
N2 | 0.0504 (8) | 0.0606 (7) | 0.0397 (6) | 0.0054 (6) | −0.0038 (6) | 0.0044 (6) |
O1 | 0.0706 (7) | 0.0528 (6) | 0.0489 (6) | 0.0175 (5) | −0.0211 (5) | −0.0124 (5) |
O2 | 0.0695 (7) | 0.0553 (6) | 0.0569 (6) | 0.0238 (5) | −0.0166 (5) | −0.0080 (5) |
O3 | 0.0620 (7) | 0.0362 (5) | 0.0573 (6) | 0.0051 (5) | −0.0152 (5) | −0.0084 (4) |
O4 | 0.0648 (7) | 0.0619 (6) | 0.0568 (6) | −0.0168 (5) | 0.0180 (5) | −0.0168 (5) |
O5 | 0.0608 (7) | 0.0591 (6) | 0.0601 (6) | −0.0213 (5) | 0.0128 (5) | −0.0099 (5) |
O6 | 0.0534 (6) | 0.0391 (5) | 0.0539 (6) | −0.0013 (5) | 0.0063 (5) | −0.0090 (4) |
C1 | 0.0552 (9) | 0.0529 (8) | 0.0428 (8) | 0.0141 (7) | −0.0048 (7) | 0.0021 (7) |
C2 | 0.0813 (12) | 0.0758 (11) | 0.0440 (9) | 0.0200 (9) | 0.0126 (8) | 0.0052 (8) |
C3 | 0.0750 (12) | 0.0837 (11) | 0.0527 (9) | 0.0042 (10) | 0.0154 (9) | 0.0216 (8) |
C4 | 0.0778 (13) | 0.0662 (10) | 0.0604 (10) | −0.0102 (9) | 0.0049 (9) | 0.0125 (8) |
C5 | 0.0700 (11) | 0.0560 (9) | 0.0512 (9) | −0.0049 (8) | 0.0038 (8) | −0.0006 (7) |
C6 | 0.0946 (14) | 0.0561 (10) | 0.0630 (10) | 0.0032 (10) | 0.0064 (10) | −0.0004 (8) |
C7 | 0.0410 (8) | 0.0408 (7) | 0.0381 (7) | 0.0031 (6) | −0.0007 (6) | 0.0011 (6) |
C8 | 0.0467 (8) | 0.0334 (7) | 0.0394 (7) | 0.0002 (6) | −0.0065 (6) | −0.0062 (6) |
C9 | 0.0412 (8) | 0.0430 (7) | 0.0365 (7) | −0.0009 (6) | −0.0084 (6) | −0.0011 (6) |
C10 | 0.0515 (9) | 0.0446 (8) | 0.0523 (9) | 0.0001 (7) | 0.0020 (7) | −0.0045 (7) |
C11 | 0.0624 (11) | 0.0581 (9) | 0.0625 (10) | 0.0151 (8) | 0.0036 (8) | −0.0076 (8) |
C12 | 0.0497 (10) | 0.0891 (12) | 0.0570 (10) | 0.0067 (9) | 0.0065 (8) | −0.0052 (9) |
C13 | 0.0515 (10) | 0.0780 (11) | 0.0626 (10) | −0.0102 (9) | 0.0055 (8) | 0.0072 (9) |
C14 | 0.0540 (10) | 0.0502 (8) | 0.0547 (9) | −0.0032 (8) | −0.0033 (8) | 0.0048 (7) |
C15 | 0.0412 (8) | 0.0429 (7) | 0.0412 (7) | 0.0080 (6) | −0.0041 (6) | −0.0027 (6) |
C16 | 0.0639 (11) | 0.0548 (9) | 0.0451 (8) | −0.0065 (8) | 0.0040 (8) | −0.0065 (7) |
C17 | 0.0726 (12) | 0.0584 (10) | 0.0685 (11) | −0.0081 (9) | 0.0087 (9) | 0.0047 (8) |
C18 | 0.0841 (13) | 0.0673 (10) | 0.0526 (9) | 0.0080 (10) | 0.0131 (9) | 0.0153 (8) |
C19 | 0.0848 (13) | 0.0802 (11) | 0.0397 (8) | 0.0088 (10) | 0.0012 (8) | 0.0052 (8) |
C20 | 0.0634 (11) | 0.0584 (9) | 0.0430 (8) | 0.0027 (8) | −0.0064 (7) | −0.0034 (7) |
C21 | 0.0503 (9) | 0.0575 (9) | 0.0439 (8) | 0.0011 (7) | −0.0013 (7) | 0.0039 (7) |
C22 | 0.0740 (12) | 0.0750 (11) | 0.0390 (8) | −0.0006 (9) | −0.0113 (8) | 0.0046 (8) |
C23 | 0.0811 (13) | 0.0871 (12) | 0.0499 (9) | 0.0129 (10) | −0.0096 (9) | 0.0196 (9) |
C24 | 0.0871 (13) | 0.0672 (10) | 0.0552 (10) | 0.0165 (10) | −0.0029 (9) | 0.0143 (8) |
C25 | 0.0689 (11) | 0.0569 (9) | 0.0499 (9) | 0.0084 (8) | −0.0045 (8) | 0.0014 (7) |
C26 | 0.0916 (14) | 0.0651 (11) | 0.0710 (11) | 0.0138 (10) | −0.0158 (10) | −0.0054 (9) |
C27 | 0.0405 (8) | 0.0405 (7) | 0.0427 (8) | −0.0025 (6) | −0.0033 (6) | 0.0003 (6) |
C28 | 0.0414 (8) | 0.0367 (7) | 0.0399 (7) | 0.0007 (6) | 0.0002 (6) | −0.0030 (6) |
C29 | 0.0399 (8) | 0.0402 (7) | 0.0348 (7) | 0.0006 (6) | 0.0018 (6) | 0.0025 (6) |
C30 | 0.0474 (9) | 0.0452 (8) | 0.0565 (9) | 0.0009 (7) | −0.0078 (7) | 0.0082 (7) |
C31 | 0.0567 (10) | 0.0550 (9) | 0.0575 (9) | −0.0141 (8) | −0.0099 (8) | 0.0053 (7) |
C32 | 0.0454 (10) | 0.0782 (11) | 0.0539 (9) | −0.0056 (9) | −0.0076 (8) | 0.0013 (8) |
C33 | 0.0500 (10) | 0.0737 (10) | 0.0552 (9) | 0.0166 (8) | −0.0096 (8) | 0.0002 (8) |
C34 | 0.0545 (10) | 0.0473 (8) | 0.0478 (8) | 0.0083 (7) | −0.0014 (7) | 0.0015 (7) |
C35 | 0.0414 (8) | 0.0443 (8) | 0.0419 (8) | −0.0060 (7) | −0.0055 (6) | 0.0013 (6) |
C36 | 0.0647 (11) | 0.0680 (10) | 0.0482 (9) | 0.0017 (9) | −0.0006 (8) | 0.0062 (8) |
C37 | 0.1015 (16) | 0.0827 (12) | 0.0470 (9) | −0.0014 (11) | −0.0054 (10) | 0.0135 (9) |
C38 | 0.0991 (15) | 0.0725 (11) | 0.0719 (11) | −0.0086 (11) | −0.0303 (11) | 0.0287 (9) |
C39 | 0.0767 (13) | 0.0532 (10) | 0.0953 (13) | 0.0076 (9) | −0.0244 (11) | 0.0110 (9) |
C40 | 0.0602 (10) | 0.0539 (9) | 0.0598 (9) | 0.0059 (8) | −0.0107 (8) | 0.0012 (8) |
N1—C1 | 1.3259 (18) | C17—C18 | 1.363 (2) |
N1—C5 | 1.334 (2) | C17—H17 | 0.9300 |
N1—H1A | 0.864 (8) | C18—C19 | 1.357 (2) |
N2—C25 | 1.333 (2) | C18—H18 | 0.9300 |
N2—C21 | 1.3361 (19) | C19—C20 | 1.379 (2) |
N2—H2A | 0.862 (8) | C19—H19 | 0.9300 |
O1—C7 | 1.2617 (16) | C20—H20 | 0.9300 |
O2—C7 | 1.2204 (17) | C21—C22 | 1.374 (2) |
O3—C8 | 1.4113 (17) | C21—C26 | 1.478 (2) |
O3—H3 | 0.816 (8) | C22—C23 | 1.362 (2) |
O4—C27 | 1.2594 (17) | C22—H22 | 0.9300 |
O5—C27 | 1.2183 (17) | C23—C24 | 1.376 (2) |
O6—C28 | 1.4163 (17) | C23—H23 | 0.9300 |
O6—H6 | 0.829 (8) | C24—C25 | 1.359 (2) |
C1—C2 | 1.374 (2) | C24—H24 | 0.9300 |
C1—C6 | 1.476 (2) | C25—H25 | 0.9300 |
C2—C3 | 1.362 (2) | C26—H26A | 0.9600 |
C2—H2 | 0.9300 | C26—H26B | 0.9600 |
C3—C4 | 1.368 (2) | C26—H26C | 0.9600 |
C3—H3A | 0.9300 | C27—C28 | 1.545 (2) |
C4—C5 | 1.358 (2) | C28—C29 | 1.528 (2) |
C4—H4 | 0.9300 | C28—C35 | 1.532 (2) |
C5—H5 | 0.9300 | C29—C30 | 1.378 (2) |
C6—H6A | 0.9600 | C29—C34 | 1.376 (2) |
C6—H6B | 0.9600 | C30—C31 | 1.384 (2) |
C6—H6C | 0.9600 | C30—H30 | 0.9300 |
C7—C8 | 1.561 (2) | C31—C32 | 1.362 (2) |
C8—C9 | 1.523 (2) | C31—H31 | 0.9300 |
C8—C15 | 1.5279 (19) | C32—C33 | 1.369 (2) |
C9—C14 | 1.382 (2) | C32—H32 | 0.9300 |
C9—C10 | 1.374 (2) | C33—C34 | 1.382 (2) |
C10—C11 | 1.388 (2) | C33—H33 | 0.9300 |
C10—H10 | 0.9300 | C34—H34 | 0.9300 |
C11—C12 | 1.363 (2) | C35—C40 | 1.374 (2) |
C11—H11 | 0.9300 | C35—C36 | 1.386 (2) |
C12—C13 | 1.367 (2) | C36—C37 | 1.373 (2) |
C12—H12 | 0.9300 | C36—H36 | 0.9300 |
C13—C14 | 1.365 (2) | C37—C38 | 1.361 (3) |
C13—H13 | 0.9300 | C37—H37 | 0.9300 |
C14—H14 | 0.9300 | C38—C39 | 1.372 (3) |
C15—C16 | 1.375 (2) | C38—H38 | 0.9300 |
C15—C20 | 1.390 (2) | C39—C40 | 1.394 (2) |
C16—C17 | 1.389 (2) | C39—H39 | 0.9300 |
C16—H16 | 0.9300 | C40—H40 | 0.9300 |
C1—N1—C5 | 122.62 (13) | C20—C19—H19 | 120.1 |
C1—N1—H1A | 121.9 (9) | C15—C20—C19 | 121.15 (15) |
C5—N1—H1A | 115.4 (9) | C15—C20—H20 | 119.4 |
C25—N2—C21 | 121.89 (13) | C19—C20—H20 | 119.4 |
C25—N2—H2A | 119.5 (9) | N2—C21—C22 | 118.51 (15) |
C21—N2—H2A | 118.6 (9) | N2—C21—C26 | 117.26 (14) |
C8—O3—H3 | 111.4 (9) | C22—C21—C26 | 124.23 (14) |
C28—O6—H6 | 104.1 (11) | C23—C22—C21 | 120.48 (15) |
N1—C1—C2 | 118.39 (14) | C23—C22—H22 | 119.8 |
N1—C1—C6 | 117.65 (14) | C21—C22—H22 | 119.8 |
C2—C1—C6 | 123.96 (14) | C22—C23—C24 | 119.61 (16) |
C3—C2—C1 | 120.08 (15) | C22—C23—H23 | 120.2 |
C3—C2—H2 | 120.0 | C24—C23—H23 | 120.2 |
C1—C2—H2 | 120.0 | C25—C24—C23 | 118.48 (16) |
C2—C3—C4 | 119.95 (16) | C25—C24—H24 | 120.8 |
C2—C3—H3A | 120.0 | C23—C24—H24 | 120.8 |
C4—C3—H3A | 120.0 | N2—C25—C24 | 121.03 (15) |
C5—C4—C3 | 118.69 (16) | N2—C25—H25 | 119.5 |
C5—C4—H4 | 120.7 | C24—C25—H25 | 119.5 |
C3—C4—H4 | 120.7 | C21—C26—H26A | 109.5 |
N1—C5—C4 | 120.28 (15) | C21—C26—H26B | 109.5 |
N1—C5—H5 | 119.9 | H26A—C26—H26B | 109.5 |
C4—C5—H5 | 119.9 | C21—C26—H26C | 109.5 |
C1—C6—H6A | 109.5 | H26A—C26—H26C | 109.5 |
C1—C6—H6B | 109.5 | H26B—C26—H26C | 109.5 |
H6A—C6—H6B | 109.5 | O5—C27—O4 | 124.52 (14) |
C1—C6—H6C | 109.5 | O5—C27—C28 | 117.26 (12) |
H6A—C6—H6C | 109.5 | O4—C27—C28 | 118.20 (12) |
H6B—C6—H6C | 109.5 | O6—C28—C29 | 107.76 (11) |
O2—C7—O1 | 124.76 (13) | O6—C28—C27 | 107.54 (10) |
O2—C7—C8 | 117.27 (11) | C29—C28—C27 | 109.94 (11) |
O1—C7—C8 | 117.96 (12) | O6—C28—C35 | 109.09 (11) |
O3—C8—C9 | 107.94 (11) | C29—C28—C35 | 111.47 (11) |
O3—C8—C15 | 109.00 (11) | C27—C28—C35 | 110.91 (12) |
C9—C8—C15 | 112.85 (11) | C30—C29—C34 | 117.69 (14) |
O3—C8—C7 | 107.33 (10) | C30—C29—C28 | 122.26 (13) |
C9—C8—C7 | 109.21 (11) | C34—C29—C28 | 119.99 (13) |
C15—C8—C7 | 110.34 (12) | C29—C30—C31 | 121.06 (14) |
C14—C9—C10 | 117.42 (14) | C29—C30—H30 | 119.5 |
C14—C9—C8 | 119.53 (13) | C31—C30—H30 | 119.5 |
C10—C9—C8 | 122.98 (12) | C32—C31—C30 | 120.43 (15) |
C11—C10—C9 | 120.79 (14) | C32—C31—H31 | 119.8 |
C11—C10—H10 | 119.6 | C30—C31—H31 | 119.8 |
C9—C10—H10 | 119.6 | C33—C32—C31 | 119.34 (16) |
C12—C11—C10 | 120.67 (16) | C33—C32—H32 | 120.3 |
C12—C11—H11 | 119.7 | C31—C32—H32 | 120.3 |
C10—C11—H11 | 119.7 | C32—C33—C34 | 120.18 (15) |
C11—C12—C13 | 118.87 (17) | C32—C33—H33 | 119.9 |
C11—C12—H12 | 120.6 | C34—C33—H33 | 119.9 |
C13—C12—H12 | 120.6 | C33—C34—C29 | 121.27 (15) |
C12—C13—C14 | 120.61 (16) | C33—C34—H34 | 119.4 |
C12—C13—H13 | 119.7 | C29—C34—H34 | 119.4 |
C14—C13—H13 | 119.7 | C40—C35—C36 | 118.14 (14) |
C13—C14—C9 | 121.65 (15) | C40—C35—C28 | 123.16 (13) |
C13—C14—H14 | 119.2 | C36—C35—C28 | 118.70 (13) |
C9—C14—H14 | 119.2 | C37—C36—C35 | 121.48 (16) |
C16—C15—C20 | 118.07 (13) | C37—C36—H36 | 119.3 |
C16—C15—C8 | 123.16 (12) | C35—C36—H36 | 119.3 |
C20—C15—C8 | 118.76 (13) | C38—C37—C36 | 119.93 (17) |
C15—C16—C17 | 120.20 (14) | C38—C37—H37 | 120.0 |
C15—C16—H16 | 119.9 | C36—C37—H37 | 120.0 |
C17—C16—H16 | 119.9 | C37—C38—C39 | 120.03 (17) |
C18—C17—C16 | 120.57 (16) | C37—C38—H38 | 120.0 |
C18—C17—H17 | 119.7 | C39—C38—H38 | 120.0 |
C16—C17—H17 | 119.7 | C38—C39—C40 | 120.08 (17) |
C17—C18—C19 | 120.13 (15) | C38—C39—H39 | 120.0 |
C17—C18—H18 | 119.9 | C40—C39—H39 | 120.0 |
C19—C18—H18 | 119.9 | C35—C40—C39 | 120.34 (16) |
C18—C19—C20 | 119.87 (15) | C35—C40—H40 | 119.8 |
C18—C19—H19 | 120.1 | C39—C40—H40 | 119.8 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4 | 0.86 (1) | 1.76 (1) | 2.6155 (19) | 172 (1) |
N2—H2A···O1 | 0.86 (1) | 1.75 (1) | 2.6081 (19) | 177 (1) |
O3—H3···O2 | 0.82 (1) | 2.12 (1) | 2.5870 (19) | 116 (1) |
O3—H3···O2i | 0.82 (1) | 2.16 (1) | 2.909 (2) | 153 (1) |
O6—H6···O5 | 0.83 (1) | 2.05 (2) | 2.5748 (19) | 120 (1) |
O6—H6···O5ii | 0.83 (1) | 2.17 (1) | 2.904 (2) | 148 (2) |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C6H8N+·C14H11O3− |
Mr | 321.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.411 (6), 12.342 (8), 16.291 (11) |
α, β, γ (°) | 91.93 (1), 90.10 (1), 95.77 (1) |
V (Å3) | 1682 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.45 × 0.21 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.963, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9222, 6472, 4128 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.156, 0.99 |
No. of reflections | 6472 |
No. of parameters | 451 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.19 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4 | 0.864 (8) | 1.757 (8) | 2.6155 (19) | 172.0 (13) |
N2—H2A···O1 | 0.862 (8) | 1.748 (8) | 2.6081 (19) | 176.6 (14) |
O3—H3···O2 | 0.816 (8) | 2.123 (13) | 2.5870 (19) | 116.0 (11) |
O3—H3···O2i | 0.816 (8) | 2.158 (9) | 2.909 (2) | 153.1 (13) |
O6—H6···O5 | 0.829 (8) | 2.053 (15) | 2.5748 (19) | 120.4 (14) |
O6—H6···O5ii | 0.829 (8) | 2.167 (11) | 2.904 (2) | 148.0 (16) |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+2. |
Supramolecular hydrogen-bonded molecular networks are of great current interest (Zhang & Chen, 2005). In this paper, we report the title supramolecular salt, (I), in which the component ions are connected by hydrogen bonds.
Compound (I) contains two pairs of 2-methylpyridinium anions and benzylate anions, in which each 2-methylpyridinium anion interacts with its adjacent benzylate anion through an intermolecular N—H···O hydrogen bond (Fig. 1 and Table 1). In addition, an intramolecular O—H···O hydrogen bond also exists in each benzylate anion and forms an S(6) ring. These O—H···O bonds are bifurcated to nearby O atoms, thus forming inversion dimers.