The title compound, C
20H
18N
4O
2·2H
2O, has an inversion center at the mid-point of the central benzene ring. The asymmetric unit consists of one-half of an
N1,
N4-bis(pyridin-4-ylmethyl)terephthalamide molecule and one water molecule. The intermolecular hydrogen bonds connect the amide molecules and water molecules to produce a self-interpenetrating hydrogen-bonding network. The crystal packing is also governed by intermolecular π–π stacking and a weak C—H
π interaction.
Supporting information
CCDC reference: 277772
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C)= 0.004 Å
- R factor = 0.050
- wR factor = 0.113
- Data-to-parameter ratio = 11.9
checkCIF/PLATON results
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Data collection: SMART (Bruker, 1997); cell refinement: SMART or SAINT-Plus? (Bruker, 1997); data reduction: SAINT-Plus and SHELXS97 (Sheldrick, 1997); program(s) used to solve structure: SHELXS97; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.
N1,
N4-bis(pyridin-4-ylmethyl)terephthalamide dihydrate
top
Crystal data top
C20H18N4O2·2H2O | F(000) = 404 |
Mr = 382.42 | Dx = 1.384 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 573 reflections |
a = 8.1173 (13) Å | θ = 3.0–19.2° |
b = 9.8449 (15) Å | µ = 0.10 mm−1 |
c = 13.6802 (17) Å | T = 298 K |
β = 122.944 (7)° | Block, colorless |
V = 917.4 (2) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1614 independent reflections |
Radiation source: fine-focus sealed tube | 969 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
φ and ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −8→9 |
Tmin = 0.980, Tmax = 0.988 | k = −7→11 |
4470 measured reflections | l = −16→15 |
Refinement top
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0437P)2] where P = (Fo2 + 2Fc2)/3 |
1614 reflections | (Δ/σ)max < 0.001 |
136 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
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 | |
C1 | 1.1628 (4) | 0.4881 (3) | 0.4382 (2) | 0.0489 (8) | |
H1 | 1.2916 | 0.4698 | 0.4980 | 0.053 (8)* | |
C2 | 1.0272 (4) | 0.3858 (3) | 0.4040 (2) | 0.0444 (7) | |
H2 | 1.0651 | 0.3015 | 0.4404 | 0.051 (8)* | |
C3 | 0.8329 (4) | 0.4085 (3) | 0.3148 (2) | 0.0360 (6) | |
C4 | 0.7902 (4) | 0.5367 (3) | 0.2655 (2) | 0.0427 (7) | |
H4 | 0.6627 | 0.5582 | 0.2056 | 0.042 (7)* | |
C5 | 0.9370 (4) | 0.6320 (3) | 0.3055 (3) | 0.0490 (8) | |
H5 | 0.9040 | 0.7171 | 0.2703 | 0.051 (8)* | |
C6 | 0.6833 (4) | 0.2970 (3) | 0.2768 (2) | 0.0410 (7) | |
H6A | 0.7259 | 0.2188 | 0.2530 | 0.043 (7)* | |
H6B | 0.6765 | 0.2700 | 0.3427 | 0.038 (7)* | |
C7 | 0.3610 (4) | 0.3997 (2) | 0.1994 (2) | 0.0364 (7) | |
C8 | 0.1765 (4) | 0.4506 (2) | 0.0941 (2) | 0.0320 (6) | |
C9 | 0.1572 (4) | 0.4784 (2) | −0.0099 (2) | 0.0368 (7) | |
H9 | 0.2632 | 0.4644 | −0.0173 | 0.035 (7)* | |
C10 | −0.0170 (4) | 0.5270 (2) | −0.1035 (2) | 0.0373 (7) | |
H10 | −0.0276 | 0.5450 | −0.1734 | 0.024 (6)* | |
N1 | 1.1223 (3) | 0.6115 (2) | 0.3913 (2) | 0.0495 (6) | |
N2 | 0.4893 (3) | 0.3366 (2) | 0.18205 (19) | 0.0387 (6) | |
H3 | 0.4552 | 0.3192 | 0.1119 | 0.037 (8)* | |
O1 | 0.3929 (3) | 0.41625 (19) | 0.29726 (16) | 0.0523 (6) | |
O2 | 0.5247 (3) | 0.23635 (19) | 0.49215 (16) | 0.0575 (6) | |
H7A | 0.4403 | 0.2605 | 0.4226 | 0.069* | |
H7B | 0.6322 | 0.2267 | 0.4962 | 0.069* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0343 (18) | 0.057 (2) | 0.0441 (19) | 0.0031 (15) | 0.0140 (16) | −0.0062 (15) |
C2 | 0.0400 (18) | 0.0402 (18) | 0.0495 (19) | 0.0093 (14) | 0.0221 (16) | 0.0047 (14) |
C3 | 0.0347 (16) | 0.0393 (16) | 0.0363 (16) | 0.0084 (13) | 0.0208 (14) | 0.0028 (13) |
C4 | 0.0376 (17) | 0.0472 (19) | 0.0409 (18) | 0.0077 (15) | 0.0200 (15) | 0.0050 (14) |
C5 | 0.053 (2) | 0.0400 (19) | 0.059 (2) | 0.0019 (16) | 0.0335 (18) | 0.0043 (15) |
C6 | 0.0366 (17) | 0.0412 (18) | 0.0445 (18) | 0.0067 (13) | 0.0216 (15) | 0.0056 (13) |
C7 | 0.0354 (16) | 0.0336 (16) | 0.0386 (17) | −0.0018 (12) | 0.0191 (14) | 0.0003 (12) |
C8 | 0.0330 (15) | 0.0274 (15) | 0.0329 (15) | −0.0029 (11) | 0.0162 (13) | −0.0031 (11) |
C9 | 0.0323 (16) | 0.0400 (17) | 0.0443 (18) | 0.0017 (12) | 0.0249 (15) | 0.0022 (12) |
C10 | 0.0405 (17) | 0.0420 (17) | 0.0331 (17) | 0.0032 (13) | 0.0223 (14) | 0.0032 (12) |
N1 | 0.0447 (15) | 0.0463 (17) | 0.0561 (17) | −0.0027 (12) | 0.0265 (14) | −0.0049 (12) |
N2 | 0.0319 (13) | 0.0432 (14) | 0.0365 (15) | 0.0047 (10) | 0.0157 (12) | −0.0005 (10) |
O1 | 0.0465 (12) | 0.0719 (15) | 0.0349 (12) | 0.0099 (10) | 0.0198 (10) | 0.0017 (10) |
O2 | 0.0449 (12) | 0.0737 (15) | 0.0547 (13) | −0.0046 (10) | 0.0276 (10) | 0.0088 (10) |
Geometric parameters (Å, º) top
C1—N1 | 1.329 (3) | C6—H6B | 0.9700 |
C1—C2 | 1.373 (4) | C7—O1 | 1.228 (3) |
C1—H1 | 0.9298 | C7—N2 | 1.340 (3) |
C2—C3 | 1.391 (3) | C7—C8 | 1.491 (3) |
C2—H2 | 0.9299 | C8—C9 | 1.371 (3) |
C3—C4 | 1.383 (3) | C8—C10i | 1.386 (3) |
C3—C6 | 1.505 (3) | C9—C10 | 1.378 (3) |
C4—C5 | 1.375 (4) | C9—H9 | 0.9297 |
C4—H4 | 0.9301 | C10—C8i | 1.386 (3) |
C5—N1 | 1.327 (3) | C10—H10 | 0.9294 |
C5—H5 | 0.9302 | N2—H3 | 0.8597 |
C6—N2 | 1.446 (3) | O2—H7A | 0.8501 |
C6—H6A | 0.9698 | O2—H7B | 0.8500 |
| | | |
N1—C1—C2 | 124.4 (3) | C3—C6—H6B | 108.8 |
N1—C1—H1 | 117.8 | H6A—C6—H6B | 107.8 |
C2—C1—H1 | 117.8 | O1—C7—N2 | 122.1 (2) |
C1—C2—C3 | 119.8 (3) | O1—C7—C8 | 121.0 (2) |
C1—C2—H2 | 120.1 | N2—C7—C8 | 117.0 (2) |
C3—C2—H2 | 120.1 | C9—C8—C10i | 118.6 (2) |
C4—C3—C2 | 116.0 (3) | C9—C8—C7 | 123.9 (2) |
C4—C3—C6 | 123.8 (2) | C10i—C8—C7 | 117.5 (2) |
C2—C3—C6 | 120.2 (2) | C8—C9—C10 | 120.9 (2) |
C5—C4—C3 | 119.7 (3) | C8—C9—H9 | 119.5 |
C5—C4—H4 | 120.2 | C10—C9—H9 | 119.6 |
C3—C4—H4 | 120.1 | C9—C10—C8i | 120.5 (2) |
N1—C5—C4 | 124.6 (3) | C9—C10—H10 | 119.8 |
N1—C5—H5 | 117.6 | C8i—C10—H10 | 119.8 |
C4—C5—H5 | 117.7 | C5—N1—C1 | 115.5 (2) |
N2—C6—C3 | 113.2 (2) | C7—N2—C6 | 122.6 (2) |
N2—C6—H6A | 109.1 | C7—N2—H3 | 118.8 |
C3—C6—H6A | 109.1 | C6—N2—H3 | 118.7 |
N2—C6—H6B | 108.8 | H7A—O2—H7B | 106.1 |
| | | |
C4—C3—C6—N2 | 0.7 (4) | C3—C6—N2—C7 | −86.2 (3) |
Symmetry code: (i) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H7A···O1 | 0.85 | 2.17 | 2.879 (3) | 140 |
O2—H7B···N1ii | 0.85 | 2.35 | 2.834 (3) | 116 |
N2—H3···O2iii | 0.86 | 2.07 | 2.856 (3) | 151 |
C4—H4···N2 | 0.93 | 2.52 | 2.849 (3) | 101 |
Symmetry codes: (ii) −x+2, −y+1, −z+1; (iii) x, −y+1/2, z−1/2. |