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The title compound, C20H18N4O2·2H2O, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017563/sg6010sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017563/sg6010Isup2.hkl
Contains datablock I

CCDC reference: 277772

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.050
  • wR factor = 0.113
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

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
C20H18N4O2·2H2OF(000) = 404
Mr = 382.42Dx = 1.384 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 573 reflections
a = 8.1173 (13) Åθ = 3.0–19.2°
b = 9.8449 (15) ŵ = 0.10 mm1
c = 13.6802 (17) ÅT = 298 K
β = 122.944 (7)°Block, colorless
V = 917.4 (2) Å30.20 × 0.10 × 0.10 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
1614 independent reflections
Radiation source: fine-focus sealed tube969 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
φ and ω scansθmax = 25.0°, θmin = 2.7°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 89
Tmin = 0.980, Tmax = 0.988k = 711
4470 measured reflectionsl = 1615
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-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 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
C11.1628 (4)0.4881 (3)0.4382 (2)0.0489 (8)
H11.29160.46980.49800.053 (8)*
C21.0272 (4)0.3858 (3)0.4040 (2)0.0444 (7)
H21.06510.30150.44040.051 (8)*
C30.8329 (4)0.4085 (3)0.3148 (2)0.0360 (6)
C40.7902 (4)0.5367 (3)0.2655 (2)0.0427 (7)
H40.66270.55820.20560.042 (7)*
C50.9370 (4)0.6320 (3)0.3055 (3)0.0490 (8)
H50.90400.71710.27030.051 (8)*
C60.6833 (4)0.2970 (3)0.2768 (2)0.0410 (7)
H6A0.72590.21880.25300.043 (7)*
H6B0.67650.27000.34270.038 (7)*
C70.3610 (4)0.3997 (2)0.1994 (2)0.0364 (7)
C80.1765 (4)0.4506 (2)0.0941 (2)0.0320 (6)
C90.1572 (4)0.4784 (2)0.0099 (2)0.0368 (7)
H90.26320.46440.01730.035 (7)*
C100.0170 (4)0.5270 (2)0.1035 (2)0.0373 (7)
H100.02760.54500.17340.024 (6)*
N11.1223 (3)0.6115 (2)0.3913 (2)0.0495 (6)
N20.4893 (3)0.3366 (2)0.18205 (19)0.0387 (6)
H30.45520.31920.11190.037 (8)*
O10.3929 (3)0.41625 (19)0.29726 (16)0.0523 (6)
O20.5247 (3)0.23635 (19)0.49215 (16)0.0575 (6)
H7A0.44030.26050.42260.069*
H7B0.63220.22670.49620.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0343 (18)0.057 (2)0.0441 (19)0.0031 (15)0.0140 (16)0.0062 (15)
C20.0400 (18)0.0402 (18)0.0495 (19)0.0093 (14)0.0221 (16)0.0047 (14)
C30.0347 (16)0.0393 (16)0.0363 (16)0.0084 (13)0.0208 (14)0.0028 (13)
C40.0376 (17)0.0472 (19)0.0409 (18)0.0077 (15)0.0200 (15)0.0050 (14)
C50.053 (2)0.0400 (19)0.059 (2)0.0019 (16)0.0335 (18)0.0043 (15)
C60.0366 (17)0.0412 (18)0.0445 (18)0.0067 (13)0.0216 (15)0.0056 (13)
C70.0354 (16)0.0336 (16)0.0386 (17)0.0018 (12)0.0191 (14)0.0003 (12)
C80.0330 (15)0.0274 (15)0.0329 (15)0.0029 (11)0.0162 (13)0.0031 (11)
C90.0323 (16)0.0400 (17)0.0443 (18)0.0017 (12)0.0249 (15)0.0022 (12)
C100.0405 (17)0.0420 (17)0.0331 (17)0.0032 (13)0.0223 (14)0.0032 (12)
N10.0447 (15)0.0463 (17)0.0561 (17)0.0027 (12)0.0265 (14)0.0049 (12)
N20.0319 (13)0.0432 (14)0.0365 (15)0.0047 (10)0.0157 (12)0.0005 (10)
O10.0465 (12)0.0719 (15)0.0349 (12)0.0099 (10)0.0198 (10)0.0017 (10)
O20.0449 (12)0.0737 (15)0.0547 (13)0.0046 (10)0.0276 (10)0.0088 (10)
Geometric parameters (Å, º) top
C1—N11.329 (3)C6—H6B0.9700
C1—C21.373 (4)C7—O11.228 (3)
C1—H10.9298C7—N21.340 (3)
C2—C31.391 (3)C7—C81.491 (3)
C2—H20.9299C8—C91.371 (3)
C3—C41.383 (3)C8—C10i1.386 (3)
C3—C61.505 (3)C9—C101.378 (3)
C4—C51.375 (4)C9—H90.9297
C4—H40.9301C10—C8i1.386 (3)
C5—N11.327 (3)C10—H100.9294
C5—H50.9302N2—H30.8597
C6—N21.446 (3)O2—H7A0.8501
C6—H6A0.9698O2—H7B0.8500
N1—C1—C2124.4 (3)C3—C6—H6B108.8
N1—C1—H1117.8H6A—C6—H6B107.8
C2—C1—H1117.8O1—C7—N2122.1 (2)
C1—C2—C3119.8 (3)O1—C7—C8121.0 (2)
C1—C2—H2120.1N2—C7—C8117.0 (2)
C3—C2—H2120.1C9—C8—C10i118.6 (2)
C4—C3—C2116.0 (3)C9—C8—C7123.9 (2)
C4—C3—C6123.8 (2)C10i—C8—C7117.5 (2)
C2—C3—C6120.2 (2)C8—C9—C10120.9 (2)
C5—C4—C3119.7 (3)C8—C9—H9119.5
C5—C4—H4120.2C10—C9—H9119.6
C3—C4—H4120.1C9—C10—C8i120.5 (2)
N1—C5—C4124.6 (3)C9—C10—H10119.8
N1—C5—H5117.6C8i—C10—H10119.8
C4—C5—H5117.7C5—N1—C1115.5 (2)
N2—C6—C3113.2 (2)C7—N2—C6122.6 (2)
N2—C6—H6A109.1C7—N2—H3118.8
C3—C6—H6A109.1C6—N2—H3118.7
N2—C6—H6B108.8H7A—O2—H7B106.1
C4—C3—C6—N20.7 (4)C3—C6—N2—C786.2 (3)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H7A···O10.852.172.879 (3)140
O2—H7B···N1ii0.852.352.834 (3)116
N2—H3···O2iii0.862.072.856 (3)151
C4—H4···N20.932.522.849 (3)101
Symmetry codes: (ii) x+2, y+1, z+1; (iii) x, y+1/2, z1/2.
 

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