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The title compound, C20H18N4O2·2H2O, an amide-containing bipyridyl-type compound, crystallizes as a dihydrate. The organic molecule is centrosymmetric. Hydro­gen-bonding and π–π stacking interactions in the crystal structure result in the formation of an infinite three-dimensional supramolecular network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017046/rn6050sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017046/rn6050Isup2.hkl
Contains datablock I

CCDC reference: 277746

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.129
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found




Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXL97.

N,N'-Bis(3-pyridylmethyl)benzene-1,4-dicarboxamide dihydrate top
Crystal data top
C20H18N4O2·2H2OF(000) = 404
Mr = 382.42Dx = 1.318 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ynCell parameters from 49 reflections
a = 7.3871 (7) Åθ = 2.9–17.9°
b = 13.8981 (16) ŵ = 0.09 mm1
c = 9.8971 (12) ÅT = 295 K
β = 108.441 (8)°Block, colourless
V = 963.92 (19) Å30.4 × 0.4 × 0.3 mm
Z = 2
Data collection top
Bruker P4
diffractometer
1125 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
ω scansh = 18
Absorption correction: ψ scan
(North et al., 1968)
k = 116
Tmin = 0.972, Tmax = 0.973l = 1111
2294 measured reflections3 standard reflections every 97 reflections
1694 independent reflections intensity decay: none
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0524P)2 + 0.1416P]
where P = (Fo2 + 2Fc2)/3
1694 reflections(Δ/σ)max < 0.001
140 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.15 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
O10.1031 (2)0.64269 (11)0.53852 (17)0.0652 (5)
N20.2308 (3)0.72784 (12)0.39663 (19)0.0514 (5)
C90.5512 (3)0.59389 (14)0.4830 (2)0.0466 (5)
H80.58610.65700.47190.056*
C20.1881 (3)0.89701 (14)0.4584 (2)0.0468 (5)
C100.6814 (3)0.52038 (14)0.4960 (2)0.0465 (5)
H90.80320.53430.49300.056*
C80.3675 (3)0.57395 (13)0.48640 (19)0.0426 (5)
C70.2230 (3)0.65153 (14)0.4759 (2)0.0458 (5)
N10.2225 (3)1.06881 (13)0.4619 (2)0.0648 (6)
C60.1000 (3)0.80877 (14)0.3750 (2)0.0531 (5)
H60.00990.78970.40230.064*
H50.05530.82480.27440.064*
C10.1550 (3)0.98634 (14)0.3954 (2)0.0550 (6)
H10.08070.98960.30010.066*
C50.3302 (4)1.06237 (18)0.5977 (3)0.0718 (7)
H40.38051.11860.64580.086*
C40.3704 (4)0.97721 (19)0.6699 (3)0.0753 (8)
H30.44480.97600.76530.090*
C30.2995 (3)0.89342 (18)0.5996 (2)0.0648 (6)
H20.32630.83470.64670.078*
O1W0.0906 (3)0.24112 (14)0.3155 (2)0.0839 (7)
H70.307 (3)0.7272 (16)0.349 (3)0.065 (7)*
H1W0.030 (4)0.2750 (19)0.364 (3)0.093 (9)*
H2W0.134 (4)0.184 (2)0.364 (3)0.107 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0712 (10)0.0551 (9)0.0850 (11)0.0114 (8)0.0469 (9)0.0103 (8)
N20.0599 (11)0.0436 (10)0.0579 (11)0.0091 (8)0.0290 (9)0.0041 (8)
C90.0499 (11)0.0373 (10)0.0534 (11)0.0019 (9)0.0172 (9)0.0018 (8)
C20.0473 (11)0.0467 (11)0.0489 (11)0.0063 (9)0.0186 (9)0.0024 (9)
C100.0447 (11)0.0443 (11)0.0520 (11)0.0019 (9)0.0173 (9)0.0011 (9)
C80.0478 (11)0.0395 (10)0.0414 (10)0.0009 (9)0.0155 (9)0.0024 (8)
C70.0512 (12)0.0405 (11)0.0479 (10)0.0002 (9)0.0187 (9)0.0025 (8)
N10.0737 (13)0.0466 (11)0.0776 (13)0.0002 (10)0.0289 (11)0.0011 (10)
C60.0578 (12)0.0440 (11)0.0553 (12)0.0084 (10)0.0147 (10)0.0048 (9)
C10.0644 (14)0.0470 (12)0.0552 (12)0.0063 (10)0.0212 (11)0.0034 (10)
C50.0634 (15)0.0606 (15)0.0888 (18)0.0051 (13)0.0205 (14)0.0224 (14)
C40.0682 (16)0.0813 (18)0.0627 (14)0.0078 (14)0.0013 (13)0.0131 (13)
C30.0700 (15)0.0596 (14)0.0556 (13)0.0101 (12)0.0068 (11)0.0053 (11)
O1W0.1330 (18)0.0609 (11)0.0824 (13)0.0178 (11)0.0687 (13)0.0086 (9)
Geometric parameters (Å, º) top
O1—C71.237 (2)C8—C71.498 (3)
N2—C71.331 (2)N1—C51.331 (3)
N2—C61.454 (3)N1—C11.337 (3)
N2—H70.84 (3)C6—H60.9700
C9—C101.381 (3)C6—H50.9700
C9—C81.395 (3)C1—H10.9300
C9—H80.9300C5—C41.366 (4)
C2—C11.376 (3)C5—H40.9300
C2—C31.380 (3)C4—C31.373 (3)
C2—C61.506 (3)C4—H30.9300
C10—C8i1.385 (3)C3—H20.9300
C10—H90.9300O1W—H1W0.89 (3)
C8—C10i1.385 (3)O1W—H2W0.93 (3)
C7—N2—C6123.57 (18)N2—C6—C2113.43 (17)
C7—N2—H7118.9 (16)N2—C6—H6108.9
C6—N2—H7117.2 (16)C2—C6—H6108.9
C10—C9—C8120.29 (18)N2—C6—H5108.9
C10—C9—H8119.9C2—C6—H5108.9
C8—C9—H8119.9H6—C6—H5107.7
C1—C2—C3117.1 (2)N1—C1—C2124.4 (2)
C1—C2—C6120.15 (18)N1—C1—H1117.8
C3—C2—C6122.78 (19)C2—C1—H1117.8
C9—C10—C8i120.68 (19)N1—C5—C4123.3 (2)
C9—C10—H9119.7N1—C5—H4118.4
C8i—C10—H9119.7C4—C5—H4118.4
C10i—C8—C9119.02 (18)C5—C4—C3119.0 (2)
C10i—C8—C7118.77 (17)C5—C4—H3120.5
C9—C8—C7122.18 (17)C3—C4—H3120.5
O1—C7—N2123.06 (19)C4—C3—C2119.5 (2)
O1—C7—C8120.09 (18)C4—C3—H2120.3
N2—C7—C8116.85 (17)C2—C3—H2120.3
C5—N1—C1116.7 (2)H1W—O1W—H2W109 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H7···O1Wii0.84 (3)2.01 (3)2.817 (3)161 (2)
O1W—H1W···O1iii0.89 (3)1.95 (3)2.837 (2)176 (3)
O1W—H2W···N1iv0.93 (3)1.88 (3)2.809 (3)179 (3)
Symmetry codes: (ii) x+1/2, y+1/2, z+1/2; (iii) x, y+1, z+1; (iv) x, y1, z.
 

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