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In the title compound, C16H18N4·2H2O, there is one half-mol­ecule (organic) and one water molecule in the asymmetric unit, the organic molecule being centrosymmetric. The separation of the two terminal N atoms is 11.296 (8) Å and the dihedral angle between the benzene and imidazole rings is 85.27 (18)°; the mol­ecule adopts a Z-shaped conformation. A one-dimensional water chain links the organic mol­ecules, forming a two-dimensional ladder-shaped network along the b-axis direction through inter­molecular O—H...O and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011706/fl2013sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011706/fl2013Isup2.hkl
Contains datablock I

CCDC reference: 608328

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.060
  • wR factor = 0.199
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) or DIAMOND (Brandenburg, 2005)?; software used to prepare material for publication: SHELXTL or SHELXL97?.

1,1'-(2,5-Dimethyl-1,4-phenylenemethylene)di-1H-imidazole dihydrate top
Crystal data top
C16H18N4·2H2OF(000) = 324
Mr = 302.38Dx = 1.205 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 689 reflections
a = 8.692 (9) Åθ = 2.7–19.8°
b = 5.083 (2) ŵ = 0.08 mm1
c = 19.068 (3) ÅT = 298 K
β = 98.4080 (18)°Plane, colourless
V = 833.3 (10) Å30.49 × 0.17 × 0.11 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
1442 independent reflections
Radiation source: fine-focus sealed tube735 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 710
Tmin = 0.961, Tmax = 0.991k = 66
3999 measured reflectionsl = 2222
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1003P)2 + 0.0713P]
where P = (Fo2 + 2Fc2)/3
1442 reflections(Δ/σ)max < 0.001
101 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.21 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
N10.2725 (3)0.6822 (5)0.12824 (13)0.0568 (8)
N20.0432 (3)0.6860 (7)0.16526 (15)0.0726 (9)
O10.7633 (3)0.5631 (6)0.21953 (16)0.1136 (12)
H80.85340.59280.24220.136*
H90.71990.71310.21880.136*
C10.1343 (4)0.5617 (7)0.12820 (18)0.0648 (10)
H10.10700.40570.10410.078*
C20.1275 (5)0.8999 (8)0.19201 (19)0.0768 (11)
H20.09271.02650.22120.092*
C30.2688 (5)0.9016 (7)0.16998 (17)0.0729 (11)
H30.34711.02590.18090.087*
C40.4000 (4)0.5964 (7)0.09165 (18)0.0636 (10)
H4A0.36830.43980.06420.076*
H4B0.48870.55050.12650.076*
C50.4481 (3)0.8055 (6)0.04286 (15)0.0517 (9)
C60.5930 (3)0.9226 (7)0.06006 (16)0.0561 (9)
H60.65630.86940.10120.067*
C70.6474 (3)1.1157 (6)0.01836 (16)0.0538 (9)
C80.8064 (3)1.2328 (8)0.04143 (19)0.0762 (11)
H8A0.87881.16100.01300.114*
H8B0.84011.19140.09040.114*
H8C0.80141.42030.03550.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0640 (18)0.0465 (17)0.0603 (16)0.0068 (14)0.0103 (13)0.0020 (13)
N20.073 (2)0.070 (2)0.078 (2)0.0036 (17)0.0211 (17)0.0078 (17)
O10.108 (2)0.107 (3)0.139 (3)0.0268 (18)0.0583 (19)0.010 (2)
C10.062 (2)0.056 (2)0.077 (2)0.0111 (19)0.0120 (18)0.0031 (18)
C20.105 (3)0.064 (3)0.066 (2)0.006 (2)0.028 (2)0.0024 (19)
C30.097 (3)0.055 (2)0.065 (2)0.016 (2)0.008 (2)0.0050 (19)
C40.061 (2)0.054 (2)0.077 (2)0.0014 (17)0.0148 (17)0.0060 (18)
C50.0488 (18)0.049 (2)0.0571 (19)0.0009 (15)0.0090 (15)0.0003 (15)
C60.0504 (19)0.062 (2)0.0542 (18)0.0014 (16)0.0013 (14)0.0014 (17)
C70.0456 (17)0.055 (2)0.0601 (19)0.0052 (15)0.0046 (15)0.0033 (16)
C80.057 (2)0.087 (3)0.081 (2)0.0143 (19)0.0006 (18)0.004 (2)
Geometric parameters (Å, º) top
N1—C11.348 (4)C4—H4A0.9700
N1—C31.373 (4)C4—H4B0.9700
N1—C41.460 (4)C5—C61.388 (4)
N2—C11.299 (4)C5—C7i1.389 (4)
N2—C21.367 (5)C6—C71.389 (5)
O1—H80.8502C6—H60.9300
O1—H90.8499C7—C5i1.389 (4)
C1—H10.9300C7—C81.510 (4)
C2—C31.355 (5)C8—H8A0.9600
C2—H20.9300C8—H8B0.9600
C3—H30.9300C8—H8C0.9600
C4—C51.511 (4)
C1—N1—C3105.8 (3)C5—C4—H4B109.1
C1—N1—C4127.1 (3)H4A—C4—H4B107.8
C3—N1—C4127.1 (3)C6—C5—C7i119.0 (3)
C1—N2—C2104.7 (3)C6—C5—C4118.6 (3)
H8—O1—H9102.9C7i—C5—C4122.4 (3)
N2—C1—N1113.1 (3)C5—C6—C7122.7 (3)
N2—C1—H1123.4C5—C6—H6118.6
N1—C1—H1123.4C7—C6—H6118.6
C3—C2—N2110.5 (3)C5i—C7—C6118.3 (3)
C3—C2—H2124.8C5i—C7—C8122.7 (3)
N2—C2—H2124.8C6—C7—C8119.0 (3)
C2—C3—N1105.9 (3)C7—C8—H8A109.5
C2—C3—H3127.1C7—C8—H8B109.5
N1—C3—H3127.1H8A—C8—H8B109.5
N1—C4—C5112.4 (3)C7—C8—H8C109.5
N1—C4—H4A109.1H8A—C8—H8C109.5
C5—C4—H4A109.1H8B—C8—H8C109.5
N1—C4—H4B109.1
Symmetry code: (i) x+1, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(1)—H(8)···N(2)0.852.412.849 (5)113
O(1)—H(9)···O(1)0.852.132.818 (5)138
 

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