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Single crystals of a new polymorph of 1,4-bis­(imidazol-1-yl­meth­yl)benzene dihydrate (bix·2H2O), C14H14N4·2H2O, have been obtained by the hydro­thermal method. The asymmetric unit is composed of two independent half-bix mol­ecules, one on an inversion center and one on a twofold axial site, and two water mol­ecules. The disordered water mol­ecules link into discrete tetra­meric water units via two O-H...O hydrogen bonds, forming planar R44(8) rings. These tetra­meric water units and bix mol­ecules are further linked by two O-H...N hydrogen bonds into a three-dimensional network in which an R_{20}^{20}(106) hydrogen-bonded ring is observed. These large rings lead to the formation of a fivefold inter­penetrated network. If both the tetra­meric water units and the bix mol­ecules can be regarded as connected nodes, one single three-dimensional net can then be rationalized as a CdSO4 network. This study indicates that topological methodology can be applied in some cases in order to understand the inherent characteristics of some hydrogen-bonded supra­molecular assemblies.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108039504/sk3264sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108039504/sk3264Isup2.hkl
Contains datablock I

CCDC reference: 718161

Comment top

The crystal structure of another polymorph of the title compound (bix.2H2O) has been reported previously [Cambridge Strcutural Database (Allen, 2002) refcode PUVQIG (Hoskins et al., 1997b; Abrahams et al., 1998). Interestingly, crystallization of bix via the hydrothermal method leads to a structure in the monoclinic space group C2/c with Z = 8 [polymorph (II)], in contrast to the previously reported structure [polymorph (I)] in space group P21/n with Z = 2, which was obtained by recrystallization from water. In this communication, we report the differences between these two polymorphs and give an illustration of their topological classification.

As a flexible ligand, bix has been often used in the synthesis of metal–organic frameworks as a linker molecule (Hoskins et al., 1997a; Abrahams et al., 2002; Carculli et al., 2005; Wen et al., 2005, Zhang et al., 2005) and in the construction of hydrogen-bonded supramolecular assemblies as hydrogen-bonding acceptors (Ma & Coppens, 2004; Ma et al., 2004; Shen et al., 2004; Aakeröy et al., 2005, 2006; Zhang et al., 2007). Recently, as a result of our interest in exploring the self-assembling nature of carboxylic acids with Lewis bases (Meng et al., 2007; Meng, Lin & Li, 2008; Meng, Xiao, Wang & Liu, 2008; Meng, Xiao, Zhang & Zhou, 2008), we have re-synthesized the N-containing Lewis base bix by the standard procedure (Hoskins et al., 1997b).

Single-crystal X-ray diffraction reveals that there are two independent half-bix molecules and two water molecules in the selected asymmetric unit of polymorph (II) (Fig. 1). In the N1-containing bix molecule, its two halves are related by an inversion center at (1/2, 1/2, 0). However, the two halves in the N2-containing bix molecule are related by a twofold axis. By comparison, the asymmetric unit of polymorph (I) consists of only one water molecule and half a bix molecule whose two halves are related by an inversion center at (0, 1, 1/2). Besides this, the cell volume (2956.0 Å3) in polymorph (II) expands to ca four times of that in polymorph (I) (733.4 Å3). The water molecules in (II) are linked into a discrete tetrameric R44(8) water ring (Fig. 2) by O—H···O hydrogen bonds. Conversely, water molecules in (I) are linked into one-dimensional water chains [O···O = 2.728 (2) and 2.782 (2) Å; symmetry codes: -x, -y + 2, -z; -x - 1, -y + 2, -z] running parallel to the [100] direction (Fig. 2). These apparent differences may mainly be attributed to (i) the crystallized [cystallization?] conditions, i.e. temperature and pressure, and (ii) the flexibility stemming from the –CH2– group (Zhang et al., 2007).

The crystal packings of polymorphs (I) and (II) are also very different from each other. In (II), bix and water molecules are linked by O—H···O and N—H···O hydrogen bonds (Table 1) into a continuous three-dimensional network. Two types of hydrogen-bonded rings are formed; one is the R44(8) ring as mentioned above and the other is a very large R1420(106) hydrogen-bond ring (Bernstein et al., 1995), which is constructed via N—H···O hydrogen bonds. Topological analysis indicates that if one considers the tetrameric water units to be four-connected nodes and the bix molecules to be bridges (Fig. 3a), one single net can then be rationalized as a three-dimensional net with CdSO4 (cds) topology. Fig. 3(b) reveals the topology displayed by this structure with short and long Schläfli symbols 65.8 and 6.6.6.6.62.*, respectively (* means there are no rings for this angle; Batten, 2001; Batten & Robson, 1998). Further analysis indicates that five independent three-dimensional networks of this type related by a translation vector of ca 2.1436 Å along the [100] direction make up the final fivefold interpenetrated network (Fig. 3b). These interpenetrated networks are strengthened by ππ and C—H···π interactions [Cg1···Cg2ii = 3.934 (2) Å, Cg3···Cg3iii = 3.593 (2) Å, and H3···Cg3iv = 2.95 Å, C3···Cg3iv = 3.829 (2) Å and C3—H3···Cg3iv = 158°; Cg1, Cg2 and Cg3 are the centroids of the rings involving C1, C8 and N4, respectively; symmetry codes: (ii) x - 1, y, z - 1, (iii) -x + 2, y, -z + 3/2; (iv) -x + 2, y, -z + 1/2]. By contrast, bix molecules in polymorph (I) are joined together by the only Owater···Nimidazole [2.821 (2) Å] hydrogen bond, which originates from two sides of the one-dimensional water chain, resulting in a simple two-dimensional sheet running parallel to the (010) plane (Fig. 4a). We can regard the two-dimensional sheet as a Shubnikov hexagonal plane (hcb) net with a total Schläfli symbol of 63 (Fig. 4b). The neighbouring sheets are linked by C1—H1···O1(-x - 1/2, y - 1/2, -z + 1/2) interactions into a simple three-dimensional network. No other interactions are observed in polymorph (I).

Related literature top

For related literature, see: Aakeröy et al. (2005, 2006); Abrahams et al. (1998, 2002); Batten (2001); Batten & Robson (1998); Bernstein et al. (1995); Carculli et al. (2005); Hoskins et al. (1997a, 1997b); Ma & Coppens (2004a); Ma et al. (2004b); Meng et al. (2007, 2008a, 2008b, 2008c); Shen et al. (2004); Wen et al. (2005); Zhang et al. (2005, 2007).

Experimental top

The title compound was prepared according to the literature method (Hoskins et al., 1997b). A 30.0 mg sample was sealed in a 23 ml Teflon-lined stainless steel autoclave, heated at 400 K for 2 d under autogenous pressure and cooled slowly to room temperature. Plate-shaped single crystals suitable for X-ray diffraction were obtained at the bottom of the autoclave.

Refinement top

In polymorph (II), the water molecules were both disordered over two positions. Because of the existence of the discrete hydrogen-bonding networks, the disorder parameters of O1 and O2 were coupled and their final occupancies were refined to be 0.59 (1):0.41 (1) for the major and minor components, respectively. All H atoms bonded to C atoms were positioned geometrically, with C—H distances of 0.93 (aromatic) and 0.97 Å (methylene), and treated as riding, with Uiso(H) set at 1.2Ueq(C). H atoms bonded to water O atoms were found in difference maps and refined with the constraints O—H = 0.82 (1) Å, H—H = 1.35 (1) Å and Uiso(H) = 1.5Ueq(O).

Computing details top

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003), Mercury (Version 1.4; Bruno et al., 2002) and DIAMOND (Brandenburg, 2004); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structures of bix.2H2O in polymorphs (I) and (II), showing the atom-numbering schemes. Displacement ellipsoids are drawn at the 10% probability level and H atoms are shown as small spheres of arbitrary radii. Hydorgen bonds are shown as dashed lines. In polymorph (II), atoms labeled with the suffixes A and B are at the symmetry positions (-x + 1, -y + 1, -z) and (-x +3, y, -z + 3/2), respectively. The minor components of the disorder water molecules have been omitted for clarity. In polymorph (I), atoms labeled with the suffix C are at the symmetry position (-x, -y + 2, -z + 1).
[Figure 2] Fig. 2. Parts of the crystal structures of bix.2H2O in polymorphs (I) (a) and (II) (b), respectively, showing the formation of the R44(8) and R1220(106) hydrogen-bond rings in (II) and the one-dimensional water chain running parallel to the [100] direction in (I). Hydrogen bonds are shown as dashed lines. The minor components of the disordered water moleculesin (II) have been omitted for clarity.
[Figure 3] Fig. 3. Simplification of the crystal structure of bix.2H2O in polymorph (II): (a) a schematic view of the formation of a single three-dimensional network and (b) a schematic view of the formation of the fivefold interpenetrated network. [In (a) in the electronic version of the paper, blue and aqua balls represent R44(8) water units and bix molecules, respectively.]
[Figure 4] Fig. 4. Simplification of the crystal structure of bix.2H2O in polymorph (I): (a) a schematic view of the formation of the two-dimensional network running parallel to the (010) plane and (b) a schematic view of the Shubnikov hexagonal plane (hcb) net. [In (a) in the electronic version of the paper, blue and aqua balls represent bix and water molecules, respectively.]
1,4-bis(imidazol-1-ylmethyl)benzene dihydrate top
Crystal data top
C14H14N4·2H2OF(000) = 1168
Mr = 274.32Dx = 1.233 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2032 reflections
a = 10.7178 (8) Åθ = 2.3–23.8°
b = 17.9925 (14) ŵ = 0.09 mm1
c = 15.3662 (12) ÅT = 299 K
β = 94.006 (2)°Prism, colorless
V = 2956.0 (4) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3369 independent reflections
Radiation source: fine focus sealed Siemens Mo tube2237 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
0.3° wide ω exposures scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 1313
Tmin = 0.965, Tmax = 0.983k = 1823
9245 measured reflectionsl = 1919
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.7501P]
where P = (Fo2 + 2Fc2)/3
3369 reflections(Δ/σ)max < 0.001
224 parametersΔρmax = 0.17 e Å3
12 restraintsΔρmin = 0.13 e Å3
Crystal data top
C14H14N4·2H2OV = 2956.0 (4) Å3
Mr = 274.32Z = 8
Monoclinic, C2/cMo Kα radiation
a = 10.7178 (8) ŵ = 0.09 mm1
b = 17.9925 (14) ÅT = 299 K
c = 15.3662 (12) Å0.30 × 0.20 × 0.20 mm
β = 94.006 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3369 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
2237 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.983Rint = 0.026
9245 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05712 restraints
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.17 e Å3
3369 reflectionsΔρmin = 0.13 e Å3
224 parameters
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*/UeqOcc. (<1)
C10.53974 (17)0.42695 (9)0.00846 (10)0.0546 (4)
C20.42190 (18)0.44231 (10)0.01619 (12)0.0630 (5)
H20.36810.40340.02730.076*
C30.61776 (17)0.48557 (11)0.02467 (12)0.0616 (5)
H30.69790.47620.04150.074*
C40.5846 (2)0.34798 (10)0.01634 (12)0.0721 (6)
H4A0.51310.31490.02130.087*
H4B0.62890.34310.06900.087*
C50.6319 (2)0.30087 (11)0.13498 (14)0.0743 (6)
H50.54910.29170.14610.089*
C60.8285 (2)0.31079 (12)0.14960 (16)0.0814 (6)
H60.91060.30970.17350.098*
C70.7936 (2)0.33287 (11)0.06809 (14)0.0727 (5)
H70.84560.34950.02610.087*
C81.37872 (15)0.45287 (11)0.77603 (10)0.0551 (4)
C91.43993 (17)0.51832 (11)0.76292 (14)0.0716 (6)
H91.39970.56320.77160.086*
C101.43998 (16)0.38752 (11)0.76313 (12)0.0624 (5)
H101.40000.34260.77220.075*
C111.24523 (17)0.45326 (14)0.80100 (12)0.0757 (6)
H11A1.22790.40750.83130.091*
H11B1.23300.49440.84030.091*
C121.12161 (18)0.52399 (12)0.68190 (13)0.0668 (5)
H121.14150.57220.69970.080*
C131.05094 (18)0.50388 (12)0.61061 (13)0.0685 (5)
H131.01280.53680.57030.082*
C141.10934 (17)0.40531 (11)0.67441 (13)0.0645 (5)
H141.12110.35530.68800.077*
N10.66770 (15)0.32609 (8)0.05926 (9)0.0606 (4)
N20.7272 (2)0.29034 (10)0.19224 (12)0.0840 (6)
N31.15841 (12)0.46048 (9)0.72304 (9)0.0569 (4)
N41.04272 (14)0.42884 (10)0.60531 (10)0.0693 (5)
O10.716 (2)0.2775 (11)0.3763 (4)0.115 (4)0.59 (1)
H1A0.717 (7)0.277 (5)0.3227 (8)0.172*0.59 (1)
H1B0.786 (4)0.276 (6)0.402 (4)0.172*0.59 (1)
O20.8981 (14)0.3183 (8)0.5088 (10)0.102 (2)0.59 (1)
H2A0.923 (8)0.358 (3)0.530 (4)0.152*0.59 (1)
H2B0.847 (8)0.296 (4)0.537 (5)0.152*0.59 (1)
O1'0.779 (3)0.2557 (8)0.3734 (5)0.108 (5)0.41 (1)
H1C0.756 (10)0.262 (6)0.3217 (17)0.162*0.41 (1)
H1D0.776 (13)0.293 (4)0.404 (5)0.162*0.41 (1)
O2'0.869 (2)0.3192 (12)0.5294 (16)0.113 (4)0.41 (1)
H2C0.921 (10)0.350 (6)0.546 (6)0.169*0.41 (1)
H2D0.831 (10)0.299 (6)0.567 (5)0.169*0.41 (1)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0723 (12)0.0509 (10)0.0390 (9)0.0055 (9)0.0087 (8)0.0010 (7)
C20.0679 (12)0.0560 (11)0.0642 (11)0.0079 (9)0.0020 (9)0.0129 (9)
C30.0609 (11)0.0673 (12)0.0568 (11)0.0079 (9)0.0061 (8)0.0083 (9)
C40.0997 (15)0.0580 (12)0.0554 (11)0.0141 (10)0.0174 (10)0.0065 (9)
C50.0941 (15)0.0609 (12)0.0672 (13)0.0047 (11)0.0011 (11)0.0089 (10)
C60.0914 (16)0.0671 (14)0.0817 (16)0.0108 (12)0.0214 (13)0.0054 (11)
C70.0808 (14)0.0658 (13)0.0709 (13)0.0088 (10)0.0017 (11)0.0025 (10)
C80.0477 (9)0.0769 (12)0.0392 (9)0.0028 (9)0.0074 (7)0.0025 (8)
C90.0575 (10)0.0633 (12)0.0910 (15)0.0105 (9)0.0159 (10)0.0108 (11)
C100.0575 (10)0.0627 (12)0.0659 (12)0.0080 (9)0.0042 (9)0.0073 (9)
C110.0524 (11)0.1278 (19)0.0459 (10)0.0071 (11)0.0029 (8)0.0009 (11)
C120.0650 (12)0.0681 (12)0.0664 (12)0.0042 (10)0.0025 (9)0.0081 (10)
C130.0630 (12)0.0832 (15)0.0580 (12)0.0108 (10)0.0046 (9)0.0029 (10)
C140.0600 (11)0.0670 (12)0.0664 (12)0.0036 (9)0.0035 (9)0.0015 (10)
N10.0847 (11)0.0452 (8)0.0503 (9)0.0111 (7)0.0064 (8)0.0004 (7)
N20.1220 (16)0.0694 (11)0.0581 (10)0.0145 (11)0.0109 (11)0.0079 (8)
N30.0441 (8)0.0784 (11)0.0476 (8)0.0012 (7)0.0013 (6)0.0043 (7)
N40.0614 (10)0.0872 (13)0.0579 (10)0.0058 (8)0.0058 (8)0.0086 (9)
O10.123 (7)0.153 (7)0.068 (3)0.010 (6)0.004 (3)0.004 (3)
O20.095 (5)0.119 (4)0.092 (5)0.035 (3)0.017 (3)0.009 (3)
O1'0.137 (12)0.134 (6)0.052 (3)0.012 (6)0.001 (4)0.002 (3)
O2'0.103 (8)0.140 (7)0.097 (8)0.071 (6)0.017 (5)0.029 (6)
Geometric parameters (Å, º) top
C1—C21.372 (3)C11—N31.470 (2)
C1—C31.379 (2)C11—H11A0.9700
C1—C41.508 (2)C11—H11B0.9700
C2—C3i1.375 (3)C12—C131.337 (3)
C2—H20.9300C12—N31.351 (2)
C3—C2i1.374 (3)C12—H120.9300
C3—H30.9300C13—N41.355 (3)
C4—N11.467 (2)C13—H130.9300
C4—H4A0.9700C14—N41.308 (2)
C4—H4B0.9700C14—N31.329 (2)
C5—N21.314 (3)C14—H140.9300
C5—N11.330 (2)O1—H1A0.824 (10)
C5—H50.9300O1—H1B0.822 (10)
C6—C71.342 (3)O1—H1C1.01 (7)
C6—N21.358 (3)O1—H1D0.80 (11)
C6—H60.9300O2—H2A0.823 (10)
C7—N11.353 (2)O2—H2B0.822 (10)
C7—H70.9300O2—H2C0.84 (7)
C8—C101.368 (2)O2—H2D1.24 (4)
C8—C91.370 (3)O1'—H1B0.58 (8)
C8—C111.507 (2)O1'—H1C0.822 (10)
C9—C9ii1.374 (4)O1'—H1D0.820 (10)
C9—H90.9300O2'—H2A0.91 (5)
C10—C10ii1.375 (3)O2'—H2C0.818 (10)
C10—H100.9300O2'—H2D0.820 (10)
C2—C1—C3118.51 (16)N3—C11—H11A109.5
C2—C1—C4121.14 (17)C8—C11—H11A109.5
C3—C1—C4120.35 (18)N3—C11—H11B109.5
C1—C2—C3i120.87 (17)C8—C11—H11B109.5
C1—C2—H2119.6H11A—C11—H11B108.1
C3i—C2—H2119.6C13—C12—N3106.53 (18)
C2i—C3—C1120.62 (17)C13—C12—H12126.7
C2i—C3—H3119.7N3—C12—H12126.7
C1—C3—H3119.7C12—C13—N4110.46 (18)
N1—C4—C1111.64 (14)C12—C13—H13124.8
N1—C4—H4A109.3N4—C13—H13124.8
C1—C4—H4A109.3N4—C14—N3112.77 (18)
N1—C4—H4B109.3N4—C14—H14123.6
C1—C4—H4B109.3N3—C14—H14123.6
H4A—C4—H4B108.0C5—N1—C7106.85 (17)
N2—C5—N1112.1 (2)C5—N1—C4126.02 (19)
N2—C5—H5123.9C7—N1—C4126.96 (18)
N1—C5—H5123.9C5—N2—C6104.38 (18)
C7—C6—N2110.5 (2)C14—N3—C12106.11 (16)
C7—C6—H6124.7C14—N3—C11126.53 (17)
N2—C6—H6124.7C12—N3—C11127.10 (17)
C6—C7—N1106.1 (2)C14—N4—C13104.13 (16)
C6—C7—H7126.9H1A—O1—H1B114 (2)
N1—C7—H7126.9H1A—O1—H1D119 (10)
C10—C8—C9118.55 (17)H1C—O1—H1D100 (9)
C10—C8—C11120.99 (18)H2A—O2—H2B115 (2)
C9—C8—C11120.42 (18)H1A—O1'—H1B112 (9)
C8—C9—C9ii120.72 (11)H1B—O1'—H1C132 (10)
C8—C9—H9119.6H1C—O1'—H1D115 (2)
C9ii—C9—H9119.6H2A—O2'—H2B162 (10)
C8—C10—C10ii120.73 (11)H2B—O2'—H2C144 (10)
C8—C10—H10119.6H2A—O2'—H2D133 (10)
C10ii—C10—H10119.6H2C—O2'—H2D116 (2)
N3—C11—C8110.55 (14)
C3—C1—C2—C3i0.1 (3)N2—C5—N1—C4175.90 (16)
C4—C1—C2—C3i178.90 (16)C6—C7—N1—C50.3 (2)
C2—C1—C3—C2i0.1 (3)C6—C7—N1—C4175.69 (16)
C4—C1—C3—C2i178.90 (16)C1—C4—N1—C584.0 (2)
C2—C1—C4—N1101.9 (2)C1—C4—N1—C790.5 (2)
C3—C1—C4—N177.0 (2)N1—C5—N2—C60.4 (2)
N2—C6—C7—N10.1 (2)C7—C6—N2—C50.2 (2)
C10—C8—C9—C9ii0.2 (3)N4—C14—N3—C120.6 (2)
C11—C8—C9—C9ii177.6 (2)N4—C14—N3—C11175.09 (16)
C9—C8—C10—C10ii0.5 (3)C13—C12—N3—C140.6 (2)
C11—C8—C10—C10ii177.3 (2)C13—C12—N3—C11175.05 (16)
C10—C8—C11—N394.3 (2)C8—C11—N3—C1489.2 (2)
C9—C8—C11—N383.5 (2)C8—C11—N3—C1284.2 (2)
N3—C12—C13—N40.4 (2)N3—C14—N4—C130.3 (2)
N2—C5—N1—C70.5 (2)C12—C13—N4—C140.1 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x+3, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N20.82 (1)2.03 (2)2.848 (7)172 (9)
O1—H1B···O20.82 (1)2.10 (5)2.815 (16)145 (8)
O2—H2A···N40.82 (1)2.10 (4)2.869 (13)157 (9)
O2—H2B···O1iii0.82 (1)2.03 (5)2.811 (17)158 (11)
O1—H1C···N20.82 (1)2.06 (3)2.868 (10)170 (13)
O1—H1D···O20.82 (1)2.15 (7)2.77 (2)132 (8)
O2—H2C···N40.82 (1)2.09 (2)2.902 (17)172 (11)
O2—H2D···O1iii0.82 (1)1.82 (3)2.625 (17)165 (11)
Symmetry code: (iii) x+3/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC14H14N4·2H2O
Mr274.32
Crystal system, space groupMonoclinic, C2/c
Temperature (K)299
a, b, c (Å)10.7178 (8), 17.9925 (14), 15.3662 (12)
β (°) 94.006 (2)
V3)2956.0 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.965, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
9245, 3369, 2237
Rint0.026
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.140, 1.04
No. of reflections3369
No. of parameters224
No. of restraints12
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.13

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), Mercury (Version 1.4; Bruno et al., 2002) and DIAMOND (Brandenburg, 2004), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N20.824 (10)2.030 (18)2.848 (7)172 (9)
O1—H1B···O20.822 (10)2.10 (5)2.815 (16)145 (8)
O2—H2A···N40.823 (10)2.10 (4)2.869 (13)157 (9)
O2—H2B···O1i0.822 (10)2.03 (5)2.811 (17)158 (11)
O1'—H1C···N20.822 (10)2.06 (3)2.868 (10)170 (13)
O1'—H1D···O2'0.820 (10)2.15 (7)2.77 (2)132 (8)
O2'—H2C···N40.818 (10)2.09 (2)2.902 (17)172 (11)
O2'—H2D···O1'i0.820 (10)1.82 (3)2.625 (17)165 (11)
Symmetry code: (i) x+3/2, y+1/2, z+1.
 

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