Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034162/cf2114sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034162/cf2114Isup2.hkl |
CCDC reference: 657803
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.122
- Data-to-parameter ratio = 10.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C2 .. 5.10 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 .. 6.40 su PLAT245_ALERT_2_C U(iso) H18 Smaller than U(eq) C18 by ... 0.01 AngSq PLAT480_ALERT_4_C Long H...A H-Bond Reported H15 .. N2 .. 2.73 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B .. N3 .. 2.67 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9 .. N4 .. 2.68 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B .. N4 .. 2.71 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Baruah et al. (2005); Johnstone et al. (1980); Maslak et al. (1999); Meijer et al. (2005); Zimmerman et al. (2002).
Dibenzyl diethylmalonate and dibenzyl malonic acid were synthesized according to the literature procedure (Maslak et al., 1999; Johnstone et al., 1980). To a solution of dibenzyl malonic acid (2.85 g, 10 mmol, 1 equiv.) in dry dichloromethane (10 ml) at 273 K, oxalyl chloride (3.5 ml, 40 mmol, 4 equiv.) was added along with a catalytic amount of N,N-dimethylformamide (DMF). After stirring the reaction mixture at room temperature for 2 h, the solvent was removed under reduced pressure. The resulting diacid chloride was dissolved in dry DMF (5 ml) and added to a solution containing 5-aminotetrazole (1.27 g, 10 mmol, 1 equiv.) and N,N-diisopropylethylamine (5.2 ml, 30 mmol, 3 equiv.) in dry DMF (5 ml) maintained at 253 K. The reaction mixture was stirred for 4 h at room temperature and poured into water. The usual work-up and purification of the crude product by column chromatography afforded a white solid (1.95 g, 81.5%). Colorless single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution in a dichloromethane-light petroleum ether mixture at room temperature.
Heterocycle-based self-assembling systems capable of forming two-, three- and four-centered hydrogen bonds are gaining interest in designing functional solids due to their high dimerization constant (Zimmerman et al., 2002; Meijer et al., 2005; Baruah et al., 2005). The tetrazole-based title compound (I) has been synthesized and we report here its crystal structure.
The title molecule adopts a 'bat-like' conformation (Fig. 1). The central tetrazole-pyrimidine-dione group is approximately planar. Molecules of (I) form centrosymmetric dimers (Fig. 2) via intermolecular N—H···O hydrogen bonds (Table 1) in which tetrazole-pyrimidine-dione groups are coplanar and the benzyl groups are approximately perpendicular to this plane.
The molecular packing viewed down the a axis (Fig. 3) shows the association of the centrosymmetric dimers via C—H···N contacts (Table 1). The C9—H9···N4iii and C15—H15···N2i interactions link the centrosymmetric dimers along the b axis, whereas along the c axis these dimers are associated via the C5—H5B···N4iv contact.
For related literature, see: Baruah et al. (2005); Johnstone et al. (1980); Maslak et al. (1999); Meijer et al. (2005); Zimmerman et al. (2002).
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Bruker, 2003).
C18H15N5O2 | F(000) = 1392 |
Mr = 333.35 | Dx = 1.334 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1821 reflections |
a = 8.6247 (13) Å | θ = 2.4–21.4° |
b = 16.777 (3) Å | µ = 0.09 mm−1 |
c = 22.950 (4) Å | T = 297 K |
V = 3320.8 (9) Å3 | Needle, colorless |
Z = 8 | 0.41 × 0.10 × 0.04 mm |
CCD area-detector diffractometer | 2932 independent reflections |
Radiation source: fine-focus sealed tube | 1813 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −10→10 |
Tmin = 0.963, Tmax = 0.997 | k = −17→19 |
15340 measured reflections | l = −20→27 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | All H-atom parameters refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0534P)2 + 0.911P] where P = (Fo2 + 2Fc2)/3 |
2932 reflections | (Δ/σ)max < 0.001 |
286 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C18H15N5O2 | V = 3320.8 (9) Å3 |
Mr = 333.35 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 8.6247 (13) Å | µ = 0.09 mm−1 |
b = 16.777 (3) Å | T = 297 K |
c = 22.950 (4) Å | 0.41 × 0.10 × 0.04 mm |
CCD area-detector diffractometer | 2932 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 1813 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.997 | Rint = 0.074 |
15340 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.122 | All H-atom parameters refined |
S = 1.01 | Δρmax = 0.19 e Å−3 |
2932 reflections | Δρmin = −0.24 e Å−3 |
286 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.1488 (2) | 0.03404 (11) | 0.54832 (7) | 0.0354 (5) | |
O2 | 0.0857 (2) | 0.13057 (11) | 0.72322 (8) | 0.0453 (5) | |
N1 | 0.1102 (2) | 0.03592 (14) | 0.56024 (9) | 0.0286 (5) | |
N2 | 0.3838 (3) | 0.03595 (14) | 0.58267 (10) | 0.0399 (6) | |
N3 | 0.4617 (3) | 0.05786 (14) | 0.63174 (10) | 0.0423 (6) | |
N4 | 0.3698 (3) | 0.08262 (14) | 0.67263 (10) | 0.0420 (6) | |
N5 | 0.2222 (2) | 0.07682 (13) | 0.64897 (9) | 0.0334 (6) | |
C1 | −0.0375 (3) | 0.04826 (15) | 0.57957 (11) | 0.0286 (6) | |
C2 | 0.2361 (3) | 0.04863 (15) | 0.59512 (11) | 0.0314 (6) | |
C3 | 0.0833 (3) | 0.09921 (15) | 0.67621 (12) | 0.0322 (6) | |
C4 | −0.0634 (3) | 0.07811 (15) | 0.64204 (10) | 0.0273 (6) | |
C5 | −0.1472 (3) | 0.00954 (16) | 0.67624 (12) | 0.0309 (7) | |
C6 | −0.0575 (3) | −0.06689 (15) | 0.68050 (10) | 0.0286 (6) | |
C7 | −0.0797 (3) | −0.12794 (16) | 0.64032 (12) | 0.0347 (7) | |
C8 | 0.0003 (4) | −0.19929 (18) | 0.64508 (13) | 0.0430 (8) | |
C9 | 0.1036 (4) | −0.21058 (19) | 0.69051 (14) | 0.0447 (8) | |
C10 | 0.1284 (4) | −0.15038 (18) | 0.73039 (14) | 0.0436 (8) | |
C11 | 0.0484 (3) | −0.07930 (18) | 0.72570 (12) | 0.0366 (7) | |
C12 | −0.1717 (3) | 0.15218 (17) | 0.64069 (12) | 0.0318 (7) | |
C13 | −0.1120 (3) | 0.22087 (16) | 0.60477 (11) | 0.0317 (6) | |
C14 | −0.0059 (4) | 0.27493 (18) | 0.62691 (13) | 0.0409 (7) | |
C15 | 0.0449 (4) | 0.33920 (19) | 0.59442 (15) | 0.0506 (9) | |
C16 | −0.0121 (4) | 0.3509 (2) | 0.53849 (14) | 0.0501 (8) | |
C17 | −0.1148 (4) | 0.29751 (19) | 0.51558 (13) | 0.0473 (8) | |
C18 | −0.1652 (4) | 0.23301 (19) | 0.54796 (12) | 0.0407 (7) | |
H1 | 0.127 (4) | 0.0115 (19) | 0.5266 (15) | 0.072 (11)* | |
H7 | −0.158 (3) | −0.1225 (16) | 0.6105 (11) | 0.041 (8)* | |
H8 | −0.014 (3) | −0.2450 (18) | 0.6191 (13) | 0.059 (9)* | |
H9 | 0.159 (3) | −0.2605 (16) | 0.6925 (11) | 0.042 (8)* | |
H10 | 0.199 (3) | −0.1603 (15) | 0.7625 (11) | 0.041 (8)* | |
H11 | 0.060 (3) | −0.0377 (15) | 0.7524 (12) | 0.036 (8)* | |
H14 | 0.033 (3) | 0.2692 (17) | 0.6642 (12) | 0.051 (9)* | |
H15 | 0.118 (3) | 0.3780 (17) | 0.6111 (11) | 0.043 (8)* | |
H16 | 0.021 (3) | 0.3982 (17) | 0.5183 (13) | 0.057 (9)* | |
H17 | −0.160 (3) | 0.3020 (17) | 0.4752 (13) | 0.057 (9)* | |
H18 | −0.232 (3) | 0.1955 (14) | 0.5325 (10) | 0.030 (7)* | |
H5A | −0.242 (3) | 0.0023 (13) | 0.6565 (10) | 0.027 (7)* | |
H12A | −0.187 (3) | 0.1670 (14) | 0.6826 (11) | 0.033 (7)* | |
H5B | −0.163 (3) | 0.0319 (13) | 0.7160 (11) | 0.029 (7)* | |
H12B | −0.269 (3) | 0.1353 (14) | 0.6252 (10) | 0.024 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0256 (10) | 0.0551 (12) | 0.0254 (9) | 0.0020 (9) | −0.0013 (8) | −0.0077 (9) |
O2 | 0.0500 (13) | 0.0565 (13) | 0.0296 (11) | −0.0135 (10) | −0.0050 (9) | −0.0048 (10) |
N1 | 0.0203 (12) | 0.0438 (14) | 0.0216 (11) | 0.0002 (10) | −0.0002 (9) | −0.0031 (10) |
N2 | 0.0284 (14) | 0.0544 (15) | 0.0370 (13) | 0.0011 (11) | −0.0047 (11) | 0.0029 (12) |
N3 | 0.0257 (14) | 0.0562 (16) | 0.0451 (15) | −0.0016 (11) | −0.0060 (12) | −0.0055 (13) |
N4 | 0.0317 (15) | 0.0536 (15) | 0.0406 (14) | −0.0056 (12) | −0.0114 (12) | 0.0014 (12) |
N5 | 0.0290 (14) | 0.0406 (13) | 0.0308 (13) | −0.0029 (11) | −0.0022 (10) | 0.0017 (11) |
C1 | 0.0292 (16) | 0.0353 (15) | 0.0212 (13) | −0.0012 (12) | −0.0001 (12) | 0.0004 (12) |
C2 | 0.0377 (18) | 0.0318 (15) | 0.0248 (14) | −0.0047 (13) | −0.0024 (12) | 0.0060 (12) |
C3 | 0.0354 (17) | 0.0293 (15) | 0.0318 (15) | −0.0039 (12) | 0.0054 (13) | 0.0055 (13) |
C4 | 0.0247 (15) | 0.0365 (15) | 0.0207 (12) | −0.0020 (12) | 0.0028 (11) | −0.0034 (12) |
C5 | 0.0268 (16) | 0.0438 (17) | 0.0222 (14) | −0.0059 (13) | 0.0031 (13) | −0.0061 (13) |
C6 | 0.0242 (15) | 0.0378 (15) | 0.0237 (13) | −0.0074 (12) | 0.0042 (11) | 0.0018 (12) |
C7 | 0.0314 (17) | 0.0429 (18) | 0.0298 (15) | −0.0081 (14) | −0.0009 (13) | −0.0043 (13) |
C8 | 0.0441 (19) | 0.0410 (18) | 0.0439 (17) | −0.0056 (15) | 0.0018 (15) | −0.0110 (15) |
C9 | 0.0374 (18) | 0.0400 (18) | 0.057 (2) | 0.0008 (16) | 0.0023 (15) | 0.0029 (17) |
C10 | 0.0365 (19) | 0.0483 (19) | 0.0462 (18) | −0.0067 (15) | −0.0112 (16) | 0.0048 (16) |
C11 | 0.0378 (18) | 0.0416 (17) | 0.0303 (15) | −0.0081 (14) | −0.0028 (13) | −0.0033 (14) |
C12 | 0.0261 (16) | 0.0416 (17) | 0.0278 (16) | 0.0004 (13) | 0.0037 (12) | −0.0023 (13) |
C13 | 0.0300 (15) | 0.0359 (15) | 0.0293 (14) | 0.0065 (13) | 0.0033 (12) | −0.0024 (12) |
C14 | 0.0439 (19) | 0.0421 (18) | 0.0367 (16) | 0.0009 (15) | −0.0073 (15) | 0.0020 (15) |
C15 | 0.052 (2) | 0.0407 (19) | 0.059 (2) | −0.0102 (16) | −0.0100 (17) | 0.0057 (17) |
C16 | 0.056 (2) | 0.0455 (19) | 0.049 (2) | 0.0007 (17) | 0.0091 (17) | 0.0103 (17) |
C17 | 0.061 (2) | 0.049 (2) | 0.0325 (17) | 0.0101 (17) | −0.0002 (16) | 0.0018 (16) |
C18 | 0.0422 (18) | 0.0431 (18) | 0.0367 (17) | 0.0000 (15) | −0.0055 (14) | −0.0038 (15) |
O1—C1 | 1.222 (3) | C8—C9 | 1.384 (4) |
O2—C3 | 1.201 (3) | C8—H8 | 0.98 (3) |
N1—C1 | 1.364 (3) | C9—C10 | 1.380 (4) |
N1—C2 | 1.366 (3) | C9—H9 | 0.97 (3) |
N1—H1 | 0.89 (3) | C10—C11 | 1.382 (4) |
N2—C2 | 1.323 (3) | C10—H10 | 0.97 (3) |
N2—N3 | 1.361 (3) | C11—H11 | 0.93 (3) |
N3—N4 | 1.297 (3) | C12—C13 | 1.507 (4) |
N4—N5 | 1.388 (3) | C12—H12A | 1.00 (2) |
N5—C2 | 1.329 (3) | C12—H12B | 0.95 (2) |
N5—C3 | 1.402 (3) | C13—C14 | 1.385 (4) |
C1—C4 | 1.535 (3) | C13—C18 | 1.397 (4) |
C3—C4 | 1.530 (4) | C14—C15 | 1.382 (4) |
C4—C12 | 1.555 (4) | C14—H14 | 0.92 (3) |
C4—C5 | 1.569 (4) | C15—C16 | 1.388 (4) |
C5—C6 | 1.501 (4) | C15—H15 | 0.98 (3) |
C5—H5A | 0.94 (3) | C16—C17 | 1.366 (4) |
C5—H5B | 1.00 (2) | C16—H16 | 0.96 (3) |
C6—C7 | 1.391 (3) | C17—C18 | 1.383 (4) |
C6—C11 | 1.397 (4) | C17—H17 | 1.01 (3) |
C7—C8 | 1.386 (4) | C18—H18 | 0.92 (2) |
C7—H7 | 0.96 (3) | ||
C1—N1—C2 | 121.9 (2) | C9—C8—C7 | 119.9 (3) |
C1—N1—H1 | 120 (2) | C9—C8—H8 | 115.7 (17) |
C2—N1—H1 | 117 (2) | C7—C8—H8 | 124.4 (18) |
C2—N2—N3 | 104.6 (2) | C10—C9—C8 | 120.0 (3) |
N4—N3—N2 | 112.6 (2) | C10—C9—H9 | 121.7 (16) |
N3—N4—N5 | 104.8 (2) | C8—C9—H9 | 118.3 (16) |
C2—N5—N4 | 107.8 (2) | C9—C10—C11 | 120.2 (3) |
C2—N5—C3 | 126.0 (2) | C9—C10—H10 | 118.3 (15) |
N4—N5—C3 | 126.2 (2) | C11—C10—H10 | 121.4 (15) |
O1—C1—N1 | 120.9 (2) | C10—C11—C6 | 120.8 (3) |
O1—C1—C4 | 119.8 (2) | C10—C11—H11 | 122.8 (16) |
N1—C1—C4 | 119.3 (2) | C6—C11—H11 | 116.4 (16) |
N2—C2—N5 | 110.2 (2) | C13—C12—C4 | 114.6 (2) |
N2—C2—N1 | 127.9 (2) | C13—C12—H12A | 112.2 (14) |
N5—C2—N1 | 121.9 (2) | C4—C12—H12A | 104.9 (14) |
O2—C3—N5 | 120.3 (2) | C13—C12—H12B | 108.8 (14) |
O2—C3—C4 | 125.1 (2) | C4—C12—H12B | 107.3 (14) |
N5—C3—C4 | 114.6 (2) | H12A—C12—H12B | 109 (2) |
C3—C4—C1 | 115.7 (2) | C14—C13—C18 | 117.6 (3) |
C3—C4—C12 | 108.8 (2) | C14—C13—C12 | 121.7 (2) |
C1—C4—C12 | 109.3 (2) | C18—C13—C12 | 120.6 (3) |
C3—C4—C5 | 107.1 (2) | C15—C14—C13 | 121.5 (3) |
C1—C4—C5 | 107.2 (2) | C15—C14—H14 | 117.8 (18) |
C12—C4—C5 | 108.6 (2) | C13—C14—H14 | 120.7 (18) |
C6—C5—C4 | 115.0 (2) | C14—C15—C16 | 119.8 (3) |
C6—C5—H5A | 111.6 (14) | C14—C15—H15 | 120.6 (15) |
C4—C5—H5A | 104.7 (14) | C16—C15—H15 | 119.5 (15) |
C6—C5—H5B | 109.4 (14) | C17—C16—C15 | 119.5 (3) |
C4—C5—H5B | 104.2 (13) | C17—C16—H16 | 123.2 (18) |
H5A—C5—H5B | 112 (2) | C15—C16—H16 | 117.2 (18) |
C7—C6—C11 | 118.2 (3) | C16—C17—C18 | 120.7 (3) |
C7—C6—C5 | 121.0 (2) | C16—C17—H17 | 123.8 (17) |
C11—C6—C5 | 120.8 (2) | C18—C17—H17 | 115.5 (18) |
C8—C7—C6 | 121.0 (3) | C17—C18—C13 | 120.8 (3) |
C8—C7—H7 | 119.0 (16) | C17—C18—H18 | 121.5 (15) |
C6—C7—H7 | 119.8 (16) | C13—C18—H18 | 117.7 (15) |
C2—N2—N3—N4 | 0.1 (3) | O1—C1—C4—C5 | 64.4 (3) |
N2—N3—N4—N5 | −0.1 (3) | N1—C1—C4—C5 | −113.8 (3) |
N3—N4—N5—C2 | 0.1 (3) | C3—C4—C5—C6 | −63.6 (3) |
N3—N4—N5—C3 | −177.9 (2) | C1—C4—C5—C6 | 61.2 (3) |
C2—N1—C1—O1 | −177.6 (2) | C12—C4—C5—C6 | 179.1 (2) |
C2—N1—C1—C4 | 0.6 (4) | C4—C5—C6—C7 | −94.0 (3) |
N3—N2—C2—N5 | −0.1 (3) | C4—C5—C6—C11 | 87.3 (3) |
N3—N2—C2—N1 | −179.9 (2) | C11—C6—C7—C8 | 0.3 (4) |
N4—N5—C2—N2 | 0.0 (3) | C5—C6—C7—C8 | −178.4 (3) |
C3—N5—C2—N2 | 178.0 (2) | C6—C7—C8—C9 | 0.3 (4) |
N4—N5—C2—N1 | 179.8 (2) | C7—C8—C9—C10 | −1.0 (5) |
C3—N5—C2—N1 | −2.1 (4) | C8—C9—C10—C11 | 1.1 (5) |
C1—N1—C2—N2 | 177.0 (3) | C9—C10—C11—C6 | −0.5 (4) |
C1—N1—C2—N5 | −2.8 (4) | C7—C6—C11—C10 | −0.2 (4) |
C2—N5—C3—O2 | −173.4 (2) | C5—C6—C11—C10 | 178.5 (3) |
N4—N5—C3—O2 | 4.3 (4) | C3—C4—C12—C13 | 68.6 (3) |
C2—N5—C3—C4 | 8.3 (3) | C1—C4—C12—C13 | −58.5 (3) |
N4—N5—C3—C4 | −174.0 (2) | C5—C4—C12—C13 | −175.1 (2) |
O2—C3—C4—C1 | 172.4 (2) | C4—C12—C13—C14 | −82.6 (3) |
N5—C3—C4—C1 | −9.4 (3) | C4—C12—C13—C18 | 98.8 (3) |
O2—C3—C4—C12 | 49.0 (3) | C18—C13—C14—C15 | 0.6 (4) |
N5—C3—C4—C12 | −132.7 (2) | C12—C13—C14—C15 | −178.0 (3) |
O2—C3—C4—C5 | −68.2 (3) | C13—C14—C15—C16 | 0.7 (5) |
N5—C3—C4—C5 | 110.0 (2) | C14—C15—C16—C17 | −1.8 (5) |
O1—C1—C4—C3 | −176.3 (2) | C15—C16—C17—C18 | 1.5 (5) |
N1—C1—C4—C3 | 5.5 (3) | C16—C17—C18—C13 | −0.2 (5) |
O1—C1—C4—C12 | −53.1 (3) | C14—C13—C18—C17 | −0.9 (4) |
N1—C1—C4—C12 | 128.6 (2) | C12—C13—C18—C17 | 177.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···N2i | 0.98 (3) | 2.73 (3) | 3.368 (4) | 123.0 (19) |
C12—H12B···N3ii | 0.95 (2) | 2.67 (3) | 3.542 (4) | 152.8 (18) |
C9—H9···N4iii | 0.97 (3) | 2.68 (3) | 3.501 (4) | 143 (2) |
C5—H5B···N4iv | 1.00 (2) | 2.71 (3) | 3.682 (4) | 165.8 (19) |
N1—H1···O1v | 0.89 (3) | 1.89 (4) | 2.774 (3) | 175 (3) |
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x−1, y, z; (iii) −x+1/2, y−1/2, z; (iv) x−1/2, y, −z+3/2; (v) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C18H15N5O2 |
Mr | 333.35 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 297 |
a, b, c (Å) | 8.6247 (13), 16.777 (3), 22.950 (4) |
V (Å3) | 3320.8 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.41 × 0.10 × 0.04 |
Data collection | |
Diffractometer | CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.963, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15340, 2932, 1813 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.122, 1.01 |
No. of reflections | 2932 |
No. of parameters | 286 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.19, −0.24 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Bruker, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···N2i | 0.98 (3) | 2.73 (3) | 3.368 (4) | 123.0 (19) |
C12—H12B···N3ii | 0.95 (2) | 2.67 (3) | 3.542 (4) | 152.8 (18) |
C9—H9···N4iii | 0.97 (3) | 2.68 (3) | 3.501 (4) | 143 (2) |
C5—H5B···N4iv | 1.00 (2) | 2.71 (3) | 3.682 (4) | 165.8 (19) |
N1—H1···O1v | 0.89 (3) | 1.89 (4) | 2.774 (3) | 175 (3) |
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x−1, y, z; (iii) −x+1/2, y−1/2, z; (iv) x−1/2, y, −z+3/2; (v) −x, −y, −z+1. |
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Heterocycle-based self-assembling systems capable of forming two-, three- and four-centered hydrogen bonds are gaining interest in designing functional solids due to their high dimerization constant (Zimmerman et al., 2002; Meijer et al., 2005; Baruah et al., 2005). The tetrazole-based title compound (I) has been synthesized and we report here its crystal structure.
The title molecule adopts a 'bat-like' conformation (Fig. 1). The central tetrazole-pyrimidine-dione group is approximately planar. Molecules of (I) form centrosymmetric dimers (Fig. 2) via intermolecular N—H···O hydrogen bonds (Table 1) in which tetrazole-pyrimidine-dione groups are coplanar and the benzyl groups are approximately perpendicular to this plane.
The molecular packing viewed down the a axis (Fig. 3) shows the association of the centrosymmetric dimers via C—H···N contacts (Table 1). The C9—H9···N4iii and C15—H15···N2i interactions link the centrosymmetric dimers along the b axis, whereas along the c axis these dimers are associated via the C5—H5B···N4iv contact.