


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810033842/ci5159sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810033842/ci5159Isup2.hkl |
CCDC reference: 792487
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.071
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 7 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 4 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 2
Alert level G PLAT793_ALERT_4_G The Model has Chirality at C2 (Verify) .... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was synthesized according the procedure reported by Pryadeina et al.(2004). A mixture of ethyl 4,4,4-trifluoro-3-oxobutanoate (0.01 mol), 4-bromobenzaldehyde (0.01 mol) and 5-aminotetrazole (0.01 mol) in ethanol (20 ml) containing a catalytic amount of hydrochloric acid was heated for 12 h under reflux. Then the solvent was removed under reduced pressure. The residue was added to a solution of p-toluenesulfonic acid (0.05 g) in 100 mL of benzene, and the mixture was heated for 8 h with simultaneous removal of water as azeotrope with benzene. The solution was filtered while hot, the filtrate was evaporated, and the precipitate was recrystallized from ethanol. Cooling the ethanol solution slowly gave single crystals suitable for X-ray diffraction.
The N-bound H atom was located in a difference map and was refined freely [refined N–H length, 0.83 (2)Å]. All other H atoms were placed in calculated positions [C–H = 0.95–1.00 Å] and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(parent atom).
The tetrazolo[1,5-a]pyrimidine core represents an interesting pharmacophore with the feature of biological and pharmacological properties, which has human neutrophil elastase inhibitory (Von Nussbaum et al., 2010), late sodium channel blocker (Abelman et al., 2009) and hepatitis B virus surface antigen secretion inhibitory activities (Dougherty et al., 2007). This led us to pay much attention to the synthesis and bioactivity of compounds containing these two significant fragments. During the synthesis of trifluoromethylated tetrazolo[1,5-a]pyrimidine derivatives, the title compound was isolated and its structure was determined by X-ray analysis. The results are presented here.
In the title molecule (Fig.1), the tetrahydropyrimidine ring is in a flattened envelope conformation, with Cremer and Pople (1975) puckering parameters Q, θ, φ of 0.125 (2) Å, 109.7 (9)° and 11.7 (9)°, respectively; atom C2 deviates from the N1/N2/C1/C3/C4 plane (r.m.s. deviation 0.018 Å) by 0.177 (3) Å. The dihedral angle between N1/N2/C1/C3/C4 and C5-C10 planes [89.53 (3)°] shows that they are nearly perpendicular.
The crystal packing is stabilized by intermolecular N—H···N hydrogen bonds (Table 1 and Fig.2).
For the biological activity of tetrazolopyrimidine derivatives, see: Von Nussbaum et al. (2010); Abelman et al. (2009); Dougherty et al. (2007). For ring puckering parameters, see: Cremer & Pople (1975). For the synthesis, see: Pryadeina et al. (2004).
Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear (Rigaku/MSC, 2002); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C14H11BrF3N5O2 | F(000) = 832 |
Mr = 418.19 | Dx = 1.797 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4823 reflections |
a = 18.773 (2) Å | θ = 2.2–27.9° |
b = 10.4716 (11) Å | µ = 2.71 mm−1 |
c = 7.8700 (8) Å | T = 113 K |
β = 92.27 (3)° | Block, colourless |
V = 1545.9 (3) Å3 | 0.32 × 0.28 × 0.18 mm |
Z = 4 |
Rigaku Saturn diffractometer | 3681 independent reflections |
Radiation source: rotating anode | 2547 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.065 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.9°, θmin = 2.2° |
ω scans | h = −24→24 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002) | k = −13→13 |
Tmin = 0.477, Tmax = 0.641 | l = −10→10 |
18785 measured reflections |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0321P)2] where P = (Fo2 + 2Fc2)/3 |
3681 reflections | (Δ/σ)max = 0.001 |
231 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.82 e Å−3 |
C14H11BrF3N5O2 | V = 1545.9 (3) Å3 |
Mr = 418.19 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.773 (2) Å | µ = 2.71 mm−1 |
b = 10.4716 (11) Å | T = 113 K |
c = 7.8700 (8) Å | 0.32 × 0.28 × 0.18 mm |
β = 92.27 (3)° |
Rigaku Saturn diffractometer | 3681 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002) | 2547 reflections with I > 2σ(I) |
Tmin = 0.477, Tmax = 0.641 | Rint = 0.065 |
18785 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | Δρmax = 0.43 e Å−3 |
3681 reflections | Δρmin = −0.82 e Å−3 |
231 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
Br1 | 0.468171 (12) | 0.24266 (2) | −0.00430 (3) | 0.02485 (8) | |
F1 | 0.04617 (6) | 0.09175 (12) | 0.60550 (15) | 0.0283 (3) | |
F2 | 0.00359 (6) | 0.18117 (13) | 0.37917 (16) | 0.0312 (3) | |
F3 | 0.10127 (7) | 0.25030 (10) | 0.49390 (17) | 0.0279 (3) | |
H1 | 0.0275 (12) | 0.055 (2) | 0.176 (3) | 0.033 (7)* | |
N1 | 0.06837 (9) | 0.02879 (16) | 0.1959 (2) | 0.0142 (4) | |
N2 | 0.16300 (9) | −0.09820 (15) | 0.1113 (2) | 0.0139 (4) | |
N3 | 0.17768 (9) | −0.17880 (16) | −0.0190 (2) | 0.0195 (4) | |
N4 | 0.12129 (9) | −0.17855 (17) | −0.1192 (2) | 0.0196 (4) | |
N5 | 0.06960 (9) | −0.09971 (15) | −0.0596 (2) | 0.0163 (4) | |
O1 | 0.18713 (8) | 0.08260 (14) | 0.67228 (18) | 0.0266 (4) | |
O2 | 0.27052 (7) | −0.04022 (14) | 0.55633 (17) | 0.0209 (3) | |
C1 | 0.09759 (10) | −0.05253 (18) | 0.0835 (2) | 0.0134 (4) | |
C2 | 0.21318 (10) | −0.06715 (18) | 0.2535 (2) | 0.0143 (4) | |
H2 | 0.2315 | −0.1483 | 0.3062 | 0.017* | |
C3 | 0.17113 (10) | 0.00649 (18) | 0.3842 (2) | 0.0147 (4) | |
C4 | 0.10521 (11) | 0.05403 (18) | 0.3465 (2) | 0.0141 (4) | |
C5 | 0.27570 (10) | 0.00933 (19) | 0.1898 (2) | 0.0143 (4) | |
C6 | 0.26514 (11) | 0.12937 (19) | 0.1182 (3) | 0.0185 (5) | |
H6 | 0.2184 | 0.1642 | 0.1091 | 0.022* | |
C7 | 0.32231 (11) | 0.1991 (2) | 0.0599 (3) | 0.0187 (5) | |
H7 | 0.3150 | 0.2809 | 0.0097 | 0.022* | |
C8 | 0.39009 (11) | 0.14732 (19) | 0.0761 (2) | 0.0172 (5) | |
C9 | 0.40180 (11) | 0.02870 (19) | 0.1482 (3) | 0.0196 (5) | |
H9 | 0.4487 | −0.0054 | 0.1587 | 0.024* | |
C10 | 0.34446 (11) | −0.03993 (19) | 0.2049 (3) | 0.0185 (5) | |
H10 | 0.3521 | −0.1216 | 0.2548 | 0.022* | |
C11 | 0.20751 (11) | 0.02294 (19) | 0.5533 (3) | 0.0174 (4) | |
C12 | 0.31205 (11) | −0.0374 (2) | 0.7163 (3) | 0.0251 (5) | |
H12A | 0.2901 | −0.0933 | 0.8012 | 0.030* | |
H12B | 0.3145 | 0.0506 | 0.7620 | 0.030* | |
C13 | 0.38555 (12) | −0.0847 (2) | 0.6780 (3) | 0.0290 (6) | |
H13A | 0.3820 | −0.1701 | 0.6276 | 0.043* | |
H13B | 0.4150 | −0.0884 | 0.7835 | 0.043* | |
H13C | 0.4074 | −0.0262 | 0.5979 | 0.043* | |
C14 | 0.06429 (11) | 0.1435 (2) | 0.4593 (3) | 0.0205 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01555 (14) | 0.03165 (14) | 0.02782 (14) | −0.00341 (9) | 0.00700 (9) | 0.00705 (10) |
F1 | 0.0232 (8) | 0.0413 (8) | 0.0212 (7) | −0.0037 (6) | 0.0114 (6) | −0.0076 (6) |
F2 | 0.0184 (7) | 0.0410 (8) | 0.0338 (8) | 0.0131 (6) | −0.0035 (6) | −0.0185 (7) |
F3 | 0.0254 (8) | 0.0205 (7) | 0.0380 (8) | −0.0022 (5) | 0.0034 (6) | −0.0136 (6) |
N1 | 0.0094 (10) | 0.0162 (9) | 0.0174 (9) | 0.0012 (7) | 0.0031 (7) | −0.0026 (7) |
N2 | 0.0110 (9) | 0.0147 (8) | 0.0163 (9) | 0.0004 (7) | 0.0036 (7) | −0.0035 (7) |
N3 | 0.0184 (10) | 0.0208 (10) | 0.0194 (9) | 0.0007 (8) | 0.0033 (8) | −0.0074 (8) |
N4 | 0.0152 (10) | 0.0220 (10) | 0.0218 (10) | 0.0018 (8) | 0.0027 (8) | −0.0063 (8) |
N5 | 0.0145 (10) | 0.0169 (9) | 0.0178 (9) | 0.0003 (7) | 0.0045 (7) | −0.0036 (7) |
O1 | 0.0224 (9) | 0.0357 (9) | 0.0217 (8) | 0.0044 (7) | 0.0022 (7) | −0.0102 (7) |
O2 | 0.0175 (8) | 0.0271 (8) | 0.0178 (8) | 0.0040 (6) | −0.0011 (6) | −0.0042 (6) |
C1 | 0.0111 (11) | 0.0130 (9) | 0.0163 (10) | −0.0016 (8) | 0.0050 (8) | 0.0019 (8) |
C2 | 0.0122 (11) | 0.0140 (10) | 0.0167 (10) | 0.0005 (8) | 0.0012 (8) | −0.0019 (8) |
C3 | 0.0132 (11) | 0.0136 (9) | 0.0176 (10) | −0.0029 (8) | 0.0051 (8) | −0.0018 (8) |
C4 | 0.0137 (11) | 0.0135 (10) | 0.0154 (10) | −0.0030 (8) | 0.0058 (8) | −0.0013 (8) |
C5 | 0.0137 (11) | 0.0164 (10) | 0.0130 (10) | −0.0005 (8) | 0.0038 (8) | −0.0029 (8) |
C6 | 0.0124 (12) | 0.0203 (11) | 0.0230 (11) | 0.0033 (9) | 0.0031 (9) | 0.0007 (9) |
C7 | 0.0197 (12) | 0.0163 (10) | 0.0204 (11) | 0.0023 (9) | 0.0038 (9) | 0.0013 (9) |
C8 | 0.0152 (12) | 0.0216 (11) | 0.0153 (10) | −0.0036 (9) | 0.0052 (8) | −0.0008 (9) |
C9 | 0.0107 (11) | 0.0248 (12) | 0.0236 (12) | 0.0045 (9) | 0.0037 (9) | 0.0011 (9) |
C10 | 0.0168 (12) | 0.0170 (10) | 0.0220 (11) | 0.0036 (9) | 0.0047 (9) | 0.0015 (9) |
C11 | 0.0148 (12) | 0.0175 (10) | 0.0203 (11) | −0.0032 (9) | 0.0037 (9) | 0.0003 (9) |
C12 | 0.0193 (13) | 0.0366 (14) | 0.0192 (11) | 0.0028 (10) | −0.0031 (9) | 0.0003 (10) |
C13 | 0.0206 (13) | 0.0371 (14) | 0.0292 (13) | 0.0054 (11) | −0.0004 (10) | 0.0039 (11) |
C14 | 0.0142 (12) | 0.0238 (11) | 0.0235 (12) | 0.0006 (9) | 0.0014 (9) | −0.0069 (10) |
Br1—C8 | 1.9025 (19) | C3—C4 | 1.356 (3) |
F1—C14 | 1.328 (2) | C3—C11 | 1.482 (3) |
F2—C14 | 1.340 (2) | C4—C14 | 1.520 (3) |
F3—C14 | 1.338 (2) | C5—C6 | 1.388 (3) |
N1—C1 | 1.359 (2) | C5—C10 | 1.391 (3) |
N1—C4 | 1.374 (3) | C6—C7 | 1.392 (3) |
N1—H1 | 0.83 (2) | C6—H6 | 0.95 |
N2—C1 | 1.328 (2) | C7—C8 | 1.385 (3) |
N2—N3 | 1.365 (2) | C7—H7 | 0.95 |
N2—C2 | 1.470 (2) | C8—C9 | 1.379 (3) |
N3—N4 | 1.295 (2) | C9—C10 | 1.383 (3) |
N4—N5 | 1.371 (2) | C9—H9 | 0.95 |
N5—C1 | 1.320 (2) | C10—H10 | 0.95 |
O1—C11 | 1.201 (2) | C12—C13 | 1.508 (3) |
O2—C11 | 1.355 (2) | C12—H12A | 0.99 |
O2—C12 | 1.455 (2) | C12—H12B | 0.99 |
C2—C5 | 1.522 (2) | C13—H13A | 0.98 |
C2—C3 | 1.530 (3) | C13—H13B | 0.98 |
C2—H2 | 1.00 | C13—H13C | 0.98 |
C1—N1—C4 | 118.68 (17) | C8—C7—H7 | 120.6 |
C1—N1—H1 | 119.1 (17) | C6—C7—H7 | 120.6 |
C4—N1—H1 | 121.9 (16) | C9—C8—C7 | 121.45 (19) |
C1—N2—N3 | 108.16 (16) | C9—C8—Br1 | 119.80 (15) |
C1—N2—C2 | 127.32 (16) | C7—C8—Br1 | 118.75 (15) |
N3—N2—C2 | 124.50 (16) | C8—C9—C10 | 119.16 (19) |
N4—N3—N2 | 105.79 (16) | C8—C9—H9 | 120.4 |
N3—N4—N5 | 111.43 (16) | C10—C9—H9 | 120.4 |
C1—N5—N4 | 104.74 (16) | C9—C10—C5 | 120.74 (19) |
C11—O2—C12 | 116.29 (15) | C9—C10—H10 | 119.6 |
N5—C1—N2 | 109.88 (17) | C5—C10—H10 | 119.6 |
N5—C1—N1 | 129.27 (18) | O1—C11—O2 | 123.05 (19) |
N2—C1—N1 | 120.84 (18) | O1—C11—C3 | 127.68 (19) |
N2—C2—C5 | 110.17 (15) | O2—C11—C3 | 109.27 (17) |
N2—C2—C3 | 106.92 (15) | O2—C12—C13 | 106.47 (17) |
C5—C2—C3 | 112.42 (16) | O2—C12—H12A | 110.4 |
N2—C2—H2 | 109.1 | C13—C12—H12A | 110.4 |
C5—C2—H2 | 109.1 | O2—C12—H12B | 110.4 |
C3—C2—H2 | 109.1 | C13—C12—H12B | 110.4 |
C4—C3—C11 | 122.55 (18) | H12A—C12—H12B | 108.6 |
C4—C3—C2 | 121.92 (18) | C12—C13—H13A | 109.5 |
C11—C3—C2 | 115.53 (17) | C12—C13—H13B | 109.5 |
C3—C4—N1 | 122.81 (17) | H13A—C13—H13B | 109.5 |
C3—C4—C14 | 125.21 (18) | C12—C13—H13C | 109.5 |
N1—C4—C14 | 111.95 (17) | H13A—C13—H13C | 109.5 |
C6—C5—C10 | 119.19 (18) | H13B—C13—H13C | 109.5 |
C6—C5—C2 | 120.69 (18) | F1—C14—F3 | 108.26 (17) |
C10—C5—C2 | 120.11 (18) | F1—C14—F2 | 106.58 (17) |
C5—C6—C7 | 120.64 (19) | F3—C14—F2 | 105.95 (17) |
C5—C6—H6 | 119.7 | F1—C14—C4 | 114.01 (17) |
C7—C6—H6 | 119.7 | F3—C14—C4 | 111.34 (17) |
C8—C7—C6 | 118.80 (19) | F2—C14—C4 | 110.28 (17) |
C1—N2—N3—N4 | 0.1 (2) | C3—C2—C5—C6 | −55.7 (2) |
C2—N2—N3—N4 | −178.49 (17) | N2—C2—C5—C10 | −117.49 (19) |
N2—N3—N4—N5 | 0.2 (2) | C3—C2—C5—C10 | 123.4 (2) |
N3—N4—N5—C1 | −0.4 (2) | C10—C5—C6—C7 | 1.0 (3) |
N4—N5—C1—N2 | 0.4 (2) | C2—C5—C6—C7 | −179.92 (18) |
N4—N5—C1—N1 | −178.44 (19) | C5—C6—C7—C8 | −0.7 (3) |
N3—N2—C1—N5 | −0.3 (2) | C6—C7—C8—C9 | 0.2 (3) |
C2—N2—C1—N5 | 178.17 (17) | C6—C7—C8—Br1 | 179.84 (15) |
N3—N2—C1—N1 | 178.65 (16) | C7—C8—C9—C10 | 0.2 (3) |
C2—N2—C1—N1 | −2.8 (3) | Br1—C8—C9—C10 | −179.52 (15) |
C4—N1—C1—N5 | 172.99 (19) | C8—C9—C10—C5 | 0.1 (3) |
C4—N1—C1—N2 | −5.8 (3) | C6—C5—C10—C9 | −0.7 (3) |
C1—N2—C2—C5 | −111.0 (2) | C2—C5—C10—C9 | −179.76 (18) |
N3—N2—C2—C5 | 67.3 (2) | C12—O2—C11—O1 | 2.7 (3) |
C1—N2—C2—C3 | 11.5 (2) | C12—O2—C11—C3 | −177.93 (16) |
N3—N2—C2—C3 | −170.26 (16) | C4—C3—C11—O1 | −4.0 (3) |
N2—C2—C3—C4 | −13.1 (2) | C2—C3—C11—O1 | 175.58 (19) |
C5—C2—C3—C4 | 108.0 (2) | C4—C3—C11—O2 | 176.71 (17) |
N2—C2—C3—C11 | 167.39 (16) | C2—C3—C11—O2 | −3.7 (2) |
C5—C2—C3—C11 | −71.6 (2) | C11—O2—C12—C13 | −166.71 (17) |
C11—C3—C4—N1 | −173.55 (17) | C3—C4—C14—F1 | −65.4 (3) |
C2—C3—C4—N1 | 6.9 (3) | N1—C4—C14—F1 | 116.58 (19) |
C11—C3—C4—C14 | 8.6 (3) | C3—C4—C14—F3 | 57.5 (3) |
C2—C3—C4—C14 | −170.92 (18) | N1—C4—C14—F3 | −120.58 (19) |
C1—N1—C4—C3 | 3.5 (3) | C3—C4—C14—F2 | 174.78 (18) |
C1—N1—C4—C14 | −178.41 (17) | N1—C4—C14—F2 | −3.3 (2) |
N2—C2—C5—C6 | 63.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N5i | 0.83 (2) | 2.06 (2) | 2.862 (2) | 163 (2) |
Symmetry code: (i) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C14H11BrF3N5O2 |
Mr | 418.19 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 113 |
a, b, c (Å) | 18.773 (2), 10.4716 (11), 7.8700 (8) |
β (°) | 92.27 (3) |
V (Å3) | 1545.9 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.71 |
Crystal size (mm) | 0.32 × 0.28 × 0.18 |
Data collection | |
Diffractometer | Rigaku Saturn |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2002) |
Tmin, Tmax | 0.477, 0.641 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18785, 3681, 2547 |
Rint | 0.065 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.071, 0.94 |
No. of reflections | 3681 |
No. of parameters | 231 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.43, −0.82 |
Computer programs: CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N5i | 0.83 (2) | 2.06 (2) | 2.862 (2) | 163 (2) |
Symmetry code: (i) −x, −y, −z. |
The tetrazolo[1,5-a]pyrimidine core represents an interesting pharmacophore with the feature of biological and pharmacological properties, which has human neutrophil elastase inhibitory (Von Nussbaum et al., 2010), late sodium channel blocker (Abelman et al., 2009) and hepatitis B virus surface antigen secretion inhibitory activities (Dougherty et al., 2007). This led us to pay much attention to the synthesis and bioactivity of compounds containing these two significant fragments. During the synthesis of trifluoromethylated tetrazolo[1,5-a]pyrimidine derivatives, the title compound was isolated and its structure was determined by X-ray analysis. The results are presented here.
In the title molecule (Fig.1), the tetrahydropyrimidine ring is in a flattened envelope conformation, with Cremer and Pople (1975) puckering parameters Q, θ, φ of 0.125 (2) Å, 109.7 (9)° and 11.7 (9)°, respectively; atom C2 deviates from the N1/N2/C1/C3/C4 plane (r.m.s. deviation 0.018 Å) by 0.177 (3) Å. The dihedral angle between N1/N2/C1/C3/C4 and C5-C10 planes [89.53 (3)°] shows that they are nearly perpendicular.
The crystal packing is stabilized by intermolecular N—H···N hydrogen bonds (Table 1 and Fig.2).