3-Benzyl-6-isopropyl-5-meth­oxy-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one

In the title compound, C₁₅H₁₇N₅O₂, all ring atoms in the triazolopyrimidinone system are almost coplanar. The packing of the mol­ecules in the crystal structure is mainly due to inter­molecular C—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.056
• wR factor = 0.145
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

3-Benzyl-6-isopropyl-5-methoxy-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one

Crystal data

C15H17N5O2	Z = 2
Mr = 299.34	F(000) = 316
Triclinic, P1	Dx = 1.301 Mg m^−3
Hall symbol: -P 1	Melting point: 395 K
a = 7.0800 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7574 (10) Å	Cell parameters from 2691 reflections
c = 13.0492 (15) Å	θ = 3.0–24.9°
α = 102.369 (2)°	µ = 0.09 mm^−1
β = 103.511 (2)°	T = 292 K
γ = 92.883 (2)°	Block, colourless
V = 764.13 (15) Å^3	0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2475 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 27.5°, θmin = 1.7°
φ and ω scans	h = −9→9
8856 measured reflections	k = −11→11
3454 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.086P)^2] where P = (Fo^2 + 2Fc^2)/3
3454 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2782 (2)	0.61421 (19)	0.67208 (13)	0.0556 (4)
H1	0.3389	0.5764	0.7316	0.067*
C2	0.3776 (3)	0.6322 (2)	0.59563 (15)	0.0669 (5)
H2	0.5049	0.6058	0.6037	0.080*
C3	0.2912 (3)	0.6883 (2)	0.50816 (15)	0.0717 (5)
H3	0.3598	0.7010	0.4573	0.086*
C4	0.1022 (3)	0.7260 (2)	0.49561 (15)	0.0708 (5)
H4	0.0419	0.7629	0.4356	0.085*
C5	0.0026 (3)	0.70911 (19)	0.57174 (13)	0.0575 (4)
H5	−0.1244	0.7364	0.5634	0.069*
C6	0.0882 (2)	0.65220 (17)	0.66051 (11)	0.0460 (4)
C7	−0.0293 (2)	0.6317 (2)	0.74010 (12)	0.0562 (4)
H7A	−0.0754	0.7317	0.7662	0.067*
H7B	−0.1432	0.5574	0.7022	0.067*
C8	0.1750 (2)	0.66179 (16)	0.93074 (11)	0.0386 (3)
C9	0.2366 (2)	0.55336 (15)	0.98909 (11)	0.0403 (3)
C10	0.3343 (2)	0.60378 (16)	1.10089 (12)	0.0416 (3)
C11	0.2999 (2)	0.86568 (15)	1.06526 (11)	0.0392 (3)
C12	0.2904 (2)	1.12757 (17)	1.04446 (14)	0.0528 (4)
H12A	0.3388	1.1017	0.9807	0.079*
H12B	0.3434	1.2321	1.0846	0.079*
H12C	0.1504	1.1221	1.0238	0.079*
C13	0.4546 (3)	0.83833 (19)	1.25289 (13)	0.0628 (5)
H13	0.4702	0.7483	1.2865	0.075*
C14	0.6594 (3)	0.9168 (2)	1.27075 (17)	0.0852 (7)
H14A	0.7331	0.8462	1.2329	0.128*
H14B	0.7223	0.9432	1.3468	0.128*
H14C	0.6524	1.0108	1.2439	0.128*
C15	0.3221 (3)	0.9396 (2)	1.30892 (15)	0.0830 (6)
H15A	0.3245	1.0403	1.2910	0.125*
H15B	0.3676	0.9535	1.3860	0.125*
H15C	0.1910	0.8887	1.2851	0.125*
N1	0.07521 (18)	0.57722 (14)	0.83268 (10)	0.0476 (3)
N2	0.0768 (2)	0.42053 (15)	0.83065 (11)	0.0551 (4)
N3	0.1742 (2)	0.40548 (14)	0.92482 (11)	0.0512 (3)
N4	0.20552 (17)	0.82079 (13)	0.96405 (10)	0.0415 (3)
N5	0.36121 (18)	0.77107 (13)	1.13574 (9)	0.0429 (3)
O1	0.38855 (17)	0.52165 (12)	1.16447 (9)	0.0563 (3)
O2	0.34870 (16)	1.01695 (11)	1.11139 (9)	0.0518 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0543 (10)	0.0589 (10)	0.0491 (9)	0.0089 (8)	0.0043 (7)	0.0117 (8)
C2	0.0580 (11)	0.0736 (12)	0.0690 (12)	0.0085 (9)	0.0193 (9)	0.0127 (10)
C3	0.0886 (15)	0.0701 (13)	0.0588 (11)	−0.0013 (10)	0.0252 (10)	0.0153 (9)
C4	0.0906 (15)	0.0683 (12)	0.0526 (11)	0.0051 (10)	0.0075 (10)	0.0242 (9)
C5	0.0609 (10)	0.0563 (10)	0.0502 (10)	0.0087 (8)	0.0019 (8)	0.0142 (8)
C6	0.0510 (9)	0.0403 (8)	0.0381 (8)	0.0022 (6)	0.0007 (6)	0.0029 (6)
C7	0.0534 (10)	0.0671 (11)	0.0442 (9)	0.0119 (8)	0.0032 (7)	0.0133 (8)
C8	0.0417 (8)	0.0358 (7)	0.0402 (8)	0.0047 (6)	0.0130 (6)	0.0093 (6)
C9	0.0465 (8)	0.0300 (7)	0.0462 (8)	0.0053 (6)	0.0135 (6)	0.0105 (6)
C10	0.0475 (8)	0.0319 (7)	0.0481 (9)	0.0066 (6)	0.0121 (6)	0.0144 (6)
C11	0.0455 (8)	0.0291 (7)	0.0458 (8)	0.0058 (6)	0.0133 (6)	0.0123 (6)
C12	0.0616 (10)	0.0327 (8)	0.0705 (11)	0.0088 (7)	0.0204 (8)	0.0205 (7)
C13	0.0984 (14)	0.0402 (9)	0.0409 (9)	0.0070 (9)	0.0011 (8)	0.0086 (7)
C14	0.0795 (14)	0.0688 (13)	0.0781 (14)	0.0102 (11)	−0.0167 (11)	−0.0062 (11)
C15	0.1261 (18)	0.0707 (13)	0.0565 (12)	0.0084 (12)	0.0382 (12)	0.0078 (10)
N1	0.0522 (7)	0.0437 (7)	0.0434 (7)	0.0054 (6)	0.0070 (6)	0.0079 (6)
N2	0.0669 (9)	0.0396 (7)	0.0531 (8)	0.0019 (6)	0.0098 (7)	0.0053 (6)
N3	0.0646 (8)	0.0357 (7)	0.0509 (8)	0.0031 (6)	0.0119 (6)	0.0081 (6)
N4	0.0476 (7)	0.0341 (6)	0.0453 (7)	0.0069 (5)	0.0111 (5)	0.0150 (5)
N5	0.0549 (7)	0.0320 (6)	0.0404 (7)	0.0043 (5)	0.0070 (5)	0.0108 (5)
O1	0.0762 (8)	0.0387 (6)	0.0527 (7)	0.0092 (5)	0.0036 (5)	0.0207 (5)
O2	0.0701 (7)	0.0283 (5)	0.0552 (7)	0.0038 (5)	0.0099 (5)	0.0126 (5)

Geometric parameters (Å, º)

C1—C2	1.378 (2)	C10—N5	1.4267 (17)
C1—C6	1.383 (2)	C11—N4	1.2978 (18)
C1—H1	0.9300	C11—O2	1.3235 (16)
C2—C3	1.365 (3)	C11—N5	1.3772 (17)
C2—H2	0.9300	C12—O2	1.4512 (17)
C3—C4	1.375 (3)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.373 (2)	C12—H12C	0.9600
C4—H4	0.9300	C13—N5	1.4912 (19)
C5—C6	1.381 (2)	C13—C14	1.518 (3)
C5—H5	0.9300	C13—C15	1.525 (3)
C6—C7	1.507 (2)	C13—H13	0.9800
C7—N1	1.4491 (19)	C14—H14A	0.9600
C7—H7A	0.9700	C14—H14B	0.9600
C7—H7B	0.9700	C14—H14C	0.9600
C8—N1	1.3432 (18)	C15—H15A	0.9600
C8—N4	1.3568 (17)	C15—H15B	0.9600
C8—C9	1.367 (2)	C15—H15C	0.9600
C9—N3	1.3711 (18)	N1—N2	1.3674 (18)
C9—C10	1.422 (2)	N2—N3	1.2982 (18)
C10—O1	1.2198 (16)
C2—C1—C6	120.13 (16)	O2—C11—N5	112.52 (12)
C2—C1—H1	119.9	O2—C12—H12A	109.5
C6—C1—H1	119.9	O2—C12—H12B	109.5
C3—C2—C1	120.75 (18)	H12A—C12—H12B	109.5
C3—C2—H2	119.6	O2—C12—H12C	109.5
C1—C2—H2	119.6	H12A—C12—H12C	109.5
C2—C3—C4	119.64 (18)	H12B—C12—H12C	109.5
C2—C3—H3	120.2	N5—C13—C14	111.94 (15)
C4—C3—H3	120.2	N5—C13—C15	112.16 (15)
C5—C4—C3	119.91 (17)	C14—C13—C15	114.52 (16)
C5—C4—H4	120.0	N5—C13—H13	105.8
C3—C4—H4	120.0	C14—C13—H13	105.8
C4—C5—C6	121.01 (17)	C15—C13—H13	105.8
C4—C5—H5	119.5	C13—C14—H14A	109.5
C6—C5—H5	119.5	C13—C14—H14B	109.5
C5—C6—C1	118.56 (15)	H14A—C14—H14B	109.5
C5—C6—C7	118.90 (14)	C13—C14—H14C	109.5
C1—C6—C7	122.54 (14)	H14A—C14—H14C	109.5
N1—C7—C6	114.88 (13)	H14B—C14—H14C	109.5
N1—C7—H7A	108.5	C13—C15—H15A	109.5
C6—C7—H7A	108.5	C13—C15—H15B	109.5
N1—C7—H7B	108.5	H15A—C15—H15B	109.5
C6—C7—H7B	108.5	C13—C15—H15C	109.5
H7A—C7—H7B	107.5	H15A—C15—H15C	109.5
N1—C8—N4	126.96 (13)	H15B—C15—H15C	109.5
N1—C8—C9	105.16 (13)	C8—N1—N2	109.48 (12)
N4—C8—C9	127.88 (13)	C8—N1—C7	128.93 (13)
C8—C9—N3	109.01 (13)	N2—N1—C7	121.55 (13)
C8—C9—C10	119.92 (13)	N3—N2—N1	108.57 (12)
N3—C9—C10	130.86 (13)	N2—N3—C9	107.77 (12)
O1—C10—C9	127.50 (13)	C11—N4—C8	111.65 (12)
O1—C10—N5	120.86 (13)	C11—N5—C10	121.68 (12)
C9—C10—N5	111.62 (12)	C11—N5—C13	121.65 (12)
N4—C11—O2	120.40 (12)	C10—N5—C13	116.65 (11)
N4—C11—N5	127.08 (12)	C11—O2—C12	117.18 (12)
C6—C1—C2—C3	0.4 (3)	C8—N1—N2—N3	0.26 (16)
C1—C2—C3—C4	−0.6 (3)	C7—N1—N2—N3	−177.54 (13)
C2—C3—C4—C5	0.9 (3)	N1—N2—N3—C9	0.07 (16)
C3—C4—C5—C6	−1.0 (3)	C8—C9—N3—N2	−0.37 (16)
C4—C5—C6—C1	0.8 (2)	C10—C9—N3—N2	174.22 (15)
C4—C5—C6—C7	−178.34 (16)	O2—C11—N4—C8	177.85 (12)
C2—C1—C6—C5	−0.5 (2)	N5—C11—N4—C8	−1.8 (2)
C2—C1—C6—C7	178.63 (15)	N1—C8—N4—C11	176.90 (13)
C5—C6—C7—N1	−177.72 (14)	C9—C8—N4—C11	−2.4 (2)
C1—C6—C7—N1	3.2 (2)	N4—C11—N5—C10	3.5 (2)
N1—C8—C9—N3	0.51 (16)	O2—C11—N5—C10	−176.11 (11)
N4—C8—C9—N3	179.92 (13)	N4—C11—N5—C13	−174.93 (14)
N1—C8—C9—C10	−174.77 (12)	O2—C11—N5—C13	5.44 (19)
N4—C8—C9—C10	4.6 (2)	O1—C10—N5—C11	−179.63 (13)
C8—C9—C10—O1	175.96 (14)	C9—C10—N5—C11	−1.09 (19)
N3—C9—C10—O1	1.9 (3)	O1—C10—N5—C13	−1.1 (2)
C8—C9—C10—N5	−2.47 (19)	C9—C10—N5—C13	177.44 (13)
N3—C9—C10—N5	−176.57 (13)	C14—C13—N5—C11	−71.65 (19)
N4—C8—N1—N2	−179.89 (13)	C15—C13—N5—C11	58.7 (2)
C9—C8—N1—N2	−0.47 (15)	C14—C13—N5—C10	109.83 (16)
N4—C8—N1—C7	−2.3 (2)	C15—C13—N5—C10	−119.85 (15)
C9—C8—N1—C7	177.12 (14)	N4—C11—O2—C12	0.63 (19)
C6—C7—N1—C8	92.87 (18)	N5—C11—O2—C12	−179.71 (11)
C6—C7—N1—N2	−89.79 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1	0.93	2.52	2.866 (2)	102
C15—H15A···O2	0.96	2.36	2.846 (2)	111
C14—H14C···O2	0.96	2.44	2.961 (2)	114
C12—H12B···O1^i	0.96	2.50	3.4322 (19)	164
C1—H1···O1^ii	0.93	2.40	3.2481 (19)	152

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+2.