4,4-Dimethyl-3,4-dihydro-pyrido[2',3':3,4]pyrazolo-[1,5-a][1,3,5]triazin-2-amine ethanol monosolvate.

In the title compound, C(10)H(12)N(6)·C(2)H(5)OH, the planarity of the heterocyclic system is slightly distorted at the triazine ring (r.m.s. deviation = 0.1191 Å), which adopts a conformation best described as inter-mediate between a flattened twisted boat and a half-boat with the tertiary Csp(3) atom at the bow. In the crystal, mol-ecules form centrosymmetric dimers connected by N⋯H-O and O⋯H-N hydrogen bonds between the amino group H atom, the ethanol solvent mol-ecule and the triazine N atom, making an R(4) (4)(12) graph-set motif. The other H atom of the amino group and the H atom on the endocyclic N atom form N⋯H-N hydrogen bonds with the N atoms of the pyrazole and pyridine rings, respectively, linking the mol-ecules into C(7)C(7) chains with the R(2) (2)(8) binary graph-set motif running along [010].

Related literature

For a review on the synthesis and biological activity of pyrazolo­[1,5-a]triazines, see: Dolzhenko et al. (2008 ▶). For the synthesis, crystal structure studies and biological activity of related fused gem-dimethyl-substituted amino-1,3,5-triazines, see: Dolzhenko et al. (2007a ▶,b ▶, 2009 ▶), Toyoda et al. (1997 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶). For a related structure, see: Sachdeva et al. (2010 ▶).

Experimental

Crystal data

C10H12N6·C2H6O

M = 262.32

Monoclinic,

a = 12.1250 (19) Å

b = 13.913 (2) Å

c = 16.598 (3) Å

β = 101.683 (4)°

V = 2742.0 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.60 × 0.38 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.950, T max = 0.991

9471 measured reflections

3129 independent reflections

2657 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.133

S = 1.06

3129 reflections

209 parameters

38 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681005097X/hg2760sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005097X/hg2760Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H12N6·C2H6O	F(000) = 1120
Mr = 262.32	Dx = 1.271 Mg m−3
Monoclinic, C2/c	Melting point: 559 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 12.1250 (19) Å	Cell parameters from 782 reflections
b = 13.913 (2) Å	θ = 2.7–27.3°
c = 16.598 (3) Å	µ = 0.09 mm−1
β = 101.683 (4)°	T = 100 K
V = 2742.0 (7) Å3	Plate, yellow
Z = 8	0.60 × 0.38 × 0.10 mm

Bruker SMART APEX CCD diffractometer	3129 independent reflections
Radiation source: fine-focus sealed tube	2657 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→14
Tmin = 0.950, Tmax = 0.991	k = −18→17
9471 measured reflections	l = −18→21

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0709P)2 + 1.8445P] where P = (Fo2 + 2Fc2)/3
3129 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.37 e Å−3
38 restraints	Δρmin = −0.21 e Å−3

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	Occ. (<1)
O1S	0.49619 (10)	0.11324 (8)	0.46397 (7)	0.0285 (3)
H1S	0.5246 (18)	0.1117 (15)	0.5165 (14)	0.039 (6)*
C1S	0.5838 (2)	0.0860 (2)	0.42339 (15)	0.0384 (7)	0.781 (6)
H1SA	0.5526	0.0769	0.3640	0.046*	0.781 (6)
H1SB	0.6169	0.0243	0.4461	0.046*	0.781 (6)
C2S	0.6736 (3)	0.1618 (3)	0.4346 (2)	0.0648 (11)	0.781 (6)
H2SA	0.7335	0.1420	0.4063	0.097*	0.781 (6)
H2SB	0.7051	0.1701	0.4934	0.097*	0.781 (6)
H2SC	0.6410	0.2226	0.4114	0.097*	0.781 (6)
C1SA	0.5898 (9)	0.1503 (9)	0.4290 (6)	0.044 (2)	0.219 (6)
H1SC	0.5651	0.1572	0.3687	0.053*	0.219 (6)
H1SD	0.6120	0.2146	0.4523	0.053*	0.219 (6)
C2SA	0.6822 (14)	0.0883 (12)	0.4464 (9)	0.077 (4)	0.219 (6)
H2SD	0.7437	0.1142	0.4227	0.116*	0.219 (6)
H2SE	0.6605	0.0250	0.4226	0.116*	0.219 (6)
H2SF	0.7072	0.0823	0.5062	0.116*	0.219 (6)
N1	0.56023 (10)	0.47488 (8)	0.67409 (7)	0.0203 (3)
N2	0.67666 (10)	0.34962 (9)	0.74160 (7)	0.0205 (3)
N3	0.68205 (10)	0.25362 (8)	0.72312 (7)	0.0187 (3)
N4	0.59745 (10)	0.13025 (8)	0.63025 (7)	0.0208 (3)
N5	0.77009 (11)	0.10579 (9)	0.72296 (8)	0.0220 (3)
H5	0.8212 (17)	0.0662 (15)	0.7465 (12)	0.034 (5)*
N6	0.68817 (13)	−0.01616 (10)	0.63779 (9)	0.0302 (3)
H6A	0.6334 (17)	−0.0354 (14)	0.6007 (12)	0.028 (5)*
H6B	0.7326 (17)	−0.0588 (15)	0.6701 (12)	0.037 (5)*
C1	0.47528 (13)	0.49206 (10)	0.61227 (9)	0.0226 (3)
H1	0.4479	0.5562	0.6059	0.027*
C2	0.42132 (13)	0.42321 (11)	0.55453 (9)	0.0235 (3)
H2	0.3604	0.4420	0.5119	0.028*
C3	0.45708 (12)	0.32946 (11)	0.56021 (9)	0.0211 (3)
H3	0.4242	0.2824	0.5212	0.025*
C4	0.54476 (12)	0.30661 (10)	0.62667 (8)	0.0182 (3)
C5	0.59298 (12)	0.38088 (10)	0.68156 (8)	0.0180 (3)
C6	0.60627 (12)	0.22357 (10)	0.65668 (8)	0.0189 (3)
C7	0.68259 (13)	0.07377 (11)	0.66450 (9)	0.0220 (3)
C8	0.75702 (12)	0.18664 (10)	0.77658 (8)	0.0210 (3)
C9	0.70180 (17)	0.15481 (14)	0.84683 (10)	0.0384 (4)
H9A	0.6953	0.2100	0.8823	0.058*
H9B	0.7480	0.1049	0.8791	0.058*
H9C	0.6266	0.1291	0.8243	0.058*
C10	0.87144 (15)	0.23234 (12)	0.80702 (12)	0.0363 (4)
H10A	0.8983	0.2606	0.7604	0.055*
H10B	0.9249	0.1832	0.8332	0.055*
H10C	0.8651	0.2827	0.8471	0.055*

	U11	U22	U33	U12	U13	U23
O1S	0.0298 (6)	0.0327 (6)	0.0198 (6)	0.0020 (5)	−0.0023 (5)	−0.0027 (4)
C1S	0.0441 (15)	0.0418 (17)	0.0304 (12)	0.0038 (12)	0.0104 (10)	−0.0026 (11)
C2S	0.050 (2)	0.101 (3)	0.0473 (17)	−0.0189 (19)	0.0193 (14)	0.0019 (18)
C1SA	0.044 (5)	0.049 (6)	0.040 (4)	−0.019 (4)	0.008 (4)	0.007 (4)
C2SA	0.089 (8)	0.077 (8)	0.069 (7)	0.018 (6)	0.021 (6)	0.022 (6)
N1	0.0230 (6)	0.0168 (6)	0.0203 (6)	−0.0004 (5)	0.0025 (5)	0.0008 (5)
N2	0.0230 (6)	0.0159 (6)	0.0205 (6)	0.0006 (5)	−0.0001 (5)	−0.0021 (5)
N3	0.0195 (6)	0.0158 (6)	0.0184 (6)	0.0010 (4)	−0.0016 (5)	−0.0014 (4)
N4	0.0233 (6)	0.0164 (6)	0.0192 (6)	0.0016 (5)	−0.0042 (5)	−0.0017 (4)
N5	0.0227 (6)	0.0180 (6)	0.0217 (6)	0.0050 (5)	−0.0042 (5)	−0.0022 (5)
N6	0.0356 (8)	0.0196 (7)	0.0273 (7)	0.0063 (6)	−0.0128 (6)	−0.0040 (5)
C1	0.0255 (8)	0.0178 (7)	0.0235 (7)	0.0024 (6)	0.0027 (6)	0.0018 (6)
C2	0.0234 (7)	0.0232 (7)	0.0209 (7)	0.0015 (6)	−0.0028 (6)	0.0024 (6)
C3	0.0223 (7)	0.0213 (7)	0.0177 (7)	−0.0012 (5)	−0.0002 (5)	−0.0009 (5)
C4	0.0190 (7)	0.0170 (7)	0.0183 (7)	−0.0008 (5)	0.0029 (5)	−0.0004 (5)
C5	0.0173 (6)	0.0190 (7)	0.0177 (6)	−0.0011 (5)	0.0033 (5)	0.0001 (5)
C6	0.0185 (7)	0.0209 (7)	0.0158 (6)	−0.0005 (5)	0.0003 (5)	0.0001 (5)
C7	0.0254 (7)	0.0201 (7)	0.0182 (7)	0.0013 (6)	−0.0011 (6)	−0.0004 (5)
C8	0.0226 (7)	0.0194 (7)	0.0179 (7)	0.0046 (5)	−0.0031 (6)	−0.0015 (5)
C9	0.0475 (11)	0.0425 (10)	0.0257 (8)	0.0202 (8)	0.0088 (8)	0.0115 (7)
C10	0.0286 (9)	0.0244 (8)	0.0466 (10)	0.0042 (7)	−0.0146 (8)	−0.0081 (7)

O1S—C1S	1.420 (3)	N5—C7	1.3596 (18)
O1S—C1SA	1.469 (9)	N5—C8	1.4628 (19)
O1S—H1S	0.87 (2)	N5—H5	0.86 (2)
C1S—C2S	1.500 (5)	N6—C7	1.334 (2)
C1S—H1SA	0.9900	N6—H6A	0.85 (2)
C1S—H1SB	0.9900	N6—H6B	0.90 (2)
C2S—H2SA	0.9800	C1—C2	1.418 (2)
C2S—H2SB	0.9800	C1—H1	0.9500
C2S—H2SC	0.9800	C2—C3	1.372 (2)
C1SA—C2SA	1.40 (2)	C2—H2	0.9500
C1SA—H1SC	0.9900	C3—C4	1.4047 (19)
C1SA—H1SD	0.9900	C3—H3	0.9500
C2SA—H2SD	0.9800	C4—C6	1.410 (2)
C2SA—H2SE	0.9800	C4—C5	1.4227 (19)
C2SA—H2SF	0.9800	C8—C10	1.517 (2)
N1—C1	1.3202 (19)	C8—C9	1.523 (2)
N1—C5	1.3651 (18)	C9—H9A	0.9800
N2—C5	1.3425 (18)	C9—H9B	0.9800
N2—N3	1.3749 (17)	C9—H9C	0.9800
N3—C6	1.3508 (17)	C10—H10A	0.9800
N3—C8	1.4682 (18)	C10—H10B	0.9800
N4—C7	1.3299 (19)	C10—H10C	0.9800
N4—C6	1.3678 (18)
C1S—O1S—C1SA	36.3 (5)	N1—C1—C2	125.71 (14)
C1S—O1S—H1S	106.7 (14)	N1—C1—H1	117.1
C1SA—O1S—H1S	102.9 (14)	C2—C1—H1	117.1
O1S—C1S—C2S	110.4 (3)	C3—C2—C1	119.98 (13)
O1S—C1S—H1SA	109.6	C3—C2—H2	120.0
C2S—C1S—H1SA	109.6	C1—C2—H2	120.0
O1S—C1S—H1SB	109.6	C2—C3—C4	116.60 (13)
C2S—C1S—H1SB	109.6	C2—C3—H3	121.7
H1SA—C1S—H1SB	108.1	C4—C3—H3	121.7
C1S—C2S—H2SA	109.5	C3—C4—C6	136.46 (13)
C1S—C2S—H2SB	109.5	C3—C4—C5	119.08 (13)
H2SA—C2S—H2SB	109.5	C6—C4—C5	104.45 (12)
C1S—C2S—H2SC	109.5	N2—C5—N1	122.69 (12)
H2SA—C2S—H2SC	109.5	N2—C5—C4	113.00 (12)
H2SB—C2S—H2SC	109.5	N1—C5—C4	124.30 (13)
C2SA—C1SA—O1S	110.6 (11)	N3—C6—N4	123.49 (12)
C2SA—C1SA—H1SC	109.5	N3—C6—C4	104.98 (12)
O1S—C1SA—H1SC	109.5	N4—C6—C4	131.53 (13)
C2SA—C1SA—H1SD	109.5	N4—C7—N6	119.96 (13)
O1S—C1SA—H1SD	109.5	N4—C7—N5	122.51 (14)
H1SC—C1SA—H1SD	108.1	N6—C7—N5	117.38 (13)
C1SA—C2SA—H2SD	109.5	N5—C8—N3	104.50 (11)
C1SA—C2SA—H2SE	109.5	N5—C8—C10	108.70 (13)
H2SD—C2SA—H2SE	109.5	N3—C8—C10	110.36 (13)
C1SA—C2SA—H2SF	109.5	N5—C8—C9	111.15 (13)
H2SD—C2SA—H2SF	109.5	N3—C8—C9	109.45 (12)
H2SE—C2SA—H2SF	109.5	C10—C8—C9	112.40 (14)
C1—N1—C5	114.26 (12)	C8—C9—H9A	109.5
C5—N2—N3	102.25 (11)	C8—C9—H9B	109.5
C6—N3—N2	115.31 (11)	H9A—C9—H9B	109.5
C6—N3—C8	122.17 (12)	C8—C9—H9C	109.5
N2—N3—C8	122.23 (11)	H9A—C9—H9C	109.5
C7—N4—C6	114.85 (12)	H9B—C9—H9C	109.5
C7—N5—C8	121.41 (12)	C8—C10—H10A	109.5
C7—N5—H5	120.0 (13)	C8—C10—H10B	109.5
C8—N5—H5	111.9 (13)	H10A—C10—H10B	109.5
C7—N6—H6A	116.8 (13)	C8—C10—H10C	109.5
C7—N6—H6B	118.9 (13)	H10A—C10—H10C	109.5
H6A—N6—H6B	120.5 (18)	H10B—C10—H10C	109.5
C1SA—O1S—C1S—C2S	21.3 (7)	C8—N3—C6—C4	174.81 (13)
C1S—O1S—C1SA—C2SA	−39.4 (9)	C7—N4—C6—N3	−12.5 (2)
C5—N2—N3—C6	−1.02 (16)	C7—N4—C6—C4	168.49 (15)
C5—N2—N3—C8	−175.06 (13)	C3—C4—C6—N3	178.26 (17)
C5—N1—C1—C2	−2.2 (2)	C5—C4—C6—N3	−0.17 (15)
N1—C1—C2—C3	−0.2 (2)	C3—C4—C6—N4	−2.6 (3)
C1—C2—C3—C4	2.3 (2)	C5—C4—C6—N4	178.95 (15)
C2—C3—C4—C6	179.72 (16)	C6—N4—C7—N6	−173.68 (14)
C2—C3—C4—C5	−2.0 (2)	C6—N4—C7—N5	1.7 (2)
N3—N2—C5—N1	−177.97 (13)	C8—N5—C7—N4	26.4 (2)
N3—N2—C5—C4	0.87 (16)	C8—N5—C7—N6	−158.08 (14)
C1—N1—C5—N2	−178.85 (14)	C7—N5—C8—N3	−37.89 (18)
C1—N1—C5—C4	2.4 (2)	C7—N5—C8—C10	−155.73 (14)
C3—C4—C5—N2	−179.23 (13)	C7—N5—C8—C9	80.06 (17)
C6—C4—C5—N2	−0.46 (17)	C6—N3—C8—N5	27.26 (18)
C3—C4—C5—N1	−0.4 (2)	N2—N3—C8—N5	−159.11 (12)
C6—C4—C5—N1	178.35 (13)	C6—N3—C8—C10	143.94 (14)
N2—N3—C6—N4	−178.45 (13)	N2—N3—C8—C10	−42.42 (19)
C8—N3—C6—N4	−4.4 (2)	C6—N3—C8—C9	−91.86 (17)
N2—N3—C6—C4	0.77 (17)	N2—N3—C8—C9	81.78 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N1i	0.86 (2)	2.16 (2)	3.0077 (18)	169.5 (18)
N6—H6B···N2i	0.90 (2)	2.08 (2)	2.9754 (18)	171.5 (18)
N6—H6A···O1Sii	0.85 (2)	2.03 (2)	2.8540 (18)	163.2 (18)
O1S—H1S···N4	0.87 (2)	1.93 (2)	2.7943 (17)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯N1i	0.86 (2)	2.16 (2)	3.0077 (18)	169.5 (18)
N6—H6B⋯N2i	0.90 (2)	2.08 (2)	2.9754 (18)	171.5 (18)
N6—H6A⋯O1Sii	0.85 (2)	2.03 (2)	2.8540 (18)	163.2 (18)
O1S—H1S⋯N4	0.87 (2)	1.93 (2)	2.7943 (17)	170 (2)

Symmetry codes: (i) ; (ii) .