5,5-Dimethyl-3-(5-methyl-1H-pyrazol-3-ylamino)cyclohex-3-en-1-one

Quiroga, J.; Insuasty, B.; Abonia, R.; Mejía, D.; Cobo, J.; Nogueras, M.; Sanchez, A.; Low, J.N.

doi:10.1107/S0108270100012300

5,5-Dimethyl-3-(5-methyl-1H-pyrazol-3-ylamino)cyclohex-3-en-1-one

J. Quiroga, B. Insuasty, R. Abonia, D. Mejía, J. Cobo, M. Nogueras, A. Sanchez and J. N. Low

The molecules of the title compound, C₁₂H₁₇N₃O, are linked by two N—H

O hydrogen bonds to form a three-dimensional network. The N

O distances are 2.804 (3) and 2.766 (3) Å, both involving a common acceptor O atom.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100012300/gs1111sup1.cif Contains datablocks global, III
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100012300/gs1111IIIsup2.hkl Contains datablock III

CCDC reference: 156158

Comment top

Recently, we reported the structures of several pyrazolo[3,4-b]pyridines prepared from 3-aminopyrazoles and substituted cyanochalcones (Quiroga et al., 1999). Continuing the study of the reactions of 3-aminopyrazoles as intermediates in the preparation of fused pyrazole heterocycles, we have carried out reactions between these compounds and 1,3-diketones. Pyrazolo[3,4-c]pyridines have been prepared from arylidineaminopyrazoles and 1,3-dicarbonyl derivatives such as dimedone. The title compound, (III), results from the reaction of 3-amino-5-methylpyrazole, (I), on dimedone, (II), as shown in the scheme below. 3-N-substituted diaminopyrazole derivatives have been reported to be a target for neuropeptide Y antagonists (Fumaki, Fukuroda, Kanatani & Ihara, 1996) and hence are used in the treatment of bulimia, obesity and diabetes (Fumaki, Fukuroda, Kanatani, Kanatani & Ihara, 1996) or as an anticonvulsant (Lankau et al., 1999). \sch

The pyrazole ring in (III) is strictly planar with the atoms attached directly to it and shows high aromaticity, although there is a slight suggestion of double-bond character, as shown in the scheme. This arises because, due to the presence of the N6—H fragment attached to C4, there is no delocalization of the lone pair on N6 towards the pyrazole ring; C4—N6 [1.400 (3) Å] is clearly a single bond.

The cyclohexenone ring is disordered, with atoms C10, C11, C12 and C14 occupying two alternate components. The major component has an occupancy of 0.760 (5) and the minor 0.240 (5). In the following description the minor atom names are given in parentheses. The two positions for C13 overlap each other. In both of these components, all atoms except C11 (C11') are nearly coplanar, the maximum and minimum deviations being 0.035 (2) Å for C8 [0.092 (5) Å for C9] and −0.033 (2) Å for C7 [−0.086 (3) Å for C8]. Atom C11 in the major component is 0.641 (7) Å below the plane of the other five atoms and in the minor component 0.56 (2) Å above the plane of the other five atoms. This means that the molecule adopts each of the two possible sofa conformations involving C11 (C11'). The mean planes of these two disordered rings, consisting of the five ring atoms but omitting C11 (C11'), are inclined to one another by 17.7°.

Another structural feature is that the lone pair on N6 is delocalized to the α,β-unsaturated ketone showing amide vinylogous behaviour, as shown by the bond distances [N6—C7 1.343 (3), C7—C8 1.372 (3), C8—C9 1.413 (3) and C9—O91 1.255 (3) Å] and the torsion angle [N6—C7—C8—C9 − 178.8 (2)°]. This π system defined by the mean plane of N6, C7, C8, C9 and O91 is isolated from the pyrazole ring and both planes are inclined to one another at 28.61 (12)°. Selected bond lengths are given in Table 1.

The molecules are linked by two strong N—H···O hydrogen bonds, each involving O91 as an acceptor, to form a three-dimensional network of intersecting infinite chains. Atom O91 at (2 − x, 1 − y, z − 1/2) acts as an acceptor for the donor atom N1, with an N.·O distance of 2.804 (3) Å. Atom O91 at (3/2 − x, 1/2 + y, z − 1/2) acts as an acceptor for atom N6, with an N.·O distance of 2.766 (3) Å. The former gives rise to a primary C(9) motif, which when translated by the screw axis at (1, 1/2, z) gives an infinite spiral chain (Fig. 2). The latter gives a C(6) chain motif, producing an infinite chain running parallel to [011], produced by the action of the n-glide plane at 3/4 along a. Full hydrogen-bond data are given in Table 2.

Examination of the structure with PLATON (Spek, 2000) showed that there were no solvent-accessible voids in the crystal lattice.

Experimental top

A solution of 3-amino-5-methylpyrazole (3.1 mmol) and dimedone (3.1 mmol) in ethanol (5 ml) was heated to reflux for 30 min. Cooling the solution to room temperature afforded yellow crystals of (III) which were filtered out, washed with fresh ethanol and dried. Suitable crystals for X-ray diffraction were obtained after recrystallization from ethanol (yield 75%, m.p. 516–518 K). Analysis calculated for C₁₂H₁₇N₃O: C 65.73, H 7.81, N 19.16%; found C 65.53, H 7.75, N 19.29%.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. A view of the major component of (III) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of the crystal structure of (III) showing the infinite spiral chain parallel to [001] arising from the C(9) primary motif. Only the major component is shown [symmetry code: (i) 2 − x, 1 − y, z − 1/2].

5,5-dimethyl-3-(5-methyl-1H-pyrazol-3-ylamino)cyclohex-3-en-1-one top

Crystal data top

C₁₂H₁₇N₃O	D_x = 1.160 Mg m⁻³
M_r = 219.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 1515 reflections
a = 12.5130 (3) Å	θ = 3.3–27.4°
b = 9.4275 (3) Å	µ = 0.08 mm⁻¹
c = 10.6441 (3) Å	T = 150 K
V = 1255.65 (6) Å³	Plate, colourless
Z = 4	0.25 × 0.15 × 0.05 mm
F(000) = 472

Data collection top

Nonius KAPPA CCD diffractometer	1515 independent reflections
Radiation source: fine-focus sealed X-ray tube	1360 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans with κ offsets	θ_max = 27.4°, θ_min = 3.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −16→15
T_min = 0.981, T_max = 0.996	k = −12→12
13142 measured reflections	l = −13→13

Refinement top

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0676P)² + 0.3673P] where P = (F_o² + 2F_c²)/3
1515 reflections	(Δ/σ)_max < 0.001
148 parameters	Δρ_max = 0.31 e Å⁻³
11 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₂H₁₇N₃O	V = 1255.65 (6) Å³
M_r = 219.29	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.5130 (3) Å	µ = 0.08 mm⁻¹
b = 9.4275 (3) Å	T = 150 K
c = 10.6441 (3) Å	0.25 × 0.15 × 0.05 mm

Data collection top

Nonius KAPPA CCD diffractometer	1515 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	1360 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.996	R_int = 0.042
13142 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	11 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.05	Δρ_max = 0.31 e Å⁻³
1515 reflections	Δρ_min = −0.34 e Å⁻³
148 parameters

Special details top

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

− 2.7701 (0.0422) x + 7.2001 (0.0036) y + 6.4544 (0.0139) z = 4.6699 (0.0407)

* −0.0068 (0.0013) N6 * 0.0061 (0.0016) C7 * 0.0070 (0.0019) C8 * −0.0050 (0.0016) C9 * −0.0013 (0.0013) O91

Rms deviation of fitted atoms = 0.0057

− 2.7142 (0.0146) x + 9.0870 (0.0031) y + 1.6446 (0.0140) z = 3.5242 (0.0179)

Angle to previous plane (with approximate e.s.d.) = 28.61 (0.12)

* −0.0026 (0.0016) N1 * 0.0005 (0.0016) C2 * 0.0018 (0.0015) C3 * −0.0034 (0.0014) C4 * 0.0037 (0.0014) N5

Rms deviation of fitted atoms = 0.0027

− 1.8613 (0.0243) x + 7.1034 (0.0088) y + 6.8167 (0.0125) z = 5.5504 (0.0210)

Angle to previous plane (with approximate e.s.d.) = 30.96 (0.13)

* −0.0327 (0.0021) C7 * 0.0353 (0.0018) C8 * −0.0186 (0.0022) C9 * 0.0014 (0.0018) C10_a * 0.0145 (0.0017) C12_a −0.6414 (0.0067) C11_a

Rms deviation of fitted atoms = 0.0240

− 5.4354 (0.0637) x + 6.8601 (0.0262) y + 5.6505 (0.0412) z = 2.0087 (0.0690)

Angle to previous plane (with approximate e.s.d.) = 17.66 (0.42)

* 0.0317 (0.0049) C7 * −0.0863 (0.0028) C8 * 0.0923 (0.0052) C9 * −0.0482 (0.0046) C10' * 0.0105 (0.0045) C12' 0.5580 (0.0197) C11'

Rms deviation of fitted atoms = 0.0623

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	1.10964 (16)	0.6399 (2)	0.4368 (2)	0.0290 (5)
C2	1.1109 (2)	0.6181 (3)	0.5613 (2)	0.0301 (6)
C21	1.2104 (2)	0.6322 (4)	0.6382 (3)	0.0458 (8)
C3	1.0084 (2)	0.5815 (3)	0.5951 (2)	0.0279 (5)
C4	0.95073 (18)	0.5843 (2)	0.4815 (2)	0.0240 (5)
N5	1.01159 (17)	0.6207 (2)	0.3848 (2)	0.0292 (5)
N6	0.84220 (15)	0.5633 (2)	0.45551 (19)	0.0260 (4)
C7	0.77125 (18)	0.4823 (2)	0.5174 (2)	0.0262 (5)
C8	0.79550 (19)	0.4000 (3)	0.6198 (2)	0.0271 (5)
C9	0.7170 (2)	0.3153 (3)	0.6787 (2)	0.0307 (6)
O91	0.74012 (15)	0.2407 (2)	0.77250 (19)	0.0410 (5)
C10	0.6014 (3)	0.3270 (4)	0.6379 (4)	0.0314 (6)	0.760 (5)
C11	0.5903 (3)	0.3668 (4)	0.4991 (4)	0.0314 (6)	0.760 (5)
C12	0.6578 (3)	0.5002 (4)	0.4748 (4)	0.0314 (6)	0.760 (5)
C13	0.4732 (4)	0.4009 (5)	0.4714 (5)	0.0482 (8)	0.760 (5)
C14	0.6256 (3)	0.2456 (5)	0.4150 (4)	0.0482 (8)	0.760 (5)
C10'	0.6147 (9)	0.2726 (14)	0.6074 (12)	0.0314 (6)	0.240 (5)
C12'	0.6653 (7)	0.4544 (14)	0.4457 (11)	0.0314 (6)	0.240 (5)
C11'	0.5716 (10)	0.3953 (12)	0.5242 (12)	0.0314 (6)	0.240 (5)
C13'	0.4790 (12)	0.3483 (19)	0.4385 (15)	0.0482 (8)	0.240 (5)
C14'	0.5378 (10)	0.5157 (14)	0.6122 (12)	0.0482 (8)	0.240 (5)
H1	1.1665	0.6642	0.3932	0.035*
H21A	1.2644	0.6846	0.5902	0.069*
H21B	1.2379	0.5377	0.6589	0.069*
H21C	1.1942	0.6837	0.7159	0.069*
H3	0.9824	0.5594	0.6767	0.033*
H6	0.8171	0.6093	0.3899	0.031*
H8	0.8664	0.4000	0.6516	0.033*
H10A	0.5652	0.3998	0.6897	0.038*	0.760 (5)
H10B	0.5652	0.2352	0.6528	0.038*	0.760 (5)
H12A	0.6570	0.5218	0.3838	0.038*	0.760 (5)
H12B	0.6254	0.5816	0.5195	0.038*	0.760 (5)
H13A	0.4653	0.4261	0.3825	0.072*	0.760 (5)
H13B	0.4502	0.4809	0.5237	0.072*	0.760 (5)
H13C	0.4290	0.3178	0.4902	0.072*	0.760 (5)
H14A	0.5785	0.1638	0.4282	0.072*	0.760 (5)
H14B	0.6993	0.2191	0.4356	0.072*	0.760 (5)
H14C	0.6217	0.2755	0.3270	0.072*	0.760 (5)
H10C	0.5590	0.2447	0.6686	0.038*	0.240 (5)
H10D	0.6302	0.1894	0.5536	0.038*	0.240 (5)
H12C	0.6419	0.5446	0.4067	0.038*	0.240 (5)
H12D	0.6802	0.3868	0.3767	0.038*	0.240 (5)
H13D	0.4162	0.3264	0.4900	0.072*	0.240 (5)
H13E	0.5003	0.2637	0.3913	0.072*	0.240 (5)
H13F	0.4615	0.4250	0.3798	0.072*	0.240 (5)
H14D	0.5083	0.5940	0.5626	0.072*	0.240 (5)
H14E	0.6001	0.5491	0.6595	0.072*	0.240 (5)
H14F	0.4834	0.4809	0.6708	0.072*	0.240 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0253 (10)	0.0349 (11)	0.0268 (11)	−0.0070 (8)	0.0009 (8)	−0.0010 (9)
C2	0.0356 (14)	0.0276 (12)	0.0270 (13)	−0.0040 (10)	−0.0045 (11)	0.0035 (10)
C21	0.0385 (15)	0.0589 (19)	0.0400 (16)	−0.0139 (13)	−0.0125 (13)	0.0093 (15)
C3	0.0312 (12)	0.0311 (12)	0.0213 (12)	−0.0056 (9)	0.0009 (10)	0.0029 (10)
C4	0.0282 (11)	0.0203 (10)	0.0233 (11)	−0.0007 (8)	0.0021 (10)	0.0019 (9)
N5	0.0293 (10)	0.0327 (10)	0.0256 (10)	−0.0064 (9)	0.0017 (9)	0.0023 (9)
N6	0.0268 (10)	0.0274 (10)	0.0237 (10)	0.0016 (7)	−0.0007 (8)	0.0091 (8)
C7	0.0270 (11)	0.0268 (11)	0.0247 (12)	−0.0013 (9)	0.0006 (9)	0.0048 (9)
C8	0.0253 (11)	0.0294 (11)	0.0267 (13)	−0.0035 (9)	−0.0021 (10)	0.0069 (10)
C9	0.0289 (12)	0.0367 (13)	0.0264 (12)	−0.0071 (10)	−0.0043 (10)	0.0087 (11)
O91	0.0418 (10)	0.0488 (12)	0.0324 (10)	−0.0190 (9)	−0.0115 (9)	0.0214 (9)
C10	0.0276 (9)	0.0347 (14)	0.0319 (13)	−0.0034 (9)	−0.0014 (8)	0.0113 (10)
C11	0.0276 (9)	0.0347 (14)	0.0319 (13)	−0.0034 (9)	−0.0014 (8)	0.0113 (10)
C12	0.0276 (9)	0.0347 (14)	0.0319 (13)	−0.0034 (9)	−0.0014 (8)	0.0113 (10)
C13	0.0458 (14)	0.058 (2)	0.0410 (17)	−0.0188 (15)	−0.0101 (13)	0.0110 (14)
C14	0.0458 (14)	0.058 (2)	0.0410 (17)	−0.0188 (15)	−0.0101 (13)	0.0110 (14)
C10'	0.0276 (9)	0.0347 (14)	0.0319 (13)	−0.0034 (9)	−0.0014 (8)	0.0113 (10)
C12'	0.0276 (9)	0.0347 (14)	0.0319 (13)	−0.0034 (9)	−0.0014 (8)	0.0113 (10)
C11'	0.0276 (9)	0.0347 (14)	0.0319 (13)	−0.0034 (9)	−0.0014 (8)	0.0113 (10)
C13'	0.0458 (14)	0.058 (2)	0.0410 (17)	−0.0188 (15)	−0.0101 (13)	0.0110 (14)
C14'	0.0458 (14)	0.058 (2)	0.0410 (17)	−0.0188 (15)	−0.0101 (13)	0.0110 (14)

Geometric parameters (Å, º) top

N1—C2	1.342 (3)	C11—C14	1.517 (6)
N1—N5	1.358 (3)	C11—C13	1.530 (6)
N1—H1	0.8800	C11—C12	1.537 (5)
C2—C3	1.376 (4)	C12—H12A	0.9900
C2—C21	1.497 (4)	C12—H12B	0.9900
C21—H21A	0.9800	C13—H13A	0.9800
C21—H21B	0.9800	C13—H13B	0.9800
C21—H21C	0.9800	C13—H13C	0.9800
C3—C4	1.409 (4)	C14—H14A	0.9800
C3—H3	0.9500	C14—H14B	0.9800
C4—N5	1.326 (3)	C14—H14C	0.9800
C4—N6	1.400 (3)	C10'—C11'	1.554 (14)
N6—C7	1.343 (3)	C10'—H10C	0.9900
N6—H6	0.8800	C10'—H10D	0.9900
C7—C8	1.372 (3)	C12'—C11'	1.544 (15)
C7—C12	1.500 (4)	C12'—H12C	0.9900
C7—C12'	1.553 (8)	C12'—H12D	0.9900
C8—C9	1.413 (3)	C11'—C14'	1.531 (15)
C8—H8	0.9500	C11'—C13'	1.539 (15)
C9—O91	1.255 (3)	C13'—H13D	0.9800
C9—C10	1.515 (4)	C13'—H13E	0.9800
C9—C10'	1.542 (12)	C13'—H13F	0.9800
C10—C11	1.530 (5)	C14'—H14D	0.9800
C10—H10A	0.9900	C14'—H14E	0.9800
C10—H10B	0.9900	C14'—H14F	0.9800

C2—N1—N5	113.1 (2)	C14—C11—C10	111.0 (3)
C2—N1—H1	123.4	C14—C11—C13	108.9 (4)
N5—N1—H1	123.4	C10—C11—C13	108.9 (4)
N1—C2—C3	106.6 (2)	C14—C11—C12	110.9 (3)
N1—C2—C21	122.5 (3)	C10—C11—C12	108.3 (4)
C3—C2—C21	130.9 (3)	C13—C11—C12	108.7 (3)
C2—C21—H21A	109.5	C7—C12—C11	112.1 (3)
C2—C21—H21B	109.5	C7—C12—H12A	109.2
H21A—C21—H21B	109.5	C11—C12—H12A	109.2
C2—C21—H21C	109.5	C7—C12—H12B	109.2
H21A—C21—H21C	109.5	C11—C12—H12B	109.2
H21B—C21—H21C	109.5	H12A—C12—H12B	107.9
C2—C3—C4	104.4 (2)	C9—C10'—C11'	112.0 (9)
C2—C3—H3	127.8	C9—C10'—H10C	109.2
C4—C3—H3	127.8	C11'—C10'—H10C	109.2
N5—C4—N6	116.1 (2)	C9—C10'—H10D	109.2
N5—C4—C3	112.1 (2)	C11'—C10'—H10D	109.2
N6—C4—C3	131.6 (2)	H10C—C10'—H10D	107.9
C4—N5—N1	103.7 (2)	C11'—C12'—C7	116.3 (9)
C7—N6—C4	128.6 (2)	C11'—C12'—H12C	108.2
C7—N6—H6	115.7	C7—C12'—H12C	108.2
C4—N6—H6	115.7	C11'—C12'—H12D	108.2
N6—C7—C8	124.4 (2)	C7—C12'—H12D	108.2
N6—C7—C12	114.4 (2)	H12C—C12'—H12D	107.4
C8—C7—C12	120.9 (2)	C14'—C11'—C13'	111.6 (11)
N6—C7—C12'	114.8 (5)	C14'—C11'—C12'	105.9 (10)
C8—C7—C12'	118.9 (5)	C13'—C11'—C12'	110.8 (11)
C12—C7—C12'	20.3 (5)	C14'—C11'—C10'	107.4 (11)
C7—C8—C9	121.2 (2)	C13'—C11'—C10'	112.6 (12)
C7—C8—H8	119.4	C12'—C11'—C10'	108.3 (10)
C9—C8—H8	119.4	C11'—C13'—H13D	109.5
O91—C9—C8	120.7 (2)	C11'—C13'—H13E	109.5
O91—C9—C10	119.3 (2)	H13D—C13'—H13E	109.5
C8—C9—C10	119.7 (2)	C11'—C13'—H13F	109.5
O91—C9—C10'	115.9 (5)	H13D—C13'—H13F	109.5
C8—C9—C10'	120.4 (5)	H13E—C13'—H13F	109.5
C10—C9—C10'	23.8 (5)	C11'—C14'—H14D	109.5
C9—C10—C11	112.4 (3)	C11'—C14'—H14E	109.5
C9—C10—H10A	109.1	H14D—C14'—H14E	109.5
C11—C10—H10A	109.1	C11'—C14'—H14F	109.5
C9—C10—H10B	109.1	H14D—C14'—H14F	109.5
C11—C10—H10B	109.1	H14E—C14'—H14F	109.5
H10A—C10—H10B	107.9

N5—N1—C2—C3	0.3 (3)	C10'—C9—C10—C11	−68.3 (12)
N5—N1—C2—C21	179.6 (2)	C9—C10—C11—C14	69.7 (4)
N1—C2—C3—C4	0.1 (3)	C9—C10—C11—C13	−170.5 (3)
C21—C2—C3—C4	−179.0 (3)	C9—C10—C11—C12	−52.4 (5)
C2—C3—C4—N5	−0.5 (3)	N6—C7—C12—C11	153.5 (3)
C2—C3—C4—N6	−176.6 (2)	C8—C7—C12—C11	−32.7 (5)
N6—C4—N5—N1	177.40 (19)	C12'—C7—C12—C11	57.8 (13)
C3—C4—N5—N1	0.7 (3)	C14—C11—C12—C7	−68.6 (4)
C2—N1—N5—C4	−0.6 (3)	C10—C11—C12—C7	53.5 (5)
N5—C4—N6—C7	154.4 (2)	C13—C11—C12—C7	171.7 (3)
C3—C4—N6—C7	−29.7 (4)	O91—C9—C10'—C11'	160.7 (8)
C4—N6—C7—C8	−1.7 (4)	C8—C9—C10'—C11'	−38.9 (12)
C4—N6—C7—C12	171.8 (3)	C10—C9—C10'—C11'	56.4 (10)
C4—N6—C7—C12'	−165.9 (6)	N6—C7—C12'—C11'	−165.1 (8)
N6—C7—C8—C9	−178.8 (2)	C8—C7—C12'—C11'	29.8 (13)
C12—C7—C8—C9	8.1 (4)	C12—C7—C12'—C11'	−71.5 (15)
C12'—C7—C8—C9	−15.2 (7)	C7—C12'—C11'—C14'	68.8 (13)
C7—C8—C9—O91	−179.9 (3)	C7—C12'—C11'—C13'	−170.1 (10)
C7—C8—C9—C10	−6.8 (4)	C7—C12'—C11'—C10'	−46.1 (15)
C7—C8—C9—C10'	20.7 (7)	C9—C10'—C11'—C14'	−64.7 (12)
O91—C9—C10—C11	−156.5 (3)	C9—C10'—C11'—C13'	172.1 (10)
C8—C9—C10—C11	30.3 (5)	C9—C10'—C11'—C12'	49.2 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O91ⁱ	0.88	1.95	2.804 (3)	162
N6—H6···O91ⁱⁱ	0.88	1.90	2.766 (3)	168

Symmetry codes: (i) −x+2, −y+1, z−1/2; (ii) −x+3/2, y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₇N₃O
M_r	219.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	150
a, b, c (Å)	12.5130 (3), 9.4275 (3), 10.6441 (3)
V (Å³)	1255.65 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.15 × 0.05

Data collection
Diffractometer	Nonius KAPPA CCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995, 1997)
T_min, T_max	0.981, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	13142, 1515, 1360
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.122, 1.05
No. of reflections	1515
No. of parameters	148
No. of restraints	11
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.34

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO (Otwinowski & Minor, 1997), DENZO, SHELXS97 (Sheldrick, 1997), PLATON (Spek, 2000), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top

C4—N6	1.400 (3)	C8—C9	1.413 (3)
N6—C7	1.343 (3)	C9—O91	1.255 (3)
C7—C8	1.372 (3)

N6—C7—C8—C9	−178.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O91ⁱ	0.88	1.95	2.804 (3)	162
N6—H6···O91ⁱⁱ	0.88	1.90	2.766 (3)	168

Symmetry codes: (i) −x+2, −y+1, z−1/2; (ii) −x+3/2, y+1/2, z−1/2.

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