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The title compound, C20H23N3O2, has a supramolecular structure of hydrogen bonding comprising N—H...O bonds which form a series of anti-parallel C(8), chains linked together by N—H...N R22(8) base-paired motifs which together form corrugated sheets containing R66(34) rings. This is one of a series of four substituted 3,7,7-tri­methyl-4,7,8,9-tetra­hydro-2H-pyrazolo­[3,4-b]­quinolin-5(6H)-one com­pounds which all have identical supramolecular structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001465/na6037sup1.cif
Contains datablocks global, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001465/na6037Isup2.hkl
Contains datablock I

CCDC reference: 159751

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.053
  • wR factor = 0.141
  • Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
PLAT_301 Alert B Main residue disorder ........................ 26.00 Perc.
Author response: ...see _publ_section_exptl_refinement for details
General Notes

FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C20 H23 N3 O2 Atom count from the _atom_site data: C20 H23.06 N3 O2 CELLZ_01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C20 H23 N3 O2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 80.00 80.00 0.00 H 92.00 92.24 -0.24 N 12.00 12.00 0.00 O 8.00 8.00 0.00 Difference between formula and atom_site contents detected. ALERT: check formula stoichiometry or atom site occupancies.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Comment top

Pyrazolo[3,4-b]quinolines are of interest as possible antiviral agents (Crenshaw et al., 1976, 1978; Smirnoff and Crenshaw, 1977). Some of their derivatives exhibit parasiticidic properties (Bristol-Meyers Co, 1973), and have been studied as potential antimalarial agents (Stein et al., 1970). Some pyrazolo[3,4-b]quinolines have shown bactericidal activity (Farghaly et al., 1989), have also been used as vasodilators (Bell & Ackerman, 1990) and evaluated for enzymatic inhibitory activity (Gatta et al., 1991).

In previous reports (Quiroga, Hormaza et al., 1998; Quiroga, Insuasty et al., 1998), we have reported an efficient and versatile synthesis of novel 4,7,8,9-tetrahydro-pyrimido- and 4,7,8,9-tetrahydropyrazolo[3,4-b]quinolin-5-ones from suitable pyrimidine and pyrazole amines to which dimedone and substituted benzaldehyde afford the ring annelation to quinoline.

Selected bond lengths and angles for the title compound, (I), are given in Table 1 and a view of the molecule is shown in Fig. 1.

The hydrogen-bonding pattern comprises anti-parallel C(8) (N2—H2···O51i) chains linked together by R22(8) (N9–H9···N1ii) base-paired motifs (Bernstein et al., 1995). This combination forms a corrugated sheet which contains R66(34) rings. This is shown in Fig. 2. The details of the hydrogen bonds are given in Table 2.

The 4-methoxyphenyl group was disordered on two sites, with occupancies of 0.65 and 0.35. The group is flipped through nearly 180° about an axis which runs close to the line passing between C4 and C420 and between the C47 and C427 methoxy atoms, the second of each atom pair being in the minor component.

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 5-aminopyrazole (1 mmol), dimedone (1 mmol) and 4-methoxybenzaldehyde (1 mmol) in 15 ml of absolute ethanol were heated to reflux for 20–50 min (thin-layer chromatography control). The reaction mixture was cooled and the solid corresponding to the title compound was filtered off, washed with ethanol, dried and recrystallized from ethanol to afford suitable crystals for diffraction (61% yield, m.p. 570 K).

Refinement top

H atoms were treated as riding atoms with C—H = 0.95–1.00 Å and N—H = 0.88 Å. In the disordered groups, each of the in the pairs C4/C420, C44/C424 and O44/O424 were given equal ADPs. The C4–C41 and C420–C421 bonds were fixed at 1.520 (5) Å. All other parameters in the groups were allowed to refine freely. Although there are some variations from normal phenyl bonds in the minor component, these lie within 3σ of the expected values so no further action was taken.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A view of the molecule with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Only the most populated disordered part of the molecule is included.
[Figure 2] Fig. 2. View of the hydrogen bonded sheets lying parallel to [010] showing the C(8) chains, the R22(8) rings and the R88(34) rings. Atom O51i is at (1.5 - x, 0.5 + y, 1.5 - z) and atom N1ii is at (2 - x, 1 - y, 2 - z).
3,7,7-Trimethyl-4-(4-methoxyphenyl)-4,7,8,9-tetrahydro-2H-pyrazolo[3,4-b]- quinolin-5(6H)-one (4). top
Crystal data top
C20H23N3O2Dx = 1.271 Mg m3
Mr = 337.41Melting point: 570 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.5820 (3) ÅCell parameters from 3956 reflections
b = 14.7031 (5) Åθ = 2.0–27.5°
c = 14.5369 (8) ŵ = 0.08 mm1
β = 106.0610 (15)°T = 150 K
V = 1762.70 (13) Å3Prism, colourless
Z = 40.38 × 0.24 × 0.18 mm
F(000) = 720
Data collection top
KappaCCD
diffractometer
3956 independent reflections
Radiation source: fine-focus sealed X-ray tube2662 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scans with κ offsetsθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1110
Tmin = 0.969, Tmax = 0.985k = 1816
11320 measured reflectionsl = 1518
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0655P)2 + 0.4575P]
where P = (Fo2 + 2Fc2)/3
3956 reflections(Δ/σ)max = 0.002
289 parametersΔρmax = 0.28 e Å3
2 restraintsΔρmin = 0.30 e Å3
Crystal data top
C20H23N3O2V = 1762.70 (13) Å3
Mr = 337.41Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.5820 (3) ŵ = 0.08 mm1
b = 14.7031 (5) ÅT = 150 K
c = 14.5369 (8) Å0.38 × 0.24 × 0.18 mm
β = 106.0610 (15)°
Data collection top
KappaCCD
diffractometer
3956 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
2662 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.985Rint = 0.029
11320 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0532 restraints
wR(F2) = 0.141H-atom parameters constrained
S = 1.03Δρmax = 0.28 e Å3
3956 reflectionsΔρmin = 0.30 e Å3
289 parameters
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. no transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.96978 (18)0.49548 (9)0.87356 (10)0.0255 (4)
N20.93258 (18)0.50561 (9)0.77707 (10)0.0249 (4)
C30.8362 (2)0.43944 (12)0.72831 (13)0.0244 (4)
C310.7756 (3)0.44108 (14)0.62201 (14)0.0348 (5)
C3A0.8090 (2)0.38006 (11)0.79599 (12)0.0223 (4)
C4A0.6997 (2)0.27021 (11)0.88876 (12)0.0215 (4)
C40.7353 (10)0.2850 (5)0.7912 (7)0.0263 (6)0.65
C410.8440 (6)0.2109 (3)0.7696 (3)0.0211 (11)0.65
C420.8013 (4)0.1640 (2)0.6848 (2)0.0263 (6)0.65
C430.8989 (12)0.0964 (9)0.6615 (10)0.024 (2)0.65
C441.0489 (4)0.0785 (2)0.7300 (2)0.0259 (7)0.65
C451.0950 (4)0.12531 (19)0.8160 (2)0.0291 (7)0.65
C460.9925 (4)0.1902 (2)0.8356 (3)0.0261 (7)0.65
C471.1192 (12)0.0368 (6)0.6313 (5)0.0367 (13)0.65
O441.1610 (3)0.01536 (14)0.71755 (15)0.0354 (5)0.65
C4200.7103 (15)0.2958 (8)0.7904 (10)0.0128 (16)0.35
O4240.9848 (5)0.0242 (2)0.6046 (3)0.0354 (5)0.35
C4210.7838 (9)0.2220 (6)0.7422 (6)0.0177 (19)0.35
C4220.7256 (6)0.2043 (3)0.6442 (4)0.0215 (11)0.35
C4230.7955 (6)0.1383 (3)0.6000 (4)0.0212 (11)0.35
C4240.936 (3)0.0882 (17)0.6586 (19)0.023 (3)0.35
C4250.9869 (8)0.1032 (4)0.7527 (4)0.0259 (13)0.35
C4260.9144 (9)0.1709 (5)0.7944 (5)0.0230 (13)0.35
C4271.106 (2)0.0355 (13)0.6578 (11)0.0367 (13)0.35
C50.5831 (2)0.20123 (11)0.89343 (13)0.0223 (4)
O510.50282 (15)0.16087 (8)0.82068 (9)0.0282 (3)
C60.5555 (2)0.17944 (12)0.98899 (13)0.0260 (4)
C70.7037 (2)0.19394 (11)1.07461 (13)0.0245 (4)
C710.6596 (3)0.18323 (13)1.16879 (14)0.0318 (5)
C720.8362 (2)0.12516 (12)1.07198 (14)0.0309 (5)
C80.7618 (2)0.29165 (11)1.06745 (12)0.0252 (4)
C8A0.7827 (2)0.31422 (11)0.97077 (13)0.0223 (4)
C9A0.8924 (2)0.41878 (11)0.88289 (12)0.0221 (4)
N90.88769 (18)0.38308 (9)0.97035 (10)0.0248 (4)
H20.96810.55110.74910.030*
H31A0.76980.37880.59730.052*
H31B0.84970.47700.59590.052*
H31C0.66740.46860.60280.052*
H40.63020.28440.73980.032*0.65
H420.70080.17790.63980.032*0.65
H430.86620.06410.60260.029*0.65
H451.19630.11290.86110.035*0.65
H461.02330.22150.89510.031*0.65
H17A1.21520.06940.62480.055*0.33
H17B1.07940.00390.57640.055*0.33
H17C1.03430.08060.63350.055*0.33
H17D1.00410.02800.59830.055*0.33
H17E1.13990.10130.64670.055*0.33
H17F1.18500.01680.58970.055*0.33
H4200.59820.30870.74930.015*0.35
H4220.63600.23820.60690.026*0.35
H4230.75370.12600.53360.025*0.35
H4251.07300.06790.79140.031*0.35
H4260.95600.18230.86110.028*0.35
H27G1.13540.07920.61430.055*0.18
H27H1.06540.06830.70500.055*0.18
H27I1.20260.00030.69080.055*0.18
H27J1.13360.01940.72580.055*0.18
H27K1.20350.03030.63510.055*0.18
H27L1.06630.09820.64920.055*0.18
H6A0.52080.11520.98850.031*
H6B0.46570.21790.99750.031*
H71A0.75320.19951.22220.048*
H71B0.62890.12001.17590.048*
H71C0.56840.22341.16870.048*
H72A0.86750.13281.01250.046*
H72B0.79520.06331.07490.046*
H72C0.93090.13531.12690.046*
H8A0.68250.33441.08180.030*
H8B0.86670.30061.11650.030*
H90.95120.40451.02420.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0316 (9)0.0218 (8)0.0238 (9)0.0019 (6)0.0089 (7)0.0022 (6)
N20.0310 (9)0.0211 (7)0.0244 (9)0.0009 (6)0.0104 (7)0.0026 (6)
C30.0251 (10)0.0244 (9)0.0248 (10)0.0014 (7)0.0089 (8)0.0002 (7)
C310.0405 (12)0.0388 (11)0.0254 (11)0.0068 (9)0.0094 (9)0.0023 (8)
C3A0.0254 (9)0.0209 (9)0.0215 (10)0.0006 (7)0.0078 (8)0.0001 (7)
C4A0.0252 (9)0.0198 (9)0.0210 (10)0.0000 (7)0.0089 (7)0.0009 (7)
C40.0264 (15)0.0275 (15)0.0258 (15)0.0055 (12)0.0087 (12)0.0036 (13)
C410.025 (3)0.021 (2)0.019 (3)0.003 (2)0.009 (2)0.000 (2)
C420.0264 (15)0.0275 (15)0.0258 (15)0.0055 (12)0.0087 (12)0.0036 (13)
C430.018 (5)0.026 (3)0.030 (3)0.004 (3)0.010 (3)0.007 (2)
C440.0303 (19)0.0201 (15)0.0309 (19)0.0009 (14)0.0147 (16)0.0009 (13)
C450.0282 (16)0.0302 (16)0.0273 (17)0.0027 (13)0.0048 (14)0.0020 (12)
C460.0304 (19)0.0266 (17)0.0225 (18)0.0026 (14)0.0095 (15)0.0025 (13)
C470.043 (2)0.0323 (12)0.040 (5)0.0062 (12)0.022 (3)0.006 (3)
O440.0403 (11)0.0314 (10)0.0356 (11)0.0097 (8)0.0125 (9)0.0046 (8)
C4200.021 (5)0.009 (3)0.011 (3)0.005 (2)0.009 (3)0.002 (2)
O4240.0403 (11)0.0314 (10)0.0356 (11)0.0097 (8)0.0125 (9)0.0046 (8)
C4210.015 (5)0.018 (3)0.020 (5)0.002 (3)0.006 (3)0.001 (3)
C4220.022 (3)0.019 (2)0.021 (3)0.001 (2)0.002 (2)0.005 (2)
C4230.027 (3)0.022 (2)0.016 (3)0.001 (2)0.008 (2)0.005 (2)
C4240.013 (7)0.020 (4)0.039 (6)0.009 (4)0.014 (5)0.011 (4)
C4250.031 (4)0.022 (3)0.028 (4)0.009 (3)0.014 (3)0.005 (2)
C4260.022 (4)0.029 (4)0.015 (3)0.002 (3)0.001 (3)0.002 (3)
C4270.043 (2)0.0323 (12)0.040 (5)0.0062 (12)0.022 (3)0.006 (3)
C50.0213 (9)0.0194 (8)0.0270 (10)0.0036 (7)0.0080 (8)0.0015 (7)
O510.0279 (7)0.0267 (7)0.0297 (8)0.0049 (5)0.0077 (6)0.0066 (5)
C60.0301 (10)0.0231 (9)0.0277 (10)0.0026 (7)0.0126 (8)0.0005 (7)
C70.0311 (10)0.0210 (9)0.0240 (10)0.0006 (7)0.0123 (8)0.0001 (7)
C710.0429 (12)0.0279 (10)0.0281 (11)0.0014 (9)0.0156 (9)0.0022 (8)
C720.0372 (11)0.0253 (10)0.0311 (11)0.0051 (8)0.0110 (9)0.0002 (8)
C80.0343 (11)0.0210 (9)0.0217 (10)0.0014 (8)0.0098 (8)0.0027 (7)
C8A0.0255 (10)0.0176 (8)0.0248 (10)0.0023 (7)0.0087 (8)0.0002 (7)
C9A0.0251 (9)0.0175 (8)0.0236 (10)0.0010 (7)0.0069 (8)0.0001 (7)
N90.0316 (9)0.0219 (7)0.0189 (8)0.0061 (6)0.0036 (6)0.0014 (6)
Geometric parameters (Å, º) top
N1—C9A1.335 (2)O424—C4241.37 (2)
N1—N21.358 (2)O424—C4271.42 (2)
N2—C31.345 (2)C421—C4261.388 (8)
N2—H20.8800C421—C4221.398 (10)
C3—C3A1.383 (2)C422—C4231.388 (7)
C3—C311.488 (3)C422—H4220.9500
C31—H31A0.9800C423—C4241.47 (2)
C31—H31B0.9800C423—H4230.9500
C31—H31C0.9800C424—C4251.33 (3)
C3A—C9A1.390 (2)C425—C4261.398 (9)
C3A—C4201.490 (15)C425—H4250.9500
C3A—C41.528 (9)C426—H4260.9500
C4A—C8A1.370 (2)C427—H27G0.9800
C4A—C51.439 (2)C427—H27H0.9800
C4A—C4201.505 (14)C427—H27I0.9800
C4A—C41.547 (10)C427—H27J0.9800
C4—C411.521 (4)C427—H27K0.9800
C4—H41.0000C427—H27L0.9800
C41—C421.371 (5)C5—O511.242 (2)
C41—C461.401 (5)C5—C61.507 (2)
C42—C431.400 (11)C6—C71.528 (3)
C42—H420.9500C6—H6A0.9900
C43—C441.418 (13)C6—H6B0.9900
C43—H430.9500C7—C711.526 (2)
C44—O441.384 (4)C7—C721.531 (2)
C44—C451.386 (4)C7—C81.534 (2)
C45—C461.381 (4)C71—H71A0.9800
C45—H450.9500C71—H71B0.9800
C46—H460.9500C71—H71C0.9800
C47—O441.428 (8)C72—H72A0.9800
C47—H17A0.9800C72—H72B0.9800
C47—H17B0.9800C72—H72C0.9800
C47—H17C0.9800C8—C8A1.502 (2)
C47—H17D0.9800C8—H8A0.9900
C47—H17E0.9800C8—H8B0.9900
C47—H17F0.9800C8A—N91.357 (2)
C420—C4211.520 (5)C9A—N91.386 (2)
C420—H4201.0000N9—H90.8800
C9A—N1—N2102.49 (14)C422—C421—C420121.8 (7)
C3—N2—N1113.55 (14)C423—C422—C421121.6 (5)
C3—N2—H2123.2C423—C422—H422119.2
N1—N2—H2123.2C421—C422—H422119.2
N2—C3—C3A106.38 (15)C422—C423—C424118.2 (10)
N2—C3—C31121.52 (16)C422—C423—H423120.9
C3A—C3—C31132.06 (17)C424—C423—H423120.9
C3—C31—H31A109.5C425—C424—O424129.6 (18)
C3—C31—H31B109.5C425—C424—C423119.8 (15)
H31A—C31—H31B109.5O424—C424—C423110.3 (18)
C3—C31—H31C109.5C424—C425—C426120.2 (11)
H31A—C31—H31C109.5C424—C425—H425119.9
H31B—C31—H31C109.5C426—C425—H425119.9
C3—C3A—C9A104.03 (15)C421—C426—C425122.5 (7)
C3—C3A—C420133.7 (5)C421—C426—H426118.8
C9A—C3A—C420122.1 (5)C425—C426—H426118.8
C3—C3A—C4134.0 (4)O424—C427—H27G109.5
C9A—C3A—C4121.3 (4)O424—C427—H27H109.5
C420—C3A—C410.0 (5)H27G—C427—H27H109.5
C8A—C4A—C5119.51 (16)O424—C427—H27I109.5
C8A—C4A—C420123.7 (6)H27G—C427—H27I109.5
C5—C4A—C420116.5 (6)H27H—C427—H27I109.5
C8A—C4A—C4123.0 (4)O424—C427—H27J109.5
C5—C4A—C4117.3 (4)H27G—C427—H27J141.1
C420—C4A—C49.8 (5)H27H—C427—H27J56.3
C41—C4—C3A113.2 (6)H27I—C427—H27J56.3
C41—C4—C4A112.2 (6)O424—C427—H27K109.5
C3A—C4—C4A105.7 (5)H27G—C427—H27K56.3
C41—C4—H4108.5H27H—C427—H27K141.1
C3A—C4—H4108.5H27I—C427—H27K56.3
C4A—C4—H4108.5H27J—C427—H27K109.5
C42—C41—C46118.2 (4)O424—C427—H27L109.5
C42—C41—C4121.3 (5)H27G—C427—H27L56.3
C46—C41—C4120.5 (4)H27H—C427—H27L56.3
C41—C42—C43123.1 (6)H27I—C427—H27L141.1
C41—C42—H42118.4H27J—C427—H27L109.5
C43—C42—H42118.4H27K—C427—H27L109.5
C42—C43—C44116.7 (9)O51—C5—C4A121.73 (16)
C42—C43—H43121.6O51—C5—C6119.43 (16)
C44—C43—H43121.6C4A—C5—C6118.82 (15)
O44—C44—C45114.6 (3)C5—C6—C7114.40 (15)
O44—C44—C43124.2 (5)C5—C6—H6A108.7
C45—C44—C43121.3 (5)C7—C6—H6A108.7
C46—C45—C44119.4 (3)C5—C6—H6B108.7
C46—C45—H45120.3C7—C6—H6B108.7
C44—C45—H45120.3H6A—C6—H6B107.6
C45—C46—C41121.3 (4)C71—C7—C6111.07 (15)
C45—C46—H46119.3C71—C7—C72108.94 (15)
C41—C46—H46119.3C6—C7—C72110.14 (15)
O44—C47—H17A109.5C71—C7—C8108.89 (14)
O44—C47—H17B109.5C6—C7—C8106.77 (14)
H17A—C47—H17B109.5C72—C7—C8111.03 (15)
O44—C47—H17C109.5C7—C71—H71A109.5
H17A—C47—H17C109.5C7—C71—H71B109.5
H17B—C47—H17C109.5H71A—C71—H71B109.5
O44—C47—H17D109.5C7—C71—H71C109.5
H17A—C47—H17D141.1H71A—C71—H71C109.5
H17B—C47—H17D56.3H71B—C71—H71C109.5
H17C—C47—H17D56.3C7—C72—H72A109.5
O44—C47—H17E109.5C7—C72—H72B109.5
H17A—C47—H17E56.3H72A—C72—H72B109.5
H17B—C47—H17E141.1C7—C72—H72C109.5
H17C—C47—H17E56.3H72A—C72—H72C109.5
H17D—C47—H17E109.5H72B—C72—H72C109.5
O44—C47—H17F109.5C8A—C8—C7113.31 (14)
H17A—C47—H17F56.3C8A—C8—H8A108.9
H17B—C47—H17F56.3C7—C8—H8A108.9
H17C—C47—H17F141.1C8A—C8—H8B108.9
H17D—C47—H17F109.5C7—C8—H8B108.9
H17E—C47—H17F109.5H8A—C8—H8B107.7
C44—O44—C47117.4 (4)N9—C8A—C4A122.31 (16)
C3A—C420—C4A109.8 (8)N9—C8A—C8114.85 (15)
C3A—C420—C421108.5 (9)C4A—C8A—C8122.82 (16)
C4A—C420—C421113.7 (8)N1—C9A—N9123.69 (15)
C3A—C420—H420108.3N1—C9A—C3A113.54 (15)
C4A—C420—H420108.3N9—C9A—C3A122.69 (16)
C421—C420—H420108.3C8A—N9—C9A118.34 (15)
C424—O424—C427114.3 (13)C8A—N9—H9120.8
C426—C421—C422117.6 (6)C9A—N9—H9120.8
C426—C421—C420120.6 (8)
C9A—N1—N2—C30.46 (19)C4A—C420—C421—C42639.6 (15)
N1—N2—C3—C3A1.1 (2)C3A—C420—C421—C42295.8 (11)
N1—N2—C3—C31176.96 (16)C4A—C420—C421—C422141.8 (9)
N2—C3—C3A—C9A1.26 (19)C426—C421—C422—C4230.3 (12)
C31—C3—C3A—C9A176.55 (19)C420—C421—C422—C423178.4 (9)
N2—C3—C3A—C420177.7 (4)C421—C422—C423—C4241.2 (13)
C31—C3—C3A—C4200.1 (5)C427—O424—C424—C4251 (3)
N2—C3—C3A—C4168.5 (4)C427—O424—C424—C423172.4 (13)
C31—C3—C3A—C413.7 (5)C422—C423—C424—C4253 (2)
C3—C3A—C4—C4172.1 (7)C422—C423—C424—O424177.9 (10)
C9A—C3A—C4—C4196.2 (6)O424—C424—C425—C426177.4 (16)
C420—C3A—C4—C41166 (5)C423—C424—C425—C4264 (2)
C3—C3A—C4—C4A164.7 (2)C422—C421—C426—C4250.4 (13)
C9A—C3A—C4—C4A26.9 (5)C420—C421—C426—C425179.1 (9)
C420—C3A—C4—C4A71 (5)C424—C425—C426—C4212.7 (16)
C8A—C4A—C4—C4198.2 (6)C8A—C4A—C5—O51178.54 (16)
C5—C4A—C4—C4176.4 (6)C420—C4A—C5—O514.4 (4)
C420—C4A—C4—C41164 (6)C4—C4A—C5—O516.6 (3)
C8A—C4A—C4—C3A25.6 (5)C8A—C4A—C5—C60.1 (2)
C5—C4A—C4—C3A159.8 (3)C420—C4A—C5—C6174.0 (3)
C420—C4A—C4—C3A72 (5)C4—C4A—C5—C6174.9 (3)
C3A—C4—C41—C42112.6 (6)O51—C5—C6—C7151.62 (15)
C4A—C4—C41—C42127.9 (6)C4A—C5—C6—C729.9 (2)
C3A—C4—C41—C4666.2 (8)C5—C6—C7—C71172.12 (14)
C4A—C4—C41—C4653.3 (8)C5—C6—C7—C7267.10 (19)
C46—C41—C42—C430.2 (9)C5—C6—C7—C853.54 (19)
C4—C41—C42—C43179.0 (8)C71—C7—C8—C8A170.63 (15)
C41—C42—C43—C440.8 (13)C6—C7—C8—C8A50.64 (19)
C42—C43—C44—O44178.6 (6)C72—C7—C8—C8A69.4 (2)
C42—C43—C44—C450.5 (13)C5—C4A—C8A—N9176.46 (15)
O44—C44—C45—C46179.7 (3)C420—C4A—C8A—N92.8 (4)
C43—C44—C45—C460.4 (8)C4—C4A—C8A—N99.0 (4)
C44—C45—C46—C411.2 (5)C5—C4A—C8A—C82.1 (3)
C42—C41—C46—C450.9 (6)C420—C4A—C8A—C8175.8 (4)
C4—C41—C46—C45177.9 (5)C4—C4A—C8A—C8172.4 (3)
C45—C44—O44—C47178.6 (4)C7—C8—C8A—N9156.14 (15)
C43—C44—O44—C472.2 (8)C7—C8—C8A—C4A25.2 (2)
C3—C3A—C420—C4A168.4 (3)N2—N1—C9A—N9176.35 (15)
C9A—C3A—C420—C4A7.5 (7)N2—N1—C9A—C3A0.42 (19)
C4—C3A—C420—C4A96 (5)C3—C3A—C9A—N11.1 (2)
C3—C3A—C420—C42166.8 (9)C420—C3A—C9A—N1178.0 (4)
C9A—C3A—C420—C421117.3 (7)C4—C3A—C9A—N1170.3 (3)
C4—C3A—C420—C42129 (4)C3—C3A—C9A—N9175.73 (15)
C8A—C4A—C420—C3A5.7 (7)C420—C3A—C9A—N91.2 (4)
C5—C4A—C420—C3A168.2 (3)C4—C3A—C9A—N912.9 (4)
C4—C4A—C420—C3A95 (5)C4A—C8A—N9—C9A9.9 (2)
C8A—C4A—C420—C421116.0 (8)C8—C8A—N9—C9A168.79 (15)
C5—C4A—C420—C42170.2 (10)N1—C9A—N9—C8A168.51 (16)
C4—C4A—C420—C42127 (4)C3A—C9A—N9—C8A8.0 (2)
C3A—C420—C421—C42682.9 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O51i0.881.962.824 (2)167
N9—H9···N1ii0.882.072.880 (2)153
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+2, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC20H23N3O2
Mr337.41
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)8.5820 (3), 14.7031 (5), 14.5369 (8)
β (°) 106.0610 (15)
V3)1762.70 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.38 × 0.24 × 0.18
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.969, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
11320, 3956, 2662
Rint0.029
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.141, 1.03
No. of reflections3956
No. of parameters289
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.30

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2000), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
N1—C9A1.335 (2)C8A—N91.357 (2)
N1—N21.358 (2)C9A—N91.386 (2)
N2—C31.345 (2)
C9A—N1—N2102.49 (14)C8A—N9—C9A118.34 (15)
C3—N2—N1113.55 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O51i0.881.962.824 (2)167
N9—H9···N1ii0.882.072.880 (2)153
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+2, y+1, z+2.
 

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