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Molecules of the title compound, C28H27ClN4O4·C2H6O, form a C(6) chain via an N—H...O hydrogen bond along the c axis by the operation of a c-glide plane, with N...O = 2.761 (3) Å and N—H...O = 165°. The mol­ecules are further linked by a weak C—H...O interaction, with C...O = 3.344 (4) Å and C—H...O = 150°. Pendant hydrogen-bonded ethanol solvent mol­ecules are attached to the chains by O—H...N hydrogen bonds, with O...N = 2.904 (3) Å and O—H...N = 175°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101014913/gg1082sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101014913/gg1082Isup2.hkl
Contains datablock I

CCDC reference: 175115

Comment top

Pyrazolo[3,4-b]quinolines are of interest as possible antiviral agents (Crenshaw et al., 1976, 1978; Smirnoff & Crenshaw, 1977). Some of their derivatives exhibit parasiticidic properties (Bristol-Meyers, 1973) and have been studied as potential antimalarial agents (Gein Stein et al., 1970). Other pyrazolo[3,4-b]quinolines have also shown bactericidal activity (Farghaly et al., 1989) and applications as vasodilators (Bell & Ackerman, 1990), and have even been evaluated for enzymatic inhibitory activity (Gatta et al., 1991). We have previously prepared diverse 4-aryl-3,7,7-trimethyl-4,7,8,9-tetrahydro- 2H-pyrazolo[3,4-b]quinolin-5-(6H)-ones and reported their structures (Cannon et al., 2001a,b,c,d). The present work was undertaken to expand the possible applications of such heterocycles, by using N-alkylation to prepare derivatives from azole systems. Here, we report the structure of the title compound, (I), which was prepared by the easy, efficient and regioselective method described below. \sch

Selected bond lengths and angles for (I) are given in Table 1 and are similar to those reported in the four structures cited above (Cannon et al., 2001a,b,c,d). Fig. 1 depicts a view of the molecule.

Molecules of (I) form C(6) chains (Bernstein et al., 1995) via the N9—H9···O5i hydrogen bond along the c axis by the operation of the c glide plane, as shown in Fig. 2 [symmetry code: (i) x, 1 - y, 1/2 + z]. The molecules in these chains are then linked by weak C12—H12···O12i interactions and this interaction, together with the N9—H9···O5i hydrogen bond, forms an R22(23) ring (Bernstein et al., 1995), as shown in Fig. 3. These linked chains are not connected to the chains related by the C-centring. Pendant hydrogen-bonded ethanol solvent molecules are attached to each molecule of (I). Details of the hydrogen bonding are given in Table 2.

There is significant ππ base-stacking between rings C131—C136 and N9/C8a/C4a/C4/C3a/C9a (at x, -y, 1/2 + z Not 1 - y?), where the distance between centres of gravity is 3.73 Å, the perpendicular distance of the centre of gravity of the former ring from the latter is 3.73 Å, the perpendicular distance of the centre of gravity of the latter from the former is 3.50 Å and the angle between the planes is 2.7°. In addition, ring C131—C136 is involved in ππ stacking with ring N1/N2/C3/C3a/C9a (at x, -y, 1/2 + z Not 1 - y?), where the distance between centres of gravity is 3.76 Å, the perpendicular distance of the centre of gravity of the former from the latter is 3.53 Å, the perpendicular distance of the centre of gravity of the latter from the former is 3.52 Å and the angle between the planes is 0.73°.

This supramolecular structure is different from those reported by Cannon et al. (2001a,b,c,d), which were all similar. This difference is due to the presence of the 2-(4-nitrobenzoyl)ethyl substituent on N1, which locks the 1H form and precludes the presence of an H atom at N2, which is involved in the formation of the supramolecular structures of the crystal structures cited above. In compound (I), the 1H configuration of the heterocyclic system results in an essentially planar pyridine ring, whereas in the published structures, it is intermediate between a boat and an envelope. Examination of the structure with PLATON (Spek, 2000) showed that there were no solvent accessible voids in the crystal lattice apart from that occupied by the solvent molecule.

Related literature top

For related literature, see: Bell & Ackerman (1990); Bernstein et al. (1995); Bristol-Meyers & Co (1973); Cannon et al. (2001a, 2001b, 2001c, 2001d); Crenshaw et al. (1976, 1978); Farghaly et al. (1989); Gatta et al. (1991); Gein Stein, Biel & Singh (1970); Smirnoff & Crenshaw (1977); Spek (2000).

Experimental top

A solution of 4-(4-chlorophenyl)-3,7,7-trimethyl-4,7,8,9-tetrahydro-2H- pyrazolo[3,4-b]quinolin-5(6H)-one (2.0 mmol) and 3-dimethylamino-4-nitropropiophenone (2.0 mmol) in absolute ethanol (15 ml) was refluxed for 50 min, and the resulting precipitate was filtered, washed with ethanol, dried and recrystallized from ethanol. Compound (I) was obtained as orange crystals (m.p. 466 K, yield 82%), from which suitable ones were selected for X-ray diffraction. Analysis calculated for C28H28ClN4O4: C 64.80, H 5.24, N 10.80%; found: C,64.87, H 5.16, N 10.73.

Refinement top

H atoms on N9 and O1A were located on a difference map; all others were placed in calculated positions. All H atoms were treated as riding, with C—H = 0.95–1.00 Å, N—H = 0.92 Å and O—H 1.05 Å. Those attached to atom C2A were calculated as six half H atoms.

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 PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A view of the crystal structure of (I) showing the C(6) chain [symmetry code: (i) x, 1 - y, 1/2 + z]. The solvent molecule has been omitted for clarity.
[Figure 3] Fig. 3. A view of the crystal structure of (I) showing the R22(23) ring [symmetry code: (i) x, 1 - y, 1/2 + z]. The solvent molecule has been omitted for clarity.
4-(4-Chlorophenyl)-3,7,7-trimethyl-1-[2-(4-nitrobenzoyl)ethyl]-4,7,8,9- tetrahydro-1H-pyrazolo[3,4-b]quinolin-5(6H)-one-ethanol (1/1) top
Crystal data top
C28H27ClN4O4·C2H6ODx = 1.34 Mg m3
Mr = 565.05Melting point: 466 K
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 23.6298 (6) ÅCell parameters from 5677 reflections
b = 9.6215 (3) Åθ = 3.1–27.5°
c = 14.2657 (4) ŵ = 0.18 mm1
β = 120.2930 (16)°T = 150 K
V = 2800.51 (14) Å3Block, orange
Z = 40.30 × 0.14 × 0.14 mm
F(000) = 1192
Data collection top
Nonius KappaCCD area-detector
diffractometer
5677 independent reflections
Radiation source: fine-focus sealed X-ray tube4821 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.04
ϕ and ω scans with κ offsetsθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 2730
Tmin = 0.947, Tmax = 0.975k = 1112
11553 measured reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0495P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
5677 reflectionsΔρmax = 0.24 e Å3
365 parametersΔρmin = 0.27 e Å3
2 restraintsAbsolute structure: Flack (1983), 3212 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (5)
Crystal data top
C28H27ClN4O4·C2H6OV = 2800.51 (14) Å3
Mr = 565.05Z = 4
Monoclinic, CcMo Kα radiation
a = 23.6298 (6) ŵ = 0.18 mm1
b = 9.6215 (3) ÅT = 150 K
c = 14.2657 (4) Å0.30 × 0.14 × 0.14 mm
β = 120.2930 (16)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
5677 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
4821 reflections with I > 2σ(I)
Tmin = 0.947, Tmax = 0.975Rint = 0.04
11553 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.098Δρmax = 0.24 e Å3
S = 1.00Δρmin = 0.27 e Å3
5677 reflectionsAbsolute structure: Flack (1983), 3212 Friedel pairs
365 parametersAbsolute structure parameter: 0.03 (5)
2 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.89438 (9)0.20346 (19)0.84225 (14)0.0202 (4)
C110.89995 (12)0.1996 (2)0.94874 (18)0.0216 (5)
C120.85271 (12)0.3010 (2)0.95531 (18)0.0228 (5)
C130.85921 (11)0.3050 (2)1.06560 (17)0.0206 (5)
O1330.89835 (8)0.23116 (17)1.13971 (13)0.0274 (4)
C1310.81675 (12)0.4049 (2)1.08372 (18)0.0217 (5)
C1320.82133 (13)0.4052 (2)1.18466 (19)0.0263 (6)
C1330.78476 (13)0.4981 (3)1.20700 (18)0.0281 (6)
C1340.74471 (12)0.5915 (2)1.12706 (19)0.0240 (5)
N130.70767 (10)0.6933 (2)1.15138 (17)0.0305 (5)
O110.68257 (9)0.79102 (19)1.08941 (16)0.0369 (4)
O120.70387 (9)0.6748 (2)1.23412 (14)0.0409 (5)
C1350.73805 (13)0.5915 (3)1.0259 (2)0.0274 (6)
C1360.77391 (12)0.4964 (3)1.00400 (18)0.0257 (5)
N20.85070 (9)0.1171 (2)0.76075 (15)0.0206 (4)
C30.85750 (11)0.1469 (2)0.67517 (17)0.0199 (5)
C310.81786 (12)0.0718 (3)0.57003 (18)0.0254 (5)
C3a0.90445 (11)0.2518 (2)0.69987 (16)0.0180 (5)
C40.93151 (11)0.3198 (2)0.63608 (17)0.0178 (5)
C410.96523 (11)0.2159 (2)0.59909 (17)0.0165 (4)
C421.01761 (12)0.1363 (2)0.67326 (18)0.0209 (5)
C431.04852 (12)0.0425 (2)0.63972 (18)0.0217 (5)
C441.02560 (11)0.0292 (2)0.52926 (18)0.0198 (5)
Cl41.06286 (3)0.09124 (6)0.48634 (4)0.02874 (15)
C450.97350 (12)0.1061 (2)0.45389 (17)0.0214 (5)
C460.94360 (12)0.1994 (2)0.48954 (18)0.0207 (5)
C4a0.97781 (11)0.4366 (2)0.70570 (17)0.0178 (5)
C51.00230 (11)0.5276 (2)0.65364 (17)0.0181 (5)
O50.98308 (8)0.51332 (16)0.55532 (11)0.0239 (4)
C61.04798 (12)0.6457 (2)0.71622 (18)0.0230 (5)
C71.08601 (12)0.6270 (2)0.83932 (18)0.0230 (5)
C711.11769 (14)0.7664 (3)0.8925 (2)0.0301 (6)
C721.13858 (13)0.5163 (3)0.8729 (2)0.0332 (6)
C81.03685 (12)0.5848 (2)0.87447 (18)0.0232 (5)
C8a0.99454 (11)0.4638 (2)0.81104 (16)0.0184 (5)
N90.97083 (10)0.38750 (18)0.86433 (14)0.0196 (4)
C9a0.92577 (11)0.2843 (2)0.80607 (17)0.0182 (5)
O1A0.79130 (9)0.12932 (19)0.79244 (14)0.0376 (5)
C1A0.72545 (15)0.1122 (3)0.7110 (2)0.0455 (8)
C2A0.68370 (15)0.2230 (3)0.7226 (3)0.0437 (7)
H11A0.94540.22331.00510.026*
H11B0.89060.10430.96340.026*
H12A0.86070.39530.93670.027*
H12B0.80730.27440.90090.027*
H1320.84970.34141.23890.032*
H1330.78710.49751.27550.034*
H1350.70950.65540.97190.033*
H1360.76920.49360.93380.031*
H31A0.78910.00430.57710.038*
H31B0.84720.02300.55130.038*
H31C0.79120.13870.51270.038*
H40.89420.36270.56990.021*
H421.03270.14610.74850.025*
H431.08460.01140.69120.026*
H450.95810.09560.37860.026*
H460.90760.25310.43780.025*
H6A1.02200.73240.69890.028*
H6B1.07980.65750.69090.028*
H71A1.14220.75550.97160.045*
H71B1.08350.83670.87220.045*
H71C1.14760.79570.86750.045*
H72A1.11830.42860.83650.050*
H72B1.16090.50320.95170.050*
H72C1.17050.54570.85210.050*
H8A1.06120.56030.95250.028*
H8B1.00840.66530.86530.028*
H90.97440.40440.93070.024*
H1A0.81020.03690.77970.045*
H1A10.72140.11950.63870.055*
H1A20.71000.01880.71720.055*
H2A10.63760.20880.66720.066*0.50
H2A20.68860.21670.79490.066*0.50
H2A30.69790.31500.71320.066*0.50
H2A40.71180.28490.78300.066*0.50
H2A50.66080.27700.65530.066*0.50
H2A60.65150.17870.73700.066*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0246 (11)0.0219 (10)0.0182 (9)0.0045 (8)0.0139 (9)0.0033 (8)
C110.0257 (13)0.0246 (12)0.0191 (11)0.0013 (10)0.0146 (11)0.0000 (9)
C120.0240 (13)0.0291 (13)0.0195 (11)0.0006 (10)0.0140 (11)0.0001 (9)
C130.0197 (13)0.0241 (12)0.0211 (12)0.0056 (10)0.0126 (11)0.0036 (9)
O1330.0296 (10)0.0308 (9)0.0238 (8)0.0020 (8)0.0149 (8)0.0024 (7)
C1310.0233 (13)0.0247 (12)0.0218 (12)0.0077 (10)0.0147 (11)0.0053 (9)
C1320.0290 (15)0.0274 (13)0.0241 (12)0.0022 (11)0.0147 (12)0.0017 (10)
C1330.0319 (15)0.0352 (14)0.0218 (12)0.0021 (12)0.0170 (12)0.0042 (10)
C1340.0213 (13)0.0260 (13)0.0286 (12)0.0049 (10)0.0154 (11)0.0076 (10)
N130.0225 (12)0.0341 (13)0.0372 (12)0.0053 (10)0.0168 (10)0.0134 (10)
O110.0340 (11)0.0293 (10)0.0523 (12)0.0025 (9)0.0254 (10)0.0058 (9)
O120.0305 (11)0.0662 (13)0.0313 (10)0.0037 (10)0.0194 (9)0.0107 (9)
C1350.0263 (14)0.0317 (14)0.0288 (13)0.0001 (11)0.0173 (12)0.0004 (11)
C1360.0272 (14)0.0339 (14)0.0207 (12)0.0006 (12)0.0155 (11)0.0013 (10)
N20.0177 (10)0.0234 (10)0.0223 (10)0.0010 (8)0.0111 (9)0.0051 (8)
C30.0195 (13)0.0199 (11)0.0220 (11)0.0018 (9)0.0117 (10)0.0014 (9)
C310.0226 (13)0.0300 (13)0.0217 (11)0.0042 (11)0.0098 (11)0.0060 (10)
C3a0.0169 (12)0.0194 (11)0.0204 (11)0.0016 (9)0.0113 (10)0.0003 (9)
C40.0196 (12)0.0183 (11)0.0170 (10)0.0011 (9)0.0104 (10)0.0013 (9)
C410.0175 (12)0.0161 (10)0.0191 (11)0.0040 (9)0.0117 (10)0.0013 (8)
C420.0235 (13)0.0242 (12)0.0167 (11)0.0010 (10)0.0113 (10)0.0017 (9)
C430.0188 (12)0.0234 (12)0.0225 (11)0.0032 (10)0.0102 (10)0.0008 (9)
C440.0203 (13)0.0195 (11)0.0247 (12)0.0044 (10)0.0152 (11)0.0053 (9)
Cl40.0286 (3)0.0284 (3)0.0332 (3)0.0027 (3)0.0185 (3)0.0073 (3)
C450.0261 (13)0.0226 (12)0.0162 (11)0.0037 (10)0.0113 (11)0.0040 (9)
C460.0207 (13)0.0226 (12)0.0166 (10)0.0012 (10)0.0079 (10)0.0001 (9)
C4a0.0194 (12)0.0184 (11)0.0182 (10)0.0019 (9)0.0112 (10)0.0008 (8)
C50.0223 (12)0.0173 (11)0.0172 (11)0.0044 (9)0.0119 (10)0.0019 (8)
O50.0329 (10)0.0232 (8)0.0191 (8)0.0009 (7)0.0158 (8)0.0015 (7)
C60.0248 (13)0.0233 (12)0.0228 (12)0.0051 (10)0.0134 (11)0.0003 (10)
C70.0230 (13)0.0248 (12)0.0214 (11)0.0054 (10)0.0114 (11)0.0023 (9)
C710.0360 (15)0.0330 (14)0.0239 (12)0.0110 (12)0.0171 (12)0.0045 (10)
C720.0245 (14)0.0376 (15)0.0310 (13)0.0026 (12)0.0092 (12)0.0040 (12)
C80.0295 (14)0.0225 (12)0.0199 (11)0.0047 (10)0.0140 (11)0.0029 (9)
C8a0.0200 (12)0.0185 (11)0.0186 (11)0.0033 (10)0.0111 (10)0.0030 (9)
N90.0275 (11)0.0215 (10)0.0144 (9)0.0035 (8)0.0139 (9)0.0025 (7)
C9a0.0187 (12)0.0200 (11)0.0181 (10)0.0005 (9)0.0108 (10)0.0011 (9)
O1A0.0351 (12)0.0364 (10)0.0334 (10)0.0086 (9)0.0113 (9)0.0020 (8)
C1A0.0377 (18)0.0539 (19)0.0383 (16)0.0098 (14)0.0143 (14)0.0097 (13)
C2A0.0441 (19)0.0423 (17)0.0548 (17)0.0079 (14)0.0324 (16)0.0034 (14)
Geometric parameters (Å, º) top
N1—N21.377 (3)C43—H430.9500
N1—C9a1.345 (3)C44—C451.372 (3)
N1—C111.458 (3)C44—Cl41.743 (2)
N2—C31.340 (3)C45—C461.388 (3)
C3—C3a1.407 (3)C45—H450.9500
C3—C311.494 (3)C46—H460.9500
C3a—C9a1.370 (3)C4a—C8a1.372 (3)
N13—O111.220 (3)C4a—C51.445 (3)
N13—O121.241 (3)C5—O51.245 (2)
N13—C1341.467 (3)C5—C61.510 (3)
C11—C121.520 (3)C6—C71.527 (3)
C11—H11A0.9900C6—H6A0.9900
C11—H11B0.9900C6—H6B0.9900
C12—C131.502 (3)C7—C721.519 (4)
C12—H12A0.9900C7—C81.534 (3)
C12—H12B0.9900C7—C711.537 (3)
C13—O1331.221 (3)C71—H71A0.9800
C13—C1311.503 (3)C71—H71B0.9800
C131—C1321.388 (3)C71—H71C0.9800
C131—C1361.389 (4)C72—H72A0.9800
C132—C1331.387 (3)C72—H72B0.9800
C132—H1320.9500C72—H72C0.9800
C133—C1341.384 (3)C8—C8a1.504 (3)
C133—H1330.9500C8—H8A0.9900
C134—C1351.371 (3)C8—H8B0.9900
C135—C1361.386 (3)C8a—N91.364 (3)
C135—H1350.9500N9—C9a1.385 (3)
C136—H1360.9500N9—H90.9216
C31—H31A0.9800O1A—C1A1.405 (4)
C31—H31B0.9800O1A—H1A1.0514
C31—H31C0.9800C1A—C2A1.518 (4)
C3a—C41.500 (3)C1A—H1A10.9900
C4—C411.528 (3)C1A—H1A20.9900
C4—C4a1.534 (3)C2A—H2A10.9800
C4—H41.0000C2A—H2A20.9800
C41—C421.384 (3)C2A—H2A30.9800
C41—C461.387 (3)C2A—H2A40.9800
C42—C431.389 (3)C2A—H2A50.9800
C42—H420.9500C2A—H2A60.9800
C43—C441.390 (3)
C9a—N1—N2110.40 (17)C45—C46—H46119.3
C9a—N1—C11129.60 (19)C8a—C4a—C5118.6 (2)
N2—N1—C11119.99 (17)C8a—C4a—C4124.49 (19)
N1—C11—C12111.40 (18)C5—C4a—C4116.83 (18)
N1—C11—H11A109.3O5—C5—C4a119.9 (2)
C12—C11—H11A109.3O5—C5—C6119.67 (19)
N1—C11—H11B109.3C4a—C5—C6120.29 (18)
C12—C11—H11B109.3C5—C6—C7114.93 (18)
H11A—C11—H11B108.0C5—C6—H6A108.5
C13—C12—C11112.99 (18)C7—C6—H6A108.5
C13—C12—H12A109.0C5—C6—H6B108.5
C11—C12—H12A109.0C7—C6—H6B108.5
C13—C12—H12B109.0H6A—C6—H6B107.5
C11—C12—H12B109.0C72—C7—C6111.0 (2)
H12A—C12—H12B107.8C72—C7—C8110.2 (2)
O133—C13—C12121.6 (2)C6—C7—C8107.69 (19)
O133—C13—C131120.19 (19)C72—C7—C71109.8 (2)
C12—C13—C131118.16 (19)C6—C7—C71108.80 (19)
C132—C131—C136119.4 (2)C8—C7—C71109.29 (19)
C132—C131—C13118.0 (2)C7—C71—H71A109.5
C136—C131—C13122.6 (2)C7—C71—H71B109.5
C133—C132—C131120.5 (2)H71A—C71—H71B109.5
C133—C132—H132119.7C7—C71—H71C109.5
C131—C132—H132119.7H71A—C71—H71C109.5
C134—C133—C132118.4 (2)H71B—C71—H71C109.5
C134—C133—H133120.8C7—C72—H72A109.5
C132—C133—H133120.8C7—C72—H72B109.5
C135—C134—C133122.4 (2)H72A—C72—H72B109.5
C135—C134—N13118.9 (2)C7—C72—H72C109.5
C133—C134—N13118.7 (2)H72A—C72—H72C109.5
O11—N13—O12123.9 (2)H72B—C72—H72C109.5
O11—N13—C134118.2 (2)C8a—C8—C7113.04 (18)
O12—N13—C134117.9 (2)C8a—C8—H8A109.0
C134—C135—C136118.6 (2)C7—C8—H8A109.0
C134—C135—H135120.7C8a—C8—H8B109.0
C136—C135—H135120.7C7—C8—H8B109.0
C135—C136—C131120.7 (2)H8A—C8—H8B107.8
C135—C136—H136119.7N9—C8a—C4a122.4 (2)
C131—C136—H136119.7N9—C8a—C8114.62 (18)
C3—N2—N1104.89 (18)C4a—C8a—C8122.90 (19)
N2—C3—C3a111.53 (18)C8a—N9—C9a117.32 (17)
N2—C3—C31120.6 (2)C8a—N9—H9128.8
C3a—C3—C31127.9 (2)C9a—N9—H9112.8
C3—C31—H31A109.5N1—C9a—C3a109.04 (19)
C3—C31—H31B109.5N1—C9a—N9126.19 (18)
H31A—C31—H31B109.5C3a—C9a—N9124.74 (19)
C3—C31—H31C109.5C1A—O1A—H1A98.5
H31A—C31—H31C109.5O1A—C1A—C2A109.7 (2)
H31B—C31—H31C109.5O1A—C1A—H1A1109.7
C9a—C3a—C3104.13 (18)C2A—C1A—H1A1109.7
C9a—C3a—C4122.7 (2)O1A—C1A—H1A2109.7
C3—C3a—C4133.16 (19)C2A—C1A—H1A2109.7
C3a—C4—C41112.37 (17)H1A1—C1A—H1A2108.2
C3a—C4—C4a108.03 (17)C1A—C2A—H2A1109.5
C41—C4—C4a112.17 (19)C1A—C2A—H2A2109.5
C3a—C4—H4108.0H2A1—C2A—H2A2109.5
C41—C4—H4108.0C1A—C2A—H2A3109.5
C4a—C4—H4108.0H2A1—C2A—H2A3109.5
C42—C41—C46118.5 (2)H2A2—C2A—H2A3109.5
C42—C41—C4121.23 (19)C1A—C2A—H2A4109.5
C46—C41—C4120.3 (2)H2A1—C2A—H2A4141.1
C41—C42—C43121.3 (2)H2A2—C2A—H2A456.3
C41—C42—H42119.4H2A3—C2A—H2A456.3
C43—C42—H42119.4C1A—C2A—H2A5109.5
C42—C43—C44118.6 (2)H2A1—C2A—H2A556.3
C42—C43—H43120.7H2A2—C2A—H2A5141.1
C44—C43—H43120.7H2A3—C2A—H2A556.3
C45—C44—C43121.4 (2)H2A4—C2A—H2A5109.5
C45—C44—Cl4119.71 (17)C1A—C2A—H2A6109.5
C43—C44—Cl4118.84 (17)H2A1—C2A—H2A656.3
C44—C45—C46118.9 (2)H2A2—C2A—H2A656.3
C44—C45—H45120.6H2A3—C2A—H2A6141.1
C46—C45—H45120.6H2A4—C2A—H2A6109.5
C41—C46—C45121.4 (2)H2A5—C2A—H2A6109.5
C41—C46—H46119.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···N21.051.862.904 (3)175
N9—H9···O5i0.921.862.761 (3)165
C12—H12B···O12ii0.992.453.344 (4)150
Symmetry codes: (i) x, y+1, z+1/2; (ii) x, y+1, z1/2.

Experimental details

Crystal data
Chemical formulaC28H27ClN4O4·C2H6O
Mr565.05
Crystal system, space groupMonoclinic, Cc
Temperature (K)150
a, b, c (Å)23.6298 (6), 9.6215 (3), 14.2657 (4)
β (°) 120.2930 (16)
V3)2800.51 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.30 × 0.14 × 0.14
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.947, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
11553, 5677, 4821
Rint0.04
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.098, 1.00
No. of reflections5677
No. of parameters365
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.27
Absolute structureFlack (1983), 3212 Friedel pairs
Absolute structure parameter0.03 (5)

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 PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
N1—N21.377 (3)N13—O121.241 (3)
N1—C9a1.345 (3)N13—C1341.467 (3)
N1—C111.458 (3)C13—O1331.221 (3)
N2—C31.340 (3)C4a—C51.445 (3)
C3—C3a1.407 (3)C5—O51.245 (2)
C3a—C9a1.370 (3)C5—C61.510 (3)
N13—O111.220 (3)
C9a—N1—N2110.40 (17)N2—C3—C3a111.53 (18)
C9a—N1—C11129.60 (19)C9a—C3a—C3104.13 (18)
N2—N1—C11119.99 (17)N1—C9a—C3a109.04 (19)
C3—N2—N1104.89 (18)N1—C9a—N9126.19 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···N21.051.862.904 (3)175
N9—H9···O5i0.921.862.761 (3)165
C12—H12B···O12ii0.992.453.344 (4)150
Symmetry codes: (i) x, y+1, z+1/2; (ii) x, y+1, z1/2.
 

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