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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 60| Part 8| August 2004| Pages o604-o607
doi:10.1107/S0108270104015616

10-(4-Chloro­phenyl)-7-methyl-5,6-di­hydro­benzo­[h]­pyrazolo­[5,1-b]­quinazoline and 2-(4-chloro­phenyl)-5-methyl-6,7-di­hydro­benzo­[h]­pyrazolo[1,5-a]­quinazoline: isomeric mol­ecules linked into hydrogen-bonded dimers or π-stacked chains

CROSSMARK_Color_square_no_text.svg
John N. Low,a Justo Cobo,b Jairo Quiroga,c Jaime Portillac and Christopher Glidewelld*

aDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, bDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain, cGrupo de Investigación de Compuestos Heterociclícos, Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia, and dSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 24 June 2004; accepted 25 June 2004; online 31 July 2004)

The isomeric title compounds 10-(4-chloro­phenyl)-7-methyl-5,6-di­hydro­benzo­[h]­pyrazolo­[5,1-b]­quinazoline, (I[link]), and 2-(4-chloro­phenyl)-5-methyl-6,7-di­hydro­benzo­[h]­pyrazolo­[1,5-a]quinazoline, (II[link]), both C21H16ClN3, exhibit peripheral delocalization in the heteroaromatic portion of the fused ring system. The mol­ecules of (I[link]) are linked into centrosymmetric dimers by a single C—H⋯π(arene) hydrogen bond, and the mol­ecules of (II[link]), where Z′ = 2, are linked by π–π stacking interactions into chains in which the two types of mol­ecules alternate.

Comment

The quinazoline skeleton is an important pharmacophore which occurs frequently in medicinal chemistry literature (Fry et al., 1994[Fry, D. W., Kraker, A. J., McMichael, A., Ambroso, L. A., Nelson, J. M., Leopold, W. R., Connors, R. W. & Bridges, A. L. (1994). Science, 265, 1093-1095.]). In particular, pyrazolo­[1,5-c]­quinazolinones have been shown to be potent amino acid antagonists (McQuaid et al., 1992[McQuaid, L., Smith, E., South, K., Mitch, C. H., Schoepp, D., True, R., Calligaro, D., O'Malley, P., Lodge, D. & Ornstein, P. (1992). J. Med. Chem. 35, 3319-3324.]), and anti-inflammatory, antiasthmatic and anti­allergenic agents and immunosuppressants (Casey et al., 1980[Casey, F. B., Abboa-Offei, B. E. & Marretta, J. (1980). J. Pharmacol. Exp. Ther. 213, 432-436.]). Continuing our studies of the application of free-solvent cyclo­condensation procedures under microwave irradiation, we have now prepared two benzo-fused pyrazolo­[5,1-b]quinazolines from a 5-amino­pyrazole and 2-acetyl-1-tetralone, resulting in a regioisomeric mixture 10-(4-chloro­phenyl)-7-methyl-5,6-di­hydro­benzo­[h]­pyrazolo­[5,1-b]­quinazoline, (I[link]), and 2-(4-chloro­phenyl)-5-methyl-6,7-di­hydro­benzo­[h]­pyrazolo[1,5-a]­quinazoline, (II[link]), in an approximate ratio of 1:4.

The isomeric compounds (I[link]) and (II[link]) both crystallize in space group P[\overline 1], but with Z′ values of 1 and 2, respectively. Within the mol­ecule of (I[link]) (Fig. 1[link]), the C10—C11 and C11—C12 bonds, which in the classically bond-localized form are double and single bonds, respectively, differ in length by only

[Scheme 1]
ca 0.01 Å (Table 1[link]). Similarly, the C12—N1 and N9—C10 bonds, which are formally double and single bonds, respectively, are nearly identical in length. At the same time, the N1a—C10 bond is much longer than the other formally single N—C bonds, N1a—C2 and N9—C10. Taken together, these observations indicate an important contribution to the overall molecular–electronic structure of the heterobicyclic portion of the mol­ecule, of a fairly delocalized 10-π periphery with a rather weak cross-ring bond. A similar pattern of distances, leading to a similar conclusion, is apparent in each of the two independent mol­ecules, 1 and 2, of compound (II[link]) (Fig. 2[link] Table 3[link]).

By contrast, the bond lengths in the terminal carbocyclic rings of the fused ring system, ring C4a/C5–C8/C8a in (I[link]) and rings Cn1c/Cn2–Cn5/Cn5a in (II[link]), where n = 1 or 2 for the mol­ecules of types 1 and 2 (Fig. 2[link]), are consistent with typical aromatic delocalization. For the intervening non-planar rings, the ring-puckering parameters (Cremer & Pople, 1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]) for the atom sequence C2a/C3/C4/C4a/C8a/C8b in (I[link]), θ = 113.7 (4)° and φ = 268.4 (4)°, correspond to a conformation intermediate between the half-chair and screw-boat forms (Evans & Boeyens, 1989[Evans, D. G. & Boeyens, J. C. A. (1989). Acta Cryst. B45, 581-590.]). For the atom sequences Cn1b/Cn1c/Cn5a/Cn6/Cn7/Cn7a in (II[link]), the corresponding values are θ = 68.6 (4)° and φ = 205.6 (4)° for n = 1, and θ = 68.5 (4)° and φ = 206.6 (4)° for n = 2, corresponding very closely to the screw-boat conformation.

The mol­ecules in (I[link]) are linked into centrosymmetric dimers by means of a single C—H⋯π(arene) hydrogen bond (Table 2[link]). Atom C3 in the mol­ecule at (x, y, z) acts as hydrogen-bond donor, via the axial atom H3A, to the chlorinated ring (C31–C36) in the mol­ecule at (1 − x, 1 − y, 1 − z), so generating a dimer centred at ([{1 \over 2}], [{1 \over 2}], [{1 \over 2}]) (Fig. 3[link]). There are no direction-specific interactions between these dimers.

In compound (II[link]), the mol­ecules are linked into chains by the concerted action of two independent π–π stacking interactions. The heterocyclic ring containing atom N19 in the type 1 mol­ecule at (x, y, z) makes a dihedral angle of 1.5 (2)° with each of the chlorinated rings in the two type 2 mol­ecules at (x, y, z) and (1 + x, y, z). The interplanar spacings are both ca 3.47 Å, and the ring-centroid separations are 3.544 (2) Å within the asymmetric unit, and 3.546 (2) Å to the mol­ecule at (1 + x, y, z). These interactions are augmented by an entirely complementary pair of interactions between the ring containing atom N29 in the type 2 mol­ecules at (x, y, z) and (1 + x, y, z), and the chlorinated ring in the type 1 mol­ecule at (x, y, z). Here, the dihedral angles between adjacent ring planes are both 7.2 (2)°, with interplanar spacings of ca 3.5 Å within the asymmetric unit and ca 3.47 Å to the adjacent unit. The respective ring-centroid separations are 3.589 (2) and 3.503 (2) Å. The effect of these interactions is to link the mol­ecules into a chain running parallel to the [100] direction, in which mol­ecules of the two types alternate. Two anti-parallel chains of this type pass through each unit cell (Fig. 4[link]), but there are no direction-specific interactions between adjacent chains.

[Figure 1]
Figure 1
A view of the mol­ecule of (I[link]), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2]
Figure 2
The two independent mol­ecules of (II[link]), showing the atom-labelling scheme in (a) a type 1 mol­ecule and (b) a type 2 mol­ecule. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 3]
Figure 3
Part of the crystal structure of (I[link]), showing the formation of a cyclic centrosymmetric dimer. For the sake of clarity, H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
[Figure 4]
Figure 4
A stereoview of part of the crystal structure of (II[link]), showing an anti-parallel pair of π-stacked chains along [100]. For the sake of clarity, H atoms have been omitted.

Experimental

Equimolar quantities of 5-amino-3-(4-chloro­phenyl)-1H-pyrazole (500 mg, 2.6 mmol) and 2-acetyl-1-tetralone (485 mg, 2.6 mmol) were placed in Pyrex open vessels and irradiated in a domestic microwave oven for 1.5 min at 600 W. The product mixture was extracted with ethanol. After the solvent had been removed, the products were separated by column chromatography on silica gel, using hexane–ethyl acetate (3:1 v/v) as eluant. Compound (I[link]) was obtained as the first fraction (yield 18%, m.p. 449 K). MS (EI, 70 eV, %): 348/346 (8/­35, M+1), 347/345 (39/100, M+), 344 (28), 166 (11), 75 (8). Analysis found: C 72.9, H 4.6, N 12.2%; C21H16ClN3 requires: C 72.9, H 4.7, N 12.2%. Yellow crystals of (I[link]) suitable for single-crystal X-ray diffraction were obtained by direct evaporation of the chromatographic eluate. Compound (II[link]) was obtained as the second fraction (yield 70%, m.p. 505 K). MS (EI, 70 eV, %): 348/346 (8/32, M+1), 347/345 (37/100, M+), 344 (24), 166 (22), 75 (30). Analysis found: C 72.8, H 4.6, N 12.1%; C21H16ClN3 requires: C 72.9, H 4.7, N 12.2%. Brown crystals of (II[link]) suitable for single-crystal X-ray diffraction were obtained by direct evaporation of the chromatographic eluate.

Compound (I)[link]

Crystal data

  • C21H16ClN3

  • Mr = 345.82

  • Triclinic, [P\overline 1]

  • a = 9.2382 (8) Å

  • b = 10.3054 (8) Å

  • c = 10.3184 (9) Å

  • α = 62.720 (4)°

  • β = 83.098 (4)°

  • γ = 70.531 (5)°

  • V = 822.54 (12) Å3

  • Z = 2

  • Dx = 1.396 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 3763 reflections

  • θ = 3.3–27.6°

  • μ = 0.24 mm−1

  • T = 120 (2) K

  • Plate, yellow

  • 0.34 × 0.19 × 0.08 mm
Data collection

  • Nonius KappaCCD area-detector diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.]) Tmin = 0.914, Tmax = 0.981

  • 17 454 measured reflections

  • 3763 independent reflections

  • 2156 reflections with I > 2σ(I)

  • Rint = 0.094

  • θmax = 27.6°

  • h = −11 → 11

  • k = −13 → 12

  • l = −13 → 13
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 0.153

  • S = 0.96

  • 3763 reflections

  • 229 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0709P)2 + 0.3108P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Selected geometric parameters (Å) for (I)[link]

N1—N1a 1.357 (3)
N1a—C2 1.365 (3)
C2—C2a 1.365 (4)
C2a—C8b 1.442 (4)
C8b—N9 1.319 (3)
N9—C10 1.351 (3)
C10—C11 1.381 (4)
C11—C12 1.393 (4)
C12—N1 1.345 (3)
N1a—C10 1.394 (3)

Table 2
Hydrogen-bonding geometry (Å, °) for (I)[link]

Cg1 is the centroid of the C31–C36 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C3—H3A⋯Cg1i 0.99 2.92 3.815 (3) 150
Symmetry code: (i) 1-x,1-y,1-z.

Compound (II)[link]

Crystal data

  • C21H16ClN3

  • Mr = 345.82

  • Triclinic, [P\overline 1]

  • a = 7.0098 (3) Å

  • b = 15.0306 (7) Å

  • c = 17.0060 (8) Å

  • α = 111.492 (2)°

  • β = 101.406 (3)°

  • γ = 97.981 (3)°

  • V = 1589.81 (13) Å3

  • Z = 4

  • Dx = 1.445 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 7321 reflections

  • θ = 3.0–27.6°

  • μ = 0.25 mm−1

  • T = 120 (2) K

  • Needle, pale brown

  • 0.14 × 0.04 × 0.03 mm
Data collection

  • Nonius KappaCCD area-detector diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.]) Tmin = 0.949, Tmax = 0.993

  • 35 785 measured reflections

  • 7321 independent reflections

  • 4073 reflections with I > 2σ(I)

  • Rint = 0.113

  • θmax = 27.6°

  • h = −8 → 9

  • k = −19 → 19

  • l = −22 → 22
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.061

  • wR(F2) = 0.152

  • S = 1.03

  • 7321 reflections

  • 453 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0614P)2 + 0.1965P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.37 e Å−3

Table 3
Selected geometric parameters (Å) for (II)[link]

N11—N11a 1.359 (3)
N11a—C11b 1.381 (3)
C11b—C17a 1.378 (4)
C17a—C18 1.419 (4)
C18—N19 1.321 (3)
N19—C19a 1.351 (3)
C19a—C110 1.379 (4)
C110—C111 1.398 (4)
C111—N11 1.348 (3)
N11a—C19a 1.393 (3)
N21—N21a 1.355 (3)
N21a—C21b 1.378 (3)
C21b—C27a 1.381 (4)
C27a—C28 1.422 (4)
C28—N29 1.316 (3)
N29—C29a 1.350 (3)
C29a—C210 1.377 (4)
C210—C211 1.390 (4)
C211—N21 1.348 (3)
N21a—C29a 1.403 (3)

Crystals of compounds (I[link]) and (II[link]) are triclinic. For each, the space group P[\overline 1] was selected and confirmed by the structure analysis. All H atoms were located from difference maps and subsequently treated as riding atoms, with C—H distances of 0.95 (aromatic and heteroaromatic), 0.98 (CH3) or 0.99 Å (CH2), and with Uiso(H) = 1.2Ueq(C), or 1.5Ueq(C) for the methyl groups.

For both compounds, data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 3-17.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information

Crystal structure: contains datablocks global, I, II. DOI: 10.1107/S0108270104015616/sk1742sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270104015616/sk1742Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S0108270104015616/sk1742IIsup3.hkl


Comment top

The quinazoline skeleton is an important pharmacophore which occurs frequently in medicinal chemistry literature (Fry et al., 1994). In particular, pyrazolo[1,5-c]quinazolinones have been shown to be potent amino acid antagonists (McQuaid et al., 1992), and antiinflammatory, antiasthmatic and antiallergenic agents and immunosuppressants (Casey et al., 1980). Continuing our studies of the application of free-solvent cyclocondensation procedures under microwave irradiation, we have now prepared two benzo-fused pyrazolo[5,1-b]quinazolines from a 5-aminopyrazole and 2-acetyl-1-tetralone, resulting in a regioisomeric mixture of 9-(4-chlorophenyl)-7-methyl-5,6-dihydrobenzo[h]pyrazolo[5,1-b]quinazoline, (I), and 2-(4-chlorophenyl)-5-methyl-6,7-dihydrobenzo[e]pyrazolo[5,1-b]quinazoline, (II), in an approximate ratio of 1:4. \sch

The isomeric compounds (I) and (II) both crystallize in space group P1, but with Z' values of 1 and 2, respectively. Within the molecule of (I) (Fig. 1), the C10—C11 and C11—C12 bonds, which in the classically bond-localized form are double and single bonds respectively, differ in length by only ca 0.01 Å (Table 1). Similarly, the C12—N1 and N9—C10 bonds, which are formally double and single bonds, respectively, are nearly identical in length. At the same time, the N1a—C10 bond is much longer than the other formally single N—C bonds, N1a—C2 and N9—C10. Taken together, these observations indicate an important contribution to the overall molecular-electronic structure of the heterobicyclic portion of the molecule, of a fairly delocalized 10-π periphery with a rather weak cross-ring bond. A similar pattern of distances, leading to a similar conclusion, is apparent in each of the two independent molecules, 1 and 2, of compound (II) (Fig. 2, Table 3).

By contrast, the bond lengths in the terminal carbocyclic rings of the fused ring system, ring C4a/C5—C8/C8a in (I) and the rings Cn1C/Cn2—Cn5/Cn5A in (II), where n = 1 or 2 for the molecules of types 1 and 2 (Fig. 2), are consistent with typical aromatic delocalization. For the intervening non-planar rings, the ring-puckering parameters (Cremer & Pople, 1975) for the atom sequence C2a/C3/C4/C4a/C8a/C8b in (I), θ = 113.7 (4)° and ϕ = 268.4 (4)°, correspond to a conformation intermediate between the half-chair and screw-boat forms (Evans & Boeyens, 1989). For the atom sequences Cn1B/Cn1C/Cn5A/Cn6/Cn7/Cn7A in (II), the corresponding values are θ = 68.6 (4)° and ϕ = 205.6 (4)° for n = 1, and θ = 68.5 (4)° and ϕ = 206.6 (4)° for n = 2, corresponding very closely to the screw-boat conformation.

The molecules in (I) are linked into centrosymmetric dimers by means of a single C—H···π(arene) hydrogen bond (Table 2). Atom C3 in the molecule at (x, y, z) acts as hydrogen-bond donor, via the axial atom H3A, to the chlorinated ring (C31—C36) in the molecule at (1 − x, 1 − y, 1 − z), so generating a dimer centred at (1/2, 1/2, 1/2) (Fig. 3). There are no direction-specific interactions between these dimers.

In compound (II), the molecules are linked into chains by the concerted action of two independent π–π stacking interactions. The heterocyclic ring containing atom N19 in the type 1 molecule at (x, y, z) makes a dihedral angle of 1.5 (2)° with each of the chlorinated rings in the two type 2 molecules at (x, y, z) and (1 + x, y, z). The interplanar spacings are both ca 3.47 Å, and the ring-centroid separations are 3.544 (2) Å within the asymmetric unit, and 3.546 (2) Å to the molecule at (1 + x, y, z). These interactions are augmented by an entirely complementary pair of interactions between the ring containing atom N29 in the type 2 molecules at (x, y, z) and (1 + x, y, z), and the chlorinated ring in the type 1 molecule at (x, y, z). Here, the dihedral angles between adjacent ring planes are both 7.2 (2)°, with interplanar spacings of ca 3.5 Å within the asymmetric unit and ca 3.47 Å to the adjacent unit. The respective ring-centroid separations are 3.589 (2) and 3.503 (2) Å. The effect of these interactions is to link the molecules into a chain running parallel to the [100] direction, in which molecules of the two types alternate. Two antiparallel chains of this type pass through each unit cell (Fig. 4), but there are no direction-specific interactions between adjacent chains.

Table 2. Hydrogen bond parameters (Å, °) for compound (I); Cg1 is centroid of ring (C31—C36)

Experimental top

Equimolar amounts of 5-amino-3-(4-chlorophenyl)-1H-pyrazole (500 mg, 2.6 mmol) and 2-acetyl-1-tetralone (485 mg, 2.6 mmol) were placed in Pyrex open vessels and irradiated in a domestic microwave oven for 1.5 min at 600 W. The product mixture was extracted with ethanol. After the solvent had been removed, the products were separated by column chromatography on silica gel, using hexane-ethyl acetate (3:1 v/v) as eluent. Compound (I) was obtained as the first fraction (yield 18%, m.p. 449 K). MS (EI, 70 eV, %): 348/346 (8/35, M+1), 347/345 (39/100, M+), 344 (28), 166 (11), 75 (8). Analysis, found: C 72.9, H 4.6, N 12.2%; C21H16ClN3 requires: C 72.9, H 4.7, N 12.2%. Yellow crystals of (I) suitable for single-crystal X-ray diffraction were obtained by direct evaporation of the chromatographic eluate. Compound (II) was obtained as the second fraction (yield 70%, m.p. 505 K). MS (EI, 70 eV, %): 348/346 (8/32, M+1), 347/345 (37/100, M+), 344 (24), 166 (22), 75 (30). Analysis, found: C 72.8, H 4.6, N 12.1%; C21H16ClN3 requires: C 72.9, H 4.7, N 12.2%. Brown crystals of (II) suitable for single-crystal X-ray diffraction were obtained by direct evaporation of the chromatographic eluate.

Refinement top

Crystals of compounds (I) and (II) are triclinic. For each, the space group P1 was selected and then confirmed by the structure analysis. All H atoms were located from difference maps and subsequently treated as riding atoms, with C—H distances of 0.95 (aromatic and heteroaromatic), 0.98 (CH3) or 0.99 Å (CH2), and with Uiso(H) = 1.2Ueq(C), or 1.5Ueq(C) for the methyl groups.

Computing details top

For both compounds, data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-labelling 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. The two independent molecules of (II), showing the atom-labelling scheme. (a) A type 1 molecule. (b) A type 2 molecule. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the formation of a cyclic centrosymmetric dimer. For the sake of clarity, H atoms not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of (II), showing an antiparallel pair of π-stacked chains along [100]. For the sake of clarity, H atoms have been omitted.
(I) 9-(4-Chlorophenyl)-7-methyl-5,6-dihydrobenzo[h]pyrazolo[3,2-b]quinazoline top
Crystal data top
C21H16ClN3Z = 2
Mr = 345.82F(000) = 360
Triclinic, P1Dx = 1.396 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2382 (8) ÅCell parameters from 3763 reflections
b = 10.3054 (8) Åθ = 3.3–27.6°
c = 10.3184 (9) ŵ = 0.24 mm−1
α = 62.720 (4)°T = 120 K
β = 83.098 (4)°Plate, yellow
γ = 70.531 (5)°0.34 × 0.19 × 0.08 mm
V = 822.54 (12) Å3
Data collection top
Nonius KappaCCD area-detector
diffractometer		3763 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2156 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.094
Detector resolution: 9.091 pixels mm-1θmax = 27.6°, θmin = 3.3°
ϕ and ω scansh = −11→11
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		k = −13→12
Tmin = 0.914, Tmax = 0.981l = −13→13
17454 measured reflections
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0709P)2 + 0.3108P]
where P = (Fo2 + 2Fc2)/3
3763 reflections(Δ/σ)max < 0.001
229 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
C21H16ClN3γ = 70.531 (5)°
Mr = 345.82V = 822.54 (12) Å3
Triclinic, P1Z = 2
a = 9.2382 (8) ÅMo Kα radiation
b = 10.3054 (8) ŵ = 0.24 mm−1
c = 10.3184 (9) ÅT = 120 K
α = 62.720 (4)°0.34 × 0.19 × 0.08 mm
β = 83.098 (4)°
Data collection top
Nonius KappaCCD area-detector
diffractometer		3763 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		2156 reflections with I > 2σ(I)
Tmin = 0.914, Tmax = 0.981Rint = 0.094
17454 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 0.96Δρmax = 0.30 e Å−3
3763 reflectionsΔρmin = −0.30 e Å−3
229 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.5577 (3)0.6152 (2)0.2713 (2)0.0255 (5)
N1a0.5130 (3)0.6765 (2)0.3669 (2)0.0243 (5)
C20.3685 (3)0.7693 (3)0.3697 (3)0.0255 (6)
C2a0.3464 (3)0.8265 (3)0.4691 (3)0.0242 (6)
C30.1939 (3)0.9296 (3)0.4859 (3)0.0264 (6)
C40.2139 (3)1.0496 (3)0.5235 (3)0.0270 (6)
C50.3036 (3)1.0335 (3)0.7534 (3)0.0286 (7)
C4a0.3231 (3)0.9742 (3)0.6536 (3)0.0246 (6)
C60.4060 (3)0.9650 (3)0.8719 (3)0.0319 (7)
C70.5291 (3)0.8343 (3)0.8922 (3)0.0301 (7)
C80.5501 (3)0.7751 (3)0.7927 (3)0.0276 (6)
C8a0.4484 (3)0.8441 (3)0.6724 (3)0.0245 (6)
C8b0.4733 (3)0.7819 (3)0.5657 (3)0.0227 (6)
N90.6107 (3)0.6882 (2)0.5635 (2)0.0252 (5)
C100.6331 (3)0.6356 (3)0.4620 (3)0.0238 (6)
C110.7595 (3)0.5459 (3)0.4217 (3)0.0267 (6)
C120.7079 (3)0.5372 (3)0.3054 (3)0.0264 (6)
C210.2530 (3)0.7957 (3)0.2637 (3)0.0323 (7)
C310.7918 (3)0.4546 (3)0.2206 (3)0.0250 (6)
C320.7111 (3)0.4332 (3)0.1301 (3)0.0284 (7)
C330.7858 (3)0.3537 (3)0.0516 (3)0.0295 (7)
C340.9444 (3)0.2940 (3)0.0637 (3)0.0286 (7)
Cl341.04079 (9)0.19353 (9)−0.03472 (9)0.0413 (3)
C351.0280 (3)0.3134 (3)0.1521 (3)0.0305 (7)
C360.9516 (3)0.3938 (3)0.2302 (3)0.0293 (7)
H3A0.13810.86670.56410.032*
H3B0.13150.98210.39380.032*
H4A0.25411.12320.43880.045 (9)*
H4B0.11291.10780.54520.030 (7)*
H50.21891.12230.74040.034*
H60.39191.00740.93890.038*
H70.59840.78580.97400.036*
H80.63500.68630.80630.033*
H110.86060.49970.46430.032*
H21A0.27790.85910.16440.048*
H21B0.15040.84860.28520.048*
H21C0.25470.69660.27190.048*
H320.60220.47430.12230.034*
H330.72930.3402−0.00980.035*
H351.13690.27200.15930.037*
H361.00860.40760.29100.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0274 (14)0.0257 (12)0.0236 (13)−0.0049 (10)0.0026 (10)−0.0139 (10)
N1a0.0261 (13)0.0252 (12)0.0228 (13)−0.0078 (10)0.0000 (10)−0.0116 (10)
C20.0233 (16)0.0258 (15)0.0229 (15)−0.0043 (12)0.0008 (12)−0.0095 (12)
C2a0.0254 (15)0.0225 (14)0.0214 (15)−0.0072 (12)0.0010 (12)−0.0073 (12)
C30.0231 (15)0.0298 (15)0.0253 (15)−0.0052 (12)−0.0020 (12)−0.0130 (12)
C40.0251 (16)0.0254 (15)0.0294 (16)−0.0071 (12)0.0002 (12)−0.0117 (13)
C50.0299 (16)0.0282 (15)0.0270 (16)−0.0091 (13)0.0042 (13)−0.0126 (13)
C4a0.0245 (15)0.0252 (14)0.0251 (15)−0.0085 (12)0.0024 (12)−0.0120 (12)
C60.0373 (18)0.0345 (16)0.0274 (17)−0.0139 (14)0.0069 (14)−0.0163 (14)
C70.0342 (17)0.0339 (16)0.0231 (16)−0.0105 (13)−0.0011 (13)−0.0130 (13)
C80.0240 (15)0.0287 (15)0.0287 (16)−0.0059 (12)0.0003 (12)−0.0131 (13)
C8a0.0240 (15)0.0279 (15)0.0227 (15)−0.0117 (12)0.0005 (12)−0.0096 (12)
C8b0.0234 (15)0.0219 (14)0.0214 (15)−0.0075 (12)0.0017 (12)−0.0084 (12)
N90.0275 (13)0.0265 (12)0.0244 (13)−0.0088 (10)0.0012 (10)−0.0134 (11)
C100.0241 (15)0.0223 (14)0.0245 (15)−0.0079 (12)−0.0008 (12)−0.0093 (12)
C110.0230 (15)0.0281 (15)0.0286 (16)−0.0061 (12)−0.0006 (12)−0.0133 (13)
C120.0254 (16)0.0244 (14)0.0280 (16)−0.0071 (12)0.0012 (12)−0.0112 (12)
C210.0261 (16)0.0375 (17)0.0315 (17)−0.0047 (13)−0.0033 (13)−0.0166 (14)
C310.0273 (16)0.0235 (14)0.0211 (15)−0.0060 (12)−0.0011 (12)−0.0081 (12)
C320.0261 (16)0.0259 (15)0.0277 (16)−0.0036 (12)−0.0006 (12)−0.0104 (13)
C330.0279 (17)0.0294 (15)0.0311 (17)−0.0061 (13)0.0000 (13)−0.0152 (13)
C340.0335 (17)0.0266 (15)0.0257 (16)−0.0075 (13)0.0011 (13)−0.0131 (13)
Cl340.0385 (5)0.0466 (5)0.0441 (5)−0.0042 (4)0.0021 (4)−0.0309 (4)
C350.0275 (16)0.0299 (16)0.0312 (17)−0.0071 (13)0.0010 (13)−0.0127 (13)
C360.0334 (18)0.0298 (15)0.0275 (16)−0.0120 (13)−0.0001 (13)−0.0132 (13)
Geometric parameters (Å, º) top
N1—N1a1.357 (3)C5—H50.95
N1a—C21.365 (3)C4a—C8a1.399 (4)
C2—C2a1.365 (4)C6—C71.389 (4)
C2a—C8b1.442 (4)C6—H60.95
C8b—N91.319 (3)C7—C81.381 (4)
N9—C101.351 (3)C7—H70.95
C10—C111.381 (4)C8—C8a1.398 (4)
C11—C121.393 (4)C8—H80.95
C12—N11.345 (3)C8a—C8b1.471 (4)
N1a—C101.394 (3)C11—H110.95
C2—C211.492 (4)C12—C311.473 (4)
C21—H21A0.98C31—C361.393 (4)
C21—H21B0.98C31—C321.394 (4)
C21—H21C0.98C32—C331.379 (4)
C2a—C31.502 (4)C32—H320.95
C3—C41.524 (4)C33—C341.383 (4)
C3—H3A0.99C33—H330.95
C3—H3B0.99C34—C351.382 (4)
C4—C4a1.507 (4)C34—Cl341.741 (3)
C4—H4A0.99C35—C361.385 (4)
C4—H4B0.99C35—H350.95
C5—C4a1.387 (4)C36—H360.95
C5—C61.390 (4)
C12—N1—N1a104.2 (2)C6—C7—H7120.2
N1—N1a—C2124.6 (2)C7—C8—C8a121.0 (3)
N1—N1a—C10112.1 (2)C7—C8—H8119.5
C2—N1a—C10123.2 (2)C8a—C8—H8119.5
N1a—C2—C2a116.5 (2)C8—C8a—C4a119.3 (2)
N1a—C2—C21115.8 (2)C8—C8a—C8b120.6 (2)
C2a—C2—C21127.7 (2)C4a—C8a—C8b120.1 (2)
C2—C21—H21A109.5N9—C8b—C2a123.5 (2)
C2—C21—H21B109.5N9—C8b—C8a118.2 (2)
H21A—C21—H21B109.5C2a—C8b—C8a118.4 (2)
C2—C21—H21C109.5C8b—N9—C10117.5 (2)
H21A—C21—H21C109.5N9—C10—C11133.9 (2)
H21B—C21—H21C109.5N9—C10—N1a120.5 (2)
C2—C2a—C8b118.7 (2)C11—C10—N1a105.6 (2)
C2—C2a—C3122.8 (2)C10—C11—C12105.6 (2)
C8b—C2a—C3118.4 (2)C10—C11—H11127.2
C2a—C3—C4111.3 (2)C12—C11—H11127.2
C2a—C3—H3A109.4N1—C12—C11112.5 (2)
C4—C3—H3A109.4N1—C12—C31117.8 (2)
C2a—C3—H3B109.4C11—C12—C31129.7 (3)
C4—C3—H3B109.4C36—C31—C32118.4 (3)
H3A—C3—H3B108.0C36—C31—C12121.6 (2)
C4a—C4—C3110.7 (2)C32—C31—C12119.9 (2)
C4a—C4—H4A109.5C33—C32—C31121.5 (3)
C3—C4—H4A109.5C33—C32—H32119.3
C4a—C4—H4B109.5C31—C32—H32119.3
C3—C4—H4B109.5C32—C33—C34118.9 (3)
H4A—C4—H4B108.1C32—C33—H33120.6
C4a—C5—C6121.0 (3)C34—C33—H33120.6
C4a—C5—H5119.5C35—C34—C33121.2 (3)
C6—C5—H5119.5C35—C34—Cl34119.3 (2)
C5—C4a—C8a119.4 (2)C33—C34—Cl34119.6 (2)
C5—C4a—C4121.2 (2)C34—C35—C36119.4 (3)
C8a—C4a—C4119.5 (2)C34—C35—H35120.3
C7—C6—C5119.8 (3)C36—C35—H35120.3
C7—C6—H6120.1C35—C36—C31120.7 (3)
C5—C6—H6120.1C35—C36—H36119.7
C8—C7—C6119.7 (3)C31—C36—H36119.7
C8—C7—H7120.2
C12—N1—N1a—C2178.2 (2)C4a—C8a—C8b—N9161.9 (2)
C12—N1—N1a—C10−0.9 (3)C8—C8a—C8b—C2a162.6 (2)
N1—N1a—C2—C2a−176.9 (2)C4a—C8a—C8b—C2a−18.0 (4)
C10—N1a—C2—C2a2.1 (4)C2a—C8b—N9—C101.9 (4)
N1—N1a—C2—C213.4 (4)C8a—C8b—N9—C10−178.1 (2)
C10—N1a—C2—C21−177.7 (2)C8b—N9—C10—C11175.6 (3)
N1a—C2—C2a—C8b−2.0 (4)C8b—N9—C10—N1a−1.8 (4)
C21—C2—C2a—C8b177.7 (3)N1—N1a—C10—N9178.9 (2)
N1a—C2—C2a—C3−179.7 (2)C2—N1a—C10—N9−0.2 (4)
C21—C2—C2a—C30.0 (4)N1—N1a—C10—C110.8 (3)
C2—C2a—C3—C4−144.8 (3)C2—N1a—C10—C11−178.3 (2)
C8b—C2a—C3—C437.5 (3)N9—C10—C11—C12−178.1 (3)
C2a—C3—C4—C4a−52.6 (3)N1a—C10—C11—C12−0.4 (3)
C6—C5—C4a—C8a−0.4 (4)N1a—N1—C12—C110.6 (3)
C6—C5—C4a—C4−179.0 (3)N1a—N1—C12—C31179.5 (2)
C3—C4—C4a—C5−146.1 (3)C10—C11—C12—N1−0.2 (3)
C3—C4—C4a—C8a35.4 (3)C10—C11—C12—C31−178.8 (3)
C4a—C5—C6—C7−0.6 (4)N1—C12—C31—C36168.5 (2)
C5—C6—C7—C81.2 (4)C11—C12—C31—C36−12.8 (4)
C6—C7—C8—C8a−0.6 (4)N1—C12—C31—C32−12.7 (4)
C7—C8—C8a—C4a−0.5 (4)C11—C12—C31—C32165.9 (3)
C7—C8—C8a—C8b178.9 (2)C36—C31—C32—C330.1 (4)
C5—C4a—C8a—C81.0 (4)C12—C31—C32—C33−178.6 (2)
C4—C4a—C8a—C8179.5 (2)C31—C32—C33—C340.1 (4)
C5—C4a—C8a—C8b−178.4 (2)C32—C33—C34—C35−0.3 (4)
C4—C4a—C8a—C8b0.1 (4)C32—C33—C34—Cl34−179.9 (2)
C2—C2a—C8b—N90.1 (4)C33—C34—C35—C360.1 (4)
C3—C2a—C8b—N9177.9 (2)Cl34—C34—C35—C36179.8 (2)
C2—C2a—C8b—C8a−180.0 (2)C34—C35—C36—C310.1 (4)
C3—C2a—C8b—C8a−2.2 (4)C32—C31—C36—C35−0.3 (4)
C8—C8a—C8b—N9−17.5 (4)C12—C31—C36—C35178.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···Cg1i0.992.923.815 (3)150
Symmetry code: (i) −x+1, −y+1, −z+1.
(II) 2-(4-Chlorophenyl)-5-methyl-6,7-dihydrobenzo[e]pyrazolo[2,3-b]quinazoline top
Crystal data top
C21H16ClN3Z = 4
Mr = 345.82F(000) = 720
Triclinic, P1Dx = 1.445 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0098 (3) ÅCell parameters from 7321 reflections
b = 15.0306 (7) Åθ = 3.0–27.6°
c = 17.0060 (8) ŵ = 0.25 mm−1
α = 111.492 (2)°T = 120 K
β = 101.406 (3)°Needle, pale brown
γ = 97.981 (3)°0.14 × 0.04 × 0.03 mm
V = 1589.81 (13) Å3
Data collection top
Nonius KappaCCD area-detector
diffractometer		7321 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode4073 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.113
Detector resolution: 9.091 pixels mm-1θmax = 27.6°, θmin = 3.0°
ϕ and ω scansh = −8→9
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		k = −19→19
Tmin = 0.949, Tmax = 0.993l = −22→22
35785 measured reflections
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0614P)2 + 0.1965P]
where P = (Fo2 + 2Fc2)/3
7321 reflections(Δ/σ)max < 0.001
453 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
C21H16ClN3γ = 97.981 (3)°
Mr = 345.82V = 1589.81 (13) Å3
Triclinic, P1Z = 4
a = 7.0098 (3) ÅMo Kα radiation
b = 15.0306 (7) ŵ = 0.25 mm−1
c = 17.0060 (8) ÅT = 120 K
α = 111.492 (2)°0.14 × 0.04 × 0.03 mm
β = 101.406 (3)°
Data collection top
Nonius KappaCCD area-detector
diffractometer		7321 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		4073 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 0.993Rint = 0.113
35785 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 1.03Δρmax = 0.30 e Å−3
7321 reflectionsΔρmin = −0.37 e Å−3
453 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl140.62859 (10)0.90803 (5)0.31741 (5)0.0308 (2)
N110.5024 (3)0.42836 (16)0.24275 (15)0.0256 (5)
N11a0.4963 (3)0.35103 (16)0.26626 (14)0.0227 (5)
N190.5274 (3)0.31548 (17)0.39424 (15)0.0263 (5)
C11b0.4606 (4)0.2532 (2)0.21034 (17)0.0229 (6)
C11c0.4432 (4)0.2215 (2)0.11577 (18)0.0244 (6)
C120.5273 (4)0.2821 (2)0.07935 (18)0.0265 (7)
C130.5161 (4)0.2454 (2)−0.00915 (18)0.0283 (7)
C140.4190 (4)0.1488 (2)−0.06282 (19)0.0311 (7)
C150.3350 (4)0.0882 (2)−0.02794 (18)0.0296 (7)
C15a0.3476 (4)0.1226 (2)0.06073 (18)0.0263 (7)
C160.2648 (4)0.0573 (2)0.10087 (18)0.0302 (7)
C170.4042 (4)0.0786 (2)0.18979 (18)0.0290 (7)
C17a0.4509 (4)0.18713 (19)0.24891 (18)0.0237 (6)
C180.4903 (4)0.2215 (2)0.34146 (18)0.0245 (6)
C19a0.5276 (4)0.3805 (2)0.35650 (18)0.0244 (6)
C1100.5556 (4)0.4814 (2)0.39119 (18)0.0261 (7)
C1110.5387 (4)0.5070 (2)0.31936 (17)0.0232 (6)
C1310.5579 (4)0.6054 (2)0.31877 (18)0.0232 (6)
C1320.5459 (4)0.6180 (2)0.24087 (18)0.0253 (6)
C1330.5664 (4)0.7099 (2)0.23978 (18)0.0274 (7)
C1340.6000 (4)0.79088 (19)0.31782 (18)0.0243 (6)
C1350.6134 (4)0.7813 (2)0.39600 (18)0.0276 (7)
C1360.5913 (4)0.6884 (2)0.39648 (18)0.0280 (7)
C1810.4976 (4)0.1508 (2)0.38531 (19)0.0319 (7)
Cl24−0.05261 (11)0.09943 (5)0.27457 (5)0.0378 (2)
N210.0130 (3)0.53992 (16)0.24916 (15)0.0275 (6)
N21a0.0454 (3)0.63920 (16)0.28162 (14)0.0234 (5)
N290.1396 (3)0.77941 (16)0.42033 (15)0.0271 (6)
C21b0.0335 (4)0.6966 (2)0.23437 (18)0.0236 (6)
C21c−0.0385 (4)0.6542 (2)0.13807 (17)0.0240 (6)
C22−0.1612 (4)0.5596 (2)0.08740 (18)0.0271 (7)
C23−0.2294 (4)0.5262 (2)−0.00278 (18)0.0285 (7)
C24−0.1771 (4)0.5858 (2)−0.04435 (19)0.0290 (7)
C25−0.0588 (4)0.6796 (2)0.00475 (19)0.0285 (7)
C25a0.0096 (4)0.7150 (2)0.09532 (19)0.0265 (7)
C260.1341 (4)0.8176 (2)0.14903 (18)0.0301 (7)
C270.0763 (4)0.8630 (2)0.23393 (18)0.0287 (7)
C27a0.0839 (4)0.7971 (2)0.28284 (18)0.0234 (6)
C280.1345 (4)0.8352 (2)0.37605 (18)0.0272 (7)
C29a0.0993 (4)0.6813 (2)0.37368 (18)0.0256 (6)
C2100.1005 (4)0.6040 (2)0.39874 (19)0.0280 (7)
C2110.0471 (4)0.5199 (2)0.32108 (18)0.0242 (6)
C2310.0242 (4)0.4165 (2)0.30983 (18)0.0240 (6)
C232−0.0117 (4)0.3414 (2)0.22687 (19)0.0278 (7)
C233−0.0363 (4)0.2443 (2)0.21597 (19)0.0294 (7)
C234−0.0228 (4)0.2223 (2)0.2884 (2)0.0285 (7)
C2350.0135 (4)0.2947 (2)0.3713 (2)0.0321 (7)
C2360.0357 (4)0.3918 (2)0.38153 (19)0.0293 (7)
C2810.1848 (4)0.9444 (2)0.42988 (19)0.0319 (7)
H120.59240.34880.11580.032*
H130.57520.2865−0.03320.034*
H140.41010.1241−0.12380.037*
H150.26770.0222−0.06540.036*
H16A0.2473−0.01240.06120.036*
H16B0.13200.06800.10810.036*
H17A0.34040.03990.21780.035*
H17B0.53000.05850.18160.035*
H18A0.56140.18720.44830.048*
H18B0.57480.10350.35970.048*
H18C0.36120.11560.37640.048*
H1100.58090.52440.45120.031*
H1320.52310.56200.18750.030*
H1330.55760.71760.18630.033*
H1350.63750.83780.44910.033*
H1360.59890.68120.45020.034*
H22−0.19770.51810.11540.033*
H23−0.31250.4621−0.03630.034*
H24−0.22240.5623−0.10640.035*
H25−0.02370.7204−0.02400.034*
H26A0.11440.85830.11500.036*
H26B0.27740.81620.16250.036*
H27A0.16900.92770.27120.034*
H27B−0.06060.87360.22070.034*
H2100.13140.60740.45690.034*
H232−0.01950.35710.17720.033*
H233−0.06230.19340.15920.035*
H2350.02310.27850.42070.038*
H2360.05920.44220.43840.035*
H28A0.19350.95710.49140.048*
H28B0.08010.97310.40790.048*
H28C0.31350.97410.42530.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0283 (13)0.0215 (13)0.0271 (14)0.0053 (10)0.0072 (10)0.0103 (11)
N11a0.0233 (12)0.0234 (13)0.0212 (13)0.0040 (10)0.0052 (10)0.0098 (11)
C11b0.0216 (14)0.0219 (15)0.0219 (16)0.0054 (11)0.0049 (11)0.0055 (13)
C11c0.0234 (15)0.0274 (16)0.0245 (16)0.0089 (12)0.0072 (12)0.0112 (13)
C120.0292 (16)0.0247 (16)0.0271 (17)0.0096 (12)0.0087 (13)0.0104 (13)
C130.0316 (16)0.0305 (17)0.0268 (17)0.0078 (13)0.0117 (13)0.0140 (14)
C140.0347 (17)0.0341 (18)0.0265 (17)0.0128 (14)0.0121 (13)0.0110 (14)
C150.0323 (17)0.0239 (16)0.0247 (17)0.0036 (13)0.0068 (13)0.0027 (13)
C15a0.0255 (15)0.0285 (16)0.0255 (17)0.0074 (12)0.0084 (12)0.0104 (13)
C160.0341 (17)0.0218 (15)0.0291 (18)0.0028 (13)0.0089 (13)0.0052 (13)
C170.0364 (17)0.0245 (16)0.0255 (17)0.0075 (13)0.0107 (13)0.0081 (13)
C17a0.0217 (14)0.0222 (15)0.0284 (17)0.0072 (12)0.0075 (12)0.0103 (13)
C180.0217 (15)0.0293 (16)0.0260 (17)0.0063 (12)0.0075 (12)0.0142 (14)
C1810.0383 (18)0.0286 (17)0.0285 (18)0.0087 (14)0.0079 (13)0.0115 (14)
N190.0298 (13)0.0268 (14)0.0230 (13)0.0076 (11)0.0073 (10)0.0105 (11)
C19a0.0235 (15)0.0262 (16)0.0224 (16)0.0038 (12)0.0050 (12)0.0099 (13)
C1100.0290 (16)0.0251 (16)0.0213 (16)0.0055 (12)0.0077 (12)0.0062 (13)
C1110.0212 (14)0.0234 (15)0.0220 (16)0.0032 (11)0.0062 (12)0.0065 (13)
C1310.0206 (14)0.0244 (15)0.0241 (16)0.0042 (12)0.0066 (12)0.0092 (13)
C1320.0268 (15)0.0204 (15)0.0240 (16)0.0040 (12)0.0067 (12)0.0045 (13)
C1330.0292 (16)0.0292 (17)0.0258 (17)0.0074 (13)0.0081 (12)0.0126 (14)
C1340.0231 (15)0.0206 (15)0.0290 (17)0.0052 (12)0.0069 (12)0.0099 (13)
Cl140.0388 (4)0.0216 (4)0.0313 (4)0.0060 (3)0.0095 (3)0.0101 (3)
C1350.0357 (17)0.0227 (16)0.0213 (16)0.0051 (13)0.0096 (13)0.0050 (13)
C1360.0351 (17)0.0254 (16)0.0222 (16)0.0058 (13)0.0096 (13)0.0078 (13)
N210.0274 (13)0.0242 (13)0.0301 (15)0.0044 (10)0.0070 (11)0.0110 (11)
N21a0.0228 (12)0.0221 (13)0.0222 (14)0.0038 (10)0.0056 (10)0.0064 (10)
C21b0.0203 (14)0.0285 (16)0.0238 (16)0.0060 (12)0.0060 (12)0.0123 (13)
C21c0.0226 (15)0.0253 (15)0.0234 (16)0.0075 (12)0.0060 (12)0.0085 (13)
C220.0264 (16)0.0258 (16)0.0300 (18)0.0055 (12)0.0093 (13)0.0118 (13)
C230.0274 (16)0.0281 (16)0.0267 (17)0.0069 (13)0.0050 (13)0.0083 (14)
C240.0316 (16)0.0319 (17)0.0212 (16)0.0087 (13)0.0036 (13)0.0095 (14)
C250.0309 (16)0.0308 (17)0.0276 (17)0.0078 (13)0.0096 (13)0.0151 (14)
C25a0.0233 (15)0.0288 (16)0.0292 (17)0.0084 (12)0.0080 (12)0.0124 (14)
C260.0354 (17)0.0264 (16)0.0286 (17)0.0048 (13)0.0092 (13)0.0119 (14)
C270.0316 (16)0.0238 (16)0.0289 (17)0.0043 (13)0.0077 (13)0.0096 (13)
C27a0.0206 (14)0.0235 (15)0.0264 (17)0.0066 (12)0.0083 (12)0.0087 (13)
C280.0235 (15)0.0269 (16)0.0282 (17)0.0067 (12)0.0077 (12)0.0073 (14)
N290.0277 (13)0.0248 (13)0.0259 (14)0.0050 (10)0.0080 (10)0.0072 (11)
C29a0.0248 (15)0.0273 (16)0.0228 (16)0.0058 (12)0.0065 (12)0.0081 (13)
C2100.0313 (16)0.0300 (17)0.0213 (16)0.0061 (13)0.0055 (12)0.0100 (14)
C2110.0218 (15)0.0282 (16)0.0235 (16)0.0043 (12)0.0083 (12)0.0107 (13)
C2310.0180 (14)0.0281 (16)0.0249 (17)0.0036 (12)0.0056 (11)0.0103 (13)
C2320.0268 (16)0.0318 (17)0.0253 (17)0.0061 (13)0.0057 (12)0.0130 (14)
C2330.0294 (16)0.0297 (17)0.0266 (17)0.0077 (13)0.0076 (13)0.0083 (14)
C2340.0221 (15)0.0286 (17)0.0377 (19)0.0059 (12)0.0085 (13)0.0163 (15)
Cl240.0397 (5)0.0290 (4)0.0461 (5)0.0074 (3)0.0098 (4)0.0178 (4)
C2350.0320 (17)0.0332 (18)0.0345 (19)0.0067 (13)0.0076 (14)0.0184 (15)
C2360.0307 (17)0.0303 (17)0.0262 (17)0.0070 (13)0.0083 (13)0.0103 (14)
C2810.0365 (18)0.0262 (16)0.0271 (17)0.0060 (13)0.0060 (13)0.0060 (14)
Geometric parameters (Å, º) top
N11—N11a1.359 (3)N21—N21a1.355 (3)
N11a—C11b1.381 (3)N21a—C21b1.378 (3)
C11b—C17a1.378 (4)C21b—C27a1.381 (4)
C17a—C181.419 (4)C27a—C281.422 (4)
C18—N191.321 (3)C28—N291.316 (3)
N19—C19a1.351 (3)N29—C29a1.350 (3)
C19a—C1101.379 (4)C29a—C2101.377 (4)
C110—C1111.398 (4)C210—C2111.390 (4)
C111—N111.348 (3)C211—N211.348 (3)
N11a—C19a1.393 (3)N21a—C29a1.403 (3)
C11b—C11c1.474 (4)C21b—C21c1.470 (4)
C11c—C121.403 (4)C21c—C221.405 (4)
C11c—C15a1.412 (4)C21c—C25a1.406 (4)
C12—C131.381 (4)C22—C231.383 (4)
C12—H120.95C22—H220.95
C13—C141.382 (4)C23—C241.382 (4)
C13—H130.95C23—H230.95
C14—C151.383 (4)C24—C251.383 (4)
C14—H140.95C24—H240.95
C15—C15a1.383 (4)C25—C25a1.386 (4)
C15—H150.95C25—H250.95
C15a—C161.502 (4)C25a—C261.501 (4)
C16—C171.522 (4)C26—C271.517 (4)
C16—H16A0.99C26—H26A0.99
C16—H16B0.99C26—H26B0.99
C17—C17a1.516 (4)C27—C27a1.509 (4)
C17—H17A0.99C27—H27A0.99
C17—H17B0.99C27—H27B0.99
C18—C1811.507 (4)C28—C2811.506 (4)
C181—H18A0.98C210—H2100.95
C181—H18B0.98C211—C2311.477 (4)
C181—H18C0.98C231—C2361.390 (4)
C110—H1100.95C231—C2321.393 (4)
C111—C1311.470 (4)C232—C2331.383 (4)
C131—C1321.393 (4)C232—H2320.95
C131—C1361.395 (4)C233—C2341.377 (4)
C132—C1331.377 (4)C233—H2330.95
C132—H1320.95C234—C2351.376 (4)
C133—C1341.382 (4)C234—Cl241.751 (3)
C133—H1330.95C235—C2361.387 (4)
C134—C1351.375 (4)C235—H2350.95
C134—Cl141.747 (3)C236—H2360.95
C135—C1361.387 (4)C281—H28A0.98
C135—H1350.95C281—H28B0.98
C136—H1360.95C281—H28C0.98
C111—N11—N11a104.0 (2)C211—N21—N21a104.2 (2)
N11—N11a—C11b126.4 (2)N21—N21a—C21b127.1 (2)
N11—N11a—C19a112.1 (2)N21—N21a—C29a111.6 (2)
C11b—N11a—C19a121.6 (2)C21b—N21a—C29a121.3 (2)
C17a—C11b—N11a115.9 (2)N21a—C21b—C27a116.2 (2)
C17a—C11b—C11c121.8 (2)N21a—C21b—C21c122.3 (2)
N11a—C11b—C11c122.2 (2)C27a—C21b—C21c121.4 (2)
C12—C11c—C15a119.0 (2)C22—C21c—C25a118.6 (3)
C12—C11c—C11b123.6 (2)C22—C21c—C21b124.1 (2)
C15a—C11c—C11b117.2 (2)C25a—C21c—C21b117.3 (2)
C13—C12—C11c120.4 (3)C23—C22—C21c120.7 (3)
C13—C12—H12119.8C23—C22—H22119.6
C11c—C12—H12119.8C21c—C22—H22119.6
C12—C13—C14120.2 (3)C24—C23—C22120.2 (3)
C12—C13—H13119.9C24—C23—H23119.9
C14—C13—H13119.9C22—C23—H23119.9
C13—C14—C15120.1 (3)C23—C24—C25119.7 (3)
C13—C14—H14119.9C23—C24—H24120.1
C15—C14—H14119.9C25—C24—H24120.1
C15a—C15—C14120.9 (3)C24—C25—C25a121.0 (3)
C15a—C15—H15119.6C24—C25—H25119.5
C14—C15—H15119.6C25a—C25—H25119.5
C15—C15a—C11c119.3 (3)C25—C25a—C21c119.7 (3)
C15—C15a—C16122.0 (2)C25—C25a—C26121.2 (3)
C11c—C15a—C16118.7 (2)C21c—C25a—C26119.1 (2)
C15a—C16—C17110.9 (2)C25a—C26—C27110.6 (2)
C15a—C16—H16A109.5C25a—C26—H26A109.5
C17—C16—H16A109.5C27—C26—H26A109.5
C15a—C16—H16B109.5C25a—C26—H26B109.5
C17—C16—H16B109.5C27—C26—H26B109.5
H16A—C16—H16B108.1H26A—C26—H26B108.1
C17a—C17—C16110.7 (2)C27a—C27—C26110.8 (2)
C17a—C17—H17A109.5C27a—C27—H27A109.5
C16—C17—H17A109.5C26—C27—H27A109.5
C17a—C17—H17B109.5C27a—C27—H27B109.5
C16—C17—H17B109.5C26—C27—H27B109.5
H17A—C17—H17B108.1H27A—C27—H27B108.1
C11b—C17a—C18120.0 (2)C21b—C27a—C28119.8 (3)
C11b—C17a—C17117.9 (2)C21b—C27a—C27118.1 (2)
C18—C17a—C17122.1 (2)C28—C27a—C27122.1 (2)
N19—C18—C17a123.3 (2)N29—C28—C27a123.4 (3)
N19—C18—C181116.1 (2)N29—C28—C281116.1 (2)
C17a—C18—C181120.7 (2)C27a—C28—C281120.5 (3)
C18—C181—H18A109.5C28—N29—C29a117.3 (2)
C18—C181—H18B109.5N29—C29a—C210132.1 (3)
H18A—C181—H18B109.5N29—C29a—N21a122.0 (2)
C18—C181—H18C109.5C210—C29a—N21a105.9 (2)
H18A—C181—H18C109.5C29a—C210—C211105.5 (2)
H18B—C181—H18C109.5C29a—C210—H210127.2
C18—N19—C19a117.1 (2)C211—C210—H210127.2
N19—C19a—C110132.0 (3)N21—C211—C210112.8 (2)
N19—C19a—N11a122.1 (2)N21—C211—C231119.0 (2)
C110—C19a—N11a106.0 (2)C210—C211—C231128.3 (3)
C19a—C110—C111105.4 (2)C236—C231—C232118.6 (3)
C19a—C110—H110127.3C236—C231—C211120.8 (3)
C111—C110—H110127.3C232—C231—C211120.6 (3)
N11—C111—C110112.6 (2)C233—C232—C231120.7 (3)
N11—C111—C131119.0 (2)C233—C232—H232119.6
C110—C111—C131128.5 (3)C231—C232—H232119.6
C132—C131—C136118.6 (3)C234—C233—C232119.3 (3)
C132—C131—C111120.8 (2)C234—C233—H233120.4
C136—C131—C111120.6 (2)C232—C233—H233120.4
C133—C132—C131121.2 (3)C235—C234—C233121.5 (3)
C133—C132—H132119.4C235—C234—Cl24119.3 (2)
C131—C132—H132119.4C233—C234—Cl24119.2 (2)
C132—C133—C134118.9 (3)C234—C235—C236118.9 (3)
C132—C133—H133120.5C234—C235—H235120.6
C134—C133—H133120.5C236—C235—H235120.6
C135—C134—C133121.4 (3)C235—C236—C231121.0 (3)
C135—C134—Cl14119.2 (2)C235—C236—H236119.5
C133—C134—Cl14119.4 (2)C231—C236—H236119.5
C134—C135—C136119.3 (3)C28—C281—H28A109.5
C134—C135—H135120.4C28—C281—H28B109.5
C136—C135—H135120.4H28A—C281—H28B109.5
C135—C136—C131120.5 (3)C28—C281—H28C109.5
C135—C136—H136119.7H28A—C281—H28C109.5
C131—C136—H136119.7H28B—C281—H28C109.5
C111—N11—N11a—C11b179.2 (2)C211—N21—N21a—C21b178.7 (2)
C111—N11—N11a—C19a0.3 (3)C211—N21—N21a—C29a−0.1 (3)
N11—N11a—C11b—C17a−176.6 (2)N21—N21a—C21b—C27a−176.7 (2)
C19a—N11a—C11b—C17a2.2 (3)C29a—N21a—C21b—C27a2.1 (3)
N11—N11a—C11b—C11c6.2 (4)N21—N21a—C21b—C21c6.4 (4)
C19a—N11a—C11b—C11c−175.0 (2)C29a—N21a—C21b—C21c−174.8 (2)
C17a—C11b—C11c—C12−153.6 (3)N21a—C21b—C21c—C2222.3 (4)
N11a—C11b—C11c—C1223.5 (4)C27a—C21b—C21c—C22−154.4 (3)
C17a—C11b—C11c—C15a22.0 (4)N21a—C21b—C21c—C25a−161.7 (2)
N11a—C11b—C11c—C15a−160.9 (2)C27a—C21b—C21c—C25a21.6 (4)
C15a—C11c—C12—C130.2 (4)C25a—C21c—C22—C231.4 (4)
C11b—C11c—C12—C13175.7 (2)C21b—C21c—C22—C23177.4 (2)
C11c—C12—C13—C141.0 (4)C21c—C22—C23—C240.1 (4)
C12—C13—C14—C15−0.8 (4)C22—C23—C24—C25−1.0 (4)
C13—C14—C15—C15a−0.5 (4)C23—C24—C25—C25a0.3 (4)
C14—C15—C15a—C11c1.7 (4)C24—C25—C25a—C21c1.3 (4)
C14—C15—C15a—C16−177.5 (3)C24—C25—C25a—C26−178.5 (3)
C12—C11c—C15a—C15−1.5 (4)C22—C21c—C25a—C25−2.1 (4)
C11b—C11c—C15a—C15−177.3 (2)C21b—C21c—C25a—C25−178.4 (2)
C12—C11c—C15a—C16177.7 (2)C22—C21c—C25a—C26177.7 (2)
C11b—C11c—C15a—C161.9 (4)C21b—C21c—C25a—C261.4 (4)
C15—C15a—C16—C17140.1 (3)C25—C25a—C26—C27141.3 (3)
C11c—C15a—C16—C17−39.1 (3)C21c—C25a—C26—C27−38.5 (3)
C15a—C16—C17—C17a53.3 (3)C25a—C26—C27—C27a53.2 (3)
N11a—C11b—C17a—C18−4.3 (4)N21a—C21b—C27a—C28−3.0 (3)
C11c—C11b—C17a—C18173.0 (2)C21c—C21b—C27a—C28174.0 (2)
N11a—C11b—C17a—C17177.8 (2)N21a—C21b—C27a—C27179.0 (2)
C11c—C11b—C17a—C17−5.0 (4)C21c—C21b—C27a—C27−4.0 (4)
C16—C17—C17a—C11b−32.8 (3)C26—C27—C27a—C21b−33.7 (3)
C16—C17—C17a—C18149.2 (2)C26—C27—C27a—C28148.3 (2)
C11b—C17a—C18—N193.5 (4)C21b—C27a—C28—N291.1 (4)
C17—C17a—C18—N19−178.6 (2)C27—C27a—C28—N29179.0 (2)
C11b—C17a—C18—C181−174.8 (2)C21b—C27a—C28—C281−178.5 (2)
C17—C17a—C18—C1813.1 (4)C27—C27a—C28—C281−0.5 (4)
C17a—C18—N19—C19a−0.3 (4)C27a—C28—N29—C29a1.8 (4)
C181—C18—N19—C19a178.1 (2)C281—C28—N29—C29a−178.6 (2)
C18—N19—C19a—C110178.3 (3)C28—N29—C29a—C210176.7 (3)
C18—N19—C19a—N11a−1.9 (4)C28—N29—C29a—N21a−2.7 (4)
N11—N11a—C19a—N19179.9 (2)N21—N21a—C29a—N29179.7 (2)
C11b—N11a—C19a—N190.9 (4)C21b—N21a—C29a—N290.8 (4)
N11—N11a—C19a—C110−0.3 (3)N21—N21a—C29a—C2100.2 (3)
C11b—N11a—C19a—C110−179.3 (2)C21b—N21a—C29a—C210−178.7 (2)
N19—C19a—C110—C111−180.0 (3)N29—C29a—C210—C211−179.6 (3)
N11a—C19a—C110—C1110.2 (3)N21a—C29a—C210—C211−0.2 (3)
N11a—N11—C111—C110−0.1 (3)N21a—N21—C211—C2100.0 (3)
N11a—N11—C111—C131179.2 (2)N21a—N21—C211—C231179.8 (2)
C19a—C110—C111—N110.0 (3)C29a—C210—C211—N210.1 (3)
C19a—C110—C111—C131−179.3 (3)C29a—C210—C211—C231−179.6 (3)
N11—C111—C131—C132−2.2 (4)N21—C211—C231—C236−172.7 (2)
C110—C111—C131—C132176.9 (3)C210—C211—C231—C2367.0 (4)
N11—C111—C131—C136178.6 (2)N21—C211—C231—C2326.5 (4)
C110—C111—C131—C136−2.2 (4)C210—C211—C231—C232−173.8 (3)
C136—C131—C132—C1330.1 (4)C236—C231—C232—C2330.3 (4)
C111—C131—C132—C133−179.1 (2)C211—C231—C232—C233−179.0 (2)
C131—C132—C133—C1340.2 (4)C231—C232—C233—C234−0.7 (4)
C132—C133—C134—C1350.0 (4)C232—C233—C234—C2350.4 (4)
C132—C133—C134—Cl14179.4 (2)C232—C233—C234—Cl24−179.6 (2)
C133—C134—C135—C136−0.4 (4)C233—C234—C235—C2360.3 (4)
Cl14—C134—C135—C136−179.8 (2)Cl24—C234—C235—C236−179.6 (2)
C134—C135—C136—C1310.7 (4)C234—C235—C236—C231−0.8 (4)
C132—C131—C136—C135−0.5 (4)C232—C231—C236—C2350.5 (4)
C111—C131—C136—C135178.7 (2)C211—C231—C236—C235179.7 (3)

Experimental details

(I)(II)
Crystal data
Chemical formulaC21H16ClN3C21H16ClN3
Mr345.82345.82
Crystal system, space groupTriclinic, P1Triclinic, P1
Temperature (K)120120
a, b, c (Å)9.2382 (8), 10.3054 (8), 10.3184 (9)7.0098 (3), 15.0306 (7), 17.0060 (8)
α, β, γ (°)62.720 (4), 83.098 (4), 70.531 (5)111.492 (2), 101.406 (3), 97.981 (3)
V (Å3)822.54 (12)1589.81 (13)
Z24
Radiation typeMo KαMo Kα
µ (mm−1)0.240.25
Crystal size (mm)0.34 × 0.19 × 0.080.14 × 0.04 × 0.03
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer		Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)		Multi-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.914, 0.9810.949, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections		17454, 3763, 2156 35785, 7321, 4073
Rint0.0940.113
(sin θ/λ)max (Å−1)0.6530.653
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.153, 0.96 0.061, 0.152, 1.03
No. of reflections37637321
No. of parameters229453
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.30, −0.300.30, −0.37

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected bond lengths (Å) for (I) top
N1—N1a1.357 (3)N9—C101.351 (3)
N1a—C21.365 (3)C10—C111.381 (4)
C2—C2a1.365 (4)C11—C121.393 (4)
C2a—C8b1.442 (4)C12—N11.345 (3)
C8b—N91.319 (3)N1a—C101.394 (3)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···Cg1i0.992.923.815 (3)150
Symmetry code: (i) −x+1, −y+1, −z+1.
Selected bond lengths (Å) for (II) top
N11—N11a1.359 (3)N21—N21a1.355 (3)
N11a—C11b1.381 (3)N21a—C21b1.378 (3)
C11b—C17a1.378 (4)C21b—C27a1.381 (4)
C17a—C181.419 (4)C27a—C281.422 (4)
C18—N191.321 (3)C28—N291.316 (3)
N19—C19a1.351 (3)N29—C29a1.350 (3)
C19a—C1101.379 (4)C29a—C2101.377 (4)
C110—C1111.398 (4)C210—C2111.390 (4)
C111—N111.348 (3)C211—N211.348 (3)
N11a—C19a1.393 (3)N21a—C29a1.403 (3)
 

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff for all their help and advice. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work. JQ and JP thank COLCIENCIAS and the Universidad de Valle for financial support. JC thanks the Consejería de Educación y Ciencia (Junta de Andalucía, Spain) for financial support.

References

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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 60| Part 8| August 2004| Pages o604-o607
doi:10.1107/S0108270104015616
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