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7-Benzyl-3-tert-butyl-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C22H25N3O, (I), and 3-tert-butyl-7-(4-methyl­benz­yl)-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C23H27N3O, (II), are isomorphous in the space group P21, and mol­ecules are linked into chains by C—H...O hydrogen bonds. In each of 3-tert-butyl-7-(4-methoxy­benz­yl)-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C23H27N3O2, (III), which has cell dimensions rather similar to those of (I) and (II), also in P21, and 3-tert-butyl-1-phenyl-7-[4-(trifluoro­meth­yl)benz­yl]-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C23H24F3N3O, (IV), there are no direction-specific inter­actions between the mol­ecules. In 3-tert-butyl-7-(4-nitro­benz­yl)-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C22H24N4O3, (V), a combination of C—H...O and C—H...N hydrogen bonds links the mol­ecules into complex sheets. There are no direction-specific inter­actions between the mol­ecules of 3-tert-butyl-7-(2,3-dimethoxy­benz­yl)-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C24H29N3O3, (VI), but a three-dimensional framework is formed in 3-tert-butyl-7-(3,4-methyl­enedioxy­benz­yl)-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C23H25N3O3, (VII), by a combination of C—H...O, C—H...N and C—H...π(arene) hydrogen bonds, while a combination of C—H...O and C—H...π(arene) hydrogen bonds links the mol­ecules of 3-tert-butyl-1-phenyl-7-(3,4,5-trimethoxy­benz­yl)-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine, C25H31N3O4, (VIII), into complex sheets. In each compound, the oxazine ring adopts a half-chair conformation, while the orientations of the pendent phenyl and tert-butyl substituents relative to the pyrazolo[3,4-d]oxazine unit are all very similar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109028017/fa3197sup1.cif
Contains datablocks global, I, II, III, IV, V, VI, VII, VIII

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270109028017/fa3197Isup2.hkl
Contains datablock I

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270109028017/fa3197IIsup3.hkl
Contains datablock II

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270109028017/fa3197IIIsup4.hkl
Contains datablock III

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270109028017/fa3197IVsup5.hkl
Contains datablock IV

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270109028017/fa3197Vsup6.hkl
Contains datablock V

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270109028017/fa3197VIsup7.hkl
Contains datablock VI

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270109028017/fa3197VIIsup8.hkl
Contains datablock VII

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270109028017/fa3197VIIIsup9.hkl
Contains datablock VIII

CCDC references: 746096; 746097; 746098; 746099; 746100; 746101; 746102; 746103

Comment top

In connection with our wider study of new synthetic routes to fused pyrazole derivatives having potential applications in fields such as drug precursors, pesticides and new materials (Elguero, 1984, 1996), we report here the structures of eight substituted pyrazolooxazines. These derivatives have been prepared following a synthetic sequence based on the condensation of a substituted 5-aminopyrazole with the appropriate aldehyde to provide (E)-3-tert-butyl-5-arylidenamino-1-phenyl-1H-pyrazole derivatives, followed by reduction of these intermediates to the corresponding 5-arylmethylamino-3-tert-butyl-1-phenyl-1H-pyrazoles (Castillo et al., 2009), and finally reaction with formaldehyde under acid catalysis.

Thus, we now report the structures of 7-benzyl-3-tert-butyl-1-phenylpyrazolo-oxazine (I) and of seven derivatives (II)–(VIII) (see scheme and Figs. 1 and2) bearing a range of simple substituents in the phenyl ring of the benzyl unit. Compounds (I) and (II) are isomorphous in space group P21; while compound (III) also crystallizes in P21 with cell dimensions and atomic coordinates similar to those in (I) and (II), it cannot be regarded as either isomorphous or isostructural with (I) and (II). Compound (VI) also crystallizes in P21 but with cell dimensions significantly different from those in compounds (I)–(III).

In each compound, the ring-puckering parameters (Cremer & Pople, 1975) show that the oxazine ring adopts an almost perfect half-chair conformation (Table 1): for this conformation, the idealized values of the puckering angles (calculated assuming equal bond distances throughout the ring) are θ = 129.2° and ϕ = (60n + 30)°, where n represents an integer. The rest of the skeletal conformation, defining the orientation of the pendent substituents relative to the pyrazolooxazine unit, can be defined in terms of just four torsional angles (Table 1). These data show the following: (i) the phenyl ring (C11–C16) adopts a very similar orientation in every compound; (ii) the orientation of the tert-butyl group is always such that one atom, C32, is close to the plane of the pyrazole ring, but always displaced from it with maximum and minimum displacements of 0.413 (3) Å in compound (VII) and 0.186 (2) Å in compound (V), respectively; the orientation of the benzyl substituent shows by far the widest range, although with no obvious systematic variation. In compound (V), the dihedral angle between the nitro group and the adjacent aryl ring is 11.2 (2)°, while the methoxy substituents exhibit different patterns of orientation in compounds (VI) and (VIII). In compound (VI) the methoxy atoms C721 and C731 are displaced from the plane of the ring (C71–C76) by 1.168 (4) and 0.009 (3) Å, respectively, while the displacements of atoms C731, C741 and C751 in compound (VIII) are 0.407 (2), 1.309 (2) and 0.262 (2) Å, respectively. In each compound, there is a short intramolecular C—H···N contact (Table 2) involving the aryl atom C12 and the ring atom N7; in every case, the C—H···N angle is narrow, 120° or less, suggesting that the interaction energy is likely to be small. This contact is probably adventitious, rather than a significant influence on the molecular conformation.

In each of compounds (I)–(VIII), the molecules have no internal symmetry and hence they are all chiral. While compounds (IV), (V), (VII) and (VIII) all crystallize as racemic mixtures of enantiomorphs, the crystals of compounds (I)–(III) and (VI) all contain a single enantiomorph. However, in the absence of significant resonant scattering, the enantiomorphs present in the crystals of compounds (I)–(III) and (VI) which had been selected for data collection cannot be identified. The synthesis of these compounds utilizes no reagents capable of imparting enantiomeric bias, and all are therefore expected to be formed as racemic mixtures, crystallizing as racemates for compounds (IV), (V), (VII) and (VIII), and as conglomerates for compounds (I)–(III) and (VI).

Despite their close similarities in both constitution and conformation, compounds (I)–(VIII) nonetheless show some interesting variations in their supramolecular aggregation, which is dominated by C—H···O and C—H···N hydrogen bonds, along with a single C—H···π(arene) hydrogen bond in each of compounds (II), (VII) and (VIII) (Table 2).

In both (I) and (II), molecules related by translation are linked into simple C(9) (Bernstein et al., 1995) chains running parallel to the [001] direction (Fig. 3). In addition, there is a rather long C—H···π(arene) hydrogen bond in (II), whose effect is to form a weak link between the chains along [001] so forming a sheet parallel to (010). No interaction of this kind can be identified in the structure of (I), so that while compounds (I) and (II) are isomorphous, they are not strictly isostructural (Acosta et al., 2009). In contrast, there are no direction-specific intermolecular interactions in the structures of compounds (III), (IV) or (VI), despite the presence of additional potential hydrogen-bond acceptor atoms in compounds (III) and (VI) [Figs. 1 and 2].

The supramolecular aggregation in compound (V) is two dimensional, in the form of deeply puckered sheets, and the formation of these sheets is readily analysed in terms of two one-dimensional substructures. In the simpler of these two substructures, molecules related by the 21 screw axis along (1/2, y, 1/4) are linked by a single C—H···O hydrogen bond (Table 2) into a simple C(6) chain running parallel to the [010] direction (Fig. 4). In the second substructure, molecules related by the c-glide plane at y = 0.75 are linked by one C—H···N hydrogen bond and one C—H···O hydrogen bond to form a C(6) C(8) [R22(17)] chain of rings running parallel to the [001] direction (Fig. 4). The combination of these two chain motifs generates a sheet parallel to (100).

There are five independent hydrogen bonds in the structure of compound (VII), which together generate a three-dimensional framework structure, whose formation can, however, be readily analysed in terms of three one-dimensional substructures, which involve, respectively, the three C—H···O hydrogen bonds, the C—H···N hydrogen bond and the C—H···π(arene) hydrogen bond. In the first substructure (Fig. 6), pairs of molecules related by inversion are linked by two independent C—H···O hydrogen bonds to form a dimeric unit containing three edge-fused hydrogen-bonded rings, with a centrosymmetric R22(14) ring centred at (1/2, 1/2, 1/2) flanked by two non-centrosymmetric but symmetry-related R22(7) rings. In addition, these units are linked by the third C—H···O hydrogen bond forming a further R22(8) ring motif, this time centrosymmetric and centred at (0, 1, 1/2). Propagation by inversion of these hydrogen bonds then generates a ribbon running parallel to the [110] direction, in which R22(8) rings centred at (n, 1- n, 1/2), where n represents an integer, alternate with R2214) rings centred at (1/2 + n, 1/2- n, 1/2), where n represents an integer (Fig. 6). A symmetry-related chain runs in the [110] direction

In the second substructure in (VII), a single C—H···N hydrogen bond links molecules related by the c-glide plane at y = 0.75 into a simple C(11) chain running parallel to the [201] direction (Fig. 7). Finally, a rather weak C—H···π(arene) hydrogen bond links molecules related by translation into a chain running along [100]. The combination of the one-dimensional substructures parallel to [100], [110], [110] and [201] is sufficient to link the molecules into a single three-dimensional framework.

Although the hydrogen-bonded supramolecular structure of compound (VIII) is only two-dimensional, as opposed to the three-dimensional structure found in compound (VII), it shares with compound (VII) the formation of a ribbon containing three types of ring, two of them centrosymmetric, built from three independent C—H···O hydrogen bonds, even though the details of the ribbon construction for the two compounds are different (Table 2). Pairs of molecules related by inversion are again linked by two C—H···O hydrogen bonds to form a dimer containing three edge-fused rings, but now with a centrosymmetric R22(24) ring flanked by two non-centrosymmetric R22(8) rings (Fig. 8). The third C—H···O hydrogen bond here generates a centrosymmetric R22(6) ring, and the combination of the these motifs generates a ribbon running parallel to the [210] direction, with R22(6) rings centred at (2n, 1/2- n, 1/2), alternating with R22(24) rings centred at (-1 + 2n, 1- n, 1/2), where n represents an integer (Fig. 8).

In the second substructure, a combination of C—H···O and C—H···π(arene) hydrogen bonds generates a chain of edge-fused rings parallel to the [100] direction, where centrosymmetric R22(6) centred at (n, 1/2, 1/2), where n represents an integer, formed by paired C—H···O hydrogen bonds alternate with centrosymmetric rings at (1/2, + n, 1/2, 1/2) formed by paired C—H···π(arene) hydrogen bonds (Fig. 9). The combination of the chains along [100] and the ribbons along [210] generates a sheet parallel to (001).

The structures reported here illustrate the subtle and often unpredictable interplay between intramolecular and intermolecular forces, particularly the interplay between intermolecular hydrogen bonding and molecular conformation, particularly as manifested here in the orientation of the aryl ring in the benzyl unit (Table 1). Thus, in compounds (III), (IV) and (VI) where there are no intermolecular hydrogen bonds, the conformations adopted by the benzyl unit are very similar. Similarly, in the isomorphous pair of compounds (I) and (II), where the chain-forming C—H···O hydrogen bond does not involve the benzyl unit, the overall conformations are very similar: the C—H···π(arene) unit in compound (II), which is to be regarded on geometric grounds as weak, appears to have little influence on the molecular conformation. The structures of compounds (VII) and (VIII) both contain a number of hydrogen bonds which involve the benzyl unit, providing both donors and acceptors in compound (VII) but only acceptors in compound (VIII). While this gives rise to a distinct benzyl ring orientation in compound (VIII), the conformation of compound (VII) is not significantly different from those of compounds (III) and (IV), where there are no direction-specific interactions of any kind between the molecules.

Related literature top

For related literature, see: Acosta et al. (2009); Bernstein et al. (1995); Castillo et al. (2009); Cremer & Pople (1975); Elguero (1984, 1996); Flack (1983).

Experimental top

A mixture of the corresponding 5-arylmethylamino-3-tert-butyl-1-phenyl-1H-pyrazole (0.29 mmol), ethanol (0.5 cm3), acetic acid (0.5 cm3) and formaldehyde (0.9 mmol, as an aqueous solution) was heated at 328 K for 10–16 h. After each reaction was complete the solvent was reduced to one-third of the initial volume and the resulting solid was collected by filtration and washed with cold ethanol. The products thus obtained were crystallized from ethanol except for (I) which was crystallized from hexane, to give colourless crystals suitable for single-crystal X-ray diffraction. 7-Benzyl-3-tert-butyl-1,4,6,7-tetrahydro-1-phenylpyrazolo[3,4-d][1,3]oxazine, (I); yield 81%, m,p, 405–406 K; MS (70 eV) m/z (%) = 347 (100) [M+], 316 (11), 302 (12), 256 (29), 228 (9), 91 (16), 77 (9) [Ph]; analysis found C 75.8, H 7.5, N 12.3%, C22H25N3O requires C 76.0, H 7.3, N 12.1%. 3-Tert-butyl-1,4,6,7-tetrahydro-7-(4-methylbenzyl)-1 -phenylpyrazolo[3,4-d][1,3]oxazine, (II); yield 86%, m.p. 403–404 K; MS (70 eV) m/z (%) = 361 (51) [M+], 256 (16), 105 (100) [C8H9]; analysis found C 76.2, H 7.5, N 11.5%, C23H27N3O requires C 76.4, H 7.5, N 11.6%. 3-Tert-butyl-1,4,6,7-tetrahydro-7-(4-methoxybenzyl)-1- phenylpyrazolo[3,4-d][1,3]oxazine, (III); yield 83%, m.p. 436–437 K; MS (70 eV) m/z (%) = 377 (10) [M+], 121 (100) [C8H9O]; analysis found C 72.9, H 7.1, N 10.9%, C23H27N3O2 requires C 73.2, H 7.2, N 11.1%. 3-Tert-butyl-7-[4-(Trifluoromethyl)benzyl]-1,4,6,7-tetrahydro- 1-phenylpyrazolo[3,4-d][1,3]oxazine, (IV), yield 87%, m.p. 425–426 K; MS (70 eV) m/z (%) = 415 (100) [M+], 370 (24), 170 (31), 159 (24) [C8H6F3]; analysis found C 66.6, H 5.9, N 9.9%, C23H24F3N3O requires C 66.5, H 5.8, N 10.1%. 3-Tert-butyl-1,4,6,7-tetrahydro-7-(4-nitrobenzyl)-1- phenylpyrazolo[3,4-d][1,3]oxazine, (V); yield 79%, m.p. 408–409 K; MS (70 eV) m/z (%) = 392 (100) [M+], 256 (41), 228 (24), 170 (25); analysis found C 67.1, H 6.3, N 14.1%, C22H24N4O3 requires C 67.3, H 6.2, N 14.3%. 3-Tert-butyl-1,4,6,7-tetrahydro-7-(2,3-Dimethoxybenzyl)-1- phenylpyrazolo[3,4-d][1,3]oxazine, (VI); yield 83%, m.p. 385–386 K; MS (70 eV) m/z (%) = 407 (34) [M+], 151 (100) [C9H11O2], 136 (81), 91 (21), 77 (10) [Ph]; analysis found C 70.5, H 7.3, N 10.2%, C24H29N3O3 requires C 70.7, H 7.2, N 10.3%. 7-[(Benzo[d][1,3]dioxol-5-yl)methyl]-3-tert-butyl-1,4,6,7- tetrahydro-1-phenylpyrazolo[3,4-d][1,3]oxazine, (VII); yield 88%, m.p. 436–437 K; MS: (70 eV) m/z (%) = 391 (11) [M+], 135 (100) [C8H7O2]; analysis found C 70.8, H 6.4, N 10.9%, C23H25N3O3 requires C 70.6, H 6.4, N 10.7%. 7-(3,4,5-Trimethoxybenzyl)-3-tert-butyl-1,4,6,7-tetrahydro-1- phenylpyrazolo[3,4-d][1,3]oxazine, (VIII); yield 79%, m.p. 439–440 K; MS (70 eV) m/z (%) = 437 (5) [M+], 181 (100) [C10H13O3]; analysis found C 68.5, H 7.1, N 9.3%, C25H31N3O4 requires C 68.6, H 7.1, N 9.6%.

Refinement top

All H atoms were located in difference maps and then treated as riding atoms in geometrically idealized positions with C—H distances 0.95 Å (aromatic), 0.98 Å (CH3) or 0.99 Å (CH2), and with Uiso(H) = kUeq(C), where k = 1.5 for methyl groups and 1.2 for all other H atoms. The methyl groups were permitted to rotate about the adjacent C—X (X = C or O) bonds but not to tilt. In the absence of significant resonant scattering, the Flack x parameters (Flack 1983) for compounds (I)–(III) and (VI) were indeterminate; accordingly the Friedel-equivalent reflections were merged, and for these compounds it is not possible to establish the absolute configurations of the molecules in the crystals which were selected for data collection. For all compounds, the reference molecules were selected to have the same absolute configuration (see Figs. 1 and 2).

Computing details top

For all compounds, data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structures of compounds (I)–(IV) showing the atom-labelling schemes. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular structures of compounds (V)–(VIII) showing the atom-labelling schemes. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of compound (I) showing the formation of a hydrogen-bonded C(9) chain along [001]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. An entirely similar chain is formed by compound (II).
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of compound (V) showing the formation of a hydrogen-bonded C(6) chain along [010]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted.
[Figure 5] Fig. 5. A stereoview of part of the crystal structure of compound (V) showing the formation of a hydrogen-bonded C(6) C(8) [R22(17)] chain of rings along [001]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted.
[Figure 6] Fig. 6. A stereoview of part of the crystal structure of compound (VII) showing the formation of a hydrogen-bonded ribbon running along [110], and containing three types of ring. For the sake of clarity, the H atoms not involved in the motif shown have been omitted. A symmetry-related chain runs parallel to the [110] direction.
[Figure 7] Fig. 7. A stereoview of part of the crystal structure of compound (VII) showing the formation of a simple hydrogen-bonded C(11) chain along [201]. For the sake of clarity, the H atoms not involved in the motif shown have been omitted.
[Figure 8] Fig. 8. A stereoview of part of the crystal structure of compound (VIII) showing the formation of a hydrogen-bonded ribbon running along [210], and containing three types of ring. For the sake of clarity, the H atoms not involved in the motif shown have been omitted.
[Figure 9] Fig. 9. A stereoview of part of the crystal structure of compound (VIII) showing the formation of a hydrogen-bonded chain of rings running along [100]. For the sake of clarity, the H atoms bonded to C atoms not involved in the motif shown have been omitted.
(I) 7-Benzyl-3-tert-butyl-1-phenyl-6,7-dihydro-1H,4H-pyrazolo[3,4-d][1,3]oxazine top
Crystal data top
C22H25N3OF(000) = 372
Mr = 347.45Dx = 1.213 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2303 reflections
a = 8.893 (1) Åθ = 2.8–27.5°
b = 11.1321 (12) ŵ = 0.08 mm1
c = 10.2078 (9) ÅT = 120 K
β = 109.749 (7)°Block, colourless
V = 951.11 (18) Å30.41 × 0.25 × 0.22 mm
Z = 2
Data collection top
Bruker Nonius KappaCCD
diffractometer
2303 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode1768 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.8°
ϕ & ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1413
Tmin = 0.885, Tmax = 0.975l = 1213
15738 measured reflections
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) = 0.103 w = 1/[σ2(Fo2) + (0.0465P)2 + 0.196P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
2303 reflectionsΔρmax = 0.20 e Å3
239 parametersΔρmin = 0.26 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.066 (6)
Crystal data top
C22H25N3OV = 951.11 (18) Å3
Mr = 347.45Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.893 (1) ŵ = 0.08 mm1
b = 11.1321 (12) ÅT = 120 K
c = 10.2078 (9) Å0.41 × 0.25 × 0.22 mm
β = 109.749 (7)°
Data collection top
Bruker Nonius KappaCCD
diffractometer
2303 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
1768 reflections with I > 2σ(I)
Tmin = 0.885, Tmax = 0.975Rint = 0.057
15738 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0431 restraint
wR(F2) = 0.103H-atom parameters constrained
S = 1.10Δρmax = 0.20 e Å3
2303 reflectionsΔρmin = 0.26 e Å3
239 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3066 (2)0.43662 (19)0.5201 (2)0.0228 (5)
N20.1674 (2)0.3775 (2)0.4516 (2)0.0241 (5)
C30.1017 (3)0.3529 (2)0.5472 (3)0.0247 (6)
C3a0.1995 (3)0.3938 (3)0.6793 (3)0.0255 (6)
C40.1927 (3)0.3853 (3)0.8237 (3)0.0330 (7)
H410.11240.44240.83470.040*
H420.16140.30310.84120.040*
O50.3468 (2)0.41360 (19)0.92027 (18)0.0350 (5)
C60.4094 (3)0.5179 (3)0.8798 (3)0.0317 (7)
H610.50300.54530.95850.038*
H620.32770.58220.85930.038*
N70.4573 (2)0.5000 (2)0.7589 (2)0.0251 (5)
C7a0.3262 (3)0.4464 (2)0.6573 (3)0.0238 (6)
C110.3994 (3)0.4817 (2)0.4425 (2)0.0233 (6)
C120.4834 (3)0.5878 (3)0.4814 (3)0.0267 (6)
H120.48040.63060.56100.032*
C130.5716 (3)0.6307 (3)0.4034 (3)0.0317 (6)
H130.63080.70300.43030.038*
C140.5746 (3)0.5703 (3)0.2875 (3)0.0365 (7)
H140.63510.60080.23400.044*
C150.4895 (3)0.4650 (3)0.2487 (3)0.0350 (7)
H150.49110.42300.16820.042*
C160.4022 (3)0.4207 (3)0.3265 (2)0.0279 (6)
H160.34390.34800.30000.034*
C310.0523 (3)0.2849 (3)0.5109 (3)0.0263 (6)
C320.1357 (3)0.2805 (3)0.3546 (3)0.0363 (7)
H32A0.06720.23910.31120.054*
H32B0.15660.36250.31800.054*
H32C0.23690.23710.33340.054*
C330.0152 (4)0.1577 (3)0.5670 (3)0.0401 (7)
H33A0.04200.16050.66750.060*
H33B0.05140.11760.52090.060*
H33C0.11520.11300.54860.060*
C340.1626 (3)0.3444 (3)0.5772 (3)0.0320 (7)
H34A0.18100.42810.54630.048*
H34B0.11320.34200.67880.048*
H34C0.26480.30140.54950.048*
C770.6042 (3)0.4273 (3)0.7886 (3)0.0290 (6)
H7710.62100.40790.69990.035*
H7720.59040.35070.83260.035*
C710.7485 (3)0.4908 (3)0.8825 (3)0.0280 (6)
C720.8324 (3)0.4444 (3)1.0119 (3)0.0319 (6)
H720.79620.37291.04240.038*
C730.9686 (3)0.5006 (3)1.0978 (3)0.0371 (7)
H731.02590.46731.18630.045*
C741.0208 (4)0.6048 (3)1.0551 (3)0.0399 (8)
H741.11430.64381.11390.048*
C750.9373 (4)0.6523 (3)0.9267 (3)0.0395 (8)
H750.97260.72460.89710.047*
C760.8025 (3)0.5952 (3)0.8409 (3)0.0347 (7)
H760.74620.62820.75200.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0193 (10)0.0246 (12)0.0227 (11)0.0022 (9)0.0048 (9)0.0021 (9)
N20.0212 (10)0.0232 (12)0.0254 (11)0.0019 (9)0.0045 (9)0.0020 (9)
C30.0246 (13)0.0219 (14)0.0277 (14)0.0023 (11)0.0088 (11)0.0005 (11)
C3a0.0234 (12)0.0272 (14)0.0253 (13)0.0011 (12)0.0076 (10)0.0013 (11)
C40.0302 (14)0.0430 (17)0.0257 (13)0.0082 (14)0.0094 (11)0.0013 (13)
O50.0335 (10)0.0457 (13)0.0231 (9)0.0084 (10)0.0060 (8)0.0029 (9)
C60.0314 (15)0.0366 (17)0.0261 (14)0.0047 (13)0.0084 (12)0.0056 (13)
N70.0232 (11)0.0267 (12)0.0233 (10)0.0003 (10)0.0052 (9)0.0028 (10)
C7a0.0228 (12)0.0247 (14)0.0219 (12)0.0023 (11)0.0051 (10)0.0012 (11)
C110.0189 (12)0.0259 (14)0.0236 (12)0.0009 (10)0.0050 (10)0.0057 (11)
C120.0248 (13)0.0263 (14)0.0278 (14)0.0013 (11)0.0074 (11)0.0022 (12)
C130.0289 (14)0.0295 (15)0.0338 (15)0.0049 (12)0.0069 (12)0.0054 (12)
C140.0329 (16)0.0472 (19)0.0303 (15)0.0047 (14)0.0119 (13)0.0068 (14)
C150.0352 (15)0.0477 (19)0.0228 (13)0.0051 (14)0.0108 (12)0.0005 (13)
C160.0269 (13)0.0334 (15)0.0211 (12)0.0024 (12)0.0050 (10)0.0006 (12)
C310.0231 (13)0.0261 (14)0.0301 (14)0.0028 (11)0.0094 (11)0.0027 (12)
C320.0277 (14)0.0468 (18)0.0327 (16)0.0115 (14)0.0079 (12)0.0058 (14)
C330.0350 (16)0.0301 (16)0.054 (2)0.0047 (13)0.0136 (15)0.0000 (15)
C340.0258 (14)0.0346 (16)0.0380 (15)0.0021 (12)0.0140 (12)0.0046 (13)
C770.0243 (13)0.0267 (14)0.0328 (14)0.0009 (11)0.0056 (11)0.0006 (12)
C710.0238 (13)0.0308 (15)0.0273 (13)0.0028 (12)0.0059 (11)0.0027 (12)
C720.0307 (14)0.0312 (16)0.0307 (14)0.0001 (12)0.0063 (12)0.0017 (12)
C730.0290 (14)0.0445 (18)0.0309 (14)0.0031 (14)0.0011 (12)0.0055 (14)
C740.0287 (15)0.049 (2)0.0379 (17)0.0047 (14)0.0053 (13)0.0116 (15)
C750.0382 (16)0.0376 (17)0.0425 (18)0.0124 (14)0.0134 (14)0.0045 (15)
C760.0347 (15)0.0347 (17)0.0314 (14)0.0032 (13)0.0068 (12)0.0008 (13)
Geometric parameters (Å, º) top
N1—C7a1.356 (3)C16—H160.9500
N1—N21.367 (3)C31—C321.517 (4)
N1—C111.415 (3)C31—C341.519 (4)
N2—C31.324 (3)C31—C331.522 (4)
C3—C3a1.410 (4)C32—H32A0.9800
C3—C311.498 (4)C32—H32B0.9800
C3a—C7a1.354 (4)C32—H32C0.9800
C3a—C41.499 (3)C33—H33A0.9800
C4—O51.427 (3)C33—H33B0.9800
C4—H410.9900C33—H33C0.9800
C4—H420.9900C34—H34A0.9800
O5—C61.408 (3)C34—H34B0.9800
C6—N71.449 (3)C34—H34C0.9800
C6—H610.9900C77—C711.494 (4)
C6—H620.9900C77—H7710.9900
N7—C7a1.405 (3)C77—H7720.9900
N7—C771.479 (3)C71—C761.378 (4)
C11—C161.372 (4)C71—C721.379 (4)
C11—C121.382 (4)C72—C731.381 (4)
C12—C131.378 (4)C72—H720.9500
C12—H120.9500C73—C741.374 (5)
C13—C141.369 (4)C73—H730.9500
C13—H130.9500C74—C751.375 (4)
C14—C151.378 (4)C74—H740.9500
C14—H140.9500C75—C761.378 (4)
C15—C161.376 (4)C75—H750.9500
C15—H150.9500C76—H760.9500
C7a—N1—N2110.2 (2)C3—C31—C34110.1 (2)
C7a—N1—C11130.8 (2)C32—C31—C34108.9 (2)
N2—N1—C11118.90 (19)C3—C31—C33108.3 (2)
C3—N2—N1105.75 (19)C32—C31—C33109.4 (2)
N2—C3—C3a110.8 (2)C34—C31—C33109.2 (2)
N2—C3—C31121.1 (2)C31—C32—H32A109.5
C3a—C3—C31128.0 (2)C31—C32—H32B109.5
C7a—C3a—C3105.1 (2)H32A—C32—H32B109.5
C7a—C3a—C4120.2 (2)C31—C32—H32C109.5
C3—C3a—C4134.7 (2)H32A—C32—H32C109.5
O5—C4—C3a108.5 (2)H32B—C32—H32C109.5
O5—C4—H41110.0C31—C33—H33A109.5
C3a—C4—H41110.0C31—C33—H33B109.5
O5—C4—H42110.0H33A—C33—H33B109.5
C3a—C4—H42110.0C31—C33—H33C109.5
H41—C4—H42108.4H33A—C33—H33C109.5
C6—O5—C4111.2 (2)H33B—C33—H33C109.5
O5—C6—N7113.3 (2)C31—C34—H34A109.5
O5—C6—H61108.9C31—C34—H34B109.5
N7—C6—H61108.9H34A—C34—H34B109.5
O5—C6—H62108.9C31—C34—H34C109.5
N7—C6—H62108.9H34A—C34—H34C109.5
H61—C6—H62107.7H34B—C34—H34C109.5
C7a—N7—C6106.1 (2)N7—C77—C71112.4 (2)
C7a—N7—C77112.0 (2)N7—C77—H771109.1
C6—N7—C77113.2 (2)C71—C77—H771109.1
C3a—C7a—N1108.2 (2)N7—C77—H772109.1
C3a—C7a—N7126.2 (2)C71—C77—H772109.1
N1—C7a—N7125.5 (2)H771—C77—H772107.9
C16—C11—C12120.3 (2)C76—C71—C72118.6 (3)
C16—C11—N1119.4 (2)C76—C71—C77121.0 (2)
C12—C11—N1120.2 (2)C72—C71—C77120.4 (3)
C13—C12—C11119.2 (3)C71—C72—C73120.8 (3)
C13—C12—H12120.4C71—C72—H72119.6
C11—C12—H12120.4C73—C72—H72119.6
C14—C13—C12120.6 (3)C74—C73—C72119.9 (3)
C14—C13—H13119.7C74—C73—H73120.0
C12—C13—H13119.7C72—C73—H73120.0
C13—C14—C15119.8 (3)C73—C74—C75119.7 (3)
C13—C14—H14120.1C73—C74—H74120.2
C15—C14—H14120.1C75—C74—H74120.2
C16—C15—C14120.1 (3)C74—C75—C76120.2 (3)
C16—C15—H15120.0C74—C75—H75119.9
C14—C15—H15120.0C76—C75—H75119.9
C11—C16—C15119.9 (3)C75—C76—C71120.8 (3)
C11—C16—H16120.0C75—C76—H76119.6
C15—C16—H16120.0C71—C76—H76119.6
C3—C31—C32110.9 (2)
C7a—N1—N2—C30.8 (3)C7a—N1—C11—C1230.7 (4)
C11—N1—N2—C3176.0 (2)N2—N1—C11—C12145.5 (2)
N1—N2—C3—C3a1.2 (3)C16—C11—C12—C130.8 (4)
N1—N2—C3—C31178.4 (2)N1—C11—C12—C13179.2 (2)
N2—C3—C3a—C7a1.2 (3)C11—C12—C13—C140.9 (4)
C31—C3—C3a—C7a178.1 (3)C12—C13—C14—C150.4 (4)
N2—C3—C3a—C4175.8 (3)C13—C14—C15—C160.2 (4)
C31—C3—C3a—C41.2 (5)C12—C11—C16—C150.3 (4)
C7a—C3a—C4—O513.0 (4)N1—C11—C16—C15178.7 (2)
C3—C3a—C4—O5163.6 (3)C14—C15—C16—C110.3 (4)
C3a—C4—O5—C646.8 (3)N2—C3—C31—C3214.8 (4)
C4—O5—C6—N771.5 (3)C3a—C3—C31—C32168.5 (3)
O5—C6—N7—C7a51.0 (3)N2—C3—C31—C34135.4 (3)
O5—C6—N7—C7772.2 (3)C3a—C3—C31—C3447.9 (4)
C3—C3a—C7a—N10.6 (3)N2—C3—C31—C33105.2 (3)
C4—C3a—C7a—N1176.9 (2)C3a—C3—C31—C3371.4 (3)
C3—C3a—C7a—N7179.5 (2)C7a—N7—C77—C71172.6 (2)
C4—C3a—C7a—N72.0 (4)C6—N7—C77—C7167.5 (3)
N2—N1—C7a—C3a0.1 (3)N7—C77—C71—C7664.3 (3)
C11—N1—C7a—C3a176.2 (3)N7—C77—C71—C72117.1 (3)
N2—N1—C7a—N7178.8 (2)C76—C71—C72—C730.5 (4)
C11—N1—C7a—N74.8 (4)C77—C71—C72—C73178.1 (3)
C6—N7—C7a—C3a15.6 (4)C71—C72—C73—C740.6 (4)
C77—N7—C7a—C3a108.3 (3)C72—C73—C74—C750.1 (4)
C6—N7—C7a—N1165.6 (3)C73—C74—C75—C760.5 (5)
C77—N7—C7a—N170.4 (3)C74—C75—C76—C710.6 (5)
C7a—N1—C11—C16150.9 (3)C72—C71—C76—C750.1 (4)
N2—N1—C11—C1633.0 (3)C77—C71—C76—C75178.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···N70.952.553.079 (4)115
C15—H15···O5i0.952.423.210 (3)140
Symmetry code: (i) x, y, z1.
(II) 3-tert-butyl-7-(4-methylbenzyl)-1-phenyl-6,7-dihydro- 1H,4H-pyrazolo[3,4-d][1,3]oxazine top
Crystal data top
C23H27N3OF(000) = 388
Mr = 361.48Dx = 1.245 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2323 reflections
a = 8.9500 (7) Åθ = 3.0–27.5°
b = 11.2146 (10) ŵ = 0.08 mm1
c = 10.0768 (9) ÅT = 120 K
β = 107.572 (5)°Block, colourless
V = 964.22 (15) Å30.32 × 0.22 × 0.15 mm
Z = 2
Data collection top
Bruker Nonius KappaCCD
diffractometer
2323 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode1443 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.096
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
ϕ & ω scansh = 1011
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1414
Tmin = 0.957, Tmax = 0.989l = 1313
15494 measured reflections
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)] = 0.052H-atom parameters constrained
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0767P)2 + 0.189P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2323 reflectionsΔρmax = 0.27 e Å3
249 parametersΔρmin = 0.30 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.032 (7)
Crystal data top
C23H27N3OV = 964.22 (15) Å3
Mr = 361.48Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.9500 (7) ŵ = 0.08 mm1
b = 11.2146 (10) ÅT = 120 K
c = 10.0768 (9) Å0.32 × 0.22 × 0.15 mm
β = 107.572 (5)°
Data collection top
Bruker Nonius KappaCCD
diffractometer
2323 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
1443 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.989Rint = 0.096
15494 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0521 restraint
wR(F2) = 0.149H-atom parameters constrained
S = 1.07Δρmax = 0.27 e Å3
2323 reflectionsΔρmin = 0.30 e Å3
249 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3078 (3)0.4332 (3)0.5203 (3)0.0238 (8)
N20.1722 (4)0.3740 (3)0.4519 (3)0.0253 (8)
C30.1017 (4)0.3517 (4)0.5478 (4)0.0247 (9)
C3a0.1920 (4)0.3949 (4)0.6797 (4)0.0266 (9)
C40.1777 (5)0.3906 (5)0.8237 (4)0.0322 (11)
H410.09560.44690.83150.039*
H420.14720.30930.84390.039*
O50.3239 (3)0.4219 (3)0.9210 (3)0.0327 (8)
C60.3895 (5)0.5233 (5)0.8770 (4)0.0325 (11)
H610.47830.55230.95510.039*
H620.30960.58730.85260.039*
N70.4445 (4)0.5000 (3)0.7580 (3)0.0254 (8)
C7a0.3193 (4)0.4460 (4)0.6571 (4)0.0263 (9)
C110.4058 (4)0.4750 (4)0.4433 (4)0.0239 (9)
C120.4847 (5)0.5823 (4)0.4768 (4)0.0283 (10)
H120.47580.62830.55320.034*
C130.5760 (4)0.6210 (5)0.3979 (4)0.0321 (11)
H130.63200.69390.42130.039*
C140.5879 (5)0.5567 (5)0.2861 (4)0.0336 (11)
H140.65140.58490.23240.040*
C150.5073 (4)0.4509 (5)0.2519 (4)0.0309 (11)
H150.51460.40650.17370.037*
C160.4164 (4)0.4091 (4)0.3303 (4)0.0278 (10)
H160.36140.33580.30710.033*
C310.0499 (4)0.2846 (4)0.5125 (4)0.0257 (10)
C320.1238 (5)0.2759 (5)0.3553 (4)0.0355 (11)
H32A0.14420.35620.31570.053*
H32B0.22270.23170.33480.053*
H32C0.05210.23400.31450.053*
C330.0154 (5)0.1602 (4)0.5737 (5)0.0370 (11)
H33A0.05520.11910.53110.055*
H33B0.11350.11530.55510.055*
H33C0.03440.16600.67450.055*
C340.1641 (5)0.3483 (4)0.5734 (4)0.0309 (10)
H34A0.11860.35420.67470.046*
H34B0.26240.30330.55140.046*
H34C0.18490.42860.53350.046*
C770.5865 (4)0.4259 (4)0.7933 (4)0.0303 (10)
H7710.60680.40050.70630.036*
H7720.56830.35330.84210.036*
C710.7286 (5)0.4891 (4)0.8836 (4)0.0280 (10)
C720.8120 (4)0.4434 (4)1.0116 (4)0.0290 (10)
H720.77370.37511.04670.035*
C730.9511 (5)0.4958 (4)1.0897 (4)0.0286 (10)
H731.00770.46211.17680.034*
C741.0079 (4)0.5955 (4)1.0428 (4)0.0291 (10)
C750.9211 (5)0.6440 (4)0.9169 (4)0.0321 (10)
H750.95630.71500.88440.039*
C760.7843 (5)0.5908 (4)0.8378 (4)0.0307 (10)
H760.72780.62460.75060.037*
C781.1619 (4)0.6482 (5)1.1232 (4)0.0323 (11)
H78A1.19650.61301.21650.048*
H78B1.15060.73471.13080.048*
H78C1.23970.63161.07500.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0211 (16)0.027 (2)0.0233 (17)0.0022 (15)0.0063 (13)0.0043 (16)
N20.0231 (17)0.026 (2)0.0257 (18)0.0024 (15)0.0060 (14)0.0018 (15)
C30.026 (2)0.023 (2)0.027 (2)0.0037 (18)0.0099 (17)0.0018 (19)
C3a0.024 (2)0.029 (3)0.027 (2)0.0038 (19)0.0085 (16)0.0003 (19)
C40.027 (2)0.043 (3)0.026 (2)0.004 (2)0.0076 (17)0.003 (2)
O50.0311 (15)0.042 (2)0.0228 (14)0.0039 (15)0.0049 (12)0.0018 (14)
C60.030 (2)0.043 (3)0.025 (2)0.003 (2)0.0078 (18)0.005 (2)
N70.0220 (17)0.031 (2)0.0202 (16)0.0021 (15)0.0014 (14)0.0020 (16)
C7a0.028 (2)0.027 (2)0.022 (2)0.0041 (19)0.0065 (16)0.0012 (19)
C110.0202 (19)0.027 (2)0.022 (2)0.0040 (17)0.0032 (16)0.0033 (18)
C120.025 (2)0.030 (3)0.028 (2)0.0012 (18)0.0052 (17)0.001 (2)
C130.023 (2)0.038 (3)0.031 (2)0.004 (2)0.0023 (17)0.007 (2)
C140.028 (2)0.045 (3)0.027 (2)0.000 (2)0.0071 (18)0.008 (2)
C150.025 (2)0.044 (3)0.024 (2)0.003 (2)0.0065 (17)0.001 (2)
C160.024 (2)0.033 (3)0.026 (2)0.0003 (19)0.0073 (16)0.000 (2)
C310.027 (2)0.027 (2)0.024 (2)0.0037 (18)0.0079 (16)0.0029 (19)
C320.028 (2)0.045 (3)0.031 (2)0.009 (2)0.0045 (18)0.009 (2)
C330.035 (2)0.032 (3)0.045 (3)0.000 (2)0.014 (2)0.001 (2)
C340.028 (2)0.035 (3)0.031 (2)0.0017 (19)0.0103 (18)0.001 (2)
C770.026 (2)0.030 (3)0.032 (2)0.0022 (19)0.0033 (17)0.000 (2)
C710.024 (2)0.033 (3)0.026 (2)0.0028 (18)0.0051 (17)0.007 (2)
C720.030 (2)0.029 (3)0.027 (2)0.0049 (19)0.0071 (17)0.002 (2)
C730.027 (2)0.034 (3)0.021 (2)0.0007 (19)0.0015 (17)0.000 (2)
C740.026 (2)0.034 (3)0.027 (2)0.0006 (19)0.0086 (18)0.006 (2)
C750.034 (2)0.028 (3)0.031 (2)0.003 (2)0.0065 (19)0.000 (2)
C760.032 (2)0.029 (3)0.027 (2)0.002 (2)0.0024 (18)0.001 (2)
C780.031 (2)0.039 (3)0.027 (2)0.004 (2)0.0081 (18)0.004 (2)
Geometric parameters (Å, º) top
N1—C7a1.358 (5)C31—C341.520 (6)
N1—N21.372 (4)C31—C321.524 (6)
N1—C111.415 (5)C32—H32A0.9800
N2—C31.328 (5)C32—H32B0.9800
C3—C3a1.416 (6)C32—H32C0.9800
C3—C311.497 (5)C33—H33A0.9800
C3a—C7a1.354 (6)C33—H33B0.9800
C3a—C41.496 (5)C33—H33C0.9800
C4—O51.422 (5)C34—H34A0.9800
C4—H410.9900C34—H34B0.9800
C4—H420.9900C34—H34C0.9800
O5—C61.411 (6)C77—C711.499 (6)
C6—N71.450 (5)C77—H7710.9900
C6—H610.9900C77—H7720.9900
C6—H620.9900C71—C721.379 (6)
N7—C7a1.403 (5)C71—C761.379 (6)
N7—C771.470 (5)C72—C731.387 (6)
C11—C121.385 (6)C72—H720.9500
C11—C161.385 (6)C73—C741.370 (6)
C12—C131.371 (6)C73—H730.9500
C12—H120.9500C74—C751.384 (6)
C13—C141.369 (7)C74—C781.494 (6)
C13—H130.9500C75—C761.379 (6)
C14—C151.377 (7)C75—H750.9500
C14—H140.9500C76—H760.9500
C15—C161.377 (6)C78—H78A0.9800
C15—H150.9500C78—H78B0.9800
C16—H160.9500C78—H78C0.9800
C31—C331.519 (7)
C7a—N1—N2110.2 (3)C33—C31—C32109.5 (4)
C7a—N1—C11130.7 (3)C34—C31—C32108.4 (3)
N2—N1—C11119.0 (3)C31—C32—H32A109.5
C3—N2—N1105.5 (3)C31—C32—H32B109.5
N2—C3—C3a110.9 (3)H32A—C32—H32B109.5
N2—C3—C31121.1 (3)C31—C32—H32C109.5
C3a—C3—C31127.9 (3)H32A—C32—H32C109.5
C7a—C3a—C3104.9 (3)H32B—C32—H32C109.5
C7a—C3a—C4120.0 (4)C31—C33—H33A109.5
C3—C3a—C4135.0 (3)C31—C33—H33B109.5
O5—C4—C3a109.3 (3)H33A—C33—H33B109.5
O5—C4—H41109.8C31—C33—H33C109.5
C3a—C4—H41109.8H33A—C33—H33C109.5
O5—C4—H42109.8H33B—C33—H33C109.5
C3a—C4—H42109.8C31—C34—H34A109.5
H41—C4—H42108.3C31—C34—H34B109.5
C6—O5—C4111.4 (3)H34A—C34—H34B109.5
O5—C6—N7113.1 (4)C31—C34—H34C109.5
O5—C6—H61109.0H34A—C34—H34C109.5
N7—C6—H61109.0H34B—C34—H34C109.5
O5—C6—H62109.0N7—C77—C71113.1 (4)
N7—C6—H62109.0N7—C77—H771109.0
H61—C6—H62107.8C71—C77—H771109.0
C7a—N7—C6106.3 (3)N7—C77—H772109.0
C7a—N7—C77112.0 (3)C71—C77—H772109.0
C6—N7—C77112.7 (3)H771—C77—H772107.8
C3a—C7a—N1108.4 (3)C72—C71—C76118.2 (4)
C3a—C7a—N7126.1 (4)C72—C71—C77120.8 (4)
N1—C7a—N7125.5 (4)C76—C71—C77120.9 (4)
C12—C11—C16120.5 (4)C71—C72—C73120.9 (4)
C12—C11—N1120.6 (4)C71—C72—H72119.6
C16—C11—N1118.8 (4)C73—C72—H72119.6
C13—C12—C11118.9 (4)C74—C73—C72120.9 (4)
C13—C12—H12120.5C74—C73—H73119.6
C11—C12—H12120.5C72—C73—H73119.6
C14—C13—C12121.2 (5)C73—C74—C75118.2 (4)
C14—C13—H13119.4C73—C74—C78120.9 (4)
C12—C13—H13119.4C75—C74—C78120.8 (4)
C13—C14—C15119.7 (4)C76—C75—C74121.0 (4)
C13—C14—H14120.2C76—C75—H75119.5
C15—C14—H14120.2C74—C75—H75119.5
C16—C15—C14120.3 (4)C75—C76—C71120.8 (4)
C16—C15—H15119.8C75—C76—H76119.6
C14—C15—H15119.8C71—C76—H76119.6
C15—C16—C11119.3 (4)C74—C78—H78A109.5
C15—C16—H16120.3C74—C78—H78B109.5
C11—C16—H16120.3H78A—C78—H78B109.5
C3—C31—C33107.8 (3)C74—C78—H78C109.5
C3—C31—C34109.8 (3)H78A—C78—H78C109.5
C33—C31—C34110.3 (4)H78B—C78—H78C109.5
C3—C31—C32111.0 (3)
C7a—N1—N2—C30.3 (4)N2—N1—C11—C1634.0 (5)
C11—N1—N2—C3176.7 (4)C16—C11—C12—C131.3 (6)
N1—N2—C3—C3a0.8 (4)N1—C11—C12—C13178.6 (4)
N1—N2—C3—C31178.5 (4)C11—C12—C13—C141.1 (6)
N2—C3—C3a—C7a0.9 (5)C12—C13—C14—C150.2 (6)
C31—C3—C3a—C7a178.4 (4)C13—C14—C15—C160.7 (6)
N2—C3—C3a—C4176.2 (5)C14—C15—C16—C110.5 (6)
C31—C3—C3a—C41.3 (8)C12—C11—C16—C150.5 (6)
C7a—C3a—C4—O512.1 (6)N1—C11—C16—C15177.9 (3)
C3—C3a—C4—O5164.7 (5)N2—C3—C31—C33106.2 (4)
C3a—C4—O5—C645.4 (5)C3a—C3—C31—C3371.1 (5)
C4—O5—C6—N770.5 (4)N2—C3—C31—C34133.6 (4)
O5—C6—N7—C7a51.7 (4)C3a—C3—C31—C3449.1 (6)
O5—C6—N7—C7771.3 (4)N2—C3—C31—C3213.7 (5)
C3—C3a—C7a—N10.7 (5)C3a—C3—C31—C32169.0 (4)
C4—C3a—C7a—N1177.0 (4)C7a—N7—C77—C71171.0 (3)
C3—C3a—C7a—N7179.0 (4)C6—N7—C77—C7169.2 (5)
C4—C3a—C7a—N71.3 (7)N7—C77—C71—C72122.1 (4)
N2—N1—C7a—C3a0.2 (5)N7—C77—C71—C7661.5 (5)
C11—N1—C7a—C3a176.9 (4)C76—C71—C72—C732.3 (6)
N2—N1—C7a—N7178.6 (4)C77—C71—C72—C73174.2 (4)
C11—N1—C7a—N74.8 (7)C71—C72—C73—C741.1 (6)
C6—N7—C7a—C3a17.2 (6)C72—C73—C74—C751.3 (6)
C77—N7—C7a—C3a106.3 (5)C72—C73—C74—C78176.7 (4)
C6—N7—C7a—N1164.7 (4)C73—C74—C75—C762.6 (6)
C77—N7—C7a—N171.8 (5)C78—C74—C75—C76175.4 (4)
C7a—N1—C11—C1232.9 (6)C74—C75—C76—C711.4 (7)
N2—N1—C11—C12143.5 (4)C72—C71—C76—C751.0 (6)
C7a—N1—C11—C16149.7 (4)C77—C71—C76—C75175.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···N70.952.603.103 (5)113
C15—H15···O5i0.952.613.258 (5)126
C4—H41···Cg1ii0.992.963.872 (5)154
Symmetry codes: (i) x, y, z1; (ii) x1, y, z.
(III) 3-tert-butyl-7-(4-methoxybenzyl)-1-phenyl-6,7-dihydro- 1H,4H-pyrazolo[3,4-d][1,3]oxazine top
Crystal data top
C23H27N3O2F(000) = 404
Mr = 377.48Dx = 1.252 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2411 reflections
a = 9.1888 (2) Åθ = 3.3–27.5°
b = 11.4499 (3) ŵ = 0.08 mm1
c = 9.7210 (2) ÅT = 120 K
β = 101.857 (1)°Plate, colourless
V = 1000.93 (4) Å30.15 × 0.12 × 0.05 mm
Z = 2
Data collection top
Bruker Nonius KappaCCD
diffractometer
2411 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode2237 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.3°
ϕ & ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1414
Tmin = 0.980, Tmax = 0.996l = 1212
12855 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.19 w = 1/[σ2(Fo2) + (0.0249P)2 + 0.3009P]
where P = (Fo2 + 2Fc2)/3
2411 reflections(Δ/σ)max = 0.001
257 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = 0.20 e Å3
Crystal data top
C23H27N3O2V = 1000.93 (4) Å3
Mr = 377.48Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.1888 (2) ŵ = 0.08 mm1
b = 11.4499 (3) ÅT = 120 K
c = 9.7210 (2) Å0.15 × 0.12 × 0.05 mm
β = 101.857 (1)°
Data collection top
Bruker Nonius KappaCCD
diffractometer
2411 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2237 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.996Rint = 0.036
12855 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.085H-atom parameters constrained
S = 1.19Δρmax = 0.17 e Å3
2411 reflectionsΔρmin = 0.20 e Å3
257 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.30851 (18)0.44062 (16)0.49961 (18)0.0181 (4)
N20.18295 (18)0.38394 (16)0.42962 (19)0.0189 (4)
C30.1054 (2)0.35873 (19)0.5281 (2)0.0184 (4)
C3a0.1815 (2)0.39726 (19)0.6624 (2)0.0193 (4)
C40.1524 (2)0.3901 (2)0.8090 (2)0.0262 (5)
H410.07300.44580.81940.031*
H420.11880.31040.82690.031*
O50.28733 (18)0.41768 (16)0.90850 (16)0.0274 (4)
C60.3562 (3)0.5198 (2)0.8664 (2)0.0242 (5)
H610.43540.54610.94530.029*
H620.28130.58290.84560.029*
N70.42067 (19)0.50000 (17)0.74260 (18)0.0200 (4)
C7a0.3087 (2)0.44813 (19)0.6400 (2)0.0188 (4)
C110.4150 (2)0.48229 (19)0.4231 (2)0.0184 (4)
C120.4883 (2)0.5878 (2)0.4598 (2)0.0229 (5)
H120.46940.63190.53710.027*
C130.5892 (2)0.6276 (2)0.3822 (3)0.0274 (5)
H130.64100.69880.40760.033*
C140.6152 (3)0.5645 (2)0.2679 (3)0.0284 (5)
H140.68400.59240.21490.034*
C150.5402 (2)0.4604 (2)0.2315 (2)0.0257 (5)
H150.55740.41740.15290.031*
C160.4403 (2)0.4185 (2)0.3089 (2)0.0224 (5)
H160.38970.34680.28400.027*
C310.0396 (2)0.29158 (19)0.4906 (2)0.0200 (4)
C320.1048 (3)0.2980 (3)0.3330 (2)0.0306 (6)
H32A0.12300.37980.30500.046*
H32B0.19870.25460.31180.046*
H32C0.03460.26360.28110.046*
C330.0074 (3)0.1635 (2)0.5327 (3)0.0297 (5)
H33A0.06260.13100.47920.045*
H33B0.10020.11870.51230.045*
H33C0.03610.15890.63340.045*
C340.1539 (3)0.3417 (2)0.5702 (3)0.0276 (5)
H34A0.11690.33220.67160.041*
H34B0.24830.29990.54190.041*
H34C0.16920.42480.54800.041*
C770.5584 (2)0.4281 (2)0.7748 (2)0.0229 (5)
H7710.58430.40240.68560.027*
H7720.53950.35750.82720.027*
C710.6879 (2)0.4941 (2)0.8603 (2)0.0211 (4)
C720.7903 (2)0.4388 (2)0.9637 (2)0.0206 (4)
H720.77360.35990.98640.025*
C730.9178 (2)0.4956 (2)1.0357 (2)0.0217 (4)
H730.98720.45571.10580.026*
C740.9419 (2)0.6107 (2)1.0038 (2)0.0217 (4)
C750.8382 (3)0.6695 (2)0.9034 (3)0.0293 (5)
H750.85310.74930.88360.035*
C760.7134 (3)0.6111 (2)0.8325 (3)0.0294 (5)
H760.64350.65160.76330.035*
O741.06483 (17)0.67453 (15)1.06569 (17)0.0273 (4)
C781.1825 (2)0.6116 (2)1.1548 (2)0.0276 (5)
H78A1.21380.54641.10230.041*
H78B1.14720.58121.23640.041*
H78C1.26700.66401.18680.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0159 (8)0.0201 (9)0.0186 (8)0.0020 (8)0.0043 (7)0.0002 (7)
N20.0165 (8)0.0183 (9)0.0223 (9)0.0034 (7)0.0048 (7)0.0019 (7)
C30.0170 (9)0.0156 (10)0.0231 (10)0.0005 (8)0.0052 (8)0.0006 (8)
C3a0.0187 (9)0.0185 (10)0.0216 (10)0.0006 (9)0.0057 (8)0.0000 (8)
C40.0260 (11)0.0307 (13)0.0223 (11)0.0057 (10)0.0058 (9)0.0024 (10)
O50.0317 (8)0.0324 (10)0.0182 (7)0.0060 (8)0.0050 (6)0.0009 (7)
C60.0284 (11)0.0246 (12)0.0196 (10)0.0034 (10)0.0054 (9)0.0029 (9)
N70.0173 (8)0.0209 (9)0.0204 (9)0.0007 (8)0.0009 (7)0.0023 (8)
C7a0.0205 (10)0.0173 (10)0.0187 (10)0.0007 (9)0.0038 (8)0.0006 (8)
C110.0126 (9)0.0216 (11)0.0210 (10)0.0002 (9)0.0033 (7)0.0039 (9)
C120.0217 (10)0.0231 (11)0.0233 (11)0.0006 (9)0.0034 (9)0.0023 (9)
C130.0196 (10)0.0263 (13)0.0348 (13)0.0049 (10)0.0017 (9)0.0069 (10)
C140.0175 (11)0.0397 (14)0.0291 (12)0.0008 (10)0.0070 (9)0.0124 (11)
C150.0201 (10)0.0366 (14)0.0211 (10)0.0034 (10)0.0054 (8)0.0018 (10)
C160.0191 (10)0.0239 (11)0.0237 (10)0.0009 (9)0.0036 (8)0.0008 (9)
C310.0183 (10)0.0190 (10)0.0230 (10)0.0031 (9)0.0048 (8)0.0001 (9)
C320.0219 (11)0.0404 (15)0.0286 (12)0.0102 (11)0.0029 (9)0.0019 (11)
C330.0264 (11)0.0184 (12)0.0443 (15)0.0047 (10)0.0071 (11)0.0011 (11)
C340.0203 (11)0.0274 (12)0.0376 (14)0.0023 (9)0.0118 (10)0.0039 (10)
C770.0198 (10)0.0205 (11)0.0266 (11)0.0011 (9)0.0008 (9)0.0012 (9)
C710.0199 (10)0.0218 (11)0.0211 (10)0.0008 (10)0.0032 (8)0.0024 (9)
C720.0215 (10)0.0184 (11)0.0224 (10)0.0006 (9)0.0060 (8)0.0012 (9)
C730.0194 (10)0.0267 (12)0.0186 (10)0.0039 (10)0.0029 (8)0.0005 (9)
C740.0196 (10)0.0233 (11)0.0215 (10)0.0008 (9)0.0027 (8)0.0033 (9)
C750.0300 (12)0.0175 (11)0.0352 (13)0.0035 (10)0.0052 (10)0.0040 (10)
C760.0280 (12)0.0223 (12)0.0316 (12)0.0005 (10)0.0087 (10)0.0048 (10)
O740.0204 (8)0.0249 (9)0.0320 (9)0.0018 (7)0.0054 (7)0.0001 (7)
C780.0202 (11)0.0325 (13)0.0283 (12)0.0028 (10)0.0005 (9)0.0016 (11)
Geometric parameters (Å, º) top
N1—C7a1.367 (3)C31—C331.535 (3)
N1—N21.376 (2)C31—C341.537 (3)
N1—C111.428 (3)C32—H32A0.9800
N2—C31.337 (3)C32—H32B0.9800
C3—C3a1.419 (3)C32—H32C0.9800
C3—C311.517 (3)C33—H33A0.9800
C3a—C7a1.363 (3)C33—H33B0.9800
C3a—C41.505 (3)C33—H33C0.9800
C4—O51.442 (3)C34—H34A0.9800
C4—H410.9900C34—H34B0.9800
C4—H420.9900C34—H34C0.9800
O5—C61.428 (3)C77—C711.507 (3)
C6—N71.464 (3)C77—H7710.9900
C6—H610.9900C77—H7720.9900
C6—H620.9900C71—C721.382 (3)
N7—C7a1.409 (3)C71—C761.397 (3)
N7—C771.488 (3)C72—C731.396 (3)
C11—C161.387 (3)C72—H720.9500
C11—C121.393 (3)C73—C741.381 (3)
C12—C131.387 (3)C73—H730.9500
C12—H120.9500C74—O741.376 (3)
C13—C141.387 (4)C74—C751.389 (3)
C13—H130.9500C75—C761.383 (3)
C14—C151.385 (4)C75—H750.9500
C14—H140.9500C76—H760.9500
C15—C161.387 (3)O74—C781.433 (3)
C15—H150.9500C78—H78A0.9800
C16—H160.9500C78—H78B0.9800
C31—C321.528 (3)C78—H78C0.9800
C7a—N1—N2110.62 (16)C32—C31—C34108.62 (19)
C7a—N1—C11129.72 (18)C33—C31—C34109.7 (2)
N2—N1—C11119.66 (16)C31—C32—H32A109.5
C3—N2—N1105.30 (16)C31—C32—H32B109.5
N2—C3—C3a110.95 (18)H32A—C32—H32B109.5
N2—C3—C31120.57 (19)C31—C32—H32C109.5
C3a—C3—C31128.40 (19)H32A—C32—H32C109.5
C7a—C3a—C3105.20 (18)H32B—C32—H32C109.5
C7a—C3a—C4119.99 (19)C31—C33—H33A109.5
C3—C3a—C4134.79 (19)C31—C33—H33B109.5
O5—C4—C3a109.12 (17)H33A—C33—H33B109.5
O5—C4—H41109.9C31—C33—H33C109.5
C3a—C4—H41109.9H33A—C33—H33C109.5
O5—C4—H42109.9H33B—C33—H33C109.5
C3a—C4—H42109.9C31—C34—H34A109.5
H41—C4—H42108.3C31—C34—H34B109.5
C6—O5—C4110.95 (17)H34A—C34—H34B109.5
O5—C6—N7112.76 (18)C31—C34—H34C109.5
O5—C6—H61109.0H34A—C34—H34C109.5
N7—C6—H61109.0H34B—C34—H34C109.5
O5—C6—H62109.0N7—C77—C71112.32 (18)
N7—C6—H62109.0N7—C77—H771109.1
H61—C6—H62107.8C71—C77—H771109.1
C7a—N7—C6106.66 (17)N7—C77—H772109.1
C7a—N7—C77112.44 (17)C71—C77—H772109.1
C6—N7—C77112.53 (17)H771—C77—H772107.9
C3a—C7a—N1107.92 (18)C72—C71—C76117.7 (2)
C3a—C7a—N7126.35 (19)C72—C71—C77121.0 (2)
N1—C7a—N7125.72 (19)C76—C71—C77121.3 (2)
C16—C11—C12120.7 (2)C71—C72—C73121.8 (2)
C16—C11—N1119.09 (19)C71—C72—H72119.1
C12—C11—N1120.18 (19)C73—C72—H72119.1
C13—C12—C11119.1 (2)C74—C73—C72119.3 (2)
C13—C12—H12120.4C74—C73—H73120.4
C11—C12—H12120.4C72—C73—H73120.4
C14—C13—C12120.6 (2)O74—C74—C73124.3 (2)
C14—C13—H13119.7O74—C74—C75115.6 (2)
C12—C13—H13119.7C73—C74—C75120.1 (2)
C15—C14—C13119.6 (2)C76—C75—C74119.7 (2)
C15—C14—H14120.2C76—C75—H75120.2
C13—C14—H14120.2C74—C75—H75120.2
C14—C15—C16120.6 (2)C75—C76—C71121.4 (2)
C14—C15—H15119.7C75—C76—H76119.3
C16—C15—H15119.7C71—C76—H76119.3
C15—C16—C11119.3 (2)C74—O74—C78116.52 (19)
C15—C16—H16120.3O74—C78—H78A109.5
C11—C16—H16120.3O74—C78—H78B109.5
C3—C31—C32111.16 (18)H78A—C78—H78B109.5
C3—C31—C33107.96 (18)O74—C78—H78C109.5
C32—C31—C33109.1 (2)H78A—C78—H78C109.5
C3—C31—C34110.31 (18)H78B—C78—H78C109.5
C7a—N1—N2—C31.0 (2)C16—C11—C12—C131.1 (3)
C11—N1—N2—C3178.62 (19)N1—C11—C12—C13178.8 (2)
N1—N2—C3—C3a0.9 (2)C11—C12—C13—C141.1 (3)
N1—N2—C3—C31177.94 (18)C12—C13—C14—C150.4 (3)
N2—C3—C3a—C7a0.5 (3)C13—C14—C15—C160.4 (3)
C31—C3—C3a—C7a177.2 (2)C14—C15—C16—C110.5 (3)
N2—C3—C3a—C4177.7 (2)C12—C11—C16—C150.3 (3)
C31—C3—C3a—C41.0 (4)N1—C11—C16—C15178.0 (2)
C7a—C3a—C4—O513.0 (3)N2—C3—C31—C3219.9 (3)
C3—C3a—C4—O5165.0 (2)C3a—C3—C31—C32163.7 (2)
C3a—C4—O5—C646.4 (2)N2—C3—C31—C3399.7 (2)
C4—O5—C6—N770.6 (2)C3a—C3—C31—C3376.7 (3)
O5—C6—N7—C7a51.0 (2)N2—C3—C31—C34140.5 (2)
O5—C6—N7—C7772.7 (2)C3a—C3—C31—C3443.1 (3)
C3—C3a—C7a—N10.1 (2)C7a—N7—C77—C71167.92 (18)
C4—C3a—C7a—N1178.65 (19)C6—N7—C77—C7171.6 (2)
C3—C3a—C7a—N7179.8 (2)N7—C77—C71—C72143.1 (2)
C4—C3a—C7a—N71.7 (3)N7—C77—C71—C7640.8 (3)
N2—N1—C7a—C3a0.7 (2)C76—C71—C72—C731.9 (3)
C11—N1—C7a—C3a178.9 (2)C77—C71—C72—C73174.37 (19)
N2—N1—C7a—N7179.6 (2)C71—C72—C73—C740.6 (3)
C11—N1—C7a—N70.8 (4)C72—C73—C74—O74178.5 (2)
C6—N7—C7a—C3a16.3 (3)C72—C73—C74—C751.5 (3)
C77—N7—C7a—C3a107.5 (2)O74—C74—C75—C76177.9 (2)
C6—N7—C7a—N1163.4 (2)C73—C74—C75—C762.1 (4)
C77—N7—C7a—N172.8 (3)C74—C75—C76—C710.6 (4)
C7a—N1—C11—C16145.6 (2)C72—C71—C76—C751.3 (4)
N2—N1—C11—C1634.8 (3)C77—C71—C76—C75175.0 (2)
C7a—N1—C11—C1236.7 (3)C73—C74—O74—C788.4 (3)
N2—N1—C11—C12142.89 (19)C75—C74—O74—C78171.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···N70.952.623.108 (3)113
(IV) 3-tert-butyl-1-phenyl-7-[4-(trifluoromethyl)benzyl]-6,7-dihydro- 1H,4H-pyrazolo[3,4-d][1,3]oxazine top
Crystal data top
C23H24F3N3OZ = 2
Mr = 415.45F(000) = 436
Triclinic, P1Dx = 1.379 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0277 (11) ÅCell parameters from 4601 reflections
b = 9.8597 (12) Åθ = 2.8–27.5°
c = 12.6835 (18) ŵ = 0.11 mm1
α = 85.531 (11)°T = 120 K
β = 74.180 (11)°Block, colourless
γ = 67.162 (9)°0.27 × 0.17 × 0.14 mm
V = 1000.6 (2) Å3
Data collection top
Bruker Nonius KappaCCD
diffractometer
4601 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode2336 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.099
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.8°
ϕ & ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1212
Tmin = 0.922, Tmax = 0.986l = 1616
24473 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) = 0.183H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0897P)2 + 0.1648P]
where P = (Fo2 + 2Fc2)/3
4601 reflections(Δ/σ)max = 0.001
274 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C23H24F3N3Oγ = 67.162 (9)°
Mr = 415.45V = 1000.6 (2) Å3
Triclinic, P1Z = 2
a = 9.0277 (11) ÅMo Kα radiation
b = 9.8597 (12) ŵ = 0.11 mm1
c = 12.6835 (18) ÅT = 120 K
α = 85.531 (11)°0.27 × 0.17 × 0.14 mm
β = 74.180 (11)°
Data collection top
Bruker Nonius KappaCCD
diffractometer
4601 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2336 reflections with I > 2σ(I)
Tmin = 0.922, Tmax = 0.986Rint = 0.099
24473 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.183H-atom parameters constrained
S = 1.04Δρmax = 0.33 e Å3
4601 reflectionsΔρmin = 0.37 e Å3
274 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.4886 (3)0.3492 (2)0.64616 (18)0.0226 (5)
N20.4261 (3)0.2466 (2)0.63566 (18)0.0238 (5)
C30.2804 (3)0.2856 (3)0.7110 (2)0.0232 (6)
C3a0.2496 (3)0.4115 (3)0.7717 (2)0.0228 (6)
C40.1138 (3)0.4986 (3)0.8648 (2)0.0305 (7)
H410.01470.55920.83890.037*
H420.08230.43160.92060.037*
O50.1680 (2)0.5917 (2)0.91230 (16)0.0307 (5)
C60.2435 (3)0.6668 (3)0.8290 (2)0.0283 (7)
H6A0.25860.74550.86340.034*
H6B0.16770.71420.78160.034*
N70.4048 (3)0.5707 (2)0.76085 (19)0.0246 (5)
C7a0.3833 (3)0.4483 (3)0.7286 (2)0.0226 (6)
C110.6426 (3)0.3405 (3)0.5741 (2)0.0231 (6)
C120.6744 (3)0.4666 (3)0.5468 (2)0.0257 (6)
H120.59220.55980.57540.031*
C130.8258 (3)0.4568 (3)0.4780 (2)0.0285 (7)
H130.84950.54300.46130.034*
C140.9425 (3)0.3229 (3)0.4335 (2)0.0300 (7)
H141.04650.31640.38560.036*
C150.9082 (4)0.1983 (3)0.4584 (2)0.0313 (7)
H150.98830.10580.42670.038*
C160.7587 (3)0.2060 (3)0.5289 (2)0.0279 (7)
H160.73590.11940.54620.033*
C310.1718 (3)0.1983 (3)0.7238 (2)0.0255 (6)
C320.2356 (4)0.0882 (3)0.6284 (3)0.0321 (7)
H32A0.22790.14120.56020.048*
H32B0.16790.02830.64050.048*
H32C0.35200.02410.62300.048*
C330.1712 (4)0.1175 (3)0.8312 (2)0.0301 (7)
H33A0.28610.05660.83260.045*
H33B0.10790.05460.83740.045*
H33C0.11940.18930.89280.045*
C340.0068 (3)0.3020 (3)0.7275 (2)0.0296 (7)
H34A0.05080.37100.79040.044*
H34B0.07630.24440.73460.044*
H34C0.00790.35700.65970.044*
C770.5422 (3)0.5334 (3)0.8124 (2)0.0247 (6)
H7710.64120.45350.76860.030*
H7720.51010.49640.88650.030*
C710.5868 (3)0.6627 (3)0.8219 (2)0.0233 (6)
C720.6432 (3)0.6755 (3)0.9100 (2)0.0290 (7)
H720.65140.60320.96460.035*
C730.6875 (3)0.7914 (3)0.9196 (2)0.0296 (7)
H730.72570.79910.98080.036*
C740.6766 (3)0.8967 (3)0.8407 (2)0.0249 (6)
C750.6195 (3)0.8858 (3)0.7531 (2)0.0273 (7)
H750.60990.95900.69920.033*
C760.5760 (3)0.7689 (3)0.7433 (2)0.0281 (7)
H760.53820.76130.68190.034*
C780.7275 (4)1.0211 (3)0.8486 (2)0.0307 (7)
F10.7478 (3)1.0370 (2)0.94488 (16)0.0558 (6)
F20.8712 (3)1.0032 (3)0.7764 (2)0.0760 (8)
F30.6198 (3)1.1491 (2)0.8290 (2)0.0623 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0216 (12)0.0219 (12)0.0267 (13)0.0109 (10)0.0053 (10)0.0027 (10)
N20.0245 (12)0.0245 (12)0.0262 (13)0.0125 (11)0.0081 (10)0.0008 (10)
C30.0242 (14)0.0269 (15)0.0215 (15)0.0115 (12)0.0091 (12)0.0050 (12)
C3a0.0213 (14)0.0247 (15)0.0246 (15)0.0117 (12)0.0052 (12)0.0009 (12)
C40.0277 (15)0.0303 (16)0.0339 (17)0.0150 (13)0.0008 (13)0.0078 (13)
O50.0303 (11)0.0329 (11)0.0310 (12)0.0180 (9)0.0002 (9)0.0083 (9)
C60.0268 (15)0.0212 (15)0.0351 (17)0.0085 (13)0.0046 (13)0.0049 (13)
N70.0215 (12)0.0221 (12)0.0317 (14)0.0096 (10)0.0065 (10)0.0031 (10)
C7a0.0233 (14)0.0219 (15)0.0248 (15)0.0103 (12)0.0077 (12)0.0013 (12)
C110.0210 (14)0.0294 (16)0.0203 (14)0.0108 (12)0.0061 (11)0.0005 (12)
C120.0264 (15)0.0258 (16)0.0261 (15)0.0096 (13)0.0103 (12)0.0036 (12)
C130.0321 (16)0.0339 (17)0.0263 (16)0.0183 (14)0.0118 (13)0.0077 (13)
C140.0242 (15)0.0397 (18)0.0286 (17)0.0150 (14)0.0074 (13)0.0028 (14)
C150.0260 (15)0.0355 (17)0.0304 (17)0.0094 (14)0.0067 (13)0.0025 (13)
C160.0272 (15)0.0289 (17)0.0289 (16)0.0122 (13)0.0074 (13)0.0007 (13)
C310.0284 (15)0.0268 (16)0.0269 (16)0.0158 (13)0.0084 (12)0.0012 (12)
C320.0324 (16)0.0327 (17)0.0351 (18)0.0160 (14)0.0076 (13)0.0063 (14)
C330.0340 (16)0.0312 (16)0.0318 (17)0.0183 (14)0.0121 (13)0.0060 (13)
C340.0280 (15)0.0310 (17)0.0340 (17)0.0153 (14)0.0096 (13)0.0034 (13)
C770.0262 (15)0.0234 (15)0.0283 (16)0.0118 (12)0.0101 (12)0.0024 (12)
C710.0228 (14)0.0206 (15)0.0278 (16)0.0092 (12)0.0074 (12)0.0011 (12)
C720.0353 (16)0.0285 (16)0.0288 (16)0.0164 (14)0.0128 (13)0.0072 (13)
C730.0324 (16)0.0311 (17)0.0320 (17)0.0167 (14)0.0130 (13)0.0034 (13)
C740.0241 (14)0.0223 (15)0.0293 (16)0.0103 (12)0.0056 (12)0.0016 (12)
C750.0298 (15)0.0241 (15)0.0318 (17)0.0125 (13)0.0111 (13)0.0032 (13)
C760.0307 (16)0.0298 (16)0.0292 (17)0.0155 (13)0.0108 (13)0.0013 (13)
C780.0322 (16)0.0311 (17)0.0327 (17)0.0149 (14)0.0105 (14)0.0018 (14)
F10.0983 (17)0.0503 (12)0.0516 (13)0.0498 (12)0.0422 (12)0.0113 (10)
F20.0706 (15)0.0792 (16)0.0866 (17)0.0622 (14)0.0262 (13)0.0350 (13)
F30.0826 (16)0.0310 (11)0.0995 (18)0.0281 (11)0.0592 (14)0.0160 (11)
Geometric parameters (Å, º) top
N1—C7a1.359 (3)C31—C331.523 (4)
N1—N21.366 (3)C31—C341.528 (4)
N1—C111.415 (3)C32—H32A0.9800
N2—C31.330 (3)C32—H32B0.9800
C3—C3a1.405 (4)C32—H32C0.9800
C3—C311.509 (4)C33—H33A0.9800
C3a—C7a1.356 (4)C33—H33B0.9800
C3a—C41.478 (4)C33—H33C0.9800
C4—O51.429 (3)C34—H34A0.9800
C4—H410.9900C34—H34B0.9800
C4—H420.9900C34—H34C0.9800
O5—C61.416 (3)C77—C711.500 (4)
C6—N71.461 (3)C77—H7710.9900
C6—H6A0.9900C77—H7720.9900
C6—H6B0.9900C71—C721.381 (4)
N7—C7a1.401 (3)C71—C761.382 (4)
N7—C771.467 (3)C72—C731.372 (4)
C11—C161.378 (4)C72—H720.9500
C11—C121.380 (4)C73—C741.379 (4)
C12—C131.379 (4)C73—H730.9500
C12—H120.9500C74—C751.373 (4)
C13—C141.373 (4)C74—C781.486 (4)
C13—H130.9500C75—C761.378 (4)
C14—C151.374 (4)C75—H750.9500
C14—H140.9500C76—H760.9500
C15—C161.378 (4)C78—F11.313 (3)
C15—H150.9500C78—F31.316 (3)
C16—H160.9500C78—F21.324 (3)
C31—C321.521 (4)
C7a—N1—N2110.5 (2)C32—C31—C34108.8 (2)
C7a—N1—C11130.3 (2)C33—C31—C34108.6 (2)
N2—N1—C11119.1 (2)C31—C32—H32A109.5
C3—N2—N1105.3 (2)C31—C32—H32B109.5
N2—C3—C3a111.1 (2)H32A—C32—H32B109.5
N2—C3—C31121.0 (2)C31—C32—H32C109.5
C3a—C3—C31127.9 (2)H32A—C32—H32C109.5
C7a—C3a—C3105.2 (2)H32B—C32—H32C109.5
C7a—C3a—C4120.5 (2)C31—C33—H33A109.5
C3—C3a—C4134.3 (2)C31—C33—H33B109.5
O5—C4—C3a109.6 (2)H33A—C33—H33B109.5
O5—C4—H41109.8C31—C33—H33C109.5
C3a—C4—H41109.8H33A—C33—H33C109.5
O5—C4—H42109.8H33B—C33—H33C109.5
C3a—C4—H42109.8C31—C34—H34A109.5
H41—C4—H42108.2C31—C34—H34B109.5
C6—O5—C4109.9 (2)H34A—C34—H34B109.5
O5—C6—N7113.4 (2)C31—C34—H34C109.5
O5—C6—H6A108.9H34A—C34—H34C109.5
N7—C6—H6A108.9H34B—C34—H34C109.5
O5—C6—H6B108.9N7—C77—C71112.4 (2)
N7—C6—H6B108.9N7—C77—H771109.1
H6A—C6—H6B107.7C71—C77—H771109.1
C7a—N7—C6107.0 (2)N7—C77—H772109.1
C7a—N7—C77114.1 (2)C71—C77—H772109.1
C6—N7—C77113.9 (2)H771—C77—H772107.9
C3a—C7a—N1107.9 (2)C72—C71—C76118.7 (2)
C3a—C7a—N7125.6 (2)C72—C71—C77119.6 (2)
N1—C7a—N7126.4 (2)C76—C71—C77121.7 (2)
C16—C11—C12120.2 (2)C73—C72—C71120.8 (3)
C16—C11—N1119.6 (2)C73—C72—H72119.6
C12—C11—N1120.2 (2)C71—C72—H72119.6
C13—C12—C11119.7 (3)C72—C73—C74120.1 (3)
C13—C12—H12120.1C72—C73—H73119.9
C11—C12—H12120.1C74—C73—H73119.9
C14—C13—C12120.3 (3)C75—C74—C73119.7 (2)
C14—C13—H13119.9C75—C74—C78119.5 (3)
C12—C13—H13119.9C73—C74—C78120.8 (3)
C13—C14—C15119.7 (3)C74—C75—C76120.1 (3)
C13—C14—H14120.2C74—C75—H75120.0
C15—C14—H14120.2C76—C75—H75120.0
C14—C15—C16120.7 (3)C75—C76—C71120.7 (3)
C14—C15—H15119.7C75—C76—H76119.7
C16—C15—H15119.7C71—C76—H76119.7
C11—C16—C15119.4 (3)F1—C78—F3105.8 (2)
C11—C16—H16120.3F1—C78—F2106.1 (2)
C15—C16—H16120.3F3—C78—F2106.2 (3)
C3—C31—C32110.7 (2)F1—C78—C74113.9 (2)
C3—C31—C33109.1 (2)F3—C78—C74113.1 (2)
C32—C31—C33109.9 (2)F2—C78—C74111.0 (2)
C3—C31—C34109.9 (2)
C7a—N1—N2—C31.1 (3)C11—C12—C13—C142.4 (4)
C11—N1—N2—C3178.1 (2)C12—C13—C14—C150.4 (4)
N1—N2—C3—C3a1.1 (3)C13—C14—C15—C161.0 (4)
N1—N2—C3—C31179.3 (2)C12—C11—C16—C151.6 (4)
N2—C3—C3a—C7a0.7 (3)N1—C11—C16—C15179.7 (3)
C31—C3—C3a—C7a179.8 (3)C14—C15—C16—C110.4 (4)
N2—C3—C3a—C4178.1 (3)N2—C3—C31—C3211.1 (4)
C31—C3—C3a—C41.4 (5)C3a—C3—C31—C32169.4 (3)
C7a—C3a—C4—O514.1 (4)N2—C3—C31—C33109.9 (3)
C3—C3a—C4—O5164.6 (3)C3a—C3—C31—C3369.6 (3)
C3a—C4—O5—C648.0 (3)N2—C3—C31—C34131.3 (3)
C4—O5—C6—N770.4 (3)C3a—C3—C31—C3449.3 (4)
O5—C6—N7—C7a49.1 (3)C7a—N7—C77—C71166.7 (2)
O5—C6—N7—C7778.1 (3)C6—N7—C77—C7170.0 (3)
C3—C3a—C7a—N10.0 (3)N7—C77—C71—C72147.0 (3)
C4—C3a—C7a—N1179.0 (2)N7—C77—C71—C7634.2 (4)
C3—C3a—C7a—N7177.6 (3)C76—C71—C72—C730.1 (4)
C4—C3a—C7a—N73.4 (4)C77—C71—C72—C73178.9 (3)
N2—N1—C7a—C3a0.7 (3)C71—C72—C73—C740.2 (4)
C11—N1—C7a—C3a178.4 (3)C72—C73—C74—C750.7 (4)
N2—N1—C7a—N7178.3 (2)C72—C73—C74—C78178.7 (3)
C11—N1—C7a—N70.9 (4)C73—C74—C75—C761.1 (4)
C6—N7—C7a—C3a13.0 (4)C78—C74—C75—C76178.3 (3)
C77—N7—C7a—C3a114.0 (3)C74—C75—C76—C711.0 (4)
C6—N7—C7a—N1164.1 (3)C72—C71—C76—C750.5 (4)
C77—N7—C7a—N168.9 (3)C77—C71—C76—C75179.2 (3)
C7a—N1—C11—C16153.5 (3)C75—C74—C78—F1167.1 (3)
N2—N1—C11—C1627.4 (4)C73—C74—C78—F113.5 (4)
C7a—N1—C11—C1228.5 (4)C75—C74—C78—F346.2 (4)
N2—N1—C11—C12150.6 (2)C73—C74—C78—F3134.5 (3)
C16—C11—C12—C133.0 (4)C75—C74—C78—F273.1 (3)
N1—C11—C12—C13179.0 (2)C73—C74—C78—F2106.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···N70.952.483.040 (4)118
(V) 3-tert-butyl-7-(4-nitrobenzyl)-1-phenyl-6,7-dihydro- 1H,4H-pyrazolo[3,4-d][1,3]oxazine top
Crystal data top
C22H24N4O3F(000) = 832
Mr = 392.45Dx = 1.350 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4417 reflections
a = 19.164 (2) Åθ = 3.0–27.5°
b = 8.7781 (7) ŵ = 0.09 mm1
c = 11.7188 (12) ÅT = 120 K
β = 101.717 (10)°Block, colourless
V = 1930.3 (3) Å30.33 × 0.22 × 0.18 mm
Z = 4
Data collection top
Bruker Nonius KappaCCD
diffractometer
4417 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode2821 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
ϕ & ω scansh = 2422
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1111
Tmin = 0.917, Tmax = 0.984l = 1515
27769 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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0417P)2 + 0.8028P]
where P = (Fo2 + 2Fc2)/3
4417 reflections(Δ/σ)max = 0.001
265 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C22H24N4O3V = 1930.3 (3) Å3
Mr = 392.45Z = 4
Monoclinic, P21/cMo Kα radiation
a = 19.164 (2) ŵ = 0.09 mm1
b = 8.7781 (7) ÅT = 120 K
c = 11.7188 (12) Å0.33 × 0.22 × 0.18 mm
β = 101.717 (10)°
Data collection top
Bruker Nonius KappaCCD
diffractometer
4417 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2821 reflections with I > 2σ(I)
Tmin = 0.917, Tmax = 0.984Rint = 0.066
27769 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.09Δρmax = 0.24 e Å3
4417 reflectionsΔρmin = 0.29 e Å3
265 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.17204 (8)0.55410 (16)0.23144 (12)0.0185 (3)
N20.13203 (8)0.44005 (16)0.17103 (12)0.0199 (3)
C30.17817 (10)0.33411 (19)0.15485 (15)0.0194 (4)
C3a0.24844 (10)0.3789 (2)0.20425 (15)0.0203 (4)
C40.31945 (10)0.3060 (2)0.21820 (18)0.0260 (4)
H4A0.32390.22390.27720.031*
H4B0.32490.26000.14330.031*
O50.37385 (7)0.41726 (14)0.25414 (12)0.0289 (3)
C60.35922 (11)0.5099 (2)0.34553 (17)0.0273 (4)
H6A0.40170.57280.37670.033*
H6B0.35030.44360.40940.033*
N70.29830 (8)0.60942 (17)0.30890 (13)0.0222 (3)
C7a0.24188 (10)0.5184 (2)0.25078 (15)0.0199 (4)
C110.13728 (10)0.67668 (19)0.27440 (15)0.0203 (4)
C120.16550 (11)0.7367 (2)0.38298 (16)0.0240 (4)
H120.20850.69720.42810.029*
C130.13052 (11)0.8542 (2)0.42479 (17)0.0294 (5)
H130.15030.89840.49820.035*
C140.06747 (11)0.9080 (2)0.36157 (18)0.0317 (5)
H140.04320.98800.39190.038*
C150.03906 (11)0.8468 (2)0.25416 (18)0.0296 (5)
H150.00490.88400.21070.035*
C160.07437 (10)0.7313 (2)0.20947 (17)0.0247 (4)
H160.05540.69000.13470.030*
C310.15406 (10)0.1929 (2)0.08541 (16)0.0228 (4)
C320.07403 (11)0.1749 (2)0.06623 (18)0.0309 (5)
H32A0.05990.16400.14160.046*
H32B0.05940.08400.01880.046*
H32C0.05090.26500.02580.046*
C330.17561 (12)0.2072 (2)0.03238 (17)0.0323 (5)
H33A0.15260.29690.07350.049*
H33B0.16060.11570.07890.049*
H33C0.22750.21810.02050.049*
C340.18954 (11)0.0537 (2)0.14942 (17)0.0278 (4)
H34A0.24120.06040.15590.042*
H34B0.17160.03850.10610.042*
H34C0.17870.04930.22750.042*
C770.31303 (11)0.7374 (2)0.23620 (16)0.0255 (4)
H77A0.26730.78190.19550.031*
H77B0.33820.69850.17620.031*
C710.35735 (10)0.8601 (2)0.30497 (16)0.0234 (4)
C720.41127 (11)0.9289 (2)0.26129 (17)0.0282 (4)
H720.42180.89380.19000.034*
C730.44993 (10)1.0475 (2)0.31949 (17)0.0278 (4)
H730.48701.09460.28930.033*
C740.43360 (10)1.0959 (2)0.42199 (16)0.0236 (4)
C750.38145 (11)1.0289 (2)0.46880 (17)0.0282 (5)
H750.37171.06320.54090.034*
C760.34339 (11)0.9108 (2)0.40930 (16)0.0281 (4)
H760.30690.86320.44060.034*
N740.47224 (9)1.22504 (18)0.48294 (14)0.0287 (4)
O410.52493 (8)1.27042 (17)0.45079 (13)0.0397 (4)
O420.44975 (8)1.28234 (16)0.56310 (13)0.0382 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0223 (8)0.0153 (7)0.0175 (7)0.0007 (6)0.0032 (6)0.0025 (6)
N20.0269 (9)0.0158 (7)0.0168 (7)0.0011 (7)0.0037 (6)0.0007 (6)
C30.0277 (10)0.0152 (8)0.0157 (8)0.0012 (8)0.0053 (7)0.0016 (7)
C3a0.0256 (10)0.0161 (8)0.0193 (9)0.0016 (8)0.0050 (7)0.0020 (7)
C40.0255 (10)0.0183 (9)0.0343 (11)0.0002 (8)0.0061 (8)0.0012 (8)
O50.0247 (7)0.0232 (7)0.0395 (8)0.0000 (6)0.0080 (6)0.0060 (6)
C60.0282 (11)0.0233 (10)0.0286 (10)0.0022 (8)0.0014 (8)0.0017 (8)
N70.0250 (9)0.0182 (8)0.0223 (8)0.0000 (7)0.0021 (6)0.0012 (6)
C7a0.0245 (10)0.0175 (9)0.0176 (8)0.0005 (8)0.0042 (7)0.0009 (7)
C110.0266 (10)0.0133 (8)0.0227 (9)0.0005 (7)0.0094 (8)0.0008 (7)
C120.0311 (11)0.0206 (9)0.0218 (9)0.0012 (8)0.0086 (8)0.0004 (8)
C130.0397 (12)0.0241 (10)0.0282 (10)0.0038 (9)0.0157 (9)0.0063 (9)
C140.0381 (12)0.0191 (10)0.0443 (12)0.0008 (9)0.0233 (10)0.0045 (9)
C150.0271 (11)0.0215 (10)0.0425 (12)0.0040 (8)0.0125 (9)0.0012 (9)
C160.0269 (10)0.0216 (9)0.0269 (10)0.0000 (8)0.0084 (8)0.0006 (8)
C310.0294 (11)0.0181 (9)0.0209 (9)0.0003 (8)0.0048 (8)0.0013 (8)
C320.0316 (11)0.0232 (10)0.0359 (11)0.0025 (9)0.0024 (9)0.0076 (9)
C330.0513 (13)0.0244 (10)0.0232 (10)0.0016 (10)0.0121 (9)0.0069 (8)
C340.0338 (11)0.0168 (9)0.0318 (10)0.0005 (8)0.0041 (9)0.0001 (8)
C770.0309 (11)0.0206 (9)0.0248 (10)0.0021 (8)0.0053 (8)0.0011 (8)
C710.0270 (10)0.0187 (9)0.0240 (9)0.0015 (8)0.0037 (8)0.0019 (8)
C720.0310 (11)0.0288 (10)0.0260 (10)0.0004 (9)0.0084 (9)0.0022 (9)
C730.0245 (10)0.0279 (10)0.0320 (11)0.0029 (8)0.0079 (8)0.0016 (9)
C740.0241 (10)0.0182 (9)0.0267 (10)0.0013 (8)0.0010 (8)0.0000 (8)
C750.0359 (12)0.0249 (10)0.0250 (10)0.0025 (9)0.0089 (9)0.0034 (8)
C760.0336 (11)0.0263 (10)0.0272 (10)0.0074 (9)0.0128 (9)0.0014 (9)
N740.0300 (10)0.0239 (8)0.0302 (9)0.0032 (7)0.0015 (8)0.0047 (8)
O410.0374 (9)0.0395 (9)0.0419 (9)0.0142 (7)0.0075 (7)0.0012 (7)
O420.0473 (9)0.0304 (8)0.0373 (8)0.0077 (7)0.0095 (7)0.0109 (7)
Geometric parameters (Å, º) top
N1—C7a1.348 (2)C31—C321.512 (3)
N1—N21.368 (2)C31—C341.521 (3)
N1—C111.411 (2)C31—C331.524 (3)
N2—C31.323 (2)C32—H32A0.9800
C3—C3a1.409 (3)C32—H32B0.9800
C3—C311.503 (2)C32—H32C0.9800
C3a—C7a1.357 (2)C33—H33A0.9800
C3a—C41.483 (3)C33—H33B0.9800
C4—O51.428 (2)C33—H33C0.9800
C4—H4A0.9900C34—H34A0.9800
C4—H4B0.9900C34—H34B0.9800
O5—C61.417 (2)C34—H34C0.9800
C6—N71.451 (2)C77—C711.501 (3)
C6—H6A0.9900C77—H77A0.9900
C6—H6B0.9900C77—H77B0.9900
N7—C7a1.404 (2)C71—C761.377 (3)
N7—C771.472 (2)C71—C721.382 (3)
C11—C161.375 (3)C72—C731.376 (3)
C11—C121.382 (3)C72—H720.9500
C12—C131.374 (3)C73—C741.369 (3)
C12—H120.9500C73—H730.9500
C13—C141.367 (3)C74—C751.367 (3)
C13—H130.9500C74—N741.459 (2)
C14—C151.375 (3)C75—C761.374 (3)
C14—H140.9500C75—H750.9500
C15—C161.380 (3)C76—H760.9500
C15—H150.9500N74—O411.214 (2)
C16—H160.9500N74—O421.219 (2)
C7a—N1—N2110.50 (14)C32—C31—C34109.12 (16)
C7a—N1—C11129.91 (15)C3—C31—C33108.22 (15)
N2—N1—C11119.14 (14)C32—C31—C33109.09 (16)
C3—N2—N1105.53 (14)C34—C31—C33109.66 (16)
N2—C3—C3a110.82 (15)C31—C32—H32A109.5
N2—C3—C31121.07 (16)C31—C32—H32B109.5
C3a—C3—C31128.00 (16)H32A—C32—H32B109.5
C7a—C3a—C3104.97 (16)C31—C32—H32C109.5
C7a—C3a—C4120.24 (17)H32A—C32—H32C109.5
C3—C3a—C4134.71 (16)H32B—C32—H32C109.5
O5—C4—C3a109.60 (14)C31—C33—H33A109.5
O5—C4—H4A109.7C31—C33—H33B109.5
C3a—C4—H4A109.7H33A—C33—H33B109.5
O5—C4—H4B109.8C31—C33—H33C109.5
C3a—C4—H4B109.7H33A—C33—H33C109.5
H4A—C4—H4B108.2H33B—C33—H33C109.5
C6—O5—C4111.76 (15)C31—C34—H34A109.5
O5—C6—N7113.11 (15)C31—C34—H34B109.5
O5—C6—H6A109.0H34A—C34—H34B109.5
N7—C6—H6A109.0C31—C34—H34C109.5
O5—C6—H6B109.0H34A—C34—H34C109.5
N7—C6—H6B109.0H34B—C34—H34C109.5
H6A—C6—H6B107.8N7—C77—C71113.03 (15)
C7a—N7—C6107.16 (14)N7—C77—H77A109.0
C7a—N7—C77111.89 (14)C71—C77—H77A109.0
C6—N7—C77113.17 (15)N7—C77—H77B109.0
N1—C7a—C3a108.17 (16)C71—C77—H77B109.0
N1—C7a—N7126.15 (16)H77A—C77—H77B107.8
C3a—C7a—N7125.68 (17)C76—C71—C72118.85 (17)
C16—C11—C12120.79 (17)C76—C71—C77121.16 (17)
C16—C11—N1119.54 (16)C72—C71—C77119.93 (17)
C12—C11—N1119.62 (16)C73—C72—C71121.00 (18)
C13—C12—C11119.11 (18)C73—C72—H72119.5
C13—C12—H12120.4C71—C72—H72119.5
C11—C12—H12120.4C74—C73—C72118.29 (18)
C14—C13—C12120.53 (19)C74—C73—H73120.9
C14—C13—H13119.7C72—C73—H73120.9
C12—C13—H13119.7C75—C74—C73122.30 (17)
C13—C14—C15120.19 (18)C75—C74—N74118.54 (17)
C13—C14—H14119.9C73—C74—N74119.15 (17)
C15—C14—H14119.9C74—C75—C76118.51 (18)
C14—C15—C16120.08 (19)C74—C75—H75120.7
C14—C15—H15120.0C76—C75—H75120.7
C16—C15—H15120.0C75—C76—C71121.03 (18)
C11—C16—C15119.26 (18)C75—C76—H76119.5
C11—C16—H16120.4C71—C76—H76119.5
C15—C16—H16120.4O41—N74—O42123.38 (17)
C3—C31—C32110.96 (16)O41—N74—C74118.32 (17)
C3—C31—C34109.77 (14)O42—N74—C74118.30 (17)
C7a—N1—N2—C30.60 (18)N1—C11—C12—C13178.85 (17)
C11—N1—N2—C3172.49 (15)C11—C12—C13—C142.0 (3)
N1—N2—C3—C3a0.23 (19)C12—C13—C14—C151.2 (3)
N1—N2—C3—C31176.79 (15)C13—C14—C15—C160.4 (3)
N2—C3—C3a—C7a0.2 (2)C12—C11—C16—C150.4 (3)
C31—C3—C3a—C7a176.05 (17)N1—C11—C16—C15177.23 (17)
N2—C3—C3a—C4176.27 (19)C14—C15—C16—C111.2 (3)
C31—C3—C3a—C47.5 (3)N2—C3—C31—C3213.8 (2)
C7a—C3a—C4—O515.8 (2)C3a—C3—C31—C32170.30 (17)
C3—C3a—C4—O5168.15 (18)N2—C3—C31—C34134.47 (18)
C3a—C4—O5—C646.1 (2)C3a—C3—C31—C3449.6 (2)
C4—O5—C6—N768.28 (19)N2—C3—C31—C33105.9 (2)
O5—C6—N7—C7a50.6 (2)C3a—C3—C31—C3370.0 (2)
O5—C6—N7—C7773.20 (19)C7a—N7—C77—C71163.49 (15)
N2—N1—C7a—C3a0.75 (19)C6—N7—C77—C7175.3 (2)
C11—N1—C7a—C3a171.38 (17)N7—C77—C71—C7644.2 (2)
N2—N1—C7a—N7179.23 (16)N7—C77—C71—C72138.65 (18)
C11—N1—C7a—N78.6 (3)C76—C71—C72—C731.0 (3)
C3—C3a—C7a—N10.57 (19)C77—C71—C72—C73176.26 (17)
C4—C3a—C7a—N1176.53 (16)C71—C72—C73—C740.1 (3)
C3—C3a—C7a—N7179.41 (17)C72—C73—C74—C751.2 (3)
C4—C3a—C7a—N73.5 (3)C72—C73—C74—N74177.83 (17)
C6—N7—C7a—N1160.40 (17)C73—C74—C75—C761.3 (3)
C77—N7—C7a—N175.0 (2)N74—C74—C75—C76177.76 (16)
C6—N7—C7a—C3a19.6 (2)C74—C75—C76—C710.2 (3)
C77—N7—C7a—C3a105.0 (2)C72—C71—C76—C750.9 (3)
C7a—N1—C11—C16151.56 (18)C77—C71—C76—C75176.30 (18)
N2—N1—C11—C1636.9 (2)C75—C74—N74—O41169.66 (18)
C7a—N1—C11—C1230.8 (3)C73—C74—N74—O4111.3 (3)
N2—N1—C11—C12140.79 (17)C75—C74—N74—O4210.7 (3)
C16—C11—C12—C131.2 (3)C73—C74—N74—O42168.33 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···N70.952.553.062 (3)114
C13—H13···N2i0.952.553.399 (2)148
C72—H72···O41ii0.952.373.293 (3)163
C75—H75···O5i0.952.503.409 (2)161
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y1/2, z+1/2.
(VI) 3-tert-butyl-7-(2,3-dimethoxybenzyl)-1-phenyl-6,7-dihydro- 1H,4H-pyrazolo[3,4-d][1,3]oxazine top
Crystal data top
C24H29N3O3F(000) = 436
Mr = 407.50Dx = 1.270 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2560 reflections
a = 8.8268 (10) Åθ = 2.9–27.5°
b = 11.6521 (10) ŵ = 0.09 mm1
c = 10.3831 (7) ÅT = 120 K
β = 93.747 (9)°Block, colourless
V = 1065.63 (17) Å30.25 × 0.20 × 0.19 mm
Z = 2
Data collection top
Bruker Nonius KappaCCD
diffractometer
2560 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode2132 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.9°
ϕ & ω scansh = 1011
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1515
Tmin = 0.972, Tmax = 0.984l = 1313
17934 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0582P)2 + 0.2363P]
where P = (Fo2 + 2Fc2)/3
2560 reflections(Δ/σ)max = 0.001
276 parametersΔρmax = 0.32 e Å3
1 restraintΔρmin = 0.27 e Å3
Crystal data top
C24H29N3O3V = 1065.63 (17) Å3
Mr = 407.50Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.8268 (10) ŵ = 0.09 mm1
b = 11.6521 (10) ÅT = 120 K
c = 10.3831 (7) Å0.25 × 0.20 × 0.19 mm
β = 93.747 (9)°
Data collection top
Bruker Nonius KappaCCD
diffractometer
2560 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2132 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.984Rint = 0.049
17934 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.112H-atom parameters constrained
S = 1.13Δρmax = 0.32 e Å3
2560 reflectionsΔρmin = 0.27 e Å3
276 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3022 (2)0.4490 (2)0.4889 (2)0.0157 (4)
N20.1865 (2)0.3913 (2)0.4230 (2)0.0174 (5)
C30.0949 (3)0.3576 (2)0.5109 (3)0.0174 (5)
C3a0.1515 (3)0.3914 (2)0.6361 (2)0.0179 (5)
C40.1027 (3)0.3716 (3)0.7690 (3)0.0240 (6)
H410.01640.42260.78560.029*
H420.06940.29110.77820.029*
O50.2274 (2)0.3952 (2)0.85908 (18)0.0269 (5)
C60.2934 (3)0.5015 (3)0.8311 (3)0.0236 (6)
H6A0.36370.52430.90480.028*
H6B0.21250.56020.82150.028*
N70.3762 (2)0.5000 (2)0.7145 (2)0.0182 (5)
C7a0.2809 (3)0.4492 (2)0.6175 (2)0.0158 (5)
C110.4128 (3)0.5039 (2)0.4180 (2)0.0170 (5)
C120.4874 (3)0.6006 (2)0.4672 (3)0.0212 (6)
H120.46590.62960.54950.025*
C130.5929 (3)0.6545 (3)0.3959 (3)0.0283 (7)
H130.64650.71940.43030.034*
C140.6210 (4)0.6144 (3)0.2752 (3)0.0330 (7)
H140.69170.65290.22530.040*
C150.5466 (4)0.5187 (3)0.2270 (3)0.0312 (7)
H150.56660.49110.14370.037*
C160.4432 (3)0.4622 (3)0.2981 (3)0.0247 (6)
H160.39330.39520.26480.030*
C310.0462 (3)0.2893 (3)0.4749 (3)0.0235 (6)
C320.0813 (4)0.2882 (4)0.3301 (4)0.0504 (11)
H32A0.00170.25060.28820.076*
H32B0.09240.36730.29850.076*
H32C0.17610.24620.30990.076*
C330.0237 (5)0.1683 (4)0.5229 (5)0.0609 (13)
H33A0.06230.13360.48220.091*
H33B0.11570.12350.50110.091*
H33C0.00290.16910.61680.091*
C340.1807 (4)0.3434 (4)0.5375 (4)0.0484 (10)
H34A0.27370.30150.51050.073*
H34B0.19100.42370.51050.073*
H34C0.16370.33950.63160.073*
C770.5243 (3)0.4430 (3)0.7320 (3)0.0214 (6)
H7710.56700.43310.64680.026*
H7720.51080.36590.76950.026*
C710.6336 (3)0.5108 (3)0.8188 (2)0.0212 (6)
C720.7422 (3)0.4524 (3)0.8952 (3)0.0212 (6)
C730.8490 (3)0.5121 (3)0.9750 (2)0.0228 (6)
C740.8468 (3)0.6304 (3)0.9762 (3)0.0267 (7)
H740.92040.67181.02840.032*
C750.7370 (4)0.6881 (3)0.9010 (3)0.0322 (7)
H750.73390.76950.90350.039*
C760.6325 (4)0.6298 (3)0.8230 (3)0.0294 (7)
H760.55860.67120.77110.035*
O720.7503 (2)0.33556 (17)0.8866 (2)0.0245 (5)
O730.9489 (2)0.4453 (2)1.04560 (19)0.0309 (5)
C7210.6800 (5)0.2777 (3)0.9867 (3)0.0417 (9)
H72A0.73650.29291.06930.063*
H72B0.67950.19490.96960.063*
H72C0.57540.30500.99040.063*
C7311.0616 (4)0.5035 (4)1.1260 (3)0.0373 (8)
H73A1.12340.55161.07250.056*
H73B1.12660.44701.17260.056*
H73C1.01200.55181.18810.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0135 (10)0.0169 (11)0.0166 (10)0.0016 (9)0.0008 (8)0.0008 (9)
N20.0145 (10)0.0183 (11)0.0190 (11)0.0019 (9)0.0010 (8)0.0031 (9)
C30.0158 (12)0.0150 (13)0.0213 (13)0.0010 (10)0.0004 (10)0.0001 (10)
C3a0.0170 (12)0.0158 (13)0.0209 (12)0.0017 (11)0.0027 (10)0.0008 (11)
C40.0253 (13)0.0272 (17)0.0200 (13)0.0067 (12)0.0045 (11)0.0003 (11)
O50.0301 (10)0.0327 (12)0.0180 (9)0.0027 (10)0.0019 (8)0.0029 (9)
C60.0271 (14)0.0257 (15)0.0177 (13)0.0002 (13)0.0008 (11)0.0038 (12)
N70.0166 (10)0.0203 (12)0.0175 (10)0.0014 (10)0.0012 (8)0.0033 (10)
C7a0.0167 (12)0.0137 (12)0.0169 (12)0.0010 (11)0.0001 (9)0.0006 (10)
C110.0156 (11)0.0175 (13)0.0177 (12)0.0005 (11)0.0001 (9)0.0021 (11)
C120.0237 (13)0.0172 (14)0.0229 (14)0.0016 (11)0.0025 (11)0.0019 (11)
C130.0239 (14)0.0260 (16)0.0353 (17)0.0055 (12)0.0032 (12)0.0038 (13)
C140.0288 (16)0.0359 (18)0.0353 (17)0.0063 (14)0.0106 (13)0.0080 (14)
C150.0317 (16)0.0391 (19)0.0239 (14)0.0013 (15)0.0104 (12)0.0044 (14)
C160.0205 (14)0.0300 (17)0.0238 (14)0.0027 (12)0.0030 (11)0.0040 (12)
C310.0187 (13)0.0232 (16)0.0288 (15)0.0074 (12)0.0021 (11)0.0039 (12)
C320.042 (2)0.071 (3)0.0373 (19)0.031 (2)0.0003 (16)0.0133 (19)
C330.059 (3)0.032 (2)0.087 (3)0.023 (2)0.028 (2)0.009 (2)
C340.0220 (16)0.059 (3)0.064 (2)0.0087 (16)0.0047 (16)0.023 (2)
C770.0191 (13)0.0219 (14)0.0222 (13)0.0007 (12)0.0061 (10)0.0006 (12)
C710.0208 (13)0.0232 (15)0.0192 (13)0.0039 (12)0.0015 (10)0.0006 (12)
C720.0199 (13)0.0262 (15)0.0177 (13)0.0001 (12)0.0021 (10)0.0014 (12)
C730.0193 (13)0.0339 (17)0.0151 (12)0.0006 (13)0.0008 (10)0.0001 (12)
C740.0263 (15)0.0326 (18)0.0206 (14)0.0117 (13)0.0037 (12)0.0013 (12)
C750.0445 (19)0.0215 (16)0.0296 (16)0.0109 (14)0.0047 (14)0.0025 (13)
C760.0346 (17)0.0236 (17)0.0284 (16)0.0031 (13)0.0106 (13)0.0017 (12)
O720.0250 (10)0.0219 (11)0.0263 (10)0.0042 (8)0.0013 (8)0.0027 (8)
O730.0230 (10)0.0419 (13)0.0261 (10)0.0027 (10)0.0107 (8)0.0065 (10)
C7210.064 (2)0.0262 (18)0.0343 (18)0.0009 (17)0.0028 (17)0.0078 (14)
C7310.0262 (15)0.057 (2)0.0270 (15)0.0041 (17)0.0093 (12)0.0048 (17)
Geometric parameters (Å, º) top
N1—C7a1.360 (3)C32—H32A0.9800
N1—N21.368 (3)C32—H32B0.9800
N1—C111.414 (3)C32—H32C0.9800
N2—C31.318 (3)C33—H33A0.9800
C3—C3a1.417 (4)C33—H33B0.9800
C3—C311.504 (4)C33—H33C0.9800
C3a—C7a1.351 (4)C34—H34A0.9800
C3a—C41.490 (4)C34—H34B0.9800
C4—O51.424 (3)C34—H34C0.9800
C4—H410.9900C77—C711.501 (4)
C4—H420.9900C77—H7710.9900
O5—C61.407 (4)C77—H7720.9900
C6—N71.454 (3)C71—C721.383 (4)
C6—H6A0.9900C71—C761.388 (5)
C6—H6B0.9900C72—O721.367 (4)
N7—C7a1.401 (3)C72—C731.398 (4)
N7—C771.466 (4)C73—O731.355 (4)
C11—C161.379 (4)C73—C741.378 (5)
C11—C121.385 (4)C74—C751.380 (5)
C12—C131.378 (4)C74—H740.9500
C12—H120.9500C75—C761.367 (4)
C13—C141.375 (5)C75—H750.9500
C13—H130.9500C76—H760.9500
C14—C151.371 (5)O72—C7211.415 (4)
C14—H140.9500O73—C7311.427 (4)
C15—C161.378 (4)C721—H72A0.9800
C15—H150.9500C721—H72B0.9800
C16—H160.9500C721—H72C0.9800
C31—C331.504 (5)C731—H73A0.9800
C31—C321.515 (5)C731—H73B0.9800
C31—C341.526 (5)C731—H73C0.9800
C7a—N1—N2110.2 (2)H32A—C32—H32B109.5
C7a—N1—C11130.9 (2)C31—C32—H32C109.5
N2—N1—C11118.7 (2)H32A—C32—H32C109.5
C3—N2—N1105.8 (2)H32B—C32—H32C109.5
N2—C3—C3a110.9 (2)C31—C33—H33A109.5
N2—C3—C31121.4 (2)C31—C33—H33B109.5
C3a—C3—C31127.7 (2)H33A—C33—H33B109.5
C7a—C3a—C3104.9 (2)C31—C33—H33C109.5
C7a—C3a—C4120.5 (2)H33A—C33—H33C109.5
C3—C3a—C4134.5 (2)H33B—C33—H33C109.5
O5—C4—C3a108.7 (2)C31—C34—H34A109.5
O5—C4—H41109.9C31—C34—H34B109.5
C3a—C4—H41109.9H34A—C34—H34B109.5
O5—C4—H42109.9C31—C34—H34C109.5
C3a—C4—H42109.9H34A—C34—H34C109.5
H41—C4—H42108.3H34B—C34—H34C109.5
C6—O5—C4110.3 (2)N7—C77—C71111.6 (2)
O5—C6—N7113.5 (2)N7—C77—H771109.3
O5—C6—H6A108.9C71—C77—H771109.3
N7—C6—H6A108.9N7—C77—H772109.3
O5—C6—H6B108.9C71—C77—H772109.3
N7—C6—H6B108.9H771—C77—H772108.0
H6A—C6—H6B107.7C72—C71—C76118.7 (3)
C7a—N7—C6107.0 (2)C72—C71—C77118.7 (3)
C7a—N7—C77112.7 (2)C76—C71—C77122.6 (3)
C6—N7—C77113.2 (2)O72—C72—C71119.3 (3)
C3a—C7a—N1108.2 (2)O72—C72—C73119.9 (3)
C3a—C7a—N7125.6 (2)C71—C72—C73120.7 (3)
N1—C7a—N7126.3 (2)O73—C73—C74125.3 (3)
C16—C11—C12120.2 (3)O73—C73—C72115.1 (3)
C16—C11—N1119.5 (2)C74—C73—C72119.6 (3)
C12—C11—N1120.3 (2)C73—C74—C75119.4 (3)
C13—C12—C11119.6 (3)C73—C74—H74120.3
C13—C12—H12120.2C75—C74—H74120.3
C11—C12—H12120.2C76—C75—C74121.0 (3)
C14—C13—C12120.2 (3)C76—C75—H75119.5
C14—C13—H13119.9C74—C75—H75119.5
C12—C13—H13119.9C75—C76—C71120.6 (3)
C15—C14—C13119.9 (3)C75—C76—H76119.7
C15—C14—H14120.1C71—C76—H76119.7
C13—C14—H14120.1C72—O72—C721113.6 (2)
C14—C15—C16120.7 (3)C73—O73—C731116.6 (3)
C14—C15—H15119.6O72—C721—H72A109.5
C16—C15—H15119.6O72—C721—H72B109.5
C15—C16—C11119.3 (3)H72A—C721—H72B109.5
C15—C16—H16120.3O72—C721—H72C109.5
C11—C16—H16120.3H72A—C721—H72C109.5
C3—C31—C33108.9 (3)H72B—C721—H72C109.5
C3—C31—C32111.3 (3)O73—C731—H73A109.5
C33—C31—C32109.6 (3)O73—C731—H73B109.5
C3—C31—C34109.3 (3)H73A—C731—H73B109.5
C33—C31—C34109.6 (3)O73—C731—H73C109.5
C32—C31—C34108.1 (3)H73A—C731—H73C109.5
C31—C32—H32A109.5H73B—C731—H73C109.5
C31—C32—H32B109.5
C7a—N1—N2—C30.6 (3)C12—C13—C14—C151.7 (5)
C11—N1—N2—C3174.8 (2)C13—C14—C15—C160.3 (5)
N1—N2—C3—C3a1.1 (3)C14—C15—C16—C111.1 (5)
N1—N2—C3—C31179.2 (2)C12—C11—C16—C151.0 (4)
N2—C3—C3a—C7a1.2 (3)N1—C11—C16—C15177.4 (3)
C31—C3—C3a—C7a179.2 (3)N2—C3—C31—C33109.2 (4)
N2—C3—C3a—C4175.6 (3)C3a—C3—C31—C3368.6 (4)
C31—C3—C3a—C42.4 (5)N2—C3—C31—C3211.7 (4)
C7a—C3a—C4—O514.6 (4)C3a—C3—C31—C32170.5 (3)
C3—C3a—C4—O5161.9 (3)N2—C3—C31—C34131.1 (3)
C3a—C4—O5—C648.6 (3)C3a—C3—C31—C3451.1 (4)
C4—O5—C6—N771.1 (3)C7a—N7—C77—C71169.9 (2)
O5—C6—N7—C7a48.8 (3)C6—N7—C77—C7168.5 (3)
O5—C6—N7—C7776.0 (3)N7—C77—C71—C72148.5 (3)
C3—C3a—C7a—N10.8 (3)N7—C77—C71—C7633.2 (4)
C4—C3a—C7a—N1176.6 (2)C76—C71—C72—O72176.2 (3)
C3—C3a—C7a—N7179.4 (3)C77—C71—C72—O722.1 (4)
C4—C3a—C7a—N73.2 (4)C76—C71—C72—C730.1 (4)
N2—N1—C7a—C3a0.2 (3)C77—C71—C72—C73178.2 (2)
C11—N1—C7a—C3a174.8 (3)O72—C72—C73—O734.2 (4)
N2—N1—C7a—N7180.0 (2)C71—C72—C73—O73179.7 (2)
C11—N1—C7a—N75.4 (5)O72—C72—C73—C74175.4 (3)
C6—N7—C7a—C3a12.7 (4)C71—C72—C73—C740.7 (4)
C77—N7—C7a—C3a112.5 (3)O73—C73—C74—C75178.9 (3)
C6—N7—C7a—N1167.6 (3)C72—C73—C74—C751.5 (4)
C77—N7—C7a—N167.3 (3)C73—C74—C75—C761.6 (5)
C7a—N1—C11—C16158.5 (3)C74—C75—C76—C710.8 (5)
N2—N1—C11—C1627.3 (4)C72—C71—C76—C750.1 (5)
C7a—N1—C11—C1223.2 (4)C77—C71—C76—C75178.2 (3)
N2—N1—C11—C12151.1 (2)C71—C72—O72—C721100.0 (3)
C16—C11—C12—C130.5 (4)C73—C72—O72—C72183.8 (3)
N1—C11—C12—C13178.8 (3)C74—C73—O73—C7310.9 (4)
C11—C12—C13—C141.8 (4)C72—C73—O73—C731178.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···N70.952.453.043 (4)120
C77—H772···O720.992.402.776 (4)102
(VII) 3-tert-butyl-7-(3,4-methylenedioxybenzyl)-1-phenyl-6,7-dihydro- 1H,4H-pyrazolo[3,4-d][1,3]oxazine top
Crystal data top
C23H25N3O3F(000) = 832
Mr = 391.46Dx = 1.297 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4592 reflections
a = 9.1164 (14) Åθ = 2.8–27.5°
b = 11.3303 (18) ŵ = 0.09 mm1
c = 19.694 (2) ÅT = 120 K
β = 99.775 (13)°Lath, colourless
V = 2004.7 (5) Å30.38 × 0.12 × 0.08 mm
Z = 4
Data collection top
Bruker Nonius KappaCCD
diffractometer
4592 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode2768 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.098
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.8°
ϕ & ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1414
Tmin = 0.977, Tmax = 0.993l = 2325
28641 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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0642P)2 + 0.7945P]
where P = (Fo2 + 2Fc2)/3
4592 reflections(Δ/σ)max = 0.001
265 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.49 e Å3
Crystal data top
C23H25N3O3V = 2004.7 (5) Å3
Mr = 391.46Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.1164 (14) ŵ = 0.09 mm1
b = 11.3303 (18) ÅT = 120 K
c = 19.694 (2) Å0.38 × 0.12 × 0.08 mm
β = 99.775 (13)°
Data collection top
Bruker Nonius KappaCCD
diffractometer
4592 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2768 reflections with I > 2σ(I)
Tmin = 0.977, Tmax = 0.993Rint = 0.098
28641 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0690 restraints
wR(F2) = 0.165H-atom parameters constrained
S = 1.16Δρmax = 0.32 e Å3
4592 reflectionsΔρmin = 0.49 e Å3
265 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.6880 (2)0.65224 (18)0.75042 (11)0.0174 (5)
N20.8125 (2)0.59907 (19)0.78572 (10)0.0185 (5)
C30.8975 (3)0.5764 (2)0.73941 (13)0.0181 (5)
C3a0.8280 (3)0.6130 (2)0.67377 (13)0.0180 (5)
C40.8665 (3)0.6095 (3)0.60356 (14)0.0261 (6)
H410.94180.67080.59920.031*
H420.90930.53160.59530.031*
O50.7352 (2)0.62995 (18)0.55362 (9)0.0294 (5)
C60.6557 (3)0.7295 (3)0.57158 (14)0.0276 (6)
H610.57790.75070.53200.033*
H620.72490.79720.58080.033*
N70.5863 (2)0.70945 (19)0.63146 (11)0.0207 (5)
C7a0.6956 (3)0.6612 (2)0.68248 (13)0.0174 (5)
C110.5799 (3)0.6977 (2)0.78769 (13)0.0197 (6)
C120.5060 (3)0.8012 (2)0.76763 (14)0.0240 (6)
H120.52480.84190.72780.029*
C130.4047 (3)0.8455 (3)0.80561 (16)0.0325 (7)
H130.35220.91620.79160.039*
C140.3797 (3)0.7872 (3)0.86379 (16)0.0352 (8)
H140.31090.81810.89040.042*
C150.4543 (3)0.6840 (3)0.88335 (14)0.0304 (7)
H150.43670.64420.92360.036*
C160.5546 (3)0.6375 (3)0.84527 (13)0.0231 (6)
H160.60490.56560.85850.028*
C311.0445 (3)0.5127 (2)0.75995 (14)0.0226 (6)
C321.0998 (3)0.5242 (3)0.83676 (16)0.0369 (8)
H32A1.02670.48950.86210.055*
H32B1.11360.60780.84890.055*
H32C1.19500.48260.84890.055*
C331.0191 (3)0.3830 (3)0.74079 (18)0.0374 (8)
H33A0.97990.37640.69140.056*
H33B0.94750.34910.76720.056*
H33C1.11360.34010.75140.056*
C341.1619 (3)0.5637 (3)0.72167 (17)0.0337 (7)
H34A1.17500.64790.73230.051*
H34B1.12970.55350.67200.051*
H34C1.25660.52240.73610.051*
C770.4522 (3)0.6343 (2)0.61669 (14)0.0226 (6)
H7710.42410.60860.66080.027*
H7720.47610.56280.59180.027*
C710.3221 (3)0.6962 (2)0.57435 (14)0.0224 (6)
C720.2228 (3)0.6307 (2)0.52777 (13)0.0209 (6)
H720.24070.54990.51920.025*
C730.0979 (3)0.6874 (2)0.49468 (13)0.0218 (6)
C740.0700 (3)0.8037 (2)0.50569 (14)0.0231 (6)
C750.1664 (3)0.8705 (3)0.54975 (16)0.0349 (7)
H750.14800.95170.55690.042*
C760.2934 (3)0.8146 (3)0.58406 (17)0.0360 (8)
H760.36290.85910.61530.043*
O730.0175 (2)0.63974 (19)0.44912 (11)0.0373 (5)
O740.0657 (2)0.83573 (18)0.46884 (10)0.0314 (5)
C780.1176 (3)0.7352 (3)0.42764 (14)0.0274 (6)
H7810.11940.75280.37830.033*
H7820.21970.71410.43420.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0166 (10)0.0164 (12)0.0195 (11)0.0031 (8)0.0034 (9)0.0004 (9)
N20.0158 (10)0.0185 (12)0.0202 (11)0.0005 (9)0.0004 (9)0.0005 (9)
C30.0189 (12)0.0130 (13)0.0235 (13)0.0024 (10)0.0068 (11)0.0011 (10)
C3a0.0206 (12)0.0130 (13)0.0214 (13)0.0026 (10)0.0068 (11)0.0011 (10)
C40.0296 (14)0.0243 (15)0.0261 (14)0.0044 (12)0.0100 (12)0.0026 (12)
O50.0411 (11)0.0286 (11)0.0189 (9)0.0091 (9)0.0066 (9)0.0011 (8)
C60.0348 (15)0.0252 (16)0.0229 (14)0.0060 (12)0.0054 (12)0.0043 (12)
N70.0229 (11)0.0205 (12)0.0181 (11)0.0029 (9)0.0017 (9)0.0009 (9)
C7a0.0220 (13)0.0114 (12)0.0193 (13)0.0028 (10)0.0048 (11)0.0020 (10)
C110.0143 (11)0.0243 (15)0.0202 (13)0.0036 (10)0.0021 (10)0.0083 (11)
C120.0231 (13)0.0224 (15)0.0269 (14)0.0016 (11)0.0055 (12)0.0029 (12)
C130.0252 (14)0.0282 (17)0.0444 (18)0.0041 (12)0.0070 (14)0.0134 (14)
C140.0232 (14)0.047 (2)0.0387 (17)0.0017 (14)0.0130 (13)0.0186 (15)
C150.0262 (14)0.0450 (19)0.0214 (14)0.0104 (13)0.0083 (12)0.0090 (13)
C160.0192 (13)0.0281 (16)0.0210 (13)0.0042 (11)0.0001 (11)0.0030 (11)
C310.0152 (12)0.0221 (15)0.0306 (15)0.0023 (11)0.0044 (11)0.0020 (12)
C320.0220 (14)0.050 (2)0.0360 (17)0.0099 (14)0.0022 (13)0.0037 (15)
C330.0293 (15)0.0226 (16)0.058 (2)0.0083 (13)0.0005 (15)0.0014 (15)
C340.0193 (13)0.0368 (18)0.0470 (19)0.0051 (12)0.0112 (14)0.0073 (15)
C770.0232 (13)0.0169 (14)0.0250 (14)0.0011 (11)0.0037 (11)0.0006 (11)
C710.0240 (13)0.0197 (14)0.0227 (13)0.0042 (11)0.0019 (11)0.0002 (11)
C720.0247 (13)0.0190 (14)0.0197 (13)0.0056 (11)0.0056 (11)0.0010 (11)
C730.0225 (13)0.0271 (15)0.0160 (12)0.0020 (11)0.0042 (11)0.0017 (11)
C740.0233 (13)0.0222 (15)0.0236 (14)0.0087 (11)0.0031 (11)0.0048 (11)
C750.0419 (17)0.0165 (15)0.0423 (18)0.0090 (13)0.0041 (14)0.0036 (13)
C760.0371 (17)0.0223 (16)0.0422 (18)0.0049 (13)0.0121 (14)0.0070 (14)
O730.0308 (11)0.0323 (13)0.0413 (12)0.0133 (9)0.0157 (9)0.0089 (10)
O740.0286 (11)0.0276 (12)0.0357 (12)0.0132 (9)0.0016 (9)0.0005 (9)
C780.0263 (14)0.0299 (16)0.0238 (14)0.0096 (12)0.0020 (12)0.0037 (12)
Geometric parameters (Å, º) top
N1—C7a1.355 (3)C31—C341.523 (4)
N1—N21.366 (3)C31—C331.526 (4)
N1—C111.421 (3)C32—H32A0.9800
N2—C31.319 (3)C32—H32B0.9800
C3—C3a1.402 (4)C32—H32C0.9800
C3—C311.516 (4)C33—H33A0.9800
C3a—C7a1.362 (3)C33—H33B0.9800
C3a—C41.484 (3)C33—H33C0.9800
C4—O51.433 (3)C34—H34A0.9800
C4—H410.9900C34—H34B0.9800
C4—H420.9900C34—H34C0.9800
O5—C61.418 (3)C77—C711.503 (4)
C6—N71.448 (3)C77—H7710.9900
C6—H610.9900C77—H7720.9900
C6—H620.9900C71—C761.386 (4)
N7—C7a1.401 (3)C71—C721.390 (4)
N7—C771.477 (3)C72—C731.372 (4)
C11—C161.376 (4)C72—H720.9500
C11—C121.377 (4)C73—C741.366 (4)
C12—C131.378 (4)C73—O731.372 (3)
C12—H120.9500C74—C751.356 (4)
C13—C141.375 (5)C74—O741.373 (3)
C13—H130.9500C75—C761.390 (4)
C14—C151.374 (4)C75—H750.9500
C14—H140.9500C76—H760.9500
C15—C161.382 (4)O73—C781.432 (3)
C15—H150.9500O74—C781.432 (4)
C16—H160.9500C78—H7810.9900
C31—C321.517 (4)C78—H7820.9900
C7a—N1—N2110.97 (19)C34—C31—C33109.4 (2)
C7a—N1—C11129.7 (2)C31—C32—H32A109.5
N2—N1—C11119.1 (2)C31—C32—H32B109.5
C3—N2—N1105.6 (2)H32A—C32—H32B109.5
N2—C3—C3a110.7 (2)C31—C32—H32C109.5
N2—C3—C31120.3 (2)H32A—C32—H32C109.5
C3a—C3—C31128.9 (2)H32B—C32—H32C109.5
C7a—C3a—C3105.9 (2)C31—C33—H33A109.5
C7a—C3a—C4118.9 (2)C31—C33—H33B109.5
C3—C3a—C4135.2 (2)H33A—C33—H33B109.5
O5—C4—C3a109.5 (2)C31—C33—H33C109.5
O5—C4—H41109.8H33A—C33—H33C109.5
C3a—C4—H41109.8H33B—C33—H33C109.5
O5—C4—H42109.8C31—C34—H34A109.5
C3a—C4—H42109.8C31—C34—H34B109.5
H41—C4—H42108.2H34A—C34—H34B109.5
C6—O5—C4111.1 (2)C31—C34—H34C109.5
O5—C6—N7113.0 (2)H34A—C34—H34C109.5
O5—C6—H61109.0H34B—C34—H34C109.5
N7—C6—H61109.0N7—C77—C71112.9 (2)
O5—C6—H62109.0N7—C77—H771109.0
N7—C6—H62109.0C71—C77—H771109.0
H61—C6—H62107.8N7—C77—H772109.0
C7a—N7—C6106.8 (2)C71—C77—H772109.0
C7a—N7—C77112.4 (2)H771—C77—H772107.8
C6—N7—C77113.0 (2)C76—C71—C72119.4 (3)
N1—C7a—C3a106.8 (2)C76—C71—C77121.7 (3)
N1—C7a—N7126.0 (2)C72—C71—C77118.8 (2)
C3a—C7a—N7127.2 (2)C73—C72—C71117.3 (3)
C16—C11—C12121.1 (2)C73—C72—H72121.4
C16—C11—N1118.3 (2)C71—C72—H72121.4
C12—C11—N1120.6 (2)C74—C73—O73109.9 (2)
C11—C12—C13119.7 (3)C74—C73—C72122.5 (3)
C11—C12—H12120.2O73—C73—C72127.5 (3)
C13—C12—H12120.2C75—C74—C73121.5 (2)
C14—C13—C12119.9 (3)C75—C74—O74128.2 (3)
C14—C13—H13120.0C73—C74—O74110.2 (2)
C12—C13—H13120.0C74—C75—C76116.9 (3)
C15—C14—C13119.9 (3)C74—C75—H75121.6
C15—C14—H14120.1C76—C75—H75121.6
C13—C14—H14120.1C71—C76—C75122.4 (3)
C14—C15—C16120.9 (3)C71—C76—H76118.8
C14—C15—H15119.5C75—C76—H76118.8
C16—C15—H15119.5C73—O73—C78106.0 (2)
C11—C16—C15118.5 (3)C74—O74—C78105.7 (2)
C11—C16—H16120.7O74—C78—O73107.5 (2)
C15—C16—H16120.7O74—C78—H781110.2
C3—C31—C32110.8 (2)O73—C78—H781110.2
C3—C31—C34110.6 (2)O74—C78—H782110.2
C32—C31—C34108.6 (2)O73—C78—H782110.2
C3—C31—C33107.6 (2)H781—C78—H782108.5
C32—C31—C33109.9 (3)
C7a—N1—N2—C30.6 (3)C13—C14—C15—C160.1 (4)
C11—N1—N2—C3174.2 (2)C12—C11—C16—C150.8 (4)
N1—N2—C3—C3a0.9 (3)N1—C11—C16—C15177.3 (2)
N1—N2—C3—C31177.8 (2)C14—C15—C16—C110.9 (4)
N2—C3—C3a—C7a0.8 (3)N2—C3—C31—C3221.5 (3)
C31—C3—C3a—C7a177.4 (3)C3a—C3—C31—C32162.2 (3)
N2—C3—C3a—C4178.9 (3)N2—C3—C31—C34141.9 (3)
C31—C3—C3a—C42.4 (5)C3a—C3—C31—C3441.8 (4)
C7a—C3a—C4—O515.9 (3)N2—C3—C31—C3398.6 (3)
C3—C3a—C4—O5163.8 (3)C3a—C3—C31—C3377.7 (3)
C3a—C4—O5—C648.3 (3)C7a—N7—C77—C71167.2 (2)
C4—O5—C6—N769.9 (3)C6—N7—C77—C7171.8 (3)
O5—C6—N7—C7a49.2 (3)N7—C77—C71—C7637.8 (4)
O5—C6—N7—C7774.9 (3)N7—C77—C71—C72146.8 (2)
N2—N1—C7a—C3a0.1 (3)C76—C71—C72—C731.5 (4)
C11—N1—C7a—C3a174.0 (2)C77—C71—C72—C73174.0 (2)
N2—N1—C7a—N7179.0 (2)C71—C72—C73—C740.5 (4)
C11—N1—C7a—N77.0 (4)C71—C72—C73—O73177.1 (2)
C3—C3a—C7a—N10.4 (3)O73—C73—C74—C75178.9 (3)
C4—C3a—C7a—N1179.4 (2)C72—C73—C74—C750.9 (4)
C3—C3a—C7a—N7179.5 (2)O73—C73—C74—O741.2 (3)
C4—C3a—C7a—N70.3 (4)C72—C73—C74—O74176.8 (2)
C6—N7—C7a—N1165.2 (2)C73—C74—C75—C761.1 (4)
C77—N7—C7a—N170.3 (3)O74—C74—C75—C76176.1 (3)
C6—N7—C7a—C3a15.9 (3)C72—C71—C76—C751.3 (5)
C77—N7—C7a—C3a108.6 (3)C77—C71—C76—C75174.1 (3)
C7a—N1—C11—C16150.9 (3)C74—C75—C76—C710.0 (5)
N2—N1—C11—C1635.4 (3)C74—C73—O73—C783.8 (3)
C7a—N1—C11—C1231.0 (4)C72—C73—O73—C78178.3 (3)
N2—N1—C11—C12142.7 (2)C75—C74—O74—C78176.8 (3)
C16—C11—C12—C130.1 (4)C73—C74—O74—C785.7 (3)
N1—C11—C12—C13178.2 (2)C74—O74—C78—O737.9 (3)
C11—C12—C13—C141.0 (4)C73—O73—C78—O747.2 (3)
C12—C13—C14—C150.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···N70.952.553.078 (3)115
C4—H42···O73i0.992.413.381 (4)167
C72—H72···O5i0.952.523.413 (3)156
C75—H75···O74ii0.952.553.456 (4)160
C78—H781···N2iii0.992.483.338 (4)145
C4—H41···Cg1iv0.992.913.799 (3)150
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+2, z+1; (iii) x1, y+3/2, z1/2; (iv) x+1, y, z.
(VIII) 3-tert-butyl-1-phenyl-7-(3,4,5-trimethoxybenzyl)-6,7-dihydro- 1H,4H-pyrazolo[3,4-d][1,3]oxazine top
Crystal data top
C25H31N3O4Z = 2
Mr = 437.53F(000) = 468
Triclinic, P1Dx = 1.333 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8189 (10) ÅCell parameters from 4970 reflections
b = 10.0499 (8) Åθ = 3.5–27.5°
c = 12.8130 (14) ŵ = 0.09 mm1
α = 68.710 (9)°T = 120 K
β = 72.537 (8)°Block, colourless
γ = 70.982 (8)°0.36 × 0.25 × 0.15 mm
V = 1089.8 (2) Å3
Data collection top
Bruker Nonius KappaCCD
diffractometer
4970 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode3754 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.5°
ϕ and ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1313
Tmin = 0.958, Tmax = 0.987l = 1616
30046 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0557P)2 + 0.4602P]
where P = (Fo2 + 2Fc2)/3
4970 reflections(Δ/σ)max = 0.001
295 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C25H31N3O4γ = 70.982 (8)°
Mr = 437.53V = 1089.8 (2) Å3
Triclinic, P1Z = 2
a = 9.8189 (10) ÅMo Kα radiation
b = 10.0499 (8) ŵ = 0.09 mm1
c = 12.8130 (14) ÅT = 120 K
α = 68.710 (9)°0.36 × 0.25 × 0.15 mm
β = 72.537 (8)°
Data collection top
Bruker Nonius KappaCCD
diffractometer
4970 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
3754 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.987Rint = 0.050
30046 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.07Δρmax = 0.24 e Å3
4970 reflectionsΔρmin = 0.32 e Å3
295 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.41871 (14)0.34127 (14)0.27052 (11)0.0161 (3)
N20.33809 (14)0.39324 (14)0.18740 (11)0.0176 (3)
C30.22352 (17)0.49451 (17)0.21906 (13)0.0162 (3)
C3a0.22777 (16)0.50813 (16)0.32347 (13)0.0153 (3)
C40.12970 (16)0.59808 (17)0.39998 (13)0.0169 (3)
H410.13950.70090.36620.020*
H420.02590.59860.40880.020*
O50.17008 (11)0.53654 (12)0.50952 (9)0.0177 (2)
C60.32479 (16)0.50649 (17)0.49670 (14)0.0174 (3)
H610.34780.48500.57220.021*
H620.35880.59530.44490.021*
N70.40461 (14)0.38370 (14)0.45118 (11)0.0156 (3)
C7a0.35277 (16)0.40948 (16)0.35319 (13)0.0146 (3)
C110.55964 (16)0.24594 (17)0.25177 (13)0.0169 (3)
C120.67425 (17)0.25633 (18)0.28799 (14)0.0198 (3)
H120.65830.32520.32790.024*
C130.81186 (17)0.16513 (18)0.26528 (14)0.0220 (4)
H130.89110.17010.29070.026*
C140.83531 (18)0.06689 (18)0.20605 (16)0.0255 (4)
H140.93050.00480.19010.031*
C150.72066 (19)0.05885 (19)0.17004 (17)0.0277 (4)
H150.73720.00870.12890.033*
C160.58224 (18)0.14747 (18)0.19286 (15)0.0218 (4)
H160.50310.14090.16830.026*
C310.10797 (17)0.57479 (18)0.14774 (14)0.0189 (3)
C320.16661 (19)0.56236 (19)0.02701 (14)0.0234 (4)
H32A0.25310.60360.00830.035*
H32B0.09020.61690.01820.035*
H32C0.19440.45850.02950.035*
C330.02341 (19)0.5062 (2)0.20305 (16)0.0320 (4)
H33A0.00740.40240.20500.048*
H33B0.10060.55860.15840.048*
H33C0.06150.51340.28130.048*
C340.0626 (2)0.7359 (2)0.14310 (18)0.0372 (5)
H34A0.01620.74520.22020.056*
H34B0.00750.79050.09240.056*
H34C0.14980.77630.11370.056*
C770.39566 (17)0.23763 (17)0.53557 (14)0.0181 (3)
H7710.41170.16610.49400.022*
H7720.29540.24540.58420.022*
C710.50591 (17)0.18036 (16)0.61098 (13)0.0166 (3)
C720.47634 (17)0.22175 (17)0.70885 (13)0.0179 (3)
H720.38540.28770.72890.021*
C730.57941 (17)0.16710 (17)0.77793 (13)0.0180 (3)
C740.70922 (17)0.06779 (17)0.75010 (13)0.0173 (3)
C750.73793 (17)0.02478 (16)0.65319 (14)0.0171 (3)
C760.63713 (17)0.08249 (17)0.58253 (13)0.0168 (3)
H760.65800.05500.51480.020*
O730.56197 (13)0.20001 (13)0.87545 (10)0.0248 (3)
O740.81068 (12)0.01173 (12)0.81828 (10)0.0215 (3)
O750.86794 (12)0.07397 (12)0.63558 (10)0.0216 (3)
C7310.45599 (19)0.32985 (18)0.89012 (15)0.0242 (4)
H73A0.47580.41350.82340.036*
H73B0.46120.34730.95910.036*
H73C0.35750.31890.89800.036*
C7410.7812 (2)0.1139 (2)0.90951 (16)0.0294 (4)
H74A0.68770.08530.96080.044*
H74B0.86070.15610.95220.044*
H74C0.77470.18720.87870.044*
C7510.89433 (19)0.14104 (19)0.54920 (15)0.0241 (4)
H75A0.81730.19230.56570.036*
H75B0.99050.21190.54720.036*
H75C0.89340.06540.47490.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0124 (6)0.0176 (6)0.0180 (7)0.0014 (5)0.0069 (5)0.0064 (5)
N20.0160 (6)0.0194 (7)0.0180 (7)0.0005 (5)0.0077 (5)0.0062 (5)
C30.0142 (7)0.0157 (7)0.0184 (8)0.0028 (6)0.0037 (6)0.0051 (6)
C3a0.0135 (7)0.0157 (7)0.0165 (7)0.0036 (6)0.0037 (6)0.0042 (6)
C40.0136 (7)0.0188 (8)0.0181 (8)0.0002 (6)0.0052 (6)0.0068 (6)
O50.0135 (5)0.0229 (6)0.0160 (5)0.0011 (4)0.0034 (4)0.0075 (5)
C60.0142 (7)0.0209 (8)0.0191 (8)0.0031 (6)0.0047 (6)0.0080 (6)
N70.0152 (6)0.0164 (6)0.0156 (6)0.0024 (5)0.0055 (5)0.0045 (5)
C7a0.0129 (7)0.0146 (7)0.0162 (7)0.0040 (6)0.0037 (6)0.0033 (6)
C110.0122 (7)0.0163 (7)0.0176 (8)0.0000 (6)0.0024 (6)0.0035 (6)
C120.0169 (8)0.0226 (8)0.0195 (8)0.0027 (6)0.0048 (6)0.0067 (7)
C130.0139 (8)0.0247 (9)0.0231 (9)0.0027 (6)0.0065 (6)0.0018 (7)
C140.0126 (8)0.0190 (8)0.0354 (10)0.0014 (6)0.0003 (7)0.0056 (7)
C150.0208 (9)0.0233 (9)0.0397 (11)0.0032 (7)0.0003 (8)0.0167 (8)
C160.0159 (8)0.0215 (8)0.0294 (9)0.0035 (6)0.0043 (7)0.0103 (7)
C310.0175 (8)0.0204 (8)0.0200 (8)0.0020 (6)0.0089 (6)0.0089 (6)
C320.0227 (8)0.0257 (9)0.0198 (8)0.0001 (7)0.0090 (7)0.0059 (7)
C330.0176 (8)0.0542 (12)0.0253 (9)0.0071 (8)0.0069 (7)0.0124 (9)
C340.0480 (12)0.0254 (10)0.0432 (12)0.0144 (9)0.0331 (10)0.0174 (9)
C770.0156 (7)0.0180 (8)0.0207 (8)0.0042 (6)0.0071 (6)0.0030 (6)
C710.0154 (7)0.0158 (7)0.0184 (8)0.0049 (6)0.0067 (6)0.0011 (6)
C720.0147 (7)0.0175 (8)0.0184 (8)0.0017 (6)0.0043 (6)0.0030 (6)
C730.0189 (8)0.0181 (8)0.0163 (8)0.0044 (6)0.0050 (6)0.0034 (6)
C740.0158 (7)0.0181 (8)0.0183 (8)0.0044 (6)0.0074 (6)0.0025 (6)
C750.0134 (7)0.0152 (7)0.0211 (8)0.0033 (6)0.0033 (6)0.0040 (6)
C760.0180 (8)0.0172 (8)0.0160 (8)0.0051 (6)0.0051 (6)0.0040 (6)
O730.0266 (6)0.0261 (6)0.0213 (6)0.0037 (5)0.0107 (5)0.0110 (5)
O740.0184 (6)0.0239 (6)0.0240 (6)0.0017 (5)0.0118 (5)0.0060 (5)
O750.0153 (6)0.0244 (6)0.0260 (6)0.0029 (5)0.0082 (5)0.0121 (5)
C7310.0256 (9)0.0222 (8)0.0234 (9)0.0016 (7)0.0034 (7)0.0101 (7)
C7410.0318 (10)0.0272 (9)0.0256 (9)0.0019 (8)0.0158 (8)0.0005 (7)
C7510.0217 (8)0.0259 (9)0.0266 (9)0.0005 (7)0.0071 (7)0.0138 (7)
Geometric parameters (Å, º) top
N1—C7a1.356 (2)C32—H32C0.9800
N1—N21.3660 (17)C33—H33A0.9800
N1—C111.4121 (19)C33—H33B0.9800
N2—C31.321 (2)C33—H33C0.9800
C3—C3a1.407 (2)C34—H34A0.9800
C3—C311.505 (2)C34—H34B0.9800
C3a—C7a1.359 (2)C34—H34C0.9800
C3a—C41.488 (2)C77—C711.501 (2)
C4—O51.4330 (18)C77—H7710.9900
C4—H410.9900C77—H7720.9900
C4—H420.9900C71—C721.383 (2)
O5—C61.4188 (18)C71—C761.383 (2)
C6—N71.448 (2)C72—C731.390 (2)
C6—H610.9900C72—H720.9500
C6—H620.9900C73—O731.3545 (19)
N7—C7a1.4014 (19)C73—C741.380 (2)
N7—C771.4854 (19)C74—O741.3682 (18)
C11—C161.377 (2)C74—C751.381 (2)
C11—C121.385 (2)C75—O751.3526 (19)
C12—C131.379 (2)C75—C761.385 (2)
C12—H120.9500C76—H760.9500
C13—C141.377 (3)O73—C7311.413 (2)
C13—H130.9500O74—C7411.417 (2)
C14—C151.373 (2)O75—C7511.415 (2)
C14—H140.9500C731—H73A0.9800
C15—C161.374 (2)C731—H73B0.9800
C15—H150.9500C731—H73C0.9800
C16—H160.9500C741—H74A0.9800
C31—C321.516 (2)C741—H74B0.9800
C31—C341.517 (2)C741—H74C0.9800
C31—C331.522 (2)C751—H75A0.9800
C32—H32A0.9800C751—H75B0.9800
C32—H32B0.9800C751—H75C0.9800
C7a—N1—N2110.66 (12)H32B—C32—H32C109.5
C7a—N1—C11130.28 (13)C31—C33—H33A109.5
N2—N1—C11118.41 (12)C31—C33—H33B109.5
C3—N2—N1105.52 (12)H33A—C33—H33B109.5
N2—C3—C3a111.01 (13)C31—C33—H33C109.5
N2—C3—C31120.42 (14)H33A—C33—H33C109.5
C3a—C3—C31128.55 (14)H33B—C33—H33C109.5
C7a—C3a—C3105.18 (14)C31—C34—H34A109.5
C7a—C3a—C4119.92 (14)C31—C34—H34B109.5
C3—C3a—C4134.88 (14)H34A—C34—H34B109.5
O5—C4—C3a109.09 (12)C31—C34—H34C109.5
O5—C4—H41109.9H34A—C34—H34C109.5
C3a—C4—H41109.9H34B—C34—H34C109.5
O5—C4—H42109.9N7—C77—C71113.19 (12)
C3a—C4—H42109.9N7—C77—H771108.9
H41—C4—H42108.3C71—C77—H771108.9
C6—O5—C4110.63 (11)N7—C77—H772108.9
O5—C6—N7113.05 (12)C71—C77—H772108.9
O5—C6—H61109.0H771—C77—H772107.8
N7—C6—H61109.0C72—C71—C76120.10 (14)
O5—C6—H62109.0C72—C71—C77120.90 (14)
N7—C6—H62109.0C76—C71—C77118.98 (14)
H61—C6—H62107.8C71—C72—C73120.11 (15)
C7a—N7—C6106.79 (12)C71—C72—H72119.9
C7a—N7—C77113.15 (12)C73—C72—H72119.9
C6—N7—C77113.82 (12)O73—C73—C74115.35 (14)
N1—C7a—C3a107.63 (13)O73—C73—C72125.07 (14)
N1—C7a—N7126.20 (13)C74—C73—C72119.55 (15)
C3a—C7a—N7126.17 (14)O74—C74—C73120.09 (14)
C16—C11—C12120.87 (14)O74—C74—C75119.57 (14)
C16—C11—N1118.91 (14)C73—C74—C75120.34 (14)
C12—C11—N1120.16 (14)O75—C75—C74114.87 (14)
C13—C12—C11118.94 (15)O75—C75—C76125.01 (15)
C13—C12—H12120.5C74—C75—C76120.12 (14)
C11—C12—H12120.5C71—C76—C75119.74 (15)
C14—C13—C12120.47 (15)C71—C76—H76120.1
C14—C13—H13119.8C75—C76—H76120.1
C12—C13—H13119.8C73—O73—C731117.19 (12)
C15—C14—C13119.79 (16)C74—O74—C741111.83 (12)
C15—C14—H14120.1C75—O75—C751117.97 (12)
C13—C14—H14120.1O73—C731—H73A109.5
C14—C15—C16120.73 (16)O73—C731—H73B109.5
C14—C15—H15119.6H73A—C731—H73B109.5
C16—C15—H15119.6O73—C731—H73C109.5
C15—C16—C11119.18 (15)H73A—C731—H73C109.5
C15—C16—H16120.4H73B—C731—H73C109.5
C11—C16—H16120.4O74—C741—H74A109.5
C3—C31—C32110.91 (13)O74—C741—H74B109.5
C3—C31—C34108.88 (13)H74A—C741—H74B109.5
C32—C31—C34109.17 (15)O74—C741—H74C109.5
C3—C31—C33108.43 (14)H74A—C741—H74C109.5
C32—C31—C33109.05 (14)H74B—C741—H74C109.5
C34—C31—C33110.40 (16)O75—C751—H75A109.5
C31—C32—H32A109.5O75—C751—H75B109.5
C31—C32—H32B109.5H75A—C751—H75B109.5
H32A—C32—H32B109.5O75—C751—H75C109.5
C31—C32—H32C109.5H75A—C751—H75C109.5
H32A—C32—H32C109.5H75B—C751—H75C109.5
C7a—N1—N2—C30.64 (16)C14—C15—C16—C110.5 (3)
C11—N1—N2—C3171.05 (13)C12—C11—C16—C150.0 (3)
N1—N2—C3—C3a0.64 (17)N1—C11—C16—C15177.21 (15)
N1—N2—C3—C31179.01 (13)N2—C3—C31—C3219.1 (2)
N2—C3—C3a—C7a0.42 (18)C3a—C3—C31—C32162.88 (15)
C31—C3—C3a—C7a178.62 (15)N2—C3—C31—C34139.21 (16)
N2—C3—C3a—C4177.99 (16)C3a—C3—C31—C3442.7 (2)
C31—C3—C3a—C40.2 (3)N2—C3—C31—C33100.64 (17)
C7a—C3a—C4—O514.00 (19)C3a—C3—C31—C3377.4 (2)
C3—C3a—C4—O5164.23 (16)C7a—N7—C77—C71154.32 (13)
C3a—C4—O5—C647.36 (15)C6—N7—C77—C7183.53 (16)
C4—O5—C6—N770.87 (16)N7—C77—C71—C7284.69 (18)
O5—C6—N7—C7a50.39 (16)N7—C77—C71—C7696.68 (16)
O5—C6—N7—C7775.21 (16)C76—C71—C72—C731.1 (2)
N2—N1—C7a—C3a0.39 (17)C77—C71—C72—C73179.70 (14)
C11—N1—C7a—C3a170.02 (14)C71—C72—C73—O73179.92 (14)
N2—N1—C7a—N7179.99 (13)C71—C72—C73—C742.0 (2)
C11—N1—C7a—N79.6 (3)O73—C73—C74—O741.1 (2)
C3—C3a—C7a—N10.01 (17)C72—C73—C74—O74179.14 (14)
C4—C3a—C7a—N1178.69 (13)O73—C73—C74—C75179.20 (14)
C3—C3a—C7a—N7179.59 (14)C72—C73—C74—C751.1 (2)
C4—C3a—C7a—N71.7 (2)O74—C74—C75—O750.9 (2)
C6—N7—C7a—N1164.15 (14)C73—C74—C75—O75179.39 (13)
C77—N7—C7a—N169.84 (19)O74—C74—C75—C76178.99 (13)
C6—N7—C7a—C3a15.4 (2)C73—C74—C75—C760.7 (2)
C77—N7—C7a—C3a110.63 (17)C72—C71—C76—C750.8 (2)
C7a—N1—C11—C16155.10 (16)C77—C71—C76—C75177.85 (13)
N2—N1—C11—C1635.1 (2)O75—C75—C76—C71178.45 (14)
C7a—N1—C11—C1227.6 (2)C74—C75—C76—C711.7 (2)
N2—N1—C11—C12142.14 (15)C74—C73—O73—C731161.62 (14)
C16—C11—C12—C130.7 (2)C72—C73—O73—C73120.4 (2)
N1—C11—C12—C13177.91 (14)C73—C74—O74—C74186.25 (18)
C11—C12—C13—C141.0 (2)C75—C74—O74—C74194.02 (18)
C12—C13—C14—C150.5 (3)C74—C75—O75—C751169.91 (14)
C13—C14—C15—C160.3 (3)C76—C75—O75—C75110.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···N70.952.533.071 (2)116
C4—H42···O5i0.992.473.354 (2)148
C13—H13···O75ii0.952.573.466 (2)157
C14—H14···O74ii0.952.463.247 (2)140
C6—H62···Cg10.992.763.737 (2)167
Symmetry codes: (i) x, y+1, z+1; (ii) x+2, y, z+1.

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC22H25N3OC23H27N3OC23H27N3O2C23H24F3N3O
Mr347.45361.48377.48415.45
Crystal system, space groupMonoclinic, P21Monoclinic, P21Monoclinic, P21Triclinic, P1
Temperature (K)120120120120
a, b, c (Å)8.893 (1), 11.1321 (12), 10.2078 (9)8.9500 (7), 11.2146 (10), 10.0768 (9)9.1888 (2), 11.4499 (3), 9.7210 (2)9.0277 (11), 9.8597 (12), 12.6835 (18)
α, β, γ (°)90, 109.749 (7), 9090, 107.572 (5), 9090, 101.857 (1), 9085.531 (11), 74.180 (11), 67.162 (9)
V3)951.11 (18)964.22 (15)1000.93 (4)1000.6 (2)
Z2222
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.080.080.080.11
Crystal size (mm)0.41 × 0.25 × 0.220.32 × 0.22 × 0.150.15 × 0.12 × 0.050.27 × 0.17 × 0.14
Data collection
DiffractometerBruker Nonius KappaCCD
diffractometer
Bruker Nonius KappaCCD
diffractometer
Bruker Nonius KappaCCD
diffractometer
Bruker Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Multi-scan
(SADABS; Sheldrick, 2003)
Multi-scan
(SADABS; Sheldrick, 2003)
Multi-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.885, 0.9750.957, 0.9890.980, 0.9960.922, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
15738, 2303, 1768 15494, 2323, 1443 12855, 2411, 2237 24473, 4601, 2336
Rint0.0570.0960.0360.099
(sin θ/λ)max1)0.6500.6490.6500.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.103, 1.10 0.052, 0.149, 1.07 0.038, 0.085, 1.19 0.061, 0.183, 1.04
No. of reflections2303232324114601
No. of parameters239249257274
No. of restraints1110
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.260.27, 0.300.17, 0.200.33, 0.37


(V)(VI)(VII)(VIII)
Crystal data
Chemical formulaC22H24N4O3C24H29N3O3C23H25N3O3C25H31N3O4
Mr392.45407.50391.46437.53
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21Monoclinic, P21/cTriclinic, P1
Temperature (K)120120120120
a, b, c (Å)19.164 (2), 8.7781 (7), 11.7188 (12)8.8268 (10), 11.6521 (10), 10.3831 (7)9.1164 (14), 11.3303 (18), 19.694 (2)9.8189 (10), 10.0499 (8), 12.8130 (14)
α, β, γ (°)90, 101.717 (10), 9090, 93.747 (9), 9090, 99.775 (13), 9068.710 (9), 72.537 (8), 70.982 (8)
V3)1930.3 (3)1065.63 (17)2004.7 (5)1089.8 (2)
Z4242
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.090.090.090.09
Crystal size (mm)0.33 × 0.22 × 0.180.25 × 0.20 × 0.190.38 × 0.12 × 0.080.36 × 0.25 × 0.15
Data collection
DiffractometerBruker Nonius KappaCCD
diffractometer
Bruker Nonius KappaCCD
diffractometer
Bruker Nonius KappaCCD
diffractometer
Bruker Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Multi-scan
(SADABS; Sheldrick, 2003)
Multi-scan
(SADABS; Sheldrick, 2003)
Multi-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.917, 0.9840.972, 0.9840.977, 0.9930.958, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
27769, 4417, 2821 17934, 2560, 2132 28641, 4592, 2768 30046, 4970, 3754
Rint0.0660.0490.0980.050
(sin θ/λ)max1)0.6500.6500.6500.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.116, 1.09 0.044, 0.112, 1.13 0.069, 0.165, 1.16 0.047, 0.120, 1.07
No. of reflections4417256045924970
No. of parameters265276265295
No. of restraints0100
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.290.32, 0.270.32, 0.490.24, 0.32

Computer programs: COLLECT (Hooft, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Conformational parameters (Å, °) for compounds (I)–(VIII) top
(a)Ring-puckering parameters
Qθϕ
(I)0.496 (3)128.3 (3)146.7 (4)
(II)0.491 (4)128.8 (5)143.9 (7)
(III)0.501 (2)128.6 (2)146.1 (3)
(IV)0.499 (3)127.6 (3)150.1 (4)
(V)0.475 (2)132.3 (2)145.3 (3)
(VI)0.498 (3)127.7 (3)151.3 (4)
(VII)0.488 (3)130.1 (4)149.6 (4)
(VIII)0.498 (2)128.6 (2)148.1 (2)
(b)Selected torsion angles
N2—N1—C11—C12N2—C3—C31—C32C6—N7—C77—C71N7—C77—C71—C72
(I)145.5 (2)-14.8 (4)-67.5 (3)117.1 (3)
(II)143.5 (4)-13.7 (5)-69.2 (5)122.1 (4)
(III)142.89 (19)-19.9 (3)-71.6 (2)143.1 (2)
(IV)150.6 (2)-11.1 (4)-70.9 (3)147.0 (3)
(V)140.79 (17)-11.8 (2)-75.3 (2)138.65 (18)
(VI)151.1 (2)-11.7 (4)-68.5 (3)148.5 (3)
(VII)142.7 (2)-21.5 (3)-71.8 (3)146.8 (2)
(VIII)142.14 (15)-19.1 (2)-83.53 (16)84.69 (18)
Puckering parameters are calculated for the atom sequence O5–C4–C3a–C7a–N7–C6
Hydrogen bonds and short intramolecular contacts (Å, °) for compounds (I)–(VIII) top
CompoundD—H···AD—HH···AD···AD—H···A
(I)C12—H12···N70.952.553.079 (4)115
C15—H15···O5i0.952.423.210 (3)140
(II)C12—H12···N70.952.603.103 (5)113
C15—H15···O5i0.952.613.258 (5)126
C4—H41···Cg1ii0.992.963.872 (5)154
(III)C12-H12···N70.952.623.108 (3)113
(IV)C12-H12···N70.952.483.040 (4)118
(V)C12—H12···N70.952.553.062 (3)114
C13—H13···N2iii0.952.553.399 (2)148
C72—H72···O41iv0.952.373.293 (3)163
C75—H75···O5iii0.952.503.409 (2)161
(VI)C12—H12···N70.952.453.043 (4)120
C77—H772···O720.992.402.776 (4)102
(VII)C12—H12···N70.952.553.078 (3)115
C4—H42···O73v0.992.413.381 (4)167
C72—H72···O5v0.952.523.413 (3)156
C75—H75···O74vi0.952.553.456 (4)160
C78—H781···N2vii0.992.483.338 (4)145
C4—H41···Cg1viii0.992.913.799 (3)150
(VIII)C12—H12···N70.952.533.071 (2)116
C4—H42···O5ix0.992.473.354 (2)148
C13—H13···O75x0.952.573.466 (2)157
C14—H14···O74x0.952.463.247 (2)140
C6—H62···Cg1v0.992.763.737 (2)167
Cg1 represents the centroid of the C71–C76 ring. Symmetry codes: (i) x, y, -1+z; (ii) -1+x, y, z; (iii) x, 1.5-y, 0.5+z; (iv) 1-x, -0.5+y, 0.5-z; (v) 1-x, 1-y, 1-z; (vi) -x, 2-y, 1-z; (vii) -1+x, 1.5-y, -0.5+z; (viii) 1+x, y, z; (ix) -x, 1-y, 1-z; (x) 2-x, -y, 1-z.
 

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