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The structures of a chalcone and of its cyclo­condensation product with guanidine are reported. In (2E)-3-(6-meth­oxy­naphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one, C19H15NO2, (I), the planes of the pyridine and naphthalene units make dihedral angles with that of the central spacer unit of 23.61 (13) and 23.57 (15)°, respectively, and a dihedral angle of 47.24 (9)° with each other. The mol­ecules of (I) are linked into sheets by a combination of C-H...O and C-H...[pi](arene) hydrogen bonds. In the cyclo­condensation product (4RS)-2-amino-4-(6-meth­oxy­naphthalen-2-yl)-6-(pyri­din-3-yl)-3,4-dihydro­pyrimidine monohydrate, C20H18N4O·H2O, (II), the di­hydro­pyrimidine ring adopts a conformation best described as a shallow boat. The mol­ecular components are linked by two N-H...O hydrogen bonds, two O-H...N hydrogen bonds and one N-H...N hydrogen bond to form complex sheets, with the meth­oxy­naphthalene inter­digitated between inversion-related pairs of sheets.

Supporting information

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Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229614021524/sk3565sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614021524/sk3565Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229614021524/sk3565IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229614021524/sk3565Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229614021524/sk3565IIsup5.cml
Supplementary material

CCDC references: 1026573; 1026574

Introduction top

Chalcones, 1,3-disubstituted prop-2-en-1-ones of the form R1COCH CHR2, which contain meth­oxy substitutents exhibit potential as effective pharmaceutical agents in a number of applications, such as anti­cancer agents (Lawrence et al., 2006) and anti-infective and anti-inflammatory agents (Nowakowska, 2007). It has been observed that, when meth­oxy groups are present in chalcones, they can act as good acceptors of hydrogen bonds, while electron-rich naphthyl rings can participate in ππ stacking inter­actions, and both of these properties can play important roles in orientating inhibitors within the active sites of enzymes (Mascarello et al., 2010). In addition, pyrimidine derivatives display a wide range of biological and pharmacological properties, such as anti­cancer (Petrie et al., 1985), anti-inflammatory (Sondhi et al., 2001) and anti­tumour (Baraldi et al., 2002) activities. Prompted by these considerations, we have now prepared and structurally characterized the title chalcone (2E)-3-(6-meth­oxy­naphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one, (I) (Fig. 1), which incorporates a meth­oxy-substituted naphthyl group. Compound (I) was prepared by Claisen condensation between 3-acetyl pyridine (A) (see scheme) and 6-meth­oxy­naphtahlene-2-carboxaldehyde (B).

Chalcones can exhibit two distinct reactivity modes, namely Michael addition at the CC double bond and condensation at the carbonyl group, and when these two modes are active in tandem new cyclic structures can result. Thus, for example, the cyclo­condensation reactions of chalcones with simple hydrazines lead to the formation of di­hydro­pyrazole derivatives (Fun et al., 2010; Jasinski, Guild et al., 2010; Jasinski, Pek et al., 2010; Samshuddin et al., 2010). Following these precedents, we have now prepared the title di­hydro­pyrimidine derivative (4RS)-2-amino-4-(6-meth­oxy­naphthalen-2-yl)-6-(pyridin-3-yl)-3,4-di­hydro­pyrimidine monohydrate, (II) (Fig. 2), by cyclo­condensation of chalcone (I) with guanidinium chloride under basic conditions (see scheme), and we report here the structure of (II) also. The aims of the present study are the conformations of the molecular constitutions of (I) and (II) and the exploration of their supra­molecular assembly, in particular the influence of both the naphthyl unit and the meth­oxy substituent on this assembly.

Experimental top

Synthesis and crystallization top

For the synthesis of (I), a solution of aqueous potassium hydroxide (15 ml of a 10% w/v solution) was added to a mixture of 3-acetyl­pyridine (0.01 mol) and 6-meth­oxy-2-naphthaldehyde (0.01 mol) in ethanol (40 ml). This mixture was then stirred at 280 K for 3 h. The resulting solid product was collected by filtration and recrystallized from ethanol (yield 87%, m.p. 433–435 K). Colourless crystals of (I) suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in air, of a solution in methanol–toluene (1:1 v/v).

For the synthesis of (II), a mixture of (I) (0.01 mol) and guanidinium chloride (0.01 mol) in ethanol (25 ml) was heated under reflux for 24 h in the presence of sodium ethoxide (3.1 ml of a 21% w/v solution in ethanol). The mixture was allowed to cool to ambient temperature and refrigerated overnight. The resulting solid product was collected by filtration and recrystallized from ethanol (yield 62%, m.p. 413–415 K). Yellow crystals of (II) suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in the presence of air, of a solution in N,N-di­methyl­formamide.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were located in difference maps and then treated as riding atoms. C-bound H atoms were treated as riding in geometrically idealized positions, with C—H = 0.95 (alkenyl, aromatic and pyridyl), 0.98 (methyl) or 1.00 Å (aliphatic C—H), and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and 1.2 for all other C-bound H atoms. N- or O-bound H atoms were permitted to ride at the positions located in difference maps, with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O), giving the N—H and O—H distances shown in Tables 3 and 5. An attempt was made to establish the correct orientation of the structure of (I) with respect to the polar axis direction by use of the Flack x parameter (Flack, 1983), calculated using 1281 quotients of type [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013), giving a value x = 0.022 (404), truncated in the CIF to 0.0 (4). Examination of the refined structures using PLATON (Spek, 2009) showed that neither of them contained any solvent-accessible voids.

Results and discussion top

Compound (I) (Fig. 1) crystallizes in the space group Pca21, but in the absence of any atom heavier than O, the Flack x parameter (Flack, 1983), even as calculated by the Parsons method (Parsons et al., 2013), was associated with a very large s.u. value. Hence, the assignment of the orientation of the structure of (I) relative to the polar axis direction cannot be regarded as robust. Compound (II) crystallizes as a monohydrate and it is possible to select a compact asymmetric unit in which the two independent components are linked by two N—H···O hydrogen bonds (Table 5), so forming an R21(6) (Bernstein et al., 1995) motif (Fig. 2). The organic component of (II) contains a stereogenic centre at atom C4 and the reference molecule was selected as one having the R configuration at atom C4. The centrosymmetric space group confirms that this compound crystallizes as a racemic mixture.

In compound (I), the central spacer unit between atoms C13 and C32 (Fig. 1) adopts a nearly planar all-trans conformation, as shown by the relevant torsion angles (Table 2). However, neither of the adjacent ring systems is coplanar with the central unit. The dihedral angle between the mean plane of the spacer unit (C1–C3/O11) and that of the pyridyl ring is 23.57 (15)°, and that between the spacer and the naphthalene unit is 23.85 (15)°. The dihedral angle between the two ring systems is 47.24 (9)°.

The di­hydro­pyrimidine ring in (II) is nonplanar, with ring-puckering parameters (Cremer & Pople, 1975; calculated for the atom sequence N1/C2/N3/C4–C6) of Q = 0.2251 (12) Å, θ = 106.9 (3)° and ϕ = 352.3 (3)°. The atomic displacements from the mean plane of this ring are such that atoms N1 and C4 are displaced to one side of the mean plane and the other four ring atoms are displaced to the other side, albeit all by different amounts. The best single description of the ring conformation is that of a shallow boat, with atoms N1 and C4 providing the bow and stern of the boat. The ring-puckering angle θ is, in fact, inter­mediate between the ideal values for boat and envelope conformations, 90.0 and 115.3°, respectively (Boeyens, 1978). The amino group in (II) adopts a markedly pyramidal geometry, with a sum of the inter­bond angles at atom N21 of 348°.

In the naphthalene units of both compounds, the bonds Cx1—Cx2, Cx3—Cx4, Cx5—Cx6 and Cx7—Cx8, where x = 3 for (I) and x = 4 for (II) (Figs. 1 and 2), are characteristically (Glidewell & Lloyd, 1984) all shorter than the other C—C bonds in these ring systems (Tables 2 and 4). In each of (I) and (II), the meth­oxy C atom lies close to the plane of the adjacent aryl ring, with displacements from this plane of 0.223 (4) Å in (I) and 0.175 (2) Å in (II). Associated with this near-coplanarity, the two exocyclic C—C—O angles in each of (I) and (II) differ by ca 10°, as usually found in such circumstances (Seip & Seip, 1973; Ferguson et al., 1996).

There are a number of short inter­molecular contacts in the structure of (I) (Table 3), but only two of these can be regarded as structurally significant. Thus, the C—H···N contact involves a C—H bond from a methyl group which is of low acidity and almost certainly undergoing rapid rotation around the adjacent C—O bond (Riddell & Rogerson, 1996, 1997). Of the four C—H···π contacts, all have quite small C—H···Cg angles (cf. Wood et al., 2009) and three of them have quite long H···Cg distances. Accordingly, only the contact involving atom C34 is regarded as structurally significant. The C—H···O hydrogen bond links molecules related by translation to form a C(15) chain running parallel to the [010] direction. The C—H···π(arene) hydrogen bond involving atom C34 links molecules related by the c-glide plane at x = 1/4 to form a chain running parallel to the [001] direction, and the combination of the [010] and [001] chains, each containing a single type of hydrogen bond, links the molecules into a sheet lying parallel to (100) (Fig. 3). These sheets lies in the domain 0 < x < 1/2, and a second such sheet, related to the first by the action of the 21 screw axes at x = 1/2, lies in the domain 1/2 < x < 1.0, but there are no significant direction-specific inter­action between adjacent sheets.

As noted above, the two molecular components in the asymmetric unit selected (II) are linked by two N—H···O hydrogen bonds (Fig. 2). These bimolecular aggregates are linked by three further hydrogen bonds, one of N—H···N type and two of O—H···N type (Table 5). The combination of these three hydrogen bonds links the bimolecular aggregates into sheets, and each of them gives rise to a characteristic substructure (Ferguson et al., 1998a,b; Gregson et al., 2000). These substructures allow straightforward analysis of the complex structure of the sheet.

In the simplest of the substructures, of zero dimensionality, inversion-related pairs of di­hydro­pyrimidine molecules are linked by inversion-related pairs of N—H···N hydrogen bonds to form an R22(8) motif, which is flanked by a pair of R21(6) rings built from the N—H···O hydrogen bonds (Fig. 4). The formation of this four-molecular aggregate utilizes fully the N—H···N and N—H···O hydrogen bonds, and thus leaves just the O—H···N hydrogen bonds available for the formation of further linkages.

Each of the two O—H···N hydrogen bonds gives rise to a chain-of-rings motif. The hydrogen bond having atom N1 as the acceptor links bimolecular aggregates (Fig. 2) which are related by translation to form a C22(6)C22(6)[R21(6)] chain of rings running parallel to the [010] direction (Fig. 5), and that having atom N61 as the acceptor links bimolecular aggregates which are related by the c-glide plane at y = 1/4 to form a C22(10)C22(10)[R21(6)] chain of rings running parallel to the [001] direction (Fig. 6). The combination of these three substructures generates a sheet lying parallel to (100). The reference sheet lies in the domain 1/2 < x < 1.0 and a second sheet, related to first by inversion, lies in the domain 0 < x < 1/2. The mutual arrangement of the sheets within the unit cell is such that the hydrogen bonds lie towards the outer margins of the domain of x, while the 6-meth­oxy­naphthalene units are inter­digited in the central part of this domain (Fig. 7). Despite this, however, there are no direction-specific inter­actions between adjacent naphthalene units, as the distances between naphthalene ring centroids in adjacent molecules are all >5 Å.

Thus, while the meth­oxy O atom in (I) acts as a hydrogen-bond acceptor, that in (II) does not. The naphthalene substituent in (I) acts as an acceptor of a C—H···π(arene) hydrogen bond, although that in (II) does not, but ππ stacking inter­actions involving the naphthalene units are absent from both structures.

Related literature top

For related literature, see: Baraldi et al. (2002); Bernstein et al. (1995); Boeyens (1978); Cremer & Pople (1975); Ferguson et al. (1996, 1998a, 1998b); Flack (1983); Fun et al. (2010); Glidewell & Lloyd (1984); Gregson et al. (2000); Jasinski, Guild, Samshuddin, Narayana & Yathirajan (2010); Jasinski, Pek, Samshuddin, Narayana & Yathirajan (2010); Lawrence et al. (2006); Mascarello et al. (2010); Nowakowska (2007); Parsons et al. (2013); Petrie et al. (1985); Riddell & Rogerson (1996, 1997); Samshuddin et al. (2010); Seip & Seip (1973); Sondhi et al. (2001); Spek (2009); Wood et al. (2009).

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2014); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009) and SHELXL2014 (Sheldrick, 2014).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The independent molecular components of (II), showing the atom-labelling scheme and the N—H···O hydrogen bonds (dashed lines) linking the components within the selected asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of (I), showing the formation of a sheet lying parallel to (100) and built from C—H···O [Not shown?] and C—H···π(arene) [thin solid lines?] hydrogen bonds. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
[Figure 4] Fig. 4. Part of the crystal structure of (II), showing the formation of a centrosymmetric aggregate built from N—H···O and N—H···N hydrogen bonds (dashed lines). For the sake of clarity, C-bound H atoms and the unit-cell outline have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (-x + 2, -y + 1, -z + 1).
[Figure 5] Fig. 5. A stereoview of part of the crystal structure of (II), showing the formation of a C22(6)C22(6)[R21(6)] chain of rings parallel to [010]. [Dashed lines indicate O—H···N hydrogen bonds?] For the sake of clarity, C-bound H atoms have been omitted.
[Figure 6] Fig. 6. A stereoview of part of the crystal structure of (II), showing the formation of a C22(10)C22(10)[R21(6)] chain of rings parallel to [001]. [Dashed lines indicate O—H···N hydrogen bonds?] For the sake of clarity, H atoms bonded to C atoms have been omitted.
[Figure 7] Fig. 7. A projection, along [010], of part of the crystal structure of (II), showing the interdigitation of the 6-methoxynaphthalene units in adjacent inversion-related sheets parallel to (100). [Dashed lines indicate O—H···N hydrogen bonds?]
(I) (2E)-3-(6-Methoxynaphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one top
Crystal data top
C19H15NO2Dx = 1.344 Mg m3
Mr = 289.32Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 3441 reflections
a = 14.2636 (6) Åθ = 1.2–28.4°
b = 16.6789 (6) ŵ = 0.09 mm1
c = 6.0084 (2) ÅT = 200 K
V = 1429.41 (9) Å3Plate, colourless
Z = 40.45 × 0.28 × 0.13 mm
F(000) = 608
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3106 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.021
ϕ and ω scansθmax = 28.4°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1913
Tmin = 0.811, Tmax = 0.989k = 2222
3474 measured reflectionsl = 88
3440 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.0517P)2 + 0.2103P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.25 e Å3
3440 reflectionsΔρmin = 0.18 e Å3
200 parametersAbsolute structure: Flack x parameter determined using 1281 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.0 (4)
Crystal data top
C19H15NO2V = 1429.41 (9) Å3
Mr = 289.32Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 14.2636 (6) ŵ = 0.09 mm1
b = 16.6789 (6) ÅT = 200 K
c = 6.0084 (2) Å0.45 × 0.28 × 0.13 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3440 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
3106 reflections with I > 2σ(I)
Tmin = 0.811, Tmax = 0.989Rint = 0.021
3474 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.100Δρmax = 0.25 e Å3
S = 1.08Δρmin = 0.18 e Å3
3440 reflectionsAbsolute structure: Flack x parameter determined using 1281 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
200 parametersAbsolute structure parameter: 0.0 (4)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.13608 (15)0.78897 (12)0.6903 (4)0.0346 (5)
O110.14016 (13)0.77917 (10)0.8914 (3)0.0456 (5)
C20.13695 (16)0.72033 (12)0.5335 (4)0.0344 (5)
H20.15250.72850.38140.041*
C30.11583 (14)0.64709 (11)0.6073 (3)0.0296 (4)
H30.09630.64350.75810.036*
N110.15568 (17)1.01214 (11)0.6698 (4)0.0512 (6)
C120.15867 (17)0.93578 (13)0.7316 (4)0.0398 (5)
H120.18130.92390.87660.048*
C130.13077 (15)0.87166 (12)0.5973 (4)0.0325 (4)
C140.09803 (17)0.88972 (14)0.3858 (4)0.0413 (5)
H140.07930.84810.28740.050*
C150.0929 (2)0.96912 (14)0.3199 (4)0.0475 (6)
H150.06950.98300.17700.057*
C160.1225 (2)1.02770 (15)0.4657 (5)0.0500 (6)
H160.11921.08200.41900.060*
C310.08734 (13)0.50274 (11)0.5847 (3)0.0260 (4)
H310.05960.50630.72810.031*
C320.11921 (13)0.57162 (10)0.4838 (3)0.0260 (4)
C330.15895 (13)0.56566 (11)0.2665 (3)0.0268 (4)
H330.17930.61290.19240.032*
C340.16819 (14)0.49323 (11)0.1636 (3)0.0271 (4)
H340.19560.49080.01970.033*
C34a0.13757 (13)0.42139 (11)0.2677 (3)0.0241 (4)
C350.14779 (14)0.34528 (11)0.1646 (3)0.0281 (4)
H350.17840.34090.02470.034*
C360.11333 (14)0.27813 (11)0.2677 (4)0.0300 (4)
C370.06901 (14)0.28379 (11)0.4781 (4)0.0316 (4)
H370.04490.23690.54700.038*
C380.06070 (13)0.35573 (11)0.5823 (3)0.0296 (4)
H380.03180.35840.72460.035*
C38a0.09457 (13)0.42696 (10)0.4814 (3)0.0244 (4)
O1360.11714 (12)0.20216 (9)0.1850 (3)0.0408 (4)
C1360.1722 (2)0.18877 (14)0.0102 (4)0.0470 (6)
H36A0.17180.13150.04680.070*
H36B0.23680.20630.01690.070*
H36C0.14580.21930.13470.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0352 (11)0.0314 (10)0.0374 (11)0.0034 (8)0.0022 (9)0.0078 (9)
O110.0639 (12)0.0394 (8)0.0334 (8)0.0061 (8)0.0013 (8)0.0058 (7)
C20.0408 (11)0.0294 (10)0.0332 (11)0.0022 (9)0.0036 (9)0.0064 (8)
C30.0287 (9)0.0305 (9)0.0296 (9)0.0022 (8)0.0004 (8)0.0047 (8)
N110.0654 (14)0.0318 (9)0.0566 (13)0.0001 (9)0.0037 (12)0.0083 (10)
C120.0446 (12)0.0340 (10)0.0408 (13)0.0004 (9)0.0025 (10)0.0078 (9)
C130.0339 (10)0.0302 (9)0.0335 (10)0.0017 (8)0.0040 (9)0.0063 (8)
C140.0486 (14)0.0392 (11)0.0362 (11)0.0040 (10)0.0018 (11)0.0078 (10)
C150.0543 (15)0.0472 (13)0.0411 (14)0.0050 (11)0.0007 (11)0.0057 (11)
C160.0596 (16)0.0311 (11)0.0593 (16)0.0038 (11)0.0056 (14)0.0018 (11)
C310.0243 (8)0.0309 (9)0.0228 (8)0.0036 (7)0.0007 (7)0.0013 (7)
C320.0248 (9)0.0250 (9)0.0281 (10)0.0024 (7)0.0016 (8)0.0037 (8)
C330.0277 (9)0.0261 (9)0.0268 (9)0.0007 (7)0.0009 (8)0.0035 (8)
C340.0277 (9)0.0310 (9)0.0227 (8)0.0008 (7)0.0017 (8)0.0000 (8)
C34a0.0245 (9)0.0261 (9)0.0217 (8)0.0017 (7)0.0018 (8)0.0001 (7)
C350.0320 (10)0.0291 (9)0.0232 (9)0.0020 (7)0.0011 (8)0.0022 (8)
C360.0327 (10)0.0252 (9)0.0321 (10)0.0022 (8)0.0041 (9)0.0017 (8)
C370.0322 (10)0.0279 (9)0.0347 (10)0.0010 (8)0.0006 (9)0.0069 (8)
C380.0290 (9)0.0333 (10)0.0264 (9)0.0023 (7)0.0026 (8)0.0041 (8)
C38a0.0227 (9)0.0275 (9)0.0231 (8)0.0023 (7)0.0017 (7)0.0009 (7)
O1360.0542 (10)0.0258 (6)0.0425 (9)0.0012 (6)0.0039 (8)0.0043 (6)
C1360.0720 (17)0.0332 (11)0.0357 (11)0.0053 (11)0.0025 (12)0.0077 (10)
Geometric parameters (Å, º) top
C1—O111.221 (3)C33—C341.363 (3)
C1—C21.482 (3)C33—H330.9500
C1—C131.490 (3)C34—C34a1.420 (3)
C2—C31.334 (3)C34—H340.9500
C2—H20.9500C34a—C351.420 (3)
C3—C321.462 (3)C35—C361.371 (3)
C3—H30.9500C35—H350.9500
N11—C121.327 (3)C36—O1361.362 (2)
N11—C161.340 (4)C36—C371.417 (3)
C12—C131.398 (3)C37—C381.359 (3)
C12—H120.9500C37—H370.9500
C13—C141.387 (3)C38—C38a1.419 (3)
C14—C151.384 (3)C38a—C311.412 (2)
C14—H140.9500C38—H380.9500
C15—C161.378 (4)C34a—C38a1.426 (2)
C15—H150.9500O136—C1361.429 (3)
C16—H160.9500C136—H36A0.9800
C31—C321.376 (3)C136—H36B0.9800
C31—H310.9500C136—H36C0.9800
C32—C331.427 (3)
O11—C1—C2121.7 (2)C34—C33—C32121.01 (17)
O11—C1—C13119.84 (19)C34—C33—H33119.5
C2—C1—C13118.48 (19)C32—C33—H33119.5
C3—C2—C1119.61 (19)C33—C34—C34a121.21 (17)
C3—C2—H2120.2C33—C34—H34119.4
C1—C2—H2120.2C34a—C34—H34119.4
C2—C3—C32127.75 (19)C35—C34a—C34122.05 (17)
C2—C3—H3116.1C35—C34a—C38a119.68 (17)
C32—C3—H3116.1C34—C34a—C38a118.27 (17)
C12—N11—C16117.0 (2)C36—C35—C34a119.77 (17)
N11—C12—C13124.3 (2)C36—C35—H35120.1
N11—C12—H12117.9C34a—C35—H35120.1
C13—C12—H12117.9O136—C36—C35125.51 (19)
C14—C13—C12117.3 (2)O136—C36—C37113.91 (17)
C14—C13—C1124.18 (19)C35—C36—C37120.58 (18)
C12—C13—C1118.5 (2)C38—C37—C36120.60 (18)
C15—C14—C13119.2 (2)C38—C37—H37119.7
C15—C14—H14120.4C36—C37—H37119.7
C13—C14—H14120.4C37—C38—C38a120.86 (18)
C16—C15—C14118.7 (2)C37—C38—H38119.6
C16—C15—H15120.7C38a—C38—H38119.6
C14—C15—H15120.7C31—C38a—C38122.48 (17)
N11—C16—C15123.5 (2)C31—C38a—C34a119.04 (16)
N11—C16—H16118.2C38—C38a—C34a118.48 (17)
C15—C16—H16118.2C36—O136—C136117.82 (17)
C32—C31—C38a122.00 (16)O136—C136—H36A109.5
C32—C31—H31119.0O136—C136—H36B109.5
C38a—C31—H31119.0H36A—C136—H36B109.5
C31—C32—C33118.41 (16)O136—C136—H36C109.5
C31—C32—C3118.98 (18)H36A—C136—H36C109.5
C33—C32—C3122.52 (17)H36B—C136—H36C109.5
O11—C1—C2—C318.8 (3)C32—C33—C34—C34a0.8 (3)
C13—C1—C2—C3161.6 (2)C33—C34—C34a—C35179.09 (18)
C1—C2—C3—C32175.30 (19)C33—C34—C34a—C38a1.5 (3)
C16—N11—C12—C130.8 (4)C34—C34a—C35—C36177.12 (18)
N11—C12—C13—C140.1 (4)C38a—C34a—C35—C362.3 (3)
N11—C12—C13—C1178.7 (2)C34a—C35—C36—O136178.79 (19)
O11—C1—C13—C14159.6 (2)C34a—C35—C36—C371.1 (3)
C2—C1—C13—C1420.9 (3)O136—C36—C37—C38179.47 (19)
O11—C1—C13—C1219.1 (3)C35—C36—C37—C380.6 (3)
C2—C1—C13—C12160.4 (2)C36—C37—C38—C38a1.2 (3)
C12—C13—C14—C151.2 (3)C32—C31—C38a—C38179.03 (18)
C1—C13—C14—C15177.6 (2)C32—C31—C38a—C34a1.0 (3)
C13—C14—C15—C161.3 (4)C37—C38—C38a—C31179.88 (19)
C12—N11—C16—C150.6 (4)C37—C38—C38a—C34a0.0 (3)
C14—C15—C16—N110.4 (4)C35—C34a—C38a—C31178.18 (18)
C38a—C31—C32—C331.2 (3)C34—C34a—C38a—C312.4 (2)
C38a—C31—C32—C3175.47 (17)C35—C34a—C38a—C381.8 (3)
C2—C3—C32—C31174.8 (2)C34—C34a—C38a—C38177.67 (18)
C2—C3—C32—C338.6 (3)C35—C36—O136—C1368.9 (3)
C31—C32—C33—C342.2 (3)C37—C36—O136—C136171.2 (2)
C3—C32—C33—C34174.39 (18)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 represent the centroids of the rings N11/C12–C16, C31–C34/C34a/C38a and C34a/C35–C38/C38a, respectively.
D—H···AD—HH···AD···AD—H···A
C16—H16···O136i0.952.453.364 (3)162
C136—H36A···N11ii0.982.633.526 (3)152
C3—H3···Cg3iii0.952.943.518 (2)121
C12—H12···Cg1iv0.952.933.555 (3)125
C31—H31···Cg2iii0.952.813.527 (2)133
C34—H34···Cg2v0.952.673.391 (2)133
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z1; (iii) x, y+1, z+1/2; (iv) x+1/2, y, z+1/2; (v) x+1/2, y, z1/2.
(II) (RS)-2-Amino-4-(6-methoxynaphthalen-2-yl)-6-(pyridin-3-yl)-3,4-dihydropyrimidine monohydrate top
Crystal data top
C20H18N4O·H2OF(000) = 736
Mr = 348.40Dx = 1.322 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.2244 (5) ÅCell parameters from 4319 reflections
b = 5.9552 (2) Åθ = 2.2–28.3°
c = 18.5173 (6) ŵ = 0.09 mm1
β = 112.830 (1)°T = 200 K
V = 1750.61 (10) Å3Block, yellow
Z = 40.67 × 0.54 × 0.32 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3596 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.014
ϕ and ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2222
Tmin = 0.895, Tmax = 0.972k = 77
15830 measured reflectionsl = 2422
4319 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0554P)2 + 0.561P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4319 reflectionsΔρmax = 0.29 e Å3
236 parametersΔρmin = 0.17 e Å3
Crystal data top
C20H18N4O·H2OV = 1750.61 (10) Å3
Mr = 348.40Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.2244 (5) ŵ = 0.09 mm1
b = 5.9552 (2) ÅT = 200 K
c = 18.5173 (6) Å0.67 × 0.54 × 0.32 mm
β = 112.830 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
4319 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
3596 reflections with I > 2σ(I)
Tmin = 0.895, Tmax = 0.972Rint = 0.014
15830 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.04Δρmax = 0.29 e Å3
4319 reflectionsΔρmin = 0.17 e Å3
236 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.89139 (6)0.52266 (17)0.41737 (5)0.0298 (2)
C20.87565 (7)0.3476 (2)0.45317 (6)0.0277 (2)
N30.80838 (6)0.21208 (18)0.42197 (6)0.0316 (2)
H30.80630.09060.45200.038*
C40.73670 (7)0.2640 (2)0.34898 (7)0.0314 (3)
H40.71750.12230.31820.038*
C50.76718 (7)0.4235 (2)0.30296 (7)0.0326 (3)
H50.73600.43940.24820.039*
C60.83758 (7)0.5437 (2)0.33777 (6)0.0286 (2)
N210.92997 (6)0.29906 (19)0.52711 (6)0.0340 (2)
H2110.92800.15990.54500.041*
H2120.98120.35930.54170.041*
C410.58418 (7)0.2716 (2)0.33298 (7)0.0313 (3)
H410.57520.13910.30230.038*
C420.66312 (7)0.3639 (2)0.36432 (7)0.0308 (3)
C430.67574 (8)0.5617 (2)0.40969 (9)0.0421 (3)
H430.73020.62760.43110.051*
C440.61107 (8)0.6597 (3)0.42323 (9)0.0455 (3)
H440.62130.79180.45430.055*
C44a0.52881 (7)0.5675 (2)0.39167 (7)0.0344 (3)
C450.46096 (8)0.6671 (2)0.40564 (8)0.0405 (3)
H450.47010.79860.43690.049*
C460.38268 (8)0.5734 (3)0.37404 (8)0.0404 (3)
C470.36847 (8)0.3804 (3)0.32683 (9)0.0446 (3)
H470.31340.31880.30420.054*
C480.43269 (8)0.2804 (3)0.31298 (8)0.0406 (3)
H480.42200.14940.28130.049*
C48a0.51539 (7)0.3709 (2)0.34562 (7)0.0311 (3)
O1460.31249 (6)0.6528 (2)0.38374 (7)0.0538 (3)
C1460.32473 (11)0.8329 (3)0.43708 (10)0.0573 (4)
H46A0.27150.86650.44250.086*
H46B0.34380.96590.41740.086*
H46C0.36740.79080.48830.086*
N610.87654 (7)0.8262 (2)0.17333 (7)0.0429 (3)
C620.85457 (8)0.6778 (2)0.21618 (7)0.0356 (3)
H620.82970.54050.19210.043*
C630.86594 (7)0.7125 (2)0.29423 (6)0.0293 (2)
C640.90497 (7)0.9109 (2)0.32890 (7)0.0331 (3)
H640.91590.94000.38240.040*
C650.92794 (9)1.0666 (2)0.28517 (8)0.0402 (3)
H650.95391.20420.30790.048*
C660.91230 (9)1.0179 (3)0.20805 (9)0.0437 (3)
H660.92761.12560.17810.052*
O710.86814 (7)0.15413 (16)0.53121 (6)0.0436 (2)
H7110.87260.22220.57510.065*
H7120.88130.25720.50200.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0284 (5)0.0340 (5)0.0245 (4)0.0007 (4)0.0077 (4)0.0021 (4)
C20.0261 (5)0.0307 (6)0.0271 (5)0.0031 (4)0.0112 (4)0.0001 (4)
N30.0279 (5)0.0325 (5)0.0327 (5)0.0003 (4)0.0099 (4)0.0045 (4)
C40.0260 (5)0.0345 (6)0.0305 (6)0.0021 (5)0.0076 (4)0.0026 (5)
C50.0286 (5)0.0416 (7)0.0257 (5)0.0015 (5)0.0085 (4)0.0012 (5)
C60.0267 (5)0.0340 (6)0.0257 (5)0.0043 (4)0.0107 (4)0.0011 (4)
N210.0312 (5)0.0375 (6)0.0292 (5)0.0024 (4)0.0072 (4)0.0065 (4)
C410.0291 (5)0.0325 (6)0.0292 (5)0.0044 (5)0.0080 (4)0.0022 (5)
C420.0267 (5)0.0334 (6)0.0302 (5)0.0018 (5)0.0086 (4)0.0014 (5)
C430.0277 (6)0.0417 (7)0.0531 (8)0.0082 (5)0.0115 (5)0.0130 (6)
C440.0333 (6)0.0423 (8)0.0566 (8)0.0063 (6)0.0128 (6)0.0191 (6)
C44a0.0287 (6)0.0372 (7)0.0341 (6)0.0007 (5)0.0086 (5)0.0003 (5)
C450.0358 (6)0.0440 (8)0.0398 (7)0.0025 (6)0.0127 (5)0.0042 (6)
C460.0305 (6)0.0530 (8)0.0380 (6)0.0062 (6)0.0137 (5)0.0092 (6)
C470.0266 (6)0.0543 (9)0.0496 (8)0.0074 (6)0.0110 (5)0.0026 (7)
C480.0313 (6)0.0439 (8)0.0428 (7)0.0095 (5)0.0103 (5)0.0048 (6)
C48a0.0263 (5)0.0344 (6)0.0291 (5)0.0042 (5)0.0070 (4)0.0024 (5)
O1460.0342 (5)0.0753 (8)0.0545 (6)0.0089 (5)0.0201 (5)0.0028 (6)
C1460.0525 (9)0.0758 (12)0.0480 (8)0.0214 (8)0.0243 (7)0.0085 (8)
N610.0432 (6)0.0574 (8)0.0340 (5)0.0101 (5)0.0215 (5)0.0100 (5)
C620.0326 (6)0.0459 (7)0.0298 (6)0.0054 (5)0.0137 (5)0.0026 (5)
C630.0227 (5)0.0387 (6)0.0272 (5)0.0066 (4)0.0105 (4)0.0050 (5)
C640.0314 (6)0.0377 (7)0.0328 (6)0.0060 (5)0.0154 (5)0.0034 (5)
C650.0393 (7)0.0381 (7)0.0480 (7)0.0037 (5)0.0222 (6)0.0058 (6)
C660.0452 (7)0.0478 (8)0.0466 (7)0.0075 (6)0.0272 (6)0.0141 (6)
O710.0618 (6)0.0328 (5)0.0380 (5)0.0013 (4)0.0215 (4)0.0009 (4)
Geometric parameters (Å, º) top
N1—C21.3189 (15)C46—O1461.3734 (16)
C2—N31.3447 (15)C46—C471.407 (2)
N3—C41.4668 (15)C47—C481.365 (2)
N3—H30.9212C47—H470.9500
C4—C51.5005 (17)C48—C48a1.4202 (16)
C4—C421.5232 (16)C48a—C411.4224 (17)
C4—H41.0000C44a—C48a1.4133 (18)
C5—C61.3389 (17)C48—H480.9500
C5—H50.9500O146—C1461.417 (2)
C6—N11.4096 (14)C146—H46A0.9800
C2—N211.3563 (14)C146—H46B0.9800
N21—H2110.8981C146—H46C0.9800
N21—H2120.8912N61—C621.3368 (17)
C6—C631.4848 (16)N61—C661.338 (2)
C41—C421.3692 (16)C62—C631.3966 (16)
C41—H410.9500C62—H620.9500
C42—C431.4141 (18)C63—C641.3877 (18)
C43—C441.3640 (19)C64—C651.3857 (18)
C43—H430.9500C64—H640.9500
C44—C44a1.4172 (17)C65—C661.378 (2)
C44—H440.9500C65—H650.9500
C44a—C451.4211 (18)C66—H660.9500
C45—C461.3637 (19)O71—H7110.8845
C45—H450.9500O71—H7120.9034
C2—N1—C6114.59 (10)C46—C45—H45120.1
N1—C2—N3124.70 (10)C44a—C45—H45120.1
N1—C2—N21118.69 (10)C45—C46—O146125.24 (14)
N3—C2—N21116.61 (10)C45—C46—C47120.38 (12)
C2—N3—C4123.13 (10)C47—C46—O146114.39 (12)
C2—N3—H3116.1C48—C47—C46120.99 (12)
C4—N3—H3120.3C48—C47—H47119.5
N3—C4—C5107.56 (9)C46—C47—H47119.5
N3—C4—C42111.98 (10)C47—C48—C48a120.42 (13)
C5—C4—C42111.00 (10)C47—C48—H48119.8
N3—C4—H4108.7C48a—C48—H48119.8
C5—C4—H4108.7C44a—C48a—C48118.25 (12)
C42—C4—H4108.7C44a—C48a—C41119.46 (11)
C6—C5—C4121.08 (10)C48—C48a—C41122.29 (12)
C6—C5—H5119.5C46—O146—C146116.82 (12)
C4—C5—H5119.5O146—C146—H46A109.5
C5—C6—N1124.13 (11)O146—C146—H46B109.5
C5—C6—C63121.87 (10)H46A—C146—H46B109.5
N1—C6—C63114.00 (10)O146—C146—H46C109.5
C2—N21—H211117.3H46A—C146—H46C109.5
C2—N21—H212115.8H46B—C146—H46C109.5
H211—N21—H212115.8C62—N61—C66117.56 (12)
C42—C41—C48a121.14 (11)N61—C62—C63123.91 (13)
C42—C41—H41119.4N61—C62—H62118.0
C48a—C41—H41119.4C63—C62—H62118.0
C41—C42—C43118.98 (11)C64—C63—C62116.95 (11)
C41—C42—C4121.70 (11)C64—C63—C6121.84 (10)
C43—C42—C4119.28 (10)C62—C63—C6121.20 (11)
C44—C43—C42121.15 (12)C65—C64—C63119.75 (12)
C44—C43—H43119.4C65—C64—H64120.1
C42—C43—H43119.4C63—C64—H64120.1
C43—C44—C44a121.04 (13)C66—C65—C64118.66 (14)
C43—C44—H44119.5C66—C65—H65120.7
C44a—C44—H44119.5C64—C65—H65120.7
C48a—C44a—C44118.23 (11)N61—C66—C65123.12 (13)
C48a—C44a—C45120.15 (11)N61—C66—H66118.4
C44—C44a—C45121.63 (12)C65—C66—H66118.4
C46—C45—C44a119.80 (13)H711—O71—H712106.6
C6—N1—C2—N38.17 (16)C44a—C45—C46—C470.9 (2)
C6—N1—C2—N21172.54 (10)C45—C46—C47—C481.4 (2)
N1—C2—N3—C410.46 (18)O146—C46—C47—C48178.96 (13)
N21—C2—N3—C4168.84 (10)C46—C47—C48—C48a0.5 (2)
C2—N3—C4—C523.21 (15)C44—C44a—C48a—C48179.05 (13)
C2—N3—C4—C4299.00 (13)C45—C44a—C48a—C481.22 (18)
N3—C4—C5—C619.82 (16)C44—C44a—C48a—C410.49 (18)
C42—C4—C5—C6103.00 (13)C45—C44a—C48a—C41179.23 (12)
C4—C5—C6—N14.27 (19)C47—C48—C48a—C44a0.7 (2)
C4—C5—C6—C63176.20 (11)C47—C48—C48a—C41179.73 (12)
C2—N1—C6—C511.10 (17)C42—C41—C48a—C44a0.35 (18)
C2—N1—C6—C63168.46 (10)C42—C41—C48a—C48179.17 (12)
C48a—C41—C42—C430.24 (18)C45—C46—O146—C1466.6 (2)
C48a—C41—C42—C4177.88 (11)C47—C46—O146—C146173.76 (13)
N3—C4—C42—C41124.93 (12)C66—N61—C62—C630.70 (19)
C5—C4—C42—C41114.84 (13)N61—C62—C63—C642.14 (18)
N3—C4—C42—C4357.43 (15)N61—C62—C63—C6178.00 (11)
C5—C4—C42—C4362.80 (14)C5—C6—C63—C64144.25 (12)
C41—C42—C43—C440.7 (2)N1—C6—C63—C6436.18 (15)
C4—C42—C43—C44178.40 (13)C5—C6—C63—C6235.90 (17)
C42—C43—C44—C44a0.6 (2)N1—C6—C63—C62143.67 (11)
C43—C44—C44a—C48a0.1 (2)C62—C63—C64—C652.19 (17)
C43—C44—C44a—C45179.67 (14)C6—C63—C64—C65177.96 (11)
C48a—C44a—C45—C460.4 (2)C63—C64—C65—C660.94 (18)
C44—C44a—C45—C46179.85 (13)C62—N61—C66—C650.7 (2)
C44a—C45—C46—O146179.50 (12)C64—C65—C66—N610.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O710.922.052.8795 (14)149
N21—H211···O710.902.102.9132 (15)150
N21—H212···N1i0.892.143.0327 (15)175
O71—H711···N61ii0.881.902.7751 (16)171
O71—H712···N1iii0.902.102.9940 (14)169
Symmetry codes: (i) x+2, y+1, z+1; (ii) x, y+1/2, z+1/2; (iii) x, y1, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC19H15NO2C20H18N4O·H2O
Mr289.32348.40
Crystal system, space groupOrthorhombic, Pca21Monoclinic, P21/c
Temperature (K)200200
a, b, c (Å)14.2636 (6), 16.6789 (6), 6.0084 (2)17.2244 (5), 5.9552 (2), 18.5173 (6)
α, β, γ (°)90, 90, 9090, 112.830 (1), 90
V3)1429.41 (9)1750.61 (10)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.090.09
Crystal size (mm)0.45 × 0.28 × 0.130.67 × 0.54 × 0.32
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Bruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Multi-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.811, 0.9890.895, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
3474, 3440, 3106 15830, 4319, 3596
Rint0.0210.014
(sin θ/λ)max1)0.6680.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.100, 1.08 0.041, 0.116, 1.04
No. of reflections34404319
No. of parameters200236
No. of restraints10
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.180.29, 0.17
Absolute structureFlack x parameter determined using 1281 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)?
Absolute structure parameter0.0 (4)?

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009) and SHELXL2014 (Sheldrick, 2014).

Selected geometric parameters (Å, º) for (I) top
C31—C321.376 (3)C36—C371.417 (3)
C32—C331.427 (3)C37—C381.359 (3)
C33—C341.363 (3)C38—C38a1.419 (3)
C34—C34a1.420 (3)C38a—C311.412 (2)
C34a—C351.420 (3)C34a—C38a1.426 (2)
C35—C361.371 (3)
O136—C36—C35125.51 (19)O136—C36—C37113.91 (17)
C13—C1—C2—C3161.6 (2)C2—C3—C32—C31174.8 (2)
C1—C2—C3—C32175.30 (19)C35—C36—O136—C1368.9 (3)
C2—C1—C13—C12160.4 (2)
Hydrogen-bond geometry (Å, º) for (I) top
Cg1, Cg2 and Cg3 represent the centroids of the rings N11/C12–C16, C31–C34/C34a/C38a and C34a/C35–C38/C38a, respectively.
D—H···AD—HH···AD···AD—H···A
C16—H16···O136i0.952.453.364 (3)162
C136—H36A···N11ii0.982.633.526 (3)152
C3—H3···Cg3iii0.952.943.518 (2)121
C12—H12···Cg1iv0.952.933.555 (3)125
C31—H31···Cg2iii0.952.813.527 (2)133
C34—H34···Cg2v0.952.673.391 (2)133
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z1; (iii) x, y+1, z+1/2; (iv) x+1/2, y, z+1/2; (v) x+1/2, y, z1/2.
Selected geometric parameters (Å, º) for (II) top
N1—C21.3189 (15)C43—C441.3640 (19)
C2—N31.3447 (15)C44—C44a1.4172 (17)
N3—C41.4668 (15)C44a—C451.4211 (18)
C4—C51.5005 (17)C45—C461.3637 (19)
C5—C61.3389 (17)C46—C471.407 (2)
C6—N11.4096 (14)C47—C481.365 (2)
C2—N211.3563 (14)C48—C48a1.4202 (16)
C41—C421.3692 (16)C48a—C411.4224 (17)
C42—C431.4141 (18)C44a—C48a1.4133 (18)
C45—C46—O146125.24 (14)C47—C46—O146114.39 (12)
C45—C46—O146—C1466.6 (2)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O710.922.052.8795 (14)149
N21—H211···O710.902.102.9132 (15)150
N21—H212···N1i0.892.143.0327 (15)175
O71—H711···N61ii0.881.902.7751 (16)171
O71—H712···N1iii0.902.102.9940 (14)169
Symmetry codes: (i) x+2, y+1, z+1; (ii) x, y+1/2, z+1/2; (iii) x, y1, z.
 

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