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In the title compound, C20H13ClN4O4, the six-membered heterocyclic ring is planar and the mol­ecular dimensions provide evidence for polarization of the mol­ecular-electronic structure. Mol­ecules are linked into a chain of rings by a combination of N-H...O and C-H...O hydrogen bonds, but the nitro group does not participate in the supra­molecular aggregation. This study illustrates the marked influence of peripheral substituents on the pattern of hydrogen-bonded aggregation in compounds of this type.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108014509/sk3236sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270108014509/sk3236Isup2.hkl
Contains datablock I

CCDC reference: 692671

Comment top

As part of a continuing search for biologically active molecules containing fused pyrazole systems, we have now (Quiroga et al., 2008) prepared the title compound, (I), by use of the Vilsmeier–Haack reaction to effect double formylation of the precursor (A) (see the first scheme), itself formed by condensation of the simple reagents (B) and (C). Product (I) is of potential value as a precursor for modified or fused polycyclic pyrazolo[1,5-a]pyrimidine systems. We report here the structure of (I) and compare it with the closely related analogue, (II) (Low et al., 2006). Both the molecular structure of (I) (Fig. 1) and its supramolecular aggregation show significant differences from those of compound (II), whose constitution differs from that of (I) not only in the nature of the 4-substituents in the aryl rings pendent from positions 2 and 5, but also in the presence of an additional unsubstituted phenyl ring at position 7.

Within the molecule of (I), the six-membered heterocyclic ring is effectively planar: the maximum deviation from the mean plane through the six ring atoms is 0.021 (3) Å for atom C6. This contrasts with the corresponding ring in compound (II), which is significantly puckered into a non-planar conformation intermediate between boat and screw-boat forms (Low et al., 2006). The overall conformation of the molecule of (I) can thus be defined in terms of five torsion angles (Table 1) which show that, apart from the nitro group which makes a dihedral angle of 9.4 (2)° with the adjacent aryl ring, the conformation of (I) is broadly similar to that of (II). In particular, the two independent carboxaldehyde groups in (I) are both nearly coplanar with the heterocyclic ring system, with deviations from the mean ring plane of 0.236 (3) Å for atom O31 and 0.106 (2) Å for atom O61. While the short intramolecular N—H···O hydrogen bond to atom O31 (Table 2) may influence the orientation of one carboxaldehyde group, there is no corresponding interaction which could influence the orientation of the carboxaldehyde group bonded to atom C6. However, the intramolecular dimensions of (I) (Table 1) provide some evidence for the polarization of its molecular structure, such that the potential for electronic delocalization is optimized when the carboxaldehyde groups are coplanar with the heterocyclic system, and this may thus be the dominant factor controlling the orientation of the carboxaldehyde groups. Firstly, the C31—O31 and C61—O61 bonds are both long for their type [mean value 1.192 Å (Allen et al., 1987)], while the C3—C31 and C6—C61 bonds are both short (mean value 1.464 Å). Secondly, the C5—C6 bond is long for its type (mean value 1.331 Å), and the C3a—N4 and N4—C5 bonds have almost identical lengths. These observations, taken all together, indicate that polarized forms such as (Ia)–(Ic) (see the second scheme) are contributors to the overall molecular-electronic structure. The molecular dimensions of compound (II) were not discussed in the original report (Low et al., 2006), but re-examination of the structure of (II) shows that it exhibits exactly the same pattern of intramolecular distances as found here for (I), pointing to a similar interpretation of the carboxaldehyde conformations.

The intramolecular hydrogen bond mentioned earlier forms an S(6) motif (Bernstein et al., 1995) and it is, in fact, the longer and weaker component of an asymmetric three-centre N—H···(O)2 system (Table 2), in which the shorter component links the molecules at (x, y, z) and (1/2 - x, 1/2 + y, 1/2 - z), which are related by the 21 screw axis along (1/4, y, 1/4). Propagation of this hydrogen bond forms a C(6) chain running parallel to the [010] direction (Fig. 2). This [010] chain is reinforced by a C—H···O hydrogen bond which forms a C(9) chain, and the combination of all these hydrogen bonds generates an S(6)C(6)C(9)[R22(5)] chain of rings (Fig. 2). In this chain, the R22(5) motif actually contains three hydrogen bonds, but atoms H4 and O31 act, respectively, as a double donor and a double acceptor. Four chains of this type pass through each unit cell, but there are no direction-specific interactions between the chains.

It is interesting to note that, despite the large excess in (I) of potential hydrogen-bond donors in the form of aromatic C—H bonds over potential hydrogen-bond acceptors, the O atoms of the nitro group play no part in the hydrogen bonding. Nor are there any dipolar nitro···nitro interactions (Garden et al., 2006; Glidewell et al., 2006), analogous to the well documented dipolar carbonyl···carbonyl interactions (Allen et al., 1998).

The action of the hydrogen bonds in (I) differs from that in (II) (Low et al., 2006). While (II) also contains an asymmetric N—H···(O)2 system, the shorter component generates a centrosymmetric dimer containing an R22(12) motif, rather than a C(6) chain as in (I). There are two C—H···O hydrogen bonds in the structure of (II), which link the R22(12) dimers into sheets, but both of these donor atoms are components of the unsubstituted phenyl ring, which is absent from the constitution of (I). Hence, the supramolecular aggregation in compounds of this type is very markedly influenced by the nature of the peripheral substituents.

Experimental top

A mixture of 5-amino-3-(4-chlorophenyl-1H-pyrazole, (B) (1.9 mmol), and 1-(4-nitrophenyl)-propenone, (C) (1.9 mmol), in dimethylformamide (1 ml) was heated under reflux for 20 min to afford the intermediate, 2-(4-chlorophenyl)-5-(4-nitrophenyl)-4,7- dihydropyrazolo[1,5-a]pyrimidine, (A). The reaction mixture was cooled to ambient temperature and the intermediate was collected by filtration, washed with ethanol and dried, and then purified by chromatography on alumina using chloroform as the eluent. Phosphoryl chloride (2.1 mmol) was then added dropwise to a suspension of the pyrazolopyrimidine intermediate (1.0 mmol) in dimethylformamide (2 ml) at 273 K. When the addition had been completed the reaction mixture was stirred vigorously for 0.5 h at ambient temperature. The resulting solid product, (I), was collected by filtration, dried and recrystallized from dimethylformamide to give yellow crystals suitable for single-crystal X-ray diffraction (yield 65%, m.p. 555–557 K). Spectroscopic analysis: MS (m/z, %) 410/408 (35/100, M+), 407 (53), 361 (51), 350 (70), 102 (31), 75 (42), 40 (82).

Refinement top

The systematic absences permitted C2/c and Cc as possible space groups. C2/c was selected, and confirmed by the subsequent structure analysis. All H atoms were located in difference maps and then treated as riding atoms, with C—H = 0.99 (CH2) or 0.95 Å (all other H atoms) and N—H 0.88 Å, and with Uiso(H) = 1.2Ueq(parent).

Computing details top

Data collection: COLLECT (Nonius, 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: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A stereoview of part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded chain of rings. For the sake of clarity, H atoms bonded to ring C atoms have been omitted.
2-(4-Chlorophenyl)-5-(4-nitrophenyl)-4,7- dihydropyrazolo[1,5-a]pyrimidine-3,6-dicarbaldehyde top
Crystal data top
C20H13ClN4O4F(000) = 1680
Mr = 408.79Dx = 1.558 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4002 reflections
a = 23.943 (5) Åθ = 3.8–27.5°
b = 13.445 (2) ŵ = 0.26 mm1
c = 12.336 (5) ÅT = 120 K
β = 118.594 (10)°Block, colourless
V = 3486.7 (17) Å30.46 × 0.36 × 0.24 mm
Z = 8
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
4002 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode2520 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.8°
ϕ and ω scansh = 3131
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1716
Tmin = 0.891, Tmax = 0.941l = 1615
40202 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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0465P)2 + 9.8005P]
where P = (Fo2 + 2Fc2)/3
4002 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C20H13ClN4O4V = 3486.7 (17) Å3
Mr = 408.79Z = 8
Monoclinic, C2/cMo Kα radiation
a = 23.943 (5) ŵ = 0.26 mm1
b = 13.445 (2) ÅT = 120 K
c = 12.336 (5) Å0.46 × 0.36 × 0.24 mm
β = 118.594 (10)°
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
4002 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2520 reflections with I > 2σ(I)
Tmin = 0.891, Tmax = 0.941Rint = 0.066
40202 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.09Δρmax = 0.36 e Å3
4002 reflectionsΔρmin = 0.43 e Å3
262 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl240.57868 (3)0.28471 (6)1.23489 (6)0.0334 (2)
O310.37089 (10)0.53108 (15)0.53537 (17)0.0328 (5)
O610.20351 (9)0.04486 (13)0.23740 (17)0.0267 (4)
O5410.06077 (10)0.47143 (16)0.24494 (19)0.0384 (5)
O5420.14516 (11)0.45976 (17)0.26641 (19)0.0397 (6)
N10.37250 (10)0.20177 (16)0.63810 (19)0.0212 (5)
N40.30105 (10)0.35687 (16)0.37383 (18)0.0209 (5)
N7a0.33309 (10)0.22484 (16)0.51655 (19)0.0201 (5)
N540.11720 (12)0.45234 (17)0.2053 (2)0.0285 (6)
C20.40156 (12)0.28667 (19)0.6894 (2)0.0192 (5)
C30.38083 (12)0.36589 (19)0.6023 (2)0.0199 (5)
C3a0.33697 (12)0.32057 (19)0.4917 (2)0.0196 (5)
C50.25899 (12)0.29502 (19)0.2826 (2)0.0184 (5)
C60.25238 (12)0.19857 (19)0.3066 (2)0.0196 (5)
C70.29180 (12)0.15067 (19)0.4309 (2)0.0214 (6)
C210.44740 (12)0.28813 (19)0.8235 (2)0.0197 (5)
C220.48543 (12)0.2050 (2)0.8789 (2)0.0214 (6)
C230.52645 (12)0.2035 (2)1.0055 (2)0.0237 (6)
C240.52908 (12)0.2853 (2)1.0757 (2)0.0235 (6)
C250.49190 (13)0.3679 (2)1.0228 (2)0.0261 (6)
C260.45100 (12)0.3691 (2)0.8968 (2)0.0237 (6)
C310.39776 (13)0.4690 (2)0.6164 (2)0.0243 (6)
C510.22207 (12)0.34056 (19)0.1571 (2)0.0198 (6)
C520.25311 (13)0.3684 (2)0.0912 (2)0.0234 (6)
C530.21878 (13)0.4055 (2)0.0271 (2)0.0241 (6)
C540.15351 (13)0.41582 (19)0.0774 (2)0.0224 (6)
C550.12178 (13)0.3914 (2)0.0134 (2)0.0240 (6)
C560.15671 (13)0.3539 (2)0.1057 (2)0.0240 (6)
C610.20890 (12)0.1314 (2)0.2131 (2)0.0228 (6)
H40.30440.41900.35510.025*
H7A0.26370.12240.46120.026*
H7B0.31760.09600.42370.026*
H220.48330.14920.82980.026*
H230.55230.14701.04320.028*
H250.49430.42351.07230.031*
H260.42510.42590.86000.028*
H310.43180.49040.69300.029*
H520.29800.36180.12750.028*
H530.23960.42370.07330.029*
H550.07700.40000.04950.029*
H560.13580.33730.15210.029*
H610.18390.15480.13100.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl240.0346 (4)0.0341 (4)0.0177 (3)0.0021 (3)0.0014 (3)0.0000 (3)
O310.0401 (12)0.0239 (11)0.0253 (10)0.0019 (9)0.0082 (9)0.0039 (9)
O610.0333 (11)0.0170 (10)0.0243 (10)0.0025 (8)0.0092 (9)0.0019 (8)
O5410.0308 (12)0.0391 (13)0.0303 (11)0.0055 (10)0.0027 (9)0.0110 (10)
O5420.0502 (14)0.0460 (14)0.0236 (11)0.0016 (11)0.0183 (10)0.0070 (10)
N10.0227 (11)0.0226 (12)0.0146 (10)0.0007 (9)0.0059 (9)0.0010 (9)
N40.0262 (12)0.0152 (11)0.0157 (10)0.0005 (9)0.0055 (9)0.0012 (9)
N7a0.0223 (11)0.0195 (11)0.0150 (10)0.0005 (9)0.0060 (9)0.0004 (9)
N540.0346 (14)0.0234 (13)0.0208 (12)0.0015 (11)0.0080 (11)0.0032 (10)
C20.0184 (12)0.0207 (13)0.0189 (12)0.0016 (10)0.0091 (11)0.0004 (11)
C30.0203 (13)0.0187 (13)0.0166 (12)0.0005 (10)0.0056 (10)0.0018 (10)
C3a0.0184 (13)0.0204 (13)0.0208 (13)0.0009 (10)0.0101 (11)0.0021 (11)
C50.0194 (12)0.0191 (13)0.0154 (12)0.0008 (10)0.0073 (10)0.0029 (10)
C60.0182 (12)0.0217 (14)0.0171 (12)0.0008 (11)0.0070 (10)0.0009 (10)
C70.0245 (14)0.0178 (13)0.0194 (13)0.0015 (11)0.0084 (11)0.0012 (10)
C210.0177 (12)0.0212 (13)0.0182 (12)0.0025 (10)0.0071 (10)0.0001 (11)
C220.0218 (13)0.0215 (14)0.0199 (13)0.0015 (11)0.0092 (11)0.0001 (11)
C230.0204 (13)0.0261 (15)0.0216 (13)0.0008 (11)0.0076 (11)0.0057 (11)
C240.0208 (13)0.0289 (15)0.0166 (12)0.0038 (11)0.0055 (11)0.0010 (11)
C250.0259 (14)0.0267 (15)0.0222 (14)0.0031 (12)0.0087 (12)0.0045 (12)
C260.0221 (14)0.0224 (14)0.0244 (14)0.0000 (11)0.0094 (11)0.0021 (11)
C310.0239 (14)0.0227 (14)0.0204 (13)0.0031 (11)0.0059 (11)0.0012 (11)
C510.0245 (14)0.0158 (13)0.0170 (12)0.0011 (10)0.0081 (11)0.0032 (10)
C520.0212 (13)0.0258 (14)0.0217 (13)0.0011 (11)0.0090 (11)0.0011 (11)
C530.0285 (15)0.0255 (15)0.0223 (13)0.0007 (12)0.0153 (12)0.0006 (11)
C540.0276 (14)0.0178 (13)0.0179 (13)0.0016 (11)0.0078 (11)0.0002 (10)
C550.0221 (13)0.0219 (14)0.0224 (14)0.0003 (11)0.0061 (11)0.0026 (11)
C560.0256 (14)0.0241 (14)0.0226 (13)0.0017 (11)0.0118 (12)0.0011 (11)
C610.0228 (14)0.0216 (14)0.0208 (13)0.0017 (11)0.0078 (11)0.0012 (11)
Geometric parameters (Å, º) top
Cl24—C241.742 (3)C21—C261.391 (4)
O541—N541.224 (3)C21—C221.396 (4)
O542—N541.229 (3)C22—C231.391 (4)
N1—C21.329 (3)C22—H220.95
C2—C31.423 (4)C23—C241.382 (4)
C3—C3a1.401 (4)C23—H230.95
C3a—N41.377 (3)C24—C251.376 (4)
N4—C51.374 (3)C25—C261.385 (4)
C5—C61.356 (4)C25—H250.95
C6—C71.507 (4)C26—H260.95
C7—N7a1.445 (3)C31—H310.95
N7a—N11.371 (3)C51—C561.390 (4)
C3a—N7a1.337 (3)C51—C521.391 (4)
C3—C311.432 (4)C52—C531.381 (4)
C31—O311.222 (3)C52—H520.95
C6—C611.442 (4)C53—C541.385 (4)
C61—O611.223 (3)C53—H530.95
N4—H40.88C54—C551.372 (4)
N54—C541.474 (3)C55—C561.392 (4)
C2—C211.484 (3)C55—H550.95
C5—C511.497 (3)C56—H560.95
C7—H7A0.99C61—H610.95
C7—H7B0.99
C2—N1—N7a104.8 (2)C24—C23—C22119.2 (2)
C5—N4—C3a119.5 (2)C24—C23—H23120.4
C5—N4—H4118.9C22—C23—H23120.4
C3a—N4—H4121.6C25—C24—C23121.3 (2)
C3a—N7a—N1112.4 (2)C25—C24—Cl24118.4 (2)
C3a—N7a—C7126.5 (2)C23—C24—Cl24120.3 (2)
N1—N7a—C7121.0 (2)C24—C25—C26119.4 (3)
O541—N54—O542124.0 (2)C24—C25—H25120.3
O541—N54—C54118.1 (2)C26—C25—H25120.3
O542—N54—C54117.9 (2)C25—C26—C21120.7 (3)
N1—C2—C3111.7 (2)C25—C26—H26119.7
N1—C2—C21118.8 (2)C21—C26—H26119.7
C3—C2—C21129.5 (2)O31—C31—C3123.7 (2)
C3a—C3—C2103.8 (2)O31—C31—H31118.2
C3a—C3—C31125.2 (2)C3—C31—H31118.2
C2—C3—C31131.1 (2)C56—C51—C52119.9 (2)
N7a—C3a—N4120.4 (2)C56—C51—C5120.2 (2)
N7a—C3a—C3107.3 (2)C52—C51—C5119.9 (2)
N4—C3a—C3132.2 (2)C53—C52—C51120.1 (2)
C6—C5—N4121.1 (2)C53—C52—H52120.0
C6—C5—C51123.0 (2)C51—C52—H52120.0
N4—C5—C51116.0 (2)C52—C53—C54118.9 (3)
C5—C6—C61122.6 (2)C52—C53—H53120.6
C5—C6—C7123.3 (2)C54—C53—H53120.6
C61—C6—C7114.0 (2)C55—C54—C53122.4 (2)
N7a—C7—C6109.0 (2)C55—C54—N54119.3 (2)
N7a—C7—H7A109.9C53—C54—N54118.3 (2)
C6—C7—H7A109.9C54—C55—C56118.4 (3)
N7a—C7—H7B109.9C54—C55—H55120.8
C6—C7—H7B109.9C56—C55—H55120.8
H7A—C7—H7B108.3C51—C56—C55120.3 (3)
C26—C21—C22119.0 (2)C51—C56—H56119.8
C26—C21—C2121.1 (2)C55—C56—H56119.8
C22—C21—C2119.7 (2)O61—C61—C6121.3 (2)
C23—C22—C21120.4 (2)O61—C61—H61119.3
C23—C22—H22119.8C6—C61—H61119.3
C21—C22—H22119.8
C2—N1—N7a—C3a0.0 (3)C26—C21—C22—C230.2 (4)
C2—N1—N7a—C7178.3 (2)C2—C21—C22—C23176.9 (2)
N7a—N1—C2—C30.7 (3)C21—C22—C23—C240.0 (4)
N7a—N1—C2—C21178.8 (2)C22—C23—C24—C250.1 (4)
N1—C2—C3—C3a1.1 (3)C22—C23—C24—Cl24178.6 (2)
C21—C2—C3—C3a179.0 (2)C23—C24—C25—C260.0 (4)
N1—C2—C3—C31178.5 (3)Cl24—C24—C25—C26178.5 (2)
C21—C2—C3—C310.6 (5)C24—C25—C26—C210.2 (4)
N1—N7a—C3a—N4179.5 (2)C22—C21—C26—C250.3 (4)
C7—N7a—C3a—N42.4 (4)C2—C21—C26—C25177.0 (2)
N1—N7a—C3a—C30.7 (3)C3a—C3—C31—O317.6 (5)
C7—N7a—C3a—C3177.5 (2)C2—C3—C31—O31171.9 (3)
C5—N4—C3a—N7a2.8 (4)C5—C6—C61—O61179.5 (3)
C5—N4—C3a—C3177.0 (3)C6—C5—C51—C5667.8 (4)
C2—C3—C3a—N7a1.0 (3)N4—C5—C51—C56112.6 (3)
C31—C3—C3a—N7a178.6 (3)C6—C5—C51—C52111.4 (3)
C2—C3—C3a—N4179.1 (3)N4—C5—C51—C5268.2 (3)
C31—C3—C3a—N41.3 (5)C56—C51—C52—C532.6 (4)
C3a—N4—C5—C60.2 (4)C5—C51—C52—C53176.6 (2)
C3a—N4—C5—C51179.8 (2)C51—C52—C53—C541.0 (4)
N4—C5—C6—C61179.8 (2)C52—C53—C54—C550.7 (4)
C51—C5—C6—C610.2 (4)C52—C53—C54—N54178.0 (2)
N4—C5—C6—C73.0 (4)O541—N54—C54—C558.9 (4)
C51—C5—C6—C7176.6 (2)O542—N54—C54—C55169.6 (2)
C3a—N7a—C7—C60.5 (4)C53—C54—N54—O541172.4 (2)
N1—N7a—C7—C6177.5 (2)O542—N54—C54—C539.1 (4)
C5—C6—C7—N7a3.2 (4)C53—C54—C55—C560.8 (4)
C61—C6—C7—N7a179.8 (2)N54—C54—C55—C56177.8 (2)
N1—C2—C21—C26141.7 (3)C52—C51—C56—C552.5 (4)
C3—C2—C21—C2636.1 (4)C5—C51—C56—C55176.7 (2)
N1—C2—C21—C2235.0 (4)C54—C55—C56—C510.8 (4)
C3—C2—C21—C22147.2 (3)C7—C6—C61—O613.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O310.882.523.011 (3)116
N4—H4···O61i0.882.002.853 (3)163
C61—H61···O31ii0.952.473.043 (3)118
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC20H13ClN4O4
Mr408.79
Crystal system, space groupMonoclinic, C2/c
Temperature (K)120
a, b, c (Å)23.943 (5), 13.445 (2), 12.336 (5)
β (°) 118.594 (10)
V3)3486.7 (17)
Z8
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.46 × 0.36 × 0.24
Data collection
DiffractometerBruker Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.891, 0.941
No. of measured, independent and
observed [I > 2σ(I)] reflections
40202, 4002, 2520
Rint0.066
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.139, 1.09
No. of reflections4002
No. of parameters262
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.43

Computer programs: COLLECT (Nonius, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005), OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 2008) and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
N1—C21.329 (3)C7—N7a1.445 (3)
C2—C31.423 (4)N7a—N11.371 (3)
C3—C3a1.401 (4)C3a—N7a1.337 (3)
C3a—N41.377 (3)C3—C311.432 (4)
N4—C51.374 (3)C31—O311.222 (3)
C5—C61.356 (4)C6—C611.442 (4)
C6—C71.507 (4)C61—O611.223 (3)
N1—C2—C21—C2235.0 (4)N4—C5—C51—C5268.2 (3)
C2—C3—C31—O31171.9 (3)C53—C54—N54—O541172.4 (2)
C5—C6—C61—O61179.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O310.882.523.011 (3)116
N4—H4···O61i0.882.002.853 (3)163
C61—H61···O31ii0.952.473.043 (3)118
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1/2, y1/2, z+1/2.
 

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