supplementary materials


lr2118 scheme

Acta Cryst. (2013). E69, o1859-o1860    [ doi:10.1107/S1600536813032212 ]

4-[(tert-Butyl­diphenyl­sil­yloxy)meth­yl]pyridazin-3(2H)-one

M. C. Costas-Lago, T. Costas, N. Vila and P. Besada

Abstract top

In the title compound, C21H24N2O2Si, the carbonyl group of the heterocyclic ring and the O atom of the silyl ether group are placed toward opposite sides and the tert-butyl and pyridazinone moieties are anti-oriented across the Si-O bond [torsion angle = -168.44 (19)°]. In the crystal, mol­ecules are assembled into inversion dimers through co-operative N-H...O hydrogen bonds between the NH groups and O atoms of the pyridazinone rings of neighbouring mol­ecules. The dimers are linked by [pi]-[pi] inter­actions involving adjacent pyridazinone rings [centroid-centroid distance = 3.8095 (19) Å], generating ladder-like chains along the b-axis direction. The chains are further linked into a two-dimensional network parallel to the ab plane through weak C-H...[pi] inter­actions.

Introduction top

Pyridazin-3(2H)-one derivatives possess a wide range of biological activities, this fact together with the easy functionalization at various ring positions makes the pyridazinone nucleus a versatile pharmacophore to design and synthesize new drugs. For instance, an important number of pyridazinones have been reported as anti­hypertensive (Siddiqui et al., 2010), anti­platelet (Costas et al., 2010), anti-inflammatory (Abouzid & Bekhit, 2008), anti­nociceptive (Cesari et al., 2006), anti­diabetic (Rathish et al., 2009), anti­cancer (Al-Tel, 2010), anti­microbial (Suree et al., 2009) or anti-histamine H3 agents (Tao et al., 2011).

Experimental top

Synthesis and crystallization top

A solution of 3-(tert-butyl­diphenyl­silyloxymethyl)-5-hy­droxy-5H-furan-2-ona (50 mg, 0.136 mmol) and hydrazine monohydrate (14 ml, 0.284 mmol) in ethanol (2 ml) was stirred at reflux for 4 h. The solvent was evaporated under reduced pressure and residue was purified by column chromatography on silica gel (hexane/ethyl acetate 4:1) to afford a colourless oil (16 mg, 32%). Single crystals suitable for X-ray analysis were grown from a chloro­form solution at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H-atoms were positioned and refined using a riding model with d(C—H)= 0.93 Å, Uiso = 1.2Ueq(C) for aromatic C—H groups,d(C—H)= 0.97 Å, Uiso = 1.2Ueq(C) for CH2 group and d(C—H)= 0.96 Å, Uiso = 1.5Ueq(C) for CH3 group; except for the hydrogen atoms of the NH group which were located from a Fourier-difference map and refined isotropically

Results and discussion top

The compound I, an isomer of the 5-(tert-butyl­diphenyl­silyloxymethyl)­pyridazin-3(2H)-one (Costas-Lago et al., 2013), was prepared in order to develop new pyridazinone analogues C4-substituted as anti­platelet agents. In the titled compound, the carbonyl group of the heterocyclic ring and the oxygen atom of the silyl ether group are placed toward opposite sides, this contrasts with the geometry found in the C5-substituted regioisomer and could explain the nearly flat disposition of the sequence C4—C1'-O1'-Si, with a torsion angle of -174.30 (15)°. The pyridazinone ring forms dihedral angles of 89.10 (8)° and 77.53 (7)°, respectively, with the C2'-C7' and C8'-C13' benzene rings, while the dihedral angle between both benzene rings is 48.41 (10)°.

The geometry of titled compound lets the assembly of molecules in supra­molecular organizations based on hydrogen bonding, ππ and CH···π inter­actions. The cooperative N—H···O hydrogen bonds between the NH group of one pyridazinone ring and the oxygen atom of an adjacent ring form supra­molecular dimers (Figure 2). These dimers are joined by ππ inter­actions involving also neighbouring pyridazinone rings [Cg(1): N1—N2—C3—C4—C5—C6; d[Cg(1)—Cg(1)ii]: 3.8095 (19) Å; d[Cg(1)···P(1)ii]: 3.4279 (8) Å; α: 0°; symmetry code ii: 1 - x, 2 - y, -z] resulting in a ladder chain along the crystallographic b axis (Figure 3). Finally, the linear chains are linked into a two-dimensional network through weak C—H···π inter­actions (Figure 4) involving CH groups of the pyridazinone rings and phenyl rings from neighbouring chains [C6—H6···Cg(2)iii; Cg(2): C8'-C9'-C10'-C11'-C12'-C13'; d[H···Cg(2)iii]: 2.890 Å; γ: 17.60°; symmetry code iii: 2 - x, -2 - y, -z]. In this case the pyridazinone ring arrangement prevents the three-dimensional growth observed in the C5-substituted regioisomer (Costas-Lago et al., 2013).

Related literature top

For background to pyridazinone analogues displaying biological activities, see: Siddiqui et al. (2010); Costas et al. (2010); Abouzid & Bekhit (2008); Cesari et al. (2006); Rathish et al. (2009); Al-Tel (2010); Suree et al. (2009); Tao et al. (2011). For related structures, see: Costas et al. (2010); Costas-Lago et al. (2013).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-numbering scheme. Displacement ellipsoids are shown at the 20% probability level.
[Figure 2] Fig. 2. View of supramolecular dimer generated by NH···O hydrogen bonds.
[Figure 3] Fig. 3. View of the ladder chain along crystallographic b axis generated by ππ interactions.
[Figure 4] Fig. 4. View of the two-dimensional organization generated by CH···π interactions (H atoms, no-involved in supramolecular structure, have been omitted to clarify).
4-[(tert-Butyldiphenylsilyloxy)methyl]pyridazin-3(2H)-one top
Crystal data top
C21H24N2O2SiF(000) = 776
Mr = 364.51Dx = 1.158 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5037 reflections
a = 10.774 (4) Åθ = 2.7–23.0°
b = 7.988 (3) ŵ = 0.13 mm1
c = 24.681 (10) ÅT = 293 K
β = 100.207 (7)°Prism, colourless
V = 2090.5 (14) Å30.48 × 0.41 × 0.23 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD
diffractometer
5045 independent reflections
Radiation source: fine-focus sealed tube3076 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 28.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.707, Tmax = 0.746k = 1010
25187 measured reflectionsl = 3232
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0628P)2 + 0.7126P]
where P = (Fo2 + 2Fc2)/3
5045 reflections(Δ/σ)max < 0.001
242 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C21H24N2O2SiV = 2090.5 (14) Å3
Mr = 364.51Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.774 (4) ŵ = 0.13 mm1
b = 7.988 (3) ÅT = 293 K
c = 24.681 (10) Å0.48 × 0.41 × 0.23 mm
β = 100.207 (7)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
5045 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3076 reflections with I > 2σ(I)
Tmin = 0.707, Tmax = 0.746Rint = 0.038
25187 measured reflectionsθmax = 28.0°
Refinement top
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148Δρmax = 0.30 e Å3
S = 1.00Δρmin = 0.24 e Å3
5045 reflectionsAbsolute structure: ?
242 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
Special details top

Experimental. 1H-RMN (400 MHz, CDCl3) δ p.p.m.: 12.32 (s, 1H), 7.90 (d, 1H, J=4.0 Hz), 7.65 (m, 4H), 7.60 (m, 1H), 7.42 (m, 6H), 4.77 (d, 2H, J=1.7 Hz), 1.14 (s, 9H).

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si0.99974 (5)0.99175 (7)0.14301 (2)0.04561 (17)
N10.52674 (18)0.8319 (2)0.06086 (7)0.0653 (5)
H20.487 (2)0.611 (4)0.0346 (11)0.086 (8)*
N20.53846 (17)0.7036 (2)0.02487 (7)0.0574 (5)
C30.62195 (19)0.6898 (3)0.02344 (8)0.0526 (5)
O30.62352 (16)0.5633 (2)0.05259 (7)0.0788 (5)
C40.70446 (17)0.8303 (2)0.03690 (8)0.0467 (4)
C50.6944 (2)0.9595 (3)0.00182 (8)0.0560 (5)
H50.74691.05210.00970.067*
C60.6037 (2)0.9546 (3)0.04720 (9)0.0669 (6)
H60.59931.04540.07100.080*
C1'0.7958 (2)0.8211 (3)0.08991 (9)0.0653 (6)
H1'10.75050.82070.12060.078*
H1'20.84440.71850.09130.078*
O1'0.87743 (14)0.96100 (19)0.09397 (6)0.0627 (4)
C2'0.95347 (19)0.9463 (3)0.21122 (8)0.0543 (5)
C3'0.8587 (3)1.0372 (4)0.22883 (12)0.0840 (8)
H3'0.81721.11980.20590.101*
C4'0.8235 (3)1.0095 (5)0.27923 (15)0.1019 (11)
H4'0.75941.07330.28970.122*
C5'0.8812 (3)0.8910 (5)0.31327 (12)0.0971 (11)
H5'0.85890.87410.34760.117*
C6'0.9719 (3)0.7968 (5)0.29721 (11)0.0973 (10)
H6'1.01090.71310.32030.117*
C7'1.0078 (2)0.8232 (4)0.24653 (10)0.0762 (7)
H7'1.07020.75590.23630.091*
C8'1.1303 (2)0.8497 (3)0.13054 (8)0.0552 (5)
C9'1.1229 (3)0.7655 (3)0.08041 (10)0.0686 (6)
H9'1.05080.77710.05370.082*
C10'1.2208 (3)0.6650 (3)0.06949 (14)0.0907 (9)
H10'1.21410.61150.03560.109*
C11'1.3262 (4)0.6449 (4)0.10820 (17)0.1030 (11)
H11'1.39100.57630.10090.124*
C12'1.3376 (3)0.7244 (4)0.15767 (15)0.0950 (10)
H12'1.41010.71050.18400.114*
C13'1.2403 (2)0.8268 (3)0.16862 (10)0.0727 (7)
H13'1.24920.88130.20240.087*
C14'1.0445 (2)1.2154 (3)0.13265 (9)0.0551 (5)
C15'1.0735 (3)1.2322 (4)0.07485 (11)0.1004 (10)
H15A1.09251.34690.06810.151*
H15B1.00161.19710.04860.151*
H15C1.14461.16330.07140.151*
C16'1.1613 (3)1.2610 (4)0.17343 (14)0.1250 (14)
H16A1.17901.37800.17020.188*
H16B1.23141.19630.16590.188*
H16C1.14771.23770.21010.188*
C17'0.9393 (4)1.3371 (4)0.1387 (2)0.1496 (19)
H17A0.92301.33250.17560.224*
H17B0.86431.30720.11340.224*
H17C0.96431.44860.13080.224*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si0.0432 (3)0.0493 (3)0.0416 (3)0.0068 (2)0.0000 (2)0.0014 (2)
N10.0713 (12)0.0678 (12)0.0512 (10)0.0148 (10)0.0044 (9)0.0040 (9)
N20.0613 (11)0.0557 (11)0.0497 (10)0.0158 (9)0.0052 (8)0.0022 (8)
C30.0539 (12)0.0536 (12)0.0476 (11)0.0110 (9)0.0012 (9)0.0008 (9)
O30.0872 (12)0.0635 (10)0.0720 (10)0.0326 (9)0.0229 (9)0.0162 (8)
C40.0433 (10)0.0514 (11)0.0443 (10)0.0101 (8)0.0048 (8)0.0012 (8)
C50.0542 (12)0.0579 (12)0.0537 (12)0.0164 (10)0.0032 (9)0.0023 (10)
C60.0732 (15)0.0685 (15)0.0541 (12)0.0161 (12)0.0021 (11)0.0137 (11)
C1'0.0649 (14)0.0621 (14)0.0607 (13)0.0267 (11)0.0119 (11)0.0113 (11)
O1'0.0576 (9)0.0637 (9)0.0584 (8)0.0250 (7)0.0126 (7)0.0132 (7)
C2'0.0464 (11)0.0659 (13)0.0495 (11)0.0099 (10)0.0057 (9)0.0012 (10)
C3'0.0783 (17)0.093 (2)0.0888 (19)0.0090 (15)0.0360 (15)0.0102 (15)
C4'0.091 (2)0.129 (3)0.098 (2)0.010 (2)0.0526 (19)0.014 (2)
C5'0.0764 (19)0.160 (3)0.0581 (16)0.042 (2)0.0211 (14)0.0041 (19)
C6'0.0731 (17)0.153 (3)0.0643 (16)0.0122 (19)0.0081 (14)0.0392 (18)
C7'0.0620 (14)0.103 (2)0.0648 (14)0.0018 (14)0.0150 (12)0.0238 (14)
C8'0.0649 (13)0.0515 (12)0.0507 (11)0.0008 (10)0.0140 (10)0.0082 (9)
C9'0.0959 (18)0.0508 (13)0.0650 (14)0.0103 (12)0.0308 (13)0.0029 (11)
C10'0.140 (3)0.0508 (14)0.099 (2)0.0047 (17)0.070 (2)0.0005 (14)
C11'0.126 (3)0.0723 (19)0.130 (3)0.0320 (19)0.077 (2)0.034 (2)
C12'0.0816 (19)0.105 (2)0.105 (2)0.0336 (17)0.0335 (17)0.0447 (19)
C13'0.0700 (15)0.0858 (18)0.0648 (14)0.0173 (13)0.0189 (12)0.0162 (13)
C14'0.0545 (12)0.0520 (12)0.0589 (12)0.0104 (10)0.0100 (10)0.0043 (10)
C15'0.164 (3)0.0717 (18)0.0710 (17)0.0341 (19)0.0367 (19)0.0069 (14)
C16'0.146 (3)0.107 (3)0.103 (2)0.080 (2)0.030 (2)0.0063 (19)
C17'0.137 (3)0.0609 (19)0.278 (6)0.0174 (19)0.109 (4)0.031 (3)
Geometric parameters (Å, º) top
Si—O1'1.6420 (15)C6'—C7'1.390 (4)
Si—C2'1.874 (2)C6'—H6'0.9300
Si—C8'1.874 (2)C7'—H7'0.9300
Si—C14'1.880 (2)C8'—C13'1.388 (3)
N1—C61.290 (3)C8'—C9'1.398 (3)
N1—N21.347 (3)C9'—C10'1.389 (4)
N2—C31.365 (3)C9'—H9'0.9300
N2—H20.93 (3)C10'—C11'1.358 (5)
C3—O31.239 (2)C10'—H10'0.9300
C3—C41.433 (3)C11'—C12'1.363 (5)
C4—C51.340 (3)C11'—H11'0.9300
C4—C1'1.493 (3)C12'—C13'1.393 (4)
C5—C61.415 (3)C12'—H12'0.9300
C5—H50.9300C13'—H13'0.9300
C6—H60.9300C14'—C16'1.510 (3)
C1'—O1'1.415 (2)C14'—C15'1.520 (3)
C1'—H1'10.9700C14'—C17'1.520 (4)
C1'—H1'20.9700C15'—H15A0.9600
C2'—C7'1.374 (3)C15'—H15B0.9600
C2'—C3'1.385 (3)C15'—H15C0.9600
C3'—C4'1.381 (4)C16'—H16A0.9600
C3'—H3'0.9300C16'—H16B0.9600
C4'—C5'1.344 (5)C16'—H16C0.9600
C4'—H4'0.9300C17'—H17A0.9600
C5'—C6'1.346 (5)C17'—H17B0.9600
C5'—H5'0.9300C17'—H17C0.9600
O1'—Si—C2'109.06 (9)C2'—C7'—H7'119.2
O1'—Si—C8'108.41 (10)C6'—C7'—H7'119.2
C2'—Si—C8'110.90 (10)C13'—C8'—C9'116.3 (2)
O1'—Si—C14'103.51 (9)C13'—C8'—Si122.96 (17)
C2'—Si—C14'114.95 (10)C9'—C8'—Si120.66 (18)
C8'—Si—C14'109.59 (10)C10'—C9'—C8'121.6 (3)
C6—N1—N2115.14 (18)C10'—C9'—H9'119.2
N1—N2—C3127.44 (18)C8'—C9'—H9'119.2
N1—N2—H2116.9 (16)C11'—C10'—C9'120.1 (3)
C3—N2—H2115.5 (16)C11'—C10'—H10'120.0
O3—C3—N2120.83 (18)C9'—C10'—H10'120.0
O3—C3—C4124.04 (18)C10'—C11'—C12'120.4 (3)
N2—C3—C4115.12 (18)C10'—C11'—H11'119.8
C5—C4—C3118.56 (18)C12'—C11'—H11'119.8
C5—C4—C1'124.70 (18)C11'—C12'—C13'119.7 (3)
C3—C4—C1'116.74 (17)C11'—C12'—H12'120.1
C4—C5—C6119.70 (19)C13'—C12'—H12'120.1
C4—C5—H5120.1C8'—C13'—C12'121.8 (3)
C6—C5—H5120.1C8'—C13'—H13'119.1
N1—C6—C5124.0 (2)C12'—C13'—H13'119.1
N1—C6—H6118.0C16'—C14'—C15'108.6 (2)
C5—C6—H6118.0C16'—C14'—C17'109.2 (3)
O1'—C1'—C4109.16 (16)C15'—C14'—C17'108.4 (3)
O1'—C1'—H1'1109.8C16'—C14'—Si110.01 (18)
C4—C1'—H1'1109.8C15'—C14'—Si108.18 (16)
O1'—C1'—H1'2109.8C17'—C14'—Si112.41 (17)
C4—C1'—H1'2109.8C14'—C15'—H15A109.5
H1'1—C1'—H1'2108.3C14'—C15'—H15B109.5
C1'—O1'—Si125.32 (13)H15A—C15'—H15B109.5
C7'—C2'—C3'115.6 (2)C14'—C15'—H15C109.5
C7'—C2'—Si123.85 (18)H15A—C15'—H15C109.5
C3'—C2'—Si120.58 (18)H15B—C15'—H15C109.5
C4'—C3'—C2'122.3 (3)C14'—C16'—H16A109.5
C4'—C3'—H3'118.8C14'—C16'—H16B109.5
C2'—C3'—H3'118.8H16A—C16'—H16B109.5
C5'—C4'—C3'120.3 (3)C14'—C16'—H16C109.5
C5'—C4'—H4'119.8H16A—C16'—H16C109.5
C3'—C4'—H4'119.8H16B—C16'—H16C109.5
C4'—C5'—C6'119.3 (3)C14'—C17'—H17A109.5
C4'—C5'—H5'120.3C14'—C17'—H17B109.5
C6'—C5'—H5'120.3H17A—C17'—H17B109.5
C5'—C6'—C7'120.8 (3)C14'—C17'—H17C109.5
C5'—C6'—H6'119.6H17A—C17'—H17C109.5
C7'—C6'—H6'119.6H17B—C17'—H17C109.5
C2'—C7'—C6'121.6 (3)
C6—N1—N2—C30.3 (3)C4'—C5'—C6'—C7'1.3 (5)
N1—N2—C3—O3179.2 (2)C3'—C2'—C7'—C6'2.0 (4)
N1—N2—C3—C40.9 (3)Si—C2'—C7'—C6'178.6 (2)
O3—C3—C4—C5179.5 (2)C5'—C6'—C7'—C2'0.5 (5)
N2—C3—C4—C50.7 (3)O1'—Si—C8'—C13'170.38 (18)
O3—C3—C4—C1'0.8 (3)C2'—Si—C8'—C13'50.7 (2)
N2—C3—C4—C1'179.02 (19)C14'—Si—C8'—C13'77.3 (2)
C3—C4—C5—C60.0 (3)O1'—Si—C8'—C9'12.29 (19)
C1'—C4—C5—C6179.7 (2)C2'—Si—C8'—C9'132.00 (17)
N2—N1—C6—C50.5 (4)C14'—Si—C8'—C9'100.04 (18)
C4—C5—C6—N10.7 (4)C13'—C8'—C9'—C10'0.1 (3)
C5—C4—C1'—O1'6.1 (3)Si—C8'—C9'—C10'177.36 (17)
C3—C4—C1'—O1'174.22 (19)C8'—C9'—C10'—C11'0.8 (4)
C4—C1'—O1'—Si174.30 (15)C9'—C10'—C11'—C12'0.8 (4)
C2'—Si—O1'—C1'45.6 (2)C10'—C11'—C12'—C13'0.2 (5)
C8'—Si—O1'—C1'75.2 (2)C9'—C8'—C13'—C12'0.5 (3)
C14'—Si—O1'—C1'168.44 (19)Si—C8'—C13'—C12'178.0 (2)
O1'—Si—C2'—C7'118.5 (2)C11'—C12'—C13'—C8'0.5 (4)
C8'—Si—C2'—C7'0.8 (2)O1'—Si—C14'—C16'177.2 (2)
C14'—Si—C2'—C7'125.8 (2)C2'—Si—C14'—C16'64.0 (2)
O1'—Si—C2'—C3'60.8 (2)C8'—Si—C14'—C16'61.7 (2)
C8'—Si—C2'—C3'179.9 (2)O1'—Si—C14'—C15'58.7 (2)
C14'—Si—C2'—C3'54.9 (2)C2'—Si—C14'—C15'177.52 (18)
C7'—C2'—C3'—C4'1.8 (4)C8'—Si—C14'—C15'56.8 (2)
Si—C2'—C3'—C4'178.8 (2)O1'—Si—C14'—C17'61.0 (3)
C2'—C3'—C4'—C5'0.1 (5)C2'—Si—C14'—C17'57.9 (3)
C3'—C4'—C5'—C6'1.5 (5)C8'—Si—C14'—C17'176.5 (3)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C8'–C13' ring
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.93 (3)1.84 (3)2.764 (2)176 (2)
C6—H6···Cg2ii0.932.763.637 (3)138
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+2, z.
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C8'–C13' ring
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.93 (3)1.84 (3)2.764 (2)176 (2)
C6—H6···Cg2ii0.932.763.637 (3)138
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+2, z.
Acknowledgements top

This work was financially supported by the Xunta de Galicia (CN 2012/184). The authors gratefully acknowledge Dr Berta Covelo, X-ray Diffraction service of the University of Vigo, for her valuable assistance. M. C. Costas-Lago and N. Vila thank the University of Vigo for their Master and PhD fellowships, respectively.

references
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