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

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

doi:10.1107/S1600536813032212

organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1859-o1860

doi:10.1107/S1600536813032212

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

María Carmen Costas-Lago,^a Tamara Costas,^a Noemí Vila ^a and Pedro Besada ^a ^*

^aDepartment of Organic Chemistry, University of Vigo, E-36310 Vigo, Spain
^*Correspondence e-mail: pbes@uvigo.es

(Received 5 November 2013; accepted 26 November 2013; online 30 November 2013)

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 π–π 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⋯π interactions.

CCDC reference: 973775

Related literature

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 ).

Experimental

Crystal data

C₂₁H₂₄N₂O₂Si
M_r = 364.51
Monoclinic, P 2₁ /n
a = 10.774 (4) Å
b = 7.988 (3) Å
c = 24.681 (10) Å
β = 100.207 (7)°
V = 2090.5 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 K
0.48 × 0.41 × 0.23 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.707, T_max = 0.746
25187 measured reflections
5045 independent reflections
3076 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.148
S = 1.00
5045 reflections
242 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8′–C13′ ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3ⁱ	0.93 (3)	1.84 (3)	2.764 (2)	176 (2)
C6—H6⋯Cg2ⁱⁱ	0.93	2.76	3.637 (3)	138
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+2, -z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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).

Supporting information

CCDC reference: 973775

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813032212/lr2118sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813032212/lr2118Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813032212/lr2118Isup3.cml

checkCIF report

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, U_iso = 1.2U_eq(C) for aromatic C—H groups,d(C—H)= 0.97 Å, U_iso = 1.2U_eq(C) for CH₂ group and d(C—H)= 0.96 Å, U_iso = 1.5U_eq(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, π–π 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 π–π 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

	Fig. 1. The molecular structure of (I) showing the atom-numbering scheme. Displacement ellipsoids are shown at the 20% probability level.
	Fig. 2. View of supramolecular dimer generated by NH···O hydrogen bonds.
	Fig. 3. View of the ladder chain along crystallographic b axis generated by π–π interactions.
	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

C₂₁H₂₄N₂O₂Si	F(000) = 776
M_r = 364.51	D_x = 1.158 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5037 reflections
a = 10.774 (4) Å	θ = 2.7–23.0°
b = 7.988 (3) Å	µ = 0.13 mm⁻¹
c = 24.681 (10) Å	T = 293 K
β = 100.207 (7)°	Prism, colourless
V = 2090.5 (14) Å³	0.48 × 0.41 × 0.23 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	5045 independent reflections
Radiation source: fine-focus sealed tube	3076 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 28.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.707, T_max = 0.746	k = −10→10
25187 measured reflections	l = −32→32

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0628P)² + 0.7126P] where P = (F_o² + 2F_c²)/3
5045 reflections	(Δ/σ)_max < 0.001
242 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₂₄N₂O₂Si	V = 2090.5 (14) Å³
M_r = 364.51	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.774 (4) Å	µ = 0.13 mm⁻¹
b = 7.988 (3) Å	T = 293 K
c = 24.681 (10) Å	0.48 × 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)
T_min = 0.707, T_max = 0.746	R_int = 0.038
25187 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.30 e Å⁻³
5045 reflections	Δρ_min = −0.24 e Å⁻³
242 parameters

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

	x	y	z	U_iso*/U_eq
Si	0.99974 (5)	0.99175 (7)	0.14301 (2)	0.04561 (17)
N1	0.52674 (18)	0.8319 (2)	−0.06086 (7)	0.0653 (5)
H2	0.487 (2)	0.611 (4)	−0.0346 (11)	0.086 (8)*
N2	0.53846 (17)	0.7036 (2)	−0.02487 (7)	0.0574 (5)
C3	0.62195 (19)	0.6898 (3)	0.02344 (8)	0.0526 (5)
O3	0.62352 (16)	0.5633 (2)	0.05259 (7)	0.0788 (5)
C4	0.70446 (17)	0.8303 (2)	0.03690 (8)	0.0467 (4)
C5	0.6944 (2)	0.9595 (3)	0.00182 (8)	0.0560 (5)
H5	0.7469	1.0521	0.0097	0.067*
C6	0.6037 (2)	0.9546 (3)	−0.04720 (9)	0.0669 (6)
H6	0.5993	1.0454	−0.0710	0.080*
C1'	0.7958 (2)	0.8211 (3)	0.08991 (9)	0.0653 (6)
H1'1	0.7505	0.8207	0.1206	0.078*
H1'2	0.8444	0.7185	0.0913	0.078*
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'	0.8172	1.1198	0.2059	0.101*
C4'	0.8235 (3)	1.0095 (5)	0.27923 (15)	0.1019 (11)
H4'	0.7594	1.0733	0.2897	0.122*
C5'	0.8812 (3)	0.8910 (5)	0.31327 (12)	0.0971 (11)
H5'	0.8589	0.8741	0.3476	0.117*
C6'	0.9719 (3)	0.7968 (5)	0.29721 (11)	0.0973 (10)
H6'	1.0109	0.7131	0.3203	0.117*
C7'	1.0078 (2)	0.8232 (4)	0.24653 (10)	0.0762 (7)
H7'	1.0702	0.7559	0.2363	0.091*
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'	1.0508	0.7771	0.0537	0.082*
C10'	1.2208 (3)	0.6650 (3)	0.06949 (14)	0.0907 (9)
H10'	1.2141	0.6115	0.0356	0.109*
C11'	1.3262 (4)	0.6449 (4)	0.10820 (17)	0.1030 (11)
H11'	1.3910	0.5763	0.1009	0.124*
C12'	1.3376 (3)	0.7244 (4)	0.15767 (15)	0.0950 (10)
H12'	1.4101	0.7105	0.1840	0.114*
C13'	1.2403 (2)	0.8268 (3)	0.16862 (10)	0.0727 (7)
H13'	1.2492	0.8813	0.2024	0.087*
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)
H15A	1.0925	1.3469	0.0681	0.151*
H15B	1.0016	1.1971	0.0486	0.151*
H15C	1.1446	1.1633	0.0714	0.151*
C16'	1.1613 (3)	1.2610 (4)	0.17343 (14)	0.1250 (14)
H16A	1.1790	1.3780	0.1702	0.188*
H16B	1.2314	1.1963	0.1659	0.188*
H16C	1.1477	1.2377	0.2101	0.188*
C17'	0.9393 (4)	1.3371 (4)	0.1387 (2)	0.1496 (19)
H17A	0.9230	1.3325	0.1756	0.224*
H17B	0.8643	1.3072	0.1134	0.224*
H17C	0.9643	1.4486	0.1308	0.224*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si	0.0432 (3)	0.0493 (3)	0.0416 (3)	−0.0068 (2)	0.0000 (2)	0.0014 (2)
N1	0.0713 (12)	0.0678 (12)	0.0512 (10)	−0.0148 (10)	−0.0044 (9)	0.0040 (9)
N2	0.0613 (11)	0.0557 (11)	0.0497 (10)	−0.0158 (9)	−0.0052 (8)	−0.0022 (8)
C3	0.0539 (12)	0.0536 (12)	0.0476 (11)	−0.0110 (9)	0.0012 (9)	−0.0008 (9)
O3	0.0872 (12)	0.0635 (10)	0.0720 (10)	−0.0326 (9)	−0.0229 (9)	0.0162 (8)
C4	0.0433 (10)	0.0514 (11)	0.0443 (10)	−0.0101 (8)	0.0048 (8)	−0.0012 (8)
C5	0.0542 (12)	0.0579 (12)	0.0537 (12)	−0.0164 (10)	0.0032 (9)	0.0023 (10)
C6	0.0732 (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—C6	1.290 (3)	C8'—C9'	1.398 (3)
N1—N2	1.347 (3)	C9'—C10'	1.389 (4)
N2—C3	1.365 (3)	C9'—H9'	0.9300
N2—H2	0.93 (3)	C10'—C11'	1.358 (5)
C3—O3	1.239 (2)	C10'—H10'	0.9300
C3—C4	1.433 (3)	C11'—C12'	1.363 (5)
C4—C5	1.340 (3)	C11'—H11'	0.9300
C4—C1'	1.493 (3)	C12'—C13'	1.393 (4)
C5—C6	1.415 (3)	C12'—H12'	0.9300
C5—H5	0.9300	C13'—H13'	0.9300
C6—H6	0.9300	C14'—C16'	1.510 (3)
C1'—O1'	1.415 (2)	C14'—C15'	1.520 (3)
C1'—H1'1	0.9700	C14'—C17'	1.520 (4)
C1'—H1'2	0.9700	C15'—H15A	0.9600
C2'—C7'	1.374 (3)	C15'—H15B	0.9600
C2'—C3'	1.385 (3)	C15'—H15C	0.9600
C3'—C4'	1.381 (4)	C16'—H16A	0.9600
C3'—H3'	0.9300	C16'—H16B	0.9600
C4'—C5'	1.344 (5)	C16'—H16C	0.9600
C4'—H4'	0.9300	C17'—H17A	0.9600
C5'—C6'	1.346 (5)	C17'—H17B	0.9600
C5'—H5'	0.9300	C17'—H17C	0.9600

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'—Si	122.96 (17)
C2'—Si—C14'	114.95 (10)	C9'—C8'—Si	120.66 (18)
C8'—Si—C14'	109.59 (10)	C10'—C9'—C8'	121.6 (3)
C6—N1—N2	115.14 (18)	C10'—C9'—H9'	119.2
N1—N2—C3	127.44 (18)	C8'—C9'—H9'	119.2
N1—N2—H2	116.9 (16)	C11'—C10'—C9'	120.1 (3)
C3—N2—H2	115.5 (16)	C11'—C10'—H10'	120.0
O3—C3—N2	120.83 (18)	C9'—C10'—H10'	120.0
O3—C3—C4	124.04 (18)	C10'—C11'—C12'	120.4 (3)
N2—C3—C4	115.12 (18)	C10'—C11'—H11'	119.8
C5—C4—C3	118.56 (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—C6	119.70 (19)	C13'—C12'—H12'	120.1
C4—C5—H5	120.1	C8'—C13'—C12'	121.8 (3)
C6—C5—H5	120.1	C8'—C13'—H13'	119.1
N1—C6—C5	124.0 (2)	C12'—C13'—H13'	119.1
N1—C6—H6	118.0	C16'—C14'—C15'	108.6 (2)
C5—C6—H6	118.0	C16'—C14'—C17'	109.2 (3)
O1'—C1'—C4	109.16 (16)	C15'—C14'—C17'	108.4 (3)
O1'—C1'—H1'1	109.8	C16'—C14'—Si	110.01 (18)
C4—C1'—H1'1	109.8	C15'—C14'—Si	108.18 (16)
O1'—C1'—H1'2	109.8	C17'—C14'—Si	112.41 (17)
C4—C1'—H1'2	109.8	C14'—C15'—H15A	109.5
H1'1—C1'—H1'2	108.3	C14'—C15'—H15B	109.5
C1'—O1'—Si	125.32 (13)	H15A—C15'—H15B	109.5
C7'—C2'—C3'	115.6 (2)	C14'—C15'—H15C	109.5
C7'—C2'—Si	123.85 (18)	H15A—C15'—H15C	109.5
C3'—C2'—Si	120.58 (18)	H15B—C15'—H15C	109.5
C4'—C3'—C2'	122.3 (3)	C14'—C16'—H16A	109.5
C4'—C3'—H3'	118.8	C14'—C16'—H16B	109.5
C2'—C3'—H3'	118.8	H16A—C16'—H16B	109.5
C5'—C4'—C3'	120.3 (3)	C14'—C16'—H16C	109.5
C5'—C4'—H4'	119.8	H16A—C16'—H16C	109.5
C3'—C4'—H4'	119.8	H16B—C16'—H16C	109.5
C4'—C5'—C6'	119.3 (3)	C14'—C17'—H17A	109.5
C4'—C5'—H5'	120.3	C14'—C17'—H17B	109.5
C6'—C5'—H5'	120.3	H17A—C17'—H17B	109.5
C5'—C6'—C7'	120.8 (3)	C14'—C17'—H17C	109.5
C5'—C6'—H6'	119.6	H17A—C17'—H17C	109.5
C7'—C6'—H6'	119.6	H17B—C17'—H17C	109.5
C2'—C7'—C6'	121.6 (3)

C6—N1—N2—C3	−0.3 (3)	C4'—C5'—C6'—C7'	1.3 (5)
N1—N2—C3—O3	−179.2 (2)	C3'—C2'—C7'—C6'	−2.0 (4)
N1—N2—C3—C4	0.9 (3)	Si—C2'—C7'—C6'	178.6 (2)
O3—C3—C4—C5	179.5 (2)	C5'—C6'—C7'—C2'	0.5 (5)
N2—C3—C4—C5	−0.7 (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—C6	0.0 (3)	O1'—Si—C8'—C9'	12.29 (19)
C1'—C4—C5—C6	−179.7 (2)	C2'—Si—C8'—C9'	132.00 (17)
N2—N1—C6—C5	−0.5 (4)	C14'—Si—C8'—C9'	−100.04 (18)
C4—C5—C6—N1	0.7 (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'—Si	−174.30 (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···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.93 (3)	1.84 (3)	2.764 (2)	176 (2)
C6—H6···Cg2ⁱⁱ	0.93	2.76	3.637 (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···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.93 (3)	1.84 (3)	2.764 (2)	176 (2)
C6—H6···Cg2ⁱⁱ	0.93	2.76	3.637 (3)	138

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+2, −z.

Acknowledgements

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. MCC-L and NV thank the University of Vigo for their Master and PhD fellowships, respectively.

References

Abouzid, K. & Bekhit, S. A. (2008). Bioorg. Med. Chem. 16, 5547–5556. Web of Science CrossRef PubMed CAS Google Scholar
Al-Tel, T. H. (2010). Eur. J. Med. Chem. 45, 5724–5731. Web of Science CAS PubMed Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madinson, Wisconsin, USA. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Cesari, N., Biancanali, C., Vergelli, C., Dal Piaz, V., Graziano, A., Biagini, P., Chelardini, C., Galeotti, N. & Giovannoni, P. (2006). J. Med. Chem. 49, 7826–7835. Web of Science CrossRef PubMed CAS Google Scholar
Costas, T., Besada, P., Piras, A., Acevedo, L., Yañez, M., Orallo, F., Laguna, R. & Terán, C. (2010). Bioorg. Med. Chem. Lett. 20, 6624–6627. Web of Science CrossRef CAS PubMed Google Scholar
Costas-Lago, M. C., Costas, T., Vila, N. & Terán, C. (2013). Acta Cryst. E69, o1826–o1827. CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Rathish, I. G., Javed, K., Bano, S., Ahmad, S., Alam, M. S. & Pillai, K. K. (2009). Eur. J. Med. Chem. 44, 2673–2678. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siddiqui, A. A., Mishra, R. & Shaharyar, M. (2010). Eur. J. Med. Chem. 45, 2283–2290. Web of Science CrossRef CAS PubMed Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suree, N., Yi, S. W., Thieu, W., Marohn, M., Damoiseaux, R., Chan, A., Jung, M. E. & Club, R. T. (2009). Bioorg. Med. Chem. 17, 7174–7185. Web of Science CrossRef PubMed CAS Google Scholar
Tao, M., Raddatz, R., Aimone, L. D. & Hudkins, R. L. (2011). Bioorg. Med. Chem. Lett. 21, 6126–6130. Web of Science CrossRef CAS PubMed Google Scholar

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Volume 69| Part 12| December 2013| Pages o1859-o1860

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