5-[(tert-Butyl-diphenyl-sil-yloxy)meth-yl]pyridazin-3(2H)-one.

In the title compound, C21H24N2O2Si, a new pyridazin-3(2H)-one derivative, the carbonyl group of the heterocyclic ring and the O atom of the silyl ether are located on the same side of the pyridazinone ring and the C-C-O-Si torsion angle is -140.69 (17)°. In the crystal, mol-ecules are linked by pairs of strong N-H⋯O hydrogen bonds into centrosymmetric dimers with graph-set notation R 2 (2)(8). Weak C-H⋯π inter-actions are also observed.

Related literature

For background to related compounds displaying biological activity, see: Siddiqui et al. (2010 ▶); Moos et al. (1987 ▶); Coelho et al. (2007 ▶); Abouzid & Bekhit (2008 ▶); Cesari et al. (2006 ▶); Rathish et al. (2009 ▶); Sivakumar et al. (2003 ▶); Al-Tel (2010 ▶); Suree et al. (2009 ▶); Tao et al. (2011 ▶); Weishaar et al. (1985 ▶). For related structures, see: Costas et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H24N2O2Si

M = 364.51

Monoclinic,

a = 7.9844 (10) Å

b = 14.1416 (17) Å

c = 18.553 (2) Å

β = 98.158 (2)°

V = 2073.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.49 × 0.47 × 0.35 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.704, T max = 0.746

25441 measured reflections

5012 independent reflections

3090 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.172

S = 1.01

5012 reflections

242 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.21 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681303167X/bx2453sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681303167X/bx2453Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681303167X/bx2453Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H24N2O2Si	F(000) = 776
Mr = 364.51	Dx = 1.168 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.9844 (10) Å	Cell parameters from 6082 reflections
b = 14.1416 (17) Å	θ = 2.2–25.6°
c = 18.553 (2) Å	µ = 0.13 mm−1
β = 98.158 (2)°	T = 293 K
V = 2073.6 (4) Å3	Prism, colourless
Z = 4	0.49 × 0.47 × 0.35 mm

Bruker SMART 1000 CCD diffractometer	5012 independent reflections
Radiation source: fine-focus sealed tube	3090 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 28.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.704, Tmax = 0.746	k = −18→18
25441 measured reflections	l = −24→24

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0697P)2 + 1.0269P] where P = (Fo2 + 2Fc2)/3
5012 reflections	(Δ/σ)max < 0.001
242 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. 1H-RMN (400 MHz, CDCl3) δ p.p.m.: 12.91 (s, 1H), 7.72 (d, 1H, J=1.9 Hz), 7.67 (m, 4H), 7.44 (m, 6H), 7.08 (m, 1H), 4.61 (d, 2H, J=1.3 Hz), 1.12 (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.

	x	y	z	Uiso*/Ueq
Si	−0.01100 (7)	0.06816 (5)	0.31744 (3)	0.0514 (2)
N1	0.1582 (3)	−0.09069 (15)	0.02092 (11)	0.0662 (5)
N2	0.2996 (3)	−0.03706 (14)	0.02689 (11)	0.0575 (5)
H2	0.358 (3)	−0.0458 (19)	−0.0097 (15)	0.073 (8)*
C4	0.2380 (3)	0.04087 (17)	0.13229 (11)	0.0544 (5)
H4	0.2632	0.0852	0.1693	0.065*
C3	0.3532 (3)	0.02690 (17)	0.08010 (11)	0.0545 (5)
O3	0.4903 (2)	0.06809 (14)	0.08028 (9)	0.0743 (5)
C5	0.0949 (3)	−0.00962 (16)	0.12787 (11)	0.0523 (5)
C6	0.0614 (3)	−0.07715 (17)	0.07036 (13)	0.0616 (6)
H6	−0.0361	−0.1137	0.0683	0.074*
C1'	−0.0338 (3)	0.0012 (2)	0.17870 (12)	0.0650 (6)
H1'1	−0.1425	0.0169	0.1510	0.078*
H1'2	−0.0458	−0.0584	0.2034	0.078*
O1'	0.0132 (2)	0.07213 (11)	0.23069 (8)	0.0597 (4)
C2'	0.0633 (4)	−0.05142 (19)	0.35288 (13)	0.0709 (7)
C3'	−0.0335 (6)	−0.1239 (3)	0.37389 (18)	0.1092 (12)
H3'	−0.1494	−0.1151	0.3724	0.131*
C4'	0.0403 (9)	−0.2126 (3)	0.3980 (2)	0.1304 (18)
H4'	−0.0254	−0.2612	0.4129	0.156*
C5'	0.2058 (10)	−0.2236 (3)	0.3983 (2)	0.145 (2)
H5'	0.2548	−0.2811	0.4138	0.174*
C6'	0.3032 (8)	−0.1568 (4)	0.3776 (3)	0.165 (2)
H6'	0.4180	−0.1676	0.3775	0.198*
C7'	0.2323 (5)	−0.0705 (3)	0.3562 (3)	0.1212 (14)
H7'	0.3028	−0.0229	0.3434	0.145*
C8'	0.1407 (3)	0.15851 (17)	0.35988 (14)	0.0613 (6)
C9'	0.2043 (4)	0.22855 (19)	0.3190 (2)	0.0853 (9)
H9'	0.1707	0.2305	0.2689	0.102*
C10'	0.3164 (5)	0.2953 (3)	0.3512 (4)	0.1315 (19)
H10'	0.3586	0.3412	0.3227	0.158*
C11'	0.3645 (5)	0.2945 (4)	0.4228 (4)	0.156 (3)
H11'	0.4399	0.3401	0.4439	0.187*
C12'	0.3054 (5)	0.2284 (4)	0.4651 (3)	0.1347 (18)
H12'	0.3393	0.2289	0.5151	0.162*
C13'	0.1941 (4)	0.1597 (3)	0.43397 (17)	0.0907 (9)
H13'	0.1548	0.1138	0.4634	0.109*
C14'	−0.2325 (3)	0.1025 (3)	0.32926 (15)	0.0812 (9)
C15'	−0.2574 (5)	0.2050 (4)	0.3026 (2)	0.1399 (18)
H15A	−0.3708	0.2249	0.3063	0.210*
H15B	−0.2382	0.2089	0.2527	0.210*
H15C	−0.1787	0.2454	0.3320	0.210*
C16'	−0.2605 (5)	0.0971 (4)	0.40913 (18)	0.1222 (15)
H16A	−0.3718	0.1197	0.4137	0.183*
H16B	−0.1777	0.1355	0.4383	0.183*
H16C	−0.2494	0.0327	0.4255	0.183*
C17'	−0.3641 (4)	0.0404 (4)	0.2832 (2)	0.1413 (19)
H17A	−0.3467	−0.0245	0.2974	0.212*
H17B	−0.3524	0.0472	0.2327	0.212*
H17C	−0.4757	0.0597	0.2907	0.212*

	U11	U22	U33	U12	U13	U23
Si	0.0496 (3)	0.0634 (4)	0.0439 (3)	−0.0037 (3)	0.0161 (2)	0.0005 (3)
N1	0.0711 (13)	0.0649 (13)	0.0656 (12)	0.0004 (10)	0.0206 (10)	−0.0141 (10)
N2	0.0594 (11)	0.0651 (12)	0.0513 (10)	0.0080 (9)	0.0197 (9)	−0.0085 (9)
C4	0.0579 (13)	0.0641 (14)	0.0436 (11)	0.0038 (10)	0.0150 (9)	−0.0058 (10)
C3	0.0551 (13)	0.0638 (14)	0.0470 (11)	0.0066 (11)	0.0154 (9)	−0.0025 (10)
O3	0.0665 (11)	0.0986 (14)	0.0636 (10)	−0.0144 (10)	0.0295 (8)	−0.0208 (9)
C5	0.0554 (12)	0.0599 (13)	0.0437 (11)	0.0069 (10)	0.0138 (9)	0.0040 (9)
C6	0.0643 (14)	0.0616 (14)	0.0613 (14)	−0.0034 (11)	0.0173 (11)	−0.0043 (11)
C1'	0.0585 (13)	0.0889 (18)	0.0508 (12)	−0.0025 (12)	0.0192 (10)	−0.0059 (12)
O1'	0.0700 (10)	0.0678 (10)	0.0463 (8)	0.0021 (8)	0.0256 (7)	0.0008 (7)
C2'	0.100 (2)	0.0637 (15)	0.0507 (13)	−0.0123 (14)	0.0163 (13)	0.0017 (11)
C3'	0.158 (3)	0.084 (2)	0.089 (2)	−0.042 (2)	0.026 (2)	0.0057 (18)
C4'	0.236 (6)	0.075 (3)	0.086 (2)	−0.041 (3)	0.041 (3)	0.0092 (19)
C5'	0.257 (7)	0.086 (3)	0.098 (3)	0.015 (4)	0.048 (4)	0.023 (2)
C6'	0.170 (5)	0.123 (4)	0.210 (6)	0.064 (4)	0.057 (4)	0.072 (4)
C7'	0.110 (3)	0.086 (2)	0.173 (4)	0.028 (2)	0.037 (3)	0.051 (2)
C8'	0.0532 (12)	0.0578 (14)	0.0755 (16)	0.0026 (11)	0.0181 (11)	−0.0091 (12)
C9'	0.0749 (18)	0.0550 (15)	0.135 (3)	0.0015 (13)	0.0461 (18)	−0.0044 (16)
C10'	0.098 (3)	0.062 (2)	0.253 (6)	−0.0135 (19)	0.087 (4)	−0.037 (3)
C11'	0.074 (3)	0.129 (4)	0.273 (8)	−0.034 (2)	0.056 (4)	−0.111 (5)
C12'	0.085 (3)	0.169 (4)	0.144 (4)	−0.006 (3)	−0.006 (2)	−0.085 (3)
C13'	0.0783 (19)	0.108 (2)	0.083 (2)	−0.0066 (17)	0.0006 (15)	−0.0245 (18)
C14'	0.0536 (14)	0.131 (3)	0.0633 (15)	0.0030 (16)	0.0236 (12)	−0.0113 (17)
C15'	0.096 (3)	0.180 (5)	0.152 (4)	0.074 (3)	0.042 (2)	0.021 (3)
C16'	0.092 (2)	0.209 (4)	0.075 (2)	−0.002 (3)	0.0472 (18)	−0.029 (2)
C17'	0.0533 (17)	0.266 (6)	0.107 (3)	−0.023 (3)	0.0197 (17)	−0.057 (3)

Si—O1'	1.6490 (15)	C6'—C7'	1.380 (5)
Si—C8'	1.857 (3)	C6'—H6'	0.9300
Si—C14'	1.877 (3)	C7'—H7'	0.9300
Si—C2'	1.880 (3)	C8'—C13'	1.380 (4)
N1—C6	1.295 (3)	C8'—C9'	1.387 (4)
N1—N2	1.351 (3)	C9'—C10'	1.378 (5)
N2—C3	1.362 (3)	C9'—H9'	0.9300
N2—H2	0.89 (3)	C10'—C11'	1.329 (8)
C4—C5	1.340 (3)	C10'—H10'	0.9300
C4—C3	1.440 (3)	C11'—C12'	1.348 (8)
C4—H4	0.9300	C11'—H11'	0.9300
C3—O3	1.240 (3)	C12'—C13'	1.386 (5)
C5—C6	1.429 (3)	C12'—H12'	0.9300
C5—C1'	1.498 (3)	C13'—H13'	0.9300
C6—H6	0.9300	C14'—C16'	1.531 (4)
C1'—O1'	1.406 (3)	C14'—C17'	1.533 (5)
C1'—H1'1	0.9700	C14'—C15'	1.535 (5)
C1'—H1'2	0.9700	C15'—H15A	0.9600
C2'—C7'	1.369 (5)	C15'—H15B	0.9600
C2'—C3'	1.373 (4)	C15'—H15C	0.9600
C3'—C4'	1.431 (6)	C16'—H16A	0.9600
C3'—H3'	0.9300	C16'—H16B	0.9600
C4'—C5'	1.329 (7)	C16'—H16C	0.9600
C4'—H4'	0.9300	C17'—H17A	0.9600
C5'—C6'	1.315 (7)	C17'—H17B	0.9600
C5'—H5'	0.9300	C17'—H17C	0.9600
O1'—Si—C8'	103.33 (10)	C2'—C7'—H7'	118.4
O1'—Si—C14'	110.38 (11)	C6'—C7'—H7'	118.4
C8'—Si—C14'	109.94 (13)	C13'—C8'—C9'	116.8 (3)
O1'—Si—C2'	107.29 (10)	C13'—C8'—Si	121.4 (2)
C8'—Si—C2'	108.43 (12)	C9'—C8'—Si	121.8 (2)
C14'—Si—C2'	116.61 (15)	C10'—C9'—C8'	121.1 (4)
C6—N1—N2	115.8 (2)	C10'—C9'—H9'	119.4
N1—N2—C3	127.22 (19)	C8'—C9'—H9'	119.4
N1—N2—H2	112.7 (17)	C11'—C10'—C9'	120.4 (5)
C3—N2—H2	120.1 (17)	C11'—C10'—H10'	119.8
C5—C4—C3	120.4 (2)	C9'—C10'—H10'	119.8
C5—C4—H4	119.8	C10'—C11'—C12'	120.8 (4)
C3—C4—H4	119.8	C10'—C11'—H11'	119.6
O3—C3—N2	120.03 (19)	C12'—C11'—H11'	119.6
O3—C3—C4	125.6 (2)	C11'—C12'—C13'	120.1 (5)
N2—C3—C4	114.4 (2)	C11'—C12'—H12'	120.0
C4—C5—C6	118.0 (2)	C13'—C12'—H12'	120.0
C4—C5—C1'	124.2 (2)	C8'—C13'—C12'	120.8 (4)
C6—C5—C1'	117.7 (2)	C8'—C13'—H13'	119.6
N1—C6—C5	124.1 (2)	C12'—C13'—H13'	119.6
N1—C6—H6	118.0	C16'—C14'—C17'	109.2 (3)
C5—C6—H6	118.0	C16'—C14'—C15'	109.2 (3)
O1'—C1'—C5	111.4 (2)	C17'—C14'—C15'	108.3 (3)
O1'—C1'—H1'1	109.4	C16'—C14'—Si	111.7 (2)
C5—C1'—H1'1	109.4	C17'—C14'—Si	111.7 (2)
O1'—C1'—H1'2	109.4	C15'—C14'—Si	106.7 (2)
C5—C1'—H1'2	109.4	C14'—C15'—H15A	109.5
H1'1—C1'—H1'2	108.0	C14'—C15'—H15B	109.5
C1'—O1'—Si	126.05 (15)	H15A—C15'—H15B	109.5
C7'—C2'—C3'	115.6 (3)	C14'—C15'—H15C	109.5
C7'—C2'—Si	116.9 (2)	H15A—C15'—H15C	109.5
C3'—C2'—Si	127.5 (3)	H15B—C15'—H15C	109.5
C2'—C3'—C4'	121.3 (4)	C14'—C16'—H16A	109.5
C2'—C3'—H3'	119.3	C14'—C16'—H16B	109.5
C4'—C3'—H3'	119.3	H16A—C16'—H16B	109.5
C5'—C4'—C3'	118.0 (4)	C14'—C16'—H16C	109.5
C5'—C4'—H4'	121.0	H16A—C16'—H16C	109.5
C3'—C4'—H4'	121.0	H16B—C16'—H16C	109.5
C6'—C5'—C4'	122.9 (5)	C14'—C17'—H17A	109.5
C6'—C5'—H5'	118.6	C14'—C17'—H17B	109.5
C4'—C5'—H5'	118.6	H17A—C17'—H17B	109.5
C5'—C6'—C7'	119.0 (5)	C14'—C17'—H17C	109.5
C5'—C6'—H6'	120.5	H17A—C17'—H17C	109.5
C7'—C6'—H6'	120.5	H17B—C17'—H17C	109.5
C2'—C7'—C6'	123.3 (4)
C6—N1—N2—C3	2.2 (4)	C3'—C2'—C7'—C6'	1.3 (6)
N1—N2—C3—O3	176.7 (2)	Si—C2'—C7'—C6'	−176.7 (4)
N1—N2—C3—C4	−3.9 (3)	C5'—C6'—C7'—C2'	−2.3 (9)
C5—C4—C3—O3	−178.2 (2)	O1'—Si—C8'—C13'	−161.8 (2)
C5—C4—C3—N2	2.5 (3)	C14'—Si—C8'—C13'	80.3 (2)
C3—C4—C5—C6	0.2 (3)	C2'—Si—C8'—C13'	−48.2 (2)
C3—C4—C5—C1'	−178.8 (2)	O1'—Si—C8'—C9'	18.9 (2)
N2—N1—C6—C5	1.0 (4)	C14'—Si—C8'—C9'	−98.9 (2)
C4—C5—C6—N1	−2.1 (4)	C2'—Si—C8'—C9'	132.6 (2)
C1'—C5—C6—N1	177.0 (2)	C13'—C8'—C9'—C10'	0.5 (4)
C4—C5—C1'—O1'	1.1 (3)	Si—C8'—C9'—C10'	179.8 (2)
C6—C5—C1'—O1'	−177.9 (2)	C8'—C9'—C10'—C11'	−0.8 (5)
C5—C1'—O1'—Si	−140.69 (17)	C9'—C10'—C11'—C12'	0.2 (7)
C8'—Si—O1'—C1'	160.37 (19)	C10'—C11'—C12'—C13'	0.5 (7)
C14'—Si—O1'—C1'	−82.1 (2)	C9'—C8'—C13'—C12'	0.3 (4)
C2'—Si—O1'—C1'	45.9 (2)	Si—C8'—C13'—C12'	−179.0 (3)
O1'—Si—C2'—C7'	66.8 (3)	C11'—C12'—C13'—C8'	−0.8 (6)
C8'—Si—C2'—C7'	−44.2 (3)	O1'—Si—C14'—C16'	178.5 (3)
C14'—Si—C2'—C7'	−168.9 (3)	C8'—Si—C14'—C16'	−68.1 (3)
O1'—Si—C2'—C3'	−110.9 (3)	C2'—Si—C14'—C16'	55.8 (3)
C8'—Si—C2'—C3'	138.1 (3)	O1'—Si—C14'—C17'	56.0 (3)
C14'—Si—C2'—C3'	13.4 (3)	C8'—Si—C14'—C17'	169.4 (3)
C7'—C2'—C3'—C4'	0.4 (5)	C2'—Si—C14'—C17'	−66.7 (3)
Si—C2'—C3'—C4'	178.2 (3)	O1'—Si—C14'—C15'	−62.1 (3)
C2'—C3'—C4'—C5'	−1.1 (6)	C8'—Si—C14'—C15'	51.2 (3)
C3'—C4'—C5'—C6'	0.1 (8)	C2'—Si—C14'—C15'	175.1 (2)
C4'—C5'—C6'—C7'	1.6 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.89 (3)	1.93 (3)	2.812 (2)	173 (2)
C6—H6···Cg3ii	0.93	3.00	3.869 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C8′–C13′ ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.89 (3)	1.93 (3)	2.812 (2)	173 (2)
C6—H6⋯Cg3ii	0.93	3.00	3.869 (3)	157

Symmetry codes: (i) ; (ii) .