2-Di­chloro­methyl-N-ethyl-5-(1-phenyl­silolan-1-yl)cyclo­pent-3-enecarboxamide

Xiao, H.; Yang, W.-Q.; Shen, L.

doi:10.1107/S160053681302446X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1530

doi:10.1107/S160053681302446X

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2-Dichloromethyl-N-ethyl-5-(1-phenylsilolan-1-yl)cyclopent-3-enecarboxamide

Han Xiao,^a ^* Wan-Qiu Yang ^a and Liang Shen ^a

^aChemical Science and Technology Department, Kunming University, Kunming 650091, People's Republic of China
^*Correspondence e-mail: blackcrossing630@vip.sina.com

(Received 2 July 2013; accepted 2 September 2013; online 12 September 2013)

In the title compound, C₁₉H₂₅Cl₂NOSi, the NH group and the carbonyl O atom of the amide fragment are involved in an intermolecular N—H⋯O hydrogen bond forming chains of molecules. The plane of the benzene ring forms a dihedral angle of 50.5 (2)° with respect to the silolane ring and an angle of 49.74 (2)° with the cyclopentyl moiety.

Related literature

For biological activity of silicon-containing compounds, see: Tacke & Wannagat (1975 , 1979 ); Voronkov (1979 ). For synthetic methods, see: Matthews et al. (2001 , 2002 ); Benkeser et al. (1962 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₂₅Cl₂NOSi
M_r = 382.39
Orthorhombic, F d d 2
a = 42.892 (9) Å
b = 13.335 (3) Å
c = 14.234 (3) Å
V = 8141 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 295 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.927, T_max = 0.963
3814 measured reflections
1925 independent reflections
1375 reflections with I > 2σ(I)
R_int = 0.045
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.106
S = 1.03
1925 reflections
219 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.10	2.945 (5)	170
Symmetry code: (i) $[-x+{\script{7\over 4}}, y-{\script{1\over 4}}, z+{\script{1\over 4}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, 1R. DOI: 10.1107/S160053681302446X/im2436sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681302446X/im2436Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681302446X/im2436Isup3.cml

checkCIF report

Comment top

It is well known that some silicon-containing compounds show extremely high biological activity, e.g. silatranes, which are much more toxic than strychnine (Tacke & Wannagat, 1975, 1979; Voronkov, 1979). In recent years, people have reported that the reaction of diphenyldichlorosilane with magnesium and butadiene yields silacyclopentenes, which are thought to be formed via a diphenylsilylene intermediate (Matthews et al., 2001, 2002). As part of this work, we synthesized the title compound derived from 1-(cyclopenta-2,4-dienyl)-1-phenylsilolane (CDP), and its structure is reported here..

The compound crystallized with a structural configuration in which the phenyl ring (C1~C6) forms a dihedral angle of 50.5 (2)° with respect to the silolane ring (C7,C8,C9,C10,Si1). The cyclopentene ring (C11~C15) is almost planar with the largest deviation being 0.074 Å for atom C15. The bond length of C12—C13 (1.294 (6) Å), agrees with the value characteristic of a double bond. in general bond lengths (Allen et al., 1987) and angles are within normal ranges. In the crystal structure, there one intermolecular hydrogen bond (N1—H1···O1) is observed.

Related literature top

For biological activity of silicon-containing compounds, see: Tacke & Wannagat (1975, 1979); Voronkov (1979). For synthetic methods, see: Matthews et al. (2001, 2002); Benkeser et al. (1962). For bond-length data, see: Allen et al. (1987).

Experimental top

1-(cyclopenta-2,4-dienyl)-1-phenylsilolane (CDP) was synthesized according to the method reported by Benkeser et al. (1962). 0.5 mol of CDP was dissolved in 20 ml n-hexane and 20 ml triethylamine in a 200 ml round flask. At 0°C 0.6 mol of 2, 2-dichloroacetyl chloride was added to the flask in 30 min. After continually stirring for 1 h, the solvent was removed and the residue was fractionated on a Todd-column (yield: 31.7%). Colourless block-shaped and needlelike crystals were obtained by slow evaporation of the solution in methanol. Colourless block-shaped single crystals suitable for X-ray structure determination were picked up and determined while the needlelike crystals were too thin to perform an X-ray diffraction experiment. Acoording to elemental analysis, colourless block-shaped and needlelike crystals show an identical composition and are therefore considered to be diastereoisomeric forms of the title compound.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Molecular structure of the title compound with thermal ellipsoids shown at the 30% probability levels).

2-Dichloromethyl-N-ethyl-5-(1-phenylsilolan-1-yl)cyclopent-3-enecarboxamide top

Crystal data top

C₁₉H₂₅Cl₂NOSi	F(000) = 3232
M_r = 382.39	D_x = 1.248 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 25 reflections
a = 42.892 (9) Å	θ = 9–13°
b = 13.335 (3) Å	µ = 0.38 mm⁻¹
c = 14.234 (3) Å	T = 295 K
V = 8141 (3) Å³	Block, colourless
Z = 16	0.20 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1375 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 25.4°, θ_min = 1.9°
ω/2θ scans	h = −51→51
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
T_min = 0.927, T_max = 0.963	l = −17→0
3814 measured reflections	3 standard reflections every 200 reflections
1925 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0512P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1925 reflections	Δρ_max = 0.17 e Å⁻³
219 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00184 (15)

Crystal data top

C₁₉H₂₅Cl₂NOSi	V = 8141 (3) Å³
M_r = 382.39	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 42.892 (9) Å	µ = 0.38 mm⁻¹
b = 13.335 (3) Å	T = 295 K
c = 14.234 (3) Å	0.20 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1375 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.045
T_min = 0.927, T_max = 0.963	3 standard reflections every 200 reflections
3814 measured reflections	intensity decay: 1%
1925 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
1925 reflections	Δρ_min = −0.22 e Å⁻³
219 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.

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
C1	0.94858 (13)	−0.0023 (4)	0.1728 (4)	0.0739 (16)
H1A	0.9458	−0.0079	0.2374	0.089*
C2	0.94605 (15)	−0.0875 (5)	0.1173 (5)	0.090 (2)
H2A	0.9415	−0.1492	0.1446	0.108*
C3	0.95014 (17)	−0.0805 (6)	0.0235 (6)	0.100 (2)
H3A	0.9488	−0.1376	−0.0137	0.120*
C4	0.95610 (19)	0.0076 (7)	−0.0158 (5)	0.116 (3)
H4A	0.9586	0.0119	−0.0805	0.139*
C5	0.95859 (15)	0.0936 (5)	0.0391 (4)	0.0888 (19)
H5A	0.9627	0.1548	0.0103	0.107*
C6	0.95507 (10)	0.0902 (4)	0.1349 (3)	0.0557 (12)
C7	0.98950 (12)	0.2923 (4)	0.1792 (4)	0.0792 (17)
H7A	1.0041	0.2612	0.1360	0.095*
H7B	0.9818	0.3542	0.1519	0.095*
C8	1.00467 (18)	0.3112 (6)	0.2756 (6)	0.123 (3)
H8A	1.0266	0.3264	0.2670	0.148*
H8B	0.9949	0.3687	0.3051	0.148*
C9	1.00157 (18)	0.2240 (8)	0.3370 (5)	0.128 (3)
H9A	1.0062	0.2434	0.4012	0.154*
H9B	1.0165	0.1731	0.3184	0.154*
C10	0.96865 (14)	0.1803 (4)	0.3323 (4)	0.0796 (16)
H10A	0.9549	0.2136	0.3764	0.096*
H10B	0.9688	0.1089	0.3455	0.096*
C11	0.91725 (10)	0.2683 (3)	0.2005 (3)	0.0526 (11)
H11A	0.9139	0.2893	0.1353	0.063*
C12	0.91344 (13)	0.3580 (4)	0.2632 (4)	0.0716 (15)
H12A	0.9276	0.4108	0.2644	0.086*
C13	0.88879 (14)	0.3557 (4)	0.3152 (4)	0.0754 (15)
H13A	0.8841	0.4044	0.3598	0.090*
C14	0.86844 (11)	0.2662 (3)	0.2964 (3)	0.0563 (12)
H14A	0.8647	0.2304	0.3554	0.068*
C15	0.88968 (9)	0.2007 (3)	0.2312 (3)	0.0448 (10)
H15A	0.8982	0.1458	0.2692	0.054*
C16	0.87364 (10)	0.1546 (3)	0.1461 (3)	0.0460 (10)
C17	0.85258 (15)	0.0022 (4)	0.0751 (4)	0.0873 (18)
H17A	0.8307	0.0203	0.0759	0.105*
H17B	0.8611	0.0230	0.0151	0.105*
C18	0.85540 (18)	−0.1051 (4)	0.0838 (6)	0.113 (2)
H18A	0.8427	−0.1371	0.0369	0.169*
H18B	0.8486	−0.1255	0.1451	0.169*
H18C	0.8768	−0.1243	0.0751	0.169*
C19	0.83734 (11)	0.2984 (4)	0.2541 (4)	0.0637 (13)
H19A	0.8411	0.3267	0.1916	0.076*
Cl1	0.81918 (4)	0.39170 (15)	0.32648 (13)	0.1198 (8)
Cl2	0.81099 (3)	0.19693 (13)	0.24396 (13)	0.0928 (6)
N1	0.86865 (8)	0.0559 (2)	0.1503 (3)	0.0522 (10)
H1	0.8751	0.0231	0.1986	0.063*
O1	0.86593 (8)	0.2069 (2)	0.0793 (2)	0.0605 (9)
Si1	0.95663 (3)	0.20524 (10)	0.20897 (9)	0.0551 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.088 (4)	0.065 (3)	0.070 (4)	0.010 (3)	0.005 (3)	−0.005 (3)
C2	0.105 (5)	0.063 (4)	0.103 (6)	0.012 (3)	−0.001 (4)	−0.011 (4)
C3	0.112 (5)	0.094 (5)	0.093 (6)	0.010 (4)	0.002 (4)	−0.038 (5)
C4	0.167 (7)	0.112 (6)	0.068 (5)	−0.006 (5)	0.024 (5)	−0.023 (4)
C5	0.115 (5)	0.080 (4)	0.071 (4)	−0.016 (4)	0.019 (4)	−0.001 (3)
C6	0.048 (2)	0.069 (3)	0.050 (3)	0.002 (2)	0.009 (2)	−0.005 (2)
C7	0.053 (3)	0.082 (4)	0.102 (5)	−0.016 (3)	0.006 (3)	−0.011 (3)
C8	0.091 (5)	0.145 (6)	0.133 (7)	−0.052 (5)	−0.030 (5)	−0.014 (6)
C9	0.104 (5)	0.190 (9)	0.091 (5)	−0.026 (6)	−0.038 (5)	−0.008 (6)
C10	0.088 (4)	0.091 (4)	0.060 (3)	0.009 (3)	−0.008 (3)	−0.010 (3)
C11	0.061 (3)	0.045 (2)	0.052 (3)	−0.009 (2)	0.001 (2)	0.000 (2)
C12	0.074 (4)	0.049 (3)	0.092 (4)	−0.005 (3)	−0.013 (3)	−0.010 (3)
C13	0.082 (4)	0.072 (3)	0.073 (4)	0.013 (3)	−0.005 (3)	−0.027 (3)
C14	0.071 (3)	0.057 (3)	0.041 (3)	0.008 (2)	0.005 (2)	−0.004 (2)
C15	0.053 (3)	0.043 (2)	0.039 (2)	0.001 (2)	0.000 (2)	0.006 (2)
C16	0.047 (2)	0.046 (3)	0.045 (3)	0.005 (2)	0.0012 (19)	0.006 (2)
C17	0.117 (5)	0.062 (3)	0.083 (4)	−0.009 (3)	−0.034 (4)	−0.007 (3)
C18	0.163 (6)	0.072 (4)	0.104 (5)	−0.024 (4)	−0.038 (5)	−0.016 (4)
C19	0.064 (3)	0.071 (3)	0.056 (3)	0.017 (3)	0.004 (3)	−0.002 (3)
Cl1	0.1200 (14)	0.1454 (16)	0.0939 (12)	0.0787 (12)	0.0007 (11)	−0.0313 (12)
Cl2	0.0573 (8)	0.1037 (11)	0.1173 (13)	0.0021 (8)	0.0057 (8)	0.0253 (10)
N1	0.062 (2)	0.043 (2)	0.051 (2)	−0.0045 (18)	−0.0147 (19)	0.0037 (18)
O1	0.084 (2)	0.0553 (18)	0.0425 (17)	0.0005 (16)	−0.0081 (16)	0.0121 (17)
Si1	0.0507 (7)	0.0603 (8)	0.0541 (7)	−0.0046 (6)	0.0019 (6)	−0.0013 (7)

Geometric parameters (Å, º) top

C1—C6	1.375 (7)	C11—C15	1.550 (6)
C1—C2	1.388 (8)	C11—Si1	1.891 (5)
C1—H1A	0.9300	C11—H11A	0.9800
C2—C3	1.350 (10)	C12—C13	1.291 (7)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.325 (10)	C13—C14	1.502 (7)
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.393 (9)	C14—C19	1.525 (7)
C4—H4A	0.9300	C14—C15	1.567 (6)
C5—C6	1.372 (8)	C14—H14A	0.9800
C5—H5A	0.9300	C15—C16	1.523 (6)
C6—Si1	1.862 (5)	C15—H15A	0.9800
C7—C8	1.539 (10)	C16—O1	1.224 (5)
C7—Si1	1.875 (5)	C16—N1	1.335 (5)
C7—H7A	0.9700	C17—C18	1.442 (8)
C7—H7B	0.9700	C17—N1	1.461 (6)
C8—C9	1.461 (10)	C17—H17A	0.9700
C8—H8A	0.9700	C17—H17B	0.9700
C8—H8B	0.9700	C18—H18A	0.9600
C9—C10	1.529 (10)	C18—H18B	0.9600
C9—H9A	0.9700	C18—H18C	0.9600
C9—H9B	0.9700	C19—Cl2	1.769 (5)
C10—Si1	1.859 (6)	C19—Cl1	1.794 (5)
C10—H10A	0.9700	C19—H19A	0.9800
C10—H10B	0.9700	N1—H1	0.8600
C11—C12	1.501 (6)

C6—C1—C2	121.8 (6)	C13—C12—C11	114.2 (4)
C6—C1—H1A	119.1	C13—C12—H12A	122.9
C2—C1—H1A	119.1	C11—C12—H12A	122.9
C3—C2—C1	119.8 (7)	C12—C13—C14	113.1 (5)
C3—C2—H2A	120.1	C12—C13—H13A	123.4
C1—C2—H2A	120.1	C14—C13—H13A	123.4
C4—C3—C2	120.2 (7)	C13—C14—C19	110.8 (4)
C4—C3—H3A	119.9	C13—C14—C15	102.2 (4)
C2—C3—H3A	119.9	C19—C14—C15	115.5 (4)
C3—C4—C5	120.6 (7)	C13—C14—H14A	109.3
C3—C4—H4A	119.7	C19—C14—H14A	109.3
C5—C4—H4A	119.7	C15—C14—H14A	109.3
C6—C5—C4	121.5 (6)	C16—C15—C11	110.8 (4)
C6—C5—H5A	119.3	C16—C15—C14	115.7 (4)
C4—C5—H5A	119.3	C11—C15—C14	106.6 (3)
C5—C6—C1	116.2 (5)	C16—C15—H15A	107.8
C5—C6—Si1	122.1 (5)	C11—C15—H15A	107.8
C1—C6—Si1	121.6 (4)	C14—C15—H15A	107.8
C8—C7—Si1	102.6 (4)	O1—C16—N1	123.6 (4)
C8—C7—H7A	111.3	O1—C16—C15	120.7 (4)
Si1—C7—H7A	111.3	N1—C16—C15	115.7 (4)
C8—C7—H7B	111.3	C18—C17—N1	112.6 (5)
Si1—C7—H7B	111.3	C18—C17—H17A	109.1
H7A—C7—H7B	109.2	N1—C17—H17A	109.1
C9—C8—C7	111.4 (5)	C18—C17—H17B	109.1
C9—C8—H8A	109.3	N1—C17—H17B	109.1
C7—C8—H8A	109.3	H17A—C17—H17B	107.8
C9—C8—H8B	109.3	C17—C18—H18A	109.5
C7—C8—H8B	109.3	C17—C18—H18B	109.5
H8A—C8—H8B	108.0	H18A—C18—H18B	109.5
C8—C9—C10	111.2 (6)	C17—C18—H18C	109.5
C8—C9—H9A	109.4	H18A—C18—H18C	109.5
C10—C9—H9A	109.4	H18B—C18—H18C	109.5
C8—C9—H9B	109.4	C14—C19—Cl2	112.1 (3)
C10—C9—H9B	109.4	C14—C19—Cl1	110.4 (3)
H9A—C9—H9B	108.0	Cl2—C19—Cl1	107.5 (3)
C9—C10—Si1	103.3 (5)	C14—C19—H19A	108.9
C9—C10—H10A	111.1	Cl2—C19—H19A	108.9
Si1—C10—H10A	111.1	Cl1—C19—H19A	108.9
C9—C10—H10B	111.1	C16—N1—C17	121.8 (4)
Si1—C10—H10B	111.1	C16—N1—H1	119.1
H10A—C10—H10B	109.1	C17—N1—H1	119.1
C12—C11—C15	102.3 (4)	C10—Si1—C6	113.4 (2)
C12—C11—Si1	114.4 (3)	C10—Si1—C7	96.6 (3)
C15—C11—Si1	113.9 (3)	C6—Si1—C7	114.2 (2)
C12—C11—H11A	108.6	C10—Si1—C11	112.8 (2)
C15—C11—H11A	108.6	C6—Si1—C11	107.3 (2)
Si1—C11—H11A	108.6	C7—Si1—C11	112.4 (2)

C6—C1—C2—C3	0.3 (10)	C14—C15—C16—N1	−107.3 (4)
C1—C2—C3—C4	−1.0 (12)	C13—C14—C19—Cl2	−173.0 (4)
C2—C3—C4—C5	0.8 (13)	C15—C14—C19—Cl2	71.5 (5)
C3—C4—C5—C6	0.1 (12)	C13—C14—C19—Cl1	−53.2 (5)
C4—C5—C6—C1	−0.8 (10)	C15—C14—C19—Cl1	−168.8 (3)
C4—C5—C6—Si1	−177.3 (5)	O1—C16—N1—C17	−1.6 (7)
C2—C1—C6—C5	0.6 (9)	C15—C16—N1—C17	178.0 (4)
C2—C1—C6—Si1	177.1 (4)	C18—C17—N1—C16	167.7 (5)
Si1—C7—C8—C9	31.3 (8)	C9—C10—Si1—C6	108.3 (5)
C7—C8—C9—C10	−44.1 (9)	C9—C10—Si1—C7	−11.6 (5)
C8—C9—C10—Si1	32.6 (7)	C9—C10—Si1—C11	−129.4 (5)
C15—C11—C12—C13	−4.7 (6)	C5—C6—Si1—C10	−154.6 (5)
Si1—C11—C12—C13	−128.3 (5)	C1—C6—Si1—C10	29.1 (5)
C11—C12—C13—C14	−3.7 (7)	C5—C6—Si1—C7	−45.2 (6)
C12—C13—C14—C19	−113.5 (5)	C1—C6—Si1—C7	138.5 (4)
C12—C13—C14—C15	10.1 (6)	C5—C6—Si1—C11	80.2 (5)
C12—C11—C15—C16	137.1 (4)	C1—C6—Si1—C11	−96.2 (4)
Si1—C11—C15—C16	−98.9 (4)	C8—C7—Si1—C10	−10.0 (5)
C12—C11—C15—C14	10.5 (4)	C8—C7—Si1—C6	−129.4 (5)
Si1—C11—C15—C14	134.5 (3)	C8—C7—Si1—C11	108.0 (5)
C13—C14—C15—C16	−135.9 (4)	C12—C11—Si1—C10	49.2 (4)
C19—C14—C15—C16	−15.5 (5)	C15—C11—Si1—C10	−68.0 (4)
C13—C14—C15—C11	−12.3 (5)	C12—C11—Si1—C6	174.8 (4)
C19—C14—C15—C11	108.1 (4)	C15—C11—Si1—C6	57.6 (4)
C11—C15—C16—O1	−49.2 (5)	C12—C11—Si1—C7	−58.8 (4)
C14—C15—C16—O1	72.3 (5)	C15—C11—Si1—C7	−176.0 (3)
C11—C15—C16—N1	131.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.10	2.945 (5)	170

Symmetry code: (i) −x+7/4, y−1/4, z+1/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.10	2.945 (5)	169.5

Symmetry code: (i) −x+7/4, y−1/4, z+1/4.

Acknowledgements

This work was supported by Yunnan Provincial Department of Science and Technology: Study on neuro-activities of gastrodin and helicid derivatives (grant No. 2013FZ102), Synthesis and Sturcture-Activity Relationship of Pulverolide and Its Analogues (grant No. 2013FZ101).

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