2-Di-chloro-methyl-N-ethyl-5-(1-phenyl-silolan-1-yl)cyclo-pent-3-enecarboxamide.

In the title compound, C19H25Cl2NOSi, the NH group and the carbonyl O atom of the amide fragment are involved in an inter-molecular N-H⋯O hydrogen bond forming chains of mol-ecules. 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 cyclo-pentyl 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 = 382.39

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.106

S = 1.03

1925 reflections

219 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, 1R. DOI: 10.1107/S160053681302446X/im2436sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302446X/im2436Isup3.cml

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

C19H25Cl2NOSi	F(000) = 3232
Mr = 382.39	Dx = 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

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

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(Fo2) + (0.0512P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1925 reflections	Δρmax = 0.17 e Å−3
219 parameters	Δρmin = −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)

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
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)

	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)

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)

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

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) .