4-(2,4-Dichloro­phen­yl)-5,5-dimethyl-2-(3-silatranyl­propyl­mino)-1,3,2-dioxa­phospho­rinane 2-oxide

Liu, Z.-R.; Tan, X.-J.; Wang, D.-J.; Wang, Y.

doi:10.1107/S1600536811044928

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3279

https://doi.org/10.1107/S1600536811044928

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4-(2,4-Dichlorophenyl)-5,5-dimethyl-2-(3-silatranylpropylmino)-1,3,2-dioxaphosphorinane 2-oxide

Zhe-Rong Liu,^a Xiao-Jing Tan,^a De-Jian Wang ^a and Yan Wang ^a ^*

^aSchool of Chemical and Environmental Engineering, Hubei University for Nationalities, Enshi, Hubei 445000, People's Republic of China
^*Correspondence e-mail: wy04971@163.com

(Received 14 October 2011; accepted 26 October 2011; online 12 November 2011)

In the title compound, C₂₀H₃₁Cl₂N₂O₆PSi, the dioxaphosphorinane ring adopts a cis conformation. The silatrane fragment forms a cage-like structure in which there exists an intramolecular Si—N donor–acceptor bond. In the crystal, centrosymmetrically related molecules are linked by pairs of N—H⋯O hydrogen bonds into inversion dimers, generating rings with graph-set motif R₂²(8). The dimers are further connected into ribbons parallel to the a axis by intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of 1,3,2-dioxaphosphorinane compounds, see: Shi et al. (2006 ); Sun et al. (2006 ) and of γ-aminopropylsilatrane, see: Puri et al. (2011 ). For the synthesis of the title compound, see: Wan et al. (2005 ).

Experimental

Crystal data

C₂₀H₃₁Cl₂N₂O₆PSi
M_r = 525.43
Triclinic, $[P \overline 1]$
a = 10.7738 (12) Å
b = 10.9320 (13) Å
c = 11.2807 (13) Å
α = 111.135 (2)°
β = 95.926 (2)°
γ = 90.424 (2)°
V = 1231.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 298 K
0.20 × 0.15 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
6745 measured reflections
4720 independent reflections
2997 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.194
S = 1.00
4720 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.86	2.05	2.857 (5)	155
C6—H6⋯O6ⁱⁱ	0.93	2.45	3.332 (6)	158
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x+1, y, z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811044928/rz2656sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811044928/rz2656Isup2.hkl

checkCIF report

Comment top

1,3,2-Dioxaphosphorinane compounds have attracted many chemists' interest owing to their stereochemistry and wide biological activities, such as fungicidal, insecticidal as well as herbicidal activities (Shi et al., 2006; Sun et al., 2006). γ-Aminopropylsilatrane has been found to have good biological activity (Puri et al., 2011). In view of this and as a continuation of our research on the stereochemistry and biological properties of this class of compounds, we investigates 1,3,2-dioxaphosphinane derivatives containing γ-aminopropyl silatrane, including the title compound, (I), whose crystal structure is reported herein.

The crystal structure of (I) (Fig. 1) reveals that the cyclic dioxaphosphorinane ring in the molecule adopts a thermodynamically stable cis conformation, while the silatrane fragment forms a cage-like structure in which there exists an intramolecular Si←N donor-acceptor bond (Si1—N2 = 2.148 (4) Å), which is remarkably longer than an usual Si—N single bond (1.7–1.8 Å). In the crystal structure, molecules are linked by pairs of complementary N—H···O hydrogen bonds into centrosymmetric dimers, forming rings of graph-set motif R₂²(8) (Table 1; Fig. 2). The dimers are further linked into ribbon parallel to the a axis by intermolecular C—H···O hydrogen bonds.

Related literature top

For the biological activity of 1,3,2-dioxaphosphorinane compounds, see: Shi et al. (2006); Sun et al. (2006) and of γ-aminopropylsilatrane, see: Puri et al. (2011). For the synthesis of the title compound, see: Wan et al. (2005).

Experimental top

The title compound was prepared according to the procedure of Wan et al. (2005). Suitable crystals were obtained by vapor diffusion of tetrahydrofuran (THF) at room temperature (m.p. 522–523 K). Elemental analysis: calculated for C₂₀H₃₁Cl₂N₂O₆PSi: C 45.72, H 5.95, N 5.33%; found: C 45.89, H 6.11, N 5.22%.

Structure description top

For the biological activity of 1,3,2-dioxaphosphorinane compounds, see: Shi et al. (2006); Sun et al. (2006) and of γ-aminopropylsilatrane, see: Puri et al. (2011). For the synthesis of the title compound, see: Wan et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.
	Fig. 2. A partial packing diagram of ther title compound, showing the intermolecular hydrogen bonds (dashed lines).

4-(2,4-Dichlorophenyl)-5,5-dimethyl-2-(3-silatranylpropylmino)- 1,3,2-dioxaphosphorinane 2-oxide top

Crystal data top

C₂₀H₃₁Cl₂N₂O₆PSi	Z = 2
M_r = 525.43	F(000) = 552
Triclinic, P1	D_x = 1.417 Mg m⁻³ D_m = 1.417 Mg m⁻³ D_m measured by not measured
Hall symbol: -P 1	Melting point = 522–523 K
a = 10.7738 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9320 (13) Å	Cell parameters from 1174 reflections
c = 11.2807 (13) Å	θ = 2.2–19.3°
α = 111.135 (2)°	µ = 0.42 mm⁻¹
β = 95.926 (2)°	T = 298 K
γ = 90.424 (2)°	Needle, colorless
V = 1231.2 (2) Å³	0.20 × 0.15 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2997 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
φ and ω scans	h = −13→6
6745 measured reflections	k = −13→13
4720 independent reflections	l = −13→13

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.194	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0969P)²] where P = (F_o² + 2F_c²)/3
4720 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₀H₃₁Cl₂N₂O₆PSi	γ = 90.424 (2)°
M_r = 525.43	V = 1231.2 (2) Å³
Triclinic, P1	Z = 2
a = 10.7738 (12) Å	Mo Kα radiation
b = 10.9320 (13) Å	µ = 0.42 mm⁻¹
c = 11.2807 (13) Å	T = 298 K
α = 111.135 (2)°	0.20 × 0.15 × 0.08 mm
β = 95.926 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2997 reflections with I > 2σ(I)
6745 measured reflections	R_int = 0.033
4720 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.194	H-atom parameters constrained
S = 1.00	Δρ_max = 0.36 e Å⁻³
4720 reflections	Δρ_min = −0.35 e Å⁻³
291 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	1.0122 (4)	0.6821 (4)	0.7954 (4)	0.0437 (11)
C2	0.9035 (4)	0.7254 (4)	0.8460 (4)	0.0358 (9)
C3	0.8260 (4)	0.7889 (4)	0.7813 (4)	0.0438 (11)
H3	0.7504	0.8184	0.8114	0.053*
C4	0.8579 (4)	0.8088 (4)	0.6755 (4)	0.0457 (11)
H4	0.8037	0.8499	0.6337	0.055*
C5	0.9678 (5)	0.7691 (5)	0.6316 (4)	0.0514 (12)
C6	1.0482 (4)	0.7019 (5)	0.6884 (4)	0.0501 (12)
H6	1.1228	0.6715	0.6563	0.060*
C7	0.8618 (4)	0.7051 (4)	0.9614 (4)	0.0379 (10)
H7	0.8979	0.6255	0.9680	0.045*
C8	0.8945 (4)	0.8210 (4)	1.0912 (4)	0.0425 (10)
C9	0.8522 (4)	0.9521 (4)	1.0853 (5)	0.0531 (12)
H9A	0.7647	0.9443	1.0554	0.080*
H9B	0.8986	0.9753	1.0277	0.080*
H9C	0.8666	1.0190	1.1690	0.080*
C10	1.0350 (4)	0.8302 (5)	1.1341 (5)	0.0645 (15)
H10A	1.0800	0.8493	1.0731	0.097*
H10B	1.0601	0.7481	1.1395	0.097*
H10C	1.0530	0.8988	1.2164	0.097*
C11	0.8290 (5)	0.7924 (5)	1.1928 (4)	0.0567 (13)
H11A	0.8597	0.7124	1.2011	0.068*
H11B	0.8499	0.8634	1.2745	0.068*
C12	0.4695 (4)	0.7914 (4)	0.9460 (4)	0.0436 (10)
H12A	0.5321	0.8633	0.9787	0.052*
H12B	0.3910	0.8250	0.9763	0.052*
C13	0.4549 (4)	0.7405 (4)	0.8012 (4)	0.0423 (10)
H13A	0.3894	0.6714	0.7699	0.051*
H13B	0.5320	0.7014	0.7720	0.051*
C14	0.4239 (4)	0.8422 (4)	0.7415 (4)	0.0454 (11)
H14A	0.4879	0.9126	0.7744	0.054*
H14B	0.3453	0.8793	0.7680	0.054*
C15	0.6068 (5)	0.6880 (5)	0.4263 (5)	0.0603 (13)
H15A	0.6707	0.6263	0.4277	0.072*
H15B	0.6443	0.7597	0.4088	0.072*
C16	0.5014 (5)	0.6206 (5)	0.3235 (4)	0.0556 (13)
H16A	0.5233	0.6140	0.2402	0.067*
H16B	0.4830	0.5330	0.3218	0.067*
C17	0.3320 (5)	0.9231 (4)	0.4212 (4)	0.0544 (13)
H17A	0.3551	1.0093	0.4219	0.065*
H17B	0.2420	0.9093	0.4015	0.065*
C18	0.3951 (5)	0.8196 (5)	0.3220 (4)	0.0540 (12)
H18A	0.3508	0.8010	0.2376	0.065*
H18B	0.4805	0.8484	0.3219	0.065*
C19	0.2604 (5)	0.5652 (5)	0.4171 (4)	0.0592 (13)
H19A	0.1737	0.5394	0.4154	0.071*
H19B	0.3090	0.4875	0.3989	0.071*
C20	0.2724 (5)	0.6263 (5)	0.3168 (4)	0.0561 (13)
H20A	0.2721	0.5589	0.2326	0.067*
H20B	0.2042	0.6832	0.3148	0.067*
Cl1	1.11497 (12)	0.59273 (13)	0.86003 (13)	0.0648 (4)
Cl2	1.01035 (15)	0.8000 (2)	0.50014 (16)	0.1002 (7)
N1	0.5068 (3)	0.6877 (3)	0.9955 (3)	0.0420 (9)
H1	0.4481	0.6388	1.0041	0.050*
N2	0.3930 (3)	0.7025 (3)	0.3565 (3)	0.0455 (9)
O1	0.7265 (2)	0.6839 (3)	0.9344 (3)	0.0386 (7)
O2	0.6939 (3)	0.7780 (3)	1.1629 (3)	0.0526 (8)
O3	0.6623 (3)	0.5297 (3)	1.0444 (3)	0.0529 (8)
O4	0.5583 (3)	0.7371 (3)	0.5471 (3)	0.0515 (8)
O5	0.3694 (3)	0.9157 (3)	0.5428 (3)	0.0493 (8)
O6	0.3041 (3)	0.6576 (3)	0.5381 (3)	0.0481 (8)
P1	0.64665 (11)	0.65882 (11)	1.03461 (10)	0.0383 (3)
Si1	0.41111 (11)	0.77709 (11)	0.56192 (11)	0.0373 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.036 (3)	0.049 (3)	0.051 (3)	−0.001 (2)	0.000 (2)	0.027 (2)
C2	0.028 (2)	0.036 (2)	0.048 (2)	0.0010 (18)	0.0038 (18)	0.0212 (19)
C3	0.033 (2)	0.050 (3)	0.055 (3)	0.000 (2)	0.001 (2)	0.028 (2)
C4	0.037 (3)	0.059 (3)	0.047 (3)	0.000 (2)	−0.001 (2)	0.027 (2)
C5	0.047 (3)	0.067 (3)	0.050 (3)	−0.003 (2)	0.005 (2)	0.033 (2)
C6	0.038 (3)	0.060 (3)	0.057 (3)	0.001 (2)	0.009 (2)	0.027 (2)
C7	0.034 (2)	0.038 (2)	0.047 (2)	−0.0011 (18)	0.0017 (19)	0.023 (2)
C8	0.036 (3)	0.047 (3)	0.045 (3)	−0.008 (2)	−0.0044 (19)	0.021 (2)
C9	0.053 (3)	0.044 (3)	0.058 (3)	−0.010 (2)	0.003 (2)	0.015 (2)
C10	0.049 (3)	0.070 (4)	0.067 (3)	−0.012 (3)	−0.016 (3)	0.021 (3)
C11	0.059 (3)	0.065 (3)	0.041 (3)	−0.019 (3)	−0.010 (2)	0.018 (2)
C12	0.045 (3)	0.043 (2)	0.046 (3)	0.007 (2)	0.011 (2)	0.018 (2)
C13	0.048 (3)	0.036 (2)	0.041 (2)	0.002 (2)	0.005 (2)	0.0121 (19)
C14	0.052 (3)	0.041 (2)	0.045 (3)	0.009 (2)	0.006 (2)	0.017 (2)
C15	0.051 (3)	0.067 (3)	0.066 (3)	0.018 (3)	0.022 (3)	0.024 (3)
C16	0.067 (4)	0.054 (3)	0.047 (3)	0.015 (3)	0.028 (2)	0.013 (2)
C17	0.062 (3)	0.047 (3)	0.060 (3)	0.002 (2)	−0.007 (2)	0.029 (2)
C18	0.066 (3)	0.053 (3)	0.046 (3)	0.001 (2)	0.005 (2)	0.023 (2)
C19	0.068 (4)	0.052 (3)	0.051 (3)	−0.016 (3)	0.007 (3)	0.012 (2)
C20	0.067 (4)	0.053 (3)	0.041 (3)	−0.009 (2)	0.003 (2)	0.009 (2)
Cl1	0.0502 (8)	0.0797 (9)	0.0828 (10)	0.0257 (7)	0.0131 (7)	0.0496 (8)
Cl2	0.0808 (12)	0.1756 (19)	0.0855 (11)	0.0259 (11)	0.0294 (9)	0.0912 (13)
N1	0.041 (2)	0.051 (2)	0.045 (2)	−0.0031 (17)	0.0070 (16)	0.0286 (18)
N2	0.054 (3)	0.041 (2)	0.043 (2)	0.0000 (18)	0.0076 (18)	0.0159 (17)
O1	0.0308 (16)	0.0466 (17)	0.0395 (16)	−0.0060 (13)	0.0009 (12)	0.0180 (13)
O2	0.052 (2)	0.066 (2)	0.0388 (17)	−0.0108 (16)	0.0013 (15)	0.0198 (16)
O3	0.0414 (19)	0.0554 (19)	0.072 (2)	−0.0042 (15)	−0.0008 (15)	0.0372 (17)
O4	0.0430 (19)	0.068 (2)	0.0493 (19)	0.0093 (16)	0.0092 (15)	0.0270 (16)
O5	0.068 (2)	0.0364 (16)	0.0422 (17)	0.0120 (15)	0.0025 (15)	0.0140 (14)
O6	0.054 (2)	0.0482 (18)	0.0408 (17)	−0.0099 (15)	0.0080 (14)	0.0145 (14)
P1	0.0384 (7)	0.0428 (7)	0.0382 (6)	−0.0051 (5)	0.0029 (5)	0.0204 (5)
Si1	0.0385 (7)	0.0367 (7)	0.0372 (6)	0.0038 (5)	0.0048 (5)	0.0140 (5)

Geometric parameters (Å, º) top

C1—C2	1.368 (6)	C14—Si1	1.879 (4)
C1—C6	1.392 (6)	C14—H14A	0.9700
C1—Cl1	1.754 (4)	C14—H14B	0.9700
C2—C3	1.400 (5)	C15—O4	1.429 (5)
C2—C7	1.508 (5)	C15—C16	1.509 (7)
C3—C4	1.365 (6)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.345 (6)	C16—N2	1.472 (6)
C4—H4	0.9300	C16—H16A	0.9700
C5—C6	1.390 (6)	C16—H16B	0.9700
C5—Cl2	1.739 (5)	C17—O5	1.420 (5)
C6—H6	0.9300	C17—C18	1.501 (7)
C7—O1	1.458 (5)	C17—H17A	0.9700
C7—C8	1.557 (6)	C17—H17B	0.9700
C7—H7	0.9800	C18—N2	1.467 (5)
C8—C11	1.527 (6)	C18—H18A	0.9700
C8—C9	1.529 (6)	C18—H18B	0.9700
C8—C10	1.532 (6)	C19—O6	1.405 (5)
C9—H9A	0.9600	C19—C20	1.522 (6)
C9—H9B	0.9600	C19—H19A	0.9700
C9—H9C	0.9600	C19—H19B	0.9700
C10—H10A	0.9600	C20—N2	1.475 (6)
C10—H10B	0.9600	C20—H20A	0.9700
C10—H10C	0.9600	C20—H20B	0.9700
C11—O2	1.454 (5)	N1—P1	1.592 (3)
C11—H11A	0.9700	N1—H1	0.8600
C11—H11B	0.9700	N2—Si1	2.148 (4)
C12—N1	1.474 (5)	O1—P1	1.585 (3)
C12—C13	1.514 (5)	O2—P1	1.590 (3)
C12—H12A	0.9700	O3—P1	1.465 (3)
C12—H12B	0.9700	O4—Si1	1.657 (3)
C13—C14	1.517 (5)	O5—Si1	1.665 (3)
C13—H13A	0.9700	O6—Si1	1.664 (3)
C13—H13B	0.9700

C2—C1—C6	123.3 (4)	O4—C15—C16	108.8 (4)
C2—C1—Cl1	121.6 (3)	O4—C15—H15A	109.9
C6—C1—Cl1	115.1 (3)	C16—C15—H15A	109.9
C1—C2—C3	116.1 (4)	O4—C15—H15B	109.9
C1—C2—C7	124.6 (4)	C16—C15—H15B	109.9
C3—C2—C7	119.3 (4)	H15A—C15—H15B	108.3
C4—C3—C2	122.1 (4)	N2—C16—C15	106.1 (4)
C4—C3—H3	119.0	N2—C16—H16A	110.5
C2—C3—H3	119.0	C15—C16—H16A	110.5
C5—C4—C3	120.0 (4)	N2—C16—H16B	110.5
C5—C4—H4	120.0	C15—C16—H16B	110.5
C3—C4—H4	120.0	H16A—C16—H16B	108.7
C4—C5—C6	121.3 (4)	O5—C17—C18	108.9 (4)
C4—C5—Cl2	119.7 (4)	O5—C17—H17A	109.9
C6—C5—Cl2	118.9 (4)	C18—C17—H17A	109.9
C5—C6—C1	117.2 (4)	O5—C17—H17B	109.9
C5—C6—H6	121.4	C18—C17—H17B	109.9
C1—C6—H6	121.4	H17A—C17—H17B	108.3
O1—C7—C2	105.1 (3)	N2—C18—C17	106.2 (4)
O1—C7—C8	109.2 (3)	N2—C18—H18A	110.5
C2—C7—C8	115.6 (3)	C17—C18—H18A	110.5
O1—C7—H7	108.9	N2—C18—H18B	110.5
C2—C7—H7	108.9	C17—C18—H18B	110.5
C8—C7—H7	108.9	H18A—C18—H18B	108.7
C11—C8—C9	108.6 (4)	O6—C19—C20	108.9 (4)
C11—C8—C10	106.7 (4)	O6—C19—H19A	109.9
C9—C8—C10	110.2 (4)	C20—C19—H19A	109.9
C11—C8—C7	108.3 (3)	O6—C19—H19B	109.9
C9—C8—C7	112.3 (3)	C20—C19—H19B	109.9
C10—C8—C7	110.5 (4)	H19A—C19—H19B	108.3
C8—C9—H9A	109.5	N2—C20—C19	105.2 (4)
C8—C9—H9B	109.5	N2—C20—H20A	110.7
H9A—C9—H9B	109.5	C19—C20—H20A	110.7
C8—C9—H9C	109.5	N2—C20—H20B	110.7
H9A—C9—H9C	109.5	C19—C20—H20B	110.7
H9B—C9—H9C	109.5	H20A—C20—H20B	108.8
C8—C10—H10A	109.5	C12—N1—P1	125.4 (3)
C8—C10—H10B	109.5	C12—N1—H1	117.3
H10A—C10—H10B	109.5	P1—N1—H1	117.3
C8—C10—H10C	109.5	C18—N2—C16	114.4 (4)
H10A—C10—H10C	109.5	C18—N2—C20	113.7 (4)
H10B—C10—H10C	109.5	C16—N2—C20	113.3 (4)
O2—C11—C8	112.8 (3)	C18—N2—Si1	104.9 (3)
O2—C11—H11A	109.0	C16—N2—Si1	104.3 (3)
C8—C11—H11A	109.0	C20—N2—Si1	104.9 (3)
O2—C11—H11B	109.0	C7—O1—P1	120.6 (2)
C8—C11—H11B	109.0	C11—O2—P1	114.1 (3)
H11A—C11—H11B	107.8	C15—O4—Si1	122.9 (3)
N1—C12—C13	111.7 (3)	C17—O5—Si1	123.0 (3)
N1—C12—H12A	109.3	C19—O6—Si1	123.8 (3)
C13—C12—H12A	109.3	O3—P1—O1	113.75 (18)
N1—C12—H12B	109.3	O3—P1—O2	113.69 (17)
C13—C12—H12B	109.3	O1—P1—O2	102.17 (16)
H12A—C12—H12B	107.9	O3—P1—N1	114.75 (18)
C12—C13—C14	115.4 (3)	O1—P1—N1	105.51 (16)
C12—C13—H13A	108.4	O2—P1—N1	105.78 (18)
C14—C13—H13A	108.4	O4—Si1—O6	118.09 (17)
C12—C13—H13B	108.4	O4—Si1—O5	117.49 (17)
C14—C13—H13B	108.4	O6—Si1—O5	120.06 (17)
H13A—C13—H13B	107.5	O4—Si1—C14	97.52 (18)
C13—C14—Si1	114.4 (3)	O6—Si1—C14	96.54 (18)
C13—C14—H14A	108.7	O5—Si1—C14	96.87 (16)
Si1—C14—H14A	108.7	O4—Si1—N2	83.46 (15)
C13—C14—H14B	108.7	O6—Si1—N2	82.74 (14)
Si1—C14—H14B	108.7	O5—Si1—N2	82.90 (14)
H14A—C14—H14B	107.6	C14—Si1—N2	178.98 (19)

C6—C1—C2—C3	1.9 (6)	C19—C20—N2—Si1	−34.7 (4)
Cl1—C1—C2—C3	−176.4 (3)	C2—C7—O1—P1	−179.8 (2)
C6—C1—C2—C7	179.8 (4)	C8—C7—O1—P1	−55.2 (4)
Cl1—C1—C2—C7	1.5 (6)	C8—C11—O2—P1	62.2 (5)
C1—C2—C3—C4	−1.2 (6)	C16—C15—O4—Si1	−26.8 (5)
C7—C2—C3—C4	−179.2 (4)	C18—C17—O5—Si1	−28.5 (5)
C2—C3—C4—C5	−1.2 (7)	C20—C19—O6—Si1	−27.5 (5)
C3—C4—C5—C6	3.1 (7)	C7—O1—P1—O3	−71.7 (3)
C3—C4—C5—Cl2	−177.7 (4)	C7—O1—P1—O2	51.2 (3)
C4—C5—C6—C1	−2.4 (7)	C7—O1—P1—N1	161.7 (3)
Cl2—C5—C6—C1	178.4 (4)	C11—O2—P1—O3	71.4 (3)
C2—C1—C6—C5	−0.2 (7)	C11—O2—P1—O1	−51.6 (3)
Cl1—C1—C6—C5	178.2 (3)	C11—O2—P1—N1	−161.7 (3)
C1—C2—C7—O1	−143.9 (4)	C12—N1—P1—O3	−162.7 (3)
C3—C2—C7—O1	33.9 (5)	C12—N1—P1—O1	−36.6 (4)
C1—C2—C7—C8	95.6 (5)	C12—N1—P1—O2	71.2 (4)
C3—C2—C7—C8	−86.5 (5)	C15—O4—Si1—O6	82.5 (4)
O1—C7—C8—C11	53.4 (4)	C15—O4—Si1—O5	−74.1 (4)
C2—C7—C8—C11	171.6 (4)	C15—O4—Si1—C14	−175.9 (4)
O1—C7—C8—C9	−66.6 (4)	C15—O4—Si1—N2	4.3 (4)
C2—C7—C8—C9	51.6 (5)	C19—O6—Si1—O4	−73.6 (4)
O1—C7—C8—C10	169.9 (3)	C19—O6—Si1—O5	82.4 (4)
C2—C7—C8—C10	−71.8 (5)	C19—O6—Si1—C14	−175.7 (4)
C9—C8—C11—O2	62.5 (5)	C19—O6—Si1—N2	5.0 (3)
C10—C8—C11—O2	−178.7 (4)	C17—O5—Si1—O4	85.1 (4)
C7—C8—C11—O2	−59.7 (5)	C17—O5—Si1—O6	−71.1 (4)
N1—C12—C13—C14	−176.7 (4)	C17—O5—Si1—C14	−172.7 (4)
C12—C13—C14—Si1	178.2 (3)	C17—O5—Si1—N2	6.3 (4)
O4—C15—C16—N2	40.0 (5)	C13—C14—Si1—O4	−64.2 (4)
O5—C17—C18—N2	39.9 (5)	C13—C14—Si1—O6	55.4 (4)
O6—C19—C20—N2	40.0 (5)	C13—C14—Si1—O5	176.8 (3)
C13—C12—N1—P1	93.0 (4)	C18—N2—Si1—O4	−101.5 (3)
C17—C18—N2—C16	−147.6 (4)	C16—N2—Si1—O4	19.1 (3)
C17—C18—N2—C20	80.1 (4)	C20—N2—Si1—O4	138.4 (3)
C17—C18—N2—Si1	−33.9 (4)	C18—N2—Si1—O6	139.0 (3)
C15—C16—N2—C18	79.0 (5)	C16—N2—Si1—O6	−100.4 (3)
C15—C16—N2—C20	−148.5 (4)	C20—N2—Si1—O6	19.0 (3)
C15—C16—N2—Si1	−35.1 (4)	C18—N2—Si1—O5	17.4 (3)
C19—C20—N2—C18	−148.7 (4)	C16—N2—Si1—O5	138.0 (3)
C19—C20—N2—C16	78.4 (5)	C20—N2—Si1—O5	−102.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.05	2.857 (5)	155
C6—H6···O6ⁱⁱ	0.93	2.45	3.332 (6)	158

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

Experimental details

Crystal data
Chemical formula	C₂₀H₃₁Cl₂N₂O₆PSi
M_r	525.43
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.7738 (12), 10.9320 (13), 11.2807 (13)
α, β, γ (°)	111.135 (2), 95.926 (2), 90.424 (2)
V (Å³)	1231.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.20 × 0.15 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6745, 4720, 2997
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.194, 1.00
No. of reflections	4720
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.35

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.05	2.857 (5)	155.4
C6—H6···O6ⁱⁱ	0.93	2.45	3.332 (6)	157.9

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

Acknowledgements

The authors acknowledge financial support from the College Students' Innovative project in School of Chemical and Environmental Engineering, Hubei University for Nationalities, China (grant No. 2011 C005).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Puri, J. K., Singh, R. & Chahal, V. K. (2011). Chem. Soc. Rev. 40, 1791–1840. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, D. Q., Feras, A., Hamdan, Y., Liu, Y. & Tan, X. S. (2006). Phosphorus Sulfur Silicon Relat. Elem. 181, 1831–1838. Web of Science CrossRef CAS Google Scholar
Sun, F. M., Shi, D. Q., Tian, M. M. & Tan, X. S. (2006). Chem. J. Chin. Univ. 27, 2092–2096. CAS Google Scholar
Wan, S. G., Yang, X. Y., Yu, Y. & liu, C. (2005). Phosphorus Sulfur Silicon Relat. Elem. 180, 2813–2821. Web of Science CrossRef CAS Google Scholar

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https://doi.org/10.1107/S1600536811044928

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-(2,4-Di­chloro­phen­yl)-5,5-di­methyl-2-(3-silatranyl­propyl­mino)-1,3,2-dioxa­phospho­rinane 2-oxide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

4-(2,4-Dichlorophenyl)-5,5-dimethyl-2-(3-silatranylpropylmino)-1,3,2-dioxaphosphorinane 2-oxide