4-(2,4-Dichloro-phen-yl)-5,5-dimethyl-2-(3-silatranyl-propyl-mino)-1,3,2-dioxa-phospho-rinane 2-oxide.

In the title compound, C(20)H(31)Cl(2)N(2)O(6)PSi, the dioxaphospho-rinane ring adopts a cis conformation. The silatrane fragment forms a cage-like structure in which there exists an intra-molecular Si-N donor-acceptor bond. In the crystal, centrosymmetrically related mol-ecules are linked by pairs of N-H⋯O hydrogen bonds into inversion dimers, generating rings with graph-set motif R(2) (2)(8). The dimers are further connected into ribbons parallel to the a axis by inter-molecular 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 = 525.43

Triclinic,

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[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.194

S = 1.00

4720 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.35 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044928/rz2656sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044928/rz2656Isup2.hkl

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

C20H31Cl2N2O6PSi	Z = 2
Mr = 525.43	F(000) = 552
Triclinic, P1	Dx = 1.417 Mg m−3Dm = 1.417 Mg m−3Dm 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

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

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(Fo2) + (0.0969P)2] where P = (Fo2 + 2Fc2)/3
4720 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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	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)

	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)

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)

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.

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) ; (ii) .