{N-[1-(2-Oxidophen­yl)ethyl­idene]-DL-alaninato}(pentane-1,5-di­yl)silicon(IV)

The title Si^IV complex, C₁₆H₂₁NO₃Si, is built up by a tridentate dinegative Schiff base ligand bound to a sila­cyclo­hexane unit. The coordination geometry of the penta­coordinated Si^IV atom is a distorted trigonal bipyramid. The presence of the sila­cyclo­hexane ring in the complex leads to an unusual coordination geometry of the Si^IV atom with the N atom from the Schiff base ligand and an alkyl-C atom in apical positions of the trigonal bipyramid. There is a disorder of the methyl group at the imine bond with two orientations resolved for the H atoms [major orientation = 0.55 (3)]. In the crystal, C—H...O inter­actions are found within corrugated layers of mol­ecules parallel to the ab plane.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.107
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.523 Check

Alert level G
PLAT412_ALERT_2_G Short Intra XH3 .. XHn     H2       ..H5D      .       2.06 Ang.
                                                      x,y,z  =      1_555 Check
PLAT412_ALERT_2_G Short Intra XH3 .. XHn     H5B      ..H11      .       2.13 Ang.
                                                      x,y,z  =      1_555 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H12B     ..O3       .       2.64 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
                0  0  1,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         33 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
               -1 -1  1,
PLAT967_ALERT_5_G Note: Two-Theta Cutoff Value in Embedded .res ..       55.0 Degree
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       2.62 Note
              Predicted wR2: Based on SigI   2  4.06 or SHELX Weight 10.01       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

{N-[1-(2-Oxidophenyl)ethylidene]-DL-alaninato}(pentane-1,5-diyl)silicon(IV)

Crystal data

C16H21NO3Si	Z = 2
Mr = 303.43	F(000) = 324
Triclinic, P1	Dx = 1.321 Mg m^−3
a = 6.7236 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.2935 (5) Å	Cell parameters from 21687 reflections
c = 16.1649 (11) Å	θ = 2.6–27.3°
α = 77.570 (6)°	µ = 0.16 mm^−1
β = 80.354 (5)°	T = 173 K
γ = 89.412 (6)°	Prism, colourless
V = 762.90 (10) Å^3	0.30 × 0.15 × 0.05 mm

Data collection

STOE IPDS 2 diffractometer	3289 independent reflections
Radiation source: fine-focus sealed tube	2700 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.090
Detector resolution: 6.67 pixels mm^-1	θmax = 26.9°, θmin = 2.6°
rotation method, ω scans	h = −8→8
Absorption correction: integration (X-RED; Stoe & Cie, 2009)	k = −9→9
Tmin = 0.832, Tmax = 0.984	l = −20→20
21687 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0375P)^2 + 0.4037P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
3289 reflections	Δρmax = 0.37 e Å^−3
197 parameters	Δρmin = −0.28 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Si1	0.46505 (7)	0.07538 (7)	0.20401 (3)	0.02309 (14)
O1	0.44797 (19)	0.20645 (18)	0.28018 (9)	0.0275 (3)
O2	0.5843 (2)	0.15539 (19)	0.09769 (8)	0.0298 (3)
O3	0.5822 (2)	0.2919 (2)	−0.04004 (9)	0.0378 (3)
N1	0.2467 (2)	0.2525 (2)	0.15507 (10)	0.0238 (3)
C1	0.4944 (3)	0.2453 (3)	0.03353 (12)	0.0284 (4)
C2	0.2731 (3)	0.2819 (3)	0.06087 (12)	0.0263 (4)
H2	0.255 (3)	0.412 (3)	0.0344 (14)	0.031 (6)*
C3	0.1425 (3)	0.1443 (3)	0.03230 (13)	0.0325 (4)
H3A	0.167965	0.015503	0.060743	0.049*
H3B	0.176307	0.158255	−0.030152	0.049*
H3C	−0.000290	0.171095	0.048014	0.049*
C4	0.1068 (3)	0.3338 (2)	0.19815 (12)	0.0249 (4)
C5	−0.0402 (3)	0.4663 (3)	0.15733 (13)	0.0334 (4)
H5A	0.032877	0.556000	0.107753	0.050*	0.55 (3)
H5B	−0.109387	0.534539	0.199364	0.050*	0.55 (3)
H5C	−0.139702	0.394647	0.138328	0.050*	0.55 (3)
H5D	−0.027028	0.463040	0.096368	0.050*	0.45 (3)
H5E	−0.011114	0.594190	0.162767	0.050*	0.45 (3)
H5F	−0.178071	0.427956	0.186311	0.050*	0.45 (3)
C6	0.0976 (3)	0.2987 (2)	0.29215 (12)	0.0252 (4)
C7	0.2700 (3)	0.2417 (2)	0.32842 (12)	0.0254 (4)
C8	0.2650 (3)	0.2224 (3)	0.41654 (13)	0.0321 (4)
H8	0.383339	0.188702	0.440518	0.039*
C9	0.0885 (3)	0.2519 (3)	0.46913 (14)	0.0375 (5)
H9	0.086339	0.237791	0.529089	0.045*
C10	−0.0865 (3)	0.3024 (3)	0.43487 (14)	0.0368 (5)
H10	−0.208071	0.320055	0.471404	0.044*
C11	−0.0815 (3)	0.3263 (3)	0.34729 (13)	0.0310 (4)
H11	−0.200135	0.361978	0.323846	0.037*
C12	0.2849 (3)	−0.1331 (2)	0.23573 (12)	0.0270 (4)
H12A	0.145209	−0.089668	0.234512	0.032*
H12B	0.316084	−0.214906	0.193935	0.032*
C13	0.3009 (3)	−0.2467 (3)	0.32707 (13)	0.0293 (4)
H13A	0.264948	−0.164827	0.368583	0.035*
H13B	0.201379	−0.352790	0.342705	0.035*
C14	0.5115 (3)	−0.3243 (3)	0.33537 (14)	0.0349 (5)
H14A	0.505593	−0.406052	0.393243	0.042*
H14B	0.548839	−0.403187	0.292686	0.042*
C15	0.6765 (3)	−0.1726 (3)	0.32199 (14)	0.0333 (4)
H15A	0.805711	−0.233738	0.330840	0.040*
H15B	0.641747	−0.095644	0.365645	0.040*
C16	0.7044 (3)	−0.0436 (3)	0.23210 (13)	0.0284 (4)
H16A	0.754746	−0.118478	0.188979	0.034*
H16B	0.808546	0.054194	0.228408	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0225 (2)	0.0213 (2)	0.0264 (3)	0.00193 (18)	−0.00397 (19)	−0.00730 (18)
O1	0.0249 (6)	0.0293 (7)	0.0323 (7)	0.0046 (5)	−0.0078 (5)	−0.0133 (5)
O2	0.0266 (7)	0.0327 (7)	0.0284 (7)	0.0029 (5)	−0.0019 (5)	−0.0051 (5)
O3	0.0418 (8)	0.0396 (8)	0.0284 (7)	−0.0018 (6)	0.0026 (6)	−0.0062 (6)
N1	0.0259 (8)	0.0206 (7)	0.0258 (8)	0.0009 (6)	−0.0055 (6)	−0.0061 (6)
C1	0.0330 (10)	0.0235 (8)	0.0294 (10)	−0.0014 (7)	−0.0039 (8)	−0.0085 (7)
C2	0.0316 (10)	0.0244 (9)	0.0235 (9)	0.0017 (7)	−0.0060 (7)	−0.0054 (7)
C3	0.0346 (10)	0.0344 (10)	0.0314 (10)	0.0003 (8)	−0.0086 (8)	−0.0110 (8)
C4	0.0259 (9)	0.0203 (8)	0.0293 (9)	0.0013 (7)	−0.0063 (7)	−0.0062 (7)
C5	0.0352 (11)	0.0316 (10)	0.0339 (10)	0.0115 (8)	−0.0088 (9)	−0.0064 (8)
C6	0.0288 (9)	0.0216 (8)	0.0272 (9)	0.0027 (7)	−0.0056 (7)	−0.0091 (7)
C7	0.0294 (9)	0.0189 (8)	0.0294 (9)	0.0029 (7)	−0.0056 (7)	−0.0082 (7)
C8	0.0372 (11)	0.0312 (10)	0.0316 (10)	0.0052 (8)	−0.0122 (8)	−0.0101 (8)
C9	0.0478 (13)	0.0388 (11)	0.0280 (10)	0.0071 (9)	−0.0080 (9)	−0.0108 (8)
C10	0.0385 (11)	0.0400 (11)	0.0309 (10)	0.0073 (9)	0.0002 (9)	−0.0105 (9)
C11	0.0309 (10)	0.0305 (9)	0.0329 (10)	0.0066 (8)	−0.0060 (8)	−0.0099 (8)
C12	0.0263 (9)	0.0238 (8)	0.0326 (10)	0.0022 (7)	−0.0069 (7)	−0.0082 (7)
C13	0.0294 (9)	0.0224 (8)	0.0341 (10)	0.0021 (7)	−0.0021 (8)	−0.0045 (7)
C14	0.0350 (11)	0.0286 (10)	0.0391 (11)	0.0064 (8)	−0.0074 (9)	−0.0027 (8)
C15	0.0304 (10)	0.0344 (10)	0.0365 (11)	0.0072 (8)	−0.0101 (8)	−0.0072 (8)
C16	0.0224 (9)	0.0275 (9)	0.0360 (10)	0.0037 (7)	−0.0052 (8)	−0.0086 (8)

Geometric parameters (Å, º)

Si1—O1	1.7029 (13)	C6—C7	1.404 (3)
Si1—O2	1.7474 (14)	C6—C11	1.413 (3)
Si1—C12	1.8804 (19)	C7—C8	1.396 (3)
Si1—C16	1.8961 (19)	C8—C9	1.383 (3)
Si1—N1	2.0883 (16)	C8—H8	0.9500
O1—C7	1.369 (2)	C9—C10	1.396 (3)
O2—C1	1.334 (2)	C9—H9	0.9500
O3—C1	1.214 (2)	C10—C11	1.383 (3)
N1—C4	1.291 (2)	C10—H10	0.9500
N1—C2	1.472 (2)	C11—H11	0.9500
C1—C2	1.518 (3)	C12—C13	1.550 (3)
C2—C3	1.532 (3)	C12—H12A	0.9900
C2—H2	0.97 (2)	C12—H12B	0.9900
C3—H3A	0.9800	C13—C14	1.536 (3)
C3—H3B	0.9800	C13—H13A	0.9900
C3—H3C	0.9800	C13—H13B	0.9900
C4—C6	1.476 (3)	C14—C15	1.531 (3)
C4—C5	1.507 (3)	C14—H14A	0.9900
C5—H5A	0.9800	C14—H14B	0.9900
C5—H5B	0.9800	C15—C16	1.535 (3)
C5—H5C	0.9800	C15—H15A	0.9900
C5—H5D	0.9800	C15—H15B	0.9900
C5—H5E	0.9800	C16—H16A	0.9900
C5—H5F	0.9800	C16—H16B	0.9900
O1—Si1—O2	123.53 (7)	C11—C6—C4	121.21 (17)
O1—Si1—C12	112.99 (8)	O1—C7—C8	117.48 (17)
O2—Si1—C12	121.46 (8)	O1—C7—C6	122.46 (17)
O1—Si1—C16	94.47 (8)	C8—C7—C6	120.05 (17)
O2—Si1—C16	90.31 (8)	C9—C8—C7	120.32 (19)
C12—Si1—C16	99.85 (8)	C9—C8—H8	119.8
O1—Si1—N1	85.08 (6)	C7—C8—H8	119.8
O2—Si1—N1	79.30 (6)	C8—C9—C10	120.56 (19)
C12—Si1—N1	92.16 (7)	C8—C9—H9	119.7
C16—Si1—N1	167.09 (8)	C10—C9—H9	119.7
C7—O1—Si1	123.83 (12)	C11—C10—C9	119.46 (19)
C1—O2—Si1	125.22 (12)	C11—C10—H10	120.3
C4—N1—C2	121.84 (16)	C9—C10—H10	120.3
C4—N1—Si1	126.93 (13)	C10—C11—C6	120.99 (19)
C2—N1—Si1	111.20 (11)	C10—C11—H11	119.5
O3—C1—O2	122.73 (18)	C6—C11—H11	119.5
O3—C1—C2	123.35 (18)	C13—C12—Si1	110.69 (13)
O2—C1—C2	113.92 (16)	C13—C12—H12A	109.5
N1—C2—C1	104.45 (15)	Si1—C12—H12A	109.5
N1—C2—C3	112.04 (15)	C13—C12—H12B	109.5
C1—C2—C3	109.48 (15)	Si1—C12—H12B	109.5
N1—C2—H2	111.4 (13)	H12A—C12—H12B	108.1
C1—C2—H2	105.5 (13)	C14—C13—C12	113.67 (16)
C3—C2—H2	113.3 (13)	C14—C13—H13A	108.8
C2—C3—H3A	109.5	C12—C13—H13A	108.8
C2—C3—H3B	109.5	C14—C13—H13B	108.8
H3A—C3—H3B	109.5	C12—C13—H13B	108.8
C2—C3—H3C	109.5	H13A—C13—H13B	107.7
H3A—C3—H3C	109.5	C15—C14—C13	114.03 (16)
H3B—C3—H3C	109.5	C15—C14—H14A	108.7
N1—C4—C6	117.34 (16)	C13—C14—H14A	108.7
N1—C4—C5	123.61 (17)	C15—C14—H14B	108.7
C6—C4—C5	119.02 (16)	C13—C14—H14B	108.7
C4—C5—H5A	109.5	H14A—C14—H14B	107.6
C4—C5—H5B	109.5	C14—C15—C16	112.77 (17)
H5A—C5—H5B	109.5	C14—C15—H15A	109.0
C4—C5—H5C	109.5	C16—C15—H15A	109.0
H5A—C5—H5C	109.5	C14—C15—H15B	109.0
H5B—C5—H5C	109.5	C16—C15—H15B	109.0
C4—C5—H5D	109.5	H15A—C15—H15B	107.8
C4—C5—H5E	109.5	C15—C16—Si1	113.81 (13)
H5D—C5—H5E	109.5	C15—C16—H16A	108.8
C4—C5—H5F	109.5	Si1—C16—H16A	108.8
H5D—C5—H5F	109.5	C15—C16—H16B	108.8
H5E—C5—H5F	109.5	Si1—C16—H16B	108.8
C7—C6—C11	118.54 (17)	H16A—C16—H16B	107.7
C7—C6—C4	120.22 (17)
O2—Si1—O1—C7	125.72 (14)	Si1—O1—C7—C8	134.77 (15)
C12—Si1—O1—C7	−38.25 (16)	Si1—O1—C7—C6	−46.4 (2)
C16—Si1—O1—C7	−140.93 (14)	C11—C6—C7—O1	178.09 (16)
N1—Si1—O1—C7	52.01 (14)	C4—C6—C7—O1	−3.7 (3)
O1—Si1—O2—C1	−90.30 (16)	C11—C6—C7—C8	−3.1 (3)
C12—Si1—O2—C1	72.36 (16)	C4—C6—C7—C8	175.16 (16)
C16—Si1—O2—C1	174.13 (15)	O1—C7—C8—C9	−178.58 (17)
N1—Si1—O2—C1	−13.60 (14)	C6—C7—C8—C9	2.5 (3)
Si1—O2—C1—O3	−177.12 (14)	C7—C8—C9—C10	−0.3 (3)
Si1—O2—C1—C2	2.3 (2)	C8—C9—C10—C11	−1.3 (3)
C4—N1—C2—C1	154.00 (16)	C9—C10—C11—C6	0.7 (3)
Si1—N1—C2—C1	−24.26 (16)	C7—C6—C11—C10	1.5 (3)
C4—N1—C2—C3	−87.6 (2)	C4—C6—C11—C10	−176.72 (18)
Si1—N1—C2—C3	94.15 (16)	O1—Si1—C12—C13	−50.11 (14)
O3—C1—C2—N1	−164.67 (17)	O2—Si1—C12—C13	145.55 (12)
O2—C1—C2—N1	15.9 (2)	C16—Si1—C12—C13	49.07 (14)
O3—C1—C2—C3	75.2 (2)	N1—Si1—C12—C13	−135.68 (13)
O2—C1—C2—C3	−104.25 (18)	Si1—C12—C13—C14	−60.40 (18)
C2—N1—C4—C6	−178.26 (15)	C12—C13—C14—C15	64.6 (2)
Si1—N1—C4—C6	−0.3 (2)	C13—C14—C15—C16	−61.2 (2)
C2—N1—C4—C5	−0.6 (3)	C14—C15—C16—Si1	56.1 (2)
Si1—N1—C4—C5	177.39 (14)	O1—Si1—C16—C15	65.85 (15)
N1—C4—C6—C7	23.1 (2)	O2—Si1—C16—C15	−170.47 (14)
C5—C4—C6—C7	−154.68 (17)	C12—Si1—C16—C15	−48.42 (16)
N1—C4—C6—C11	−158.72 (17)	N1—Si1—C16—C15	153.3 (3)
C5—C4—C6—C11	23.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3^i	0.97 (2)	2.45 (2)	3.197 (2)	133.1 (17)
C12—H12B···O3^ii	0.99	2.64	3.571 (2)	155

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