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Syntheses of tetraethyl iso­cyanato­methyl­enedi­phospho­nate and the title compound, C14H37NO7P2Si4, are reported. The structure of the latter shows disorder of the isocyanate group, but bond lengths and angles within this group are normal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013735/ac6169sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013735/ac61693sup2.hkl
Contains datablock 3

CCDC reference: 274316

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](N-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.102
  • Data-to-parameter ratio = 21.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.90 Ratio PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for Si22 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C2A PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C2B
Alert level C PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.88 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.89 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Si11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Si12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Si21 PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 41 C1 -N1 -C2A -O1A 160.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 42 C1 -N1 -C2B -O1B -95.00 20.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

tetrakis(trimethylsilyl) isocyanatomethylenebisphosphonate top
Crystal data top
C14H37NO7P2Si4F(000) = 1080
Mr = 505.75Dx = 1.169 Mg m3
Monoclinic, P21/nMelting point: 317 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.2012 (6) ÅCell parameters from 6971 reflections
b = 26.7355 (15) Åθ = 2.4–26.4°
c = 11.0576 (6) ŵ = 0.35 mm1
β = 107.6500 (9)°T = 193 K
V = 2873.8 (3) Å3Prism, pale yellow
Z = 40.47 × 0.43 × 0.43 mm
Data collection top
Bruker SMART 1000 CCD area-detector/PLATFORM
diffractometer
5905 independent reflections
Radiation source: fine-focus sealed tube5076 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 2.1°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 3333
Tmin = 0.854, Tmax = 0.865l = 1313
21491 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0569P)2 + 0.9513P]
where P = (Fo2 + 2Fc2)/3
5905 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.24 e Å3
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 > 2σ(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.

Part of the isocyanato group was found to be disordered. Refinement proceeded with splitting of the isocyanato C and O atoms into two sets of positions ({C2A, O1A} and {C2B, O1B}) given respective occupancy factors of 65% and 35%. Occupancy factors were chosen that allowed the Ueq's for like atoms (O1A and O1B; C2A and C2B) to refine to comparable values, and produced roughly-equivalent N—C and C—O distances in the disordered fragments.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.16510 (5)0.366963 (16)0.00836 (5)0.03749 (12)
P20.00014 (4)0.428934 (15)0.13513 (5)0.03561 (12)
Si110.15821 (5)0.266444 (18)0.11064 (5)0.04444 (14)
Si120.23621 (6)0.37441 (2)0.25130 (5)0.04931 (15)
Si210.26759 (5)0.45995 (2)0.31968 (5)0.04371 (13)
Si220.24519 (5)0.374731 (19)0.16611 (5)0.04155 (13)
O1A0.2497 (4)0.34869 (16)0.2112 (5)0.1116 (14)0.65
O1B0.2168 (8)0.3665 (3)0.2879 (8)0.110 (3)0.35
O100.30368 (13)0.38001 (5)0.07023 (13)0.0466 (3)
O110.10047 (13)0.31917 (4)0.02900 (14)0.0477 (3)
O120.14793 (15)0.35854 (5)0.15210 (13)0.0532 (3)
O200.06485 (13)0.47804 (4)0.13110 (13)0.0455 (3)
O210.13909 (12)0.42171 (4)0.24077 (11)0.0388 (3)
O220.08802 (13)0.38365 (4)0.15233 (15)0.0498 (3)
N10.08936 (18)0.40675 (7)0.11039 (18)0.0585 (5)
C10.03922 (17)0.41573 (6)0.01222 (16)0.0374 (4)
H10.07760.44730.03610.045*
C2A0.1615 (9)0.3755 (3)0.1572 (7)0.0537 (15)0.65
C2B0.1529 (18)0.3857 (5)0.1943 (12)0.052 (3)0.35
C110.0381 (3)0.21805 (8)0.0251 (2)0.0687 (6)
H11A0.04930.21310.05900.082*
H11B0.05650.22860.01570.082*
H11C0.05730.18660.07280.082*
C120.1488 (3)0.27728 (10)0.2724 (2)0.0712 (6)
H12A0.05300.28350.26890.085*
H12B0.20510.30640.30940.085*
H12C0.18320.24770.32490.085*
C130.3360 (3)0.25459 (11)0.1100 (4)0.0916 (10)
H13A0.33670.24840.02290.110*
H13B0.37260.22530.16260.110*
H13C0.39330.28380.14420.110*
C140.2837 (2)0.44083 (8)0.2280 (2)0.0588 (5)
H14A0.34830.44560.14280.071*
H14B0.20100.46090.23700.071*
H14C0.32720.45130.29160.071*
C150.3887 (3)0.33372 (11)0.2147 (3)0.0907 (9)
H15A0.45160.34260.13120.109*
H15B0.43540.33820.27940.109*
H15C0.36020.29870.21390.109*
C160.1129 (3)0.36125 (15)0.4088 (3)0.1003 (11)
H16A0.09150.32540.41590.120*
H16B0.15360.37100.47510.120*
H16C0.02830.38040.41900.120*
C210.3325 (2)0.49424 (8)0.2050 (2)0.0559 (5)
H21A0.26120.51710.15570.067*
H21B0.35630.47040.14760.067*
H21C0.41440.51340.25070.067*
C220.3988 (2)0.41718 (10)0.4186 (3)0.0705 (7)
H22A0.36070.39930.47760.085*
H22B0.47940.43650.46670.085*
H22C0.42610.39300.36400.085*
C230.1957 (3)0.50294 (10)0.4143 (2)0.0737 (7)
H23A0.12710.52480.35720.088*
H23B0.26980.52340.46920.088*
H23C0.15200.48350.46670.088*
C240.2344 (4)0.3879 (2)0.3305 (3)0.146 (2)
H24A0.21290.42340.34860.175*
H24B0.16190.36740.38700.175*
H24C0.32270.38010.34420.175*
C250.2812 (3)0.30887 (10)0.1249 (4)0.1027 (12)
H25A0.21250.28790.18470.123*
H25B0.27750.30300.03860.123*
H25C0.37310.30040.12950.123*
C260.3699 (2)0.41662 (9)0.0585 (3)0.0677 (6)
H26A0.34680.45140.08410.081*
H26B0.46250.40910.06250.081*
H26C0.36690.41170.02850.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0373 (2)0.0314 (2)0.0475 (3)0.00030 (17)0.01844 (19)0.00179 (17)
P20.0276 (2)0.0286 (2)0.0531 (3)0.00047 (15)0.01592 (18)0.00313 (17)
Si110.0404 (3)0.0332 (2)0.0597 (3)0.00166 (19)0.0150 (2)0.0083 (2)
Si120.0483 (3)0.0576 (3)0.0460 (3)0.0044 (2)0.0201 (2)0.0114 (2)
Si210.0372 (3)0.0455 (3)0.0475 (3)0.0027 (2)0.0114 (2)0.0006 (2)
Si220.0307 (2)0.0491 (3)0.0482 (3)0.00714 (19)0.0170 (2)0.0001 (2)
O1A0.080 (2)0.102 (3)0.131 (4)0.034 (2)0.001 (2)0.056 (3)
O1B0.090 (5)0.129 (7)0.095 (5)0.019 (4)0.001 (4)0.059 (5)
O100.0360 (6)0.0489 (7)0.0581 (8)0.0009 (5)0.0192 (6)0.0020 (6)
O110.0420 (7)0.0334 (6)0.0722 (9)0.0041 (5)0.0240 (6)0.0122 (6)
O120.0621 (9)0.0523 (8)0.0506 (8)0.0092 (7)0.0253 (7)0.0084 (6)
O200.0420 (7)0.0332 (6)0.0655 (8)0.0048 (5)0.0226 (6)0.0026 (6)
O210.0337 (6)0.0395 (6)0.0453 (7)0.0010 (5)0.0150 (5)0.0024 (5)
O220.0335 (6)0.0335 (6)0.0892 (10)0.0019 (5)0.0289 (7)0.0077 (6)
N10.0497 (10)0.0456 (9)0.0642 (12)0.0073 (8)0.0066 (8)0.0049 (8)
C10.0349 (8)0.0294 (8)0.0455 (9)0.0004 (6)0.0085 (7)0.0027 (7)
C2A0.050 (2)0.055 (4)0.055 (4)0.000 (3)0.014 (3)0.009 (3)
C2B0.062 (5)0.040 (5)0.051 (7)0.000 (4)0.012 (5)0.001 (4)
C110.0854 (17)0.0392 (11)0.0712 (15)0.0057 (11)0.0083 (13)0.0018 (10)
C120.0742 (16)0.0763 (16)0.0557 (13)0.0036 (13)0.0085 (12)0.0064 (11)
C130.0602 (15)0.0695 (16)0.157 (3)0.0282 (13)0.0505 (17)0.0426 (18)
C140.0600 (13)0.0577 (12)0.0631 (13)0.0018 (10)0.0251 (11)0.0064 (10)
C150.0765 (18)0.0759 (18)0.129 (3)0.0140 (14)0.0448 (18)0.0312 (17)
C160.093 (2)0.154 (3)0.0522 (15)0.050 (2)0.0200 (14)0.0219 (17)
C210.0502 (11)0.0466 (11)0.0761 (14)0.0100 (9)0.0271 (10)0.0023 (10)
C220.0473 (12)0.0800 (16)0.0733 (16)0.0019 (11)0.0022 (11)0.0183 (13)
C230.0814 (17)0.0774 (16)0.0655 (15)0.0043 (13)0.0269 (13)0.0235 (13)
C240.088 (2)0.294 (7)0.0624 (19)0.012 (3)0.0344 (17)0.025 (3)
C250.0580 (15)0.0480 (13)0.194 (4)0.0162 (12)0.0252 (19)0.0049 (17)
C260.0355 (10)0.0665 (14)0.1011 (19)0.0032 (9)0.0207 (11)0.0142 (13)
Geometric parameters (Å, º) top
P1—O101.4596 (14)C12—H12A0.9800
P1—O111.5502 (12)C12—H12B0.9800
P1—O121.5617 (14)C12—H12C0.9800
P1—C11.8214 (17)C13—H13A0.9800
P2—O201.4653 (12)C13—H13B0.9800
P2—O211.5514 (13)C13—H13C0.9800
P2—O221.5539 (12)C14—H14A0.9800
P2—C11.8253 (18)C14—H14B0.9800
Si11—O111.6813 (13)C14—H14C0.9800
Si11—C111.835 (2)C15—H15A0.9800
Si11—C121.843 (3)C15—H15B0.9800
Si11—C131.843 (2)C15—H15C0.9800
Si12—O121.6713 (14)C16—H16A0.9800
Si12—C141.838 (2)C16—H16B0.9800
Si12—C151.840 (3)C16—H16C0.9800
Si12—C161.846 (3)C21—H21A0.9800
Si21—O211.6826 (13)C21—H21B0.9800
Si21—C211.843 (2)C21—H21C0.9800
Si21—C221.846 (2)C22—H22A0.9800
Si21—C231.849 (2)C22—H22B0.9800
Si22—O221.6730 (12)C22—H22C0.9800
Si22—C241.822 (3)C23—H23A0.9800
Si22—C251.828 (3)C23—H23B0.9800
Si22—C261.836 (2)C23—H23C0.9800
O1A—C2A1.164 (9)C24—H24A0.9800
O1B—C2B1.162 (17)C24—H24B0.9800
N1—C11.447 (2)C24—H24C0.9800
N1—C2A1.129 (9)C25—H25A0.9800
N1—C2B1.111 (17)C25—H25B0.9800
C1—H11.0000C25—H25C0.9800
C11—H11A0.9800C26—H26A0.9800
C11—H11B0.9800C26—H26B0.9800
C11—H11C0.9800C26—H26C0.9800
O10—P1—O11116.85 (8)H12B—C12—H12C109.5
O10—P1—O12115.46 (8)Si11—C13—H13A109.5
O11—P1—O12103.12 (8)Si11—C13—H13B109.5
O10—P1—C1113.06 (8)Si11—C13—H13C109.5
O11—P1—C1104.03 (7)H13A—C13—H13B109.5
O12—P1—C1102.63 (8)H13A—C13—H13C109.5
O20—P2—O21115.85 (7)H13B—C13—H13C109.5
O20—P2—O22115.37 (7)Si12—C14—H14A109.5
O21—P2—O22103.97 (7)Si12—C14—H14B109.5
O20—P2—C1111.43 (8)Si12—C14—H14C109.5
O21—P2—C1104.54 (7)H14A—C14—H14B109.5
O22—P2—C1104.46 (8)H14A—C14—H14C109.5
O11—Si11—C11104.11 (9)H14B—C14—H14C109.5
O11—Si11—C12106.05 (10)Si12—C15—H15A109.5
O11—Si11—C13109.09 (10)Si12—C15—H15B109.5
C11—Si11—C12112.83 (12)Si12—C15—H15C109.5
C11—Si11—C13112.38 (15)H15A—C15—H15B109.5
C12—Si11—C13111.82 (15)H15A—C15—H15C109.5
O12—Si12—C14108.94 (9)H15B—C15—H15C109.5
O12—Si12—C15107.05 (13)Si12—C16—H16A109.5
O12—Si12—C16102.84 (11)Si12—C16—H16B109.5
C14—Si12—C15111.78 (13)Si12—C16—H16C109.5
C14—Si12—C16113.06 (14)H16A—C16—H16B109.5
C15—Si12—C16112.55 (16)H16A—C16—H16C109.5
O21—Si21—C21109.35 (9)H16B—C16—H16C109.5
O21—Si21—C22104.00 (10)Si21—C21—H21A109.5
O21—Si21—C23106.90 (10)Si21—C21—H21B109.5
C21—Si21—C22111.63 (11)Si21—C21—H21C109.5
C21—Si21—C23111.53 (12)H21A—C21—H21B109.5
C22—Si21—C23112.99 (13)H21A—C21—H21C109.5
O22—Si22—C24107.08 (14)H21B—C21—H21C109.5
O22—Si22—C25103.92 (11)Si21—C22—H22A109.5
O22—Si22—C26110.42 (9)Si21—C22—H22B109.5
C24—Si22—C25112.4 (2)Si21—C22—H22C109.5
C24—Si22—C26110.41 (18)H22A—C22—H22B109.5
C25—Si22—C26112.25 (14)H22A—C22—H22C109.5
P1—O11—Si11136.56 (9)H22B—C22—H22C109.5
P1—O12—Si12135.64 (10)Si21—C23—H23A109.5
P2—O21—Si21134.84 (8)Si21—C23—H23B109.5
P2—O22—Si22136.75 (8)Si21—C23—H23C109.5
C1—N1—C2A141.6 (4)H23A—C23—H23B109.5
C1—N1—C2B151.4 (9)H23A—C23—H23C109.5
P1—C1—P2117.44 (9)H23B—C23—H23C109.5
P1—C1—N1111.79 (12)Si22—C24—H24A109.5
P1—C1—H1106.3Si22—C24—H24B109.5
P2—C1—N1107.95 (13)Si22—C24—H24C109.5
P2—C1—H1106.3H24A—C24—H24B109.5
N1—C1—H1106.3H24A—C24—H24C109.5
N1—C2A—O1A170.3 (9)H24B—C24—H24C109.5
N1—C2B—O1B174.8 (12)Si22—C25—H25A109.5
Si11—C11—H11A109.5Si22—C25—H25B109.5
Si11—C11—H11B109.5Si22—C25—H25C109.5
Si11—C11—H11C109.5H25A—C25—H25B109.5
H11A—C11—H11B109.5H25A—C25—H25C109.5
H11A—C11—H11C109.5H25B—C25—H25C109.5
H11B—C11—H11C109.5Si22—C26—H26A109.5
Si11—C12—H12A109.5Si22—C26—H26B109.5
Si11—C12—H12B109.5Si22—C26—H26C109.5
Si11—C12—H12C109.5H26A—C26—H26B109.5
H12A—C12—H12B109.5H26A—C26—H26C109.5
H12A—C12—H12C109.5H26B—C26—H26C109.5
O10—P1—O11—Si1122.75 (17)O21—P2—C1—N1162.96 (11)
O12—P1—O11—Si11105.04 (14)O22—P2—C1—P173.40 (11)
C1—P1—O11—Si11148.13 (13)O22—P2—C1—N154.03 (13)
O10—P1—O12—Si1219.63 (17)C11—Si11—O11—P1143.80 (15)
O11—P1—O12—Si12148.28 (13)C12—Si11—O11—P196.95 (16)
C1—P1—O12—Si12103.82 (14)C13—Si11—O11—P123.6 (2)
O10—P1—C1—P266.63 (12)C14—Si12—O12—P146.20 (17)
O10—P1—C1—N1167.82 (13)C15—Si12—O12—P174.84 (17)
O11—P1—C1—P261.13 (11)C16—Si12—O12—P1166.39 (18)
O11—P1—C1—N164.43 (15)C21—Si21—O21—P255.71 (13)
O12—P1—C1—P2168.33 (9)C22—Si21—O21—P2175.07 (13)
O12—P1—C1—N142.77 (15)C23—Si21—O21—P265.17 (15)
O20—P2—O21—Si2128.29 (14)C24—Si22—O22—P280.8 (2)
O22—P2—O21—Si21155.97 (11)C25—Si22—O22—P2160.02 (19)
C1—P2—O21—Si2194.74 (12)C26—Si22—O22—P239.45 (19)
O20—P2—O22—Si221.19 (19)C2A—N1—C1—P138.5 (7)
O21—P2—O22—Si22129.17 (14)C2A—N1—C1—P292.2 (7)
C1—P2—O22—Si22121.48 (15)C2B—N1—C1—P18.3 (12)
O20—P2—C1—P1161.39 (9)C2B—N1—C1—P2138.9 (12)
O20—P2—C1—N171.18 (13)C1—N1—C2A—O1A160 (4)
O21—P2—C1—P135.53 (11)C1—N1—C2B—O1B95 (20)
 

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