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The title compound, also known as P,P'-di[3-(trimethylsilyl)-1-propyl] methylenebisphosphonic acid, H2DTMSP[MBP], C13H34O6P2Si2, was crystallized from a neat oil. The compound exists in the solid state as a hydrogen-bonded infinite chain along the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028028/br6168sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028028/br6168Isup2.hkl
Contains datablock I

CCDC reference: 259117

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.061
  • wR factor = 0.178
  • Data-to-parameter ratio = 23.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for Si2 - C10 .. 5.29 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis[3-(trimethylsilyl)propyl] methylenebisphosphonate top
Crystal data top
C13H34O6P2Si2Z = 2
Mr = 404.52F(000) = 436
Triclinic, P1Dx = 1.236 Mg m3
Hall symbol: -P 1Melting point: 313(1) K
a = 6.534 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.130 (2) ÅCell parameters from 3959 reflections
c = 16.325 (2) Åθ = 1.8–29.4°
α = 100.64 (1)°µ = 0.33 mm1
β = 100.25 (1)°T = 100 K
γ = 106.23 (2)°Prism, colorless
V = 1086.6 (4) Å30.37 × 0.13 × 0.02 mm
Data collection top
Oxford Diffraction Xcalibur3
diffractometer equipped with a CCD detector
4971 independent reflections
Radiation source: Enhance (Mo) X-ray Source3556 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scansθmax = 27.5°, θmin = 4.2°
Absorption correction: numerical
(Clark & Reid, 1995)
h = 87
Tmin = 0.888, Tmax = 0.983k = 1414
10850 measured reflectionsl = 2121
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
4971 reflections(Δ/σ)max < 0.001
214 parametersΔρmax = 1.00 e Å3
0 restraintsΔρmin = 0.57 e Å3
Special details top

Experimental. Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R·C. Clark & J·S. Reid. (Clark & Reid, 1995)

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
xyzUiso*/Ueq
C10.7308 (4)0.9586 (3)0.07610 (19)0.0266 (7)
H1A0.74301.03990.06060.032*
H1B0.76280.90200.03090.032*
C20.8949 (5)0.9821 (3)0.15949 (18)0.0245 (6)
H2A0.90090.89980.16960.029*
H2B0.84671.02470.20620.029*
C31.1261 (5)1.0657 (3)0.15930 (18)0.0236 (6)
H3A1.11671.14470.14430.028*
H3B1.17761.01970.11520.028*
C41.2286 (5)1.1882 (4)0.3517 (2)0.0333 (7)
H4A1.09401.12930.35570.050*
H4B1.20251.26420.33890.050*
H4C1.33591.21180.40530.050*
C51.3742 (5)0.9597 (3)0.2894 (2)0.0306 (7)
H5A1.41990.91520.24350.046*
H5B1.23890.90450.29570.046*
H5C1.48520.98240.34190.046*
C61.5974 (5)1.2221 (3)0.2584 (2)0.0290 (7)
H6A1.70991.23220.30820.043*
H6B1.58061.30460.25630.043*
H6C1.63811.18790.20760.043*
C70.0968 (5)0.4456 (3)0.21447 (19)0.0249 (6)
H7A0.17270.38310.22070.030*
H7B0.05110.40000.17940.030*
C80.0894 (5)0.5167 (3)0.30150 (18)0.0232 (6)
H8A0.23870.56190.33530.028*
H8B0.02030.45420.33080.028*
C90.0351 (5)0.6139 (3)0.29746 (18)0.0233 (6)
H9A0.17720.57070.25720.028*
H9B0.04520.68210.27470.028*
C100.1891 (6)0.7757 (4)0.4815 (2)0.0385 (8)
H10A0.26690.71570.49010.058*
H10B0.16370.81300.53510.058*
H10C0.27510.84270.46030.058*
C110.2517 (5)0.5594 (3)0.4417 (2)0.0327 (7)
H11A0.38370.51100.39810.049*
H11B0.28890.59770.49230.049*
H11C0.17080.50290.45550.049*
C120.2285 (6)0.8063 (4)0.3837 (2)0.0378 (8)
H12A0.14190.87210.36180.057*
H12B0.25300.84520.43700.057*
H12C0.36720.76180.34290.057*
C130.5061 (5)0.6658 (3)0.10563 (18)0.0217 (6)
H13A0.63400.65760.08560.026*
H13B0.55770.71690.16470.026*
O10.3779 (3)0.7121 (2)0.04950 (12)0.0251 (5)
O20.1511 (3)0.7452 (2)0.05977 (13)0.0249 (5)
H20.06830.67040.04230.037*
O30.5065 (3)0.89973 (19)0.08340 (13)0.0228 (4)
O40.1958 (3)0.4386 (2)0.01683 (13)0.0244 (5)
O50.4835 (3)0.4356 (2)0.14237 (12)0.0246 (5)
H50.56600.42470.11130.037*
O60.2130 (3)0.5408 (2)0.17442 (13)0.0277 (5)
P10.37690 (11)0.75255 (7)0.04168 (5)0.0198 (2)
P20.33550 (12)0.50793 (7)0.10407 (5)0.0200 (2)
Si11.33252 (13)1.10894 (8)0.26433 (5)0.0212 (2)
Si20.08000 (13)0.68904 (8)0.40161 (5)0.0236 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0178 (15)0.0302 (17)0.0289 (16)0.0015 (13)0.0037 (12)0.0123 (13)
C20.0235 (15)0.0252 (16)0.0216 (14)0.0052 (12)0.0027 (11)0.0044 (12)
C30.0243 (15)0.0240 (15)0.0247 (14)0.0090 (12)0.0075 (12)0.0078 (12)
C40.0358 (18)0.043 (2)0.0252 (16)0.0194 (16)0.0097 (14)0.0057 (15)
C50.0346 (18)0.0248 (17)0.0325 (17)0.0086 (14)0.0051 (14)0.0117 (14)
C60.0266 (16)0.0293 (17)0.0299 (16)0.0074 (13)0.0025 (13)0.0116 (14)
C70.0310 (16)0.0208 (15)0.0257 (15)0.0072 (13)0.0119 (12)0.0095 (12)
C80.0266 (15)0.0233 (15)0.0221 (14)0.0089 (12)0.0071 (12)0.0092 (12)
C90.0275 (15)0.0213 (15)0.0209 (14)0.0082 (12)0.0047 (11)0.0052 (12)
C100.047 (2)0.036 (2)0.0280 (17)0.0114 (17)0.0048 (15)0.0051 (15)
C110.0334 (18)0.0332 (18)0.0359 (18)0.0126 (15)0.0164 (14)0.0091 (15)
C120.047 (2)0.036 (2)0.0412 (19)0.0241 (17)0.0195 (16)0.0119 (16)
C130.0199 (14)0.0232 (15)0.0213 (14)0.0075 (12)0.0038 (11)0.0044 (12)
O10.0296 (11)0.0285 (12)0.0210 (10)0.0155 (9)0.0052 (8)0.0071 (9)
O20.0177 (10)0.0238 (11)0.0323 (11)0.0070 (9)0.0082 (8)0.0026 (9)
O30.0174 (10)0.0204 (11)0.0280 (11)0.0059 (8)0.0021 (8)0.0029 (9)
O40.0193 (10)0.0255 (11)0.0270 (11)0.0076 (9)0.0040 (8)0.0041 (9)
O50.0298 (11)0.0274 (12)0.0214 (10)0.0163 (9)0.0056 (8)0.0073 (9)
O60.0383 (13)0.0240 (11)0.0311 (12)0.0154 (10)0.0206 (10)0.0116 (9)
P10.0187 (4)0.0202 (4)0.0208 (4)0.0085 (3)0.0034 (3)0.0041 (3)
P20.0217 (4)0.0206 (4)0.0212 (4)0.0108 (3)0.0065 (3)0.0063 (3)
Si10.0209 (4)0.0210 (4)0.0219 (4)0.0073 (3)0.0037 (3)0.0065 (3)
Si20.0264 (5)0.0247 (5)0.0220 (4)0.0109 (4)0.0072 (3)0.0061 (3)
Geometric parameters (Å, º) top
C1—O31.464 (3)C8—H8B0.9700
C1—C21.505 (4)C9—Si21.861 (3)
C1—H1A0.9700C9—H9A0.9700
C1—H1B0.9700C9—H9B0.9700
C2—C31.538 (4)C10—Si21.869 (4)
C2—H2A0.9700C10—H10A0.9600
C2—H2B0.9700C10—H10B0.9600
C3—Si11.871 (3)C10—H10C0.9600
C3—H3A0.9700C11—Si21.864 (3)
C3—H3B0.9700C11—H11A0.9600
C4—Si11.867 (3)C11—H11B0.9600
C4—H4A0.9600C11—H11C0.9600
C4—H4B0.9600C12—Si21.865 (3)
C4—H4C0.9600C12—H12A0.9600
C5—Si11.862 (3)C12—H12B0.9600
C5—H5A0.9600C12—H12C0.9600
C5—H5B0.9600C13—P21.791 (3)
C5—H5C0.9600C13—P11.803 (3)
C6—Si11.865 (3)C13—H13A0.9700
C6—H6A0.9600C13—H13B0.9700
C6—H6B0.9600O1—P11.475 (2)
C6—H6C0.9600O2—P11.539 (2)
C7—O61.453 (3)O2—H20.8200
C7—C81.509 (4)O3—P11.572 (2)
C7—H7A0.9700O4—P21.481 (2)
C7—H7B0.9700O5—P21.543 (2)
C8—C91.529 (4)O5—H50.8200
C8—H8A0.9700O6—P21.559 (2)
O3—C1—C2110.9 (2)H9A—C9—H9B107.5
O3—C1—H1A109.5Si2—C10—H10A109.5
C2—C1—H1A109.5Si2—C10—H10B109.5
O3—C1—H1B109.5H10A—C10—H10B109.5
C2—C1—H1B109.5Si2—C10—H10C109.5
H1A—C1—H1B108.1H10A—C10—H10C109.5
C1—C2—C3112.1 (2)H10B—C10—H10C109.5
C1—C2—H2A109.2Si2—C11—H11A109.5
C3—C2—H2A109.2Si2—C11—H11B109.5
C1—C2—H2B109.2H11A—C11—H11B109.5
C3—C2—H2B109.2Si2—C11—H11C109.5
H2A—C2—H2B107.9H11A—C11—H11C109.5
C2—C3—Si1114.02 (19)H11B—C11—H11C109.5
C2—C3—H3A108.7Si2—C12—H12A109.5
Si1—C3—H3A108.7Si2—C12—H12B109.5
C2—C3—H3B108.7H12A—C12—H12B109.5
Si1—C3—H3B108.7Si2—C12—H12C109.5
H3A—C3—H3B107.6H12A—C12—H12C109.5
Si1—C4—H4A109.5H12B—C12—H12C109.5
Si1—C4—H4B109.5P2—C13—P1115.45 (15)
H4A—C4—H4B109.5P2—C13—H13A108.4
Si1—C4—H4C109.5P1—C13—H13A108.4
H4A—C4—H4C109.5P2—C13—H13B108.4
H4B—C4—H4C109.5P1—C13—H13B108.4
Si1—C5—H5A109.5H13A—C13—H13B107.5
Si1—C5—H5B109.5P1—O2—H2109.5
H5A—C5—H5B109.5C1—O3—P1121.46 (19)
Si1—C5—H5C109.5P2—O5—H5109.5
H5A—C5—H5C109.5C7—O6—P2123.21 (18)
H5B—C5—H5C109.5O1—P1—O2115.79 (12)
Si1—C6—H6A109.5O1—P1—O3113.16 (12)
Si1—C6—H6B109.5O2—P1—O3100.31 (11)
H6A—C6—H6B109.5O1—P1—C13111.17 (13)
Si1—C6—H6C109.5O2—P1—C13109.79 (12)
H6A—C6—H6C109.5O3—P1—C13105.72 (12)
H6B—C6—H6C109.5O4—P2—O5113.86 (12)
O6—C7—C8107.5 (2)O4—P2—O6116.29 (12)
O6—C7—H7A110.2O5—P2—O6104.70 (11)
C8—C7—H7A110.2O4—P2—C13111.41 (12)
O6—C7—H7B110.2O5—P2—C13108.38 (13)
C8—C7—H7B110.2O6—P2—C13101.16 (13)
H7A—C7—H7B108.5C5—Si1—C6110.22 (15)
C7—C8—C9113.7 (2)C5—Si1—C4108.40 (15)
C7—C8—H8A108.8C6—Si1—C4109.39 (16)
C9—C8—H8A108.8C5—Si1—C3109.60 (14)
C7—C8—H8B108.8C6—Si1—C3109.63 (13)
C9—C8—H8B108.8C4—Si1—C3109.59 (14)
H8A—C8—H8B107.7C9—Si2—C11108.58 (15)
C8—C9—Si2115.46 (19)C9—Si2—C12108.90 (14)
C8—C9—H9A108.4C11—Si2—C12109.31 (16)
Si2—C9—H9A108.4C9—Si2—C10110.31 (15)
C8—C9—H9B108.4C11—Si2—C10110.35 (16)
Si2—C9—H9B108.4C12—Si2—C10109.37 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O4i0.821.782.518 (3)148
O5—H5···O1ii0.821.832.493 (3)137
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z.
 

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