Download citation
Download citation
link to html
In the title compound, C27H36N2O6Si, the angle between the two least-squares planes of the nitro­phenyl groups is 34.65 (9)°. Owing to the presence of an approximate non-crystallographic mirror plane, the title compound is an example of an achiral mol­ecule crystallizing in a chiral space group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001137/ob6109sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001137/ob6109Isup2.hkl
Contains datablock I

CCDC reference: 182608

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.081
  • Data-to-parameter ratio = 14.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 4610 Count of symmetry unique reflns 2636 Completeness (_total/calc) 174.89% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1974 Fraction of Friedel pairs measured 0.749 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Comment top

The title compound, (I), was prepared as part of an ongoing study into the Lewis-acid-mediated additions of silylated methylenecyclopropanes to aldehydes. It is an example of an achiral molecule crystalizing in a chiral space group and the angle between the two least-squares planes of the nitrophenyl groups is 34.65 (9)°.

Experimental top

The synthesis of the title compound were carried out by the BF3·Et2O-mediated addition of triisopropyl(2-methylidenecyclopropyl)silane to 4-nitrobenzaldehyde in dichloromethane in 29% yield.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO, COLLECT and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin, et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1998).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) (30% probability displacement ellipsoids).
[(2R,5S)-2,5-Bis(4-nitrophenyl)perhydrofuro[2,3-b]furan-3-yl]triisopropylsilane top
Crystal data top
C27H36N2O6SiDx = 1.294 Mg m3
Mr = 512.67Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4610 reflections
a = 11.4829 (3) Åθ = 2.9–25.0°
b = 14.5419 (3) ŵ = 0.13 mm1
c = 15.7595 (4) ÅT = 120 K
V = 2631.57 (11) Å3Block, colourless
Z = 40.2 × 0.15 × 0.1 mm
F(000) = 1096
Data collection top
Nonius KappaCCD area-detector
diffractometer
4610 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode4150 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 9.091 pixels/mm pixels mm-1θmax = 25.0°, θmin = 2.9°
Φ and ω scans to fill asymmetric unith = 1313
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
k = 1717
Tmin = 0.974, Tmax = 0.987l = 1818
14158 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0435P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.081(Δ/σ)max = 0.011
S = 1.08Δρmax = 0.28 e Å3
4610 reflectionsΔρmin = 0.19 e Å3
326 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0054 (9)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1974 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.04 (11)
Crystal data top
C27H36N2O6SiV = 2631.57 (11) Å3
Mr = 512.67Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.4829 (3) ŵ = 0.13 mm1
b = 14.5419 (3) ÅT = 120 K
c = 15.7595 (4) Å0.2 × 0.15 × 0.1 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
4610 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
4150 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.987Rint = 0.043
14158 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.081Δρmax = 0.28 e Å3
S = 1.08Δρmin = 0.19 e Å3
4610 reflectionsAbsolute structure: Flack (1983), 1974 Friedel pairs
326 parametersAbsolute structure parameter: 0.04 (11)
0 restraints
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
xyzUiso*/Ueq
C10.24588 (18)0.30746 (12)0.55009 (12)0.0181 (4)
C20.31673 (18)0.37229 (13)0.58709 (13)0.0215 (5)
H20.38410.35430.61780.026*
C30.28775 (18)0.46467 (13)0.57859 (12)0.0203 (4)
H30.33570.51040.60380.024*
C40.18880 (17)0.49060 (13)0.53334 (12)0.0170 (4)
C50.11883 (18)0.42272 (13)0.49717 (12)0.0207 (4)
H50.05100.44000.46650.025*
C60.14686 (18)0.33031 (13)0.50535 (12)0.0208 (5)
H60.09910.28410.48080.025*
C70.15625 (16)0.59048 (12)0.52233 (12)0.0164 (4)
H70.13850.60260.46120.020*
C80.05374 (17)0.62342 (12)0.57714 (12)0.0173 (4)
H8A0.04880.58720.63020.021*
H8B0.02070.61720.54590.021*
C90.07986 (16)0.72624 (12)0.59682 (11)0.0159 (4)
C100.01647 (17)0.79106 (13)0.53383 (12)0.0181 (4)
H10A0.06040.76580.51750.022*
H10B0.00540.85290.55870.022*
C110.09817 (16)0.79477 (13)0.45799 (12)0.0175 (4)
H110.08870.73760.42340.021*
C120.20914 (17)0.73603 (13)0.56837 (11)0.0170 (4)
H120.25620.76330.61550.020*
C130.08396 (16)0.87798 (12)0.40158 (12)0.0171 (4)
C140.12278 (18)0.96456 (13)0.42599 (13)0.0210 (5)
H140.15950.97260.47950.025*
C150.10802 (18)1.03917 (13)0.37240 (14)0.0239 (5)
H150.13391.09870.38870.029*
C160.05479 (17)1.02531 (13)0.29475 (13)0.0218 (4)
C170.01480 (17)0.94038 (13)0.26911 (13)0.0215 (5)
H170.02150.93250.21540.026*
C180.02910 (17)0.86714 (13)0.32398 (13)0.0205 (4)
H180.00080.80820.30820.025*
C190.09741 (18)0.66025 (13)0.78274 (12)0.0213 (4)
H190.05380.60540.76130.026*
C200.0647 (2)0.67037 (17)0.87670 (13)0.0352 (6)
H20A0.01820.68560.88150.053*
H20B0.11130.71960.90230.053*
H20C0.08020.61240.90640.053*
C210.22669 (18)0.63654 (15)0.77507 (14)0.0267 (5)
H21A0.24700.62890.71510.040*
H21B0.24250.57920.80560.040*
H21C0.27340.68630.79960.040*
C220.10770 (17)0.78267 (13)0.73423 (12)0.0217 (5)
H220.11240.79770.79600.026*
C230.18196 (18)0.69638 (15)0.72297 (15)0.0304 (5)
H23A0.14470.64460.75210.046*
H23B0.18940.68230.66240.046*
H23C0.25940.70690.74720.046*
C240.16472 (18)0.86470 (16)0.68855 (14)0.0306 (5)
H24A0.11660.91970.69640.046*
H24B0.24240.87560.71230.046*
H24C0.17150.85110.62790.046*
C250.14086 (18)0.86623 (13)0.74331 (12)0.0212 (4)
H250.21970.84300.75960.025*
C260.0912 (2)0.91336 (15)0.82286 (14)0.0321 (5)
H26A0.07830.86730.86730.048*
H26B0.01710.94310.80870.048*
H26C0.14650.95970.84330.048*
C270.1611 (2)0.93941 (14)0.67450 (14)0.0275 (5)
H27A0.19310.91010.62360.041*
H27B0.21610.98560.69550.041*
H27C0.08700.96920.66050.041*
N10.28088 (16)0.20983 (11)0.55630 (11)0.0237 (4)
N20.04039 (15)1.10398 (12)0.23780 (13)0.0305 (4)
O10.37431 (14)0.19131 (10)0.58978 (11)0.0350 (4)
O20.21487 (14)0.15148 (10)0.52703 (11)0.0373 (4)
O30.05978 (15)1.18119 (10)0.26650 (12)0.0455 (5)
O40.00971 (16)1.09004 (12)0.16447 (11)0.0468 (5)
O50.25208 (11)0.64728 (8)0.54841 (8)0.0180 (3)
O60.21199 (11)0.79525 (9)0.49660 (8)0.0179 (3)
Si10.05191 (5)0.76050 (3)0.71299 (3)0.01668 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0241 (11)0.0119 (9)0.0181 (10)0.0022 (8)0.0072 (9)0.0008 (8)
C20.0235 (12)0.0210 (11)0.0201 (10)0.0003 (9)0.0010 (9)0.0006 (9)
C30.0228 (11)0.0169 (10)0.0213 (10)0.0015 (8)0.0007 (9)0.0015 (8)
C40.0223 (11)0.0164 (10)0.0123 (9)0.0007 (8)0.0036 (8)0.0003 (8)
C50.0220 (11)0.0224 (11)0.0176 (10)0.0006 (8)0.0005 (9)0.0003 (9)
C60.0219 (11)0.0191 (10)0.0215 (10)0.0049 (8)0.0046 (9)0.0053 (9)
C70.0177 (10)0.0174 (10)0.0139 (9)0.0020 (8)0.0003 (8)0.0011 (8)
C80.0174 (10)0.0182 (10)0.0161 (9)0.0025 (8)0.0013 (9)0.0013 (8)
C90.0142 (10)0.0178 (10)0.0157 (9)0.0002 (7)0.0001 (8)0.0006 (8)
C100.0184 (11)0.0197 (10)0.0160 (9)0.0003 (8)0.0022 (8)0.0003 (8)
C110.0197 (11)0.0149 (10)0.0178 (10)0.0003 (8)0.0008 (8)0.0003 (8)
C120.0211 (11)0.0139 (9)0.0159 (9)0.0006 (8)0.0013 (8)0.0008 (8)
C130.0184 (11)0.0148 (10)0.0182 (10)0.0025 (8)0.0041 (8)0.0015 (8)
C140.0243 (12)0.0193 (11)0.0193 (10)0.0019 (9)0.0029 (9)0.0009 (8)
C150.0233 (11)0.0169 (10)0.0315 (12)0.0024 (9)0.0032 (10)0.0014 (9)
C160.0172 (10)0.0203 (10)0.0279 (11)0.0022 (9)0.0026 (9)0.0096 (9)
C170.0206 (11)0.0248 (11)0.0189 (10)0.0015 (8)0.0025 (9)0.0017 (9)
C180.0208 (11)0.0185 (10)0.0222 (10)0.0019 (8)0.0015 (9)0.0011 (9)
C190.0236 (11)0.0239 (10)0.0165 (10)0.0017 (8)0.0030 (9)0.0008 (9)
C200.0375 (14)0.0486 (15)0.0194 (11)0.0095 (11)0.0011 (10)0.0076 (10)
C210.0248 (12)0.0267 (10)0.0286 (12)0.0023 (9)0.0026 (10)0.0070 (10)
C220.0182 (11)0.0315 (11)0.0155 (10)0.0034 (9)0.0007 (8)0.0030 (8)
C230.0207 (12)0.0411 (13)0.0293 (12)0.0052 (10)0.0000 (10)0.0009 (11)
C240.0208 (12)0.0436 (13)0.0275 (12)0.0125 (10)0.0016 (10)0.0014 (10)
C250.0196 (11)0.0226 (10)0.0215 (10)0.0006 (8)0.0016 (9)0.0047 (9)
C260.0370 (14)0.0316 (12)0.0278 (11)0.0013 (10)0.0015 (11)0.0131 (10)
C270.0319 (13)0.0201 (11)0.0306 (12)0.0025 (9)0.0019 (10)0.0037 (10)
N10.0284 (11)0.0193 (9)0.0234 (9)0.0012 (8)0.0057 (8)0.0013 (7)
N20.0189 (10)0.0299 (11)0.0428 (12)0.0001 (8)0.0028 (9)0.0184 (9)
O10.0315 (10)0.0229 (8)0.0506 (10)0.0066 (7)0.0021 (8)0.0029 (8)
O20.0450 (10)0.0170 (7)0.0499 (10)0.0040 (7)0.0044 (8)0.0083 (7)
O30.0451 (11)0.0230 (9)0.0684 (12)0.0070 (7)0.0170 (10)0.0192 (9)
O40.0561 (12)0.0480 (11)0.0364 (10)0.0013 (9)0.0134 (9)0.0239 (9)
O50.0163 (7)0.0143 (6)0.0233 (7)0.0002 (6)0.0022 (6)0.0004 (6)
O60.0169 (7)0.0176 (7)0.0192 (7)0.0000 (5)0.0021 (6)0.0052 (6)
Si10.0156 (3)0.0203 (3)0.0141 (3)0.0008 (2)0.0006 (2)0.0016 (2)
Geometric parameters (Å, º) top
C1—C21.375 (3)C17—C181.382 (3)
C1—C61.379 (3)C17—H170.9500
C1—N11.479 (2)C18—H180.9500
C2—C31.390 (3)C19—C211.529 (3)
C2—H20.9500C19—C201.535 (3)
C3—C41.393 (3)C19—Si11.899 (2)
C3—H30.9500C19—H191.0000
C4—C51.395 (3)C20—H20A0.9800
C4—C71.510 (3)C20—H20B0.9800
C5—C61.388 (3)C20—H20C0.9800
C5—H50.9500C21—H21A0.9800
C6—H60.9500C21—H21B0.9800
C7—O51.436 (2)C21—H21C0.9800
C7—C81.537 (3)C22—C231.527 (3)
C7—H71.0000C22—C241.539 (3)
C8—C91.556 (3)C22—Si11.891 (2)
C8—H8A0.9900C22—H221.0000
C8—H8B0.9900C23—H23A0.9800
C9—C101.550 (3)C23—H23B0.9800
C9—C121.557 (3)C23—H23C0.9800
C9—Si11.9244 (19)C24—H24A0.9800
C10—C111.520 (3)C24—H24B0.9800
C10—H10A0.9900C24—H24C0.9800
C10—H10B0.9900C25—C261.538 (3)
C11—O61.442 (2)C25—C271.537 (3)
C11—C131.510 (3)C25—Si11.907 (2)
C11—H111.0000C25—H251.0000
C12—O51.417 (2)C26—H26A0.9800
C12—O61.422 (2)C26—H26B0.9800
C12—H121.0000C26—H26C0.9800
C13—C181.385 (3)C27—H27A0.9800
C13—C141.390 (3)C27—H27B0.9800
C14—C151.385 (3)C27—H27C0.9800
C14—H140.9500N1—O11.225 (2)
C15—C161.383 (3)N1—O21.228 (2)
C15—H150.9500N2—O41.225 (3)
C16—C171.378 (3)N2—O31.231 (2)
C16—N21.464 (3)
C2—C1—C6122.66 (18)C17—C18—H18119.4
C2—C1—N1118.00 (18)C13—C18—H18119.4
C6—C1—N1119.30 (17)C21—C19—C20109.59 (18)
C1—C2—C3118.68 (19)C21—C19—Si1113.24 (14)
C1—C2—H2120.7C20—C19—Si1114.69 (14)
C3—C2—H2120.7C21—C19—H19106.2
C2—C3—C4120.39 (19)C20—C19—H19106.2
C2—C3—H3119.8Si1—C19—H19106.2
C4—C3—H3119.8C19—C20—H20A109.5
C3—C4—C5119.17 (18)C19—C20—H20B109.5
C3—C4—C7121.40 (17)H20A—C20—H20B109.5
C5—C4—C7119.42 (17)C19—C20—H20C109.5
C6—C5—C4120.91 (19)H20A—C20—H20C109.5
C6—C5—H5119.5H20B—C20—H20C109.5
C4—C5—H5119.5C19—C21—H21A109.5
C1—C6—C5118.18 (18)C19—C21—H21B109.5
C1—C6—H6120.9H21A—C21—H21B109.5
C5—C6—H6120.9C19—C21—H21C109.5
O5—C7—C4109.31 (15)H21A—C21—H21C109.5
O5—C7—C8104.29 (14)H21B—C21—H21C109.5
C4—C7—C8115.15 (16)C23—C22—C24110.17 (17)
O5—C7—H7109.3C23—C22—Si1112.37 (14)
C4—C7—H7109.3C24—C22—Si1117.49 (14)
C8—C7—H7109.3C23—C22—H22105.2
C7—C8—C9105.30 (15)C24—C22—H22105.2
C7—C8—H8A110.7Si1—C22—H22105.2
C9—C8—H8A110.7C22—C23—H23A109.5
C7—C8—H8B110.7C22—C23—H23B109.5
C9—C8—H8B110.7H23A—C23—H23B109.5
H8A—C8—H8B108.8C22—C23—H23C109.5
C10—C9—C8111.47 (15)H23A—C23—H23C109.5
C10—C9—C12101.98 (14)H23B—C23—H23C109.5
C8—C9—C12102.37 (14)C22—C24—H24A109.5
C10—C9—Si1111.93 (12)C22—C24—H24B109.5
C8—C9—Si1113.97 (12)H24A—C24—H24B109.5
C12—C9—Si1114.16 (12)C22—C24—H24C109.5
C11—C10—C9103.60 (15)H24A—C24—H24C109.5
C11—C10—H10A111.0H24B—C24—H24C109.5
C9—C10—H10A111.0C26—C25—C27108.82 (17)
C11—C10—H10B111.0C26—C25—Si1111.40 (14)
C9—C10—H10B111.0C27—C25—Si1117.54 (14)
H10A—C10—H10B109.0C26—C25—H25106.1
O6—C11—C13110.03 (15)C27—C25—H25106.1
O6—C11—C10103.17 (15)Si1—C25—H25106.1
C13—C11—C10115.11 (16)C25—C26—H26A109.5
O6—C11—H11109.4C25—C26—H26B109.5
C13—C11—H11109.4H26A—C26—H26B109.5
C10—C11—H11109.4C25—C26—H26C109.5
O5—C12—O6111.53 (14)H26A—C26—H26C109.5
O5—C12—C9108.20 (14)H26B—C26—H26C109.5
O6—C12—C9107.84 (14)C25—C27—H27A109.5
O5—C12—H12109.7C25—C27—H27B109.5
O6—C12—H12109.7H27A—C27—H27B109.5
C9—C12—H12109.7C25—C27—H27C109.5
C18—C13—C14119.57 (18)H27A—C27—H27C109.5
C18—C13—C11118.54 (17)H27B—C27—H27C109.5
C14—C13—C11121.89 (18)O1—N1—O2123.39 (17)
C15—C14—C13120.10 (19)O1—N1—C1118.51 (16)
C15—C14—H14119.9O2—N1—C1118.09 (17)
C13—C14—H14119.9O4—N2—O3123.35 (18)
C16—C15—C14118.65 (19)O4—N2—C16118.79 (18)
C16—C15—H15120.7O3—N2—C16117.86 (18)
C14—C15—H15120.7C12—O5—C7108.71 (14)
C17—C16—C15122.51 (18)C12—O6—C11108.17 (13)
C17—C16—N2118.88 (18)C22—Si1—C19107.17 (9)
C15—C16—N2118.60 (18)C22—Si1—C25109.72 (9)
C16—C17—C18117.88 (18)C19—Si1—C25109.06 (9)
C16—C17—H17121.1C22—Si1—C9111.98 (8)
C18—C17—H17121.1C19—Si1—C9107.82 (8)
C17—C18—C13121.27 (18)C25—Si1—C9110.97 (8)

Experimental details

Crystal data
Chemical formulaC27H36N2O6Si
Mr512.67
Crystal system, space groupOrthorhombic, P212121
Temperature (K)120
a, b, c (Å)11.4829 (3), 14.5419 (3), 15.7595 (4)
V3)2631.57 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.2 × 0.15 × 0.1
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1997)
Tmin, Tmax0.974, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
14158, 4610, 4150
Rint0.043
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.081, 1.08
No. of reflections4610
No. of parameters326
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.19
Absolute structureFlack (1983), 1974 Friedel pairs
Absolute structure parameter0.04 (11)

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, DENZO, COLLECT and maXus (Mackay et al., 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CAMERON (Watkin, et al., 1993), WinGX (Farrugia, 1998).

 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds