[(2R,5R)-2,5-Bis(4-nitro­phenyl)­per­hydro­furo[2,3-b]­furan-3-yl]­triiso­propyl­silane

The title mol­ecule, C₂₇H₃₆N₂O₆Si, contains a pair of fused tetra­hydro­furan rings, symmetrically substituted by p-nitro­phenyl groups at centres of R chirality. The crystal structure is composed of dimers interacting through π-stacking to form columns.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.128
• Data-to-parameter ratio = 17.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: DENZO (Hooft, 1998) and COLLECT (Otwinowski & Minor, 1997); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PLATON.

(I)

Crystal data

C27H36N2O6Si	Z = 2
Mr = 512.67	F(000) = 548
Triclinic, P1	Dx = 1.307 Mg m^−3
a = 7.9703 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.128 (2) Å	Cell parameters from 9132 reflections
c = 14.121 (3) Å	θ = 2.9–27.5°
α = 79.14 (3)°	µ = 0.14 mm^−1
β = 83.06 (3)°	T = 120 K
γ = 77.29 (3)°	Block, colourless
V = 1303.2 (4) Å^3	0.38 × 0.14 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer	4879 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.050
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	θmax = 27.5°, θmin = 3.0°
Tmin = 0.951, Tmax = 0.992	h = −10→10
19904 measured reflections	k = −15→15
5893 independent reflections	l = −18→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0702P)^2 + 0.5256P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.128	(Δ/σ)max = 0.023
S = 1.02	Δρmax = 0.67 e Å^−3
5893 reflections	Δρmin = −0.37 e Å^−3
332 parameters

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	0.19127 (18)	0.81773 (12)	0.24030 (10)	0.0169 (3)
C2	0.31726 (19)	0.70920 (12)	0.28815 (11)	0.0186 (3)
H2	0.4103	0.7328	0.3165	0.022*
C3	0.04386 (19)	0.67705 (13)	0.33902 (11)	0.0202 (3)
H3	0.0284	0.636	0.2865	0.024*
C4	0.01894 (18)	0.80596 (12)	0.30108 (11)	0.0190 (3)
H4A	−0.0001	0.8502	0.355	0.023*
H4B	−0.0799	0.8326	0.2605	0.023*
C5	0.34403 (19)	0.69788 (13)	0.12162 (11)	0.0199 (3)
H5	0.4407	0.7335	0.0864	0.024*
C6	0.18500 (19)	0.79205 (12)	0.13737 (11)	0.0184 (3)
H6A	0.0779	0.7654	0.1329	0.022*
H6B	0.1891	0.8616	0.0883	0.022*
C7	−0.0787 (2)	0.65004 (13)	0.42593 (11)	0.0217 (3)
C8	−0.0426 (2)	0.65256 (13)	0.51978 (12)	0.0246 (3)
H8	0.0686	0.6608	0.5314	0.029*
C9	−0.1684 (2)	0.64306 (13)	0.59587 (12)	0.0261 (4)
H9	−0.145	0.6453	0.6598	0.031*
C10	−0.3293 (2)	0.63023 (13)	0.57713 (12)	0.0246 (3)
C11	−0.3662 (2)	0.62176 (14)	0.48604 (12)	0.0261 (3)
H11	−0.4757	0.6096	0.4754	0.031*
C12	−0.2393 (2)	0.63155 (14)	0.41051 (12)	0.0245 (3)
H12	−0.2618	0.6256	0.3473	0.029*
C13	0.30829 (18)	0.61183 (13)	0.06597 (11)	0.0179 (3)
C14	0.33627 (18)	0.62753 (13)	−0.03453 (11)	0.0197 (3)
H14	0.385	0.6903	−0.0678	0.024*
C15	0.29371 (19)	0.55254 (14)	−0.08670 (11)	0.0210 (3)
H15	0.3106	0.5638	−0.1553	0.025*
C16	0.22599 (18)	0.46094 (13)	−0.03533 (11)	0.0201 (3)
C17	0.19931 (19)	0.44168 (13)	0.06449 (11)	0.0209 (3)
H17	0.1542	0.3773	0.0976	0.025*
C18	0.23984 (19)	0.51823 (13)	0.11482 (11)	0.0194 (3)
H18	0.2209	0.5071	0.1834	0.023*
C19	0.4367 (2)	0.97993 (13)	0.14535 (12)	0.0224 (3)
H19	0.4038	0.9572	0.0867	0.027*
C20	0.6085 (2)	0.90035 (16)	0.17067 (15)	0.0341 (4)
H20A	0.6937	0.9067	0.1148	0.051*
H20B	0.5922	0.821	0.1877	0.051*
H20C	0.6497	0.9223	0.2257	0.051*
C21	0.4645 (2)	1.10360 (15)	0.11479 (14)	0.0308 (4)
H21A	0.4881	1.132	0.1713	0.046*
H21B	0.3605	1.1525	0.0876	0.046*
H21C	0.5627	1.1051	0.0659	0.046*
C22	0.0700 (2)	1.08596 (14)	0.21359 (13)	0.0273 (4)
H22	0.1213	1.1559	0.2038	0.033*
C23	0.0003 (2)	1.08686 (15)	0.11646 (14)	0.0332 (4)
H23A	−0.0558	1.0214	0.122	0.05*
H23B	0.096	1.0815	0.0659	0.05*
H23C	−0.0837	1.1583	0.0996	0.05*
C24	−0.0799 (3)	1.10447 (17)	0.29217 (16)	0.0442 (5)
H24A	−0.1589	1.1773	0.2721	0.066*
H24B	−0.0342	1.1065	0.3531	0.066*
H24C	−0.1421	1.0415	0.3014	0.066*
C25	0.3409 (3)	0.95501 (15)	0.36494 (13)	0.0329 (4)
H25	0.4612	0.9087	0.3614	0.04*
C26	0.3579 (4)	1.07440 (17)	0.37917 (15)	0.0501 (6)
H26A	0.2453	1.1268	0.3745	0.075*
H26B	0.4411	1.1033	0.329	0.075*
H26C	0.3981	1.0693	0.4431	0.075*
C27	0.2487 (3)	0.89806 (18)	0.45464 (13)	0.0397 (5)
H27A	0.3084	0.8976	0.5115	0.06*
H27B	0.2483	0.8191	0.4482	0.06*
H27C	0.1295	0.9406	0.4624	0.06*
N1	−0.4682 (2)	0.62935 (12)	0.65594 (10)	0.0301 (3)
N2	0.17936 (17)	0.38074 (12)	−0.08868 (11)	0.0269 (3)
O1	0.22103 (14)	0.64699 (9)	0.36191 (8)	0.0238 (3)
O2	0.39047 (14)	0.64166 (10)	0.21635 (8)	0.0250 (3)
O3	−0.44662 (18)	0.65988 (11)	0.73097 (9)	0.0369 (3)
O4	−0.60067 (18)	0.60044 (14)	0.64261 (10)	0.0456 (4)
O5	0.17938 (17)	0.40609 (13)	−0.17666 (10)	0.0384 (3)
O6	0.14076 (17)	0.29202 (11)	−0.04211 (11)	0.0383 (3)
Si1	0.25547 (5)	0.96039 (3)	0.24340 (3)	0.01786 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0148 (7)	0.0168 (7)	0.0192 (7)	−0.0024 (5)	−0.0047 (5)	−0.0023 (5)
C2	0.0178 (7)	0.0169 (7)	0.0220 (7)	−0.0041 (5)	−0.0049 (6)	−0.0031 (6)
C3	0.0178 (7)	0.0188 (7)	0.0244 (8)	−0.0048 (6)	−0.0034 (6)	−0.0028 (6)
C4	0.0152 (7)	0.0183 (7)	0.0226 (8)	−0.0024 (5)	−0.0034 (5)	−0.0011 (6)
C5	0.0174 (7)	0.0207 (7)	0.0224 (8)	−0.0042 (6)	−0.0029 (6)	−0.0048 (6)
C6	0.0181 (7)	0.0167 (7)	0.0212 (7)	−0.0035 (5)	−0.0048 (6)	−0.0032 (6)
C7	0.0249 (8)	0.0150 (7)	0.0249 (8)	−0.0051 (6)	−0.0015 (6)	−0.0020 (6)
C8	0.0277 (8)	0.0200 (8)	0.0270 (8)	−0.0084 (6)	−0.0047 (6)	−0.0007 (6)
C9	0.0358 (9)	0.0198 (8)	0.0229 (8)	−0.0084 (7)	−0.0049 (7)	0.0003 (6)
C10	0.0288 (8)	0.0181 (7)	0.0240 (8)	−0.0059 (6)	0.0021 (6)	0.0026 (6)
C11	0.0246 (8)	0.0253 (8)	0.0274 (8)	−0.0086 (6)	−0.0029 (6)	0.0023 (6)
C12	0.0259 (8)	0.0261 (8)	0.0219 (8)	−0.0080 (6)	−0.0030 (6)	−0.0012 (6)
C13	0.0127 (6)	0.0187 (7)	0.0222 (7)	−0.0017 (5)	−0.0015 (5)	−0.0049 (6)
C14	0.0167 (7)	0.0184 (7)	0.0230 (8)	−0.0042 (5)	−0.0001 (6)	−0.0018 (6)
C15	0.0176 (7)	0.0263 (8)	0.0188 (7)	−0.0031 (6)	−0.0002 (6)	−0.0055 (6)
C16	0.0124 (6)	0.0201 (7)	0.0293 (8)	−0.0009 (5)	−0.0034 (6)	−0.0100 (6)
C17	0.0158 (7)	0.0182 (7)	0.0282 (8)	−0.0042 (6)	−0.0015 (6)	−0.0020 (6)
C18	0.0173 (7)	0.0199 (7)	0.0198 (7)	−0.0035 (6)	−0.0004 (5)	−0.0011 (6)
C19	0.0197 (7)	0.0206 (8)	0.0289 (8)	−0.0074 (6)	−0.0030 (6)	−0.0050 (6)
C20	0.0202 (8)	0.0296 (9)	0.0519 (12)	−0.0040 (7)	−0.0018 (7)	−0.0071 (8)
C21	0.0301 (9)	0.0252 (9)	0.0384 (10)	−0.0125 (7)	0.0026 (7)	−0.0039 (7)
C22	0.0256 (8)	0.0172 (8)	0.0351 (9)	−0.0006 (6)	0.0000 (7)	−0.0009 (7)
C23	0.0260 (8)	0.0259 (9)	0.0430 (11)	0.0002 (7)	−0.0105 (7)	0.0045 (7)
C24	0.0366 (10)	0.0307 (10)	0.0546 (13)	0.0055 (8)	0.0120 (9)	−0.0047 (9)
C25	0.0498 (11)	0.0253 (9)	0.0282 (9)	−0.0140 (8)	−0.0094 (8)	−0.0041 (7)
C26	0.0944 (18)	0.0320 (11)	0.0351 (11)	−0.0276 (11)	−0.0218 (11)	−0.0057 (8)
C27	0.0534 (12)	0.0425 (11)	0.0274 (10)	−0.0168 (9)	−0.0063 (8)	−0.0060 (8)
N1	0.0356 (8)	0.0259 (7)	0.0243 (8)	−0.0073 (6)	0.0027 (6)	0.0052 (6)
N2	0.0164 (6)	0.0314 (8)	0.0368 (8)	−0.0030 (5)	−0.0033 (6)	−0.0164 (6)
O1	0.0195 (5)	0.0192 (5)	0.0298 (6)	−0.0032 (4)	−0.0051 (4)	0.0044 (4)
O2	0.0249 (6)	0.0239 (6)	0.0245 (6)	0.0066 (4)	−0.0106 (4)	−0.0082 (5)
O3	0.0501 (8)	0.0351 (7)	0.0224 (6)	−0.0105 (6)	0.0051 (6)	−0.0001 (5)
O4	0.0346 (8)	0.0649 (10)	0.0368 (8)	−0.0204 (7)	0.0055 (6)	−0.0007 (7)
O5	0.0334 (7)	0.0568 (9)	0.0336 (7)	−0.0163 (6)	0.0015 (5)	−0.0233 (6)
O6	0.0393 (7)	0.0236 (6)	0.0584 (9)	−0.0105 (5)	−0.0163 (6)	−0.0100 (6)
Si1	0.0197 (2)	0.0145 (2)	0.0198 (2)	−0.00336 (15)	−0.00414 (15)	−0.00249 (15)

Geometric parameters (Å, º)

C1—C4	1.549 (2)	C17—C18	1.381 (2)
C1—C6	1.551 (2)	C17—H17	0.95
C1—C2	1.564 (2)	C18—H18	0.95
C1—Si1	1.9186 (15)	C19—C20	1.530 (2)
C2—O2	1.4138 (19)	C19—C21	1.538 (2)
C2—O1	1.4169 (19)	C19—Si1	1.8980 (17)
C2—H2	1	C19—H19	1
C3—O1	1.4391 (18)	C20—H20A	0.98
C3—C7	1.506 (2)	C20—H20B	0.98
C3—C4	1.531 (2)	C20—H20C	0.98
C3—H3	1	C21—H21A	0.98
C4—H4A	0.99	C21—H21B	0.98
C4—H4B	0.99	C21—H21C	0.98
C5—O2	1.4339 (19)	C22—C24	1.537 (3)
C5—C13	1.510 (2)	C22—C23	1.538 (3)
C5—C6	1.533 (2)	C22—Si1	1.8975 (18)
C5—H5	1	C22—H22	1
C6—H6A	0.99	C23—H23A	0.98
C6—H6B	0.99	C23—H23B	0.98
C7—C8	1.397 (2)	C23—H23C	0.98
C7—C12	1.395 (2)	C24—H24A	0.98
C8—C9	1.385 (2)	C24—H24B	0.98
C8—H8	0.95	C24—H24C	0.98
C9—C10	1.387 (2)	C25—C27	1.513 (3)
C9—H9	0.95	C25—C26	1.536 (2)
C10—C11	1.381 (2)	C25—Si1	1.9061 (18)
C10—N1	1.472 (2)	C25—H25	1
C11—C12	1.386 (2)	C26—H26A	0.98
C11—H11	0.95	C26—H26B	0.98
C12—H12	0.95	C26—H26C	0.98
C13—C14	1.393 (2)	C27—H27A	0.98
C13—C18	1.396 (2)	C27—H27B	0.98
C14—C15	1.391 (2)	C27—H27C	0.98
C14—H14	0.95	N1—O3	1.229 (2)
C15—C16	1.385 (2)	N1—O4	1.228 (2)
C15—H15	0.95	N2—O5	1.222 (2)
C16—C17	1.383 (2)	N2—O6	1.231 (2)
C16—N2	1.468 (2)
C4—C1—C6	109.80 (12)	C17—C18—H18	119.7
C4—C1—C2	101.54 (12)	C13—C18—H18	119.7
C6—C1—C2	102.77 (12)	C20—C19—C21	109.23 (13)
C4—C1—Si1	112.28 (10)	C20—C19—Si1	112.69 (12)
C6—C1—Si1	114.81 (10)	C21—C19—Si1	115.11 (12)
C2—C1—Si1	114.49 (10)	C20—C19—H19	106.4
O2—C2—O1	110.25 (12)	C21—C19—H19	106.4
O2—C2—C1	108.49 (12)	Si1—C19—H19	106.4
O1—C2—C1	108.19 (12)	C19—C20—H20A	109.5
O2—C2—H2	110	C19—C20—H20B	109.5
O1—C2—H2	110	H20A—C20—H20B	109.5
C1—C2—H2	110	C19—C20—H20C	109.5
O1—C3—C7	112.24 (13)	H20A—C20—H20C	109.5
O1—C3—C4	102.82 (12)	H20B—C20—H20C	109.5
C7—C3—C4	112.14 (13)	C19—C21—H21A	109.5
O1—C3—H3	109.8	C19—C21—H21B	109.5
C7—C3—H3	109.8	H21A—C21—H21B	109.5
C4—C3—H3	109.8	C19—C21—H21C	109.5
C3—C4—C1	103.18 (12)	H21A—C21—H21C	109.5
C3—C4—H4A	111.1	H21B—C21—H21C	109.5
C1—C4—H4A	111.1	C24—C22—C23	110.25 (16)
C3—C4—H4B	111.1	C24—C22—Si1	117.14 (13)
C1—C4—H4B	111.1	C23—C22—Si1	112.24 (12)
H4A—C4—H4B	109.1	C24—C22—H22	105.4
O2—C5—C13	109.71 (12)	C23—C22—H22	105.4
O2—C5—C6	105.91 (12)	Si1—C22—H22	105.4
C13—C5—C6	112.50 (12)	C22—C23—H23A	109.5
O2—C5—H5	109.5	C22—C23—H23B	109.5
C13—C5—H5	109.5	H23A—C23—H23B	109.5
C6—C5—H5	109.5	C22—C23—H23C	109.5
C5—C6—C1	105.75 (12)	H23A—C23—H23C	109.5
C5—C6—H6A	110.6	H23B—C23—H23C	109.5
C1—C6—H6A	110.6	C22—C24—H24A	109.5
C5—C6—H6B	110.6	C22—C24—H24B	109.5
C1—C6—H6B	110.6	H24A—C24—H24B	109.5
H6A—C6—H6B	108.7	C22—C24—H24C	109.5
C8—C7—C12	119.40 (15)	H24A—C24—H24C	109.5
C8—C7—C3	122.13 (14)	H24B—C24—H24C	109.5
C12—C7—C3	118.25 (14)	C27—C25—C26	109.54 (17)
C9—C8—C7	120.13 (15)	C27—C25—Si1	117.65 (13)
C9—C8—H8	119.9	C26—C25—Si1	111.40 (13)
C7—C8—H8	119.9	C27—C25—H25	105.8
C8—C9—C10	118.84 (15)	C26—C25—H25	105.8
C8—C9—H9	120.6	Si1—C25—H25	105.8
C10—C9—H9	120.6	C25—C26—H26A	109.5
C11—C10—C9	122.36 (15)	C25—C26—H26B	109.5
C11—C10—N1	118.33 (15)	H26A—C26—H26B	109.5
C9—C10—N1	119.28 (15)	C25—C26—H26C	109.5
C10—C11—C12	118.17 (15)	H26A—C26—H26C	109.5
C10—C11—H11	120.9	H26B—C26—H26C	109.5
C12—C11—H11	120.9	C25—C27—H27A	109.5
C11—C12—C7	120.95 (15)	C25—C27—H27B	109.5
C11—C12—H12	119.5	H27A—C27—H27B	109.5
C7—C12—H12	119.5	C25—C27—H27C	109.5
C14—C13—C18	119.40 (14)	H27A—C27—H27C	109.5
C14—C13—C5	120.52 (13)	H27B—C27—H27C	109.5
C18—C13—C5	120.02 (13)	O3—N1—O4	123.48 (15)
C15—C14—C13	120.84 (14)	O3—N1—C10	118.06 (15)
C15—C14—H14	119.6	O4—N1—C10	118.44 (15)
C13—C14—H14	119.6	O5—N2—O6	123.60 (15)
C16—C15—C14	117.81 (14)	O5—N2—C16	118.33 (14)
C16—C15—H15	121.1	O6—N2—C16	118.07 (14)
C14—C15—H15	121.1	C2—O1—C3	107.52 (11)
C15—C16—C17	122.86 (14)	C2—O2—C5	112.11 (11)
C15—C16—N2	118.90 (14)	C19—Si1—C22	106.57 (8)
C17—C16—N2	118.24 (14)	C19—Si1—C25	107.94 (8)
C18—C17—C16	118.40 (14)	C22—Si1—C25	113.16 (9)
C18—C17—H17	120.8	C19—Si1—C1	108.20 (7)
C16—C17—H17	120.8	C22—Si1—C1	111.10 (7)
C17—C18—C13	120.67 (14)	C25—Si1—C1	109.67 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O6^i	0.99	2.56	3.481 (2)	154
C12—H12···O5^i	0.95	2.50	3.381 (2)	155

Symmetry code: (i) −x, −y+1, −z.