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The title compound, BINAP oxide, C44H32O2P2, (I), was synthesized by direct oxidation of (R)-(+)-2,2'-bis­(di­phenyl­phosphino)-1,1'-bi­naphthyl (BINAP) with tert-butyl hydro­peroxide in toluene solution. The angle between the naphthyl planes of the bi­naphthyl group is 94.17 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006508/qa0294sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006508/qa0294Isup2.hkl
Contains datablock I

CCDC reference: 146102

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(R)-(+)-2,2'-bis(diphenylphosphinoyl)-1,1'-binaphthyl top
Crystal data top
C44H32O2P2F(000) = 684
Mr = 654.64Dx = 1.279 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.0719 (2) ÅCell parameters from 16714 reflections
b = 18.9903 (8) Åθ = 2.6–32.0°
c = 10.1528 (3) ŵ = 0.17 mm1
β = 103.620 (2)°T = 150 K
V = 1699.92 (10) Å3Block cut from neeedle, colourless
Z = 20.34 × 0.30 × 0.20 mm
Data collection top
Nonius KappaCDD
diffractometer
10057 independent reflections
Radiation source: fine-focus sealed tube7746 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scans with κ offsetsθmax = 32.0°, θmin = 2.6°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1313
Tmin = 0.946, Tmax = 0.968k = 2528
16714 measured reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0192P)2 + 0.3419P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
10057 reflectionsΔρmax = 0.32 e Å3
434 parametersΔρmin = 0.37 e Å3
1 restraintAbsolute structure: Flack (1983); 4058 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (6)
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
P10.38718 (6)0.11271 (3)0.09531 (5)0.02064 (11)
P20.46092 (6)0.25701 (3)0.43790 (5)0.02034 (11)
O10.39653 (15)0.08055 (9)0.23009 (14)0.0262 (3)
O20.39496 (15)0.28703 (8)0.30197 (13)0.0254 (3)
C10.6220 (2)0.20572 (11)0.21129 (18)0.0187 (4)
C20.5082 (2)0.18876 (12)0.09794 (19)0.0196 (4)
C30.4856 (2)0.23184 (12)0.01941 (19)0.0218 (4)
H3A0.41020.21920.09770.026*
C40.5700 (2)0.29108 (12)0.0221 (2)0.0238 (4)
H4A0.54990.32010.10060.029*
C50.6872 (2)0.30965 (12)0.0912 (2)0.0225 (4)
C60.7771 (2)0.37096 (13)0.0916 (2)0.0284 (5)
H6A0.75570.40180.01570.034*
C70.8946 (3)0.38616 (14)0.2005 (3)0.0382 (6)
H7A0.95400.42730.19970.046*
C80.9271 (3)0.34084 (15)0.3134 (2)0.0375 (6)
H8A1.01060.35070.38720.045*
C90.8398 (2)0.28302 (13)0.3177 (2)0.0290 (5)
H9A0.86180.25370.39570.035*
C100.7166 (2)0.26566 (12)0.20790 (18)0.0211 (4)
C110.6484 (2)0.16290 (11)0.33892 (18)0.0188 (4)
C120.5825 (2)0.18048 (12)0.44404 (19)0.0199 (4)
C130.6046 (2)0.13633 (12)0.56012 (19)0.0226 (4)
H13A0.56030.14890.63280.027*
C140.6887 (2)0.07609 (12)0.56889 (19)0.0230 (4)
H14A0.69900.04650.64600.028*
C150.7602 (2)0.05723 (12)0.4647 (2)0.0237 (4)
C160.8472 (2)0.00510 (13)0.4718 (2)0.0314 (5)
H16A0.85570.03590.54700.038*
C170.9197 (3)0.02172 (15)0.3709 (3)0.0400 (6)
H17A0.97850.06350.37680.048*
C180.9062 (3)0.02348 (15)0.2593 (2)0.0379 (6)
H18A0.95700.01210.19020.046*
C190.8213 (2)0.08342 (13)0.2484 (2)0.0290 (5)
H19A0.81400.11330.17210.035*
C200.7435 (2)0.10180 (12)0.34986 (19)0.0214 (4)
C210.1953 (2)0.13983 (13)0.01918 (19)0.0236 (4)
C220.1457 (2)0.20685 (14)0.0442 (2)0.0304 (5)
H22A0.21610.24110.08920.036*
C230.0077 (3)0.22327 (16)0.0030 (2)0.0394 (6)
H23A0.04170.26920.01810.047*
C240.1110 (3)0.17319 (17)0.0599 (2)0.0400 (7)
H24A0.21560.18490.08770.048*
C250.0634 (3)0.10659 (18)0.0826 (2)0.0408 (7)
H25A0.13480.07210.12470.049*
C260.0910 (2)0.08985 (14)0.0434 (2)0.0319 (5)
H26A0.12440.04400.05980.038*
C310.4421 (2)0.05061 (13)0.0201 (2)0.0264 (5)
C320.3958 (3)0.05595 (14)0.1612 (2)0.0331 (5)
H32A0.33320.09400.20160.040*
C330.4419 (3)0.00526 (15)0.2422 (3)0.0416 (6)
H33A0.40890.00820.33810.050*
C340.5357 (3)0.04938 (15)0.1837 (3)0.0470 (7)
H34A0.56590.08420.23920.056*
C350.5854 (3)0.05318 (15)0.0438 (3)0.0437 (7)
H35A0.65350.08940.00370.052*
C360.5360 (2)0.00430 (13)0.0374 (3)0.0325 (5)
H36A0.56680.00840.13330.039*
C410.3149 (2)0.22762 (13)0.52049 (19)0.0245 (4)
C420.2696 (2)0.26796 (15)0.6187 (2)0.0324 (6)
H42A0.32070.31060.65010.039*
C430.1476 (3)0.24489 (18)0.6708 (2)0.0429 (7)
H43A0.11480.27250.73650.051*
C440.0756 (3)0.18276 (18)0.6274 (2)0.0436 (7)
H44A0.00530.16700.66480.052*
C450.1198 (3)0.14301 (17)0.5300 (3)0.0423 (7)
H45A0.06870.10030.49970.051*
C460.2394 (2)0.16534 (14)0.4759 (2)0.0323 (5)
H46A0.26930.13790.40840.039*
C510.5729 (2)0.32112 (12)0.55000 (19)0.0220 (4)
C520.7075 (2)0.30618 (13)0.6440 (2)0.0268 (5)
H52A0.74690.25960.65200.032*
C530.7844 (3)0.35944 (14)0.7260 (2)0.0314 (5)
H53A0.87730.34930.78890.038*
C540.7267 (2)0.42708 (13)0.7169 (2)0.0305 (5)
H54A0.77890.46300.77460.037*
C550.5933 (3)0.44237 (14)0.6238 (2)0.0362 (6)
H55A0.55390.48890.61690.043*
C560.5172 (3)0.38986 (13)0.5407 (2)0.0315 (5)
H56A0.42570.40070.47640.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0222 (2)0.0189 (3)0.0204 (2)0.0001 (2)0.00404 (18)0.0013 (2)
P20.0231 (2)0.0192 (3)0.0193 (2)0.0008 (2)0.00613 (18)0.0002 (2)
O10.0300 (8)0.0234 (8)0.0243 (7)0.0027 (7)0.0047 (6)0.0064 (7)
O20.0311 (8)0.0238 (9)0.0208 (7)0.0040 (7)0.0053 (6)0.0027 (6)
C10.0203 (9)0.0196 (11)0.0171 (9)0.0037 (8)0.0059 (7)0.0023 (8)
C20.0210 (9)0.0180 (11)0.0206 (9)0.0001 (8)0.0063 (7)0.0012 (8)
C30.0228 (10)0.0233 (11)0.0187 (9)0.0020 (9)0.0037 (7)0.0022 (8)
C40.0278 (10)0.0227 (12)0.0212 (9)0.0035 (9)0.0065 (8)0.0058 (9)
C50.0260 (10)0.0203 (11)0.0231 (10)0.0011 (9)0.0096 (8)0.0020 (9)
C60.0327 (12)0.0221 (12)0.0308 (11)0.0008 (10)0.0084 (9)0.0044 (9)
C70.0409 (14)0.0272 (14)0.0447 (14)0.0130 (11)0.0064 (11)0.0045 (11)
C80.0389 (14)0.0344 (16)0.0335 (13)0.0104 (12)0.0029 (10)0.0010 (11)
C90.0304 (11)0.0289 (13)0.0258 (10)0.0059 (10)0.0027 (8)0.0018 (9)
C100.0232 (9)0.0193 (11)0.0215 (9)0.0001 (9)0.0068 (7)0.0004 (8)
C110.0197 (9)0.0162 (10)0.0194 (9)0.0034 (8)0.0025 (7)0.0016 (8)
C120.0212 (10)0.0177 (11)0.0201 (9)0.0015 (8)0.0034 (7)0.0008 (8)
C130.0258 (10)0.0241 (12)0.0177 (9)0.0027 (9)0.0045 (8)0.0012 (8)
C140.0235 (10)0.0224 (11)0.0209 (9)0.0004 (9)0.0010 (7)0.0070 (9)
C150.0198 (9)0.0243 (12)0.0256 (10)0.0016 (9)0.0029 (8)0.0048 (9)
C160.0286 (11)0.0274 (13)0.0383 (12)0.0069 (10)0.0084 (9)0.0109 (11)
C170.0394 (13)0.0334 (15)0.0492 (15)0.0181 (12)0.0143 (11)0.0059 (12)
C180.0357 (13)0.0419 (17)0.0391 (13)0.0158 (12)0.0148 (10)0.0041 (12)
C190.0274 (11)0.0338 (14)0.0267 (10)0.0061 (10)0.0084 (8)0.0067 (10)
C200.0183 (9)0.0206 (12)0.0236 (9)0.0013 (8)0.0015 (7)0.0019 (8)
C210.0224 (10)0.0280 (12)0.0202 (9)0.0002 (9)0.0046 (8)0.0027 (9)
C220.0259 (11)0.0330 (14)0.0331 (12)0.0015 (10)0.0087 (9)0.0021 (10)
C230.0328 (12)0.0463 (17)0.0418 (13)0.0139 (12)0.0141 (10)0.0106 (13)
C240.0232 (11)0.069 (2)0.0292 (12)0.0089 (13)0.0082 (9)0.0107 (13)
C250.0281 (11)0.065 (2)0.0278 (11)0.0072 (13)0.0037 (9)0.0009 (13)
C260.0297 (11)0.0376 (15)0.0275 (11)0.0011 (10)0.0051 (9)0.0038 (10)
C310.0269 (10)0.0218 (12)0.0325 (11)0.0031 (9)0.0110 (9)0.0023 (9)
C320.0425 (13)0.0303 (14)0.0308 (11)0.0039 (11)0.0172 (10)0.0024 (10)
C330.0565 (16)0.0364 (16)0.0404 (14)0.0114 (13)0.0288 (12)0.0110 (12)
C340.0571 (17)0.0310 (15)0.0651 (18)0.0071 (13)0.0388 (14)0.0174 (14)
C350.0402 (14)0.0272 (15)0.0696 (19)0.0016 (12)0.0249 (13)0.0057 (14)
C360.0299 (12)0.0237 (13)0.0452 (14)0.0010 (10)0.0112 (10)0.0003 (11)
C410.0220 (9)0.0305 (12)0.0202 (9)0.0021 (9)0.0037 (7)0.0060 (9)
C420.0318 (11)0.0418 (16)0.0243 (10)0.0069 (11)0.0083 (8)0.0026 (10)
C430.0344 (12)0.069 (2)0.0283 (12)0.0155 (14)0.0142 (9)0.0094 (13)
C440.0260 (12)0.070 (2)0.0371 (13)0.0040 (13)0.0123 (10)0.0242 (14)
C450.0248 (12)0.0510 (18)0.0483 (15)0.0053 (12)0.0030 (10)0.0153 (13)
C460.0249 (11)0.0382 (15)0.0331 (12)0.0014 (10)0.0057 (9)0.0076 (11)
C510.0252 (10)0.0206 (11)0.0215 (9)0.0018 (9)0.0083 (8)0.0017 (8)
C520.0271 (11)0.0217 (12)0.0314 (11)0.0024 (9)0.0064 (9)0.0023 (9)
C530.0264 (11)0.0356 (15)0.0316 (12)0.0035 (10)0.0055 (9)0.0041 (10)
C540.0364 (12)0.0261 (13)0.0302 (11)0.0072 (11)0.0105 (9)0.0082 (10)
C550.0480 (15)0.0235 (13)0.0367 (13)0.0017 (12)0.0093 (11)0.0063 (11)
C560.0352 (12)0.0267 (13)0.0301 (11)0.0058 (10)0.0028 (9)0.0014 (10)
Geometric parameters (Å, º) top
P1—O11.4824 (14)C17—C181.404 (3)
P1—C211.806 (2)C18—C191.364 (3)
P1—C21.811 (2)C19—C201.422 (3)
P1—C311.813 (2)C21—C261.384 (3)
P2—O21.4828 (14)C21—C221.393 (3)
P2—C511.807 (2)C22—C231.391 (3)
P2—C411.814 (2)C23—C241.381 (4)
P2—C121.817 (2)C24—C251.373 (4)
C1—C21.391 (3)C25—C261.399 (3)
C1—C101.430 (3)C31—C361.386 (3)
C1—C111.501 (3)C31—C321.399 (3)
C2—C31.420 (3)C32—C331.393 (3)
C3—C41.365 (3)C33—C341.384 (4)
C4—C51.415 (3)C34—C351.387 (4)
C5—C61.421 (3)C35—C361.385 (3)
C5—C101.423 (3)C41—C461.388 (3)
C6—C71.374 (3)C41—C421.394 (3)
C7—C81.408 (3)C42—C431.404 (3)
C8—C91.360 (3)C43—C441.370 (4)
C9—C101.419 (3)C44—C451.377 (4)
C11—C121.382 (3)C45—C461.392 (3)
C11—C201.435 (3)C51—C521.390 (3)
C12—C131.422 (3)C51—C561.395 (3)
C13—C141.366 (3)C52—C531.389 (3)
C14—C151.412 (3)C53—C541.382 (3)
C15—C161.415 (3)C54—C551.379 (3)
C15—C201.420 (3)C55—C561.382 (3)
C16—C171.378 (3)
O1—P1—C21110.64 (9)C16—C15—C20119.41 (19)
O1—P1—C2114.34 (9)C17—C16—C15120.8 (2)
C21—P1—C2107.40 (10)C16—C17—C18119.6 (2)
O1—P1—C31111.34 (10)C19—C18—C17121.1 (2)
C21—P1—C31107.03 (10)C18—C19—C20120.9 (2)
C2—P1—C31105.69 (9)C15—C20—C19118.25 (19)
O2—P2—C51111.77 (10)C15—C20—C11119.44 (17)
O2—P2—C41111.71 (8)C19—C20—C11122.30 (18)
C51—P2—C41106.23 (10)C26—C21—C22119.66 (19)
O2—P2—C12116.63 (9)C26—C21—P1119.12 (18)
C51—P2—C12105.70 (9)C22—C21—P1120.19 (17)
C41—P2—C12103.97 (10)C23—C22—C21119.5 (2)
C2—C1—C10119.79 (17)C24—C23—C22120.4 (3)
C2—C1—C11121.69 (18)C25—C24—C23120.4 (2)
C10—C1—C11118.52 (16)C24—C25—C26119.7 (3)
C1—C2—C3119.56 (19)C21—C26—C25120.3 (2)
C1—C2—P1121.76 (15)C36—C31—C32119.5 (2)
C3—C2—P1118.69 (15)C36—C31—P1116.91 (17)
C4—C3—C2121.39 (18)C32—C31—P1123.57 (19)
C3—C4—C5120.47 (19)C33—C32—C31119.7 (2)
C4—C5—C6121.83 (19)C34—C33—C32120.3 (2)
C4—C5—C10119.22 (19)C33—C34—C35119.8 (2)
C6—C5—C10118.95 (19)C36—C35—C34120.2 (3)
C7—C6—C5120.7 (2)C35—C36—C31120.4 (2)
C6—C7—C8120.1 (2)C46—C41—C42119.7 (2)
C9—C8—C7120.5 (2)C46—C41—P2118.01 (17)
C8—C9—C10121.3 (2)C42—C41—P2122.13 (19)
C9—C10—C5118.43 (19)C41—C42—C43119.3 (3)
C9—C10—C1122.12 (18)C44—C43—C42120.4 (2)
C5—C10—C1119.45 (17)C43—C44—C45120.4 (2)
C12—C11—C20119.84 (18)C44—C45—C46120.1 (3)
C12—C11—C1121.75 (18)C41—C46—C45120.1 (2)
C20—C11—C1118.41 (16)C52—C51—C56118.9 (2)
C11—C12—C13119.70 (19)C52—C51—P2124.57 (18)
C11—C12—P2122.45 (15)C56—C51—P2116.54 (16)
C13—C12—P2117.81 (15)C53—C52—C51119.9 (2)
C14—C13—C12121.06 (18)C54—C53—C52120.5 (2)
C13—C14—C15120.79 (19)C55—C54—C53119.9 (2)
C14—C15—C16121.6 (2)C54—C55—C56119.9 (2)
C14—C15—C20119.0 (2)C55—C56—C51120.9 (2)
 

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