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The title compound, C32H23N2O2, is a moisture- and oxy­gen-sensitive phosphite ligand. It has been shown to be effective in asymmetric conjugate addition of diorganozinc reagents to α,β-unsatuated cyclic enones.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803006640/ww6066sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803006640/ww6066Isup2.hkl
Contains datablock I

CCDC reference: 214593

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.058
  • Data-to-parameter ratio = 17.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.59 From the CIF: _reflns_number_total 5805 Count of symmetry unique reflns 3312 Completeness (_total/calc) 175.27% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2493 Fraction of Friedel pairs measured 0.753 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

Recently, some striking results have been obtained in the Cu-catalyzed enantioselective conjugate addition of organometallic reagents. In particular, diorganozinc reagents, to α,β-unsaturated esters, acyclic and cyclic enones by using chiral phosphoramidite ligands (Feringa et al., 1997). Our research shows that the phosphoramidite ligands derived from 2-aminopyridine and binaphthol is an efficient ligand in 1,4-conjugate addition of diphenyzinc to cyclic enones. Herein, as part of our investigation, we report the crystal structure of the title compound, (I). The crystal structure (Fig. 1) showed that both bond lengths and angles are within normal range (Table 1).

Experimental top

All reaction was carried out under N2 with Schlenk skill. To a cooled solution (213 K) of PCl3 (270 ml, 3.0 mmol), EtN3(860 ml, 6.0 mmol), and toluene (5 ml) was added a warm solution (333 K) of (R)-2,2'-binaphthol (860 mg, 3.0 mmol) in toluene (25 ml) in 25 min. After stirring for 2 h, the reaction mixture was warmed up to room temperature and filtered under a nitrogen atmosphere. The filtrate was a solution of chlorophosphite. The title compound was prepared by the reaction of the chlorophosphite and 2.9 mmol of the benzyl-2-pyridine compounds at 233 K in the presence of Et3N (410 ml, 2.9 mmol) and 4-dimethylaminopyridine. The crude products were purified by flash silica-gel chromatography. 1185 mg of white solid was obtained (yield: 82%). A colorless crystal suitable for X-ray diffraction was obtained by recrystallization from a solution in CH2Cl2 and ether. 31P NMR (CD2Cl2): δ 144.47 p.p.m.

Refinement top

H atoms were included in the riding-model approximation, with Uiso values equal to the Ueq of the atom to which they were bound.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing ellipsoids at the 50% probability level (Bruker, 1995).
O,O'-(R)-(1,1'-Dinaphthyl-2,2'-diyl)-N,N'-benzyl-2- pyridinephosphoramidite top
Crystal data top
C32H23N2O2PF(000) = 1040
Mr = 498.49Dx = 1.318 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3922 reflections
a = 9.5168 (11) Åθ = 1–27.5°
b = 10.3952 (11) ŵ = 0.14 mm1
c = 25.398 (3) ÅT = 294 K
V = 2512.6 (5) Å3Block, colorless
Z = 40.36 × 0.32 × 0.30 mm
Data collection top
Siemens CCD area-detector
diffractometer
5805 independent reflections
Radiation source: fine-focus sealed tube2424 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
ϕ and ω scansθmax = 27.6°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.950, Tmax = 0.958k = 1313
17396 measured reflectionsl = 2233
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)] = 0.043H-atom parameters constrained
wR(F2) = 0.058 w = 1/[σ2(Fo2) + (0.002P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.90(Δ/σ)max < 0.001
5805 reflectionsΔρmax = 0.17 e Å3
334 parametersΔρmin = 0.21 e Å3
0 restraintsAbsolute structure: Flack (1983), 0000 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.15 (9)
Crystal data top
C32H23N2O2PV = 2512.6 (5) Å3
Mr = 498.49Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.5168 (11) ŵ = 0.14 mm1
b = 10.3952 (11) ÅT = 294 K
c = 25.398 (3) Å0.36 × 0.32 × 0.30 mm
Data collection top
Siemens CCD area-detector
diffractometer
5805 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2424 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.958Rint = 0.075
17396 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.058Δρmax = 0.17 e Å3
S = 0.90Δρmin = 0.21 e Å3
5805 reflectionsAbsolute structure: Flack (1983), 0000 Friedel pairs
334 parametersAbsolute structure parameter: 0.15 (9)
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
P10.66445 (9)0.61190 (8)0.36427 (3)0.0541 (2)
O10.76541 (18)0.57650 (17)0.41530 (7)0.0509 (5)
O20.50965 (18)0.56757 (17)0.38756 (6)0.0504 (5)
N10.7194 (2)0.4796 (2)0.32824 (9)0.0508 (7)
N20.5646 (3)0.5582 (2)0.26716 (10)0.0574 (7)
C10.7180 (3)0.6057 (3)0.46575 (11)0.0481 (8)
C20.7870 (3)0.7062 (3)0.49163 (13)0.0563 (9)
H2A0.85820.75150.47480.068*
C30.7491 (4)0.7369 (3)0.54130 (14)0.0670 (10)
H3A0.79770.80130.55910.080*
C40.6381 (4)0.6736 (3)0.56656 (13)0.0579 (10)
C50.5882 (4)0.7115 (3)0.61673 (15)0.0882 (13)
H5A0.63380.77750.63460.106*
C60.4770 (5)0.6546 (4)0.63892 (15)0.0978 (16)
H6A0.44720.68100.67210.117*
C70.4045 (4)0.5555 (3)0.61301 (14)0.0824 (12)
H7A0.32590.51810.62850.099*
C80.4508 (3)0.5140 (3)0.56437 (12)0.0612 (10)
H8A0.40360.44760.54740.073*
C90.5692 (3)0.5714 (3)0.54004 (12)0.0493 (8)
C100.6160 (3)0.5325 (2)0.48892 (11)0.0423 (8)
C110.5537 (3)0.4233 (3)0.45931 (11)0.0416 (7)
C120.5526 (3)0.2947 (3)0.47914 (11)0.0458 (8)
C130.6151 (3)0.2591 (3)0.52724 (12)0.0547 (9)
H13A0.65880.32140.54780.066*
C140.6126 (3)0.1335 (3)0.54441 (13)0.0717 (10)
H14A0.65540.11160.57610.086*
C150.5457 (4)0.0382 (3)0.51422 (15)0.0801 (12)
H15A0.54300.04610.52650.096*
C160.4858 (4)0.0674 (3)0.46800 (14)0.0739 (10)
H16A0.44210.00290.44860.089*
C170.4875 (3)0.1964 (3)0.44780 (13)0.0534 (8)
C180.4289 (3)0.2278 (3)0.39870 (12)0.0667 (10)
H18A0.38410.16430.37910.080*
C190.4365 (3)0.3493 (3)0.37947 (12)0.0632 (10)
H19A0.39980.36890.34650.076*
C200.5010 (3)0.4453 (3)0.41031 (12)0.0485 (8)
C210.8067 (3)0.3748 (3)0.34823 (10)0.0588 (9)
H21A0.75480.29490.34510.071*
H21B0.82470.38950.38530.071*
C220.9451 (3)0.3603 (3)0.32018 (11)0.0491 (8)
C231.0182 (3)0.4652 (3)0.30047 (11)0.0611 (9)
H23A0.98080.54750.30370.073*
C241.1463 (4)0.4476 (3)0.27607 (12)0.0746 (10)
H24A1.19450.51870.26320.090*
C251.2042 (3)0.3277 (4)0.27040 (13)0.0725 (11)
H25A1.28970.31760.25320.087*
C261.1352 (4)0.2233 (3)0.29017 (13)0.0723 (11)
H26A1.17410.14160.28710.087*
C271.0071 (4)0.2401 (3)0.31473 (11)0.0655 (9)
H27A0.96080.16840.32810.079*
C280.6557 (3)0.4649 (3)0.27951 (12)0.0492 (8)
C290.6813 (3)0.3612 (3)0.24616 (13)0.0636 (9)
H29A0.74760.29880.25470.076*
C300.6050 (4)0.3540 (3)0.20010 (14)0.0726 (10)
H30A0.61790.28450.17760.087*
C310.5108 (4)0.4478 (4)0.18723 (13)0.0741 (10)
H31A0.45870.44360.15630.089*
C320.4958 (3)0.5490 (3)0.22190 (14)0.0675 (10)
H32A0.43370.61460.21300.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0581 (5)0.0525 (5)0.0517 (5)0.0052 (5)0.0089 (5)0.0073 (5)
O10.0466 (13)0.0578 (13)0.0485 (13)0.0003 (11)0.0043 (11)0.0001 (11)
O20.0456 (12)0.0594 (13)0.0463 (12)0.0073 (11)0.0027 (10)0.0073 (10)
N10.0547 (18)0.0509 (16)0.0469 (16)0.0148 (13)0.0115 (13)0.0048 (13)
N20.0604 (19)0.0614 (19)0.0503 (18)0.0016 (15)0.0014 (14)0.0115 (15)
C10.053 (2)0.0418 (19)0.049 (2)0.0063 (17)0.0060 (17)0.0004 (18)
C20.059 (3)0.041 (2)0.070 (2)0.0011 (17)0.0074 (19)0.0027 (18)
C30.074 (3)0.050 (2)0.077 (3)0.010 (2)0.021 (2)0.013 (2)
C40.075 (3)0.054 (2)0.045 (2)0.023 (2)0.007 (2)0.0074 (18)
C50.120 (4)0.081 (3)0.064 (3)0.030 (3)0.018 (3)0.010 (2)
C60.144 (5)0.101 (4)0.048 (3)0.045 (3)0.007 (3)0.005 (3)
C70.101 (3)0.081 (3)0.065 (3)0.036 (3)0.035 (2)0.031 (2)
C80.075 (3)0.055 (2)0.054 (2)0.0206 (19)0.0083 (19)0.0085 (18)
C90.051 (2)0.050 (2)0.047 (2)0.0104 (17)0.0010 (17)0.0095 (17)
C100.042 (2)0.0386 (18)0.046 (2)0.0012 (15)0.0003 (15)0.0044 (16)
C110.0407 (19)0.0395 (19)0.0445 (19)0.0010 (15)0.0032 (15)0.0019 (16)
C120.0334 (19)0.050 (2)0.054 (2)0.0000 (16)0.0081 (16)0.0009 (18)
C130.047 (2)0.049 (2)0.068 (3)0.0041 (17)0.0040 (18)0.0044 (18)
C140.055 (2)0.065 (2)0.095 (3)0.001 (2)0.0054 (19)0.018 (2)
C150.074 (3)0.049 (2)0.117 (4)0.007 (2)0.005 (2)0.014 (2)
C160.069 (3)0.054 (2)0.098 (3)0.013 (2)0.011 (2)0.007 (2)
C170.049 (2)0.050 (2)0.061 (2)0.0057 (18)0.0108 (18)0.0034 (19)
C180.063 (3)0.080 (3)0.057 (3)0.021 (2)0.0062 (19)0.016 (2)
C190.059 (2)0.080 (3)0.051 (2)0.014 (2)0.0033 (17)0.001 (2)
C200.0423 (19)0.052 (2)0.051 (2)0.0024 (17)0.0120 (17)0.0002 (18)
C210.064 (2)0.056 (2)0.057 (2)0.0081 (19)0.0107 (17)0.0077 (18)
C220.053 (2)0.049 (2)0.0451 (19)0.0059 (18)0.0058 (16)0.0008 (17)
C230.056 (2)0.056 (2)0.072 (2)0.0005 (19)0.002 (2)0.0014 (19)
C240.056 (3)0.081 (3)0.086 (3)0.003 (2)0.006 (2)0.013 (2)
C250.043 (2)0.108 (3)0.067 (3)0.011 (2)0.0079 (18)0.012 (2)
C260.067 (3)0.070 (3)0.080 (3)0.013 (2)0.001 (2)0.016 (2)
C270.068 (3)0.051 (2)0.077 (3)0.001 (2)0.006 (2)0.0047 (19)
C280.044 (2)0.055 (2)0.049 (2)0.0068 (19)0.0085 (18)0.0125 (18)
C290.062 (2)0.058 (2)0.070 (2)0.0003 (19)0.003 (2)0.008 (2)
C300.067 (3)0.071 (3)0.080 (3)0.004 (2)0.006 (2)0.014 (2)
C310.072 (3)0.089 (3)0.061 (3)0.010 (2)0.002 (2)0.007 (2)
C320.056 (2)0.077 (3)0.069 (3)0.000 (2)0.004 (2)0.019 (2)
Geometric parameters (Å, º) top
P1—O21.6530 (18)C14—C151.405 (4)
P1—O11.6549 (18)C14—H14A0.9300
P1—N11.733 (2)C15—C161.340 (4)
O1—C11.392 (3)C15—H15A0.9300
O2—C201.399 (3)C16—C171.436 (4)
N1—C281.387 (3)C16—H16A0.9300
N1—C211.460 (3)C17—C181.405 (3)
N2—C321.326 (3)C18—C191.356 (3)
N2—C281.338 (3)C18—H18A0.9300
C1—C101.367 (3)C19—C201.409 (3)
C1—C21.398 (3)C19—H19A0.9300
C2—C31.350 (4)C21—C221.505 (3)
C2—H2A0.9300C21—H21A0.9700
C3—C41.401 (4)C21—H21B0.9700
C3—H3A0.9300C22—C231.387 (3)
C4—C51.416 (4)C22—C271.389 (3)
C4—C91.418 (4)C23—C241.380 (4)
C5—C61.337 (4)C23—H23A0.9300
C5—H5A0.9300C24—C251.370 (4)
C6—C71.403 (4)C24—H24A0.9300
C6—H6A0.9300C25—C261.364 (4)
C7—C81.381 (4)C25—H25A0.9300
C7—H7A0.9300C26—C271.380 (4)
C8—C91.417 (4)C26—H26A0.9300
C8—H8A0.9300C27—H27A0.9300
C9—C101.431 (4)C28—C291.393 (3)
C10—C111.485 (3)C29—C301.379 (4)
C11—C201.361 (3)C29—H29A0.9300
C11—C121.428 (3)C30—C311.364 (4)
C12—C131.408 (3)C30—H30A0.9300
C12—C171.436 (3)C31—C321.379 (4)
C13—C141.376 (3)C31—H31A0.9300
C13—H13A0.9300C32—H32A0.9300
O2—P1—O1100.09 (9)C15—C16—C17121.3 (3)
O2—P1—N1103.69 (10)C15—C16—H16A119.3
O1—P1—N193.54 (11)C17—C16—H16A119.3
C1—O1—P1118.97 (16)C18—C17—C16122.0 (3)
C20—O2—P1116.99 (17)C18—C17—C12119.9 (3)
C28—N1—C21118.5 (2)C16—C17—C12118.1 (3)
C28—N1—P1115.2 (2)C19—C18—C17121.0 (3)
C21—N1—P1125.45 (19)C19—C18—H18A119.5
C32—N2—C28118.1 (3)C17—C18—H18A119.5
C10—C1—O1120.3 (3)C18—C19—C20118.8 (3)
C10—C1—C2123.2 (3)C18—C19—H19A120.6
O1—C1—C2116.3 (3)C20—C19—H19A120.6
C3—C2—C1119.4 (3)C11—C20—O2120.5 (3)
C3—C2—H2A120.3C11—C20—C19123.4 (3)
C1—C2—H2A120.3O2—C20—C19116.1 (3)
C2—C3—C4121.2 (3)N1—C21—C22114.1 (2)
C2—C3—H3A119.4N1—C21—H21A108.7
C4—C3—H3A119.4C22—C21—H21A108.7
C3—C4—C5122.3 (4)N1—C21—H21B108.7
C3—C4—C9118.9 (3)C22—C21—H21B108.7
C5—C4—C9118.8 (4)H21A—C21—H21B107.6
C6—C5—C4121.4 (4)C23—C22—C27117.3 (3)
C6—C5—H5A119.3C23—C22—C21122.1 (3)
C4—C5—H5A119.3C27—C22—C21120.6 (3)
C5—C6—C7121.1 (4)C24—C23—C22120.1 (3)
C5—C6—H6A119.5C24—C23—H23A120.0
C7—C6—H6A119.5C22—C23—H23A120.0
C8—C7—C6119.5 (4)C25—C24—C23121.5 (3)
C8—C7—H7A120.3C25—C24—H24A119.2
C6—C7—H7A120.3C23—C24—H24A119.2
C7—C8—C9120.8 (3)C26—C25—C24119.5 (3)
C7—C8—H8A119.6C26—C25—H25A120.3
C9—C8—H8A119.6C24—C25—H25A120.3
C8—C9—C4118.4 (3)C25—C26—C27119.4 (3)
C8—C9—C10121.6 (3)C25—C26—H26A120.3
C4—C9—C10119.9 (3)C27—C26—H26A120.3
C1—C10—C9117.0 (3)C26—C27—C22122.3 (3)
C1—C10—C11119.4 (3)C26—C27—H27A118.9
C9—C10—C11123.5 (3)C22—C27—H27A118.9
C20—C11—C12118.4 (3)N2—C28—N1114.4 (3)
C20—C11—C10118.8 (3)N2—C28—C29122.1 (3)
C12—C11—C10122.7 (3)N1—C28—C29123.5 (3)
C13—C12—C11123.3 (3)C30—C29—C28117.7 (3)
C13—C12—C17118.4 (3)C30—C29—H29A121.1
C11—C12—C17118.3 (3)C28—C29—H29A121.1
C14—C13—C12121.1 (3)C31—C30—C29120.7 (3)
C14—C13—H13A119.4C31—C30—H30A119.6
C12—C13—H13A119.4C29—C30—H30A119.6
C13—C14—C15120.2 (3)C30—C31—C32117.4 (3)
C13—C14—H14A119.9C30—C31—H31A121.3
C15—C14—H14A119.9C32—C31—H31A121.3
C16—C15—C14120.7 (3)N2—C32—C31123.9 (3)
C16—C15—H15A119.6N2—C32—H32A118.1
C14—C15—H15A119.6C31—C32—H32A118.1
O2—P1—O1—C141.8 (2)C12—C13—C14—C150.7 (5)
N1—P1—O1—C1146.4 (2)C13—C14—C15—C161.2 (5)
O1—P1—O2—C2049.4 (2)C14—C15—C16—C170.1 (6)
N1—P1—O2—C2046.8 (2)C15—C16—C17—C18178.0 (3)
O2—P1—N1—C2876.7 (2)C15—C16—C17—C121.5 (5)
O1—P1—N1—C28178.00 (19)C13—C12—C17—C18177.6 (3)
O2—P1—N1—C2192.7 (2)C11—C12—C17—C180.9 (4)
O1—P1—N1—C218.6 (2)C13—C12—C17—C161.9 (4)
P1—O1—C1—C1074.9 (3)C11—C12—C17—C16179.6 (3)
P1—O1—C1—C2109.3 (2)C16—C17—C18—C19177.4 (3)
C10—C1—C2—C32.4 (4)C12—C17—C18—C192.1 (5)
O1—C1—C2—C3178.0 (3)C17—C18—C19—C201.8 (5)
C1—C2—C3—C42.8 (5)C12—C11—C20—O2175.0 (2)
C2—C3—C4—C5174.2 (3)C10—C11—C20—O22.2 (4)
C2—C3—C4—C93.0 (5)C12—C11—C20—C194.5 (4)
C3—C4—C5—C6176.2 (3)C10—C11—C20—C19178.3 (3)
C9—C4—C5—C61.0 (5)P1—O2—C20—C1176.0 (3)
C4—C5—C6—C70.6 (6)P1—O2—C20—C19103.5 (2)
C5—C6—C7—C81.6 (6)C18—C19—C20—C111.6 (5)
C6—C7—C8—C90.9 (5)C18—C19—C20—O2178.0 (3)
C7—C8—C9—C40.8 (4)C28—N1—C21—C2272.2 (3)
C7—C8—C9—C10178.0 (3)P1—N1—C21—C22118.7 (2)
C3—C4—C9—C8175.6 (3)N1—C21—C22—C2333.8 (4)
C5—C4—C9—C81.7 (4)N1—C21—C22—C27148.5 (3)
C3—C4—C9—C101.6 (4)C27—C22—C23—C240.7 (4)
C5—C4—C9—C10179.0 (3)C21—C22—C23—C24178.5 (3)
O1—C1—C10—C9177.8 (2)C22—C23—C24—C250.3 (5)
C2—C1—C10—C96.8 (4)C23—C24—C25—C261.3 (5)
O1—C1—C10—C111.4 (4)C24—C25—C26—C271.1 (5)
C2—C1—C10—C11176.8 (2)C25—C26—C27—C220.0 (5)
C8—C9—C10—C1170.9 (2)C23—C22—C27—C260.9 (5)
C4—C9—C10—C16.3 (4)C21—C22—C27—C26178.7 (3)
C8—C9—C10—C115.4 (4)C32—N2—C28—N1177.8 (3)
C4—C9—C10—C11177.5 (3)C32—N2—C28—C291.1 (4)
C1—C10—C11—C2052.8 (4)C21—N1—C28—N2172.3 (2)
C9—C10—C11—C20123.4 (3)P1—N1—C28—N22.1 (3)
C1—C10—C11—C12124.2 (3)C21—N1—C28—C296.6 (4)
C9—C10—C11—C1259.6 (4)P1—N1—C28—C29176.8 (2)
C20—C11—C12—C13174.4 (3)N2—C28—C29—C302.5 (4)
C10—C11—C12—C132.7 (4)N1—C28—C29—C30176.3 (3)
C20—C11—C12—C174.0 (4)C28—C29—C30—C311.9 (5)
C10—C11—C12—C17178.9 (3)C29—C30—C31—C320.1 (5)
C11—C12—C13—C14179.3 (3)C28—N2—C32—C311.1 (5)
C17—C12—C13—C140.9 (4)C30—C31—C32—N21.7 (5)

Experimental details

Crystal data
Chemical formulaC32H23N2O2P
Mr498.49
Crystal system, space groupOrthorhombic, P212121
Temperature (K)294
a, b, c (Å)9.5168 (11), 10.3952 (11), 25.398 (3)
V3)2512.6 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.36 × 0.32 × 0.30
Data collection
DiffractometerSiemens CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.950, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections
17396, 5805, 2424
Rint0.075
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.058, 0.90
No. of reflections5805
No. of parameters334
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.21
Absolute structureFlack (1983), 0000 Friedel pairs
Absolute structure parameter0.15 (9)

Computer programs: SMART (Siemens, 1995), SMART, SHELXTL (Siemens, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
P1—N11.733 (2)C1—C21.398 (3)
O1—C11.392 (3)C2—C31.350 (4)
N1—C281.387 (3)C4—C51.416 (4)
N1—C211.460 (3)C4—C91.418 (4)
N2—C281.338 (3)C5—C61.337 (4)
O2—P1—O1100.09 (9)C3—C2—C1119.4 (3)
O2—P1—N1103.69 (10)C2—C3—C4121.2 (3)
O1—P1—N193.54 (11)C6—C5—C4121.4 (4)
C1—O1—P1118.97 (16)C7—C8—C9120.8 (3)
C10—C1—C2123.2 (3)C8—C9—C10121.6 (3)
N1—P1—O2—C2046.8 (2)P1—O1—C1—C1074.9 (3)
O2—P1—N1—C2876.7 (2)C1—C10—C11—C2052.8 (4)
O2—P1—N1—C2192.7 (2)C9—C10—C11—C1259.6 (4)
 

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