Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042092/hk2318sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042092/hk2318Isup2.hkl |
CCDC reference: 663732
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.004 Å
- R factor = 0.054
- wR factor = 0.152
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.15 su
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 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the preparation of the title compound, (I), o-(Dipheny1phosphino)aniline (2.46 g, 8.9 mmol) and dry pyridine (2.12 g, 26.7 mmol) (Wilson et al., 1978) were dissolved in dry THF (10 ml), under nitrogen atmosphere. Benzoyl chloride (1.25 g, 8.9 mmol) was rapidly added to the stirred solution, the suspension containing pyridine·HCl was stirred for 2 h. The precipitate was filtered and washed with dry THF. Solvent removal left an viscous oil. The oil was washed with water (6× 25 ml), then dissolved in dichloromethane (15 ml) and the solution dried over MgSO4. The filtered solution was reduced in volume to 3 ml, hexane (100 ml) was added, and the cloudy solution was stored at 263 K. The resulting white needles were collected by filtration, lightly washed with hexane (10 ml), and dried in vacuo at 298 K (yield; 1.90 g, 56.3%, m.p. 377–379 K).
H atoms were positioned geometrically with N—H = 0.86 Å (for NH) and C—H = 0.93 Å for aromatic H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N)
The title compound, (I), a new hybrid phosphine amide ligand, has various applications in the fields of synthesis and homogeneous catalysis, and a series of new phosphine amido chelate complexes have been synthesized (Hedden & Roundhill, 1982; Soonheum et al., 1986; Hedden et al., 1986), especially in the reactions of chelate-assisted N—H oxidative addition (Hedden et al., 1984; Roundhill, 1970). The chelate ligands have mixed functionality types in coordination chemistry. We report herein the crystal structure of the title compound, (I).
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles (Table 1) are generally within normal ranges (Allen et al., 1987). The coordination around P1 atom is a distorted trigonal pyramid.
Rings 1 (C8–C13), 2 (C14–C19), 3 (C20–C25) and 4 (C1–C6) are, of course, planar and the dihedral angles between them are 1/2 = 88.71 (3)°, 1/3 = 77.92 (3)°, 1/4 = 12.78 (3)°, 2/3 = 88.77 (2)°, 2/4 = 83.93 (2)° and 3/4 = 88.26 (3)°.
In the crystal structure, the molecules are elongated along the b axis and stacked along the a axis (Fig. 2).
For related literature, see: Hedden & Roundhill (1982); Soonheum et al. (1986); Hedden et al. (1986, 1984); Roundhill (1970); Wilson et al. (1978). For bond-length data, see: Allen et al. (1987).
Data collection: TEXSAN-PC (Molecular Structure Corporation, 1998); cell refinement: TEXSAN-PC (Molecular Structure Corporation, 1998); data reduction: TEXSAN-PC (Molecular Structure Corporation, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. A packing diagram for (I). |
C25H20NOP | F(000) = 800 |
Mr = 381.39 | Dx = 1.240 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2yn | Cell parameters from 4530 reflections |
a = 9.936 (5) Å | θ = 3.0–27.5° |
b = 10.819 (4) Å | µ = 0.15 mm−1 |
c = 19.038 (11) Å | T = 153 K |
β = 93.49 (2)° | Needle, colourless |
V = 2042.7 (17) Å3 | 0.16 × 0.12 × 0.10 mm |
Z = 4 |
Rigaku Weissenberg IP diffractometer | 4530 independent reflections |
Radiation source: fine-focus sealed tube | 2495 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
scintillation counter scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (correct reference required) | h = −12→12 |
Tmin = 0.975, Tmax = 0.985 | k = −13→13 |
18607 measured reflections | l = −24→24 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0651P)2 + 0.0657P] where P = (Fo2 + 2Fc2)/3 |
4530 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C25H20NOP | V = 2042.7 (17) Å3 |
Mr = 381.39 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.936 (5) Å | µ = 0.15 mm−1 |
b = 10.819 (4) Å | T = 153 K |
c = 19.038 (11) Å | 0.16 × 0.12 × 0.10 mm |
β = 93.49 (2)° |
Rigaku Weissenberg IP diffractometer | 4530 independent reflections |
Absorption correction: multi-scan (correct reference required) | 2495 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.985 | Rint = 0.067 |
18607 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.44 e Å−3 |
4530 reflections | Δρmin = −0.27 e Å−3 |
253 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.18732 (6) | 0.27331 (6) | 0.03471 (3) | 0.0569 (2) | |
N1 | 0.0906 (2) | 0.43689 (17) | −0.08083 (10) | 0.0608 (5) | |
H1A | 0.1580 | 0.4486 | −0.0510 | 0.073* | |
O1 | 0.0171 (2) | 0.47614 (19) | −0.19282 (10) | 0.0928 (6) | |
C1 | 0.2309 (3) | 0.5556 (2) | −0.15335 (14) | 0.0686 (7) | |
C2 | 0.3507 (3) | 0.5288 (3) | −0.11613 (17) | 0.0820 (8) | |
H2A | 0.3546 | 0.4631 | −0.0846 | 0.098* | |
C3 | 0.4651 (3) | 0.5985 (3) | −0.1250 (2) | 0.1004 (11) | |
H3A | 0.5457 | 0.5793 | −0.0999 | 0.121* | |
C4 | 0.4590 (5) | 0.6954 (4) | −0.1709 (3) | 0.1107 (13) | |
H4A | 0.5353 | 0.7433 | −0.1765 | 0.133* | |
C5 | 0.3424 (5) | 0.7225 (3) | −0.2085 (2) | 0.1027 (11) | |
H5A | 0.3399 | 0.7883 | −0.2399 | 0.123* | |
C6 | 0.2267 (3) | 0.6534 (3) | −0.20064 (15) | 0.0847 (8) | |
H6A | 0.1473 | 0.6723 | −0.2268 | 0.102* | |
C7 | 0.1032 (3) | 0.4862 (2) | −0.14497 (14) | 0.0647 (6) | |
C8 | −0.0174 (2) | 0.36881 (19) | −0.05563 (12) | 0.0551 (6) | |
C9 | −0.1477 (3) | 0.3825 (2) | −0.08339 (14) | 0.0649 (6) | |
H9A | −0.1663 | 0.4346 | −0.1216 | 0.078* | |
C10 | −0.2506 (3) | 0.3187 (2) | −0.05418 (15) | 0.0699 (7) | |
H10A | −0.3385 | 0.3279 | −0.0730 | 0.084* | |
C11 | −0.2251 (3) | 0.2416 (2) | 0.00228 (14) | 0.0679 (7) | |
H11A | −0.2953 | 0.2000 | 0.0222 | 0.081* | |
C12 | −0.0945 (2) | 0.2267 (2) | 0.02899 (13) | 0.0598 (6) | |
H12A | −0.0773 | 0.1740 | 0.0671 | 0.072* | |
C13 | 0.0125 (2) | 0.28804 (19) | 0.00078 (12) | 0.0526 (5) | |
C14 | 0.1732 (2) | 0.1743 (2) | 0.11078 (12) | 0.0578 (6) | |
C15 | 0.1525 (3) | 0.2295 (3) | 0.17442 (14) | 0.0797 (8) | |
H15A | 0.1461 | 0.3151 | 0.1769 | 0.096* | |
C16 | 0.1410 (4) | 0.1604 (4) | 0.23404 (16) | 0.1054 (11) | |
H16A | 0.1239 | 0.1989 | 0.2762 | 0.127* | |
C17 | 0.1549 (4) | 0.0342 (4) | 0.23152 (19) | 0.1050 (11) | |
H17A | 0.1508 | −0.0127 | 0.2723 | 0.126* | |
C18 | 0.1746 (4) | −0.0215 (3) | 0.16908 (19) | 0.0964 (10) | |
H18A | 0.1815 | −0.1072 | 0.1672 | 0.116* | |
C19 | 0.1845 (3) | 0.0459 (2) | 0.10894 (14) | 0.0733 (7) | |
H19A | 0.1987 | 0.0061 | 0.0667 | 0.088* | |
C20 | 0.2567 (2) | 0.1730 (2) | −0.03078 (12) | 0.0565 (6) | |
C21 | 0.3957 (3) | 0.1668 (3) | −0.03155 (16) | 0.0778 (8) | |
H21A | 0.4488 | 0.2108 | 0.0017 | 0.093* | |
C22 | 0.4562 (3) | 0.0962 (3) | −0.08090 (18) | 0.0908 (9) | |
H22A | 0.5497 | 0.0920 | −0.0803 | 0.109* | |
C23 | 0.3801 (3) | 0.0328 (2) | −0.13041 (16) | 0.0815 (8) | |
H23A | 0.4213 | −0.0140 | −0.1640 | 0.098* | |
C24 | 0.2432 (3) | 0.0381 (3) | −0.13059 (15) | 0.0815 (8) | |
H24A | 0.1911 | −0.0056 | −0.1644 | 0.098* | |
C25 | 0.1812 (3) | 0.1074 (2) | −0.08124 (14) | 0.0697 (7) | |
H25A | 0.0876 | 0.1100 | −0.0819 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0542 (4) | 0.0626 (4) | 0.0536 (4) | 0.0002 (3) | 0.0002 (3) | −0.0031 (3) |
N1 | 0.0624 (13) | 0.0649 (11) | 0.0546 (12) | −0.0059 (9) | −0.0010 (10) | 0.0008 (9) |
O1 | 0.0976 (16) | 0.1228 (16) | 0.0570 (12) | −0.0254 (12) | −0.0040 (11) | 0.0088 (11) |
C1 | 0.0824 (19) | 0.0681 (15) | 0.0569 (15) | −0.0070 (13) | 0.0170 (14) | −0.0125 (12) |
C2 | 0.075 (2) | 0.0842 (18) | 0.089 (2) | −0.0015 (15) | 0.0167 (17) | −0.0088 (15) |
C3 | 0.075 (2) | 0.107 (2) | 0.121 (3) | −0.0128 (18) | 0.022 (2) | −0.027 (2) |
C4 | 0.108 (3) | 0.096 (3) | 0.133 (3) | −0.029 (2) | 0.048 (3) | −0.032 (2) |
C5 | 0.130 (3) | 0.083 (2) | 0.099 (3) | −0.028 (2) | 0.039 (3) | −0.0034 (18) |
C6 | 0.103 (2) | 0.0836 (19) | 0.0696 (19) | −0.0125 (16) | 0.0173 (17) | −0.0018 (15) |
C7 | 0.0755 (19) | 0.0650 (14) | 0.0537 (15) | −0.0006 (12) | 0.0054 (13) | −0.0064 (11) |
C8 | 0.0566 (14) | 0.0553 (12) | 0.0533 (14) | 0.0012 (10) | 0.0030 (11) | −0.0035 (10) |
C9 | 0.0664 (17) | 0.0652 (14) | 0.0622 (16) | 0.0044 (12) | −0.0031 (13) | 0.0030 (11) |
C10 | 0.0504 (16) | 0.0820 (17) | 0.0762 (19) | 0.0060 (12) | −0.0039 (13) | −0.0016 (14) |
C11 | 0.0550 (16) | 0.0782 (16) | 0.0711 (18) | −0.0010 (12) | 0.0081 (13) | −0.0022 (13) |
C12 | 0.0595 (16) | 0.0632 (13) | 0.0572 (14) | 0.0007 (11) | 0.0064 (12) | 0.0011 (11) |
C13 | 0.0567 (14) | 0.0519 (12) | 0.0493 (13) | 0.0012 (10) | 0.0045 (11) | −0.0056 (10) |
C14 | 0.0476 (14) | 0.0733 (15) | 0.0520 (14) | 0.0003 (10) | −0.0015 (10) | 0.0001 (11) |
C15 | 0.094 (2) | 0.0893 (18) | 0.0558 (17) | −0.0006 (15) | 0.0018 (15) | −0.0094 (14) |
C16 | 0.118 (3) | 0.149 (3) | 0.0502 (19) | −0.004 (2) | 0.0071 (18) | −0.0022 (19) |
C17 | 0.114 (3) | 0.126 (3) | 0.074 (2) | −0.008 (2) | −0.002 (2) | 0.032 (2) |
C18 | 0.111 (3) | 0.088 (2) | 0.089 (2) | 0.0025 (17) | 0.000 (2) | 0.0226 (18) |
C19 | 0.082 (2) | 0.0716 (16) | 0.0657 (17) | 0.0064 (13) | 0.0006 (14) | 0.0077 (13) |
C20 | 0.0562 (15) | 0.0604 (13) | 0.0529 (14) | 0.0010 (10) | 0.0032 (11) | 0.0030 (10) |
C21 | 0.0542 (17) | 0.0925 (18) | 0.086 (2) | 0.0031 (13) | 0.0027 (14) | −0.0219 (16) |
C22 | 0.0651 (19) | 0.106 (2) | 0.103 (2) | 0.0102 (16) | 0.0181 (17) | −0.0206 (19) |
C23 | 0.091 (2) | 0.0790 (18) | 0.077 (2) | 0.0086 (15) | 0.0274 (17) | −0.0072 (15) |
C24 | 0.091 (2) | 0.0877 (18) | 0.0656 (18) | −0.0050 (15) | 0.0055 (16) | −0.0180 (14) |
C25 | 0.0623 (17) | 0.0840 (17) | 0.0629 (16) | −0.0032 (13) | 0.0050 (13) | −0.0131 (13) |
P1—C14 | 1.814 (3) | C11—H11A | 0.9300 |
P1—C20 | 1.820 (2) | C12—C13 | 1.389 (3) |
P1—C13 | 1.823 (3) | C12—H12A | 0.9300 |
N1—C7 | 1.345 (3) | C14—C15 | 1.378 (3) |
N1—C8 | 1.410 (3) | C14—C19 | 1.394 (3) |
N1—H1A | 0.8600 | C15—C16 | 1.370 (4) |
O1—C7 | 1.216 (3) | C15—H15A | 0.9300 |
C1—C2 | 1.378 (4) | C16—C17 | 1.374 (5) |
C1—C6 | 1.388 (4) | C16—H16A | 0.9300 |
C1—C7 | 1.492 (4) | C17—C18 | 1.357 (5) |
C2—C3 | 1.383 (4) | C17—H17A | 0.9300 |
C2—H2A | 0.9300 | C18—C19 | 1.366 (4) |
C3—C4 | 1.364 (5) | C18—H18A | 0.9300 |
C3—H3A | 0.9300 | C19—H19A | 0.9300 |
C4—C5 | 1.356 (5) | C20—C25 | 1.378 (3) |
C4—H4A | 0.9300 | C20—C21 | 1.384 (4) |
C5—C6 | 1.386 (5) | C21—C22 | 1.377 (4) |
C5—H5A | 0.9300 | C21—H21A | 0.9300 |
C6—H6A | 0.9300 | C22—C23 | 1.358 (4) |
C8—C9 | 1.377 (3) | C22—H22A | 0.9300 |
C8—C13 | 1.402 (3) | C23—C24 | 1.361 (4) |
C9—C10 | 1.378 (4) | C23—H23A | 0.9300 |
C9—H9A | 0.9300 | C24—C25 | 1.377 (4) |
C10—C11 | 1.372 (4) | C24—H24A | 0.9300 |
C10—H10A | 0.9300 | C25—H25A | 0.9300 |
C11—C12 | 1.374 (4) | ||
C14—P1—C20 | 104.20 (11) | C13—C12—H12A | 119.0 |
C14—P1—C13 | 102.48 (11) | C12—C13—C8 | 117.5 (2) |
C20—P1—C13 | 101.64 (11) | C12—C13—P1 | 123.83 (18) |
C7—N1—C8 | 129.1 (2) | C8—C13—P1 | 118.60 (17) |
C7—N1—H1A | 115.5 | C15—C14—C19 | 118.1 (2) |
C8—N1—H1A | 115.5 | C15—C14—P1 | 118.0 (2) |
C2—C1—C6 | 119.0 (3) | C19—C14—P1 | 123.95 (19) |
C2—C1—C7 | 123.6 (3) | C16—C15—C14 | 121.1 (3) |
C6—C1—C7 | 117.5 (3) | C16—C15—H15A | 119.5 |
C1—C2—C3 | 120.9 (3) | C14—C15—H15A | 119.5 |
C1—C2—H2A | 119.6 | C15—C16—C17 | 120.0 (3) |
C3—C2—H2A | 119.6 | C15—C16—H16A | 120.0 |
C4—C3—C2 | 119.5 (4) | C17—C16—H16A | 120.0 |
C4—C3—H3A | 120.3 | C18—C17—C16 | 119.5 (3) |
C2—C3—H3A | 120.3 | C18—C17—H17A | 120.3 |
C5—C4—C3 | 120.5 (3) | C16—C17—H17A | 120.3 |
C5—C4—H4A | 119.8 | C17—C18—C19 | 121.2 (3) |
C3—C4—H4A | 119.8 | C17—C18—H18A | 119.4 |
C4—C5—C6 | 121.0 (4) | C19—C18—H18A | 119.4 |
C4—C5—H5A | 119.5 | C18—C19—C14 | 120.1 (3) |
C6—C5—H5A | 119.5 | C18—C19—H19A | 120.0 |
C5—C6—C1 | 119.2 (3) | C14—C19—H19A | 120.0 |
C5—C6—H6A | 120.4 | C25—C20—C21 | 117.9 (2) |
C1—C6—H6A | 120.4 | C25—C20—P1 | 124.89 (19) |
O1—C7—N1 | 123.0 (2) | C21—C20—P1 | 117.12 (19) |
O1—C7—C1 | 122.0 (2) | C22—C21—C20 | 120.8 (3) |
N1—C7—C1 | 115.0 (2) | C22—C21—H21A | 119.6 |
C9—C8—C13 | 120.8 (2) | C20—C21—H21A | 119.6 |
C9—C8—N1 | 122.1 (2) | C23—C22—C21 | 120.4 (3) |
C13—C8—N1 | 117.1 (2) | C23—C22—H22A | 119.8 |
C8—C9—C10 | 119.6 (2) | C21—C22—H22A | 119.8 |
C8—C9—H9A | 120.2 | C22—C23—C24 | 119.6 (3) |
C10—C9—H9A | 120.2 | C22—C23—H23A | 120.2 |
C11—C10—C9 | 121.0 (2) | C24—C23—H23A | 120.2 |
C11—C10—H10A | 119.5 | C23—C24—C25 | 120.7 (3) |
C9—C10—H10A | 119.5 | C23—C24—H24A | 119.7 |
C10—C11—C12 | 119.1 (2) | C25—C24—H24A | 119.7 |
C10—C11—H11A | 120.4 | C24—C25—C20 | 120.6 (3) |
C12—C11—H11A | 120.4 | C24—C25—H25A | 119.7 |
C11—C12—C13 | 121.9 (2) | C20—C25—H25A | 119.7 |
C11—C12—H12A | 119.0 | ||
C6—C1—C2—C3 | 0.5 (4) | C20—P1—C13—C12 | 104.1 (2) |
C7—C1—C2—C3 | −178.5 (2) | C14—P1—C13—C8 | 174.36 (17) |
C1—C2—C3—C4 | 0.5 (5) | C20—P1—C13—C8 | −78.05 (19) |
C2—C3—C4—C5 | −1.1 (5) | C20—P1—C14—C15 | 165.6 (2) |
C3—C4—C5—C6 | 0.7 (6) | C13—P1—C14—C15 | −88.8 (2) |
C4—C5—C6—C1 | 0.3 (5) | C20—P1—C14—C19 | −13.2 (2) |
C2—C1—C6—C5 | −0.9 (4) | C13—P1—C14—C19 | 92.4 (2) |
C7—C1—C6—C5 | 178.2 (3) | C19—C14—C15—C16 | −1.0 (4) |
C8—N1—C7—O1 | −0.8 (4) | P1—C14—C15—C16 | −179.9 (2) |
C8—N1—C7—C1 | 178.7 (2) | C14—C15—C16—C17 | 2.3 (5) |
C2—C1—C7—O1 | −151.3 (3) | C15—C16—C17—C18 | −2.6 (6) |
C6—C1—C7—O1 | 29.7 (4) | C16—C17—C18—C19 | 1.7 (6) |
C2—C1—C7—N1 | 29.2 (4) | C17—C18—C19—C14 | −0.5 (5) |
C6—C1—C7—N1 | −149.8 (2) | C15—C14—C19—C18 | 0.2 (4) |
C7—N1—C8—C9 | −26.4 (4) | P1—C14—C19—C18 | 179.0 (2) |
C7—N1—C8—C13 | 155.3 (2) | C14—P1—C20—C25 | 93.4 (2) |
C13—C8—C9—C10 | 1.7 (4) | C13—P1—C20—C25 | −12.9 (2) |
N1—C8—C9—C10 | −176.4 (2) | C14—P1—C20—C21 | −89.6 (2) |
C8—C9—C10—C11 | 0.1 (4) | C13—P1—C20—C21 | 164.2 (2) |
C9—C10—C11—C12 | −1.2 (4) | C25—C20—C21—C22 | −0.6 (4) |
C10—C11—C12—C13 | 0.4 (4) | P1—C20—C21—C22 | −177.8 (2) |
C11—C12—C13—C8 | 1.3 (3) | C20—C21—C22—C23 | 0.9 (5) |
C11—C12—C13—P1 | 179.21 (19) | C21—C22—C23—C24 | −0.7 (5) |
C9—C8—C13—C12 | −2.4 (3) | C22—C23—C24—C25 | 0.2 (5) |
N1—C8—C13—C12 | 175.86 (19) | C23—C24—C25—C20 | 0.1 (4) |
C9—C8—C13—P1 | 179.58 (18) | C21—C20—C25—C24 | 0.1 (4) |
N1—C8—C13—P1 | −2.1 (3) | P1—C20—C25—C24 | 177.1 (2) |
C14—P1—C13—C12 | −3.5 (2) |
Experimental details
Crystal data | |
Chemical formula | C25H20NOP |
Mr | 381.39 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 153 |
a, b, c (Å) | 9.936 (5), 10.819 (4), 19.038 (11) |
β (°) | 93.49 (2) |
V (Å3) | 2042.7 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.16 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Rigaku Weissenberg IP |
Absorption correction | Multi-scan (correct reference required) |
Tmin, Tmax | 0.975, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18607, 4530, 2495 |
Rint | 0.067 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.152, 1.03 |
No. of reflections | 4530 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.27 |
Computer programs: TEXSAN-PC (Molecular Structure Corporation, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).
P1—C14 | 1.814 (3) | C1—C2 | 1.378 (4) |
P1—C20 | 1.820 (2) | C1—C7 | 1.492 (4) |
P1—C13 | 1.823 (3) | C8—C13 | 1.402 (3) |
N1—C7 | 1.345 (3) | C14—C15 | 1.378 (3) |
N1—C8 | 1.410 (3) | C20—C21 | 1.384 (4) |
O1—C7 | 1.216 (3) | ||
C14—P1—C20 | 104.20 (11) | O1—C7—N1 | 123.0 (2) |
C14—P1—C13 | 102.48 (11) | N1—C7—C1 | 115.0 (2) |
C20—P1—C13 | 101.64 (11) | C13—C8—N1 | 117.1 (2) |
C7—N1—C8 | 129.1 (2) | C8—C13—P1 | 118.60 (17) |
The title compound, (I), a new hybrid phosphine amide ligand, has various applications in the fields of synthesis and homogeneous catalysis, and a series of new phosphine amido chelate complexes have been synthesized (Hedden & Roundhill, 1982; Soonheum et al., 1986; Hedden et al., 1986), especially in the reactions of chelate-assisted N—H oxidative addition (Hedden et al., 1984; Roundhill, 1970). The chelate ligands have mixed functionality types in coordination chemistry. We report herein the crystal structure of the title compound, (I).
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles (Table 1) are generally within normal ranges (Allen et al., 1987). The coordination around P1 atom is a distorted trigonal pyramid.
Rings 1 (C8–C13), 2 (C14–C19), 3 (C20–C25) and 4 (C1–C6) are, of course, planar and the dihedral angles between them are 1/2 = 88.71 (3)°, 1/3 = 77.92 (3)°, 1/4 = 12.78 (3)°, 2/3 = 88.77 (2)°, 2/4 = 83.93 (2)° and 3/4 = 88.26 (3)°.
In the crystal structure, the molecules are elongated along the b axis and stacked along the a axis (Fig. 2).