organic compounds
The title compound, C26H22NP, is a Schiff base derived from triphenylphosphine with a 4-methylphenylamine group attached to one of the benzene rings of the phosphine in the o-position. The azomethine C=N bond length is 1.259 (3) Å and the dihedral angle between the benzene ring and its 4-methylphenylamine substituent is 40.02 (2) Å. The geometry at the P atom is approximately tetrahedral.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019422/sj6103sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019422/sj6103Isup2.hkl |
CCDC reference: 277791
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
(2-Diphenylphosphanylbenzylidene)-4-methylphenylamine top
Crystal data top
C26H22NP | F(000) = 800 |
Mr = 379.42 | Dx = 1.193 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2598 reflections |
a = 13.938 (4) Å | θ = 1.9–25.0° |
b = 10.414 (3) Å | µ = 0.14 mm−1 |
c = 19.311 (4) Å | T = 298 K |
β = 131.108 (13)° | Block, pale yellow |
V = 2112.0 (10) Å3 | 0.47 × 0.17 × 0.15 mm |
Z = 4 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3724 independent reflections |
Radiation source: fine-focus sealed tube | 2686 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.0°, θmin = 1.9° |
ω scans | h = −16→16 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→12 |
Tmin = 0.936, Tmax = 0.979 | l = −22→22 |
15172 measured reflections |
Refinement top
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.19 | w = 1/[σ2(Fo2) + (0.0425P)2 + 0.7448P] where P = (Fo2 + 2Fc2)/3 |
3724 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
P1 | 0.19292 (7) | 0.01396 (7) | 0.41902 (5) | 0.0527 (3) | |
N1 | 0.1979 (3) | 0.1788 (2) | 0.62555 (17) | 0.0665 (7) | |
C1 | −0.0324 (3) | 0.2261 (3) | 0.5111 (2) | 0.0676 (9) | |
H1B | −0.0479 | 0.1494 | 0.4806 | 0.081* | |
C2 | −0.1326 (3) | 0.3067 (4) | 0.4799 (2) | 0.0742 (10) | |
H2A | −0.2150 | 0.2830 | 0.4285 | 0.089* | |
C3 | −0.1133 (4) | 0.4214 (3) | 0.5230 (2) | 0.0689 (9) | |
C4 | 0.0094 (4) | 0.4529 (3) | 0.5985 (2) | 0.0737 (10) | |
H4A | 0.0251 | 0.5303 | 0.6285 | 0.088* | |
C5 | 0.1097 (3) | 0.3729 (3) | 0.6310 (2) | 0.0714 (9) | |
H5A | 0.1916 | 0.3962 | 0.6832 | 0.086* | |
C6 | 0.0906 (3) | 0.2589 (3) | 0.5875 (2) | 0.0584 (8) | |
C7 | −0.2241 (4) | 0.5064 (4) | 0.4887 (3) | 0.1048 (14) | |
H7A | −0.1934 | 0.5823 | 0.5261 | 0.157* | |
H7B | −0.2808 | 0.4611 | 0.4922 | 0.157* | |
H7C | −0.2687 | 0.5302 | 0.4261 | 0.157* | |
C8 | 0.2030 (3) | 0.1171 (3) | 0.5720 (2) | 0.0585 (8) | |
H8A | 0.1401 | 0.1321 | 0.5092 | 0.070* | |
C9 | 0.3026 (3) | 0.0231 (3) | 0.60298 (19) | 0.0523 (7) | |
C10 | 0.3902 (3) | −0.0120 (3) | 0.6952 (2) | 0.0669 (9) | |
H10A | 0.3865 | 0.0264 | 0.7368 | 0.080* | |
C11 | 0.4823 (3) | −0.1028 (3) | 0.7256 (2) | 0.0725 (10) | |
H11A | 0.5392 | −0.1270 | 0.7871 | 0.087* | |
C12 | 0.4897 (3) | −0.1575 (3) | 0.6644 (2) | 0.0682 (9) | |
H12A | 0.5524 | −0.2181 | 0.6848 | 0.082* | |
C13 | 0.4050 (3) | −0.1229 (3) | 0.5736 (2) | 0.0584 (8) | |
H13A | 0.4111 | −0.1608 | 0.5331 | 0.070* | |
C14 | 0.3103 (3) | −0.0326 (3) | 0.54064 (19) | 0.0498 (7) | |
C15 | 0.2194 (3) | −0.1029 (3) | 0.36263 (18) | 0.0493 (7) | |
C16 | 0.1552 (3) | −0.2182 (3) | 0.3378 (2) | 0.0728 (9) | |
H16A | 0.1076 | −0.2350 | 0.3548 | 0.087* | |
C17 | 0.1604 (4) | −0.3088 (4) | 0.2882 (3) | 0.0901 (12) | |
H17A | 0.1179 | −0.3866 | 0.2730 | 0.108* | |
C18 | 0.2284 (4) | −0.2837 (4) | 0.2615 (2) | 0.0830 (11) | |
H18A | 0.2302 | −0.3435 | 0.2266 | 0.100* | |
C19 | 0.2933 (3) | −0.1714 (4) | 0.2861 (2) | 0.0746 (10) | |
H19A | 0.3409 | −0.1555 | 0.2690 | 0.089* | |
C20 | 0.2893 (3) | −0.0807 (3) | 0.3363 (2) | 0.0597 (8) | |
H20A | 0.3339 | −0.0041 | 0.3525 | 0.072* | |
C21 | 0.2654 (3) | 0.1583 (3) | 0.4178 (2) | 0.0525 (7) | |
C22 | 0.1956 (3) | 0.2277 (3) | 0.3372 (2) | 0.0734 (10) | |
H22A | 0.1137 | 0.2010 | 0.2870 | 0.088* | |
C23 | 0.2450 (5) | 0.3362 (4) | 0.3295 (3) | 0.0907 (12) | |
H23A | 0.1969 | 0.3807 | 0.2741 | 0.109* | |
C24 | 0.3637 (5) | 0.3783 (4) | 0.4024 (3) | 0.0902 (12) | |
H24A | 0.3970 | 0.4512 | 0.3971 | 0.108* | |
C25 | 0.4334 (4) | 0.3129 (3) | 0.4833 (3) | 0.0836 (11) | |
H25A | 0.5142 | 0.3420 | 0.5336 | 0.100* | |
C26 | 0.3852 (3) | 0.2038 (3) | 0.4912 (2) | 0.0661 (9) | |
H26A | 0.4341 | 0.1601 | 0.5469 | 0.079* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0468 (5) | 0.0590 (5) | 0.0498 (5) | 0.0023 (4) | 0.0306 (4) | −0.0026 (4) |
N1 | 0.0707 (18) | 0.0736 (18) | 0.0631 (16) | 0.0053 (15) | 0.0475 (16) | −0.0067 (14) |
C1 | 0.067 (2) | 0.073 (2) | 0.071 (2) | −0.0054 (19) | 0.049 (2) | −0.0120 (18) |
C2 | 0.063 (2) | 0.093 (3) | 0.073 (2) | −0.002 (2) | 0.047 (2) | −0.002 (2) |
C3 | 0.081 (3) | 0.076 (2) | 0.073 (2) | 0.017 (2) | 0.060 (2) | 0.015 (2) |
C4 | 0.088 (3) | 0.068 (2) | 0.071 (2) | 0.007 (2) | 0.055 (2) | −0.0063 (19) |
C5 | 0.072 (2) | 0.076 (2) | 0.062 (2) | 0.003 (2) | 0.0422 (19) | −0.0117 (18) |
C6 | 0.066 (2) | 0.065 (2) | 0.0559 (19) | 0.0037 (17) | 0.0448 (19) | −0.0034 (16) |
C7 | 0.106 (3) | 0.113 (3) | 0.113 (3) | 0.036 (3) | 0.080 (3) | 0.023 (3) |
C8 | 0.064 (2) | 0.065 (2) | 0.0567 (18) | −0.0009 (17) | 0.0442 (17) | −0.0044 (16) |
C9 | 0.0524 (18) | 0.0541 (18) | 0.0528 (18) | −0.0027 (15) | 0.0356 (16) | −0.0026 (14) |
C10 | 0.069 (2) | 0.075 (2) | 0.053 (2) | −0.0005 (19) | 0.0389 (18) | −0.0038 (17) |
C11 | 0.060 (2) | 0.085 (3) | 0.0499 (19) | 0.001 (2) | 0.0263 (18) | 0.0088 (18) |
C12 | 0.056 (2) | 0.072 (2) | 0.064 (2) | 0.0089 (17) | 0.0348 (19) | 0.0068 (18) |
C13 | 0.0530 (19) | 0.066 (2) | 0.059 (2) | 0.0033 (16) | 0.0381 (17) | −0.0020 (16) |
C14 | 0.0480 (17) | 0.0500 (17) | 0.0539 (17) | −0.0038 (14) | 0.0345 (15) | −0.0046 (14) |
C15 | 0.0432 (17) | 0.0527 (18) | 0.0428 (16) | 0.0022 (14) | 0.0243 (15) | 0.0004 (13) |
C16 | 0.076 (2) | 0.067 (2) | 0.086 (2) | −0.0128 (19) | 0.057 (2) | −0.0179 (19) |
C17 | 0.091 (3) | 0.068 (2) | 0.107 (3) | −0.014 (2) | 0.063 (3) | −0.029 (2) |
C18 | 0.085 (3) | 0.083 (3) | 0.066 (2) | 0.018 (2) | 0.043 (2) | −0.015 (2) |
C19 | 0.081 (3) | 0.086 (3) | 0.070 (2) | 0.018 (2) | 0.056 (2) | 0.003 (2) |
C20 | 0.066 (2) | 0.0567 (19) | 0.0613 (19) | 0.0090 (16) | 0.0439 (18) | 0.0042 (16) |
C21 | 0.059 (2) | 0.0500 (17) | 0.0520 (18) | 0.0091 (15) | 0.0378 (17) | 0.0016 (15) |
C22 | 0.083 (2) | 0.062 (2) | 0.064 (2) | 0.0004 (19) | 0.044 (2) | −0.0014 (18) |
C23 | 0.136 (4) | 0.060 (2) | 0.080 (3) | 0.010 (3) | 0.073 (3) | 0.008 (2) |
C24 | 0.136 (4) | 0.051 (2) | 0.118 (3) | −0.011 (3) | 0.099 (3) | −0.012 (2) |
C25 | 0.084 (3) | 0.063 (2) | 0.105 (3) | −0.011 (2) | 0.063 (3) | −0.012 (2) |
C26 | 0.062 (2) | 0.056 (2) | 0.072 (2) | 0.0019 (17) | 0.041 (2) | −0.0005 (17) |
Geometric parameters (Å, º) top
P1—C21 | 1.820 (3) | C12—C13 | 1.370 (4) |
P1—C15 | 1.825 (3) | C12—H12A | 0.9300 |
P1—C14 | 1.837 (3) | C13—C14 | 1.388 (4) |
N1—C8 | 1.259 (3) | C13—H13A | 0.9300 |
N1—C6 | 1.423 (4) | C15—C16 | 1.382 (4) |
C1—C6 | 1.381 (4) | C15—C20 | 1.382 (4) |
C1—C2 | 1.382 (4) | C16—C17 | 1.380 (5) |
C1—H1B | 0.9300 | C16—H16A | 0.9300 |
C2—C3 | 1.377 (5) | C17—C18 | 1.370 (5) |
C2—H2A | 0.9300 | C17—H17A | 0.9300 |
C3—C4 | 1.371 (5) | C18—C19 | 1.359 (5) |
C3—C7 | 1.505 (5) | C18—H18A | 0.9300 |
C4—C5 | 1.374 (4) | C19—C20 | 1.380 (4) |
C4—H4A | 0.9300 | C19—H19A | 0.9300 |
C5—C6 | 1.376 (4) | C20—H20A | 0.9300 |
C5—H5A | 0.9300 | C21—C22 | 1.379 (4) |
C7—H7A | 0.9600 | C21—C26 | 1.382 (4) |
C7—H7B | 0.9600 | C22—C23 | 1.382 (5) |
C7—H7C | 0.9600 | C22—H22A | 0.9300 |
C8—C9 | 1.467 (4) | C23—C24 | 1.360 (5) |
C8—H8A | 0.9300 | C23—H23A | 0.9300 |
C9—C10 | 1.391 (4) | C24—C25 | 1.361 (5) |
C9—C14 | 1.403 (4) | C24—H24A | 0.9300 |
C10—C11 | 1.378 (4) | C25—C26 | 1.380 (5) |
C10—H10A | 0.9300 | C25—H25A | 0.9300 |
C11—C12 | 1.374 (4) | C26—H26A | 0.9300 |
C11—H11A | 0.9300 | ||
C21—P1—C15 | 102.18 (13) | C12—C13—C14 | 121.7 (3) |
C21—P1—C14 | 101.49 (13) | C12—C13—H13A | 119.2 |
C15—P1—C14 | 103.14 (13) | C14—C13—H13A | 119.2 |
C8—N1—C6 | 118.8 (3) | C13—C14—C9 | 118.2 (3) |
C6—C1—C2 | 120.3 (3) | C13—C14—P1 | 123.0 (2) |
C6—C1—H1B | 119.8 | C9—C14—P1 | 118.8 (2) |
C2—C1—H1B | 119.8 | C16—C15—C20 | 118.1 (3) |
C3—C2—C1 | 121.5 (3) | C16—C15—P1 | 116.5 (2) |
C3—C2—H2A | 119.3 | C20—C15—P1 | 125.2 (2) |
C1—C2—H2A | 119.3 | C17—C16—C15 | 121.1 (3) |
C4—C3—C2 | 117.6 (3) | C17—C16—H16A | 119.5 |
C4—C3—C7 | 121.9 (4) | C15—C16—H16A | 119.5 |
C2—C3—C7 | 120.5 (4) | C18—C17—C16 | 119.8 (4) |
C3—C4—C5 | 121.5 (3) | C18—C17—H17A | 120.1 |
C3—C4—H4A | 119.2 | C16—C17—H17A | 120.1 |
C5—C4—H4A | 119.2 | C19—C18—C17 | 119.9 (3) |
C4—C5—C6 | 121.0 (3) | C19—C18—H18A | 120.0 |
C4—C5—H5A | 119.5 | C17—C18—H18A | 120.0 |
C6—C5—H5A | 119.5 | C18—C19—C20 | 120.6 (3) |
C5—C6—C1 | 118.1 (3) | C18—C19—H19A | 119.7 |
C5—C6—N1 | 118.4 (3) | C20—C19—H19A | 119.7 |
C1—C6—N1 | 123.5 (3) | C19—C20—C15 | 120.5 (3) |
C3—C7—H7A | 109.5 | C19—C20—H20A | 119.7 |
C3—C7—H7B | 109.5 | C15—C20—H20A | 119.7 |
H7A—C7—H7B | 109.5 | C22—C21—C26 | 117.3 (3) |
C3—C7—H7C | 109.5 | C22—C21—P1 | 117.5 (2) |
H7A—C7—H7C | 109.5 | C26—C21—P1 | 125.2 (2) |
H7B—C7—H7C | 109.5 | C21—C22—C23 | 121.2 (3) |
N1—C8—C9 | 123.7 (3) | C21—C22—H22A | 119.4 |
N1—C8—H8A | 118.1 | C23—C22—H22A | 119.4 |
C9—C8—H8A | 118.1 | C24—C23—C22 | 120.4 (4) |
C10—C9—C14 | 119.4 (3) | C24—C23—H23A | 119.8 |
C10—C9—C8 | 119.8 (3) | C22—C23—H23A | 119.8 |
C14—C9—C8 | 120.8 (3) | C23—C24—C25 | 119.5 (4) |
C11—C10—C9 | 120.9 (3) | C23—C24—H24A | 120.3 |
C11—C10—H10A | 119.5 | C25—C24—H24A | 120.3 |
C9—C10—H10A | 119.5 | C24—C25—C26 | 120.5 (4) |
C12—C11—C10 | 119.6 (3) | C24—C25—H25A | 119.7 |
C12—C11—H11A | 120.2 | C26—C25—H25A | 119.7 |
C10—C11—H11A | 120.2 | C25—C26—C21 | 121.1 (3) |
C13—C12—C11 | 120.2 (3) | C25—C26—H26A | 119.4 |
C13—C12—H12A | 119.9 | C21—C26—H26A | 119.4 |
C11—C12—H12A | 119.9 | ||
C6—C1—C2—C3 | 0.3 (5) | C15—P1—C14—C13 | 9.4 (3) |
C1—C2—C3—C4 | −0.1 (5) | C21—P1—C14—C9 | 85.3 (2) |
C1—C2—C3—C7 | −178.9 (3) | C15—P1—C14—C9 | −169.1 (2) |
C2—C3—C4—C5 | −0.7 (5) | C21—P1—C15—C16 | −168.8 (2) |
C7—C3—C4—C5 | 178.1 (3) | C14—P1—C15—C16 | 86.2 (2) |
C3—C4—C5—C6 | 1.4 (5) | C21—P1—C15—C20 | 5.4 (3) |
C4—C5—C6—C1 | −1.1 (5) | C14—P1—C15—C20 | −99.6 (3) |
C4—C5—C6—N1 | −178.6 (3) | C20—C15—C16—C17 | 0.0 (5) |
C2—C1—C6—C5 | 0.3 (5) | P1—C15—C16—C17 | 174.7 (3) |
C2—C1—C6—N1 | 177.7 (3) | C15—C16—C17—C18 | −1.2 (6) |
C8—N1—C6—C5 | −143.6 (3) | C16—C17—C18—C19 | 1.9 (6) |
C8—N1—C6—C1 | 39.0 (4) | C17—C18—C19—C20 | −1.4 (5) |
C6—N1—C8—C9 | −174.3 (3) | C18—C19—C20—C15 | 0.2 (5) |
N1—C8—C9—C10 | 6.9 (5) | C16—C15—C20—C19 | 0.5 (4) |
N1—C8—C9—C14 | −173.4 (3) | P1—C15—C20—C19 | −173.7 (2) |
C14—C9—C10—C11 | −1.6 (5) | C15—P1—C21—C22 | 79.9 (2) |
C8—C9—C10—C11 | 178.1 (3) | C14—P1—C21—C22 | −173.8 (2) |
C9—C10—C11—C12 | 1.5 (5) | C15—P1—C21—C26 | −99.9 (3) |
C10—C11—C12—C13 | −0.7 (5) | C14—P1—C21—C26 | 6.4 (3) |
C11—C12—C13—C14 | 0.1 (5) | C26—C21—C22—C23 | 1.8 (5) |
C12—C13—C14—C9 | −0.2 (4) | P1—C21—C22—C23 | −178.0 (3) |
C12—C13—C14—P1 | −178.7 (2) | C21—C22—C23—C24 | −1.2 (5) |
C10—C9—C14—C13 | 0.9 (4) | C22—C23—C24—C25 | −0.2 (6) |
C8—C9—C14—C13 | −178.8 (3) | C23—C24—C25—C26 | 0.8 (6) |
C10—C9—C14—P1 | 179.5 (2) | C24—C25—C26—C21 | −0.1 (5) |
C8—C9—C14—P1 | −0.2 (4) | C22—C21—C26—C25 | −1.2 (4) |
C21—P1—C14—C13 | −96.2 (3) | P1—C21—C26—C25 | 178.6 (2) |