N-[2-(Diphenyl­phosphanyl)benzyl­idene]-4-methyl­aniline

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.067
• wR factor = 0.140
• Data-to-parameter ratio = 14.7

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    C21    -   C22     ..       5.37 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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

Crystal data

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) Å^3	0.47 × 0.17 × 0.15 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0425P)^2 + 0.7448P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···P1	0.93	2.60	3.059 (4)	111