2-(2H-Benzotriazol-2-yl)-4-methyl-phenyl diphenyl-phosphinate.

In the title mol-ecule, C(25)H(20)N(3)O(2)P, the dihedral angle between the mean planes of the benzotriazol ring system and the N-bonded benzene ring is 45.8 (2)°. All but one of the angles at the P atom show slight distortions from an ideal tetra-hedral geometry.

Related literature

For background to the use of pan class="Chemical">2-(2H-benzotriazol-2H-yl)phenoln> (pan class="Chemical">BTP-H) derivatives, see: Li et al. (2009 ▶); Tsai et al. (2009 ▶). For related structures, see: pan class="Chemical">Al-Farhan (1992 ▶); Cheng et al. (2007 ▶).

Experimental

Crystal data

pan class="Chemical">C25H20N3O2Pn>

M = 425.41

Orthorhombic,

a = 12.7691 (7) Å

b = 9.4064 (5) Å

c = 18.6362 (10) Å

V = 2238.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 296 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker SMART-1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.963, T max = 0.974

11920 measured reflections

3684 independent reflections

3343 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.05

3684 reflections

280 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1412 Friedel pairs

Flack parameter: 0.01 (7)

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); n class="Chemical">program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029870/lh2871sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029870/lh2871Isup2.hkl

Additional supn class="Chemical">plementary materials: crystallographic information; 3D view; checkCIF report

C25H20N3O2P	F(000) = 888
Mr = 425.41	Dx = 1.262 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 6495 reflections
a = 12.7691 (7) Å	θ = 2.7–26.0°
b = 9.4064 (5) Å	µ = 0.15 mm−1
c = 18.6362 (10) Å	T = 296 K
V = 2238.4 (2) Å3	Block, colourless
Z = 4	0.30 × 0.20 × 0.15 mm

Bruker SMART-1000 CCD diffractometer	3684 independent reflections
Radiation source: fine-focus sealed tube	3343 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
Tmin = 0.963, Tmax = 0.974	k = −11→11
11920 measured reflections	l = −19→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3684 reflections	Δρmax = 0.14 e Å−3
280 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: Flack (1983), 1412 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (7)

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
P	−0.78562 (3)	−0.27388 (4)	−0.41236 (3)	0.04851 (13)
O1	−0.74629 (11)	−0.25123 (13)	−0.49386 (7)	0.0523 (3)
O2	−0.89556 (10)	−0.23744 (14)	−0.39862 (10)	0.0724 (4)
N1	−0.54417 (13)	−0.30745 (18)	−0.54995 (9)	0.0573 (4)
N2	−0.58778 (12)	−0.21611 (16)	−0.59589 (8)	0.0510 (3)
N3	−0.56809 (15)	−0.23649 (17)	−0.66558 (9)	0.0617 (4)
C1	−0.73324 (14)	−0.11822 (19)	−0.52534 (11)	0.0498 (4)
C2	−0.65289 (15)	−0.10047 (19)	−0.57421 (10)	0.0536 (4)
C3	−0.63716 (18)	0.0309 (2)	−0.60682 (12)	0.0641 (5)
H3B	−0.5823	0.0422	−0.6391	0.077*
C4	−0.7020 (2)	0.1451 (2)	−0.59187 (13)	0.0675 (6)
C5	−0.78319 (19)	0.1244 (2)	−0.54483 (14)	0.0710 (6)
H5A	−0.8283	0.1996	−0.5351	0.085*
C6	−0.80000 (17)	−0.0052 (2)	−0.51143 (12)	0.0652 (5)
H6A	−0.8558	−0.0163	−0.4798	0.078*
C7	−0.49173 (14)	−0.3965 (2)	−0.59453 (10)	0.0543 (4)
C8	−0.4308 (2)	−0.5185 (3)	−0.57796 (13)	0.0768 (6)
H8A	−0.4209	−0.5492	−0.5310	0.092*
C9	−0.3876 (2)	−0.5879 (3)	−0.63507 (16)	0.0861 (7)
H9A	−0.3471	−0.6683	−0.6265	0.103*
C10	−0.4020 (2)	−0.5427 (3)	−0.70636 (15)	0.0862 (7)
H10A	−0.3709	−0.5943	−0.7432	0.103*
C11	−0.45980 (19)	−0.4263 (3)	−0.72317 (13)	0.0762 (6)
H11A	−0.4683	−0.3963	−0.7704	0.091*
C12	−0.50631 (15)	−0.3531 (2)	−0.66534 (11)	0.0561 (4)
C13	−0.6860 (3)	0.2874 (3)	−0.6283 (2)	0.0984 (9)
H13A	−0.7377	0.3535	−0.6114	0.148*
H13B	−0.6929	0.2760	−0.6793	0.148*
H13C	−0.6173	0.3227	−0.6173	0.148*
C14	−0.75764 (14)	−0.45832 (18)	−0.40115 (10)	0.0511 (4)
C15	−0.66460 (14)	−0.5202 (2)	−0.42229 (12)	0.0612 (5)
H15A	−0.6144	−0.4658	−0.4459	0.073*
C16	−0.64533 (18)	−0.6626 (2)	−0.40869 (16)	0.0746 (6)
H16A	−0.5822	−0.7036	−0.4226	0.089*
C17	−0.7204 (3)	−0.7429 (2)	−0.37445 (17)	0.0840 (8)
H17A	−0.7086	−0.8391	−0.3663	0.101*
C18	−0.8118 (3)	−0.6822 (3)	−0.35251 (19)	0.0982 (9)
H18A	−0.8609	−0.7367	−0.3281	0.118*
C19	−0.83227 (19)	−0.5408 (3)	−0.36614 (16)	0.0811 (7)
H19A	−0.8956	−0.5008	−0.3520	0.097*
C20	−0.69692 (13)	−0.17140 (17)	−0.35845 (9)	0.0460 (4)
C21	−0.73139 (19)	−0.1249 (2)	−0.29154 (12)	0.0636 (6)
H21A	−0.7985	−0.1470	−0.2757	0.076*
C22	−0.6643 (2)	−0.0451 (3)	−0.24858 (12)	0.0791 (7)
H22A	−0.6865	−0.0153	−0.2035	0.095*
C23	−0.5668 (2)	−0.0102 (2)	−0.27184 (15)	0.0770 (6)
H23A	−0.5234	0.0449	−0.2430	0.092*
C24	−0.53189 (18)	−0.0559 (2)	−0.33777 (13)	0.0677 (5)
H24A	−0.4653	−0.0310	−0.3535	0.081*
C25	−0.59558 (14)	−0.1389 (2)	−0.38062 (11)	0.0562 (4)
H25A	−0.5708	−0.1731	−0.4243	0.067*

	U11	U22	U33	U12	U13	U23
P	0.0399 (2)	0.0488 (2)	0.0569 (3)	−0.00062 (15)	0.0029 (2)	−0.0003 (2)
O1	0.0566 (7)	0.0499 (6)	0.0504 (7)	0.0003 (5)	−0.0023 (6)	0.0000 (5)
O2	0.0446 (7)	0.0726 (9)	0.0998 (14)	0.0035 (6)	0.0074 (7)	0.0013 (8)
N1	0.0617 (9)	0.0667 (10)	0.0436 (8)	0.0101 (8)	−0.0017 (7)	0.0031 (7)
N2	0.0576 (9)	0.0532 (8)	0.0424 (8)	0.0008 (6)	−0.0003 (6)	0.0025 (6)
N3	0.0772 (11)	0.0662 (10)	0.0416 (9)	0.0011 (8)	0.0019 (8)	0.0047 (7)
C1	0.0529 (10)	0.0484 (10)	0.0481 (10)	0.0013 (7)	−0.0086 (8)	−0.0012 (8)
C2	0.0621 (10)	0.0524 (10)	0.0462 (10)	0.0023 (8)	−0.0080 (8)	0.0007 (8)
C3	0.0749 (13)	0.0586 (12)	0.0588 (12)	−0.0026 (9)	−0.0006 (9)	0.0065 (9)
C4	0.0864 (14)	0.0510 (11)	0.0650 (14)	0.0023 (9)	−0.0146 (11)	0.0061 (10)
C5	0.0842 (14)	0.0547 (11)	0.0742 (15)	0.0183 (10)	−0.0125 (12)	−0.0007 (10)
C6	0.0687 (12)	0.0643 (12)	0.0625 (13)	0.0107 (9)	−0.0018 (10)	0.0021 (10)
C7	0.0533 (10)	0.0600 (10)	0.0498 (10)	0.0030 (8)	−0.0007 (8)	−0.0018 (8)
C8	0.0810 (13)	0.0845 (15)	0.0650 (13)	0.0261 (12)	0.0004 (12)	0.0052 (12)
C9	0.0862 (16)	0.0871 (16)	0.0849 (18)	0.0310 (13)	0.0016 (14)	−0.0089 (14)
C10	0.0905 (17)	0.0927 (17)	0.0752 (17)	0.0148 (14)	0.0108 (13)	−0.0277 (14)
C11	0.0877 (16)	0.0905 (17)	0.0504 (12)	0.0048 (13)	0.0065 (11)	−0.0092 (11)
C12	0.0598 (10)	0.0610 (11)	0.0476 (10)	−0.0026 (8)	0.0029 (8)	−0.0012 (8)
C13	0.124 (2)	0.0571 (13)	0.114 (2)	0.0010 (14)	0.0021 (19)	0.0205 (14)
C14	0.0516 (8)	0.0477 (8)	0.0540 (11)	−0.0075 (7)	−0.0029 (8)	−0.0012 (8)
C15	0.0549 (10)	0.0556 (10)	0.0731 (14)	0.0019 (7)	0.0007 (9)	0.0058 (10)
C16	0.0793 (13)	0.0602 (11)	0.0842 (15)	0.0131 (10)	−0.0135 (13)	−0.0024 (12)
C17	0.110 (2)	0.0502 (12)	0.0916 (19)	−0.0074 (12)	−0.0226 (15)	0.0083 (12)
C18	0.112 (2)	0.0664 (14)	0.116 (3)	−0.0274 (15)	0.0132 (18)	0.0180 (15)
C19	0.0705 (13)	0.0671 (14)	0.106 (2)	−0.0147 (10)	0.0195 (13)	0.0097 (13)
C20	0.0529 (9)	0.0382 (8)	0.0467 (9)	0.0036 (7)	0.0034 (7)	−0.0001 (7)
C21	0.0804 (16)	0.0569 (12)	0.0534 (13)	0.0099 (10)	0.0133 (10)	0.0009 (9)
C22	0.122 (2)	0.0656 (14)	0.0500 (12)	0.0125 (14)	−0.0011 (13)	−0.0161 (11)
C23	0.0982 (17)	0.0576 (12)	0.0752 (15)	−0.0024 (11)	−0.0260 (14)	−0.0107 (11)
C24	0.0624 (12)	0.0676 (13)	0.0733 (14)	−0.0109 (9)	−0.0138 (10)	−0.0027 (11)
C25	0.0527 (9)	0.0622 (11)	0.0536 (10)	−0.0032 (8)	0.0018 (8)	−0.0064 (8)

P—O2	1.4675 (14)	C11—C12	1.410 (3)
P—O1	1.6138 (15)	C11—H11A	0.9300
P—C14	1.7835 (18)	C13—H13A	0.9600
P—C20	1.7948 (18)	C13—H13B	0.9600
O1—C1	1.392 (2)	C13—H13C	0.9600
N1—N2	1.335 (2)	C14—C15	1.380 (3)
N1—C7	1.357 (2)	C14—C19	1.391 (3)
N2—N3	1.337 (2)	C15—C16	1.385 (3)
N2—C2	1.427 (2)	C15—H15A	0.9300
N3—C12	1.351 (3)	C16—C17	1.377 (4)
C1—C2	1.382 (3)	C16—H16A	0.9300
C1—C6	1.387 (3)	C17—C18	1.362 (4)
C2—C3	1.392 (3)	C17—H17A	0.9300
C3—C4	1.385 (3)	C18—C19	1.379 (4)
C3—H3B	0.9300	C18—H18A	0.9300
C4—C5	1.371 (4)	C19—H19A	0.9300
C4—C13	1.515 (3)	C20—C25	1.392 (3)
C5—C6	1.385 (3)	C20—C21	1.393 (3)
C5—H5A	0.9300	C21—C22	1.392 (4)
C6—H6A	0.9300	C21—H21A	0.9300
C7—C12	1.394 (3)	C22—C23	1.359 (4)
C7—C8	1.420 (3)	C22—H22A	0.9300
C8—C9	1.365 (4)	C23—C24	1.376 (4)
C8—H8A	0.9300	C23—H23A	0.9300
C9—C10	1.407 (4)	C24—C25	1.381 (3)
C9—H9A	0.9300	C24—H24A	0.9300
C10—C11	1.357 (4)	C25—H25A	0.9300
C10—H10A	0.9300
O2—P—O1	115.53 (10)	N3—C12—C7	108.62 (16)
O2—P—C14	113.48 (8)	N3—C12—C11	129.8 (2)
O1—P—C14	100.15 (8)	C7—C12—C11	121.60 (19)
O2—P—C20	112.37 (9)	C4—C13—H13A	109.5
O1—P—C20	105.04 (8)	C4—C13—H13B	109.5
C14—P—C20	109.30 (8)	H13A—C13—H13B	109.5
C1—O1—P	123.55 (12)	C4—C13—H13C	109.5
N2—N1—C7	102.17 (15)	H13A—C13—H13C	109.5
N1—N2—N3	116.91 (16)	H13B—C13—H13C	109.5
N1—N2—C2	123.51 (16)	C15—C14—C19	119.22 (18)
N3—N2—C2	119.59 (15)	C15—C14—P	123.30 (13)
N2—N3—C12	102.88 (15)	C19—C14—P	117.40 (16)
C2—C1—C6	119.13 (19)	C14—C15—C16	120.55 (19)
C2—C1—O1	118.37 (16)	C14—C15—H15A	119.7
C6—C1—O1	122.45 (18)	C16—C15—H15A	119.7
C1—C2—C3	120.14 (18)	C17—C16—C15	119.5 (2)
C1—C2—N2	121.79 (16)	C17—C16—H16A	120.3
C3—C2—N2	117.97 (18)	C15—C16—H16A	120.3
C4—C3—C2	121.0 (2)	C18—C17—C16	120.3 (2)
C4—C3—H3B	119.5	C18—C17—H17A	119.8
C2—C3—H3B	119.5	C16—C17—H17A	119.8
C5—C4—C3	118.1 (2)	C17—C18—C19	120.8 (2)
C5—C4—C13	120.9 (2)	C17—C18—H18A	119.6
C3—C4—C13	121.0 (3)	C19—C18—H18A	119.6
C4—C5—C6	122.0 (2)	C18—C19—C14	119.6 (2)
C4—C5—H5A	119.0	C18—C19—H19A	120.2
C6—C5—H5A	119.0	C14—C19—H19A	120.2
C5—C6—C1	119.7 (2)	C25—C20—C21	119.38 (18)
C5—C6—H6A	120.2	C25—C20—P	122.57 (13)
C1—C6—H6A	120.2	C21—C20—P	118.05 (15)
N1—C7—C12	109.42 (16)	C22—C21—C20	119.3 (2)
N1—C7—C8	129.50 (19)	C22—C21—H21A	120.3
C12—C7—C8	121.07 (18)	C20—C21—H21A	120.3
C9—C8—C7	116.0 (2)	C23—C22—C21	120.7 (2)
C9—C8—H8A	122.0	C23—C22—H22A	119.7
C7—C8—H8A	122.0	C21—C22—H22A	119.7
C8—C9—C10	122.6 (2)	C22—C23—C24	120.4 (2)
C8—C9—H9A	118.7	C22—C23—H23A	119.8
C10—C9—H9A	118.7	C24—C23—H23A	119.8
C11—C10—C9	122.2 (2)	C23—C24—C25	120.1 (2)
C11—C10—H10A	118.9	C23—C24—H24A	119.9
C9—C10—H10A	118.9	C25—C24—H24A	119.9
C10—C11—C12	116.5 (2)	C24—C25—C20	119.98 (19)
C10—C11—H11A	121.7	C24—C25—H25A	120.0
C12—C11—H11A	121.7	C20—C25—H25A	120.0
O2—P—O1—C1	69.76 (16)	N1—C7—C12—N3	0.0 (2)
C14—P—O1—C1	−167.96 (14)	C8—C7—C12—N3	179.2 (2)
C20—P—O1—C1	−54.64 (15)	N1—C7—C12—C11	179.55 (19)
C7—N1—N2—N3	−0.5 (2)	C8—C7—C12—C11	−1.2 (3)
C7—N1—N2—C2	179.47 (16)	C10—C11—C12—N3	−179.2 (2)
N1—N2—N3—C12	0.5 (2)	C10—C11—C12—C7	1.3 (3)
C2—N2—N3—C12	−179.50 (16)	O2—P—C14—C15	169.14 (18)
P—O1—C1—C2	145.53 (15)	O1—P—C14—C15	45.41 (19)
P—O1—C1—C6	−36.9 (2)	C20—P—C14—C15	−64.59 (19)
C6—C1—C2—C3	2.4 (3)	O2—P—C14—C19	−14.0 (2)
O1—C1—C2—C3	−179.93 (17)	O1—P—C14—C19	−137.76 (18)
C6—C1—C2—N2	−174.01 (18)	C20—P—C14—C19	112.24 (19)
O1—C1—C2—N2	3.7 (3)	C19—C14—C15—C16	−0.2 (3)
N1—N2—C2—C1	−47.2 (3)	P—C14—C15—C16	176.57 (17)
N3—N2—C2—C1	132.8 (2)	C14—C15—C16—C17	0.7 (4)
N1—N2—C2—C3	136.33 (19)	C15—C16—C17—C18	−1.6 (4)
N3—N2—C2—C3	−43.7 (2)	C16—C17—C18—C19	2.1 (5)
C1—C2—C3—C4	−0.9 (3)	C17—C18—C19—C14	−1.6 (5)
N2—C2—C3—C4	175.64 (18)	C15—C14—C19—C18	0.6 (4)
C2—C3—C4—C5	−1.0 (3)	P—C14—C19—C18	−176.3 (2)
C2—C3—C4—C13	−179.0 (2)	O2—P—C20—C25	−151.46 (15)
C3—C4—C5—C6	1.4 (4)	O1—P—C20—C25	−25.08 (17)
C13—C4—C5—C6	179.3 (3)	C14—P—C20—C25	81.63 (17)
C4—C5—C6—C1	0.1 (4)	O2—P—C20—C21	29.44 (18)
C2—C1—C6—C5	−2.0 (3)	O1—P—C20—C21	155.82 (14)
O1—C1—C6—C5	−179.60 (18)	C14—P—C20—C21	−97.47 (16)
N2—N1—C7—C12	0.33 (19)	C25—C20—C21—C22	1.0 (3)
N2—N1—C7—C8	−178.8 (2)	P—C20—C21—C22	−179.91 (17)
N1—C7—C8—C9	179.6 (2)	C20—C21—C22—C23	1.2 (3)
C12—C7—C8—C9	0.6 (3)	C21—C22—C23—C24	−1.4 (4)
C7—C8—C9—C10	0.0 (4)	C22—C23—C24—C25	−0.6 (4)
C8—C9—C10—C11	0.2 (5)	C23—C24—C25—C20	2.7 (3)
C9—C10—C11—C12	−0.8 (4)	C21—C20—C25—C24	−2.9 (3)
N2—N3—C12—C7	−0.3 (2)	P—C20—C25—C24	178.04 (16)
N2—N3—C12—C11	−179.8 (2)

Table 1

Selected bond angles (°)

O2—P—O1	115.53 (10)
O2—P—C14	113.48 (8)
O1—P—C14	100.15 (8)
O2—P—C20	112.37 (9)
O1—P—C20	105.04 (8)
C14—P—C20	109.30 (8)