2-Methyl-1,3-benzoxazol-4-yl diphenyl-phosphinate.

The title compound, C(20)H(16)NO(3)P, was synthesized by the addition of diphenyl-phosphine chloride to a tetra-hydro-furan solution of Et(3)N and 2-methyl-1,3-benzoxazol-4-ol at 233 K. In the mol-ecule, the almost planar (r.m.s. deviation = 0.010 Å) benzoxazole moiety is attached to the slightly distorted tetra-hedral P atom [C-P-C-C torsion angle = 132.20 (18)°]. The crystal structure does not exhibit any significant inter-molecular inter-actions.

Related literature

For reference structural data, see: Bruno et al. (2004 ▶). For related benzoxazole structures, see: Dreher et al. (1982 ▶); Mrozek et al. (1999 ▶); Qu et al. (2008 ▶).

Experimental

Crystal data

C20H16NO3P

M = 349.31

Orthorhombic,

a = 9.4239 (4) Å

b = 15.7574 (6) Å

c = 23.5398 (8) Å

V = 3495.6 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.18 mm−1

T = 294 K

0.39 × 0.28 × 0.19 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.934, T max = 0.968

17406 measured reflections

4323 independent reflections

2395 reflections with I > 2sI)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.119

S = 1.01

4323 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶; Atwood & Barbour, 2003 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000420/bh2332sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000420/bh2332Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H16NO3P	F(000) = 1456
Mr = 349.31	Dx = 1.327 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2232 reflections
a = 9.4239 (4) Å	θ = 2.6–21.4°
b = 15.7574 (6) Å	µ = 0.18 mm−1
c = 23.5398 (8) Å	T = 294 K
V = 3495.6 (2) Å3	Shard, colourless
Z = 8	0.39 × 0.28 × 0.19 mm

Bruker APEX CCD area-detector diffractometer	4323 independent reflections
Radiation source: fine-focus sealed tube	2395 reflections with I > 2s˘I)
graphite	Rint = 0.048
ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→12
Tmin = 0.934, Tmax = 0.968	k = −20→20
17406 measured reflections	l = −31→27

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0424P)2 + 0.590P] where P = (Fo2 + 2Fc2)/3
4323 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.26 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	1.0692 (3)	0.38155 (17)	0.26208 (12)	0.0919 (9)
H1A	1.0661	0.4112	0.2977	0.138*
H1B	1.0397	0.4190	0.2321	0.138*
H1C	1.1643	0.3625	0.2549	0.138*
C2	0.9726 (2)	0.30737 (14)	0.26439 (10)	0.0637 (6)
O3	0.95849 (15)	0.26057 (10)	0.21540 (6)	0.0675 (5)
C4	0.8664 (2)	0.19615 (14)	0.22996 (9)	0.0542 (5)
C5	0.8185 (2)	0.13016 (16)	0.19692 (9)	0.0648 (6)
H5	0.8464	0.1232	0.1593	0.078*
C6	0.7269 (2)	0.07556 (15)	0.22317 (10)	0.0665 (6)
H6	0.6905	0.0301	0.2026	0.080*
C7	0.6858 (2)	0.08550 (14)	0.28007 (9)	0.0599 (6)
H7	0.6227	0.0472	0.2964	0.072*
C8	0.7383 (2)	0.15153 (13)	0.31183 (8)	0.0505 (5)
C9	0.8305 (2)	0.20841 (12)	0.28635 (8)	0.0477 (5)
N10	0.89952 (18)	0.28056 (11)	0.30715 (7)	0.0575 (5)
O11	0.70042 (15)	0.16648 (8)	0.36812 (5)	0.0582 (4)
P12	0.66708 (6)	0.09284 (4)	0.41346 (2)	0.0517 (2)
C13	0.6671 (2)	0.15461 (13)	0.47700 (8)	0.0502 (5)
C14	0.5843 (2)	0.12659 (15)	0.52184 (9)	0.0617 (6)
H14	0.5311	0.0772	0.5180	0.074*
C15	0.5800 (2)	0.17110 (17)	0.57194 (9)	0.0698 (7)
H15	0.5233	0.1519	0.6016	0.084*
C16	0.6584 (2)	0.24348 (16)	0.57858 (10)	0.0678 (7)
H16	0.6545	0.2735	0.6126	0.081*
C17	0.7424 (3)	0.27171 (15)	0.53511 (11)	0.0726 (7)
H17	0.7968	0.3205	0.5398	0.087*
C18	0.7468 (3)	0.22806 (13)	0.48430 (9)	0.0639 (6)
H18	0.8035	0.2479	0.4548	0.077*
C19	0.8204 (2)	0.02618 (12)	0.41212 (8)	0.0505 (5)
C20	0.8072 (3)	−0.05892 (14)	0.39910 (10)	0.0702 (7)
H20	0.7181	−0.0814	0.3913	0.084*
C21	0.9249 (3)	−0.11072 (16)	0.39760 (12)	0.0866 (8)
H21	0.9150	−0.1678	0.3885	0.104*
C22	1.0558 (3)	−0.07849 (18)	0.40944 (11)	0.0839 (8)
H22	1.1348	−0.1139	0.4088	0.101*
C23	1.0718 (3)	0.00536 (19)	0.42221 (11)	0.0834 (8)
H23	1.1616	0.0272	0.4297	0.100*
C24	0.9548 (3)	0.05755 (15)	0.42402 (10)	0.0709 (7)
H24	0.9659	0.1145	0.4333	0.085*
O25	0.53499 (15)	0.04578 (9)	0.40384 (6)	0.0670 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0868 (19)	0.0779 (18)	0.111 (2)	−0.0161 (15)	0.0206 (16)	0.0018 (16)
C2	0.0600 (13)	0.0646 (14)	0.0665 (16)	0.0027 (12)	0.0041 (12)	0.0027 (13)
O3	0.0706 (10)	0.0740 (11)	0.0577 (10)	0.0022 (8)	0.0158 (8)	0.0062 (8)
C4	0.0541 (12)	0.0603 (13)	0.0482 (12)	0.0089 (10)	0.0040 (10)	0.0085 (11)
C5	0.0728 (15)	0.0778 (16)	0.0439 (12)	0.0118 (13)	0.0024 (11)	−0.0043 (12)
C6	0.0727 (15)	0.0687 (15)	0.0582 (14)	0.0022 (12)	−0.0032 (12)	−0.0118 (12)
C7	0.0651 (14)	0.0592 (14)	0.0555 (13)	−0.0002 (11)	0.0025 (10)	0.0012 (11)
C8	0.0595 (12)	0.0517 (12)	0.0403 (11)	0.0081 (10)	0.0028 (9)	0.0025 (10)
C9	0.0501 (11)	0.0517 (12)	0.0413 (11)	0.0090 (9)	−0.0010 (9)	0.0041 (9)
N10	0.0582 (11)	0.0588 (11)	0.0555 (11)	0.0024 (9)	0.0006 (9)	0.0028 (9)
O11	0.0817 (10)	0.0508 (8)	0.0422 (8)	0.0052 (7)	0.0118 (7)	0.0046 (6)
P12	0.0586 (4)	0.0516 (4)	0.0449 (4)	−0.0010 (3)	0.0046 (2)	0.0041 (2)
C13	0.0532 (11)	0.0504 (12)	0.0470 (12)	0.0049 (10)	0.0059 (9)	0.0031 (10)
C14	0.0590 (13)	0.0721 (15)	0.0538 (14)	−0.0065 (11)	0.0063 (10)	−0.0019 (12)
C15	0.0622 (14)	0.0961 (19)	0.0512 (14)	0.0002 (13)	0.0122 (11)	−0.0042 (13)
C16	0.0688 (15)	0.0790 (17)	0.0555 (14)	0.0165 (13)	0.0034 (11)	−0.0161 (12)
C17	0.0850 (17)	0.0587 (14)	0.0740 (17)	−0.0007 (13)	0.0058 (14)	−0.0115 (13)
C18	0.0788 (15)	0.0540 (13)	0.0589 (14)	−0.0003 (12)	0.0163 (11)	0.0014 (11)
C19	0.0635 (13)	0.0450 (11)	0.0432 (11)	−0.0031 (10)	0.0061 (9)	0.0025 (9)
C20	0.0791 (16)	0.0538 (14)	0.0777 (16)	−0.0058 (12)	0.0103 (12)	−0.0039 (12)
C21	0.109 (2)	0.0509 (15)	0.100 (2)	0.0125 (15)	0.0238 (17)	−0.0060 (14)
C22	0.091 (2)	0.080 (2)	0.0803 (18)	0.0298 (16)	0.0098 (15)	0.0116 (15)
C23	0.0668 (16)	0.088 (2)	0.095 (2)	0.0125 (15)	−0.0068 (14)	−0.0001 (16)
C24	0.0698 (15)	0.0566 (14)	0.0864 (18)	0.0029 (12)	−0.0041 (13)	−0.0074 (13)
O25	0.0622 (9)	0.0766 (11)	0.0620 (10)	−0.0109 (8)	−0.0011 (7)	0.0023 (8)

P12—C13	1.785 (2)	C5—C6	1.366 (3)
P12—C19	1.786 (2)	C5—H5	0.9300
P12—O11	1.6075 (14)	C24—C23	1.377 (3)
P12—O25	1.4665 (15)	C24—H24	0.9300
C19—C20	1.381 (3)	C18—C17	1.380 (3)
C19—C24	1.388 (3)	C18—H18	0.9300
O11—C8	1.392 (2)	C15—C14	1.373 (3)
C13—C14	1.385 (3)	C15—H15	0.9300
C13—C18	1.390 (3)	C14—H14	0.9300
C9—C4	1.383 (3)	C20—C21	1.378 (3)
C9—C8	1.385 (3)	C20—H20	0.9300
C9—N10	1.398 (2)	C6—H6	0.9300
O3—C2	1.375 (3)	C2—C1	1.483 (3)
O3—C4	1.379 (2)	C17—H17	0.9300
N10—C2	1.291 (3)	C21—C22	1.363 (4)
C8—C7	1.373 (3)	C21—H21	0.9300
C7—C6	1.403 (3)	C22—C23	1.363 (4)
C7—H7	0.9300	C22—H22	0.9300
C4—C5	1.375 (3)	C23—H23	0.9300
C16—C15	1.368 (3)	C1—H1A	0.9600
C16—C17	1.368 (3)	C1—H1B	0.9600
C16—H16	0.9300	C1—H1C	0.9600
C13—P12—C19	109.59 (9)	C17—C18—C13	120.4 (2)
O11—P12—C13	99.36 (8)	C17—C18—H18	119.8
O25—P12—C13	113.91 (9)	C13—C18—H18	119.8
O11—P12—C19	104.76 (8)	C16—C15—C14	120.6 (2)
O25—P12—C19	112.73 (9)	C16—C15—H15	119.7
O25—P12—O11	115.37 (8)	C14—C15—H15	119.7
C20—C19—C24	118.2 (2)	C15—C14—C13	120.5 (2)
C20—C19—P12	120.14 (17)	C15—C14—H14	119.7
C24—C19—P12	121.66 (16)	C13—C14—H14	119.7
C8—O11—P12	124.04 (13)	C21—C20—C19	120.6 (2)
C14—C13—C18	118.41 (19)	C21—C20—H20	119.7
C14—C13—P12	117.69 (16)	C19—C20—H20	119.7
C18—C13—P12	123.90 (15)	C5—C6—C7	122.4 (2)
C4—C9—C8	118.61 (19)	C5—C6—H6	118.8
C4—C9—N10	109.61 (18)	C7—C6—H6	118.8
C8—C9—N10	131.78 (18)	N10—C2—O3	115.3 (2)
C2—O3—C4	104.30 (16)	N10—C2—C1	127.9 (2)
C2—N10—C9	103.96 (18)	O3—C2—C1	116.8 (2)
C7—C8—C9	118.71 (18)	C16—C17—C18	120.2 (2)
C7—C8—O11	123.65 (19)	C16—C17—H17	119.9
C9—C8—O11	117.61 (18)	C18—C17—H17	119.9
C8—C7—C6	120.3 (2)	C22—C21—C20	120.2 (2)
C8—C7—H7	119.8	C22—C21—H21	119.9
C6—C7—H7	119.8	C20—C21—H21	119.9
C5—C4—O3	128.53 (19)	C21—C22—C23	120.4 (3)
C5—C4—C9	124.6 (2)	C21—C22—H22	119.8
O3—C4—C9	106.86 (19)	C23—C22—H22	119.8
C15—C16—C17	119.9 (2)	C22—C23—C24	119.8 (3)
C15—C16—H16	120.1	C22—C23—H23	120.1
C17—C16—H16	120.1	C24—C23—H23	120.1
C6—C5—C4	115.3 (2)	C2—C1—H1A	109.5
C6—C5—H5	122.3	C2—C1—H1B	109.5
C4—C5—H5	122.3	H1A—C1—H1B	109.5
C23—C24—C19	120.8 (2)	C2—C1—H1C	109.5
C23—C24—H24	119.6	H1A—C1—H1C	109.5
C19—C24—H24	119.6	H1B—C1—H1C	109.5
O25—P12—C19—C20	4.2 (2)	N10—C9—C4—C5	179.05 (19)
O11—P12—C19—C20	−122.00 (18)	C8—C9—C4—O3	−179.84 (16)
C13—P12—C19—C20	132.20 (18)	N10—C9—C4—O3	0.2 (2)
O25—P12—C19—C24	−175.71 (17)	O3—C4—C5—C6	−179.98 (19)
O11—P12—C19—C24	58.08 (19)	C9—C4—C5—C6	1.4 (3)
C13—P12—C19—C24	−47.7 (2)	C20—C19—C24—C23	0.7 (3)
O25—P12—O11—C8	−70.10 (17)	P12—C19—C24—C23	−179.33 (18)
C13—P12—O11—C8	167.71 (15)	C14—C13—C18—C17	−0.2 (3)
C19—P12—O11—C8	54.45 (17)	P12—C13—C18—C17	−179.16 (17)
O25—P12—C13—C14	28.64 (19)	C17—C16—C15—C14	−0.3 (4)
O11—P12—C13—C14	151.88 (16)	C16—C15—C14—C13	−0.5 (3)
C19—P12—C13—C14	−98.69 (17)	C18—C13—C14—C15	0.8 (3)
O25—P12—C13—C18	−152.41 (17)	P12—C13—C14—C15	179.80 (17)
O11—P12—C13—C18	−29.17 (19)	C24—C19—C20—C21	−0.5 (3)
C19—P12—C13—C18	80.26 (19)	P12—C19—C20—C21	179.57 (19)
C4—C9—N10—C2	−0.6 (2)	C4—C5—C6—C7	−0.7 (3)
C8—C9—N10—C2	179.4 (2)	C8—C7—C6—C5	−0.4 (3)
C4—C9—C8—C7	−0.2 (3)	C9—N10—C2—O3	0.9 (2)
N10—C9—C8—C7	179.73 (19)	C9—N10—C2—C1	−178.8 (2)
C4—C9—C8—O11	−178.21 (17)	C4—O3—C2—N10	−0.8 (2)
N10—C9—C8—O11	1.8 (3)	C4—O3—C2—C1	178.93 (19)
P12—O11—C8—C7	34.9 (3)	C15—C16—C17—C18	0.9 (4)
P12—O11—C8—C9	−147.28 (15)	C13—C18—C17—C16	−0.6 (3)
C9—C8—C7—C6	0.9 (3)	C19—C20—C21—C22	0.5 (4)
O11—C8—C7—C6	178.74 (19)	C20—C21—C22—C23	−0.8 (4)
C2—O3—C4—C5	−178.5 (2)	C21—C22—C23—C24	1.0 (4)
C2—O3—C4—C9	0.3 (2)	C19—C24—C23—C22	−1.0 (4)
C8—C9—C4—C5	−1.0 (3)

P12—C13	1.785 (2)
P12—C19	1.786 (2)
P12—O11	1.6075 (14)
P12—O25	1.4665 (15)

C13—P12—C19	109.59 (9)
O11—P12—C13	99.36 (8)
O25—P12—C13	113.91 (9)
O11—P12—C19	104.76 (8)
O25—P12—C19	112.73 (9)
O25—P12—O11	115.37 (8)