3-(6-Methyl-2-pyrid-yl)-2-phen-oxy-3,4-dihydro-1,3,2-benzoxaza-phosphirine 2-oxide.

In the title compound, C(19)H(17)N(2)O(3)P, the six-membered 1,3,2-oxaza-phospho-rine ring adopts a twist-boat conformation with the phosphoryl O atom in an equatorial position. The P=O(oxide) bond length is 1.457 (1) Å and the average value of the P-O distances is 1.588 Å. The crystal structure is stabilized by C-H⋯O and C-H⋯π inter-actions.

Related literature

For the chemistry of organophospho­rus heterocyclic compounds, see: Przybylski et al. (1977 ▶); Riffel et al. (1984 ▶); Kleemann & Fluck (1985 ▶); Bettemann et al. (1987 ▶); He et al. (1998 ▶).

Experimental

Crystal data

C19H17N2O3P

M = 352.33

Monoclinic,

a = 9.2852 (7) Å

b = 14.2972 (11) Å

c = 13.3446 (8) Å

β = 104.545 (7)°

V = 1714.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.30 × 0.24 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: none

14565 measured reflections

4922 independent reflections

4064 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.149

S = 1.08

4922 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029018/jh2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029018/jh2088Isup2.hkl

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

C19H17N2O3P	F(000) = 736
Mr = 352.33	Dx = 1.365 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4064 reflections
a = 9.2852 (7) Å	θ = 3.2–30.1°
b = 14.2972 (11) Å	µ = 0.18 mm−1
c = 13.3446 (8) Å	T = 293 K
β = 104.545 (7)°	Rectangular, colourless
V = 1714.8 (2) Å3	0.30 × 0.24 × 0.18 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer	Rint = 0.017
ω–2θ scans	θmax = 30.1°, θmin = 3.2°
14565 measured reflections	h = −13→13
4922 independent reflections	k = −19→20
4064 reflections with I > 2σ(I)	l = −18→18

Refinement on F2	0 restraints
Least-squares matrix: full	0 constraints
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0646P)2 + 0.9398P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
4922 reflections	Δρmax = 0.53 e Å−3
227 parameters	Δρmin = −0.35 e Å−3

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.

	x	y	z	Uiso*/Ueq
O3	0.05137 (15)	0.29221 (11)	0.30611 (10)	0.0431 (3)
P1	0.15450 (5)	0.32614 (3)	0.24817 (3)	0.03212 (13)
O2	0.29805 (14)	0.26052 (10)	0.27286 (10)	0.0408 (3)
N2	0.10589 (16)	0.32584 (11)	0.11909 (11)	0.0342 (3)
N1	−0.08432 (16)	0.42593 (11)	0.12856 (11)	0.0366 (3)
O1	0.22025 (15)	0.42756 (10)	0.27690 (10)	0.0409 (3)
C4	−0.0855 (2)	0.36620 (14)	−0.04067 (13)	0.0391 (4)
H4	−0.0437	0.3271	−0.0814	0.047*
C13	0.40587 (19)	0.26785 (13)	0.21602 (14)	0.0358 (4)
C5	−0.02466 (18)	0.37381 (12)	0.06657 (13)	0.0320 (3)
C8	0.35786 (19)	0.27514 (13)	0.10910 (14)	0.0363 (4)
C3	−0.2102 (2)	0.41944 (15)	−0.08287 (15)	0.0450 (4)
H3	−0.2522	0.4182	−0.1539	0.054*
C2	−0.2726 (2)	0.47435 (15)	−0.02010 (17)	0.0471 (5)
H2	−0.3565	0.5103	−0.0482	0.057*
C9	0.4650 (2)	0.27788 (16)	0.05260 (15)	0.0439 (4)
H9	0.436	0.2836	−0.0191	0.053*
C1	−0.2078 (2)	0.47521 (14)	0.08637 (16)	0.0414 (4)
C11	0.6595 (2)	0.26582 (18)	0.21010 (19)	0.0546 (5)
H11	0.7603	0.2627	0.2432	0.065*
C14	0.2129 (2)	0.47435 (14)	0.36794 (15)	0.0417 (4)
C7	0.1947 (2)	0.27754 (18)	0.05690 (16)	0.0496 (5)
H7A	0.1803	0.309	−0.0093	0.06*
H7B	0.1586	0.2139	0.0436	0.06*
C10	0.6146 (2)	0.27217 (16)	0.10275 (18)	0.0482 (5)
H10	0.6856	0.2726	0.0644	0.058*
C12	0.5546 (2)	0.26421 (17)	0.26780 (16)	0.0499 (5)
H12	0.5836	0.2608	0.3397	0.06*
C19	0.1181 (3)	0.5491 (2)	0.3572 (3)	0.0860 (10)
H19	0.0597	0.5665	0.2926	0.103*
C6	−0.2732 (3)	0.5295 (2)	0.1604 (2)	0.0663 (7)
H6A	−0.2875	0.4887	0.2143	0.099*
H6B	−0.3673	0.5554	0.1241	0.099*
H6C	−0.2068	0.5792	0.1904	0.099*
C16	0.2972 (7)	0.5017 (3)	0.5483 (3)	0.1263 (18)
H16	0.3597	0.4863	0.6122	0.152*
C18	0.1120 (5)	0.5980 (3)	0.4456 (5)	0.136 (2)
H18	0.0477	0.6486	0.4405	0.163*
C17	0.2005 (7)	0.5726 (4)	0.5416 (4)	0.131 (2)
H17	0.1929	0.6044	0.6008	0.157*
C15	0.3051 (4)	0.4509 (2)	0.4605 (2)	0.0841 (10)
H15	0.3724	0.4019	0.4653	0.101*

	U11	U22	U33	U12	U13	U23
O3	0.0409 (7)	0.0518 (8)	0.0405 (7)	−0.0031 (6)	0.0173 (5)	0.0077 (6)
P1	0.0333 (2)	0.0364 (2)	0.0278 (2)	−0.00139 (17)	0.00979 (15)	0.00310 (16)
O2	0.0383 (6)	0.0486 (8)	0.0376 (6)	0.0065 (6)	0.0135 (5)	0.0127 (6)
N2	0.0328 (7)	0.0418 (8)	0.0282 (6)	0.0032 (6)	0.0079 (5)	−0.0012 (6)
N1	0.0345 (7)	0.0399 (8)	0.0352 (7)	0.0003 (6)	0.0083 (6)	−0.0003 (6)
O1	0.0492 (7)	0.0427 (7)	0.0329 (6)	−0.0091 (6)	0.0145 (5)	−0.0034 (5)
C4	0.0400 (9)	0.0458 (10)	0.0310 (8)	−0.0047 (8)	0.0080 (7)	0.0007 (7)
C13	0.0346 (8)	0.0349 (8)	0.0392 (8)	0.0019 (7)	0.0117 (7)	0.0049 (7)
C5	0.0308 (7)	0.0337 (8)	0.0314 (7)	−0.0042 (6)	0.0078 (6)	0.0019 (6)
C8	0.0342 (8)	0.0379 (9)	0.0377 (8)	0.0003 (7)	0.0107 (7)	−0.0025 (7)
C3	0.0459 (10)	0.0507 (11)	0.0339 (9)	−0.0058 (8)	0.0018 (7)	0.0082 (8)
C2	0.0395 (10)	0.0432 (10)	0.0534 (11)	0.0020 (8)	0.0017 (8)	0.0109 (9)
C9	0.0438 (10)	0.0511 (11)	0.0397 (9)	0.0029 (8)	0.0160 (8)	−0.0003 (8)
C1	0.0385 (9)	0.0375 (9)	0.0475 (10)	0.0004 (7)	0.0096 (7)	0.0000 (8)
C11	0.0326 (9)	0.0686 (15)	0.0609 (13)	0.0015 (9)	0.0089 (9)	0.0047 (11)
C14	0.0473 (10)	0.0404 (10)	0.0404 (9)	−0.0088 (8)	0.0165 (8)	−0.0073 (8)
C7	0.0351 (9)	0.0737 (15)	0.0393 (9)	0.0042 (9)	0.0081 (7)	−0.0191 (10)
C10	0.0389 (9)	0.0512 (12)	0.0597 (12)	−0.0003 (8)	0.0221 (9)	0.0022 (10)
C12	0.0397 (10)	0.0657 (14)	0.0419 (10)	0.0061 (9)	0.0055 (8)	0.0082 (9)
C19	0.0632 (16)	0.077 (2)	0.114 (3)	0.0136 (15)	0.0152 (16)	−0.0319 (19)
C6	0.0618 (14)	0.0702 (17)	0.0664 (15)	0.0237 (13)	0.0150 (12)	−0.0107 (13)
C16	0.220 (5)	0.113 (3)	0.0428 (15)	−0.033 (4)	0.028 (2)	−0.0242 (19)
C18	0.104 (3)	0.113 (3)	0.209 (6)	−0.006 (3)	0.075 (4)	−0.095 (4)
C17	0.190 (5)	0.115 (3)	0.124 (4)	−0.075 (4)	0.104 (4)	−0.083 (3)
C15	0.129 (3)	0.0735 (18)	0.0397 (12)	0.0134 (18)	0.0022 (14)	−0.0051 (12)

O3—P1	1.4567 (13)	C1—C6	1.500 (3)
P1—O1	1.5825 (14)	C11—C12	1.385 (3)
P1—O2	1.5953 (14)	C11—C10	1.391 (3)
P1—N2	1.6675 (14)	C11—H11	0.93
O2—C13	1.404 (2)	C14—C15	1.356 (3)
N2—C5	1.416 (2)	C14—C19	1.369 (4)
N2—C7	1.479 (2)	C7—H7A	0.97
N1—C5	1.333 (2)	C7—H7B	0.97
N1—C1	1.343 (2)	C10—H10	0.93
O1—C14	1.404 (2)	C12—H12	0.93
C4—C3	1.382 (3)	C19—C18	1.385 (5)
C4—C5	1.405 (2)	C19—H19	0.93
C4—H4	0.93	C6—H6A	0.96
C13—C12	1.381 (3)	C6—H6B	0.96
C13—C8	1.388 (2)	C6—H6C	0.96
C8—C9	1.391 (2)	C16—C17	1.342 (7)
C8—C7	1.501 (3)	C16—C15	1.396 (5)
C3—C2	1.377 (3)	C16—H16	0.93
C3—H3	0.93	C18—C17	1.384 (8)
C2—C1	1.397 (3)	C18—H18	0.93
C2—H2	0.93	C17—H17	0.93
C9—C10	1.385 (3)	C15—H15	0.93
C9—H9	0.93
O3—P1—O1	116.20 (8)	C10—C11—H11	119.9
O3—P1—O2	108.72 (8)	C15—C14—C19	122.0 (3)
O1—P1—O2	103.73 (8)	C15—C14—O1	120.9 (2)
O3—P1—N2	120.26 (8)	C19—C14—O1	116.8 (2)
O1—P1—N2	103.92 (7)	N2—C7—C8	112.96 (15)
O2—P1—N2	101.96 (7)	N2—C7—H7A	109
C13—O2—P1	121.11 (11)	C8—C7—H7A	109
C5—N2—C7	118.48 (14)	N2—C7—H7B	109
C5—N2—P1	119.09 (12)	C8—C7—H7B	109
C7—N2—P1	122.43 (12)	H7A—C7—H7B	107.8
C5—N1—C1	118.50 (15)	C9—C10—C11	120.42 (18)
C14—O1—P1	123.14 (12)	C9—C10—H10	119.8
C3—C4—C5	117.00 (18)	C11—C10—H10	119.8
C3—C4—H4	121.5	C13—C12—C11	118.40 (19)
C5—C4—H4	121.5	C13—C12—H12	120.8
C12—C13—C8	122.67 (17)	C11—C12—H12	120.8
C12—C13—O2	119.08 (16)	C14—C19—C18	117.9 (4)
C8—C13—O2	118.21 (15)	C14—C19—H19	121
N1—C5—C4	123.51 (16)	C18—C19—H19	121
N1—C5—N2	113.65 (14)	C1—C6—H6A	109.5
C4—C5—N2	122.83 (16)	C1—C6—H6B	109.5
C13—C8—C9	118.07 (16)	H6A—C6—H6B	109.5
C13—C8—C7	120.34 (16)	C1—C6—H6C	109.5
C9—C8—C7	121.58 (17)	H6A—C6—H6C	109.5
C2—C3—C4	120.22 (18)	H6B—C6—H6C	109.5
C2—C3—H3	119.9	C17—C16—C15	120.8 (4)
C4—C3—H3	119.9	C17—C16—H16	119.6
C3—C2—C1	118.98 (18)	C15—C16—H16	119.6
C3—C2—H2	120.5	C17—C18—C19	120.9 (4)
C1—C2—H2	120.5	C17—C18—H18	119.5
C10—C9—C8	120.23 (18)	C19—C18—H18	119.5
C10—C9—H9	119.9	C16—C17—C18	119.4 (3)
C8—C9—H9	119.9	C16—C17—H17	120.3
N1—C1—C2	121.71 (18)	C18—C17—H17	120.3
N1—C1—C6	116.08 (18)	C14—C15—C16	118.8 (4)
C2—C1—C6	122.20 (19)	C14—C15—H15	120.6
C12—C11—C10	120.19 (18)	C16—C15—H15	120.6
C12—C11—H11	119.9

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3i	0.93	2.57	3.497 (3)	174
C9—H9···O2i	0.93	2.82	3.706 (2)	159
C7—H7A···O3i	0.97	2.85	3.425 (2)	119
C3—H3···O1ii	0.93	2.81	3.373 (3)	120
C11—H11···O3iii	0.93	2.66	3.561 (2)	165
C6—H6C···O2iv	0.96	2.81	3.443 (3)	124
C18—H18···N2iv	0.93	2.92	3.818 (5)	163
C10—H10···Cg2iii	0.93	2.78	3.437 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3i	0.93	2.57	3.497 (3)	174
C9—H9⋯O2i	0.93	2.82	3.706 (2)	159
C7—H7A⋯O3i	0.97	2.85	3.425 (2)	119
C3—H3⋯O1ii	0.93	2.81	3.373 (3)	120
C11—H11⋯O3iii	0.93	2.66	3.561 (2)	165
C6—H6C⋯O2iv	0.96	2.81	3.443 (3)	124
C18—H18⋯N2iv	0.93	2.92	3.818 (5)	163
C10—H10⋯Cg2iii	0.93	2.78	3.437 (2)	128

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the N1,C1–C5 ring.