3-(6-Methyl-2-pyrid­yl)-2-phen­oxy-3,4-dihydro-1,3,2-benzoxaza­phosphirine 2-oxide

Kant, R.; Kohli, S.; Sarmal, L.; Krishnaiah, M.; Babu, V.H.H.S.

doi:10.1107/S1600536809029018

organic compounds

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Volume 65| Part 8| August 2009| Page o2003

doi:10.1107/S1600536809029018

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3-(6-Methyl-2-pyridyl)-2-phenoxy-3,4-dihydro-1,3,2-benzoxazaphosphirine 2-oxide

Rajni Kant,^a ^* Sabeta Kohli,^a Lovely Sarmal,^a M. Krishnaiah ^b and V. H. H. Surendra Babu ^b

^aDepartment of Physics, University of Jammu, Jammu Tawi 180 006, India, and ^bDepartment of Physics, S.V. University, Tirupati 517 502, India
^*Correspondence e-mail: rk_paper@rediffmail.com

(Received 26 June 2009; accepted 22 July 2009; online 25 July 2009)

In the title compound, C₁₉H₁₇N₂O₃P, the six-membered 1,3,2-oxazaphosphorine 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 interactions.

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_r = 352.33
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.149
S = 1.08
4922 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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⋯O2^iv	0.96	2.81	3.443 (3)	124
C18—H18⋯N2^iv	0.93	2.92	3.818 (5)	163
C10—H10⋯Cg2ⁱⁱⁱ	0.93	2.78	3.437 (2)	128
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) x+1, y, z; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg2 is the centroid of the N1,C1–C5 ring.

Data collection: CrysAlis Pro (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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 ).

Supporting information

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

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

checkCIF report

Comment top

Organophosphorus heterocycle compounds containing O and N in a six membered ring have gained much attention because of anti-cancer, anti-tumor and their most significant biological activities as pesticides and drugs(Riffel et al.1984, Kleemann et al.1985, Bettemann et al. 1987, He et al.1998).).

Various compounds of this class viz. cyclophosphamide(2-bis(2-chloroethyl)amino tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide),ifosfamide(3-(2-chloroethyl)-2-(2-chloroethylamino)tetrahydro-2H-1,3,1-oxazaphosphorine2-oxide) and trofosfamide(3-(2-chloroethyl)-2-(bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2oxazaphosphorine2-oxide) act as antitumor agents (Przybylski et al.,1977).

Because of these significant properties of organophosphorus heterocycle compounds a new compound of this class, i.e., 3-(6-methyl-pyrindin-2-yl)-2-phenoxy-3, 4-dihydrobenzo[e][1,3,2]oxazaphosphirine 2-oxide[I] has been synthesized and its crystal structure is reported here.

In the title compound, [C₁₉H₁₇ N₂O₃ P], the six membered oxazaphosphorine ring adopts a twist boat conformation with phosphoryl oxygen atom at equatorial position. The PO(3) bond length is 1.457 (1)Å and the average value of P—O distance is 1.588 Å. The crystal structure is stabilized by C—H···O and C—H···Π interactions.

Related literature top

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

Experimental top

The title compound was synthesized by adding a solution of phenylphosphorodichloridate (0.002 mole) in 25 ml of dry tetrahydrofuran dropwise over a period of twenty minutes to a stirred solution of 2-{[(6-methyl-2-pyridyl)amino]methyl}phenol (0.002 mole) and triethylamine (0.004 mole) in 30 ml of dry tetrahydrofuran at 0°C. After completion of the addition, the temperature of the reaction mixture was slowly raised to room temperature and stirred for 30 min. Later the reaction mixture was heated to 45–50°C and maintained at that temperature for three hours with stirring. Completion of the reaction was monitored by TLC analysis. Triethylamine- hydrochloride was separated from the reaction mixture by filtration and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (100–200 mesh) as adsorbent and ethyl acetate:hexane as eluent to afford pure product. Suitable colourless transparent rectangular crystals were obtained from 2-propanol by slow evaporation technique.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); 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).

Figures top

	Fig. 1. View of (I) (50% probability displacement ellipsoids)
	Fig. 2. Depiction of C—H..O interactions in the title compound(I)

3-(6-Methyl-2-pyridyl)-2-phenoxy-3,4-dihydro-1,3,2-benzoxazaphosphirine 2-oxide top

Crystal data top

C₁₉H₁₇N₂O₃P	F(000) = 736
M_r = 352.33	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0646P)² + 0.9398P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
4922 reflections	Δρ_max = 0.53 e Å⁻³
227 parameters	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₉H₁₇N₂O₃P	V = 1714.8 (2) Å³
M_r = 352.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2852 (7) Å	µ = 0.18 mm⁻¹
b = 14.2972 (11) Å	T = 293 K
c = 13.3446 (8) Å	0.30 × 0.24 × 0.18 mm
β = 104.545 (7)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	4064 reflections with I > 2σ(I)
14565 measured reflections	R_int = 0.017
4922 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.08	Δρ_max = 0.53 e Å⁻³
4922 reflections	Δρ_min = −0.35 e Å⁻³
227 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.96	2.81	3.443 (3)	124
C18—H18···N2^iv	0.93	2.92	3.818 (5)	163
C10—H10···Cg2ⁱⁱⁱ	0.93	2.78	3.437 (2)	128

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y+1, −z; (iii) x+1, y, z; (iv) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇N₂O₃P
M_r	352.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.2852 (7), 14.2972 (11), 13.3446 (8)
β (°)	104.545 (7)
V (Å³)	1714.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.30 × 0.24 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14565, 4922, 4064
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.149, 1.08
No. of reflections	4922
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.35

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.96	2.81	3.443 (3)	124
C18—H18···N2^iv	0.93	2.92	3.818 (5)	163
C10—H10···Cg2ⁱⁱⁱ	0.93	2.78	3.437 (2)	128

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y+1, −z; (iii) x+1, y, z; (iv) −x, y+1/2, −z+1/2.

Acknowledgements

The authors are grateful to the Department of Science and Technology of the Government of India for funding under research project SR/S2/CMP-47/2003.

References

Bettemann, G., Look, P. & Schomburg, D. (1987). Phosphorus Sulfur, 30, 499–502. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
He, L., Zhuo, R., Cai, F. & Lu, A. (1998). Wuhan Univ. J. Nat. Sci. 3, 126–128. CAS Google Scholar
Kleemann, S. & Fluck, E. (1985). Z. Anorg. Allg. Chem. 562, 141–144. CrossRef Web of Science Google Scholar
Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Przybylski, M., Ringsdorf, H., Lenssen, U., Peter, G., Voelcker, G., Wagner, T. & Hohorst, H. J. (1977). Biomed. Mass Spectr. 4, 209–215. CrossRef CAS Web of Science Google Scholar
Riffel, H., Kleemam, S. & Hess, H. (1984). Z. Anorg. Allg. Chem. 508, 61–72. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Page o2003

doi:10.1107/S1600536809029018

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-(6-Methyl-2-pyrid­yl)-2-phen­­oxy-3,4-di­hydro-1,3,2-benzoxaza­phosphirine 2-oxide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(6-Methyl-2-pyridyl)-2-phenoxy-3,4-dihydro-1,3,2-benzoxazaphosphirine 2-oxide