Diethyl [hydr-oxy(2-nitro-phen-yl)-meth-yl]phospho-nate.

In the title mol-ecule, C(11)H(16)NO(6)P, the nitro group is twisted out of the mean plane of the benzene ring at 29.91 (3)°. The two ethyl groups are disordered between two orientations in the ratios 0.784 (7)/0.216 (7) and 0.733 (6)/0.267 (6). Inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For general background, see: Allen et al. (1978 ▶); Hirschmann et al. (1994 ▶).

Experimental

Crystal data

C11H16NO6P

M = 289.22

Triclinic,

a = 7.5659 (13) Å

b = 8.3844 (15) Å

c = 12.557 (2) Å

α = 73.356 (3)°

β = 87.391 (3)°

γ = 64.432 (3)°

V = 685.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 291 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: none

6168 measured reflections

2800 independent reflections

2381 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.157

S = 1.05

2800 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063453/cv2361sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063453/cv2361Isup2.hkl

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

C11H16NO6P	Z = 2
Mr = 289.22	F000 = 304
Triclinic, P1	Dx = 1.401 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.5659 (13) Å	Cell parameters from 3014 reflections
b = 8.3844 (15) Å	θ = 2.8–28.0º
c = 12.557 (2) Å	µ = 0.22 mm−1
α = 73.356 (3)º	T = 291 (2) K
β = 87.391 (3)º	Block, colourless
γ = 64.432 (3)º	0.30 × 0.20 × 0.20 mm
V = 685.6 (2) Å3

Bruker SMART 4K CCD area-detector diffractometer	2381 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Monochromator: graphite	θmax = 26.5º
T = 291(2) K	θmin = 1.7º
φ and ω scans	h = −9→9
Absorption correction: none	k = −10→10
6168 measured reflections	l = −15→15
2800 independent reflections

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.157	w = 1/[σ2(Fo2) + (0.0955P)2 + 0.1438P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2800 reflections	Δρmax = 0.38 e Å−3
193 parameters	Δρmin = −0.20 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	Occ. (<1)
P1	0.33556 (9)	0.33802 (9)	0.13960 (4)	0.0648 (2)
C1	0.6327 (3)	0.2053 (3)	0.31083 (16)	0.0521 (4)
C2	0.5564 (3)	0.2596 (3)	0.40485 (16)	0.0548 (5)
C3	0.6201 (4)	0.1419 (3)	0.51225 (18)	0.0691 (6)
H3	0.5640	0.1819	0.5728	0.083*
C4	0.7655 (4)	−0.0332 (3)	0.5291 (2)	0.0760 (6)
H4	0.8103	−0.1125	0.6012	0.091*
C5	0.8460 (4)	−0.0924 (3)	0.4386 (2)	0.0782 (7)
H5	0.9455	−0.2115	0.4495	0.094*
C6	0.7784 (3)	0.0256 (3)	0.3323 (2)	0.0676 (5)
H6	0.8328	−0.0171	0.2723	0.081*
N1	0.4048 (3)	0.4469 (3)	0.39566 (16)	0.0673 (5)
C7	0.5651 (3)	0.3239 (3)	0.19053 (16)	0.0574 (5)
H7	0.5481	0.4491	0.1839	0.069*
C8	0.0059 (6)	0.5738 (7)	0.1961 (3)	0.0961 (13)	0.784 (7)
H8A	−0.0469	0.6001	0.1208	0.115*	0.784 (7)
H8B	0.0354	0.6744	0.1987	0.115*	0.784 (7)
C9	−0.1387 (9)	0.5585 (11)	0.2750 (7)	0.1132 (17)	0.784 (7)
H9A	−0.1731	0.4637	0.2688	0.170*	0.784 (7)
H9B	−0.2543	0.6746	0.2584	0.170*	0.784 (7)
H9C	−0.0833	0.5271	0.3496	0.170*	0.784 (7)
C10	0.2216 (8)	0.0840 (9)	0.1406 (5)	0.1275 (19)	0.733 (6)
H10A	0.1865	0.0309	0.2129	0.153*	0.733 (6)
H10B	0.1072	0.1975	0.1039	0.153*	0.733 (6)
C11	0.2598 (15)	−0.0343 (12)	0.0801 (5)	0.133 (2)	0.733 (6)
H11A	0.2744	0.0237	0.0046	0.199*	0.733 (6)
H11B	0.1531	−0.0677	0.0811	0.199*	0.733 (6)
H11C	0.3792	−0.1436	0.1115	0.199*	0.733 (6)
C8'	−0.024 (2)	0.471 (3)	0.2069 (13)	0.0961 (13)	0.216 (7)
H8C	−0.0615	0.5126	0.1274	0.115*	0.216 (7)
H8D	−0.0636	0.3735	0.2412	0.115*	0.216 (7)
C9'	−0.112 (4)	0.604 (4)	0.247 (3)	0.1132 (17)	0.216 (7)
H9D	−0.1637	0.5624	0.3148	0.170*	0.216 (7)
H9E	−0.2174	0.7016	0.1941	0.170*	0.216 (7)
H9F	−0.0209	0.6482	0.2619	0.170*	0.216 (7)
C10'	0.340 (2)	0.050 (2)	0.0838 (15)	0.1275 (19)	0.267 (6)
H10C	0.2555	0.1460	0.0194	0.153*	0.267 (6)
H10D	0.4623	−0.0245	0.0579	0.153*	0.267 (6)
C11'	0.254 (5)	−0.055 (4)	0.1332 (16)	0.133 (2)	0.267 (6)
H11D	0.3195	−0.1279	0.2064	0.199*	0.267 (6)
H11E	0.2613	−0.1348	0.0901	0.199*	0.267 (6)
H11F	0.1188	0.0221	0.1394	0.199*	0.267 (6)
O1	0.2928 (3)	0.4664 (3)	0.46827 (17)	0.0988 (6)
O2	0.3979 (3)	0.5760 (2)	0.31795 (16)	0.0925 (6)
O3	0.7091 (3)	0.2488 (3)	0.12000 (14)	0.0823 (5)
H3A	0.711 (6)	0.338 (3)	0.072 (2)	0.123*
O4	0.2695 (3)	0.4578 (3)	0.02454 (13)	0.0976 (7)
O5	0.1853 (2)	0.3993 (2)	0.22587 (12)	0.0713 (4)
O6	0.3792 (3)	0.1322 (3)	0.15899 (16)	0.0909 (6)

	U11	U22	U33	U12	U13	U23
P1	0.0644 (4)	0.0939 (5)	0.0463 (3)	−0.0471 (3)	0.0061 (2)	−0.0157 (3)
C1	0.0521 (10)	0.0583 (10)	0.0551 (10)	−0.0320 (8)	0.0044 (8)	−0.0172 (8)
C2	0.0544 (11)	0.0607 (11)	0.0555 (10)	−0.0299 (9)	0.0010 (8)	−0.0181 (8)
C3	0.0756 (15)	0.0867 (15)	0.0526 (11)	−0.0434 (13)	−0.0008 (10)	−0.0178 (10)
C4	0.0763 (15)	0.0768 (14)	0.0667 (14)	−0.0378 (13)	−0.0155 (11)	0.0005 (11)
C5	0.0650 (14)	0.0618 (12)	0.0967 (18)	−0.0248 (11)	−0.0065 (13)	−0.0101 (12)
C6	0.0627 (13)	0.0669 (12)	0.0765 (14)	−0.0292 (10)	0.0083 (10)	−0.0249 (11)
N1	0.0710 (12)	0.0710 (11)	0.0634 (11)	−0.0281 (9)	0.0009 (9)	−0.0288 (9)
C7	0.0570 (11)	0.0715 (12)	0.0523 (10)	−0.0357 (10)	0.0109 (8)	−0.0193 (9)
C8	0.069 (2)	0.089 (3)	0.091 (2)	−0.0168 (18)	0.0057 (17)	0.001 (2)
C9	0.070 (3)	0.132 (5)	0.152 (5)	−0.049 (2)	0.049 (3)	−0.061 (4)
C10	0.105 (4)	0.176 (5)	0.175 (5)	−0.095 (4)	0.042 (3)	−0.107 (4)
C11	0.192 (5)	0.146 (4)	0.114 (5)	−0.114 (4)	−0.006 (6)	−0.048 (5)
C8'	0.069 (2)	0.089 (3)	0.091 (2)	−0.0168 (18)	0.0057 (17)	0.001 (2)
C9'	0.070 (3)	0.132 (5)	0.152 (5)	−0.049 (2)	0.049 (3)	−0.061 (4)
C10'	0.105 (4)	0.176 (5)	0.175 (5)	−0.095 (4)	0.042 (3)	−0.107 (4)
C11'	0.192 (5)	0.146 (4)	0.114 (5)	−0.114 (4)	−0.006 (6)	−0.048 (5)
O1	0.0921 (14)	0.1054 (14)	0.0858 (12)	−0.0239 (11)	0.0255 (11)	−0.0433 (11)
O2	0.1164 (16)	0.0613 (9)	0.0886 (12)	−0.0296 (10)	0.0086 (11)	−0.0210 (9)
O3	0.0725 (11)	0.1066 (14)	0.0690 (10)	−0.0401 (10)	0.0278 (8)	−0.0296 (9)
O4	0.0928 (13)	0.1595 (19)	0.0495 (9)	−0.0782 (13)	0.0003 (8)	−0.0059 (10)
O5	0.0563 (9)	0.0873 (10)	0.0569 (8)	−0.0282 (8)	0.0041 (7)	−0.0067 (7)
O6	0.0959 (14)	0.1074 (14)	0.1021 (14)	−0.0641 (12)	0.0083 (10)	−0.0463 (11)

P1—O4	1.4653 (18)	C9—H9B	0.9600
P1—O6	1.556 (2)	C9—H9C	0.9600
P1—O5	1.5598 (16)	C10—C11	1.345 (9)
P1—C7	1.822 (2)	C10—O6	1.461 (5)
C1—C6	1.386 (3)	C10—H10A	0.9700
C1—C2	1.398 (3)	C10—H10B	0.9700
C1—C7	1.518 (3)	C11—H11A	0.9600
C2—C3	1.383 (3)	C11—H11B	0.9600
C2—N1	1.466 (3)	C11—H11C	0.9600
C3—C4	1.364 (4)	C8'—C9'	1.26 (3)
C3—H3	0.9300	C8'—O5	1.435 (15)
C4—C5	1.381 (4)	C8'—H8C	0.9700
C4—H4	0.9300	C8'—H8D	0.9700
C5—C6	1.375 (3)	C9'—H9D	0.9600
C5—H5	0.9300	C9'—H9E	0.9600
C6—H6	0.9300	C9'—H9F	0.9600
N1—O1	1.213 (3)	C10'—C11'	1.31 (3)
N1—O2	1.215 (3)	C10'—O6	1.426 (13)
C7—O3	1.417 (2)	C10'—H10C	0.9700
C7—H7	0.9800	C10'—H10D	0.9700
C8—O5	1.463 (4)	C11'—H11D	0.9600
C8—C9	1.465 (7)	C11'—H11E	0.9600
C8—H8A	0.9700	C11'—H11F	0.9600
C8—H8B	0.9700	O3—H3A	0.817 (10)
C9—H9A	0.9600
O4—P1—O6	115.38 (12)	H8A—C8—H8B	108.3
O4—P1—O5	114.16 (11)	C11—C10—O6	116.7 (6)
O6—P1—O5	103.70 (10)	C11—C10—H10A	108.1
O4—P1—C7	112.67 (10)	O6—C10—H10A	108.1
O6—P1—C7	103.71 (10)	C11—C10—H10B	108.1
O5—P1—C7	106.13 (9)	O6—C10—H10B	108.1
C6—C1—C2	115.53 (19)	H10A—C10—H10B	107.3
C6—C1—C7	118.91 (18)	C9'—C8'—O5	111 (2)
C2—C1—C7	125.53 (17)	C9'—C8'—H8C	109.4
C3—C2—C1	122.48 (19)	O5—C8'—H8C	109.4
C3—C2—N1	115.65 (18)	C9'—C8'—H8D	109.4
C1—C2—N1	121.86 (17)	O5—C8'—H8D	109.4
C4—C3—C2	119.8 (2)	H8C—C8'—H8D	108.0
C4—C3—H3	120.1	C8'—C9'—H9D	109.5
C2—C3—H3	120.1	C8'—C9'—H9E	109.5
C3—C4—C5	119.7 (2)	H9D—C9'—H9E	109.5
C3—C4—H4	120.2	C8'—C9'—H9F	109.5
C5—C4—H4	120.2	H9D—C9'—H9F	109.5
C6—C5—C4	119.7 (2)	H9E—C9'—H9F	109.5
C6—C5—H5	120.1	C11'—C10'—O6	110.4 (15)
C4—C5—H5	120.1	C11'—C10'—H10C	109.6
C5—C6—C1	122.8 (2)	O6—C10'—H10C	109.6
C5—C6—H6	118.6	C11'—C10'—H10D	109.6
C1—C6—H6	118.6	O6—C10'—H10D	109.6
O1—N1—O2	122.7 (2)	H10C—C10'—H10D	108.1
O1—N1—C2	117.8 (2)	C10'—C11'—H11D	109.5
O2—N1—C2	119.50 (19)	C10'—C11'—H11E	109.5
O3—C7—C1	109.76 (17)	H11D—C11'—H11E	109.5
O3—C7—P1	106.87 (14)	C10'—C11'—H11F	109.5
C1—C7—P1	113.49 (13)	H11D—C11'—H11F	109.5
O3—C7—H7	108.9	H11E—C11'—H11F	109.5
C1—C7—H7	108.9	C7—O3—H3A	106 (3)
P1—C7—H7	108.9	C8'—O5—P1	125.3 (7)
O5—C8—C9	109.0 (4)	C8—O5—P1	122.36 (19)
O5—C8—H8A	109.9	C10'—O6—C10	45.2 (6)
C9—C8—H8A	109.9	C10'—O6—P1	128.7 (8)
O5—C8—H8B	109.9	C10—O6—P1	120.3 (3)
C9—C8—H8B	109.9
C6—C1—C2—C3	−0.6 (3)	O6—P1—C7—C1	−56.38 (16)
C7—C1—C2—C3	177.55 (19)	O5—P1—C7—C1	52.54 (17)
C6—C1—C2—N1	178.54 (19)	C9'—C8'—O5—C8	−39.6 (17)
C7—C1—C2—N1	−3.3 (3)	C9'—C8'—O5—P1	−139.1 (16)
C1—C2—C3—C4	1.3 (3)	C9—C8—O5—C8'	49.1 (11)
N1—C2—C3—C4	−177.8 (2)	C9—C8—O5—P1	156.6 (4)
C2—C3—C4—C5	−0.9 (4)	O4—P1—O5—C8'	39.3 (10)
C3—C4—C5—C6	−0.2 (4)	O6—P1—O5—C8'	−87.1 (10)
C4—C5—C6—C1	1.0 (4)	C7—P1—O5—C8'	164.0 (10)
C2—C1—C6—C5	−0.6 (3)	O4—P1—O5—C8	−7.3 (3)
C7—C1—C6—C5	−178.8 (2)	O6—P1—O5—C8	−133.7 (3)
C3—C2—N1—O1	−29.3 (3)	C7—P1—O5—C8	117.4 (3)
C1—C2—N1—O1	151.6 (2)	C11'—C10'—O6—C10	−35.3 (18)
C3—C2—N1—O2	149.4 (2)	C11'—C10'—O6—P1	−131.9 (19)
C1—C2—N1—O2	−29.8 (3)	C11—C10—O6—C10'	16.3 (12)
C6—C1—C7—O3	−19.2 (2)	C11—C10—O6—P1	132.5 (6)
C2—C1—C7—O3	162.69 (18)	O4—P1—O6—C10'	−8.9 (8)
C6—C1—C7—P1	100.3 (2)	O5—P1—O6—C10'	116.7 (8)
C2—C1—C7—P1	−77.8 (2)	C7—P1—O6—C10'	−132.6 (8)
O4—P1—C7—O3	−60.70 (19)	O4—P1—O6—C10	−63.6 (3)
O6—P1—C7—O3	64.75 (16)	O5—P1—O6—C10	62.0 (3)
O5—P1—C7—O3	173.68 (13)	C7—P1—O6—C10	172.7 (3)
O4—P1—C7—C1	178.17 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4i	0.82 (1)	1.857 (11)	2.671 (3)	174 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4i	0.82 (1)	1.857 (11)	2.671 (3)	174 (4)

Symmetry code: (i) .