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

In the title compound, C(9)H(12)NO(6)P, intra-molecular C-H⋯O hydrogen bonds form five- and six-membered rings. In the crystal, inversion dimers lined by pairs of C-H⋯O hydrogen bonds occur with ring motifs R(2) (2)(10). The O atom of the hydr-oxy group behaves as an accepter and the benzene ring as donor. Adjacent dimers are connected through O-H⋯O links.

Related literature

For related structures, see: Acar et al. (2009 ▶); Tahir et al. (2007 ▶); Chen et al. (2008 ▶); Maliha et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H12NO6P

M = 261.17

Monoclinic,

a = 9.8685 (12) Å

b = 7.5081 (11) Å

c = 16.1052 (12) Å

β = 90.341 (1)°

V = 1193.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.26 × 0.20 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (MolEN; Fair, 1990 ▶) T min = 0.939, T max = 0.959

2222 measured reflections

2093 independent reflections

1873 reflections with I > 2σ(I)

R int = 0.017

3 standard reflections frequency: 120 min intensity decay: −1.6%

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.231

S = 1.00

2093 reflections

162 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1992 ▶); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005467/at2724sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005467/at2724Isup2.hkl

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

C9H12NO6P	F(000) = 544
Mr = 261.17	Dx = 1.454 Mg m−3
Monoclinic, P21/c	Melting point: 383 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.8685 (12) Å	Cell parameters from 25 reflections
b = 7.5081 (11) Å	θ = 11.7–21.0°
c = 16.1052 (12) Å	µ = 0.25 mm−1
β = 90.341 (1)°	T = 296 K
V = 1193.3 (2) Å3	Prismatic, brown
Z = 4	0.26 × 0.20 × 0.18 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.017
ω/2θ scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: ψ scan (MolEN; Fair, 1990)	h = −11→0
Tmin = 0.939, Tmax = 0.959	k = −8→0
2222 measured reflections	l = −19→19
2093 independent reflections	3 standard reflections every 120 min
1873 reflections with I > 2σ(I)	intensity decay: −1.6%

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)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.231	w = 1/[σ2(Fo2) + (0.199P)2 + 0.3221P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2093 reflections	Δρmax = 0.70 e Å−3
162 parameters	Δρmin = −0.50 e Å−3
0 restraints

Experimental. the structure was solved by Patterson method using SHELX86 (Sheldrick, 2008); the whole molecule was recognized

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

	x	y	z	Uiso*/Ueq
P1	0.11199 (7)	0.14188 (9)	0.16915 (4)	0.0429 (3)
O1	0.0588 (2)	0.4641 (3)	0.12234 (12)	0.0541 (7)
O2	0.4424 (3)	0.3284 (5)	0.20368 (16)	0.0854 (12)
O3	0.5644 (3)	0.1418 (5)	0.1375 (2)	0.0989 (14)
O4	0.0391 (2)	0.1450 (3)	0.24822 (14)	0.0574 (8)
O5	0.0264 (2)	0.0741 (3)	0.09399 (13)	0.0590 (8)
O6	0.2419 (2)	0.0229 (3)	0.16653 (17)	0.0679 (9)
N1	0.4732 (2)	0.2487 (4)	0.14047 (16)	0.0590 (9)
C1	0.2651 (3)	0.3507 (3)	0.06417 (15)	0.0380 (8)
C2	0.3983 (3)	0.2905 (4)	0.06340 (16)	0.0449 (8)
C3	0.4703 (3)	0.2673 (5)	−0.0095 (2)	0.0580 (10)
C4	0.4101 (4)	0.3092 (5)	−0.08461 (19)	0.0639 (11)
C5	0.2801 (3)	0.3732 (5)	−0.08579 (19)	0.0590 (11)
C6	0.2083 (3)	0.3926 (4)	−0.01258 (16)	0.0485 (9)
C7	0.1759 (3)	0.3618 (3)	0.14019 (16)	0.0394 (8)
C8	−0.1193 (4)	0.0865 (7)	0.0912 (3)	0.0860 (16)
C9	0.2422 (4)	−0.1632 (5)	0.1836 (3)	0.0822 (14)
H1	0.031 (4)	0.514 (5)	0.168 (2)	0.0650*
H3	0.55850	0.22381	−0.00787	0.0697*
H4	0.45732	0.29422	−0.13392	0.0768*
H5	0.23957	0.40382	−0.13609	0.0710*
H6	0.11979	0.43474	−0.01489	0.0582*
H7	0.220 (3)	0.409 (4)	0.186 (2)	0.0472*
H8A	−0.15277	0.02578	0.04276	0.1289*
H8B	−0.14567	0.20944	0.08889	0.1289*
H8C	−0.15650	0.03237	0.14001	0.1289*
H9A	0.33363	−0.20263	0.19280	0.1231*
H9B	0.20387	−0.22632	0.13727	0.1231*
H9C	0.18939	−0.18618	0.23233	0.1231*

	U11	U22	U33	U12	U13	U23
P1	0.0397 (5)	0.0498 (6)	0.0394 (6)	−0.0010 (3)	0.0118 (3)	0.0050 (2)
O1	0.0612 (13)	0.0632 (12)	0.0381 (11)	0.0208 (10)	0.0100 (9)	−0.0029 (8)
O2	0.0730 (17)	0.135 (3)	0.0482 (14)	0.0101 (15)	−0.0100 (12)	−0.0049 (14)
O3	0.0687 (19)	0.134 (3)	0.094 (2)	0.0365 (17)	−0.0079 (17)	0.0130 (18)
O4	0.0558 (13)	0.0733 (14)	0.0432 (12)	−0.0081 (10)	0.0176 (10)	0.0110 (9)
O5	0.0521 (13)	0.0700 (14)	0.0551 (13)	−0.0075 (10)	0.0116 (9)	−0.0146 (10)
O6	0.0453 (12)	0.0551 (13)	0.1034 (19)	0.0036 (9)	0.0211 (11)	0.0248 (12)
N1	0.0437 (13)	0.0792 (18)	0.0541 (15)	−0.0038 (12)	0.0011 (11)	0.0101 (13)
C1	0.0422 (14)	0.0397 (13)	0.0322 (13)	−0.0045 (9)	0.0082 (10)	0.0001 (8)
C2	0.0403 (13)	0.0502 (14)	0.0443 (14)	−0.0063 (11)	0.0059 (10)	0.0011 (11)
C3	0.0421 (15)	0.073 (2)	0.0590 (17)	−0.0008 (13)	0.0181 (13)	−0.0008 (14)
C4	0.0621 (19)	0.086 (2)	0.0439 (16)	−0.0039 (17)	0.0213 (13)	−0.0057 (15)
C5	0.065 (2)	0.080 (2)	0.0322 (14)	−0.0026 (15)	0.0077 (12)	0.0027 (12)
C6	0.0500 (16)	0.0613 (16)	0.0341 (14)	0.0044 (12)	0.0052 (11)	0.0036 (11)
C7	0.0442 (14)	0.0449 (14)	0.0291 (13)	0.0009 (10)	0.0065 (10)	0.0001 (9)
C8	0.056 (2)	0.114 (3)	0.088 (3)	−0.004 (2)	−0.0030 (18)	−0.033 (2)
C9	0.068 (2)	0.060 (2)	0.119 (3)	0.0109 (16)	0.025 (2)	0.025 (2)

P1—O4	1.467 (2)	C3—C4	1.381 (5)
P1—O5	1.557 (2)	C4—C5	1.370 (5)
P1—O6	1.563 (2)	C5—C6	1.387 (4)
P1—C7	1.829 (2)	C3—H3	0.9300
O1—C7	1.416 (3)	C4—H4	0.9300
O2—N1	1.221 (4)	C5—H5	0.9300
O3—N1	1.207 (4)	C6—H6	0.9300
O5—C8	1.441 (4)	C7—H7	0.93 (3)
O6—C9	1.424 (4)	C8—H8A	0.9600
O1—H1	0.87 (3)	C8—H8B	0.9600
N1—C2	1.475 (4)	C8—H8C	0.9600
C1—C6	1.390 (4)	C9—H9A	0.9600
C1—C7	1.515 (4)	C9—H9B	0.9600
C1—C2	1.390 (4)	C9—H9C	0.9600
C2—C3	1.387 (4)
P1···H1i	3.14 (3)	N1···O6	2.876 (3)
O1···O4	3.145 (3)	N1···H7	2.87 (3)
O1···O5	2.981 (3)	C2···O6	3.035 (4)
O1···C8	3.372 (5)	C2···C4ix	3.566 (5)
O1···O4ii	2.674 (3)	C3···C3ix	3.556 (5)
O1···C6iii	3.343 (4)	C4···C2ix	3.566 (5)
O2···C7	2.827 (4)	C6···O1iii	3.343 (4)
O2···O6	3.086 (4)	C7···O2	2.827 (4)
O3···C8iv	3.240 (5)	C8···O1	3.372 (5)
O4···O1	3.145 (3)	C8···O3x	3.240 (5)
O4···O1i	2.674 (3)	C8···O5v	3.350 (5)
O4···C9ii	3.320 (5)	C9···O4i	3.320 (5)
O5···C8v	3.350 (5)	H1···P1ii	3.14 (3)
O5···O1	2.981 (3)	H1···O4ii	1.81 (3)
O6···O2	3.086 (4)	H3···O3	2.4200
O6···C2	3.035 (4)	H4···H9Axi	2.3800
O6···N1	2.876 (3)	H4···O2xii	2.7800
O1···H6iii	2.5800	H5···O4xii	2.7300
O1···H6	2.3000	H6···O1	2.3000
O1···H8B	2.8300	H6···O1iii	2.5800
O1···H9Bvi	2.7400	H7···O2	2.29 (3)
O2···H7	2.29 (3)	H7···N1	2.87 (3)
O2···H9Avii	2.7700	H8A···O5v	2.6500
O2···H4viii	2.7800	H8B···O1	2.8300
O3···H3	2.4200	H8C···O3x	2.8700
O3···H8Civ	2.8700	H8C···O4	2.7300
O4···H5viii	2.7300	H9A···O2xiii	2.7700
O4···H9C	2.9100	H9A···H4xi	2.3800
O4···H9Cii	2.6100	H9B···O1xiv	2.7400
O4···H8C	2.7300	H9C···O4	2.9100
O4···H1i	1.81 (3)	H9C···O4i	2.6100
O5···H8Av	2.6500
O4—P1—O5	114.43 (12)	P1—C7—O1	105.03 (19)
O4—P1—O6	116.05 (14)	C2—C3—H3	120.00
O4—P1—C7	112.25 (13)	C4—C3—H3	120.00
O5—P1—O6	103.49 (13)	C3—C4—H4	120.00
O5—P1—C7	106.44 (12)	C5—C4—H4	120.00
O6—P1—C7	103.00 (13)	C4—C5—H5	120.00
P1—O5—C8	122.7 (2)	C6—C5—H5	120.00
P1—O6—C9	123.8 (2)	C1—C6—H6	119.00
C7—O1—H1	109 (2)	C5—C6—H6	119.00
O2—N1—O3	123.3 (3)	P1—C7—H7	107.7 (19)
O3—N1—C2	118.6 (3)	O1—C7—H7	109.5 (18)
O2—N1—C2	118.1 (3)	C1—C7—H7	113.1 (19)
C2—C1—C7	125.4 (2)	O5—C8—H8A	109.00
C6—C1—C7	118.2 (3)	O5—C8—H8B	109.00
C2—C1—C6	116.2 (2)	O5—C8—H8C	109.00
N1—C2—C3	115.4 (3)	H8A—C8—H8B	109.00
C1—C2—C3	122.5 (3)	H8A—C8—H8C	109.00
N1—C2—C1	122.1 (2)	H8B—C8—H8C	110.00
C2—C3—C4	119.5 (3)	O6—C9—H9A	109.00
C3—C4—C5	119.3 (3)	O6—C9—H9B	110.00
C4—C5—C6	120.5 (3)	O6—C9—H9C	109.00
C1—C6—C5	121.8 (3)	H9A—C9—H9B	109.00
P1—C7—C1	111.07 (16)	H9A—C9—H9C	109.00
O1—C7—C1	110.1 (2)	H9B—C9—H9C	109.00
O4—P1—O5—C8	25.6 (3)	C6—C1—C2—N1	177.3 (3)
O6—P1—O5—C8	152.8 (3)	C6—C1—C2—C3	−2.1 (4)
C7—P1—O5—C8	−99.0 (3)	C7—C1—C2—N1	−7.1 (4)
O4—P1—O6—C9	58.0 (3)	C7—C1—C2—C3	173.6 (3)
O5—P1—O6—C9	−68.2 (3)	C2—C1—C6—C5	0.8 (4)
C7—P1—O6—C9	−179.0 (3)	C7—C1—C6—C5	−175.2 (3)
O4—P1—C7—O1	−68.02 (19)	C2—C1—C7—P1	−76.9 (3)
O4—P1—C7—C1	173.00 (18)	C2—C1—C7—O1	167.2 (2)
O5—P1—C7—O1	57.90 (19)	C6—C1—C7—P1	98.6 (2)
O5—P1—C7—C1	−61.1 (2)	C6—C1—C7—O1	−17.3 (3)
O6—P1—C7—O1	166.43 (17)	N1—C2—C3—C4	−177.7 (3)
O6—P1—C7—C1	47.5 (2)	C1—C2—C3—C4	1.7 (5)
O2—N1—C2—C1	−28.4 (4)	C2—C3—C4—C5	0.1 (5)
O2—N1—C2—C3	151.0 (3)	C3—C4—C5—C6	−1.3 (6)
O3—N1—C2—C1	153.8 (3)	C4—C5—C6—C1	0.9 (5)
O3—N1—C2—C3	−26.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ii	0.87 (3)	1.81 (3)	2.674 (3)	171 (4)
C6—H6···O1	0.9300	2.3000	2.688 (3)	104.00
C6—H6···O1iii	0.9300	2.5800	3.343 (4)	140.00
C7—H7···O2	0.93 (3)	2.29 (3)	2.827 (4)	116 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.87 (3)	1.81 (3)	2.674 (3)	171 (4)
C6—H6⋯O1	0.93	2.30	2.688 (3)	104
C6—H6⋯O1ii	0.93	2.58	3.343 (4)	140
C7—H7⋯O2	0.93 (3)	2.29 (3)	2.827 (4)	116 (2)

Symmetry codes: (i) ; (ii) .