Dimethyl [hydr­oxy(2-nitro­phen­yl)meth­yl]phospho­nate

Tahir, M.N.; Acar, N.; Yilmaz, H.; Tariq, M.I.; Ülkü, D.

doi:10.1107/S1600536809005467

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o562

doi:10.1107/S1600536809005467

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Dimethyl [hydroxy(2-nitrophenyl)methyl]phosphonate

M. Nawaz Tahir,^a ^* Nurcan Acar,^b Hamza Yilmaz,^b Muhammad Ilyas Tariq ^c and Dinçer Ülkü ^d

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Chemistry, Faculty of Science, University of Ankara, Ankara, Turkey, ^cDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^dDepartment of Physics Engineering, Hacettepe University, Beytepe 06532, Ankara, Turkey
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 14 February 2009; accepted 16 February 2009; online 21 February 2009)

In the title compound, C₉H₁₂NO₆P, intramolecular 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 R₂²(10). The O atom of the hydroxy 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_r = 261.17
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.057
wR(F²) = 0.231
S = 1.00
2093 reflections
162 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.50 e Å⁻³

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) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

(R)-Dimethyl [(2-chlorophenyl)hydroxymethyl]phosphonate (Tahir et al., 2007) and Dimethyl (1-hydroxy-1,2-diphenylethyl)phosphonate (Acar et al., 2009) have been reported by us. In continuation to the study of phosphonate compounds, we herein report the preparation and crystal structure of the title compound (I), (Fig 1).

Diethyl [hydroxy(2-nitrophenyl)methyl]phosphonate (II) (Chen et al., 2008) have also been published which have similar coordination around the C-atom having α-hydroxy group. But it is observed that the change of diethylphosphonate (II) with dimethylphosphonate (I) results in the S-conformation at the methine. In (I), the P═O is 1.467 (2) Å, whereas P–O and P–C have values of [1.557 (2), 1.563 (2) Å] and 1.829 (2) Å, respectively. The nitro group is oriented at an angle of 27.96 (23)° with the benzene ring A(C1—C6). There exist two intramolecular H-bondings which form five B(O1/C7/C1/C6/H6···O1) and six C(O2/N1/C2/C1/C7/H7···O2) membered rings. The title compound is dimerized (Fig 2) forming ring motifs R₂²(10) (Bernstein et al., 1995) if only intermolecular H-bonding is concerned. This ten membered ring is splitted into three rings through intramolecular H-bonding resulting in the formation of central four membered ring [O···H···O···H···O]. A similar ring has already been observed in 3-[(methylcarbamoyl)amino]-1H-isoindolium chloride (Maliha et al., 2009). The O-atom of hydroxy group behaves as an accepter and the benzene ring as donar. The adjacent dimers are connected through intermolecular H-bonds of O–H···O type, where the accepter is doubly bonded O the phosphonate group.

Related literature top

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 top

A solution of O-nitrobenzaldehide (3.01 g, 20 mmole) and dimethylphosphonate (2.20 g, 20 mmole) was prepared in THF (50 ml). To this solution, a powder mixture of an equal amount of KF and commercial Al₂O₃ (2.5 g + 2.5 g) was added slowly and stirred for 48 h at 273 K. The product was filtered and the filtrate was evaporated at room temperature. The crystalline material obtained after two days was washed with ether and recrystallized in a solution mixture of petroleum ether and THF(1:1), [m.p: 383 K].

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1992); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1992); 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).

Figures top

	Fig. 1. ORTEP drawing of the title compound, (C₉H₁₂NO₆P), with the atom numbering scheme. The thermal ellpsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. The broken lines indicate the intermolecular H-bondings.
	Fig. 2. The partial packing figure (PLATON: Spek, 2009) shows the formation of ring motifs through hydrogen bonding.

Dimethyl [(S)-hydroxy(2-nitrophenyl)methyl]phosphonate top

Crystal data top

C₉H₁₂NO₆P	F(000) = 544
M_r = 261.17	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.017
ω/2θ scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: ψ scan (MolEN; Fair, 1990)	h = −11→0
T_min = 0.939, T_max = 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 top

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(F_o²) + (0.199P)² + 0.3221P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2093 reflections	Δρ_max = 0.70 e Å⁻³
162 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints

Crystal data top

C₉H₁₂NO₆P	V = 1193.3 (2) Å³
M_r = 261.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8685 (12) Å	µ = 0.25 mm⁻¹
b = 7.5081 (11) Å	T = 296 K
c = 16.1052 (12) Å	0.26 × 0.20 × 0.18 mm
β = 90.341 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1873 reflections with I > 2σ(I)
Absorption correction: ψ scan (MolEN; Fair, 1990)	R_int = 0.017
T_min = 0.939, T_max = 0.959	3 standard reflections every 120 min
2222 measured reflections	intensity decay: −1.6%
2093 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.231	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.70 e Å⁻³
2093 reflections	Δρ_min = −0.50 e Å⁻³
162 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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···C4^ix	3.566 (5)
O1···O4ⁱⁱ	2.674 (3)	C3···C3^ix	3.556 (5)
O1···C6ⁱⁱⁱ	3.343 (4)	C4···C2^ix	3.566 (5)
O2···C7	2.827 (4)	C6···O1ⁱⁱⁱ	3.343 (4)
O2···O6	3.086 (4)	C7···O2	2.827 (4)
O3···C8^iv	3.240 (5)	C8···O1	3.372 (5)
O4···O1	3.145 (3)	C8···O3^x	3.240 (5)
O4···O1ⁱ	2.674 (3)	C8···O5^v	3.350 (5)
O4···C9ⁱⁱ	3.320 (5)	C9···O4ⁱ	3.320 (5)
O5···C8^v	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···H9A^xi	2.3800
O6···N1	2.876 (3)	H4···O2^xii	2.7800
O1···H6ⁱⁱⁱ	2.5800	H5···O4^xii	2.7300
O1···H6	2.3000	H6···O1	2.3000
O1···H8B	2.8300	H6···O1ⁱⁱⁱ	2.5800
O1···H9B^vi	2.7400	H7···O2	2.29 (3)
O2···H7	2.29 (3)	H7···N1	2.87 (3)
O2···H9A^vii	2.7700	H8A···O5^v	2.6500
O2···H4^viii	2.7800	H8B···O1	2.8300
O3···H3	2.4200	H8C···O3^x	2.8700
O3···H8C^iv	2.8700	H8C···O4	2.7300
O4···H5^viii	2.7300	H9A···O2^xiii	2.7700
O4···H9C	2.9100	H9A···H4^xi	2.3800
O4···H9Cⁱⁱ	2.6100	H9B···O1^xiv	2.7400
O4···H8C	2.7300	H9C···O4	2.9100
O4···H1ⁱ	1.81 (3)	H9C···O4ⁱ	2.6100
O5···H8A^v	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)

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, −y+1, −z; (iv) x+1, y, z; (v) −x, −y, −z; (vi) x, y+1, z; (vii) −x+1, y+1/2, −z+1/2; (viii) x, −y+1/2, z+1/2; (ix) −x+1, −y+1, −z; (x) x−1, y, z; (xi) −x+1, −y, −z; (xii) x, −y+1/2, z−1/2; (xiii) −x+1, y−1/2, −z+1/2; (xiv) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

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)

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

Experimental details

Crystal data
Chemical formula	C₉H₁₂NO₆P
M_r	261.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.8685 (12), 7.5081 (11), 16.1052 (12)
β (°)	90.341 (1)
V (Å³)	1193.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.26 × 0.20 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (MolEN; Fair, 1990)
T_min, T_max	0.939, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	2222, 2093, 1873
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.231, 1.00
No. of reflections	2093
No. of parameters	162
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.50

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1992), MolEN (Fair, 1990), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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	0.9300	2.3000	2.688 (3)	104.00
C6—H6···O1ⁱⁱ	0.9300	2.5800	3.343 (4)	140.00
C7—H7···O2	0.93 (3)	2.29 (3)	2.827 (4)	116 (2)

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

References

Acar, N., Tahir, M. N., Yılmaz, H., Chishti, M. S. A. & Malik, M. A. (2009). Acta Cryst. E65, o481. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Enraf–Nonius (1992). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Fair, C. K. (1990). MolEN. Enraf–Nonius, Delft, The Netherlands. Google Scholar
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Volume 65| Part 3| March 2009| Page o562

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