6-Formyl-2-meth­oxy-3-nitro­phenyl 4-toluene­sulfonate

Ramachandran, G.; Suresh, R.; Sreedevi, S.; Kanakam, C.C.; Ramkumar, V.

doi:10.1107/S1600536808029711

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2046

doi:10.1107/S1600536808029711

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6-Formyl-2-methoxy-3-nitrophenyl 4-toluenesulfonate

G. Ramachandran,^a R. Suresh,^b S. Sreedevi,^a Charles C Kanakam ^a ^* and V. Ramkumar ^c

^aDepartment of Chemistry, Valliammai Engineering College, SRM Nagar, Chennai, Tamil Nadu, India, ^bDepartment of Chemistry, Presidency College, Chennai, India, and ^cDepartment of Chemistry, Indian Institute of Technology Madras, Chennai-36, Tamil Nadu, India
^*Correspondence e-mail: charlesckin@yahoo.com

(Received 6 September 2008; accepted 16 September 2008; online 30 September 2008)

In the title compound, C₁₅H₁₃NO₇S, the interplanar angle between the two aromatic rings is 26.04 (3)°. The crystal structure is stabilized by C—H⋯O interactions.

Related literature

For general background, see: Alford et al. (1991 ); Baldessarini (1987 ); Jiang et al. (1990 ); Spungin et al. (1992 ); Tharakan et al. (1992 ); Yachi et al. (1989 ). For related structures, see: Ramachandran et al. (2007 ); Ramachandran, Kanakam & Manivannan (2008 ); Ramachandran, Kanakam, Gunasekaran & Manivannan (2008 ); Ramachandran, Suresh, Chakkaravarthi et al. (2008 ); Manivannan et al. (2005a ,b ).

Experimental

Crystal data

C₁₅H₁₃NO₇S
M_r = 351.32
Triclinic, $[P \overline 1]$
a = 8.1883 (16) Å
b = 9.5511 (19) Å
c = 10.530 (2) Å
α = 86.022 (3)°
β = 87.294 (3)°
γ = 73.588 (3)°
V = 787.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 (2) K
0.42 × 0.32 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.905, T_max = 0.951
9176 measured reflections
3647 independent reflections
2897 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.129
S = 1.02
3647 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O6ⁱ	0.93	2.70	3.335 (3)	125
Symmetry code: (i) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029711/bx2179sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029711/bx2179Isup2.hkl

checkCIF report

Comment top

Several compounds containing p-toluene sulfonate (PTS) moiety were used in the fields of biology and industry. The merging of lipids can be monitored using derivatives of p-toluene sulfonates (Yachi, et al., 1989). This method has been used in studying the membrane fusion during the acrosome reaction (Spungin, et al., 1992). PTS are used to purify human coagulation factor (Tharakan, et al., 1992) in the study of viruses (Alford, et al., 1991) and in the development of technology for linking photosensitizer to a model of monoclonal antibody (Jiang, et al., 1990). In the field of pharmacology for the study of neuro pharmacology of s-adenosyl –L– methionine, PTS is used (Baldessarini, 1987). Because of the wide variety of biological importance of PTS, the synthesis of several substituted sulfonates and the study of their single-crystal XRD studies continues to be an interesting field of research. In the present paper, the synthesis and characterization by single-crystal study of the title compound is reported. In the title compound, the dihedral angle between the two aromatic rings is 26.04 (3)°.The geometric parameters agree with the reported values of similar structures (Manivannan et al., 2005a, b; Ramachandran et al., 2007). The angle between the O7—S1—O6 is 119.12 (11)°, which is greater than the tetrahedral angle, leading to the decrease in the O5—S1—C9 angle which is 97.9 (8)°. The eclipsed conformation of the sulfonyl moiety is confirmed by the torsion angle of O7—S1—C9—C14 = -19.3 (3)° and O6—S1—C9—C10 = 26.04 (19)°. The crystal packing is stabilized by Van der Waals interaction.

Related literature top

For related literature, see: Alford et al. (1991); Baldessarini (1987); Jiang et al. (1990); Ramachandran et al. (2007); Ramachandran, Kanakam & Manivannan (2008); Ramachandran, Kanakam, Gunasekaran & Manivannan (2008); Ramachandran, Suresh, Chakkaravarthi et al. (2008); Manivannan et al. (2005a,b); Spungin et al. (1992); Tharakan et al. (1992); Yachi et al. (1989).

Experimental top

Acetylation of vanillin with acetic anhydride in presence of sodium acetate yielded acetyl vanillin. Powdered o-vanillin acetate was added to a stirred mixture of fuming HNO₃ and concentrate H₂SO₄. The nitrated material was then hydrolyzed in 2% sodium hydroxide. The orange yellow solid was filtered and the filtrate was acidified to get the 4-nitro-2-hydroxy-3methoxy benzaldehyde. The benzaldehyde and triethylamine were dissolved in acetone and treated with 4-toluene sulfonyl chloride. The residue obtained was washed with 2% aqueous triethylamine solution to obtain the crude product. Diffraction quality crystals were obtained by recrystallizing the crude product from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP of the molecule with atoms represented as 30% probability ellipsoids.

6-Formyl-2-methoxy-3-nitrophenyl 4-toluenesulfonate top

Crystal data top

C₁₅H₁₃NO₇S	Z = 2
M_r = 351.32	F(000) = 364
Triclinic, P1	D_x = 1.481 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1883 (16) Å	Cell parameters from 873 reflections
b = 9.5511 (19) Å	θ = 2.6–26.3°
c = 10.530 (2) Å	µ = 0.24 mm⁻¹
α = 86.022 (3)°	T = 298 K
β = 87.294 (3)°	Block, yellow
γ = 73.588 (3)°	0.42 × 0.32 × 0.21 mm
V = 787.8 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3647 independent reflections
Radiation source: fine-focus sealed tube	2897 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 28.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −10→10
T_min = 0.905, T_max = 0.951	k = −12→12
9176 measured reflections	l = −13→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0677P)² + 0.1932P] where P = (F_o² + 2F_c²)/3
3647 reflections	(Δ/σ)_max = 0.001
223 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₃NO₇S	γ = 73.588 (3)°
M_r = 351.32	V = 787.8 (3) Å³
Triclinic, P1	Z = 2
a = 8.1883 (16) Å	Mo Kα radiation
b = 9.5511 (19) Å	µ = 0.24 mm⁻¹
c = 10.530 (2) Å	T = 298 K
α = 86.022 (3)°	0.42 × 0.32 × 0.21 mm
β = 87.294 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3647 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2897 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.951	R_int = 0.018
9176 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.25 e Å⁻³
3647 reflections	Δρ_min = −0.24 e Å⁻³
223 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.7558 (2)	−0.10359 (19)	0.96696 (18)	0.0478 (4)
C2	0.6751 (2)	−0.1421 (2)	1.0781 (2)	0.0538 (5)
H2	0.6431	−0.2284	1.0839	0.065*
C3	0.6428 (2)	−0.0544 (2)	1.1783 (2)	0.0562 (5)
H3	0.5877	−0.0801	1.2517	0.067*
C4	0.6923 (2)	0.0729 (2)	1.17052 (18)	0.0517 (4)
C5	0.7671 (2)	0.12023 (18)	1.06001 (18)	0.0456 (4)
C6	0.7967 (2)	0.02845 (18)	0.95936 (17)	0.0426 (4)
C7	0.7991 (3)	−0.2053 (2)	0.8626 (2)	0.0658 (6)
C8	0.6935 (3)	0.3798 (2)	1.0658 (3)	0.0804 (7)
H8A	0.5854	0.3754	1.0375	0.121*
H8B	0.7267	0.4572	1.0182	0.121*
H8C	0.6844	0.3981	1.1547	0.121*
C9	0.9340 (2)	0.2467 (2)	0.67574 (17)	0.0476 (4)
C10	0.9440 (3)	0.3730 (2)	0.7267 (2)	0.0585 (5)
H10	0.8676	0.4155	0.7907	0.070*
C11	1.0702 (3)	0.4352 (2)	0.6806 (2)	0.0613 (5)
H11	1.0771	0.5211	0.7136	0.074*
C12	1.1854 (3)	0.3732 (2)	0.58733 (19)	0.0541 (5)
C13	1.1713 (3)	0.2464 (2)	0.5368 (2)	0.0603 (5)
H13	1.2477	0.2039	0.4729	0.072*
C14	1.0458 (3)	0.1830 (2)	0.58002 (19)	0.0569 (5)
H14	1.0366	0.0987	0.5453	0.068*
C15	1.3252 (3)	0.4399 (3)	0.5411 (3)	0.0757 (7)
H15A	1.2901	0.5427	0.5541	0.114*
H15B	1.3482	0.4254	0.4520	0.114*
H15C	1.4263	0.3940	0.5876	0.114*
N1	0.6741 (3)	0.1525 (2)	1.28715 (19)	0.0734 (5)
S1	0.77841 (6)	0.16535 (5)	0.73509 (5)	0.05360 (17)
O1	0.7587 (3)	−0.3163 (2)	0.8658 (2)	0.1075 (7)
O2	0.5469 (3)	0.1609 (3)	1.3527 (2)	0.1279 (9)
O3	0.7902 (3)	0.1989 (2)	1.31513 (18)	0.0950 (6)
O4	0.81953 (17)	0.24287 (14)	1.04624 (14)	0.0588 (4)
O5	0.88441 (15)	0.06651 (13)	0.85158 (12)	0.0497 (3)
O6	0.63603 (17)	0.26914 (17)	0.78802 (15)	0.0685 (4)
O7	0.7507 (2)	0.0679 (2)	0.64859 (16)	0.0786 (5)
H7	0.862 (3)	−0.182 (3)	0.796 (2)	0.074 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0396 (8)	0.0408 (8)	0.0614 (11)	−0.0089 (7)	−0.0029 (8)	−0.0005 (8)
C2	0.0463 (10)	0.0454 (9)	0.0704 (12)	−0.0169 (8)	−0.0019 (9)	0.0074 (9)
C3	0.0443 (10)	0.0623 (11)	0.0601 (11)	−0.0158 (8)	0.0031 (8)	0.0110 (9)
C4	0.0417 (9)	0.0566 (10)	0.0536 (10)	−0.0085 (8)	0.0008 (8)	−0.0053 (8)
C5	0.0359 (8)	0.0404 (8)	0.0597 (10)	−0.0099 (7)	−0.0024 (7)	0.0002 (8)
C6	0.0331 (8)	0.0425 (8)	0.0507 (9)	−0.0098 (6)	−0.0006 (7)	0.0032 (7)
C7	0.0707 (14)	0.0507 (11)	0.0770 (15)	−0.0181 (10)	0.0055 (12)	−0.0123 (10)
C8	0.0891 (17)	0.0435 (11)	0.1050 (19)	−0.0107 (11)	−0.0060 (15)	−0.0103 (12)
C9	0.0500 (10)	0.0507 (9)	0.0465 (9)	−0.0226 (8)	−0.0023 (7)	0.0022 (7)
C10	0.0620 (12)	0.0551 (11)	0.0620 (12)	−0.0225 (9)	0.0110 (9)	−0.0115 (9)
C11	0.0699 (13)	0.0498 (10)	0.0722 (13)	−0.0295 (10)	0.0039 (10)	−0.0093 (9)
C12	0.0572 (11)	0.0548 (10)	0.0553 (10)	−0.0262 (9)	−0.0025 (9)	0.0082 (9)
C13	0.0651 (12)	0.0697 (12)	0.0516 (11)	−0.0289 (10)	0.0128 (9)	−0.0075 (9)
C14	0.0693 (12)	0.0589 (11)	0.0516 (10)	−0.0324 (10)	0.0041 (9)	−0.0100 (9)
C15	0.0691 (14)	0.0796 (15)	0.0879 (16)	−0.0416 (12)	0.0041 (12)	0.0126 (13)
N1	0.0743 (13)	0.0818 (13)	0.0614 (11)	−0.0165 (11)	0.0068 (10)	−0.0140 (10)
S1	0.0482 (3)	0.0630 (3)	0.0554 (3)	−0.0270 (2)	−0.0066 (2)	0.0082 (2)
O1	0.1421 (19)	0.0669 (11)	0.1292 (17)	−0.0530 (12)	0.0317 (14)	−0.0372 (11)
O2	0.1049 (16)	0.185 (2)	0.0988 (16)	−0.0444 (17)	0.0474 (14)	−0.0604 (17)
O3	0.1123 (15)	0.1068 (14)	0.0786 (12)	−0.0459 (13)	−0.0068 (11)	−0.0262 (11)
O4	0.0565 (8)	0.0453 (7)	0.0785 (9)	−0.0205 (6)	0.0023 (7)	−0.0070 (6)
O5	0.0402 (6)	0.0538 (7)	0.0535 (7)	−0.0130 (5)	0.0029 (5)	0.0052 (6)
O6	0.0433 (7)	0.0758 (9)	0.0808 (10)	−0.0136 (7)	−0.0020 (7)	0.0215 (8)
O7	0.0926 (12)	0.0985 (12)	0.0683 (9)	−0.0644 (10)	−0.0141 (8)	0.0003 (9)

Geometric parameters (Å, º) top

C1—C6	1.390 (2)	C9—C14	1.381 (3)
C1—C2	1.395 (3)	C9—S1	1.7417 (18)
C1—C7	1.481 (3)	C10—C11	1.385 (3)
C2—C3	1.362 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.372 (3)
C3—C4	1.382 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.391 (3)
C4—C5	1.397 (3)	C12—C15	1.507 (3)
C4—N1	1.469 (3)	C13—C14	1.378 (3)
C5—O4	1.353 (2)	C13—H13	0.9300
C5—C6	1.391 (3)	C14—H14	0.9300
C6—O5	1.396 (2)	C15—H15A	0.9600
C7—O1	1.195 (3)	C15—H15B	0.9600
C7—H7	0.90 (3)	C15—H15C	0.9600
C8—O4	1.439 (3)	N1—O2	1.208 (3)
C8—H8A	0.9600	N1—O3	1.212 (3)
C8—H8B	0.9600	S1—O7	1.4157 (17)
C8—H8C	0.9600	S1—O6	1.4194 (16)
C9—C10	1.378 (3)	S1—O5	1.6206 (13)

C6—C1—C2	118.45 (17)	C9—C10—H10	120.7
C6—C1—C7	122.12 (18)	C11—C10—H10	120.7
C2—C1—C7	119.42 (18)	C12—C11—C10	121.56 (18)
C3—C2—C1	120.55 (17)	C12—C11—H11	119.2
C3—C2—H2	119.7	C10—C11—H11	119.2
C1—C2—H2	119.7	C11—C12—C13	118.60 (17)
C2—C3—C4	119.79 (18)	C11—C12—C15	120.86 (19)
C2—C3—H3	120.1	C13—C12—C15	120.5 (2)
C4—C3—H3	120.1	C14—C13—C12	121.05 (19)
C3—C4—C5	122.26 (18)	C14—C13—H13	119.5
C3—C4—N1	117.05 (18)	C12—C13—H13	119.5
C5—C4—N1	120.54 (18)	C13—C14—C9	118.86 (18)
O4—C5—C6	118.41 (16)	C13—C14—H14	120.6
O4—C5—C4	125.31 (17)	C9—C14—H14	120.6
C6—C5—C4	116.20 (16)	C12—C15—H15A	109.5
C1—C6—C5	122.61 (16)	C12—C15—H15B	109.5
C1—C6—O5	119.59 (16)	H15A—C15—H15B	109.5
C5—C6—O5	117.56 (15)	C12—C15—H15C	109.5
O1—C7—C1	122.8 (2)	H15A—C15—H15C	109.5
O1—C7—H7	120.0 (16)	H15B—C15—H15C	109.5
C1—C7—H7	117.2 (16)	O2—N1—O3	124.0 (2)
O4—C8—H8A	109.5	O2—N1—C4	117.3 (2)
O4—C8—H8B	109.5	O3—N1—C4	118.5 (2)
H8A—C8—H8B	109.5	O7—S1—O6	119.12 (11)
O4—C8—H8C	109.5	O7—S1—O5	107.06 (9)
H8A—C8—H8C	109.5	O6—S1—O5	107.89 (8)
H8B—C8—H8C	109.5	O7—S1—C9	111.02 (10)
C10—C9—C14	121.31 (17)	O6—S1—C9	111.53 (9)
C10—C9—S1	119.04 (15)	O5—S1—C9	97.91 (8)
C14—C9—S1	119.64 (14)	C5—O4—C8	117.22 (16)
C9—C10—C11	118.60 (19)	C6—O5—S1	119.51 (10)

C6—C1—C2—C3	−2.3 (3)	C10—C11—C12—C15	−178.1 (2)
C7—C1—C2—C3	176.22 (18)	C11—C12—C13—C14	−0.7 (3)
C1—C2—C3—C4	−0.8 (3)	C15—C12—C13—C14	178.8 (2)
C2—C3—C4—C5	3.5 (3)	C12—C13—C14—C9	−0.5 (3)
C2—C3—C4—N1	−172.22 (18)	C10—C9—C14—C13	1.1 (3)
C3—C4—C5—O4	−179.50 (17)	S1—C9—C14—C13	−178.09 (17)
N1—C4—C5—O4	−3.9 (3)	C3—C4—N1—O2	−40.7 (3)
C3—C4—C5—C6	−2.9 (3)	C5—C4—N1—O2	143.5 (2)
N1—C4—C5—C6	172.72 (16)	C3—C4—N1—O3	135.6 (2)
C2—C1—C6—C5	2.9 (3)	C5—C4—N1—O3	−40.2 (3)
C7—C1—C6—C5	−175.55 (17)	C10—C9—S1—O7	161.44 (16)
C2—C1—C6—O5	177.10 (15)	C14—C9—S1—O7	−19.3 (2)
C7—C1—C6—O5	−1.3 (3)	C10—C9—S1—O6	26.04 (19)
O4—C5—C6—C1	176.49 (15)	C14—C9—S1—O6	−154.70 (16)
C4—C5—C6—C1	−0.4 (2)	C10—C9—S1—O5	−86.80 (17)
O4—C5—C6—O5	2.2 (2)	C14—C9—S1—O5	92.45 (17)
C4—C5—C6—O5	−174.69 (14)	C6—C5—O4—C8	124.5 (2)
C6—C1—C7—O1	−176.9 (2)	C4—C5—O4—C8	−58.9 (3)
C2—C1—C7—O1	4.7 (3)	C1—C6—O5—S1	93.43 (17)
C14—C9—C10—C11	−0.5 (3)	C5—C6—O5—S1	−92.07 (17)
S1—C9—C10—C11	178.74 (17)	O7—S1—O5—C6	−92.32 (14)
C9—C10—C11—C12	−0.8 (3)	O6—S1—O5—C6	37.02 (15)
C10—C11—C12—C13	1.4 (3)	C9—S1—O5—C6	152.75 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6ⁱ	0.93	2.70	3.335 (3)	125

Symmetry code: (i) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₇S
M_r	351.32
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.1883 (16), 9.5511 (19), 10.530 (2)
α, β, γ (°)	86.022 (3), 87.294 (3), 73.588 (3)
V (Å³)	787.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.42 × 0.32 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.905, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	9176, 3647, 2897
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.129, 1.03
No. of reflections	3647
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.24

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6ⁱ	0.93	2.70	3.335 (3)	125

Symmetry code: (i) −x+1, −y, −z+2.

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Volume 64| Part 10| October 2008| Page o2046

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