2,2′-(Biphenyl-4,4′-diyldi­oxy)diacetic acid N,N-dimethyl­formamide solvate

Cao, Y.-J.

doi:10.1107/S1600536809025914

organic compounds

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Volume 65| Part 8| August 2009| Page o1851

doi:10.1107/S1600536809025914

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2,2′-(Biphenyl-4,4′-diyldioxy)diacetic acid N,N-dimethylformamide solvate

Yu-Juan Cao ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: caoyj@scnu.edu.cn

(Received 29 May 2009; accepted 4 July 2009; online 15 July 2009)

In the crystal struture of the title compound, C₁₆H₁₄O₆·C₃H₇NO, the two crystallographically independent benzene rings are coplanar [dihedral angle = 1.00 (2)°]. The crystal structure is stabilized by O—H⋯O hydrogen bonds between the diacid and the solvate dimethylformamide molecule, resulting in the formation of a zigzag chain structure extending parallel to [001].

Related literature

For general background to biphenyl carbinols and their biological applications, see: Kamoda et al. (2006 ); Mikami & Yamanaka (2003 ); Sallam et al. (2006 ). For the crystal structures of related compounds, see: Rabnawaz et al. (2008 ); Tan et al. (2005 ). For the preparation of the title compound, see: Hayes & Branch (1943 ).

Experimental

Crystal data

C₁₆H₁₄O₆·C₃H₇NO
M_r = 375.37
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.7471 (15) Å
b = 8.1758 (16) Å
c = 28.625 (6) Å
V = 1813.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.32 × 0.25 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.971, T_max = 0.984
9412 measured reflections
2079 independent reflections
1778 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.116
S = 1.05
2079 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O7ⁱ	0.82	1.87	2.685 (3)	174
O2—H2⋯O7ⁱⁱ	0.82	1.81	2.626 (3)	176
C15—H15a⋯O1ⁱⁱⁱ	0.97	2.44	3.149 (2)	129
C17—H17⋯O1^iv	0.93	2.56	3.248 (3)	131
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{3\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ ; (iv) $[-x+1, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025914/zl2216sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025914/zl2216Isup2.hkl

checkCIF report

Comment top

Biphenyl carbinols are valuable intermediates in the preparation of new ligands (Mikami et al., 2003; Rabnawaz et al., 2008; Tan et al., 2005) and have shown important biological activities (Kamoda et al., 2006; Sallam et al., 2006). As part of our ongoing study of such biphenyl carbinol compounds, the crystal structure of the title compound is reported in this work.

The molecular structure of the title compound is shown in Fig. 1. The two crystallographically independent benzene rings are coplanar (dihedral angle = 1.00 (2)°) and the two carboxylic acid groups are oriented in different directions. There are no unusual bonds lengths and angles. The C1—O1 and C16—O5 distances in the title compound are 1.197 (3)Å and 1.184 (4)Å, respectively, typical of double bonds.

The –OCH₂COOH substituents show torsion angles of 176.0 (2)° (C2—O3—C3—C8) and 169.7 (2)° (C15—O4—C12—C11) with respect to the phenyl rings. Intermolecular O—H···O hydrogen bonds between the hydroxyl groups of the diacid and the carbonyl group of the DMF molecule (Table 1) are observed in this structure, thereby forming a one-dimensional zigzag chain structure along the c-axial direction (Fig. 2).

The crystal structure is further stabilized by weak intermolecular hydrogen bonding interactions between the diacids, thus forming a sandwich structure as represented in Fig. 3.

Related literature top

For general background and biological applications, see: Kamoda et al. (2006); Mikami et al. (2003); Sallam et al. (2006). For the crystal structures of related compounds, see: Rabnawaz et al. (2008); Tan et al. (2005). For thepreparation of the title compound, see: Hayes & Branch (1943).

Experimental top

The title compound was prepared according to the general procedure reported by Hayes & Branch (1943). 2-Chloroacetic acid (114 mg, 1.2 mmol) and sodium hydroxide (40 mg, 10 mmol) in 20 ml of N,N-dimethylformamide (DMF) were stirred for 10 min, followed by addition of 2,2'-dihydroxybiphenyl (186 mg, 1 mmol). The reaction mixture was stirred at 100 °C for 3 h. After cooling, the solution was acidified and extracted with ether. Slow evaporation of ether at room temperature yielded colorless crystals of the title compound. IR(KBr pellet, cm^-1): 3428.47, 3042.21, 2905.29, 2787.94,1740.59, 1707.78, 1607.65, 1500.03, 1430.90, 1234.94, 830.29, 797.57.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 50% probability level. All H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. A one-dimensional zigzag chain generated by the hydrogen bonds along the c-axial direction in the title compound. All H atoms are omitted for clarity.
	Fig. 3. A crystallographic packing diagram of the title compound.

2,2'-(Biphenyl-4,4'-diyldioxy)diacetic acid N,N-dimethylformamide solvate top

Crystal data top

C₁₆H₁₄O₆·C₃H₇NO	D_x = 1.375 Mg m⁻³
M_r = 375.37	Melting point = 524.9–525.8 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3913 reflections
a = 7.7471 (15) Å	θ = 1.4–27.8°
b = 8.1758 (16) Å	µ = 0.11 mm⁻¹
c = 28.625 (6) Å	T = 298 K
V = 1813.1 (6) Å³	Block, colorless
Z = 4	0.32 × 0.25 × 0.18 mm
F(000) = 792

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2079 independent reflections
Radiation source: fine-focus sealed tube	1778 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
T_min = 0.971, T_max = 0.984	k = −10→9
9412 measured reflections	l = −29→35

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0655P)² + 0.2914P] where P = (F_o² + 2F_c²)/3
2079 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₆H₁₄O₆·C₃H₇NO	V = 1813.1 (6) Å³
M_r = 375.37	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.7471 (15) Å	µ = 0.11 mm⁻¹
b = 8.1758 (16) Å	T = 298 K
c = 28.625 (6) Å	0.32 × 0.25 × 0.18 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2079 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1778 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.984	R_int = 0.028
9412 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	Δρ_max = 0.22 e Å⁻³
2079 reflections	Δρ_min = −0.19 e Å⁻³
246 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.0567 (4)	−0.7098 (3)	0.65314 (10)	0.0437 (7)
C2	0.0253 (4)	−0.5895 (3)	0.61484 (10)	0.0480 (7)
H2A	0.0508	−0.6406	0.5850	0.058*
H2B	−0.0957	−0.5588	0.6148	0.058*
C3	0.1124 (3)	−0.3291 (3)	0.58665 (9)	0.0385 (6)
C4	0.0138 (4)	−0.3432 (4)	0.54660 (10)	0.0508 (8)
H4	−0.0507	−0.4372	0.5411	0.061*
C5	0.0120 (4)	−0.2161 (4)	0.51477 (10)	0.0506 (8)
H5	−0.0555	−0.2268	0.4881	0.061*
C6	0.1058 (3)	−0.0739 (3)	0.52075 (9)	0.0355 (6)
C7	0.2023 (4)	−0.0632 (3)	0.56174 (9)	0.0415 (6)
H7	0.2664	0.0308	0.5675	0.050*
C8	0.2051 (4)	−0.1875 (3)	0.59386 (9)	0.0427 (6)
H8	0.2705	−0.1762	0.6209	0.051*
C9	0.1043 (3)	0.0598 (3)	0.48540 (9)	0.0353 (6)
C10	0.0092 (3)	0.0467 (3)	0.44397 (9)	0.0409 (6)
H10	−0.0528	−0.0486	0.4383	0.049*
C11	0.0048 (3)	0.1697 (4)	0.41162 (9)	0.0434 (6)
H11	−0.0601	0.1567	0.3845	0.052*
C12	0.0958 (3)	0.3135 (3)	0.41877 (8)	0.0367 (6)
C13	0.1927 (4)	0.3298 (3)	0.45907 (9)	0.0457 (7)
H13	0.2558	0.4248	0.4645	0.055*
C14	0.1950 (4)	0.2043 (3)	0.49115 (10)	0.0481 (7)
H14	0.2609	0.2173	0.5181	0.058*
C15	0.1904 (4)	0.5669 (3)	0.38615 (9)	0.0452 (7)
H15A	0.3090	0.5326	0.3909	0.054*
H15B	0.1579	0.6398	0.4114	0.054*
C16	0.1717 (4)	0.6512 (4)	0.33992 (10)	0.0480 (7)
C17	0.8034 (4)	0.4650 (3)	0.76651 (10)	0.0467 (7)
H17	0.8715	0.4520	0.7930	0.056*
C18	0.7724 (5)	0.1739 (4)	0.76798 (13)	0.0648 (9)
H18A	0.6666	0.1321	0.7807	0.097*
H18B	0.8570	0.1827	0.7924	0.097*
H18C	0.8139	0.1009	0.7442	0.097*
C19	0.6242 (5)	0.3421 (4)	0.70858 (11)	0.0618 (9)
H19A	0.6722	0.2833	0.6826	0.093*
H19B	0.6064	0.4543	0.6999	0.093*
H19C	0.5158	0.2939	0.7172	0.093*
N1	0.7419 (3)	0.3344 (3)	0.74773 (7)	0.0437 (6)
O1	−0.0176 (3)	−0.8381 (3)	0.65378 (8)	0.0711 (7)
O2	0.1679 (3)	−0.6642 (3)	0.68480 (7)	0.0616 (6)
H2	0.1823	−0.7387	0.7036	0.092*
O3	0.1272 (3)	−0.4482 (2)	0.61989 (6)	0.0458 (5)
O4	0.0795 (3)	0.4294 (2)	0.38492 (6)	0.0468 (5)
O5	0.0680 (5)	0.6151 (4)	0.31136 (10)	0.1098 (12)
O6	0.2858 (4)	0.7658 (3)	0.33427 (8)	0.0768 (8)
H6	0.2834	0.7982	0.3072	0.115*
O7	0.7798 (3)	0.6075 (2)	0.75226 (6)	0.0565 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0502 (16)	0.0377 (15)	0.0433 (15)	0.0007 (13)	0.0004 (13)	0.0008 (13)
C2	0.0553 (17)	0.0427 (16)	0.0461 (16)	−0.0061 (14)	−0.0045 (14)	0.0050 (14)
C3	0.0408 (13)	0.0347 (13)	0.0399 (13)	0.0016 (12)	−0.0011 (11)	0.0039 (12)
C4	0.0592 (18)	0.0400 (16)	0.0533 (16)	−0.0170 (15)	−0.0174 (14)	0.0059 (14)
C5	0.0581 (18)	0.0478 (16)	0.0459 (16)	−0.0142 (15)	−0.0207 (14)	0.0058 (14)
C6	0.0337 (12)	0.0357 (13)	0.0372 (13)	0.0027 (11)	0.0011 (11)	−0.0001 (12)
C7	0.0457 (15)	0.0375 (14)	0.0411 (14)	−0.0062 (12)	−0.0066 (12)	0.0010 (12)
C8	0.0468 (15)	0.0463 (15)	0.0350 (13)	−0.0014 (14)	−0.0063 (12)	0.0008 (12)
C9	0.0333 (12)	0.0365 (13)	0.0361 (13)	0.0013 (11)	0.0018 (11)	0.0003 (12)
C10	0.0419 (14)	0.0407 (15)	0.0400 (14)	−0.0089 (13)	−0.0011 (12)	−0.0023 (12)
C11	0.0428 (14)	0.0536 (17)	0.0339 (13)	−0.0037 (14)	−0.0044 (11)	0.0031 (13)
C12	0.0384 (13)	0.0377 (14)	0.0340 (13)	0.0037 (12)	0.0042 (11)	0.0033 (11)
C13	0.0553 (16)	0.0371 (14)	0.0446 (15)	−0.0066 (14)	−0.0071 (13)	0.0052 (13)
C14	0.0561 (16)	0.0479 (17)	0.0403 (15)	−0.0079 (15)	−0.0119 (13)	0.0049 (13)
C15	0.0533 (16)	0.0402 (15)	0.0420 (14)	0.0025 (14)	0.0030 (13)	0.0020 (13)
C16	0.0502 (16)	0.0475 (16)	0.0462 (16)	0.0002 (15)	−0.0003 (14)	0.0065 (14)
C17	0.0606 (18)	0.0434 (16)	0.0360 (14)	0.0003 (15)	−0.0080 (14)	0.0035 (13)
C18	0.082 (2)	0.0402 (17)	0.072 (2)	0.0019 (17)	0.003 (2)	0.0110 (16)
C19	0.068 (2)	0.058 (2)	0.0588 (19)	0.0028 (17)	−0.0166 (16)	−0.0103 (17)
N1	0.0493 (13)	0.0403 (13)	0.0413 (12)	0.0008 (11)	−0.0014 (11)	−0.0021 (10)
O1	0.0894 (17)	0.0499 (13)	0.0740 (15)	−0.0250 (14)	−0.0256 (13)	0.0132 (12)
O2	0.0847 (15)	0.0422 (11)	0.0579 (12)	−0.0134 (12)	−0.0230 (12)	0.0114 (10)
O3	0.0523 (11)	0.0415 (10)	0.0436 (10)	−0.0074 (9)	−0.0085 (9)	0.0107 (9)
O4	0.0498 (11)	0.0469 (11)	0.0436 (10)	−0.0045 (9)	−0.0043 (9)	0.0110 (10)
O5	0.119 (2)	0.123 (3)	0.0881 (19)	−0.058 (2)	−0.0515 (19)	0.060 (2)
O6	0.1004 (19)	0.0726 (16)	0.0573 (14)	−0.0360 (16)	−0.0152 (14)	0.0243 (12)
O7	0.0860 (16)	0.0393 (11)	0.0444 (12)	−0.0036 (11)	−0.0131 (11)	0.0042 (9)

Geometric parameters (Å, º) top

C1—O1	1.197 (3)	C12—O4	1.361 (3)
C1—O2	1.305 (4)	C12—C13	1.383 (4)
C1—C2	1.493 (4)	C13—C14	1.377 (4)
C2—O3	1.407 (3)	C13—H13	0.9300
C2—H2A	0.9700	C14—H14	0.9300
C2—H2B	0.9700	C15—O4	1.415 (3)
C3—O3	1.366 (3)	C15—C16	1.499 (4)
C3—C8	1.377 (4)	C15—H15A	0.9700
C3—C4	1.383 (4)	C15—H15B	0.9700
C4—C5	1.382 (4)	C16—O5	1.184 (4)
C4—H4	0.9300	C16—O6	1.298 (4)
C5—C6	1.382 (4)	C17—O7	1.248 (3)
C5—H5	0.9300	C17—N1	1.287 (4)
C6—C7	1.394 (4)	C17—H17	0.9300
C6—C9	1.489 (4)	C18—N1	1.454 (4)
C7—C8	1.371 (4)	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—H8	0.9300	C18—H18C	0.9600
C9—C14	1.385 (4)	C19—N1	1.446 (4)
C9—C10	1.400 (3)	C19—H19A	0.9600
C10—C11	1.368 (4)	C19—H19B	0.9600
C10—H10	0.9300	C19—H19C	0.9600
C11—C12	1.386 (4)	O2—H2	0.8201
C11—H11	0.9300	O6—H6	0.8200

O1—C1—O2	123.9 (3)	C13—C12—C11	118.8 (2)
O1—C1—C2	120.7 (3)	C14—C13—C12	119.4 (3)
O2—C1—C2	115.4 (2)	C14—C13—H13	120.3
O3—C2—C1	112.0 (2)	C12—C13—H13	120.3
O3—C2—H2A	109.2	C13—C14—C9	123.4 (3)
C1—C2—H2A	109.2	C13—C14—H14	118.3
O3—C2—H2B	109.2	C9—C14—H14	118.3
C1—C2—H2B	109.2	O4—C15—C16	106.5 (2)
H2A—C2—H2B	107.9	O4—C15—H15A	110.4
O3—C3—C8	116.8 (2)	C16—C15—H15A	110.4
O3—C3—C4	124.4 (2)	O4—C15—H15B	110.4
C8—C3—C4	118.8 (2)	C16—C15—H15B	110.4
C5—C4—C3	119.3 (3)	H15A—C15—H15B	108.6
C5—C4—H4	120.3	O5—C16—O6	123.8 (3)
C3—C4—H4	120.3	O5—C16—C15	124.1 (3)
C4—C5—C6	123.1 (2)	O6—C16—C15	112.1 (3)
C4—C5—H5	118.5	O7—C17—N1	125.7 (3)
C6—C5—H5	118.5	O7—C17—H17	117.1
C5—C6—C7	116.0 (2)	N1—C17—H17	117.1
C5—C6—C9	121.9 (2)	N1—C18—H18A	109.5
C7—C6—C9	122.0 (2)	N1—C18—H18B	109.5
C8—C7—C6	121.8 (2)	H18A—C18—H18B	109.5
C8—C7—H7	119.1	N1—C18—H18C	109.5
C6—C7—H7	119.1	H18A—C18—H18C	109.5
C7—C8—C3	120.9 (2)	H18B—C18—H18C	109.5
C7—C8—H8	119.5	N1—C19—H19A	109.5
C3—C8—H8	119.5	N1—C19—H19B	109.5
C14—C9—C10	115.7 (2)	H19A—C19—H19B	109.5
C14—C9—C6	122.8 (2)	N1—C19—H19C	109.5
C10—C9—C6	121.6 (2)	H19A—C19—H19C	109.5
C11—C10—C9	122.0 (2)	H19B—C19—H19C	109.5
C11—C10—H10	119.0	C17—N1—C19	121.4 (2)
C9—C10—H10	119.0	C17—N1—C18	121.4 (2)
C10—C11—C12	120.7 (2)	C19—N1—C18	116.8 (3)
C10—C11—H11	119.6	C1—O2—H2	109.4
C12—C11—H11	119.6	C3—O3—C2	117.8 (2)
O4—C12—C13	125.2 (2)	C12—O4—C15	118.6 (2)
O4—C12—C11	116.0 (2)	C16—O6—H6	109.6

O1—C1—C2—O3	−178.9 (3)	C9—C10—C11—C12	0.2 (4)
O2—C1—C2—O3	1.4 (4)	C10—C11—C12—O4	−178.6 (2)
O3—C3—C4—C5	−178.3 (3)	C10—C11—C12—C13	0.6 (4)
C8—C3—C4—C5	0.6 (4)	O4—C12—C13—C14	178.4 (3)
C3—C4—C5—C6	0.4 (5)	C11—C12—C13—C14	−0.7 (4)
C4—C5—C6—C7	−1.1 (4)	C12—C13—C14—C9	0.0 (5)
C4—C5—C6—C9	178.8 (3)	C10—C9—C14—C13	0.8 (4)
C5—C6—C7—C8	0.7 (4)	C6—C9—C14—C13	−179.0 (3)
C9—C6—C7—C8	−179.1 (3)	O4—C15—C16—O5	7.5 (5)
C6—C7—C8—C3	0.2 (4)	O4—C15—C16—O6	−170.6 (2)
O3—C3—C8—C7	178.1 (2)	O7—C17—N1—C19	−4.7 (5)
C4—C3—C8—C7	−0.9 (4)	O7—C17—N1—C18	−178.0 (3)
C5—C6—C9—C14	178.9 (3)	C8—C3—O3—C2	176.0 (2)
C7—C6—C9—C14	−1.3 (4)	C4—C3—O3—C2	−5.0 (4)
C5—C6—C9—C10	−0.9 (4)	C1—C2—O3—C3	179.1 (2)
C7—C6—C9—C10	178.9 (2)	C13—C12—O4—C15	11.2 (4)
C14—C9—C10—C11	−0.8 (4)	C11—C12—O4—C15	−169.7 (2)
C6—C9—C10—C11	179.0 (2)	C16—C15—O4—C12	167.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O7ⁱ	0.82	1.87	2.685 (3)	174
O2—H2···O7ⁱⁱ	0.82	1.81	2.626 (3)	176
C15—H15a···O1ⁱⁱⁱ	0.97	2.44	3.149 (2)	129
C17—H17···O1^iv	0.93	2.56	3.248 (3)	131

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1, y−3/2, −z+3/2; (iii) x+1/2, −y−1/2, −z+1; (iv) −x+1, y+3/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄O₆·C₃H₇NO
M_r	375.37
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.7471 (15), 8.1758 (16), 28.625 (6)
V (Å³)	1813.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.32 × 0.25 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.971, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9412, 2079, 1778
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.116, 1.05
No. of reflections	2079
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O7ⁱ	0.82	1.87	2.685 (3)	174.4
O2—H2···O7ⁱⁱ	0.82	1.81	2.626 (3)	176.0
C15—H15a···O1ⁱⁱⁱ	0.97	2.44	3.149 (2)	129.0
C17—H17···O1^iv	0.93	2.56	3.248 (3)	131.0

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1, y−3/2, −z+3/2; (iii) x+1/2, −y−1/2, −z+1; (iv) −x+1, y+3/2, −z+3/2.

References

Bruker (2004). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Kamoda, O., Anzai, K., Mizoguchi, J., Shiojiri, M., Yanagi, T., Nishino, T. & Kamiya, S. (2006). Antimicrob. Agents Chemother. 50, 3062–3069. Web of Science CrossRef PubMed CAS Google Scholar
Mikami, K. & Yamanaka, M. (2003). Chem. Rev. 103, 3369–3400. Web of Science CrossRef PubMed CAS Google Scholar
Rabnawaz, M., Ali, Q., Shah, M. R. & Singh, K. (2008). Acta Cryst. E64, o1909. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sallam, M. M., El-Sayed, B. A. & Abdel-Shafi, A. A. (2006). Curr. Appl. Phys. 6, 71–75. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tan, T.-F., Zhang, J.-X. & Meng, J.-B. (2005). Acta Cryst. E61, o1210–o1211. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Page o1851

doi:10.1107/S1600536809025914

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