2,2'-(Biphenyl-4,4'-diyldi-oxy)diacetic acid N,N-dimethyl-formamide solvate.

In the crystal struture of the title compound, C(16)H(14)O(6)·C(3)H(7)NO, 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 mol-ecule, 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 = 375.37

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.05

2079 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

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.

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

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

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

C16H14O6·C3H7NO	Dx = 1.375 Mg m−3
Mr = 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

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

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(Fo2) + (0.0655P)2 + 0.2914P] where P = (Fo2 + 2Fc2)/3
2079 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)	129.0
C17—H17···O1iv	0.93	2.56	3.248 (3)	131

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⋯O1iv	0.93	2.56	3.248 (3)	131

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .