2,2'-Dihydroxybiphenyl-3,3'-di-carb-aldehyde dioxime.

The mol-ecule of the title compound, C(14)H(12)N(2)O(4), lies across a crystallographic inversion centre situated at the mid-point of the C-C intra-annular bond. The mol-ecule is not planar, the dihedral angle between the aromatic rings being 50.1 (1)°. The oxime group is in an E position with respect to the -OH group and forms an intra-molecular O-H⋯N hydrogen bond. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link mol-ecules into chains propagating along [001]. The crystal structure is further stabilized by inter-molecular stacking inter-actions between the rings [centroid-to-centroid distance = 3.93 (1) Å], resulting in layers parallel to the bc plane.

Related literature

For the use of oximes as chelating ligands in coordination and analytical chemistry and extraction metallurgy, see: Kukushkin et al. (1996 ▶); Chaudhuri (2003 ▶). For the use of oxime ligands to obtain polynuclear compounds in the fields of mol­ecular magnetism and supra­molecular chemistry, see: Cervera et al. (1997 ▶); Costes et al. (1998 ▶). Oxime-containing ligands have been found to efficiently stabilize high oxidation states of metal ions such as Cu(III) and Ni(III), see: Fritsky et al. (2006 ▶); Kanderal et al. (2005 ▶). For C=N and N—O bond lengths in oximes, see: Mokhir et al. (2002 ▶); Onindo et al. (1995 ▶); Sliva et al. (1997 ▶). For the synthesis of 2,2′-dihydroxy­biphenyl-3,3′-dicarbaldehyde, see: Wünnemann et al. (2008 ▶).

Experimental

Crystal data

C14H12N2O4

M = 272.26

Monoclinic,

a = 24.2780 (14) Å

b = 3.9279 (4) Å

c = 16.6466 (12) Å

β = 129.652 (6)°

V = 1222.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 120 K

0.19 × 0.09 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.976, T max = 0.993

4331 measured reflections

1388 independent reflections

812 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.146

S = 1.02

1388 reflections

99 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Bruker–Nonius, 2004 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029298/jh2095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029298/jh2095Isup2.hkl

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

C14H12N2O4	F(000) = 568
Mr = 272.26	Dx = 1.480 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 516 reflections
a = 24.2780 (14) Å	θ = 4.5–27.0°
b = 3.9279 (4) Å	µ = 0.11 mm−1
c = 16.6466 (12) Å	T = 120 K
β = 129.652 (6)°	Block, pale-yellow
V = 1222.2 (2) Å3	0.19 × 0.09 × 0.06 mm
Z = 4

Nonius KappaCCD diffractometer	1388 independent reflections
Radiation source: fine-focus sealed tube	812 reflections with I > 2σ(I)
horizontally mounted graphite crystal	Rint = 0.073
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 4.4°
φ scans and ω scans with κ offset	h = −30→30
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	k = −5→4
Tmin = 0.976, Tmax = 0.993	l = −18→21
4331 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0673P)2] where P = (Fo2 + 2Fc2)/3
1388 reflections	(Δ/σ)max < 0.001
99 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.50535 (8)	0.1656 (4)	0.11701 (11)	0.0286 (5)
O2	0.64023 (9)	−0.1055 (4)	0.07166 (13)	0.0350 (5)
N1	0.60748 (10)	0.0232 (5)	0.11062 (14)	0.0279 (5)
C1	0.55751 (12)	0.2918 (5)	0.21487 (16)	0.0236 (6)
C2	0.53803 (11)	0.4208 (6)	0.27199 (16)	0.0235 (6)
C3	0.59205 (12)	0.5499 (6)	0.37151 (16)	0.0265 (6)
H3	0.5795	0.6439	0.4105	0.032*
C4	0.66275 (12)	0.5455 (6)	0.41490 (17)	0.0269 (6)
H4	0.6983	0.6329	0.4832	0.032*
C5	0.68185 (12)	0.4140 (6)	0.35911 (16)	0.0272 (6)
H5	0.7308	0.4102	0.3893	0.033*
C6	0.62978 (11)	0.2855 (6)	0.25813 (16)	0.0237 (6)
C7	0.65242 (12)	0.1435 (6)	0.20269 (17)	0.0265 (6)
H7	0.7019	0.1402	0.2358	0.032*
H1	0.5270 (14)	0.081 (7)	0.0923 (19)	0.042 (8)*
H2	0.5979 (18)	−0.165 (8)	−0.002 (3)	0.067 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0229 (9)	0.0387 (10)	0.0217 (9)	−0.0034 (7)	0.0132 (8)	−0.0059 (7)
O2	0.0324 (10)	0.0468 (11)	0.0296 (10)	0.0008 (8)	0.0217 (9)	−0.0042 (8)
N1	0.0299 (11)	0.0321 (11)	0.0277 (11)	0.0015 (9)	0.0212 (10)	−0.0001 (8)
C1	0.0244 (13)	0.0233 (12)	0.0192 (12)	−0.0006 (9)	0.0121 (11)	0.0013 (9)
C2	0.0235 (12)	0.0218 (12)	0.0213 (11)	−0.0002 (9)	0.0124 (11)	0.0017 (9)
C3	0.0306 (14)	0.0266 (13)	0.0231 (12)	−0.0015 (10)	0.0176 (11)	0.0000 (10)
C4	0.0253 (13)	0.0301 (13)	0.0178 (11)	−0.0044 (10)	0.0103 (10)	−0.0024 (9)
C5	0.0211 (12)	0.0290 (14)	0.0257 (12)	−0.0018 (10)	0.0123 (11)	0.0011 (10)
C6	0.0237 (13)	0.0246 (12)	0.0204 (12)	−0.0012 (9)	0.0130 (11)	0.0020 (9)
C7	0.0207 (12)	0.0311 (13)	0.0252 (12)	−0.0008 (10)	0.0136 (11)	0.0008 (10)

O1—C1	1.368 (3)	C3—C4	1.373 (3)
O1—H1	0.91 (3)	C3—H3	0.9500
O2—N1	1.402 (2)	C4—C5	1.376 (3)
O2—H2	1.00 (3)	C4—H4	0.9500
N1—C7	1.276 (3)	C5—C6	1.402 (3)
C1—C2	1.399 (3)	C5—H5	0.9500
C1—C6	1.409 (3)	C6—C7	1.453 (3)
C2—C3	1.396 (3)	C7—H7	0.9500
C2—C2i	1.490 (4)
C1—O1—H1	107.9 (16)	C3—C4—C5	119.7 (2)
N1—O2—H2	101.8 (18)	C3—C4—H4	120.1
C7—N1—O2	112.73 (17)	C5—C4—H4	120.1
O1—C1—C2	118.89 (19)	C4—C5—C6	120.7 (2)
O1—C1—C6	120.46 (19)	C4—C5—H5	119.7
C2—C1—C6	120.6 (2)	C6—C5—H5	119.7
C3—C2—C1	118.0 (2)	C5—C6—C1	118.83 (19)
C3—C2—C2i	120.9 (2)	C5—C6—C7	118.8 (2)
C1—C2—C2i	121.1 (2)	C1—C6—C7	122.31 (19)
C4—C3—C2	122.1 (2)	N1—C7—C6	121.6 (2)
C4—C3—H3	118.9	N1—C7—H7	119.2
C2—C3—H3	118.9	C6—C7—H7	119.2
O1—C1—C2—C3	−179.69 (18)	C4—C5—C6—C7	−178.9 (2)
C6—C1—C2—C3	1.6 (3)	O1—C1—C6—C5	−179.3 (2)
O1—C1—C2—C2i	0.3 (3)	C2—C1—C6—C5	−0.6 (3)
C6—C1—C2—C2i	−178.47 (16)	O1—C1—C6—C7	−0.8 (3)
C1—C2—C3—C4	−1.7 (3)	C2—C1—C6—C7	177.9 (2)
C2i—C2—C3—C4	178.39 (17)	O2—N1—C7—C6	−179.16 (18)
C2—C3—C4—C5	0.8 (3)	C5—C6—C7—N1	−179.9 (2)
C3—C4—C5—C6	0.3 (3)	C1—C6—C7—N1	1.5 (3)
C4—C5—C6—C1	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.91 (3)	1.79 (3)	2.609 (2)	148 (2)
O2—H2···O1ii	1.00 (3)	1.96 (3)	2.871 (2)	151 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.91 (3)	1.79 (3)	2.609 (2)	148 (2)
O2—H2⋯O1i	1.00 (3)	1.96 (3)	2.871 (2)	151 (3)

Symmetry code: (i) .