Biphenyl-4,4′-dicarb­oxy­lic acid N,N-dimethyl­formamide monosolvate

Jakobsen, S.; Wragg, D.S.; Lillerud, K.P.

doi:10.1107/S1600536810030515

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2209

https://doi.org/10.1107/S1600536810030515

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Biphenyl-4,4′-dicarboxylic acid N,N-dimethylformamide monosolvate

Søren Jakobsen,^a David Stephen Wragg ^a ^* and Karl Petter Lillerud ^a

^ainGAP Centre for Research Based Innovation, Department of Chemistry, University of Oslo, 0315 Oslo, Norway
^*Correspondence e-mail: david.wragg@smn.uio.no

(Received 24 June 2010; accepted 30 July 2010; online 4 August 2010)

Biphenyl-4,4′-dicarboxylic acid was recrystallized from N,N-dimethylformamide (DMF) yielding the title compound, C₁₄H₁₀O₄·2C₃H₇NO. The acid molecules are located on crystallographic centres of inversion and are hydrogen bonded to DMF molecules. These hydrogen-bonded units form infinite chains although there is no interaction between the methyl groups of neighboring DMF molecules.

Related literature

The title compound is a popular linker for the synthesis of metal-organic framework materials, for example IRMOF 10 (Eddaoudi et al., 2002 ) and UIO-67 (Cavka et al., 2008 ).

Experimental

Crystal data

C₁₄H₁₀O₄·2C₃H₇NO
M_r = 388.41
Triclinic, $[P \overline 1]$
a = 7.666 (7) Å
b = 7.774 (7) Å
c = 9.099 (8) Å
α = 88.549 (10)°
β = 73.596 (10)°
γ = 65.208 (7)°
V = 469.6 (7) Å³
Z = 1
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 K
0.2 × 0.2 × 0.1 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.980, T_max = 0.990
3968 measured reflections
2136 independent reflections
1635 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.175
S = 1.11
2136 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3ⁱ	0.82	1.76	2.575 (2)	172
Symmetry code: (i) x, y+1, z-1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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 and enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810030515/bt5277sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030515/bt5277Isup2.hkl

checkCIF report

Comment top

The title compound, (I) (Fig. 1), which is a popular linker for the synthesis of metal-organic framework materials, for example IRMOF 10 (Eddaoudi et al., 2002) and UIO-67 (Cavka et al., 2008), comprises units of one biphenyl-4,4'-dicarboxylic acid molecule hydrogen bonded to two DMF molecules via O—H···O links. These units pack as chains (Fig. 2), although there is no interaction between the methyl groups of neighboring DMF molecules. The chains are arranged in layers with no stacking interactions between the benzene rings (Fig. 3).

Related literature top

The title compound is a popular linker for the synthesis of metal-organic framework materials, for example IRMOF 10 (Eddaoudi et al., 2002) and UIO-67 (Cavka et al., 2008).

Experimental top

Biphenyl-4,4'-dicarboxylic acid and N,N-Dimethylformamide (DMF) were purchased from Sigma-Aldrich and used without further purification. 1.0 g Biphenyl-4,4'dicarboxylic acid was suspended in 100 ml DMF and heated to 100°C. DMF was added in small portions until the acid had just dissolved (app. 50 ml) and the solution left in aluminium foil over night for slow cool-down to RT. Filtration of the now 125 ml DMF suspension yielded 0.57 g white powder of Biphenyl-4,4-dicarboxylic acid after drying under vacuum. The mother liquor was placed at 5°C over night which gave a small amount of colourless crystals, which gave the structure presented here.

Structure description top

The title compound is a popular linker for the synthesis of metal-organic framework materials, for example IRMOF 10 (Eddaoudi et al., 2002) and UIO-67 (Cavka et al., 2008).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. Unlabeled atoms are related to the labeled ones by an inversion centre.
	Fig. 2. The packing of (I), showing the hydrogen bonded chains. Hydrogen atoms are omitted and hydrogen bonds are shown as dashed lines.
	Fig. 3. The packing of (I), showing the layers formed by the chains. Hydrogen atoms are omitted and hydrogen bonds are shown as dashed lines.

Biphenyl-4,4'-dicarboxylic acid N,N-dimethylformamide monosolvate top

Crystal data top

C₁₄H₁₀O₄·2C₃H₇NO	Z = 1
M_r = 388.41	F(000) = 206
Triclinic, P1	D_x = 1.374 Mg m⁻³
a = 7.666 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.774 (7) Å	Cell parameters from 1412 reflections
c = 9.099 (8) Å	θ = 2.4–28.2°
α = 88.549 (10)°	µ = 0.10 mm⁻¹
β = 73.596 (10)°	T = 150 K
γ = 65.208 (7)°	Prism, colourless
V = 469.6 (7) Å³	0.2 × 0.2 × 0.1 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	2136 independent reflections
Radiation source: sealed tube	1635 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
phi and ω scans	θ_max = 28.8°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→10
T_min = 0.980, T_max = 0.990	k = −10→10
3968 measured reflections	l = −12→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.1177P)²] where P = (F_o² + 2F_c²)/3
2136 reflections	(Δ/σ)_max < 0.001
129 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₄H₁₀O₄·2C₃H₇NO	γ = 65.208 (7)°
M_r = 388.41	V = 469.6 (7) Å³
Triclinic, P1	Z = 1
a = 7.666 (7) Å	Mo Kα radiation
b = 7.774 (7) Å	µ = 0.10 mm⁻¹
c = 9.099 (8) Å	T = 150 K
α = 88.549 (10)°	0.2 × 0.2 × 0.1 mm
β = 73.596 (10)°

Data collection top

Bruker APEX CCD area-detector diffractometer	2136 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1635 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.990	R_int = 0.015
3968 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.11	Δρ_max = 0.40 e Å⁻³
2136 reflections	Δρ_min = −0.32 e Å⁻³
129 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.1394 (2)	0.7816 (2)	0.21617 (19)	0.0217 (4)
C2	−0.0126 (3)	0.8677 (2)	0.3535 (2)	0.0260 (4)
H2	−0.0795	0.9999	0.3711	0.031*
C3	−0.0653 (3)	0.7578 (2)	0.4645 (2)	0.0265 (4)
H3	−0.1653	0.8178	0.5567	0.032*
C4	0.0289 (2)	0.5590 (2)	0.44054 (18)	0.0208 (4)
C5	0.1794 (3)	0.4743 (2)	0.30105 (19)	0.0252 (4)
H5	0.2442	0.3421	0.2816	0.030*
C6	0.2336 (2)	0.5847 (2)	0.1908 (2)	0.0251 (4)
H6	0.3344	0.5255	0.0989	0.030*
C7	0.1957 (2)	0.9059 (2)	0.10229 (19)	0.0240 (4)
O1	0.1055 (2)	1.07728 (18)	0.11935 (16)	0.0363 (4)
O2	0.35493 (18)	0.80786 (17)	−0.01629 (14)	0.0282 (3)
H2A	0.3804	0.8814	−0.0753	0.042*
O3	0.44518 (19)	0.01439 (18)	0.77730 (15)	0.0333 (4)
N1	0.3688 (2)	0.3198 (2)	0.72336 (17)	0.0249 (4)
C8	0.3490 (3)	0.1893 (2)	0.8138 (2)	0.0267 (4)
H8	0.2566	0.2312	0.9116	0.032*
C9	0.5089 (3)	0.2649 (3)	0.5689 (2)	0.0292 (4)
H9A	0.4432	0.3379	0.4976	0.044*
H9B	0.5531	0.1317	0.5410	0.044*
H9C	0.6229	0.2888	0.5657	0.044*
C10	0.2551 (3)	0.5215 (2)	0.7753 (2)	0.0304 (4)
H10A	0.1787	0.5833	0.7065	0.046*
H10B	0.3461	0.5763	0.7765	0.046*
H10C	0.1653	0.5386	0.8773	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0211 (8)	0.0194 (8)	0.0226 (8)	−0.0075 (6)	−0.0056 (6)	0.0033 (6)
C2	0.0264 (8)	0.0157 (8)	0.0281 (9)	−0.0054 (6)	−0.0020 (7)	0.0009 (6)
C3	0.0262 (8)	0.0204 (8)	0.0242 (8)	−0.0076 (6)	0.0015 (6)	−0.0006 (6)
C4	0.0199 (8)	0.0187 (8)	0.0218 (8)	−0.0066 (6)	−0.0061 (6)	0.0033 (6)
C5	0.0274 (8)	0.0155 (8)	0.0243 (8)	−0.0045 (6)	−0.0029 (7)	0.0016 (6)
C6	0.0267 (8)	0.0178 (8)	0.0224 (8)	−0.0054 (6)	−0.0012 (6)	0.0010 (6)
C7	0.0244 (8)	0.0186 (8)	0.0247 (8)	−0.0069 (6)	−0.0047 (6)	0.0029 (6)
O1	0.0389 (8)	0.0173 (7)	0.0360 (8)	−0.0057 (6)	0.0031 (6)	0.0042 (5)
O2	0.0307 (7)	0.0185 (6)	0.0252 (7)	−0.0071 (5)	0.0006 (5)	0.0045 (5)
O3	0.0358 (7)	0.0216 (7)	0.0326 (7)	−0.0083 (5)	−0.0024 (6)	0.0065 (5)
N1	0.0260 (7)	0.0190 (7)	0.0265 (7)	−0.0084 (6)	−0.0053 (6)	0.0036 (6)
C8	0.0254 (8)	0.0238 (9)	0.0260 (9)	−0.0080 (7)	−0.0047 (7)	0.0051 (6)
C9	0.0308 (9)	0.0251 (9)	0.0274 (9)	−0.0108 (7)	−0.0045 (7)	0.0061 (7)
C10	0.0342 (9)	0.0199 (9)	0.0342 (9)	−0.0095 (7)	−0.0090 (7)	−0.0001 (7)

Geometric parameters (Å, º) top

C1—C6	1.383 (3)	C7—O2	1.324 (2)
C1—C2	1.390 (2)	O2—H2A	0.8200
C1—C7	1.497 (2)	O3—C8	1.244 (2)
C2—C3	1.389 (3)	N1—C8	1.321 (2)
C2—H2	0.9300	N1—C10	1.449 (2)
C3—C4	1.396 (3)	N1—C9	1.451 (2)
C3—H3	0.9300	C8—H8	0.9300
C4—C5	1.398 (2)	C9—H9A	0.9600
C4—C4ⁱ	1.493 (3)	C9—H9B	0.9600
C5—C6	1.392 (2)	C9—H9C	0.9600
C5—H5	0.9300	C10—H10A	0.9600
C6—H6	0.9300	C10—H10B	0.9600
C7—O1	1.206 (2)	C10—H10C	0.9600

C6—C1—C2	118.77 (15)	O2—C7—C1	112.84 (15)
C6—C1—C7	122.67 (15)	C7—O2—H2A	109.5
C2—C1—C7	118.56 (16)	C8—N1—C10	121.51 (15)
C3—C2—C1	120.52 (16)	C8—N1—C9	120.74 (15)
C3—C2—H2	119.7	C10—N1—C9	117.75 (14)
C1—C2—H2	119.7	O3—C8—N1	124.59 (17)
C2—C3—C4	121.27 (16)	O3—C8—H8	117.7
C2—C3—H3	119.4	N1—C8—H8	117.7
C4—C3—H3	119.4	N1—C9—H9A	109.5
C3—C4—C5	117.62 (14)	N1—C9—H9B	109.5
C3—C4—C4ⁱ	121.26 (18)	H9A—C9—H9B	109.5
C5—C4—C4ⁱ	121.12 (18)	N1—C9—H9C	109.5
C6—C5—C4	120.95 (15)	H9A—C9—H9C	109.5
C6—C5—H5	119.5	H9B—C9—H9C	109.5
C4—C5—H5	119.5	N1—C10—H10A	109.5
C1—C6—C5	120.84 (16)	N1—C10—H10B	109.5
C1—C6—H6	119.6	H10A—C10—H10B	109.5
C5—C6—H6	119.6	N1—C10—H10C	109.5
O1—C7—O2	124.29 (16)	H10A—C10—H10C	109.5
O1—C7—C1	122.87 (16)	H10B—C10—H10C	109.5

C6—C1—C2—C3	1.5 (3)	C7—C1—C6—C5	178.71 (15)
C7—C1—C2—C3	−177.92 (15)	C4—C5—C6—C1	−0.2 (3)
C1—C2—C3—C4	−1.4 (3)	C6—C1—C7—O1	175.06 (16)
C2—C3—C4—C5	0.4 (3)	C2—C1—C7—O1	−5.5 (3)
C2—C3—C4—C4ⁱ	−179.51 (17)	C6—C1—C7—O2	−5.8 (2)
C3—C4—C5—C6	0.4 (3)	C2—C1—C7—O2	173.65 (15)
C4ⁱ—C4—C5—C6	−179.67 (17)	C10—N1—C8—O3	−178.38 (16)
C2—C1—C6—C5	−0.7 (3)	C9—N1—C8—O3	0.5 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱⁱ	0.82	1.76	2.575 (2)	172

Symmetry code: (ii) x, y+1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀O₄·2C₃H₇NO
M_r	388.41
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	7.666 (7), 7.774 (7), 9.099 (8)
α, β, γ (°)	88.549 (10), 73.596 (10), 65.208 (7)
V (Å³)	469.6 (7)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.2 × 0.2 × 0.1

Data collection
Diffractometer	Bruker APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.980, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	3968, 2136, 1635
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.677

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.175, 1.11
No. of reflections	2136
No. of parameters	129
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.32

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), SHELXL97 (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱ	0.82	1.76	2.575 (2)	172.0

Symmetry code: (i) x, y+1, z−1.

Acknowledgements

The authors thank The Research Council of Norway, SMN and inGAP for funding.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cavka, J. H., Jakobsen, S., Olsbye, U., Guillou, N., Lamberti, C., Bordiga, S. & Lillerud, K. P. (2008). J. Am. Chem. Soc. 130, 13850–13851. Web of Science CSD CrossRef PubMed Google Scholar
Eddaoudi, M., Kim, J., Rosi, N. L., Vodak, B. T., Wachter, J., O'Keeffe, M. & Yaghi, O. M. (2002). Science, 295, 469–472. Web of Science CSD CrossRef PubMed CAS 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