4,4'-(Anthracene-9,10-di-yl)dibenzoic acid dimethyl-formamide disolvate.

In the title compound, C(28)H(18)O(4)·2C(3)H(7)NO, the dihedral angle between the benzene rings and the anthracene system is 74.05 (12)°. A crystallographic inversion centre is located in the middle of the anthracene unit. The dimethyl-formamide solvent mol-ecules are partially disordered over two positions of approximately equal occupancy [0.529 (6):0.471 (6)]. Inter-molecular O-H⋯O hydrogen bonds with the major occupancy formamide O atom as acceptor result in the formation of 2:1 solvate-complex aggregates, which are alternately linked to shorter solvate units via weak inter-molecular C-H⋯O contacts generated from the rotational disorder of the formamide O atom (minor occupancy component). Weak C-H⋯π inter-actions between the solvent mol-ecules as the donor and the outer anthracene rings support these contacts in the crystal structure for both disorder components.

Related literature

For the structure of 4-(2,5-dihexyl­oxyphen­yl)benzoic acid and the syntheses of related compounds, see: Li et al. (2008 ▶). For palladium-catalysed Suzuki coupling reactions, see: Xu et al. (2006 ▶, 2008 ▶); Li et al. (2006 ▶) and literature cited therein.

Experimental

Crystal data

C28H18O4·2C3H7NO

M = 564.62

Triclinic,

a = 7.3692 (15) Å

b = 8.9981 (18) Å

c = 12.124 (2) Å

α = 71.157 (3)°

β = 77.640 (3)°

γ = 79.754 (3)°

V = 738.0 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.23 × 0.16 × 0.06 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.980, T max = 0.994

5691 measured reflections

2721 independent reflections

1467 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.162

S = 1.02

2721 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.20 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014858/si2166sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014858/si2166Isup2.hkl

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

C28H18O4·2C3H7NO	Z = 1
Mr = 564.62	F(000) = 298
Triclinic, P1	Dx = 1.270 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3692 (15) Å	Cell parameters from 879 reflections
b = 8.9981 (18) Å	θ = 2.9–22.0°
c = 12.124 (2) Å	µ = 0.09 mm−1
α = 71.157 (3)°	T = 295 K
β = 77.640 (3)°	Block, colourless
γ = 79.754 (3)°	0.23 × 0.16 × 0.06 mm
V = 738.0 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	2721 independent reflections
Radiation source: fine-focus sealed tube	1467 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.980, Tmax = 0.994	k = −10→9
5691 measured reflections	l = −14→14

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0732P)2 + 0.04P] where P = (Fo2 + 2Fc2)/3
2721 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.20 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 > 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	Occ. (<1)
C15	0.5707 (5)	0.2790 (4)	0.4860 (3)	0.0742 (9)	0.529 (6)
H15	0.4771	0.2595	0.4536	0.089*	0.529 (6)
O3	0.5840 (5)	0.2039 (5)	0.5938 (4)	0.0918 (18)	0.529 (6)
C15'	0.5707 (5)	0.2790 (4)	0.4860 (3)	0.0742 (9)	0.471 (6)
H15'	0.5944	0.2141	0.5598	0.089*	0.471 (6)
O3'	0.4309 (7)	0.2700 (6)	0.4479 (4)	0.096 (2)	0.471 (6)
N1	0.6843 (3)	0.3826 (3)	0.41928 (19)	0.0637 (6)
C16	0.6620 (5)	0.4705 (4)	0.2994 (3)	0.0999 (12)
H16A	0.5498	0.4476	0.2831	0.150*
H16B	0.7677	0.4407	0.2459	0.150*
H16C	0.6535	0.5816	0.2895	0.150*
C17	0.8377 (4)	0.4104 (5)	0.4627 (3)	0.0945 (11)
H17A	0.8375	0.3450	0.5429	0.142*
H17B	0.8249	0.5196	0.4598	0.142*
H17C	0.9532	0.3852	0.4146	0.142*
O1	−0.1924 (3)	−0.0937 (3)	0.42504 (19)	0.1024 (9)
O2	−0.3377 (3)	−0.0181 (3)	0.2730 (2)	0.1090 (9)
H2D	−0.4140	−0.0728	0.3213	0.163*
C1	−0.0616 (3)	0.0915 (3)	0.2520 (2)	0.0496 (6)
C2	−0.0651 (4)	0.1757 (3)	0.1348 (2)	0.0638 (8)
H2	−0.1589	0.1662	0.0978	0.077*
C3	0.0713 (4)	0.2746 (3)	0.0719 (2)	0.0594 (7)
H3	0.0669	0.3313	−0.0068	0.071*
C4	0.2133 (3)	0.2901 (3)	0.1243 (2)	0.0445 (6)
C5	0.2169 (3)	0.2037 (3)	0.2414 (2)	0.0525 (7)
H5	0.3117	0.2117	0.2783	0.063*
C6	0.0805 (3)	0.1053 (3)	0.3045 (2)	0.0537 (7)
H6	0.0852	0.0480	0.3831	0.064*
C7	−0.2053 (4)	−0.0146 (3)	0.3219 (3)	0.0643 (8)
C8	0.6573 (4)	0.1754 (3)	−0.1369 (2)	0.0640 (8)
H8	0.6611	0.0821	−0.1552	0.077*
C9	0.5159 (4)	0.2148 (3)	−0.0568 (2)	0.0549 (7)
H9	0.4239	0.1477	−0.0204	0.066*
C10	0.5040 (3)	0.3575 (3)	−0.02629 (19)	0.0432 (6)
C11	0.3592 (3)	0.3985 (3)	0.05850 (19)	0.0419 (6)
C12	0.3533 (3)	0.5398 (3)	0.08512 (19)	0.0419 (6)
C13	0.2061 (3)	0.5896 (3)	0.1681 (2)	0.0514 (7)
H13	0.1110	0.5259	0.2059	0.062*
C14	0.2008 (4)	0.7263 (3)	0.1932 (2)	0.0620 (8)
H14	0.1031	0.7554	0.2478	0.074*

	U11	U22	U33	U12	U13	U23
C15	0.066 (2)	0.089 (2)	0.066 (2)	−0.0197 (18)	−0.0072 (17)	−0.0164 (19)
O3	0.082 (3)	0.114 (4)	0.071 (3)	−0.054 (3)	−0.012 (2)	0.006 (3)
C15'	0.066 (2)	0.089 (2)	0.066 (2)	−0.0197 (18)	−0.0072 (17)	−0.0164 (19)
O3'	0.087 (4)	0.120 (4)	0.079 (3)	−0.060 (3)	−0.015 (3)	0.000 (3)
N1	0.0574 (14)	0.0753 (17)	0.0547 (14)	−0.0202 (12)	−0.0040 (11)	−0.0113 (12)
C16	0.088 (2)	0.119 (3)	0.071 (2)	−0.022 (2)	−0.0099 (18)	0.004 (2)
C17	0.079 (2)	0.125 (3)	0.086 (2)	−0.045 (2)	−0.0063 (19)	−0.028 (2)
O1	0.0933 (16)	0.128 (2)	0.0722 (15)	−0.0639 (15)	−0.0176 (13)	0.0188 (14)
O2	0.0826 (16)	0.137 (2)	0.0938 (17)	−0.0672 (15)	−0.0245 (14)	0.0188 (15)
C1	0.0454 (14)	0.0470 (15)	0.0548 (16)	−0.0134 (12)	−0.0041 (12)	−0.0114 (12)
C2	0.0535 (16)	0.0701 (19)	0.0652 (18)	−0.0227 (14)	−0.0159 (14)	−0.0045 (15)
C3	0.0605 (16)	0.0624 (18)	0.0512 (15)	−0.0233 (14)	−0.0133 (13)	−0.0001 (13)
C4	0.0460 (14)	0.0408 (14)	0.0468 (14)	−0.0098 (11)	−0.0061 (11)	−0.0115 (12)
C5	0.0541 (15)	0.0553 (16)	0.0474 (15)	−0.0189 (13)	−0.0085 (12)	−0.0077 (13)
C6	0.0593 (16)	0.0519 (16)	0.0453 (14)	−0.0170 (13)	−0.0041 (12)	−0.0058 (12)
C7	0.0506 (17)	0.0634 (19)	0.074 (2)	−0.0191 (14)	−0.0030 (15)	−0.0121 (16)
C8	0.085 (2)	0.0442 (16)	0.0605 (17)	−0.0144 (14)	0.0043 (15)	−0.0192 (14)
C9	0.0667 (17)	0.0400 (15)	0.0549 (16)	−0.0186 (12)	0.0012 (13)	−0.0107 (12)
C10	0.0494 (14)	0.0359 (14)	0.0416 (13)	−0.0110 (11)	−0.0061 (11)	−0.0054 (11)
C11	0.0453 (13)	0.0386 (14)	0.0391 (13)	−0.0119 (10)	−0.0083 (11)	−0.0034 (11)
C12	0.0426 (13)	0.0404 (14)	0.0404 (13)	−0.0080 (10)	−0.0063 (10)	−0.0074 (11)
C13	0.0485 (14)	0.0494 (16)	0.0499 (15)	−0.0125 (12)	0.0041 (12)	−0.0104 (12)
C14	0.0724 (18)	0.0492 (17)	0.0573 (17)	−0.0080 (14)	0.0079 (14)	−0.0178 (14)

C15—O3	1.279 (4)	C3—H3	0.9300
C15—N1	1.314 (4)	C4—C5	1.385 (3)
C15—H15	0.9300	C4—C11	1.499 (3)
N1—C17	1.434 (4)	C5—C6	1.389 (3)
N1—C16	1.441 (3)	C5—H5	0.9300
C16—H16A	0.9600	C6—H6	0.9300
C16—H16B	0.9600	C8—C9	1.346 (3)
C16—H16C	0.9600	C8—C14i	1.406 (4)
C17—H17A	0.9600	C8—H8	0.9300
C17—H17B	0.9600	C9—C10	1.430 (3)
C17—H17C	0.9600	C9—H9	0.9300
O1—C7	1.238 (3)	C10—C11	1.403 (3)
O2—C7	1.255 (3)	C10—C12i	1.438 (3)
O2—H2D	0.8200	C11—C12	1.401 (3)
C1—C6	1.378 (3)	C12—C13	1.428 (3)
C1—C2	1.381 (3)	C12—C10i	1.438 (3)
C1—C7	1.485 (3)	C13—C14	1.353 (3)
C2—C3	1.392 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—C8i	1.406 (4)
C3—C4	1.382 (3)	C14—H14	0.9300
O3—C15—N1	122.5 (4)	C4—C5—C6	120.7 (2)
O3—C15—H15	118.8	C4—C5—H5	119.6
N1—C15—H15	118.8	C6—C5—H5	119.6
C15—N1—C17	121.0 (3)	C1—C6—C5	120.8 (2)
C15—N1—C16	121.5 (3)	C1—C6—H6	119.6
C17—N1—C16	117.5 (2)	C5—C6—H6	119.6
N1—C16—H16A	109.5	O1—C7—O2	122.7 (3)
N1—C16—H16B	109.5	O1—C7—C1	119.7 (3)
H16A—C16—H16B	109.5	O2—C7—C1	117.6 (3)
N1—C16—H16C	109.5	C9—C8—C14i	120.8 (3)
H16A—C16—H16C	109.5	C9—C8—H8	119.6
H16B—C16—H16C	109.5	C14i—C8—H8	119.6
N1—C17—H17A	109.5	C8—C9—C10	121.5 (2)
N1—C17—H17B	109.5	C8—C9—H9	119.2
H17A—C17—H17B	109.5	C10—C9—H9	119.2
N1—C17—H17C	109.5	C11—C10—C9	122.0 (2)
H17A—C17—H17C	109.5	C11—C10—C12i	119.9 (2)
H17B—C17—H17C	109.5	C9—C10—C12i	118.1 (2)
C7—O2—H2D	109.5	C12—C11—C10	119.9 (2)
C6—C1—C2	118.9 (2)	C12—C11—C4	119.3 (2)
C6—C1—C7	119.4 (2)	C10—C11—C4	120.8 (2)
C2—C1—C7	121.6 (2)	C11—C12—C13	122.3 (2)
C1—C2—C3	120.2 (2)	C11—C12—C10i	120.2 (2)
C1—C2—H2	119.9	C13—C12—C10i	117.5 (2)
C3—C2—H2	119.9	C14—C13—C12	122.0 (2)
C4—C3—C2	121.2 (2)	C14—C13—H13	119.0
C4—C3—H3	119.4	C12—C13—H13	119.0
C2—C3—H3	119.4	C13—C14—C8i	120.0 (2)
C3—C4—C5	118.1 (2)	C13—C14—H14	120.0
C3—C4—C11	121.9 (2)	C8i—C14—H14	120.0
C5—C4—C11	119.9 (2)
O3—C15—N1—C17	3.6 (5)	C8—C9—C10—C11	−178.9 (2)
O3—C15—N1—C16	−177.4 (4)	C8—C9—C10—C12i	0.9 (4)
C6—C1—C2—C3	−1.1 (4)	C9—C10—C11—C12	−179.8 (2)
C7—C1—C2—C3	179.7 (2)	C12i—C10—C11—C12	0.4 (4)
C1—C2—C3—C4	0.5 (4)	C9—C10—C11—C4	2.2 (3)
C2—C3—C4—C5	0.3 (4)	C12i—C10—C11—C4	−177.6 (2)
C2—C3—C4—C11	−178.8 (2)	C3—C4—C11—C12	106.8 (3)
C3—C4—C5—C6	−0.5 (4)	C5—C4—C11—C12	−72.3 (3)
C11—C4—C5—C6	178.6 (2)	C3—C4—C11—C10	−75.2 (3)
C2—C1—C6—C5	0.9 (4)	C5—C4—C11—C10	105.7 (3)
C7—C1—C6—C5	−179.9 (2)	C10—C11—C12—C13	178.1 (2)
C4—C5—C6—C1	−0.1 (4)	C4—C11—C12—C13	−3.9 (3)
C6—C1—C7—O1	−2.6 (4)	C10—C11—C12—C10i	−0.4 (4)
C2—C1—C7—O1	176.6 (3)	C4—C11—C12—C10i	177.6 (2)
C6—C1—C7—O2	176.5 (3)	C11—C12—C13—C14	−179.8 (2)
C2—C1—C7—O2	−4.3 (4)	C10i—C12—C13—C14	−1.3 (4)
C14i—C8—C9—C10	0.3 (4)	C12—C13—C14—C8i	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2D···O3ii	0.82	1.79	2.603 (4)	170
C5—H5···O3'	0.93	2.63	3.478 (5)	152
C16—H16A···Cg1	0.96	2.91	3.485 (3)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2D⋯O3i	0.82	1.79	2.603 (4)	170
C5—H5⋯O3′	0.93	2.63	3.478 (5)	152
C16—H16A⋯Cg1	0.96	2.91	3.485 (3)	120

Symmetry code: (i) . Cg1 is the centroid of the anthracene ring C8,C9,C10,C12A–C14A.