Experimental. Crystal data
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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Terephthalic acid 2,2 0 -dimethyl-1,1 0 - (butane-1,4-diyl)dibenzimidazole (2/3) Hui Jiang and Xian-Wu Dong* Department of Chemistry, Jilin Agriculture Science and Technology College, Jilin , People s Republic of China Correspondence jiangh_468@yahoo.com.cn Received 22 November 2007; accepted 8 April 2008 Key indicators: single-crystal X-ray study; T = 293 K; mean (C C) = Å; R factor = 0.071; wr factor = 0.164; data-to-parameter ratio = In the crystal structure of the title compound, 2C 8 H 6 O 4-3C 20 H 22 N 4, there are three independent 2,2 0 -dimethyl-1,1 0 - (butane-1,4-diyl)dibenzimidazole molecules, each of which lies on an inversion centre. The terephthalic acid molecules are linked to adjacent 2,2 0 -dimethyl-1,1 0 -(butane-1,4-diyl)dibenzimidazole molecules via O HN hydrogen bonds. Related literature For related literature, see: Dale & Elsegood (2004); Ma et al. (2000). Experimental Crystal data 2C 8 H 6 O 4 3C 20 H 22 N 4 M r = Triclinic, P1 a = (5) Å b = (8) Å c = (7) Å = (2) = (16) Data collection Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T min = 0.963, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections Table 1 Hydrogen-bond geometry (Å, ). = (2) V = (16) Å 3 Z =1 Mo K radiation = 0.08 mm 1 T = 293 (2) K mm measured reflections 7573 independent reflections 3739 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.23 e Å 3 min = 0.21 e Å 3 D HA D H HA DA D HA O1 H1N1 i (3) 157 O3 H3AN3 ii (3) 165 Symmetry codes: (i) x þ 1; y þ 1; z þ 1; (ii) x 1; y 1; z. Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97. The authors thank the Analysis and Testing Foundation of Northeast Normal University for support. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2066). References Dale, S. H. & Elsegood, M. R. J. (2004). Acta Cryst. C60, o444 o448. Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Ma, J.-F., Liu, J.-F., Liu, Y.-C., Xing, Y., Jia, H.-Q. & Lin, Y.-H. (2000). New J. Chem. 24, Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Sheldrick, G. M. (2008). Acta Cryst. A64, o838 # 2008 International Union of Crystallography doi: /s
2 supporting information [doi: /s ] Terephthalic acid 2,2 -dimethyl-1,1 -(butane-1,4-diyl)dibenzimidazole (2/3) Hui Jiang and Xian-Wu Dong S1. Comment The title compound is composed of terephthalic acid and 2,2 -dimethyl-1,1 -(butane-1,4-diyl)dibenzimidazole (Fig. 1). The bond distances and angles are normal (Dale & Elsegood, 2004; Ma et al., 2000). There are three independent 2,2 -dimethyl-1,1 -(butane-1,4-diyl)dibenzimidazole molecules, which extend in different directions, sitting around independent symmetry centres. The terephthalic acids are hydrogen bonded to the 2,2 -dimethyl-1,1 -(butane-1,4-diyl)dibenzimidazole (Table 1) via O H N hydrogen bonds into the chains (Fig. 2). S2. Experimental A mixture of terephthalic acid (0.033 g, 0.2 mmol), 2,2 -dimethyl-1,1 -(butane-1,4-diyl)dibenzimidazole (0.064 g, 0.2 mmol) in 1:4 (v/v) EtOH/H 2 O (10 ml) was placed in a Teflon-lined autoclave. The mixture was heated at 430 K for 1 days, and then it was gradually cooled to room temperature at a rate of 10 K.h -1. Colorless single crystals of the title compound were obtained. S3. Refinement All H-atoms bound to carbon were refined using a riding model with d(c H) = 0.93 Å, U iso = 1.2U eq (C) for aromatic, 0.97 Å, U iso = 1.5U eq (C) for CH 2 atoms and 0.96 Å, U iso = 1.5U eq (C) for CH 3 atoms. Hydroxyl H atoms were refined using a riding model with d(o H) = 0.82 Å, U iso = 1.5U eq (O). sup-1
3 Figure 1 A view of the title clathrate. The displacement ellipsoids are drawn at the 30% probability level.(i) -x, -y, -z + 1. (ii) -x, -y + 1, -z + 1. (iii) -x + 1, -y + 1, -z. (iv) -x + 2, -y, -z. Figure 2 A one-dimensional chain linked by hydrogen bonds. The H-bonds are shown as dashed lines. sup-2
4 Terephthalic acid 2,2 -dimethyl-1,1 -(butane-1,4-diyl)dibenzimidazole (2/3) Crystal data 2C 8 H 6 O 4 3C 20 H 22 N 4 M r = Triclinic, P1 Hall symbol: -P 1 a = (5) Å b = (8) Å c = (7) Å α = (2) β = (16) γ = (2) V = (16) Å 3 Data collection Rigaku R-AXIS RAPID diffractometer Radiation source: rotation-anode tube Graphite monochromator Detector resolution: 10.0 pixels mm -1 ω scans Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T min = 0.963, T max = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 437 parameters 0 restraints Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Z = 1 F(000) = 682 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 7573 reflections θ = µ = 0.08 mm 1 T = 293 K Plate, colourless mm measured reflections 7573 independent reflections 3739 reflections with I > 2σ(I) R int = θ max = 27.5, θ min = 3.0 h = k = l = Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0674P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max < Δρ max = 0.23 e Å 3 Δρ min = 0.21 e Å 3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc * =kfc[ xfc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: (15) Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq C (3) (2) (16) (6) C (3) (2) (16) (6) C (3) (2) (18) (7) H * C (4) (3) (2) (10) H * C (4) (3) (2) (9) H * C (3) (3) (18) (8) H * sup-3
5 C (3) (2) (18) (7) C (3) (3) (2) (10) H8A * H8B * H8C * C (2) (2) (16) (6) C (2) (2) (15) (6) C (3) (2) (18) (7) H * C (3) (2) (2) (8) H * C (3) (3) (18) (8) H * C (3) (2) (17) (7) H * C (2) (2) (16) (6) C (3) (2) (2) (8) H16A * H16B * H16C * C (2) (2) (18) (7) H17A * H17B * C (2) (2) (17) (7) H18A * H18B * C (2) (2) (16) (7) H19A * H19B * C (2) (2) (15) (6) H20A * H20B * C (3) (2) (19) (7) C (3) (2) (18) (6) C (3) (3) (2) (8) H * C (4) (4) (3) (12) H * C (5) (4) (3) (13) H * C (4) (3) (3) (10) H * C (3) (2) (2) (7) C (4) (4) (2) (13) H28A * H28B * H28C * C (3) (3) (3) (10) sup-4
6 H29A * H29B * C (3) (2) (3) (10) H30A * H30B * C (3) (2) (16) (6) C (3) (2) (17) (7) H * C (3) (2) (17) (7) H * C (3) (2) (16) (6) C (3) (2) (18) (7) H * C (3) (2) (17) (7) H * C (3) (2) (18) (7) C (3) (2) (19) (7) N (2) (18) (15) (6) N (2) (18) (13) (5) N (2) (17) (14) (5) N (19) (16) (13) (5) N (2) (18) (17) (6) N (2) (19) (15) (6) O (2) (16) (14) (6) H * O (2) (17) (16) (7) O (2) (16) (13) (6) H3A * O (2) (18) (17) (8) Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 C (13) (17) (14) (12) (12) (12) C (13) (17) (14) (12) (12) (12) C (17) (19) (17) (14) (15) (14) C (2) (3) (18) (2) (18) (17) C (2) (3) (16) (2) (15) (18) C (15) (2) (17) (14) (14) (16) C (14) (18) (16) (13) (13) (13) C (2) (3) (2) (18) (18) (18) C (12) (15) (13) (10) (11) (11) C (11) (15) (13) (10) (11) (11) C (15) (18) (16) (13) (14) (13) C (2) (17) (19) (15) (17) (14) C (19) (2) (17) (16) (15) (15) C (15) (2) (15) (14) (13) (14) C (12) (15) (14) (11) (12) (12) sup-5
7 C (16) (18) (2) (13) (16) (15) C (13) (2) (15) (13) (12) (13) C (13) (19) (15) (12) (12) (13) C (13) (19) (14) (12) (12) (12) C (12) (16) (13) (11) (11) (11) C (13) (17) (19) (11) (14) (14) C (13) (16) (17) (11) (13) (13) C (18) (2) (2) (16) (17) (17) C (3) (4) (3) (2) (2) (2) C (3) (4) (2) (3) (2) (2) C (2) (2) (3) (16) (2) (2) C (16) (19) (18) (14) (15) (15) C (3) (4) (2) (3) (2) (2) C (14) (2) (3) (13) (17) (19) C (14) (2) (3) (13) (17) (19) C (14) (15) (14) (11) (12) (11) C (14) (17) (16) (12) (13) (13) C (15) (16) (16) (12) (14) (12) C (14) (15) (14) (12) (12) (12) C (14) (18) (16) (12) (13) (13) C (15) (17) (16) (12) (14) (13) C (15) (18) (16) (13) (14) (13) C (15) (17) (17) (13) (14) (13) N (12) (14) (14) (10) (11) (11) N (10) (14) (12) (10) (10) (10) N (11) (13) (13) (9) (10) (10) N (10) (13) (11) (9) (9) (9) N (11) (14) (16) (10) (12) (12) N (13) (16) (15) (11) (12) (12) O (12) (13) (15) (10) (12) (10) O (14) (13) (19) (11) (13) (12) O (12) (13) (14) (10) (11) (11) O (14) (17) (19) (12) (15) (14) Geometric parameters (Å, º) C1 N (3) C20 C20 ii (4) C1 C (4) C20 H20A C1 C (4) C20 H20B C2 N (3) C21 N (3) C2 C (4) C21 C (4) C3 C (4) C21 C (3) C3 H C22 C (4) C4 C (5) C22 N (3) C4 H C23 C (5) C5 C (4) C23 H C5 H C24 C (5) C6 H C24 H sup-6
8 C7 N (3) C25 C (5) C7 N (3) C25 H C7 C (4) C26 H C8 H8A C27 N (3) C8 H8B C27 N (3) C8 H8C C27 C (4) C9 N (3) C28 H28A C9 C (3) C28 H28B C9 C (3) C28 H28C C10 C (4) C29 N (3) C10 N (3) C29 C (4) C11 C (4) C29 H29A C11 H C29 H29B C12 C (4) C30 C30 iii (5) C12 H C30 H30A C13 C (4) C30 H30B C13 H C31 C (3) C14 H C31 C (3) C15 N (3) C31 C (4) C15 N (3) C32 C (4) C15 C (4) C32 H C16 H16A C33 C (3) C16 H16B C33 H C16 H16C C34 C (4) C17 N (3) C34 C (4) C17 C (3) C35 C (4) C17 H17A C35 H C17 H17B C36 H C18 C18 i (5) C37 O (3) C18 H18A C37 O (3) C18 H18B C38 O (3) C19 N (3) C38 O (3) C19 C (3) O1 H C19 H19A O3 H3A C19 H19B N1 C1 C (2) N5 C21 C (3) N1 C1 C (3) N5 C21 C (2) C2 C1 C (3) C26 C21 C (3) N2 C2 C (3) C23 C22 N (2) N2 C2 C (2) C23 C22 C (3) C3 C2 C (3) N6 C22 C (2) C4 C3 C (3) C24 C23 C (3) C4 C3 H C24 C23 H C2 C3 H C22 C23 H C3 C4 C (3) C23 C24 C (4) C3 C4 H C23 C24 H C5 C4 H C25 C24 H sup-7
9 C6 C5 C (3) C26 C25 C (3) C6 C5 H C26 C25 H C4 C5 H C24 C25 H C5 C6 C (3) C25 C26 C (3) C5 C6 H C25 C26 H C1 C6 H C21 C26 H N1 C7 N (2) N6 C27 N (3) N1 C7 C (3) N6 C27 C (3) N2 C7 C (3) N5 C27 C (3) C7 C8 H8A C27 C28 H28A C7 C8 H8B C27 C28 H28B H8A C8 H8B H28A C28 H28B C7 C8 H8C C27 C28 H28C H8A C8 H8C H28A C28 H28C H8B C8 H8C H28B C28 H28C N3 C9 C (2) N5 C29 C (2) N3 C9 C (19) N5 C29 H29A C14 C9 C (2) C30 C29 H29A C11 C10 N (2) N5 C29 H29B C11 C10 C (2) C30 C29 H29B N4 C10 C (2) H29A C29 H29B C12 C11 C (2) C29 C30 C30 iii (3) C12 C11 H C29 C30 H30A C10 C11 H C30 iii C30 H30A C11 C12 C (3) C29 C30 H30B C11 C12 H C30 iii C30 H30B C13 C12 H H30A C30 H30B C14 C13 C (2) C36 C31 C (2) C14 C13 H C36 C31 C (2) C12 C13 H C32 C31 C (2) C13 C14 C (2) C31 C32 C (2) C13 C14 H C31 C32 H C9 C14 H C33 C32 H N3 C15 N (2) C34 C33 C (2) N3 C15 C (2) C34 C33 H N4 C15 C (2) C32 C33 H C15 C16 H16A C33 C34 C (2) C15 C16 H16B C33 C34 C (2) H16A C16 H16B C35 C34 C (2) C15 C16 H16C C36 C35 C (2) H16A C16 H16C C36 C35 H H16B C16 H16C C34 C35 H N2 C17 C (2) C35 C36 C (2) N2 C17 H17A C35 C36 H C18 C17 H17A C31 C36 H N2 C17 H17B O2 C37 O (3) C18 C17 H17B O2 C37 C (2) H17A C17 H17B O1 C37 C (2) sup-8
10 C17 C18 C18 i (3) O4 C38 O (3) C17 C18 H18A O4 C38 C (3) C18 i C18 H18A O3 C38 C (2) C17 C18 H18B C7 N1 C (2) C18 i C18 H18B C7 N2 C (2) H18A C18 H18B C7 N2 C (2) N4 C19 C (19) C2 N2 C (2) N4 C19 H19A C15 N3 C (19) C20 C19 H19A C15 N4 C (18) N4 C19 H19B C15 N4 C (2) C20 C19 H19B C10 N4 C (2) H19A C19 H19B C27 N5 C (2) C20 ii C20 C (2) C27 N5 C (3) C20 ii C20 H20A C21 N5 C (3) C19 C20 H20A C27 N6 C (2) C20 ii C20 H20B C37 O1 H C19 C20 H20B C38 O3 H3A H20A C20 H20B Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z; (iii) x+2, y, z. Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A O1 H1 N1 iv (3) 157 O3 H3A N3 v (3) 165 Symmetry codes: (iv) x+1, y+1, z+1; (v) x 1, y 1, z. sup-9
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SUPPORTING INFORMATION Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes Eric J. Uzelac, Casey B. McCausland, and Seth C. Rasmussen*
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