organic compounds
Terephthalic acid–2,2′-dimethyl-1,1′-(butane-1,4-diyl)dibenzimidazole (2/3)
aDepartment of Chemistry, Jilin Agriculture Science and Technology College, Jilin 132101, People's Republic of China
*Correspondence e-mail: jiangh_468@yahoo.com.cn
In the 8H6O4·3C20H22N4, there are three independent 2,2′-dimethyl-1,1′-(butane-1,4-diyl)dibenzimidazole molecules, each of which lies on an inversion centre. The terephthalic acid molecules are linked to adjacent 2,2′-dimethyl-1,1′-(butane-1,4-diyl)dibenzimidazole molecules via O—H⋯N hydrogen bonds.
of the title compound, 2CExperimental
Crystal data
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Refinement
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Data collection: PROCESS-AUTO (Rigaku, 1998); cell 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.
Supporting information
10.1107/S1600536808009665/cs2066sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009665/cs2066Isup2.hkl
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/H2O (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.
All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93 Å, Uiso = 1.2Ueq (C) for aromatic, 0.97 Å, Uiso = 1.5Ueq (C) for CH2 atoms and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms. Hydroxyl H atoms were refined using a riding model with d(O—H) = 0.82 Å, Uiso = 1.5Ueq (O).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell
PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).2C8H6O4·3C20H22N4 | Z = 1 |
Mr = 1286.88 | F(000) = 682 |
Triclinic, P1 | Dx = 1.268 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 9.225 (5) Å | Cell parameters from 7573 reflections |
b = 12.298 (8) Å | θ = 3.0–27.5° |
c = 14.883 (7) Å | µ = 0.08 mm−1 |
α = 87.17 (2)° | T = 293 K |
β = 87.768 (16)° | Plate, colourless |
γ = 89.33 (2)° | 0.49 × 0.38 × 0.26 mm |
V = 1685.0 (16) Å3 |
Rigaku R-AXIS RAPID diffractometer | 7573 independent reflections |
Radiation source: rotation-anode tube | 3739 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −11→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −15→15 |
Tmin = 0.963, Tmax = 0.977 | l = −19→19 |
16449 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.071 | H-atom parameters constrained |
wR(F2) = 0.163 | w = 1/[σ2(Fo2) + (0.0674P)2 + 0.1144P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
7573 reflections | Δρmax = 0.23 e Å−3 |
437 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0101 (15) |
2C8H6O4·3C20H22N4 | γ = 89.33 (2)° |
Mr = 1286.88 | V = 1685.0 (16) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.225 (5) Å | Mo Kα radiation |
b = 12.298 (8) Å | µ = 0.08 mm−1 |
c = 14.883 (7) Å | T = 293 K |
α = 87.17 (2)° | 0.49 × 0.38 × 0.26 mm |
β = 87.768 (16)° |
Rigaku R-AXIS RAPID diffractometer | 7573 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3739 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.977 | Rint = 0.055 |
16449 measured reflections |
R[F2 > 2σ(F2)] = 0.071 | 0 restraints |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.23 e Å−3 |
7573 reflections | Δρmin = −0.21 e Å−3 |
437 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4952 (3) | 0.6452 (2) | 0.39701 (16) | 0.0443 (6) | |
C2 | 0.4004 (3) | 0.5588 (2) | 0.41249 (16) | 0.0436 (6) | |
C3 | 0.4031 (3) | 0.4701 (2) | 0.35876 (18) | 0.0565 (7) | |
H3 | 0.3405 | 0.4119 | 0.3701 | 0.068* | |
C4 | 0.5025 (4) | 0.4726 (3) | 0.2882 (2) | 0.0728 (10) | |
H4 | 0.5074 | 0.4144 | 0.2505 | 0.087* | |
C5 | 0.5956 (4) | 0.5585 (3) | 0.2710 (2) | 0.0713 (9) | |
H5 | 0.6609 | 0.5570 | 0.2218 | 0.086* | |
C6 | 0.5948 (3) | 0.6460 (3) | 0.32422 (18) | 0.0592 (8) | |
H6 | 0.6581 | 0.7037 | 0.3123 | 0.071* | |
C7 | 0.3629 (3) | 0.6799 (2) | 0.51495 (18) | 0.0481 (7) | |
C8 | 0.2974 (3) | 0.7342 (3) | 0.5937 (2) | 0.0756 (10) | |
H8A | 0.3136 | 0.6901 | 0.6475 | 0.113* | |
H8B | 0.1949 | 0.7435 | 0.5864 | 0.113* | |
H8C | 0.3410 | 0.8041 | 0.5982 | 0.113* | |
C9 | 0.9763 (2) | 0.4712 (2) | 0.16737 (16) | 0.0383 (6) | |
C10 | 0.8777 (2) | 0.4183 (2) | 0.11664 (15) | 0.0368 (6) | |
C11 | 0.8522 (3) | 0.3085 (2) | 0.12836 (18) | 0.0521 (7) | |
H11 | 0.7845 | 0.2741 | 0.0951 | 0.063* | |
C12 | 0.9318 (3) | 0.2525 (2) | 0.1917 (2) | 0.0611 (8) | |
H12 | 0.9170 | 0.1782 | 0.2021 | 0.073* | |
C13 | 1.0343 (3) | 0.3039 (3) | 0.24080 (18) | 0.0621 (8) | |
H13 | 1.0883 | 0.2627 | 0.2819 | 0.074* | |
C14 | 1.0571 (3) | 0.4128 (2) | 0.22996 (17) | 0.0529 (7) | |
H14 | 1.1247 | 0.4469 | 0.2635 | 0.063* | |
C15 | 0.8801 (2) | 0.5945 (2) | 0.08040 (16) | 0.0416 (6) | |
C16 | 0.8408 (3) | 0.7004 (2) | 0.0362 (2) | 0.0604 (8) | |
H16A | 0.8748 | 0.7024 | −0.0256 | 0.091* | |
H16B | 0.8848 | 0.7580 | 0.0664 | 0.091* | |
H16C | 0.7373 | 0.7096 | 0.0392 | 0.091* | |
C17 | 0.1997 (2) | 0.5149 (2) | 0.52713 (18) | 0.0519 (7) | |
H17A | 0.1880 | 0.5270 | 0.5909 | 0.062* | |
H17B | 0.2251 | 0.4388 | 0.5207 | 0.062* | |
C18 | 0.0580 (2) | 0.5394 (2) | 0.48259 (17) | 0.0511 (7) | |
H18A | 0.0717 | 0.5344 | 0.4180 | 0.061* | |
H18B | 0.0269 | 0.6132 | 0.4944 | 0.061* | |
C19 | 0.7073 (2) | 0.4862 (2) | −0.00500 (16) | 0.0469 (7) | |
H19A | 0.7158 | 0.4139 | −0.0281 | 0.056* | |
H19B | 0.7226 | 0.5386 | −0.0553 | 0.056* | |
C20 | 0.5564 (2) | 0.5015 (2) | 0.03514 (15) | 0.0410 (6) | |
H20A | 0.5369 | 0.4444 | 0.0812 | 0.049* | |
H20B | 0.5502 | 0.5708 | 0.0635 | 0.049* | |
C21 | 0.6099 (3) | 0.0780 (2) | 0.09565 (19) | 0.0499 (7) | |
C22 | 0.5086 (3) | 0.1624 (2) | 0.08891 (18) | 0.0463 (6) | |
C23 | 0.4243 (3) | 0.1903 (3) | 0.1628 (2) | 0.0667 (8) | |
H23 | 0.3561 | 0.2464 | 0.1585 | 0.080* | |
C24 | 0.4434 (4) | 0.1336 (4) | 0.2417 (3) | 0.0917 (12) | |
H24 | 0.3872 | 0.1516 | 0.2922 | 0.110* | |
C25 | 0.5439 (5) | 0.0499 (4) | 0.2497 (3) | 0.0946 (13) | |
H25 | 0.5544 | 0.0133 | 0.3053 | 0.114* | |
C26 | 0.6290 (4) | 0.0197 (3) | 0.1766 (3) | 0.0764 (10) | |
H26 | 0.6960 | −0.0372 | 0.1814 | 0.092* | |
C27 | 0.6126 (3) | 0.1528 (2) | −0.0416 (2) | 0.0569 (7) | |
C28 | 0.6558 (4) | 0.1745 (4) | −0.1375 (2) | 0.0991 (13) | |
H28A | 0.7523 | 0.2031 | −0.1420 | 0.149* | |
H28B | 0.5899 | 0.2266 | −0.1641 | 0.149* | |
H28C | 0.6531 | 0.1081 | −0.1685 | 0.149* | |
C29 | 0.7922 (3) | −0.0014 (3) | −0.0138 (3) | 0.0739 (10) | |
H29A | 0.7951 | −0.0081 | −0.0785 | 0.089* | |
H29B | 0.7731 | −0.0729 | 0.0143 | 0.089* | |
C30 | 0.9373 (3) | 0.0365 (2) | 0.0140 (3) | 0.0741 (10) | |
H30A | 0.9350 | 0.0407 | 0.0790 | 0.089* | |
H30B | 0.9541 | 0.1093 | −0.0121 | 0.089* | |
C31 | 0.1777 (3) | 0.0473 (2) | 0.42478 (16) | 0.0420 (6) | |
C32 | 0.2506 (3) | −0.0499 (2) | 0.41235 (17) | 0.0493 (7) | |
H32 | 0.3417 | −0.0616 | 0.4358 | 0.059* | |
C33 | 0.1875 (3) | −0.1296 (2) | 0.36497 (17) | 0.0490 (7) | |
H33 | 0.2373 | −0.1947 | 0.3563 | 0.059* | |
C34 | 0.0517 (3) | −0.1139 (2) | 0.33031 (16) | 0.0449 (6) | |
C35 | −0.0224 (3) | −0.0178 (2) | 0.34588 (18) | 0.0504 (7) | |
H35 | −0.1151 | −0.0069 | 0.3245 | 0.060* | |
C36 | 0.0403 (3) | 0.0617 (2) | 0.39292 (17) | 0.0507 (7) | |
H36 | −0.0107 | 0.1258 | 0.4033 | 0.061* | |
C37 | 0.2471 (3) | 0.1394 (2) | 0.46745 (18) | 0.0497 (7) | |
C38 | −0.0130 (3) | −0.1938 (2) | 0.27258 (19) | 0.0518 (7) | |
N1 | 0.4693 (2) | 0.72048 (18) | 0.46235 (15) | 0.0498 (6) | |
N2 | 0.3174 (2) | 0.58270 (18) | 0.48811 (13) | 0.0442 (5) | |
N3 | 0.9751 (2) | 0.58143 (17) | 0.14404 (14) | 0.0445 (5) | |
N4 | 0.81999 (19) | 0.49945 (16) | 0.05991 (13) | 0.0393 (5) | |
N5 | 0.6745 (2) | 0.07253 (18) | 0.01097 (17) | 0.0530 (6) | |
N6 | 0.5129 (2) | 0.20832 (19) | 0.00184 (15) | 0.0567 (6) | |
O1 | 0.3721 (2) | 0.11390 (16) | 0.50186 (14) | 0.0674 (6) | |
H1 | 0.4049 | 0.1675 | 0.5244 | 0.081* | |
O2 | 0.1950 (2) | 0.22979 (17) | 0.46676 (16) | 0.0793 (7) | |
O3 | 0.0626 (2) | −0.28314 (16) | 0.26517 (13) | 0.0667 (6) | |
H3A | 0.0214 | −0.3237 | 0.2325 | 0.080* | |
O4 | −0.1239 (2) | −0.17682 (18) | 0.23391 (17) | 0.0881 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0354 (13) | 0.0509 (17) | 0.0473 (14) | −0.0004 (12) | −0.0090 (12) | −0.0023 (12) |
C2 | 0.0352 (13) | 0.0505 (17) | 0.0462 (14) | −0.0008 (12) | −0.0111 (12) | −0.0054 (12) |
C3 | 0.0593 (17) | 0.0555 (19) | 0.0567 (17) | −0.0048 (14) | −0.0188 (15) | −0.0092 (14) |
C4 | 0.086 (2) | 0.082 (3) | 0.0530 (18) | 0.008 (2) | −0.0140 (18) | −0.0234 (17) |
C5 | 0.067 (2) | 0.101 (3) | 0.0458 (16) | 0.007 (2) | 0.0036 (15) | −0.0110 (18) |
C6 | 0.0447 (15) | 0.077 (2) | 0.0550 (17) | −0.0084 (14) | −0.0038 (14) | 0.0042 (16) |
C7 | 0.0386 (14) | 0.0508 (18) | 0.0563 (16) | 0.0061 (13) | −0.0086 (13) | −0.0128 (13) |
C8 | 0.073 (2) | 0.083 (3) | 0.073 (2) | 0.0173 (18) | −0.0005 (18) | −0.0272 (18) |
C9 | 0.0306 (12) | 0.0401 (15) | 0.0448 (13) | 0.0012 (10) | −0.0050 (11) | −0.0063 (11) |
C10 | 0.0303 (11) | 0.0393 (15) | 0.0413 (13) | 0.0020 (10) | −0.0022 (11) | −0.0058 (11) |
C11 | 0.0502 (15) | 0.0467 (18) | 0.0603 (16) | −0.0047 (13) | −0.0004 (14) | −0.0116 (13) |
C12 | 0.074 (2) | 0.0376 (17) | 0.0702 (19) | 0.0023 (15) | 0.0017 (17) | 0.0047 (14) |
C13 | 0.0659 (19) | 0.064 (2) | 0.0545 (17) | 0.0139 (16) | −0.0068 (15) | 0.0121 (15) |
C14 | 0.0465 (15) | 0.062 (2) | 0.0512 (15) | 0.0058 (14) | −0.0139 (13) | −0.0031 (14) |
C15 | 0.0321 (12) | 0.0407 (15) | 0.0520 (14) | −0.0006 (11) | −0.0035 (12) | −0.0019 (12) |
C16 | 0.0524 (16) | 0.0495 (18) | 0.079 (2) | 0.0006 (13) | −0.0095 (16) | 0.0099 (15) |
C17 | 0.0347 (13) | 0.067 (2) | 0.0529 (15) | −0.0090 (13) | −0.0040 (12) | 0.0059 (13) |
C18 | 0.0348 (13) | 0.0659 (19) | 0.0522 (15) | −0.0069 (12) | −0.0052 (12) | 0.0051 (13) |
C19 | 0.0336 (13) | 0.0634 (19) | 0.0452 (14) | −0.0010 (12) | −0.0112 (12) | −0.0094 (12) |
C20 | 0.0348 (12) | 0.0491 (16) | 0.0399 (13) | −0.0020 (11) | −0.0075 (11) | −0.0051 (11) |
C21 | 0.0346 (13) | 0.0450 (17) | 0.0704 (19) | −0.0064 (11) | −0.0049 (14) | −0.0025 (14) |
C22 | 0.0335 (13) | 0.0458 (16) | 0.0601 (17) | −0.0004 (11) | −0.0031 (13) | −0.0071 (13) |
C23 | 0.0556 (18) | 0.074 (2) | 0.071 (2) | 0.0005 (16) | 0.0074 (17) | −0.0108 (17) |
C24 | 0.081 (3) | 0.118 (4) | 0.075 (3) | −0.013 (2) | 0.014 (2) | −0.008 (2) |
C25 | 0.092 (3) | 0.117 (4) | 0.073 (2) | −0.026 (3) | −0.008 (2) | 0.029 (2) |
C26 | 0.064 (2) | 0.060 (2) | 0.104 (3) | −0.0069 (16) | −0.018 (2) | 0.021 (2) |
C27 | 0.0495 (16) | 0.0558 (19) | 0.0654 (18) | −0.0039 (14) | 0.0031 (15) | −0.0061 (15) |
C28 | 0.099 (3) | 0.130 (4) | 0.068 (2) | −0.011 (3) | 0.016 (2) | −0.008 (2) |
C29 | 0.0360 (14) | 0.053 (2) | 0.135 (3) | 0.0018 (13) | 0.0092 (17) | −0.0380 (19) |
C30 | 0.0364 (14) | 0.053 (2) | 0.135 (3) | −0.0005 (13) | 0.0082 (17) | −0.0372 (19) |
C31 | 0.0445 (14) | 0.0370 (15) | 0.0443 (14) | −0.0032 (11) | −0.0018 (12) | 0.0001 (11) |
C32 | 0.0450 (14) | 0.0439 (17) | 0.0599 (16) | 0.0015 (12) | −0.0139 (13) | −0.0032 (13) |
C33 | 0.0487 (15) | 0.0383 (16) | 0.0607 (16) | 0.0024 (12) | −0.0113 (14) | −0.0041 (12) |
C34 | 0.0452 (14) | 0.0405 (15) | 0.0488 (14) | −0.0043 (12) | −0.0051 (12) | 0.0039 (12) |
C35 | 0.0419 (14) | 0.0489 (18) | 0.0606 (16) | −0.0020 (12) | −0.0092 (13) | 0.0005 (13) |
C36 | 0.0465 (15) | 0.0448 (17) | 0.0608 (16) | 0.0066 (12) | −0.0019 (14) | −0.0033 (13) |
C37 | 0.0494 (15) | 0.0449 (18) | 0.0549 (16) | −0.0024 (13) | −0.0004 (14) | −0.0028 (13) |
C38 | 0.0482 (15) | 0.0445 (17) | 0.0636 (17) | −0.0044 (13) | −0.0095 (14) | −0.0044 (13) |
N1 | 0.0382 (12) | 0.0499 (14) | 0.0623 (14) | −0.0034 (10) | −0.0078 (11) | −0.0085 (11) |
N2 | 0.0304 (10) | 0.0540 (14) | 0.0484 (12) | −0.0042 (10) | −0.0031 (10) | −0.0044 (10) |
N3 | 0.0361 (11) | 0.0408 (13) | 0.0579 (13) | −0.0021 (9) | −0.0122 (10) | −0.0067 (10) |
N4 | 0.0298 (10) | 0.0412 (13) | 0.0478 (11) | −0.0028 (9) | −0.0090 (9) | −0.0061 (9) |
N5 | 0.0352 (11) | 0.0444 (14) | 0.0801 (16) | −0.0001 (10) | 0.0049 (12) | −0.0153 (12) |
N6 | 0.0486 (13) | 0.0566 (16) | 0.0644 (15) | 0.0090 (11) | −0.0013 (12) | −0.0023 (12) |
O1 | 0.0630 (12) | 0.0492 (13) | 0.0933 (15) | −0.0026 (10) | −0.0258 (12) | −0.0187 (10) |
O2 | 0.0744 (14) | 0.0431 (13) | 0.1239 (19) | 0.0057 (11) | −0.0263 (13) | −0.0218 (12) |
O3 | 0.0662 (12) | 0.0494 (13) | 0.0883 (14) | 0.0003 (10) | −0.0303 (11) | −0.0199 (11) |
O4 | 0.0714 (14) | 0.0772 (17) | 0.1216 (19) | 0.0137 (12) | −0.0481 (15) | −0.0336 (14) |
C1—N1 | 1.388 (3) | C20—C20ii | 1.506 (4) |
C1—C2 | 1.388 (4) | C20—H20A | 0.9700 |
C1—C6 | 1.393 (4) | C20—H20B | 0.9700 |
C2—N2 | 1.378 (3) | C21—N5 | 1.377 (3) |
C2—C3 | 1.384 (4) | C21—C26 | 1.387 (4) |
C3—C4 | 1.367 (4) | C21—C22 | 1.392 (3) |
C3—H3 | 0.9300 | C22—C23 | 1.377 (4) |
C4—C5 | 1.377 (5) | C22—N6 | 1.387 (3) |
C4—H4 | 0.9300 | C23—C24 | 1.353 (5) |
C5—C6 | 1.367 (4) | C23—H23 | 0.9300 |
C5—H5 | 0.9300 | C24—C25 | 1.381 (5) |
C6—H6 | 0.9300 | C24—H24 | 0.9300 |
C7—N1 | 1.319 (3) | C25—C26 | 1.380 (5) |
C7—N2 | 1.355 (3) | C25—H25 | 0.9300 |
C7—C8 | 1.482 (4) | C26—H26 | 0.9300 |
C8—H8A | 0.9600 | C27—N6 | 1.308 (3) |
C8—H8B | 0.9600 | C27—N5 | 1.363 (3) |
C8—H8C | 0.9600 | C27—C28 | 1.479 (4) |
C9—N3 | 1.382 (3) | C28—H28A | 0.9600 |
C9—C14 | 1.384 (3) | C28—H28B | 0.9600 |
C9—C10 | 1.391 (3) | C28—H28C | 0.9600 |
C10—C11 | 1.375 (4) | C29—N5 | 1.456 (3) |
C10—N4 | 1.390 (3) | C29—C30 | 1.502 (4) |
C11—C12 | 1.371 (4) | C29—H29A | 0.9700 |
C11—H11 | 0.9300 | C29—H29B | 0.9700 |
C12—C13 | 1.393 (4) | C30—C30iii | 1.515 (5) |
C12—H12 | 0.9300 | C30—H30A | 0.9700 |
C13—C14 | 1.359 (4) | C30—H30B | 0.9700 |
C13—H13 | 0.9300 | C31—C36 | 1.377 (3) |
C14—H14 | 0.9300 | C31—C32 | 1.381 (3) |
C15—N3 | 1.318 (3) | C31—C37 | 1.488 (4) |
C15—N4 | 1.353 (3) | C32—C33 | 1.382 (4) |
C15—C16 | 1.477 (4) | C32—H32 | 0.9300 |
C16—H16A | 0.9600 | C33—C34 | 1.382 (3) |
C16—H16B | 0.9600 | C33—H33 | 0.9300 |
C16—H16C | 0.9600 | C34—C35 | 1.383 (4) |
C17—N2 | 1.462 (3) | C34—C38 | 1.482 (4) |
C17—C18 | 1.510 (3) | C35—C36 | 1.376 (4) |
C17—H17A | 0.9700 | C35—H35 | 0.9300 |
C17—H17B | 0.9700 | C36—H36 | 0.9300 |
C18—C18i | 1.511 (5) | C37—O2 | 1.206 (3) |
C18—H18A | 0.9700 | C37—O1 | 1.308 (3) |
C18—H18B | 0.9700 | C38—O4 | 1.205 (3) |
C19—N4 | 1.463 (3) | C38—O3 | 1.301 (3) |
C19—C20 | 1.507 (3) | O1—H1 | 0.8199 |
C19—H19A | 0.9700 | O3—H3A | 0.8197 |
C19—H19B | 0.9700 | ||
N1—C1—C2 | 109.2 (2) | N5—C21—C26 | 133.3 (3) |
N1—C1—C6 | 130.6 (3) | N5—C21—C22 | 105.5 (2) |
C2—C1—C6 | 120.2 (3) | C26—C21—C22 | 121.2 (3) |
N2—C2—C3 | 132.0 (3) | C23—C22—N6 | 129.6 (2) |
N2—C2—C1 | 105.9 (2) | C23—C22—C21 | 120.7 (3) |
C3—C2—C1 | 122.1 (3) | N6—C22—C21 | 109.7 (2) |
C4—C3—C2 | 116.5 (3) | C24—C23—C22 | 118.1 (3) |
C4—C3—H3 | 121.8 | C24—C23—H23 | 121.0 |
C2—C3—H3 | 121.8 | C22—C23—H23 | 121.0 |
C3—C4—C5 | 122.1 (3) | C23—C24—C25 | 122.0 (4) |
C3—C4—H4 | 118.9 | C23—C24—H24 | 119.0 |
C5—C4—H4 | 118.9 | C25—C24—H24 | 119.0 |
C6—C5—C4 | 121.8 (3) | C26—C25—C24 | 121.1 (3) |
C6—C5—H5 | 119.1 | C26—C25—H25 | 119.4 |
C4—C5—H5 | 119.1 | C24—C25—H25 | 119.4 |
C5—C6—C1 | 117.2 (3) | C25—C26—C21 | 117.0 (3) |
C5—C6—H6 | 121.4 | C25—C26—H26 | 121.5 |
C1—C6—H6 | 121.4 | C21—C26—H26 | 121.5 |
N1—C7—N2 | 112.3 (2) | N6—C27—N5 | 113.0 (3) |
N1—C7—C8 | 124.5 (3) | N6—C27—C28 | 124.1 (3) |
N2—C7—C8 | 123.2 (3) | N5—C27—C28 | 122.9 (3) |
C7—C8—H8A | 109.5 | C27—C28—H28A | 109.5 |
C7—C8—H8B | 109.5 | C27—C28—H28B | 109.5 |
H8A—C8—H8B | 109.5 | H28A—C28—H28B | 109.5 |
C7—C8—H8C | 109.5 | C27—C28—H28C | 109.5 |
H8A—C8—H8C | 109.5 | H28A—C28—H28C | 109.5 |
H8B—C8—H8C | 109.5 | H28B—C28—H28C | 109.5 |
N3—C9—C14 | 130.0 (2) | N5—C29—C30 | 112.6 (2) |
N3—C9—C10 | 109.79 (19) | N5—C29—H29A | 109.1 |
C14—C9—C10 | 120.2 (2) | C30—C29—H29A | 109.1 |
C11—C10—N4 | 132.6 (2) | N5—C29—H29B | 109.1 |
C11—C10—C9 | 122.3 (2) | C30—C29—H29B | 109.1 |
N4—C10—C9 | 105.0 (2) | H29A—C29—H29B | 107.8 |
C12—C11—C10 | 116.4 (2) | C29—C30—C30iii | 113.8 (3) |
C12—C11—H11 | 121.8 | C29—C30—H30A | 108.8 |
C10—C11—H11 | 121.8 | C30iii—C30—H30A | 108.8 |
C11—C12—C13 | 121.8 (3) | C29—C30—H30B | 108.8 |
C11—C12—H12 | 119.1 | C30iii—C30—H30B | 108.8 |
C13—C12—H12 | 119.1 | H30A—C30—H30B | 107.7 |
C14—C13—C12 | 121.4 (2) | C36—C31—C32 | 119.4 (2) |
C14—C13—H13 | 119.3 | C36—C31—C37 | 119.0 (2) |
C12—C13—H13 | 119.3 | C32—C31—C37 | 121.6 (2) |
C13—C14—C9 | 117.8 (2) | C31—C32—C33 | 119.8 (2) |
C13—C14—H14 | 121.1 | C31—C32—H32 | 120.1 |
C9—C14—H14 | 121.1 | C33—C32—H32 | 120.1 |
N3—C15—N4 | 112.5 (2) | C34—C33—C32 | 120.9 (2) |
N3—C15—C16 | 124.6 (2) | C34—C33—H33 | 119.6 |
N4—C15—C16 | 122.9 (2) | C32—C33—H33 | 119.6 |
C15—C16—H16A | 109.5 | C33—C34—C35 | 118.8 (2) |
C15—C16—H16B | 109.5 | C33—C34—C38 | 122.0 (2) |
H16A—C16—H16B | 109.5 | C35—C34—C38 | 119.1 (2) |
C15—C16—H16C | 109.5 | C36—C35—C34 | 120.3 (2) |
H16A—C16—H16C | 109.5 | C36—C35—H35 | 119.8 |
H16B—C16—H16C | 109.5 | C34—C35—H35 | 119.8 |
N2—C17—C18 | 112.0 (2) | C35—C36—C31 | 120.7 (2) |
N2—C17—H17A | 109.2 | C35—C36—H36 | 119.6 |
C18—C17—H17A | 109.2 | C31—C36—H36 | 119.6 |
N2—C17—H17B | 109.2 | O2—C37—O1 | 123.6 (3) |
C18—C17—H17B | 109.2 | O2—C37—C31 | 122.7 (2) |
H17A—C17—H17B | 107.9 | O1—C37—C31 | 113.7 (2) |
C17—C18—C18i | 110.9 (3) | O4—C38—O3 | 122.7 (3) |
C17—C18—H18A | 109.5 | O4—C38—C34 | 123.2 (3) |
C18i—C18—H18A | 109.5 | O3—C38—C34 | 114.1 (2) |
C17—C18—H18B | 109.5 | C7—N1—C1 | 105.6 (2) |
C18i—C18—H18B | 109.5 | C7—N2—C2 | 107.1 (2) |
H18A—C18—H18B | 108.0 | C7—N2—C17 | 128.4 (2) |
N4—C19—C20 | 112.81 (19) | C2—N2—C17 | 124.5 (2) |
N4—C19—H19A | 109.0 | C15—N3—C9 | 105.54 (19) |
C20—C19—H19A | 109.0 | C15—N4—C10 | 107.14 (18) |
N4—C19—H19B | 109.0 | C15—N4—C19 | 126.2 (2) |
C20—C19—H19B | 109.0 | C10—N4—C19 | 126.5 (2) |
H19A—C19—H19B | 107.8 | C27—N5—C21 | 106.6 (2) |
C20ii—C20—C19 | 111.6 (2) | C27—N5—C29 | 127.9 (3) |
C20ii—C20—H20A | 109.3 | C21—N5—C29 | 125.4 (3) |
C19—C20—H20A | 109.3 | C27—N6—C22 | 105.1 (2) |
C20ii—C20—H20B | 109.3 | C37—O1—H1 | 109.3 |
C19—C20—H20B | 109.3 | C38—O3—H3A | 109.4 |
H20A—C20—H20B | 108.0 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1iv | 0.82 | 1.83 | 2.609 (3) | 157 |
O3—H3A···N3v | 0.82 | 1.87 | 2.668 (3) | 165 |
Symmetry codes: (iv) −x+1, −y+1, −z+1; (v) x−1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | 2C8H6O4·3C20H22N4 |
Mr | 1286.88 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.225 (5), 12.298 (8), 14.883 (7) |
α, β, γ (°) | 87.17 (2), 87.768 (16), 89.33 (2) |
V (Å3) | 1685.0 (16) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.49 × 0.38 × 0.26 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.963, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16449, 7573, 3739 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.071, 0.163, 1.01 |
No. of reflections | 7573 |
No. of parameters | 437 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.21 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 1.83 | 2.609 (3) | 157.1 |
O3—H3A···N3ii | 0.82 | 1.87 | 2.668 (3) | 165.2 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y−1, z. |
Acknowledgements
The authors thank the Analysis and Testing Foundation of Northeast Normal University for support.
References
Dale, S. H. & Elsegood, M. R. J. (2004). Acta Cryst. C60, o444–o448. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Ma, J.-F., Liu, J.-F., Liu, Y.-C., Xing, Y., Jia, H.-Q. & Lin, Y.-H. (2000). New J. Chem. 24, 759–763. Web of Science CrossRef CAS Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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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).