Crystals of the title compound, 2C
26H
18N
4O
2·C
7H
8, were obtained from the reaction of 8-hydroxyquinoline with 1,2-phenylenediamine in methanol and recrystallized from toluene. The compound contains three essentially planar ring systems: the benzimidazole ring (r.m.s. deviation = 0.039 Å) and two 8-hydroxyquinoline rings (r.m.s. deviations of 0.0056 Å in both rings). The benzimidazole ring and one 8-hydroxyquinoline ring are almost co-planar, forming a dihdral angle of 3.1 (2)°. The other 8-hydroxyquinoline ring is almost perpendicular to the benzimidazole plane with a dihedral angle of 86.2 (2)°. Intramolecular O—H

N contacts are present. The crystal structure is stabilized by intermolecular O—H

N interactions. The complete toluene molecule is generated by crystallographic inversion symmetry; therefore its methyl group is disordered over two sites of equal occupancy.
Supporting information
CCDC reference: 770050
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.004 Å
- H-atom completeness 98%
- Disorder in solvent or counterion
- R factor = 0.051
- wR factor = 0.156
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C28 -C30_a 1.36 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.596 42
PLAT041_ALERT_1_C Calc. and Reported SumFormula Strings Differ ?
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C59 H44 N8 O4
Atom count from the _atom_site data: C59 H43 N8 O4
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 1
From the CIF: _chemical_formula_sum C59 H44 N8 O4
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 59.00 59.00 0.00
H 44.00 43.00 1.00
N 8.00 8.00 0.00
O 4.00 4.00 0.00
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ................... 13.00 Perc.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
5 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
A solution of 1,2-diaminobenzene (0.001 mol) in absolute methanol (20 ml) was
added in small portions to a solution of 8-hydroxyquinoline-2-aldehyde (0.003 mol) in absolute methanol (30 ml). The reaction mixture was maintained at 348 K for 2 h,and was monitored by TLC. The resulting precipitation was washed
with methanol, dried and recrystallized from toluene. 1H
NMR(d6-DMSO):9.46(s,1H),9.33(s,1H),8.56(d,1H),8.47(d,1H),8.15(d,1H),
7.82–7.85(m,2H),7.42–7.48(m,2H),7.08–7.40(m,7H),6.73(s,2H).
Toluene molecule is located at a symmetrical center, so 4-H of toluene is
not present. H atoms attached to C atoms were placed in geometrically idealized
positions with Csp2—H = 0.93 Å and Csp3—H = 0.96 Å,
and were constrained to ride on their parent atoms.
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).
Bis{2-[1-(8-hydroxy-2-quinolylmethyl)-1
H-benzimidazol-2-yl]quinolin-
8-ol} toluene solvate
top
Crystal data top
2C26H18N4O2·C7H8 | Z = 1 |
Mr = 929.02 | F(000) = 486 |
Triclinic, P1 | Dx = 1.327 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.014 (7) Å | Cell parameters from 2466 reflections |
b = 12.669 (11) Å | θ = 3.0–25.9° |
c = 12.727 (11) Å | µ = 0.09 mm−1 |
α = 112.979 (10)° | T = 295 K |
β = 90.881 (11)° | Block, yellow |
γ = 100.966 (11)° | 0.30 × 0.20 × 0.15 mm |
V = 1162.1 (17) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4077 independent reflections |
Radiation source: fine-focus sealed tube | 3049 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
phi and ω scans | θmax = 25.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −9→7 |
Tmin = 0.975, Tmax = 0.987 | k = −15→14 |
6333 measured reflections | l = −12→15 |
Refinement top
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)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.156 | w = 1/[σ2(Fo2) + (0.0768P)2 + 0.2872P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4077 reflections | Δρmax = 0.40 e Å−3 |
329 parameters | Δρmin = −0.32 e Å−3 |
2 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.033 (4) |
Crystal data top
2C26H18N4O2·C7H8 | γ = 100.966 (11)° |
Mr = 929.02 | V = 1162.1 (17) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.014 (7) Å | Mo Kα radiation |
b = 12.669 (11) Å | µ = 0.09 mm−1 |
c = 12.727 (11) Å | T = 295 K |
α = 112.979 (10)° | 0.30 × 0.20 × 0.15 mm |
β = 90.881 (11)° | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4077 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 3049 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.987 | Rint = 0.024 |
6333 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.051 | 2 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.40 e Å−3 |
4077 reflections | Δρmin = −0.32 e Å−3 |
329 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.5707 (3) | 0.12196 (18) | −0.05782 (17) | 0.0455 (5) | |
C2 | 0.7346 (3) | 0.0952 (2) | −0.0469 (2) | 0.0535 (6) | |
C3 | 0.7601 (3) | −0.0148 (2) | −0.1092 (2) | 0.0624 (6) | |
H3 | 0.8668 | −0.0316 | −0.1027 | 0.075* | |
C4 | 0.6260 (4) | −0.1028 (2) | −0.1830 (2) | 0.0676 (7) | |
H4 | 0.6453 | −0.1773 | −0.2248 | 0.081* | |
C5 | 0.4679 (3) | −0.0808 (2) | −0.1944 (2) | 0.0633 (6) | |
H5 | 0.3807 | −0.1402 | −0.2435 | 0.076* | |
C6 | 0.4366 (3) | 0.03220 (19) | −0.13169 (18) | 0.0509 (5) | |
C7 | 0.2767 (3) | 0.0626 (2) | −0.13557 (19) | 0.0556 (6) | |
H7 | 0.1833 | 0.0059 | −0.1805 | 0.067* | |
C8 | 0.2582 (3) | 0.17396 (19) | −0.07426 (19) | 0.0524 (6) | |
H8 | 0.1532 | 0.1942 | −0.0774 | 0.063* | |
C9 | 0.4018 (2) | 0.25868 (18) | −0.00545 (17) | 0.0434 (5) | |
C10 | 0.3807 (2) | 0.37994 (17) | 0.05742 (16) | 0.0421 (5) | |
C11 | 0.2623 (3) | 0.52959 (18) | 0.12008 (18) | 0.0462 (5) | |
C12 | 0.1518 (3) | 0.6075 (2) | 0.1430 (2) | 0.0554 (6) | |
H12 | 0.0394 | 0.5825 | 0.1100 | 0.066* | |
C13 | 0.2159 (3) | 0.7227 (2) | 0.2162 (2) | 0.0625 (6) | |
H13 | 0.1452 | 0.7763 | 0.2325 | 0.075* | |
C14 | 0.3845 (3) | 0.7607 (2) | 0.2665 (2) | 0.0652 (7) | |
H14 | 0.4228 | 0.8390 | 0.3160 | 0.078* | |
C15 | 0.4960 (3) | 0.6855 (2) | 0.2448 (2) | 0.0569 (6) | |
H15 | 0.6081 | 0.7112 | 0.2783 | 0.068* | |
C16 | 0.4318 (2) | 0.56921 (18) | 0.16998 (17) | 0.0441 (5) | |
C17 | 0.6860 (2) | 0.47670 (18) | 0.15656 (18) | 0.0437 (5) | |
H17A | 0.7497 | 0.5569 | 0.1811 | 0.052* | |
H17B | 0.7314 | 0.4293 | 0.0878 | 0.052* | |
C18 | 0.7154 (2) | 0.43377 (16) | 0.24939 (16) | 0.0411 (5) | |
C19 | 0.5972 (3) | 0.43317 (19) | 0.33017 (18) | 0.0511 (5) | |
H19 | 0.4935 | 0.4545 | 0.3249 | 0.061* | |
C20 | 0.6374 (3) | 0.4007 (2) | 0.41619 (19) | 0.0557 (6) | |
H20 | 0.5605 | 0.4004 | 0.4701 | 0.067* | |
C21 | 0.7938 (3) | 0.36783 (18) | 0.42466 (17) | 0.0481 (5) | |
C22 | 0.8471 (3) | 0.3341 (2) | 0.5118 (2) | 0.0632 (6) | |
H22 | 0.7776 | 0.3338 | 0.5695 | 0.076* | |
C23 | 1.0006 (4) | 0.3022 (2) | 0.5104 (2) | 0.0702 (7) | |
H23 | 1.0346 | 0.2799 | 0.5675 | 0.084* | |
C24 | 1.1081 (3) | 0.3024 (2) | 0.4245 (2) | 0.0680 (7) | |
H24 | 1.2123 | 0.2804 | 0.4252 | 0.082* | |
C25 | 1.0602 (3) | 0.3348 (2) | 0.3397 (2) | 0.0556 (6) | |
C26 | 0.9023 (2) | 0.36878 (17) | 0.33817 (17) | 0.0440 (5) | |
C27 | 0.6666 (8) | 0.9326 (7) | 0.5448 (6) | 0.109 (2) | 0.50 |
H27A | 0.6352 | 0.8484 | 0.5116 | 0.163* | 0.50 |
H27B | 0.5904 | 0.9635 | 0.5112 | 0.163* | 0.50 |
H27C | 0.6590 | 0.9610 | 0.6260 | 0.163* | 0.50 |
C28 | 0.8398 (8) | 0.9701 (3) | 0.5231 (4) | 0.1311 (17) | |
C29 | 0.8662 (8) | 0.9652 (4) | 0.4163 (4) | 0.151 (2) | |
H29 | 0.7753 | 0.9409 | 0.3601 | 0.181* | |
C30 | 1.0280 (8) | 0.9965 (4) | 0.3939 (4) | 0.141 (2) | |
H30 | 1.0493 | 0.9953 | 0.3219 | 0.169* | |
N1 | 0.5530 (2) | 0.23373 (15) | 0.00443 (14) | 0.0448 (4) | |
N2 | 0.2332 (2) | 0.41096 (15) | 0.05066 (15) | 0.0486 (5) | |
N3 | 0.5069 (2) | 0.47278 (14) | 0.12805 (14) | 0.0426 (4) | |
N4 | 0.8615 (2) | 0.40046 (14) | 0.25095 (14) | 0.0437 (4) | |
O1 | 0.8628 (2) | 0.17832 (16) | 0.02683 (16) | 0.0740 (5) | |
H1 | 0.8293 | 0.2394 | 0.0589 | 0.111* | |
O2 | 1.1662 (2) | 0.3371 (2) | 0.25782 (18) | 0.0811 (6) | |
H2 | 1.1174 | 0.3512 | 0.2093 | 0.122* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0529 (12) | 0.0487 (12) | 0.0422 (12) | 0.0166 (9) | 0.0120 (9) | 0.0232 (10) |
C2 | 0.0539 (13) | 0.0595 (14) | 0.0556 (14) | 0.0219 (11) | 0.0143 (10) | 0.0271 (11) |
C3 | 0.0682 (16) | 0.0667 (16) | 0.0672 (16) | 0.0343 (13) | 0.0272 (12) | 0.0325 (13) |
C4 | 0.091 (2) | 0.0566 (15) | 0.0625 (16) | 0.0302 (14) | 0.0287 (14) | 0.0244 (12) |
C5 | 0.0789 (17) | 0.0514 (14) | 0.0552 (14) | 0.0112 (12) | 0.0127 (12) | 0.0176 (11) |
C6 | 0.0610 (14) | 0.0511 (13) | 0.0430 (12) | 0.0117 (10) | 0.0097 (10) | 0.0214 (10) |
C7 | 0.0552 (13) | 0.0541 (14) | 0.0526 (13) | 0.0027 (10) | −0.0015 (10) | 0.0204 (11) |
C8 | 0.0441 (12) | 0.0589 (14) | 0.0560 (13) | 0.0092 (10) | −0.0010 (10) | 0.0260 (11) |
C9 | 0.0438 (11) | 0.0506 (12) | 0.0424 (11) | 0.0128 (9) | 0.0048 (8) | 0.0243 (9) |
C10 | 0.0395 (11) | 0.0515 (12) | 0.0420 (11) | 0.0120 (9) | 0.0034 (8) | 0.0249 (9) |
C11 | 0.0455 (11) | 0.0545 (13) | 0.0492 (12) | 0.0162 (9) | 0.0099 (9) | 0.0291 (10) |
C12 | 0.0471 (12) | 0.0673 (15) | 0.0682 (15) | 0.0250 (11) | 0.0153 (10) | 0.0383 (13) |
C13 | 0.0691 (16) | 0.0657 (16) | 0.0717 (16) | 0.0334 (13) | 0.0234 (12) | 0.0382 (13) |
C14 | 0.0793 (17) | 0.0525 (14) | 0.0670 (16) | 0.0222 (12) | 0.0132 (13) | 0.0236 (12) |
C15 | 0.0582 (14) | 0.0547 (14) | 0.0584 (14) | 0.0136 (11) | 0.0034 (11) | 0.0227 (11) |
C16 | 0.0465 (11) | 0.0502 (12) | 0.0455 (12) | 0.0166 (9) | 0.0089 (9) | 0.0267 (10) |
C17 | 0.0359 (10) | 0.0505 (12) | 0.0486 (12) | 0.0099 (8) | 0.0023 (8) | 0.0236 (9) |
C18 | 0.0375 (10) | 0.0424 (11) | 0.0410 (11) | 0.0084 (8) | 0.0008 (8) | 0.0142 (9) |
C19 | 0.0423 (11) | 0.0665 (14) | 0.0477 (13) | 0.0199 (10) | 0.0052 (9) | 0.0225 (11) |
C20 | 0.0548 (13) | 0.0716 (15) | 0.0456 (13) | 0.0202 (11) | 0.0140 (10) | 0.0254 (11) |
C21 | 0.0557 (13) | 0.0482 (12) | 0.0412 (12) | 0.0143 (10) | 0.0029 (9) | 0.0173 (9) |
C22 | 0.0791 (17) | 0.0717 (16) | 0.0489 (14) | 0.0247 (13) | 0.0084 (12) | 0.0309 (12) |
C23 | 0.0856 (19) | 0.0767 (17) | 0.0633 (16) | 0.0304 (14) | −0.0019 (13) | 0.0381 (14) |
C24 | 0.0625 (15) | 0.0780 (17) | 0.0804 (18) | 0.0291 (13) | 0.0023 (13) | 0.0431 (14) |
C25 | 0.0489 (13) | 0.0634 (14) | 0.0669 (15) | 0.0196 (11) | 0.0063 (11) | 0.0357 (12) |
C26 | 0.0437 (11) | 0.0418 (11) | 0.0466 (12) | 0.0084 (9) | −0.0012 (9) | 0.0184 (9) |
C27 | 0.126 (6) | 0.111 (6) | 0.093 (5) | 0.052 (5) | 0.008 (5) | 0.033 (4) |
C28 | 0.243 (5) | 0.064 (2) | 0.083 (3) | 0.045 (3) | −0.029 (3) | 0.0222 (18) |
C29 | 0.262 (7) | 0.096 (3) | 0.094 (3) | 0.027 (4) | −0.041 (4) | 0.044 (2) |
C30 | 0.268 (7) | 0.085 (3) | 0.069 (3) | 0.036 (4) | −0.027 (4) | 0.031 (2) |
N1 | 0.0448 (10) | 0.0504 (10) | 0.0444 (10) | 0.0156 (8) | 0.0062 (7) | 0.0220 (8) |
N2 | 0.0403 (9) | 0.0540 (11) | 0.0579 (11) | 0.0146 (8) | 0.0035 (8) | 0.0270 (9) |
N3 | 0.0383 (9) | 0.0491 (10) | 0.0464 (10) | 0.0136 (7) | 0.0035 (7) | 0.0237 (8) |
N4 | 0.0381 (9) | 0.0495 (10) | 0.0473 (10) | 0.0131 (7) | 0.0031 (7) | 0.0217 (8) |
O1 | 0.0539 (10) | 0.0736 (12) | 0.0870 (13) | 0.0276 (9) | 0.0027 (9) | 0.0180 (10) |
O2 | 0.0540 (10) | 0.1300 (17) | 0.1009 (15) | 0.0461 (11) | 0.0256 (10) | 0.0773 (13) |
Geometric parameters (Å, º) top
C1—N1 | 1.363 (3) | C17—C18 | 1.513 (3) |
C1—C6 | 1.415 (3) | C17—H17A | 0.9700 |
C1—C2 | 1.435 (3) | C17—H17B | 0.9700 |
C2—O1 | 1.354 (3) | C18—N4 | 1.320 (3) |
C2—C3 | 1.365 (3) | C18—C19 | 1.410 (3) |
C3—C4 | 1.406 (4) | C19—C20 | 1.365 (3) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.365 (4) | C20—C21 | 1.409 (3) |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—C6 | 1.414 (3) | C21—C26 | 1.416 (3) |
C5—H5 | 0.9300 | C21—C22 | 1.421 (3) |
C6—C7 | 1.411 (3) | C22—C23 | 1.365 (4) |
C7—C8 | 1.358 (3) | C22—H22 | 0.9300 |
C7—H7 | 0.9300 | C23—C24 | 1.403 (4) |
C8—C9 | 1.418 (3) | C23—H23 | 0.9300 |
C8—H8 | 0.9300 | C24—C25 | 1.369 (3) |
C9—N1 | 1.325 (3) | C24—H24 | 0.9300 |
C9—C10 | 1.474 (3) | C25—O2 | 1.361 (3) |
C10—N2 | 1.327 (3) | C25—C26 | 1.414 (3) |
C10—N3 | 1.381 (3) | C26—N4 | 1.374 (3) |
C11—N2 | 1.385 (3) | C27—C28 | 1.4463 (15) |
C11—C12 | 1.400 (3) | C27—H27A | 0.9600 |
C11—C16 | 1.402 (3) | C27—H27B | 0.9600 |
C12—C13 | 1.378 (4) | C27—H27C | 0.9600 |
C12—H12 | 0.9300 | C28—C29 | 1.358 (6) |
C13—C14 | 1.398 (4) | C28—C30i | 1.365 (6) |
C13—H13 | 0.9300 | C29—C30 | 1.351 (9) |
C14—C15 | 1.381 (3) | C29—H29 | 0.9300 |
C14—H14 | 0.9300 | C30—C28i | 1.365 (6) |
C15—C16 | 1.394 (3) | C30—H30 | 0.9300 |
C15—H15 | 0.9300 | O1—H1 | 0.8200 |
C16—N3 | 1.385 (3) | O2—H2 | 0.8200 |
C17—N3 | 1.462 (3) | | |
| | | |
N1—C1—C6 | 123.4 (2) | C18—C17—H17B | 108.7 |
N1—C1—C2 | 117.63 (19) | H17A—C17—H17B | 107.6 |
C6—C1—C2 | 119.0 (2) | N4—C18—C19 | 122.82 (19) |
O1—C2—C3 | 120.0 (2) | N4—C18—C17 | 115.06 (17) |
O1—C2—C1 | 120.0 (2) | C19—C18—C17 | 122.09 (18) |
C3—C2—C1 | 120.0 (2) | C20—C19—C18 | 118.8 (2) |
C2—C3—C4 | 120.4 (2) | C20—C19—H19 | 120.6 |
C2—C3—H3 | 119.8 | C18—C19—H19 | 120.6 |
C4—C3—H3 | 119.8 | C19—C20—C21 | 121.0 (2) |
C5—C4—C3 | 121.2 (2) | C19—C20—H20 | 119.5 |
C5—C4—H4 | 119.4 | C21—C20—H20 | 119.5 |
C3—C4—H4 | 119.4 | C20—C21—C26 | 115.94 (19) |
C4—C5—C6 | 120.1 (2) | C20—C21—C22 | 124.9 (2) |
C4—C5—H5 | 119.9 | C26—C21—C22 | 119.2 (2) |
C6—C5—H5 | 119.9 | C23—C22—C21 | 119.8 (2) |
C7—C6—C5 | 124.3 (2) | C23—C22—H22 | 120.1 |
C7—C6—C1 | 116.4 (2) | C21—C22—H22 | 120.1 |
C5—C6—C1 | 119.3 (2) | C22—C23—C24 | 121.2 (2) |
C8—C7—C6 | 120.6 (2) | C22—C23—H23 | 119.4 |
C8—C7—H7 | 119.7 | C24—C23—H23 | 119.4 |
C6—C7—H7 | 119.7 | C25—C24—C23 | 120.2 (2) |
C7—C8—C9 | 118.8 (2) | C25—C24—H24 | 119.9 |
C7—C8—H8 | 120.6 | C23—C24—H24 | 119.9 |
C9—C8—H8 | 120.6 | O2—C25—C24 | 120.1 (2) |
N1—C9—C8 | 123.0 (2) | O2—C25—C26 | 119.5 (2) |
N1—C9—C10 | 118.97 (18) | C24—C25—C26 | 120.3 (2) |
C8—C9—C10 | 117.98 (18) | N4—C26—C25 | 117.61 (19) |
N2—C10—N3 | 112.54 (18) | N4—C26—C21 | 123.14 (19) |
N2—C10—C9 | 122.02 (18) | C25—C26—C21 | 119.2 (2) |
N3—C10—C9 | 125.44 (17) | C28—C27—H27A | 109.5 |
N2—C11—C12 | 129.9 (2) | C28—C27—H27B | 109.5 |
N2—C11—C16 | 109.73 (17) | H27A—C27—H27B | 109.5 |
C12—C11—C16 | 120.4 (2) | C28—C27—H27C | 109.5 |
C13—C12—C11 | 117.5 (2) | H27A—C27—H27C | 109.5 |
C13—C12—H12 | 121.2 | H27B—C27—H27C | 109.5 |
C11—C12—H12 | 121.2 | C29—C28—C30i | 121.6 (5) |
C12—C13—C14 | 121.5 (2) | C29—C28—C27 | 117.7 (6) |
C12—C13—H13 | 119.2 | C30i—C28—C27 | 120.6 (6) |
C14—C13—H13 | 119.2 | C30—C29—C28 | 118.3 (5) |
C15—C14—C13 | 121.9 (2) | C30—C29—H29 | 120.9 |
C15—C14—H14 | 119.0 | C28—C29—H29 | 120.9 |
C13—C14—H14 | 119.0 | C29—C30—C28i | 120.1 (5) |
C14—C15—C16 | 116.6 (2) | C29—C30—H30 | 120.0 |
C14—C15—H15 | 121.7 | C28i—C30—H30 | 120.0 |
C16—C15—H15 | 121.7 | C9—N1—C1 | 117.77 (18) |
N3—C16—C15 | 132.0 (2) | C10—N2—C11 | 105.48 (17) |
N3—C16—C11 | 106.02 (18) | C10—N3—C16 | 106.21 (16) |
C15—C16—C11 | 122.00 (19) | C10—N3—C17 | 129.92 (17) |
N3—C17—C18 | 114.36 (16) | C16—N3—C17 | 123.86 (16) |
N3—C17—H17A | 108.7 | C18—N4—C26 | 118.16 (17) |
C18—C17—H17A | 108.7 | C2—O1—H1 | 109.5 |
N3—C17—H17B | 108.7 | C25—O2—H2 | 109.5 |
| | | |
N1—C1—C2—O1 | 2.7 (3) | C19—C20—C21—C22 | 179.3 (2) |
C6—C1—C2—O1 | −177.24 (19) | C20—C21—C22—C23 | 179.0 (2) |
N1—C1—C2—C3 | −178.68 (19) | C26—C21—C22—C23 | −0.6 (3) |
C6—C1—C2—C3 | 1.4 (3) | C21—C22—C23—C24 | 0.3 (4) |
O1—C2—C3—C4 | 177.8 (2) | C22—C23—C24—C25 | −0.1 (4) |
C1—C2—C3—C4 | −0.8 (3) | C23—C24—C25—O2 | 178.7 (2) |
C2—C3—C4—C5 | 0.0 (4) | C23—C24—C25—C26 | 0.2 (4) |
C3—C4—C5—C6 | 0.2 (4) | O2—C25—C26—N4 | 1.5 (3) |
C4—C5—C6—C7 | −178.4 (2) | C24—C25—C26—N4 | 179.9 (2) |
C4—C5—C6—C1 | 0.4 (3) | O2—C25—C26—C21 | −179.1 (2) |
N1—C1—C6—C7 | −2.3 (3) | C24—C25—C26—C21 | −0.6 (3) |
C2—C1—C6—C7 | 177.70 (19) | C20—C21—C26—N4 | 0.6 (3) |
N1—C1—C6—C5 | 178.91 (19) | C22—C21—C26—N4 | −179.78 (19) |
C2—C1—C6—C5 | −1.1 (3) | C20—C21—C26—C25 | −178.89 (19) |
C5—C6—C7—C8 | −178.7 (2) | C22—C21—C26—C25 | 0.8 (3) |
C1—C6—C7—C8 | 2.5 (3) | C30i—C28—C29—C30 | −1.2 (8) |
C6—C7—C8—C9 | −0.7 (3) | C27—C28—C29—C30 | −178.0 (5) |
C7—C8—C9—N1 | −1.8 (3) | C28—C29—C30—C28i | 1.2 (8) |
C7—C8—C9—C10 | 178.01 (19) | C8—C9—N1—C1 | 2.2 (3) |
N1—C9—C10—N2 | 179.53 (18) | C10—C9—N1—C1 | −177.69 (17) |
C8—C9—C10—N2 | −0.3 (3) | C6—C1—N1—C9 | 0.0 (3) |
N1—C9—C10—N3 | −0.2 (3) | C2—C1—N1—C9 | 180.00 (18) |
C8—C9—C10—N3 | 179.92 (18) | N3—C10—N2—C11 | −0.2 (2) |
N2—C11—C12—C13 | −179.8 (2) | C9—C10—N2—C11 | −179.95 (17) |
C16—C11—C12—C13 | −0.5 (3) | C12—C11—N2—C10 | 178.8 (2) |
C11—C12—C13—C14 | −0.3 (3) | C16—C11—N2—C10 | −0.6 (2) |
C12—C13—C14—C15 | 0.6 (4) | N2—C10—N3—C16 | 0.8 (2) |
C13—C14—C15—C16 | −0.1 (4) | C9—C10—N3—C16 | −179.41 (18) |
C14—C15—C16—N3 | 178.5 (2) | N2—C10—N3—C17 | −178.58 (18) |
C14—C15—C16—C11 | −0.8 (3) | C9—C10—N3—C17 | 1.2 (3) |
N2—C11—C16—N3 | 1.0 (2) | C15—C16—N3—C10 | 179.6 (2) |
C12—C11—C16—N3 | −178.36 (18) | C11—C16—N3—C10 | −1.1 (2) |
N2—C11—C16—C15 | −179.55 (19) | C15—C16—N3—C17 | −1.0 (3) |
C12—C11—C16—C15 | 1.1 (3) | C11—C16—N3—C17 | 178.35 (17) |
N3—C17—C18—N4 | 158.92 (17) | C18—C17—N3—C10 | −81.6 (3) |
N3—C17—C18—C19 | −23.0 (3) | C18—C17—N3—C16 | 99.1 (2) |
N4—C18—C19—C20 | 2.3 (3) | C19—C18—N4—C26 | −2.8 (3) |
C17—C18—C19—C20 | −175.59 (19) | C17—C18—N4—C26 | 175.22 (16) |
C18—C19—C20—C21 | −0.3 (3) | C25—C26—N4—C18 | −179.18 (18) |
C19—C20—C21—C26 | −1.1 (3) | C21—C26—N4—C18 | 1.4 (3) |
Symmetry code: (i) −x+2, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 2.29 | 2.745 (3) | 116 |
O1—H1···N4 | 0.82 | 2.47 | 3.131 (3) | 139 |
O2—H2···N4 | 0.82 | 2.27 | 2.722 (3) | 116 |
O2—H2···N2ii | 0.82 | 2.55 | 3.145 (3) | 131 |
Symmetry code: (ii) x+1, y, z. |
Experimental details
Crystal data |
Chemical formula | 2C26H18N4O2·C7H8 |
Mr | 929.02 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.014 (7), 12.669 (11), 12.727 (11) |
α, β, γ (°) | 112.979 (10), 90.881 (11), 100.966 (11) |
V (Å3) | 1162.1 (17) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.15 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.975, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6333, 4077, 3049 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.596 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.156, 1.03 |
No. of reflections | 4077 |
No. of parameters | 329 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.32 |
Selected geometric parameters (Å, º) topC9—C10 | 1.474 (3) | C16—N3 | 1.385 (3) |
C10—N2 | 1.327 (3) | C17—N3 | 1.462 (3) |
C10—N3 | 1.381 (3) | C17—C18 | 1.513 (3) |
| | | |
N2—C10—N3 | 112.54 (18) | C10—N3—C17 | 129.92 (17) |
C9—N1—C1 | 117.77 (18) | C16—N3—C17 | 123.86 (16) |
C10—N2—C11 | 105.48 (17) | C18—N4—C26 | 118.16 (17) |
C10—N3—C16 | 106.21 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 2.29 | 2.745 (3) | 115.6 |
O1—H1···N4 | 0.82 | 2.47 | 3.131 (3) | 138.6 |
O2—H2···N4 | 0.82 | 2.27 | 2.722 (3) | 115.5 |
O2—H2···N2i | 0.82 | 2.55 | 3.145 (3) | 130.8 |
Symmetry code: (i) x+1, y, z. |
In most cases, without oxidant, the reaction of o-phenylenediamine with excess aldehyde produces a Shiff-base compound containing two —N═CH— bonds (Chen et al.,1987; Wang et al.,1994). However, in our case, the reaction of o-phenylenediamine with 3 equivalents of 8-hydroxyquinoline-2-aldehyde did not form the desired compound. Instead, the reaction produced a novel 2-substituted benzimidazole. Similar benzimidazole derivatives were also obtained by Dege and Yang (Dege et al., 2006; Yang et al., 2004). Usually, one of the general routes for synthesis of benzimidazole involves the reaction of a carboxylic acid with o-phenylenediamine in the presence of a strong acid (Grimmet et al., 1997; Boufatah et al., 2004). Another typical procedure involves heating o-phenylenediamine with an aldehyde in the presence of oxidant, such as Pb(OAc)4 (Kumar et al., 1981), BaMnO4 (Srivastava et al., 1988).
The molecular structure and a packing diagram of the title compound are illustrated in Figs 1 and 2, respectively. Selected geometric parameters are listed in Table 1.The compound contains 3 planar rings. One is the benzimidazole ring (N2, N3, C10—C16); the others are the 8-hydroxyquinoline rings. The 8-hydroxyquinoline ring [A(N1,O1,C1—C9)] attached to C10, is almost coplanar with the benzimidazole ring (with a dihedral angle of 3.1 (2)°). The other 8-hydroxyquinoline group [B(N4,O2,C18—C26)], was attached to the C17 methylene group almost perpendicular to the benzimidazole plane (with a dihedral angle of 93.8 (2)°). Two 8-hydroxyquinoline rings (A and B) form a dihedral angle of 96.5 (2)°. The C17—C18,C17—N3 and N2—C10 bond distances are 1.513 (3), 1.462 (3) and 1.327 (3) Å, which are similar to the corresponding bond lengths in 1-(thiophen-2-ylmethyl)-2-(thiophen-2-yl)-1H-benzimidazole (1.501 (3), 1.452 (3) and 1.315 (3) Å) (Dege et al., 2006). There is a strong intermolecular between O2—H2···N2(x + 1,y,z), with a H2···N2 distance of 2.55 Å (Figure 2, Table 2).