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Crystals of the title compound, 2C26H18N4O2·C7H8, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810004794/bv2138sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810004794/bv2138Isup2.hkl
Contains datablock I

CCDC reference: 770050

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

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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

Comment top

In most cases, without oxidant, the reaction of o-phenylenediamine with excess aldehyde produces a Shiff-base compound containing two —NCH— 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).

Related literature top

In most cases, without an oxidant the reaction of o-phenylenediamine with excess aldehyde produces a Shiff base compound containing two —NCH— bonds, see: Chen & Martell (1987); Wang et al. (1994). Similar benzimidazole derivatives have been obtained, see: Dege et al. (2006); Yang et al. (2004). For the preparation of benzimidazole, see: Boufatah et al. (2004); Grimmet (1997); Kumar et al. (1981); Srivastava & Venkataramair (1988);

Experimental top

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).

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The structure of the title compound,with the atom-numbering scheme.Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The packing view of the title compound.
Bis{2-[1-(8-hydroxy-2-quinolylmethyl)-1H-benzimidazol-2-yl]quinolin- 8-ol} toluene solvate top
Crystal data top
2C26H18N4O2·C7H8Z = 1
Mr = 929.02F(000) = 486
Triclinic, P1Dx = 1.327 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.014 (7) ÅCell parameters from 2466 reflections
b = 12.669 (11) Åθ = 3.0–25.9°
c = 12.727 (11) ŵ = 0.09 mm1
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 tube3049 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
phi and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 97
Tmin = 0.975, Tmax = 0.987k = 1514
6333 measured reflectionsl = 1215
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-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 reflectionsΔρmax = 0.40 e Å3
329 parametersΔρmin = 0.32 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.033 (4)
Crystal data top
2C26H18N4O2·C7H8γ = 100.966 (11)°
Mr = 929.02V = 1162.1 (17) Å3
Triclinic, P1Z = 1
a = 8.014 (7) ÅMo Kα radiation
b = 12.669 (11) ŵ = 0.09 mm1
c = 12.727 (11) ÅT = 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 = 0.987Rint = 0.024
6333 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0512 restraints
wR(F2) = 0.156H-atom parameters constrained
S = 1.03Δρmax = 0.40 e Å3
4077 reflectionsΔρmin = 0.32 e Å3
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
xyzUiso*/UeqOcc. (<1)
C10.5707 (3)0.12196 (18)0.05782 (17)0.0455 (5)
C20.7346 (3)0.0952 (2)0.0469 (2)0.0535 (6)
C30.7601 (3)0.0148 (2)0.1092 (2)0.0624 (6)
H30.86680.03160.10270.075*
C40.6260 (4)0.1028 (2)0.1830 (2)0.0676 (7)
H40.64530.17730.22480.081*
C50.4679 (3)0.0808 (2)0.1944 (2)0.0633 (6)
H50.38070.14020.24350.076*
C60.4366 (3)0.03220 (19)0.13169 (18)0.0509 (5)
C70.2767 (3)0.0626 (2)0.13557 (19)0.0556 (6)
H70.18330.00590.18050.067*
C80.2582 (3)0.17396 (19)0.07426 (19)0.0524 (6)
H80.15320.19420.07740.063*
C90.4018 (2)0.25868 (18)0.00545 (17)0.0434 (5)
C100.3807 (2)0.37994 (17)0.05742 (16)0.0421 (5)
C110.2623 (3)0.52959 (18)0.12008 (18)0.0462 (5)
C120.1518 (3)0.6075 (2)0.1430 (2)0.0554 (6)
H120.03940.58250.11000.066*
C130.2159 (3)0.7227 (2)0.2162 (2)0.0625 (6)
H130.14520.77630.23250.075*
C140.3845 (3)0.7607 (2)0.2665 (2)0.0652 (7)
H140.42280.83900.31600.078*
C150.4960 (3)0.6855 (2)0.2448 (2)0.0569 (6)
H150.60810.71120.27830.068*
C160.4318 (2)0.56921 (18)0.16998 (17)0.0441 (5)
C170.6860 (2)0.47670 (18)0.15656 (18)0.0437 (5)
H17A0.74970.55690.18110.052*
H17B0.73140.42930.08780.052*
C180.7154 (2)0.43377 (16)0.24939 (16)0.0411 (5)
C190.5972 (3)0.43317 (19)0.33017 (18)0.0511 (5)
H190.49350.45450.32490.061*
C200.6374 (3)0.4007 (2)0.41619 (19)0.0557 (6)
H200.56050.40040.47010.067*
C210.7938 (3)0.36783 (18)0.42466 (17)0.0481 (5)
C220.8471 (3)0.3341 (2)0.5118 (2)0.0632 (6)
H220.77760.33380.56950.076*
C231.0006 (4)0.3022 (2)0.5104 (2)0.0702 (7)
H231.03460.27990.56750.084*
C241.1081 (3)0.3024 (2)0.4245 (2)0.0680 (7)
H241.21230.28040.42520.082*
C251.0602 (3)0.3348 (2)0.3397 (2)0.0556 (6)
C260.9023 (2)0.36878 (17)0.33817 (17)0.0440 (5)
C270.6666 (8)0.9326 (7)0.5448 (6)0.109 (2)0.50
H27A0.63520.84840.51160.163*0.50
H27B0.59040.96350.51120.163*0.50
H27C0.65900.96100.62600.163*0.50
C280.8398 (8)0.9701 (3)0.5231 (4)0.1311 (17)
C290.8662 (8)0.9652 (4)0.4163 (4)0.151 (2)
H290.77530.94090.36010.181*
C301.0280 (8)0.9965 (4)0.3939 (4)0.141 (2)
H301.04930.99530.32190.169*
N10.5530 (2)0.23373 (15)0.00443 (14)0.0448 (4)
N20.2332 (2)0.41096 (15)0.05066 (15)0.0486 (5)
N30.5069 (2)0.47278 (14)0.12805 (14)0.0426 (4)
N40.8615 (2)0.40046 (14)0.25095 (14)0.0437 (4)
O10.8628 (2)0.17832 (16)0.02683 (16)0.0740 (5)
H10.82930.23940.05890.111*
O21.1662 (2)0.3371 (2)0.25782 (18)0.0811 (6)
H21.11740.35120.20930.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0529 (12)0.0487 (12)0.0422 (12)0.0166 (9)0.0120 (9)0.0232 (10)
C20.0539 (13)0.0595 (14)0.0556 (14)0.0219 (11)0.0143 (10)0.0271 (11)
C30.0682 (16)0.0667 (16)0.0672 (16)0.0343 (13)0.0272 (12)0.0325 (13)
C40.091 (2)0.0566 (15)0.0625 (16)0.0302 (14)0.0287 (14)0.0244 (12)
C50.0789 (17)0.0514 (14)0.0552 (14)0.0112 (12)0.0127 (12)0.0176 (11)
C60.0610 (14)0.0511 (13)0.0430 (12)0.0117 (10)0.0097 (10)0.0214 (10)
C70.0552 (13)0.0541 (14)0.0526 (13)0.0027 (10)0.0015 (10)0.0204 (11)
C80.0441 (12)0.0589 (14)0.0560 (13)0.0092 (10)0.0010 (10)0.0260 (11)
C90.0438 (11)0.0506 (12)0.0424 (11)0.0128 (9)0.0048 (8)0.0243 (9)
C100.0395 (11)0.0515 (12)0.0420 (11)0.0120 (9)0.0034 (8)0.0249 (9)
C110.0455 (11)0.0545 (13)0.0492 (12)0.0162 (9)0.0099 (9)0.0291 (10)
C120.0471 (12)0.0673 (15)0.0682 (15)0.0250 (11)0.0153 (10)0.0383 (13)
C130.0691 (16)0.0657 (16)0.0717 (16)0.0334 (13)0.0234 (12)0.0382 (13)
C140.0793 (17)0.0525 (14)0.0670 (16)0.0222 (12)0.0132 (13)0.0236 (12)
C150.0582 (14)0.0547 (14)0.0584 (14)0.0136 (11)0.0034 (11)0.0227 (11)
C160.0465 (11)0.0502 (12)0.0455 (12)0.0166 (9)0.0089 (9)0.0267 (10)
C170.0359 (10)0.0505 (12)0.0486 (12)0.0099 (8)0.0023 (8)0.0236 (9)
C180.0375 (10)0.0424 (11)0.0410 (11)0.0084 (8)0.0008 (8)0.0142 (9)
C190.0423 (11)0.0665 (14)0.0477 (13)0.0199 (10)0.0052 (9)0.0225 (11)
C200.0548 (13)0.0716 (15)0.0456 (13)0.0202 (11)0.0140 (10)0.0254 (11)
C210.0557 (13)0.0482 (12)0.0412 (12)0.0143 (10)0.0029 (9)0.0173 (9)
C220.0791 (17)0.0717 (16)0.0489 (14)0.0247 (13)0.0084 (12)0.0309 (12)
C230.0856 (19)0.0767 (17)0.0633 (16)0.0304 (14)0.0019 (13)0.0381 (14)
C240.0625 (15)0.0780 (17)0.0804 (18)0.0291 (13)0.0023 (13)0.0431 (14)
C250.0489 (13)0.0634 (14)0.0669 (15)0.0196 (11)0.0063 (11)0.0357 (12)
C260.0437 (11)0.0418 (11)0.0466 (12)0.0084 (9)0.0012 (9)0.0184 (9)
C270.126 (6)0.111 (6)0.093 (5)0.052 (5)0.008 (5)0.033 (4)
C280.243 (5)0.064 (2)0.083 (3)0.045 (3)0.029 (3)0.0222 (18)
C290.262 (7)0.096 (3)0.094 (3)0.027 (4)0.041 (4)0.044 (2)
C300.268 (7)0.085 (3)0.069 (3)0.036 (4)0.027 (4)0.031 (2)
N10.0448 (10)0.0504 (10)0.0444 (10)0.0156 (8)0.0062 (7)0.0220 (8)
N20.0403 (9)0.0540 (11)0.0579 (11)0.0146 (8)0.0035 (8)0.0270 (9)
N30.0383 (9)0.0491 (10)0.0464 (10)0.0136 (7)0.0035 (7)0.0237 (8)
N40.0381 (9)0.0495 (10)0.0473 (10)0.0131 (7)0.0031 (7)0.0217 (8)
O10.0539 (10)0.0736 (12)0.0870 (13)0.0276 (9)0.0027 (9)0.0180 (10)
O20.0540 (10)0.1300 (17)0.1009 (15)0.0461 (11)0.0256 (10)0.0773 (13)
Geometric parameters (Å, º) top
C1—N11.363 (3)C17—C181.513 (3)
C1—C61.415 (3)C17—H17A0.9700
C1—C21.435 (3)C17—H17B0.9700
C2—O11.354 (3)C18—N41.320 (3)
C2—C31.365 (3)C18—C191.410 (3)
C3—C41.406 (4)C19—C201.365 (3)
C3—H30.9300C19—H190.9300
C4—C51.365 (4)C20—C211.409 (3)
C4—H40.9300C20—H200.9300
C5—C61.414 (3)C21—C261.416 (3)
C5—H50.9300C21—C221.421 (3)
C6—C71.411 (3)C22—C231.365 (4)
C7—C81.358 (3)C22—H220.9300
C7—H70.9300C23—C241.403 (4)
C8—C91.418 (3)C23—H230.9300
C8—H80.9300C24—C251.369 (3)
C9—N11.325 (3)C24—H240.9300
C9—C101.474 (3)C25—O21.361 (3)
C10—N21.327 (3)C25—C261.414 (3)
C10—N31.381 (3)C26—N41.374 (3)
C11—N21.385 (3)C27—C281.4463 (15)
C11—C121.400 (3)C27—H27A0.9600
C11—C161.402 (3)C27—H27B0.9600
C12—C131.378 (4)C27—H27C0.9600
C12—H120.9300C28—C291.358 (6)
C13—C141.398 (4)C28—C30i1.365 (6)
C13—H130.9300C29—C301.351 (9)
C14—C151.381 (3)C29—H290.9300
C14—H140.9300C30—C28i1.365 (6)
C15—C161.394 (3)C30—H300.9300
C15—H150.9300O1—H10.8200
C16—N31.385 (3)O2—H20.8200
C17—N31.462 (3)
N1—C1—C6123.4 (2)C18—C17—H17B108.7
N1—C1—C2117.63 (19)H17A—C17—H17B107.6
C6—C1—C2119.0 (2)N4—C18—C19122.82 (19)
O1—C2—C3120.0 (2)N4—C18—C17115.06 (17)
O1—C2—C1120.0 (2)C19—C18—C17122.09 (18)
C3—C2—C1120.0 (2)C20—C19—C18118.8 (2)
C2—C3—C4120.4 (2)C20—C19—H19120.6
C2—C3—H3119.8C18—C19—H19120.6
C4—C3—H3119.8C19—C20—C21121.0 (2)
C5—C4—C3121.2 (2)C19—C20—H20119.5
C5—C4—H4119.4C21—C20—H20119.5
C3—C4—H4119.4C20—C21—C26115.94 (19)
C4—C5—C6120.1 (2)C20—C21—C22124.9 (2)
C4—C5—H5119.9C26—C21—C22119.2 (2)
C6—C5—H5119.9C23—C22—C21119.8 (2)
C7—C6—C5124.3 (2)C23—C22—H22120.1
C7—C6—C1116.4 (2)C21—C22—H22120.1
C5—C6—C1119.3 (2)C22—C23—C24121.2 (2)
C8—C7—C6120.6 (2)C22—C23—H23119.4
C8—C7—H7119.7C24—C23—H23119.4
C6—C7—H7119.7C25—C24—C23120.2 (2)
C7—C8—C9118.8 (2)C25—C24—H24119.9
C7—C8—H8120.6C23—C24—H24119.9
C9—C8—H8120.6O2—C25—C24120.1 (2)
N1—C9—C8123.0 (2)O2—C25—C26119.5 (2)
N1—C9—C10118.97 (18)C24—C25—C26120.3 (2)
C8—C9—C10117.98 (18)N4—C26—C25117.61 (19)
N2—C10—N3112.54 (18)N4—C26—C21123.14 (19)
N2—C10—C9122.02 (18)C25—C26—C21119.2 (2)
N3—C10—C9125.44 (17)C28—C27—H27A109.5
N2—C11—C12129.9 (2)C28—C27—H27B109.5
N2—C11—C16109.73 (17)H27A—C27—H27B109.5
C12—C11—C16120.4 (2)C28—C27—H27C109.5
C13—C12—C11117.5 (2)H27A—C27—H27C109.5
C13—C12—H12121.2H27B—C27—H27C109.5
C11—C12—H12121.2C29—C28—C30i121.6 (5)
C12—C13—C14121.5 (2)C29—C28—C27117.7 (6)
C12—C13—H13119.2C30i—C28—C27120.6 (6)
C14—C13—H13119.2C30—C29—C28118.3 (5)
C15—C14—C13121.9 (2)C30—C29—H29120.9
C15—C14—H14119.0C28—C29—H29120.9
C13—C14—H14119.0C29—C30—C28i120.1 (5)
C14—C15—C16116.6 (2)C29—C30—H30120.0
C14—C15—H15121.7C28i—C30—H30120.0
C16—C15—H15121.7C9—N1—C1117.77 (18)
N3—C16—C15132.0 (2)C10—N2—C11105.48 (17)
N3—C16—C11106.02 (18)C10—N3—C16106.21 (16)
C15—C16—C11122.00 (19)C10—N3—C17129.92 (17)
N3—C17—C18114.36 (16)C16—N3—C17123.86 (16)
N3—C17—H17A108.7C18—N4—C26118.16 (17)
C18—C17—H17A108.7C2—O1—H1109.5
N3—C17—H17B108.7C25—O2—H2109.5
N1—C1—C2—O12.7 (3)C19—C20—C21—C22179.3 (2)
C6—C1—C2—O1177.24 (19)C20—C21—C22—C23179.0 (2)
N1—C1—C2—C3178.68 (19)C26—C21—C22—C230.6 (3)
C6—C1—C2—C31.4 (3)C21—C22—C23—C240.3 (4)
O1—C2—C3—C4177.8 (2)C22—C23—C24—C250.1 (4)
C1—C2—C3—C40.8 (3)C23—C24—C25—O2178.7 (2)
C2—C3—C4—C50.0 (4)C23—C24—C25—C260.2 (4)
C3—C4—C5—C60.2 (4)O2—C25—C26—N41.5 (3)
C4—C5—C6—C7178.4 (2)C24—C25—C26—N4179.9 (2)
C4—C5—C6—C10.4 (3)O2—C25—C26—C21179.1 (2)
N1—C1—C6—C72.3 (3)C24—C25—C26—C210.6 (3)
C2—C1—C6—C7177.70 (19)C20—C21—C26—N40.6 (3)
N1—C1—C6—C5178.91 (19)C22—C21—C26—N4179.78 (19)
C2—C1—C6—C51.1 (3)C20—C21—C26—C25178.89 (19)
C5—C6—C7—C8178.7 (2)C22—C21—C26—C250.8 (3)
C1—C6—C7—C82.5 (3)C30i—C28—C29—C301.2 (8)
C6—C7—C8—C90.7 (3)C27—C28—C29—C30178.0 (5)
C7—C8—C9—N11.8 (3)C28—C29—C30—C28i1.2 (8)
C7—C8—C9—C10178.01 (19)C8—C9—N1—C12.2 (3)
N1—C9—C10—N2179.53 (18)C10—C9—N1—C1177.69 (17)
C8—C9—C10—N20.3 (3)C6—C1—N1—C90.0 (3)
N1—C9—C10—N30.2 (3)C2—C1—N1—C9180.00 (18)
C8—C9—C10—N3179.92 (18)N3—C10—N2—C110.2 (2)
N2—C11—C12—C13179.8 (2)C9—C10—N2—C11179.95 (17)
C16—C11—C12—C130.5 (3)C12—C11—N2—C10178.8 (2)
C11—C12—C13—C140.3 (3)C16—C11—N2—C100.6 (2)
C12—C13—C14—C150.6 (4)N2—C10—N3—C160.8 (2)
C13—C14—C15—C160.1 (4)C9—C10—N3—C16179.41 (18)
C14—C15—C16—N3178.5 (2)N2—C10—N3—C17178.58 (18)
C14—C15—C16—C110.8 (3)C9—C10—N3—C171.2 (3)
N2—C11—C16—N31.0 (2)C15—C16—N3—C10179.6 (2)
C12—C11—C16—N3178.36 (18)C11—C16—N3—C101.1 (2)
N2—C11—C16—C15179.55 (19)C15—C16—N3—C171.0 (3)
C12—C11—C16—C151.1 (3)C11—C16—N3—C17178.35 (17)
N3—C17—C18—N4158.92 (17)C18—C17—N3—C1081.6 (3)
N3—C17—C18—C1923.0 (3)C18—C17—N3—C1699.1 (2)
N4—C18—C19—C202.3 (3)C19—C18—N4—C262.8 (3)
C17—C18—C19—C20175.59 (19)C17—C18—N4—C26175.22 (16)
C18—C19—C20—C210.3 (3)C25—C26—N4—C18179.18 (18)
C19—C20—C21—C261.1 (3)C21—C26—N4—C181.4 (3)
Symmetry code: (i) x+2, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.822.292.745 (3)116
O1—H1···N40.822.473.131 (3)139
O2—H2···N40.822.272.722 (3)116
O2—H2···N2ii0.822.553.145 (3)131
Symmetry code: (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula2C26H18N4O2·C7H8
Mr929.02
Crystal system, space groupTriclinic, 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)
V3)1162.1 (17)
Z1
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.975, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
6333, 4077, 3049
Rint0.024
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.156, 1.03
No. of reflections4077
No. of parameters329
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.32

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
C9—C101.474 (3)C16—N31.385 (3)
C10—N21.327 (3)C17—N31.462 (3)
C10—N31.381 (3)C17—C181.513 (3)
N2—C10—N3112.54 (18)C10—N3—C17129.92 (17)
C9—N1—C1117.77 (18)C16—N3—C17123.86 (16)
C10—N2—C11105.48 (17)C18—N4—C26118.16 (17)
C10—N3—C16106.21 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.822.292.745 (3)115.6
O1—H1···N40.822.473.131 (3)138.6
O2—H2···N40.822.272.722 (3)115.5
O2—H2···N2i0.822.553.145 (3)130.8
Symmetry code: (i) x+1, y, z.
 

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