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In the title compound, C26H19BrN2O2, all bond lengths and angles show normal values. Two hydr­oxy groups are involved in intra­molecular O—H...N hydrogen bonds, which influence the mol­ecular conformation. In the crystal structure, weak inter­molecular C—H...O hydrogen bonds link the mol­ecules into zigzag chains along the [101] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055018/cv2333sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055018/cv2333Isup2.hkl
Contains datablock I

CCDC reference: 672869

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.034
  • wR factor = 0.091
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.12 Ratio PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C26 H19 Br N2 O2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Schiff bases exhibit often important biological activities such as antibacterial (Abu-Hussen et al., 2006), antifungal (Singh et al., 2006) and antitumor (Mladenova et al., 2002). Radio-labeled (bio) molecules are potentially useful tools for cancer diagnosis and therapy. Many efforts have been made to develop diagnostic pharmaceuticals of 99mTc-labelled small molecular complexes because of the superior medico-imaging characteristics (biological t1/2, Low energy content) and the availability of radionuclide (Jurisson et al., 1999). Since the small size of the complex is very important for the retention of the bioactivity, one of the strategies in the investigation is to explore novel complexes with small size, multifunctional ligands that possess specific bioactivities. Amino acids, mono/disaccharides and vitamins are good examples for these applications. Some applications of these Schiff bases with favorable cell membrane permeability have been exploited in cancer multidrug resistance (Jurisson et al., 1999). We describe here the structure of the title compound.

In the title compound, bond lengths are slightly different from those in similar compounds. The C—Br bond length [1.905 (2) Å] is longer than others reported [1.865 (1) (Dale et al., 1999) and 1.884 (2) Å (Wiktor et al., 2000)]. The C—N bond lengths [1.276 (3) and 1.291 (3) Å] are shorter than that of 1.335 (2) Å reported by Sanjay et al. (2004). Two hydroxy groups are involved in intramolecular O—H···N hydrogen-bonding (Table 1).

The mean planes of the rings C1—C6 (P1), C8—C13 (P2), C14—C19 (P3) and C21—C26 (P4) make the following dihedral angles - P1/P4 78.3 (2)°, P2/P4 68.9 (4) and P3/P4 11.1 (2)°.

In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into zigzag chains along direction [101].

Related literature top

For related literature, see: Abu-Hussen (2006); Dale et al. (1999); Jurisson & Lydon (1999); Mladenova et al. (2002); Sanjay et al. (2004); Singh et al. (2006); Wiktor et al. (2000).

Experimental top

5-Bromo-2-hydroxybenzophenone (27.7 g, 0.1 mol), 1,2-diaminobenzene (10.8 g, 0.1 mol), piperidine (10.2 g, 0.12 mol) and triethylorthoformate (12 ml) were refluxed in absolute ethanol (120 ml) resulting in red-orange product of HBBP-PHEN. The title compound was prepared by the reaction of HBBP-PHEN (22.0 g, 0.06 mol), salicylaldehyde (12.2 g, 0.1 mol) with piperidine (10.2 g, 0.12 mol) at room temperature. The precipitated yellow solid was collected by filtration and washed twice with hot methanol. Single crystals suitable for X-ray measurements were obtained by recrystallization from absolute ethanol and acetic ether (1:1,v/v) at room temperature.

Refinement top

C-bound H atoms were fixed geometrically (C—H 0.93 Å) and allowed to ride on their parent atoms, with Uiso(H)=1.2Ueq(C). Atoms H1 and H2 were located on difference map and refined isotropically with bond restraint O—H = 0.80 (3) Å.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
4-Bromo-2-{[2-(2-hydroxybenzylideneamino)phenylimino]phenylmethyl}phenol top
Crystal data top
C26H19BrN2O2Z = 2
Mr = 471.34F(000) = 480
Triclinic, P1Dx = 1.436 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1682 (18) ÅCell parameters from 25 reflections
b = 9.7011 (19) Åθ = 4–14°
c = 12.986 (3) ŵ = 1.91 mm1
α = 90.87 (3)°T = 295 K
β = 108.79 (3)°Block, colourless
γ = 94.09 (3)°0.25 × 0.20 × 0.20 mm
V = 1089.8 (4) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.018
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.7°
Graphite monochromatorh = 1010
ω scansk = 117
4501 measured reflectionsl = 1512
3742 independent reflections3 standard reflections every 100 reflections
2837 reflections with I > 2σ(I) intensity decay: none
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)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0443P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3742 reflectionsΔρmax = 0.26 e Å3
289 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0051 (14)
Crystal data top
C26H19BrN2O2γ = 94.09 (3)°
Mr = 471.34V = 1089.8 (4) Å3
Triclinic, P1Z = 2
a = 9.1682 (18) ÅMo Kα radiation
b = 9.7011 (19) ŵ = 1.91 mm1
c = 12.986 (3) ÅT = 295 K
α = 90.87 (3)°0.25 × 0.20 × 0.20 mm
β = 108.79 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.018
4501 measured reflections3 standard reflections every 100 reflections
3742 independent reflections intensity decay: none
2837 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.26 e Å3
3742 reflectionsΔρmin = 0.30 e Å3
289 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*/Ueq
Br10.10044 (3)0.19363 (3)0.02361 (3)0.06928 (16)
O10.4811 (3)0.3545 (2)0.0968 (2)0.0759 (7)
O20.2232 (3)0.3849 (3)0.4416 (2)0.0907 (8)
N10.4694 (3)0.2214 (2)0.41956 (17)0.0535 (6)
N20.4777 (3)0.1461 (2)0.21221 (16)0.0518 (5)
C10.3534 (3)0.3110 (3)0.0812 (2)0.0536 (7)
C20.2881 (3)0.3884 (3)0.0147 (2)0.0619 (8)
H2C0.33490.46550.01830.074*
C30.1559 (3)0.3518 (3)0.0024 (2)0.0562 (7)
H3A0.11280.40430.04620.067*
C40.0870 (3)0.2371 (3)0.0456 (2)0.0474 (6)
C50.1511 (3)0.1557 (3)0.10858 (19)0.0462 (6)
H5A0.10420.07730.13890.055*
C60.2872 (3)0.1906 (2)0.12716 (18)0.0436 (6)
C70.3600 (3)0.1023 (3)0.19163 (18)0.0442 (6)
C80.2987 (3)0.0321 (3)0.2296 (2)0.0487 (6)
C90.3297 (4)0.1462 (3)0.1588 (3)0.0759 (9)
H9A0.38420.13780.08550.091*
C100.2800 (5)0.2733 (4)0.1967 (4)0.0986 (13)
H10A0.30170.35020.14910.118*
C110.1981 (5)0.2849 (4)0.3055 (4)0.1011 (14)
H11A0.16500.37000.33120.121*
C120.1656 (4)0.1727 (4)0.3750 (3)0.0879 (11)
H12A0.10940.18110.44800.106*
C130.2157 (3)0.0453 (3)0.3376 (2)0.0647 (8)
H13A0.19320.03120.38570.078*
C140.2425 (4)0.4371 (3)0.5333 (2)0.0647 (8)
C150.1351 (4)0.5408 (3)0.5954 (3)0.0794 (9)
H15A0.05260.57390.57330.095*
C160.1522 (4)0.5937 (3)0.6893 (3)0.0823 (10)
H16A0.08050.66260.73040.099*
C170.2734 (4)0.5464 (4)0.7236 (3)0.0815 (10)
H17A0.28290.58290.78750.098*
C180.3795 (4)0.4459 (3)0.6633 (2)0.0716 (9)
H18A0.46170.41470.68640.086*
C190.3663 (3)0.3888 (3)0.5670 (2)0.0546 (7)
C200.4790 (3)0.2801 (3)0.5055 (2)0.0580 (7)
H20A0.56120.25210.52960.070*
C210.5766 (3)0.1108 (3)0.3638 (2)0.0495 (6)
C220.6821 (3)0.0394 (3)0.4052 (2)0.0671 (8)
H22A0.68670.06660.47300.081*
C230.7793 (3)0.0705 (3)0.3476 (3)0.0684 (8)
H23A0.85080.11470.37560.082*
C240.7710 (3)0.1143 (3)0.2498 (2)0.0647 (8)
H24A0.83520.18960.21180.078*
C250.6669 (3)0.0467 (3)0.2071 (2)0.0617 (7)
H25A0.66170.07700.14010.074*
C260.5700 (3)0.0657 (3)0.2628 (2)0.0474 (6)
H10.500 (4)0.301 (3)0.139 (3)0.080 (11)*
H20.290 (4)0.323 (4)0.415 (3)0.105 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0561 (2)0.0758 (3)0.0844 (3)0.00471 (15)0.03481 (16)0.00113 (17)
O10.0859 (16)0.0664 (15)0.1017 (17)0.0342 (12)0.0595 (14)0.0357 (13)
O20.0899 (17)0.1015 (19)0.0897 (17)0.0397 (16)0.0532 (14)0.0303 (15)
N10.0595 (14)0.0516 (14)0.0530 (13)0.0048 (11)0.0252 (11)0.0004 (11)
N20.0615 (14)0.0484 (13)0.0531 (12)0.0059 (11)0.0288 (11)0.0048 (10)
C10.0584 (16)0.0456 (16)0.0644 (17)0.0116 (13)0.0288 (14)0.0078 (13)
C20.074 (2)0.0489 (17)0.0747 (19)0.0162 (15)0.0370 (16)0.0188 (15)
C30.0667 (18)0.0491 (17)0.0593 (16)0.0040 (14)0.0309 (14)0.0064 (14)
C40.0466 (14)0.0464 (15)0.0495 (14)0.0015 (12)0.0169 (12)0.0028 (12)
C50.0523 (15)0.0406 (14)0.0461 (14)0.0041 (12)0.0166 (12)0.0003 (12)
C60.0509 (14)0.0400 (14)0.0414 (13)0.0035 (12)0.0172 (11)0.0005 (11)
C70.0506 (15)0.0432 (14)0.0391 (13)0.0002 (12)0.0161 (11)0.0048 (11)
C80.0547 (15)0.0456 (16)0.0546 (16)0.0063 (13)0.0290 (13)0.0078 (13)
C90.100 (3)0.0517 (19)0.080 (2)0.0100 (18)0.0338 (19)0.0046 (17)
C100.130 (3)0.049 (2)0.142 (4)0.015 (2)0.078 (3)0.008 (2)
C110.113 (3)0.083 (3)0.146 (4)0.044 (3)0.087 (3)0.056 (3)
C120.081 (2)0.107 (3)0.093 (3)0.037 (2)0.044 (2)0.052 (3)
C130.0644 (18)0.074 (2)0.0624 (18)0.0141 (16)0.0278 (15)0.0177 (16)
C140.0684 (19)0.0620 (19)0.0627 (18)0.0044 (16)0.0221 (15)0.0041 (15)
C150.069 (2)0.075 (2)0.090 (2)0.0137 (18)0.0232 (18)0.006 (2)
C160.088 (3)0.065 (2)0.074 (2)0.0004 (19)0.0017 (19)0.0128 (18)
C170.093 (3)0.077 (2)0.068 (2)0.007 (2)0.0176 (19)0.0120 (18)
C180.082 (2)0.067 (2)0.0681 (19)0.0057 (18)0.0270 (17)0.0061 (17)
C190.0590 (17)0.0490 (16)0.0559 (16)0.0049 (14)0.0184 (13)0.0025 (14)
C200.0591 (17)0.0592 (18)0.0609 (17)0.0014 (14)0.0273 (14)0.0044 (15)
C210.0500 (15)0.0480 (16)0.0546 (15)0.0036 (13)0.0226 (13)0.0033 (13)
C220.076 (2)0.070 (2)0.0663 (18)0.0111 (17)0.0420 (16)0.0019 (16)
C230.0593 (18)0.068 (2)0.085 (2)0.0085 (16)0.0358 (16)0.0062 (17)
C240.0604 (18)0.0603 (19)0.0660 (18)0.0094 (15)0.0132 (15)0.0002 (15)
C250.0691 (19)0.0618 (19)0.0517 (16)0.0018 (16)0.0179 (14)0.0012 (14)
C260.0474 (15)0.0470 (15)0.0514 (15)0.0067 (12)0.0200 (12)0.0096 (13)
Geometric parameters (Å, º) top
Br1—C41.905 (2)C12—C131.389 (4)
O1—C11.346 (3)C12—H12A0.9300
O1—H10.80 (3)C13—H13A0.9300
O2—C141.354 (3)C14—C191.397 (4)
O2—H20.81 (3)C14—C151.398 (4)
N1—C201.276 (3)C15—C161.375 (4)
N1—C211.418 (3)C15—H15A0.9300
N2—C71.291 (3)C16—C171.377 (5)
N2—C261.427 (3)C16—H16A0.9300
C1—C21.399 (4)C17—C181.364 (4)
C1—C61.406 (3)C17—H17A0.9300
C2—C31.370 (4)C18—C191.404 (4)
C2—H2C0.9300C18—H18A0.9300
C3—C41.376 (4)C19—C201.451 (4)
C3—H3A0.9300C20—N11.276 (3)
C4—C51.379 (3)C20—H20A0.9300
C5—C61.407 (3)C21—C221.398 (3)
C5—H5A0.9300C21—C261.398 (3)
C6—C71.477 (3)C21—N11.418 (3)
C7—N21.291 (3)C22—C231.379 (4)
C7—C81.485 (4)C22—H22A0.9300
C8—C131.377 (4)C23—C241.359 (4)
C8—C91.380 (4)C23—H23A0.9300
C9—C101.387 (5)C24—C251.383 (4)
C9—H9A0.9300C24—H24A0.9300
C10—C111.381 (6)C25—C261.388 (4)
C10—H10A0.9300C25—H25A0.9300
C11—C121.355 (5)C26—N21.427 (3)
C11—H11A0.9300
C1—O1—H1104 (2)O2—C14—C19121.4 (3)
C14—O2—H2110 (3)O2—C14—C15118.9 (3)
C20—N1—C21121.4 (2)C19—C14—C15119.7 (3)
C7—N2—C26123.7 (2)C16—C15—C14119.6 (3)
O1—C1—C2117.7 (2)C16—C15—H15A120.2
O1—C1—C6122.4 (2)C14—C15—H15A120.2
C2—C1—C6119.9 (2)C15—C16—C17121.2 (3)
C3—C2—C1120.7 (3)C15—C16—H16A119.4
C3—C2—H2C119.6C17—C16—H16A119.4
C1—C2—H2C119.6C18—C17—C16119.7 (3)
C2—C3—C4119.7 (2)C18—C17—H17A120.1
C2—C3—H3A120.1C16—C17—H17A120.1
C4—C3—H3A120.1C17—C18—C19120.9 (3)
C3—C4—C5121.1 (2)C17—C18—H18A119.5
C3—C4—Br1118.32 (19)C19—C18—H18A119.5
C5—C4—Br1120.6 (2)C14—C19—C18118.8 (3)
C4—C5—C6120.3 (2)C14—C19—C20121.3 (2)
C4—C5—H5A119.8C18—C19—C20119.9 (3)
C6—C5—H5A119.8N1—C20—C19122.4 (2)
C1—C6—C5118.1 (2)N1—C20—C19122.4 (2)
C1—C6—C7120.8 (2)N1—C20—H20A118.8
C5—C6—C7121.1 (2)N1—C20—H20A118.8
N2—C7—C6117.6 (2)C19—C20—H20A118.8
N2—C7—C6117.6 (2)C22—C21—C26118.0 (2)
N2—C7—C8122.2 (2)C22—C21—N1124.7 (2)
N2—C7—C8122.2 (2)C26—C21—N1117.2 (2)
C6—C7—C8120.2 (2)C22—C21—N1124.7 (2)
C13—C8—C9119.3 (3)C26—C21—N1117.2 (2)
C13—C8—C7119.8 (2)C23—C22—C21121.3 (3)
C9—C8—C7120.8 (2)C23—C22—H22A119.4
C8—C9—C10120.3 (3)C21—C22—H22A119.3
C8—C9—H9A119.9C24—C23—C22120.2 (3)
C10—C9—H9A119.9C24—C23—H23A119.9
C11—C10—C9119.6 (4)C22—C23—H23A119.9
C11—C10—H10A120.2C23—C24—C25119.9 (3)
C9—C10—H10A120.2C23—C24—H24A120.1
C12—C11—C10120.3 (4)C25—C24—H24A120.1
C12—C11—H11A119.8C24—C25—C26120.8 (3)
C10—C11—H11A119.8C24—C25—H25A119.6
C11—C12—C13120.3 (4)C26—C25—H25A119.6
C11—C12—H12A119.8C25—C26—C21119.7 (2)
C13—C12—H12A119.8C25—C26—N2120.5 (2)
C8—C13—C12120.1 (3)C21—C26—N2119.3 (2)
C8—C13—H13A119.9C25—C26—N2120.5 (2)
C12—C13—H13A119.9C21—C26—N2119.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.80 (3)1.79 (3)2.530 (3)154 (3)
O2—H2···N10.81 (3)1.87 (3)2.596 (3)148 (3)
C2—H2C···O1i0.932.513.419 (4)166
C15—H15A···O2ii0.932.603.497 (4)162
Symmetry codes: (i) x1, y+1, z; (ii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC26H19BrN2O2
Mr471.34
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)9.1682 (18), 9.7011 (19), 12.986 (3)
α, β, γ (°)90.87 (3), 108.79 (3), 94.09 (3)
V3)1089.8 (4)
Z2
Radiation typeMo Kα
µ (mm1)1.91
Crystal size (mm)0.25 × 0.20 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4501, 3742, 2837
Rint0.018
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.091, 1.07
No. of reflections3742
No. of parameters289
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.26, 0.30

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1990), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.80 (3)1.79 (3)2.530 (3)154 (3)
O2—H2···N10.81 (3)1.87 (3)2.596 (3)148 (3)
C2—H2C···O1i0.932.513.419 (4)165.6
C15—H15A···O2ii0.932.603.497 (4)162.0
Symmetry codes: (i) x1, y+1, z; (ii) x, y+1, z+1.
 

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