Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055018/cv2333sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055018/cv2333Isup2.hkl |
CCDC reference: 672869
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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).
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.
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.
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).
Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
C26H19BrN2O2 | Z = 2 |
Mr = 471.34 | F(000) = 480 |
Triclinic, P1 | Dx = 1.436 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1682 (18) Å | Cell parameters from 25 reflections |
b = 9.7011 (19) Å | θ = 4–14° |
c = 12.986 (3) Å | µ = 1.91 mm−1 |
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 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.018 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.7° |
Graphite monochromator | h = −10→10 |
ω scans | k = −11→7 |
4501 measured reflections | l = −15→12 |
3742 independent reflections | 3 standard reflections every 100 reflections |
2837 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.034 | H 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 reflections | Δρmax = 0.26 e Å−3 |
289 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0051 (14) |
C26H19BrN2O2 | γ = 94.09 (3)° |
Mr = 471.34 | V = 1089.8 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.1682 (18) Å | Mo Kα radiation |
b = 9.7011 (19) Å | µ = 1.91 mm−1 |
c = 12.986 (3) Å | T = 295 K |
α = 90.87 (3)° | 0.25 × 0.20 × 0.20 mm |
β = 108.79 (3)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.018 |
4501 measured reflections | 3 standard reflections every 100 reflections |
3742 independent reflections | intensity decay: none |
2837 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.26 e Å−3 |
3742 reflections | Δρmin = −0.30 e Å−3 |
289 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.10044 (3) | 0.19363 (3) | 0.02361 (3) | 0.06928 (16) | |
O1 | −0.4811 (3) | 0.3545 (2) | 0.0968 (2) | 0.0759 (7) | |
O2 | −0.2232 (3) | 0.3849 (3) | 0.4416 (2) | 0.0907 (8) | |
N1 | −0.4694 (3) | 0.2214 (2) | 0.41956 (17) | 0.0535 (6) | |
N2 | −0.4777 (3) | 0.1461 (2) | 0.21221 (16) | 0.0518 (5) | |
C1 | −0.3534 (3) | 0.3110 (3) | 0.0812 (2) | 0.0536 (7) | |
C2 | −0.2881 (3) | 0.3884 (3) | 0.0147 (2) | 0.0619 (8) | |
H2C | −0.3349 | 0.4655 | −0.0183 | 0.074* | |
C3 | −0.1559 (3) | 0.3518 (3) | −0.0024 (2) | 0.0562 (7) | |
H3A | −0.1128 | 0.4043 | −0.0462 | 0.067* | |
C4 | −0.0870 (3) | 0.2371 (3) | 0.0456 (2) | 0.0474 (6) | |
C5 | −0.1511 (3) | 0.1557 (3) | 0.10858 (19) | 0.0462 (6) | |
H5A | −0.1042 | 0.0773 | 0.1389 | 0.055* | |
C6 | −0.2872 (3) | 0.1906 (2) | 0.12716 (18) | 0.0436 (6) | |
C7 | −0.3600 (3) | 0.1023 (3) | 0.19163 (18) | 0.0442 (6) | |
C8 | −0.2987 (3) | −0.0321 (3) | 0.2296 (2) | 0.0487 (6) | |
C9 | −0.3297 (4) | −0.1462 (3) | 0.1588 (3) | 0.0759 (9) | |
H9A | −0.3842 | −0.1378 | 0.0855 | 0.091* | |
C10 | −0.2800 (5) | −0.2733 (4) | 0.1967 (4) | 0.0986 (13) | |
H10A | −0.3017 | −0.3502 | 0.1491 | 0.118* | |
C11 | −0.1981 (5) | −0.2849 (4) | 0.3055 (4) | 0.1011 (14) | |
H11A | −0.1650 | −0.3700 | 0.3312 | 0.121* | |
C12 | −0.1656 (4) | −0.1727 (4) | 0.3750 (3) | 0.0879 (11) | |
H12A | −0.1094 | −0.1811 | 0.4480 | 0.106* | |
C13 | −0.2157 (3) | −0.0453 (3) | 0.3376 (2) | 0.0647 (8) | |
H13A | −0.1932 | 0.0312 | 0.3857 | 0.078* | |
C14 | −0.2425 (4) | 0.4371 (3) | 0.5333 (2) | 0.0647 (8) | |
C15 | −0.1351 (4) | 0.5408 (3) | 0.5954 (3) | 0.0794 (9) | |
H15A | −0.0526 | 0.5739 | 0.5733 | 0.095* | |
C16 | −0.1522 (4) | 0.5937 (3) | 0.6893 (3) | 0.0823 (10) | |
H16A | −0.0805 | 0.6626 | 0.7304 | 0.099* | |
C17 | −0.2734 (4) | 0.5464 (4) | 0.7236 (3) | 0.0815 (10) | |
H17A | −0.2829 | 0.5829 | 0.7875 | 0.098* | |
C18 | −0.3795 (4) | 0.4459 (3) | 0.6633 (2) | 0.0716 (9) | |
H18A | −0.4617 | 0.4147 | 0.6864 | 0.086* | |
C19 | −0.3663 (3) | 0.3888 (3) | 0.5670 (2) | 0.0546 (7) | |
C20 | −0.4790 (3) | 0.2801 (3) | 0.5055 (2) | 0.0580 (7) | |
H20A | −0.5612 | 0.2521 | 0.5296 | 0.070* | |
C21 | −0.5766 (3) | 0.1108 (3) | 0.3638 (2) | 0.0495 (6) | |
C22 | −0.6821 (3) | 0.0394 (3) | 0.4052 (2) | 0.0671 (8) | |
H22A | −0.6867 | 0.0666 | 0.4730 | 0.081* | |
C23 | −0.7793 (3) | −0.0705 (3) | 0.3476 (3) | 0.0684 (8) | |
H23A | −0.8508 | −0.1147 | 0.3756 | 0.082* | |
C24 | −0.7710 (3) | −0.1143 (3) | 0.2498 (2) | 0.0647 (8) | |
H24A | −0.8352 | −0.1896 | 0.2118 | 0.078* | |
C25 | −0.6669 (3) | −0.0467 (3) | 0.2071 (2) | 0.0617 (7) | |
H25A | −0.6617 | −0.0770 | 0.1401 | 0.074* | |
C26 | −0.5700 (3) | 0.0657 (3) | 0.2628 (2) | 0.0474 (6) | |
H1 | −0.500 (4) | 0.301 (3) | 0.139 (3) | 0.080 (11)* | |
H2 | −0.290 (4) | 0.323 (4) | 0.415 (3) | 0.105 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0561 (2) | 0.0758 (3) | 0.0844 (3) | 0.00471 (15) | 0.03481 (16) | −0.00113 (17) |
O1 | 0.0859 (16) | 0.0664 (15) | 0.1017 (17) | 0.0342 (12) | 0.0595 (14) | 0.0357 (13) |
O2 | 0.0899 (17) | 0.1015 (19) | 0.0897 (17) | −0.0397 (16) | 0.0532 (14) | −0.0303 (15) |
N1 | 0.0595 (14) | 0.0516 (14) | 0.0530 (13) | −0.0048 (11) | 0.0252 (11) | 0.0004 (11) |
N2 | 0.0615 (14) | 0.0484 (13) | 0.0531 (12) | 0.0059 (11) | 0.0288 (11) | 0.0048 (10) |
C1 | 0.0584 (16) | 0.0456 (16) | 0.0644 (17) | 0.0116 (13) | 0.0288 (14) | 0.0078 (13) |
C2 | 0.074 (2) | 0.0489 (17) | 0.0747 (19) | 0.0162 (15) | 0.0370 (16) | 0.0188 (15) |
C3 | 0.0667 (18) | 0.0491 (17) | 0.0593 (16) | −0.0040 (14) | 0.0309 (14) | 0.0064 (14) |
C4 | 0.0466 (14) | 0.0464 (15) | 0.0495 (14) | 0.0015 (12) | 0.0169 (12) | −0.0028 (12) |
C5 | 0.0523 (15) | 0.0406 (14) | 0.0461 (14) | 0.0041 (12) | 0.0166 (12) | −0.0003 (12) |
C6 | 0.0509 (14) | 0.0400 (14) | 0.0414 (13) | 0.0035 (12) | 0.0172 (11) | 0.0005 (11) |
C7 | 0.0506 (15) | 0.0432 (14) | 0.0391 (13) | 0.0002 (12) | 0.0161 (11) | −0.0048 (11) |
C8 | 0.0547 (15) | 0.0456 (16) | 0.0546 (16) | 0.0063 (13) | 0.0290 (13) | 0.0078 (13) |
C9 | 0.100 (3) | 0.0517 (19) | 0.080 (2) | 0.0100 (18) | 0.0338 (19) | 0.0046 (17) |
C10 | 0.130 (3) | 0.049 (2) | 0.142 (4) | 0.015 (2) | 0.078 (3) | 0.008 (2) |
C11 | 0.113 (3) | 0.083 (3) | 0.146 (4) | 0.044 (3) | 0.087 (3) | 0.056 (3) |
C12 | 0.081 (2) | 0.107 (3) | 0.093 (3) | 0.037 (2) | 0.044 (2) | 0.052 (3) |
C13 | 0.0644 (18) | 0.074 (2) | 0.0624 (18) | 0.0141 (16) | 0.0278 (15) | 0.0177 (16) |
C14 | 0.0684 (19) | 0.0620 (19) | 0.0627 (18) | −0.0044 (16) | 0.0221 (15) | −0.0041 (15) |
C15 | 0.069 (2) | 0.075 (2) | 0.090 (2) | −0.0137 (18) | 0.0232 (18) | −0.006 (2) |
C16 | 0.088 (3) | 0.065 (2) | 0.074 (2) | −0.0004 (19) | 0.0017 (19) | −0.0128 (18) |
C17 | 0.093 (3) | 0.077 (2) | 0.068 (2) | 0.007 (2) | 0.0176 (19) | −0.0120 (18) |
C18 | 0.082 (2) | 0.067 (2) | 0.0681 (19) | 0.0057 (18) | 0.0270 (17) | −0.0061 (17) |
C19 | 0.0590 (17) | 0.0490 (16) | 0.0559 (16) | 0.0049 (14) | 0.0184 (13) | 0.0025 (14) |
C20 | 0.0591 (17) | 0.0592 (18) | 0.0609 (17) | 0.0014 (14) | 0.0273 (14) | 0.0044 (15) |
C21 | 0.0500 (15) | 0.0480 (16) | 0.0546 (15) | 0.0036 (13) | 0.0226 (13) | 0.0033 (13) |
C22 | 0.076 (2) | 0.070 (2) | 0.0663 (18) | −0.0111 (17) | 0.0420 (16) | −0.0019 (16) |
C23 | 0.0593 (18) | 0.068 (2) | 0.085 (2) | −0.0085 (16) | 0.0358 (16) | 0.0062 (17) |
C24 | 0.0604 (18) | 0.0603 (19) | 0.0660 (18) | −0.0094 (15) | 0.0132 (15) | 0.0002 (15) |
C25 | 0.0691 (19) | 0.0618 (19) | 0.0517 (16) | −0.0018 (16) | 0.0179 (14) | −0.0012 (14) |
C26 | 0.0474 (15) | 0.0470 (15) | 0.0514 (15) | 0.0067 (12) | 0.0200 (12) | 0.0096 (13) |
Br1—C4 | 1.905 (2) | C12—C13 | 1.389 (4) |
O1—C1 | 1.346 (3) | C12—H12A | 0.9300 |
O1—H1 | 0.80 (3) | C13—H13A | 0.9300 |
O2—C14 | 1.354 (3) | C14—C19 | 1.397 (4) |
O2—H2 | 0.81 (3) | C14—C15 | 1.398 (4) |
N1—C20 | 1.276 (3) | C15—C16 | 1.375 (4) |
N1—C21 | 1.418 (3) | C15—H15A | 0.9300 |
N2—C7 | 1.291 (3) | C16—C17 | 1.377 (5) |
N2—C26 | 1.427 (3) | C16—H16A | 0.9300 |
C1—C2 | 1.399 (4) | C17—C18 | 1.364 (4) |
C1—C6 | 1.406 (3) | C17—H17A | 0.9300 |
C2—C3 | 1.370 (4) | C18—C19 | 1.404 (4) |
C2—H2C | 0.9300 | C18—H18A | 0.9300 |
C3—C4 | 1.376 (4) | C19—C20 | 1.451 (4) |
C3—H3A | 0.9300 | C20—N1 | 1.276 (3) |
C4—C5 | 1.379 (3) | C20—H20A | 0.9300 |
C5—C6 | 1.407 (3) | C21—C22 | 1.398 (3) |
C5—H5A | 0.9300 | C21—C26 | 1.398 (3) |
C6—C7 | 1.477 (3) | C21—N1 | 1.418 (3) |
C7—N2 | 1.291 (3) | C22—C23 | 1.379 (4) |
C7—C8 | 1.485 (4) | C22—H22A | 0.9300 |
C8—C13 | 1.377 (4) | C23—C24 | 1.359 (4) |
C8—C9 | 1.380 (4) | C23—H23A | 0.9300 |
C9—C10 | 1.387 (5) | C24—C25 | 1.383 (4) |
C9—H9A | 0.9300 | C24—H24A | 0.9300 |
C10—C11 | 1.381 (6) | C25—C26 | 1.388 (4) |
C10—H10A | 0.9300 | C25—H25A | 0.9300 |
C11—C12 | 1.355 (5) | C26—N2 | 1.427 (3) |
C11—H11A | 0.9300 | ||
C1—O1—H1 | 104 (2) | O2—C14—C19 | 121.4 (3) |
C14—O2—H2 | 110 (3) | O2—C14—C15 | 118.9 (3) |
C20—N1—C21 | 121.4 (2) | C19—C14—C15 | 119.7 (3) |
C7—N2—C26 | 123.7 (2) | C16—C15—C14 | 119.6 (3) |
O1—C1—C2 | 117.7 (2) | C16—C15—H15A | 120.2 |
O1—C1—C6 | 122.4 (2) | C14—C15—H15A | 120.2 |
C2—C1—C6 | 119.9 (2) | C15—C16—C17 | 121.2 (3) |
C3—C2—C1 | 120.7 (3) | C15—C16—H16A | 119.4 |
C3—C2—H2C | 119.6 | C17—C16—H16A | 119.4 |
C1—C2—H2C | 119.6 | C18—C17—C16 | 119.7 (3) |
C2—C3—C4 | 119.7 (2) | C18—C17—H17A | 120.1 |
C2—C3—H3A | 120.1 | C16—C17—H17A | 120.1 |
C4—C3—H3A | 120.1 | C17—C18—C19 | 120.9 (3) |
C3—C4—C5 | 121.1 (2) | C17—C18—H18A | 119.5 |
C3—C4—Br1 | 118.32 (19) | C19—C18—H18A | 119.5 |
C5—C4—Br1 | 120.6 (2) | C14—C19—C18 | 118.8 (3) |
C4—C5—C6 | 120.3 (2) | C14—C19—C20 | 121.3 (2) |
C4—C5—H5A | 119.8 | C18—C19—C20 | 119.9 (3) |
C6—C5—H5A | 119.8 | N1—C20—C19 | 122.4 (2) |
C1—C6—C5 | 118.1 (2) | N1—C20—C19 | 122.4 (2) |
C1—C6—C7 | 120.8 (2) | N1—C20—H20A | 118.8 |
C5—C6—C7 | 121.1 (2) | N1—C20—H20A | 118.8 |
N2—C7—C6 | 117.6 (2) | C19—C20—H20A | 118.8 |
N2—C7—C6 | 117.6 (2) | C22—C21—C26 | 118.0 (2) |
N2—C7—C8 | 122.2 (2) | C22—C21—N1 | 124.7 (2) |
N2—C7—C8 | 122.2 (2) | C26—C21—N1 | 117.2 (2) |
C6—C7—C8 | 120.2 (2) | C22—C21—N1 | 124.7 (2) |
C13—C8—C9 | 119.3 (3) | C26—C21—N1 | 117.2 (2) |
C13—C8—C7 | 119.8 (2) | C23—C22—C21 | 121.3 (3) |
C9—C8—C7 | 120.8 (2) | C23—C22—H22A | 119.4 |
C8—C9—C10 | 120.3 (3) | C21—C22—H22A | 119.3 |
C8—C9—H9A | 119.9 | C24—C23—C22 | 120.2 (3) |
C10—C9—H9A | 119.9 | C24—C23—H23A | 119.9 |
C11—C10—C9 | 119.6 (4) | C22—C23—H23A | 119.9 |
C11—C10—H10A | 120.2 | C23—C24—C25 | 119.9 (3) |
C9—C10—H10A | 120.2 | C23—C24—H24A | 120.1 |
C12—C11—C10 | 120.3 (4) | C25—C24—H24A | 120.1 |
C12—C11—H11A | 119.8 | C24—C25—C26 | 120.8 (3) |
C10—C11—H11A | 119.8 | C24—C25—H25A | 119.6 |
C11—C12—C13 | 120.3 (4) | C26—C25—H25A | 119.6 |
C11—C12—H12A | 119.8 | C25—C26—C21 | 119.7 (2) |
C13—C12—H12A | 119.8 | C25—C26—N2 | 120.5 (2) |
C8—C13—C12 | 120.1 (3) | C21—C26—N2 | 119.3 (2) |
C8—C13—H13A | 119.9 | C25—C26—N2 | 120.5 (2) |
C12—C13—H13A | 119.9 | C21—C26—N2 | 119.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.80 (3) | 1.79 (3) | 2.530 (3) | 154 (3) |
O2—H2···N1 | 0.81 (3) | 1.87 (3) | 2.596 (3) | 148 (3) |
C2—H2C···O1i | 0.93 | 2.51 | 3.419 (4) | 166 |
C15—H15A···O2ii | 0.93 | 2.60 | 3.497 (4) | 162 |
Symmetry codes: (i) −x−1, −y+1, −z; (ii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C26H19BrN2O2 |
Mr | 471.34 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1089.8 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.91 |
Crystal size (mm) | 0.25 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4501, 3742, 2837 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.091, 1.07 |
No. of reflections | 3742 |
No. of parameters | 289 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.80 (3) | 1.79 (3) | 2.530 (3) | 154 (3) |
O2—H2···N1 | 0.81 (3) | 1.87 (3) | 2.596 (3) | 148 (3) |
C2—H2C···O1i | 0.93 | 2.51 | 3.419 (4) | 165.6 |
C15—H15A···O2ii | 0.93 | 2.60 | 3.497 (4) | 162.0 |
Symmetry codes: (i) −x−1, −y+1, −z; (ii) −x, −y+1, −z+1. |
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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].