Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024348/at2297sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024348/at2297Isup2.hkl |
CCDC reference: 651773
A mixture of 2-bromo-5-methoxybenzohydrazide (0.735 g, 0.003 mol) and 4-fluorobenzaldehyde (0.372 g, 0.003 mol) in 15 ml of absolute alcohol containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h (see scheme). On cooling, the solid separated was filtered off and recrystallized from ethyl acetate (m.p.: 440–442 K). Analysis for C15H12BrFN2O2.H2O: Found (calculated): C 48.71 (48.80), H 3.76 (3.82), N 7.51 (7.59) %.
H atoms were found in a difference map, but they were refined using a riding model with C—H = 0.95 Å, N—H = 0.88 Å, O—H = 0.84Å and Uiso(H) = 1.2Ueq(C,N,O) or C—H = 0.98Å and Uiso(H) = 1.5Ueq(Cmethyl).
Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives were reported to possess antimicrobial, anti-inflammatory and central nervous system activities. Moreover, Schiff bases are also known to have biological activities such as antimicrobial, antifungal, antitumor, and as herbicides. A new Schiff base, (I), C15H12BrFN2O2.H2O is synthesized and its crystal structure is reported.
The two molecules in the asymmetric unit differ in the dihedral angle between the two aromatic rings, which are 62.3 (2)° and 49.9 (2)°. The crystal packing is stabilized by N—H···O and O—H···O hydrogen bonds.
For related structures, see: 2'-[1-(4-fluorophenyl)ethyl]isonicotino-KN-hydrazide-cyanoborane (Bruno et al., 1998); 1-(2-bromo-5-methoxyphenyl)-8-chloro-6-(2-fluorophenyl)-4H-1,2,4-triazolo[4,3-a] [1,4]benzodiazepine (Harrison et al., 2005); 2-bromo-5-methoxy-N'-[(E)-(2-nitrophenyl)methylene]benzohydrazide (Yathirajan, Sarojini et al., 2007); N'-[(1E)-(4-fluorophenyl)methylene]-6-methoxy-2-naphthohydrazide (Yathirajan, Narayana, et al., 2007). For related literature, see: Varma et al. (1986); Misra et al. (1981); Agarwal et al. (1983); Singh et al. (1988); Hodnett et al. (1970).
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Fig. 1. The structure of the two independent molecules in the asymmetric unit of the title compound, with the atom numbering. Displacement ellipsoids are at the 50% probability level. |
C15H12BrFN2O2.H2O | F(000) = 1488 |
Mr = 369.19 | Dx = 1.625 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 11319 reflections |
a = 30.1171 (18) Å | θ = 3.6–25.1° |
b = 8.0187 (7) Å | µ = 2.75 mm−1 |
c = 13.4661 (8) Å | T = 173 K |
β = 111.902 (4)° | Block, colourless |
V = 3017.3 (4) Å3 | 0.37 × 0.35 × 0.33 mm |
Z = 8 |
STOE IPDS II two-circle- diffractometer | 5477 independent reflections |
Radiation source: fine-focus sealed tube | 4843 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ω scans | θmax = 25.6°, θmin = 3.5° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −36→35 |
Tmin = 0.379, Tmax = 0.394 | k = −9→9 |
16531 measured reflections | l = −16→16 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.080 | w = 1/[σ2(Fo2) + (0.163P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.202 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.56 e Å−3 |
5477 reflections | Δρmin = −0.76 e Å−3 |
400 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0062 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 2642 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.018 (17) |
C15H12BrFN2O2.H2O | V = 3017.3 (4) Å3 |
Mr = 369.19 | Z = 8 |
Monoclinic, Cc | Mo Kα radiation |
a = 30.1171 (18) Å | µ = 2.75 mm−1 |
b = 8.0187 (7) Å | T = 173 K |
c = 13.4661 (8) Å | 0.37 × 0.35 × 0.33 mm |
β = 111.902 (4)° |
STOE IPDS II two-circle- diffractometer | 5477 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | 4843 reflections with I > 2σ(I) |
Tmin = 0.379, Tmax = 0.394 | Rint = 0.059 |
16531 measured reflections |
R[F2 > 2σ(F2)] = 0.080 | H-atom parameters constrained |
wR(F2) = 0.202 | Δρmax = 0.56 e Å−3 |
S = 1.02 | Δρmin = −0.76 e Å−3 |
5477 reflections | Absolute structure: Flack (1983), 2642 Friedel pairs |
400 parameters | Absolute structure parameter: 0.018 (17) |
2 restraints |
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 | 0.52393 (3) | 0.24296 (11) | 0.77882 (6) | 0.0677 (3) | |
F1 | 0.82483 (19) | 0.6614 (8) | 0.6074 (5) | 0.0838 (15) | |
O1 | 0.5622 (2) | 0.5636 (7) | 0.6968 (4) | 0.0603 (12) | |
O2 | 0.3807 (2) | 0.4246 (8) | 0.3428 (5) | 0.0697 (14) | |
N1 | 0.5647 (3) | 0.4797 (9) | 0.5375 (5) | 0.0578 (14) | |
H1 | 0.5499 | 0.4312 | 0.4752 | 0.069* | |
N2 | 0.6106 (2) | 0.5460 (8) | 0.5654 (5) | 0.0548 (13) | |
C1 | 0.5439 (3) | 0.4937 (9) | 0.6110 (6) | 0.0557 (15) | |
C2 | 0.6317 (3) | 0.5090 (10) | 0.5039 (7) | 0.0594 (17) | |
H2 | 0.6153 | 0.4475 | 0.4404 | 0.071* | |
C11 | 0.4947 (3) | 0.4167 (8) | 0.5755 (6) | 0.0540 (15) | |
C12 | 0.4806 (3) | 0.3189 (9) | 0.6429 (5) | 0.0555 (15) | |
C13 | 0.4333 (3) | 0.2595 (9) | 0.6109 (7) | 0.0584 (17) | |
H13 | 0.4237 | 0.1914 | 0.6571 | 0.070* | |
C14 | 0.4013 (3) | 0.3030 (12) | 0.5107 (7) | 0.0623 (19) | |
H14 | 0.3689 | 0.2680 | 0.4893 | 0.075* | |
C15 | 0.4150 (3) | 0.3964 (10) | 0.4402 (7) | 0.0605 (17) | |
C16 | 0.4613 (3) | 0.4553 (9) | 0.4731 (6) | 0.0568 (16) | |
H16 | 0.4707 | 0.5222 | 0.4261 | 0.068* | |
C17 | 0.3953 (3) | 0.5087 (12) | 0.2651 (7) | 0.070 (2) | |
H17A | 0.4090 | 0.6176 | 0.2933 | 0.105* | |
H17B | 0.3674 | 0.5243 | 0.1986 | 0.105* | |
H17C | 0.4193 | 0.4412 | 0.2506 | 0.105* | |
C21 | 0.6819 (3) | 0.5605 (10) | 0.5292 (6) | 0.0554 (15) | |
C22 | 0.7068 (3) | 0.4959 (10) | 0.4660 (7) | 0.0625 (17) | |
H22 | 0.6901 | 0.4297 | 0.4049 | 0.075* | |
C23 | 0.7554 (3) | 0.5292 (11) | 0.4933 (7) | 0.0629 (18) | |
H23 | 0.7725 | 0.4847 | 0.4528 | 0.076* | |
C24 | 0.7774 (3) | 0.6282 (11) | 0.5806 (7) | 0.0648 (19) | |
C25 | 0.7545 (3) | 0.6977 (11) | 0.6432 (7) | 0.0661 (18) | |
H25 | 0.7712 | 0.7684 | 0.7019 | 0.079* | |
C26 | 0.7071 (3) | 0.6607 (9) | 0.6175 (6) | 0.0583 (16) | |
H26 | 0.6910 | 0.7039 | 0.6605 | 0.070* | |
Br1A | 0.15181 (3) | 0.26881 (10) | 0.25235 (4) | 0.0646 (3) | |
C1A | 0.1256 (3) | 0.4374 (10) | 0.0114 (6) | 0.0569 (16) | |
F1A | −0.1718 (2) | 0.6188 (9) | −0.1250 (5) | 0.0903 (17) | |
O1A | 0.1093 (2) | 0.3990 (7) | −0.0840 (4) | 0.0620 (12) | |
O2A | 0.2918 (2) | 0.3916 (8) | 0.0344 (5) | 0.0682 (14) | |
N1A | 0.0998 (2) | 0.5084 (9) | 0.0612 (5) | 0.0583 (14) | |
H1A | 0.1135 | 0.5470 | 0.1268 | 0.070* | |
N2A | 0.0509 (3) | 0.5199 (8) | 0.0075 (5) | 0.0576 (15) | |
C2A | 0.0269 (3) | 0.5737 (10) | 0.0615 (6) | 0.0597 (16) | |
H2A | 0.0430 | 0.6068 | 0.1339 | 0.072* | |
C11A | 0.1769 (3) | 0.3985 (8) | 0.0781 (6) | 0.0543 (15) | |
C12A | 0.1936 (3) | 0.3191 (9) | 0.1777 (6) | 0.0551 (15) | |
C13A | 0.2403 (3) | 0.2667 (10) | 0.2268 (7) | 0.0604 (17) | |
H13A | 0.2504 | 0.2118 | 0.2941 | 0.072* | |
C14A | 0.2724 (3) | 0.2947 (10) | 0.1770 (8) | 0.0645 (18) | |
H14A | 0.3048 | 0.2601 | 0.2108 | 0.077* | |
C15A | 0.2577 (3) | 0.3727 (10) | 0.0784 (6) | 0.0606 (16) | |
C16A | 0.2104 (3) | 0.4230 (10) | 0.0277 (6) | 0.0565 (16) | |
H16A | 0.2004 | 0.4739 | −0.0409 | 0.068* | |
C17A | 0.2772 (3) | 0.4652 (12) | −0.0697 (7) | 0.071 (2) | |
H17D | 0.2507 | 0.4004 | −0.1200 | 0.107* | |
H17E | 0.3042 | 0.4654 | −0.0936 | 0.107* | |
H17F | 0.2666 | 0.5800 | −0.0667 | 0.107* | |
C21A | −0.0256 (3) | 0.5847 (10) | 0.0117 (7) | 0.0625 (18) | |
C22A | −0.0509 (3) | 0.6564 (10) | 0.0689 (8) | 0.0665 (18) | |
H22A | −0.0343 | 0.6958 | 0.1397 | 0.080* | |
C23A | −0.1008 (3) | 0.6706 (12) | 0.0220 (9) | 0.073 (2) | |
H23A | −0.1185 | 0.7223 | 0.0590 | 0.088* | |
C24A | −0.1232 (3) | 0.6070 (13) | −0.0792 (8) | 0.077 (2) | |
C25A | −0.0994 (3) | 0.5372 (13) | −0.1390 (8) | 0.073 (2) | |
H25A | −0.1163 | 0.5000 | −0.2101 | 0.088* | |
C26A | −0.0501 (3) | 0.5231 (9) | −0.0922 (7) | 0.0611 (17) | |
H26A | −0.0328 | 0.4717 | −0.1302 | 0.073* | |
O1W | 0.5235 (2) | 0.2938 (8) | 0.3394 (5) | 0.0634 (12) | |
H1W1 | 0.5349 | 0.3360 | 0.2969 | 0.076* | |
H1W2 | 0.5488 | 0.2372 | 0.3619 | 0.076* | |
O1WA | 0.1404 (2) | 0.7000 (7) | 0.2531 (4) | 0.0585 (12) | |
H1W3 | 0.1178 | 0.7686 | 0.2367 | 0.070* | |
H1W4 | 0.1311 | 0.6703 | 0.3020 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0677 (5) | 0.0716 (5) | 0.0613 (5) | −0.0041 (4) | 0.0213 (4) | 0.0093 (3) |
F1 | 0.055 (3) | 0.098 (4) | 0.102 (4) | −0.007 (2) | 0.033 (3) | 0.007 (3) |
O1 | 0.059 (3) | 0.067 (3) | 0.060 (3) | −0.003 (2) | 0.027 (2) | −0.004 (2) |
O2 | 0.056 (3) | 0.081 (4) | 0.068 (3) | −0.003 (3) | 0.019 (3) | 0.005 (3) |
N1 | 0.057 (4) | 0.059 (3) | 0.055 (3) | −0.004 (3) | 0.018 (3) | −0.004 (3) |
N2 | 0.051 (3) | 0.057 (3) | 0.055 (3) | 0.001 (2) | 0.019 (3) | 0.001 (2) |
C1 | 0.057 (4) | 0.053 (3) | 0.057 (4) | 0.000 (3) | 0.020 (3) | −0.003 (3) |
C2 | 0.058 (4) | 0.055 (4) | 0.060 (4) | 0.001 (3) | 0.017 (3) | 0.001 (3) |
C11 | 0.049 (4) | 0.048 (3) | 0.068 (4) | 0.002 (3) | 0.025 (3) | −0.003 (3) |
C12 | 0.056 (4) | 0.060 (4) | 0.045 (3) | 0.007 (3) | 0.013 (3) | 0.002 (3) |
C13 | 0.063 (4) | 0.055 (4) | 0.065 (4) | −0.003 (3) | 0.032 (4) | −0.003 (3) |
C14 | 0.050 (4) | 0.066 (5) | 0.076 (5) | −0.002 (3) | 0.029 (4) | −0.006 (3) |
C15 | 0.062 (4) | 0.054 (4) | 0.066 (4) | 0.000 (3) | 0.025 (4) | −0.004 (3) |
C16 | 0.065 (4) | 0.051 (3) | 0.061 (4) | −0.004 (3) | 0.032 (3) | 0.001 (3) |
C17 | 0.062 (5) | 0.079 (5) | 0.061 (4) | −0.004 (4) | 0.015 (4) | 0.003 (4) |
C21 | 0.054 (4) | 0.057 (4) | 0.058 (4) | 0.003 (3) | 0.024 (3) | 0.010 (3) |
C22 | 0.071 (5) | 0.055 (4) | 0.062 (4) | −0.002 (3) | 0.025 (4) | 0.004 (3) |
C23 | 0.062 (4) | 0.067 (4) | 0.071 (4) | 0.007 (3) | 0.038 (4) | 0.007 (3) |
C24 | 0.058 (4) | 0.070 (5) | 0.070 (4) | 0.003 (3) | 0.029 (4) | 0.017 (4) |
C25 | 0.066 (5) | 0.064 (4) | 0.063 (4) | −0.006 (4) | 0.018 (4) | 0.006 (3) |
C26 | 0.058 (4) | 0.056 (4) | 0.067 (4) | 0.005 (3) | 0.030 (3) | 0.007 (3) |
Br1A | 0.0716 (5) | 0.0638 (4) | 0.0619 (5) | 0.0006 (4) | 0.0291 (4) | 0.0058 (4) |
C1A | 0.058 (4) | 0.052 (4) | 0.060 (4) | −0.001 (3) | 0.021 (3) | 0.001 (3) |
F1A | 0.059 (3) | 0.117 (5) | 0.097 (4) | 0.014 (3) | 0.031 (3) | 0.027 (3) |
O1A | 0.055 (3) | 0.076 (3) | 0.053 (2) | 0.003 (2) | 0.019 (2) | −0.004 (2) |
O2A | 0.055 (3) | 0.073 (3) | 0.077 (4) | 0.001 (3) | 0.026 (3) | −0.001 (3) |
N1A | 0.055 (3) | 0.061 (3) | 0.056 (3) | 0.001 (3) | 0.018 (3) | −0.005 (2) |
N2A | 0.056 (4) | 0.057 (3) | 0.058 (3) | 0.000 (3) | 0.018 (3) | −0.001 (3) |
C2A | 0.059 (4) | 0.053 (4) | 0.063 (4) | 0.003 (3) | 0.018 (3) | 0.002 (3) |
C11A | 0.054 (4) | 0.048 (3) | 0.061 (4) | −0.001 (3) | 0.022 (3) | −0.002 (3) |
C12A | 0.058 (4) | 0.056 (3) | 0.058 (4) | −0.004 (3) | 0.029 (3) | 0.000 (3) |
C13A | 0.062 (5) | 0.060 (4) | 0.054 (4) | 0.007 (3) | 0.017 (3) | 0.000 (3) |
C14A | 0.059 (4) | 0.056 (4) | 0.074 (5) | 0.004 (3) | 0.019 (4) | −0.006 (3) |
C15A | 0.057 (4) | 0.058 (4) | 0.068 (4) | −0.002 (3) | 0.025 (3) | −0.010 (3) |
C16A | 0.058 (4) | 0.054 (4) | 0.054 (3) | −0.001 (3) | 0.017 (3) | −0.004 (3) |
C17A | 0.069 (5) | 0.075 (5) | 0.074 (5) | 0.000 (4) | 0.031 (4) | 0.000 (4) |
C21A | 0.059 (4) | 0.055 (4) | 0.074 (5) | 0.002 (3) | 0.026 (4) | 0.003 (3) |
C22A | 0.065 (5) | 0.061 (4) | 0.079 (5) | −0.001 (3) | 0.033 (4) | −0.001 (3) |
C23A | 0.071 (5) | 0.055 (4) | 0.106 (7) | 0.007 (3) | 0.046 (5) | 0.009 (4) |
C24A | 0.059 (5) | 0.087 (6) | 0.085 (6) | 0.003 (4) | 0.026 (4) | 0.021 (5) |
C25A | 0.062 (5) | 0.087 (6) | 0.072 (5) | −0.009 (4) | 0.027 (4) | 0.004 (4) |
C26A | 0.061 (4) | 0.057 (4) | 0.069 (4) | 0.005 (3) | 0.029 (4) | 0.012 (3) |
O1W | 0.062 (3) | 0.067 (3) | 0.062 (3) | 0.002 (2) | 0.023 (3) | −0.003 (2) |
O1WA | 0.060 (3) | 0.060 (3) | 0.057 (3) | 0.006 (2) | 0.023 (2) | 0.004 (2) |
Br1—C12 | 1.908 (7) | C1A—N1A | 1.331 (11) |
F1—C24 | 1.363 (10) | C1A—C11A | 1.501 (11) |
O1—C1 | 1.216 (9) | F1A—C24A | 1.363 (11) |
O2—C15 | 1.352 (11) | O2A—C15A | 1.371 (10) |
O2—C17 | 1.444 (11) | O2A—C17A | 1.431 (11) |
N1—C1 | 1.358 (10) | N1A—N2A | 1.378 (10) |
N1—N2 | 1.396 (10) | N1A—H1A | 0.8800 |
N1—H1 | 0.8800 | N2A—C2A | 1.276 (11) |
N2—C2 | 1.254 (11) | C2A—C21A | 1.474 (12) |
C1—C11 | 1.510 (10) | C2A—H2A | 0.9500 |
C2—C21 | 1.480 (12) | C11A—C12A | 1.398 (10) |
C2—H2 | 0.9500 | C11A—C16A | 1.425 (11) |
C11—C12 | 1.381 (11) | C12A—C13A | 1.380 (12) |
C11—C16 | 1.405 (11) | C13A—C14A | 1.385 (14) |
C12—C13 | 1.408 (12) | C13A—H13A | 0.9500 |
C13—C14 | 1.379 (13) | C14A—C15A | 1.382 (13) |
C13—H13 | 0.9500 | C14A—H14A | 0.9500 |
C14—C15 | 1.386 (12) | C15A—C16A | 1.390 (12) |
C14—H14 | 0.9500 | C16A—H16A | 0.9500 |
C15—C16 | 1.380 (11) | C17A—H17D | 0.9800 |
C16—H16 | 0.9500 | C17A—H17E | 0.9800 |
C17—H17A | 0.9800 | C17A—H17F | 0.9800 |
C17—H17B | 0.9800 | C21A—C22A | 1.393 (12) |
C17—H17C | 0.9800 | C21A—C26A | 1.405 (12) |
C21—C26 | 1.401 (12) | C22A—C23A | 1.400 (13) |
C21—C22 | 1.423 (12) | C22A—H22A | 0.9500 |
C22—C23 | 1.396 (13) | C23A—C24A | 1.373 (16) |
C22—H22 | 0.9500 | C23A—H23A | 0.9500 |
C23—C24 | 1.368 (13) | C24A—C25A | 1.382 (15) |
C23—H23 | 0.9500 | C25A—C26A | 1.384 (13) |
C24—C25 | 1.389 (13) | C25A—H25A | 0.9500 |
C25—C26 | 1.370 (12) | C26A—H26A | 0.9500 |
C25—H25 | 0.9500 | O1W—H1W1 | 0.8401 |
C26—H26 | 0.9500 | O1W—H1W2 | 0.8424 |
Br1A—C12A | 1.923 (7) | O1WA—H1W3 | 0.8399 |
C1A—O1A | 1.231 (10) | O1WA—H1W4 | 0.8400 |
C15—O2—C17 | 116.9 (6) | O1A—C1A—C11A | 119.5 (7) |
C1—N1—N2 | 116.9 (6) | N1A—C1A—C11A | 116.8 (7) |
C1—N1—H1 | 121.6 | C15A—O2A—C17A | 117.5 (7) |
N2—N1—H1 | 121.6 | C1A—N1A—N2A | 118.3 (7) |
C2—N2—N1 | 115.4 (7) | C1A—N1A—H1A | 120.8 |
O1—C1—N1 | 124.3 (7) | N2A—N1A—H1A | 120.8 |
O1—C1—C11 | 122.1 (7) | C2A—N2A—N1A | 116.4 (7) |
N1—C1—C11 | 113.6 (6) | N2A—C2A—C21A | 120.1 (7) |
N2—C2—C21 | 120.6 (8) | N2A—C2A—H2A | 120.0 |
N2—C2—H2 | 119.7 | C21A—C2A—H2A | 120.0 |
C21—C2—H2 | 119.7 | C12A—C11A—C16A | 117.0 (7) |
C12—C11—C16 | 119.2 (7) | C12A—C11A—C1A | 126.2 (7) |
C12—C11—C1 | 122.1 (7) | C16A—C11A—C1A | 116.1 (6) |
C16—C11—C1 | 118.6 (6) | C13A—C12A—C11A | 122.4 (7) |
C11—C12—C13 | 121.0 (7) | C13A—C12A—Br1A | 115.8 (6) |
C11—C12—Br1 | 122.9 (6) | C11A—C12A—Br1A | 121.7 (6) |
C13—C12—Br1 | 116.0 (6) | C12A—C13A—C14A | 119.4 (8) |
C14—C13—C12 | 118.2 (7) | C12A—C13A—H13A | 120.3 |
C14—C13—H13 | 120.9 | C14A—C13A—H13A | 120.3 |
C12—C13—H13 | 120.9 | C15A—C14A—C13A | 120.4 (8) |
C13—C14—C15 | 121.9 (7) | C15A—C14A—H14A | 119.8 |
C13—C14—H14 | 119.0 | C13A—C14A—H14A | 119.8 |
C15—C14—H14 | 119.0 | O2A—C15A—C14A | 116.1 (8) |
O2—C15—C16 | 124.6 (7) | O2A—C15A—C16A | 123.4 (7) |
O2—C15—C14 | 116.2 (7) | C14A—C15A—C16A | 120.4 (8) |
C16—C15—C14 | 119.2 (7) | C15A—C16A—C11A | 120.3 (7) |
C15—C16—C11 | 120.4 (7) | C15A—C16A—H16A | 119.9 |
C15—C16—H16 | 119.8 | C11A—C16A—H16A | 119.9 |
C11—C16—H16 | 119.8 | O2A—C17A—H17D | 109.5 |
O2—C17—H17A | 109.5 | O2A—C17A—H17E | 109.5 |
O2—C17—H17B | 109.5 | H17D—C17A—H17E | 109.5 |
H17A—C17—H17B | 109.5 | O2A—C17A—H17F | 109.5 |
O2—C17—H17C | 109.5 | H17D—C17A—H17F | 109.5 |
H17A—C17—H17C | 109.5 | H17E—C17A—H17F | 109.5 |
H17B—C17—H17C | 109.5 | C22A—C21A—C26A | 120.3 (8) |
C26—C21—C22 | 118.6 (7) | C22A—C21A—C2A | 119.2 (8) |
C26—C21—C2 | 122.6 (7) | C26A—C21A—C2A | 120.5 (7) |
C22—C21—C2 | 118.7 (8) | C21A—C22A—C23A | 120.0 (9) |
C23—C22—C21 | 120.4 (8) | C21A—C22A—H22A | 120.0 |
C23—C22—H22 | 119.8 | C23A—C22A—H22A | 120.0 |
C21—C22—H22 | 119.8 | C24A—C23A—C22A | 117.8 (9) |
C24—C23—C22 | 117.5 (8) | C24A—C23A—H23A | 121.1 |
C24—C23—H23 | 121.3 | C22A—C23A—H23A | 121.1 |
C22—C23—H23 | 121.3 | F1A—C24A—C23A | 118.1 (9) |
F1—C24—C23 | 117.7 (8) | F1A—C24A—C25A | 117.9 (9) |
F1—C24—C25 | 117.9 (8) | C23A—C24A—C25A | 123.9 (9) |
C23—C24—C25 | 124.3 (8) | C24A—C25A—C26A | 118.1 (9) |
C26—C25—C24 | 117.7 (8) | C24A—C25A—H25A | 121.0 |
C26—C25—H25 | 121.1 | C26A—C25A—H25A | 121.0 |
C24—C25—H25 | 121.1 | C25A—C26A—C21A | 119.9 (8) |
C25—C26—C21 | 121.5 (7) | C25A—C26A—H26A | 120.0 |
C25—C26—H26 | 119.3 | C21A—C26A—H26A | 120.0 |
C21—C26—H26 | 119.3 | H1W1—O1W—H1W2 | 85.1 |
O1A—C1A—N1A | 123.6 (8) | H1W3—O1WA—H1W4 | 85.2 |
C1—N1—N2—C2 | 169.4 (7) | O1A—C1A—N1A—N2A | 8.9 (12) |
N2—N1—C1—O1 | 2.2 (11) | C11A—C1A—N1A—N2A | −169.1 (6) |
N2—N1—C1—C11 | −179.1 (6) | C1A—N1A—N2A—C2A | 173.4 (7) |
N1—N2—C2—C21 | −175.2 (6) | N1A—N2A—C2A—C21A | −177.9 (7) |
O1—C1—C11—C12 | −45.4 (10) | O1A—C1A—C11A—C12A | −130.6 (8) |
N1—C1—C11—C12 | 135.9 (7) | N1A—C1A—C11A—C12A | 47.4 (11) |
O1—C1—C11—C16 | 130.4 (8) | O1A—C1A—C11A—C16A | 39.6 (10) |
N1—C1—C11—C16 | −48.4 (9) | N1A—C1A—C11A—C16A | −142.4 (7) |
C16—C11—C12—C13 | −0.8 (10) | C16A—C11A—C12A—C13A | 0.3 (11) |
C1—C11—C12—C13 | 174.9 (7) | C1A—C11A—C12A—C13A | 170.5 (7) |
C16—C11—C12—Br1 | 174.6 (5) | C16A—C11A—C12A—Br1A | −177.3 (5) |
C1—C11—C12—Br1 | −9.7 (10) | C1A—C11A—C12A—Br1A | −7.1 (10) |
C11—C12—C13—C14 | −0.6 (11) | C11A—C12A—C13A—C14A | 0.8 (12) |
Br1—C12—C13—C14 | −176.3 (6) | Br1A—C12A—C13A—C14A | 178.5 (6) |
C12—C13—C14—C15 | 2.8 (12) | C12A—C13A—C14A—C15A | −0.8 (12) |
C17—O2—C15—C16 | 6.1 (12) | C17A—O2A—C15A—C14A | 177.3 (7) |
C17—O2—C15—C14 | −174.6 (8) | C17A—O2A—C15A—C16A | −0.8 (11) |
C13—C14—C15—O2 | 177.2 (7) | C13A—C14A—C15A—O2A | −178.6 (7) |
C13—C14—C15—C16 | −3.5 (13) | C13A—C14A—C15A—C16A | −0.4 (12) |
O2—C15—C16—C11 | −178.8 (7) | O2A—C15A—C16A—C11A | 179.6 (7) |
C14—C15—C16—C11 | 1.9 (12) | C14A—C15A—C16A—C11A | 1.6 (11) |
C12—C11—C16—C15 | 0.2 (11) | C12A—C11A—C16A—C15A | −1.6 (10) |
C1—C11—C16—C15 | −175.7 (7) | C1A—C11A—C16A—C15A | −172.7 (7) |
N2—C2—C21—C26 | −4.3 (12) | N2A—C2A—C21A—C22A | −174.8 (8) |
N2—C2—C21—C22 | 171.0 (7) | N2A—C2A—C21A—C26A | 5.4 (12) |
C26—C21—C22—C23 | 1.4 (11) | C26A—C21A—C22A—C23A | −1.4 (12) |
C2—C21—C22—C23 | −174.1 (7) | C2A—C21A—C22A—C23A | 178.8 (8) |
C21—C22—C23—C24 | −1.5 (12) | C21A—C22A—C23A—C24A | 2.0 (13) |
C22—C23—C24—F1 | −179.8 (7) | C22A—C23A—C24A—F1A | 179.4 (8) |
C22—C23—C24—C25 | −0.2 (13) | C22A—C23A—C24A—C25A | −3.1 (14) |
F1—C24—C25—C26 | −178.5 (7) | F1A—C24A—C25A—C26A | −179.1 (8) |
C23—C24—C25—C26 | 1.9 (13) | C23A—C24A—C25A—C26A | 3.3 (15) |
C24—C25—C26—C21 | −1.9 (12) | C24A—C25A—C26A—C21A | −2.4 (13) |
C22—C21—C26—C25 | 0.4 (11) | C22A—C21A—C26A—C25A | 1.6 (12) |
C2—C21—C26—C25 | 175.7 (7) | C2A—C21A—C26A—C25A | −178.6 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1W | 0.88 | 2.03 | 2.901 (9) | 172 |
N1A—H1A···O1WA | 0.88 | 2.01 | 2.860 (9) | 163 |
O1W—H1W1···O1i | 0.84 | 1.99 | 2.832 (8) | 180 |
O1W—H1W2···O1Aii | 0.84 | 2.01 | 2.856 (8) | 180 |
O1WA—H1W3···O1iii | 0.84 | 2.06 | 2.897 (8) | 180 |
O1WA—H1W4···O1Aiv | 0.84 | 1.96 | 2.802 (7) | 180 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+3/2, z−1/2; (iv) x, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H12BrFN2O2.H2O |
Mr | 369.19 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 173 |
a, b, c (Å) | 30.1171 (18), 8.0187 (7), 13.4661 (8) |
β (°) | 111.902 (4) |
V (Å3) | 3017.3 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 2.75 |
Crystal size (mm) | 0.37 × 0.35 × 0.33 |
Data collection | |
Diffractometer | STOE IPDS II two-circle- diffractometer |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.379, 0.394 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16531, 5477, 4843 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.080, 0.202, 1.02 |
No. of reflections | 5477 |
No. of parameters | 400 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.56, −0.76 |
Absolute structure | Flack (1983), 2642 Friedel pairs |
Absolute structure parameter | 0.018 (17) |
Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1W | 0.88 | 2.03 | 2.901 (9) | 171.6 |
N1A—H1A···O1WA | 0.88 | 2.01 | 2.860 (9) | 162.9 |
O1W—H1W1···O1i | 0.84 | 1.99 | 2.832 (8) | 179.8 |
O1W—H1W2···O1Aii | 0.84 | 2.01 | 2.856 (8) | 179.7 |
O1WA—H1W3···O1iii | 0.84 | 2.06 | 2.897 (8) | 179.9 |
O1WA—H1W4···O1Aiv | 0.84 | 1.96 | 2.802 (7) | 179.9 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+3/2, z−1/2; (iv) x, −y+1, z+1/2. |
Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives were reported to possess antimicrobial, anti-inflammatory and central nervous system activities. Moreover, Schiff bases are also known to have biological activities such as antimicrobial, antifungal, antitumor, and as herbicides. A new Schiff base, (I), C15H12BrFN2O2.H2O is synthesized and its crystal structure is reported.
The two molecules in the asymmetric unit differ in the dihedral angle between the two aromatic rings, which are 62.3 (2)° and 49.9 (2)°. The crystal packing is stabilized by N—H···O and O—H···O hydrogen bonds.