Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025524/hk2252sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025524/hk2252Isup2.hkl |
CCDC reference: 651540
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.145
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT355_ALERT_3_B Long O-H Bond (0.82A) O12 - H12A ... 1.08 Ang.
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.70 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.75 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.04 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT355_ALERT_3_C Long O-H Bond (0.82A) O11 - H11A ... 1.01 Ang. PLAT414_ALERT_2_C Short Intra D-H..H-X H4B .. H30A .. 1.96 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the preparation of (I), 4-fluorobenzoyl chloride (0.8 g, 5.1 mmol) was added in portions to a suspension of 3,4,5-trimethoxybenzoic hydrazide monohydrate (1.22 g, 5.0 mmol) in dry acetonitrile (50 ml), and the reaction mixture stirred for 7 h at 296 K. Then, the mixture was concentrated, and the solid product filtered and recrystallized from aqueous ethanol to afford the title compound (yield; 93%, m.p. 464–465 K). Suitable crystals were grown from a solution of (I) in ethanol by slow evaporation at room temperature.
H atoms of water molecules were located in difference syntheses and refined isotropically [O—H = 0.91 (4)–1.08 (5) Å and Uiso(H) = 0.150 (18)–0.21 (3) Å2]. The remaining H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93 and 0.96 Å for aromatic and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.
N,N-Diacylhydrazines are important intermediates especially for the synthesis of various biologically active five-membered heterocycles such as 2,5-disubstituted-1,3,4-oxadiazoles (Zheng et al., 2003; Al-Talib et al., 1990) and 5-substituted-2-mercapto-1,3,4-oxadiazoles (Yousif et al., 1986; Ahmad et al., 2001; Al-Soud et al., 2004; El-Emam et al., 2004). In view of the versatility of these compounds, we have synthesized the title compound, (I), using a literature method (Zareef & Iqbal, 2007) and reported its crystal structure.
The asymmetric unit of the title compound, (I), contains two N'-(4-fluorobenzoyl)-3,4,5-trimethoxybenzohydrazide and two water molecules (Fig. 1), in which the bond lengths and angles are within normal ranges (Allen et al., 1987).
Rings A (C1—C6), B (C12—C17) and C (C18—C23), D (C29—C34) are, of course, planar and the dihedral angles between them are A/B = 65.52 (3)° and C/D = 68.48 (3)°.
In the crystal structure, the intramolecular N—H···O and intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) link the molecules to form a supramolecular structure, in which they may be effective in the stabilization of the structure.
For general backgroud, see: Zheng et al. (2003); Al-Talib et al. (1990); Yousif et al. (1986); Ahmad et al. (2001); Al-Soud et al. (2004); El-Emam et al. (2004); Allen et al. (1987). For related literature, see: Zareef & Iqbal (2007).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C17H17FN2O5·H2O | F(000) = 1536 |
Mr = 366.34 | Dx = 1.379 Mg m−3 |
Monoclinic, P21/c | Melting point: 464(1) K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3845 (5) Å | Cell parameters from 876 reflections |
b = 13.2688 (9) Å | θ = 2.3–24.1° |
c = 31.833 (2) Å | µ = 0.11 mm−1 |
β = 94.615 (1)° | T = 294 K |
V = 3530.0 (4) Å3 | Plate, colorless |
Z = 8 | 0.34 × 0.23 × 0.16 mm |
Bruker SMART CCD diffractometer | 6146 independent reflections |
Radiation source: fine-focus sealed tube | 4451 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω and φ scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.97, Tmax = 0.98 | k = −15→15 |
16960 measured reflections | l = −37→29 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0788P)2 + 0.8812P] where P = (Fo2 + 2Fc2)/3 |
6146 reflections | (Δ/σ)max = 0.007 |
485 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C17H17FN2O5·H2O | V = 3530.0 (4) Å3 |
Mr = 366.34 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.3845 (5) Å | µ = 0.11 mm−1 |
b = 13.2688 (9) Å | T = 294 K |
c = 31.833 (2) Å | 0.34 × 0.23 × 0.16 mm |
β = 94.615 (1)° |
Bruker SMART CCD diffractometer | 6146 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4451 reflections with I > 2σ(I) |
Tmin = 0.97, Tmax = 0.98 | Rint = 0.033 |
16960 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.31 e Å−3 |
6146 reflections | Δρmin = −0.23 e Å−3 |
485 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 | ||
C1 | 0.1353 (3) | 0.62029 (16) | 0.07074 (6) | 0.0405 (5) | |
C2 | 0.2948 (3) | 0.59103 (15) | 0.07040 (6) | 0.0394 (5) | |
C3 | 0.3980 (2) | 0.59930 (15) | 0.10683 (6) | 0.0361 (5) | |
C4 | 0.3424 (2) | 0.63769 (15) | 0.14381 (6) | 0.0347 (5) | |
H4A | 0.4112 | 0.6443 | 0.1681 | 0.042* | |
C5 | 0.1821 (2) | 0.66597 (14) | 0.14378 (6) | 0.0324 (4) | |
C6 | 0.0785 (3) | 0.65717 (16) | 0.10768 (6) | 0.0377 (5) | |
H6A | −0.0283 | 0.6758 | 0.1082 | 0.045* | |
C7 | −0.1246 (3) | 0.6025 (2) | 0.03532 (8) | 0.0664 (8) | |
H7A | −0.1742 | 0.5944 | 0.0073 | 0.100* | |
H7B | −0.1631 | 0.6632 | 0.0474 | 0.100* | |
H7C | −0.1505 | 0.5458 | 0.0522 | 0.100* | |
C8 | 0.3834 (4) | 0.6156 (2) | 0.00231 (9) | 0.0735 (9) | |
H8A | 0.4212 | 0.5784 | −0.0208 | 0.110* | |
H8B | 0.4637 | 0.6630 | 0.0127 | 0.110* | |
H8C | 0.2874 | 0.6512 | −0.0072 | 0.110* | |
C9 | 0.6570 (3) | 0.5665 (2) | 0.14045 (8) | 0.0581 (7) | |
H9A | 0.7592 | 0.5409 | 0.1339 | 0.087* | |
H9B | 0.6152 | 0.5250 | 0.1617 | 0.087* | |
H9C | 0.6692 | 0.6343 | 0.1507 | 0.087* | |
C10 | 0.1128 (2) | 0.70154 (14) | 0.18295 (6) | 0.0329 (5) | |
C11 | 0.1289 (2) | 0.71749 (15) | 0.27885 (6) | 0.0356 (5) | |
C12 | 0.0682 (3) | 0.75824 (16) | 0.31808 (6) | 0.0390 (5) | |
C13 | 0.0654 (4) | 0.6931 (2) | 0.35163 (8) | 0.0656 (8) | |
H13A | 0.1003 | 0.6271 | 0.3489 | 0.079* | |
C14 | 0.0112 (5) | 0.7247 (3) | 0.38937 (9) | 0.0876 (11) | |
H14A | 0.0098 | 0.6807 | 0.4121 | 0.105* | |
C15 | −0.0398 (4) | 0.8209 (3) | 0.39262 (9) | 0.0763 (9) | |
C16 | −0.0401 (4) | 0.8875 (2) | 0.36048 (9) | 0.0693 (8) | |
H16A | −0.0765 | 0.9530 | 0.3637 | 0.083* | |
C17 | 0.0147 (3) | 0.85632 (17) | 0.32281 (7) | 0.0520 (6) | |
H17A | 0.0157 | 0.9014 | 0.3004 | 0.062* | |
C18 | 0.6326 (3) | 0.88247 (16) | 0.06547 (6) | 0.0404 (5) | |
C19 | 0.7901 (3) | 0.91489 (16) | 0.06329 (6) | 0.0410 (5) | |
C20 | 0.8925 (3) | 0.92140 (16) | 0.09979 (7) | 0.0395 (5) | |
C21 | 0.8393 (2) | 0.89549 (15) | 0.13871 (6) | 0.0374 (5) | |
H21A | 0.9079 | 0.8993 | 0.1631 | 0.045* | |
C22 | 0.6817 (2) | 0.86384 (14) | 0.14043 (6) | 0.0331 (4) | |
C23 | 0.5787 (3) | 0.85736 (16) | 0.10412 (6) | 0.0387 (5) | |
H23A | 0.4736 | 0.8362 | 0.1057 | 0.046* | |
C24 | 0.3742 (3) | 0.8852 (2) | 0.02942 (9) | 0.0699 (8) | |
H24A | 0.3242 | 0.8818 | 0.0012 | 0.105* | |
H24B | 0.3470 | 0.9478 | 0.0421 | 0.105* | |
H24C | 0.3373 | 0.8302 | 0.0457 | 0.105* | |
C25 | 0.8852 (5) | 0.8736 (3) | −0.00250 (10) | 0.0913 (11) | |
H25A | 0.9205 | 0.9053 | −0.0272 | 0.137* | |
H25B | 0.7937 | 0.8321 | −0.0103 | 0.137* | |
H25C | 0.9698 | 0.8327 | 0.0105 | 0.137* | |
C26 | 1.1576 (3) | 0.9561 (2) | 0.12892 (8) | 0.0651 (8) | |
H26A | 1.2562 | 0.9837 | 0.1207 | 0.098* | |
H26B | 1.1747 | 0.8879 | 0.1383 | 0.098* | |
H26C | 1.1206 | 0.9957 | 0.1514 | 0.098* | |
C27 | 0.6136 (2) | 0.84363 (14) | 0.18144 (6) | 0.0332 (5) | |
C28 | 0.6198 (2) | 0.71404 (15) | 0.26891 (6) | 0.0364 (5) | |
C29 | 0.5681 (3) | 0.71889 (15) | 0.31265 (6) | 0.0378 (5) | |
C30 | 0.5624 (3) | 0.80734 (17) | 0.33588 (7) | 0.0569 (7) | |
H30A | 0.5917 | 0.8679 | 0.3240 | 0.068* | |
C31 | 0.5136 (4) | 0.8065 (2) | 0.37639 (8) | 0.0707 (9) | |
H31A | 0.5091 | 0.8659 | 0.3918 | 0.085* | |
C32 | 0.4727 (4) | 0.7175 (2) | 0.39295 (8) | 0.0637 (7) | |
C33 | 0.4743 (3) | 0.62851 (19) | 0.37147 (8) | 0.0605 (7) | |
H33A | 0.4433 | 0.5688 | 0.3837 | 0.073* | |
C34 | 0.5231 (3) | 0.62949 (17) | 0.33105 (7) | 0.0486 (6) | |
H34A | 0.5259 | 0.5696 | 0.3160 | 0.058* | |
F1 | −0.0941 (3) | 0.85145 (18) | 0.42954 (6) | 0.1304 (9) | |
F2 | 0.4249 (3) | 0.71612 (15) | 0.43261 (5) | 0.1053 (7) | |
H11A | 0.227 (6) | 1.024 (4) | 0.2480 (16) | 0.21 (3)* | |
H12A | 0.524 (6) | 0.029 (4) | 0.2616 (14) | 0.166 (19)* | |
H11B | 0.020 (6) | 1.030 (4) | 0.2369 (15) | 0.17 (2)* | |
H12B | 0.732 (5) | 0.038 (4) | 0.2605 (13) | 0.150 (18)* | |
N1 | 0.2139 (2) | 0.75011 (13) | 0.21121 (5) | 0.0383 (4) | |
H1A | 0.3115 | 0.7602 | 0.2059 | 0.046* | |
N2 | 0.1603 (2) | 0.78397 (13) | 0.24905 (5) | 0.0386 (4) | |
H2A | 0.1475 | 0.8474 | 0.2532 | 0.046* | |
N3 | 0.7156 (2) | 0.80515 (13) | 0.21211 (5) | 0.0392 (4) | |
H3A | 0.8085 | 0.7838 | 0.2066 | 0.047* | |
N4 | 0.6678 (2) | 0.80059 (13) | 0.25281 (5) | 0.0399 (4) | |
H4B | 0.6692 | 0.8544 | 0.2679 | 0.048* | |
O1 | 0.0433 (2) | 0.60855 (14) | 0.03384 (5) | 0.0601 (5) | |
O2 | 0.3502 (2) | 0.54784 (12) | 0.03520 (5) | 0.0515 (4) | |
O3 | 0.55010 (18) | 0.56535 (12) | 0.10374 (5) | 0.0499 (4) | |
O4 | −0.02783 (17) | 0.68598 (12) | 0.18909 (5) | 0.0460 (4) | |
O5 | 0.1502 (2) | 0.62589 (11) | 0.27442 (5) | 0.0493 (4) | |
O6 | 0.5408 (2) | 0.87890 (15) | 0.02826 (5) | 0.0631 (5) | |
O7 | 0.8433 (2) | 0.94808 (13) | 0.02612 (5) | 0.0571 (5) | |
O8 | 1.04171 (19) | 0.95777 (14) | 0.09416 (5) | 0.0576 (5) | |
O9 | 0.47413 (17) | 0.86429 (12) | 0.18701 (5) | 0.0448 (4) | |
O10 | 0.6223 (2) | 0.63466 (11) | 0.24890 (5) | 0.0556 (5) | |
O11 | 0.1199 (3) | 0.99373 (14) | 0.23830 (7) | 0.0737 (6) | |
O12 | 0.6459 (3) | 0.00454 (12) | 0.26922 (5) | 0.0567 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0457 (13) | 0.0455 (12) | 0.0300 (11) | −0.0021 (10) | 0.0022 (9) | −0.0024 (9) |
C2 | 0.0484 (14) | 0.0371 (11) | 0.0343 (11) | 0.0001 (10) | 0.0132 (9) | −0.0059 (9) |
C3 | 0.0339 (12) | 0.0360 (11) | 0.0398 (12) | 0.0024 (9) | 0.0115 (9) | −0.0010 (9) |
C4 | 0.0334 (12) | 0.0372 (11) | 0.0337 (11) | −0.0007 (9) | 0.0047 (8) | −0.0037 (8) |
C5 | 0.0325 (11) | 0.0325 (10) | 0.0331 (11) | −0.0004 (8) | 0.0074 (8) | −0.0019 (8) |
C6 | 0.0340 (12) | 0.0426 (12) | 0.0368 (12) | 0.0024 (9) | 0.0054 (9) | −0.0008 (9) |
C7 | 0.0518 (17) | 0.092 (2) | 0.0533 (16) | −0.0062 (14) | −0.0099 (12) | −0.0093 (14) |
C8 | 0.098 (2) | 0.0757 (19) | 0.0520 (16) | 0.0077 (17) | 0.0375 (15) | 0.0017 (14) |
C9 | 0.0367 (14) | 0.0726 (17) | 0.0648 (16) | 0.0087 (12) | 0.0016 (12) | −0.0125 (13) |
C10 | 0.0325 (12) | 0.0340 (10) | 0.0329 (11) | 0.0031 (8) | 0.0067 (8) | 0.0006 (8) |
C11 | 0.0357 (12) | 0.0336 (11) | 0.0378 (11) | −0.0021 (9) | 0.0039 (9) | −0.0024 (9) |
C12 | 0.0393 (12) | 0.0433 (12) | 0.0349 (11) | −0.0050 (9) | 0.0060 (9) | −0.0057 (9) |
C13 | 0.094 (2) | 0.0544 (15) | 0.0513 (16) | 0.0097 (14) | 0.0241 (14) | 0.0082 (12) |
C14 | 0.136 (3) | 0.085 (2) | 0.0462 (17) | 0.009 (2) | 0.0385 (18) | 0.0165 (15) |
C15 | 0.105 (3) | 0.086 (2) | 0.0426 (16) | −0.0062 (18) | 0.0323 (15) | −0.0172 (15) |
C16 | 0.098 (2) | 0.0535 (15) | 0.0608 (18) | −0.0028 (15) | 0.0338 (16) | −0.0194 (13) |
C17 | 0.0719 (17) | 0.0432 (13) | 0.0433 (13) | 0.0008 (12) | 0.0189 (12) | −0.0027 (10) |
C18 | 0.0456 (13) | 0.0433 (12) | 0.0318 (11) | 0.0008 (10) | −0.0001 (9) | −0.0005 (9) |
C19 | 0.0515 (14) | 0.0390 (11) | 0.0338 (11) | 0.0031 (10) | 0.0109 (10) | 0.0068 (9) |
C20 | 0.0372 (12) | 0.0406 (11) | 0.0421 (12) | −0.0018 (9) | 0.0118 (9) | 0.0062 (9) |
C21 | 0.0360 (12) | 0.0417 (12) | 0.0348 (11) | −0.0021 (9) | 0.0044 (9) | 0.0046 (9) |
C22 | 0.0341 (12) | 0.0332 (10) | 0.0328 (11) | 0.0007 (8) | 0.0067 (8) | 0.0018 (8) |
C23 | 0.0336 (12) | 0.0429 (12) | 0.0399 (12) | −0.0025 (9) | 0.0053 (9) | 0.0007 (9) |
C24 | 0.0629 (19) | 0.086 (2) | 0.0573 (17) | 0.0096 (15) | −0.0176 (13) | −0.0017 (14) |
C25 | 0.133 (3) | 0.086 (2) | 0.0627 (19) | −0.009 (2) | 0.054 (2) | −0.0037 (17) |
C26 | 0.0387 (14) | 0.089 (2) | 0.0673 (17) | −0.0166 (14) | 0.0037 (12) | 0.0139 (15) |
C27 | 0.0322 (12) | 0.0315 (10) | 0.0364 (11) | −0.0038 (8) | 0.0066 (9) | −0.0020 (8) |
C28 | 0.0364 (12) | 0.0345 (11) | 0.0387 (11) | 0.0035 (9) | 0.0051 (9) | −0.0004 (9) |
C29 | 0.0423 (13) | 0.0372 (11) | 0.0345 (11) | 0.0032 (9) | 0.0073 (9) | 0.0063 (9) |
C30 | 0.091 (2) | 0.0363 (12) | 0.0460 (14) | −0.0039 (12) | 0.0246 (13) | 0.0037 (10) |
C31 | 0.122 (3) | 0.0474 (15) | 0.0465 (15) | 0.0005 (15) | 0.0322 (16) | −0.0049 (12) |
C32 | 0.091 (2) | 0.0657 (17) | 0.0374 (14) | 0.0067 (15) | 0.0253 (13) | 0.0089 (12) |
C33 | 0.087 (2) | 0.0482 (14) | 0.0496 (15) | −0.0017 (13) | 0.0222 (13) | 0.0181 (12) |
C34 | 0.0644 (16) | 0.0367 (12) | 0.0461 (13) | 0.0004 (11) | 0.0129 (11) | 0.0033 (10) |
F1 | 0.205 (3) | 0.1345 (18) | 0.0614 (12) | 0.0040 (18) | 0.0715 (14) | −0.0247 (12) |
F2 | 0.181 (2) | 0.0936 (13) | 0.0492 (10) | 0.0023 (13) | 0.0573 (11) | 0.0106 (9) |
N1 | 0.0356 (10) | 0.0485 (10) | 0.0327 (9) | −0.0055 (8) | 0.0138 (7) | −0.0089 (8) |
N2 | 0.0494 (11) | 0.0326 (9) | 0.0352 (9) | −0.0036 (8) | 0.0124 (8) | −0.0065 (7) |
N3 | 0.0387 (10) | 0.0498 (11) | 0.0309 (9) | 0.0065 (8) | 0.0138 (8) | 0.0039 (8) |
N4 | 0.0548 (12) | 0.0353 (9) | 0.0314 (9) | −0.0017 (8) | 0.0141 (8) | −0.0013 (7) |
O1 | 0.0526 (11) | 0.0931 (13) | 0.0337 (9) | 0.0022 (9) | −0.0013 (7) | −0.0112 (8) |
O2 | 0.0663 (11) | 0.0540 (10) | 0.0363 (9) | 0.0052 (8) | 0.0180 (7) | −0.0095 (7) |
O3 | 0.0385 (9) | 0.0629 (10) | 0.0497 (10) | 0.0115 (7) | 0.0117 (7) | −0.0084 (8) |
O4 | 0.0300 (9) | 0.0627 (10) | 0.0464 (9) | −0.0008 (7) | 0.0102 (7) | −0.0091 (7) |
O5 | 0.0638 (11) | 0.0341 (9) | 0.0513 (10) | 0.0055 (7) | 0.0138 (8) | −0.0020 (7) |
O6 | 0.0544 (11) | 0.0962 (14) | 0.0374 (9) | −0.0030 (10) | −0.0036 (8) | 0.0010 (9) |
O7 | 0.0713 (12) | 0.0643 (11) | 0.0379 (9) | −0.0013 (9) | 0.0181 (8) | 0.0126 (8) |
O8 | 0.0398 (9) | 0.0815 (12) | 0.0524 (10) | −0.0144 (8) | 0.0102 (7) | 0.0173 (9) |
O9 | 0.0314 (9) | 0.0547 (9) | 0.0496 (9) | −0.0010 (7) | 0.0115 (7) | 0.0003 (7) |
O10 | 0.0804 (13) | 0.0363 (9) | 0.0528 (10) | −0.0035 (8) | 0.0222 (9) | −0.0072 (7) |
O11 | 0.0760 (15) | 0.0430 (10) | 0.1049 (16) | 0.0036 (10) | 0.0246 (12) | 0.0115 (10) |
O12 | 0.0779 (14) | 0.0358 (9) | 0.0578 (11) | −0.0084 (9) | 0.0150 (9) | 0.0026 (7) |
C1—O1 | 1.361 (3) | C20—O8 | 1.366 (3) |
C1—C6 | 1.393 (3) | C20—C21 | 1.393 (3) |
C1—C2 | 1.393 (3) | C21—C22 | 1.392 (3) |
C2—O2 | 1.373 (2) | C21—H21A | 0.9300 |
C2—C3 | 1.394 (3) | C22—C23 | 1.389 (3) |
C3—O3 | 1.364 (2) | C22—C27 | 1.490 (3) |
C3—C4 | 1.396 (3) | C23—H23A | 0.9300 |
C4—C5 | 1.396 (3) | C24—O6 | 1.403 (3) |
C4—H4A | 0.9300 | C24—H24A | 0.9600 |
C5—C6 | 1.389 (3) | C24—H24B | 0.9600 |
C5—C10 | 1.494 (3) | C24—H24C | 0.9600 |
C6—H6A | 0.9300 | C25—O7 | 1.407 (3) |
C7—O1 | 1.415 (3) | C25—H25A | 0.9600 |
C7—H7A | 0.9600 | C25—H25B | 0.9600 |
C7—H7B | 0.9600 | C25—H25C | 0.9600 |
C7—H7C | 0.9600 | C26—O8 | 1.413 (3) |
C8—O2 | 1.425 (3) | C26—H26A | 0.9600 |
C8—H8A | 0.9600 | C26—H26B | 0.9600 |
C8—H8B | 0.9600 | C26—H26C | 0.9600 |
C8—H8C | 0.9600 | C27—O9 | 1.228 (2) |
C9—O3 | 1.415 (3) | C27—N3 | 1.346 (3) |
C9—H9A | 0.9600 | C28—O10 | 1.232 (2) |
C9—H9B | 0.9600 | C28—N4 | 1.333 (3) |
C9—H9C | 0.9600 | C28—C29 | 1.493 (3) |
C10—O4 | 1.228 (2) | C29—C34 | 1.389 (3) |
C10—N1 | 1.349 (3) | C29—C30 | 1.390 (3) |
C11—O5 | 1.238 (2) | C30—C31 | 1.384 (3) |
C11—N2 | 1.337 (3) | C30—H30A | 0.9300 |
C11—C12 | 1.488 (3) | C31—C32 | 1.349 (4) |
C12—C13 | 1.376 (3) | C31—H31A | 0.9300 |
C12—C17 | 1.389 (3) | C32—F2 | 1.355 (3) |
C13—C14 | 1.383 (4) | C32—C33 | 1.365 (4) |
C13—H13A | 0.9300 | C33—C34 | 1.381 (3) |
C14—C15 | 1.353 (4) | C33—H33A | 0.9300 |
C14—H14A | 0.9300 | C34—H34A | 0.9300 |
C15—C16 | 1.351 (4) | N1—N2 | 1.393 (2) |
C15—F1 | 1.356 (3) | N1—H1A | 0.8600 |
C16—C17 | 1.381 (3) | N2—H2A | 0.8600 |
C16—H16A | 0.9300 | N3—N4 | 1.388 (2) |
C17—H17A | 0.9300 | N3—H3A | 0.8600 |
C18—O6 | 1.360 (3) | N4—H4B | 0.8600 |
C18—C23 | 1.385 (3) | O11—H11A | 1.01 (6) |
C18—C19 | 1.396 (3) | O11—H11B | 0.97 (6) |
C19—O7 | 1.370 (2) | O12—H12A | 1.08 (5) |
C19—C20 | 1.391 (3) | O12—H12B | 0.91 (4) |
O1—C1—C6 | 124.0 (2) | C22—C21—H21A | 120.6 |
O1—C1—C2 | 116.06 (18) | C20—C21—H21A | 120.6 |
C6—C1—C2 | 119.88 (19) | C23—C22—C21 | 120.98 (18) |
O2—C2—C1 | 120.72 (19) | C23—C22—C27 | 117.48 (18) |
O2—C2—C3 | 118.93 (19) | C21—C22—C27 | 121.36 (18) |
C1—C2—C3 | 120.23 (18) | C18—C23—C22 | 119.9 (2) |
O3—C3—C2 | 115.82 (17) | C18—C23—H23A | 120.0 |
O3—C3—C4 | 123.94 (19) | C22—C23—H23A | 120.0 |
C2—C3—C4 | 120.21 (19) | O6—C24—H24A | 109.5 |
C5—C4—C3 | 118.95 (19) | O6—C24—H24B | 109.5 |
C5—C4—H4A | 120.5 | H24A—C24—H24B | 109.5 |
C3—C4—H4A | 120.5 | O6—C24—H24C | 109.5 |
C6—C5—C4 | 121.08 (18) | H24A—C24—H24C | 109.5 |
C6—C5—C10 | 117.25 (18) | H24B—C24—H24C | 109.5 |
C4—C5—C10 | 121.59 (17) | O7—C25—H25A | 109.5 |
C5—C6—C1 | 119.6 (2) | O7—C25—H25B | 109.5 |
C5—C6—H6A | 120.2 | H25A—C25—H25B | 109.5 |
C1—C6—H6A | 120.2 | O7—C25—H25C | 109.5 |
O1—C7—H7A | 109.5 | H25A—C25—H25C | 109.5 |
O1—C7—H7B | 109.5 | H25B—C25—H25C | 109.5 |
H7A—C7—H7B | 109.5 | O8—C26—H26A | 109.5 |
O1—C7—H7C | 109.5 | O8—C26—H26B | 109.5 |
H7A—C7—H7C | 109.5 | H26A—C26—H26B | 109.5 |
H7B—C7—H7C | 109.5 | O8—C26—H26C | 109.5 |
O2—C8—H8A | 109.5 | H26A—C26—H26C | 109.5 |
O2—C8—H8B | 109.5 | H26B—C26—H26C | 109.5 |
H8A—C8—H8B | 109.5 | O9—C27—N3 | 122.46 (18) |
O2—C8—H8C | 109.5 | O9—C27—C22 | 121.52 (18) |
H8A—C8—H8C | 109.5 | N3—C27—C22 | 115.97 (17) |
H8B—C8—H8C | 109.5 | O10—C28—N4 | 121.32 (19) |
O3—C9—H9A | 109.5 | O10—C28—C29 | 122.51 (19) |
O3—C9—H9B | 109.5 | N4—C28—C29 | 116.15 (18) |
H9A—C9—H9B | 109.5 | C34—C29—C30 | 118.3 (2) |
O3—C9—H9C | 109.5 | C34—C29—C28 | 117.77 (19) |
H9A—C9—H9C | 109.5 | C30—C29—C28 | 123.89 (19) |
H9B—C9—H9C | 109.5 | C31—C30—C29 | 121.0 (2) |
O4—C10—N1 | 122.27 (18) | C31—C30—H30A | 119.5 |
O4—C10—C5 | 121.50 (18) | C29—C30—H30A | 119.5 |
N1—C10—C5 | 116.22 (17) | C32—C31—C30 | 118.3 (2) |
O5—C11—N2 | 121.91 (19) | C32—C31—H31A | 120.8 |
O5—C11—C12 | 120.96 (19) | C30—C31—H31A | 120.8 |
N2—C11—C12 | 117.12 (18) | C31—C32—F2 | 118.6 (2) |
C13—C12—C17 | 118.6 (2) | C31—C32—C33 | 123.3 (2) |
C13—C12—C11 | 116.9 (2) | F2—C32—C33 | 118.1 (2) |
C17—C12—C11 | 124.5 (2) | C32—C33—C34 | 118.3 (2) |
C12—C13—C14 | 120.7 (3) | C32—C33—H33A | 120.8 |
C12—C13—H13A | 119.6 | C34—C33—H33A | 120.8 |
C14—C13—H13A | 119.6 | C33—C34—C29 | 120.8 (2) |
C15—C14—C13 | 118.7 (3) | C33—C34—H34A | 119.6 |
C15—C14—H14A | 120.6 | C29—C34—H34A | 119.6 |
C13—C14—H14A | 120.6 | C10—N1—N2 | 120.11 (16) |
C16—C15—C14 | 122.7 (2) | C10—N1—H1A | 119.9 |
C16—C15—F1 | 118.7 (3) | N2—N1—H1A | 119.9 |
C14—C15—F1 | 118.6 (3) | C11—N2—N1 | 119.74 (17) |
C15—C16—C17 | 118.8 (3) | C11—N2—H2A | 120.1 |
C15—C16—H16A | 120.6 | N1—N2—H2A | 120.1 |
C17—C16—H16A | 120.6 | C27—N3—N4 | 118.66 (17) |
C16—C17—C12 | 120.5 (2) | C27—N3—H3A | 120.7 |
C16—C17—H17A | 119.8 | N4—N3—H3A | 120.7 |
C12—C17—H17A | 119.8 | C28—N4—N3 | 121.00 (17) |
O6—C18—C23 | 124.3 (2) | C28—N4—H4B | 119.5 |
O6—C18—C19 | 116.01 (19) | N3—N4—H4B | 119.5 |
C23—C18—C19 | 119.73 (19) | C1—O1—C7 | 118.31 (18) |
O7—C19—C20 | 118.6 (2) | C2—O2—C8 | 115.80 (18) |
O7—C19—C18 | 121.13 (19) | C3—O3—C9 | 118.12 (17) |
C20—C19—C18 | 120.05 (18) | C18—O6—C24 | 118.01 (19) |
O8—C20—C19 | 115.02 (18) | C19—O7—C25 | 116.67 (19) |
O8—C20—C21 | 124.5 (2) | C20—O8—C26 | 118.12 (18) |
C19—C20—C21 | 120.5 (2) | H11A—O11—H11B | 124 (4) |
C22—C21—C20 | 118.83 (19) | H12A—O12—H12B | 123 (4) |
O1—C1—C2—O2 | −3.5 (3) | C20—C21—C22—C27 | −174.65 (19) |
C6—C1—C2—O2 | 175.32 (19) | O6—C18—C23—C22 | −179.8 (2) |
O1—C1—C2—C3 | −179.37 (19) | C19—C18—C23—C22 | −0.5 (3) |
C6—C1—C2—C3 | −0.5 (3) | C21—C22—C23—C18 | 0.1 (3) |
O2—C2—C3—O3 | 1.8 (3) | C27—C22—C23—C18 | 175.33 (18) |
C1—C2—C3—O3 | 177.72 (19) | C23—C22—C27—O9 | −31.8 (3) |
O2—C2—C3—C4 | −176.40 (18) | C21—C22—C27—O9 | 143.4 (2) |
C1—C2—C3—C4 | −0.5 (3) | C23—C22—C27—N3 | 150.57 (19) |
O3—C3—C4—C5 | −177.07 (18) | C21—C22—C27—N3 | −34.2 (3) |
C2—C3—C4—C5 | 1.0 (3) | O10—C28—C29—C34 | 0.7 (3) |
C3—C4—C5—C6 | −0.5 (3) | N4—C28—C29—C34 | −177.6 (2) |
C3—C4—C5—C10 | 176.16 (18) | O10—C28—C29—C30 | −179.3 (2) |
C4—C5—C6—C1 | −0.5 (3) | N4—C28—C29—C30 | 2.4 (3) |
C10—C5—C6—C1 | −177.29 (18) | C34—C29—C30—C31 | 0.2 (4) |
O1—C1—C6—C5 | 179.8 (2) | C28—C29—C30—C31 | −179.8 (2) |
C2—C1—C6—C5 | 1.0 (3) | C29—C30—C31—C32 | 0.5 (5) |
C6—C5—C10—O4 | 28.4 (3) | C30—C31—C32—F2 | 179.9 (3) |
C4—C5—C10—O4 | −148.3 (2) | C30—C31—C32—C33 | −1.2 (5) |
C6—C5—C10—N1 | −152.48 (19) | C31—C32—C33—C34 | 1.3 (5) |
C4—C5—C10—N1 | 30.8 (3) | F2—C32—C33—C34 | −179.9 (3) |
O5—C11—C12—C13 | 11.6 (3) | C32—C33—C34—C29 | −0.5 (4) |
N2—C11—C12—C13 | −167.8 (2) | C30—C29—C34—C33 | −0.2 (4) |
O5—C11—C12—C17 | −168.1 (2) | C28—C29—C34—C33 | 179.9 (2) |
N2—C11—C12—C17 | 12.4 (3) | O4—C10—N1—N2 | 0.5 (3) |
C17—C12—C13—C14 | −0.4 (4) | C5—C10—N1—N2 | −178.61 (17) |
C11—C12—C13—C14 | 179.8 (3) | O5—C11—N2—N1 | 2.0 (3) |
C12—C13—C14—C15 | 0.3 (5) | C12—C11—N2—N1 | −178.50 (18) |
C13—C14—C15—C16 | 0.1 (6) | C10—N1—N2—C11 | 71.4 (3) |
C13—C14—C15—F1 | 179.5 (3) | O9—C27—N3—N4 | −8.4 (3) |
C14—C15—C16—C17 | −0.4 (5) | C22—C27—N3—N4 | 169.24 (16) |
F1—C15—C16—C17 | −179.8 (3) | O10—C28—N4—N3 | 2.9 (3) |
C15—C16—C17—C12 | 0.3 (4) | C29—C28—N4—N3 | −178.77 (18) |
C13—C12—C17—C16 | 0.0 (4) | C27—N3—N4—C28 | 102.7 (2) |
C11—C12—C17—C16 | 179.8 (2) | C6—C1—O1—C7 | −20.6 (3) |
O6—C18—C19—O7 | 4.7 (3) | C2—C1—O1—C7 | 158.2 (2) |
C23—C18—C19—O7 | −174.6 (2) | C1—C2—O2—C8 | 78.9 (3) |
O6—C18—C19—C20 | 179.7 (2) | C3—C2—O2—C8 | −105.2 (3) |
C23—C18—C19—C20 | 0.3 (3) | C2—C3—O3—C9 | −176.3 (2) |
O7—C19—C20—O8 | −2.4 (3) | C4—C3—O3—C9 | 1.8 (3) |
C18—C19—C20—O8 | −177.52 (19) | C23—C18—O6—C24 | 23.3 (3) |
O7—C19—C20—C21 | 175.25 (19) | C19—C18—O6—C24 | −156.0 (2) |
C18—C19—C20—C21 | 0.2 (3) | C20—C19—O7—C25 | 104.8 (3) |
O8—C20—C21—C22 | 176.9 (2) | C18—C19—O7—C25 | −80.2 (3) |
C19—C20—C21—C22 | −0.5 (3) | C19—C20—O8—C26 | −173.2 (2) |
C20—C21—C22—C23 | 0.4 (3) | C21—C20—O8—C26 | 9.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O9 | 0.86 | 2.06 | 2.814 (2) | 145 |
N2—H2A···O11 | 0.86 | 2.01 | 2.821 (3) | 157 |
N3—H3A···O4i | 0.86 | 2.00 | 2.814 (2) | 157 |
N4—H4B···O12ii | 0.86 | 2.00 | 2.765 (2) | 147 |
O11—H11A···O10iii | 1.01 (5) | 1.93 (5) | 2.862 (3) | 152 (4) |
O11—H11B···O5iv | 0.96 (5) | 1.92 (5) | 2.867 (3) | 165 (5) |
O12—H12A···O10v | 1.08 (5) | 1.88 (5) | 2.857 (3) | 149 (4) |
O12—H12B···O5v | 0.91 (5) | 1.94 (5) | 2.798 (3) | 157 (4) |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+1/2; (iv) −x, y+1/2, −z+1/2; (v) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H17FN2O5·H2O |
Mr | 366.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 8.3845 (5), 13.2688 (9), 31.833 (2) |
β (°) | 94.615 (1) |
V (Å3) | 3530.0 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.34 × 0.23 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.97, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16960, 6146, 4451 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.145, 1.02 |
No. of reflections | 6146 |
No. of parameters | 485 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.23 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O9 | 0.86 | 2.06 | 2.814 (2) | 145 |
N2—H2A···O11 | 0.86 | 2.01 | 2.821 (3) | 157 |
N3—H3A···O4i | 0.86 | 2.00 | 2.814 (2) | 157 |
N4—H4B···O12ii | 0.86 | 2.00 | 2.765 (2) | 147 |
O11—H11A···O10iii | 1.01 (5) | 1.93 (5) | 2.862 (3) | 152 (4) |
O11—H11B···O5iv | 0.96 (5) | 1.92 (5) | 2.867 (3) | 165 (5) |
O12—H12A···O10v | 1.08 (5) | 1.88 (5) | 2.857 (3) | 149 (4) |
O12—H12B···O5v | 0.91 (5) | 1.94 (5) | 2.798 (3) | 157 (4) |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+1/2; (iv) −x, y+1/2, −z+1/2; (v) −x+1, y−1/2, −z+1/2. |
N,N-Diacylhydrazines are important intermediates especially for the synthesis of various biologically active five-membered heterocycles such as 2,5-disubstituted-1,3,4-oxadiazoles (Zheng et al., 2003; Al-Talib et al., 1990) and 5-substituted-2-mercapto-1,3,4-oxadiazoles (Yousif et al., 1986; Ahmad et al., 2001; Al-Soud et al., 2004; El-Emam et al., 2004). In view of the versatility of these compounds, we have synthesized the title compound, (I), using a literature method (Zareef & Iqbal, 2007) and reported its crystal structure.
The asymmetric unit of the title compound, (I), contains two N'-(4-fluorobenzoyl)-3,4,5-trimethoxybenzohydrazide and two water molecules (Fig. 1), in which the bond lengths and angles are within normal ranges (Allen et al., 1987).
Rings A (C1—C6), B (C12—C17) and C (C18—C23), D (C29—C34) are, of course, planar and the dihedral angles between them are A/B = 65.52 (3)° and C/D = 68.48 (3)°.
In the crystal structure, the intramolecular N—H···O and intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) link the molecules to form a supramolecular structure, in which they may be effective in the stabilization of the structure.