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organic compounds
N′-[(E)-4-(Diethylamino)benzylidene]-4-nitrobenzohydrazide monohydrate
aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan, and cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
*Correspondence e-mail: rehman_pcsir@hotmail.com
In the title compound, C18H20N4O3·H2O, the two aromatic rings are linked through a methylidenehydrazide fragment, which is fully extended with C—C—N—N, C—N—N=C and N—N=C—C torsion angles of 179.4 (2), 174.7 (2) and 178.3 (2)°, respectively. The dihedral angle between the two aromatic rings is 7.01 (8)°. In the the water of hydration is involved in extensive hydrogen bonding. Intermolecular O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds link the components of the structure into a two-dimensional network and additional stabilization is provided by weak intermolecular C—H⋯O hydrogen bonds.
Related literature
For the synthesis of related compounds, see: Ahmad et al. (2010). For the coordinating capability of see: Rodríguez-Argüelles et al. (2004
). For the biological activity of benzohydrazides, see: Zia-ur-Rehman et al. (2009
); Galal et al. (2009
); Bordoloi et al. (2009
). For closely related structures, see: Fun et al. (2008
); Bessy et al. (2006
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: COLLECT (Hooft, 1998); cell DENZO (Otwinowski & Minor, 1997
); data reduction: SCALEPACK (Otwinowski & Minor, 1997
); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997
); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536810011554/bt5231sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810011554/bt5231Isup2.hkl
A mixture of para nitrobenzohydrazide (0.5 g, 2.76 mmoles), p-(diethylamino)benzaldehyde (0.49 g, 2.76 mmoles), orthophosphoric acid (0.2 ml) and methanol (50.0 ml) was refluxed for a period of 5.5 hours followed by removal of the solvent under vacuum. The contents were cooled and washed with cold methanol followed by crystallization from the same solvent at room temperature by slow evaporation. Yield: 91%. M.p. 491 K.
Though all the H atoms could be distinguished in the difference Fourier map the H-atoms bonded to C-atoms were included at geometrically idealized positions and refined in riding-model approximation with C—H = 0.95, 0.98 and 0.99 Å, for aryl, methyl and methylene H-atoms, respectively; the coordinates of the H-atoms bonded to N2 and O4 were allowed to refine. The Uiso(H) were allowed at 1.5Ueq(methyl-C and water-O) and 1.2Ueq(the rest of the parent atoms). The final difference map was essentially featurless.
Data collection: COLLECT (Hooft, 1998); cell
DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C18H20N4O3·H2O | F(000) = 1520 |
Mr = 358.40 | Dx = 1.333 Mg m−3 |
Monoclinic, C2/c | Melting point: 491 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 38.3142 (12) Å | Cell parameters from 3855 reflections |
b = 7.4563 (3) Å | θ = 1.0–27.5° |
c = 12.6332 (5) Å | µ = 0.10 mm−1 |
β = 98.215 (2)° | T = 173 K |
V = 3572.0 (2) Å3 | Prism, orange |
Z = 8 | 0.08 × 0.06 × 0.04 mm |
Nonius KappaCCD diffractometer | 4048 independent reflections |
Radiation source: fine-focus sealed tube | 3182 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω and ϕ scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −49→49 |
Tmin = 0.992, Tmax = 0.996 | k = −6→9 |
5710 measured reflections | l = −16→16 |
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)] = 0.059 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0299P)2 + 6.8806P] where P = (Fo2 + 2Fc2)/3 |
4048 reflections | (Δ/σ)max < 0.001 |
246 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C18H20N4O3·H2O | V = 3572.0 (2) Å3 |
Mr = 358.40 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 38.3142 (12) Å | µ = 0.10 mm−1 |
b = 7.4563 (3) Å | T = 173 K |
c = 12.6332 (5) Å | 0.08 × 0.06 × 0.04 mm |
β = 98.215 (2)° |
Nonius KappaCCD diffractometer | 4048 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 3182 reflections with I > 2σ(I) |
Tmin = 0.992, Tmax = 0.996 | Rint = 0.021 |
5710 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.29 e Å−3 |
4048 reflections | Δρmin = −0.19 e Å−3 |
246 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
O4 | 0.24370 (5) | 0.6548 (3) | 0.29158 (14) | 0.0491 (5) | |
H4A | 0.2524 (8) | 0.625 (5) | 0.236 (3) | 0.074* | |
H4B | 0.2376 (9) | 0.762 (5) | 0.289 (3) | 0.074* | |
O1 | 0.44265 (4) | 0.7990 (3) | 0.48843 (14) | 0.0504 (5) | |
O2 | 0.42219 (4) | 0.7098 (3) | 0.32907 (14) | 0.0529 (5) | |
O3 | 0.29243 (4) | 0.4979 (3) | 0.66984 (12) | 0.0470 (5) | |
N1 | 0.41920 (5) | 0.7349 (3) | 0.42338 (15) | 0.0382 (4) | |
N2 | 0.26157 (4) | 0.5178 (2) | 0.50392 (14) | 0.0309 (4) | |
H2N | 0.2601 (6) | 0.555 (3) | 0.4374 (19) | 0.037* | |
N3 | 0.23060 (4) | 0.4687 (2) | 0.54236 (14) | 0.0329 (4) | |
N4 | 0.06636 (4) | 0.2626 (3) | 0.54414 (14) | 0.0385 (5) | |
C1 | 0.35196 (5) | 0.6469 (3) | 0.60129 (16) | 0.0360 (5) | |
H1 | 0.3497 | 0.6546 | 0.6750 | 0.043* | |
C2 | 0.38313 (5) | 0.6981 (3) | 0.56723 (17) | 0.0376 (5) | |
H2 | 0.4023 | 0.7423 | 0.6165 | 0.045* | |
C3 | 0.38577 (5) | 0.6834 (3) | 0.45998 (16) | 0.0317 (4) | |
C4 | 0.35855 (5) | 0.6218 (3) | 0.38607 (16) | 0.0355 (5) | |
H4 | 0.3611 | 0.6134 | 0.3125 | 0.043* | |
C5 | 0.32730 (5) | 0.5720 (3) | 0.42139 (16) | 0.0331 (5) | |
H5 | 0.3081 | 0.5294 | 0.3716 | 0.040* | |
C6 | 0.32385 (5) | 0.5841 (3) | 0.52888 (15) | 0.0286 (4) | |
C7 | 0.29128 (5) | 0.5290 (3) | 0.57364 (16) | 0.0308 (4) | |
C8 | 0.20420 (5) | 0.4474 (3) | 0.46932 (17) | 0.0330 (4) | |
H8 | 0.2075 | 0.4627 | 0.3968 | 0.040* | |
C9 | 0.16922 (5) | 0.4008 (3) | 0.49284 (16) | 0.0313 (4) | |
C10 | 0.16034 (5) | 0.3932 (3) | 0.59596 (16) | 0.0324 (5) | |
H10 | 0.1778 | 0.4189 | 0.6553 | 0.039* | |
C11 | 0.12662 (5) | 0.3491 (3) | 0.61358 (16) | 0.0327 (5) | |
H11 | 0.1213 | 0.3454 | 0.6847 | 0.039* | |
C12 | 0.09998 (5) | 0.3094 (3) | 0.52795 (16) | 0.0326 (5) | |
C13 | 0.10887 (5) | 0.3192 (3) | 0.42407 (17) | 0.0371 (5) | |
H13 | 0.0915 | 0.2945 | 0.3644 | 0.044* | |
C14 | 0.14265 (6) | 0.3645 (3) | 0.40804 (17) | 0.0373 (5) | |
H14 | 0.1480 | 0.3711 | 0.3370 | 0.045* | |
C15 | 0.05774 (6) | 0.2167 (3) | 0.64950 (17) | 0.0387 (5) | |
H15A | 0.0788 | 0.1621 | 0.6922 | 0.046* | |
H15B | 0.0388 | 0.1253 | 0.6410 | 0.046* | |
C16 | 0.04582 (6) | 0.3745 (4) | 0.7111 (2) | 0.0502 (6) | |
H16A | 0.0392 | 0.3322 | 0.7789 | 0.075* | |
H16B | 0.0255 | 0.4321 | 0.6686 | 0.075* | |
H16C | 0.0651 | 0.4613 | 0.7256 | 0.075* | |
C17 | 0.03658 (6) | 0.2743 (4) | 0.45771 (18) | 0.0449 (6) | |
H17A | 0.0415 | 0.3697 | 0.4073 | 0.054* | |
H17B | 0.0152 | 0.3095 | 0.4884 | 0.054* | |
C18 | 0.02924 (7) | 0.1007 (4) | 0.3964 (2) | 0.0595 (8) | |
H18A | 0.0493 | 0.0714 | 0.3595 | 0.089* | |
H18B | 0.0080 | 0.1144 | 0.3438 | 0.089* | |
H18C | 0.0257 | 0.0040 | 0.4463 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0535 (10) | 0.0650 (12) | 0.0311 (8) | 0.0156 (9) | 0.0143 (7) | 0.0043 (9) |
O1 | 0.0315 (8) | 0.0661 (12) | 0.0534 (10) | −0.0138 (8) | 0.0055 (7) | 0.0024 (9) |
O2 | 0.0483 (10) | 0.0704 (13) | 0.0443 (9) | −0.0106 (9) | 0.0216 (8) | 0.0001 (9) |
O3 | 0.0312 (8) | 0.0813 (13) | 0.0286 (7) | −0.0081 (8) | 0.0043 (6) | 0.0116 (8) |
N1 | 0.0316 (9) | 0.0399 (11) | 0.0443 (10) | −0.0039 (8) | 0.0098 (8) | 0.0046 (9) |
N2 | 0.0241 (8) | 0.0398 (10) | 0.0297 (8) | −0.0028 (7) | 0.0063 (7) | 0.0027 (8) |
N3 | 0.0241 (8) | 0.0379 (10) | 0.0376 (9) | −0.0030 (7) | 0.0072 (7) | 0.0018 (8) |
N4 | 0.0248 (8) | 0.0575 (13) | 0.0325 (9) | −0.0085 (8) | 0.0011 (7) | 0.0024 (9) |
C1 | 0.0307 (10) | 0.0519 (14) | 0.0248 (9) | −0.0055 (10) | 0.0017 (8) | 0.0008 (9) |
C2 | 0.0286 (10) | 0.0512 (14) | 0.0317 (10) | −0.0083 (10) | 0.0002 (8) | −0.0005 (10) |
C3 | 0.0261 (9) | 0.0335 (11) | 0.0359 (10) | −0.0018 (8) | 0.0062 (8) | 0.0034 (9) |
C4 | 0.0333 (11) | 0.0469 (13) | 0.0270 (10) | −0.0019 (9) | 0.0071 (8) | −0.0027 (9) |
C5 | 0.0282 (10) | 0.0419 (12) | 0.0287 (10) | −0.0041 (9) | 0.0023 (8) | −0.0033 (9) |
C6 | 0.0258 (9) | 0.0313 (10) | 0.0290 (9) | −0.0006 (8) | 0.0049 (8) | 0.0010 (8) |
C7 | 0.0287 (10) | 0.0354 (11) | 0.0289 (10) | −0.0029 (8) | 0.0061 (8) | 0.0009 (8) |
C8 | 0.0294 (10) | 0.0361 (11) | 0.0343 (10) | −0.0021 (9) | 0.0075 (8) | 0.0009 (9) |
C9 | 0.0249 (9) | 0.0347 (11) | 0.0340 (10) | −0.0024 (8) | 0.0028 (8) | 0.0010 (9) |
C10 | 0.0258 (9) | 0.0377 (11) | 0.0322 (10) | −0.0012 (8) | −0.0006 (8) | −0.0009 (9) |
C11 | 0.0263 (10) | 0.0415 (12) | 0.0299 (10) | −0.0007 (9) | 0.0027 (8) | 0.0032 (9) |
C12 | 0.0257 (9) | 0.0379 (11) | 0.0339 (10) | −0.0035 (8) | 0.0028 (8) | 0.0025 (9) |
C13 | 0.0291 (10) | 0.0489 (13) | 0.0314 (10) | −0.0071 (9) | −0.0023 (8) | 0.0022 (10) |
C14 | 0.0338 (11) | 0.0466 (13) | 0.0314 (10) | −0.0067 (10) | 0.0047 (9) | −0.0001 (9) |
C15 | 0.0280 (10) | 0.0515 (14) | 0.0363 (11) | −0.0080 (10) | 0.0039 (8) | 0.0067 (10) |
C16 | 0.0405 (13) | 0.0680 (18) | 0.0436 (13) | 0.0061 (12) | 0.0114 (11) | 0.0064 (13) |
C17 | 0.0287 (10) | 0.0637 (16) | 0.0407 (12) | −0.0069 (11) | −0.0006 (9) | 0.0075 (11) |
C18 | 0.0498 (15) | 0.080 (2) | 0.0464 (14) | −0.0243 (14) | −0.0024 (12) | −0.0023 (14) |
O4—H4A | 0.85 (3) | C8—C9 | 1.456 (3) |
O4—H4B | 0.83 (4) | C8—H8 | 0.9500 |
O1—N1 | 1.225 (2) | C9—C10 | 1.394 (3) |
O2—N1 | 1.228 (2) | C9—C14 | 1.395 (3) |
O3—C7 | 1.232 (2) | C10—C11 | 1.382 (3) |
N1—C3 | 1.473 (3) | C10—H10 | 0.9500 |
N2—C7 | 1.339 (2) | C11—C12 | 1.409 (3) |
N2—N3 | 1.394 (2) | C11—H11 | 0.9500 |
N2—H2N | 0.88 (2) | C12—C13 | 1.404 (3) |
N3—C8 | 1.278 (3) | C13—C14 | 1.380 (3) |
N4—C12 | 1.378 (3) | C13—H13 | 0.9500 |
N4—C15 | 1.457 (3) | C14—H14 | 0.9500 |
N4—C17 | 1.465 (3) | C15—C16 | 1.517 (4) |
C1—C2 | 1.380 (3) | C15—H15A | 0.9900 |
C1—C6 | 1.391 (3) | C15—H15B | 0.9900 |
C1—H1 | 0.9500 | C16—H16A | 0.9800 |
C2—C3 | 1.377 (3) | C16—H16B | 0.9800 |
C2—H2 | 0.9500 | C16—H16C | 0.9800 |
C3—C4 | 1.376 (3) | C17—C18 | 1.514 (4) |
C4—C5 | 1.387 (3) | C17—H17A | 0.9900 |
C4—H4 | 0.9500 | C17—H17B | 0.9900 |
C5—C6 | 1.386 (3) | C18—H18A | 0.9800 |
C5—H5 | 0.9500 | C18—H18B | 0.9800 |
C6—C7 | 1.499 (3) | C18—H18C | 0.9800 |
H4A—O4—H4B | 111 (3) | C11—C10—H10 | 119.4 |
O1—N1—O2 | 123.34 (19) | C9—C10—H10 | 119.4 |
O1—N1—C3 | 118.57 (18) | C10—C11—C12 | 121.19 (19) |
O2—N1—C3 | 118.09 (18) | C10—C11—H11 | 119.4 |
C7—N2—N3 | 118.26 (17) | C12—C11—H11 | 119.4 |
C7—N2—H2N | 122.7 (15) | N4—C12—C13 | 120.59 (18) |
N3—N2—H2N | 118.4 (15) | N4—C12—C11 | 121.96 (19) |
C8—N3—N2 | 113.98 (17) | C13—C12—C11 | 117.45 (18) |
C12—N4—C15 | 122.27 (17) | C14—C13—C12 | 120.52 (19) |
C12—N4—C17 | 121.30 (18) | C14—C13—H13 | 119.7 |
C15—N4—C17 | 116.15 (17) | C12—C13—H13 | 119.7 |
C2—C1—C6 | 120.75 (19) | C13—C14—C9 | 122.1 (2) |
C2—C1—H1 | 119.6 | C13—C14—H14 | 118.9 |
C6—C1—H1 | 119.6 | C9—C14—H14 | 118.9 |
C3—C2—C1 | 118.25 (19) | N4—C15—C16 | 114.2 (2) |
C3—C2—H2 | 120.9 | N4—C15—H15A | 108.7 |
C1—C2—H2 | 120.9 | C16—C15—H15A | 108.7 |
C4—C3—C2 | 122.61 (19) | N4—C15—H15B | 108.7 |
C4—C3—N1 | 118.86 (19) | C16—C15—H15B | 108.7 |
C2—C3—N1 | 118.52 (18) | H15A—C15—H15B | 107.6 |
C3—C4—C5 | 118.47 (19) | C15—C16—H16A | 109.5 |
C3—C4—H4 | 120.8 | C15—C16—H16B | 109.5 |
C5—C4—H4 | 120.8 | H16A—C16—H16B | 109.5 |
C6—C5—C4 | 120.35 (18) | C15—C16—H16C | 109.5 |
C6—C5—H5 | 119.8 | H16A—C16—H16C | 109.5 |
C4—C5—H5 | 119.8 | H16B—C16—H16C | 109.5 |
C5—C6—C1 | 119.55 (18) | N4—C17—C18 | 113.5 (2) |
C5—C6—C7 | 123.55 (17) | N4—C17—H17A | 108.9 |
C1—C6—C7 | 116.88 (18) | C18—C17—H17A | 108.9 |
O3—C7—N2 | 122.99 (18) | N4—C17—H17B | 108.9 |
O3—C7—C6 | 120.63 (17) | C18—C17—H17B | 108.9 |
N2—C7—C6 | 116.38 (17) | H17A—C17—H17B | 107.7 |
N3—C8—C9 | 122.62 (19) | C17—C18—H18A | 109.5 |
N3—C8—H8 | 118.7 | C17—C18—H18B | 109.5 |
C9—C8—H8 | 118.7 | H18A—C18—H18B | 109.5 |
C10—C9—C14 | 117.46 (18) | C17—C18—H18C | 109.5 |
C10—C9—C8 | 123.73 (18) | H18A—C18—H18C | 109.5 |
C14—C9—C8 | 118.80 (19) | H18B—C18—H18C | 109.5 |
C11—C10—C9 | 121.26 (18) | ||
C7—N2—N3—C8 | −174.7 (2) | N2—N3—C8—C9 | −178.3 (2) |
C6—C1—C2—C3 | −0.7 (4) | N3—C8—C9—C10 | 6.9 (3) |
C1—C2—C3—C4 | 0.6 (4) | N3—C8—C9—C14 | −174.4 (2) |
C1—C2—C3—N1 | −178.9 (2) | C14—C9—C10—C11 | 0.8 (3) |
O1—N1—C3—C4 | 176.0 (2) | C8—C9—C10—C11 | 179.6 (2) |
O2—N1—C3—C4 | −4.6 (3) | C9—C10—C11—C12 | 0.2 (3) |
O1—N1—C3—C2 | −4.4 (3) | C15—N4—C12—C13 | 167.7 (2) |
O2—N1—C3—C2 | 175.0 (2) | C17—N4—C12—C13 | −18.6 (3) |
C2—C3—C4—C5 | −0.2 (4) | C15—N4—C12—C11 | −12.3 (3) |
N1—C3—C4—C5 | 179.4 (2) | C17—N4—C12—C11 | 161.3 (2) |
C3—C4—C5—C6 | −0.2 (3) | C10—C11—C12—N4 | 179.1 (2) |
C4—C5—C6—C1 | 0.1 (3) | C10—C11—C12—C13 | −1.0 (3) |
C4—C5—C6—C7 | −178.5 (2) | N4—C12—C13—C14 | −179.4 (2) |
C2—C1—C6—C5 | 0.3 (3) | C11—C12—C13—C14 | 0.6 (3) |
C2—C1—C6—C7 | 179.1 (2) | C12—C13—C14—C9 | 0.5 (4) |
N3—N2—C7—O3 | 0.1 (3) | C10—C9—C14—C13 | −1.2 (3) |
N3—N2—C7—C6 | −179.4 (2) | C8—C9—C14—C13 | 179.9 (2) |
C5—C6—C7—O3 | 160.9 (2) | C12—N4—C15—C16 | 91.3 (3) |
C1—C6—C7—O3 | −17.8 (3) | C17—N4—C15—C16 | −82.7 (3) |
C5—C6—C7—N2 | −19.6 (3) | C12—N4—C17—C18 | 93.1 (3) |
C1—C6—C7—N2 | 161.7 (2) | C15—N4—C17—C18 | −92.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4B···O3i | 0.83 (4) | 2.23 (4) | 3.009 (3) | 156 (3) |
N2—H2N···O4 | 0.88 (2) | 2.00 (2) | 2.861 (2) | 165 (2) |
O4—H4A···O3ii | 0.85 (3) | 2.06 (4) | 2.823 (2) | 149 (3) |
O4—H4A···N3ii | 0.85 (3) | 2.57 (3) | 3.250 (3) | 138 (3) |
C5—H5···O3ii | 0.95 | 2.54 | 3.308 (2) | 138 |
C8—H8···O4 | 0.95 | 2.50 | 3.270 (3) | 138 |
C13—H13···O2iii | 0.95 | 2.51 | 3.350 (3) | 148 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x, −y+1, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H20N4O3·H2O |
Mr | 358.40 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 173 |
a, b, c (Å) | 38.3142 (12), 7.4563 (3), 12.6332 (5) |
β (°) | 98.215 (2) |
V (Å3) | 3572.0 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.08 × 0.06 × 0.04 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.992, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5710, 4048, 3182 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.138, 1.11 |
No. of reflections | 4048 |
No. of parameters | 246 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.19 |
Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4B···O3i | 0.83 (4) | 2.23 (4) | 3.009 (3) | 156 (3) |
N2—H2N···O4 | 0.88 (2) | 2.00 (2) | 2.861 (2) | 165 (2) |
O4—H4A···O3ii | 0.85 (3) | 2.06 (4) | 2.823 (2) | 149 (3) |
O4—H4A···N3ii | 0.85 (3) | 2.57 (3) | 3.250 (3) | 138 (3) |
C5—H5···O3ii | 0.95 | 2.54 | 3.308 (2) | 138 |
C8—H8···O4 | 0.95 | 2.50 | 3.270 (3) | 138 |
C13—H13···O2iii | 0.95 | 2.51 | 3.350 (3) | 148 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x, −y+1, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2. |
Acknowledgements
HLS is grateful to the Institute of Chemistry, University of the Punjab, for financial support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The chemistry of hydrazones is being investigated continuously due to their excellent coordinating capability (Rodríguez-Argüelles et al., 2004) and biological activities (Zia-ur-Rehman et al., 2009; Galal et al., 2009; Bordoloi et al., 2009). In continuation of our studies on the synthesis of various heterocyclic compounds (Ahmad et al., 2010), the title compound, (I), has been synthesized and its crystal structure determined by X-ray crystallographic method which is presented in this article.
In the the title compound (Fig. 1) the bond distances and angles agree with the corresponding bond distances and angles reported in closely related compounds (Fun et al., 2008; Bessy et al., 2006). The benzene rings in (I) are linked through a methylidenehydrazide fragment, C6/C7/N2/N3/C8, which is fully extended with torsion angles C6–C7–N2–N3, C7–N2–N3\ C8 and N2–N3═C8–C9 179.4 (2), 174.7 (2) and 178.3 (2)°, respectively. The dihedral angle between the two benzene rings is 7.01 (8)°. In the crystal structure, the water of hydration is extensively involved in hydrogen bonding. Thus, intermolecular O—H···O, N—H···O and O—H···N hydrogen bonds link the components of the structure into a two-dimensional network and additional stabilization is provided by weak intermolecular C—H···O hydrogen bonds; details have been provided in Table. 1. and Fig. 2.