The organic molecule of the title compound, C
24H
22N
4O
6·2H
2O, is centrosymmetric. The dihedral angle between the two benzene rings is 3.25 (7)°. The structure is stabilized by intramolecular O—H
O, and intermolecular N—H
O and O—H
O hydrogen bonds, forming an intricate three-dimensional network.
Supporting information
CCDC reference: 643622
Key indicators
- Single-crystal X-ray study
- T = 298 K
- R factor = 0.055
- wR factor = 0.133
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
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Compound (I) was synthesized by the reaction of terephthalohydrazide (5 mmol)
with 2-hydroxy-3-methoxybenzaldehyde (10 mmol). Single crystals of (I)
suitable for X-ray diffraction were obtained by slow evaporation of an ethanol
solution.
All H atoms attached to C atoms and N atom were fixed geometrically and treated
as riding with C—H = 0.93 Å (aromatic), C—H = 0.96 Å (methylaromatic)
and N—H = 0.86 Å with Uiso(H) = 1.2 or 1.5Ueq (C or N).
H atoms of water molecule were located in difference Fourier maps and included
in the subsequent refinement using restraints [O—H = 0.85 (1) Å and H···H =
1.39 (2) Å] with Uiso(H) = 1.5Ueq(O).
Data collection: SMART (Siemens, 1996); cell refinement: SMART or SAINT? (Siemens, 1996); data reduction: SMART or SAINT? (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
N2,
N2'-Bis(2-hydroxy-3-
methoxybenzylidene)terephthalohydrazide dihydrate
top
Crystal data top
C24H22N4O6·2H2O | F(000) = 524 |
Mr = 498.49 | Dx = 1.398 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1112 reflections |
a = 7.2854 (12) Å | θ = 2.9–27.6° |
b = 25.711 (2) Å | µ = 0.11 mm−1 |
c = 6.4780 (11) Å | T = 298 K |
β = 102.613 (2)° | Block, colourless |
V = 1184.1 (3) Å3 | 0.28 × 0.17 × 0.14 mm |
Z = 2 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2052 independent reflections |
Radiation source: fine-focus sealed tube | 1003 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.971, Tmax = 0.985 | k = −30→28 |
5724 measured reflections | l = −7→7 |
Refinement top
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0526P)2] where P = (Fo2 + 2Fc2)/3 |
2052 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Crystal data top
C24H22N4O6·2H2O | V = 1184.1 (3) Å3 |
Mr = 498.49 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.2854 (12) Å | µ = 0.11 mm−1 |
b = 25.711 (2) Å | T = 298 K |
c = 6.4780 (11) Å | 0.28 × 0.17 × 0.14 mm |
β = 102.613 (2)° | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2052 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1003 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.985 | Rint = 0.067 |
5724 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.21 e Å−3 |
2052 reflections | Δρmin = −0.23 e Å−3 |
163 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | −0.0134 (4) | 0.57438 (9) | −0.0098 (4) | 0.0298 (7) | |
H1 | −0.1305 | 0.5725 | −0.0711 | 0.036* | |
N2 | 0.0440 (4) | 0.60098 (9) | 0.1775 (4) | 0.0299 (7) | |
O1 | 0.2850 (3) | 0.55158 (9) | −0.0035 (4) | 0.0475 (7) | |
O2 | 0.3017 (3) | 0.63702 (8) | 0.4869 (4) | 0.0415 (7) | |
H2 | 0.2621 | 0.6214 | 0.3757 | 0.062* | |
O3 | 0.3871 (3) | 0.68755 (8) | 0.8377 (4) | 0.0427 (7) | |
O4 | 0.5917 (3) | 0.58503 (9) | 0.8496 (4) | 0.0513 (7) | |
H13 | 0.5422 | 0.6126 | 0.7893 | 0.077* | |
H14 | 0.5073 | 0.5706 | 0.9022 | 0.077* | |
C1 | 0.1207 (5) | 0.55120 (12) | −0.0950 (5) | 0.0306 (9) | |
C2 | 0.0522 (5) | 0.52507 (11) | −0.3037 (5) | 0.0286 (8) | |
C3 | 0.1867 (5) | 0.50515 (12) | −0.4035 (6) | 0.0367 (9) | |
H3 | 0.3134 | 0.5085 | −0.3394 | 0.044* | |
C4 | 0.1356 (5) | 0.48038 (12) | −0.5968 (5) | 0.0343 (9) | |
H4 | 0.2283 | 0.4672 | −0.6610 | 0.041* | |
C5 | −0.0843 (5) | 0.62087 (12) | 0.2609 (5) | 0.0354 (9) | |
H5 | −0.2104 | 0.6168 | 0.1955 | 0.042* | |
C6 | −0.0321 (5) | 0.64951 (12) | 0.4562 (5) | 0.0282 (8) | |
C7 | 0.1552 (5) | 0.65613 (11) | 0.5602 (5) | 0.0284 (8) | |
C8 | 0.1981 (5) | 0.68380 (11) | 0.7509 (5) | 0.0302 (8) | |
C9 | 0.0568 (5) | 0.70477 (12) | 0.8354 (6) | 0.0378 (9) | |
H9 | 0.0861 | 0.7234 | 0.9614 | 0.045* | |
C10 | −0.1276 (5) | 0.69803 (13) | 0.7330 (6) | 0.0402 (9) | |
H10 | −0.2226 | 0.7122 | 0.7908 | 0.048* | |
C11 | −0.1739 (5) | 0.67075 (12) | 0.5469 (6) | 0.0369 (9) | |
H11 | −0.2996 | 0.6663 | 0.4804 | 0.044* | |
C12 | 0.4402 (6) | 0.71070 (15) | 1.0399 (6) | 0.0602 (12) | |
H12A | 0.3977 | 0.7461 | 1.0325 | 0.090* | |
H12B | 0.5747 | 0.7098 | 1.0860 | 0.090* | |
H12C | 0.3844 | 0.6918 | 1.1385 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0271 (16) | 0.0405 (17) | 0.0199 (17) | −0.0041 (13) | 0.0008 (13) | −0.0077 (14) |
N2 | 0.0338 (18) | 0.0308 (16) | 0.0243 (18) | −0.0018 (13) | 0.0046 (15) | −0.0073 (13) |
O1 | 0.0263 (16) | 0.0760 (19) | 0.0380 (17) | −0.0021 (13) | 0.0022 (14) | −0.0161 (14) |
O2 | 0.0286 (15) | 0.0549 (15) | 0.0391 (16) | 0.0065 (12) | 0.0029 (13) | −0.0126 (12) |
O3 | 0.0401 (16) | 0.0468 (15) | 0.0379 (16) | −0.0051 (12) | 0.0013 (13) | −0.0162 (13) |
O4 | 0.0289 (15) | 0.0623 (16) | 0.0606 (19) | 0.0045 (12) | 0.0054 (14) | 0.0005 (15) |
C1 | 0.036 (2) | 0.032 (2) | 0.025 (2) | −0.0032 (17) | 0.0081 (19) | −0.0007 (17) |
C2 | 0.031 (2) | 0.0276 (18) | 0.027 (2) | −0.0023 (15) | 0.0053 (18) | −0.0008 (15) |
C3 | 0.026 (2) | 0.048 (2) | 0.036 (2) | −0.0066 (17) | 0.0047 (18) | −0.0127 (19) |
C4 | 0.032 (2) | 0.042 (2) | 0.030 (2) | −0.0017 (16) | 0.0083 (19) | −0.0098 (18) |
C5 | 0.032 (2) | 0.040 (2) | 0.033 (2) | 0.0029 (17) | 0.0032 (18) | −0.0064 (18) |
C6 | 0.030 (2) | 0.0297 (19) | 0.024 (2) | 0.0040 (15) | 0.0028 (18) | −0.0010 (16) |
C7 | 0.035 (2) | 0.0237 (18) | 0.027 (2) | −0.0002 (16) | 0.0092 (19) | 0.0016 (16) |
C8 | 0.033 (2) | 0.0237 (18) | 0.031 (2) | −0.0014 (16) | 0.0009 (18) | 0.0011 (16) |
C9 | 0.047 (3) | 0.039 (2) | 0.027 (2) | −0.0007 (18) | 0.006 (2) | −0.0081 (17) |
C10 | 0.046 (3) | 0.047 (2) | 0.030 (2) | 0.0123 (18) | 0.013 (2) | −0.0019 (19) |
C11 | 0.031 (2) | 0.043 (2) | 0.038 (2) | 0.0076 (17) | 0.0081 (19) | −0.0022 (18) |
C12 | 0.059 (3) | 0.083 (3) | 0.032 (3) | −0.012 (2) | −0.004 (2) | −0.022 (2) |
Geometric parameters (Å, º) top
N1—C1 | 1.360 (4) | C4—C2i | 1.387 (4) |
N1—N2 | 1.376 (3) | C4—H4 | 0.9300 |
N1—H1 | 0.8600 | C5—C6 | 1.441 (4) |
N2—C5 | 1.283 (4) | C5—H5 | 0.9300 |
O1—C1 | 1.214 (4) | C6—C7 | 1.394 (4) |
O2—C7 | 1.352 (3) | C6—C11 | 1.406 (4) |
O2—H2 | 0.8200 | C7—C8 | 1.400 (4) |
O3—C8 | 1.372 (4) | C8—C9 | 1.377 (4) |
O3—C12 | 1.414 (4) | C9—C10 | 1.373 (5) |
O4—H13 | 0.8500 | C9—H9 | 0.9300 |
O4—H14 | 0.8500 | C10—C11 | 1.372 (5) |
C1—C2 | 1.495 (5) | C10—H10 | 0.9300 |
C2—C3 | 1.384 (4) | C11—H11 | 0.9300 |
C2—C4i | 1.387 (4) | C12—H12A | 0.9600 |
C3—C4 | 1.381 (4) | C12—H12B | 0.9600 |
C3—H3 | 0.9300 | C12—H12C | 0.9600 |
| | | |
C1—N1—N2 | 118.0 (3) | C7—C6—C5 | 122.0 (3) |
C1—N1—H1 | 121.0 | C11—C6—C5 | 119.2 (3) |
N2—N1—H1 | 121.0 | O2—C7—C6 | 123.4 (3) |
C5—N2—N1 | 117.4 (3) | O2—C7—C8 | 117.0 (3) |
C7—O2—H2 | 109.5 | C6—C7—C8 | 119.7 (3) |
C8—O3—C12 | 117.2 (3) | O3—C8—C9 | 125.4 (3) |
H13—O4—H14 | 106.0 | O3—C8—C7 | 114.1 (3) |
O1—C1—N1 | 121.2 (3) | C9—C8—C7 | 120.5 (3) |
O1—C1—C2 | 122.9 (3) | C10—C9—C8 | 119.7 (3) |
N1—C1—C2 | 115.9 (3) | C10—C9—H9 | 120.1 |
C3—C2—C4i | 118.2 (3) | C8—C9—H9 | 120.1 |
C3—C2—C1 | 117.3 (3) | C11—C10—C9 | 121.1 (3) |
C4i—C2—C1 | 124.5 (3) | C11—C10—H10 | 119.5 |
C4—C3—C2 | 121.1 (3) | C9—C10—H10 | 119.5 |
C4—C3—H3 | 119.5 | C10—C11—C6 | 120.3 (3) |
C2—C3—H3 | 119.5 | C10—C11—H11 | 119.9 |
C3—C4—C2i | 120.7 (3) | C6—C11—H11 | 119.9 |
C3—C4—H4 | 119.6 | O3—C12—H12A | 109.5 |
C2i—C4—H4 | 119.6 | O3—C12—H12B | 109.5 |
N2—C5—C6 | 119.8 (3) | H12A—C12—H12B | 109.5 |
N2—C5—H5 | 120.1 | O3—C12—H12C | 109.5 |
C6—C5—H5 | 120.1 | H12A—C12—H12C | 109.5 |
C7—C6—C11 | 118.8 (3) | H12B—C12—H12C | 109.5 |
| | | |
C1—N1—N2—C5 | −177.2 (3) | C11—C6—C7—C8 | −0.3 (4) |
N2—N1—C1—O1 | 3.8 (4) | C5—C6—C7—C8 | −179.3 (3) |
N2—N1—C1—C2 | −177.0 (2) | C12—O3—C8—C9 | 6.1 (5) |
O1—C1—C2—C3 | −6.5 (5) | C12—O3—C8—C7 | −174.2 (3) |
N1—C1—C2—C3 | 174.4 (3) | O2—C7—C8—O3 | −0.1 (4) |
O1—C1—C2—C4i | 173.6 (3) | C6—C7—C8—O3 | 179.9 (3) |
N1—C1—C2—C4i | −5.5 (4) | O2—C7—C8—C9 | 179.6 (3) |
C4i—C2—C3—C4 | −0.1 (5) | C6—C7—C8—C9 | −0.4 (5) |
C1—C2—C3—C4 | 180.0 (3) | O3—C8—C9—C10 | −179.7 (3) |
C2—C3—C4—C2i | 0.1 (5) | C7—C8—C9—C10 | 0.7 (5) |
N1—N2—C5—C6 | −179.5 (3) | C8—C9—C10—C11 | −0.1 (5) |
N2—C5—C6—C7 | −0.5 (5) | C9—C10—C11—C6 | −0.6 (5) |
N2—C5—C6—C11 | −179.5 (3) | C7—C6—C11—C10 | 0.8 (5) |
C11—C6—C7—O2 | 179.7 (3) | C5—C6—C11—C10 | 179.8 (3) |
C5—C6—C7—O2 | 0.7 (5) | | |
Symmetry code: (i) −x, −y+1, −z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4ii | 0.86 | 2.00 | 2.835 (3) | 163 |
O4—H14···O1iii | 0.85 | 1.92 | 2.751 (3) | 167 |
O2—H2···N2 | 0.82 | 1.89 | 2.599 (4) | 145 |
O4—H13···O3 | 0.85 | 2.29 | 3.021 (3) | 144 |
O4—H13···O2 | 0.85 | 2.41 | 3.099 (3) | 139 |
Symmetry codes: (ii) x−1, y, z−1; (iii) x, y, z+1. |
Experimental details
Crystal data |
Chemical formula | C24H22N4O6·2H2O |
Mr | 498.49 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 7.2854 (12), 25.711 (2), 6.4780 (11) |
β (°) | 102.613 (2) |
V (Å3) | 1184.1 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.28 × 0.17 × 0.14 |
|
Data collection |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.971, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5724, 2052, 1003 |
Rint | 0.067 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.133, 1.00 |
No. of reflections | 2052 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.23 |
Selected geometric parameters (Å, º) topN1—C1 | 1.360 (4) | N2—C5 | 1.283 (4) |
N1—N2 | 1.376 (3) | O1—C1 | 1.214 (4) |
| | | |
C1—N1—N2 | 118.0 (3) | C5—N2—N1 | 117.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.86 | 2.00 | 2.835 (3) | 162.6 |
O4—H14···O1ii | 0.85 | 1.92 | 2.751 (3) | 167.2 |
O2—H2···N2 | 0.82 | 1.89 | 2.599 (4) | 144.7 |
O4—H13···O3 | 0.85 | 2.29 | 3.021 (3) | 144.1 |
O4—H13···O2 | 0.85 | 2.41 | 3.099 (3) | 138.7 |
Symmetry codes: (i) x−1, y, z−1; (ii) x, y, z+1. |
Recently, we have reported some organotin(IV) complexes with Schiff base of o-vanillin-2-thiophenoylhydrazone (Yin & Chen, 2006). As an extension of our work on the structural characterization of Schiff base compounds, the title compound, (I), is reported here (Fig. 1).
In Fig. 1, it can be viewed as a centrosymmetric configuration, where one half of the molecule comprises the crystallographic asymmetric unit and the other half is generated by an inversion centre. In the compound, the N2═C5 bond length of 1.283 (4) Å (Table 1) conforms to the value for a double bond, while the N1—C1 bond [1.360 (4) Å] and N1—N2 bond [1.376 (3) Å] are intermediate between a double bond and a single bond because of conjugation effects in the molecule. The two benzene rings make a dihedral angle of 3.2 °.
The occurrence O—H···O and N—H···–O hydrogen bonds (Table 2) results in the formation of an intricated three dimensionnal network (Fig. 2).