




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680800130X/su2040sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S160053680800130X/su2040Isup2.hkl |
CCDC reference: 677612
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.131
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was obtained by stirring of 4-dimethylaminobenzaldehyde (0.1 mmol, 14.9 mg) and 3-hydroxybenzoic acid hydrazide (0.1 mmol, 15.2 mg) in a methanol solution (10 ml) at room temperature. Yellow block-shaped single crystals suitable for X-ray diffraction were formed from the solution after seven days.
H3A was located from a difference Fourier map and refined with the N–H distance restrained to 0.90 (1) Å, and Uiso(H) = 0.08 Å2. Other H atoms were positioned geometrically (C–H = 0.93–0.96Å and O–H = 0.82 Å) and treated as riding atoms, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O and methyl-C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Version 5.1; Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C16H17N3O2 | F(000) = 600 |
Mr = 283.33 | Dx = 1.329 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4593 reflections |
a = 13.397 (3) Å | θ = 2.5–27.7° |
b = 9.663 (2) Å | µ = 0.09 mm−1 |
c = 11.183 (2) Å | T = 298 K |
β = 101.97 (3)° | Block, yellow |
V = 1416.2 (5) Å3 | 0.28 × 0.27 × 0.27 mm |
Z = 4 |
Bruker SMART APEX area-detector diffractometer | 3094 independent reflections |
Radiation source: fine-focus sealed tube | 2579 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 27.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→17 |
Tmin = 0.975, Tmax = 0.976 | k = −12→12 |
11531 measured reflections | l = −14→14 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0773P)2 + 0.1729P] where P = (Fo2 + 2Fc2)/3 |
3094 reflections | (Δ/σ)max < 0.001 |
196 parameters | Δρmax = 0.21 e Å−3 |
1 restraint | Δρmin = −0.29 e Å−3 |
C16H17N3O2 | V = 1416.2 (5) Å3 |
Mr = 283.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.397 (3) Å | µ = 0.09 mm−1 |
b = 9.663 (2) Å | T = 298 K |
c = 11.183 (2) Å | 0.28 × 0.27 × 0.27 mm |
β = 101.97 (3)° |
Bruker SMART APEX area-detector diffractometer | 3094 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2579 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.976 | Rint = 0.021 |
11531 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 1 restraint |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.21 e Å−3 |
3094 reflections | Δρmin = −0.29 e Å−3 |
196 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 | ||
O1 | 0.51231 (8) | 0.27675 (11) | 0.29293 (9) | 0.0574 (3) | |
O2 | 0.28657 (7) | 0.69755 (10) | 0.22473 (9) | 0.0486 (3) | |
H2 | 0.3315 | 0.7006 | 0.1849 | 0.073* | |
N1 | 0.97117 (10) | −0.30631 (15) | 0.63913 (13) | 0.0654 (4) | |
N2 | 0.60441 (8) | 0.13189 (10) | 0.48763 (10) | 0.0416 (3) | |
N3 | 0.52359 (8) | 0.22033 (11) | 0.49046 (10) | 0.0420 (3) | |
C1 | 0.72192 (9) | −0.03254 (12) | 0.59700 (11) | 0.0379 (3) | |
C2 | 0.78863 (10) | −0.03161 (13) | 0.51647 (11) | 0.0430 (3) | |
H2A | 0.7774 | 0.0302 | 0.4513 | 0.052* | |
C3 | 0.87041 (10) | −0.11981 (14) | 0.53134 (12) | 0.0445 (3) | |
H3 | 0.9138 | −0.1157 | 0.4764 | 0.053* | |
C4 | 0.89036 (9) | −0.21613 (13) | 0.62715 (12) | 0.0425 (3) | |
C5 | 0.82405 (10) | −0.21577 (14) | 0.70911 (12) | 0.0456 (3) | |
H5 | 0.8352 | −0.2770 | 0.7747 | 0.055* | |
C6 | 0.74284 (10) | −0.12595 (14) | 0.69358 (11) | 0.0424 (3) | |
H6 | 0.7004 | −0.1277 | 0.7496 | 0.051* | |
C7 | 0.99119 (16) | −0.4061 (2) | 0.73523 (17) | 0.0793 (6) | |
H7A | 1.0129 | −0.3597 | 0.8121 | 0.119* | |
H7B | 1.0439 | −0.4679 | 0.7219 | 0.119* | |
H7C | 0.9302 | −0.4578 | 0.7363 | 0.119* | |
C8 | 1.04154 (15) | −0.2992 (2) | 0.5584 (2) | 0.0903 (7) | |
H8A | 1.0063 | −0.3194 | 0.4764 | 0.135* | |
H8B | 1.0952 | −0.3655 | 0.5835 | 0.135* | |
H8C | 1.0702 | −0.2079 | 0.5612 | 0.135* | |
C9 | 0.63422 (9) | 0.05897 (13) | 0.58348 (11) | 0.0411 (3) | |
H9 | 0.5988 | 0.0645 | 0.6466 | 0.049* | |
C10 | 0.48449 (9) | 0.29458 (12) | 0.38962 (12) | 0.0397 (3) | |
C11 | 0.40510 (9) | 0.39961 (12) | 0.40150 (11) | 0.0375 (3) | |
C12 | 0.38258 (9) | 0.49733 (12) | 0.30887 (11) | 0.0375 (3) | |
H12 | 0.4168 | 0.4954 | 0.2446 | 0.045* | |
C13 | 0.30939 (9) | 0.59770 (12) | 0.31174 (11) | 0.0380 (3) | |
C14 | 0.25681 (10) | 0.59887 (14) | 0.40629 (12) | 0.0453 (3) | |
H14 | 0.2067 | 0.6651 | 0.4080 | 0.054* | |
C15 | 0.27927 (11) | 0.50121 (16) | 0.49776 (13) | 0.0530 (4) | |
H15 | 0.2440 | 0.5021 | 0.5611 | 0.064* | |
C16 | 0.35350 (10) | 0.40181 (14) | 0.49689 (12) | 0.0469 (3) | |
H16 | 0.3686 | 0.3372 | 0.5596 | 0.056* | |
H3A | 0.5095 (14) | 0.2388 (19) | 0.5637 (11) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0646 (6) | 0.0592 (6) | 0.0572 (6) | 0.0197 (5) | 0.0327 (5) | 0.0044 (5) |
O2 | 0.0480 (5) | 0.0487 (5) | 0.0530 (6) | 0.0081 (4) | 0.0192 (4) | 0.0094 (4) |
N1 | 0.0552 (7) | 0.0751 (9) | 0.0698 (8) | 0.0289 (7) | 0.0219 (6) | 0.0220 (7) |
N2 | 0.0369 (5) | 0.0388 (6) | 0.0501 (6) | 0.0050 (4) | 0.0114 (4) | −0.0082 (4) |
N3 | 0.0380 (5) | 0.0417 (6) | 0.0485 (6) | 0.0072 (4) | 0.0137 (5) | −0.0065 (5) |
C1 | 0.0368 (6) | 0.0382 (6) | 0.0391 (6) | −0.0001 (5) | 0.0087 (5) | −0.0057 (5) |
C2 | 0.0452 (7) | 0.0451 (7) | 0.0400 (6) | 0.0056 (5) | 0.0115 (5) | 0.0069 (5) |
C3 | 0.0427 (7) | 0.0535 (8) | 0.0407 (7) | 0.0056 (5) | 0.0162 (5) | 0.0024 (5) |
C4 | 0.0388 (6) | 0.0447 (7) | 0.0432 (7) | 0.0046 (5) | 0.0067 (5) | 0.0001 (5) |
C5 | 0.0467 (7) | 0.0504 (7) | 0.0397 (7) | 0.0023 (6) | 0.0085 (5) | 0.0086 (5) |
C6 | 0.0428 (7) | 0.0499 (7) | 0.0373 (6) | −0.0026 (5) | 0.0149 (5) | −0.0027 (5) |
C7 | 0.0834 (12) | 0.0834 (13) | 0.0713 (11) | 0.0421 (10) | 0.0162 (9) | 0.0196 (9) |
C8 | 0.0656 (11) | 0.1028 (15) | 0.1139 (16) | 0.0410 (11) | 0.0449 (11) | 0.0305 (13) |
C9 | 0.0394 (6) | 0.0403 (6) | 0.0456 (7) | 0.0004 (5) | 0.0131 (5) | −0.0074 (5) |
C10 | 0.0359 (6) | 0.0369 (6) | 0.0497 (7) | 0.0000 (5) | 0.0165 (5) | −0.0046 (5) |
C11 | 0.0332 (6) | 0.0371 (6) | 0.0442 (7) | −0.0012 (5) | 0.0122 (5) | −0.0055 (5) |
C12 | 0.0352 (6) | 0.0394 (6) | 0.0412 (6) | −0.0024 (5) | 0.0156 (5) | −0.0044 (5) |
C13 | 0.0345 (6) | 0.0378 (6) | 0.0423 (6) | −0.0024 (5) | 0.0095 (5) | −0.0018 (5) |
C14 | 0.0393 (6) | 0.0472 (7) | 0.0530 (7) | 0.0094 (5) | 0.0182 (5) | −0.0002 (6) |
C15 | 0.0532 (8) | 0.0630 (9) | 0.0511 (8) | 0.0150 (6) | 0.0302 (6) | 0.0071 (6) |
C16 | 0.0486 (7) | 0.0502 (7) | 0.0464 (7) | 0.0102 (6) | 0.0199 (6) | 0.0079 (6) |
O1—C10 | 1.2267 (15) | C6—H6 | 0.9300 |
O2—C13 | 1.3593 (15) | C7—H7A | 0.9600 |
O2—H2 | 0.8200 | C7—H7B | 0.9600 |
N1—C4 | 1.3745 (17) | C7—H7C | 0.9600 |
N1—C7 | 1.427 (2) | C8—H8A | 0.9600 |
N1—C8 | 1.436 (2) | C8—H8B | 0.9600 |
N2—C9 | 1.2757 (16) | C8—H8C | 0.9600 |
N2—N3 | 1.3848 (14) | C9—H9 | 0.9300 |
N3—C10 | 1.3475 (17) | C10—C11 | 1.4958 (16) |
N3—H3A | 0.895 (9) | C11—C16 | 1.3864 (18) |
C1—C6 | 1.3907 (17) | C11—C12 | 1.3878 (17) |
C1—C2 | 1.3942 (17) | C12—C13 | 1.3842 (17) |
C1—C9 | 1.4531 (17) | C12—H12 | 0.9300 |
C2—C3 | 1.3706 (17) | C13—C14 | 1.3868 (17) |
C2—H2A | 0.9300 | C14—C15 | 1.3783 (19) |
C3—C4 | 1.4025 (18) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—C16 | 1.3841 (18) |
C4—C5 | 1.4025 (19) | C15—H15 | 0.9300 |
C5—C6 | 1.3744 (18) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | ||
C13—O2—H2 | 109.5 | H7B—C7—H7C | 109.5 |
C4—N1—C7 | 121.53 (13) | N1—C8—H8A | 109.5 |
C4—N1—C8 | 120.99 (13) | N1—C8—H8B | 109.5 |
C7—N1—C8 | 117.43 (13) | H8A—C8—H8B | 109.5 |
C9—N2—N3 | 115.57 (10) | N1—C8—H8C | 109.5 |
C10—N3—N2 | 118.66 (10) | H8A—C8—H8C | 109.5 |
C10—N3—H3A | 122.7 (12) | H8B—C8—H8C | 109.5 |
N2—N3—H3A | 117.2 (12) | N2—C9—C1 | 121.94 (11) |
C6—C1—C2 | 116.93 (11) | N2—C9—H9 | 119.0 |
C6—C1—C9 | 120.27 (11) | C1—C9—H9 | 119.0 |
C2—C1—C9 | 122.80 (11) | O1—C10—N3 | 121.76 (11) |
C3—C2—C1 | 121.39 (12) | O1—C10—C11 | 121.68 (12) |
C3—C2—H2A | 119.3 | N3—C10—C11 | 116.56 (10) |
C1—C2—H2A | 119.3 | C16—C11—C12 | 119.87 (11) |
C2—C3—C4 | 121.75 (11) | C16—C11—C10 | 123.77 (11) |
C2—C3—H3 | 119.1 | C12—C11—C10 | 116.35 (10) |
C4—C3—H3 | 119.1 | C13—C12—C11 | 120.32 (10) |
N1—C4—C5 | 122.05 (12) | C13—C12—H12 | 119.8 |
N1—C4—C3 | 121.11 (12) | C11—C12—H12 | 119.8 |
C5—C4—C3 | 116.84 (11) | O2—C13—C12 | 122.41 (10) |
C6—C5—C4 | 120.73 (12) | O2—C13—C14 | 117.75 (11) |
C6—C5—H5 | 119.6 | C12—C13—C14 | 119.84 (11) |
C4—C5—H5 | 119.6 | C15—C14—C13 | 119.55 (11) |
C5—C6—C1 | 122.33 (11) | C15—C14—H14 | 120.2 |
C5—C6—H6 | 118.8 | C13—C14—H14 | 120.2 |
C1—C6—H6 | 118.8 | C14—C15—C16 | 121.09 (12) |
N1—C7—H7A | 109.5 | C14—C15—H15 | 119.5 |
N1—C7—H7B | 109.5 | C16—C15—H15 | 119.5 |
H7A—C7—H7B | 109.5 | C15—C16—C11 | 119.32 (12) |
N1—C7—H7C | 109.5 | C15—C16—H16 | 120.3 |
H7A—C7—H7C | 109.5 | C11—C16—H16 | 120.3 |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 2.18 | 2.8470 (14) | 138 |
O2—H2···N2i | 0.82 | 2.36 | 3.1008 (16) | 150 |
N3—H3A···O1ii | 0.90 (1) | 2.56 (1) | 3.4172 (16) | 160 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H17N3O2 |
Mr | 283.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 13.397 (3), 9.663 (2), 11.183 (2) |
β (°) | 101.97 (3) |
V (Å3) | 1416.2 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.28 × 0.27 × 0.27 |
Data collection | |
Diffractometer | Bruker SMART APEX area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.975, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11531, 3094, 2579 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.130, 1.05 |
No. of reflections | 3094 |
No. of parameters | 196 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.29 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Version 5.1; Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 2.18 | 2.8470 (14) | 138.1 |
O2—H2···N2i | 0.82 | 2.36 | 3.1008 (16) | 149.9 |
N3—H3A···O1ii | 0.895 (9) | 2.561 (11) | 3.4172 (16) | 160.4 (16) |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2. |
Schiff base compounds have been widely investigated due to their easy synthesis, versatile structures and wide applications (Sigman & Jacobsen, 1998; Akitsu & Einaga, 2006; Pradeep, 2005; Butcher et al., 2005). The excellent antibacterial and antitumor properties of such compounds have attracted much interest in recent years (Hodnett & Mooney, 1970; Bahner et al., 1968; Merchant & Chothia, 1970). In order to investigate further the structures of such compounds, the new title Schiff base compound is reported on here.
The dihedral angle between the two benzene rings in the molecule (Fig. 1) of the title compound is 9.2 (2)°. In the crystal structure, molecules are linked through intermolecular O–H···O, O–H···N and N–H···O hydrogen bonds (Table 1), forming layers parallel to the bc plane (Fig. 2).