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In the title mol­ecule, C17H18ClN3O3, the phenol and 2-chloro-5-nitro­phenyl groups are coplanar with each other and also with the imine linkage. Crystal packing is stabilized by inter­molecular C—H...O hydrogen bonds between a chloro­phenyl H atom and a nitro O atom which link the mol­ecules into a chain along the c axis of the unit cell. Intra­molecular O—H...N hydrogen bonding also occurs between the hydroxyl H atom and the imine N atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038901/at2365sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038901/at2365Isup2.hkl
Contains datablock I

CCDC reference: 660242

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.056
  • wR factor = 0.162
  • Data-to-parameter ratio = 24.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.939 Tmax scaled 0.939 Tmin scaled 0.882
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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

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), C17H18ClN3O3 has been synthesized and herein its crystal structure is reported.

The phenol and 2-chloro-5-nitrophenyl groups of the title molecule (I) (Fig. 1) are coplanar with each other [dihedral angle = 5.1 (4)°] and also with the imine linkage, forming torsion angles C7—N2—C6—C5 and N2—C7—C8—C9 of 5.0 (2)° and 0.2 (2)(18)°, respectively.

Intermolecular C—H···O hydrogen bonding between a chlorophenyl hydrogen (C2–H2A) and O2 from the nitro group link the molecules into a chain along the c axis of the unit cell and stabilize crystal packing (Fig. 2). Intramolecular O—H···N hydrogen bonding also occurs between the hydroxyl hydrogen (H3) and the imine nitrogen (N2) within the asymmetric unit (Fig. 1, Tablo 1).

Related literature top

For related structures, see: Odabaşoğlu et al. (2007); Yathirajan et al. (2007). For related literature, see: Hodnett & Dunn (1970); Misra et al. (1981); Agarwal et al. (1983); Varma et al. (1986); Singh & Dash (1988).

Experimental top

A mixture of 2-chloro-5-nitroaniline (0.345 g, 0.002 mol) and 4-(diethylamino)-2-hydroxybenzaldehyde (0.386 g, 0.002 mol) in 15 ml of absolute ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h. On cooling, the solid separated, was filtered and recrystallized from acetone (m.p.: 441–445 K). Analysis found: C 58.59, H 5.16, N 12.01%; C17H18ClN3O3 requires: C 58.71, H 5.22, N 12.08%.

Refinement top

All H atoms were refined using a riding model with O—H = 0.83 Å and C—H = 0.94–0.97 Å, and with Uiso(H) = 1.19–1.50Ueq(C, O).

Structure description top

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), C17H18ClN3O3 has been synthesized and herein its crystal structure is reported.

The phenol and 2-chloro-5-nitrophenyl groups of the title molecule (I) (Fig. 1) are coplanar with each other [dihedral angle = 5.1 (4)°] and also with the imine linkage, forming torsion angles C7—N2—C6—C5 and N2—C7—C8—C9 of 5.0 (2)° and 0.2 (2)(18)°, respectively.

Intermolecular C—H···O hydrogen bonding between a chlorophenyl hydrogen (C2–H2A) and O2 from the nitro group link the molecules into a chain along the c axis of the unit cell and stabilize crystal packing (Fig. 2). Intramolecular O—H···N hydrogen bonding also occurs between the hydroxyl hydrogen (H3) and the imine nitrogen (N2) within the asymmetric unit (Fig. 1, Tablo 1).

For related structures, see: Odabaşoğlu et al. (2007); Yathirajan et al. (2007). For related literature, see: Hodnett & Dunn (1970); Misra et al. (1981); Agarwal et al. (1983); Varma et al. (1986); Singh & Dash (1988).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound (I), showing atom labelling and 50% probability displacement ellipsoids. Dashed lines indicate N—H···O intramolecular hydrogen bonds.
[Figure 2] Fig. 2. Packing diagram of (I), viewed down the b axis. Dashed lines indicate C—H···O intermolecular hydrogen bonds.
2-{(E)-[(2-Chloro-5-nitrophenyl)imino]methyl}-5-(diethylamino)phenol top
Crystal data top
C17H18ClN3O3F(000) = 728
Mr = 347.79Dx = 1.404 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9461 reflections
a = 7.4956 (3) Åθ = 4.9–32.3°
b = 23.3915 (7) ŵ = 0.25 mm1
c = 10.0552 (5) ÅT = 203 K
β = 111.008 (5)°Plate, yellow
V = 1645.82 (12) Å30.49 × 0.45 × 0.25 mm
Z = 4
Data collection top
Oxford Diffraction Gemini R
diffractometer
5364 independent reflections
Radiation source: fine-focus sealed tube3914 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
Detector resolution: 10.5081 pixels mm-1θmax = 32.3°, θmin = 4.9°
φ and ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 3433
Tmin = 0.940, Tmax = 1.000l = 1514
17009 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0722P)2 + 0.8483P]
where P = (Fo2 + 2Fc2)/3
5364 reflections(Δ/σ)max = 0.001
220 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C17H18ClN3O3V = 1645.82 (12) Å3
Mr = 347.79Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.4956 (3) ŵ = 0.25 mm1
b = 23.3915 (7) ÅT = 203 K
c = 10.0552 (5) Å0.49 × 0.45 × 0.25 mm
β = 111.008 (5)°
Data collection top
Oxford Diffraction Gemini R
diffractometer
5364 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
3914 reflections with I > 2σ(I)
Tmin = 0.940, Tmax = 1.000Rint = 0.054
17009 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.162H-atom parameters constrained
S = 1.10Δρmax = 0.41 e Å3
5364 reflectionsΔρmin = 0.31 e Å3
220 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl1.34352 (6)0.00398 (2)0.80924 (6)0.03748 (14)
O10.6102 (2)0.14212 (7)0.38511 (19)0.0513 (4)
O20.45852 (19)0.08230 (6)0.46828 (16)0.0390 (3)
O31.19131 (17)0.09886 (5)1.04607 (14)0.0301 (3)
H31.16810.07480.98150.036*
N10.6067 (2)0.10152 (6)0.46062 (16)0.0273 (3)
N20.97949 (19)0.03280 (5)0.83664 (15)0.0230 (3)
N30.8752 (2)0.22171 (6)1.26954 (17)0.0307 (3)
C11.1265 (2)0.02557 (7)0.70757 (18)0.0230 (3)
C21.1238 (2)0.06546 (7)0.60541 (19)0.0272 (3)
H2A1.23780.07530.59200.033*
C30.9525 (2)0.09101 (7)0.52241 (18)0.0265 (3)
H3A0.94780.11840.45280.032*
C40.7889 (2)0.07449 (6)0.54647 (17)0.0218 (3)
C50.7879 (2)0.03435 (6)0.64667 (17)0.0213 (3)
H5A0.67280.02450.65830.026*
C60.9605 (2)0.00830 (6)0.73132 (17)0.0204 (3)
C70.8315 (2)0.05334 (6)0.85754 (17)0.0231 (3)
H7A0.70960.04000.80090.028*
C80.8467 (2)0.09556 (6)0.96367 (17)0.0218 (3)
C91.0257 (2)0.11792 (6)1.05438 (17)0.0217 (3)
C101.0346 (2)0.15990 (6)1.15374 (18)0.0243 (3)
H10A1.15400.17481.21070.029*
C110.8672 (2)0.18063 (6)1.17092 (17)0.0237 (3)
C120.6883 (2)0.15741 (7)1.08184 (19)0.0268 (3)
H12A0.57460.16991.09190.032*
C130.6820 (2)0.11718 (7)0.98224 (18)0.0265 (3)
H13A0.56210.10320.92320.032*
C141.0565 (3)0.24648 (8)1.36135 (19)0.0336 (4)
H14A1.04310.26001.44960.040*
H14B1.15500.21671.38670.040*
C151.1208 (4)0.29595 (9)1.2914 (3)0.0470 (5)
H15A1.23910.31161.35760.070*
H15B1.14120.28241.20680.070*
H15C1.02320.32541.26500.070*
C160.7024 (3)0.24621 (8)1.2819 (2)0.0365 (4)
H16A0.73090.28481.32180.044*
H16B0.60400.24951.18660.044*
C170.6245 (4)0.21056 (10)1.3756 (3)0.0480 (5)
H17A0.51520.22981.38540.072*
H17B0.58550.17341.33220.072*
H17C0.72300.20581.46890.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0244 (2)0.0427 (3)0.0451 (3)0.00914 (16)0.01210 (19)0.00777 (19)
O10.0425 (8)0.0488 (9)0.0589 (10)0.0079 (7)0.0136 (7)0.0329 (8)
O20.0258 (6)0.0482 (8)0.0409 (8)0.0009 (5)0.0093 (6)0.0095 (6)
O30.0257 (6)0.0334 (6)0.0320 (7)0.0020 (5)0.0114 (5)0.0096 (5)
N10.0294 (7)0.0263 (6)0.0250 (7)0.0028 (5)0.0082 (6)0.0048 (5)
N20.0259 (6)0.0210 (6)0.0221 (6)0.0019 (5)0.0089 (5)0.0038 (5)
N30.0401 (8)0.0247 (6)0.0304 (8)0.0011 (6)0.0164 (7)0.0075 (6)
C10.0206 (7)0.0225 (7)0.0264 (8)0.0021 (5)0.0090 (6)0.0006 (6)
C20.0261 (7)0.0285 (7)0.0320 (9)0.0031 (6)0.0166 (7)0.0013 (6)
C30.0305 (8)0.0259 (7)0.0262 (8)0.0017 (6)0.0139 (7)0.0048 (6)
C40.0244 (7)0.0199 (6)0.0210 (7)0.0002 (5)0.0081 (6)0.0008 (5)
C50.0206 (6)0.0206 (6)0.0234 (7)0.0007 (5)0.0086 (6)0.0014 (5)
C60.0237 (7)0.0177 (6)0.0208 (7)0.0001 (5)0.0090 (6)0.0006 (5)
C70.0249 (7)0.0217 (7)0.0228 (7)0.0023 (5)0.0087 (6)0.0031 (6)
C80.0261 (7)0.0186 (6)0.0205 (7)0.0007 (5)0.0081 (6)0.0021 (5)
C90.0251 (7)0.0205 (6)0.0210 (7)0.0007 (5)0.0099 (6)0.0001 (5)
C100.0289 (7)0.0201 (6)0.0239 (7)0.0039 (5)0.0096 (6)0.0022 (6)
C110.0331 (8)0.0166 (6)0.0229 (7)0.0003 (5)0.0119 (6)0.0002 (5)
C120.0280 (7)0.0259 (7)0.0275 (8)0.0033 (6)0.0112 (6)0.0025 (6)
C130.0255 (7)0.0264 (7)0.0264 (8)0.0004 (6)0.0079 (6)0.0031 (6)
C140.0484 (11)0.0286 (8)0.0227 (8)0.0032 (7)0.0115 (8)0.0083 (6)
C150.0610 (14)0.0342 (10)0.0476 (13)0.0148 (9)0.0217 (11)0.0096 (9)
C160.0481 (11)0.0279 (8)0.0370 (10)0.0063 (7)0.0197 (9)0.0065 (7)
C170.0527 (13)0.0499 (12)0.0525 (13)0.0034 (10)0.0324 (11)0.0039 (10)
Geometric parameters (Å, º) top
Cl—C11.7251 (16)C8—C131.407 (2)
O1—N11.222 (2)C8—C91.424 (2)
O2—N11.2258 (19)C9—C101.385 (2)
O3—C91.3495 (19)C10—C111.412 (2)
O3—H30.8300C10—H10A0.9400
N1—C41.472 (2)C11—C121.426 (2)
N2—C71.293 (2)C12—C131.363 (2)
N2—C61.3993 (19)C12—H12A0.9400
N3—C111.367 (2)C13—H13A0.9400
N3—C141.461 (2)C14—C151.520 (3)
N3—C161.462 (2)C14—H14A0.9800
C1—C21.382 (2)C14—H14B0.9800
C1—C61.408 (2)C15—H15A0.9700
C2—C31.391 (2)C15—H15B0.9700
C2—H2A0.9400C15—H15C0.9700
C3—C41.387 (2)C16—C171.523 (3)
C3—H3A0.9400C16—H16A0.9800
C4—C51.379 (2)C16—H16B0.9800
C5—C61.407 (2)C17—H17A0.9700
C5—H5A0.9400C17—H17B0.9700
C7—C81.428 (2)C17—H17C0.9700
C7—H7A0.9400
C9—O3—H3109.5C9—C10—H10A119.5
O1—N1—O2123.10 (15)C11—C10—H10A119.5
O1—N1—C4118.42 (14)N3—C11—C10121.36 (15)
O2—N1—C4118.48 (14)N3—C11—C12120.67 (15)
C7—N2—C6121.17 (14)C10—C11—C12117.97 (14)
C11—N3—C14121.75 (15)C13—C12—C11120.09 (15)
C11—N3—C16121.84 (15)C13—C12—H12A120.0
C14—N3—C16116.27 (14)C11—C12—H12A120.0
C2—C1—C6122.75 (14)C12—C13—C8123.02 (15)
C2—C1—Cl118.06 (12)C12—C13—H13A118.5
C6—C1—Cl119.18 (12)C8—C13—H13A118.5
C1—C2—C3120.04 (14)N3—C14—C15112.76 (16)
C1—C2—H2A120.0N3—C14—H14A109.0
C3—C2—H2A120.0C15—C14—H14A109.0
C4—C3—C2117.34 (14)N3—C14—H14B109.0
C4—C3—H3A121.3C15—C14—H14B109.0
C2—C3—H3A121.3H14A—C14—H14B107.8
C5—C4—C3123.63 (14)C14—C15—H15A109.5
C5—C4—N1118.29 (13)C14—C15—H15B109.5
C3—C4—N1118.09 (14)H15A—C15—H15B109.5
C4—C5—C6119.49 (13)C14—C15—H15C109.5
C4—C5—H5A120.3H15A—C15—H15C109.5
C6—C5—H5A120.3H15B—C15—H15C109.5
N2—C6—C5125.29 (13)N3—C16—C17112.71 (16)
N2—C6—C1117.97 (14)N3—C16—H16A109.1
C5—C6—C1116.74 (14)C17—C16—H16A109.1
N2—C7—C8122.36 (14)N3—C16—H16B109.1
N2—C7—H7A118.8C17—C16—H16B109.1
C8—C7—H7A118.8H16A—C16—H16B107.8
C13—C8—C9116.94 (14)C16—C17—H17A109.5
C13—C8—C7120.60 (14)C16—C17—H17B109.5
C9—C8—C7122.46 (14)H17A—C17—H17B109.5
O3—C9—C10118.11 (14)C16—C17—H17C109.5
O3—C9—C8121.03 (14)H17A—C17—H17C109.5
C10—C9—C8120.86 (14)H17B—C17—H17C109.5
C9—C10—C11121.09 (15)
C6—C1—C2—C31.0 (3)C13—C8—C9—O3178.67 (15)
Cl—C1—C2—C3179.07 (13)C7—C8—C9—O31.6 (2)
C1—C2—C3—C40.4 (2)C13—C8—C9—C101.3 (2)
C2—C3—C4—C50.3 (2)C7—C8—C9—C10178.35 (15)
C2—C3—C4—N1179.38 (15)O3—C9—C10—C11178.20 (14)
O1—N1—C4—C5170.73 (17)C8—C9—C10—C111.8 (2)
O2—N1—C4—C59.2 (2)C14—N3—C11—C100.4 (2)
O1—N1—C4—C39.0 (2)C16—N3—C11—C10175.88 (16)
O2—N1—C4—C3171.05 (16)C14—N3—C11—C12179.56 (15)
C3—C4—C5—C60.4 (2)C16—N3—C11—C124.1 (2)
N1—C4—C5—C6179.30 (13)C9—C10—C11—N3179.47 (15)
C7—N2—C6—C55.0 (2)C9—C10—C11—C120.6 (2)
C7—N2—C6—C1175.37 (15)N3—C11—C12—C13178.87 (16)
C4—C5—C6—N2179.86 (14)C10—C11—C12—C131.1 (2)
C4—C5—C6—C10.2 (2)C11—C12—C13—C81.6 (3)
C2—C1—C6—N2179.40 (15)C9—C8—C13—C120.4 (2)
Cl—C1—C6—N20.5 (2)C7—C8—C13—C12179.95 (16)
C2—C1—C6—C50.9 (2)C11—N3—C14—C1585.2 (2)
Cl—C1—C6—C5179.17 (11)C16—N3—C14—C1590.5 (2)
C6—N2—C7—C8179.62 (14)C11—N3—C16—C1785.1 (2)
N2—C7—C8—C13179.46 (15)C14—N3—C16—C1799.1 (2)
N2—C7—C8—C90.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O2i0.942.413.291 (2)157
O3—H3···N20.831.902.6356 (18)147
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC17H18ClN3O3
Mr347.79
Crystal system, space groupMonoclinic, P21/c
Temperature (K)203
a, b, c (Å)7.4956 (3), 23.3915 (7), 10.0552 (5)
β (°) 111.008 (5)
V3)1645.82 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.49 × 0.45 × 0.25
Data collection
DiffractometerOxford Diffraction Gemini R
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.940, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
17009, 5364, 3914
Rint0.054
(sin θ/λ)max1)0.752
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.162, 1.10
No. of reflections5364
No. of parameters220
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.31

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O2i0.942.413.291 (2)156.8
O3—H3···N20.831.902.6356 (18)147.2
Symmetry code: (i) x+1, y, z.
 

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