


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989014026978/hb7335sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989014026978/hb7335Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989014026978/hb7335Isup3.cml |
CCDC reference: 1038374
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.097
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 11 Report
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT093_ALERT_1_G No su's on H-positions, refinement reported as . mixed PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) ..... 1 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 5 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 7 ALERT level G = General information/check it is not something unexpected 3 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
An ethanol solution (25 ml) of chlorophenyl amine (0.25 mole) was mixed with hydroxy benzaldehyde (0.25 mole) and the contents were refluxed for 3 h and kept aside for crystallization. After a few days a pale yellow colour precipitate was formed. Recrystallization was from CHCl3/ethanol solution to form yellow needles. FT—IR (KBr pellet) in cm-1: 3437(O—H), 1614 cm-1(C=N stretching); 1H—NMR (400 MHz, DMSO– d6) in δ (p.p.m.) 13.17 (s,1H, aromatic O—H), 8.63 (s, 1H,C=N), 6.93 - 7.50 (m,8H, CH aromatic),13C—NMR (400 MHz, DMSO-d6) in δ (p.p.m.): 163.3 (C=N), 161.4 (phenolic OH), Electronic spectrum, λmax: 275 and 340 nm (due to intraligand π–π* and n–π* transitions); fluorescence spectra, 432 nm (attributed to the n–π* transition).
All H atoms were positioned geometrically and treated as riding. The C—H and O—H bond lengths are 0.93 Å and 0.82 Å respectively.
As part of our ongoing studies of Schiff bases (Arunagiri et al., 2013a,b), we now describe the synthesis and structure of the title compound.
An ORTEP view of the asymmetric unit is shown in Figure 1. The asymmetric unit contains a molecule of Schiff base. The compound crystallizes in the orthorhombic space group P212121. The dihedral angle between the salicylidene moiety and amino phenyl plane is 51.42 (9)°. The two torsional angles τ1 (N—C—C—C) and τ2 (C—N—C—C) defining the confirmation of the molecule. In the present crystal structure, the torsion angles are 3.2 (3)° (N1—C7—C8—C9), -179.23 (2)° (N1—C7—C8—C13), 47.5 (2)° (C7—N1—C1—C6), -174.48 (2)° (C8—C7—N1—C1) and -135.60 (2)° (N1—C7—C1—C2). The N1—C7 distance of 1.275 (2) Å is normal double bond values and agree well with those observed in other azomethines. The C1—N1—C7 bond angle of 118.70 (2)° in the Schiff base ligand has a normal value. The C3—C2—C1 angle is 121.15 (2)° is larger than typical hexagonal of 120°. The C8—C9—C10 angle is 119.53 (2)° is smaller than typical hexagonal of 120°. This is due to effect of substitution on Cl & OH of the two aromatic rings. The two benzene rings (amino phenyl and salicylaldehyde) and the azomethine group are practically coplanar, as a result of intramolecular O—H···N (O1—H1···N1 with bond length of 2.611 (2) Å and bond angle of 147°) hydrogen bond involving the hydroxy O-atom and azomethine N-atom with graph-set notation S(6), as shown in Figure 2. Similar intramolecular hydrogen bonds are reported for the crystal structures of 2-(naphthalene-2-yliminomethyl) phenol and N-acetyl-4-[(2-hydroxybenzylidene)-amino]benzenesulfonamide monohydrate (Arunagiri et al., 2013 (a); Chumakov et al., 2005).
For related structures recently reported by us and background to Schiff bases, see: Arunagiri et al. (2013a,b). For a related structure, see: Chumakov et al. (2005).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).
C13H10ClNO | F(000) = 480 |
Mr = 231.67 | Dx = 1.360 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 45 reflections |
a = 6.8591 (2) Å | θ = 3.0–28.3° |
b = 12.1829 (4) Å | µ = 0.31 mm−1 |
c = 13.5405 (5) Å | T = 293 K |
V = 1131.50 (6) Å3 | Cut needle, yellow |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 2315 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 28.3°, θmin = 3.0° |
ω scans | h = −9→7 |
6509 measured reflections | k = −13→16 |
2744 independent reflections | l = −18→10 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0488P)2 + 0.0823P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2744 reflections | Δρmax = 0.17 e Å−3 |
146 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (7) |
C13H10ClNO | V = 1131.50 (6) Å3 |
Mr = 231.67 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.8591 (2) Å | µ = 0.31 mm−1 |
b = 12.1829 (4) Å | T = 293 K |
c = 13.5405 (5) Å | 0.30 × 0.25 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 2315 reflections with I > 2σ(I) |
6509 measured reflections | Rint = 0.017 |
2744 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.097 | Δρmax = 0.17 e Å−3 |
S = 1.06 | Δρmin = −0.17 e Å−3 |
2744 reflections | Absolute structure: Flack (1983) |
146 parameters | Absolute structure parameter: 0.01 (7) |
0 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
Cl1 | 0.22873 (7) | 0.87326 (5) | 0.81891 (4) | 0.0781 (2) | |
O1 | 0.41345 (19) | 0.60666 (15) | 0.63294 (11) | 0.0742 (5) | |
N1 | 0.0830 (2) | 0.68972 (13) | 0.69278 (10) | 0.0531 (4) | |
C1 | −0.0473 (2) | 0.72426 (14) | 0.76845 (12) | 0.0486 (5) | |
C2 | 0.0066 (2) | 0.80739 (14) | 0.83346 (13) | 0.0513 (5) | |
C3 | −0.1161 (3) | 0.84060 (16) | 0.90860 (14) | 0.0606 (6) | |
C4 | −0.2937 (3) | 0.78949 (18) | 0.92067 (14) | 0.0672 (7) | |
C5 | −0.3476 (3) | 0.70587 (18) | 0.85879 (16) | 0.0668 (7) | |
C6 | −0.2258 (3) | 0.67361 (15) | 0.78292 (13) | 0.0563 (5) | |
C7 | 0.0161 (2) | 0.67467 (14) | 0.60596 (13) | 0.0506 (5) | |
C8 | 0.1350 (2) | 0.63031 (15) | 0.52664 (12) | 0.0501 (5) | |
C9 | 0.3282 (3) | 0.59651 (15) | 0.54312 (14) | 0.0556 (5) | |
C10 | 0.4336 (3) | 0.54992 (17) | 0.46648 (17) | 0.0676 (7) | |
C11 | 0.3501 (3) | 0.53771 (17) | 0.37489 (16) | 0.0716 (8) | |
C12 | 0.1616 (3) | 0.57133 (18) | 0.35676 (15) | 0.0701 (7) | |
C13 | 0.0551 (3) | 0.61655 (16) | 0.43201 (13) | 0.0597 (6) | |
H1 | 0.33750 | 0.63660 | 0.67120 | 0.1110* | |
H3 | −0.07910 | 0.89710 | 0.95080 | 0.0730* | |
H4 | −0.37710 | 0.81180 | 0.97090 | 0.0810* | |
H5 | −0.46660 | 0.67070 | 0.86790 | 0.0800* | |
H6 | −0.26410 | 0.61710 | 0.74100 | 0.0680* | |
H7 | −0.11310 | 0.69270 | 0.59300 | 0.0610* | |
H10 | 0.56110 | 0.52680 | 0.47710 | 0.0810* | |
H11 | 0.42230 | 0.50620 | 0.32410 | 0.0860* | |
H12 | 0.10740 | 0.56340 | 0.29420 | 0.0840* | |
H13 | −0.07260 | 0.63860 | 0.42020 | 0.0720* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0627 (3) | 0.0739 (3) | 0.0977 (4) | −0.0117 (2) | −0.0077 (2) | −0.0088 (3) |
O1 | 0.0569 (7) | 0.0894 (11) | 0.0762 (9) | 0.0072 (8) | −0.0098 (6) | −0.0086 (8) |
N1 | 0.0541 (7) | 0.0507 (8) | 0.0545 (7) | 0.0050 (6) | −0.0011 (6) | −0.0023 (6) |
C1 | 0.0520 (9) | 0.0442 (9) | 0.0496 (8) | 0.0093 (7) | −0.0039 (7) | 0.0014 (7) |
C2 | 0.0536 (8) | 0.0423 (8) | 0.0579 (9) | 0.0038 (7) | −0.0103 (7) | 0.0030 (7) |
C3 | 0.0738 (12) | 0.0493 (10) | 0.0588 (10) | 0.0110 (8) | −0.0099 (8) | −0.0079 (8) |
C4 | 0.0715 (12) | 0.0656 (12) | 0.0644 (11) | 0.0088 (10) | 0.0122 (9) | −0.0050 (10) |
C5 | 0.0633 (10) | 0.0610 (12) | 0.0761 (12) | −0.0017 (9) | 0.0086 (9) | −0.0019 (10) |
C6 | 0.0597 (9) | 0.0477 (9) | 0.0614 (9) | 0.0011 (8) | −0.0033 (8) | −0.0063 (8) |
C7 | 0.0516 (8) | 0.0436 (8) | 0.0566 (9) | 0.0050 (7) | −0.0025 (7) | 0.0009 (7) |
C8 | 0.0578 (8) | 0.0392 (8) | 0.0533 (9) | −0.0004 (7) | 0.0033 (7) | 0.0024 (7) |
C9 | 0.0547 (8) | 0.0453 (9) | 0.0667 (10) | −0.0036 (7) | 0.0040 (8) | 0.0034 (8) |
C10 | 0.0609 (10) | 0.0551 (11) | 0.0869 (14) | 0.0012 (9) | 0.0190 (10) | 0.0028 (10) |
C11 | 0.0956 (15) | 0.0490 (11) | 0.0703 (13) | 0.0000 (11) | 0.0317 (11) | −0.0017 (9) |
C12 | 0.0957 (14) | 0.0612 (12) | 0.0533 (10) | −0.0001 (12) | 0.0053 (10) | −0.0001 (9) |
C13 | 0.0702 (10) | 0.0531 (10) | 0.0559 (9) | 0.0019 (9) | 0.0001 (8) | 0.0025 (8) |
Cl1—C2 | 1.7333 (15) | C9—C10 | 1.386 (3) |
O1—C9 | 1.355 (2) | C10—C11 | 1.374 (3) |
O1—H1 | 0.8200 | C11—C12 | 1.378 (3) |
N1—C7 | 1.275 (2) | C12—C13 | 1.369 (3) |
N1—C1 | 1.423 (2) | C3—H3 | 0.9300 |
C1—C6 | 1.385 (2) | C4—H4 | 0.9300 |
C1—C2 | 1.392 (2) | C5—H5 | 0.9300 |
C2—C3 | 1.381 (3) | C6—H6 | 0.9300 |
C3—C4 | 1.378 (3) | C7—H7 | 0.9300 |
C4—C5 | 1.370 (3) | C10—H10 | 0.9300 |
C5—C6 | 1.381 (3) | C11—H11 | 0.9300 |
C7—C8 | 1.453 (2) | C12—H12 | 0.9300 |
C8—C13 | 1.404 (2) | C13—H13 | 0.9300 |
C8—C9 | 1.406 (2) | ||
C9—O1—H1 | 109.00 | C11—C12—C13 | 119.17 (19) |
C1—N1—C7 | 118.70 (13) | C8—C13—C12 | 121.26 (18) |
N1—C1—C6 | 121.68 (15) | C2—C3—H3 | 120.00 |
C2—C1—C6 | 118.00 (15) | C4—C3—H3 | 120.00 |
N1—C1—C2 | 120.24 (13) | C3—C4—H4 | 120.00 |
Cl1—C2—C3 | 118.93 (14) | C5—C4—H4 | 120.00 |
C1—C2—C3 | 121.15 (15) | C4—C5—H5 | 120.00 |
Cl1—C2—C1 | 119.90 (12) | C6—C5—H5 | 120.00 |
C2—C3—C4 | 119.59 (17) | C1—C6—H6 | 120.00 |
C3—C4—C5 | 120.14 (19) | C5—C6—H6 | 120.00 |
C4—C5—C6 | 120.22 (19) | N1—C7—H7 | 119.00 |
C1—C6—C5 | 120.87 (17) | C8—C7—H7 | 119.00 |
N1—C7—C8 | 122.21 (13) | C9—C10—H10 | 120.00 |
C7—C8—C13 | 120.01 (14) | C11—C10—H10 | 120.00 |
C9—C8—C13 | 118.56 (16) | C10—C11—H11 | 119.00 |
C7—C8—C9 | 121.39 (15) | C12—C11—H11 | 119.00 |
O1—C9—C10 | 118.96 (18) | C11—C12—H12 | 120.00 |
C8—C9—C10 | 119.53 (18) | C13—C12—H12 | 120.00 |
O1—C9—C8 | 121.51 (17) | C8—C13—H13 | 119.00 |
C9—C10—C11 | 120.17 (19) | C12—C13—H13 | 119.00 |
C10—C11—C12 | 121.3 (2) | ||
C7—N1—C1—C2 | −135.60 (17) | N1—C7—C8—C9 | 3.2 (3) |
C7—N1—C1—C6 | 47.5 (2) | N1—C7—C8—C13 | −179.23 (17) |
C1—N1—C7—C8 | −174.48 (16) | C7—C8—C9—O1 | −1.9 (3) |
N1—C1—C2—Cl1 | 2.9 (2) | C7—C8—C9—C10 | 177.01 (17) |
C6—C1—C2—Cl1 | 179.83 (13) | C13—C8—C9—O1 | −179.45 (18) |
C6—C1—C2—C3 | −1.7 (3) | C13—C8—C9—C10 | −0.6 (3) |
N1—C1—C2—C3 | −178.70 (16) | C7—C8—C13—C12 | −177.66 (18) |
C2—C1—C6—C5 | 0.9 (3) | C9—C8—C13—C12 | 0.0 (3) |
N1—C1—C6—C5 | 177.85 (17) | O1—C9—C10—C11 | 179.40 (19) |
Cl1—C2—C3—C4 | 179.58 (15) | C8—C9—C10—C11 | 0.5 (3) |
C1—C2—C3—C4 | 1.1 (3) | C9—C10—C11—C12 | 0.2 (3) |
C2—C3—C4—C5 | 0.3 (3) | C10—C11—C12—C13 | −0.8 (3) |
C3—C4—C5—C6 | −1.1 (3) | C11—C12—C13—C8 | 0.7 (3) |
C4—C5—C6—C1 | 0.5 (3) |
As part of our ongoing studies of Schiff bases (Arunagiri et al., 2013a,b), we now describe the synthesis and structure of the title compound.
An ORTEP view of the asymmetric unit is shown in Figure 1. The asymmetric unit contains a molecule of Schiff base. The compound crystallizes in the orthorhombic space group P212121. The dihedral angle between the salicylidene moiety and amino phenyl plane is 51.42 (9)°. The two torsional angles τ1 (N—C—C—C) and τ2 (C—N—C—C) defining the confirmation of the molecule. In the present crystal structure, the torsion angles are 3.2 (3)° (N1—C7—C8—C9), -179.23 (2)° (N1—C7—C8—C13), 47.5 (2)° (C7—N1—C1—C6), -174.48 (2)° (C8—C7—N1—C1) and -135.60 (2)° (N1—C7—C1—C2). The N1—C7 distance of 1.275 (2) Å is normal double bond values and agree well with those observed in other azomethines. The C1—N1—C7 bond angle of 118.70 (2)° in the Schiff base ligand has a normal value. The C3—C2—C1 angle is 121.15 (2)° is larger than typical hexagonal of 120°. The C8—C9—C10 angle is 119.53 (2)° is smaller than typical hexagonal of 120°. This is due to effect of substitution on Cl & OH of the two aromatic rings. The two benzene rings (amino phenyl and salicylaldehyde) and the azomethine group are practically coplanar, as a result of intramolecular O—H···N (O1—H1···N1 with bond length of 2.611 (2) Å and bond angle of 147°) hydrogen bond involving the hydroxy O-atom and azomethine N-atom with graph-set notation S(6), as shown in Figure 2. Similar intramolecular hydrogen bonds are reported for the crystal structures of 2-(naphthalene-2-yliminomethyl) phenol and N-acetyl-4-[(2-hydroxybenzylidene)-amino]benzenesulfonamide monohydrate (Arunagiri et al., 2013 (a); Chumakov et al., 2005).