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The title compound, C17H12ClNO, is a Schiff base compound derived from the condensation of equimolar quantities of 5-chloro­salicyl­aldehyde and 1-naphthyl­amine. The structure displays a trans configuration with respect to the imine C=N double bond. The N atom is also involved in an intramolecular O—H...N hydrogen bond. In the crystal structure, the mol­ecules stack along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006392/su6175sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006392/su6175Isup2.hkl
Contains datablock I

CCDC reference: 270550

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.055
  • wR factor = 0.125
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

4-Chloro-2-(1-naphthyliminomethyl)phenol top
Crystal data top
C17H12ClNOF(000) = 584
Mr = 281.73Dx = 1.383 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1012 reflections
a = 24.733 (9) Åθ = 2.2–22.4°
b = 4.420 (2) ŵ = 0.28 mm1
c = 12.376 (4) ÅT = 298 K
β = 90.720 (6)°Block, yellow
V = 1352.8 (9) Å30.48 × 0.32 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2391 independent reflections
Radiation source: fine-focus sealed tube1522 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2923
Tmin = 0.879, Tmax = 0.968k = 45
5273 measured reflectionsl = 914
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0509P)2]
where P = (Fo2 + 2Fc2)/3
2391 reflections(Δ/σ)max < 0.001
182 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.16 e Å3
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
Cl10.03427 (3)0.39243 (19)0.83960 (7)0.0721 (3)
O10.19416 (9)0.3534 (6)1.06843 (15)0.0686 (6)
H10.21960.39281.02910.103*
N10.24917 (9)0.3722 (5)0.88814 (17)0.0479 (6)
C10.20960 (12)0.2278 (6)0.8442 (2)0.0469 (7)
H1A0.21010.19390.77010.056*
C20.16439 (11)0.1157 (6)0.9047 (2)0.0433 (7)
C30.15770 (12)0.1819 (7)1.0136 (2)0.0503 (8)
C40.11334 (13)0.0730 (7)1.0673 (2)0.0587 (8)
H40.10900.11991.14000.070*
C50.07540 (13)0.1038 (7)1.0155 (3)0.0603 (9)
H50.04570.17731.05250.072*
C60.08215 (12)0.1707 (6)0.9070 (3)0.0506 (8)
C70.12580 (12)0.0627 (6)0.8527 (2)0.0501 (7)
H70.12980.10910.77990.060*
C80.29027 (12)0.4870 (6)0.8213 (2)0.0468 (7)
C90.27781 (13)0.6525 (7)0.7304 (2)0.0582 (8)
H90.24190.67680.70870.070*
C100.31936 (15)0.7851 (7)0.6701 (3)0.0689 (10)
H100.31060.90020.60950.083*
C110.37128 (15)0.7482 (7)0.6985 (3)0.0686 (9)
H110.39800.84130.65820.082*
C120.38615 (12)0.5697 (7)0.7890 (2)0.0534 (8)
C130.44047 (14)0.5154 (8)0.8177 (3)0.0678 (10)
H130.46770.60070.77650.081*
C140.45397 (14)0.3422 (8)0.9037 (3)0.0762 (10)
H140.49010.30910.92160.091*
C150.41305 (14)0.2125 (8)0.9661 (3)0.0683 (9)
H150.42240.09321.02530.082*
C160.36038 (12)0.2580 (7)0.9414 (2)0.0540 (8)
H160.33390.16850.98340.065*
C170.34499 (12)0.4411 (6)0.8520 (2)0.0460 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0564 (6)0.0718 (6)0.0881 (7)0.0119 (5)0.0042 (4)0.0025 (5)
O10.0663 (16)0.0974 (17)0.0422 (12)0.0188 (14)0.0054 (10)0.0077 (12)
N10.0462 (15)0.0537 (15)0.0440 (14)0.0020 (13)0.0099 (11)0.0036 (12)
C10.0505 (19)0.0501 (17)0.0403 (17)0.0078 (15)0.0056 (14)0.0012 (13)
C20.0433 (17)0.0468 (16)0.0398 (17)0.0053 (14)0.0021 (13)0.0007 (14)
C30.0501 (19)0.0566 (19)0.0444 (18)0.0038 (16)0.0032 (14)0.0013 (15)
C40.056 (2)0.076 (2)0.0442 (18)0.0029 (18)0.0089 (15)0.0075 (16)
C50.050 (2)0.068 (2)0.063 (2)0.0009 (18)0.0122 (16)0.0166 (18)
C60.0429 (18)0.0469 (17)0.062 (2)0.0069 (15)0.0035 (14)0.0075 (15)
C70.052 (2)0.0519 (18)0.0463 (18)0.0047 (15)0.0046 (14)0.0017 (14)
C80.052 (2)0.0437 (16)0.0445 (18)0.0007 (15)0.0114 (14)0.0062 (13)
C90.062 (2)0.0564 (19)0.056 (2)0.0065 (17)0.0108 (16)0.0015 (16)
C100.082 (3)0.060 (2)0.066 (2)0.005 (2)0.0201 (19)0.0132 (17)
C110.077 (3)0.056 (2)0.073 (2)0.0106 (19)0.0322 (19)0.0009 (18)
C120.051 (2)0.0493 (19)0.060 (2)0.0080 (16)0.0172 (15)0.0132 (16)
C130.056 (2)0.068 (2)0.080 (3)0.0127 (18)0.0227 (18)0.0175 (19)
C140.052 (2)0.091 (3)0.085 (3)0.003 (2)0.003 (2)0.022 (2)
C150.064 (2)0.082 (2)0.059 (2)0.008 (2)0.0004 (18)0.0066 (18)
C160.053 (2)0.0608 (19)0.0489 (19)0.0019 (16)0.0089 (14)0.0086 (16)
C170.053 (2)0.0417 (17)0.0439 (18)0.0032 (14)0.0102 (14)0.0114 (13)
Geometric parameters (Å, º) top
Cl1—C61.742 (3)C8—C171.416 (4)
O1—C31.354 (3)C9—C101.405 (4)
O1—H10.8200C9—H90.9300
N1—C11.283 (3)C10—C111.337 (4)
N1—C81.413 (3)C10—H100.9300
C1—C21.441 (4)C11—C121.415 (4)
C1—H1A0.9300C11—H110.9300
C2—C71.390 (4)C12—C131.406 (4)
C2—C31.391 (4)C12—C171.410 (4)
C3—C41.377 (4)C13—C141.350 (4)
C4—C51.374 (4)C13—H130.9300
C4—H40.9300C14—C151.403 (4)
C5—C61.387 (4)C14—H140.9300
C5—H50.9300C15—C161.349 (4)
C6—C71.365 (4)C15—H150.9300
C7—H70.9300C16—C171.419 (4)
C8—C91.373 (4)C16—H160.9300
C3—O1—H1109.5C8—C9—H9120.0
C1—N1—C8118.7 (2)C10—C9—H9120.0
N1—C1—C2122.9 (3)C11—C10—C9121.0 (3)
N1—C1—H1A118.5C11—C10—H10119.5
C2—C1—H1A118.5C9—C10—H10119.5
C7—C2—C3118.6 (3)C10—C11—C12121.0 (3)
C7—C2—C1119.1 (3)C10—C11—H11119.5
C3—C2—C1122.2 (3)C12—C11—H11119.5
O1—C3—C4118.9 (3)C13—C12—C17119.1 (3)
O1—C3—C2121.1 (3)C13—C12—C11122.2 (3)
C4—C3—C2120.0 (3)C17—C12—C11118.7 (3)
C5—C4—C3121.1 (3)C14—C13—C12121.5 (3)
C5—C4—H4119.4C14—C13—H13119.3
C3—C4—H4119.4C12—C13—H13119.3
C4—C5—C6118.9 (3)C13—C14—C15119.5 (3)
C4—C5—H5120.5C13—C14—H14120.2
C6—C5—H5120.5C15—C14—H14120.2
C7—C6—C5120.5 (3)C16—C15—C14121.1 (3)
C7—C6—Cl1119.9 (2)C16—C15—H15119.5
C5—C6—Cl1119.6 (2)C14—C15—H15119.5
C6—C7—C2120.9 (3)C15—C16—C17120.7 (3)
C6—C7—H7119.6C15—C16—H16119.7
C2—C7—H7119.6C17—C16—H16119.7
C9—C8—N1121.0 (3)C12—C17—C8119.2 (3)
C9—C8—C17120.0 (3)C12—C17—C16118.2 (3)
N1—C8—C17118.9 (3)C8—C17—C16122.5 (3)
C8—C9—C10119.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.902.629 (3)147
 

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