(E)-4-Chloro-2-[(cyclo­pentyl­imino)meth­yl]phenol

The title mol­ecule, C₁₂H₁₄ClNO, forms an intra­molecular O—H...N hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.075
• wR factor = 0.235
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =      10.96
            Cell volume su given      =       7.00
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

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S1. Comment

Schiff bases of salicylaldehyde and its derivatives play an important role in organic chemistry (Shi et al., 2007). Recently, we have reported the structural characterization of one Schiff base compound derived from the condensation of 5-chloro-salicylaldehyde and a primary amine (Li et al., 2006). As an extension of this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). An intramolecular O—H···N hydrogen bond is formed between atoms O1 and N1.

Related literature

For related literature, see: Allen et al. (1987); Li et al. (2006); Shi et al. (2007).

S2. Experimental

Cyclopentanamine (85 mg, 1 mmol) and 5-chlorosalicylaldehyde (156 mg, 1 mmol) were dissolved in methanol (10 ml) at 323 K. The mixture was stirred for 10 min to give a clear yellow solution. After keeping the solution in air for 7 d, yellow block crystals were formed at the bottom of the vessel, in about 72% yield, on slow evaporation of the solvent. The crystals were isolated, washed three times with methanol and dried in a vacuum desiccator containing anhydrous CaCl₂.

S3. Refinement

All H atoms were positioned geometrically (C—H = 0.93 Å for the aromatic H atoms, C—H = 0.96 Å for the aliphatic H atoms, and O—H = 0.82 Å) and were refined as riding, with U_iso(H) = 1.2U_eq(C) and U_iso(H) = 1.2U_eq(O).

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. The structure of the title compound (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme

(E)-4-Chloro-2-[(cyclopentylimino)methyl]phenol

Crystal data

C12H14ClNO	F(000) = 944
Mr = 223.69	Dx = 1.261 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.958 (3) Å	Cell parameters from 500 reflections
b = 5.5569 (12) Å	θ = 2.5–25.5°
c = 21.617 (3) Å	µ = 0.30 mm^−1
β = 125.03 (3)°	T = 293 K
V = 2356.5 (7) Å^3	Block, yellow
Z = 8	0.50 × 0.24 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer	2251 independent reflections
Radiation source: fine-focus sealed tube	908 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan SADABS (Bruker, 2001)	h = 0→29
Tmin = 0.865, Tmax = 0.965	k = 0→6
2307 measured reflections	l = −26→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.235	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0965P)^2 + 0.6082P] where P = (Fo^2 + 2Fc^2)/3
2251 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.7766 (2)	0.0513 (8)	0.6790 (3)	0.0646 (12)
C2	0.8024 (3)	−0.1674 (9)	0.6717 (3)	0.0766 (13)
C3	0.8592 (3)	−0.2654 (10)	0.7361 (4)	0.0953 (17)
H3	0.8772	−0.4089	0.7325	0.114*
C4	0.8897 (3)	−0.1555 (11)	0.8053 (3)	0.0895 (16)
H4	0.9281	−0.2240	0.8478	0.107*
C5	0.8634 (3)	0.0567 (10)	0.8115 (3)	0.0798 (14)
C6	0.8080 (2)	0.1560 (9)	0.7495 (3)	0.0729 (13)
H6	0.7905	0.2986	0.7542	0.088*
C7	0.7176 (2)	0.1615 (9)	0.6126 (3)	0.0727 (13)
H7	0.7009	0.3040	0.6186	0.087*
C8	0.6300 (3)	0.1967 (10)	0.4828 (3)	0.0884 (15)
H8	0.6152	0.3291	0.5001	0.106*
C9	0.6461 (3)	0.2912 (10)	0.4289 (3)	0.0997 (17)
H9A	0.6676	0.4482	0.4448	0.120*
H9B	0.6762	0.1819	0.4261	0.120*
C10	0.5788 (3)	0.3068 (11)	0.3548 (3)	0.1093 (18)
H10A	0.5837	0.2844	0.3137	0.131*
H10B	0.5578	0.4622	0.3490	0.131*
C11	0.5366 (3)	0.1083 (15)	0.3557 (3)	0.135 (3)
H11A	0.4914	0.1676	0.3368	0.162*
H11B	0.5320	−0.0229	0.3235	0.162*
C12	0.5706 (3)	0.0228 (13)	0.4339 (3)	0.124 (2)
H12A	0.5873	−0.1402	0.4389	0.148*
H12B	0.5393	0.0251	0.4487	0.148*
Cl1	0.90235 (8)	0.1923 (3)	0.89900 (8)	0.1142 (7)
N1	0.6879 (2)	0.0740 (7)	0.5473 (3)	0.0781 (11)
O1	0.77407 (19)	−0.2775 (6)	0.6054 (2)	0.0977 (12)
H1	0.7420	−0.1970	0.5722	0.147*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.067 (3)	0.052 (3)	0.085 (3)	−0.002 (2)	0.050 (3)	0.001 (3)
C2	0.083 (3)	0.052 (3)	0.103 (4)	0.000 (3)	0.058 (3)	−0.002 (3)
C3	0.101 (4)	0.061 (4)	0.128 (5)	0.016 (3)	0.069 (4)	0.013 (4)
C4	0.082 (3)	0.080 (4)	0.098 (4)	0.007 (3)	0.046 (3)	0.024 (3)
C5	0.083 (3)	0.075 (4)	0.090 (4)	−0.006 (3)	0.054 (3)	0.006 (3)
C6	0.082 (3)	0.060 (3)	0.092 (3)	−0.005 (3)	0.059 (3)	0.000 (3)
C7	0.080 (3)	0.056 (3)	0.098 (4)	−0.001 (3)	0.060 (3)	−0.008 (3)
C8	0.081 (3)	0.089 (4)	0.088 (3)	0.015 (3)	0.045 (3)	−0.006 (3)
C9	0.096 (4)	0.088 (4)	0.108 (4)	−0.011 (3)	0.055 (4)	0.008 (3)
C10	0.111 (4)	0.101 (5)	0.107 (4)	−0.011 (4)	0.058 (4)	−0.003 (4)
C11	0.111 (5)	0.172 (7)	0.098 (4)	−0.040 (5)	0.046 (4)	−0.001 (5)
C12	0.078 (4)	0.150 (6)	0.109 (5)	−0.025 (4)	0.034 (3)	0.021 (4)
Cl1	0.1253 (13)	0.1249 (14)	0.0904 (10)	−0.0230 (10)	0.0607 (9)	−0.0078 (9)
N1	0.077 (3)	0.067 (3)	0.090 (3)	0.001 (2)	0.047 (2)	−0.005 (2)
O1	0.113 (3)	0.059 (2)	0.111 (3)	0.0075 (19)	0.057 (2)	−0.016 (2)

Geometric parameters (Å, º)

C1—C6	1.382 (6)	C8—C9	1.516 (7)
C1—C2	1.412 (6)	C8—C12	1.533 (7)
C1—C7	1.451 (6)	C8—H8	0.980
C2—O1	1.332 (5)	C9—C10	1.485 (7)
C2—C3	1.383 (7)	C9—H9A	0.970
C3—C4	1.374 (7)	C9—H9B	0.970
C3—H3	0.930	C10—C11	1.504 (8)
C4—C5	1.380 (7)	C10—H10A	0.970
C4—H4	0.930	C10—H10B	0.970
C5—C6	1.349 (6)	C11—C12	1.472 (7)
C5—Cl1	1.729 (5)	C11—H11A	0.970
C6—H6	0.930	C11—H11B	0.970
C7—N1	1.259 (5)	C12—H12A	0.970
C7—H7	0.930	C12—H12B	0.970
C8—N1	1.453 (6)	O1—H1	0.820
C6—C1—C2	119.3 (5)	C10—C9—C8	104.5 (4)
C6—C1—C7	121.2 (5)	C10—C9—H9A	110.9
C2—C1—C7	119.6 (5)	C8—C9—H9A	110.9
O1—C2—C3	120.1 (5)	C10—C9—H9B	110.9
O1—C2—C1	122.0 (5)	C8—C9—H9B	110.9
C3—C2—C1	117.9 (5)	H9A—C9—H9B	108.9
C4—C3—C2	121.4 (5)	C9—C10—C11	105.4 (5)
C4—C3—H3	119.3	C9—C10—H10A	110.7
C2—C3—H3	119.3	C11—C10—H10A	110.7
C3—C4—C5	119.9 (5)	C9—C10—H10B	110.7
C3—C4—H4	120.0	C11—C10—H10B	110.7
C5—C4—H4	120.0	H10A—C10—H10B	108.8
C6—C5—C4	119.7 (5)	C12—C11—C10	108.5 (5)
C6—C5—Cl1	121.0 (5)	C12—C11—H11A	110.0
C4—C5—Cl1	119.3 (5)	C10—C11—H11A	110.0
C5—C6—C1	121.7 (5)	C12—C11—H11B	110.0
C5—C6—H6	119.1	C10—C11—H11B	110.0
C1—C6—H6	119.1	H11A—C11—H11B	108.4
N1—C7—C1	123.3 (5)	C11—C12—C8	105.7 (5)
N1—C7—H7	118.3	C11—C12—H12A	110.6
C1—C7—H7	118.3	C8—C12—H12A	110.6
N1—C8—C9	112.1 (4)	C11—C12—H12B	110.6
N1—C8—C12	111.3 (5)	C8—C12—H12B	110.6
C9—C8—C12	103.5 (4)	H12A—C12—H12B	108.7
N1—C8—H8	109.9	C7—N1—C8	120.6 (4)
C9—C8—H8	109.9	C2—O1—H1	109.5
C12—C8—H8	109.9
C6—C1—C2—O1	179.6 (4)	C6—C1—C7—N1	179.2 (4)
C7—C1—C2—O1	0.0 (6)	C2—C1—C7—N1	−1.2 (7)
C6—C1—C2—C3	−1.1 (6)	N1—C8—C9—C10	155.3 (4)
C7—C1—C2—C3	179.2 (4)	C12—C8—C9—C10	35.3 (6)
O1—C2—C3—C4	179.7 (5)	C8—C9—C10—C11	−31.1 (6)
C1—C2—C3—C4	0.4 (7)	C9—C10—C11—C12	14.8 (8)
C2—C3—C4—C5	0.4 (8)	C10—C11—C12—C8	7.3 (8)
C3—C4—C5—C6	−0.4 (7)	N1—C8—C12—C11	−146.6 (5)
C3—C4—C5—Cl1	179.9 (4)	C9—C8—C12—C11	−26.1 (7)
C4—C5—C6—C1	−0.3 (7)	C1—C7—N1—C8	−178.5 (4)
Cl1—C5—C6—C1	179.4 (3)	C9—C8—N1—C7	112.8 (5)
C2—C1—C6—C5	1.1 (7)	C12—C8—N1—C7	−131.9 (5)
C7—C1—C6—C5	−179.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.584 (5)	148