4-Chloro-2-(p-tolyl­imino­meth­yl)phenol

The title compound, C₁₄H₁₂ClNO, is a Schiff base compound, derived from the condensation of 5-chloro­salicylaldehyde and p-methoxy­benzenamine in MeOH. The two benzene rings are linked by a C=N bond and form a dihedral angle of 44.4 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.037
• wR factor = 0.099
• Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C14
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C14 H12 Cl N O
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.00

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               1531
           Count of symmetry unique reflns         1047
           Completeness (_total/calc)            146.23%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       484
           Fraction of Friedel pairs measured     0.462
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   1 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); 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-(p-tolyliminomethyl)phenol

Crystal data

C14H12ClNO	F(000) = 256
Mr = 245.70	Dx = 1.374 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 13.846 (11) Å	Cell parameters from 1088 reflections
b = 6.986 (6) Å	θ = 2.9–26.2°
c = 6.176 (5) Å	µ = 0.30 mm^−1
β = 96.363 (10)°	T = 298 K
V = 593.7 (8) Å^3	Block, yellow
Z = 2	0.42 × 0.25 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1531 independent reflections
Radiation source: fine-focus sealed tube	1195 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→12
Tmin = 0.883, Tmax = 0.970	k = −8→8
2956 measured reflections	l = −7→7

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0547P)^2 + 0.04P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
1531 reflections	Δρmax = 0.15 e Å^−3
154 parameters	Δρmin = −0.21 e Å^−3
2 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.000 (2)

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
Cl1	0.93150 (11)	0.18308 (14)	0.3570 (2)	0.0697 (4)
N1	1.3830 (2)	0.2245 (4)	0.2947 (5)	0.0361 (8)
O1	1.2828 (2)	0.3195 (4)	−0.0659 (5)	0.0512 (9)
H1	1.3315	0.2910	0.0157	0.077*
C1	1.3043 (3)	0.1960 (5)	0.3787 (7)	0.0371 (11)
H1A	1.3071	0.1618	0.5247	0.045*
C2	1.2107 (3)	0.2157 (5)	0.2518 (6)	0.0331 (9)
C3	1.2028 (3)	0.2853 (5)	0.0348 (6)	0.0355 (10)
C4	1.1114 (4)	0.3225 (5)	−0.0744 (7)	0.0415 (10)
H4	1.1063	0.3717	−0.2151	0.050*
C5	1.0297 (3)	0.2878 (5)	0.0214 (7)	0.0438 (10)
H5	0.9691	0.3107	−0.0550	0.053*
C6	1.0362 (3)	0.2185 (5)	0.2323 (7)	0.0436 (9)
C7	1.1254 (3)	0.1834 (5)	0.3462 (6)	0.0380 (9)
H7	1.1288	0.1375	0.4882	0.046*
C8	1.4733 (3)	0.2323 (5)	0.4252 (6)	0.0346 (9)
C9	1.4833 (3)	0.3120 (4)	0.6326 (5)	0.0380 (8)
H9	1.4286	0.3549	0.6929	0.046*
C10	1.5740 (3)	0.3280 (5)	0.7505 (7)	0.0398 (11)
H10	1.5793	0.3795	0.8901	0.048*
C11	1.6567 (3)	0.2684 (5)	0.6634 (7)	0.0433 (11)
C12	1.6468 (3)	0.1901 (6)	0.4581 (8)	0.0450 (11)
H12	1.7018	0.1479	0.3982	0.054*
C13	1.5563 (3)	0.1729 (5)	0.3385 (6)	0.0374 (11)
H13	1.5514	0.1211	0.1990	0.045*
C14	1.7553 (4)	0.2920 (7)	0.7912 (9)	0.0655 (16)
H14A	1.7480	0.3496	0.9296	0.098*
H14B	1.7950	0.3725	0.7116	0.098*
H14C	1.7855	0.1689	0.8138	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0381 (5)	0.0885 (7)	0.0848 (7)	−0.0030 (7)	0.0176 (5)	0.0076 (9)
N1	0.036 (2)	0.0379 (18)	0.0351 (18)	0.0002 (15)	0.0053 (15)	−0.0006 (14)
O1	0.0458 (19)	0.073 (2)	0.0367 (17)	0.0010 (15)	0.0115 (13)	0.0104 (14)
C1	0.038 (3)	0.039 (2)	0.035 (2)	−0.0002 (16)	0.002 (2)	0.0036 (16)
C2	0.032 (2)	0.0337 (19)	0.034 (2)	−0.0015 (16)	0.0021 (16)	0.0006 (17)
C3	0.037 (2)	0.039 (2)	0.031 (2)	−0.0006 (17)	0.0023 (18)	−0.0005 (18)
C4	0.051 (3)	0.0425 (19)	0.030 (2)	−0.0035 (18)	0.0009 (19)	0.0026 (18)
C5	0.034 (2)	0.044 (2)	0.050 (2)	0.0012 (15)	−0.0099 (18)	0.0004 (18)
C6	0.034 (2)	0.042 (2)	0.054 (3)	−0.0032 (16)	0.0060 (18)	−0.0032 (19)
C7	0.037 (2)	0.0415 (18)	0.036 (2)	−0.0038 (15)	0.0056 (16)	0.0038 (15)
C8	0.032 (2)	0.033 (2)	0.039 (2)	0.0007 (17)	0.0041 (19)	−0.0025 (17)
C9	0.0370 (19)	0.0394 (18)	0.039 (2)	0.0021 (15)	0.0087 (16)	0.0008 (16)
C10	0.044 (3)	0.037 (2)	0.038 (2)	−0.0031 (17)	0.003 (2)	−0.0019 (17)
C11	0.036 (3)	0.039 (2)	0.054 (3)	−0.0009 (18)	0.0021 (19)	0.0026 (19)
C12	0.035 (3)	0.047 (2)	0.054 (3)	0.0069 (18)	0.012 (2)	−0.003 (2)
C13	0.042 (3)	0.035 (2)	0.036 (2)	0.0003 (16)	0.0061 (19)	−0.0024 (16)
C14	0.043 (3)	0.071 (3)	0.078 (4)	−0.007 (2)	−0.014 (3)	−0.002 (3)

Geometric parameters (Å, º)

Cl1—C6	1.733 (4)	C7—H7	0.9300
N1—C1	1.273 (5)	C8—C13	1.384 (6)
N1—C8	1.412 (4)	C8—C9	1.389 (5)
O1—C3	1.351 (5)	C9—C10	1.384 (5)
O1—H1	0.8200	C9—H9	0.9300
C1—C2	1.444 (5)	C10—C11	1.382 (6)
C1—H1A	0.9300	C10—H10	0.9300
C2—C7	1.393 (5)	C11—C12	1.374 (7)
C2—C3	1.418 (5)	C11—C14	1.509 (6)
C3—C4	1.392 (6)	C12—C13	1.387 (6)
C4—C5	1.355 (6)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.383 (6)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.374 (5)	C14—H14C	0.9600
C1—N1—C8	121.2 (3)	C13—C8—N1	119.3 (3)
C3—O1—H1	109.5	C9—C8—N1	122.2 (3)
N1—C1—C2	121.4 (4)	C10—C9—C8	120.6 (4)
N1—C1—H1A	119.3	C10—C9—H9	119.7
C2—C1—H1A	119.3	C8—C9—H9	119.7
C7—C2—C3	118.1 (4)	C11—C10—C9	120.9 (4)
C7—C2—C1	120.6 (4)	C11—C10—H10	119.6
C3—C2—C1	121.0 (4)	C9—C10—H10	119.6
O1—C3—C4	119.5 (4)	C12—C11—C10	118.5 (4)
O1—C3—C2	121.0 (4)	C12—C11—C14	121.2 (4)
C4—C3—C2	119.5 (4)	C10—C11—C14	120.3 (4)
C5—C4—C3	120.9 (4)	C11—C12—C13	121.1 (4)
C5—C4—H4	119.6	C11—C12—H12	119.4
C3—C4—H4	119.6	C13—C12—H12	119.4
C4—C5—C6	120.3 (3)	C8—C13—C12	120.5 (4)
C4—C5—H5	119.9	C8—C13—H13	119.7
C6—C5—H5	119.9	C12—C13—H13	119.7
C7—C6—C5	120.4 (3)	C11—C14—H14A	109.5
C7—C6—Cl1	119.7 (3)	C11—C14—H14B	109.5
C5—C6—Cl1	119.9 (3)	H14A—C14—H14B	109.5
C6—C7—C2	120.8 (4)	C11—C14—H14C	109.5
C6—C7—H7	119.6	H14A—C14—H14C	109.5
C2—C7—H7	119.6	H14B—C14—H14C	109.5
C13—C8—C9	118.3 (4)
C8—N1—C1—C2	170.8 (3)	C3—C2—C7—C6	−0.2 (5)
N1—C1—C2—C7	179.8 (3)	C1—C2—C7—C6	174.1 (3)
N1—C1—C2—C3	−6.1 (6)	C1—N1—C8—C13	149.4 (3)
C7—C2—C3—O1	180.0 (3)	C1—N1—C8—C9	−35.9 (6)
C1—C2—C3—O1	5.8 (5)	C13—C8—C9—C10	−1.1 (5)
C7—C2—C3—C4	1.3 (5)	N1—C8—C9—C10	−175.9 (4)
C1—C2—C3—C4	−172.9 (4)	C8—C9—C10—C11	1.1 (5)
O1—C3—C4—C5	179.3 (3)	C9—C10—C11—C12	−1.0 (6)
C2—C3—C4—C5	−1.9 (5)	C9—C10—C11—C14	178.2 (4)
C3—C4—C5—C6	1.4 (5)	C10—C11—C12—C13	0.8 (6)
C4—C5—C6—C7	−0.3 (5)	C14—C11—C12—C13	−178.4 (4)
C4—C5—C6—Cl1	177.6 (3)	C9—C8—C13—C12	1.0 (6)
C5—C6—C7—C2	−0.4 (5)	N1—C8—C13—C12	176.0 (4)
Cl1—C6—C7—C2	−178.2 (3)	C11—C12—C13—C8	−0.9 (6)