Crystal structure, DFT and MEP study of (E)-2-{[(3-chloro­phen­yl)imino]­meth­yl}-6-methyl­phenol

In the crystal structure of the title compound, mol­ecules are linked through C—H...O hydrogen bonds and C—H...π inter­actions, forming chains parallel to the [010] direction. The mol­ecular geometry in the ground state was been calculated using DFT. Additionally, frontier mol­ecular orbital and mol­ecular electrostatic potential map analyses were performed.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.117
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5859
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.558 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.586          8 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        55% Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   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
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

(E)-2-{[(3-Chlorophenyl)imino]methyl}-6-methylphenol

Crystal data

C14H12ClNO	Dx = 1.337 Mg m^−3
Mr = 245.70	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 15471 reflections
a = 14.0717 (8) Å	θ = 1.5–25.2°
b = 6.4811 (4) Å	µ = 0.29 mm^−1
c = 26.767 (2) Å	T = 296 K
V = 2441.1 (3) Å^3	Prism, orange
Z = 8	0.45 × 0.43 × 0.38 mm
F(000) = 1024

Data collection

Stoe IPDS 2 diffractometer	2052 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1669 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.033
Detector resolution: 6.67 pixels mm^-1	θmax = 24.6°, θmin = 1.5°
rotation method scans	h = −16→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −6→7
Tmin = 0.820, Tmax = 0.907	l = −30→31
10011 measured reflections

Refinement

Refinement on F^2	Primary atom site location: other
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0666P)^2 + 0.3364P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2052 reflections	Δρmax = 0.16 e Å^−3
155 parameters	Δρmin = −0.24 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.33517 (5)	0.79127 (10)	0.03649 (2)	0.0888 (3)
C12	0.32979 (13)	0.7525 (3)	0.13616 (8)	0.0632 (5)
H12	0.296569	0.876559	0.136229	0.076*
C13	0.35979 (13)	0.6646 (3)	0.09213 (7)	0.0565 (5)
C11	0.35033 (14)	0.6518 (3)	0.18009 (8)	0.0655 (5)
H11	0.330163	0.707801	0.210266	0.079*
C14	0.40948 (13)	0.4816 (3)	0.09088 (7)	0.0554 (5)
H14	0.428370	0.425004	0.060536	0.067*
C9	0.43105 (12)	0.3826 (3)	0.13554 (6)	0.0501 (4)
C10	0.40037 (13)	0.4690 (3)	0.18002 (7)	0.0581 (5)
H10	0.413635	0.403110	0.210087	0.070*
C8	0.51952 (12)	0.1055 (3)	0.10169 (7)	0.0533 (4)
H8	0.511386	0.163728	0.070226	0.064*
N1	0.48348 (10)	0.1964 (2)	0.13929 (5)	0.0524 (4)
C4	0.60571 (14)	−0.1837 (3)	0.06298 (7)	0.0617 (5)
H4	0.594284	−0.124767	0.031869	0.074*
C5	0.57270 (12)	−0.0849 (3)	0.10589 (6)	0.0507 (4)
C3	0.65470 (14)	−0.3660 (3)	0.06587 (8)	0.0658 (5)
H3	0.676683	−0.430204	0.037024	0.079*
C6	0.59085 (12)	−0.1759 (3)	0.15252 (6)	0.0511 (4)
O1	0.56117 (10)	−0.0861 (2)	0.19521 (4)	0.0668 (4)
H1	0.533250	0.021525	0.188623	0.100*
C2	0.67106 (13)	−0.4535 (3)	0.11231 (8)	0.0631 (5)
H2	0.703893	−0.577825	0.114078	0.076*
C1	0.64031 (13)	−0.3625 (3)	0.15602 (7)	0.0563 (5)
C7	0.65775 (16)	−0.4616 (4)	0.20614 (9)	0.0763 (6)
H7A	0.694377	−0.585261	0.201724	0.114*
H7B	0.598004	−0.495240	0.221426	0.114*
H7C	0.691973	−0.367515	0.227197	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1145 (5)	0.0730 (4)	0.0790 (4)	0.0241 (3)	−0.0112 (3)	0.0176 (3)
C12	0.0587 (11)	0.0503 (11)	0.0807 (15)	0.0027 (9)	0.0037 (9)	−0.0065 (10)
C13	0.0583 (10)	0.0475 (11)	0.0637 (11)	0.0008 (8)	−0.0049 (8)	0.0044 (9)
C11	0.0684 (12)	0.0645 (13)	0.0635 (12)	0.0014 (10)	0.0096 (9)	−0.0150 (10)
C14	0.0651 (11)	0.0511 (11)	0.0502 (10)	0.0032 (9)	−0.0001 (8)	0.0002 (8)
C9	0.0527 (9)	0.0450 (10)	0.0526 (9)	−0.0037 (8)	−0.0025 (7)	0.0014 (8)
C10	0.0644 (11)	0.0594 (12)	0.0506 (10)	−0.0040 (9)	0.0028 (8)	−0.0030 (9)
C8	0.0620 (11)	0.0483 (10)	0.0498 (9)	−0.0007 (8)	−0.0023 (8)	0.0062 (8)
N1	0.0595 (9)	0.0461 (9)	0.0517 (8)	0.0007 (7)	−0.0021 (6)	0.0006 (7)
C4	0.0693 (11)	0.0610 (13)	0.0546 (11)	0.0007 (10)	0.0075 (9)	0.0022 (9)
C5	0.0545 (9)	0.0454 (10)	0.0520 (10)	−0.0020 (8)	0.0018 (7)	0.0011 (8)
C3	0.0676 (12)	0.0597 (12)	0.0702 (13)	0.0030 (10)	0.0129 (9)	−0.0078 (10)
C6	0.0532 (9)	0.0483 (11)	0.0518 (10)	−0.0016 (8)	−0.0018 (7)	0.0006 (8)
O1	0.0889 (10)	0.0615 (9)	0.0500 (7)	0.0148 (7)	−0.0033 (6)	0.0003 (6)
C2	0.0545 (10)	0.0492 (11)	0.0854 (14)	0.0022 (8)	0.0064 (9)	0.0017 (10)
C1	0.0521 (9)	0.0512 (11)	0.0655 (11)	−0.0010 (8)	−0.0028 (8)	0.0064 (9)
C7	0.0836 (15)	0.0674 (14)	0.0779 (14)	0.0115 (11)	−0.0107 (11)	0.0173 (11)

Geometric parameters (Å, º)

Cl1—C13	1.7357 (19)	C4—C3	1.370 (3)
C12—C13	1.375 (3)	C4—C5	1.395 (2)
C12—C11	1.376 (3)	C4—H4	0.9300
C12—H12	0.9300	C5—C6	1.404 (2)
C13—C14	1.377 (3)	C3—C2	1.386 (3)
C11—C10	1.378 (3)	C3—H3	0.9300
C11—H11	0.9300	C6—O1	1.348 (2)
C14—C9	1.390 (2)	C6—C1	1.399 (3)
C14—H14	0.9300	O1—H1	0.8200
C9—C10	1.385 (2)	C2—C1	1.380 (3)
C9—N1	1.418 (2)	C2—H2	0.9300
C10—H10	0.9300	C1—C7	1.507 (3)
C8—N1	1.271 (2)	C7—H7A	0.9600
C8—C5	1.448 (2)	C7—H7B	0.9600
C8—H8	0.9300	C7—H7C	0.9600
C13—C12—C11	118.11 (18)	C5—C4—H4	119.4
C13—C12—H12	120.9	C4—C5—C6	118.61 (16)
C11—C12—H12	120.9	C4—C5—C8	119.96 (16)
C12—C13—C14	122.25 (18)	C6—C5—C8	121.42 (16)
C12—C13—Cl1	118.56 (15)	C4—C3—C2	119.16 (19)
C14—C13—Cl1	119.19 (15)	C4—C3—H3	120.4
C12—C11—C10	120.94 (18)	C2—C3—H3	120.4
C12—C11—H11	119.5	O1—C6—C1	118.05 (15)
C10—C11—H11	119.5	O1—C6—C5	121.05 (16)
C13—C14—C9	119.17 (17)	C1—C6—C5	120.90 (16)
C13—C14—H14	120.4	C6—O1—H1	109.5
C9—C14—H14	120.4	C1—C2—C3	122.26 (18)
C10—C9—C14	118.98 (17)	C1—C2—H2	118.9
C10—C9—N1	116.45 (16)	C3—C2—H2	118.9
C14—C9—N1	124.57 (16)	C2—C1—C6	117.95 (17)
C11—C10—C9	120.54 (18)	C2—C1—C7	121.44 (18)
C11—C10—H10	119.7	C6—C1—C7	120.61 (17)
C9—C10—H10	119.7	C1—C7—H7A	109.5
N1—C8—C5	122.65 (16)	C1—C7—H7B	109.5
N1—C8—H8	118.7	H7A—C7—H7B	109.5
C5—C8—H8	118.7	C1—C7—H7C	109.5
C8—N1—C9	123.07 (15)	H7A—C7—H7C	109.5
C3—C4—C5	121.12 (18)	H7B—C7—H7C	109.5
C3—C4—H4	119.4
C11—C12—C13—C14	−0.3 (3)	N1—C8—C5—C4	176.22 (18)
C11—C12—C13—Cl1	−179.48 (15)	N1—C8—C5—C6	−2.7 (3)
C13—C12—C11—C10	0.6 (3)	C5—C4—C3—C2	0.3 (3)
C12—C13—C14—C9	−0.6 (3)	C4—C5—C6—O1	179.49 (16)
Cl1—C13—C14—C9	178.56 (14)	C8—C5—C6—O1	−1.6 (3)
C13—C14—C9—C10	1.2 (3)	C4—C5—C6—C1	−0.5 (3)
C13—C14—C9—N1	−178.54 (16)	C8—C5—C6—C1	178.43 (16)
C12—C11—C10—C9	−0.1 (3)	C4—C3—C2—C1	−0.5 (3)
C14—C9—C10—C11	−0.9 (3)	C3—C2—C1—C6	0.2 (3)
N1—C9—C10—C11	178.88 (16)	C3—C2—C1—C7	179.21 (19)
C5—C8—N1—C9	−179.81 (15)	O1—C6—C1—C2	−179.65 (16)
C10—C9—N1—C8	−176.76 (17)	C5—C6—C1—C2	0.3 (3)
C14—C9—N1—C8	3.0 (3)	O1—C6—C1—C7	1.3 (3)
C3—C4—C5—C6	0.2 (3)	C5—C6—C1—C7	−178.70 (17)
C3—C4—C5—C8	−178.79 (17)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.605 (2)	148
C10—H10···O1^i	0.93	2.56	3.402 (2)	151
C2—H2···Cg1^ii	0.93	2.75	3.561 (2)	147
C12—H12···Cg2^iii	0.93	2.78	3.589 (2)	147

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, z; (iii) −x+1/2, y+1/2, z.