Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(4-methyl­phen­yl)imino]­meth­yl}phenol

The title compound, C₁₅H₁₅NO, shows an intra­molecular O—H...N hydrogen bond and the aromatic rings are tilted by 45.73 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.068
• wR factor = 0.199
• Data-to-parameter ratio = 26.5

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.500
           From the CIF: _refine_ls_abs_structure_Flack_su    0.000
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0058 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C15 H15 N O
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.555 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.247 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.75 mm
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....         C1 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C15 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       0.41 Check
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2018/3 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2020); software used to prepare material for publication: WinGX (Farrugia, 2012), PLATON (Spek, 2020), SHELXL2018 (Sheldrick, 2015b) and publCIF (Westrip, 2010).

(E)-4-Methyl-2-{[(4-methylphenyl)imino]methyl}phenol

Crystal data

C15H15NO	F(000) = 240
Mr = 225.28	Dx = 1.235 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 13.8433 (10) Å	Cell parameters from 12502 reflections
b = 7.0774 (6) Å	θ = 2.9–32.2°
c = 6.2142 (5) Å	µ = 0.08 mm^−1
β = 95.517 (6)°	T = 296 K
V = 606.01 (8) Å^3	Prism, yellow
Z = 2	0.75 × 0.53 × 0.14 mm

Data collection

STOE IPDS 2 diffractometer	4081 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2430 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.063
Detector resolution: 6.67 pixels mm^-1	θmax = 31.9°, θmin = 3.0°
rotation method scans	h = −20→20
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.944, Tmax = 0.989	l = −9→9
9856 measured reflections

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)] = 0.068	H-atom parameters constrained
wR(F^2) = 0.199	w = 1/[σ^2(Fo^2) + (0.0974P)^2 + 0.0159P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4081 reflections	Δρmax = 0.22 e Å^−3
154 parameters	Δρmin = −0.18 e Å^−3
2 restraints	Absolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.5

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
O1	1.5639 (2)	1.6821 (5)	1.9220 (4)	0.0603 (8)
H1	1.515349	1.711085	1.842779	0.090*
C14	1.6429 (3)	1.7148 (5)	1.8202 (5)	0.0440 (8)
N1	1.4649 (2)	1.7758 (4)	1.5628 (5)	0.0469 (8)
C7	1.2034 (3)	1.8103 (6)	1.3960 (8)	0.0518 (10)
H7	1.148245	1.853517	1.454950	0.062*
C5	1.3754 (3)	1.7675 (5)	1.4311 (6)	0.0429 (8)
C10	1.7225 (3)	1.8176 (5)	1.5071 (6)	0.0436 (7)
H10	1.718715	1.864633	1.366824	0.052*
C8	1.5439 (2)	1.8060 (6)	1.4792 (5)	0.0425 (8)
H8	1.542131	1.842677	1.335168	0.051*
C9	1.6373 (3)	1.7836 (5)	1.6074 (6)	0.0424 (8)
C3	1.2783 (3)	1.6698 (6)	1.1093 (7)	0.0511 (9)
H3	1.274388	1.616264	0.972030	0.061*
C6	1.2917 (3)	1.8269 (6)	1.5136 (6)	0.0510 (10)
H6	1.295318	1.878997	1.651540	0.061*
C2	1.1939 (3)	1.7306 (6)	1.1904 (6)	0.0507 (10)
C13	1.7325 (3)	1.6749 (6)	1.9267 (6)	0.0522 (10)
H13	1.737103	1.626082	2.066301	0.063*
C4	1.3679 (3)	1.6860 (5)	1.2251 (6)	0.0475 (8)
H4	1.423221	1.642909	1.166639	0.057*
C12	1.8156 (3)	1.7078 (6)	1.8251 (7)	0.0537 (11)
H12	1.875444	1.679660	1.899117	0.064*
C15	1.9044 (3)	1.8119 (7)	1.5057 (9)	0.0700 (12)
H15A	1.886555	1.863232	1.364448	0.105*
H15B	1.946511	1.898674	1.587855	0.105*
H15C	1.937339	1.693734	1.492355	0.105*
C11	1.8135 (3)	1.7801 (5)	1.6204 (7)	0.0485 (9)
C1	1.0972 (3)	1.7067 (8)	1.0630 (9)	0.0758 (15)
H1A	1.047278	1.756598	1.143908	0.114*
H1B	1.096915	1.773211	0.928331	0.114*
H1C	1.085349	1.574848	1.035150	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0522 (14)	0.087 (2)	0.0425 (13)	−0.0019 (15)	0.0088 (11)	0.0087 (15)
C14	0.052 (2)	0.0442 (19)	0.0359 (17)	−0.0002 (15)	0.0035 (15)	0.0015 (15)
N1	0.0464 (16)	0.0464 (18)	0.0479 (19)	−0.0010 (14)	0.0045 (13)	0.0029 (14)
C7	0.0372 (18)	0.054 (2)	0.065 (3)	0.0014 (16)	0.0097 (17)	−0.007 (2)
C5	0.0459 (18)	0.0420 (18)	0.0406 (19)	−0.0030 (16)	0.0037 (15)	0.0054 (16)
C10	0.0442 (16)	0.0428 (17)	0.0435 (18)	−0.0017 (15)	0.0030 (14)	0.0031 (15)
C8	0.0434 (18)	0.0474 (19)	0.0359 (17)	−0.0036 (14)	−0.0001 (14)	0.0054 (14)
C9	0.0421 (16)	0.0426 (18)	0.042 (2)	−0.0034 (15)	0.0014 (15)	−0.0044 (16)
C3	0.054 (2)	0.051 (2)	0.048 (2)	−0.0009 (18)	−0.0012 (17)	−0.0079 (18)
C6	0.057 (2)	0.050 (2)	0.048 (2)	0.0011 (18)	0.0102 (18)	0.0016 (18)
C2	0.046 (2)	0.045 (2)	0.060 (2)	0.0003 (16)	0.0012 (18)	0.0048 (18)
C13	0.059 (2)	0.0455 (19)	0.050 (2)	−0.0028 (18)	−0.0029 (19)	−0.0017 (17)
C4	0.0477 (19)	0.0468 (19)	0.050 (2)	0.0037 (15)	0.0117 (15)	0.0010 (16)
C12	0.045 (2)	0.052 (3)	0.061 (3)	0.0010 (15)	−0.0061 (18)	−0.0008 (18)
C15	0.051 (2)	0.078 (3)	0.082 (3)	−0.001 (2)	0.010 (2)	0.007 (3)
C11	0.0428 (18)	0.0413 (18)	0.062 (2)	−0.0055 (14)	0.0066 (17)	−0.0073 (16)
C1	0.046 (2)	0.081 (3)	0.096 (4)	−0.002 (2)	−0.014 (2)	−0.002 (3)

Geometric parameters (Å, º)

O1—C14	1.335 (5)	C3—C2	1.384 (6)
O1—H1	0.8200	C3—H3	0.9300
C14—C13	1.378 (5)	C6—H6	0.9300
C14—C9	1.404 (5)	C2—C1	1.499 (5)
N1—C8	1.273 (4)	C13—C12	1.384 (6)
N1—C5	1.419 (5)	C13—H13	0.9300
C7—C6	1.368 (6)	C4—H4	0.9300
C7—C2	1.391 (6)	C12—C11	1.369 (6)
C7—H7	0.9300	C12—H12	0.9300
C5—C6	1.376 (5)	C15—C11	1.521 (6)
C5—C4	1.399 (6)	C15—H15A	0.9600
C10—C9	1.407 (5)	C15—H15B	0.9600
C10—C11	1.408 (5)	C15—H15C	0.9600
C10—H10	0.9300	C1—H1A	0.9600
C8—C9	1.460 (5)	C1—H1B	0.9600
C8—H8	0.9300	C1—H1C	0.9600
C3—C4	1.378 (5)
C14—O1—H1	109.5	C3—C2—C1	121.0 (4)
O1—C14—C13	118.5 (3)	C7—C2—C1	122.1 (4)
O1—C14—C9	122.2 (3)	C14—C13—C12	119.7 (4)
C13—C14—C9	119.3 (3)	C14—C13—H13	120.2
C8—N1—C5	120.6 (3)	C12—C13—H13	120.2
C6—C7—C2	121.7 (4)	C3—C4—C5	119.7 (4)
C6—C7—H7	119.1	C3—C4—H4	120.1
C2—C7—H7	119.1	C5—C4—H4	120.1
C6—C5—C4	118.4 (4)	C11—C12—C13	122.9 (3)
C6—C5—N1	119.5 (3)	C11—C12—H12	118.6
C4—C5—N1	121.9 (3)	C13—C12—H12	118.6
C9—C10—C11	119.6 (4)	C11—C15—H15A	109.5
C9—C10—H10	120.2	C11—C15—H15B	109.5
C11—C10—H10	120.2	H15A—C15—H15B	109.5
N1—C8—C9	120.6 (3)	C11—C15—H15C	109.5
N1—C8—H8	119.7	H15A—C15—H15C	109.5
C9—C8—H8	119.7	H15B—C15—H15C	109.5
C14—C9—C10	120.2 (3)	C12—C11—C10	118.2 (4)
C14—C9—C8	121.2 (3)	C12—C11—C15	123.1 (3)
C10—C9—C8	118.4 (3)	C10—C11—C15	118.6 (4)
C4—C3—C2	122.2 (4)	C2—C1—H1A	109.5
C4—C3—H3	118.9	C2—C1—H1B	109.5
C2—C3—H3	118.9	H1A—C1—H1B	109.5
C7—C6—C5	121.0 (4)	C2—C1—H1C	109.5
C7—C6—H6	119.5	H1A—C1—H1C	109.5
C5—C6—H6	119.5	H1B—C1—H1C	109.5
C3—C2—C7	116.9 (3)
C8—N1—C5—C6	−148.2 (4)	C4—C3—C2—C7	0.2 (6)
C8—N1—C5—C4	37.2 (6)	C4—C3—C2—C1	−178.4 (4)
C5—N1—C8—C9	−169.8 (3)	C6—C7—C2—C3	−0.5 (6)
O1—C14—C9—C10	179.4 (4)	C6—C7—C2—C1	178.1 (4)
C13—C14—C9—C10	−2.2 (5)	O1—C14—C13—C12	−179.9 (3)
O1—C14—C9—C8	−5.9 (5)	C9—C14—C13—C12	1.7 (6)
C13—C14—C9—C8	172.5 (4)	C2—C3—C4—C5	−0.5 (6)
C11—C10—C9—C14	0.8 (5)	C6—C5—C4—C3	1.0 (6)
C11—C10—C9—C8	−174.0 (3)	N1—C5—C4—C3	175.6 (4)
N1—C8—C9—C14	4.9 (6)	C14—C13—C12—C11	0.2 (6)
N1—C8—C9—C10	179.6 (3)	C13—C12—C11—C10	−1.7 (6)
C2—C7—C6—C5	1.0 (7)	C13—C12—C11—C15	−178.4 (4)
C4—C5—C6—C7	−1.3 (6)	C9—C10—C11—C12	1.1 (5)
N1—C5—C6—C7	−176.0 (4)	C9—C10—C11—C15	178.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.87	2.591 (4)	146
C4—H4···O1^i	0.93	2.60	3.448 (5)	152

Symmetry code: (i) x, y, z−1.