Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one

Kansiz, S.; Aydin, A.S.; Dege, N.; Agar, E.; Fritsky, I.O.

doi:10.1107/S2056989019006583

Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one

S. Kansiz, A. S. Aydin, N. Dege, E. Agar and I. O. Fritsky

In the crystal structure of the title compound, the molecules are linked by pairs of O—H

O hydrogen bonds, forming inversion dimers with an $R_{2}^{2}$ (18) ring motif.

Keywords: crystal structure; Schiff base; hydrogen bonding; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019006583/wm5504sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019006583/wm5504Isup2.hkl Contains datablock I

CCDC reference: 1902148

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.064
wR factor = 0.156
Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00487 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     36.309 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      6.744 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.757 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         15 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT309_ALERT_2_G Single Bonded Oxygen (C-O > 1.3 Ang) ...........         O2 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 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
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012), SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(Z)-6-[(2-Hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one top

Crystal data top

C₁₅H₁₅NO₂	F(000) = 512
M_r = 241.28	D_x = 1.292 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.3954 (19) Å	Cell parameters from 15101 reflections
b = 11.746 (2) Å	θ = 2.8–30.9°
c = 10.3067 (17) Å	µ = 0.09 mm⁻¹
β = 115.940 (12)°	T = 296 K
V = 1240.6 (4) Å³	Prism, red
Z = 4	0.57 × 0.50 × 0.44 mm

Data collection top

Stoe IPDS 2 diffractometer	2417 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1261 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.061
rotation method scans	θ_max = 26.0°, θ_min = 2.8°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −14→13
T_min = 0.962, T_max = 0.975	k = −14→11
6997 measured reflections	l = −12→12

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.064	w = 1/[σ²(F_o²) + (0.0717P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.156	(Δ/σ)_max < 0.001
S = 0.99	Δρ_max = 0.16 e Å⁻³
2417 reflections	Δρ_min = −0.14 e Å⁻³
171 parameters	Extinction correction: SHELXL2017 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.007 (2)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.3892 (2)	0.58075 (18)	0.4721 (3)	0.0775 (7)
H1	0.379271	0.539357	0.530605	0.116*
O2	0.6238 (2)	0.57505 (18)	0.3518 (2)	0.0735 (7)
N1	0.4922 (3)	0.7437 (3)	0.3822 (3)	0.0581 (7)
C9	0.6549 (3)	0.7665 (2)	0.2975 (3)	0.0544 (7)
C1	0.3454 (3)	0.6868 (3)	0.4791 (3)	0.0563 (7)
C8	0.5565 (3)	0.8082 (3)	0.3317 (3)	0.0599 (8)
H8	0.536018	0.885293	0.317983	0.072*
C6	0.3978 (3)	0.7746 (2)	0.4288 (3)	0.0546 (7)
C2	0.2544 (3)	0.7113 (3)	0.5301 (3)	0.0613 (8)
H2A	0.219587	0.652120	0.562261	0.074*
C3	0.2140 (3)	0.8211 (3)	0.5343 (3)	0.0592 (8)
C11	0.8287 (3)	0.8104 (3)	0.2270 (3)	0.0603 (8)
C14	0.6898 (3)	0.6484 (3)	0.3155 (3)	0.0599 (8)
C10	0.7254 (3)	0.8436 (3)	0.2515 (3)	0.0628 (8)
H10	0.700067	0.919577	0.237683	0.075*
C5	0.3571 (3)	0.8851 (3)	0.4324 (3)	0.0642 (8)
H5	0.390952	0.944514	0.399559	0.077*
C4	0.2668 (3)	0.9080 (3)	0.4843 (3)	0.0670 (8)
H4	0.240644	0.982737	0.485967	0.080*
C12	0.8638 (3)	0.6949 (3)	0.2488 (3)	0.0681 (9)
H12	0.934719	0.670249	0.234291	0.082*
C13	0.7972 (3)	0.6170 (3)	0.2906 (3)	0.0688 (9)
H13	0.823971	0.541368	0.302935	0.083*
C7	0.1151 (3)	0.8461 (3)	0.5909 (3)	0.0762 (10)
H7A	0.031563	0.816866	0.524800	0.114*
H7B	0.109049	0.926922	0.600598	0.114*
H7C	0.141812	0.810509	0.683322	0.114*
C15	0.9064 (3)	0.8936 (3)	0.1829 (4)	0.0769 (10)
H15A	0.861304	0.965184	0.157474	0.115*
H15B	0.916047	0.863810	0.101333	0.115*
H15C	0.990962	0.904493	0.261813	0.115*
H1A	0.516 (4)	0.673 (4)	0.387 (4)	0.088 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1026 (18)	0.0475 (13)	0.1056 (17)	0.0073 (13)	0.0671 (15)	0.0093 (11)
O2	0.0894 (16)	0.0526 (13)	0.0949 (14)	−0.0002 (12)	0.0555 (13)	0.0079 (11)
N1	0.0611 (17)	0.0488 (17)	0.0674 (15)	0.0035 (14)	0.0308 (13)	0.0064 (12)
C9	0.0583 (18)	0.0501 (18)	0.0558 (16)	0.0016 (15)	0.0259 (15)	0.0034 (13)
C1	0.0612 (19)	0.0484 (18)	0.0586 (16)	0.0013 (16)	0.0254 (15)	0.0019 (13)
C8	0.0620 (19)	0.0505 (18)	0.0669 (17)	−0.0019 (16)	0.0281 (15)	0.0050 (14)
C6	0.0550 (18)	0.0498 (18)	0.0602 (16)	0.0033 (15)	0.0262 (14)	0.0031 (13)
C2	0.068 (2)	0.056 (2)	0.0655 (17)	−0.0049 (16)	0.0342 (16)	0.0039 (14)
C3	0.0591 (19)	0.063 (2)	0.0557 (16)	0.0044 (17)	0.0251 (14)	0.0027 (14)
C11	0.063 (2)	0.063 (2)	0.0601 (16)	−0.0045 (17)	0.0318 (15)	−0.0012 (14)
C14	0.065 (2)	0.0535 (19)	0.0620 (16)	−0.0024 (16)	0.0288 (15)	−0.0002 (14)
C10	0.067 (2)	0.0563 (19)	0.0648 (17)	−0.0033 (17)	0.0283 (16)	0.0005 (14)
C5	0.0658 (19)	0.0512 (19)	0.0800 (19)	−0.0004 (17)	0.0359 (17)	0.0060 (15)
C4	0.072 (2)	0.0526 (19)	0.084 (2)	0.0078 (17)	0.0406 (18)	0.0011 (16)
C12	0.071 (2)	0.069 (2)	0.0735 (19)	0.0016 (18)	0.0400 (17)	−0.0055 (16)
C13	0.082 (2)	0.0532 (19)	0.081 (2)	0.0030 (18)	0.0450 (19)	−0.0030 (16)
C7	0.073 (2)	0.085 (3)	0.078 (2)	0.0082 (19)	0.0403 (18)	0.0022 (17)
C15	0.078 (2)	0.081 (3)	0.084 (2)	−0.011 (2)	0.0477 (19)	−0.0013 (18)

Geometric parameters (Å, º) top

O1—C1	1.356 (3)	C11—C10	1.365 (4)
O1—H1	0.8200	C11—C12	1.405 (4)
O2—C14	1.302 (4)	C11—C15	1.516 (4)
N1—C8	1.310 (4)	C14—C13	1.404 (4)
N1—C6	1.404 (4)	C10—H10	0.9300
N1—H1A	0.87 (4)	C5—C4	1.377 (4)
C9—C8	1.403 (4)	C5—H5	0.9300
C9—C10	1.422 (4)	C4—H4	0.9300
C9—C14	1.433 (4)	C12—C13	1.373 (4)
C1—C2	1.383 (4)	C12—H12	0.9300
C1—C6	1.400 (4)	C13—H13	0.9300
C8—H8	0.9300	C7—H7A	0.9600
C6—C5	1.385 (4)	C7—H7B	0.9600
C2—C3	1.377 (4)	C7—H7C	0.9600
C2—H2A	0.9300	C15—H15A	0.9600
C3—C4	1.393 (4)	C15—H15B	0.9600
C3—C7	1.506 (4)	C15—H15C	0.9600

C1—O1—H1	109.5	C11—C10—C9	122.6 (3)
C8—N1—C6	129.1 (3)	C11—C10—H10	118.7
C8—N1—H1A	111 (2)	C9—C10—H10	118.7
C6—N1—H1A	120 (2)	C4—C5—C6	120.6 (3)
C8—C9—C10	119.4 (3)	C4—C5—H5	119.7
C8—C9—C14	120.9 (2)	C6—C5—H5	119.7
C10—C9—C14	119.6 (3)	C5—C4—C3	121.2 (3)
O1—C1—C2	124.5 (3)	C5—C4—H4	119.4
O1—C1—C6	115.5 (2)	C3—C4—H4	119.4
C2—C1—C6	120.0 (3)	C13—C12—C11	122.4 (3)
N1—C8—C9	123.0 (3)	C13—C12—H12	118.8
N1—C8—H8	118.5	C11—C12—H12	118.8
C9—C8—H8	118.5	C12—C13—C14	121.9 (3)
C5—C6—C1	118.5 (3)	C12—C13—H13	119.1
C5—C6—N1	124.6 (3)	C14—C13—H13	119.1
C1—C6—N1	116.8 (3)	C3—C7—H7A	109.5
C3—C2—C1	121.6 (3)	C3—C7—H7B	109.5
C3—C2—H2A	119.2	H7A—C7—H7B	109.5
C1—C2—H2A	119.2	C3—C7—H7C	109.5
C2—C3—C4	118.0 (3)	H7A—C7—H7C	109.5
C2—C3—C7	120.8 (3)	H7B—C7—H7C	109.5
C4—C3—C7	121.2 (3)	C11—C15—H15A	109.5
C10—C11—C12	117.0 (3)	C11—C15—H15B	109.5
C10—C11—C15	122.4 (3)	H15A—C15—H15B	109.5
C12—C11—C15	120.5 (3)	C11—C15—H15C	109.5
O2—C14—C13	122.6 (3)	H15A—C15—H15C	109.5
O2—C14—C9	121.0 (3)	H15B—C15—H15C	109.5
C13—C14—C9	116.4 (3)

C6—N1—C8—C9	175.8 (3)	C10—C9—C14—C13	2.3 (4)
C10—C9—C8—N1	−176.2 (3)	C12—C11—C10—C9	0.1 (4)
C14—C9—C8—N1	0.5 (4)	C15—C11—C10—C9	−177.9 (3)
O1—C1—C6—C5	179.8 (3)	C8—C9—C10—C11	174.9 (3)
C2—C1—C6—C5	0.4 (4)	C14—C9—C10—C11	−1.8 (4)
O1—C1—C6—N1	−2.2 (4)	C1—C6—C5—C4	−0.1 (4)
C2—C1—C6—N1	178.4 (3)	N1—C6—C5—C4	−177.9 (3)
C8—N1—C6—C5	−1.7 (5)	C6—C5—C4—C3	0.0 (5)
C8—N1—C6—C1	−179.5 (3)	C2—C3—C4—C5	−0.2 (4)
O1—C1—C2—C3	180.0 (3)	C7—C3—C4—C5	−179.9 (3)
C6—C1—C2—C3	−0.7 (4)	C10—C11—C12—C13	1.0 (5)
C1—C2—C3—C4	0.6 (4)	C15—C11—C12—C13	179.1 (3)
C1—C2—C3—C7	−179.7 (3)	C11—C12—C13—C14	−0.5 (5)
C8—C9—C14—O2	6.1 (4)	O2—C14—C13—C12	178.3 (3)
C10—C9—C14—O2	−177.2 (3)	C9—C14—C13—C12	−1.2 (4)
C8—C9—C14—C13	−174.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.82	2.627 (3)	168
N1—H1A···O2	0.87 (4)	1.83 (4)	2.585 (4)	144 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

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Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hy­droxy-4-methyl­anilino)­methyl­idene]-4-methyl­cyclo­hexa-2,4-dien-1-one

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one