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In the title com­pound, a benzyl­ideneaniline Schiff base, the planes of the p-substituted aromatic rings subtend a dihedral angle of 46.01 (6)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989024000574/hb8091sup1.cif
Contains datablocks I, Global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989024000574/hb8091Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2056989024000574/hb8091sup3.pdf
Table S1. Short contacts in the crystal structures of com­pounds I, II and III. Figs. S1-S10. Energy frameworks and FTIR, NMR and DSC and TGA data

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989024000574/hb8091Isup4.cml
Supplementary material

CCDC reference: 2325829

Computing details top

(E)-N,N-Diethyl-4-{[(4-methoxyphenyl)imino]methyl}aniline top
Crystal data top
C18H22N2OZ = 2
Mr = 282.37F(000) = 304
Triclinic, P1Dx = 1.179 Mg m3
a = 8.3830 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.2872 (7) ÅCell parameters from 8317 reflections
c = 11.2981 (9) Åθ = 1.9–26.6°
α = 78.991 (6)°µ = 0.07 mm1
β = 71.009 (6)°T = 250 K
γ = 74.174 (6)°Prism, yellow
V = 795.14 (12) Å30.68 × 0.47 × 0.28 mm
Data collection top
STOE IPDS II
diffractometer
3183 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2453 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.030
Detector resolution: 6.67 pixels mm-1θmax = 26.2°, θmin = 1.9°
rotation method, ω scansh = 1010
Absorption correction: multi-scan
[X-RED32 (Stoe & Cie, 2018) and X-AREA LANA (Stoe & Cie, 2018)]
k = 1111
Tmin = 0.697, Tmax = 0.989l = 1314
11520 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0477P)2 + 0.076P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3183 reflectionsΔρmax = 0.11 e Å3
194 parametersΔρmin = 0.10 e Å3
0 restraintsExtinction correction: (SHELXL2018; Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: dualExtinction coefficient: 0.06 (1)
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
xyzUiso*/Ueq
O10.90654 (10)0.86089 (9)0.06035 (8)0.0546 (2)
N10.34566 (12)0.58694 (11)0.23619 (9)0.0508 (3)
N20.20580 (13)0.16536 (11)0.38486 (9)0.0527 (3)
C10.77767 (14)0.78348 (12)0.10357 (10)0.0454 (3)
C20.61011 (15)0.87089 (12)0.12118 (11)0.0502 (3)
H20.5918110.9762430.1039210.060*
C30.47095 (15)0.80443 (13)0.16366 (11)0.0513 (3)
H30.3582180.8651530.1764490.062*
C40.49434 (14)0.64815 (12)0.18812 (10)0.0462 (3)
C50.66201 (14)0.56221 (12)0.17208 (11)0.0490 (3)
H50.6802410.4569270.1900730.059*
C60.80332 (14)0.62806 (12)0.13011 (11)0.0486 (3)
H60.9159700.5677720.1196720.058*
C70.34757 (14)0.46457 (13)0.19969 (10)0.0491 (3)
H70.4466010.4211050.1382150.059*
C80.20522 (14)0.38883 (12)0.24788 (10)0.0459 (3)
C90.05732 (14)0.43984 (12)0.34505 (10)0.0470 (3)
H90.0498920.5259240.3806010.056*
C100.07673 (14)0.36818 (12)0.38981 (11)0.0474 (3)
H100.1739240.4061920.4550660.057*
C110.07201 (14)0.23796 (12)0.33985 (10)0.0445 (3)
C120.07565 (15)0.18844 (13)0.24069 (11)0.0519 (3)
H120.0831490.1036740.2034070.062*
C130.20913 (15)0.26207 (13)0.19749 (11)0.0520 (3)
H130.3062920.2254580.1316480.062*
C141.07994 (16)0.77581 (15)0.04265 (14)0.0675 (4)
H14A1.1063390.7051150.0178500.101*
H14B1.0931690.7210300.1223300.101*
H14C1.1585920.8432440.0113810.101*
C150.20452 (17)0.03482 (13)0.33003 (12)0.0570 (3)
H15A0.1539110.0503890.2385320.068*
H15B0.3242340.0270420.3463490.068*
C160.1037 (2)0.11202 (15)0.38128 (16)0.0778 (4)
H16A0.1524340.1280650.4719440.117*
H16B0.0165710.1074210.3613910.117*
H16C0.1106560.1945220.3433120.117*
C170.34025 (16)0.19415 (14)0.50416 (11)0.0563 (3)
H17A0.2977300.2415880.5546420.068*
H17B0.3621820.0977890.5510200.068*
C180.50769 (18)0.29363 (18)0.48748 (15)0.0770 (4)
H18A0.5513520.2470130.4382930.115*
H18B0.4880230.3907290.4439970.115*
H18C0.5917890.3073710.5693740.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0506 (5)0.0498 (5)0.0639 (5)0.0138 (4)0.0168 (4)0.0036 (4)
N10.0456 (6)0.0515 (6)0.0536 (6)0.0091 (4)0.0137 (4)0.0055 (4)
N20.0531 (6)0.0540 (6)0.0532 (6)0.0159 (5)0.0113 (4)0.0133 (4)
C10.0484 (6)0.0478 (6)0.0415 (6)0.0113 (5)0.0146 (5)0.0054 (5)
C20.0542 (7)0.0418 (6)0.0536 (7)0.0063 (5)0.0176 (5)0.0057 (5)
C30.0449 (6)0.0499 (6)0.0549 (7)0.0006 (5)0.0156 (5)0.0090 (5)
C40.0447 (6)0.0500 (6)0.0429 (6)0.0086 (5)0.0125 (5)0.0063 (5)
C50.0498 (7)0.0429 (6)0.0522 (6)0.0072 (5)0.0151 (5)0.0045 (5)
C60.0433 (6)0.0478 (6)0.0514 (6)0.0039 (5)0.0150 (5)0.0053 (5)
C70.0447 (6)0.0547 (7)0.0457 (6)0.0067 (5)0.0133 (5)0.0065 (5)
C80.0458 (6)0.0494 (6)0.0424 (6)0.0074 (5)0.0154 (5)0.0052 (5)
C90.0508 (7)0.0436 (6)0.0475 (6)0.0077 (5)0.0152 (5)0.0099 (5)
C100.0463 (6)0.0469 (6)0.0457 (6)0.0054 (5)0.0099 (5)0.0110 (5)
C110.0463 (6)0.0452 (6)0.0435 (6)0.0077 (5)0.0172 (5)0.0052 (5)
C120.0559 (7)0.0516 (6)0.0503 (6)0.0089 (5)0.0146 (5)0.0169 (5)
C130.0473 (6)0.0591 (7)0.0466 (6)0.0063 (5)0.0090 (5)0.0155 (5)
C140.0482 (7)0.0648 (8)0.0862 (10)0.0149 (6)0.0186 (7)0.0009 (7)
C150.0620 (8)0.0554 (7)0.0608 (7)0.0179 (6)0.0205 (6)0.0118 (6)
C160.0840 (10)0.0547 (8)0.0908 (11)0.0109 (7)0.0250 (8)0.0068 (7)
C170.0576 (7)0.0601 (7)0.0518 (7)0.0212 (6)0.0100 (5)0.0065 (6)
C180.0587 (8)0.0865 (10)0.0785 (10)0.0084 (7)0.0123 (7)0.0176 (8)
Geometric parameters (Å, º) top
O1—C11.3669 (13)C9—H90.9400
O1—C141.4220 (14)C10—C111.4153 (15)
N1—C71.2754 (15)C10—H100.9400
N1—C41.4140 (14)C11—C121.4081 (16)
N2—C111.3716 (14)C12—C131.3756 (16)
N2—C151.4592 (14)C12—H120.9400
N2—C171.4639 (15)C13—H130.9400
C1—C61.3882 (16)C14—H14A0.9700
C1—C21.3891 (15)C14—H14B0.9700
C2—C31.3739 (16)C14—H14C0.9700
C2—H20.9400C15—C161.5158 (19)
C3—C41.3958 (16)C15—H15A0.9800
C3—H30.9400C15—H15B0.9800
C4—C51.3868 (15)C16—H16A0.9700
C5—C61.3859 (15)C16—H16B0.9700
C5—H50.9400C16—H16C0.9700
C6—H60.9400C17—C181.5025 (19)
C7—C81.4505 (16)C17—H17A0.9800
C7—H70.9400C17—H17B0.9800
C8—C131.3907 (15)C18—H18A0.9700
C8—C91.3997 (15)C18—H18B0.9700
C9—C101.3678 (15)C18—H18C0.9700
C1—O1—C14117.48 (9)C12—C11—C10116.55 (10)
C7—N1—C4119.31 (10)C13—C12—C11121.08 (10)
C11—N2—C15121.61 (9)C13—C12—H12119.5
C11—N2—C17122.15 (9)C11—C12—H12119.5
C15—N2—C17115.20 (9)C12—C13—C8122.25 (10)
O1—C1—C6124.99 (10)C12—C13—H13118.9
O1—C1—C2115.67 (9)C8—C13—H13118.9
C6—C1—C2119.35 (10)O1—C14—H14A109.5
C3—C2—C1120.45 (10)O1—C14—H14B109.5
C3—C2—H2119.8H14A—C14—H14B109.5
C1—C2—H2119.8O1—C14—H14C109.5
C2—C3—C4121.04 (10)H14A—C14—H14C109.5
C2—C3—H3119.5H14B—C14—H14C109.5
C4—C3—H3119.5N2—C15—C16113.41 (11)
C5—C4—C3117.97 (10)N2—C15—H15A108.9
C5—C4—N1123.58 (10)C16—C15—H15A108.9
C3—C4—N1118.30 (10)N2—C15—H15B108.9
C6—C5—C4121.49 (10)C16—C15—H15B108.9
C6—C5—H5119.3H15A—C15—H15B107.7
C4—C5—H5119.3C15—C16—H16A109.5
C5—C6—C1119.68 (10)C15—C16—H16B109.5
C5—C6—H6120.2H16A—C16—H16B109.5
C1—C6—H6120.2C15—C16—H16C109.5
N1—C7—C8123.56 (11)H16A—C16—H16C109.5
N1—C7—H7118.2H16B—C16—H16C109.5
C8—C7—H7118.2N2—C17—C18113.31 (11)
C13—C8—C9116.81 (10)N2—C17—H17A108.9
C13—C8—C7120.93 (10)C18—C17—H17A108.9
C9—C8—C7122.25 (10)N2—C17—H17B108.9
C10—C9—C8121.97 (10)C18—C17—H17B108.9
C10—C9—H9119.0H17A—C17—H17B107.7
C8—C9—H9119.0C17—C18—H18A109.5
C9—C10—C11121.32 (10)C17—C18—H18B109.5
C9—C10—H10119.3H18A—C18—H18B109.5
C11—C10—H10119.3C17—C18—H18C109.5
N2—C11—C12121.94 (10)H18A—C18—H18C109.5
N2—C11—C10121.51 (10)H18B—C18—H18C109.5
C14—O1—C1—C60.78 (16)C7—C8—C9—C10179.79 (10)
C14—O1—C1—C2179.17 (10)C8—C9—C10—C110.15 (17)
O1—C1—C2—C3179.63 (10)C15—N2—C11—C121.67 (16)
C6—C1—C2—C30.42 (16)C17—N2—C11—C12166.16 (11)
C1—C2—C3—C41.05 (17)C15—N2—C11—C10177.40 (10)
C2—C3—C4—C52.01 (17)C17—N2—C11—C1014.76 (16)
C2—C3—C4—N1177.64 (10)C9—C10—C11—N2179.70 (10)
C7—N1—C4—C541.89 (16)C9—C10—C11—C121.18 (16)
C7—N1—C4—C3142.74 (11)N2—C11—C12—C13179.49 (10)
C3—C4—C5—C61.56 (17)C10—C11—C12—C131.38 (17)
N1—C4—C5—C6176.95 (10)C11—C12—C13—C80.58 (18)
C4—C5—C6—C10.15 (17)C9—C8—C13—C120.49 (17)
O1—C1—C6—C5179.19 (10)C7—C8—C13—C12179.59 (11)
C2—C1—C6—C50.86 (16)C11—N2—C15—C1683.50 (15)
C4—N1—C7—C8176.85 (10)C17—N2—C15—C1685.13 (14)
N1—C7—C8—C13174.93 (11)C11—N2—C17—C18102.52 (13)
N1—C7—C8—C94.12 (17)C15—N2—C17—C1888.92 (13)
C13—C8—C9—C100.70 (16)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C13—H13···Cg1i0.942.983.659 (1)130
Symmetry code: (i) x+1, y+1, z.
Relative percentage contributions of close contacts to the Hirshfeld surfaces of compounds I, II and III. top
IIa and IIb refer to the two independent molecules of compound II'
ContactIIIIIaIIbIII
H···H62.558.153.955.259.5
C···H/H···C26.629.434.332.029.8
N···H/H···N5.16.35.66.55.9
O···H/H···O5.46.06.06.24.6
 

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