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
CCDC reference: 2325829
(
E)-
N,
N-Diethyl-4-{[(4-methoxyphenyl)imino]methyl}aniline
top
Crystal data top
C18H22N2O | Z = 2 |
Mr = 282.37 | F(000) = 304 |
Triclinic, P1 | Dx = 1.179 Mg m−3 |
a = 8.3830 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.2872 (7) Å | Cell parameters from 8317 reflections |
c = 11.2981 (9) Å | θ = 1.9–26.6° |
α = 78.991 (6)° | µ = 0.07 mm−1 |
β = 71.009 (6)° | T = 250 K |
γ = 74.174 (6)° | Prism, yellow |
V = 795.14 (12) Å3 | 0.68 × 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 focus | 2453 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.030 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.2°, θmin = 1.9° |
rotation method, ω scans | h = −10→10 |
Absorption correction: multi-scan [X-RED32 (Stoe & Cie, 2018) and
X-AREA LANA (Stoe & Cie, 2018)] | k = −11→11 |
Tmin = 0.697, Tmax = 0.989 | l = −13→14 |
11520 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-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 reflections | Δρmax = 0.11 e Å−3 |
194 parameters | Δρmin = −0.10 e Å−3 |
0 restraints | Extinction correction: (SHELXL2018; Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: dual | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.90654 (10) | 0.86089 (9) | 0.06035 (8) | 0.0546 (2) | |
N1 | 0.34566 (12) | 0.58694 (11) | 0.23619 (9) | 0.0508 (3) | |
N2 | −0.20580 (13) | 0.16536 (11) | 0.38486 (9) | 0.0527 (3) | |
C1 | 0.77767 (14) | 0.78348 (12) | 0.10357 (10) | 0.0454 (3) | |
C2 | 0.61011 (15) | 0.87089 (12) | 0.12118 (11) | 0.0502 (3) | |
H2 | 0.591811 | 0.976243 | 0.103921 | 0.060* | |
C3 | 0.47095 (15) | 0.80443 (13) | 0.16366 (11) | 0.0513 (3) | |
H3 | 0.358218 | 0.865153 | 0.176449 | 0.062* | |
C4 | 0.49434 (14) | 0.64815 (12) | 0.18812 (10) | 0.0462 (3) | |
C5 | 0.66201 (14) | 0.56221 (12) | 0.17208 (11) | 0.0490 (3) | |
H5 | 0.680241 | 0.456927 | 0.190073 | 0.059* | |
C6 | 0.80332 (14) | 0.62806 (12) | 0.13011 (11) | 0.0486 (3) | |
H6 | 0.915970 | 0.567772 | 0.119672 | 0.058* | |
C7 | 0.34757 (14) | 0.46457 (13) | 0.19969 (10) | 0.0491 (3) | |
H7 | 0.446601 | 0.421105 | 0.138215 | 0.059* | |
C8 | 0.20522 (14) | 0.38883 (12) | 0.24788 (10) | 0.0459 (3) | |
C9 | 0.05732 (14) | 0.43984 (12) | 0.34505 (10) | 0.0470 (3) | |
H9 | 0.049892 | 0.525924 | 0.380601 | 0.056* | |
C10 | −0.07673 (14) | 0.36818 (12) | 0.38981 (11) | 0.0474 (3) | |
H10 | −0.173924 | 0.406192 | 0.455066 | 0.057* | |
C11 | −0.07201 (14) | 0.23796 (12) | 0.33985 (10) | 0.0445 (3) | |
C12 | 0.07565 (15) | 0.18844 (13) | 0.24069 (11) | 0.0519 (3) | |
H12 | 0.083149 | 0.103674 | 0.203407 | 0.062* | |
C13 | 0.20913 (15) | 0.26207 (13) | 0.19749 (11) | 0.0520 (3) | |
H13 | 0.306292 | 0.225458 | 0.131648 | 0.062* | |
C14 | 1.07994 (16) | 0.77581 (15) | 0.04265 (14) | 0.0675 (4) | |
H14A | 1.106339 | 0.705115 | −0.017850 | 0.101* | |
H14B | 1.093169 | 0.721030 | 0.122330 | 0.101* | |
H14C | 1.158592 | 0.843244 | 0.011381 | 0.101* | |
C15 | −0.20452 (17) | 0.03482 (13) | 0.33003 (12) | 0.0570 (3) | |
H15A | −0.153911 | 0.050389 | 0.238532 | 0.068* | |
H15B | −0.324234 | 0.027042 | 0.346349 | 0.068* | |
C16 | −0.1037 (2) | −0.11202 (15) | 0.38128 (16) | 0.0778 (4) | |
H16A | −0.152434 | −0.128065 | 0.471944 | 0.117* | |
H16B | 0.016571 | −0.107421 | 0.361391 | 0.117* | |
H16C | −0.110656 | −0.194522 | 0.343312 | 0.117* | |
C17 | −0.34025 (16) | 0.19415 (14) | 0.50416 (11) | 0.0563 (3) | |
H17A | −0.297730 | 0.241588 | 0.554642 | 0.068* | |
H17B | −0.362182 | 0.097789 | 0.551020 | 0.068* | |
C18 | −0.50769 (18) | 0.29363 (18) | 0.48748 (15) | 0.0770 (4) | |
H18A | −0.551352 | 0.247013 | 0.438293 | 0.115* | |
H18B | −0.488023 | 0.390729 | 0.443997 | 0.115* | |
H18C | −0.591789 | 0.307371 | 0.569374 | 0.115* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0506 (5) | 0.0498 (5) | 0.0639 (5) | −0.0138 (4) | −0.0168 (4) | −0.0036 (4) |
N1 | 0.0456 (6) | 0.0515 (6) | 0.0536 (6) | −0.0091 (4) | −0.0137 (4) | −0.0055 (4) |
N2 | 0.0531 (6) | 0.0540 (6) | 0.0532 (6) | −0.0159 (5) | −0.0113 (4) | −0.0133 (4) |
C1 | 0.0484 (6) | 0.0478 (6) | 0.0415 (6) | −0.0113 (5) | −0.0146 (5) | −0.0054 (5) |
C2 | 0.0542 (7) | 0.0418 (6) | 0.0536 (7) | −0.0063 (5) | −0.0176 (5) | −0.0057 (5) |
C3 | 0.0449 (6) | 0.0499 (6) | 0.0549 (7) | −0.0006 (5) | −0.0156 (5) | −0.0090 (5) |
C4 | 0.0447 (6) | 0.0500 (6) | 0.0429 (6) | −0.0086 (5) | −0.0125 (5) | −0.0063 (5) |
C5 | 0.0498 (7) | 0.0429 (6) | 0.0522 (6) | −0.0072 (5) | −0.0151 (5) | −0.0045 (5) |
C6 | 0.0433 (6) | 0.0478 (6) | 0.0514 (6) | −0.0039 (5) | −0.0150 (5) | −0.0053 (5) |
C7 | 0.0447 (6) | 0.0547 (7) | 0.0457 (6) | −0.0067 (5) | −0.0133 (5) | −0.0065 (5) |
C8 | 0.0458 (6) | 0.0494 (6) | 0.0424 (6) | −0.0074 (5) | −0.0154 (5) | −0.0052 (5) |
C9 | 0.0508 (7) | 0.0436 (6) | 0.0475 (6) | −0.0077 (5) | −0.0152 (5) | −0.0099 (5) |
C10 | 0.0463 (6) | 0.0469 (6) | 0.0457 (6) | −0.0054 (5) | −0.0099 (5) | −0.0110 (5) |
C11 | 0.0463 (6) | 0.0452 (6) | 0.0435 (6) | −0.0077 (5) | −0.0172 (5) | −0.0052 (5) |
C12 | 0.0559 (7) | 0.0516 (6) | 0.0503 (6) | −0.0089 (5) | −0.0146 (5) | −0.0169 (5) |
C13 | 0.0473 (6) | 0.0591 (7) | 0.0466 (6) | −0.0063 (5) | −0.0090 (5) | −0.0155 (5) |
C14 | 0.0482 (7) | 0.0648 (8) | 0.0862 (10) | −0.0149 (6) | −0.0186 (7) | 0.0009 (7) |
C15 | 0.0620 (8) | 0.0554 (7) | 0.0608 (7) | −0.0179 (6) | −0.0205 (6) | −0.0118 (6) |
C16 | 0.0840 (10) | 0.0547 (8) | 0.0908 (11) | −0.0109 (7) | −0.0250 (8) | −0.0068 (7) |
C17 | 0.0576 (7) | 0.0601 (7) | 0.0518 (7) | −0.0212 (6) | −0.0100 (5) | −0.0065 (6) |
C18 | 0.0587 (8) | 0.0865 (10) | 0.0785 (10) | −0.0084 (7) | −0.0123 (7) | −0.0176 (8) |
Geometric parameters (Å, º) top
O1—C1 | 1.3669 (13) | C9—H9 | 0.9400 |
O1—C14 | 1.4220 (14) | C10—C11 | 1.4153 (15) |
N1—C7 | 1.2754 (15) | C10—H10 | 0.9400 |
N1—C4 | 1.4140 (14) | C11—C12 | 1.4081 (16) |
N2—C11 | 1.3716 (14) | C12—C13 | 1.3756 (16) |
N2—C15 | 1.4592 (14) | C12—H12 | 0.9400 |
N2—C17 | 1.4639 (15) | C13—H13 | 0.9400 |
C1—C6 | 1.3882 (16) | C14—H14A | 0.9700 |
C1—C2 | 1.3891 (15) | C14—H14B | 0.9700 |
C2—C3 | 1.3739 (16) | C14—H14C | 0.9700 |
C2—H2 | 0.9400 | C15—C16 | 1.5158 (19) |
C3—C4 | 1.3958 (16) | C15—H15A | 0.9800 |
C3—H3 | 0.9400 | C15—H15B | 0.9800 |
C4—C5 | 1.3868 (15) | C16—H16A | 0.9700 |
C5—C6 | 1.3859 (15) | C16—H16B | 0.9700 |
C5—H5 | 0.9400 | C16—H16C | 0.9700 |
C6—H6 | 0.9400 | C17—C18 | 1.5025 (19) |
C7—C8 | 1.4505 (16) | C17—H17A | 0.9800 |
C7—H7 | 0.9400 | C17—H17B | 0.9800 |
C8—C13 | 1.3907 (15) | C18—H18A | 0.9700 |
C8—C9 | 1.3997 (15) | C18—H18B | 0.9700 |
C9—C10 | 1.3678 (15) | C18—H18C | 0.9700 |
| | | |
C1—O1—C14 | 117.48 (9) | C12—C11—C10 | 116.55 (10) |
C7—N1—C4 | 119.31 (10) | C13—C12—C11 | 121.08 (10) |
C11—N2—C15 | 121.61 (9) | C13—C12—H12 | 119.5 |
C11—N2—C17 | 122.15 (9) | C11—C12—H12 | 119.5 |
C15—N2—C17 | 115.20 (9) | C12—C13—C8 | 122.25 (10) |
O1—C1—C6 | 124.99 (10) | C12—C13—H13 | 118.9 |
O1—C1—C2 | 115.67 (9) | C8—C13—H13 | 118.9 |
C6—C1—C2 | 119.35 (10) | O1—C14—H14A | 109.5 |
C3—C2—C1 | 120.45 (10) | O1—C14—H14B | 109.5 |
C3—C2—H2 | 119.8 | H14A—C14—H14B | 109.5 |
C1—C2—H2 | 119.8 | O1—C14—H14C | 109.5 |
C2—C3—C4 | 121.04 (10) | H14A—C14—H14C | 109.5 |
C2—C3—H3 | 119.5 | H14B—C14—H14C | 109.5 |
C4—C3—H3 | 119.5 | N2—C15—C16 | 113.41 (11) |
C5—C4—C3 | 117.97 (10) | N2—C15—H15A | 108.9 |
C5—C4—N1 | 123.58 (10) | C16—C15—H15A | 108.9 |
C3—C4—N1 | 118.30 (10) | N2—C15—H15B | 108.9 |
C6—C5—C4 | 121.49 (10) | C16—C15—H15B | 108.9 |
C6—C5—H5 | 119.3 | H15A—C15—H15B | 107.7 |
C4—C5—H5 | 119.3 | C15—C16—H16A | 109.5 |
C5—C6—C1 | 119.68 (10) | C15—C16—H16B | 109.5 |
C5—C6—H6 | 120.2 | H16A—C16—H16B | 109.5 |
C1—C6—H6 | 120.2 | C15—C16—H16C | 109.5 |
N1—C7—C8 | 123.56 (11) | H16A—C16—H16C | 109.5 |
N1—C7—H7 | 118.2 | H16B—C16—H16C | 109.5 |
C8—C7—H7 | 118.2 | N2—C17—C18 | 113.31 (11) |
C13—C8—C9 | 116.81 (10) | N2—C17—H17A | 108.9 |
C13—C8—C7 | 120.93 (10) | C18—C17—H17A | 108.9 |
C9—C8—C7 | 122.25 (10) | N2—C17—H17B | 108.9 |
C10—C9—C8 | 121.97 (10) | C18—C17—H17B | 108.9 |
C10—C9—H9 | 119.0 | H17A—C17—H17B | 107.7 |
C8—C9—H9 | 119.0 | C17—C18—H18A | 109.5 |
C9—C10—C11 | 121.32 (10) | C17—C18—H18B | 109.5 |
C9—C10—H10 | 119.3 | H18A—C18—H18B | 109.5 |
C11—C10—H10 | 119.3 | C17—C18—H18C | 109.5 |
N2—C11—C12 | 121.94 (10) | H18A—C18—H18C | 109.5 |
N2—C11—C10 | 121.51 (10) | H18B—C18—H18C | 109.5 |
| | | |
C14—O1—C1—C6 | −0.78 (16) | C7—C8—C9—C10 | 179.79 (10) |
C14—O1—C1—C2 | 179.17 (10) | C8—C9—C10—C11 | 0.15 (17) |
O1—C1—C2—C3 | 179.63 (10) | C15—N2—C11—C12 | −1.67 (16) |
C6—C1—C2—C3 | −0.42 (16) | C17—N2—C11—C12 | 166.16 (11) |
C1—C2—C3—C4 | −1.05 (17) | C15—N2—C11—C10 | 177.40 (10) |
C2—C3—C4—C5 | 2.01 (17) | C17—N2—C11—C10 | −14.76 (16) |
C2—C3—C4—N1 | 177.64 (10) | C9—C10—C11—N2 | 179.70 (10) |
C7—N1—C4—C5 | −41.89 (16) | C9—C10—C11—C12 | −1.18 (16) |
C7—N1—C4—C3 | 142.74 (11) | N2—C11—C12—C13 | −179.49 (10) |
C3—C4—C5—C6 | −1.56 (17) | C10—C11—C12—C13 | 1.38 (17) |
N1—C4—C5—C6 | −176.95 (10) | C11—C12—C13—C8 | −0.58 (18) |
C4—C5—C6—C1 | 0.15 (17) | C9—C8—C13—C12 | −0.49 (17) |
O1—C1—C6—C5 | −179.19 (10) | C7—C8—C13—C12 | −179.59 (11) |
C2—C1—C6—C5 | 0.86 (16) | C11—N2—C15—C16 | 83.50 (15) |
C4—N1—C7—C8 | 176.85 (10) | C17—N2—C15—C16 | −85.13 (14) |
N1—C7—C8—C13 | 174.93 (11) | C11—N2—C17—C18 | 102.52 (13) |
N1—C7—C8—C9 | −4.12 (17) | C15—N2—C17—C18 | −88.92 (13) |
C13—C8—C9—C10 | 0.70 (16) | | |
Hydrogen-bond geometry (Å, º) topCg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···Cg1i | 0.94 | 2.98 | 3.659 (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. topIIa and IIb refer to the two independent molecules
of compound II' |
Contact | I | II | IIa | IIb | III |
H···H | 62.5 | 58.1 | 53.9 | 55.2 | 59.5 |
C···H/H···C | 26.6 | 29.4 | 34.3 | 32.0 | 29.8 |
N···H/H···N | 5.1 | 6.3 | 5.6 | 6.5 | 5.9 |
O···H/H···O | 5.4 | 6.0 | 6.0 | 6.2 | 4.6 |