In the title compound, C
15H
16N
2O, the crystal packing is stabilized by intra- and intermolecular O—H

N, N—H

O and C—H

N hydrogen-bond interactions.
Supporting information
CCDC reference: 610873
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.114
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT355_ALERT_3_C Long O-H Bond (0.82A) O1 - H1 ... 1.04 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
(
E)-2-[1-(3-Amino-2-methylphenylimino)ethyl]phenol
top
Crystal data top
C15H16N2O | F(000) = 512 |
Mr = 240.30 | Dx = 1.213 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 23872 reflections |
a = 11.6558 (7) Å | θ = 2.0–28.0° |
b = 7.9917 (6) Å | µ = 0.08 mm−1 |
c = 16.0978 (10) Å | T = 296 K |
β = 118.619 (4)° | Prism, light yellow |
V = 1316.30 (16) Å3 | 0.55 × 0.46 × 0.39 mm |
Z = 4 | |
Data collection top
Stoe IPDS-2 diffractometer | 2097 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.053 |
Plane graphite monochromator | θmax = 26.0°, θmin = 2.0° |
Detector resolution: 6.67 pixels mm-1 | h = −14→13 |
ω scans | k = −9→9 |
17381 measured reflections | l = −19→19 |
2583 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0574P)2 + 0.1559P] where P = (Fo2 + 2Fc2)/3 |
2583 reflections | (Δ/σ)max < 0.001 |
177 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on
F, and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.82079 (11) | 0.43037 (13) | 0.50437 (8) | 0.0673 (4) | |
N1 | 0.86515 (16) | 0.90998 (18) | 0.85055 (10) | 0.0681 (5) | |
N2 | 0.72074 (10) | 0.47996 (13) | 0.60911 (7) | 0.0469 (3) | |
C1 | 0.79558 (12) | 0.69351 (15) | 0.73072 (9) | 0.0458 (4) | |
C2 | 0.69241 (12) | 0.60305 (15) | 0.66088 (8) | 0.0450 (4) | |
C3 | 0.56379 (13) | 0.63621 (19) | 0.63760 (10) | 0.0572 (5) | |
C4 | 0.53795 (14) | 0.75761 (19) | 0.68707 (11) | 0.0617 (5) | |
C5 | 0.63771 (14) | 0.84460 (17) | 0.75854 (10) | 0.0549 (5) | |
C6 | 0.76681 (13) | 0.81478 (15) | 0.78094 (9) | 0.0479 (4) | |
C7 | 0.93448 (15) | 0.6613 (2) | 0.75372 (12) | 0.0688 (5) | |
C8 | 0.6519 (2) | 0.2527 (2) | 0.67742 (14) | 0.0782 (7) | |
C9 | 0.70056 (13) | 0.32290 (16) | 0.61409 (9) | 0.0481 (4) | |
C10 | 0.73295 (13) | 0.20788 (16) | 0.55736 (9) | 0.0492 (4) | |
C11 | 0.79437 (13) | 0.26690 (18) | 0.50597 (9) | 0.0533 (4) | |
C12 | 0.83099 (17) | 0.1558 (2) | 0.45672 (11) | 0.0712 (6) | |
C13 | 0.8053 (2) | −0.0119 (2) | 0.45639 (13) | 0.0851 (7) | |
C14 | 0.7433 (2) | −0.0716 (2) | 0.50434 (14) | 0.0878 (7) | |
C15 | 0.70838 (18) | 0.03636 (18) | 0.55471 (12) | 0.0697 (6) | |
H1 | 0.784 (2) | 0.489 (2) | 0.5441 (15) | 0.102 (6)* | |
H1A | 0.8409 (17) | 0.963 (2) | 0.8916 (13) | 0.078 (5)* | |
H1B | 0.949 (2) | 0.873 (2) | 0.8732 (13) | 0.083 (6)* | |
H3 | 0.49580 | 0.57730 | 0.58920 | 0.0690* | |
H4 | 0.45190 | 0.78080 | 0.67180 | 0.0740* | |
H5 | 0.61890 | 0.92430 | 0.79240 | 0.0660* | |
H7A | 0.93580 | 0.59450 | 0.70460 | 0.0820* | |
H7B | 0.97890 | 0.60280 | 0.81290 | 0.0820* | |
H7C | 0.97770 | 0.76590 | 0.75840 | 0.0820* | |
H8A | 0.56610 | 0.20670 | 0.63970 | 0.0940* | |
H8B | 0.64820 | 0.33990 | 0.71700 | 0.0940* | |
H8C | 0.71010 | 0.16620 | 0.71620 | 0.0940* | |
H12 | 0.87300 | 0.19490 | 0.42390 | 0.0850* | |
H13 | 0.83010 | −0.08580 | 0.42330 | 0.1020* | |
H14 | 0.72500 | −0.18510 | 0.50270 | 0.1050* | |
H15 | 0.66750 | −0.00560 | 0.58780 | 0.0840* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0876 (8) | 0.0620 (6) | 0.0748 (7) | −0.0032 (5) | 0.0571 (6) | −0.0021 (5) |
N1 | 0.0715 (9) | 0.0663 (8) | 0.0697 (8) | −0.0100 (7) | 0.0363 (7) | −0.0230 (7) |
N2 | 0.0529 (6) | 0.0451 (6) | 0.0451 (6) | 0.0011 (4) | 0.0255 (5) | −0.0016 (4) |
C1 | 0.0500 (7) | 0.0427 (6) | 0.0488 (7) | 0.0013 (5) | 0.0269 (6) | 0.0012 (5) |
C2 | 0.0522 (7) | 0.0435 (6) | 0.0434 (6) | 0.0032 (5) | 0.0263 (6) | 0.0025 (5) |
C3 | 0.0489 (8) | 0.0663 (8) | 0.0534 (8) | 0.0016 (6) | 0.0220 (6) | −0.0054 (6) |
C4 | 0.0522 (8) | 0.0724 (9) | 0.0649 (9) | 0.0116 (7) | 0.0316 (7) | 0.0001 (7) |
C5 | 0.0676 (9) | 0.0505 (7) | 0.0578 (8) | 0.0091 (6) | 0.0391 (7) | 0.0005 (6) |
C6 | 0.0595 (8) | 0.0417 (6) | 0.0479 (7) | −0.0013 (5) | 0.0300 (6) | 0.0008 (5) |
C7 | 0.0526 (8) | 0.0735 (10) | 0.0795 (10) | −0.0028 (7) | 0.0311 (8) | −0.0207 (8) |
C8 | 0.1208 (15) | 0.0567 (9) | 0.0876 (11) | −0.0004 (9) | 0.0745 (12) | 0.0057 (8) |
C9 | 0.0522 (7) | 0.0474 (7) | 0.0438 (6) | 0.0024 (5) | 0.0222 (6) | 0.0025 (5) |
C10 | 0.0535 (7) | 0.0474 (7) | 0.0423 (6) | 0.0049 (5) | 0.0193 (6) | −0.0002 (5) |
C11 | 0.0552 (8) | 0.0569 (8) | 0.0455 (7) | 0.0078 (6) | 0.0223 (6) | −0.0016 (6) |
C12 | 0.0785 (11) | 0.0815 (11) | 0.0596 (9) | 0.0144 (8) | 0.0378 (8) | −0.0082 (8) |
C13 | 0.1053 (14) | 0.0758 (11) | 0.0717 (10) | 0.0225 (10) | 0.0403 (10) | −0.0187 (9) |
C14 | 0.1220 (16) | 0.0517 (9) | 0.0877 (13) | 0.0073 (9) | 0.0487 (12) | −0.0122 (8) |
C15 | 0.0916 (12) | 0.0488 (8) | 0.0699 (10) | 0.0021 (7) | 0.0396 (9) | −0.0011 (7) |
Geometric parameters (Å, º) top
O1—C11 | 1.3453 (18) | C11—C12 | 1.387 (2) |
O1—H1 | 1.04 (2) | C12—C13 | 1.373 (2) |
N1—C6 | 1.385 (2) | C13—C14 | 1.371 (3) |
N2—C2 | 1.4265 (17) | C14—C15 | 1.373 (3) |
N2—C9 | 1.2866 (17) | C3—H3 | 0.9300 |
N1—H1A | 0.94 (2) | C4—H4 | 0.9300 |
N1—H1B | 0.91 (2) | C5—H5 | 0.9300 |
C1—C7 | 1.500 (2) | C7—H7A | 0.9600 |
C1—C2 | 1.3920 (18) | C7—H7B | 0.9600 |
C1—C6 | 1.4018 (19) | C7—H7C | 0.9600 |
C2—C3 | 1.386 (2) | C8—H8A | 0.9600 |
C3—C4 | 1.377 (2) | C8—H8B | 0.9600 |
C4—C5 | 1.370 (2) | C8—H8C | 0.9600 |
C5—C6 | 1.390 (2) | C12—H12 | 0.9300 |
C8—C9 | 1.493 (3) | C13—H13 | 0.9300 |
C9—C10 | 1.467 (2) | C14—H14 | 0.9300 |
C10—C15 | 1.397 (2) | C15—H15 | 0.9300 |
C10—C11 | 1.410 (2) | | |
| | | |
O1···N2 | 2.4987 (18) | H1···N2 | 1.54 (2) |
O1···N1i | 3.270 (2) | H1···C2 | 2.73 (2) |
O1···N1ii | 3.042 (2) | H1···C9 | 2.24 (2) |
O1···H1Bi | 2.50 (2) | H1···H7A | 2.4800 |
O1···H1Aii | 2.118 (19) | H1A···H5 | 2.3200 |
N1···O1iii | 3.042 (2) | H1A···O1iii | 2.118 (19) |
N1···O1iv | 3.270 (2) | H1A···C11iii | 3.050 (18) |
N2···O1 | 2.4987 (18) | H1B···C7 | 2.506 (18) |
N1···H7C | 2.6700 | H1B···H7B | 2.4600 |
N1···H8Cv | 2.9000 | H1B···H7C | 2.2000 |
N2···H1 | 1.54 (2) | H1B···O1iv | 2.50 (2) |
N2···H7A | 2.4100 | H1B···C11iv | 2.81 (2) |
C3···C8 | 3.198 (2) | H3···C8 | 3.1000 |
C5···C8v | 3.546 (2) | H3···C9 | 3.0100 |
C6···C13vi | 3.581 (2) | H3···C9ix | 3.0700 |
C8···C5vii | 3.546 (2) | H3···C10ix | 3.1000 |
C8···C3 | 3.198 (2) | H4···C11ix | 2.9500 |
C13···C6viii | 3.581 (2) | H4···C12ix | 2.9800 |
C1···H13vi | 3.0500 | H5···H1A | 2.3200 |
C2···H1 | 2.73 (2) | H7A···N2 | 2.4100 |
C2···H8B | 2.4400 | H7A···H1 | 2.4800 |
C3···H8B | 2.6500 | H7B···H1B | 2.4600 |
C5···H8Cv | 2.8900 | H7C···N1 | 2.6700 |
C6···H8Cv | 2.9600 | H7C···H1B | 2.2000 |
C6···H13vi | 2.7400 | H8A···C15 | 2.9400 |
C7···H1B | 2.506 (18) | H8A···H15 | 2.4300 |
C8···H15 | 2.5700 | H8B···C2 | 2.4400 |
C8···H3 | 3.1000 | H8B···C3 | 2.6500 |
C9···H1 | 2.24 (2) | H8C···N1vii | 2.9000 |
C9···H3ix | 3.0700 | H8C···C5vii | 2.8900 |
C9···H3 | 3.0100 | H8C···C6vii | 2.9600 |
C10···H3ix | 3.1000 | H8C···C15 | 2.7900 |
C11···H1Bi | 2.81 (2) | H8C···H15 | 2.3300 |
C11···H1Aii | 3.050 (18) | H13···C1viii | 3.0500 |
C11···H4ix | 2.9500 | H13···C6viii | 2.7400 |
C12···H4ix | 2.9800 | H15···C8 | 2.5700 |
C15···H8A | 2.9400 | H15···H8A | 2.4300 |
C15···H8C | 2.7900 | H15···H8C | 2.3300 |
| | | |
C11—O1—H1 | 105.1 (10) | C13—C14—C15 | 119.95 (16) |
C2—N2—C9 | 122.41 (12) | C10—C15—C14 | 121.36 (18) |
C6—N1—H1A | 114.0 (13) | C2—C3—H3 | 120.00 |
C6—N1—H1B | 117.3 (11) | C4—C3—H3 | 120.00 |
H1A—N1—H1B | 119.5 (17) | C3—C4—H4 | 120.00 |
C2—C1—C7 | 121.53 (13) | C5—C4—H4 | 120.00 |
C6—C1—C7 | 120.29 (13) | C4—C5—H5 | 120.00 |
C2—C1—C6 | 118.17 (14) | C6—C5—H5 | 120.00 |
N2—C2—C1 | 118.54 (13) | C1—C7—H7A | 109.00 |
N2—C2—C3 | 119.81 (12) | C1—C7—H7B | 109.00 |
C1—C2—C3 | 121.56 (13) | C1—C7—H7C | 109.00 |
C2—C3—C4 | 119.10 (14) | H7A—C7—H7B | 109.00 |
C3—C4—C5 | 120.69 (16) | H7A—C7—H7C | 110.00 |
C4—C5—C6 | 120.58 (14) | H7B—C7—H7C | 109.00 |
N1—C6—C1 | 120.83 (15) | C9—C8—H8A | 109.00 |
N1—C6—C5 | 119.30 (14) | C9—C8—H8B | 109.00 |
C1—C6—C5 | 119.82 (13) | C9—C8—H8C | 109.00 |
C8—C9—C10 | 119.00 (12) | H8A—C8—H8B | 109.00 |
N2—C9—C8 | 123.34 (13) | H8A—C8—H8C | 109.00 |
N2—C9—C10 | 117.60 (13) | H8B—C8—H8C | 109.00 |
C9—C10—C15 | 121.59 (15) | C11—C12—H12 | 120.00 |
C11—C10—C15 | 117.70 (14) | C13—C12—H12 | 120.00 |
C9—C10—C11 | 120.68 (12) | C12—C13—H13 | 120.00 |
O1—C11—C10 | 121.43 (13) | C14—C13—H13 | 120.00 |
O1—C11—C12 | 118.35 (15) | C13—C14—H14 | 120.00 |
C10—C11—C12 | 120.21 (14) | C15—C14—H14 | 120.00 |
C11—C12—C13 | 120.07 (18) | C10—C15—H15 | 119.00 |
C12—C13—C14 | 120.69 (18) | C14—C15—H15 | 119.00 |
| | | |
C2—N2—C9—C10 | 179.77 (12) | C4—C5—C6—N1 | 177.03 (14) |
C9—N2—C2—C3 | −68.42 (17) | C8—C9—C10—C15 | 5.8 (2) |
C2—N2—C9—C8 | −3.0 (2) | N2—C9—C10—C15 | −176.82 (15) |
C9—N2—C2—C1 | 114.99 (15) | C8—C9—C10—C11 | −172.00 (15) |
C7—C1—C6—C5 | 179.47 (13) | N2—C9—C10—C11 | 5.4 (2) |
C7—C1—C2—N2 | −1.46 (18) | C15—C10—C11—C12 | −1.4 (2) |
C7—C1—C2—C3 | −177.99 (13) | C9—C10—C15—C14 | −177.54 (17) |
C2—C1—C6—C5 | −1.68 (19) | C9—C10—C11—C12 | 176.49 (14) |
C7—C1—C6—N1 | 1.8 (2) | C15—C10—C11—O1 | 179.60 (15) |
C2—C1—C6—N1 | −179.31 (12) | C11—C10—C15—C14 | 0.4 (3) |
C6—C1—C2—C3 | 3.17 (19) | C9—C10—C11—O1 | −2.5 (2) |
C6—C1—C2—N2 | 179.70 (11) | O1—C11—C12—C13 | −179.77 (16) |
C1—C2—C3—C4 | −2.3 (2) | C10—C11—C12—C13 | 1.2 (2) |
N2—C2—C3—C4 | −178.78 (13) | C11—C12—C13—C14 | 0.1 (3) |
C2—C3—C4—C5 | −0.1 (2) | C12—C13—C14—C15 | −1.2 (3) |
C3—C4—C5—C6 | 1.6 (2) | C13—C14—C15—C10 | 0.9 (3) |
C4—C5—C6—C1 | −0.7 (2) | | |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+2, y+1/2, −z+3/2; (v) x, y+1, z; (vi) x, −y+1/2, z+1/2; (vii) x, y−1, z; (viii) x, −y+1/2, z−1/2; (ix) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 1.04 (2) | 1.54 (2) | 2.4987 (18) | 150.4 (15) |
N1—H1A···O1iii | 0.94 (2) | 2.118 (19) | 3.042 (2) | 169.4 (17) |
N1—H1B···O1iv | 0.91 (2) | 2.50 (2) | 3.270 (2) | 142.8 (14) |
C7—H7A···N2 | 0.96 | 2.41 | 2.858 (2) | 108 |
Symmetry codes: (iii) x, −y+3/2, z+1/2; (iv) −x+2, y+1/2, −z+3/2. |