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In the title compound, C15H16N2O, the crystal packing is stabilized by intra- and inter­molecular O—H...N, N—H...O and C—H...N hydrogen-bond inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015650/rz2021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015650/rz2021Isup2.hkl
Contains datablock I

CCDC reference: 610873

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Computing details top

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
C15H16N2OF(000) = 512
Mr = 240.30Dx = 1.213 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 23872 reflections
a = 11.6558 (7) Åθ = 2.0–28.0°
b = 7.9917 (6) ŵ = 0.08 mm1
c = 16.0978 (10) ÅT = 296 K
β = 118.619 (4)°Prism, light yellow
V = 1316.30 (16) Å30.55 × 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 focusRint = 0.053
Plane graphite monochromatorθmax = 26.0°, θmin = 2.0°
Detector resolution: 6.67 pixels mm-1h = 1413
ω scansk = 99
17381 measured reflectionsl = 1919
2583 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H 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 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.16 e Å3
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
xyzUiso*/Ueq
O10.82079 (11)0.43037 (13)0.50437 (8)0.0673 (4)
N10.86515 (16)0.90998 (18)0.85055 (10)0.0681 (5)
N20.72074 (10)0.47996 (13)0.60911 (7)0.0469 (3)
C10.79558 (12)0.69351 (15)0.73072 (9)0.0458 (4)
C20.69241 (12)0.60305 (15)0.66088 (8)0.0450 (4)
C30.56379 (13)0.63621 (19)0.63760 (10)0.0572 (5)
C40.53795 (14)0.75761 (19)0.68707 (11)0.0617 (5)
C50.63771 (14)0.84460 (17)0.75854 (10)0.0549 (5)
C60.76681 (13)0.81478 (15)0.78094 (9)0.0479 (4)
C70.93448 (15)0.6613 (2)0.75372 (12)0.0688 (5)
C80.6519 (2)0.2527 (2)0.67742 (14)0.0782 (7)
C90.70056 (13)0.32290 (16)0.61409 (9)0.0481 (4)
C100.73295 (13)0.20788 (16)0.55736 (9)0.0492 (4)
C110.79437 (13)0.26690 (18)0.50597 (9)0.0533 (4)
C120.83099 (17)0.1558 (2)0.45672 (11)0.0712 (6)
C130.8053 (2)0.0119 (2)0.45639 (13)0.0851 (7)
C140.7433 (2)0.0716 (2)0.50434 (14)0.0878 (7)
C150.70838 (18)0.03636 (18)0.55471 (12)0.0697 (6)
H10.784 (2)0.489 (2)0.5441 (15)0.102 (6)*
H1A0.8409 (17)0.963 (2)0.8916 (13)0.078 (5)*
H1B0.949 (2)0.873 (2)0.8732 (13)0.083 (6)*
H30.495800.577300.589200.0690*
H40.451900.780800.671800.0740*
H50.618900.924300.792400.0660*
H7A0.935800.594500.704600.0820*
H7B0.978900.602800.812900.0820*
H7C0.977700.765900.758400.0820*
H8A0.566100.206700.639700.0940*
H8B0.648200.339900.717000.0940*
H8C0.710100.166200.716200.0940*
H120.873000.194900.423900.0850*
H130.830100.085800.423300.1020*
H140.725000.185100.502700.1050*
H150.667500.005600.587800.0840*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0876 (8)0.0620 (6)0.0748 (7)0.0032 (5)0.0571 (6)0.0021 (5)
N10.0715 (9)0.0663 (8)0.0697 (8)0.0100 (7)0.0363 (7)0.0230 (7)
N20.0529 (6)0.0451 (6)0.0451 (6)0.0011 (4)0.0255 (5)0.0016 (4)
C10.0500 (7)0.0427 (6)0.0488 (7)0.0013 (5)0.0269 (6)0.0012 (5)
C20.0522 (7)0.0435 (6)0.0434 (6)0.0032 (5)0.0263 (6)0.0025 (5)
C30.0489 (8)0.0663 (8)0.0534 (8)0.0016 (6)0.0220 (6)0.0054 (6)
C40.0522 (8)0.0724 (9)0.0649 (9)0.0116 (7)0.0316 (7)0.0001 (7)
C50.0676 (9)0.0505 (7)0.0578 (8)0.0091 (6)0.0391 (7)0.0005 (6)
C60.0595 (8)0.0417 (6)0.0479 (7)0.0013 (5)0.0300 (6)0.0008 (5)
C70.0526 (8)0.0735 (10)0.0795 (10)0.0028 (7)0.0311 (8)0.0207 (8)
C80.1208 (15)0.0567 (9)0.0876 (11)0.0004 (9)0.0745 (12)0.0057 (8)
C90.0522 (7)0.0474 (7)0.0438 (6)0.0024 (5)0.0222 (6)0.0025 (5)
C100.0535 (7)0.0474 (7)0.0423 (6)0.0049 (5)0.0193 (6)0.0002 (5)
C110.0552 (8)0.0569 (8)0.0455 (7)0.0078 (6)0.0223 (6)0.0016 (6)
C120.0785 (11)0.0815 (11)0.0596 (9)0.0144 (8)0.0378 (8)0.0082 (8)
C130.1053 (14)0.0758 (11)0.0717 (10)0.0225 (10)0.0403 (10)0.0187 (9)
C140.1220 (16)0.0517 (9)0.0877 (13)0.0073 (9)0.0487 (12)0.0122 (8)
C150.0916 (12)0.0488 (8)0.0699 (10)0.0021 (7)0.0396 (9)0.0011 (7)
Geometric parameters (Å, º) top
O1—C111.3453 (18)C11—C121.387 (2)
O1—H11.04 (2)C12—C131.373 (2)
N1—C61.385 (2)C13—C141.371 (3)
N2—C21.4265 (17)C14—C151.373 (3)
N2—C91.2866 (17)C3—H30.9300
N1—H1A0.94 (2)C4—H40.9300
N1—H1B0.91 (2)C5—H50.9300
C1—C71.500 (2)C7—H7A0.9600
C1—C21.3920 (18)C7—H7B0.9600
C1—C61.4018 (19)C7—H7C0.9600
C2—C31.386 (2)C8—H8A0.9600
C3—C41.377 (2)C8—H8B0.9600
C4—C51.370 (2)C8—H8C0.9600
C5—C61.390 (2)C12—H120.9300
C8—C91.493 (3)C13—H130.9300
C9—C101.467 (2)C14—H140.9300
C10—C151.397 (2)C15—H150.9300
C10—C111.410 (2)
O1···N22.4987 (18)H1···N21.54 (2)
O1···N1i3.270 (2)H1···C22.73 (2)
O1···N1ii3.042 (2)H1···C92.24 (2)
O1···H1Bi2.50 (2)H1···H7A2.4800
O1···H1Aii2.118 (19)H1A···H52.3200
N1···O1iii3.042 (2)H1A···O1iii2.118 (19)
N1···O1iv3.270 (2)H1A···C11iii3.050 (18)
N2···O12.4987 (18)H1B···C72.506 (18)
N1···H7C2.6700H1B···H7B2.4600
N1···H8Cv2.9000H1B···H7C2.2000
N2···H11.54 (2)H1B···O1iv2.50 (2)
N2···H7A2.4100H1B···C11iv2.81 (2)
C3···C83.198 (2)H3···C83.1000
C5···C8v3.546 (2)H3···C93.0100
C6···C13vi3.581 (2)H3···C9ix3.0700
C8···C5vii3.546 (2)H3···C10ix3.1000
C8···C33.198 (2)H4···C11ix2.9500
C13···C6viii3.581 (2)H4···C12ix2.9800
C1···H13vi3.0500H5···H1A2.3200
C2···H12.73 (2)H7A···N22.4100
C2···H8B2.4400H7A···H12.4800
C3···H8B2.6500H7B···H1B2.4600
C5···H8Cv2.8900H7C···N12.6700
C6···H8Cv2.9600H7C···H1B2.2000
C6···H13vi2.7400H8A···C152.9400
C7···H1B2.506 (18)H8A···H152.4300
C8···H152.5700H8B···C22.4400
C8···H33.1000H8B···C32.6500
C9···H12.24 (2)H8C···N1vii2.9000
C9···H3ix3.0700H8C···C5vii2.8900
C9···H33.0100H8C···C6vii2.9600
C10···H3ix3.1000H8C···C152.7900
C11···H1Bi2.81 (2)H8C···H152.3300
C11···H1Aii3.050 (18)H13···C1viii3.0500
C11···H4ix2.9500H13···C6viii2.7400
C12···H4ix2.9800H15···C82.5700
C15···H8A2.9400H15···H8A2.4300
C15···H8C2.7900H15···H8C2.3300
C11—O1—H1105.1 (10)C13—C14—C15119.95 (16)
C2—N2—C9122.41 (12)C10—C15—C14121.36 (18)
C6—N1—H1A114.0 (13)C2—C3—H3120.00
C6—N1—H1B117.3 (11)C4—C3—H3120.00
H1A—N1—H1B119.5 (17)C3—C4—H4120.00
C2—C1—C7121.53 (13)C5—C4—H4120.00
C6—C1—C7120.29 (13)C4—C5—H5120.00
C2—C1—C6118.17 (14)C6—C5—H5120.00
N2—C2—C1118.54 (13)C1—C7—H7A109.00
N2—C2—C3119.81 (12)C1—C7—H7B109.00
C1—C2—C3121.56 (13)C1—C7—H7C109.00
C2—C3—C4119.10 (14)H7A—C7—H7B109.00
C3—C4—C5120.69 (16)H7A—C7—H7C110.00
C4—C5—C6120.58 (14)H7B—C7—H7C109.00
N1—C6—C1120.83 (15)C9—C8—H8A109.00
N1—C6—C5119.30 (14)C9—C8—H8B109.00
C1—C6—C5119.82 (13)C9—C8—H8C109.00
C8—C9—C10119.00 (12)H8A—C8—H8B109.00
N2—C9—C8123.34 (13)H8A—C8—H8C109.00
N2—C9—C10117.60 (13)H8B—C8—H8C109.00
C9—C10—C15121.59 (15)C11—C12—H12120.00
C11—C10—C15117.70 (14)C13—C12—H12120.00
C9—C10—C11120.68 (12)C12—C13—H13120.00
O1—C11—C10121.43 (13)C14—C13—H13120.00
O1—C11—C12118.35 (15)C13—C14—H14120.00
C10—C11—C12120.21 (14)C15—C14—H14120.00
C11—C12—C13120.07 (18)C10—C15—H15119.00
C12—C13—C14120.69 (18)C14—C15—H15119.00
C2—N2—C9—C10179.77 (12)C4—C5—C6—N1177.03 (14)
C9—N2—C2—C368.42 (17)C8—C9—C10—C155.8 (2)
C2—N2—C9—C83.0 (2)N2—C9—C10—C15176.82 (15)
C9—N2—C2—C1114.99 (15)C8—C9—C10—C11172.00 (15)
C7—C1—C6—C5179.47 (13)N2—C9—C10—C115.4 (2)
C7—C1—C2—N21.46 (18)C15—C10—C11—C121.4 (2)
C7—C1—C2—C3177.99 (13)C9—C10—C15—C14177.54 (17)
C2—C1—C6—C51.68 (19)C9—C10—C11—C12176.49 (14)
C7—C1—C6—N11.8 (2)C15—C10—C11—O1179.60 (15)
C2—C1—C6—N1179.31 (12)C11—C10—C15—C140.4 (3)
C6—C1—C2—C33.17 (19)C9—C10—C11—O12.5 (2)
C6—C1—C2—N2179.70 (11)O1—C11—C12—C13179.77 (16)
C1—C2—C3—C42.3 (2)C10—C11—C12—C131.2 (2)
N2—C2—C3—C4178.78 (13)C11—C12—C13—C140.1 (3)
C2—C3—C4—C50.1 (2)C12—C13—C14—C151.2 (3)
C3—C4—C5—C61.6 (2)C13—C14—C15—C100.9 (3)
C4—C5—C6—C10.7 (2)
Symmetry codes: (i) x+2, y1/2, z+3/2; (ii) x, y+3/2, z1/2; (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, y1, z; (viii) x, y+1/2, z1/2; (ix) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N21.04 (2)1.54 (2)2.4987 (18)150.4 (15)
N1—H1A···O1iii0.94 (2)2.118 (19)3.042 (2)169.4 (17)
N1—H1B···O1iv0.91 (2)2.50 (2)3.270 (2)142.8 (14)
C7—H7A···N20.962.412.858 (2)108
Symmetry codes: (iii) x, y+3/2, z+1/2; (iv) x+2, y+1/2, z+3/2.
 

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