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The title compound, C15H15NO2, has been synthesized and characterized by elemental analysis and single-crystal X-ray diffraction. In the crystal structure, the mol­ecules are linked via inter­molecular O—H...O hydrogen bonds into a zigzag chain structure along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001905/rz6166sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001905/rz6166Isup2.hkl
Contains datablock I

CCDC reference: 298530

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.061
  • wR factor = 0.197
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.79
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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

2-[(E)-2-(4-Hydroxyphenyl)ethyliminomethyl]phenol top
Crystal data top
C15H15NO2F(000) = 1024
Mr = 241.28Dx = 1.241 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3701 reflections
a = 15.9378 (13) Åθ = 3.0–25.2°
b = 12.946 (1) ŵ = 0.08 mm1
c = 14.5886 (12) ÅT = 292 K
β = 120.865 (1)°Block, brown
V = 2583.8 (4) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Bruker APEX area-detector
diffractometer
1931 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 26.0°, θmin = 2.2°
φ and ω scansh = 1919
13287 measured reflectionsk = 1515
2545 independent reflectionsl = 1717
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1177P)2 + 0.463P]
where P = (Fo2 + 2Fc2)/3
2545 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
O10.47234 (11)0.19196 (10)0.11912 (12)0.0623 (5)
H10.44660.22760.14440.093*
O20.13146 (13)0.51344 (12)0.45704 (13)0.0712 (5)
H2A0.10230.56760.43050.107*
N10.38766 (12)0.34751 (13)0.14507 (14)0.0569 (5)
C10.46813 (13)0.23996 (14)0.03821 (14)0.0476 (5)
C20.50390 (15)0.19527 (16)0.02223 (17)0.0578 (5)
H20.53260.13020.00370.069*
C30.49757 (17)0.24487 (19)0.10735 (19)0.0704 (6)
H30.52180.21300.14620.085*
C40.4555 (2)0.3426 (2)0.1378 (2)0.0800 (7)
H40.45170.37560.19650.096*
C50.42010 (18)0.38920 (18)0.08107 (19)0.0713 (7)
H50.39180.45430.10150.086*
C60.42559 (13)0.34071 (14)0.00785 (15)0.0508 (5)
C70.38679 (14)0.38956 (15)0.06497 (16)0.0563 (5)
H70.35950.45500.04350.068*
C80.34866 (15)0.39718 (17)0.20564 (18)0.0623 (6)
H8A0.32140.46390.17420.075*
H8B0.40130.40860.27850.075*
C90.27036 (16)0.33156 (18)0.20620 (19)0.0668 (6)
H9A0.21660.32240.13350.080*
H9B0.29700.26390.23510.080*
C100.23295 (14)0.38065 (15)0.27200 (17)0.0550 (5)
C110.17223 (14)0.46685 (16)0.23556 (16)0.0562 (5)
H110.15430.49430.16910.067*
C120.13785 (14)0.51268 (15)0.29529 (16)0.0529 (5)
H120.09770.57050.26920.064*
C130.16327 (14)0.47237 (14)0.39430 (16)0.0511 (5)
C140.22393 (16)0.38712 (15)0.43208 (18)0.0604 (6)
H140.24190.35970.49860.072*
C150.25803 (15)0.34246 (16)0.37121 (18)0.0614 (6)
H150.29890.28520.39780.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0786 (10)0.0514 (8)0.0665 (10)0.0152 (7)0.0441 (8)0.0089 (7)
O20.0983 (12)0.0624 (10)0.0760 (11)0.0095 (8)0.0613 (10)0.0068 (7)
N10.0529 (10)0.0611 (10)0.0593 (10)0.0034 (7)0.0306 (8)0.0084 (8)
C10.0428 (10)0.0480 (10)0.0483 (10)0.0003 (7)0.0207 (8)0.0024 (8)
C20.0540 (11)0.0545 (11)0.0625 (13)0.0059 (9)0.0282 (10)0.0053 (9)
C30.0705 (14)0.0865 (17)0.0629 (13)0.0056 (12)0.0404 (12)0.0063 (12)
C40.0983 (19)0.0885 (17)0.0695 (15)0.0121 (14)0.0548 (15)0.0162 (13)
C50.0820 (16)0.0638 (14)0.0718 (15)0.0149 (11)0.0421 (13)0.0165 (11)
C60.0469 (10)0.0489 (10)0.0540 (11)0.0024 (8)0.0241 (9)0.0023 (8)
C70.0498 (11)0.0514 (11)0.0613 (12)0.0074 (8)0.0240 (10)0.0016 (9)
C80.0548 (12)0.0655 (13)0.0698 (13)0.0005 (9)0.0341 (11)0.0165 (10)
C90.0586 (12)0.0655 (13)0.0790 (15)0.0017 (10)0.0372 (11)0.0167 (11)
C100.0464 (10)0.0554 (12)0.0641 (12)0.0030 (8)0.0289 (9)0.0084 (9)
C110.0528 (11)0.0635 (12)0.0512 (11)0.0058 (9)0.0260 (9)0.0037 (9)
C120.0474 (10)0.0513 (11)0.0581 (12)0.0087 (8)0.0257 (9)0.0049 (9)
C130.0526 (11)0.0465 (10)0.0598 (12)0.0054 (8)0.0328 (9)0.0014 (8)
C140.0665 (13)0.0566 (12)0.0615 (12)0.0039 (10)0.0353 (11)0.0137 (10)
C150.0548 (12)0.0490 (11)0.0781 (15)0.0085 (9)0.0325 (11)0.0065 (10)
Geometric parameters (Å, º) top
O1—C11.305 (2)C7—H70.9300
O1—H10.8200C8—C91.513 (3)
O2—C131.362 (2)C8—H8A0.9700
O2—H2A0.8200C8—H8B0.9700
N1—C71.283 (3)C9—C101.506 (3)
N1—C81.464 (2)C9—H9A0.9700
C1—C21.398 (3)C9—H9B0.9700
C1—C61.431 (3)C10—C151.380 (3)
C2—C31.355 (3)C10—C111.392 (3)
C2—H20.9300C11—C121.379 (3)
C3—C41.394 (3)C11—H110.9300
C3—H30.9300C12—C131.387 (3)
C4—C51.359 (3)C12—H120.9300
C4—H40.9300C13—C141.382 (3)
C5—C61.403 (3)C14—C151.383 (3)
C5—H50.9300C14—H140.9300
C6—C71.416 (3)C15—H150.9300
C1—O1—H1109.5N1—C8—H8B109.4
C13—O2—H2A109.5C9—C8—H8B109.4
C7—N1—C8123.63 (19)H8A—C8—H8B108.0
O1—C1—C2121.69 (17)C10—C9—C8111.34 (17)
O1—C1—C6120.68 (16)C10—C9—H9A109.4
C2—C1—C6117.63 (18)C8—C9—H9A109.4
C3—C2—C1121.30 (19)C10—C9—H9B109.4
C3—C2—H2119.4C8—C9—H9B109.4
C1—C2—H2119.4H9A—C9—H9B108.0
C2—C3—C4121.3 (2)C15—C10—C11117.27 (18)
C2—C3—H3119.3C15—C10—C9121.39 (19)
C4—C3—H3119.3C11—C10—C9121.3 (2)
C5—C4—C3119.4 (2)C12—C11—C10121.84 (19)
C5—C4—H4120.3C12—C11—H11119.1
C3—C4—H4120.3C10—C11—H11119.1
C4—C5—C6121.1 (2)C11—C12—C13119.86 (18)
C4—C5—H5119.5C11—C12—H12120.1
C6—C5—H5119.5C13—C12—H12120.1
C5—C6—C7120.36 (19)O2—C13—C14117.99 (18)
C5—C6—C1119.26 (19)O2—C13—C12122.88 (18)
C7—C6—C1120.36 (18)C14—C13—C12119.13 (18)
N1—C7—C6122.86 (18)C13—C14—C15120.18 (19)
N1—C7—H7118.6C13—C14—H14119.9
C6—C7—H7118.6C15—C14—H14119.9
N1—C8—C9111.30 (17)C10—C15—C14121.71 (19)
N1—C8—H8A109.4C10—C15—H15119.1
C9—C8—H8A109.4C14—C15—H15119.1
O1—C1—C2—C3178.74 (19)C7—N1—C8—C9122.6 (2)
C6—C1—C2—C30.8 (3)N1—C8—C9—C10177.81 (18)
C1—C2—C3—C40.3 (4)C8—C9—C10—C15106.2 (2)
C2—C3—C4—C50.0 (4)C8—C9—C10—C1173.4 (3)
C3—C4—C5—C60.2 (4)C15—C10—C11—C120.2 (3)
C4—C5—C6—C7178.9 (2)C9—C10—C11—C12179.74 (18)
C4—C5—C6—C10.8 (4)C10—C11—C12—C130.4 (3)
O1—C1—C6—C5178.50 (19)C11—C12—C13—O2179.61 (17)
C2—C1—C6—C51.0 (3)C11—C12—C13—C140.7 (3)
O1—C1—C6—C70.4 (3)O2—C13—C14—C15179.87 (18)
C2—C1—C6—C7179.11 (17)C12—C13—C14—C150.5 (3)
C8—N1—C7—C6179.46 (16)C11—C10—C15—C140.5 (3)
C5—C6—C7—N1178.17 (19)C9—C10—C15—C14179.98 (18)
C1—C6—C7—N10.1 (3)C13—C14—C15—C100.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.822.558 (2)150
O2—H2A···O1i0.821.912.725 (2)173
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

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