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The title compound, C16H15NO2·C2H5OH, has been synthesized by the reaction of benzoyl­acetone with 2-amino­phenol in ethanol. The en­amino­ne structure is stabilized by a strong intramolecular hydrogen bond (N—H...O=C), while the one-dimensional infinite chain in the [010] direction is formed by the intermolecular O—H...O hydrogen bond between the en­amino­ne and the ethanol solvent mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008925/wn6333sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008925/wn6333Isup2.hkl
Contains datablock I

CCDC reference: 270568

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.058
  • wR factor = 0.189
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C17
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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 for Windows (Farrugia, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

3-[(2-Hydroxyphenyl)amino]-1-phenylbut-3-en-1-one ethanol solvate top
Crystal data top
C16H15NO2·C2H6OF(000) = 640
Mr = 299.36Dx = 1.172 Mg m3
Monoclinic, P21/nMelting point = 443–444 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 7.663 (4) ÅCell parameters from 874 reflections
b = 12.119 (7) Åθ = 2.8–24.6°
c = 18.303 (9) ŵ = 0.08 mm1
β = 93.217 (14)°T = 293 K
V = 1697.1 (16) Å3Block, yellow
Z = 40.24 × 0.22 × 0.16 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
3484 independent reflections
Radiation source: fine-focus sealed tube1948 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 96
Tmin = 0.967, Tmax = 0.987k = 1115
9539 measured reflectionsl = 2123
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.098P)2 + 0.1387P]
where P = (Fo2 + 2Fc2)/3
3484 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.36 e Å3
13 restraintsΔρmin = 0.31 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
O10.6993 (2)0.60400 (15)0.15996 (9)0.0606 (5)
O20.5231 (2)0.31564 (16)0.16477 (12)0.0697 (6)
H20.55040.25150.17400.105*
O30.6332 (3)0.11673 (17)0.20749 (11)0.0768 (6)
H30.68620.11330.24760.115*
N10.3945 (2)0.51182 (17)0.12723 (11)0.0537 (6)
H10.48670.51990.15580.064*
C10.2313 (3)0.5726 (2)0.01485 (15)0.0677 (8)
H1A0.19210.49750.01020.102*
H1B0.26420.59890.03190.102*
H1C0.13860.61760.03170.102*
C20.3856 (3)0.5783 (2)0.06868 (14)0.0523 (6)
C30.5203 (3)0.6510 (2)0.05637 (14)0.0545 (6)
H3A0.50850.69650.01550.065*
C40.6751 (3)0.6606 (2)0.10225 (13)0.0492 (6)
C50.8168 (3)0.73719 (19)0.08121 (13)0.0507 (6)
C60.8361 (4)0.7725 (2)0.00976 (16)0.0637 (7)
H60.75540.74990.02710.076*
C70.9716 (4)0.8400 (3)0.00749 (18)0.0794 (9)
H70.98130.86330.05550.095*
C81.0937 (4)0.8734 (3)0.04651 (19)0.0822 (9)
H81.18590.91880.03480.099*
C91.0785 (4)0.8395 (3)0.11698 (18)0.0821 (9)
H91.16020.86200.15340.098*
C100.9416 (4)0.7716 (2)0.13416 (15)0.0674 (8)
H100.93310.74850.18230.081*
C110.2765 (3)0.4305 (2)0.14960 (13)0.0511 (6)
C120.3469 (3)0.3287 (2)0.17103 (13)0.0528 (6)
C130.2397 (4)0.2478 (3)0.19730 (14)0.0666 (8)
H130.28630.18020.21250.080*
C140.0624 (4)0.2680 (3)0.20077 (16)0.0753 (9)
H140.00970.21340.21830.090*
C150.0079 (4)0.3668 (3)0.17883 (18)0.0806 (9)
H150.12750.37880.18050.097*
C160.0985 (3)0.4490 (3)0.15419 (15)0.0687 (8)
H160.05100.51700.14060.082*
C170.6818 (5)0.0288 (4)0.16451 (18)0.1028 (12)
H17A0.69010.03770.19400.123*
H17B0.79580.04320.14610.123*
C180.5478 (6)0.0114 (5)0.0999 (2)0.167 (2)
H18A0.43820.01130.11800.250*
H18B0.58940.04450.06810.250*
H18C0.53200.07930.07330.250*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0579 (10)0.0660 (12)0.0560 (10)0.0125 (8)0.0152 (8)0.0128 (9)
O20.0450 (10)0.0721 (13)0.0915 (14)0.0060 (8)0.0006 (9)0.0250 (11)
O30.0950 (15)0.0672 (14)0.0654 (12)0.0201 (11)0.0197 (10)0.0035 (11)
N10.0409 (10)0.0580 (13)0.0607 (13)0.0023 (9)0.0117 (9)0.0001 (11)
C10.0520 (15)0.0749 (19)0.0737 (18)0.0073 (13)0.0185 (13)0.0008 (15)
C20.0454 (13)0.0507 (15)0.0595 (15)0.0119 (11)0.0086 (11)0.0053 (12)
C30.0495 (14)0.0513 (15)0.0610 (15)0.0050 (11)0.0115 (11)0.0058 (12)
C40.0530 (14)0.0427 (13)0.0510 (14)0.0043 (11)0.0056 (10)0.0016 (12)
C50.0545 (14)0.0424 (14)0.0545 (15)0.0023 (11)0.0030 (11)0.0016 (12)
C60.0712 (17)0.0572 (17)0.0619 (17)0.0027 (14)0.0042 (13)0.0026 (14)
C70.094 (2)0.070 (2)0.075 (2)0.0103 (17)0.0106 (17)0.0158 (17)
C80.078 (2)0.072 (2)0.097 (2)0.0240 (16)0.0057 (17)0.0154 (19)
C90.080 (2)0.082 (2)0.083 (2)0.0323 (17)0.0109 (16)0.0111 (18)
C100.0714 (17)0.0690 (19)0.0606 (17)0.0185 (15)0.0076 (13)0.0096 (14)
C110.0415 (12)0.0615 (17)0.0496 (14)0.0042 (11)0.0038 (10)0.0044 (12)
C120.0411 (13)0.0696 (18)0.0468 (14)0.0046 (12)0.0054 (10)0.0011 (12)
C130.0626 (16)0.072 (2)0.0643 (17)0.0130 (14)0.0015 (13)0.0059 (15)
C140.0576 (17)0.095 (2)0.074 (2)0.0240 (17)0.0044 (14)0.0000 (18)
C150.0436 (15)0.106 (3)0.092 (2)0.0090 (17)0.0095 (14)0.015 (2)
C160.0449 (14)0.077 (2)0.084 (2)0.0050 (14)0.0017 (13)0.0113 (16)
C170.122 (3)0.099 (3)0.087 (2)0.020 (2)0.001 (2)0.010 (2)
C180.163 (4)0.182 (5)0.149 (4)0.027 (4)0.044 (3)0.076 (4)
Geometric parameters (Å, º) top
O1—C41.264 (3)C8—C91.365 (4)
O2—C121.370 (3)C8—H80.9300
O2—H20.8200C9—C101.383 (4)
O3—C171.387 (4)C9—H90.9300
O3—H30.8200C10—H100.9300
N1—C21.339 (3)C11—C161.389 (3)
N1—C111.414 (3)C11—C121.394 (4)
N1—H10.8600C12—C131.383 (4)
C1—C21.498 (3)C13—C141.386 (4)
C1—H1A0.9600C13—H130.9300
C1—H1B0.9600C14—C151.365 (5)
C1—H1C0.9600C14—H140.9300
C2—C31.385 (4)C15—C161.378 (4)
C3—C41.420 (3)C15—H150.9300
C3—H3A0.9300C16—H160.9300
C4—C51.496 (3)C17—C181.537 (5)
C5—C101.387 (3)C17—H17A0.9700
C5—C61.392 (4)C17—H17B0.9700
C6—C71.373 (4)C18—H18A0.9600
C6—H60.9300C18—H18B0.9600
C7—C81.383 (4)C18—H18C0.9600
C7—H70.9300
C12—O2—H2109.5C10—C9—H9120.0
C17—O3—H3109.5C9—C10—C5121.5 (3)
C2—N1—C11130.3 (2)C9—C10—H10119.3
C2—N1—H1114.9C5—C10—H10119.3
C11—N1—H1114.9C16—C11—C12119.5 (2)
C2—C1—H1A109.5C16—C11—N1123.5 (3)
C2—C1—H1B109.5C12—C11—N1117.0 (2)
H1A—C1—H1B109.5O2—C12—C13123.7 (3)
C2—C1—H1C109.5O2—C12—C11116.5 (2)
H1A—C1—H1C109.5C13—C12—C11119.8 (2)
H1B—C1—H1C109.5C12—C13—C14119.6 (3)
N1—C2—C3120.6 (2)C12—C13—H13120.2
N1—C2—C1120.1 (2)C14—C13—H13120.2
C3—C2—C1119.4 (2)C15—C14—C13120.9 (3)
C2—C3—C4124.1 (2)C15—C14—H14119.6
C2—C3—H3A117.9C13—C14—H14119.6
C4—C3—H3A117.9C14—C15—C16119.9 (3)
O1—C4—C3121.9 (2)C14—C15—H15120.0
O1—C4—C5118.5 (2)C16—C15—H15120.0
C3—C4—C5119.6 (2)C15—C16—C11120.3 (3)
C10—C5—C6117.3 (2)C15—C16—H16119.9
C10—C5—C4119.3 (2)C11—C16—H16119.9
C6—C5—C4123.3 (2)O3—C17—C18110.7 (3)
C7—C6—C5121.4 (3)O3—C17—H17A109.5
C7—C6—H6119.3C18—C17—H17A109.5
C5—C6—H6119.3O3—C17—H17B109.5
C6—C7—C8120.0 (3)C18—C17—H17B109.5
C6—C7—H7120.0H17A—C17—H17B108.1
C8—C7—H7120.0C17—C18—H18A109.5
C9—C8—C7119.8 (3)C17—C18—H18B109.5
C9—C8—H8120.1H18A—C18—H18B109.5
C7—C8—H8120.1C17—C18—H18C109.5
C8—C9—C10120.0 (3)H18A—C18—H18C109.5
C8—C9—H9120.0H18B—C18—H18C109.5
C11—N1—C2—C3178.3 (2)C6—C5—C10—C90.9 (4)
C11—N1—C2—C10.2 (4)C4—C5—C10—C9177.8 (3)
N1—C2—C3—C40.8 (4)C2—N1—C11—C1649.8 (4)
C1—C2—C3—C4177.7 (2)C2—N1—C11—C12133.2 (3)
C2—C3—C4—O12.0 (4)C16—C11—C12—O2179.6 (2)
C2—C3—C4—C5176.3 (2)N1—C11—C12—O23.2 (3)
O1—C4—C5—C1020.6 (4)C16—C11—C12—C130.7 (4)
C3—C4—C5—C10161.0 (2)N1—C11—C12—C13176.5 (2)
O1—C4—C5—C6156.1 (2)O2—C12—C13—C14179.2 (2)
C3—C4—C5—C622.2 (4)C11—C12—C13—C141.2 (4)
C10—C5—C6—C70.9 (4)C12—C13—C14—C150.2 (4)
C4—C5—C6—C7177.8 (3)C13—C14—C15—C161.3 (5)
C5—C6—C7—C80.7 (5)C14—C15—C16—C111.8 (4)
C6—C7—C8—C90.3 (5)C12—C11—C16—C150.8 (4)
C7—C8—C9—C100.3 (5)N1—C11—C16—C15177.8 (3)
C8—C9—C10—C50.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.922.628 (3)139
O2—H2···O30.821.842.657 (3)171
O3—H3···O1i0.821.862.685 (3)178
Symmetry code: (i) x+3/2, y1/2, z+1/2.
 

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