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In the title mol­ecule, C17H20N2O2, the angle between the mean planes of the 3-hydroxy­phenyl and cyclo­hexa-2,4-dien-1-one rings is 10.7 (7)°. Intra­molecular N—H...O hydrogen bonding involving the amine H atom and the carbonyl O atom affects the conformation of the mol­ecule. One of the ethyl arms is disordered over two conformations with occupancies of 0.766 (8) and 0.234 (8). Crystal packing is stabilized by inter­molecular C—H...O hydrogen bonding between the major component of the disordered ethyl C atom and a nearby carbonyl O atom, and by O—H...O hydrogen bonding between the hydroxyl H atom and the carbonyl O atom. This links the molecules into chains in an alternate inverted pattern, parallel, oblique and diagonal to the bc face of the unit cell.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053652/sj2389sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053652/sj2389Isup2.hkl
Contains datablock I

CCDC reference: 672839

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.083
  • wR factor = 0.270
  • Data-to-parameter ratio = 24.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 38 Perc.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.827 1.000 Tmin(prime) and Tmax expected: 0.954 0.978 RR(prime) = 0.847 Please check that your absorption correction is appropriate. RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.270 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT084_ALERT_2_C High R2 Value .................................. 0.27 PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14B PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.978 Tmax scaled 0.978 Tmin scaled 0.808
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives are also known to have biological activities such as antimicrobial (El-Masry et al. 2000; Pandey et al. 1999); antifungal (Singh & Dash 1988; Varma et al. 1986); antitumor (Hodnett & Dunn 1970; Misra et al. 1981; Agarwal et al. 1983) and as herbicides (Samadhiya & Halve, 2001). The crystal structures of (E)-2-hydroxy-5-methyl-3-[(4-methyl-2 pyridyl)iminomethyl] benzaldehyde (Büyükgüngör, et al. 2007); (E)-2-hydroxy-5-methyl-3-[(2-pyridylimino) methyl]benzaldehyde (Odabaşoğlu, et al. 2007); 1-(4-{[(E)-(4-diethylamino-2-hydroxy phenyl)methylene]amino}phenyl)ethanone (Yathirajan et al. 2007) and 2-{(E)-[(2-chloro-5-nitrophenyl)imino]methyl}-5-(diethylamino)phenol (Butcher et al. 2007); 6(Z)-((2-hydroxyphenylamino)methylene)-3-(diethylamino)cyclohexyl-2,4-dien-1-one (Bohme & Fels, 2006) and N-(2-hydroxybenzylidene)-4-diethylamino-2-hydroxyaniline (Nagao et al. 2002) have been reported previously. The title compound (6Z)-3-(diethylamino)-6-{[(3-hydroxyphenyl)amino]methylene} cyclohexa-2,4-dien-1-one, (I), C17H20N2O2 was the unexpected product of an attempt to synthesize a new Schiff base, 5-(diethylamino)-2-{(E)-[(3-hydroxyphenyl)imino]methyl}phenol by enolization and its crystal structure is reported here.

The angle between the mean planes of the planar 3-hydroxyphenyl and cyclohexa-2,4-dien-1-one groups of the title molecule is 10.7 (7)° Fig. 1). These two rings are twisted slightly about the methylene amino group with torsion angles of -9.5 (4) [C7—N1—C5—C4] and 178.9 (2) [N1—C7—C8—C9], respectively. Intramolecular N1—H1A···O2 hydrogen bonding contributes to the overall planarity of the molecule. One of the ethyl arms is disordered over two conformations which are constrained to have similar metrical parameters with occupancies of 0.234 (8) [C14A] and 0.766 (8) [C15A] respectively. Crystal packing is stabilized by intermolecular C15A—H1A···O2 and O1—H1B···O2 hydrogen bonds (Fig 2) that link the molecules into chains in an alternate inverted pattern, which is parallel and oblique to the bc face and diagonal to the a axis of the unit cell (Fig. 2).

Related literature top

For related structures, see: Nagao et al. (2002); Bohme & Fels (2006); Butcher et al. (2007); Büyükgüngör et al. (2007); Odabaşoğlu et al. (2007); Yathirajan et al. (2007); For details of the biological activities of Schiff base derivatives, see: Hodnett & Dunn (1970); Misra et al. (1981); Agarwal et al. (1983); Varma et al. (1986); Singh & Dash (1988); Pandey et al. (1999); El-Masry et al. (2000); Samadhiya & Halve (2001).

Experimental top

A mixture of 3-aminophenol (1.09 g, 0.01 mol) and 4-(diethylamino)-2-hydroxybenzaldehyde (1.92 g, 0.01 mol) in 25 ml of absolute ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 4 h (Fig. 3). On cooling, the solid separated was filtered and recrystallized from acetone (m.p.: 467–473 K). The expected product was 5-(diethylamino)-2-{(E)-[(3-hydroxyphenyl)imino]methyl}phenol, but the structure observed is that of its tautomeric form, (6Z)-3-(diethylamino)-6-{[(3-hydroxyphenyl)amino]methylene}cyclohexa-2,4- dien-1-one. Analysis found: C 70.73, H 7.01, N 9.78%; C17H20N2O2 requires: C 70.81, H 7.09, N 9.85%.

Refinement top

The C14A–C15A ethyl group was disordered over two positions A and B and the occupancy factors refined to 0.766 (8) and 0.234 (8); the two components were constrained to have similar metrical parameters. Owing to the poor diffraction qualities of the crystal, the ratio of observed to unique reflelctions is low (38%).

All H atoms were placed in calculated positions except H1A and H1B which were found in a difference map. All H atoms were refined using a riding model with O—H = 0.82 Å, N—H = 0.86 Å and C—H = 0.93 to 0.97 Å, and with Uiso(H) = 1.0–1.5Ueq(C,O,N).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing atom labeling and 50% probability displacement ellipsoids. Only the major disorder components C14A and C15A are displayed. The dashed line indicates the intramolecular hydrogen bond.
[Figure 2] Fig. 2. Packing diagram for (I), viewed down the b axis with hydrogen bonds drawn as dashed lines.
[Figure 3] Fig. 3. Synthesis of the title compound.
(6Z)-3-Diethylamino-6-(3-hydroxyanilinomethylene)cyclohexa-2,4-dien-1-one top
Crystal data top
C17H20N2O2F(000) = 608
Mr = 284.35Dx = 1.266 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabCell parameters from 3116 reflections
a = 7.4780 (6) Åθ = 4.8–32.5°
b = 15.822 (2) ŵ = 0.08 mm1
c = 12.6372 (13) ÅT = 296 K
β = 94.149 (9)°Chunk, pale yellow
V = 1491.3 (3) Å30.55 × 0.43 × 0.27 mm
Z = 4
Data collection top
Oxford Diffraction Gemini
diffractometer
4836 independent reflections
Radiation source: fine-focus sealed tube1828 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 10.5081 pixels mm-1θmax = 32.6°, θmin = 4.8°
ϕ and ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 2222
Tmin = 0.827, Tmax = 1.000l = 1919
13075 measured 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)] = 0.083Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.270H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1294P)2]
where P = (Fo2 + 2Fc2)/3
4836 reflections(Δ/σ)max = 0.004
201 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C17H20N2O2V = 1491.3 (3) Å3
Mr = 284.35Z = 4
Monoclinic, P21/aMo Kα radiation
a = 7.4780 (6) ŵ = 0.08 mm1
b = 15.822 (2) ÅT = 296 K
c = 12.6372 (13) Å0.55 × 0.43 × 0.27 mm
β = 94.149 (9)°
Data collection top
Oxford Diffraction Gemini
diffractometer
4836 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
1828 reflections with I > 2σ(I)
Tmin = 0.827, Tmax = 1.000Rint = 0.058
13075 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0830 restraints
wR(F2) = 0.270H-atom parameters constrained
S = 1.02Δρmax = 0.37 e Å3
4836 reflectionsΔρmin = 0.19 e Å3
201 parameters
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*/UeqOcc. (<1)
O10.7397 (2)0.07199 (13)1.24994 (15)0.0716 (6)
H1B0.75970.03881.20070.107*
O20.17605 (19)0.04039 (11)0.89295 (12)0.0577 (5)
N10.1930 (2)0.10814 (12)1.07924 (14)0.0480 (5)
H1A0.23860.07461.03100.058*
N20.3053 (3)0.11735 (17)0.68516 (17)0.0750 (7)
C10.5685 (3)0.09987 (15)1.25042 (18)0.0511 (6)
C20.4974 (3)0.14220 (17)1.3390 (2)0.0617 (7)
H2A0.56650.15001.39650.074*
C30.3255 (3)0.17289 (19)1.3430 (2)0.0713 (8)
H3A0.27940.20131.40340.086*
C40.2198 (3)0.16219 (19)1.2589 (2)0.0655 (7)
H4A0.10330.18311.26200.079*
C50.2913 (3)0.11953 (14)1.16938 (17)0.0451 (5)
C60.4639 (3)0.08804 (14)1.16547 (17)0.0474 (6)
H6A0.51010.05891.10570.057*
C70.0377 (3)0.14383 (15)1.06111 (18)0.0496 (6)
H7A0.01810.17761.11390.060*
C80.0459 (3)0.13346 (14)0.96764 (17)0.0456 (5)
C90.2103 (3)0.17529 (17)0.9547 (2)0.0616 (7)
H9A0.26160.20761.01040.074*
C100.2951 (3)0.16995 (19)0.8644 (2)0.0684 (8)
H10A0.40250.19870.85890.082*
C110.2219 (3)0.12066 (16)0.77704 (18)0.0533 (6)
C120.0630 (3)0.07688 (15)0.78963 (17)0.0499 (6)
H12A0.01530.04330.73410.060*
C130.0277 (3)0.08148 (14)0.88289 (17)0.0451 (5)
C14A0.4495 (4)0.1786 (2)0.6598 (3)0.0623 (12)0.766 (8)
H14A0.42710.19890.58760.075*0.766 (8)
H14B0.44830.22680.70720.075*0.766 (8)
C15A0.6271 (5)0.1367 (4)0.6718 (4)0.1014 (19)0.766 (8)
H15A0.71880.17670.65740.152*0.766 (8)
H15B0.62940.09050.62280.152*0.766 (8)
H15C0.64800.11590.74300.152*0.766 (8)
C14B0.5209 (15)0.1174 (9)0.6931 (10)0.0623 (12)0.234 (8)
H14C0.57080.11670.76610.075*0.234 (8)
H14D0.56890.07040.65480.075*0.234 (8)
C15B0.5501 (19)0.1965 (12)0.6427 (15)0.1014 (19)0.234 (8)
H15D0.67610.20400.63560.152*0.234 (8)
H15E0.50660.24150.68480.152*0.234 (8)
H15F0.48730.19710.57370.152*0.234 (8)
C160.2402 (3)0.06431 (19)0.5966 (2)0.0686 (8)
H16A0.19150.01260.62400.082*
H16B0.34010.04920.55560.082*
C170.0984 (4)0.1068 (2)0.5251 (2)0.0825 (9)
H17A0.07940.07520.46040.124*
H17B0.13660.16310.50920.124*
H17C0.01140.10940.55990.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0535 (10)0.0900 (15)0.0739 (12)0.0143 (9)0.0228 (8)0.0231 (10)
O20.0493 (9)0.0725 (12)0.0530 (9)0.0226 (8)0.0151 (7)0.0032 (8)
N10.0441 (9)0.0575 (12)0.0431 (10)0.0080 (9)0.0086 (7)0.0054 (9)
N20.0532 (11)0.1144 (19)0.0599 (13)0.0330 (12)0.0211 (9)0.0154 (13)
C10.0454 (12)0.0495 (14)0.0588 (14)0.0043 (10)0.0067 (10)0.0068 (11)
C20.0662 (16)0.0635 (17)0.0575 (14)0.0039 (13)0.0194 (12)0.0164 (13)
C30.0636 (16)0.091 (2)0.0596 (15)0.0096 (14)0.0055 (12)0.0296 (15)
C40.0516 (13)0.0794 (19)0.0659 (15)0.0145 (13)0.0072 (11)0.0186 (14)
C50.0497 (11)0.0401 (12)0.0461 (11)0.0013 (10)0.0069 (9)0.0014 (10)
C60.0493 (11)0.0503 (13)0.0436 (11)0.0060 (10)0.0110 (9)0.0108 (10)
C70.0440 (12)0.0531 (14)0.0511 (12)0.0028 (10)0.0000 (9)0.0023 (11)
C80.0378 (10)0.0518 (13)0.0474 (12)0.0039 (10)0.0053 (9)0.0050 (10)
C90.0496 (13)0.0783 (18)0.0561 (14)0.0193 (13)0.0019 (11)0.0089 (13)
C100.0446 (12)0.093 (2)0.0675 (16)0.0293 (13)0.0037 (11)0.0005 (15)
C110.0409 (11)0.0651 (16)0.0542 (13)0.0123 (11)0.0059 (9)0.0013 (12)
C120.0433 (11)0.0593 (15)0.0477 (12)0.0139 (10)0.0079 (9)0.0013 (11)
C130.0366 (10)0.0475 (13)0.0513 (12)0.0020 (9)0.0048 (9)0.0075 (10)
C14A0.046 (2)0.075 (3)0.068 (2)0.0068 (16)0.0144 (15)0.0042 (17)
C15A0.037 (2)0.122 (4)0.145 (4)0.001 (2)0.008 (2)0.017 (3)
C14B0.046 (2)0.075 (3)0.068 (2)0.0068 (16)0.0144 (15)0.0042 (17)
C15B0.037 (2)0.122 (4)0.145 (4)0.001 (2)0.008 (2)0.017 (3)
C160.0639 (15)0.077 (2)0.0674 (17)0.0133 (14)0.0226 (13)0.0083 (15)
C170.0799 (19)0.095 (2)0.0738 (19)0.0132 (17)0.0118 (15)0.0002 (17)
Geometric parameters (Å, º) top
O1—C11.353 (3)C9—H9A0.9300
O1—H1B0.8200C10—C111.428 (3)
O2—C131.300 (2)C10—H10A0.9300
N1—C71.326 (3)C11—C121.394 (3)
N1—C51.411 (3)C12—C131.404 (3)
N1—H1A0.8600C12—H12A0.9300
N2—C111.358 (3)C14A—C15A1.482 (5)
N2—C161.454 (3)C14A—H14A0.9700
N2—C14A1.502 (4)C14A—H14B0.9700
N2—C14B1.609 (11)C15A—H15A0.9600
C1—C21.378 (3)C15A—H15B0.9600
C1—C61.386 (3)C15A—H15C0.9600
C2—C31.372 (3)C14B—C15B1.43 (2)
C2—H2A0.9300C14B—H14C0.9700
C3—C41.381 (3)C14B—H14D0.9700
C3—H3A0.9300C15B—H15D0.9600
C4—C51.390 (3)C15B—H15E0.9600
C4—H4A0.9300C15B—H15F0.9600
C5—C61.382 (3)C16—C171.502 (4)
C6—H6A0.9300C16—H16A0.9700
C7—C81.386 (3)C16—H16B0.9700
C7—H7A0.9300C17—H17A0.9600
C8—C91.416 (3)C17—H17B0.9600
C8—C131.429 (3)C17—H17C0.9600
C9—C101.347 (3)
C1—O1—H1B109.5N2—C11—C12121.7 (2)
C7—N1—C5126.78 (19)N2—C11—C10120.52 (19)
C7—N1—H1A116.6C12—C11—C10117.7 (2)
C5—N1—H1A116.6C11—C12—C13122.5 (2)
C11—N2—C16122.10 (19)C11—C12—H12A118.7
C11—N2—C14A122.6 (2)C13—C12—H12A118.7
C16—N2—C14A114.5 (2)O2—C13—C12121.6 (2)
C11—N2—C14B117.8 (5)O2—C13—C8120.00 (19)
C16—N2—C14B109.1 (5)C12—C13—C8118.40 (18)
O1—C1—C2118.1 (2)C15A—C14A—N2109.9 (3)
O1—C1—C6122.6 (2)C15A—C14A—H14A109.7
C2—C1—C6119.3 (2)N2—C14A—H14A109.7
C3—C2—C1120.5 (2)C15A—C14A—H14B109.7
C3—C2—H2A119.7N2—C14A—H14B109.7
C1—C2—H2A119.7H14A—C14A—H14B108.2
C2—C3—C4121.0 (2)C15B—C14B—N299.1 (10)
C2—C3—H3A119.5C15B—C14B—H14C112.0
C4—C3—H3A119.5N2—C14B—H14C112.0
C3—C4—C5118.6 (2)C15B—C14B—H14D112.0
C3—C4—H4A120.7N2—C14B—H14D112.0
C5—C4—H4A120.7H14C—C14B—H14D109.6
C6—C5—C4120.49 (19)C14B—C15B—H15D109.5
C6—C5—N1117.71 (18)C14B—C15B—H15E109.5
C4—C5—N1121.78 (19)H15D—C15B—H15E109.5
C5—C6—C1120.1 (2)C14B—C15B—H15F109.5
C5—C6—H6A119.9H15D—C15B—H15F109.5
C1—C6—H6A119.9H15E—C15B—H15F109.5
N1—C7—C8123.5 (2)N2—C16—C17112.8 (2)
N1—C7—H7A118.3N2—C16—H16A109.0
C8—C7—H7A118.3C17—C16—H16A109.0
C7—C8—C9119.5 (2)N2—C16—H16B109.0
C7—C8—C13122.26 (19)C17—C16—H16B109.0
C9—C8—C13118.24 (19)H16A—C16—H16B107.8
C10—C9—C8122.3 (2)C16—C17—H17A109.5
C10—C9—H9A118.9C16—C17—H17B109.5
C8—C9—H9A118.9H17A—C17—H17B109.5
C9—C10—C11120.7 (2)C16—C17—H17C109.5
C9—C10—H10A119.6H17A—C17—H17C109.5
C11—C10—H10A119.6H17B—C17—H17C109.5
O1—C1—C2—C3179.0 (2)C14A—N2—C11—C1014.6 (4)
C6—C1—C2—C30.4 (4)C14B—N2—C11—C1036.5 (7)
C1—C2—C3—C40.0 (4)C9—C10—C11—N2178.2 (3)
C2—C3—C4—C50.0 (4)C9—C10—C11—C121.6 (4)
C3—C4—C5—C60.5 (4)N2—C11—C12—C13178.1 (2)
C3—C4—C5—N1178.3 (2)C10—C11—C12—C131.6 (4)
C7—N1—C5—C6169.4 (2)C11—C12—C13—O2179.8 (2)
C7—N1—C5—C49.5 (4)C11—C12—C13—C80.3 (3)
C4—C5—C6—C11.0 (4)C7—C8—C13—O21.6 (3)
N1—C5—C6—C1177.9 (2)C9—C8—C13—O2178.3 (2)
O1—C1—C6—C5178.5 (2)C7—C8—C13—C12177.9 (2)
C2—C1—C6—C50.9 (4)C9—C8—C13—C122.3 (3)
C5—N1—C7—C8176.0 (2)C11—N2—C14A—C15A105.3 (4)
N1—C7—C8—C9178.9 (2)C16—N2—C14A—C15A85.1 (4)
N1—C7—C8—C131.3 (3)C14B—N2—C14A—C15A7.5 (7)
C7—C8—C9—C10177.8 (3)C11—N2—C14B—C15B115.0 (10)
C13—C8—C9—C102.4 (4)C16—N2—C14B—C15B100.1 (10)
C8—C9—C10—C110.4 (4)C14A—N2—C14B—C15B5.7 (8)
C16—N2—C11—C123.6 (4)C11—N2—C16—C1785.9 (3)
C14A—N2—C11—C12165.2 (3)C14A—N2—C16—C1783.8 (3)
C14B—N2—C11—C12143.7 (6)C14B—N2—C16—C17131.0 (5)
C16—N2—C11—C10176.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O2i0.821.772.580 (2)172
N1—H1A···O20.861.922.598 (2)135
C15A—H15C···O2ii0.962.533.422 (5)155
Symmetry codes: (i) x1, y, z+2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC17H20N2O2
Mr284.35
Crystal system, space groupMonoclinic, P21/a
Temperature (K)296
a, b, c (Å)7.4780 (6), 15.822 (2), 12.6372 (13)
β (°) 94.149 (9)
V3)1491.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.55 × 0.43 × 0.27
Data collection
DiffractometerOxford Diffraction Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.827, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
13075, 4836, 1828
Rint0.058
(sin θ/λ)max1)0.758
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.083, 0.270, 1.02
No. of reflections4836
No. of parameters201
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O2i0.821.772.580 (2)171.6
N1—H1A···O20.861.922.598 (2)135.1
C15A—H15C···O2ii0.962.533.422 (5)154.8
Symmetry codes: (i) x1, y, z+2; (ii) x+1, y, z.
 

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