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The mol­ecule of the title compound, C18H15NO3, adopts the keto–amine tautomeric form, with strong intra­molecular N—H...O hydrogen bonds classified as resonance-assisted hydrogen bonds (RAHBs). In the crystal structure, the mol­ecules are stabilized by C—H...O, C—H...π and π–π interactions, forming rings and chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041511/hk2133sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041511/hk2133Isup2.hkl
Contains datablock I

CCDC reference: 605553

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.039
  • wR factor = 0.110
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: WIN-XPOSE in X-AREA (Stoe & Cie, 2000); cell refinement: WIN-CELL in X-AREA; data reduction: WIN-INTEGRATE in X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PARST97 (Nardelli, 1996).

3-[(1-Benzylamino)ethylidene]-2H-chromene-2,4(3H)-dione top
Crystal data top
C18H15NO3Z = 2
Mr = 293.32F(000) = 308
Triclinic, P1Dx = 1.378 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.385 (2) ÅCell parameters from 894 reflections
b = 9.403 (2) Åθ = 2.7–26.2°
c = 9.871 (2) ŵ = 0.09 mm1
α = 81.60 (2)°T = 193 K
β = 85.35 (2)°Block, colorless
γ = 66.75 (2)°0.53 × 0.45 × 0.45 mm
V = 707.1 (3) Å3
Data collection top
Stoe IPDS-II
diffractometer
1910 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.064
Graphite monochromatorθmax = 26.3°, θmin = 2.1°
Detector resolution: 150 pixels mm-1h = 1010
φ scansk = 1111
7530 measured reflectionsl = 1212
2659 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.065P)2]
where P = (Fo2 + 2Fc2)/3
2659 reflections(Δ/σ)max = 0.001
200 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.18 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
O10.06317 (13)0.29380 (11)1.20970 (9)0.0347 (3)
C30.24242 (18)0.21866 (15)1.00482 (13)0.0300 (3)
O40.36679 (14)0.39510 (11)0.89615 (10)0.0372 (3)
N320.40595 (15)0.14402 (13)0.80209 (11)0.0328 (3)
H320.42370.22820.80120.039*
O20.09519 (14)0.07399 (11)1.14150 (10)0.0389 (3)
C100.19424 (18)0.46657 (15)1.09428 (13)0.0306 (3)
C90.09226 (19)0.42884 (15)1.19914 (14)0.0314 (3)
C3110.2868 (2)0.03957 (17)0.91521 (15)0.0367 (3)
H31C0.35280.09780.84320.055*
H31B0.16580.01710.90600.055*
H31A0.32480.09981.00230.055*
C40.27465 (19)0.35958 (16)0.99045 (13)0.0309 (3)
C80.0137 (2)0.52555 (16)1.29998 (14)0.0364 (4)
H80.05480.49871.36950.044*
C60.1423 (2)0.70305 (16)1.19065 (15)0.0394 (4)
H60.15930.79541.18820.047*
C20.13324 (19)0.18661 (16)1.11615 (13)0.0311 (3)
C70.0400 (2)0.66227 (17)1.29447 (15)0.0393 (4)
H70.01150.72811.36120.047*
C310.31298 (18)0.10978 (15)0.90596 (13)0.0307 (3)
C50.2185 (2)0.60584 (16)1.09127 (14)0.0353 (3)
H50.28660.63321.02170.042*
C330.4821 (2)0.05289 (17)0.68793 (14)0.0378 (4)
H33B0.39540.02500.65220.045*
H33A0.57760.04270.72040.045*
C3310.5471 (2)0.14451 (16)0.57560 (14)0.0346 (3)
C3320.4312 (2)0.27368 (18)0.49745 (15)0.0429 (4)
H3320.31260.30520.51630.052*
C3360.7220 (2)0.09983 (19)0.54473 (15)0.0449 (4)
H3360.80150.01450.59670.054*
C3340.6652 (2)0.30889 (19)0.36051 (15)0.0435 (4)
H3340.70480.36300.28850.052*
C3330.4907 (2)0.35618 (18)0.39147 (16)0.0458 (4)
H3330.41200.44380.34120.055*
C3350.7809 (2)0.1805 (2)0.43708 (16)0.0516 (5)
H3350.89930.14780.41650.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0426 (6)0.0329 (5)0.0331 (5)0.0199 (5)0.0084 (4)0.0076 (4)
C30.0313 (8)0.0309 (7)0.0280 (7)0.0128 (6)0.0001 (5)0.0026 (5)
O40.0453 (6)0.0371 (5)0.0336 (5)0.0224 (5)0.0080 (4)0.0041 (4)
N320.0380 (7)0.0340 (6)0.0290 (6)0.0171 (5)0.0035 (5)0.0051 (5)
O20.0492 (7)0.0351 (5)0.0382 (6)0.0238 (5)0.0095 (5)0.0065 (4)
C100.0326 (8)0.0295 (7)0.0299 (7)0.0122 (6)0.0021 (5)0.0024 (5)
C90.0348 (8)0.0285 (7)0.0319 (7)0.0134 (6)0.0016 (6)0.0033 (5)
C3110.0433 (9)0.0359 (7)0.0352 (7)0.0195 (7)0.0050 (6)0.0085 (6)
C40.0327 (8)0.0326 (7)0.0278 (7)0.0140 (6)0.0015 (5)0.0006 (5)
C80.0374 (9)0.0377 (8)0.0329 (7)0.0137 (7)0.0038 (6)0.0059 (6)
C60.0457 (10)0.0308 (7)0.0432 (8)0.0159 (7)0.0030 (7)0.0054 (6)
C20.0337 (8)0.0307 (7)0.0294 (7)0.0134 (6)0.0001 (5)0.0034 (5)
C70.0415 (9)0.0360 (8)0.0399 (8)0.0126 (7)0.0003 (6)0.0114 (6)
C310.0309 (8)0.0325 (7)0.0285 (7)0.0125 (6)0.0032 (5)0.0011 (5)
C50.0389 (9)0.0339 (7)0.0341 (7)0.0162 (6)0.0008 (6)0.0013 (6)
C330.0432 (9)0.0380 (7)0.0327 (7)0.0159 (7)0.0060 (6)0.0096 (6)
C3310.0402 (9)0.0364 (7)0.0278 (7)0.0147 (6)0.0022 (6)0.0080 (5)
C3320.0359 (9)0.0420 (8)0.0429 (9)0.0081 (7)0.0051 (6)0.0040 (6)
C3360.0368 (9)0.0517 (9)0.0388 (8)0.0125 (7)0.0012 (6)0.0037 (7)
C3340.0522 (10)0.0497 (9)0.0319 (7)0.0253 (8)0.0025 (7)0.0015 (6)
C3330.0494 (10)0.0397 (8)0.0404 (8)0.0113 (7)0.0005 (7)0.0010 (6)
C3350.0377 (10)0.0684 (11)0.0441 (9)0.0207 (8)0.0034 (7)0.0050 (8)
Geometric parameters (Å, º) top
O1—C91.3727 (17)C6—C51.380 (2)
O1—C21.3894 (16)C6—C71.391 (2)
C3—C311.4389 (19)C6—H60.9300
C3—C41.439 (2)C7—H70.9300
C3—C21.4471 (19)C5—H50.9300
O4—C41.2534 (18)C33—C3311.504 (2)
N32—C311.3171 (18)C33—H33B0.9700
N32—C331.4647 (17)C33—H33A0.9700
N32—H320.8600C331—C3361.378 (2)
O2—C21.2092 (17)C331—C3321.389 (2)
C10—C91.385 (2)C332—C3331.389 (2)
C10—C51.398 (2)C332—H3320.9300
C10—C41.4733 (19)C336—C3351.387 (2)
C9—C81.392 (2)C336—H3360.9300
C311—C311.494 (2)C334—C3331.373 (2)
C311—H31C0.9600C334—C3351.378 (2)
C311—H31B0.9600C334—H3340.9300
C311—H31A0.9600C333—H3330.9300
C8—C71.380 (2)C335—H3350.9300
C8—H80.9300
C9—O1—C2122.40 (11)C8—C7—H7119.5
C31—C3—C4120.60 (12)C6—C7—H7119.5
C31—C3—C2118.77 (12)N32—C31—C3117.97 (13)
C4—C3—C2120.60 (12)N32—C31—C311118.49 (12)
C31—N32—C33126.43 (13)C3—C31—C311123.54 (13)
C31—N32—H32116.8C6—C5—C10120.60 (14)
C33—N32—H32116.8C6—C5—H5119.7
C9—C10—C5118.41 (13)C10—C5—H5119.7
C9—C10—C4119.57 (13)N32—C33—C331110.79 (12)
C5—C10—C4122.02 (13)N32—C33—H33B109.5
O1—C9—C10121.91 (12)C331—C33—H33B109.5
O1—C9—C8116.22 (13)N32—C33—H33A109.5
C10—C9—C8121.87 (13)C331—C33—H33A109.5
C31—C311—H31C109.5H33B—C33—H33A108.1
C31—C311—H31B109.5C336—C331—C332118.39 (14)
H31C—C311—H31B109.5C336—C331—C33121.01 (13)
C31—C311—H31A109.5C332—C331—C33120.57 (14)
H31C—C311—H31A109.5C333—C332—C331120.68 (15)
H31B—C311—H31A109.5C333—C332—H332119.7
O4—C4—C3123.93 (13)C331—C332—H332119.7
O4—C4—C10118.90 (13)C331—C336—C335120.85 (14)
C3—C4—C10117.16 (12)C331—C336—H336119.6
C7—C8—C9118.46 (14)C335—C336—H336119.6
C7—C8—H8120.8C333—C334—C335119.41 (15)
C9—C8—H8120.8C333—C334—H334120.3
C5—C6—C7119.67 (14)C335—C334—H334120.3
C5—C6—H6120.2C334—C333—C332120.29 (14)
C7—C6—H6120.2C334—C333—H333119.9
O2—C2—O1113.58 (12)C332—C333—H333119.9
O2—C2—C3128.06 (13)C334—C335—C336120.36 (16)
O1—C2—C3118.35 (12)C334—C335—H335119.8
C8—C7—C6120.99 (14)C336—C335—H335119.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N32—H32···O40.861.832.554 (2)141
C6—H6···O2i0.932.443.318 (2)158
C334—H334···O4ii0.932.603.420 (2)148
C311—H31B···O2iii0.962.553.440 (2)156
C333—H333···Cg2iv0.932.723.528 (2)147
C33—H33B···Cg3v0.972.813.572 (2)136
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1; (iii) x, y, z+2; (iv) x, y, z4; (v) x+1, y, z+1.
 

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