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The two crystallographically independent mol­ecules in the asymmetric unit of the title compound, C17H14N2O2, have nearly the same molecular geometry. The planarity of the oxazoline ring is not affected by substitutions at the 2 and 4 positions. The structure is stabilized by N—H...O type intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100109X/ci6003sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680100109X/ci6003Isup2.hkl
Contains datablock I

CCDC reference: 159724

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.125
  • Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

ABSTM_02 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 0.934 Tmax scaled 0.933 Tmin scaled 0.913

Comment top

The structure determination of the title compound, (I), was undertaken to study the effect of substitutions at 2 and 4 positions on the oxazoline ring and the nature of hydrogen bonding. There are two crystallographically independent molecules in the asymmetric unit, Molecules I and II (atoms are labelled with addition letter A to the corresponding atoms of molecule II). The planarity of the oxazoline ring is not affected by the substitutions on the 2 and 4 positions. The dihedral angle between the phenyl ring and the oxazoline ring is 17.29 (10)° [13.35 (10)°]. The dihedral angle between the oxazoline ring and the toluidino moiety is 26.68 (10)° [19.10 (9)°]. The N7—C6 bond {1.329 (2) Å [1.322 (2) Å]} shows a partial double-bond character. This may be due to the delocalization of the lone pair of electrons of the N atom over the N7—C6C4 moiety (Thiruvalluvar et al., 1995). The exocyclic bond angles N3—C2—C15 and N3A–C2A—C15A are 128.0 (2) and 128.1 (2)°, respectively. This increase from the normal 120° may be the consequence of the repulsion between the lone pair of electrons of the N and the H atom of C20 and C20A (Vijayalakshmi et al., 1998). In the crystal, the N—H group of the molecules are involved in N—H···O type intermolecular hydrogen bonds (Table 2).

Experimental top

Triethylorthoformate (3.32 ml, 20 mmol) and acetic anhydride (3.57 ml, 38 mmol) were added to N-benzoylglycine (3.580 g, 20 mmol). The resulting reaction mixture was refluxed for 30 min and then kept in a freezer overnight. The precipitate of 4-(ethoxymethylene)-2-phenyl-5-oxazolone was filtered and washed with petroleum ether and dried. Equimolar quantity of 4-(ethoxymethylene)-2-phenyl-5-oxazolone and p-toluidine were taken in 10 ml of ethanol and the reaction mixture was refluxed for 2 h. On cooling, the precipitate of the title compound was obtained, which was washed with petroleum ether and ethanol and then recrystallized with ethanol.

Refinement top

All but methyl group H atoms were located from the difference map and were included in the structure-factor calculations with isotropic displacement parameters equal to 1.1Ueq of their respective carrier atom, but their positional parameters were not refined (C—H distances are in the range 0.95–1.10 Å), whereas the methyl H atoms were geometrically fixed and ariding model was used for their refinement.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1994); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.
4-(p-toluidinomethylene)-2-phenyl-2-oxazolin-5-one top
Crystal data top
C17H14N2O2F(000) = 1168
Mr = 278.30Dx = 1.283 Mg m3
Monoclinic, P21/aCu Kα radiation, λ = 1.54180 Å
a = 19.457 (2) ÅCell parameters from 25 reflections
b = 6.442 (1) Åθ = 25–35°
c = 24.619 (1) ŵ = 0.69 mm1
β = 110.95 (8)°T = 293 K
V = 2882.1 (5) Å3Plate, green
Z = 80.3 × 0.15 × 0.1 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
4460 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.014
Graphite monochromatorθmax = 68.0°, θmin = 3.9°
ω–2θ scansh = 2221
Absorption correction: ψ scan
(North et al., 1968)
k = 07
Tmin = 0.977, Tmax = 0.999l = 029
5422 measured reflections2 standard reflections every 120 min
5130 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0634P)2 + 0.9752P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
5130 reflectionsΔρmax = 0.25 e Å3
380 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0016 (1)
Crystal data top
C17H14N2O2V = 2882.1 (5) Å3
Mr = 278.30Z = 8
Monoclinic, P21/aCu Kα radiation
a = 19.457 (2) ŵ = 0.69 mm1
b = 6.442 (1) ÅT = 293 K
c = 24.619 (1) Å0.3 × 0.15 × 0.1 mm
β = 110.95 (8)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
4460 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.014
Tmin = 0.977, Tmax = 0.9992 standard reflections every 120 min
5422 measured reflections intensity decay: none
5130 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.06Δρmax = 0.25 e Å3
5130 reflectionsΔρmin = 0.17 e Å3
380 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*/Ueq
O10.43879 (6)0.27315 (18)0.38929 (5)0.0533 (3)
N30.47554 (7)0.6043 (2)0.40946 (6)0.0472 (3)
N70.61569 (8)0.7326 (2)0.49721 (6)0.0498 (4)
O50.53821 (9)0.0981 (2)0.44839 (8)0.0928 (6)
C20.42435 (9)0.4823 (3)0.37932 (7)0.0426 (4)
C40.53157 (9)0.4731 (3)0.44386 (7)0.0463 (4)
C50.50944 (10)0.2635 (3)0.43137 (9)0.0555 (4)
C60.59694 (9)0.5355 (3)0.48394 (7)0.0473 (4)
C80.68379 (9)0.8018 (3)0.53787 (7)0.0470 (4)
C90.68608 (10)0.9963 (3)0.56300 (8)0.0544 (4)
C100.75212 (11)1.0679 (3)0.60274 (8)0.0615 (5)
C110.81564 (11)0.9500 (4)0.61962 (8)0.0654 (6)
C120.81179 (10)0.7566 (4)0.59401 (9)0.0678 (6)
C130.74677 (10)0.6835 (3)0.55276 (8)0.0568 (5)
C140.88665 (13)1.0293 (5)0.66413 (11)0.1000 (9)
H14A0.87871.16480.67700.150*
H14B0.92371.03710.64690.150*
H14C0.90260.93630.69670.150*
C150.35400 (9)0.5370 (3)0.33492 (7)0.0431 (4)
C160.29725 (10)0.3927 (3)0.31555 (7)0.0528 (4)
C170.23185 (10)0.4470 (3)0.27260 (8)0.0631 (5)
C180.22251 (10)0.6428 (4)0.24812 (8)0.0626 (5)
C190.27832 (11)0.7864 (3)0.26766 (8)0.0609 (5)
C200.34405 (10)0.7358 (3)0.31125 (8)0.0522 (4)
H60.63550.42790.50700.051*
H70.58140.83430.47550.052*
H90.63741.08820.55320.059*
H100.74821.20300.62210.065*
H120.85300.66500.60300.074*
H130.74670.55790.53280.061*
H160.30340.24590.33290.059*
H170.19360.34800.25740.066*
H180.17810.67990.21790.068*
H190.27180.93120.24900.066*
H200.38520.83730.32650.055*
O1A0.57198 (6)0.49562 (18)0.14322 (5)0.0500 (3)
N3A0.60747 (7)0.1633 (2)0.14250 (6)0.0427 (3)
O5A0.64575 (8)0.6621 (2)0.10399 (7)0.0711 (4)
N7A0.72455 (7)0.0257 (2)0.10218 (6)0.0461 (3)
C2A0.56458 (8)0.2891 (2)0.15540 (7)0.0405 (3)
C4A0.64991 (8)0.2894 (2)0.12023 (7)0.0416 (4)
C5A0.62771 (9)0.4999 (3)0.12003 (8)0.0480 (4)
C6A0.70500 (9)0.2223 (3)0.10212 (7)0.0427 (4)
C8A0.78082 (8)0.0529 (3)0.08402 (7)0.0434 (4)
C9A0.80931 (9)0.2478 (3)0.10414 (8)0.0522 (4)
C10A0.86373 (10)0.3329 (3)0.08697 (9)0.0608 (5)
C11A0.89198 (10)0.2252 (4)0.05074 (8)0.0612 (5)
C12A0.86336 (10)0.0308 (4)0.03175 (8)0.0609 (5)
C13A0.80754 (10)0.0554 (3)0.04723 (7)0.0507 (4)
C14A0.95183 (12)0.3198 (5)0.03262 (11)0.0915 (9)
H14D0.96440.45450.05000.137*
H14E0.99450.23210.04540.137*
H14F0.93440.33260.00900.137*
C15A0.51220 (8)0.2426 (3)0.18397 (7)0.0427 (4)
C16A0.46261 (10)0.3918 (3)0.18790 (8)0.0524 (4)
C17A0.41542 (11)0.3463 (4)0.21708 (9)0.0632 (5)
C18A0.41809 (12)0.1549 (4)0.24253 (10)0.0688 (6)
C19A0.46700 (12)0.0060 (4)0.23851 (10)0.0718 (6)
C20A0.51375 (10)0.0482 (3)0.20875 (9)0.0588 (5)
H6A0.73320.33110.08590.046*
H7A0.69820.07000.11410.048*
H9A0.78980.32570.13200.057*
H10A0.88270.48970.10330.064*
H12A0.87960.05010.00400.064*
H13A0.78650.19140.03160.054*
H16A0.46250.52250.16710.055*
H17A0.37920.45130.22070.067*
H18A0.38950.12970.26840.076*
H19A0.47110.13920.25920.079*
H20A0.55520.05990.20970.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0498 (7)0.0391 (7)0.0635 (7)0.0022 (5)0.0111 (6)0.0029 (5)
N30.0454 (7)0.0418 (8)0.0493 (7)0.0008 (6)0.0110 (6)0.0006 (6)
N70.0478 (8)0.0423 (8)0.0512 (8)0.0025 (6)0.0077 (6)0.0030 (6)
O50.0759 (10)0.0421 (8)0.1279 (14)0.0080 (7)0.0030 (9)0.0145 (9)
C20.0454 (8)0.0388 (9)0.0453 (8)0.0000 (7)0.0184 (7)0.0021 (7)
C40.0448 (9)0.0413 (9)0.0501 (9)0.0027 (7)0.0136 (7)0.0026 (7)
C50.0495 (9)0.0448 (10)0.0650 (11)0.0030 (8)0.0119 (8)0.0069 (8)
C60.0471 (9)0.0437 (10)0.0485 (9)0.0021 (7)0.0140 (7)0.0041 (7)
C80.0466 (9)0.0515 (10)0.0419 (8)0.0029 (7)0.0145 (7)0.0038 (7)
C90.0593 (10)0.0499 (10)0.0507 (9)0.0033 (9)0.0158 (8)0.0005 (8)
C100.0688 (12)0.0664 (13)0.0497 (10)0.0152 (10)0.0215 (9)0.0089 (9)
C110.0538 (11)0.0927 (16)0.0504 (10)0.0184 (11)0.0197 (8)0.0088 (10)
C120.0463 (10)0.0906 (16)0.0669 (12)0.0029 (10)0.0209 (9)0.0002 (11)
C130.0513 (10)0.0618 (12)0.0586 (10)0.0003 (9)0.0213 (8)0.0047 (9)
C140.0663 (14)0.153 (3)0.0730 (14)0.0285 (16)0.0158 (12)0.0309 (17)
C150.0433 (8)0.0471 (9)0.0408 (8)0.0010 (7)0.0174 (7)0.0002 (7)
C160.0534 (10)0.0535 (11)0.0488 (9)0.0080 (8)0.0149 (8)0.0028 (8)
C170.0530 (10)0.0726 (14)0.0547 (10)0.0159 (10)0.0084 (8)0.0027 (10)
C180.0505 (10)0.0799 (14)0.0492 (10)0.0006 (10)0.0077 (8)0.0095 (10)
C190.0590 (11)0.0614 (12)0.0573 (10)0.0032 (9)0.0146 (9)0.0147 (9)
C200.0484 (9)0.0511 (10)0.0544 (10)0.0038 (8)0.0149 (8)0.0050 (8)
O1A0.0560 (7)0.0365 (6)0.0704 (7)0.0010 (5)0.0386 (6)0.0010 (5)
N3A0.0426 (7)0.0401 (7)0.0496 (7)0.0020 (6)0.0215 (6)0.0020 (6)
O5A0.0869 (10)0.0373 (7)0.1162 (12)0.0080 (7)0.0692 (9)0.0027 (7)
N7A0.0466 (7)0.0385 (8)0.0617 (8)0.0011 (6)0.0297 (6)0.0013 (6)
C2A0.0395 (8)0.0386 (8)0.0443 (8)0.0003 (7)0.0162 (6)0.0006 (7)
C4A0.0414 (8)0.0377 (8)0.0495 (8)0.0012 (7)0.0208 (7)0.0019 (7)
C5A0.0507 (9)0.0397 (9)0.0634 (10)0.0034 (7)0.0323 (8)0.0051 (8)
C6A0.0428 (8)0.0382 (9)0.0507 (9)0.0013 (7)0.0209 (7)0.0030 (7)
C8A0.0381 (8)0.0436 (9)0.0495 (8)0.0025 (7)0.0170 (7)0.0056 (7)
C9A0.0469 (9)0.0452 (10)0.0644 (11)0.0041 (8)0.0199 (8)0.0021 (8)
C10A0.0489 (10)0.0573 (12)0.0694 (12)0.0128 (9)0.0126 (9)0.0103 (9)
C11A0.0427 (9)0.0818 (15)0.0548 (10)0.0127 (9)0.0121 (8)0.0186 (10)
C12A0.0551 (10)0.0808 (14)0.0539 (10)0.0039 (10)0.0280 (9)0.0061 (10)
C13A0.0528 (9)0.0532 (11)0.0506 (9)0.0065 (8)0.0237 (8)0.0000 (8)
C14A0.0584 (12)0.129 (2)0.0864 (16)0.0292 (14)0.0256 (11)0.0273 (16)
C15A0.0384 (8)0.0486 (9)0.0424 (8)0.0008 (7)0.0161 (6)0.0007 (7)
C16A0.0543 (10)0.0563 (11)0.0530 (9)0.0098 (8)0.0269 (8)0.0094 (8)
C17A0.0606 (11)0.0735 (14)0.0685 (12)0.0131 (10)0.0389 (10)0.0090 (10)
C18A0.0704 (13)0.0771 (15)0.0763 (13)0.0009 (11)0.0477 (11)0.0089 (11)
C19A0.0799 (14)0.0634 (13)0.0892 (15)0.0005 (11)0.0511 (13)0.0163 (11)
C20A0.0570 (10)0.0536 (11)0.0744 (12)0.0034 (9)0.0339 (9)0.0110 (9)
Geometric parameters (Å, º) top
O1—C21.380 (2)O1A—C2A1.383 (2)
O1—C51.396 (2)O1A—C5A1.3947 (19)
N3—C21.277 (2)N3A—C2A1.282 (2)
N3—C41.400 (2)N3A—C4A1.402 (2)
N7—C61.329 (2)O5A—C5A1.212 (2)
N7—C81.417 (2)N7A—C6A1.322 (2)
N7—H70.9512N7A—C8A1.416 (2)
O5—C51.206 (2)N7A—H7A0.9147
C2—C151.457 (2)C2A—C15A1.462 (2)
C4—C61.362 (2)C4A—C6A1.370 (2)
C4—C51.418 (3)C4A—C5A1.423 (2)
C6—H61.0301C6A—H6A1.0529
C8—C131.377 (3)C8A—C13A1.384 (2)
C8—C91.391 (3)C8A—C9A1.390 (2)
C9—C101.386 (3)C9A—C10A1.386 (2)
C9—H91.0689C9A—H9A1.0259
C10—C111.382 (3)C10A—C11A1.389 (3)
C10—H101.008C10A—H10A1.101
C11—C121.386 (3)C11A—C12A1.382 (3)
C11—C141.513 (3)C11A—C14A1.516 (3)
C12—C131.391 (3)C12A—C13A1.389 (2)
C12—H120.956C12A—H12A0.996
C13—H130.946C13A—H13A0.9855
C14—H14A0.9600C14A—H14D0.9600
C14—H14B0.9600C14A—H14E0.9600
C14—H14C0.9600C14A—H14F0.9600
C15—C161.391 (2)C15A—C20A1.389 (3)
C15—C201.392 (2)C15A—C16A1.389 (2)
C16—C171.377 (3)C16A—C17A1.385 (2)
C16—H161.0268C16A—H16A0.9851
C17—C181.382 (3)C17A—C18A1.376 (3)
C17—H170.9494C17A—H17A1.0035
C18—C191.376 (3)C18A—C19A1.379 (3)
C18—H180.9474C18A—H18A0.9974
C19—C201.383 (2)C19A—C20A1.384 (3)
C19—H191.028C19A—H19A1.054
C20—H200.9972C20A—H20A1.0595
C2—O1—C5105.04 (13)C2A—O1A—C5A105.33 (12)
C2—N3—C4104.90 (14)C2A—N3A—C4A104.89 (13)
C6—N7—C8125.39 (14)C6A—N7A—C8A126.65 (14)
C6—N7—H7116.36C6A—N7A—H7A116.86
C8—N7—H7118.11C8A—N7A—H7A116.47
N3—C2—O1115.49 (14)N3A—C2A—O1A115.29 (13)
N3—C2—C15127.97 (16)N3A—C2A—C15A128.13 (15)
O1—C2—C15116.52 (14)O1A—C2A—C15A116.50 (13)
C6—C4—N3125.73 (16)C6A—C4A—N3A125.66 (15)
C6—C4—C5124.79 (16)C6A—C4A—C5A124.88 (15)
N3—C4—C5109.47 (14)N3A—C4A—C5A109.46 (13)
O5—C5—O1120.59 (17)O5A—C5A—O1A120.56 (15)
O5—C5—C4134.31 (17)O5A—C5A—C4A134.40 (15)
O1—C5—C4105.10 (14)O1A—C5A—C4A105.02 (13)
N7—C6—C4124.25 (16)N7A—C6A—C4A124.09 (15)
N7—C6—H6115.20N7A—C6A—H6A116.70
C4—C6—H6120.54C4A—C6A—H6A119.19
C13—C8—C9119.76 (17)C13A—C8A—C9A119.56 (15)
C13—C8—N7122.15 (17)C13A—C8A—N7A122.71 (15)
C9—C8—N7118.09 (16)C9A—C8A—N7A117.73 (15)
C10—C9—C8119.20 (18)C10A—C9A—C8A119.95 (18)
C10—C9—H9119.87C10A—C9A—H9A121.08
C8—C9—H9120.90C8A—C9A—H9A118.97
C11—C10—C9122.2 (2)C9A—C10A—C11A121.28 (18)
C11—C10—H10122.88C9A—C10A—H10A116.38
C9—C10—H10114.4C11A—C10A—H10A122.34
C10—C11—C12117.40 (18)C12A—C11A—C10A117.76 (17)
C10—C11—C14121.3 (2)C12A—C11A—C14A121.6 (2)
C12—C11—C14121.3 (2)C10A—C11A—C14A120.7 (2)
C11—C12—C13121.56 (19)C11A—C12A—C13A121.96 (18)
C11—C12—H12123.0C11A—C12A—H12A121.19
C13—C12—H12115.4C13A—C12A—H12A116.7
C8—C13—C12119.83 (19)C8A—C13A—C12A119.47 (17)
C8—C13—H13119.95C8A—C13A—H13A120.20
C12—C13—H13120.04C12A—C13A—H13A120.32
C11—C14—H14A109.5C11A—C14A—H14D109.5
C11—C14—H14B109.5C11A—C14A—H14E109.5
H14A—C14—H14B109.5H14D—C14A—H14E109.5
C11—C14—H14C109.5C11A—C14A—H14F109.5
H14A—C14—H14C109.5H14D—C14A—H14F109.5
H14B—C14—H14C109.5H14E—C14A—H14F109.5
C16—C15—C20119.82 (16)C20A—C15A—C16A120.00 (15)
C16—C15—C2120.87 (16)C20A—C15A—C2A119.13 (15)
C20—C15—C2119.31 (15)C16A—C15A—C2A120.85 (15)
C17—C16—C15119.71 (18)C17A—C16A—C15A119.70 (17)
C17—C16—H16119.43C17A—C16A—H16A124.90
C15—C16—H16120.86C15A—C16A—H16A115.31
C16—C17—C18120.53 (18)C18A—C17A—C16A120.14 (18)
C16—C17—H17120.7C18A—C17A—H17A118.51
C18—C17—H17118.62C16A—C17A—H17A121.4
C19—C18—C17119.81 (17)C17A—C18A—C19A120.35 (17)
C19—C18—H18119.3C17A—C18A—H18A119.8
C17—C18—H18120.9C19A—C18A—H18A119.3
C18—C19—C20120.56 (18)C18A—C19A—C20A120.16 (19)
C18—C19—H19119.89C18A—C19A—H19A121.14
C20—C19—H19119.53C20A—C19A—H19A118.7
C19—C20—C15119.56 (17)C19A—C20A—C15A119.64 (18)
C19—C20—H20122.21C19A—C20A—H20A119.90
C15—C20—H20118.23C15A—C20A—H20A119.97
C4—N3—C2—O10.18 (19)C4A—N3A—C2A—O1A1.05 (18)
C4—N3—C2—C15177.98 (16)C4A—N3A—C2A—C15A175.35 (15)
C5—O1—C2—N30.6 (2)C5A—O1A—C2A—N3A0.66 (19)
C5—O1—C2—C15177.81 (14)C5A—O1A—C2A—C15A176.18 (13)
C2—N3—C4—C6178.72 (17)C2A—N3A—C4A—C6A178.13 (16)
C2—N3—C4—C50.29 (19)C2A—N3A—C4A—C5A1.03 (18)
C2—O1—C5—O5178.5 (2)C2A—O1A—C5A—O5A178.60 (17)
C2—O1—C5—C40.68 (19)C2A—O1A—C5A—C4A0.05 (18)
C6—C4—C5—O52.6 (4)C6A—C4A—C5A—O5A3.1 (3)
N3—C4—C5—O5178.4 (2)N3A—C4A—C5A—O5A177.7 (2)
C6—C4—C5—O1178.40 (16)C6A—C4A—C5A—O1A178.51 (15)
N3—C4—C5—O10.6 (2)N3A—C4A—C5A—O1A0.66 (19)
C8—N7—C6—C4178.7 (2)C8A—N7A—C6A—C4A180.0 (2)
N3—C4—C6—N72.1 (3)N3A—C4A—C6A—N7A1.5 (3)
C5—C4—C6—N7176.73 (18)C5A—C4A—C6A—N7A179.45 (17)
C6—N7—C8—C1323.7 (3)C6A—N7A—C8A—C13A20.9 (3)
C6—N7—C8—C9156.48 (17)C6A—N7A—C8A—C9A159.59 (17)
C13—C8—C9—C100.1 (3)C13A—C8A—C9A—C10A0.5 (3)
N7—C8—C9—C10179.75 (16)N7A—C8A—C9A—C10A179.08 (16)
C8—C9—C10—C111.9 (3)C8A—C9A—C10A—C11A1.4 (3)
C9—C10—C11—C121.7 (3)C9A—C10A—C11A—C12A0.7 (3)
C9—C10—C11—C14178.5 (2)C9A—C10A—C11A—C14A179.63 (18)
C10—C11—C12—C130.2 (3)C10A—C11A—C12A—C13A0.9 (3)
C14—C11—C12—C13179.6 (2)C14A—C11A—C12A—C13A178.74 (19)
C9—C8—C13—C121.8 (3)C9A—C8A—C13A—C12A1.1 (3)
N7—C8—C13—C12178.41 (17)N7A—C8A—C13A—C12A179.36 (16)
C11—C12—C13—C81.9 (3)C11A—C12A—C13A—C8A1.8 (3)
N3—C2—C15—C16164.89 (17)N3A—C2A—C15A—C20A10.4 (3)
O1—C2—C15—C1617.0 (2)O1A—C2A—C15A—C20A165.94 (16)
N3—C2—C15—C2015.9 (3)N3A—C2A—C15A—C16A171.31 (16)
O1—C2—C15—C20162.28 (15)O1A—C2A—C15A—C16A12.3 (2)
C20—C15—C16—C170.7 (3)C20A—C15A—C16A—C17A0.6 (3)
C2—C15—C16—C17178.54 (17)C2A—C15A—C16A—C17A177.60 (17)
C15—C16—C17—C180.8 (3)C15A—C16A—C17A—C18A0.6 (3)
C16—C17—C18—C191.4 (3)C16A—C17A—C18A—C19A0.9 (3)
C17—C18—C19—C200.6 (3)C17A—C18A—C19A—C20A0.0 (4)
C18—C19—C20—C150.9 (3)C18A—C19A—C20A—C15A1.3 (3)
C16—C15—C20—C191.5 (3)C16A—C15A—C20A—C19A1.6 (3)
C2—C15—C20—C19177.73 (16)C2A—C15A—C20A—C19A176.70 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···O5i0.951.912.822 (2)161
N7A—H7A···O5Aii0.921.982.809 (2)151
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC17H14N2O2
Mr278.30
Crystal system, space groupMonoclinic, P21/a
Temperature (K)293
a, b, c (Å)19.457 (2), 6.442 (1), 24.619 (1)
β (°) 110.95 (8)
V3)2882.1 (5)
Z8
Radiation typeCu Kα
µ (mm1)0.69
Crystal size (mm)0.3 × 0.15 × 0.1
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.977, 0.999
No. of measured, independent and
observed [I > 2σ(I)] reflections
5422, 5130, 4460
Rint0.014
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.125, 1.06
No. of reflections5130
No. of parameters380
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.17

Computer programs: CAD-4 Software (Enraf-Nonius, 1994), CAD-4 Software, MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), SHELXL97.

Selected geometric parameters (Å, º) top
N3—C21.277 (2)N3A—C2A1.282 (2)
N3—C41.400 (2)N3A—C4A1.402 (2)
N7—C81.417 (2)N7A—C8A1.416 (2)
C4—C61.362 (2)C4A—C6A1.370 (2)
C8—N7—C6—C4178.7 (2)C8A—N7A—C6A—C4A180.0 (2)
C6—N7—C8—C1323.7 (3)C6A—N7A—C8A—C13A20.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7···O5i0.951.912.822 (2)161
N7A—H7A···O5Aii0.921.982.809 (2)151
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
 

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