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The title compound, C9H8N2O, was synthesized from 2-cyano­aniline and acetyl chloride in dry acetone. The crystal structure is stabilized by an intra­molecular C—H...O hydrogen-bond contact, which forms a six-membered ring, and two inter­molecular N—H...N and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013152/at6007sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013152/at6007Isup2.hkl
Contains datablock I

CCDC reference: 274323

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.079
  • Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.40 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C9 ... 1.43 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16 C2 -C1 -C9 -N1 8.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 17 C6 -C1 -C9 -N1 10.00 0.00 1.555 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 977 Count of symmetry unique reflns 978 Completeness (_total/calc) 99.90% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-Acetamidobenzonitrile top
Crystal data top
C9H8N2OF(000) = 336
Mr = 160.17Dx = 1.310 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4911 reflections
a = 3.8956 (3) Åθ = 1.8–27.8°
b = 11.3796 (14) ŵ = 0.09 mm1
c = 18.3249 (18) ÅT = 296 K
V = 812.35 (14) Å3Needle, colourless
Z = 40.60 × 0.36 × 0.10 mm
Data collection top
Toe IPDS II
diffractometer
766 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 26.0°, θmin = 2.1°
Detector resolution: 6.67 pixels mm-1h = 44
ω scansk = 014
1591 measured reflectionsl = 022
977 independent reflections
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)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.0515P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
977 reflectionsΔρmax = 0.12 e Å3
132 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.049 (7)
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
H50.358 (7)1.082 (2)0.6750 (12)0.062 (6)*
H40.459 (7)1.012 (2)0.7955 (12)0.068 (7)*
H220.094 (6)0.9233 (19)0.5325 (11)0.049 (6)*
H30.315 (8)0.819 (2)0.8291 (13)0.077 (8)*
H20.124 (7)0.6938 (19)0.7403 (11)0.061 (7)*
O10.1136 (6)1.15411 (12)0.59490 (8)0.0693 (6)
N10.1967 (7)0.67472 (17)0.56496 (11)0.0716 (7)
N20.0726 (6)0.97049 (13)0.56821 (9)0.0480 (5)
C10.0823 (6)0.81464 (15)0.65785 (10)0.0431 (5)
C20.1570 (7)0.77324 (18)0.72712 (12)0.0519 (6)
C30.2957 (7)0.8470 (2)0.77863 (12)0.0582 (6)
C40.3595 (7)0.96279 (19)0.76015 (11)0.0565 (6)
C50.2899 (7)1.00477 (18)0.69145 (11)0.0501 (6)
C60.1482 (5)0.93177 (15)0.63905 (10)0.0411 (5)
C70.0545 (6)1.07864 (16)0.55012 (10)0.0484 (5)
C80.1195 (8)1.0953 (2)0.47024 (11)0.0642 (7)
H8A0.08321.02220.44520.096*
H8B0.03491.15350.45140.096*
H8C0.35201.12070.46300.096*
C90.0720 (7)0.73657 (16)0.60597 (11)0.0493 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1057 (15)0.0417 (8)0.0606 (9)0.0143 (10)0.0126 (11)0.0022 (7)
N10.0998 (18)0.0519 (11)0.0632 (11)0.0131 (12)0.0114 (13)0.0107 (10)
N20.0729 (13)0.0336 (8)0.0375 (9)0.0052 (9)0.0034 (9)0.0024 (7)
C10.0517 (13)0.0355 (9)0.0421 (10)0.0004 (9)0.0018 (10)0.0039 (8)
C20.0661 (16)0.0409 (11)0.0487 (11)0.0043 (11)0.0001 (12)0.0042 (9)
C30.0737 (17)0.0578 (13)0.0431 (11)0.0014 (13)0.0042 (11)0.0030 (10)
C40.0689 (16)0.0552 (12)0.0456 (11)0.0094 (12)0.0035 (12)0.0108 (10)
C50.0643 (16)0.0392 (10)0.0468 (11)0.0094 (11)0.0054 (11)0.0050 (8)
C60.0488 (12)0.0360 (9)0.0385 (9)0.0007 (9)0.0048 (9)0.0021 (8)
C70.0594 (13)0.0367 (10)0.0490 (11)0.0013 (11)0.0104 (10)0.0038 (9)
C80.0810 (19)0.0569 (13)0.0545 (12)0.0079 (14)0.0014 (14)0.0134 (10)
C90.0651 (14)0.0353 (9)0.0476 (10)0.0019 (11)0.0011 (12)0.0011 (9)
Geometric parameters (Å, º) top
O1—C71.210 (2)C3—C41.383 (3)
N1—C91.138 (3)C3—H30.98 (2)
N2—C71.367 (3)C4—C51.373 (3)
N2—C61.402 (2)C4—H40.94 (2)
N2—H220.85 (2)C5—C61.385 (3)
C1—C21.385 (3)C5—H50.96 (2)
C1—C61.400 (2)C7—C81.498 (3)
C1—C91.433 (3)C8—H8A0.9600
C2—C31.374 (3)C8—H8B0.9600
C2—H20.94 (2)C8—H8C0.9600
C7—N2—C6125.69 (17)C4—C5—H5123.3 (14)
C7—N2—H22114.6 (14)C6—C5—H5115.9 (13)
C6—N2—H22119.6 (14)C5—C6—C1118.27 (18)
C2—C1—C6120.71 (19)C5—C6—N2122.50 (17)
C2—C1—C9119.04 (17)C1—C6—N2119.23 (17)
C6—C1—C9120.24 (17)O1—C7—N2122.91 (19)
C3—C2—C1120.31 (19)O1—C7—C8122.76 (19)
C3—C2—H2117.6 (14)N2—C7—C8114.33 (18)
C1—C2—H2122.1 (14)C7—C8—H8A109.5
C2—C3—C4119.0 (2)C7—C8—H8B109.5
C2—C3—H3118.7 (15)H8A—C8—H8B109.5
C4—C3—H3121.8 (14)C7—C8—H8C109.5
C5—C4—C3121.4 (2)H8A—C8—H8C109.5
C5—C4—H4120.1 (14)H8B—C8—H8C109.5
C3—C4—H4118.5 (14)N1—C9—C1179.5 (3)
C4—C5—C6120.38 (19)
C6—C1—C2—C30.4 (4)C2—C1—C6—N2179.4 (2)
C9—C1—C2—C3178.1 (3)C9—C1—C6—N22.2 (3)
C1—C2—C3—C40.1 (4)C7—N2—C6—C537.9 (4)
C2—C3—C4—C50.6 (4)C7—N2—C6—C1142.9 (2)
C3—C4—C5—C61.0 (4)C6—N2—C7—O10.6 (4)
C4—C5—C6—C10.7 (4)C6—N2—C7—C8178.6 (2)
C4—C5—C6—N2180.0 (2)C2—C1—C9—N183 (28)
C2—C1—C6—C50.0 (3)C6—C1—C9—N195 (28)
C9—C1—C6—C5178.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H22···N1i0.85 (2)2.26 (2)3.081 (3)163 (2)
C3—H3···O1ii0.98 (2)2.47 (2)3.270 (3)139 (2)
C5—H5···O10.97 (2)2.49 (3)2.914 (3)106.3 (18)
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x, y1/2, z+3/2.
 

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