2-Acetamido­benzonitrile

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.

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

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Computing details

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

Crystal data

C9H8N2O	F(000) = 336
Mr = 160.17	Dx = 1.310 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4911 reflections
a = 3.8956 (3) Å	θ = 1.8–27.8°
b = 11.3796 (14) Å	µ = 0.09 mm^−1
c = 18.3249 (18) Å	T = 296 K
V = 812.35 (14) Å^3	Needle, colourless
Z = 4	0.60 × 0.36 × 0.10 mm

Data collection

Toe IPDS II diffractometer	766 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 26.0°, θmin = 2.1°
Detector resolution: 6.67 pixels mm^-1	h = −4→4
ω scans	k = 0→14
1591 measured reflections	l = 0→22
977 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0515P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max < 0.001
977 reflections	Δρmax = 0.12 e Å^−3
132 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.049 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
H5	0.358 (7)	1.082 (2)	0.6750 (12)	0.062 (6)*
H4	0.459 (7)	1.012 (2)	0.7955 (12)	0.068 (7)*
H22	0.094 (6)	0.9233 (19)	0.5325 (11)	0.049 (6)*
H3	0.315 (8)	0.819 (2)	0.8291 (13)	0.077 (8)*
H2	0.124 (7)	0.6938 (19)	0.7403 (11)	0.061 (7)*
O1	−0.1136 (6)	1.15411 (12)	0.59490 (8)	0.0693 (6)
N1	−0.1967 (7)	0.67472 (17)	0.56496 (11)	0.0716 (7)
N2	0.0726 (6)	0.97049 (13)	0.56821 (9)	0.0480 (5)
C1	0.0823 (6)	0.81464 (15)	0.65785 (10)	0.0431 (5)
C2	0.1570 (7)	0.77324 (18)	0.72712 (12)	0.0519 (6)
C3	0.2957 (7)	0.8470 (2)	0.77863 (12)	0.0582 (6)
C4	0.3595 (7)	0.96279 (19)	0.76015 (11)	0.0565 (6)
C5	0.2899 (7)	1.00477 (18)	0.69145 (11)	0.0501 (6)
C6	0.1482 (5)	0.93177 (15)	0.63905 (10)	0.0411 (5)
C7	−0.0545 (6)	1.07864 (16)	0.55012 (10)	0.0484 (5)
C8	−0.1195 (8)	1.0953 (2)	0.47024 (11)	0.0642 (7)
H8A	−0.0832	1.0222	0.4452	0.096*
H8B	0.0349	1.1535	0.4514	0.096*
H8C	−0.3520	1.1207	0.4630	0.096*
C9	−0.0720 (7)	0.73657 (16)	0.60597 (11)	0.0493 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1057 (15)	0.0417 (8)	0.0606 (9)	0.0143 (10)	0.0126 (11)	−0.0022 (7)
N1	0.0998 (18)	0.0519 (11)	0.0632 (11)	−0.0131 (12)	−0.0114 (13)	−0.0107 (10)
N2	0.0729 (13)	0.0336 (8)	0.0375 (9)	0.0052 (9)	0.0034 (9)	−0.0024 (7)
C1	0.0517 (13)	0.0355 (9)	0.0421 (10)	−0.0004 (9)	0.0018 (10)	−0.0039 (8)
C2	0.0661 (16)	0.0409 (11)	0.0487 (11)	−0.0043 (11)	−0.0001 (12)	0.0042 (9)
C3	0.0737 (17)	0.0578 (13)	0.0431 (11)	−0.0014 (13)	−0.0042 (11)	0.0030 (10)
C4	0.0689 (16)	0.0552 (12)	0.0456 (11)	−0.0094 (12)	−0.0035 (12)	−0.0108 (10)
C5	0.0643 (16)	0.0392 (10)	0.0468 (11)	−0.0094 (11)	0.0054 (11)	−0.0050 (8)
C6	0.0488 (12)	0.0360 (9)	0.0385 (9)	0.0007 (9)	0.0048 (9)	−0.0021 (8)
C7	0.0594 (13)	0.0367 (10)	0.0490 (11)	0.0013 (11)	0.0104 (10)	0.0038 (9)
C8	0.0810 (19)	0.0569 (13)	0.0545 (12)	0.0079 (14)	0.0014 (14)	0.0134 (10)
C9	0.0651 (14)	0.0353 (9)	0.0476 (10)	−0.0019 (11)	−0.0011 (12)	−0.0011 (9)

Geometric parameters (Å, º)

O1—C7	1.210 (2)	C3—C4	1.383 (3)
N1—C9	1.138 (3)	C3—H3	0.98 (2)
N2—C7	1.367 (3)	C4—C5	1.373 (3)
N2—C6	1.402 (2)	C4—H4	0.94 (2)
N2—H22	0.85 (2)	C5—C6	1.385 (3)
C1—C2	1.385 (3)	C5—H5	0.96 (2)
C1—C6	1.400 (2)	C7—C8	1.498 (3)
C1—C9	1.433 (3)	C8—H8A	0.9600
C2—C3	1.374 (3)	C8—H8B	0.9600
C2—H2	0.94 (2)	C8—H8C	0.9600
C7—N2—C6	125.69 (17)	C4—C5—H5	123.3 (14)
C7—N2—H22	114.6 (14)	C6—C5—H5	115.9 (13)
C6—N2—H22	119.6 (14)	C5—C6—C1	118.27 (18)
C2—C1—C6	120.71 (19)	C5—C6—N2	122.50 (17)
C2—C1—C9	119.04 (17)	C1—C6—N2	119.23 (17)
C6—C1—C9	120.24 (17)	O1—C7—N2	122.91 (19)
C3—C2—C1	120.31 (19)	O1—C7—C8	122.76 (19)
C3—C2—H2	117.6 (14)	N2—C7—C8	114.33 (18)
C1—C2—H2	122.1 (14)	C7—C8—H8A	109.5
C2—C3—C4	119.0 (2)	C7—C8—H8B	109.5
C2—C3—H3	118.7 (15)	H8A—C8—H8B	109.5
C4—C3—H3	121.8 (14)	C7—C8—H8C	109.5
C5—C4—C3	121.4 (2)	H8A—C8—H8C	109.5
C5—C4—H4	120.1 (14)	H8B—C8—H8C	109.5
C3—C4—H4	118.5 (14)	N1—C9—C1	179.5 (3)
C4—C5—C6	120.38 (19)
C6—C1—C2—C3	0.4 (4)	C2—C1—C6—N2	179.4 (2)
C9—C1—C2—C3	−178.1 (3)	C9—C1—C6—N2	−2.2 (3)
C1—C2—C3—C4	−0.1 (4)	C7—N2—C6—C5	−37.9 (4)
C2—C3—C4—C5	−0.6 (4)	C7—N2—C6—C1	142.9 (2)
C3—C4—C5—C6	1.0 (4)	C6—N2—C7—O1	0.6 (4)
C4—C5—C6—C1	−0.7 (4)	C6—N2—C7—C8	−178.6 (2)
C4—C5—C6—N2	180.0 (2)	C2—C1—C9—N1	83 (28)
C2—C1—C6—C5	0.0 (3)	C6—C1—C9—N1	−95 (28)
C9—C1—C6—C5	178.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H22···N1^i	0.85 (2)	2.26 (2)	3.081 (3)	163 (2)
C3—H3···O1^ii	0.98 (2)	2.47 (2)	3.270 (3)	139 (2)
C5—H5···O1	0.97 (2)	2.49 (3)	2.914 (3)	106.3 (18)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x, y−1/2, −z+3/2.