2-Methyl­benzamidoxime

In the crystal structure of the title compound, C₈H₁₀N₂O, which is a benzonitrile derivative, an intra­molecular N—H...O hydrogen bond and inter­molecular N—H...O and O—H...N hydrogen bonds are present.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.060
• wR factor = 0.189
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97.

2-Methylbenzamidoxime

Crystal data

C8H10N2O	F(000) = 320
Mr = 150.18	Dx = 1.218 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 9.751 (2) Å	θ = 9–12°
b = 7.0880 (14) Å	µ = 0.08 mm^−1
c = 11.982 (2) Å	T = 293 K
β = 98.60 (3)°	Block, yellow
V = 818.8 (3) Å^3	0.40 × 0.20 × 0.20 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	1124 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
Graphite monochromator	θmax = 26.0°, θmin = 2.5°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
Tmin = 0.968, Tmax = 0.984	l = −14→14
1694 measured reflections	3 standard reflections every 200 reflections
1600 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.189	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1125P)^2 + 0.0887P] where P = (Fo^2 + 2Fc^2)/3
1600 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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
O	0.65920 (16)	0.0065 (2)	0.06365 (14)	0.0565 (5)
H1w	0.6228	−0.0688	0.0163	0.085*
N1	0.7473 (2)	0.2577 (3)	0.2082 (2)	0.0756 (8)
H1A	0.8035	0.1803	0.1832	0.091*
H1B	0.7785	0.3408	0.2578	0.091*
N2	0.55481 (18)	0.1307 (2)	0.09602 (15)	0.0464 (5)
C1	0.5160 (4)	0.1785 (4)	0.3878 (2)	0.0726 (8)
H1C	0.4771	0.1823	0.4568	0.109*
H1D	0.6152	0.1704	0.4049	0.109*
H1E	0.4810	0.0703	0.3445	0.109*
C2	0.4765 (2)	0.3548 (3)	0.32086 (18)	0.0464 (6)
C3	0.3938 (2)	0.4922 (3)	0.3610 (2)	0.0547 (6)
H3A	0.3647	0.4744	0.4307	0.066*
C4	0.3537 (3)	0.6534 (4)	0.3007 (2)	0.0613 (7)
H4A	0.2981	0.7421	0.3295	0.074*
C5	0.3960 (3)	0.6826 (4)	0.1984 (2)	0.0655 (7)
H5A	0.3699	0.7916	0.1574	0.079*
C6	0.4778 (2)	0.5489 (3)	0.1564 (2)	0.0540 (6)
H6A	0.5062	0.5686	0.0866	0.065*
C7	0.5183 (2)	0.3863 (3)	0.21620 (17)	0.0406 (5)
C8	0.6110 (2)	0.2487 (3)	0.16958 (17)	0.0424 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O	0.0542 (10)	0.0507 (10)	0.0641 (10)	0.0093 (7)	0.0072 (8)	−0.0163 (8)
N1	0.0493 (12)	0.0692 (16)	0.1029 (18)	0.0081 (11)	−0.0061 (12)	−0.0343 (13)
N2	0.0491 (10)	0.0419 (10)	0.0481 (10)	0.0061 (8)	0.0077 (8)	−0.0084 (8)
C1	0.105 (2)	0.0529 (15)	0.0619 (16)	−0.0035 (15)	0.0182 (15)	0.0129 (12)
C2	0.0518 (12)	0.0411 (12)	0.0451 (12)	−0.0076 (10)	0.0032 (9)	−0.0033 (9)
C3	0.0542 (13)	0.0604 (15)	0.0504 (13)	−0.0077 (11)	0.0112 (10)	−0.0113 (11)
C4	0.0534 (14)	0.0608 (16)	0.0685 (16)	0.0121 (12)	0.0051 (12)	−0.0155 (13)
C5	0.0745 (17)	0.0509 (14)	0.0682 (17)	0.0214 (13)	0.0013 (13)	0.0019 (12)
C6	0.0631 (14)	0.0504 (14)	0.0474 (13)	0.0088 (11)	0.0048 (10)	0.0036 (10)
C7	0.0404 (11)	0.0325 (11)	0.0467 (11)	−0.0024 (8)	−0.0003 (8)	−0.0053 (9)
C8	0.0457 (11)	0.0351 (11)	0.0456 (11)	−0.0005 (9)	0.0042 (9)	0.0024 (9)

Geometric parameters (Å, º)

O—N2	1.442 (2)	C2—C3	1.395 (3)
O—H1w	0.8200	C3—C4	1.377 (4)
N1—C8	1.342 (3)	C3—H3A	0.9300
N1—H1A	0.8600	C4—C5	1.366 (4)
N1—H1B	0.8600	C4—H4A	0.9300
N2—C8	1.278 (3)	C5—C6	1.381 (3)
C1—C2	1.504 (3)	C5—H5A	0.9300
C1—H1C	0.9600	C6—C7	1.383 (3)
C1—H1D	0.9600	C6—H6A	0.9300
C1—H1E	0.9600	C7—C8	1.494 (3)
C2—C7	1.393 (3)
N2—O—H1w	109.5	C2—C3—H3A	118.9
C8—N1—H1A	120.0	C5—C4—C3	119.8 (2)
C8—N1—H1B	120.0	C5—C4—H4A	120.1
H1A—N1—H1B	120.0	C3—C4—H4A	120.1
C8—N2—O	109.75 (17)	C4—C5—C6	119.4 (2)
C2—C1—H1C	109.5	C4—C5—H5A	120.3
C2—C1—H1D	109.5	C6—C5—H5A	120.3
H1C—C1—H1D	109.5	C5—C6—C7	121.3 (2)
C2—C1—H1E	109.5	C5—C6—H6A	119.4
H1C—C1—H1E	109.5	C7—C6—H6A	119.4
H1D—C1—H1E	109.5	C6—C7—C2	120.0 (2)
C7—C2—C3	117.4 (2)	C6—C7—C8	119.48 (19)
C7—C2—C1	121.8 (2)	C2—C7—C8	120.47 (18)
C3—C2—C1	120.8 (2)	N2—C8—N1	124.7 (2)
C4—C3—C2	122.1 (2)	N2—C8—C7	117.66 (18)
C4—C3—H3A	118.9	N1—C8—C7	117.65 (18)
C7—C2—C3—C4	0.1 (3)	C3—C2—C7—C8	177.87 (19)
C1—C2—C3—C4	−178.8 (2)	C1—C2—C7—C8	−3.3 (3)
C2—C3—C4—C5	−0.4 (4)	O—N2—C8—N1	1.6 (3)
C3—C4—C5—C6	0.5 (4)	O—N2—C8—C7	−178.25 (16)
C4—C5—C6—C7	−0.3 (4)	C6—C7—C8—N2	−82.6 (3)
C5—C6—C7—C2	0.0 (3)	C2—C7—C8—N2	99.6 (2)
C5—C6—C7—C8	−177.8 (2)	C6—C7—C8—N1	97.6 (3)
C3—C2—C7—C6	0.1 (3)	C2—C7—C8—N1	−80.2 (3)
C1—C2—C7—C6	178.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O^i	0.86	2.44	3.267 (3)	163
N1—H1A···O	0.86	2.22	2.542 (3)	102
O—H1w···N2^ii	0.82	2.08	2.787 (3)	145

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