(E)-N-(1,3-Oxazolidin-2-yl­idene)­benzamide

The aryl and oxazolidine rings in the title compound, C₁₀H₁₀N₂O₂, are essentially coplanar [dihedral angle = 3.8 (6)°]. The crystal structure involves intra- and intermolecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.122
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

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Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C8      ..       5.96 su

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
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The X-ray crystallographic structure of the title compound, (I) (Fig. 1), has not been published previously, although the deprotonated molecule has been reported in two metal complexes, namely, trans-bis(2-benzamido)oxazoline metal(II) where M = Ni (Jiang et al., 2006) and M = Cu (Zhang et al., 2004).

The bond lengths and angles have the usual values found for structurally similar molecules in the Cambridge Structural Database (CSD Version 5.24; Allen, 2002). Because of the existence of a conjugated system, the N1—C8 [1.314 (2) Å] and N2—C8 [1.301 (2) Å] bond distances are significantly shorter than the typical Csp²—N bond distance (1.426 Å; Lorente et al., 1995). The dihedral angle between the aryl rings and the oxazolidine ring is 2.856 (3)° and the C4—C7—N2—C8 torsion angle is 175.45 (2)°.

An intramolecular N1—H11···O1 hydrogen bond is found and centrosymmetrically related molecules are connected via N—H···O hydrogen bonds involving the same atoms (Table 1).

Related literature

For related literature, see: Allen (2002); Jiang et al. (2006); Lorente et al. (1995); Zhang et al. (2004).

S2. Experimental

N-Benzoyl-N'-(2-hydroxy-ethyl)thiourea was reacted with dicyclohexylcarbodiimide under weakly basic conditions in CH₃CN to give (I) in 90% yield. Single crystals suitable for the X-ray diffraction study were obtained by slow evaporation of an acetone/water solution of (I).

S3. Refinement

All the H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93–0.97 Å and and N—H = 0.86 Å, and with U_iso(H) = 1.2U_eq(carrier atom).

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and 30% probability displacement ellipsoids.

(E)—N-(1,3-Oxazolidin-2-ylidene)benzamide

Crystal data

C10H10N2O2	Dx = 1.338 Mg m^−3
Mr = 190.20	Melting point = 411–412 K
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 1672 reflections
a = 11.4194 (18) Å	θ = 3.3–22.3°
b = 20.590 (3) Å	µ = 0.10 mm^−1
c = 8.0325 (13) Å	T = 293 K
V = 1888.7 (5) Å^3	Block, colorless
Z = 8	0.25 × 0.23 × 0.18 mm
F(000) = 800

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1850 independent reflections
Radiation source: sealed tube	1091 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→14
Tmin = 0.973, Tmax = 0.988	k = −25→25
9475 measured reflections	l = −9→9

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)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.064P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max < 0.001
1850 reflections	Δρmax = 0.15 e Å^−3
128 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (12)

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
C1	0.34177 (19)	0.35640 (11)	0.2998 (3)	0.0796 (7)
H1	0.3107	0.3467	0.1958	0.096*
C2	0.33903 (19)	0.41901 (11)	0.3592 (3)	0.0792 (7)
H2	0.3060	0.4518	0.2948	0.095*
C3	0.38492 (17)	0.43353 (9)	0.5133 (2)	0.0652 (5)
H3	0.3824	0.4760	0.5523	0.078*
C4	0.43460 (15)	0.38564 (8)	0.6105 (2)	0.0518 (5)
C5	0.43765 (17)	0.32282 (9)	0.5492 (2)	0.0606 (5)
H5	0.4716	0.2900	0.6123	0.073*
C6	0.3907 (2)	0.30858 (10)	0.3953 (3)	0.0734 (6)
H6	0.3923	0.2661	0.3561	0.088*
C7	0.48292 (16)	0.40198 (8)	0.7777 (2)	0.0539 (5)
C8	0.58435 (15)	0.35996 (8)	1.0000 (2)	0.0514 (5)
C9	0.6620 (2)	0.39852 (9)	1.2444 (2)	0.0701 (6)
H9A	0.6106	0.4059	1.3387	0.084*
H9B	0.7325	0.4243	1.2574	0.084*
C10	0.69031 (19)	0.32699 (9)	1.2239 (2)	0.0709 (6)
H10A	0.7742	0.3204	1.2149	0.085*
H10B	0.6611	0.3021	1.3177	0.085*
N1	0.60390 (14)	0.41239 (7)	1.08905 (18)	0.0630 (5)
H11	0.5746	0.4494	1.0618	0.076*
N2	0.53248 (13)	0.35040 (7)	0.85798 (18)	0.0557 (4)
O1	0.47644 (13)	0.45792 (6)	0.83169 (16)	0.0782 (5)
O2	0.63240 (12)	0.30804 (6)	1.07298 (15)	0.0702 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0837 (16)	0.0822 (17)	0.0728 (14)	0.0054 (13)	−0.0193 (12)	−0.0120 (12)
C2	0.0868 (16)	0.0684 (15)	0.0823 (15)	0.0118 (12)	−0.0207 (13)	0.0051 (12)
C3	0.0741 (13)	0.0489 (11)	0.0725 (12)	0.0070 (10)	−0.0089 (11)	−0.0020 (10)
C4	0.0559 (11)	0.0425 (10)	0.0568 (10)	0.0018 (8)	0.0024 (9)	−0.0010 (8)
C5	0.0740 (13)	0.0465 (11)	0.0613 (11)	0.0053 (9)	−0.0016 (10)	−0.0052 (9)
C6	0.0869 (15)	0.0582 (13)	0.0749 (13)	0.0031 (11)	−0.0054 (12)	−0.0148 (10)
C7	0.0604 (12)	0.0413 (10)	0.0601 (11)	0.0024 (8)	0.0036 (9)	−0.0008 (8)
C8	0.0566 (11)	0.0381 (10)	0.0595 (11)	0.0041 (8)	0.0055 (9)	−0.0014 (8)
C9	0.0838 (15)	0.0544 (12)	0.0723 (13)	0.0090 (10)	−0.0162 (11)	−0.0075 (10)
C10	0.0814 (14)	0.0557 (12)	0.0756 (13)	0.0105 (10)	−0.0195 (11)	−0.0054 (10)
N1	0.0832 (12)	0.0403 (9)	0.0655 (9)	0.0110 (8)	−0.0120 (9)	−0.0057 (7)
N2	0.0694 (10)	0.0404 (9)	0.0572 (9)	0.0036 (7)	−0.0051 (8)	−0.0042 (7)
O1	0.1163 (12)	0.0400 (8)	0.0782 (9)	0.0130 (8)	−0.0197 (8)	−0.0105 (6)
O2	0.0925 (10)	0.0420 (7)	0.0760 (9)	0.0129 (6)	−0.0233 (8)	−0.0034 (6)

Geometric parameters (Å, º)

C1—C6	1.367 (3)	C7—N2	1.365 (2)
C1—C2	1.375 (3)	C8—N2	1.301 (2)
C1—H1	0.9300	C8—N1	1.314 (2)
C2—C3	1.377 (3)	C8—O2	1.3368 (19)
C2—H2	0.9300	C9—N1	1.442 (2)
C3—C4	1.380 (2)	C9—C10	1.517 (2)
C3—H3	0.9300	C9—H9A	0.9700
C4—C5	1.384 (2)	C9—H9B	0.9700
C4—C7	1.491 (2)	C10—O2	1.435 (2)
C5—C6	1.379 (2)	C10—H10A	0.9700
C5—H5	0.9300	C10—H10B	0.9700
C6—H6	0.9300	N1—H11	0.8599
C7—O1	1.2328 (19)
C6—C1—C2	119.4 (2)	N2—C8—N1	132.76 (16)
C6—C1—H1	120.3	N2—C8—O2	116.77 (15)
C2—C1—H1	120.3	N1—C8—O2	110.42 (16)
C1—C2—C3	120.44 (19)	N1—C9—C10	101.33 (15)
C1—C2—H2	119.8	N1—C9—H9A	111.5
C3—C2—H2	119.8	C10—C9—H9A	111.5
C2—C3—C4	120.66 (18)	N1—C9—H9B	111.5
C2—C3—H3	119.7	C10—C9—H9B	111.5
C4—C3—H3	119.7	H9A—C9—H9B	109.3
C3—C4—C5	118.47 (17)	O2—C10—C9	104.92 (14)
C3—C4—C7	120.05 (16)	O2—C10—H10A	110.8
C5—C4—C7	121.48 (16)	C9—C10—H10A	110.8
C6—C5—C4	120.52 (17)	O2—C10—H10B	110.8
C6—C5—H5	119.7	C9—C10—H10B	110.8
C4—C5—H5	119.7	H10A—C10—H10B	108.8
C1—C6—C5	120.6 (2)	C8—N1—C9	112.72 (15)
C1—C6—H6	119.7	C8—N1—H11	121.5
C5—C6—H6	119.7	C9—N1—H11	125.1
O1—C7—N2	125.85 (17)	C8—N2—C7	119.04 (14)
O1—C7—C4	120.36 (16)	C8—O2—C10	109.99 (14)
N2—C7—C4	113.79 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O1	0.86	2.17	2.696 (2)	119
N1—H11···O1^i	0.86	2.17	2.8944 (19)	142

Symmetry code: (i) −x+1, −y+1, −z+2.