Benzaldehyde propionylhydrazone

The title compound, C₁₀H₁₂N₂O, was prepared by the reaction between benzaldehyde and propionylhydrazine. The crystal structure is stabilized by inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.165
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTY03_ALERT_1_C  The _exptl_absorpt_correction_type has been given as none.
            However values have been given for Tmin and Tmax. Remove
            these if an absorption correction has not been applied.
  From the CIF: _exptl_absorpt_correction_T_min   0.983
  From the CIF: _exptl_absorpt_correction_T_max   0.989
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        900 Deg.

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

   6 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

As an extension of our work on the structural characterization of Schiff base compounds, we here report the structure of the title molecule (I). The title compound (I), is nearly planar. In (I) (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). The C7—N1 distance of 1.273 (3) Å is similar to the distance of 1.287 Å reported by Tucker et al. (1975). The C8—O1 distance of 1.228 (3) Å is shorter than the reported distance of 1.298 Å by Sutherland & Hoy (1968).

The crystal structure of (I) is stabilized by intermolecular N—H···O hydrogen bonds (Table 1).

Related literature

For related literature, see: Allen et al. (1987); Sutherland & Hoy (1968); Tucker et al. (1975).

S2. Experimental

A mixture of the benzaldehyde (0.1 mol), and propionylhydrazine (0.1 mol) was stirred in refluxing ethanol (30 ml) for 5 h to afford the title compound (I) (0.087 mol, yield 87%). Single crystals of (I) suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

S3. Refinement

H atoms were located geometrically and allowed to ride on their attached atoms, with C—H = 0.93–0.97 Å, N—H = 0.86 Å and with U_iso(H) = 1.2–1.5U_eq(C, N).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

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

Benzaldehyde propionylhydrazone

Crystal data

C10H12N2O	V = 493.7 (5) Å^3
Mr = 176.22	Z = 2
Triclinic, P1	F(000) = 188
Hall symbol: -P 1	Dx = 1.185 Mg m^−3
a = 5.210 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.838 (5) Å	θ = 1.9–25.0°
c = 11.530 (6) Å	µ = 0.08 mm^−1
α = 111.419 (9)°	T = 293 K
β = 91.916 (9)°	Block, colourless
γ = 91.139 (9)°	0.22 × 0.20 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	882 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
φ and ω scans	h = −6→6
2478 measured reflections	k = −10→10
1715 independent reflections	l = −13→10

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0829P)^2] where P = (Fo^2 + 2Fc^2)/3
1715 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.18 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
O1	−0.4450 (3)	−0.0595 (2)	0.33336 (16)	0.0687 (6)
N1	−0.0417 (4)	0.2515 (2)	0.5372 (2)	0.0556 (6)
N2	−0.2421 (4)	0.1394 (2)	0.49157 (19)	0.0597 (6)
H2	−0.3550	0.1312	0.5419	0.072*
C1	0.1970 (6)	0.5178 (4)	0.8455 (3)	0.0775 (9)
H1	0.0842	0.4834	0.8924	0.093*
C2	0.3860 (7)	0.6354 (4)	0.9060 (3)	0.0863 (10)
H2A	0.3992	0.6788	0.9927	0.104*
C3	0.5519 (6)	0.6874 (4)	0.8390 (3)	0.0784 (10)
H3	0.6796	0.7657	0.8795	0.094*
C4	0.5301 (6)	0.6234 (4)	0.7106 (3)	0.0813 (10)
H4	0.6419	0.6596	0.6643	0.098*
C5	0.3428 (5)	0.5058 (3)	0.6507 (3)	0.0682 (9)
H5	0.3307	0.4626	0.5640	0.082*
C6	0.1727 (5)	0.4508 (3)	0.7172 (2)	0.0535 (7)
C7	−0.0300 (5)	0.3266 (3)	0.6549 (3)	0.0596 (7)
H7	−0.1529	0.3024	0.7027	0.071*
C8	−0.2668 (5)	0.0419 (3)	0.3702 (3)	0.0536 (7)
C9	−0.0709 (5)	0.0639 (3)	0.2847 (2)	0.0641 (8)
H9A	0.0980	0.0440	0.3131	0.077*
H9B	−0.0703	0.1757	0.2893	0.077*
C10	−0.1205 (7)	−0.0485 (4)	0.1498 (3)	0.0891 (11)
H10A	−0.1256	−0.1594	0.1447	0.134*
H10B	0.0147	−0.0328	0.1003	0.134*
H10C	−0.2820	−0.0242	0.1191	0.134*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0640 (13)	0.0637 (12)	0.0708 (13)	−0.0252 (10)	−0.0097 (10)	0.0181 (10)
N1	0.0564 (14)	0.0497 (12)	0.0561 (14)	−0.0141 (10)	−0.0086 (11)	0.0157 (11)
N2	0.0586 (14)	0.0567 (13)	0.0576 (14)	−0.0214 (11)	−0.0017 (11)	0.0149 (12)
C1	0.096 (2)	0.076 (2)	0.0572 (19)	−0.0216 (18)	−0.0023 (17)	0.0216 (17)
C2	0.104 (3)	0.075 (2)	0.061 (2)	−0.018 (2)	−0.018 (2)	0.0056 (18)
C3	0.070 (2)	0.0627 (19)	0.084 (2)	−0.0173 (16)	−0.0155 (19)	0.0081 (19)
C4	0.077 (2)	0.074 (2)	0.078 (2)	−0.0273 (17)	−0.0031 (17)	0.0126 (18)
C5	0.0701 (19)	0.0655 (18)	0.0564 (17)	−0.0216 (15)	0.0000 (15)	0.0090 (15)
C6	0.0602 (17)	0.0448 (14)	0.0523 (16)	−0.0039 (13)	−0.0010 (14)	0.0147 (14)
C7	0.0617 (18)	0.0545 (16)	0.0608 (18)	−0.0142 (13)	−0.0019 (14)	0.0203 (15)
C8	0.0488 (16)	0.0488 (15)	0.0606 (18)	−0.0080 (13)	−0.0070 (14)	0.0183 (14)
C9	0.0638 (19)	0.0571 (16)	0.0630 (18)	−0.0106 (14)	−0.0018 (15)	0.0129 (15)
C10	0.117 (3)	0.078 (2)	0.063 (2)	−0.0226 (19)	0.0082 (18)	0.0168 (17)

Geometric parameters (Å, º)

O1—C8	1.228 (3)	C4—H4	0.9300
N1—C7	1.273 (3)	C5—C6	1.382 (4)
N1—N2	1.374 (3)	C5—H5	0.9300
N2—C8	1.349 (3)	C6—C7	1.471 (3)
N2—H2	0.8600	C7—H7	0.9300
C1—C6	1.378 (3)	C8—C9	1.500 (4)
C1—C2	1.386 (4)	C9—C10	1.519 (3)
C1—H1	0.9300	C9—H9A	0.9700
C2—C3	1.358 (4)	C9—H9B	0.9700
C2—H2A	0.9300	C10—H10A	0.9600
C3—C4	1.378 (4)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600
C4—C5	1.378 (3)
C7—N1—N2	115.5 (2)	C1—C6—C7	120.5 (3)
C8—N2—N1	121.9 (2)	C5—C6—C7	121.9 (2)
C8—N2—H2	119.0	N1—C7—C6	121.7 (3)
N1—N2—H2	119.0	N1—C7—H7	119.1
C6—C1—C2	121.4 (3)	C6—C7—H7	119.1
C6—C1—H1	119.3	O1—C8—N2	120.1 (2)
C2—C1—H1	119.3	O1—C8—C9	122.5 (2)
C3—C2—C1	120.1 (3)	N2—C8—C9	117.4 (2)
C3—C2—H2A	119.9	C8—C9—C10	113.1 (2)
C1—C2—H2A	119.9	C8—C9—H9A	109.0
C2—C3—C4	119.6 (3)	C10—C9—H9A	109.0
C2—C3—H3	120.2	C8—C9—H9B	109.0
C4—C3—H3	120.2	C10—C9—H9B	109.0
C5—C4—C3	120.1 (3)	H9A—C9—H9B	107.8
C5—C4—H4	120.0	C9—C10—H10A	109.5
C3—C4—H4	120.0	C9—C10—H10B	109.5
C4—C5—C6	121.2 (3)	H10A—C10—H10B	109.5
C4—C5—H5	119.4	C9—C10—H10C	109.5
C6—C5—H5	119.4	H10A—C10—H10C	109.5
C1—C6—C5	117.6 (3)	H10B—C10—H10C	109.5
C7—N1—N2—C8	−174.7 (2)	C4—C5—C6—C7	179.3 (3)
C6—C1—C2—C3	0.2 (5)	N2—N1—C7—C6	−179.6 (2)
C1—C2—C3—C4	0.5 (5)	C1—C6—C7—N1	−173.1 (3)
C2—C3—C4—C5	−0.8 (5)	C5—C6—C7—N1	7.6 (4)
C3—C4—C5—C6	0.6 (5)	N1—N2—C8—O1	178.2 (2)
C2—C1—C6—C5	−0.4 (4)	N1—N2—C8—C9	−2.0 (4)
C2—C1—C6—C7	−179.7 (3)	O1—C8—C9—C10	1.3 (4)
C4—C5—C6—C1	0.0 (4)	N2—C8—C9—C10	−178.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.86	2.07	2.906 (3)	163

Symmetry code: (i) −x−1, −y, −z+1.