Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038925/at2367sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038925/at2367Isup2.hkl |
CCDC reference: 660274
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
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 Uiso(H) = 1.2–1.5Ueq(C, N).
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).
For related literature, see: Allen et al. (1987); Sutherland & Hoy (1968); Tucker et al. (1975).
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).
Fig. 1. The structure of the title compound (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
C10H12N2O | V = 493.7 (5) Å3 |
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 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0829P)2] where P = (Fo2 + 2Fc2)/3 |
1715 reflections | (Δ/σ)max < 0.001 |
119 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C10H12N2O | γ = 91.139 (9)° |
Mr = 176.22 | V = 493.7 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.210 (3) Å | Mo Kα radiation |
b = 8.838 (5) Å | µ = 0.08 mm−1 |
c = 11.530 (6) Å | T = 293 K |
α = 111.419 (9)° | 0.22 × 0.20 × 0.14 mm |
β = 91.916 (9)° |
Bruker SMART CCD area-detector diffractometer | 882 reflections with I > 2σ(I) |
2478 measured reflections | Rint = 0.020 |
1715 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.17 e Å−3 |
1715 reflections | Δρmin = −0.18 e Å−3 |
119 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.86 | 2.07 | 2.906 (3) | 163 |
Symmetry code: (i) −x−1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H12N2O |
Mr | 176.22 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 5.210 (3), 8.838 (5), 11.530 (6) |
α, β, γ (°) | 111.419 (9), 91.916 (9), 91.139 (9) |
V (Å3) | 493.7 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.22 × 0.20 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2478, 1715, 882 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.165, 1.02 |
No. of reflections | 1715 |
No. of parameters | 119 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.18 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.86 | 2.07 | 2.906 (3) | 163.0 |
Symmetry code: (i) −x−1, −y, −z+1. |
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).