Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032989/bx2094sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032989/bx2094Isup2.hkl |
CCDC reference: 657738
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.032
- wR factor = 0.087
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT093_ALERT_1_A No su's on H-atoms, but refinement reported as . mixed
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 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
A mixture of the p-bromobenzaldehyde(0.1 mol, 18,502 g,), and propionylhydrazine (0.1 mol, 8.810 g) was stirred in refluxing ethanol (30 ml) for 5 h to afford the title compound (0.087 mol, yield 81%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.
H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances=0.93–0.97 Å, N—H distances=0.8600 Å and with Uiso=1.2–1.5Ueq.
As an extension of our work on the structural characterization of Schiff base compound, (I), is reported here. The title compound C10H11BrN2O, is roughly planar. In (I), the bond lengths are within normal ranges (Allen et al., 1987) (Fig.1). C7=N1 bond length of 1.279 (4) Å conforms to the value for a double bond and similar to the distance reported by Qiu et al., 2006. The bond length of 1.346 (4) Å is greater than the value for a double bond, and less than the value for a single bond, because of conjugation effects in the molecule. The crystal structure is stabilized by intermolecular N—H—O hydrogen bonds (Table 1).
Scheme I
For related literature, see: Allen et al. (1987); Qiu et al. (2006).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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 showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
C10H11BrN2O | Z = 4 |
Mr = 255.12 | F(000) = 512 |
Monoclinic, P21/n | Dx = 1.568 Mg m−3 |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 4.7749 (10) Å | θ = 1.8–25.0° |
b = 10.253 (2) Å | µ = 3.77 mm−1 |
c = 22.183 (4) Å | T = 294 K |
β = 95.514 (4)° | Block, colourless |
V = 1081.0 (4) Å3 | 0.28 × 0.16 × 0.14 mm |
CCD area-detector diffractometer | 1906 independent reflections |
Radiation source: fine-focus sealed tube | 1363 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
phi and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −5→5 |
Tmin = 0.418, Tmax = 0.620 | k = −12→9 |
5443 measured reflections | l = −23→26 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0412P)2 + 0.4567P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
1906 reflections | Δρmax = 0.41 e Å−3 |
129 parameters | Δρmin = −0.34 e Å−3 |
6 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0194 (15) |
C10H11BrN2O | V = 1081.0 (4) Å3 |
Mr = 255.12 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.7749 (10) Å | µ = 3.77 mm−1 |
b = 10.253 (2) Å | T = 294 K |
c = 22.183 (4) Å | 0.28 × 0.16 × 0.14 mm |
β = 95.514 (4)° |
CCD area-detector diffractometer | 1906 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1363 reflections with I > 2σ(I) |
Tmin = 0.418, Tmax = 0.620 | Rint = 0.035 |
5443 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 6 restraints |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.41 e Å−3 |
1906 reflections | Δρmin = −0.34 e Å−3 |
129 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 | ||
Br1 | 0.77061 (8) | 0.21453 (4) | 0.196101 (18) | 0.0605 (2) | |
N1 | −0.0531 (6) | 0.1549 (3) | 0.43391 (13) | 0.0441 (7) | |
O1 | −0.4993 (5) | 0.1484 (3) | 0.54910 (11) | 0.0573 (7) | |
N2 | −0.2420 (6) | 0.1110 (3) | 0.47212 (13) | 0.0471 (8) | |
H2 | −0.3080 | 0.0331 | 0.4679 | 0.057* | |
C1 | 0.3146 (7) | 0.2337 (3) | 0.34522 (16) | 0.0465 (9) | |
H1 | 0.2713 | 0.2969 | 0.3729 | 0.056* | |
C2 | 0.4859 (8) | 0.2653 (4) | 0.30103 (17) | 0.0477 (9) | |
H2A | 0.5590 | 0.3491 | 0.2989 | 0.057* | |
C3 | 0.5480 (7) | 0.1711 (4) | 0.25989 (15) | 0.0429 (9) | |
C4 | 0.4499 (7) | 0.0465 (4) | 0.26351 (17) | 0.0500 (9) | |
H4 | 0.4975 | −0.0166 | 0.2362 | 0.060* | |
C5 | 0.2792 (7) | 0.0152 (4) | 0.30818 (16) | 0.0501 (10) | |
H5 | 0.2130 | −0.0697 | 0.3109 | 0.060* | |
C6 | 0.2049 (7) | 0.1087 (3) | 0.34909 (14) | 0.0396 (8) | |
C7 | 0.0139 (7) | 0.0733 (3) | 0.39412 (15) | 0.0427 (8) | |
H7 | −0.0606 | −0.0105 | 0.3938 | 0.051* | |
C8 | −0.3254 (7) | 0.1882 (3) | 0.51608 (16) | 0.0446 (9) | |
C9 | −0.1936 (9) | 0.3205 (4) | 0.5226 (2) | 0.0647 (12) | |
H9A | −0.2210 | 0.3649 | 0.4839 | 0.078* | |
H9B | 0.0074 | 0.3101 | 0.5327 | 0.078* | |
C10 | −0.3091 (10) | 0.4053 (4) | 0.5702 (2) | 0.0781 (14) | |
H10A | −0.2727 | 0.3648 | 0.6092 | 0.117* | |
H10B | −0.5083 | 0.4158 | 0.5608 | 0.117* | |
H10C | −0.2195 | 0.4892 | 0.5708 | 0.117* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0552 (3) | 0.0728 (4) | 0.0571 (3) | −0.0027 (2) | 0.02439 (19) | 0.0049 (2) |
N1 | 0.0437 (16) | 0.0492 (18) | 0.0415 (17) | −0.0020 (14) | 0.0153 (14) | 0.0055 (14) |
O1 | 0.0602 (16) | 0.0590 (17) | 0.0574 (16) | −0.0039 (14) | 0.0288 (14) | 0.0030 (13) |
N2 | 0.0523 (17) | 0.0448 (19) | 0.0473 (17) | −0.0056 (14) | 0.0199 (15) | 0.0033 (14) |
C1 | 0.052 (2) | 0.042 (2) | 0.046 (2) | 0.0005 (17) | 0.0097 (17) | −0.0070 (17) |
C2 | 0.053 (2) | 0.039 (2) | 0.053 (2) | −0.0070 (17) | 0.0108 (18) | −0.0007 (17) |
C3 | 0.0373 (18) | 0.051 (2) | 0.041 (2) | 0.0030 (16) | 0.0108 (16) | 0.0058 (16) |
C4 | 0.056 (2) | 0.041 (2) | 0.056 (2) | 0.0054 (18) | 0.0200 (18) | −0.0042 (18) |
C5 | 0.053 (2) | 0.038 (2) | 0.062 (2) | −0.0045 (17) | 0.0194 (19) | −0.0004 (18) |
C6 | 0.0382 (18) | 0.042 (2) | 0.0391 (19) | 0.0023 (16) | 0.0053 (15) | 0.0014 (16) |
C7 | 0.0431 (19) | 0.041 (2) | 0.045 (2) | −0.0002 (16) | 0.0081 (16) | 0.0037 (16) |
C8 | 0.045 (2) | 0.047 (2) | 0.043 (2) | 0.0059 (16) | 0.0118 (17) | 0.0063 (17) |
C9 | 0.074 (3) | 0.053 (3) | 0.072 (3) | −0.006 (2) | 0.033 (2) | −0.007 (2) |
C10 | 0.083 (3) | 0.069 (3) | 0.087 (3) | −0.006 (2) | 0.030 (3) | −0.019 (2) |
Br1—C3 | 1.903 (3) | C4—H4 | 0.9300 |
N1—C7 | 1.279 (4) | C5—C6 | 1.389 (5) |
N1—N2 | 1.372 (3) | C5—H5 | 0.9300 |
O1—C8 | 1.228 (4) | C6—C7 | 1.462 (4) |
N2—C8 | 1.346 (4) | C7—H7 | 0.9300 |
N2—H2 | 0.8600 | C8—C9 | 1.497 (5) |
C1—C2 | 1.374 (5) | C9—C10 | 1.513 (5) |
C1—C6 | 1.391 (5) | C9—H9A | 0.9700 |
C1—H1 | 0.9300 | C9—H9B | 0.9700 |
C2—C3 | 1.381 (5) | C10—H10A | 0.9600 |
C2—H2A | 0.9300 | C10—H10B | 0.9600 |
C3—C4 | 1.366 (5) | C10—H10C | 0.9600 |
C4—C5 | 1.380 (4) | ||
C7—N1—N2 | 115.8 (3) | C5—C6—C7 | 119.4 (3) |
C8—N2—N1 | 120.8 (3) | C1—C6—C7 | 122.3 (3) |
C8—N2—H2 | 119.6 | N1—C7—C6 | 121.6 (3) |
N1—N2—H2 | 119.6 | N1—C7—H7 | 119.2 |
C2—C1—C6 | 121.0 (3) | C6—C7—H7 | 119.2 |
C2—C1—H1 | 119.5 | O1—C8—N2 | 120.1 (3) |
C6—C1—H1 | 119.5 | O1—C8—C9 | 123.0 (3) |
C1—C2—C3 | 119.1 (3) | N2—C8—C9 | 116.9 (3) |
C1—C2—H2A | 120.4 | C8—C9—C10 | 114.3 (3) |
C3—C2—H2A | 120.4 | C8—C9—H9A | 108.7 |
C4—C3—C2 | 121.3 (3) | C10—C9—H9A | 108.7 |
C4—C3—Br1 | 118.8 (3) | C8—C9—H9B | 108.7 |
C2—C3—Br1 | 119.9 (3) | C10—C9—H9B | 108.7 |
C3—C4—C5 | 119.3 (3) | H9A—C9—H9B | 107.6 |
C3—C4—H4 | 120.4 | C9—C10—H10A | 109.5 |
C5—C4—H4 | 120.4 | C9—C10—H10B | 109.5 |
C4—C5—C6 | 121.0 (3) | H10A—C10—H10B | 109.5 |
C4—C5—H5 | 119.5 | C9—C10—H10C | 109.5 |
C6—C5—H5 | 119.5 | H10A—C10—H10C | 109.5 |
C5—C6—C1 | 118.3 (3) | H10B—C10—H10C | 109.5 |
C7—N1—N2—C8 | 179.4 (3) | C2—C1—C6—C5 | 1.8 (5) |
C6—C1—C2—C3 | 0.3 (5) | C2—C1—C6—C7 | −177.7 (3) |
C1—C2—C3—C4 | −2.1 (5) | N2—N1—C7—C6 | 177.7 (3) |
C1—C2—C3—Br1 | 177.2 (3) | C5—C6—C7—N1 | 177.7 (3) |
C2—C3—C4—C5 | 1.8 (6) | C1—C6—C7—N1 | −2.8 (5) |
Br1—C3—C4—C5 | −177.5 (3) | N1—N2—C8—O1 | 178.4 (3) |
C3—C4—C5—C6 | 0.4 (5) | N1—N2—C8—C9 | −2.5 (5) |
C4—C5—C6—C1 | −2.1 (5) | O1—C8—C9—C10 | −4.5 (6) |
C4—C5—C6—C7 | 177.4 (3) | N2—C8—C9—C10 | 176.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.86 | 2.09 | 2.951 (4) | 174 |
Symmetry code: (i) −x−1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H11BrN2O |
Mr | 255.12 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 4.7749 (10), 10.253 (2), 22.183 (4) |
β (°) | 95.514 (4) |
V (Å3) | 1081.0 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.77 |
Crystal size (mm) | 0.28 × 0.16 × 0.14 |
Data collection | |
Diffractometer | CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.418, 0.620 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5443, 1906, 1363 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.087, 1.00 |
No. of reflections | 1906 |
No. of parameters | 129 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.41, −0.34 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, 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 | 2.09 | 2.951 (4) | 174.0 |
Symmetry code: (i) −x−1, −y, −z+1. |
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As an extension of our work on the structural characterization of Schiff base compound, (I), is reported here. The title compound C10H11BrN2O, is roughly planar. In (I), the bond lengths are within normal ranges (Allen et al., 1987) (Fig.1). C7=N1 bond length of 1.279 (4) Å conforms to the value for a double bond and similar to the distance reported by Qiu et al., 2006. The bond length of 1.346 (4) Å is greater than the value for a double bond, and less than the value for a single bond, because of conjugation effects in the molecule. The crystal structure is stabilized by intermolecular N—H—O hydrogen bonds (Table 1).
Scheme I