Literature DB >> 24046691

N'-[(E)-4-Bromo-benzyl-idene]pyrazine-2-carbohydrazide.

Shahid Hameed¹, Mushtaq Ahmad, M Nawaz Tahir, Muhammad Abdullah Shah, Hazoor Ahmad Shad.

Abstract

In the title compound, C12H9BrN4O, the N'-methyl-idene-pyrazine-2-carbohydrazide and 4-bromobenzene groups are oriented at a dihedral angle of 10.57 (7)°. The hydrazide N-H group is involved in intra-molecular N-H⋯N inter-action, which generates an S(5) motif. A short C-H⋯O inter-action is formed between the methyl-idene H atom and the carbonyl O atom. It connects mol-ecules into chains extending along [100]. In addition, mol-ecules are arranged into stacks extending along [010] via π-π inter-actions between pyrazine and benzene rings, with centroid-centroid distances of 3.837 (2) and 3.860 (2) Å.

Entities: Chemical Disease Species

Year: 2013 PMID： 24046691 PMCID： PMC3770406 DOI： 10.1107/S1600536813016917

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For a related crystal structure and related studies, see: Hearn & Cynamon (2004 ▶); Jin et al. (2006 ▶); Yuan et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H9BrN4O M = 305.14 Triclinic, a = 5.8947 (9) Å b = 7.6941 (12) Å c = 14.029 (2) Å α = 83.273 (7)° β = 80.086 (7)° γ = 72.440 (6)° V = 596.11 (16) Å3 Z = 2 Mo Kα radiation μ = 3.44 mm−1 T = 296 K 0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.425, T max = 0.503 7382 measured reflections 2529 independent reflections 1403 reflections with I > 2σ(I) R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.084 S = 0.94 2529 reflections 163 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.30 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016917/gk2580sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016917/gk2580Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813016917/gk2580Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₂H₉BrN₄O	Z = 2
M_r = 305.14	F(000) = 304
Triclinic, P1	D_x = 1.700 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8947 (9) Å	Cell parameters from 1403 reflections
b = 7.6941 (12) Å	θ = 2.1–25.5°
c = 14.029 (2) Å	µ = 3.44 mm⁻¹
α = 83.273 (7)°	T = 296 K
β = 80.086 (7)°	Prism, white
γ = 72.440 (6)°	0.26 × 0.22 × 0.20 mm
V = 596.11 (16) Å³

Bruker Kappa APEXII CCD diffractometer	2529 independent reflections
Radiation source: fine-focus sealed tube	1403 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
Detector resolution: 8.10 pixels mm^-1	θ_max = 27.1°, θ_min = 1.5°
ω scans	h = −7→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
T_min = 0.425, T_max = 0.503	l = −17→17
7382 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0355P)²] where P = (F_o² + 2F_c²)/3
2529 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

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	U_iso*/U_eq
Br1	0.36405 (7)	0.25644 (5)	0.47485 (3)	0.07332 (19)
O1	−0.4594 (4)	0.8146 (3)	−0.03918 (16)	0.0633 (7)
N1	−0.0274 (4)	0.9547 (3)	−0.21291 (18)	0.0486 (7)
N2	−0.4307 (5)	1.1093 (4)	−0.3071 (2)	0.0599 (8)
N3	−0.0701 (5)	0.7949 (3)	−0.03380 (18)	0.0523 (7)
H3A	0.0565	0.8198	−0.0649	0.063*
N4	−0.0613 (5)	0.7038 (3)	0.05682 (19)	0.0508 (7)
C1	−0.2458 (5)	0.9456 (4)	−0.1727 (2)	0.0401 (8)
C2	−0.0148 (6)	1.0405 (4)	−0.3008 (2)	0.0538 (9)
H2	0.1337	1.0501	−0.3321	0.065*
C3	−0.2126 (6)	1.1151 (4)	−0.3467 (2)	0.0549 (9)
H3	−0.1927	1.1724	−0.4084	0.066*
C4	−0.4426 (6)	1.0230 (4)	−0.2191 (3)	0.0540 (9)
H4	−0.5918	1.0148	−0.1877	0.065*
C5	−0.2732 (6)	0.8455 (4)	−0.0745 (2)	0.0476 (8)
C6	0.1460 (6)	0.6511 (4)	0.0827 (2)	0.0496 (9)
H6	0.2748	0.6734	0.0398	0.060*
C7	0.1898 (6)	0.5575 (4)	0.1764 (2)	0.0449 (8)
C8	0.0083 (6)	0.5360 (4)	0.2494 (2)	0.0496 (8)
H8	−0.1509	0.5833	0.2386	0.060*
C9	0.0571 (6)	0.4466 (4)	0.3372 (2)	0.0524 (9)
H9	−0.0679	0.4339	0.3853	0.063*
C10	0.2919 (6)	0.3757 (4)	0.3537 (2)	0.0500 (8)
C11	0.4775 (6)	0.3941 (4)	0.2827 (2)	0.0555 (9)
H11	0.6361	0.3455	0.2939	0.067*
C12	0.4264 (6)	0.4854 (4)	0.1945 (2)	0.0543 (9)
H12	0.5516	0.4989	0.1467	0.065*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0815 (3)	0.0777 (3)	0.0601 (3)	−0.0224 (2)	−0.0225 (2)	0.01461 (19)
O1	0.0580 (15)	0.0762 (17)	0.0622 (15)	−0.0398 (13)	0.0071 (13)	0.0006 (12)
N1	0.0420 (16)	0.0576 (17)	0.0482 (17)	−0.0216 (13)	−0.0063 (13)	0.0069 (13)
N2	0.0479 (18)	0.070 (2)	0.064 (2)	−0.0208 (15)	−0.0186 (16)	0.0107 (15)
N3	0.0564 (19)	0.0604 (18)	0.0429 (16)	−0.0271 (14)	−0.0057 (15)	0.0106 (13)
N4	0.0555 (19)	0.0552 (17)	0.0433 (17)	−0.0238 (14)	−0.0035 (14)	0.0059 (13)
C1	0.0373 (19)	0.0392 (18)	0.0455 (19)	−0.0143 (15)	−0.0058 (16)	−0.0009 (14)
C2	0.048 (2)	0.066 (2)	0.050 (2)	−0.0259 (17)	−0.0076 (18)	0.0125 (17)
C3	0.057 (2)	0.061 (2)	0.051 (2)	−0.0225 (18)	−0.0159 (19)	0.0060 (17)
C4	0.041 (2)	0.062 (2)	0.062 (2)	−0.0221 (17)	−0.0034 (18)	−0.0014 (18)
C5	0.052 (2)	0.047 (2)	0.048 (2)	−0.0234 (17)	−0.0001 (18)	−0.0048 (16)
C6	0.055 (2)	0.053 (2)	0.045 (2)	−0.0293 (17)	−0.0008 (18)	0.0027 (16)
C7	0.048 (2)	0.0429 (18)	0.048 (2)	−0.0225 (15)	−0.0039 (17)	−0.0031 (15)
C8	0.0401 (19)	0.053 (2)	0.057 (2)	−0.0192 (16)	−0.0062 (17)	0.0068 (17)
C9	0.048 (2)	0.059 (2)	0.051 (2)	−0.0221 (17)	−0.0024 (18)	0.0051 (17)
C10	0.052 (2)	0.049 (2)	0.051 (2)	−0.0199 (16)	−0.0092 (18)	0.0019 (15)
C11	0.043 (2)	0.060 (2)	0.065 (2)	−0.0157 (17)	−0.0119 (19)	−0.0025 (18)
C12	0.048 (2)	0.064 (2)	0.054 (2)	−0.0247 (17)	0.0008 (18)	−0.0048 (18)

Br1—C10	1.886 (3)	C3—H3	0.9300
O1—C5	1.204 (3)	C4—H4	0.9300
N1—C2	1.329 (4)	C6—C7	1.447 (4)
N1—C1	1.332 (3)	C6—H6	0.9300
N2—C3	1.322 (4)	C7—C8	1.383 (4)
N2—C4	1.332 (4)	C7—C12	1.393 (4)
N3—C5	1.346 (4)	C8—C9	1.370 (4)
N3—N4	1.379 (3)	C8—H8	0.9300
N3—H3A	0.8600	C9—C10	1.376 (4)
N4—C6	1.268 (4)	C9—H9	0.9300
C1—C4	1.370 (4)	C10—C11	1.377 (4)
C1—C5	1.506 (4)	C11—C12	1.382 (4)
C2—C3	1.368 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300

C2—N1—C1	115.4 (3)	N4—C6—C7	122.5 (3)
C3—N2—C4	114.6 (3)	N4—C6—H6	118.7
C5—N3—N4	121.3 (3)	C7—C6—H6	118.7
C5—N3—H3A	119.4	C8—C7—C12	117.9 (3)
N4—N3—H3A	119.4	C8—C7—C6	123.3 (3)
C6—N4—N3	114.5 (3)	C12—C7—C6	118.7 (3)
N1—C1—C4	121.5 (3)	C9—C8—C7	121.6 (3)
N1—C1—C5	118.5 (3)	C9—C8—H8	119.2
C4—C1—C5	119.9 (3)	C7—C8—H8	119.2
N1—C2—C3	122.4 (3)	C8—C9—C10	119.7 (3)
N1—C2—H2	118.8	C8—C9—H9	120.2
C3—C2—H2	118.8	C10—C9—H9	120.2
N2—C3—C2	122.8 (3)	C9—C10—C11	120.4 (3)
N2—C3—H3	118.6	C9—C10—Br1	120.6 (3)
C2—C3—H3	118.6	C11—C10—Br1	119.0 (3)
N2—C4—C1	123.2 (3)	C10—C11—C12	119.5 (3)
N2—C4—H4	118.4	C10—C11—H11	120.2
C1—C4—H4	118.4	C12—C11—H11	120.2
O1—C5—N3	125.4 (3)	C11—C12—C7	120.9 (3)
O1—C5—C1	121.7 (3)	C11—C12—H12	119.6
N3—C5—C1	112.9 (3)	C7—C12—H12	119.6

C5—N3—N4—C6	174.4 (3)	C4—C1—C5—N3	−173.2 (3)
C2—N1—C1—C4	−1.1 (4)	N3—N4—C6—C7	178.3 (3)
C2—N1—C1—C5	178.2 (3)	N4—C6—C7—C8	−7.6 (5)
C1—N1—C2—C3	0.3 (5)	N4—C6—C7—C12	172.5 (3)
C4—N2—C3—C2	−0.7 (5)	C12—C7—C8—C9	−0.1 (5)
N1—C2—C3—N2	0.7 (5)	C6—C7—C8—C9	−180.0 (3)
C3—N2—C4—C1	−0.1 (5)	C7—C8—C9—C10	−0.1 (5)
N1—C1—C4—N2	1.0 (5)	C8—C9—C10—C11	0.0 (5)
C5—C1—C4—N2	−178.2 (3)	C8—C9—C10—Br1	178.7 (2)
N4—N3—C5—O1	−1.9 (5)	C9—C10—C11—C12	0.4 (5)
N4—N3—C5—C1	179.1 (2)	Br1—C10—C11—C12	−178.3 (2)
N1—C1—C5—O1	−171.5 (3)	C10—C11—C12—C7	−0.6 (5)
C4—C1—C5—O1	7.8 (5)	C8—C7—C12—C11	0.5 (5)
N1—C1—C5—N3	7.6 (4)	C6—C7—C12—C11	−179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.24	3.132 (4)	161
N3—H3A···N1	0.86	2.27	2.671 (3)	108

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.24	3.132 (4)	161
N3—H3A⋯N1	0.86	2.27	2.671 (3)	108

Symmetry code: (i) .

4 in total

1. Synthesis, structure, and bioactivity of N'-substituted benzylidene-3,4,5-trimethoxybenzohydrazide and 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole derivatives.

Authors: Linhong Jin; Jiang Chen; Baoan Song; Zhuo Chen; Song Yang; Qianzhu Li; Deyu Hu; Ruiqing Xu
Journal: Bioorg Med Chem Lett Date: 2006-07-28 Impact factor: 2.823

2. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

3. Design and synthesis of antituberculars: preparation and evaluation against Mycobacterium tuberculosis of an isoniazid Schiff base.

Authors: Michael J Hearn; Michael H Cynamon
Journal: J Antimicrob Chemother Date: 2003-12-19 Impact factor: 5.790

4. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20