Literature DB >> 23795067

2-(4-Bromo-phen-yl)-N-(pyrazin-2-yl)acetamide.

Prakash S Nayak¹, B Narayana, Jerry P Jasinski, H S Yathirajan, B K Sarojini.

Abstract

In the title compound, C12H10BrN3O, the dihedral angle between the mean planes of the 4-bromo-phenyl and pyrazin-2-yl rings is 54.6 (3)°. An intra-molecular C-H⋯O hydrogen bond generates an S(6) graph-set motif. In the crystal, weak N-H⋯N hydrogen bonds link the mol-ecules into chains along [100]. The chains are linked via C-H⋯N and C-H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to the ab plane.

Entities: Chemical Disease Species

Year: 2013 PMID： 23795067 PMCID： PMC3685048 DOI： 10.1107/S1600536813012531

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

Related literature

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2008 ▶). For the coordination abilities of amides, see: Wu et al. (2008 ▶, 2010 ▶). For related structures, see: Fun et al. (2012a ▶,b ▶,c ▶,d ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H10BrN3O M = 292.14 Orthorhombic, a = 10.6804 (4) Å b = 7.5196 (3) Å c = 29.1355 (10) Å V = 2339.94 (14) Å3 Z = 8 Cu Kα radiation μ = 4.69 mm−1 T = 173 K 0.16 × 0.08 × 0.06 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.388, T max = 1.000 13941 measured reflections 2317 independent reflections 2036 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.095 S = 1.03 2317 reflections 158 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.75 e Å−3 Δρmin = −0.81 e Å−3 Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2. Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012531/bt6905sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012531/bt6905Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813012531/bt6905Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₂H₁₀BrN₃O	D_x = 1.659 Mg m⁻³
M_r = 292.14	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 5193 reflections
a = 10.6804 (4) Å	θ = 4.1–72.4°
b = 7.5196 (3) Å	µ = 4.69 mm⁻¹
c = 29.1355 (10) Å	T = 173 K
V = 2339.94 (14) Å³	Chunk, colorless
Z = 8	0.16 × 0.08 × 0.06 mm
F(000) = 1168

Agilent Xcalibur Eos Gemini diffractometer	2036 reflections with I > 2σ(I)
Detector resolution: 16.1500 pixels mm^-1	R_int = 0.036
ω scans	θ_max = 72.6°, θ_min = 5.1°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −7→13
T_min = 0.388, T_max = 1.000	k = −9→9
13941 measured reflections	l = −35→33
2317 independent reflections

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.0494P)² + 2.0499P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.095	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.75 e Å⁻³
2317 reflections	Δρ_min = −0.81 e Å⁻³
158 parameters

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	U_iso*/U_eq
Br1	0.64022 (3)	0.29843 (4)	0.81514 (2)	0.04987 (14)
O1	0.77445 (16)	0.3961 (3)	0.58151 (7)	0.0473 (5)
N1	0.5962 (2)	0.3332 (3)	0.54173 (7)	0.0339 (5)
H1	0.524 (3)	0.340 (4)	0.5413 (10)	0.033 (8)*
N2	0.55700 (18)	0.1871 (3)	0.47422 (8)	0.0357 (5)
N3	0.81075 (18)	0.1345 (3)	0.45762 (7)	0.0351 (5)
C1	0.6614 (2)	0.4063 (4)	0.57735 (9)	0.0346 (5)
C2	0.6436 (2)	0.2438 (4)	0.50359 (9)	0.0315 (5)
C3	0.7716 (2)	0.2175 (3)	0.49533 (9)	0.0332 (5)
H3	0.8300	0.2586	0.5165	0.040*
C4	0.7231 (2)	0.0759 (3)	0.42843 (9)	0.0367 (6)
H4	0.7475	0.0161	0.4019	0.044*
C5	0.5977 (2)	0.1023 (4)	0.43686 (9)	0.0378 (6)
H5	0.5395	0.0597	0.4158	0.045*
C6	0.5806 (2)	0.5067 (4)	0.61136 (9)	0.0374 (6)
H6A	0.5997	0.6326	0.6093	0.045*
H6B	0.4933	0.4910	0.6031	0.045*
C7	0.5995 (2)	0.4464 (3)	0.66018 (9)	0.0315 (5)
C8	0.7040 (2)	0.5003 (3)	0.68536 (8)	0.0326 (5)
H8	0.7653	0.5691	0.6713	0.039*
C9	0.7177 (2)	0.4531 (3)	0.73080 (9)	0.0341 (5)
H9	0.7876	0.4897	0.7473	0.041*
C10	0.6263 (2)	0.3510 (3)	0.75151 (9)	0.0323 (5)
C11	0.5237 (2)	0.2907 (3)	0.72733 (10)	0.0384 (6)
H11	0.4639	0.2191	0.7414	0.046*
C12	0.5116 (2)	0.3387 (4)	0.68182 (10)	0.0389 (6)
H12	0.4430	0.2980	0.6652	0.047*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0638 (2)	0.0486 (2)	0.0372 (2)	−0.00515 (14)	0.00523 (12)	0.00487 (12)
O1	0.0237 (9)	0.0708 (14)	0.0474 (11)	0.0046 (9)	−0.0071 (7)	−0.0090 (10)
N1	0.0180 (10)	0.0469 (13)	0.0367 (11)	0.0001 (9)	0.0016 (8)	0.0025 (9)
N2	0.0227 (10)	0.0453 (12)	0.0390 (12)	0.0003 (9)	−0.0018 (8)	0.0025 (9)
N3	0.0256 (10)	0.0398 (12)	0.0398 (11)	0.0027 (9)	0.0021 (8)	0.0073 (9)
C1	0.0286 (12)	0.0399 (14)	0.0355 (13)	0.0008 (10)	−0.0016 (10)	0.0050 (11)
C2	0.0225 (11)	0.0376 (12)	0.0344 (13)	−0.0009 (9)	−0.0017 (9)	0.0088 (10)
C3	0.0229 (11)	0.0410 (14)	0.0356 (12)	−0.0003 (10)	0.0008 (9)	0.0081 (10)
C4	0.0336 (13)	0.0408 (14)	0.0357 (13)	0.0025 (11)	0.0005 (10)	0.0038 (11)
C5	0.0314 (12)	0.0438 (14)	0.0382 (14)	−0.0006 (11)	−0.0045 (10)	0.0026 (11)
C6	0.0274 (12)	0.0422 (14)	0.0428 (14)	0.0065 (11)	−0.0032 (10)	0.0007 (12)
C7	0.0230 (11)	0.0306 (12)	0.0409 (13)	0.0042 (9)	−0.0002 (9)	−0.0021 (10)
C8	0.0258 (11)	0.0306 (12)	0.0413 (13)	−0.0057 (10)	0.0028 (9)	−0.0013 (10)
C9	0.0319 (12)	0.0290 (12)	0.0414 (13)	−0.0045 (10)	−0.0040 (10)	−0.0023 (10)
C10	0.0362 (13)	0.0278 (11)	0.0330 (12)	0.0035 (9)	0.0044 (10)	0.0000 (10)
C11	0.0261 (12)	0.0335 (13)	0.0556 (16)	−0.0048 (10)	0.0068 (11)	0.0036 (11)
C12	0.0246 (12)	0.0392 (14)	0.0529 (16)	−0.0038 (10)	−0.0053 (10)	−0.0013 (12)

Br1—C10	1.901 (3)	C5—H5	0.9300
O1—C1	1.216 (3)	C6—C7	1.507 (4)
N1—C1	1.365 (3)	C6—H6A	0.9700
N1—C2	1.394 (3)	C6—H6B	0.9700
N1—H1	0.78 (3)	C7—C12	1.391 (4)
N2—C2	1.330 (3)	C7—C8	1.396 (3)
N2—C5	1.334 (3)	C8—C9	1.378 (4)
N3—C3	1.331 (3)	C8—H8	0.9300
N3—C4	1.339 (3)	C9—C10	1.381 (3)
C1—C6	1.516 (4)	C9—H9	0.9300
C2—C3	1.402 (3)	C10—C11	1.379 (4)
C3—H3	0.9300	C11—C12	1.380 (4)
C4—C5	1.376 (4)	C11—H11	0.9300
C4—H4	0.9300	C12—H12	0.9300

C1—N1—C2	128.0 (2)	C1—C6—H6A	109.0
C1—N1—H1	120 (2)	C7—C6—H6B	109.0
C2—N1—H1	113 (2)	C1—C6—H6B	109.0
C2—N2—C5	116.8 (2)	H6A—C6—H6B	107.8
C3—N3—C4	117.3 (2)	C12—C7—C8	118.1 (2)
O1—C1—N1	123.8 (3)	C12—C7—C6	120.9 (2)
O1—C1—C6	122.1 (2)	C8—C7—C6	121.1 (2)
N1—C1—C6	114.0 (2)	C9—C8—C7	121.0 (2)
N2—C2—N1	114.5 (2)	C9—C8—H8	119.5
N2—C2—C3	121.5 (2)	C7—C8—H8	119.5
N1—C2—C3	124.0 (2)	C8—C9—C10	119.2 (2)
N3—C3—C2	120.9 (2)	C8—C9—H9	120.4
N3—C3—H3	119.5	C10—C9—H9	120.4
C2—C3—H3	119.5	C11—C10—C9	121.4 (2)
N3—C4—C5	121.3 (2)	C11—C10—Br1	119.5 (2)
N3—C4—H4	119.4	C9—C10—Br1	119.10 (19)
C5—C4—H4	119.4	C10—C11—C12	118.6 (2)
N2—C5—C4	122.1 (2)	C10—C11—H11	120.7
N2—C5—H5	118.9	C12—C11—H11	120.7
C4—C5—H5	118.9	C11—C12—C7	121.6 (2)
C7—C6—C1	113.0 (2)	C11—C12—H12	119.2
C7—C6—H6A	109.0	C7—C12—H12	119.2

C2—N1—C1—O1	−3.2 (4)	N1—C1—C6—C7	127.0 (2)
C2—N1—C1—C6	175.4 (2)	C1—C6—C7—C12	−103.9 (3)
C5—N2—C2—N1	179.3 (2)	C1—C6—C7—C8	77.7 (3)
C5—N2—C2—C3	0.8 (4)	C12—C7—C8—C9	−2.1 (4)
C1—N1—C2—N2	−179.9 (2)	C6—C7—C8—C9	176.4 (2)
C1—N1—C2—C3	−1.4 (4)	C7—C8—C9—C10	0.0 (4)
C4—N3—C3—C2	−0.8 (4)	C8—C9—C10—C11	2.0 (4)
N2—C2—C3—N3	0.0 (4)	C8—C9—C10—Br1	−176.14 (19)
N1—C2—C3—N3	−178.4 (2)	C9—C10—C11—C12	−1.8 (4)
C3—N3—C4—C5	0.8 (4)	Br1—C10—C11—C12	176.3 (2)
C2—N2—C5—C4	−0.8 (4)	C10—C11—C12—C7	−0.4 (4)
N3—C4—C5—N2	0.0 (4)	C8—C7—C12—C11	2.3 (4)
O1—C1—C6—C7	−54.4 (4)	C6—C7—C12—C11	−176.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.78 (3)	2.28 (3)	3.059 (3)	178 (3)
C3—H3···O1	0.93	2.24	2.848 (3)	123
C3—H3···N2ⁱⁱ	0.93	2.47	3.255 (3)	142
C6—H6A···O1ⁱⁱⁱ	0.97	2.53	3.424 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3ⁱ	0.78 (3)	2.28 (3)	3.059 (3)	178 (3)
C3—H3⋯O1	0.93	2.24	2.848 (3)	123
C3—H3⋯N2ⁱⁱ	0.93	2.47	3.255 (3)	142
C6—H6A⋯O1ⁱⁱⁱ	0.97	2.53	3.424 (4)	154

Symmetry codes: (i) ; (ii) ; (iii) .

6 in total

1 in total

1. Crystal structures of two C,N-disubstituted acetamides: 2-(4-chloro-phen-yl)-N-(2-iodo-phen-yl)acetamide and 2-(4-chloro-phen-yl)-N-(pyrazin-2-yl)acetamide.

Authors: Badiadka Narayana; Hemmige S Yathirajan; Ravindranath Rathore; Christopher Glidewell
Journal: Acta Crystallogr E Crystallogr Commun Date: 2016-08-09

1 in total

2-(4-Bromo-phen-yl)-N-(pyrazin-2-yl)acetamide.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. Aqua-[N-phenyl-2-(quinolin-8-yl-oxy)acetamide]dinitratozinc(II).

3. N-(4-Bromo-phen-yl)-2-(4-chloro-phen-yl)acetamide.

4. N-(3,4-Difluoro-phen-yl)-2,2-diphenyl-acetamide.

5. 2-(4-Bromo-phen-yl)-N-(5-methyl-pyridin-2-yl)acetamide.

6. 2-(4-Bromo-phen-yl)-N-(3-chloro-4-fluoro-phen-yl)acetamide.

1. Crystal structures of two C,N-disubstituted acetamides: 2-(4-chloro-phen-yl)-N-(2-iodo-phen-yl)acetamide and 2-(4-chloro-phen-yl)-N-(pyrazin-2-yl)acetamide.