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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 7| July 2014| Page o770
https://doi.org/10.1107/S1600536814012094

3-Bromo-N-(3,5-di-tert-butyl­phen­yl)propanamide

Anwar Abo-Amer,a Mahmoud Al-Refai,a Richard J. Puddephattb and Basem F. Alia*

aDepartment of Chemistry, Al al-Bayt University, Mafraq 25113, Jordan, and bDepartment of Chemistry, University of Western Ontario, London, N6A 5B7, Canada
*Correspondence e-mail: bfali@aabu.edu.jo

(Received 27 March 2014; accepted 25 May 2014; online 14 June 2014)

The title compound, C17H26BrNO, exhibits a small twist between the amide residue and the benzene ring [C—N—C—C torsion angle = 29.4 (5)°]. In the crystal, the amido NH group is involved in N—H⋯O hydrogen bonding, which connects mol­ecules into chains parallel to the c axis.

CCDC reference: 1005148

Related literature

For the related structure of a derivative with an alkyl-N-aryl substituent, see: Palakshamurthy et al. (2014[Palakshamurthy, B. S., Suchetan, P. A., Sreenivasa, S., Lokanath, N. K. & Madhu Chakrapani Rao, T. (2014). Acta Cryst. E70, o223.]), with an alkyl-N-phenyl­sulfonyl substituent, see: Shakuntala et al. (2011[Shakuntala, K., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o536.]) and with a chloro-N-phenyl substituent, see: Betz et al. (2011[Betz, R., Gerber, T., Hosten, E., Siddegowda, M. S. & Yathirajan, H. S. (2011). Acta Cryst. E67, o2868.]). For details of the synthesis, see: Bentiss & Lagrenée (1999[Bentiss, F. & Lagrenée, M. (1999). J. Heterocycl. Chem. 36, 1029-1032.]); Hill et al. (2007[Hill, G. S., Irwin, M. J., Levy, C. J., Rendina, L. M., Puddephatt, R. J., Andersen, R. A. & Mclean, L. (2007). Platinum(II) Complexes of Dimethyl Sulfide, in Inorganic Syntheses. New York: John Wiley & Sons Inc.]).

[Scheme 1]

Experimental

Crystal data

  • C17H26BrNO

  • Mr = 340.30

  • Monoclinic, P 21 /c

  • a = 15.666 (2) Å

  • b = 11.4885 (16) Å

  • c = 9.7829 (14) Å

  • β = 97.436 (4)°

  • V = 1745.9 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.35 mm−1

  • T = 150 K

  • 0.40 × 0.20 × 0.11 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.455, Tmax = 0.789

  • 21557 measured reflections

  • 4005 independent reflections

  • 2738 reflections with I > 2σ(I)

  • Rint = 0.055
Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.145

  • S = 1.04

  • 4005 reflections

  • 187 parameters

  • H-atom parameters constrained

  • Δρmax = 1.08 e Å−3

  • Δρmin = −0.65 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1C⋯O1i 0.88 2.01 2.889 (3) 174
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalMaker (CrystalMaker, 2014[CrystalMaker Software (2014). CrystalMaker. CrystalMaker Software, Bicester, Oxfordshire, England. www.crystalmaker.com]); software used to prepare material for publication: local programs.

Supporting information

CCDC reference: 1005148

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536814012094/nk2223sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814012094/nk2223Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814012094/nk2223Isup3.cml

checkCIF report


Comment top

The title compound C17H25BrNO, is a brominated derivative of a secondary amide bearing a di-tert-butylbenzene ring. It exhibits a small twist between the amide residue and benzene ring [the C3—N1—C4—C5 torsion angle = 29.5 (4)°]. The N—H and C=O bonds are anti to each other (Fig. 1), as observed in many other derivatives (Shakuntala et al., 2011). In the structure, bond distances and angles are within normal range (Table 1) and comparable to reported values in amide derivatives (Palakshamurthy et al., 2014, Betz et al., 2011). The torsion angle of C3—N1—C4—C9 and C3—N1—C4—C5 are -153.2 (3)° and 29.5 (4)°, respectively. The amido NH group is involved in N—H···O [2.01 Å] hydrogen bonding, which connects molecules into chains parallel to c axis (Fig. 2).

Related literature top

For related structures of a derivative with an alkyl-N-aryl substituent, see: Palakshamurthy et al. (2014), with an alkyl-N-phenylsulfonyl substituent, see: Shakuntala et al. (2011) and with a chloro-N-phenyl substituent, see: Betz et al. (2011). For details of the synthesis, see: Bentiss & Lagrenée (1999); Hill et al. (2007).

Experimental top

Synthesis of (2,5-Bis(2-pyridyl)-1,3,4-oxadiazole)dimethylplatinum(II), [PtMe2(ox)]

A mixture of [Pt2Me4(µ-SMe2)2] (50 mg, 0.087 mmol)) (Hill et al., 2007) and ox (ox = 2,5-bis(2-pyridyl)-1,3,4-oxadiazole) (38 mg, 0.170Dr mmol) (Bentiss and Lagrenée, 1999) in dry ether (10 ml) was stirred for 1 h. A red precipitate resulted. The precipitate was isolated and washed with acetone (3 × 5 ml). The product was recrystallized from CH2Cl2. A yellow solid was produced and dried in vacuo.

The title compound was crystallized unintentionally from the reaction mixture of the complex (2,5-Bis(2-pyridyl)-1,3,4-oxadiazole)dimethylplatinum(II), [PtMe2(ox)] (0.05 g, 0.112 mmol) and, the commercially available N-(3,5-di-tert-butylphenyl)-3-bromopropanamide (0.052 g, 0.129 mmol) in acetone (15 ml) was stirred for 5 h at room temperature. The reaction color changed to yellow suspension. The solvent was evaporated under vacuum and the resulting solid was washed with water (2 × 10 ml) and pentane (3 × 10 ml). The isolated yellow solid is highly soluble in CH2Cl2 solvent, which was dried under high vacuum. Yield 87%. A suitable crystal for X-ray diffraction analysis was selected for data collection.

Refinement top

The hydrogen atoms were introduced at idealized positions and were allowed to ride on the parent atom, with C—H = 0.95–0.99 Å and N—H = 0.88 Å and Uiso(H) = 1.2–1.5Ueq(C,N).

Structure description top

The title compound C17H25BrNO, is a brominated derivative of a secondary amide bearing a di-tert-butylbenzene ring. It exhibits a small twist between the amide residue and benzene ring [the C3—N1—C4—C5 torsion angle = 29.5 (4)°]. The N—H and C=O bonds are anti to each other (Fig. 1), as observed in many other derivatives (Shakuntala et al., 2011). In the structure, bond distances and angles are within normal range (Table 1) and comparable to reported values in amide derivatives (Palakshamurthy et al., 2014, Betz et al., 2011). The torsion angle of C3—N1—C4—C9 and C3—N1—C4—C5 are -153.2 (3)° and 29.5 (4)°, respectively. The amido NH group is involved in N—H···O [2.01 Å] hydrogen bonding, which connects molecules into chains parallel to c axis (Fig. 2).

For related structures of a derivative with an alkyl-N-aryl substituent, see: Palakshamurthy et al. (2014), with an alkyl-N-phenylsulfonyl substituent, see: Shakuntala et al. (2011) and with a chloro-N-phenyl substituent, see: Betz et al. (2011). For details of the synthesis, see: Bentiss & Lagrenée (1999); Hill et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: CrystalMaker (CrystalMaker, 2014); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
[Figure 2] Fig. 2. Partial molecular packing, showing the chains, parallel to c axis, formed via N—H···O hydrogen bonding (multi-rendered cylinders).
3-Bromo-N-(3,5-di-tert-butylphenyl)propanamide top
Crystal data top
C17H26BrNOF(000) = 712
Mr = 340.30Dx = 1.295 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.666 (2) ÅCell parameters from 5619 reflections
b = 11.4885 (16) Åθ = 2.2–26.0°
c = 9.7829 (14) ŵ = 2.35 mm−1
β = 97.436 (4)°T = 150 K
V = 1745.9 (4) Å3Needle, colourless
Z = 40.40 × 0.20 × 0.11 mm
Data collection top
Bruker APEXII CCD
diffractometer		2738 reflections with I > 2σ(I)
φ and ω scansRint = 0.055
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		θmax = 27.6°, θmin = 2.2°
Tmin = 0.455, Tmax = 0.789h = −20→19
21557 measured reflectionsk = −14→14
4005 independent reflectionsl = −8→12
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.0743P)2 + 1.5001P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4005 reflectionsΔρmax = 1.08 e Å−3
187 parametersΔρmin = −0.65 e Å−3
Crystal data top
C17H26BrNOV = 1745.9 (4) Å3
Mr = 340.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.666 (2) ŵ = 2.35 mm−1
b = 11.4885 (16) ÅT = 150 K
c = 9.7829 (14) Å0.40 × 0.20 × 0.11 mm
β = 97.436 (4)°
Data collection top
Bruker APEXII CCD
diffractometer		4005 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)		2738 reflections with I > 2σ(I)
Tmin = 0.455, Tmax = 0.789Rint = 0.055
21557 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 1.04Δρmax = 1.08 e Å−3
4005 reflectionsΔρmin = −0.65 e Å−3
187 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.58935 (3)0.54272 (3)0.85526 (5)0.04516 (17)
N10.61402 (17)0.2102 (2)0.8672 (2)0.0205 (6)
H1C0.59900.21310.95080.025*
O10.57853 (15)0.2805 (2)0.6495 (2)0.0292 (6)
C10.4854 (2)0.4604 (3)0.7774 (4)0.0303 (8)
H1A0.43440.49740.80920.036*
H1B0.47900.46530.67560.036*
C20.4901 (2)0.3353 (3)0.8208 (3)0.0234 (7)
H2A0.43580.29570.78400.028*
H2B0.49610.33080.92270.028*
C30.56518 (19)0.2730 (3)0.7699 (3)0.0201 (6)
C40.68642 (19)0.1401 (3)0.8510 (3)0.0201 (6)
C50.74057 (19)0.1639 (3)0.7525 (3)0.0219 (7)
H50.72820.22700.69040.026*
C60.81286 (19)0.0950 (3)0.7452 (3)0.0226 (7)
C70.8718 (2)0.1217 (3)0.6355 (3)0.0267 (7)
C80.8922 (3)0.2519 (4)0.6334 (5)0.0476 (11)
H8A0.92990.26740.56310.071*
H8B0.92110.27570.72400.071*
H8C0.83860.29590.61180.071*
C90.8285 (2)0.0018 (3)0.8365 (3)0.0240 (7)
H90.8774−0.04600.83080.029*
C100.7749 (2)−0.0236 (3)0.9359 (3)0.0222 (7)
C110.7922 (2)−0.1243 (3)1.0380 (3)0.0263 (7)
C120.7155 (3)−0.2089 (4)1.0182 (5)0.0467 (10)
H12A0.6632−0.16821.03670.070*
H12B0.7267−0.27451.08200.070*
H12C0.7077−0.23780.92320.070*
C130.8033 (3)−0.0751 (3)1.1850 (4)0.0364 (9)
H13A0.8532−0.02311.19750.055*
H13B0.8122−0.13931.25140.055*
H13C0.7515−0.03161.20010.055*
C140.8740 (2)−0.1920 (3)1.0187 (4)0.0355 (9)
H14A0.8691−0.22260.92450.053*
H14B0.8813−0.25671.08440.053*
H14C0.9238−0.14001.03490.053*
C150.7037 (2)0.0485 (3)0.9422 (3)0.0218 (6)
H150.66660.03441.01000.026*
C160.8254 (2)0.0852 (4)0.4948 (4)0.0385 (9)
H16A0.77200.12990.47440.058*
H16B0.81190.00200.49610.058*
H16C0.86260.10040.42360.058*
C170.9571 (2)0.0552 (4)0.6613 (4)0.0412 (10)
H17A0.9459−0.02850.65090.062*
H17B0.98490.07120.75490.062*
H17C0.99490.08020.59450.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0416 (3)0.0352 (2)0.0631 (3)−0.00389 (17)0.0234 (2)−0.00846 (19)
N10.0228 (13)0.0298 (15)0.0107 (12)0.0051 (11)0.0087 (10)−0.0011 (10)
O10.0302 (13)0.0479 (15)0.0109 (10)0.0089 (11)0.0083 (9)0.0029 (10)
C10.0244 (17)0.038 (2)0.0295 (18)0.0105 (15)0.0071 (14)0.0062 (15)
C20.0170 (15)0.0324 (18)0.0221 (16)0.0020 (13)0.0082 (12)−0.0002 (13)
C30.0179 (15)0.0277 (17)0.0157 (15)−0.0025 (12)0.0057 (12)−0.0035 (12)
C40.0169 (15)0.0278 (17)0.0164 (14)−0.0003 (12)0.0055 (12)−0.0042 (13)
C50.0202 (16)0.0322 (17)0.0142 (14)0.0000 (13)0.0059 (12)0.0012 (13)
C60.0182 (15)0.0329 (18)0.0175 (15)−0.0009 (13)0.0053 (12)−0.0063 (13)
C70.0209 (16)0.039 (2)0.0216 (16)0.0031 (14)0.0092 (13)−0.0050 (14)
C80.044 (3)0.047 (3)0.059 (3)−0.0080 (19)0.034 (2)−0.004 (2)
C90.0204 (16)0.0315 (16)0.0205 (16)0.0034 (13)0.0040 (13)−0.0070 (14)
C100.0228 (16)0.0280 (18)0.0158 (15)−0.0019 (13)0.0027 (12)−0.0049 (13)
C110.0258 (17)0.0294 (18)0.0236 (16)0.0040 (14)0.0021 (13)0.0014 (14)
C120.044 (2)0.037 (2)0.058 (3)−0.0040 (18)0.001 (2)0.012 (2)
C130.045 (2)0.044 (2)0.0216 (17)0.0137 (17)0.0070 (16)0.0071 (16)
C140.042 (2)0.036 (2)0.0290 (19)0.0125 (17)0.0032 (16)0.0002 (16)
C150.0222 (16)0.0289 (17)0.0158 (14)−0.0024 (13)0.0084 (12)−0.0026 (13)
C160.036 (2)0.061 (3)0.0204 (17)−0.0049 (18)0.0109 (15)−0.0013 (17)
C170.028 (2)0.064 (3)0.035 (2)0.0075 (18)0.0159 (16)−0.0010 (19)
Geometric parameters (Å, º) top
Br1—C11.951 (4)C9—C101.396 (5)
N1—C31.350 (4)C9—H90.9500
N1—C41.416 (4)C10—C151.397 (4)
N1—H1C0.8800C10—C111.529 (5)
O1—C31.226 (4)C11—C141.531 (5)
C1—C21.498 (5)C11—C131.534 (5)
C1—H1A0.9900C11—C121.538 (5)
C1—H1B0.9900C12—H12A0.9800
C2—C31.515 (4)C12—H12B0.9800
C2—H2A0.9900C12—H12C0.9800
C2—H2B0.9900C13—H13A0.9800
C4—C151.384 (4)C13—H13B0.9800
C4—C51.391 (4)C13—H13C0.9800
C5—C61.391 (4)C14—H14A0.9800
C5—H50.9500C14—H14B0.9800
C6—C91.396 (5)C14—H14C0.9800
C6—C71.534 (4)C15—H150.9500
C7—C81.530 (6)C16—H16A0.9800
C7—C161.530 (5)C16—H16B0.9800
C7—C171.531 (5)C16—H16C0.9800
C8—H8A0.9800C17—H17A0.9800
C8—H8B0.9800C17—H17B0.9800
C8—H8C0.9800C17—H17C0.9800
C3—N1—C4127.9 (2)C9—C10—C15117.6 (3)
C3—N1—H1C116.1C9—C10—C11122.7 (3)
C4—N1—H1C116.1C15—C10—C11119.7 (3)
C2—C1—Br1110.3 (2)C10—C11—C14112.6 (3)
C2—C1—H1A109.6C10—C11—C13108.8 (3)
Br1—C1—H1A109.6C14—C11—C13107.9 (3)
C2—C1—H1B109.6C10—C11—C12109.0 (3)
Br1—C1—H1B109.6C14—C11—C12108.4 (3)
H1A—C1—H1B108.1C13—C11—C12110.0 (3)
C1—C2—C3111.8 (3)C11—C12—H12A109.5
C1—C2—H2A109.2C11—C12—H12B109.5
C3—C2—H2A109.2H12A—C12—H12B109.5
C1—C2—H2B109.2C11—C12—H12C109.5
C3—C2—H2B109.2H12A—C12—H12C109.5
H2A—C2—H2B107.9H12B—C12—H12C109.5
O1—C3—N1124.3 (3)C11—C13—H13A109.5
O1—C3—C2121.2 (3)C11—C13—H13B109.5
N1—C3—C2114.5 (3)H13A—C13—H13B109.5
C15—C4—C5120.7 (3)C11—C13—H13C109.5
C15—C4—N1116.9 (3)H13A—C13—H13C109.5
C5—C4—N1122.3 (3)H13B—C13—H13C109.5
C4—C5—C6119.9 (3)C11—C14—H14A109.5
C4—C5—H5120.1C11—C14—H14B109.5
C6—C5—H5120.1H14A—C14—H14B109.5
C5—C6—C9118.7 (3)C11—C14—H14C109.5
C5—C6—C7119.4 (3)H14A—C14—H14C109.5
C9—C6—C7121.9 (3)H14B—C14—H14C109.5
C8—C7—C16109.3 (3)C4—C15—C10120.9 (3)
C8—C7—C17108.2 (3)C4—C15—H15119.6
C16—C7—C17108.3 (3)C10—C15—H15119.6
C8—C7—C6110.5 (3)C7—C16—H16A109.5
C16—C7—C6108.4 (3)C7—C16—H16B109.5
C17—C7—C6112.1 (3)H16A—C16—H16B109.5
C7—C8—H8A109.5C7—C16—H16C109.5
C7—C8—H8B109.5H16A—C16—H16C109.5
H8A—C8—H8B109.5H16B—C16—H16C109.5
C7—C8—H8C109.5C7—C17—H17A109.5
H8A—C8—H8C109.5C7—C17—H17B109.5
H8B—C8—H8C109.5H17A—C17—H17B109.5
C6—C9—C10122.3 (3)C7—C17—H17C109.5
C6—C9—H9118.9H17A—C17—H17C109.5
C10—C9—H9118.9H17B—C17—H17C109.5
Br1—C1—C2—C3−61.5 (3)C9—C6—C7—C17−13.4 (4)
C4—N1—C3—O1−1.8 (5)C5—C6—C9—C10−0.9 (5)
C4—N1—C3—C2178.0 (3)C7—C6—C9—C10−179.6 (3)
C1—C2—C3—O1−48.6 (4)C6—C9—C10—C15−0.2 (5)
C1—C2—C3—N1131.6 (3)C6—C9—C10—C11−179.0 (3)
C3—N1—C4—C15−153.2 (3)C9—C10—C11—C140.3 (4)
C3—N1—C4—C529.4 (5)C15—C10—C11—C14−178.5 (3)
C15—C4—C5—C60.0 (5)C9—C10—C11—C13119.9 (3)
N1—C4—C5—C6177.3 (3)C15—C10—C11—C13−58.9 (4)
C4—C5—C6—C91.0 (5)C9—C10—C11—C12−120.1 (4)
C4—C5—C6—C7179.7 (3)C15—C10—C11—C1261.1 (4)
C5—C6—C7—C847.2 (4)C5—C4—C15—C10−1.2 (5)
C9—C6—C7—C8−134.1 (3)N1—C4—C15—C10−178.6 (3)
C5—C6—C7—C16−72.6 (4)C9—C10—C15—C41.3 (5)
C9—C6—C7—C16106.1 (4)C11—C10—C15—C4−179.9 (3)
C5—C6—C7—C17167.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O1i0.882.012.889 (3)174
C5—H5···O10.952.412.931 (4)115
Symmetry code: (i) x, −y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O1i0.882.012.889 (3)174.0
Symmetry code: (i) x, −y+1/2, z+1/2.
 

Acknowledgements

The authors would like to thank Dr Aneta Borecki and Dr Paul Boyle (University of Western Ontario) for their help in data collection and refinement.

References

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Volume 70| Part 7| July 2014| Page o770
https://doi.org/10.1107/S1600536814012094
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