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

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.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.145
• Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Why ?
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          1 Why ?
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         39 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 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
   1 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

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).

Computing details

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

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	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

Crystal data

C17H26BrNO	F(000) = 712
Mr = 340.30	Dx = 1.295 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.666 (2) Å	Cell parameters from 5619 reflections
b = 11.4885 (16) Å	θ = 2.2–26.0°
c = 9.7829 (14) Å	µ = 2.35 mm^−1
β = 97.436 (4)°	T = 150 K
V = 1745.9 (4) Å^3	Needle, colourless
Z = 4	0.40 × 0.20 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer	2738 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.055
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 27.6°, θmin = 2.2°
Tmin = 0.455, Tmax = 0.789	h = −20→19
21557 measured reflections	k = −14→14
4005 independent reflections	l = −8→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0743P)^2 + 1.5001P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4005 reflections	Δρmax = 1.08 e Å^−3
187 parameters	Δρmin = −0.65 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.58935 (3)	0.54272 (3)	0.85526 (5)	0.04516 (17)
N1	0.61402 (17)	0.2102 (2)	0.8672 (2)	0.0205 (6)
H1C	0.5990	0.2131	0.9508	0.025*
O1	0.57853 (15)	0.2805 (2)	0.6495 (2)	0.0292 (6)
C1	0.4854 (2)	0.4604 (3)	0.7774 (4)	0.0303 (8)
H1A	0.4344	0.4974	0.8092	0.036*
H1B	0.4790	0.4653	0.6756	0.036*
C2	0.4901 (2)	0.3353 (3)	0.8208 (3)	0.0234 (7)
H2A	0.4358	0.2957	0.7840	0.028*
H2B	0.4961	0.3308	0.9227	0.028*
C3	0.56518 (19)	0.2730 (3)	0.7699 (3)	0.0201 (6)
C4	0.68642 (19)	0.1401 (3)	0.8510 (3)	0.0201 (6)
C5	0.74057 (19)	0.1639 (3)	0.7525 (3)	0.0219 (7)
H5	0.7282	0.2270	0.6904	0.026*
C6	0.81286 (19)	0.0950 (3)	0.7452 (3)	0.0226 (7)
C7	0.8718 (2)	0.1217 (3)	0.6355 (3)	0.0267 (7)
C8	0.8922 (3)	0.2519 (4)	0.6334 (5)	0.0476 (11)
H8A	0.9299	0.2674	0.5631	0.071*
H8B	0.9211	0.2757	0.7240	0.071*
H8C	0.8386	0.2959	0.6118	0.071*
C9	0.8285 (2)	0.0018 (3)	0.8365 (3)	0.0240 (7)
H9	0.8774	−0.0460	0.8308	0.029*
C10	0.7749 (2)	−0.0236 (3)	0.9359 (3)	0.0222 (7)
C11	0.7922 (2)	−0.1243 (3)	1.0380 (3)	0.0263 (7)
C12	0.7155 (3)	−0.2089 (4)	1.0182 (5)	0.0467 (10)
H12A	0.6632	−0.1682	1.0367	0.070*
H12B	0.7267	−0.2745	1.0820	0.070*
H12C	0.7077	−0.2378	0.9232	0.070*
C13	0.8033 (3)	−0.0751 (3)	1.1850 (4)	0.0364 (9)
H13A	0.8532	−0.0231	1.1975	0.055*
H13B	0.8122	−0.1393	1.2514	0.055*
H13C	0.7515	−0.0316	1.2001	0.055*
C14	0.8740 (2)	−0.1920 (3)	1.0187 (4)	0.0355 (9)
H14A	0.8691	−0.2226	0.9245	0.053*
H14B	0.8813	−0.2567	1.0844	0.053*
H14C	0.9238	−0.1400	1.0349	0.053*
C15	0.7037 (2)	0.0485 (3)	0.9422 (3)	0.0218 (6)
H15	0.6666	0.0344	1.0100	0.026*
C16	0.8254 (2)	0.0852 (4)	0.4948 (4)	0.0385 (9)
H16A	0.7720	0.1299	0.4744	0.058*
H16B	0.8119	0.0020	0.4961	0.058*
H16C	0.8626	0.1004	0.4236	0.058*
C17	0.9571 (2)	0.0552 (4)	0.6613 (4)	0.0412 (10)
H17A	0.9459	−0.0285	0.6509	0.062*
H17B	0.9849	0.0712	0.7549	0.062*
H17C	0.9949	0.0802	0.5945	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0416 (3)	0.0352 (2)	0.0631 (3)	−0.00389 (17)	0.0234 (2)	−0.00846 (19)
N1	0.0228 (13)	0.0298 (15)	0.0107 (12)	0.0051 (11)	0.0087 (10)	−0.0011 (10)
O1	0.0302 (13)	0.0479 (15)	0.0109 (10)	0.0089 (11)	0.0083 (9)	0.0029 (10)
C1	0.0244 (17)	0.038 (2)	0.0295 (18)	0.0105 (15)	0.0071 (14)	0.0062 (15)
C2	0.0170 (15)	0.0324 (18)	0.0221 (16)	0.0020 (13)	0.0082 (12)	−0.0002 (13)
C3	0.0179 (15)	0.0277 (17)	0.0157 (15)	−0.0025 (12)	0.0057 (12)	−0.0035 (12)
C4	0.0169 (15)	0.0278 (17)	0.0164 (14)	−0.0003 (12)	0.0055 (12)	−0.0042 (13)
C5	0.0202 (16)	0.0322 (17)	0.0142 (14)	0.0000 (13)	0.0059 (12)	0.0012 (13)
C6	0.0182 (15)	0.0329 (18)	0.0175 (15)	−0.0009 (13)	0.0053 (12)	−0.0063 (13)
C7	0.0209 (16)	0.039 (2)	0.0216 (16)	0.0031 (14)	0.0092 (13)	−0.0050 (14)
C8	0.044 (3)	0.047 (3)	0.059 (3)	−0.0080 (19)	0.034 (2)	−0.004 (2)
C9	0.0204 (16)	0.0315 (16)	0.0205 (16)	0.0034 (13)	0.0040 (13)	−0.0070 (14)
C10	0.0228 (16)	0.0280 (18)	0.0158 (15)	−0.0019 (13)	0.0027 (12)	−0.0049 (13)
C11	0.0258 (17)	0.0294 (18)	0.0236 (16)	0.0040 (14)	0.0021 (13)	0.0014 (14)
C12	0.044 (2)	0.037 (2)	0.058 (3)	−0.0040 (18)	0.001 (2)	0.012 (2)
C13	0.045 (2)	0.044 (2)	0.0216 (17)	0.0137 (17)	0.0070 (16)	0.0071 (16)
C14	0.042 (2)	0.036 (2)	0.0290 (19)	0.0125 (17)	0.0032 (16)	0.0002 (16)
C15	0.0222 (16)	0.0289 (17)	0.0158 (14)	−0.0024 (13)	0.0084 (12)	−0.0026 (13)
C16	0.036 (2)	0.061 (3)	0.0204 (17)	−0.0049 (18)	0.0109 (15)	−0.0013 (17)
C17	0.028 (2)	0.064 (3)	0.035 (2)	0.0075 (18)	0.0159 (16)	−0.0010 (19)

Geometric parameters (Å, º)

Br1—C1	1.951 (4)	C9—C10	1.396 (5)
N1—C3	1.350 (4)	C9—H9	0.9500
N1—C4	1.416 (4)	C10—C15	1.397 (4)
N1—H1C	0.8800	C10—C11	1.529 (5)
O1—C3	1.226 (4)	C11—C14	1.531 (5)
C1—C2	1.498 (5)	C11—C13	1.534 (5)
C1—H1A	0.9900	C11—C12	1.538 (5)
C1—H1B	0.9900	C12—H12A	0.9800
C2—C3	1.515 (4)	C12—H12B	0.9800
C2—H2A	0.9900	C12—H12C	0.9800
C2—H2B	0.9900	C13—H13A	0.9800
C4—C15	1.384 (4)	C13—H13B	0.9800
C4—C5	1.391 (4)	C13—H13C	0.9800
C5—C6	1.391 (4)	C14—H14A	0.9800
C5—H5	0.9500	C14—H14B	0.9800
C6—C9	1.396 (5)	C14—H14C	0.9800
C6—C7	1.534 (4)	C15—H15	0.9500
C7—C8	1.530 (6)	C16—H16A	0.9800
C7—C16	1.530 (5)	C16—H16B	0.9800
C7—C17	1.531 (5)	C16—H16C	0.9800
C8—H8A	0.9800	C17—H17A	0.9800
C8—H8B	0.9800	C17—H17B	0.9800
C8—H8C	0.9800	C17—H17C	0.9800
C3—N1—C4	127.9 (2)	C9—C10—C15	117.6 (3)
C3—N1—H1C	116.1	C9—C10—C11	122.7 (3)
C4—N1—H1C	116.1	C15—C10—C11	119.7 (3)
C2—C1—Br1	110.3 (2)	C10—C11—C14	112.6 (3)
C2—C1—H1A	109.6	C10—C11—C13	108.8 (3)
Br1—C1—H1A	109.6	C14—C11—C13	107.9 (3)
C2—C1—H1B	109.6	C10—C11—C12	109.0 (3)
Br1—C1—H1B	109.6	C14—C11—C12	108.4 (3)
H1A—C1—H1B	108.1	C13—C11—C12	110.0 (3)
C1—C2—C3	111.8 (3)	C11—C12—H12A	109.5
C1—C2—H2A	109.2	C11—C12—H12B	109.5
C3—C2—H2A	109.2	H12A—C12—H12B	109.5
C1—C2—H2B	109.2	C11—C12—H12C	109.5
C3—C2—H2B	109.2	H12A—C12—H12C	109.5
H2A—C2—H2B	107.9	H12B—C12—H12C	109.5
O1—C3—N1	124.3 (3)	C11—C13—H13A	109.5
O1—C3—C2	121.2 (3)	C11—C13—H13B	109.5
N1—C3—C2	114.5 (3)	H13A—C13—H13B	109.5
C15—C4—C5	120.7 (3)	C11—C13—H13C	109.5
C15—C4—N1	116.9 (3)	H13A—C13—H13C	109.5
C5—C4—N1	122.3 (3)	H13B—C13—H13C	109.5
C4—C5—C6	119.9 (3)	C11—C14—H14A	109.5
C4—C5—H5	120.1	C11—C14—H14B	109.5
C6—C5—H5	120.1	H14A—C14—H14B	109.5
C5—C6—C9	118.7 (3)	C11—C14—H14C	109.5
C5—C6—C7	119.4 (3)	H14A—C14—H14C	109.5
C9—C6—C7	121.9 (3)	H14B—C14—H14C	109.5
C8—C7—C16	109.3 (3)	C4—C15—C10	120.9 (3)
C8—C7—C17	108.2 (3)	C4—C15—H15	119.6
C16—C7—C17	108.3 (3)	C10—C15—H15	119.6
C8—C7—C6	110.5 (3)	C7—C16—H16A	109.5
C16—C7—C6	108.4 (3)	C7—C16—H16B	109.5
C17—C7—C6	112.1 (3)	H16A—C16—H16B	109.5
C7—C8—H8A	109.5	C7—C16—H16C	109.5
C7—C8—H8B	109.5	H16A—C16—H16C	109.5
H8A—C8—H8B	109.5	H16B—C16—H16C	109.5
C7—C8—H8C	109.5	C7—C17—H17A	109.5
H8A—C8—H8C	109.5	C7—C17—H17B	109.5
H8B—C8—H8C	109.5	H17A—C17—H17B	109.5
C6—C9—C10	122.3 (3)	C7—C17—H17C	109.5
C6—C9—H9	118.9	H17A—C17—H17C	109.5
C10—C9—H9	118.9	H17B—C17—H17C	109.5
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—C2	178.0 (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—N1	131.6 (3)	C6—C9—C10—C11	−179.0 (3)
C3—N1—C4—C15	−153.2 (3)	C9—C10—C11—C14	0.3 (4)
C3—N1—C4—C5	29.4 (5)	C15—C10—C11—C14	−178.5 (3)
C15—C4—C5—C6	0.0 (5)	C9—C10—C11—C13	119.9 (3)
N1—C4—C5—C6	177.3 (3)	C15—C10—C11—C13	−58.9 (4)
C4—C5—C6—C9	1.0 (5)	C9—C10—C11—C12	−120.1 (4)
C4—C5—C6—C7	179.7 (3)	C15—C10—C11—C12	61.1 (4)
C5—C6—C7—C8	47.2 (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—C4	1.3 (5)
C9—C6—C7—C16	106.1 (4)	C11—C10—C15—C4	−179.9 (3)
C5—C6—C7—C17	167.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1^i	0.88	2.01	2.889 (3)	174
C5—H5···O1	0.95	2.41	2.931 (4)	115

Symmetry code: (i) x, −y+1/2, z+1/2.