3-Bromo-N-(3,5-di-tert-butyl-phen-yl)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 mol-ecules into chains parallel to the c axis.

Related literature

For the related structure 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

Crystal data

C17H26BrNO

M = 340.30

Monoclinic,

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 ▶) T min = 0.455, T max = 0.789

21557 measured reflections

4005 independent reflections

2738 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 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

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; 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: local programs.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814012094/nk2223sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012094/nk2223Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012094/nk2223Isup3.cml

CCDC reference: 1005148

Additional supporting information: crystallographic information; 3D view; checkCIF report

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) Å3	Needle, colourless
Z = 4	0.40 × 0.20 × 0.11 mm

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 on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-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 reflections	Δρmax = 1.08 e Å−3
187 parameters	Δρmin = −0.65 e Å−3

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	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*

	U11	U22	U33	U12	U13	U23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1i	0.88	2.01	2.889 (3)	174
C5—H5···O1	0.95	2.41	2.931 (4)	115

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) .