4-{[1-(4-Bromo-phen-yl)eth-yl]amino-meth-yl}phenol.

The title compound, C(15)H(16)BrNO, obtained from a two-step reaction, was prepared for use in transition metal chemistry as a phenolic ligand with bulky substituents. Inter-molecular N-H⋯O and O-H⋯N hydrogen bonds are present in the crystal structure.

Related literature

For chirality induction in metal complexes, see: Fan et al. (2010 ▶); Amendola et al. (2010 ▶). For imine reduction, see: Menta & Prabhakar (1995 ▶).

Experimental

Crystal data

C15H16BrNO

M = 306.20

Monoclinic,

a = 12.1753 (10) Å

b = 8.1939 (7) Å

c = 14.0326 (11) Å

β = 93.333 (1)°

V = 1397.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.93 mm−1

T = 296 K

0.20 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.592, T max = 0.685

14961 measured reflections

3094 independent reflections

2119 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.077

S = 1.00

3094 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028339/fy2015sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811028339/fy2015Isup2.cml

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028339/fy2015Isup3.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H16BrNO	F(000) = 624
Mr = 306.20	Dx = 1.455 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5896 reflections
a = 12.1753 (10) Å	θ = 2.3–26.2°
b = 8.1939 (7) Å	µ = 2.93 mm−1
c = 14.0326 (11) Å	T = 296 K
β = 93.333 (1)°	Block, colourless
V = 1397.6 (2) Å3	0.20 × 0.16 × 0.14 mm
Z = 4

Bruker APEXII CCD diffractometer	3094 independent reflections
Radiation source: fine-focus sealed tube	2119 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 27.2°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −15→15
Tmin = 0.592, Tmax = 0.685	k = −10→10
14961 measured reflections	l = −17→18

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.031P)2 + 0.5405P] where P = (Fo2 + 2Fc2)/3
3094 reflections	(Δ/σ)max = 0.002
168 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. IR (KBr cm-1): 3448 (m), 3280 (m), 2970 (m), 2824 (m), 1613 (m, C=C), 1592 (m), 1516 (s), 1469 (m), 1373 (m), 1251 (s), 1174 (m), 1009 (s), 862 (w), 829 (s), 635 (w), 501 (w). 1H-NMR (500 MHz, d6-acetone) p.p.m.: 1.28–1.30 (d, 3H, CH3), 3.44–3.52 (dd, 2H, –CH2NH), 3.77–3.81 (m, 1H, CHCH3), 6.75–6.77 (d, 2H, aromatic protons in the phenyl ring), 7.10–7.11 (d, 2H, aromatic protons in bromophenyl ring), 7.35–7.37 (d, 2H, aromatic protons in bromophenyl ring), 7.48–7.50 (d, 2H, aromatic protons in the phenyl ring). 13C-NMR (125 MHz, d6-acetone) p.p.m.: 24.7 (CH3CH–), 51.5 (–CH2NH), 57.5 (–CHCH3), 115.8 and 132.1 (aromatic carbons in the phenyl ring), 132.1 (quaternary carbon), 120.6 (quaternary carbon, Br), 129.7 and 130.1 (aromatic carbons in the bromophenyl ring), 157.1 (quaternary carbon, OH).

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	Uiso*/Ueq
Br1	0.50613 (2)	1.10683 (4)	0.22306 (2)	0.07679 (13)
C1	0.57389 (19)	0.9552 (3)	0.14304 (16)	0.0493 (5)
C2	0.51175 (19)	0.8545 (3)	0.08329 (17)	0.0548 (6)
H2	0.4354	0.8616	0.0801	0.066*
C3	0.56405 (18)	0.7419 (3)	0.02779 (16)	0.0491 (5)
H3	0.5220	0.6728	−0.0123	0.059*
C4	0.67743 (17)	0.7301 (3)	0.03077 (15)	0.0433 (5)
C5	0.73784 (19)	0.8363 (3)	0.09060 (18)	0.0585 (6)
H5	0.8143	0.8322	0.0927	0.070*
C6	0.6869 (2)	0.9475 (3)	0.14675 (18)	0.0574 (6)
H6	0.7285	1.0170	0.1869	0.069*
C7	0.73506 (19)	0.6046 (3)	−0.02810 (15)	0.0477 (5)
H7	0.6796	0.5310	−0.0577	0.057*
C8	0.7982 (2)	0.6822 (3)	−0.10623 (18)	0.0675 (7)
H8A	0.8519	0.7565	−0.0783	0.101*
H8B	0.7481	0.7406	−0.1492	0.101*
H8C	0.8346	0.5988	−0.1406	0.101*
C9	0.75156 (18)	0.3972 (3)	0.09742 (17)	0.0533 (6)
H9A	0.7273	0.3024	0.0606	0.064*
H9B	0.6866	0.4527	0.1178	0.064*
C10	0.81988 (17)	0.3415 (3)	0.18429 (15)	0.0433 (5)
C11	0.78927 (19)	0.3829 (3)	0.27448 (17)	0.0533 (6)
H11	0.7270	0.4470	0.2805	0.064*
C12	0.8484 (2)	0.3320 (3)	0.35547 (17)	0.0567 (6)
H12	0.8266	0.3631	0.4152	0.068*
C13	0.94031 (17)	0.2344 (3)	0.34832 (16)	0.0464 (5)
C14	0.97270 (17)	0.1923 (3)	0.25915 (16)	0.0511 (6)
H14	1.0348	0.1279	0.2533	0.061*
C15	0.91298 (18)	0.2458 (3)	0.17840 (16)	0.0518 (6)
H15	0.9359	0.2168	0.1186	0.062*
N1	0.81141 (15)	0.5077 (2)	0.03586 (14)	0.0449 (4)
O1	0.99339 (13)	0.1835 (2)	0.43153 (11)	0.0617 (4)
H1A	1.0488	0.1325	0.4195	0.093*
H1	0.8475 (17)	0.456 (3)	0.0064 (14)	0.033 (6)*

	U11	U22	U33	U12	U13	U23
Br1	0.0736 (2)	0.0705 (2)	0.0891 (2)	0.00063 (14)	0.02858 (15)	−0.02241 (16)
C1	0.0551 (13)	0.0417 (12)	0.0522 (13)	0.0010 (10)	0.0123 (11)	0.0010 (11)
C2	0.0435 (12)	0.0577 (15)	0.0637 (15)	−0.0006 (11)	0.0079 (11)	−0.0007 (12)
C3	0.0467 (12)	0.0487 (13)	0.0512 (13)	−0.0049 (10)	−0.0029 (10)	−0.0018 (11)
C4	0.0472 (12)	0.0412 (11)	0.0411 (12)	0.0027 (10)	−0.0006 (9)	0.0042 (10)
C5	0.0421 (12)	0.0566 (14)	0.0763 (17)	0.0020 (11)	−0.0012 (12)	−0.0133 (13)
C6	0.0556 (14)	0.0496 (13)	0.0665 (16)	−0.0027 (11)	−0.0014 (12)	−0.0107 (12)
C7	0.0506 (12)	0.0489 (12)	0.0427 (12)	0.0025 (10)	−0.0040 (10)	0.0009 (11)
C8	0.0771 (18)	0.0749 (18)	0.0510 (14)	0.0131 (15)	0.0094 (13)	0.0074 (13)
C9	0.0430 (12)	0.0539 (13)	0.0626 (15)	−0.0028 (11)	−0.0008 (11)	0.0085 (12)
C10	0.0399 (11)	0.0394 (11)	0.0506 (13)	−0.0017 (9)	0.0035 (10)	0.0084 (10)
C11	0.0475 (13)	0.0493 (13)	0.0641 (15)	0.0123 (10)	0.0108 (11)	0.0055 (12)
C12	0.0605 (15)	0.0623 (15)	0.0489 (14)	0.0114 (12)	0.0153 (12)	0.0037 (12)
C13	0.0433 (11)	0.0479 (12)	0.0483 (13)	0.0001 (10)	0.0070 (10)	0.0112 (10)
C14	0.0435 (12)	0.0584 (14)	0.0524 (14)	0.0099 (10)	0.0107 (11)	0.0078 (11)
C15	0.0477 (13)	0.0623 (15)	0.0462 (13)	0.0050 (11)	0.0091 (10)	0.0009 (11)
N1	0.0432 (10)	0.0470 (11)	0.0448 (11)	0.0061 (9)	0.0044 (9)	0.0020 (9)
O1	0.0559 (10)	0.0796 (12)	0.0501 (9)	0.0145 (9)	0.0084 (8)	0.0167 (9)

Br1—C1	1.895 (2)	C9—N1	1.473 (3)
C1—C6	1.375 (3)	C9—C10	1.506 (3)
C1—C2	1.372 (3)	C9—H9A	0.9700
C2—C3	1.386 (3)	C9—H9B	0.9700
C2—H2	0.9300	C10—C11	1.382 (3)
C3—C4	1.382 (3)	C10—C15	1.384 (3)
C3—H3	0.9300	C11—C12	1.375 (3)
C4—C5	1.390 (3)	C11—H11	0.9300
C4—C7	1.516 (3)	C12—C13	1.384 (3)
C5—C6	1.376 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—O1	1.366 (3)
C6—H6	0.9300	C13—C14	1.377 (3)
C7—N1	1.484 (3)	C14—C15	1.382 (3)
C7—C8	1.515 (3)	C14—H14	0.9300
C7—H7	0.9800	C15—H15	0.9300
C8—H8A	0.9600	N1—H1	0.75 (2)
C8—H8B	0.9600	O1—H1A	0.8200
C8—H8C	0.9600
C6—C1—C2	120.7 (2)	H8B—C8—H8C	109.5
C6—C1—Br1	118.46 (18)	N1—C9—C10	113.10 (18)
C2—C1—Br1	120.85 (18)	N1—C9—H9A	109.0
C1—C2—C3	119.3 (2)	C10—C9—H9A	109.0
C1—C2—H2	120.4	N1—C9—H9B	109.0
C3—C2—H2	120.4	C10—C9—H9B	109.0
C4—C3—C2	121.3 (2)	H9A—C9—H9B	107.8
C4—C3—H3	119.3	C11—C10—C15	117.3 (2)
C2—C3—H3	119.3	C11—C10—C9	120.04 (19)
C3—C4—C5	117.8 (2)	C15—C10—C9	122.6 (2)
C3—C4—C7	121.6 (2)	C12—C11—C10	121.7 (2)
C5—C4—C7	120.55 (19)	C12—C11—H11	119.1
C6—C5—C4	121.3 (2)	C10—C11—H11	119.1
C6—C5—H5	119.3	C11—C12—C13	120.2 (2)
C4—C5—H5	119.3	C11—C12—H12	119.9
C1—C6—C5	119.5 (2)	C13—C12—H12	119.9
C1—C6—H6	120.3	O1—C13—C14	123.6 (2)
C5—C6—H6	120.3	O1—C13—C12	117.3 (2)
N1—C7—C4	109.06 (17)	C14—C13—C12	119.1 (2)
N1—C7—C8	109.62 (19)	C13—C14—C15	120.1 (2)
C4—C7—C8	112.33 (19)	C13—C14—H14	120.0
N1—C7—H7	108.6	C15—C14—H14	120.0
C4—C7—H7	108.6	C10—C15—C14	121.6 (2)
C8—C7—H7	108.6	C10—C15—H15	119.2
C7—C8—H8A	109.5	C14—C15—H15	119.2
C7—C8—H8B	109.5	C9—N1—C7	111.68 (17)
H8A—C8—H8B	109.5	C9—N1—H1	107.4 (16)
C7—C8—H8C	109.5	C7—N1—H1	109.6 (16)
H8A—C8—H8C	109.5	C13—O1—H1A	109.5
C6—C1—C2—C3	1.3 (4)	N1—C9—C10—C15	−64.5 (3)
Br1—C1—C2—C3	−178.17 (17)	C15—C10—C11—C12	0.1 (3)
C1—C2—C3—C4	−0.6 (3)	C9—C10—C11—C12	178.9 (2)
C2—C3—C4—C5	−0.7 (3)	C10—C11—C12—C13	−1.0 (4)
C2—C3—C4—C7	178.6 (2)	C11—C12—C13—O1	−177.9 (2)
C3—C4—C5—C6	1.4 (4)	C11—C12—C13—C14	1.4 (4)
C7—C4—C5—C6	−178.0 (2)	O1—C13—C14—C15	178.5 (2)
C2—C1—C6—C5	−0.7 (4)	C12—C13—C14—C15	−0.8 (4)
Br1—C1—C6—C5	178.81 (19)	C11—C10—C15—C14	0.5 (3)
C4—C5—C6—C1	−0.7 (4)	C9—C10—C15—C14	−178.2 (2)
C3—C4—C7—N1	−126.1 (2)	C13—C14—C15—C10	−0.2 (4)
C5—C4—C7—N1	53.2 (3)	C10—C9—N1—C7	−160.10 (19)
C3—C4—C7—C8	112.2 (2)	C4—C7—N1—C9	71.1 (2)
C5—C4—C7—C8	−68.5 (3)	C8—C7—N1—C9	−165.5 (2)
N1—C9—C10—C11	116.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1i	0.82	2.05	2.794 (2)	150.
N1—H1···O1ii	0.75 (2)	2.40 (2)	3.144 (3)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.82	2.05	2.794 (2)	150
N1—H1⋯O1ii	0.75 (2)	2.40 (2)	3.144 (3)	168 (2)

Symmetry codes: (i) ; (ii) .