1-Methyl-amino-3-(2,4,6-trimethyl-phen-yl)propan-2-ol.

The methyl-amino-propyl chain in the title compound, C(13)H(21)NO, adopts an extended zigzag conformation and the N atom shows a trigonal coordination. The N atom acts as hydrogen-bond acceptor to the hy-droxy group of an adjacent mol-ecule, generating a helical chain running along the b axis. The amino H atom is not involved in hydrogen bonding.

Related literature

For background to the synthesis: see: Yadigarov et al. (2010 ▶). For the structure of 1-(piperidin-1-yl)-3-(2,4,6-trimethyl­phen­yl)propan-2-ol, see: Maharramov et al. (2011 ▶).

Experimental

Crystal data

C13H21NO

M = 207.31

Monoclinic,

a = 14.408 (1) Å

b = 5.8150 (4) Å

c = 14.4503 (10) Å

β = 91.371 (1)°

V = 1210.34 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII diffractometer

9964 measured reflections

2775 independent reflections

2384 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.04

2775 reflections

148 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007513/bt5484sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007513/bt5484Isup2.hkl

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

C13H21NO	F(000) = 456
Mr = 207.31	Dx = 1.138 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4648 reflections
a = 14.408 (1) Å	θ = 2.8–28.3°
b = 5.8150 (4) Å	µ = 0.07 mm−1
c = 14.4503 (10) Å	T = 100 K
β = 91.371 (1)°	Block, colorless
V = 1210.34 (14) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII diffractometer	2384 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 27.5°, θmin = 2.8°
φ and ω scans	h = −18→18
9964 measured reflections	k = −7→7
2775 independent reflections	l = −18→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.3427P] where P = (Fo2 + 2Fc2)/3
2775 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.29 e Å−3
2 restraints	Δρmin = −0.15 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.40834 (5)	0.62853 (13)	0.68021 (5)	0.02485 (19)
H1	0.4176 (12)	0.690 (3)	0.7345 (8)	0.054 (5)*
N1	0.54856 (6)	0.29883 (16)	0.64351 (6)	0.0236 (2)
H2	0.5558 (9)	0.4495 (15)	0.6437 (9)	0.032 (4)*
C1	0.60577 (8)	0.1994 (2)	0.57080 (8)	0.0292 (3)
H1A	0.6715	0.2278	0.5856	0.044*
H1B	0.5893	0.2709	0.5112	0.044*
H1C	0.5947	0.0334	0.5671	0.044*
C2	0.44967 (7)	0.25622 (18)	0.62563 (7)	0.0240 (2)
H2A	0.4369	0.0898	0.6320	0.029*
H2B	0.4332	0.3018	0.5613	0.029*
C3	0.39001 (7)	0.38978 (18)	0.69225 (7)	0.0222 (2)
H3	0.4073	0.3446	0.7572	0.027*
C4	0.28756 (7)	0.3311 (2)	0.67318 (8)	0.0265 (2)
H4A	0.2725	0.3660	0.6075	0.032*
H4B	0.2792	0.1636	0.6820	0.032*
C5	0.21865 (7)	0.45598 (19)	0.73277 (7)	0.0233 (2)
C6	0.19897 (7)	0.37481 (19)	0.82164 (7)	0.0246 (2)
C7	0.13219 (7)	0.4868 (2)	0.87371 (7)	0.0260 (2)
H7	0.1190	0.4302	0.9337	0.031*
C8	0.08455 (7)	0.6778 (2)	0.84056 (8)	0.0261 (2)
C9	0.10519 (8)	0.75788 (19)	0.75269 (8)	0.0266 (2)
H9	0.0734	0.8891	0.7289	0.032*
C10	0.17130 (7)	0.65081 (19)	0.69854 (7)	0.0246 (2)
C11	0.18859 (9)	0.7448 (2)	0.60308 (8)	0.0316 (3)
H11A	0.1554	0.8907	0.5949	0.047*
H11B	0.1664	0.6344	0.5564	0.047*
H11C	0.2553	0.7704	0.5960	0.047*
C12	0.01217 (8)	0.7968 (2)	0.89726 (9)	0.0340 (3)
H12A	0.0111	0.7277	0.9591	0.051*
H12B	−0.0489	0.7795	0.8668	0.051*
H12C	0.0274	0.9606	0.9028	0.051*
C13	0.24826 (8)	0.1699 (2)	0.86386 (8)	0.0303 (3)
H13A	0.2144	0.1166	0.9179	0.045*
H13B	0.3115	0.2139	0.8831	0.045*
H13C	0.2509	0.0459	0.8180	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0301 (4)	0.0223 (4)	0.0221 (4)	−0.0012 (3)	−0.0007 (3)	−0.0008 (3)
N1	0.0252 (5)	0.0231 (5)	0.0225 (4)	0.0006 (4)	0.0033 (3)	−0.0003 (3)
C1	0.0308 (6)	0.0302 (6)	0.0268 (5)	0.0043 (5)	0.0060 (4)	−0.0012 (4)
C2	0.0263 (5)	0.0241 (5)	0.0217 (5)	0.0004 (4)	0.0004 (4)	−0.0024 (4)
C3	0.0242 (5)	0.0218 (5)	0.0206 (5)	−0.0002 (4)	0.0000 (4)	−0.0008 (4)
C4	0.0254 (5)	0.0274 (5)	0.0267 (5)	−0.0013 (4)	−0.0003 (4)	−0.0061 (4)
C5	0.0199 (5)	0.0254 (5)	0.0245 (5)	−0.0033 (4)	−0.0018 (4)	−0.0045 (4)
C6	0.0211 (5)	0.0252 (5)	0.0273 (5)	−0.0039 (4)	−0.0028 (4)	−0.0009 (4)
C7	0.0222 (5)	0.0323 (6)	0.0235 (5)	−0.0045 (4)	−0.0001 (4)	0.0000 (4)
C8	0.0197 (5)	0.0316 (6)	0.0270 (5)	−0.0020 (4)	−0.0011 (4)	−0.0060 (4)
C9	0.0237 (5)	0.0278 (5)	0.0282 (5)	0.0013 (4)	−0.0045 (4)	−0.0011 (4)
C10	0.0236 (5)	0.0280 (5)	0.0221 (5)	−0.0029 (4)	−0.0033 (4)	−0.0027 (4)
C11	0.0339 (6)	0.0369 (6)	0.0240 (5)	0.0013 (5)	−0.0023 (4)	0.0015 (5)
C12	0.0267 (6)	0.0412 (7)	0.0342 (6)	0.0045 (5)	0.0030 (5)	−0.0061 (5)
C13	0.0285 (6)	0.0284 (6)	0.0339 (6)	−0.0016 (4)	−0.0003 (5)	0.0047 (5)

O1—C3	1.4247 (13)	C6—C7	1.3966 (15)
O1—H1	0.870 (9)	C6—C13	1.5087 (16)
N1—C2	1.4632 (14)	C7—C8	1.3854 (16)
N1—C1	1.4693 (14)	C7—H7	0.9500
N1—H2	0.882 (9)	C8—C9	1.3912 (16)
C1—H1A	0.9800	C8—C12	1.5094 (15)
C1—H1B	0.9800	C9—C10	1.3939 (15)
C1—H1C	0.9800	C9—H9	0.9500
C2—C3	1.5193 (14)	C10—C11	1.5100 (15)
C2—H2A	0.9900	C11—H11A	0.9800
C2—H2B	0.9900	C11—H11B	0.9800
C3—C4	1.5334 (14)	C11—H11C	0.9800
C3—H3	1.0000	C12—H12A	0.9800
C4—C5	1.5149 (15)	C12—H12B	0.9800
C4—H4A	0.9900	C12—H12C	0.9800
C4—H4B	0.9900	C13—H13A	0.9800
C5—C6	1.4036 (15)	C13—H13B	0.9800
C5—C10	1.4062 (15)	C13—H13C	0.9800
C3—O1—H1	108.4 (11)	C7—C6—C13	118.31 (10)
C2—N1—C1	111.57 (9)	C5—C6—C13	122.15 (10)
C2—N1—H2	106.4 (9)	C8—C7—C6	121.98 (10)
C1—N1—H2	109.0 (9)	C8—C7—H7	119.0
N1—C1—H1A	109.5	C6—C7—H7	119.0
N1—C1—H1B	109.5	C7—C8—C9	117.96 (10)
H1A—C1—H1B	109.5	C7—C8—C12	121.53 (10)
N1—C1—H1C	109.5	C9—C8—C12	120.51 (11)
H1A—C1—H1C	109.5	C8—C9—C10	121.79 (10)
H1B—C1—H1C	109.5	C8—C9—H9	119.1
N1—C2—C3	111.40 (8)	C10—C9—H9	119.1
N1—C2—H2A	109.3	C9—C10—C5	119.65 (10)
C3—C2—H2A	109.3	C9—C10—C11	118.75 (10)
N1—C2—H2B	109.3	C5—C10—C11	121.59 (10)
C3—C2—H2B	109.3	C10—C11—H11A	109.5
H2A—C2—H2B	108.0	C10—C11—H11B	109.5
O1—C3—C2	108.14 (8)	H11A—C11—H11B	109.5
O1—C3—C4	112.04 (9)	C10—C11—H11C	109.5
C2—C3—C4	109.23 (8)	H11A—C11—H11C	109.5
O1—C3—H3	109.1	H11B—C11—H11C	109.5
C2—C3—H3	109.1	C8—C12—H12A	109.5
C4—C3—H3	109.1	C8—C12—H12B	109.5
C5—C4—C3	115.63 (9)	H12A—C12—H12B	109.5
C5—C4—H4A	108.4	C8—C12—H12C	109.5
C3—C4—H4A	108.4	H12A—C12—H12C	109.5
C5—C4—H4B	108.4	H12B—C12—H12C	109.5
C3—C4—H4B	108.4	C6—C13—H13A	109.5
H4A—C4—H4B	107.4	C6—C13—H13B	109.5
C6—C5—C10	119.07 (10)	H13A—C13—H13B	109.5
C6—C5—C4	120.56 (10)	C6—C13—H13C	109.5
C10—C5—C4	120.34 (10)	H13A—C13—H13C	109.5
C7—C6—C5	119.54 (10)	H13B—C13—H13C	109.5
C1—N1—C2—C3	−171.17 (9)	C13—C6—C7—C8	179.21 (10)
N1—C2—C3—O1	60.20 (11)	C6—C7—C8—C9	−0.18 (16)
N1—C2—C3—C4	−177.63 (9)	C6—C7—C8—C12	179.70 (10)
O1—C3—C4—C5	−58.72 (12)	C7—C8—C9—C10	0.23 (16)
C2—C3—C4—C5	−178.53 (9)	C12—C8—C9—C10	−179.64 (10)
C3—C4—C5—C6	−82.99 (12)	C8—C9—C10—C5	0.23 (16)
C3—C4—C5—C10	99.05 (12)	C8—C9—C10—C11	178.81 (10)
C10—C5—C6—C7	0.81 (15)	C6—C5—C10—C9	−0.75 (15)
C4—C5—C6—C7	−177.18 (9)	C4—C5—C10—C9	177.24 (9)
C10—C5—C6—C13	−178.73 (10)	C6—C5—C10—C11	−179.29 (10)
C4—C5—C6—C13	3.28 (15)	C4—C5—C10—C11	−1.30 (15)
C5—C6—C7—C8	−0.35 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.87 (1)	1.93 (1)	2.789 (1)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.87 (1)	1.93 (1)	2.789 (1)	173 (2)

Symmetry code: (i) .