Literature DB >> 21200807

N-[(S)-1-(3,5-Dimethyl-2-hydroxy-phenyl)-ethyl]-N-[(R)-2-hydr-oxy-1-phenyl-ethyl]ammonium chloride.

Guangyou Zhang, Xungang Gu, Xiangbo Wang, Wanhui Wang, Shuchun Li.

Abstract

In the title compound, C(18)H(24)NO(2) (+)·Cl(-), the absolute configuration of the new stereogenic centre (the C atom with a CH(2)OH substituent) was unambiguously determined to have an R configuration. The dihedral angle between the two aromatic rings is 30.82 (2)°. Inter-molecular N-H⋯Cl and O-H⋯Cl hydrogen bonds and intra-molecular N-H⋯O hydrogen bonds stabilize the crystal structure.

Entities: Chemical Disease Gene

Year: 2007 PMID： 21200807 PMCID： PMC2915299 DOI： 10.1107/S1600536807063106

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For related literature, see: Cimarelli & Palmieri (1998 ▶, 2000 ▶); Cimarelli et al. (2002 ▶); Demir et al. (1999 ▶); Palmieri (1999 ▶, 2000 ▶); Rijnberg et al. (1997 ▶); Sola et al. (1998 ▶); Tümerdem et al. (2005 ▶); Tseng & Yang (2004 ▶); Xu et al. (2002 ▶); Zhang et al. (2006a ▶,b ▶).

Experimental

Crystal data

C18H24NO2 +·Cl− M = 321.83 Orthorhombic, a = 7.6500 (15) Å b = 13.764 (3) Å c = 16.420 (3) Å V = 1728.9 (6) Å3 Z = 4 Mo Kα radiation μ = 0.23 mm−1 T = 298 (2) K 0.44 × 0.32 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.906, T max = 0.955 8842 measured reflections 3202 independent reflections 2738 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.097 S = 1.02 3202 reflections 204 parameters H-atom parameters constrained Δρmax = 0.21 e Å−3 Δρmin = −0.12 e Å−3 Absolute structure: Flack (1983 ▶), with 1204 Friedel pairs Flack parameter: −0.01 (7) Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2001 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063106/bv2080sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063106/bv2080Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₂₄NO₂⁺·Cl^–	F₀₀₀ = 688
M_r = 321.83	D_x = 1.236 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P2ac2ab	Cell parameters from 2408 reflections
a = 7.6500 (15) Å	θ = 2.5–22.3º
b = 13.764 (3) Å	µ = 0.23 mm⁻¹
c = 16.420 (3) Å	T = 298 (2) K
V = 1728.9 (6) Å³	Block, colourless
Z = 4	0.44 × 0.32 × 0.21 mm

Bruker SMART CCD area-detector diffractometer	3202 independent reflections
Radiation source: fine-focus sealed tube	2738 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.034
T = 298(2) K	θ_max = 25.5º
φ and ω scans	θ_min = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.906, T_max = 0.955	k = −16→16
8842 measured reflections	l = −19→19

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.048P)² + 0.1178P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.097	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.21 e Å⁻³
3202 reflections	Δρ_min = −0.12 e Å⁻³
204 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with how many Friedel pairs?
Secondary atom site location: difference Fourier map	Flack parameter: −0.01 (7)

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	U_iso*/U_eq
C1	0.1767 (4)	0.09660 (19)	0.63609 (17)	0.0640 (8)
H1C	0.1916	0.1312	0.5879	0.077*
C2	0.1117 (5)	0.1430 (2)	0.7031 (2)	0.0778 (10)
H2A	0.0825	0.2085	0.6998	0.093*
C3	0.0893 (4)	0.0945 (2)	0.77455 (17)	0.0644 (8)
H3	0.0458	0.1263	0.8202	0.077*
C4	0.1318 (4)	−0.0016 (2)	0.77788 (15)	0.0597 (7)
H4	0.1172	−0.0354	0.8265	0.072*
C5	0.1958 (4)	−0.04971 (18)	0.71078 (14)	0.0507 (7)
H5	0.2225	−0.1155	0.7142	0.061*
C6	0.2206 (3)	−0.00047 (17)	0.63832 (13)	0.0393 (5)
C7	0.2868 (3)	−0.04882 (17)	0.56183 (13)	0.0417 (6)
H7	0.3156	0.0023	0.5226	0.050*
C8	0.1534 (3)	−0.1151 (2)	0.52276 (15)	0.0537 (7)
H8A	0.1227	−0.1673	0.5598	0.064*
H8B	0.0482	−0.0790	0.5098	0.064*
C9	0.5988 (3)	−0.05219 (16)	0.61594 (12)	0.0368 (5)
H9	0.5552	−0.0224	0.6662	0.044*
C10	0.7415 (3)	−0.1235 (2)	0.63911 (15)	0.0502 (6)
H10A	0.6954	−0.1706	0.6765	0.075*
H10B	0.8363	−0.0891	0.6644	0.075*
H10C	0.7831	−0.1559	0.5911	0.075*
C11	0.6644 (3)	0.02824 (16)	0.56161 (13)	0.0369 (5)
C12	0.6896 (3)	0.12039 (17)	0.59373 (15)	0.0442 (6)
H12	0.6527	0.1333	0.6466	0.053*
C13	0.7678 (3)	0.19304 (18)	0.54931 (15)	0.0467 (6)
C14	0.7978 (4)	0.29279 (19)	0.58643 (18)	0.0665 (8)
H14A	0.7111	0.3372	0.5664	0.100*
H14B	0.9120	0.3157	0.5717	0.100*
H14C	0.7892	0.2885	0.6446	0.100*
C15	0.8203 (4)	0.17215 (17)	0.47075 (15)	0.0491 (7)
H15	0.8747	0.2208	0.4407	0.059*
C16	0.7957 (3)	0.08221 (16)	0.43472 (13)	0.0423 (6)
C17	0.8537 (4)	0.0637 (2)	0.34898 (14)	0.0615 (8)
H17A	0.8875	0.1239	0.3241	0.092*
H17B	0.7592	0.0353	0.3187	0.092*
H17C	0.9514	0.0199	0.3492	0.092*
C18	0.7165 (3)	0.01038 (16)	0.48159 (13)	0.0389 (5)
Cl1	0.60116 (9)	0.19629 (5)	0.83115 (4)	0.0548 (2)
N1	0.4501 (2)	−0.10661 (13)	0.57750 (11)	0.0371 (4)
H1A	0.4225	−0.1570	0.6100	0.044*
H1B	0.4874	−0.1313	0.5298	0.044*
O1	0.6813 (2)	−0.08114 (12)	0.45252 (9)	0.0517 (5)
H1	0.7531	−0.0954	0.4174	0.078*
O2	0.2279 (3)	−0.15362 (19)	0.45100 (12)	0.0837 (7)
H2	0.1519	−0.1591	0.4160	0.125*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.084 (2)	0.0547 (16)	0.0531 (16)	0.0138 (16)	0.0037 (16)	0.0089 (13)
C2	0.103 (3)	0.0589 (17)	0.072 (2)	0.0279 (18)	−0.001 (2)	−0.0061 (16)
C3	0.0637 (18)	0.0781 (19)	0.0514 (16)	0.0197 (17)	−0.0026 (15)	−0.0144 (14)
C4	0.0643 (19)	0.0749 (18)	0.0398 (13)	0.0120 (16)	0.0072 (13)	0.0048 (13)
C5	0.0531 (17)	0.0521 (14)	0.0468 (14)	0.0073 (13)	0.0037 (13)	0.0062 (11)
C6	0.0308 (12)	0.0480 (13)	0.0391 (12)	0.0000 (11)	−0.0009 (10)	0.0018 (11)
C7	0.0373 (14)	0.0512 (14)	0.0367 (12)	−0.0033 (11)	−0.0014 (11)	0.0071 (10)
C8	0.0357 (15)	0.0822 (19)	0.0431 (14)	−0.0022 (13)	−0.0044 (11)	−0.0101 (13)
C9	0.0322 (12)	0.0499 (13)	0.0282 (10)	−0.0036 (11)	0.0016 (10)	−0.0064 (9)
C10	0.0377 (14)	0.0660 (15)	0.0470 (14)	−0.0032 (12)	−0.0022 (11)	0.0041 (12)
C11	0.0275 (12)	0.0459 (13)	0.0373 (12)	−0.0011 (9)	0.0012 (10)	−0.0018 (10)
C12	0.0403 (14)	0.0504 (14)	0.0419 (13)	0.0001 (12)	−0.0007 (11)	−0.0106 (11)
C13	0.0419 (14)	0.0435 (13)	0.0546 (15)	−0.0024 (12)	−0.0026 (12)	−0.0037 (12)
C14	0.073 (2)	0.0509 (16)	0.0755 (19)	−0.0086 (15)	−0.0006 (17)	−0.0123 (14)
C15	0.0480 (16)	0.0439 (15)	0.0554 (16)	−0.0025 (12)	0.0001 (13)	0.0095 (11)
C16	0.0401 (14)	0.0469 (13)	0.0400 (13)	−0.0018 (11)	0.0016 (12)	0.0057 (11)
C17	0.075 (2)	0.0663 (16)	0.0430 (14)	−0.0121 (14)	0.0128 (14)	0.0065 (12)
C18	0.0346 (13)	0.0432 (13)	0.0388 (12)	−0.0016 (11)	0.0004 (10)	−0.0041 (10)
Cl1	0.0623 (4)	0.0520 (4)	0.0501 (3)	0.0092 (3)	−0.0014 (3)	−0.0007 (3)
N1	0.0323 (11)	0.0466 (11)	0.0323 (9)	−0.0016 (8)	0.0035 (8)	−0.0002 (8)
O1	0.0625 (12)	0.0517 (10)	0.0410 (9)	−0.0134 (9)	0.0150 (9)	−0.0109 (8)
O2	0.0571 (14)	0.142 (2)	0.0522 (12)	0.0003 (13)	−0.0057 (11)	−0.0414 (12)

C1—C2	1.366 (4)	C10—H10B	0.9600
C1—C6	1.378 (3)	C10—H10C	0.9600
C1—H1C	0.9300	C11—C12	1.387 (3)
C2—C3	1.361 (4)	C11—C18	1.395 (3)
C2—H2A	0.9300	C12—C13	1.375 (3)
C3—C4	1.363 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C15	1.381 (3)
C4—C5	1.375 (3)	C13—C14	1.520 (3)
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.382 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—C7	1.509 (3)	C15—C16	1.385 (3)
C7—N1	1.503 (3)	C15—H15	0.9300
C7—C8	1.512 (3)	C16—C18	1.392 (3)
C7—H7	0.9800	C16—C17	1.498 (3)
C8—O2	1.412 (3)	C17—H17A	0.9600
C8—H8A	0.9700	C17—H17B	0.9600
C8—H8B	0.9700	C17—H17C	0.9600
C9—N1	1.501 (3)	C18—O1	1.374 (3)
C9—C11	1.508 (3)	N1—H1A	0.9000
C9—C10	1.516 (3)	N1—H1B	0.9000
C9—H9	0.9800	O1—H1	0.8200
C10—H10A	0.9600	O2—H2	0.8200

C2—C1—C6	121.4 (3)	H10A—C10—H10C	109.5
C2—C1—H1C	119.3	H10B—C10—H10C	109.5
C6—C1—H1C	119.3	C12—C11—C18	118.7 (2)
C3—C2—C1	120.7 (3)	C12—C11—C9	119.52 (19)
C3—C2—H2A	119.6	C18—C11—C9	121.54 (19)
C1—C2—H2A	119.6	C13—C12—C11	121.6 (2)
C2—C3—C4	118.7 (3)	C13—C12—H12	119.2
C2—C3—H3	120.6	C11—C12—H12	119.2
C4—C3—H3	120.6	C12—C13—C15	118.1 (2)
C3—C4—C5	121.3 (2)	C12—C13—C14	120.7 (2)
C3—C4—H4	119.3	C15—C13—C14	121.2 (2)
C5—C4—H4	119.3	C13—C14—H14A	109.5
C4—C5—C6	120.2 (2)	C13—C14—H14B	109.5
C4—C5—H5	119.9	H14A—C14—H14B	109.5
C6—C5—H5	119.9	C13—C14—H14C	109.5
C1—C6—C5	117.7 (2)	H14A—C14—H14C	109.5
C1—C6—C7	119.2 (2)	H14B—C14—H14C	109.5
C5—C6—C7	123.1 (2)	C13—C15—C16	123.1 (2)
N1—C7—C6	111.72 (18)	C13—C15—H15	118.5
N1—C7—C8	108.31 (18)	C16—C15—H15	118.5
C6—C7—C8	113.11 (19)	C15—C16—C18	117.3 (2)
N1—C7—H7	107.8	C15—C16—C17	120.9 (2)
C6—C7—H7	107.8	C18—C16—C17	121.8 (2)
C8—C7—H7	107.8	C16—C17—H17A	109.5
O2—C8—C7	108.0 (2)	C16—C17—H17B	109.5
O2—C8—H8A	110.1	H17A—C17—H17B	109.5
C7—C8—H8A	110.1	C16—C17—H17C	109.5
O2—C8—H8B	110.1	H17A—C17—H17C	109.5
C7—C8—H8B	110.1	H17B—C17—H17C	109.5
H8A—C8—H8B	108.4	O1—C18—C16	123.0 (2)
N1—C9—C11	111.72 (17)	O1—C18—C11	115.65 (19)
N1—C9—C10	109.15 (18)	C16—C18—C11	121.3 (2)
C11—C9—C10	112.58 (19)	C9—N1—C7	115.96 (16)
N1—C9—H9	107.7	C9—N1—H1A	108.3
C11—C9—H9	107.7	C7—N1—H1A	108.3
C10—C9—H9	107.7	C9—N1—H1B	108.3
C9—C10—H10A	109.5	C7—N1—H1B	108.3
C9—C10—H10B	109.5	H1A—N1—H1B	107.4
H10A—C10—H10B	109.5	C18—O1—H1	109.5
C9—C10—H10C	109.5	C8—O2—H2	109.5

C6—C1—C2—C3	0.4 (6)	C9—C11—C12—C13	172.5 (2)
C1—C2—C3—C4	−0.4 (5)	C11—C12—C13—C15	0.4 (4)
C2—C3—C4—C5	−0.2 (5)	C11—C12—C13—C14	−178.6 (2)
C3—C4—C5—C6	0.9 (4)	C12—C13—C15—C16	0.9 (4)
C2—C1—C6—C5	0.3 (4)	C14—C13—C15—C16	179.9 (3)
C2—C1—C6—C7	178.2 (3)	C13—C15—C16—C18	−1.0 (4)
C4—C5—C6—C1	−0.9 (4)	C13—C15—C16—C17	179.4 (2)
C4—C5—C6—C7	−178.7 (2)	C15—C16—C18—O1	178.6 (2)
C1—C6—C7—N1	131.7 (2)	C17—C16—C18—O1	−1.8 (4)
C5—C6—C7—N1	−50.5 (3)	C15—C16—C18—C11	−0.2 (3)
C1—C6—C7—C8	−105.8 (3)	C17—C16—C18—C11	179.4 (2)
C5—C6—C7—C8	72.0 (3)	C12—C11—C18—O1	−177.4 (2)
N1—C7—C8—O2	−57.3 (3)	C9—C11—C18—O1	8.7 (3)
C6—C7—C8—O2	178.3 (2)	C12—C11—C18—C16	1.4 (3)
N1—C9—C11—C12	131.8 (2)	C9—C11—C18—C16	−172.5 (2)
C10—C9—C11—C12	−105.0 (2)	C11—C9—N1—C7	−63.3 (2)
N1—C9—C11—C18	−54.4 (3)	C10—C9—N1—C7	171.52 (17)
C10—C9—C11—C18	68.8 (3)	C6—C7—N1—C9	−55.1 (2)
C18—C11—C12—C13	−1.5 (3)	C8—C7—N1—C9	179.62 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl1ⁱ	0.82	2.44	3.249 (2)	169
O1—H1···Cl1ⁱⁱ	0.82	2.28	3.0417 (18)	156
N1—H1A···Cl1ⁱⁱⁱ	0.90	2.25	3.125 (2)	165
N1—H1B···O1	0.90	2.07	2.732 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯Cl1ⁱ	0.82	2.44	3.249 (2)	169
O1—H1⋯Cl1ⁱⁱ	0.82	2.28	3.0417 (18)	156
N1—H1A⋯Cl1ⁱⁱⁱ	0.90	2.25	3.125 (2)	165
N1—H1B⋯O1	0.90	2.07	2.732 (2)	129

Symmetry codes: (i) ; (ii) ; (iii) .

1 in total

1. A Superior, Readily Available Enantiopure Ligand for the Catalytic Enantioselective Addition of Diethylzinc to alpha-Substituted Aldehydes.

Authors: Lluís Solà; Katamreddy Subba Reddy; Anton Vidal-Ferran; Albert Moyano; Miquel A. Pericàs; Antoni Riera; Angel Alvarez-Larena; Joan-F. Piniella
Journal: J Org Chem Date: 1998-10-02 Impact factor: 4.354

1 in total