Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C25H30NO2+·Cl, has been synthesized, and the crystal structure shows that it is mainly stabilized through inter­molecular N—H...Cl and O—H...Cl and intra­molecular N—H...O hydrogen bonds. The absolute configuration of the new stereogenic center (the C atom adjacent to the N atom on the phenol side) was determined to have an R configuration.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105005676/hj1041sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105005676/hj1041IIsup2.hkl
Contains datablock II

CCDC reference: 248251

Comment top

The synthesis of enantiopure amines is an important subject of research because this class of compounds has found widespread application in biological systems showing pharmacological activity, and these compounds are used as resolving agents, chiral bases and auxiliaries in asymmetric synthesis (Juraristi, 1997; Clifton et al., 1982; Palmieri, 1999, 2000; Cimarelli & Palmieri, 1998, 2000). Most of them have been derived from a few readily available natural products (Soai & Niwa, 1992; Ager et al., 1996). To increase the understanding of asymmetric reactions, the design and synthesis of chiral ligands from non-natural resources is an essential research area in the field of synthetic organic chemistry (Vidal-Ferran et al., 1997; Bolm et al., 1998; Reddy et al., 1999; Paleo et al., 2000; Nugent, 2002) and chiral aminoalkylphenols are gaining increasing importance (Palmieri, 2000; Vyskocil et al., 1998; Cardellicchio et al., 1998, 1999; Bernardinelli et al., 2000; Liu et al., 2001; Cimarelli et al., 2001; Zhang et al., 2003).

We report here the molecular structure of one example of this class of aminoalkylphenols, namely 2-{(R)-1-[(R)-1-(2-methoxy-5-methylphenyl)-2-phenylethylamino]ethyl}-4- methylphenol, (I). The aminoalkylphenol was prepared by conventional condensation of (R)-(-)-[(2-methoxy-5-methyl)-phenyl]-2- phenyl ethylamine with 2-hydroxy-5-methyl acetophenone (both purchased from J&K Chemical Ltd), andthen reduction using sodium borohydride in a tetrahydrofuran (THF)/ethanol (1:1, v/v) mixture. The (R,R)-diastereoisomer is obtained as the main product; the chemical yield of purified and isolated (R,R)-(I) and the diastereoisomeric excess, d.e. (determined by 1HMR of the crude reaction mixture), are 89.2 and 99.0%, respectively. Generally, the reduction should take place after the boron coordinates the imine N atom, activating the C N double bond, which assumes predominantly an E configuration, to nucleophilic attack. Subsequently, an intramolecular hydride transfer from NaBH4 to the C atom both on the si or re face of the CN double bond takes place. Calculations were performed to find the energies of the transition states (R,R)–(I)—Ts and (S,R)–(I)–Ts, minimized at the PM3 semiempirical level, corresponding to the two different situations. Transition state (R,R)–(I)–Ts was more stable, with a difference of 1.35 kcal mol−1, and this value is in satisfactory accordance with experimental d.e., which shows (R,R)–(I) as major product. This is in agreement with the fact that for si attack, the hydride enters on the less hindered side, on the same side of the H atom of the chiral auxiliary (R)-(2-methoxy-5-methyl)phenyl benzyl group. At the same time the N-atom lone pair is gauche between the (2-hydroxy-5-methyl)phenyl and the methyl group of the same chiral group, in a very favourable position. On the other hand, the attack on the re face is on the more hindered side (Me) and with the N-atom lone pair in a less convenient position between (2-hydroxy-5-methyl)phenyl and hydrogen.

It is noteworthy that a novel chiral aminoalkylphenol, (I), was synthesized. To confirm the structure of (I), an X-ray study of the title compound, (II), was carried out (Fig. 1).

The molecular structure of Despite the large number of hydrogen bonds within the asymmetric unit, t(II) is shown in Fig. 1. Thes C1–C6 and C11–C16 aromatic ring are approximately parallel (Fig. 2), the dihedral angle between their planes being 4.5°. The dihehral angle between the planes of the C1–C6 and C19–C24 aromatic rings is 20.0°, while the dihedral angle between the C11–C16 and C19–C24 planes is 14.0°.

Selected bond lengths and angles, including those of the new stereogenic carbon center (C17), are reported in Table 1. The absolute configuration of (I) and (II) is (R,R), as shown in Fig. 1.

N—H···O hydrogen bonds are present within the asymmetric unit; atom N1 act as a hydrogen-bond donor to phenolyl atom O2 (Fig. 2 and Table 2). The molecular structure depends on two further pairs of N—H···Cl and O—H···Cl hydrogen bonds, from atoms N1 and O2 in the cation to atom Cl1 (Fig. 2 and Table 2).

Experimental top

(R)-(-)-[(2-methoxy-5-methyl)phenyl]-2-phenyl ethylamine (3 mmol) and 2-hydroxy-5-methyl acetophenone (3 mmol) (both purchased from J&K Chemical Ltd) were dissolved in me thanol (20 ml) and reacted at room temperature for 12 h. Solvent was removed and NaBH4 (15 mmol) was added to the solution in an THF/ethanol (20 ml, 1:1 v/v) mixture. The reaction was allowed to stand and was monitored by thin-layer chromatography and gel chromatography. After a variable period, the reaction was stopped at constant conversion of starting material. 6 M HCl was then added dropwise to the reaction mixture until hydrogen production ceased, and the mixture was then neutralized with Na2CO3. The aqueous solution was extracted with CHCl3. The organic layer was dried with anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure. Further purification was carried out by thin-layer silica gel chromatography [first time: chloroform/methanol (40:1 v/v); second time: chloroform/methanol (60:1, v/v)] to give chiral 2-{(R)-1-[(R)-1-(2-methoxy-5-methylphenyl)-2-phenylethyl- amino]ethyl}-4-methylphenol (canary oil, 89.2%, [a]D18= −19.5(c 1/2, CHCl3)). Since only the major diastereoisomer was obtained pure by thin-lay silica gel chromatography, the 1H NMR signals for the minor diastereoisomer was deduced from the spectra of the crude reaction mixture. Compound (I) and concentrated HCl were reacted at room temperature, and a white solid was precipitated. The solvent was removed and the solid residue was recrystallized from ethanol to yield compound (II) (m.p. 473.0–473.2 K).

Refinement top

H atoms were visible in difference maps and were subsequently treated as riding atoms, with C—H distances of 0.93 (aromatic H atoms), 0.96 (CH3), 0.97 (CH2) and 0.98 Å (CH).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1995); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of (II), with the atom-numbering scheme for non-H atoms. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted.
[Figure 2] Fig. 2. A view of the packing in (II). Hydrogen bonds are shown as dashed lines For clarity, H atoms have been omitted.
N-[(R)-1-(2-Hydroxy-5-methylphenyl)ethyl]-N-[(R)-1-(2-methoxy-5- methylphenyl)-2-phenylethyl]aminium chloride top
Crystal data top
C25H30NO2+·ClDx = 1.173 Mg m3
Mr = 411.95Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 3690 reflections
a = 9.227 (3) Åθ = 2.5–22.3°
b = 15.323 (6) ŵ = 0.18 mm1
c = 16.504 (6) ÅT = 298 K
V = 2333.4 (15) Å3Block, colorless
Z = 40.43 × 0.35 × 0.31 mm
F(000) = 880
Data collection top
Bruker SMART CCD area-detector
diffractometer
4115 independent reflections
Radiation source: fine-focus sealed tube3080 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.926, Tmax = 0.946k = 1818
12327 measured reflectionsl = 1914
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038Geom
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0695P)2 + 0.2951P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
4115 reflectionsΔρmax = 0.14 e Å3
263 parametersΔρmin = 0.13 e Å3
18 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (7)
Crystal data top
C25H30NO2+·ClV = 2333.4 (15) Å3
Mr = 411.95Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.227 (3) ŵ = 0.18 mm1
b = 15.323 (6) ÅT = 298 K
c = 16.504 (6) Å0.43 × 0.35 × 0.31 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4115 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3080 reflections with I > 2σ(I)
Tmin = 0.926, Tmax = 0.946Rint = 0.031
12327 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038Geom
wR(F2) = 0.097Δρmax = 0.14 e Å3
S = 1.01Δρmin = 0.13 e Å3
4115 reflectionsAbsolute structure: Flack (1983)
263 parametersAbsolute structure parameter: 0.03 (7)
18 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.54726 (8)0.28032 (4)0.32748 (4)0.0603 (2)
N10.3272 (2)0.03250 (12)0.18827 (11)0.0386 (5)
H1A0.39990.00550.21460.046*
H1B0.35490.08800.17950.046*
O10.0697 (2)0.04598 (18)0.24767 (15)0.0941 (7)
O20.4320 (2)0.13496 (10)0.21243 (10)0.0540 (5)
H20.45950.17450.24220.081*
C10.0673 (3)0.0311 (2)0.20648 (19)0.0714 (9)
C20.0664 (3)0.07331 (18)0.20186 (15)0.0520 (7)
C30.0750 (3)0.15326 (19)0.16279 (18)0.0647 (8)
H30.16390.18180.16100.078*
C40.0439 (5)0.1925 (2)0.1261 (2)0.0829 (11)
C50.1739 (5)0.1497 (3)0.1314 (2)0.0980 (14)
H50.25550.17480.10800.118*
C60.1872 (4)0.0713 (3)0.1698 (2)0.0954 (13)
H60.27720.04410.17170.114*
C70.0299 (5)0.2790 (3)0.0838 (3)0.1263 (17)
H7A0.06890.29840.08640.152*0.50
H7B0.05830.27280.02810.152*0.50
H7C0.09140.32110.10980.152*0.50
H7D0.12280.29640.06320.152*0.50
H7E0.00440.32200.12150.152*0.50
H7F0.03750.27380.03980.152*0.50
C80.1921 (4)0.1014 (3)0.2371 (3)0.1235 (17)
H8A0.18030.15300.26930.148*0.50
H8B0.27820.07110.25370.148*0.50
H8C0.20030.11730.18100.148*0.50
H8D0.25890.07460.20000.148*0.50
H8E0.16100.15650.21560.148*0.50
H8F0.23890.11030.28840.148*0.50
C90.1955 (3)0.03336 (16)0.24276 (15)0.0452 (6)
H90.17140.02730.25590.054*
C100.2371 (3)0.07938 (16)0.32176 (15)0.0519 (7)
H10A0.15440.07900.35810.062*
H10B0.26070.13980.31000.062*
C110.3634 (3)0.03745 (16)0.36337 (14)0.0467 (6)
C120.3491 (4)0.04298 (19)0.40086 (17)0.0645 (8)
H120.25920.07040.40170.077*
C130.4655 (5)0.0828 (2)0.43680 (19)0.0817 (11)
H130.45370.13660.46200.098*
C140.5989 (5)0.0439 (3)0.4358 (2)0.0869 (11)
H140.67800.07130.45980.104*
C150.6149 (4)0.0348 (3)0.3995 (2)0.0826 (10)
H150.70530.06160.39910.099*
C160.4983 (3)0.07581 (19)0.36311 (17)0.0607 (8)
H160.51120.12970.33830.073*
C170.3070 (3)0.01147 (14)0.10722 (14)0.0381 (6)
H170.23600.02250.07630.046*
C180.4506 (3)0.00799 (17)0.06186 (16)0.0542 (7)
H18A0.43750.03030.00800.065*
H18B0.48370.05130.05910.065*
H18C0.52110.04280.08990.065*
C190.3103 (3)0.16121 (14)0.17134 (15)0.0416 (6)
C200.2470 (3)0.10201 (14)0.11831 (14)0.0378 (5)
C210.1238 (3)0.12697 (16)0.07632 (15)0.0465 (6)
H210.08080.08720.04110.056*
C220.0621 (3)0.20900 (17)0.08478 (16)0.0571 (7)
C230.1256 (3)0.26526 (17)0.13990 (17)0.0600 (8)
H230.08440.31990.14830.072*
C240.2482 (3)0.24274 (15)0.18272 (17)0.0524 (7)
H240.28910.28200.21910.063*
C250.0707 (4)0.2348 (2)0.0372 (2)0.0946 (12)
H25A0.09880.18750.00240.114*0.50
H25B0.04930.28530.00500.114*0.50
H25C0.14840.24790.07390.114*0.50
H25D0.09890.29300.05180.114*0.50
H25E0.14840.19520.04920.114*0.50
H25F0.04920.23260.01970.114*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0633 (4)0.0449 (3)0.0726 (5)0.0110 (3)0.0108 (4)0.0020 (3)
N10.0369 (11)0.0352 (10)0.0437 (12)0.0005 (8)0.0036 (9)0.0017 (9)
O10.0617 (14)0.128 (2)0.0923 (17)0.0378 (15)0.0039 (14)0.0002 (16)
O20.0532 (11)0.0449 (9)0.0639 (11)0.0038 (9)0.0171 (10)0.0082 (8)
C10.0463 (19)0.108 (3)0.0599 (19)0.0007 (19)0.0017 (16)0.0267 (19)
C20.0386 (15)0.0654 (17)0.0519 (16)0.0092 (14)0.0011 (13)0.0183 (13)
C30.0518 (17)0.0684 (19)0.074 (2)0.0231 (15)0.0078 (16)0.0191 (17)
C40.081 (3)0.094 (3)0.073 (2)0.050 (2)0.022 (2)0.0294 (19)
C50.069 (3)0.144 (4)0.081 (3)0.057 (3)0.020 (2)0.041 (3)
C60.0409 (19)0.164 (4)0.081 (3)0.007 (2)0.0077 (19)0.044 (3)
C70.162 (4)0.097 (3)0.120 (3)0.073 (3)0.043 (3)0.013 (2)
C80.083 (3)0.155 (4)0.132 (4)0.062 (3)0.020 (3)0.033 (3)
C90.0426 (14)0.0461 (14)0.0470 (15)0.0000 (12)0.0038 (12)0.0056 (12)
C100.0558 (17)0.0551 (15)0.0450 (15)0.0053 (13)0.0031 (14)0.0097 (13)
C110.0620 (18)0.0433 (14)0.0348 (14)0.0007 (13)0.0002 (12)0.0087 (11)
C120.090 (2)0.0535 (17)0.0507 (18)0.0096 (17)0.0023 (17)0.0027 (14)
C130.134 (4)0.0563 (19)0.055 (2)0.021 (2)0.010 (2)0.0042 (15)
C140.099 (3)0.100 (3)0.062 (2)0.041 (2)0.014 (2)0.004 (2)
C150.068 (2)0.109 (3)0.071 (2)0.004 (2)0.0105 (18)0.007 (2)
C160.066 (2)0.0612 (17)0.0547 (18)0.0054 (15)0.0047 (14)0.0078 (14)
C170.0431 (14)0.0352 (12)0.0361 (14)0.0007 (11)0.0062 (11)0.0005 (10)
C180.0598 (17)0.0543 (15)0.0485 (15)0.0052 (14)0.0049 (15)0.0041 (12)
C190.0407 (14)0.0394 (13)0.0446 (14)0.0020 (10)0.0032 (13)0.0031 (12)
C200.0452 (15)0.0329 (12)0.0353 (13)0.0010 (11)0.0017 (12)0.0021 (10)
C210.0514 (15)0.0450 (14)0.0432 (14)0.0056 (12)0.0095 (13)0.0006 (12)
C220.0638 (18)0.0530 (16)0.0544 (16)0.0178 (15)0.0064 (15)0.0009 (13)
C230.069 (2)0.0445 (16)0.0668 (19)0.0164 (14)0.0035 (16)0.0040 (14)
C240.0637 (18)0.0387 (13)0.0548 (16)0.0014 (12)0.0030 (15)0.0079 (12)
C250.103 (3)0.079 (2)0.102 (3)0.046 (2)0.040 (2)0.0132 (19)
Geometric parameters (Å, º) top
N1—C171.509 (3)C10—H10B0.9700
N1—C91.512 (3)C11—C161.377 (4)
N1—H1A0.9000C11—C121.385 (4)
N1—H1B0.9000C12—C131.370 (5)
O1—C11.363 (4)C12—H120.9300
O1—C81.423 (4)C13—C141.368 (5)
O2—C191.372 (3)C13—H130.9300
O2—H20.8200C14—C151.354 (5)
C1—C21.395 (4)C14—H140.9300
C1—C61.404 (5)C15—C161.383 (4)
C2—C31.387 (4)C15—H150.9300
C2—C91.500 (3)C16—H160.9300
C3—C41.389 (4)C17—C201.505 (3)
C3—H30.9300C17—C181.523 (4)
C4—C51.369 (6)C17—H170.9800
C4—C71.505 (5)C18—H18A0.9600
C5—C61.363 (6)C18—H18B0.9600
C5—H50.9300C18—H18C0.9600
C6—H60.9300C19—C241.387 (3)
C7—H7A0.9600C19—C201.389 (3)
C7—H7B0.9600C20—C211.385 (3)
C7—H7C0.9600C21—C221.387 (3)
C7—H7D0.9600C21—H210.9300
C7—H7E0.9600C22—C231.384 (4)
C7—H7F0.9600C22—C251.508 (4)
C8—H8A0.9600C23—C241.377 (4)
C8—H8B0.9600C23—H230.9300
C8—H8C0.9600C24—H240.9300
C8—H8D0.9600C25—H25A0.9600
C8—H8E0.9600C25—H25B0.9600
C8—H8F0.9600C25—H25C0.9600
C9—C101.531 (3)C25—H25D0.9600
C9—H90.9800C25—H25E0.9600
C10—C111.497 (4)C25—H25F0.9600
C10—H10A0.9700
C17—N1—C9115.59 (18)C11—C10—H10A109.0
C17—N1—H1A108.4C9—C10—H10A109.0
C9—N1—H1A108.4C11—C10—H10B109.0
C17—N1—H1B108.4C9—C10—H10B109.0
C9—N1—H1B108.4H10A—C10—H10B107.8
H1A—N1—H1B107.4C16—C11—C12117.8 (3)
C1—O1—C8117.9 (3)C16—C11—C10121.3 (2)
C19—O2—H2109.5C12—C11—C10120.9 (3)
O1—C1—C2116.3 (3)C13—C12—C11121.0 (3)
O1—C1—C6125.7 (3)C13—C12—H12119.5
C2—C1—C6118.0 (4)C11—C12—H12119.5
C3—C2—C1119.1 (3)C14—C13—C12120.4 (3)
C3—C2—C9121.6 (2)C14—C13—H13119.8
C1—C2—C9119.3 (3)C12—C13—H13119.8
C2—C3—C4122.6 (3)C15—C14—C13119.4 (3)
C2—C3—H3118.7C15—C14—H14120.3
C4—C3—H3118.7C13—C14—H14120.3
C5—C4—C3117.2 (4)C14—C15—C16120.8 (3)
C5—C4—C7121.8 (4)C14—C15—H15119.6
C3—C4—C7121.0 (4)C16—C15—H15119.6
C6—C5—C4122.0 (4)C11—C16—C15120.5 (3)
C6—C5—H5119.0C11—C16—H16119.7
C4—C5—H5119.0C15—C16—H16119.7
C5—C6—C1121.1 (4)C20—C17—N1110.44 (19)
C5—C6—H6119.5C20—C17—C18114.34 (19)
C1—C6—H6119.5N1—C17—C18108.22 (19)
C4—C7—H7A109.5C20—C17—H17107.9
C4—C7—H7B109.5N1—C17—H17107.9
H7A—C7—H7B109.5C18—C17—H17107.9
C4—C7—H7C109.5C17—C18—H18A109.5
H7A—C7—H7C109.5C17—C18—H18B109.5
H7B—C7—H7C109.5H18A—C18—H18B109.5
C4—C7—H7D109.5C17—C18—H18C109.5
H7A—C7—H7D141.1H18A—C18—H18C109.5
H7B—C7—H7D56.3H18B—C18—H18C109.5
H7C—C7—H7D56.3O2—C19—C24122.4 (2)
C4—C7—H7E109.5O2—C19—C20117.7 (2)
H7A—C7—H7E56.3C24—C19—C20120.0 (2)
H7B—C7—H7E141.1C21—C20—C19118.7 (2)
H7C—C7—H7E56.3C21—C20—C17119.7 (2)
H7D—C7—H7E109.5C19—C20—C17121.6 (2)
C4—C7—H7F109.5C20—C21—C22122.5 (2)
H7A—C7—H7F56.3C20—C21—H21118.8
H7B—C7—H7F56.3C22—C21—H21118.8
H7C—C7—H7F141.1C23—C22—C21117.2 (3)
H7D—C7—H7F109.5C23—C22—C25121.6 (3)
H7E—C7—H7F109.5C21—C22—C25121.2 (3)
O1—C8—H8A109.5C24—C23—C22122.0 (2)
O1—C8—H8B109.5C24—C23—H23119.0
H8A—C8—H8B109.5C22—C23—H23119.0
O1—C8—H8C109.5C23—C24—C19119.7 (2)
H8A—C8—H8C109.5C23—C24—H24120.2
H8B—C8—H8C109.5C19—C24—H24120.2
O1—C8—H8D109.5C22—C25—H25A109.5
H8A—C8—H8D141.1C22—C25—H25B109.5
H8B—C8—H8D56.3H25A—C25—H25B109.5
H8C—C8—H8D56.3C22—C25—H25C109.5
O1—C8—H8E109.5H25A—C25—H25C109.5
H8A—C8—H8E56.3H25B—C25—H25C109.5
H8B—C8—H8E141.1C22—C25—H25D109.5
H8C—C8—H8E56.3H25A—C25—H25D141.1
H8D—C8—H8E109.5H25B—C25—H25D56.3
O1—C8—H8F109.5H25C—C25—H25D56.3
H8A—C8—H8F56.3C22—C25—H25E109.5
H8B—C8—H8F56.3H25A—C25—H25E56.3
H8C—C8—H8F141.1H25B—C25—H25E141.1
H8D—C8—H8F109.5H25C—C25—H25E56.3
H8E—C8—H8F109.5H25D—C25—H25E109.5
C2—C9—N1112.0 (2)C22—C25—H25F109.5
C2—C9—C10113.2 (2)H25A—C25—H25F56.3
N1—C9—C10108.01 (19)H25B—C25—H25F56.3
C2—C9—H9107.8H25C—C25—H25F141.1
N1—C9—H9107.8H25D—C25—H25F109.5
C10—C9—H9107.8H25E—C25—H25F109.5
C11—C10—C9112.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.902.182.771 (3)123
N1—H1B···Cl1i0.902.213.104 (2)170
O2—H2···Cl10.822.293.114 (2)177
Symmetry code: (i) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC25H30NO2+·Cl
Mr411.95
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)9.227 (3), 15.323 (6), 16.504 (6)
V3)2333.4 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.43 × 0.35 × 0.31
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.926, 0.946
No. of measured, independent and
observed [I > 2σ(I)] reflections
12327, 4115, 3080
Rint0.031
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.097, 1.01
No. of reflections4115
No. of parameters263
No. of restraints18
H-atom treatmentGEOM
Δρmax, Δρmin (e Å3)0.14, 0.13
Absolute structureFlack (1983)
Absolute structure parameter0.03 (7)

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1995), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.902.182.771 (3)123
N1—H1B···Cl1i0.902.213.104 (2)170
O2—H2···Cl10.822.293.114 (2)177
Symmetry code: (i) x+1, y1/2, z+1/2.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds