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2,4-Dimethyl-6-[(1R)-1-{[(1R)-2-methyl-1-phenyl­propyl]amino}­ethyl]phenol, (I), has been synthesized and its absolute configuration has been determined by reference to the crystal structure of the title compound, C20H28NO+·Cl, (II), the hydro­chloride of (I). The new stereogenic centre (the C atom adjacent to the N atom on the phenol side) was unambiguously determined to have an R configuration.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010002/dn2012sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010002/dn2012IIsup2.hkl
Contains datablock II

CCDC reference: 605056

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.103
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 38.00 A   3
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.49 From the CIF: _reflns_number_total 3687 Count of symmetry unique reflns 2116 Completeness (_total/calc) 174.24% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1571 Fraction of Friedel pairs measured 0.742 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

N-[(R)-1-(2-Hydroxy-3,5-dimethylphenyl)ethyl]-N-[(R)-2-methyl-1- phenylpropyl]ammonium chloride top
Crystal data top
C20H28NO+·ClF(000) = 720
Mr = 333.88Dx = 1.114 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ac2abCell parameters from 5813 reflections
a = 9.0404 (12) Åθ = 2.5–27.8°
b = 11.7373 (15) ŵ = 0.20 mm1
c = 18.768 (2) ÅT = 298 K
V = 1991.5 (4) Å3Block, colourless
Z = 40.50 × 0.34 × 0.25 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3558 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 25.5°, θmin = 2.1°
φ and ω scansh = 106
10401 measured reflectionsk = 1414
3687 independent reflectionsl = 2221
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0466P)2 + 0.2784P]
where P = (Fo2 + 2Fc2)/3
S = 1.19(Δ/σ)max = 0.001
3687 reflectionsΔρmax = 0.20 e Å3
214 parametersΔρmin = 0.21 e Å3
0 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (6)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7867 (2)1.00420 (18)0.59293 (11)0.0346 (5)
C20.7601 (3)1.08093 (19)0.53810 (10)0.0393 (5)
C30.8773 (3)1.1627 (2)0.51366 (13)0.0581 (7)
H3A0.90471.21170.55240.087*
H3B0.83971.20780.47500.087*
H3C0.96251.12090.49790.087*
C40.6203 (3)1.08120 (19)0.50680 (11)0.0439 (5)
H40.60091.13340.47070.053*
C50.5093 (3)1.0069 (2)0.52732 (12)0.0445 (5)
C60.3561 (3)1.0118 (3)0.49533 (15)0.0641 (7)
H6A0.31600.93620.49250.096*
H6B0.36141.04410.44840.096*
H6C0.29351.05810.52480.096*
C70.5420 (2)0.9293 (2)0.58019 (11)0.0406 (5)
H70.46980.87740.59400.049*
C80.6788 (2)0.92612 (18)0.61338 (10)0.0361 (5)
C90.7089 (3)0.83649 (18)0.66925 (11)0.0395 (5)
H90.61570.79710.67920.047*
C100.8211 (3)0.7479 (2)0.64618 (14)0.0597 (7)
H10A0.91420.78430.63680.090*
H10B0.78680.71080.60370.090*
H10C0.83330.69260.68340.090*
C110.6566 (2)0.97554 (17)0.77096 (11)0.0346 (4)
H110.65031.04140.73900.042*
C120.7206 (2)1.01646 (19)0.84199 (12)0.0424 (5)
H120.72250.95160.87490.051*
C130.8779 (3)1.0610 (3)0.83406 (15)0.0633 (7)
H13A0.88111.11660.79660.095*
H13B0.94290.99890.82260.095*
H13C0.90891.09540.87800.095*
C140.6213 (4)1.1080 (3)0.87370 (17)0.0749 (9)
H14A0.66101.13240.91860.112*
H14B0.52381.07760.88070.112*
H14C0.61641.17180.84170.112*
C150.5039 (2)0.92488 (19)0.77748 (11)0.0373 (5)
C160.4803 (3)0.8275 (2)0.81781 (12)0.0433 (5)
H160.55940.79170.84020.052*
C170.3381 (3)0.7837 (2)0.82465 (13)0.0552 (7)
H170.32240.71840.85170.066*
C180.2212 (3)0.8359 (3)0.79186 (16)0.0632 (8)
H180.12630.80610.79650.076*
C190.2444 (3)0.9327 (3)0.75190 (16)0.0619 (7)
H190.16500.96840.72970.074*
C200.3847 (2)0.9767 (2)0.74479 (13)0.0469 (6)
H200.39951.04210.71770.056*
N10.76150 (18)0.89025 (15)0.73773 (9)0.0345 (4)
H1A0.84820.92540.72930.041*
H1B0.77870.83450.76960.041*
O10.91879 (17)1.00074 (15)0.62997 (8)0.0470 (4)
H10.96571.05930.62230.071*
Cl10.85722 (7)0.70061 (5)0.84406 (3)0.04755 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0353 (11)0.0352 (11)0.0333 (10)0.0017 (10)0.0011 (9)0.0024 (8)
C20.0504 (13)0.0383 (11)0.0292 (9)0.0031 (11)0.0023 (10)0.0023 (9)
C30.0709 (18)0.0581 (15)0.0454 (13)0.0188 (15)0.0022 (12)0.0128 (11)
C40.0598 (14)0.0405 (12)0.0313 (10)0.0030 (12)0.0062 (10)0.0002 (9)
C50.0467 (13)0.0486 (13)0.0381 (11)0.0078 (11)0.0051 (10)0.0089 (10)
C60.0543 (15)0.0728 (18)0.0653 (16)0.0049 (16)0.0148 (15)0.0036 (14)
C70.0381 (12)0.0416 (12)0.0421 (11)0.0055 (10)0.0015 (10)0.0046 (10)
C80.0400 (12)0.0333 (10)0.0348 (10)0.0010 (9)0.0002 (9)0.0015 (8)
C90.0399 (11)0.0350 (11)0.0436 (12)0.0051 (10)0.0030 (10)0.0017 (9)
C100.079 (2)0.0425 (13)0.0581 (14)0.0150 (13)0.0070 (14)0.0004 (11)
C110.0340 (11)0.0306 (10)0.0393 (10)0.0022 (9)0.0008 (9)0.0076 (8)
C120.0435 (12)0.0403 (11)0.0435 (11)0.0012 (10)0.0007 (11)0.0023 (10)
C130.0570 (16)0.0727 (17)0.0604 (16)0.0205 (15)0.0073 (13)0.0024 (14)
C140.074 (2)0.0728 (19)0.0776 (19)0.0112 (18)0.0037 (16)0.0280 (16)
C150.0355 (11)0.0376 (11)0.0388 (10)0.0014 (10)0.0019 (9)0.0007 (9)
C160.0403 (12)0.0443 (13)0.0452 (12)0.0001 (11)0.0016 (10)0.0061 (10)
C170.0572 (16)0.0511 (13)0.0572 (14)0.0125 (13)0.0174 (12)0.0055 (11)
C180.0345 (13)0.0753 (19)0.0798 (19)0.0129 (14)0.0130 (13)0.0100 (16)
C190.0348 (13)0.0749 (19)0.0761 (18)0.0104 (13)0.0022 (13)0.0066 (15)
C200.0383 (13)0.0484 (13)0.0541 (14)0.0089 (11)0.0025 (11)0.0086 (11)
N10.0298 (9)0.0345 (9)0.0392 (9)0.0001 (7)0.0001 (7)0.0068 (7)
O10.0403 (9)0.0501 (10)0.0507 (9)0.0103 (8)0.0055 (7)0.0130 (8)
Cl10.0462 (3)0.0451 (3)0.0514 (3)0.0079 (3)0.0075 (3)0.0077 (2)
Geometric parameters (Å, º) top
C1—O11.383 (2)C11—C121.531 (3)
C1—C21.388 (3)C11—H110.9800
C1—C81.392 (3)C12—C141.522 (4)
C2—C41.394 (3)C12—C131.522 (3)
C2—C31.501 (3)C12—H120.9800
C3—H3A0.9600C13—H13A0.9600
C3—H3B0.9600C13—H13B0.9600
C3—H3C0.9600C13—H13C0.9600
C4—C51.384 (3)C14—H14A0.9600
C4—H40.9300C14—H14B0.9600
C5—C71.379 (3)C14—H14C0.9600
C5—C61.511 (3)C15—C201.381 (3)
C6—H6A0.9600C15—C161.387 (3)
C6—H6B0.9600C16—C171.390 (4)
C6—H6C0.9600C16—H160.9300
C7—C81.385 (3)C17—C181.368 (4)
C7—H70.9300C17—H170.9300
C8—C91.510 (3)C18—C191.377 (4)
C9—N11.508 (3)C18—H180.9300
C9—C101.515 (3)C19—C201.376 (4)
C9—H90.9800C19—H190.9300
C10—H10A0.9600C20—H200.9300
C10—H10B0.9600N1—H1A0.9000
C10—H10C0.9600N1—H1B0.9000
C11—C151.509 (3)O1—H10.8200
C11—N11.513 (3)
O1—C1—C2122.77 (19)N1—C11—H11107.9
O1—C1—C8116.56 (18)C12—C11—H11107.9
C2—C1—C8120.67 (19)C14—C12—C13110.3 (2)
C1—C2—C4118.1 (2)C14—C12—C11109.8 (2)
C1—C2—C3121.3 (2)C13—C12—C11112.1 (2)
C4—C2—C3120.6 (2)C14—C12—H12108.2
C2—C3—H3A109.5C13—C12—H12108.2
C2—C3—H3B109.5C11—C12—H12108.2
H3A—C3—H3B109.5C12—C13—H13A109.5
C2—C3—H3C109.5C12—C13—H13B109.5
H3A—C3—H3C109.5H13A—C13—H13B109.5
H3B—C3—H3C109.5C12—C13—H13C109.5
C5—C4—C2122.6 (2)H13A—C13—H13C109.5
C5—C4—H4118.7H13B—C13—H13C109.5
C2—C4—H4118.7C12—C14—H14A109.5
C7—C5—C4117.4 (2)C12—C14—H14B109.5
C7—C5—C6120.5 (2)H14A—C14—H14B109.5
C4—C5—C6122.0 (2)C12—C14—H14C109.5
C5—C6—H6A109.5H14A—C14—H14C109.5
C5—C6—H6B109.5H14B—C14—H14C109.5
H6A—C6—H6B109.5C20—C15—C16119.1 (2)
C5—C6—H6C109.5C20—C15—C11120.29 (19)
H6A—C6—H6C109.5C16—C15—C11120.64 (19)
H6B—C6—H6C109.5C15—C16—C17119.8 (2)
C5—C7—C8122.2 (2)C15—C16—H16120.1
C5—C7—H7118.9C17—C16—H16120.1
C8—C7—H7118.9C18—C17—C16120.5 (2)
C7—C8—C1118.9 (2)C18—C17—H17119.8
C7—C8—C9119.5 (2)C16—C17—H17119.8
C1—C8—C9121.57 (19)C17—C18—C19119.8 (2)
N1—C9—C8110.92 (17)C17—C18—H18120.1
N1—C9—C10108.65 (19)C19—C18—H18120.1
C8—C9—C10113.59 (18)C20—C19—C18120.2 (2)
N1—C9—H9107.8C20—C19—H19119.9
C8—C9—H9107.8C18—C19—H19119.9
C10—C9—H9107.8C19—C20—C15120.7 (2)
C9—C10—H10A109.5C19—C20—H20119.7
C9—C10—H10B109.5C15—C20—H20119.7
H10A—C10—H10B109.5C9—N1—C11115.49 (16)
C9—C10—H10C109.5C9—N1—H1A108.4
H10A—C10—H10C109.5C11—N1—H1A108.4
H10B—C10—H10C109.5C9—N1—H1B108.4
C15—C11—N1110.26 (16)C11—N1—H1B108.4
C15—C11—C12113.52 (17)H1A—N1—H1B107.5
N1—C11—C12109.25 (16)C1—O1—H1109.5
C15—C11—H11107.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.902.162.792 (2)127
N1—H1B···Cl10.902.223.1122 (18)171
O1—H1···Cl1i0.822.393.1371 (17)152
Symmetry code: (i) x+2, y+1/2, z+3/2.
 

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