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The title compound, C20H28NO+·Cl, was synthesized by a condensation reaction. The absolute configuration of the new stereogenic centre (the C atom between the N atom and the phenol ring) was determined as R. The crystal structure is stabilized through N—H...Cl and O—H...Cl hydrogen bonds and intra­molecular N—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020848/ob2018sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020848/ob2018IIsup2.hkl
Contains datablock II

CCDC reference: 613783

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.039
  • wR factor = 0.102
  • Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.00 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.73 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C10 PLAT414_ALERT_2_C Short Intra D-H..H-X H1B .. H13A .. 1.95 Ang.
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 25.02 From the CIF: _reflns_number_total 3434 Count of symmetry unique reflns 1991 Completeness (_total/calc) 172.48% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1443 Fraction of Friedel pairs measured 0.725 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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, 1997); software used to prepare material for publication: SHELXTL.

(+)-N-[(R)-1-(2-Hydroxy-5-methylphenyl)propyl]-N-[(R)-2-methyl-1- phenylpropyl]ammonium chloride top
Crystal data top
C20H28NO+·ClDx = 1.131 Mg m3
Mr = 333.88Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 3718 reflections
a = 8.725 (2) Åθ = 2.4–25.3°
b = 11.641 (3) ŵ = 0.20 mm1
c = 19.313 (5) ÅT = 298 K
V = 1961.7 (9) Å3Block, colourless
Z = 40.33 × 0.21 × 0.13 mm
F(000) = 720
Data collection top
Bruker SMART CCD area-detector
diffractometer
3434 independent reflections
Radiation source: fine-focus sealed tube2439 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 910
Tmin = 0.937, Tmax = 0.975k = 1313
10299 measured reflectionsl = 2220
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)] = 0.039H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.0453P)2 + 0.4485P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1975 reflectionsΔρmax = 0.20 e Å3
208 parametersΔρmin = 0.16 e Å3
0 restraintsAbsolute structure: Flack (1983), with 1469 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (9)
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*/Ueq
Cl10.08193 (11)0.39063 (9)0.85876 (5)0.0633 (3)
N10.7928 (3)0.5364 (2)0.81730 (14)0.0396 (6)
H1A0.86100.48570.83430.048*
H1B0.84490.58820.79200.048*
O10.7910 (3)0.6689 (2)0.70025 (13)0.0550 (7)
H10.81310.72440.67620.082*
C10.6828 (4)0.4733 (3)0.77035 (17)0.0379 (8)
H1C0.61920.42320.79930.045*
C20.7740 (4)0.3970 (3)0.72055 (17)0.0493 (9)
H2A0.84050.44490.69250.059*
H2B0.83820.34520.74710.059*
C30.6704 (5)0.3275 (4)0.6735 (2)0.0674 (12)
H3A0.73180.28110.64320.101*
H3B0.60800.37850.64650.101*
H3C0.60580.27890.70110.101*
C40.5784 (4)0.5557 (3)0.73363 (16)0.0373 (7)
C50.6363 (4)0.6483 (3)0.69579 (18)0.0415 (8)
C60.5393 (4)0.7150 (3)0.65665 (18)0.0477 (9)
H60.57800.77650.63130.057*
C70.3844 (4)0.6907 (3)0.65492 (19)0.0502 (10)
H70.32060.73540.62730.060*
C80.3217 (4)0.6018 (3)0.69301 (19)0.0473 (9)
C90.4212 (4)0.5348 (3)0.73203 (17)0.0415 (8)
H90.38180.47420.75780.050*
C100.1522 (4)0.5787 (4)0.6945 (2)0.0675 (12)
H10A0.10070.63230.66480.101*
H10B0.11490.58720.74100.101*
H10C0.13300.50190.67870.101*
C110.7169 (4)0.5976 (3)0.87708 (16)0.0415 (8)
H110.63500.64530.85770.050*
C120.8309 (5)0.6788 (4)0.9128 (2)0.0605 (11)
H120.91160.63250.93440.073*
C130.9045 (8)0.7626 (5)0.8638 (3)0.112 (2)
H13A0.95600.72130.82760.168*
H13B0.97730.80890.88850.168*
H13C0.82720.81120.84390.168*
C140.7458 (8)0.7445 (5)0.9698 (3)0.111 (2)
H14A0.69840.69091.00090.166*
H14B0.66850.79240.94930.166*
H14C0.81700.79150.99500.166*
C150.6431 (4)0.5133 (3)0.92531 (18)0.0426 (8)
C160.4852 (4)0.5110 (3)0.9331 (2)0.0525 (10)
H160.42500.56040.90670.063*
C170.4152 (6)0.4367 (4)0.9792 (2)0.0667 (12)
H170.30920.43690.98430.080*
C180.5041 (6)0.3625 (4)1.0172 (2)0.0750 (14)
H180.45770.31171.04800.090*
C190.6604 (6)0.3627 (4)1.0104 (2)0.0732 (14)
H190.71950.31201.03630.088*
C200.7304 (5)0.4381 (3)0.96486 (19)0.0563 (11)
H200.83660.43850.96070.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0559 (5)0.0658 (6)0.0682 (6)0.0229 (5)0.0059 (5)0.0010 (5)
N10.0339 (14)0.0382 (15)0.0467 (16)0.0038 (13)0.0001 (13)0.0036 (13)
O10.0377 (13)0.0633 (17)0.0639 (16)0.0063 (13)0.0017 (12)0.0218 (14)
C10.0350 (17)0.0383 (18)0.0403 (18)0.0006 (16)0.0045 (15)0.0035 (16)
C20.049 (2)0.049 (2)0.050 (2)0.008 (2)0.0019 (17)0.0030 (18)
C30.080 (3)0.067 (3)0.055 (2)0.006 (2)0.004 (2)0.016 (2)
C40.0329 (16)0.0376 (18)0.0414 (18)0.0038 (16)0.0011 (16)0.0017 (15)
C50.0336 (17)0.046 (2)0.0452 (19)0.0011 (15)0.0006 (15)0.0064 (18)
C60.051 (2)0.044 (2)0.047 (2)0.0021 (17)0.0004 (17)0.0130 (17)
C70.048 (2)0.051 (2)0.052 (2)0.0112 (18)0.0086 (18)0.0055 (19)
C80.0366 (18)0.054 (2)0.051 (2)0.0044 (18)0.0064 (17)0.001 (2)
C90.0392 (17)0.0412 (19)0.0442 (18)0.0008 (18)0.0006 (17)0.0034 (16)
C100.043 (2)0.073 (3)0.087 (3)0.001 (2)0.012 (2)0.010 (3)
C110.0420 (18)0.0378 (18)0.0449 (19)0.0019 (17)0.0030 (15)0.0000 (16)
C120.066 (3)0.053 (2)0.062 (3)0.014 (2)0.004 (2)0.006 (2)
C130.136 (5)0.098 (4)0.102 (4)0.072 (4)0.008 (4)0.003 (3)
C140.149 (6)0.092 (4)0.091 (4)0.032 (4)0.015 (4)0.048 (3)
C150.052 (2)0.038 (2)0.0374 (19)0.0019 (17)0.0012 (16)0.0033 (16)
C160.051 (2)0.056 (2)0.051 (2)0.0036 (19)0.0056 (18)0.010 (2)
C170.068 (3)0.071 (3)0.062 (3)0.013 (3)0.019 (2)0.014 (2)
C180.105 (4)0.065 (3)0.055 (3)0.018 (3)0.025 (3)0.000 (2)
C190.109 (4)0.062 (3)0.048 (2)0.014 (3)0.007 (3)0.010 (2)
C200.062 (2)0.060 (3)0.047 (2)0.008 (2)0.000 (2)0.006 (2)
Geometric parameters (Å, º) top
N1—C111.510 (4)C10—H10B0.9600
N1—C11.511 (4)C10—H10C0.9600
N1—H1A0.9000C11—C151.498 (5)
N1—H1B0.9000C11—C121.537 (5)
O1—C51.373 (4)C11—H110.9800
O1—H10.8200C12—C131.504 (6)
C1—C41.500 (4)C12—C141.532 (6)
C1—C21.532 (5)C12—H120.9800
C1—H1C0.9800C13—H13A0.9600
C2—C31.515 (5)C13—H13B0.9600
C2—H2A0.9700C13—H13C0.9600
C2—H2B0.9700C14—H14A0.9600
C3—H3A0.9600C14—H14B0.9600
C3—H3B0.9600C14—H14C0.9600
C3—H3C0.9600C15—C161.387 (5)
C4—C91.393 (5)C15—C201.389 (5)
C4—C51.397 (5)C16—C171.384 (5)
C5—C61.375 (5)C16—H160.9300
C6—C71.381 (5)C17—C181.374 (6)
C6—H60.9300C17—H170.9300
C7—C81.382 (5)C18—C191.370 (6)
C7—H70.9300C18—H180.9300
C8—C91.390 (5)C19—C201.385 (6)
C8—C101.503 (5)C19—H190.9300
C9—H90.9300C20—H200.9300
C10—H10A0.9600
C11—N1—C1114.2 (2)C8—C10—H10C109.5
C11—N1—H1A108.7H10A—C10—H10C109.5
C1—N1—H1A108.7H10B—C10—H10C109.5
C11—N1—H1B108.7C15—C11—N1110.8 (3)
C1—N1—H1B108.7C15—C11—C12113.7 (3)
H1A—N1—H1B107.6N1—C11—C12110.5 (3)
C5—O1—H1109.5C15—C11—H11107.2
C4—C1—N1111.0 (3)N1—C11—H11107.2
C4—C1—C2112.9 (3)C12—C11—H11107.2
N1—C1—C2109.2 (2)C13—C12—C14109.6 (4)
C4—C1—H1C107.9C13—C12—C11113.1 (3)
N1—C1—H1C107.9C14—C12—C11108.4 (4)
C2—C1—H1C107.9C13—C12—H12108.5
C3—C2—C1112.1 (3)C14—C12—H12108.5
C3—C2—H2A109.2C11—C12—H12108.5
C1—C2—H2A109.2C12—C13—H13A109.5
C3—C2—H2B109.2C12—C13—H13B109.5
C1—C2—H2B109.2H13A—C13—H13B109.5
H2A—C2—H2B107.9C12—C13—H13C109.5
C2—C3—H3A109.5H13A—C13—H13C109.5
C2—C3—H3B109.5H13B—C13—H13C109.5
H3A—C3—H3B109.5C12—C14—H14A109.5
C2—C3—H3C109.5C12—C14—H14B109.5
H3A—C3—H3C109.5H14A—C14—H14B109.5
H3B—C3—H3C109.5C12—C14—H14C109.5
C9—C4—C5118.6 (3)H14A—C14—H14C109.5
C9—C4—C1119.8 (3)H14B—C14—H14C109.5
C5—C4—C1121.4 (3)C16—C15—C20118.3 (4)
O1—C5—C6122.8 (3)C16—C15—C11120.5 (4)
O1—C5—C4117.2 (3)C20—C15—C11121.3 (3)
C6—C5—C4120.1 (3)C17—C16—C15121.3 (4)
C5—C6—C7120.0 (3)C17—C16—H16119.3
C5—C6—H6120.0C15—C16—H16119.3
C7—C6—H6120.0C18—C17—C16119.2 (4)
C6—C7—C8121.9 (3)C18—C17—H17120.4
C6—C7—H7119.1C16—C17—H17120.4
C8—C7—H7119.1C19—C18—C17120.7 (5)
C7—C8—C9117.4 (3)C19—C18—H18119.7
C7—C8—C10122.3 (3)C17—C18—H18119.7
C9—C8—C10120.3 (4)C18—C19—C20120.1 (5)
C8—C9—C4122.0 (3)C18—C19—H19120.0
C8—C9—H9119.0C20—C19—H19120.0
C4—C9—H9119.0C19—C20—C15120.5 (4)
C8—C10—H10A109.5C19—C20—H20119.8
C8—C10—H10B109.5C15—C20—H20119.8
H10A—C10—H10B109.5
C11—N1—C1—C465.5 (3)C1—C4—C9—C8173.4 (3)
C11—N1—C1—C2169.4 (3)C1—N1—C11—C1564.8 (3)
C4—C1—C2—C358.2 (4)C1—N1—C11—C12168.3 (3)
N1—C1—C2—C3177.8 (3)C15—C11—C12—C13179.8 (4)
N1—C1—C4—C9132.3 (3)N1—C11—C12—C1354.5 (5)
C2—C1—C4—C9104.7 (4)C15—C11—C12—C1458.4 (5)
N1—C1—C4—C553.1 (4)N1—C11—C12—C14176.3 (4)
C2—C1—C4—C569.8 (4)N1—C11—C15—C16114.1 (4)
C9—C4—C5—O1177.9 (3)C12—C11—C15—C16120.7 (4)
C1—C4—C5—O17.4 (5)N1—C11—C15—C2067.8 (4)
C9—C4—C5—C61.6 (5)C12—C11—C15—C2057.3 (4)
C1—C4—C5—C6173.0 (3)C20—C15—C16—C170.4 (6)
O1—C5—C6—C7179.3 (4)C11—C15—C16—C17177.6 (3)
C4—C5—C6—C70.3 (6)C15—C16—C17—C181.0 (6)
C5—C6—C7—C81.5 (6)C16—C17—C18—C190.7 (7)
C6—C7—C8—C91.9 (5)C17—C18—C19—C200.1 (7)
C6—C7—C8—C10176.6 (4)C18—C19—C20—C150.7 (7)
C7—C8—C9—C40.4 (5)C16—C15—C20—C190.4 (6)
C10—C8—C9—C4178.1 (4)C11—C15—C20—C19178.5 (3)
C5—C4—C9—C81.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1i0.902.273.144 (3)163
N1—H1B···O10.902.062.737 (4)131
O1—H1···Cl1ii0.822.243.032 (3)161
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1/2, z+3/2.
 

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