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The title compound, C16H19ClNO2+·Cl·C4H8O2, was synthesised and its mol­ecular structure determined. The absolute configuration of a new stereogenic centre is determined to be S. N+—H...Cl and O—H...Cl inter­actions connect structural components, generating a hydrogen-bonded spiral along the twofold screw axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016308/kp2016sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016308/kp2016Isup2.hkl
Contains datablock I

CCDC reference: 610826

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.067
  • wR factor = 0.178
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.08 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C18 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT731_ALERT_1_C Bond Calc 1.49(2), Rep 1.486(9) ...... 2.22 su-Rat C19 -C20 1.555 1.555
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 25.03 From the CIF: _reflns_number_total 3294 Count of symmetry unique reflns 2099 Completeness (_total/calc) 156.93% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1195 Fraction of Friedel pairs measured 0.569 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 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 1 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: 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 (Bruker, 1998); software used to prepare material for publication: SHELXTL.

N-[(S)-1-(5-Chloro-2-hydroxyphenyl)ethyl]-N-[(R)-2-hydroxy-1- phenylethyl]aminium chloride ethyl acetate solvate top
Crystal data top
C16H19ClNO2+·Cl·C4H8O2F(000) = 440
Mr = 416.33Dx = 1.258 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.912 (3) ÅCell parameters from 2280 reflections
b = 7.7221 (18) Åθ = 2.7–23.7°
c = 12.312 (3) ŵ = 0.32 mm1
β = 103.993 (3)°T = 298 K
V = 1098.9 (4) Å3Block, colourless
Z = 20.35 × 0.21 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3294 independent reflections
Radiation source: fine-focus sealed tube3077 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1412
Tmin = 0.897, Tmax = 0.945k = 59
4637 measured reflectionsl = 1414
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)] = 0.067H-atom parameters constrained
wR(F2) = 0.178 w = 1/[σ2(Fo2) + (0.1181P)2 + 0.0672P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
3294 reflectionsΔρmax = 0.47 e Å3
249 parametersΔρmin = 0.23 e Å3
162 restraintsAbsolute structure: Flack (1983), 1195 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (11)
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
C10.6610 (4)0.0959 (6)0.1409 (3)0.0513 (11)
H1C0.73520.05860.14080.062*
C20.5941 (5)0.1785 (7)0.0487 (4)0.0663 (14)
C30.4853 (6)0.2350 (8)0.0464 (4)0.0722 (16)
H30.44170.29140.01650.087*
C40.4404 (5)0.2079 (8)0.1381 (4)0.0681 (14)
H40.36610.24570.13720.082*
C50.5052 (4)0.1253 (6)0.2302 (3)0.0482 (10)
C60.6170 (4)0.0687 (5)0.2338 (3)0.0412 (9)
C70.6956 (3)0.0040 (5)0.3387 (3)0.0376 (8)
H70.76380.05410.31940.045*
C80.7359 (4)0.1351 (6)0.4279 (4)0.0495 (11)
H8A0.78640.08410.49270.074*
H8B0.77660.22410.39860.074*
H8C0.67000.18450.44830.074*
C90.6258 (3)0.3153 (5)0.3292 (3)0.0406 (9)
H90.58390.29680.25120.049*
C100.5528 (4)0.4321 (6)0.3839 (5)0.0541 (11)
H10A0.59380.45680.46040.065*
H10B0.53790.54080.34350.065*
C110.7411 (4)0.3918 (5)0.3297 (4)0.0432 (9)
C120.8310 (4)0.3977 (6)0.4243 (4)0.0542 (11)
H120.82240.34720.49040.065*
C130.9331 (4)0.4778 (7)0.4214 (6)0.0721 (15)
H130.99320.48090.48570.086*
C140.9475 (5)0.5524 (9)0.3264 (8)0.093 (2)
H141.01730.60580.32560.111*
C150.8588 (6)0.5495 (9)0.2305 (6)0.0860 (19)
H150.86840.60140.16510.103*
C160.7567 (5)0.4694 (7)0.2323 (5)0.0620 (13)
H160.69700.46680.16770.074*
C171.1496 (8)0.1596 (17)0.2869 (6)0.136 (3)
H17A1.14770.18610.36260.204*
H17B1.17940.25730.25450.204*
H17C1.19870.06110.28630.204*
C181.0315 (10)0.1200 (18)0.2212 (8)0.141 (3)
C190.9137 (11)0.126 (3)0.0510 (11)0.204 (5)
H19A0.85360.16980.08460.245*
H19B0.90530.00170.04150.245*
C200.9118 (10)0.214 (4)0.0567 (11)0.255 (9)
H20A0.86390.31550.06360.383*
H20B0.88130.13680.11760.383*
H20C0.98910.24740.05830.383*
N10.6353 (2)0.1448 (4)0.3886 (2)0.0362 (7)
H1A0.56360.10800.38880.043*
H1B0.67390.16090.46040.043*
O10.4650 (3)0.0948 (5)0.3240 (3)0.0610 (9)
H10.40820.15560.32230.091*
O20.4481 (3)0.3491 (5)0.3827 (4)0.0719 (11)
H20.39620.42110.37390.108*
O30.9439 (8)0.0464 (14)0.2347 (9)0.196 (4)
O41.0259 (6)0.1716 (15)0.1154 (4)0.165 (3)
Cl10.6497 (2)0.2121 (3)0.06806 (13)0.1158 (8)
Cl20.27524 (8)0.66531 (15)0.34878 (8)0.0489 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.068 (3)0.047 (3)0.043 (2)0.001 (2)0.0192 (19)0.0010 (18)
C20.101 (4)0.054 (3)0.044 (2)0.003 (3)0.018 (2)0.004 (2)
C30.099 (4)0.062 (3)0.047 (2)0.019 (3)0.000 (3)0.003 (2)
C40.069 (3)0.069 (4)0.056 (3)0.025 (3)0.006 (2)0.005 (3)
C50.053 (2)0.040 (2)0.049 (2)0.0105 (19)0.0091 (18)0.0026 (18)
C60.046 (2)0.028 (2)0.050 (2)0.0031 (16)0.0114 (17)0.0033 (16)
C70.0352 (19)0.030 (2)0.050 (2)0.0019 (16)0.0143 (16)0.0018 (16)
C80.053 (2)0.036 (2)0.055 (2)0.0091 (19)0.0053 (19)0.0069 (19)
C90.043 (2)0.033 (2)0.0457 (19)0.0000 (17)0.0097 (16)0.0022 (17)
C100.048 (2)0.035 (2)0.082 (3)0.0033 (18)0.021 (2)0.004 (2)
C110.047 (2)0.027 (2)0.061 (2)0.0028 (17)0.0234 (19)0.0003 (18)
C120.042 (2)0.044 (3)0.074 (3)0.0014 (19)0.010 (2)0.002 (2)
C130.039 (2)0.055 (3)0.121 (4)0.001 (2)0.017 (3)0.000 (3)
C140.058 (3)0.062 (4)0.176 (7)0.006 (3)0.062 (4)0.001 (4)
C150.093 (4)0.065 (4)0.123 (5)0.008 (3)0.073 (4)0.007 (4)
C160.071 (3)0.049 (3)0.074 (3)0.000 (2)0.033 (3)0.006 (2)
C170.166 (7)0.136 (8)0.085 (4)0.020 (8)0.010 (5)0.014 (6)
C180.146 (6)0.167 (10)0.120 (5)0.033 (7)0.051 (5)0.005 (6)
C190.149 (8)0.299 (15)0.168 (7)0.081 (10)0.045 (6)0.045 (10)
C200.122 (8)0.46 (3)0.148 (8)0.016 (14)0.028 (7)0.022 (13)
N10.0363 (14)0.0285 (17)0.0447 (15)0.0014 (13)0.0115 (12)0.0053 (14)
O10.0541 (19)0.068 (2)0.0643 (18)0.0261 (17)0.0209 (15)0.0132 (17)
O20.0456 (18)0.053 (2)0.125 (3)0.0058 (15)0.036 (2)0.007 (2)
O30.164 (6)0.182 (8)0.279 (10)0.033 (6)0.128 (7)0.020 (8)
O40.143 (5)0.255 (9)0.087 (3)0.054 (6)0.009 (3)0.026 (5)
Cl10.173 (2)0.1265 (17)0.0612 (8)0.0197 (15)0.0533 (10)0.0294 (10)
Cl20.0398 (5)0.0544 (7)0.0514 (5)0.0072 (5)0.0090 (4)0.0064 (5)
Geometric parameters (Å, º) top
C1—C21.376 (7)C12—C131.372 (7)
C1—C61.384 (6)C12—H120.9300
C1—H1C0.9300C13—C141.351 (10)
C2—C31.361 (8)C13—H130.9300
C2—Cl11.742 (5)C14—C151.382 (10)
C3—C41.377 (8)C14—H140.9300
C3—H30.9300C15—C161.369 (8)
C4—C51.366 (6)C15—H150.9300
C4—H40.9300C16—H160.9300
C5—O11.373 (5)C17—C181.476 (13)
C5—C61.392 (6)C17—H17A0.9600
C6—C71.509 (5)C17—H17B0.9600
C7—N11.513 (5)C17—H17C0.9600
C7—C81.527 (6)C18—O31.235 (11)
C7—H70.9800C18—O41.348 (11)
C8—H8A0.9600C19—O41.423 (13)
C8—H8B0.9600C19—C201.486 (9)
C8—H8C0.9600C19—H19A0.9700
C9—C111.494 (6)C19—H19B0.9700
C9—N11.498 (5)C20—H20A0.9600
C9—C101.518 (6)C20—H20B0.9600
C9—H90.9800C20—H20C0.9600
C10—O21.398 (6)N1—H1A0.9000
C10—H10A0.9700N1—H1B0.9000
C10—H10B0.9700O1—H10.8200
C11—C121.380 (7)O2—H20.8200
C11—C161.392 (7)
C2—C1—C6119.5 (5)C13—C12—C11120.3 (5)
C2—C1—H1C120.3C13—C12—H12119.9
C6—C1—H1C120.3C11—C12—H12119.9
C3—C2—C1121.7 (5)C14—C13—C12120.9 (6)
C3—C2—Cl1119.0 (4)C14—C13—H13119.5
C1—C2—Cl1119.3 (4)C12—C13—H13119.5
C2—C3—C4119.4 (5)C13—C14—C15120.1 (5)
C2—C3—H3120.3C13—C14—H14119.9
C4—C3—H3120.3C15—C14—H14119.9
C5—C4—C3119.9 (5)C16—C15—C14119.5 (6)
C5—C4—H4120.0C16—C15—H15120.3
C3—C4—H4120.0C14—C15—H15120.3
C4—C5—O1122.5 (4)C15—C16—C11120.8 (6)
C4—C5—C6121.1 (4)C15—C16—H16119.6
O1—C5—C6116.4 (4)C11—C16—H16119.6
C1—C6—C5118.5 (4)C18—C17—H17A109.5
C1—C6—C7118.9 (4)C18—C17—H17B109.5
C5—C6—C7122.3 (4)H17A—C17—H17B109.5
C6—C7—N1110.9 (3)C18—C17—H17C109.5
C6—C7—C8112.1 (3)H17A—C17—H17C109.5
N1—C7—C8108.1 (3)H17B—C17—H17C109.5
C6—C7—H7108.5O3—C18—O4114.8 (11)
N1—C7—H7108.5O3—C18—C17138.3 (11)
C8—C7—H7108.5O4—C18—C17106.7 (8)
C7—C8—H8A109.5O4—C19—C20101.1 (9)
C7—C8—H8B109.5O4—C19—H19A111.5
H8A—C8—H8B109.5C20—C19—H19A111.5
C7—C8—H8C109.5O4—C19—H19B111.5
H8A—C8—H8C109.5C20—C19—H19B111.5
H8B—C8—H8C109.5H19A—C19—H19B109.4
C11—C9—N1112.6 (3)C19—C20—H20A109.5
C11—C9—C10112.9 (3)C19—C20—H20B109.5
N1—C9—C10106.8 (3)H20A—C20—H20B109.5
C11—C9—H9108.1C19—C20—H20C109.5
N1—C9—H9108.1H20A—C20—H20C109.5
C10—C9—H9108.1H20B—C20—H20C109.5
O2—C10—C9109.1 (4)C9—N1—C7114.9 (3)
O2—C10—H10A109.9C9—N1—H1A108.5
C9—C10—H10A109.9C7—N1—H1A108.5
O2—C10—H10B109.9C9—N1—H1B108.5
C9—C10—H10B109.9C7—N1—H1B108.5
H10A—C10—H10B108.3H1A—N1—H1B107.5
C12—C11—C16118.4 (4)C5—O1—H1109.5
C12—C11—C9122.8 (4)C10—O2—H2109.5
C16—C11—C9118.7 (4)C18—O4—C19106.6 (9)
C6—C1—C2—C30.2 (8)N1—C9—C11—C1245.5 (5)
C6—C1—C2—Cl1179.9 (4)C10—C9—C11—C1275.5 (5)
C1—C2—C3—C40.5 (9)N1—C9—C11—C16138.3 (4)
Cl1—C2—C3—C4179.5 (5)C10—C9—C11—C16100.7 (5)
C2—C3—C4—C50.2 (9)C16—C11—C12—C130.3 (7)
C3—C4—C5—O1179.9 (5)C9—C11—C12—C13176.5 (4)
C3—C4—C5—C60.5 (8)C11—C12—C13—C140.1 (8)
C2—C1—C6—C50.5 (7)C12—C13—C14—C150.3 (10)
C2—C1—C6—C7173.3 (4)C13—C14—C15—C160.5 (10)
C4—C5—C6—C10.8 (7)C14—C15—C16—C110.3 (9)
O1—C5—C6—C1179.7 (4)C12—C11—C16—C150.1 (7)
C4—C5—C6—C7172.7 (5)C9—C11—C16—C15176.4 (5)
O1—C5—C6—C76.8 (6)C11—C9—N1—C761.2 (4)
C1—C6—C7—N1135.6 (4)C10—C9—N1—C7174.3 (3)
C5—C6—C7—N151.0 (5)C6—C7—N1—C976.3 (4)
C1—C6—C7—C8103.5 (4)C8—C7—N1—C9160.4 (3)
C5—C6—C7—C870.0 (5)O3—C18—O4—C191.6 (17)
C11—C9—C10—O2178.4 (4)C17—C18—O4—C19177.4 (12)
N1—C9—C10—O254.1 (5)C20—C19—O4—C18171.1 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···Cl2i0.902.283.154 (3)163
O1—H1···Cl2ii0.822.192.995 (3)169
O2—H2···Cl20.822.353.156 (4)169
N1—H1A···O10.902.002.718 (4)135
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x, y1, z.
 

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