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The title compound, C12H15Cl2FNO2+·Cl, has been synthesized from 2-(2,4-dichloro-5-fluoro­phen­yl)-4-(2-hydroxy­ethyl)morpholin-2-ol via reduction by formic acid and acidification by hydrogen chloride. The morpholine unit adopts an almost ideal chair conformation. The crystal structure is consolidated by N—H...Cl and O—H...Cl inter­molecular hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045272/xu2149sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045272/xu2149Isup2.hkl
Contains datablock I

CCDC reference: 630515

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.035
  • wR factor = 0.091
  • Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; 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.

2-(2,4-dichloro-5-fluorophenyl)-4-(2-hydroxyethyl)morpholin-4-ium chloride top
Crystal data top
C12H15Cl2FNO2+·ClF(000) = 680
Mr = 330.60Dx = 1.557 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4650 reflections
a = 14.1063 (8) Åθ = 2.9–26.9°
b = 7.2927 (4) ŵ = 0.66 mm1
c = 13.8748 (8) ÅT = 294 K
β = 98.834 (1)°Block, colorless
V = 1410.41 (14) Å30.48 × 0.45 × 0.40 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD
diffractometer
3064 independent reflections
Radiation source: fine-focus sealed tube2288 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 27.1°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1617
Tmin = 0.735, Tmax = 0.771k = 99
11388 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0365P)2 + 0.6923P]
where P = (Fo2 + 2Fc2)/3
3064 reflections(Δ/σ)max = 0.001
173 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.35 e Å3
Special details top

Experimental. Spectroscopic analysis: 1H-NMR (CD3SOCD3, 400 MHz) (p.p.m.): 3.17–3.26 (m, 4H, morpholine ring 5-H, NCH2), 3.42–3.64 (m, 2H, morpholine ring 3-H), 3.79–4.01 (m, 4H, CH2O, morpholine ring 6-H), 5.35 (dd, J= 9.8 Hz, J= 3.8 Hz, 1H, morpholine ring 2-H), 6.73(s, 1H, OH), 7.59 (d, J= 10 Hz, 1H, benzene ring 6-H), 7.89 (d, J= 6.8 Hz, 1H, benzene ring 3-H), 10.64(br s, 1H, N+H). M.p. 462–464 K. The crystals suitable for X-ray structure determination were obtained by slow evaporation of an ethanol solution at room temperature.

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
C10.80231 (13)0.8701 (3)0.58018 (14)0.0351 (4)
H10.77470.92070.51660.042*
C20.74569 (14)0.7015 (3)0.60124 (14)0.0345 (4)
H2A0.74720.61170.54990.041*
H2B0.77510.64690.66230.041*
C30.64082 (14)0.9030 (3)0.67910 (13)0.0363 (4)
H3A0.66460.85940.74440.044*
H3B0.57520.94370.67760.044*
C40.70137 (14)1.0603 (3)0.65452 (15)0.0413 (5)
H4A0.67481.10870.59100.050*
H4B0.70001.15720.70210.050*
C50.58902 (14)0.5839 (3)0.63134 (14)0.0383 (5)
H5A0.62020.53280.69270.046*
H5B0.59130.49210.58110.046*
C60.48533 (15)0.6240 (3)0.63917 (15)0.0428 (5)
H6A0.45300.51040.65060.051*
H6B0.48260.70410.69450.051*
C70.90687 (14)0.8267 (3)0.57974 (14)0.0362 (4)
C80.94133 (14)0.7640 (3)0.49689 (15)0.0380 (5)
C91.03812 (15)0.7322 (3)0.49693 (16)0.0430 (5)
H91.05960.69150.44060.052*
C101.10220 (14)0.7610 (3)0.58061 (17)0.0424 (5)
C111.06879 (15)0.8221 (3)0.66266 (15)0.0430 (5)
C120.97307 (15)0.8548 (3)0.66340 (15)0.0425 (5)
H120.95250.89600.72010.051*
Cl10.86278 (4)0.72887 (9)0.38958 (4)0.05085 (17)
Cl21.22350 (4)0.72822 (9)0.58072 (5)0.05733 (18)
Cl30.59218 (4)0.88210 (8)0.39437 (3)0.04703 (16)
F11.13133 (9)0.8565 (2)0.74429 (10)0.0613 (4)
N10.64350 (11)0.7502 (2)0.60754 (10)0.0300 (3)
H1A0.61590.79150.54790.036*
O10.79812 (10)1.0050 (2)0.65362 (10)0.0424 (4)
O20.43736 (11)0.7079 (2)0.55396 (11)0.0493 (4)
H20.43190.81800.56360.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0325 (10)0.0405 (11)0.0323 (9)0.0035 (9)0.0050 (8)0.0002 (8)
C20.0334 (10)0.0388 (11)0.0318 (9)0.0060 (8)0.0062 (8)0.0004 (8)
C30.0332 (10)0.0449 (12)0.0308 (9)0.0038 (9)0.0046 (8)0.0088 (8)
C40.0371 (11)0.0402 (12)0.0457 (11)0.0044 (9)0.0031 (9)0.0095 (9)
C50.0418 (11)0.0376 (11)0.0350 (10)0.0039 (9)0.0045 (8)0.0022 (9)
C60.0408 (12)0.0485 (13)0.0398 (11)0.0100 (10)0.0091 (9)0.0006 (9)
C70.0335 (11)0.0387 (11)0.0367 (10)0.0011 (8)0.0063 (8)0.0057 (8)
C80.0355 (11)0.0398 (12)0.0390 (10)0.0019 (9)0.0067 (8)0.0024 (9)
C90.0400 (12)0.0432 (12)0.0490 (12)0.0007 (10)0.0171 (10)0.0015 (10)
C100.0298 (10)0.0399 (12)0.0580 (13)0.0011 (9)0.0085 (9)0.0137 (10)
C110.0355 (11)0.0475 (13)0.0436 (11)0.0003 (9)0.0014 (9)0.0114 (10)
C120.0390 (12)0.0528 (14)0.0357 (10)0.0036 (10)0.0058 (9)0.0060 (9)
Cl10.0464 (3)0.0653 (4)0.0403 (3)0.0030 (3)0.0049 (2)0.0074 (3)
Cl20.0309 (3)0.0645 (4)0.0780 (4)0.0021 (3)0.0128 (3)0.0158 (3)
Cl30.0558 (3)0.0527 (3)0.0302 (2)0.0041 (3)0.0011 (2)0.0015 (2)
F10.0425 (7)0.0822 (10)0.0538 (8)0.0026 (7)0.0095 (6)0.0088 (7)
N10.0294 (8)0.0358 (9)0.0243 (7)0.0025 (7)0.0028 (6)0.0004 (6)
O10.0318 (7)0.0442 (9)0.0506 (8)0.0007 (6)0.0041 (6)0.0107 (7)
O20.0447 (9)0.0566 (10)0.0437 (8)0.0010 (8)0.0023 (7)0.0045 (7)
Geometric parameters (Å, º) top
C1—O11.424 (2)C5—H5B0.9700
C1—C71.509 (3)C6—O21.409 (2)
C1—C21.519 (3)C6—H6A0.9700
C1—H10.9800C6—H6B0.9700
C2—N11.500 (2)C7—C121.389 (3)
C2—H2A0.9700C7—C81.392 (3)
C2—H2B0.9700C8—C91.385 (3)
C3—N11.496 (2)C8—Cl11.733 (2)
C3—C41.501 (3)C9—C101.374 (3)
C3—H3A0.9700C9—H90.9300
C3—H3B0.9700C10—C111.372 (3)
C4—O11.425 (2)C10—Cl21.728 (2)
C4—H4A0.9700C11—F11.348 (2)
C4—H4B0.9700C11—C121.373 (3)
C5—N11.500 (2)C12—H120.9300
C5—C61.512 (3)N1—H1A0.9100
C5—H5A0.9700O2—H20.8200
O1—C1—C7107.19 (15)O2—C6—H6A109.3
O1—C1—C2109.92 (15)C5—C6—H6A109.3
C7—C1—C2111.97 (16)O2—C6—H6B109.3
O1—C1—H1109.2C5—C6—H6B109.3
C7—C1—H1109.2H6A—C6—H6B107.9
C2—C1—H1109.2C12—C7—C8117.61 (18)
N1—C2—C1110.95 (16)C12—C7—C1119.86 (18)
N1—C2—H2A109.4C8—C7—C1122.51 (17)
C1—C2—H2A109.4C9—C8—C7121.59 (19)
N1—C2—H2B109.4C9—C8—Cl1118.42 (16)
C1—C2—H2B109.4C7—C8—Cl1119.98 (15)
H2A—C2—H2B108.0C10—C9—C8119.70 (19)
N1—C3—C4110.19 (15)C10—C9—H9120.2
N1—C3—H3A109.6C8—C9—H9120.2
C4—C3—H3A109.6C11—C10—C9119.07 (19)
N1—C3—H3B109.6C11—C10—Cl2120.72 (17)
C4—C3—H3B109.6C9—C10—Cl2120.17 (17)
H3A—C3—H3B108.1F1—C11—C10119.59 (19)
O1—C4—C3111.41 (17)F1—C11—C12118.6 (2)
O1—C4—H4A109.3C10—C11—C12121.76 (19)
C3—C4—H4A109.3C11—C12—C7120.3 (2)
O1—C4—H4B109.3C11—C12—H12119.9
C3—C4—H4B109.3C7—C12—H12119.9
H4A—C4—H4B108.0C3—N1—C5112.96 (14)
N1—C5—C6113.15 (17)C3—N1—C2109.72 (14)
N1—C5—H5A108.9C5—N1—C2110.51 (15)
C6—C5—H5A108.9C3—N1—H1A107.8
N1—C5—H5B108.9C5—N1—H1A107.8
C6—C5—H5B108.9C2—N1—H1A107.8
H5A—C5—H5B107.8C1—O1—C4110.30 (14)
O2—C6—C5111.66 (16)C6—O2—H2109.5
O1—C1—C2—N157.40 (19)Cl2—C10—C11—F10.1 (3)
C7—C1—C2—N1176.42 (15)C9—C10—C11—C120.1 (3)
N1—C3—C4—O157.9 (2)Cl2—C10—C11—C12177.86 (18)
N1—C5—C6—O255.4 (2)F1—C11—C12—C7177.92 (19)
O1—C1—C7—C1225.0 (3)C10—C11—C12—C70.1 (3)
C2—C1—C7—C1295.6 (2)C8—C7—C12—C110.4 (3)
O1—C1—C7—C8152.87 (19)C1—C7—C12—C11177.64 (19)
C2—C1—C7—C886.5 (2)C4—C3—N1—C5176.60 (15)
C12—C7—C8—C90.7 (3)C4—C3—N1—C252.8 (2)
C1—C7—C8—C9177.28 (19)C6—C5—N1—C356.4 (2)
C12—C7—C8—Cl1179.16 (16)C6—C5—N1—C2179.75 (15)
C1—C7—C8—Cl11.2 (3)C1—C2—N1—C353.09 (19)
C7—C8—C9—C100.7 (3)C1—C2—N1—C5178.29 (15)
Cl1—C8—C9—C10179.21 (16)C7—C1—O1—C4176.77 (16)
C8—C9—C10—C110.4 (3)C2—C1—O1—C461.3 (2)
C8—C9—C10—Cl2178.16 (17)C3—C4—O1—C162.4 (2)
C9—C10—C11—F1177.89 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl30.912.213.0886 (15)163
O2—H2···Cl3i0.822.303.1178 (18)173
Symmetry code: (i) x+1, y+2, z+1.
 

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