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The crystal structure of the title compound, C12H14Cl2FNO4S, shows that, although there are no intra- or inter­molecular π–π stacking inter­actions, there are O—H...O, C—H...F and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031831/rn6067sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031831/rn6067Isup2.hkl
Contains datablock I

CCDC reference: 289874

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.053
  • wR factor = 0.155
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Cl2 .. F1 .. 2.91 Ang.
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 2.10 Deg. F1' -C10 -H10B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 7.00 Deg. F1 -C10 -H10C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 3.10 Deg. H10A -C10 -H10D 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 13.70 Deg. C10 -F1 -H10C 1.555 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 25.98 From the CIF: _reflns_number_total 2839 Count of symmetry unique reflns 1643 Completeness (_total/calc) 172.79% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1196 Fraction of Friedel pairs measured 0.728 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 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 6 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); 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, 2001); software used to prepare material for publication: SHELXTL.

[R-(R*,S*)]-2,2-Dichloro-N-[1-(fluoromethyl)-2-hydroxy-2-[4- (methylsulfonyl)phenyl]ethylacetamide top
Crystal data top
C12H13Cl2FNO4SF(000) = 366
Mr = 357.19Dx = 1.587 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ybCell parameters from 1667 reflections
a = 11.2407 (18) Åθ = 2.7–24.1°
b = 5.0994 (8) ŵ = 0.60 mm1
c = 13.412 (2) ÅT = 292 K
β = 103.499 (3)°Plate, colorless
V = 747.6 (2) Å30.30 × 0.20 × 0.14 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
2839 independent reflections
Radiation source: fine-focus sealed tube2427 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
φ and ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1311
Tmin = 0.841, Tmax = 0.921k = 66
4249 measured reflectionsl = 1615
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)] = 0.053H-atom parameters constrained
wR(F2) = 0.155 w = 1/[σ2(Fo2) + (0.0885P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2839 reflectionsΔρmax = 0.38 e Å3
196 parametersΔρmin = 0.29 e Å3
2 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (12)
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)
C10.1090 (4)0.9154 (13)0.6128 (3)0.0575 (13)
H1A0.02460.87160.58580.086*
H1B0.11901.10230.61170.086*
H1C0.13440.85330.68210.086*
C20.3531 (4)0.8279 (8)0.6015 (3)0.0378 (10)
C30.4122 (4)0.6518 (9)0.6751 (3)0.0416 (10)
H30.36990.51220.69520.050*
C40.4136 (4)1.0409 (9)0.5725 (3)0.0429 (11)
H40.37231.15940.52390.052*
C50.5359 (4)0.6876 (8)0.7184 (3)0.0397 (10)
H50.57650.57020.76790.048*
C60.5372 (4)1.0743 (8)0.6174 (3)0.0414 (10)
H60.57861.21780.59920.050*
C70.6000 (4)0.8950 (9)0.6894 (3)0.0345 (9)
C80.7373 (4)0.9282 (9)0.7287 (3)0.0370 (9)
H80.77640.85510.67680.044*
C90.7931 (4)0.7922 (9)0.8300 (3)0.0384 (10)
H90.77710.60370.82150.046*
C100.9311 (5)0.8338 (14)0.8597 (4)0.0710 (19)
H10A0.95111.01860.86910.085*0.516 (5)
H10B0.96790.74020.92220.085*0.516 (5)
H10C0.96650.77870.80370.085*0.484 (5)
H10D0.94871.01870.87210.085*0.484 (5)
C120.7131 (4)0.7128 (9)0.9798 (3)0.0400 (10)
C130.6792 (4)0.8451 (9)1.0724 (3)0.0454 (11)
H130.64181.01601.05140.054*
Cl10.57592 (14)0.6518 (4)1.12025 (10)0.0810 (5)
Cl20.81408 (14)0.8918 (4)1.16698 (10)0.0815 (6)
F10.9721 (5)0.728 (2)0.7734 (5)0.103 (2)0.516 (5)
F1'0.9840 (6)0.690 (2)0.9482 (5)0.103 (2)0.484 (5)
N10.7403 (3)0.8869 (8)0.9141 (2)0.0374 (8)
O10.1797 (3)0.4903 (7)0.5373 (3)0.0715 (12)
O20.1734 (3)0.8979 (8)0.4395 (2)0.0579 (9)
O30.7686 (3)1.2008 (6)0.7394 (2)0.0461 (8)
H3A0.79941.24600.69240.069*
O40.7148 (3)0.4780 (7)0.9714 (2)0.0588 (10)
S10.19842 (10)0.7680 (2)0.53801 (8)0.0427 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.052 (3)0.076 (4)0.048 (3)0.008 (3)0.017 (2)0.001 (3)
C20.049 (2)0.035 (3)0.031 (2)0.0003 (17)0.0110 (17)0.0001 (16)
C30.047 (2)0.042 (2)0.036 (2)0.005 (2)0.0107 (18)0.001 (2)
C40.056 (3)0.042 (3)0.030 (2)0.007 (2)0.008 (2)0.0023 (18)
C50.051 (2)0.035 (2)0.0315 (19)0.0006 (19)0.0063 (18)0.0054 (17)
C60.059 (3)0.035 (2)0.033 (2)0.003 (2)0.018 (2)0.0027 (18)
C70.047 (2)0.034 (2)0.0246 (18)0.0005 (19)0.0125 (16)0.0053 (17)
C80.049 (2)0.039 (2)0.0263 (19)0.0022 (19)0.0159 (17)0.0014 (17)
C90.044 (2)0.042 (2)0.032 (2)0.0032 (19)0.0158 (17)0.0034 (19)
C100.054 (3)0.111 (6)0.048 (3)0.011 (3)0.014 (2)0.019 (3)
C120.054 (3)0.037 (3)0.0281 (19)0.0028 (19)0.0096 (18)0.0035 (17)
C130.062 (3)0.047 (3)0.029 (2)0.000 (2)0.0127 (19)0.0019 (18)
Cl10.0826 (10)0.1118 (13)0.0605 (8)0.0343 (9)0.0405 (7)0.0261 (8)
Cl20.0751 (9)0.1241 (14)0.0452 (7)0.0289 (10)0.0140 (6)0.0266 (8)
F10.061 (3)0.176 (7)0.075 (3)0.035 (4)0.020 (2)0.036 (4)
F1'0.061 (3)0.176 (7)0.075 (3)0.035 (4)0.020 (2)0.036 (4)
N10.046 (2)0.0423 (19)0.0251 (15)0.0009 (17)0.0110 (14)0.0031 (15)
O10.059 (2)0.041 (2)0.101 (3)0.0016 (17)0.009 (2)0.008 (2)
O20.069 (2)0.075 (2)0.0280 (15)0.008 (2)0.0061 (14)0.0005 (17)
O30.066 (2)0.0375 (19)0.0381 (15)0.0143 (15)0.0180 (14)0.0030 (13)
O40.100 (3)0.0352 (19)0.051 (2)0.0004 (18)0.038 (2)0.0024 (15)
S10.0472 (6)0.0390 (6)0.0390 (6)0.0040 (5)0.0040 (4)0.0046 (5)
Geometric parameters (Å, º) top
C1—S11.747 (5)C9—N11.473 (5)
C1—H1A0.9600C9—C101.524 (6)
C1—H1B0.9600C9—H90.9800
C1—H1C0.9600C10—F1'1.404 (8)
C2—C41.384 (6)C10—F11.445 (8)
C2—C31.385 (6)C10—H10A0.9700
C2—S11.775 (4)C10—H10B0.9700
C3—C51.387 (5)C10—H10C0.9700
C3—H30.9300C10—H10D0.9700
C4—C61.389 (6)C12—O41.203 (6)
C4—H40.9300C12—N11.336 (5)
C5—C71.385 (6)C12—C131.537 (5)
C5—H50.9300C13—Cl21.751 (5)
C6—C71.397 (6)C13—Cl11.755 (5)
C6—H60.9300C13—H130.9800
C7—C81.519 (6)F1—H10C0.4965
C8—O31.433 (5)O1—S11.431 (4)
C8—C91.524 (5)O2—S11.446 (3)
C8—H80.9800O3—H3A0.8200
S1—C1—H1A109.5F1—C10—C9103.6 (4)
S1—C1—H1B109.5F1'—C10—H10A111.0
H1A—C1—H1B109.5F1—C10—H10A111.0
S1—C1—H1C109.5C9—C10—H10A111.0
H1A—C1—H1C109.5F1'—C10—H10B2.1
H1B—C1—H1C109.5F1—C10—H10B111.0
C4—C2—C3121.6 (4)C9—C10—H10B111.0
C4—C2—S1119.4 (3)H10A—C10—H10B109.0
C3—C2—S1118.9 (3)F1'—C10—H10C109.5
C2—C3—C5118.7 (4)F1—C10—H10C7.0
C2—C3—H3120.6C9—C10—H10C109.5
C5—C3—H3120.6H10A—C10—H10C105.0
C2—C4—C6118.8 (4)H10B—C10—H10C111.0
C2—C4—H4120.6F1'—C10—H10D109.5
C6—C4—H4120.6F1—C10—H10D114.1
C7—C5—C3121.3 (4)C9—C10—H10D109.5
C7—C5—H5119.4H10A—C10—H10D3.1
C3—C5—H5119.4H10B—C10—H10D107.5
C4—C6—C7120.8 (4)H10C—C10—H10D108.1
C4—C6—H6119.6O4—C12—N1126.1 (4)
C7—C6—H6119.6O4—C12—C13121.7 (4)
C5—C7—C6118.8 (4)N1—C12—C13112.3 (4)
C5—C7—C8122.7 (4)C12—C13—Cl2108.0 (3)
C6—C7—C8118.4 (4)C12—C13—Cl1111.0 (3)
O3—C8—C7110.4 (4)Cl2—C13—Cl1110.3 (2)
O3—C8—C9108.1 (3)C12—C13—H13109.2
C7—C8—C9115.6 (3)Cl2—C13—H13109.2
O3—C8—H8107.4Cl1—C13—H13109.2
C7—C8—H8107.4C10—F1—H10C13.7
C9—C8—H8107.4C12—N1—C9118.8 (4)
N1—C9—C10108.8 (3)C8—O3—H3A109.5
N1—C9—C8112.2 (3)O1—S1—O2116.7 (2)
C10—C9—C8110.6 (4)O1—S1—C1109.0 (3)
N1—C9—H9108.4O2—S1—C1108.2 (2)
C10—C9—H9108.4O1—S1—C2107.4 (2)
C8—C9—H9108.4O2—S1—C2108.6 (2)
F1'—C10—F1109.4 (7)C1—S1—C2106.3 (2)
F1'—C10—C9110.6 (5)
C4—C2—C3—C51.7 (6)N1—C9—C10—F1'61.5 (7)
S1—C2—C3—C5174.8 (3)C8—C9—C10—F1'174.9 (6)
C3—C2—C4—C61.3 (6)N1—C9—C10—F1178.6 (5)
S1—C2—C4—C6175.2 (3)C8—C9—C10—F157.8 (7)
C2—C3—C5—C70.1 (6)O4—C12—C13—Cl290.8 (5)
C2—C4—C6—C70.8 (6)N1—C12—C13—Cl288.6 (4)
C3—C5—C7—C61.9 (6)O4—C12—C13—Cl130.2 (6)
C3—C5—C7—C8174.9 (4)N1—C12—C13—Cl1150.4 (3)
C4—C6—C7—C52.3 (6)O4—C12—N1—C98.8 (7)
C4—C6—C7—C8174.6 (4)C13—C12—N1—C9170.5 (3)
C5—C7—C8—O3146.2 (4)C10—C9—N1—C1299.8 (5)
C6—C7—C8—O337.0 (5)C8—C9—N1—C12137.6 (4)
C5—C7—C8—C923.1 (6)C4—C2—S1—O1148.5 (4)
C6—C7—C8—C9160.1 (4)C3—C2—S1—O128.1 (4)
O3—C8—C9—N164.5 (4)C4—C2—S1—O221.3 (4)
C7—C8—C9—N159.9 (5)C3—C2—S1—O2155.2 (3)
O3—C8—C9—C1057.2 (5)C4—C2—S1—C194.9 (4)
C7—C8—C9—C10178.5 (4)C3—C2—S1—C188.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O2i0.822.022.815 (4)164
C1—H1A···O1ii0.962.573.418 (6)148
C1—H1B···O1iii0.962.393.260 (8)151
C1—H1C···F1iv0.962.513.077 (9)118
C9—H9···O3v0.982.323.239 (5)156
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y+1/2, z+1; (iii) x, y+1, z; (iv) x1, y, z; (v) x, y1, z.
 

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