2,2-Dichloro-N-{[1-(fluoro­meth­yl)-2-hydr­oxy-2-[4-(methyl­sulfon­yl)phen­yl]ethyl}­acetamide

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.

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

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

Crystal data

C12H13Cl2FNO4S	F(000) = 366
Mr = 357.19	Dx = 1.587 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2yb	Cell parameters from 1667 reflections
a = 11.2407 (18) Å	θ = 2.7–24.1°
b = 5.0994 (8) Å	µ = 0.60 mm^−1
c = 13.412 (2) Å	T = 292 K
β = 103.499 (3)°	Plate, colorless
V = 747.6 (2) Å^3	0.30 × 0.20 × 0.14 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	2839 independent reflections
Radiation source: fine-focus sealed tube	2427 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→11
Tmin = 0.841, Tmax = 0.921	k = −6→6
4249 measured reflections	l = −16→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.155	w = 1/[σ^2(Fo^2) + (0.0885P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2839 reflections	Δρmax = 0.38 e Å^−3
196 parameters	Δρmin = −0.29 e Å^−3
2 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.07 (12)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.1090 (4)	0.9154 (13)	0.6128 (3)	0.0575 (13)
H1A	0.0246	0.8716	0.5858	0.086*
H1B	0.1190	1.1023	0.6117	0.086*
H1C	0.1344	0.8533	0.6821	0.086*
C2	0.3531 (4)	0.8279 (8)	0.6015 (3)	0.0378 (10)
C3	0.4122 (4)	0.6518 (9)	0.6751 (3)	0.0416 (10)
H3	0.3699	0.5122	0.6952	0.050*
C4	0.4136 (4)	1.0409 (9)	0.5725 (3)	0.0429 (11)
H4	0.3723	1.1594	0.5239	0.052*
C5	0.5359 (4)	0.6876 (8)	0.7184 (3)	0.0397 (10)
H5	0.5765	0.5702	0.7679	0.048*
C6	0.5372 (4)	1.0743 (8)	0.6174 (3)	0.0414 (10)
H6	0.5786	1.2178	0.5992	0.050*
C7	0.6000 (4)	0.8950 (9)	0.6894 (3)	0.0345 (9)
C8	0.7373 (4)	0.9282 (9)	0.7287 (3)	0.0370 (9)
H8	0.7764	0.8551	0.6768	0.044*
C9	0.7931 (4)	0.7922 (9)	0.8300 (3)	0.0384 (10)
H9	0.7771	0.6037	0.8215	0.046*
C10	0.9311 (5)	0.8338 (14)	0.8597 (4)	0.0710 (19)
H10A	0.9511	1.0186	0.8691	0.085*	0.516 (5)
H10B	0.9679	0.7402	0.9222	0.085*	0.516 (5)
H10C	0.9665	0.7787	0.8037	0.085*	0.484 (5)
H10D	0.9487	1.0187	0.8721	0.085*	0.484 (5)
C12	0.7131 (4)	0.7128 (9)	0.9798 (3)	0.0400 (10)
C13	0.6792 (4)	0.8451 (9)	1.0724 (3)	0.0454 (11)
H13	0.6418	1.0160	1.0514	0.054*
Cl1	0.57592 (14)	0.6518 (4)	1.12025 (10)	0.0810 (5)
Cl2	0.81408 (14)	0.8918 (4)	1.16698 (10)	0.0815 (6)
F1	0.9721 (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)
N1	0.7403 (3)	0.8869 (8)	0.9141 (2)	0.0374 (8)
O1	0.1797 (3)	0.4903 (7)	0.5373 (3)	0.0715 (12)
O2	0.1734 (3)	0.8979 (8)	0.4395 (2)	0.0579 (9)
O3	0.7686 (3)	1.2008 (6)	0.7394 (2)	0.0461 (8)
H3A	0.7994	1.2460	0.6924	0.069*
O4	0.7148 (3)	0.4780 (7)	0.9714 (2)	0.0588 (10)
S1	0.19842 (10)	0.7680 (2)	0.53801 (8)	0.0427 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.052 (3)	0.076 (4)	0.048 (3)	0.008 (3)	0.017 (2)	0.001 (3)
C2	0.049 (2)	0.035 (3)	0.031 (2)	−0.0003 (17)	0.0110 (17)	−0.0001 (16)
C3	0.047 (2)	0.042 (2)	0.036 (2)	−0.005 (2)	0.0107 (18)	−0.001 (2)
C4	0.056 (3)	0.042 (3)	0.030 (2)	0.007 (2)	0.008 (2)	0.0023 (18)
C5	0.051 (2)	0.035 (2)	0.0315 (19)	0.0006 (19)	0.0063 (18)	0.0054 (17)
C6	0.059 (3)	0.035 (2)	0.033 (2)	−0.003 (2)	0.018 (2)	0.0027 (18)
C7	0.047 (2)	0.034 (2)	0.0246 (18)	−0.0005 (19)	0.0125 (16)	−0.0053 (17)
C8	0.049 (2)	0.039 (2)	0.0263 (19)	−0.0022 (19)	0.0159 (17)	−0.0014 (17)
C9	0.044 (2)	0.042 (2)	0.032 (2)	0.0032 (19)	0.0158 (17)	0.0034 (19)
C10	0.054 (3)	0.111 (6)	0.048 (3)	0.011 (3)	0.014 (2)	0.019 (3)
C12	0.054 (3)	0.037 (3)	0.0281 (19)	0.0028 (19)	0.0096 (18)	−0.0035 (17)
C13	0.062 (3)	0.047 (3)	0.029 (2)	0.000 (2)	0.0127 (19)	−0.0019 (18)
Cl1	0.0826 (10)	0.1118 (13)	0.0605 (8)	−0.0343 (9)	0.0405 (7)	−0.0261 (8)
Cl2	0.0751 (9)	0.1241 (14)	0.0452 (7)	−0.0289 (10)	0.0140 (6)	−0.0266 (8)
F1	0.061 (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)
N1	0.046 (2)	0.0423 (19)	0.0251 (15)	−0.0009 (17)	0.0110 (14)	−0.0031 (15)
O1	0.059 (2)	0.041 (2)	0.101 (3)	−0.0016 (17)	−0.009 (2)	−0.008 (2)
O2	0.069 (2)	0.075 (2)	0.0280 (15)	0.008 (2)	0.0061 (14)	−0.0005 (17)
O3	0.066 (2)	0.0375 (19)	0.0381 (15)	−0.0143 (15)	0.0180 (14)	−0.0030 (13)
O4	0.100 (3)	0.0352 (19)	0.051 (2)	0.0004 (18)	0.038 (2)	0.0024 (15)
S1	0.0472 (6)	0.0390 (6)	0.0390 (6)	0.0040 (5)	0.0040 (4)	−0.0046 (5)

Geometric parameters (Å, º)

C1—S1	1.747 (5)	C9—N1	1.473 (5)
C1—H1A	0.9600	C9—C10	1.524 (6)
C1—H1B	0.9600	C9—H9	0.9800
C1—H1C	0.9600	C10—F1'	1.404 (8)
C2—C4	1.384 (6)	C10—F1	1.445 (8)
C2—C3	1.385 (6)	C10—H10A	0.9700
C2—S1	1.775 (4)	C10—H10B	0.9700
C3—C5	1.387 (5)	C10—H10C	0.9700
C3—H3	0.9300	C10—H10D	0.9700
C4—C6	1.389 (6)	C12—O4	1.203 (6)
C4—H4	0.9300	C12—N1	1.336 (5)
C5—C7	1.385 (6)	C12—C13	1.537 (5)
C5—H5	0.9300	C13—Cl2	1.751 (5)
C6—C7	1.397 (6)	C13—Cl1	1.755 (5)
C6—H6	0.9300	C13—H13	0.9800
C7—C8	1.519 (6)	F1—H10C	0.4965
C8—O3	1.433 (5)	O1—S1	1.431 (4)
C8—C9	1.524 (5)	O2—S1	1.446 (3)
C8—H8	0.9800	O3—H3A	0.8200
S1—C1—H1A	109.5	F1—C10—C9	103.6 (4)
S1—C1—H1B	109.5	F1'—C10—H10A	111.0
H1A—C1—H1B	109.5	F1—C10—H10A	111.0
S1—C1—H1C	109.5	C9—C10—H10A	111.0
H1A—C1—H1C	109.5	F1'—C10—H10B	2.1
H1B—C1—H1C	109.5	F1—C10—H10B	111.0
C4—C2—C3	121.6 (4)	C9—C10—H10B	111.0
C4—C2—S1	119.4 (3)	H10A—C10—H10B	109.0
C3—C2—S1	118.9 (3)	F1'—C10—H10C	109.5
C2—C3—C5	118.7 (4)	F1—C10—H10C	7.0
C2—C3—H3	120.6	C9—C10—H10C	109.5
C5—C3—H3	120.6	H10A—C10—H10C	105.0
C2—C4—C6	118.8 (4)	H10B—C10—H10C	111.0
C2—C4—H4	120.6	F1'—C10—H10D	109.5
C6—C4—H4	120.6	F1—C10—H10D	114.1
C7—C5—C3	121.3 (4)	C9—C10—H10D	109.5
C7—C5—H5	119.4	H10A—C10—H10D	3.1
C3—C5—H5	119.4	H10B—C10—H10D	107.5
C4—C6—C7	120.8 (4)	H10C—C10—H10D	108.1
C4—C6—H6	119.6	O4—C12—N1	126.1 (4)
C7—C6—H6	119.6	O4—C12—C13	121.7 (4)
C5—C7—C6	118.8 (4)	N1—C12—C13	112.3 (4)
C5—C7—C8	122.7 (4)	C12—C13—Cl2	108.0 (3)
C6—C7—C8	118.4 (4)	C12—C13—Cl1	111.0 (3)
O3—C8—C7	110.4 (4)	Cl2—C13—Cl1	110.3 (2)
O3—C8—C9	108.1 (3)	C12—C13—H13	109.2
C7—C8—C9	115.6 (3)	Cl2—C13—H13	109.2
O3—C8—H8	107.4	Cl1—C13—H13	109.2
C7—C8—H8	107.4	C10—F1—H10C	13.7
C9—C8—H8	107.4	C12—N1—C9	118.8 (4)
N1—C9—C10	108.8 (3)	C8—O3—H3A	109.5
N1—C9—C8	112.2 (3)	O1—S1—O2	116.7 (2)
C10—C9—C8	110.6 (4)	O1—S1—C1	109.0 (3)
N1—C9—H9	108.4	O2—S1—C1	108.2 (2)
C10—C9—H9	108.4	O1—S1—C2	107.4 (2)
C8—C9—H9	108.4	O2—S1—C2	108.6 (2)
F1'—C10—F1	109.4 (7)	C1—S1—C2	106.3 (2)
F1'—C10—C9	110.6 (5)
C4—C2—C3—C5	−1.7 (6)	N1—C9—C10—F1'	61.5 (7)
S1—C2—C3—C5	174.8 (3)	C8—C9—C10—F1'	−174.9 (6)
C3—C2—C4—C6	1.3 (6)	N1—C9—C10—F1	178.6 (5)
S1—C2—C4—C6	−175.2 (3)	C8—C9—C10—F1	−57.8 (7)
C2—C3—C5—C7	0.1 (6)	O4—C12—C13—Cl2	90.8 (5)
C2—C4—C6—C7	0.8 (6)	N1—C12—C13—Cl2	−88.6 (4)
C3—C5—C7—C6	1.9 (6)	O4—C12—C13—Cl1	−30.2 (6)
C3—C5—C7—C8	−174.9 (4)	N1—C12—C13—Cl1	150.4 (3)
C4—C6—C7—C5	−2.3 (6)	O4—C12—N1—C9	−8.8 (7)
C4—C6—C7—C8	174.6 (4)	C13—C12—N1—C9	170.5 (3)
C5—C7—C8—O3	−146.2 (4)	C10—C9—N1—C12	−99.8 (5)
C6—C7—C8—O3	37.0 (5)	C8—C9—N1—C12	137.6 (4)
C5—C7—C8—C9	−23.1 (6)	C4—C2—S1—O1	148.5 (4)
C6—C7—C8—C9	160.1 (4)	C3—C2—S1—O1	−28.1 (4)
O3—C8—C9—N1	64.5 (4)	C4—C2—S1—O2	21.3 (4)
C7—C8—C9—N1	−59.9 (5)	C3—C2—S1—O2	−155.2 (3)
O3—C8—C9—C10	−57.2 (5)	C4—C2—S1—C1	−94.9 (4)
C7—C8—C9—C10	178.5 (4)	C3—C2—S1—C1	88.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2^i	0.82	2.02	2.815 (4)	164
C1—H1A···O1^ii	0.96	2.57	3.418 (6)	148
C1—H1B···O1^iii	0.96	2.39	3.260 (8)	151
C1—H1C···F1^iv	0.96	2.51	3.077 (9)	118
C9—H9···O3^v	0.98	2.32	3.239 (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) x−1, y, z; (v) x, y−1, z.