Structural systematics of 4,4′-disubstituted benzenesulfonamidobenzenes. 1. Overview and dimer-based isostructures

One hundred 4,4′-disubstituted benzenesulfonamidobenzenes, X–C₆H₅–SO₂–NH–C₆H₅–Y, where X, Y = NO₂, CN, CF₃, I, Br, Cl, F, H, Me, OMe, have been synthesized and their crystal structures determined. The resulting set of 133 structures, which includes polymorphic forms, is used to make a comparative study of the molecular packing and the nature of the intermolecular interactions, including the formation of hydrogen-bonding motifs and the influence of the two substituents X and Y on these features. Nine distinct supramolecular connectivity motifs of hydrogen bonding are encountered. There are 74% of all the structures investigated which exhibit one of two motifs based on N—H...O=S interactions, a dimer or a chain. There are three other, infrequent motifs, also employing N—H...O=S links, which exhibit more complexity. Four different chain motifs result from either N—H...O=N, N—H...C[triple bond]N or N—H...OMe interactions, arising from the presence of a nitro (position Y), nitrile (X or Y) or methoxy (Y) substituent. The program XPac [Gelbrich & Hursthouse (2005). CrystEngComm, 7, 324–336] was used to systematically analyse the packing relationships between crystal structures. Similar discrete (zero-dimensional) and extended (one-dimensional and two-dimensional) structure components, as well as cases of isostructurality were identified. A hierarchy for the classification of the 56 distinct structure types of this set is presented. The most common type, a series of 22 isostructures containing the simple centrosymmetric N—H...O=S-bonded dimer, is discussed in detail.

Computing details

Data collection: COLLECT (Hooft, 1998) for Br~Br, Br~CF3, Br~I, Cl~Br, Cl~CCH, Cl~CF3, Cl~Cl0.2Cl~F0.8, CN~Br, CN~CF3, CN~Cl, CN~I, CN~Me, F~Br, F~CF3, F~Cl, F~F, F~I, Me~Br, Me~CF3, Me~Cl, Me~I, MeO~I. Cell refinement: DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998) for Br~Br, Br~CF3, Br~I, Cl~Br, Cl~CCH, Cl~CF3, Cl~Cl0.2Cl~F0.8, Cl~I, CN~Br, CN~CF3, CN~Cl, CN~I, CN~Me, F~Br, F~CF3, F~Cl, F~F, F~I, Me~Br, Me~CF3, Me~Cl, Me~I, MeO~I. Data reduction: DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998) for Br~Br, Br~CF3, Br~I, Cl~Br, Cl~CCH, Cl~CF3, Cl~Cl0.2Cl~F0.8, Cl~I, CN~Br, CN~CF3, CN~Cl, CN~I, CN~Me, F~Br, F~CF3, F~Cl, F~F, F~I, Me~Br, Me~CF3, Me~Cl, Me~I, MeO~I. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for Br~Br, Br~CF3, Br~I, Cl~Br, Cl~CCH, Cl~CF3, Cl~Cl0.2Cl~F0.8, Cl~I, CN~Br, CN~CF3, CN~Cl, CN~I, CN~Me, F~Br, F~CF3, F~Cl, F~F, F~I, Me~Br, Me~CF3, Me~Cl, Me~I, MeO~I; SHELXS97 (Sheldrick, 1990) for Cl~Cl. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: Mercury (Bruno et al., 2002) for Br~Br, Br~CF3, Br~I, Cl~Br, Cl~CCH, Cl~CF3, Cl~Cl0.2Cl~F0.8, Cl~I, CN~Br, CN~CF3, CN~Cl, CN~I, CN~Me, F~Br, F~CF3, F~Cl, F~F, F~I, Me~Br, Me~CF3, Me~Cl, Me~I, MeO~I.

(Br~Br)

Crystal data

C12H9Br2NO2S	F(000) = 3420
Mr = 391.08	Dx = 1.953 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.3197 (11) Å	µ = 6.24 mm^−1
c = 9.2582 (6) Å	T = 120 K
V = 5984.2 (5) Å^3	0.40 × 0.20 × 0.10 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	1962 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1475 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.186
φ & ω scans	θmax = 25.0°, θmin = 4.0°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −15→31
Tmin = 0.176, Tmax = 0.534	k = −29→31
3490 measured reflections	l = −8→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.206	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0002P)^2 + 450.P] where P = (Fo^2 + 2Fc^2)/3
1962 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 1.62 e Å^−3
1 restraint	Δρmin = −1.60 e Å^−3

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
Br1	0.86717 (5)	0.11346 (5)	0.53975 (13)	0.0316 (4)
Br2	0.93435 (5)	0.02581 (5)	1.32402 (16)	0.0375 (4)
S1	0.67776 (11)	−0.08437 (11)	0.9259 (3)	0.0243 (6)
O1	0.6367 (3)	−0.1296 (3)	0.8333 (9)	0.0308 (19)
O2	0.6567 (3)	−0.0595 (3)	1.0262 (9)	0.0274 (17)
N1	0.7102 (4)	−0.1123 (4)	1.0093 (11)	0.026 (2)
H1N	0.710 (6)	−0.142 (4)	0.964 (13)	0.031*
C1	0.7293 (5)	−0.0294 (4)	0.8180 (12)	0.022 (2)
C2	0.7334 (5)	0.0234 (5)	0.8157 (12)	0.025 (2)
H2	0.7092	0.0305	0.8747	0.030*
C3	0.7724 (5)	0.0652 (6)	0.7279 (13)	0.032 (3)
H3	0.7746	0.1009	0.7202	0.039*
C4	0.8089 (5)	0.0527 (5)	0.6501 (12)	0.026 (2)
C5	0.8078 (5)	0.0026 (5)	0.6533 (13)	0.029 (2)
H5	0.8345	−0.0031	0.6012	0.035*
C6	0.7656 (5)	−0.0403 (5)	0.7362 (13)	0.033 (3)
H6	0.7616	−0.0769	0.7370	0.039*
C7	0.7634 (5)	−0.0792 (4)	1.0828 (12)	0.025 (2)
C8	0.8046 (5)	−0.0927 (5)	1.0648 (13)	0.030 (3)
H8	0.7985	−0.1227	1.0019	0.036*
C9	0.8562 (5)	−0.0624 (5)	1.1389 (14)	0.029 (3)
H9	0.8845	−0.0728	1.1328	0.035*
C10	0.8640 (5)	−0.0168 (5)	1.2211 (12)	0.026 (2)
C11	0.8228 (5)	−0.0023 (5)	1.2400 (12)	0.027 (2)
H11	0.8292	0.0283	1.3010	0.033*
C12	0.7716 (5)	−0.0333 (5)	1.1682 (12)	0.026 (2)
H12	0.7429	−0.0236	1.1768	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0312 (7)	0.0280 (6)	0.0305 (7)	0.0109 (5)	−0.0014 (5)	−0.0005 (5)
Br2	0.0275 (7)	0.0298 (7)	0.0525 (9)	0.0123 (5)	−0.0125 (5)	−0.0040 (5)
S1	0.0218 (13)	0.0242 (13)	0.0275 (14)	0.0120 (11)	−0.0027 (11)	−0.0057 (11)
O1	0.023 (4)	0.026 (4)	0.042 (5)	0.012 (3)	−0.009 (4)	−0.011 (4)
O2	0.019 (4)	0.029 (4)	0.033 (4)	0.011 (3)	0.004 (3)	−0.005 (3)
N1	0.024 (5)	0.024 (5)	0.031 (5)	0.013 (4)	−0.010 (4)	−0.008 (4)
C1	0.032 (6)	0.021 (5)	0.025 (5)	0.022 (5)	−0.004 (4)	0.003 (4)
C2	0.029 (6)	0.028 (6)	0.023 (6)	0.019 (5)	−0.004 (4)	−0.003 (4)
C3	0.037 (7)	0.045 (7)	0.028 (6)	0.029 (6)	−0.004 (5)	−0.011 (5)
C4	0.036 (6)	0.027 (6)	0.018 (5)	0.019 (5)	−0.004 (4)	0.000 (4)
C5	0.029 (6)	0.036 (6)	0.025 (6)	0.018 (5)	0.004 (5)	−0.002 (5)
C6	0.041 (7)	0.032 (6)	0.028 (6)	0.021 (6)	0.002 (5)	−0.001 (5)
C7	0.035 (6)	0.017 (5)	0.022 (5)	0.013 (5)	0.002 (5)	0.003 (4)
C8	0.029 (6)	0.029 (6)	0.032 (6)	0.014 (5)	−0.013 (5)	−0.002 (5)
C9	0.020 (5)	0.023 (5)	0.043 (7)	0.009 (5)	−0.001 (5)	0.002 (5)
C10	0.035 (6)	0.027 (6)	0.021 (5)	0.018 (5)	0.004 (5)	0.013 (5)
C11	0.036 (6)	0.022 (5)	0.030 (6)	0.020 (5)	0.004 (5)	0.007 (5)
C12	0.033 (6)	0.024 (5)	0.026 (6)	0.017 (5)	−0.001 (5)	−0.004 (4)

Geometric parameters (Å, º)

Br1—C4	1.922 (12)	C3—C4	1.403 (16)
Br2—C10	1.929 (12)	C4—C5	1.354 (17)
S1—O2	1.430 (8)	C5—C6	1.393 (18)
S1—O1	1.461 (8)	C7—C8	1.359 (17)
S1—N1	1.625 (9)	C7—C12	1.402 (16)
S1—C1	1.767 (11)	C8—C9	1.407 (16)
N1—C7	1.442 (14)	C9—C10	1.383 (17)
C1—C2	1.390 (15)	C10—C11	1.378 (16)
C1—C6	1.393 (16)	C11—C12	1.388 (17)
C2—C3	1.372 (18)
O2—S1—O1	117.5 (5)	C3—C4—Br1	116.4 (9)
O2—S1—N1	111.0 (5)	C4—C5—C6	117.0 (11)
O1—S1—N1	104.5 (5)	C5—C6—C1	119.8 (11)
O2—S1—C1	107.6 (5)	C8—C7—C12	121.8 (11)
O1—S1—C1	109.6 (5)	C8—C7—N1	118.9 (10)
N1—S1—C1	106.1 (5)	C12—C7—N1	119.3 (10)
C7—N1—S1	123.0 (8)	C7—C8—C9	120.3 (11)
C2—C1—C6	121.2 (11)	C10—C9—C8	117.0 (11)
C2—C1—S1	120.4 (9)	C11—C10—C9	123.4 (11)
C6—C1—S1	118.4 (8)	C11—C10—Br2	118.4 (9)
C3—C2—C1	119.9 (11)	C9—C10—Br2	118.2 (9)
C2—C3—C4	116.9 (11)	C10—C11—C12	118.8 (11)
C5—C4—C3	125.1 (11)	C11—C12—C7	118.6 (11)
C5—C4—Br1	118.4 (9)

(Br~CF3)

Crystal data

C13H9BrF3NO2S	F(000) = 3384
Mr = 380.18	Dx = 1.752 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 28.0220 (6) Å	µ = 3.03 mm^−1
c = 9.5386 (3) Å	T = 293 K
V = 6486.5 (3) Å^3	0.30 × 0.22 × 0.17 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2552 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1820 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ & ω scans	θmax = 25.1°, θmin = 3.1°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −33→31
Tmin = 0.440, Tmax = 0.595	k = −33→33
14120 measured reflections	l = −11→9

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 6.4178P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
2552 reflections	Δρmax = 0.31 e Å^−3
231 parameters	Δρmin = −0.46 e Å^−3
55 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00067 (11)

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)
Br1	0.85984 (2)	0.74850 (3)	0.05093 (6)	0.0849 (3)
S1	0.67574 (4)	0.76077 (4)	0.41791 (11)	0.0536 (3)
O1	0.63740 (11)	0.76575 (12)	0.3275 (3)	0.0677 (8)
O2	0.65481 (12)	0.71658 (11)	0.5158 (3)	0.0654 (8)
N1	0.70830 (13)	0.81984 (14)	0.4980 (4)	0.0531 (8)
H1N	0.7056 (17)	0.8465 (13)	0.453 (4)	0.058 (12)*
C1	0.72571 (16)	0.75680 (15)	0.3140 (4)	0.0514 (9)
C2	0.7603 (2)	0.80062 (18)	0.2304 (5)	0.0678 (12)
H2	0.7570	0.8320	0.2276	0.102 (18)*
C3	0.8000 (2)	0.7979 (2)	0.1507 (5)	0.0750 (13)
H3	0.8237	0.8273	0.0941	0.078 (14)*
C4	0.80397 (18)	0.75099 (18)	0.1566 (4)	0.0594 (11)
C5	0.7693 (2)	0.70737 (19)	0.2371 (5)	0.0734 (13)
H5	0.7721	0.6757	0.2374	0.083 (15)*
C6	0.73002 (19)	0.70986 (18)	0.3181 (5)	0.0663 (12)
H6	0.7067	0.6803	0.3750	0.081 (15)*
C7	0.75830 (15)	0.83804 (15)	0.5717 (4)	0.0460 (9)
C8	0.79862 (17)	0.89284 (16)	0.5611 (5)	0.0588 (11)
H8	0.7924	0.9168	0.5072	0.061 (12)*
C9	0.84784 (18)	0.91190 (18)	0.6298 (5)	0.0621 (11)
H9	0.8748	0.9488	0.6224	0.067 (13)*
C10	0.85771 (17)	0.87693 (17)	0.7094 (4)	0.0567 (10)
C11	0.81719 (18)	0.82250 (17)	0.7221 (5)	0.0591 (11)
H11	0.8236	0.7988	0.7768	0.058 (12)*
C12	0.76750 (17)	0.80281 (16)	0.6552 (4)	0.0541 (10)
H12	0.7402	0.7661	0.6656	0.063 (12)*
C13	0.9109 (2)	0.89691 (18)	0.7820 (6)	0.0792 (15)
F1	0.9269 (3)	0.9395 (3)	0.8610 (8)	0.101 (3)	0.581 (11)
F2	0.9520 (3)	0.9214 (5)	0.6846 (8)	0.137 (4)	0.581 (11)
F3	0.9192 (5)	0.8598 (4)	0.8403 (16)	0.155 (5)	0.581 (11)
F1'	0.9033 (3)	0.8918 (6)	0.9227 (7)	0.113 (4)	0.419 (11)
F2'	0.9327 (4)	0.8660 (4)	0.7604 (12)	0.086 (4)	0.419 (11)
F3'	0.9480 (5)	0.9461 (4)	0.753 (2)	0.144 (6)	0.419 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0859 (4)	0.1065 (5)	0.0778 (4)	0.0597 (4)	−0.0033 (3)	−0.0157 (3)
S1	0.0434 (5)	0.0429 (5)	0.0714 (7)	0.0191 (4)	−0.0083 (5)	0.0040 (5)
O1	0.0498 (16)	0.0523 (17)	0.096 (2)	0.0218 (14)	−0.0209 (15)	0.0033 (15)
O2	0.0571 (17)	0.0498 (16)	0.082 (2)	0.0209 (14)	0.0021 (15)	0.0139 (14)
N1	0.0502 (19)	0.0456 (19)	0.068 (2)	0.0273 (16)	−0.0066 (16)	0.0029 (16)
C1	0.053 (2)	0.041 (2)	0.059 (2)	0.0224 (18)	−0.0128 (18)	−0.0023 (17)
C2	0.087 (3)	0.054 (3)	0.068 (3)	0.040 (2)	0.008 (3)	0.012 (2)
C3	0.090 (4)	0.066 (3)	0.068 (3)	0.038 (3)	0.014 (3)	0.010 (2)
C4	0.063 (3)	0.066 (3)	0.056 (2)	0.038 (2)	−0.015 (2)	−0.014 (2)
C5	0.084 (3)	0.055 (3)	0.091 (3)	0.042 (3)	−0.005 (3)	0.001 (2)
C6	0.066 (3)	0.047 (2)	0.084 (3)	0.027 (2)	−0.003 (2)	0.004 (2)
C7	0.046 (2)	0.045 (2)	0.050 (2)	0.0254 (17)	0.0035 (16)	0.0007 (17)
C8	0.059 (3)	0.047 (2)	0.069 (3)	0.026 (2)	−0.001 (2)	0.011 (2)
C9	0.055 (2)	0.046 (2)	0.075 (3)	0.017 (2)	−0.003 (2)	0.002 (2)
C10	0.052 (2)	0.053 (2)	0.064 (3)	0.027 (2)	−0.0093 (19)	−0.0098 (19)
C11	0.064 (3)	0.052 (2)	0.069 (3)	0.035 (2)	−0.016 (2)	−0.005 (2)
C12	0.053 (2)	0.037 (2)	0.070 (3)	0.0208 (19)	−0.008 (2)	−0.0001 (18)
C13	0.064 (3)	0.065 (3)	0.104 (4)	0.029 (3)	−0.016 (3)	−0.010 (3)
F1	0.094 (5)	0.108 (6)	0.094 (5)	0.045 (4)	−0.038 (4)	−0.048 (4)
F2	0.063 (4)	0.180 (8)	0.142 (6)	0.043 (5)	−0.016 (4)	−0.054 (6)
F3	0.132 (7)	0.112 (6)	0.210 (10)	0.054 (5)	−0.072 (7)	0.023 (6)
F1'	0.075 (5)	0.176 (10)	0.076 (5)	0.052 (6)	−0.034 (4)	−0.035 (6)
F2'	0.070 (5)	0.114 (7)	0.110 (6)	0.072 (5)	−0.036 (4)	−0.031 (5)
F3'	0.102 (7)	0.086 (7)	0.206 (11)	0.018 (5)	−0.058 (8)	0.013 (7)

Geometric parameters (Å, º)

Br1—C4	1.893 (4)	C7—C12	1.389 (5)
S1—O2	1.422 (3)	C8—C9	1.371 (6)
S1—O1	1.438 (3)	C9—C10	1.373 (6)
S1—N1	1.626 (3)	C10—C11	1.378 (6)
S1—C1	1.764 (4)	C10—C13	1.477 (7)
N1—C7	1.415 (5)	C11—C12	1.372 (6)
C1—C2	1.376 (6)	C13—F3'	1.273 (7)
C1—C6	1.380 (6)	C13—F1	1.287 (6)
C2—C3	1.381 (7)	C13—F2'	1.300 (7)
C3—C4	1.374 (6)	C13—F3	1.300 (7)
C4—C5	1.356 (6)	C13—F1'	1.355 (7)
C5—C6	1.375 (7)	C13—F2	1.368 (7)
C7—C8	1.382 (6)
O2—S1—O1	118.39 (18)	C11—C10—C13	119.7 (4)
O2—S1—N1	110.80 (19)	C12—C11—C10	120.9 (4)
O1—S1—N1	104.43 (17)	C11—C12—C7	119.5 (4)
O2—S1—C1	107.97 (18)	F3'—C13—F1	53.6 (8)
O1—S1—C1	108.94 (19)	F3'—C13—F2'	106.6 (10)
N1—S1—C1	105.59 (18)	F1—C13—F2'	130.4 (6)
C7—N1—S1	123.4 (3)	F3'—C13—F3	125.6 (9)
C2—C1—C6	120.6 (4)	F1—C13—F3	111.9 (8)
C2—C1—S1	119.8 (3)	F2'—C13—F3	37.2 (6)
C6—C1—S1	119.7 (3)	F3'—C13—F1'	109.2 (10)
C1—C2—C3	119.8 (4)	F1—C13—F1'	58.8 (6)
C4—C3—C2	118.9 (4)	F2'—C13—F1'	100.8 (7)
C5—C4—C3	121.4 (4)	F3—C13—F1'	64.7 (7)
C5—C4—Br1	120.1 (3)	F3'—C13—F2	44.2 (8)
C3—C4—Br1	118.5 (4)	F1—C13—F2	96.8 (6)
C4—C5—C6	120.2 (4)	F2'—C13—F2	70.6 (7)
C5—C6—C1	119.1 (4)	F3—C13—F2	104.4 (8)
C8—C7—C12	119.5 (4)	F1'—C13—F2	140.7 (6)
C8—C7—N1	118.4 (3)	F3'—C13—C10	115.6 (7)
C12—C7—N1	122.1 (3)	F1—C13—C10	116.3 (5)
C9—C8—C7	120.1 (4)	F2'—C13—C10	113.2 (5)
C8—C9—C10	120.6 (4)	F3—C13—C10	116.7 (6)
C9—C10—C11	119.4 (4)	F1'—C13—C10	110.5 (5)
C9—C10—C13	120.9 (4)	F2—C13—C10	108.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.90 (2)	1.99 (2)	2.892 (4)	175 (4)

Symmetry code: (i) −x+4/3, −y+5/3, −z+2/3.

(Br~I)

Crystal data

C12H9BrINO2S	F(000) = 3744
Mr = 438.07	Dx = 2.117 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 28.134 (4) Å	µ = 5.38 mm^−1
c = 9.0240 (18) Å	T = 120 K
V = 6185.8 (18) Å^3	0.20 × 0.20 × 0.10 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2401 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2080 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.120
φ & ω scans	θmax = 25.1°, θmin = 3.8°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −33→22
Tmin = 0.390, Tmax = 0.584	k = −33→30
5868 measured reflections	l = −10→10

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)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.180	w = 1/[σ^2(Fo^2) + (0.1042P)^2 + 104.7106P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
2401 reflections	Δρmax = 2.45 e Å^−3
176 parameters	Δρmin = −2.25 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00042 (10)

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
I1	0.90318 (2)	0.96785 (2)	0.17678 (6)	0.0301 (3)
Br1	0.74908 (4)	0.88450 (3)	0.95747 (8)	0.0302 (3)
S1	0.76065 (8)	1.08379 (8)	0.58577 (19)	0.0230 (5)
O1	0.7655 (2)	1.1265 (2)	0.6841 (6)	0.0291 (12)
O2	0.7159 (2)	1.0611 (2)	0.4830 (6)	0.0300 (13)
N1	0.8196 (3)	1.1106 (3)	0.4998 (7)	0.0236 (13)
H1N	0.849 (3)	1.142 (3)	0.538 (9)	0.03 (2)*
C1	0.7562 (3)	1.0281 (3)	0.6909 (8)	0.0223 (15)
C2	0.8018 (4)	1.0369 (4)	0.7713 (8)	0.0295 (18)
H2	0.8340	1.0720	0.7719	0.04 (3)*
C3	0.7996 (4)	0.9932 (4)	0.8521 (8)	0.0309 (18)
H3	0.8307	0.9976	0.9054	0.04 (3)*
C4	0.7519 (3)	0.9444 (3)	0.8520 (7)	0.0209 (15)
C5	0.7053 (3)	0.9354 (4)	0.7745 (9)	0.0279 (17)
H5	0.6725	0.9008	0.7783	0.04 (3)*
C6	0.7080 (3)	0.9785 (4)	0.6910 (9)	0.0283 (17)
H6	0.6772	0.9737	0.6355	0.05 (3)*
C7	0.8372 (3)	1.0776 (3)	0.4236 (7)	0.0184 (14)
C8	0.8925 (3)	1.0920 (3)	0.4384 (8)	0.0238 (15)
H8	0.9169	1.1227	0.4970	0.06 (4)*
C9	0.9112 (4)	1.0611 (4)	0.3671 (8)	0.0284 (17)
H9	0.9488	1.0713	0.3741	0.02 (2)*
C10	0.8750 (3)	1.0150 (3)	0.2844 (8)	0.0238 (16)
C11	0.8206 (3)	1.0007 (3)	0.2693 (8)	0.0234 (16)
H11	0.7961	0.9693	0.2129	0.05 (3)*
C12	0.8016 (4)	1.0333 (3)	0.3389 (8)	0.0280 (18)
H12	0.7645	1.0245	0.3271	0.06 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0313 (4)	0.0261 (4)	0.0353 (4)	0.0161 (3)	0.0083 (2)	−0.00037 (19)
Br1	0.0367 (5)	0.0296 (5)	0.0248 (5)	0.0170 (4)	0.0012 (3)	0.0011 (3)
S1	0.0245 (10)	0.0234 (10)	0.0218 (9)	0.0124 (8)	−0.0008 (7)	−0.0047 (7)
O1	0.031 (3)	0.027 (3)	0.034 (3)	0.018 (3)	0.001 (2)	−0.006 (2)
O2	0.034 (3)	0.027 (3)	0.026 (3)	0.013 (3)	−0.005 (2)	−0.003 (2)
N1	0.020 (3)	0.019 (3)	0.027 (3)	0.007 (3)	0.001 (3)	−0.004 (3)
C1	0.025 (4)	0.025 (4)	0.023 (3)	0.016 (3)	−0.002 (3)	−0.003 (3)
C2	0.030 (4)	0.029 (4)	0.020 (4)	0.008 (4)	−0.005 (3)	−0.005 (3)
C3	0.031 (4)	0.033 (5)	0.021 (3)	0.011 (4)	0.002 (3)	0.003 (3)
C4	0.034 (4)	0.013 (3)	0.021 (3)	0.016 (3)	0.002 (3)	−0.002 (3)
C5	0.017 (4)	0.034 (5)	0.029 (4)	0.010 (3)	−0.001 (3)	0.000 (3)
C6	0.027 (4)	0.034 (4)	0.028 (4)	0.018 (4)	0.000 (3)	0.000 (3)
C7	0.019 (4)	0.020 (4)	0.019 (3)	0.011 (3)	0.003 (3)	0.002 (3)
C8	0.026 (4)	0.027 (4)	0.022 (3)	0.015 (3)	−0.002 (3)	−0.002 (3)
C9	0.026 (4)	0.034 (4)	0.020 (3)	0.011 (4)	0.001 (3)	−0.002 (3)
C10	0.034 (4)	0.016 (4)	0.021 (3)	0.012 (3)	0.008 (3)	0.003 (3)
C11	0.018 (4)	0.021 (4)	0.022 (3)	0.002 (3)	0.007 (3)	0.000 (3)
C12	0.040 (5)	0.025 (4)	0.020 (3)	0.017 (4)	0.000 (3)	−0.003 (3)

Geometric parameters (Å, º)

I1—C10	2.093 (8)	C4—C5	1.393 (11)
Br1—C4	1.903 (7)	C5—C6	1.397 (12)
S1—O2	1.432 (6)	C5—H5	0.9500
S1—O1	1.443 (6)	C6—H6	0.9500
S1—N1	1.633 (7)	C7—C12	1.376 (11)
S1—C1	1.781 (8)	C7—C8	1.406 (10)
N1—C7	1.430 (9)	C8—C9	1.378 (12)
N1—H1N	0.92 (7)	C8—H8	0.9500
C1—C6	1.378 (11)	C9—C10	1.398 (11)
C1—C2	1.383 (11)	C9—H9	0.9500
C2—C3	1.406 (12)	C10—C11	1.383 (11)
C2—H2	0.9500	C11—C12	1.418 (11)
C3—C4	1.358 (11)	C11—H11	0.9500
C3—H3	0.9500	C12—H12	0.9500
O2—S1—O1	117.8 (4)	C6—C5—H5	120.8
O2—S1—N1	111.2 (3)	C1—C6—C5	118.5 (7)
O1—S1—N1	104.8 (4)	C1—C6—H6	120.7
O2—S1—C1	107.1 (4)	C5—C6—H6	120.7
O1—S1—C1	109.9 (3)	C12—C7—C8	120.9 (7)
N1—S1—C1	105.5 (4)	C12—C7—N1	121.7 (7)
C7—N1—S1	122.0 (5)	C8—C7—N1	117.4 (6)
C7—N1—H1N	110 (6)	C9—C8—C7	119.3 (7)
S1—N1—H1N	120 (6)	C9—C8—H8	120.4
C6—C1—C2	122.5 (7)	C7—C8—H8	120.4
C6—C1—S1	119.4 (6)	C8—C9—C10	120.4 (8)
C2—C1—S1	118.1 (6)	C8—C9—H9	119.8
C1—C2—C3	119.0 (8)	C10—C9—H9	119.8
C1—C2—H2	120.5	C11—C10—C9	120.6 (7)
C3—C2—H2	120.5	C11—C10—I1	119.0 (5)
C4—C3—C2	118.2 (8)	C9—C10—I1	120.4 (6)
C4—C3—H3	120.9	C10—C11—C12	119.2 (7)
C2—C3—H3	120.9	C10—C11—H11	120.4
C3—C4—C5	123.3 (7)	C12—C11—H11	120.4
C3—C4—Br1	118.5 (6)	C7—C12—C11	119.6 (8)
C5—C4—Br1	118.2 (6)	C7—C12—H12	120.2
C4—C5—C6	118.4 (7)	C11—C12—H12	120.2
C4—C5—H5	120.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.92 (7)	1.96 (7)	2.864 (9)	168 (9)

Symmetry code: (i) −x+5/3, −y+7/3, −z+4/3.

(Cl~Br)

Crystal data

C12H9BrClNO2S	F(000) = 3096
Mr = 346.62	Dx = 1.786 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.045 (4) Å	µ = 3.55 mm^−1
c = 9.1556 (10) Å	T = 120 K
V = 5799.5 (13) Å^3	0.50 × 0.15 × 0.02 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2049 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1337 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
φ & ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −32→30
Tmin = 0.270, Tmax = 0.932	k = −30→32
6040 measured reflections	l = −10→10

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0467P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max = 0.003
2049 reflections	Δρmax = 0.46 e Å^−3
172 parameters	Δρmin = −0.62 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00030 (7)

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
S1	0.98949 (6)	0.41760 (6)	0.40495 (16)	0.0230 (4)
Br1	0.73103 (3)	0.30532 (3)	0.00523 (8)	0.0350 (3)
Cl1	0.80272 (7)	0.22322 (7)	0.78723 (17)	0.0314 (4)
O1	1.03061 (17)	0.46238 (17)	0.4981 (4)	0.0278 (10)
O2	1.00980 (17)	0.39220 (17)	0.3024 (4)	0.0262 (10)
N1	0.9565 (2)	0.4457 (2)	0.3208 (5)	0.0242 (12)
H1N	0.959 (3)	0.4758 (17)	0.369 (6)	0.029*
C1	0.9376 (3)	0.3630 (2)	0.5148 (6)	0.0231 (14)
C2	0.9020 (3)	0.3742 (3)	0.6000 (7)	0.0275 (15)
H2	0.9058	0.4111	0.5990	0.034 (18)*
C3	0.8606 (3)	0.3314 (3)	0.6864 (6)	0.0285 (15)
H3	0.8361	0.3386	0.7457	0.021 (15)*
C4	0.8557 (2)	0.2777 (2)	0.6848 (6)	0.0234 (14)
C5	0.8907 (3)	0.2661 (3)	0.5989 (7)	0.0282 (15)
H5	0.8865	0.2290	0.5988	0.034*
C6	0.9326 (3)	0.3096 (3)	0.5117 (7)	0.0257 (14)
H6	0.9570	0.3025	0.4517	0.028 (17)*
C7	0.9037 (2)	0.4118 (2)	0.2472 (6)	0.0228 (14)
C8	0.8609 (2)	0.4248 (2)	0.2675 (6)	0.0232 (14)
H8	0.8668	0.4552	0.3302	0.038 (18)*
C9	0.8087 (3)	0.3928 (3)	0.1952 (7)	0.0296 (15)
H9	0.7789	0.4013	0.2082	0.036*
C10	0.8012 (3)	0.3490 (3)	0.1053 (7)	0.0274 (14)
C11	0.8435 (3)	0.3357 (2)	0.0869 (6)	0.0253 (14)
H11	0.8373	0.3046	0.0260	0.030*
C12	0.8954 (2)	0.3675 (2)	0.1572 (6)	0.0215 (13)
H12	0.9251	0.3588	0.1436	0.020 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0210 (8)	0.0221 (8)	0.0268 (9)	0.0113 (7)	−0.0029 (6)	−0.0054 (6)
Br1	0.0260 (4)	0.0276 (4)	0.0481 (5)	0.0109 (3)	−0.0109 (3)	−0.0034 (3)
Cl1	0.0288 (9)	0.0291 (9)	0.0311 (9)	0.0105 (7)	−0.0001 (6)	0.0010 (6)
O1	0.018 (2)	0.026 (2)	0.039 (2)	0.0111 (19)	−0.0078 (18)	−0.0100 (19)
O2	0.026 (2)	0.030 (2)	0.028 (3)	0.017 (2)	−0.0021 (17)	−0.0059 (17)
N1	0.029 (3)	0.022 (3)	0.026 (3)	0.017 (3)	−0.007 (2)	−0.005 (2)
C1	0.026 (3)	0.021 (3)	0.023 (3)	0.013 (3)	−0.003 (2)	0.000 (2)
C2	0.034 (4)	0.021 (4)	0.031 (4)	0.017 (3)	−0.003 (3)	−0.004 (3)
C3	0.037 (4)	0.032 (4)	0.021 (4)	0.021 (3)	0.005 (3)	0.003 (3)
C4	0.023 (3)	0.022 (3)	0.021 (4)	0.008 (3)	−0.003 (2)	−0.002 (2)
C5	0.026 (4)	0.024 (4)	0.036 (4)	0.014 (3)	−0.006 (3)	−0.004 (3)
C6	0.023 (4)	0.028 (4)	0.030 (4)	0.016 (3)	−0.005 (3)	−0.004 (3)
C7	0.021 (3)	0.025 (4)	0.018 (3)	0.009 (3)	0.001 (2)	−0.001 (2)
C8	0.026 (4)	0.016 (3)	0.027 (4)	0.011 (3)	−0.008 (3)	−0.003 (2)
C9	0.022 (4)	0.032 (4)	0.036 (4)	0.014 (3)	0.005 (3)	0.005 (3)
C10	0.025 (4)	0.022 (4)	0.033 (4)	0.010 (3)	−0.004 (3)	0.001 (3)
C11	0.035 (4)	0.017 (3)	0.022 (4)	0.012 (3)	−0.006 (3)	−0.003 (2)
C12	0.024 (3)	0.024 (3)	0.021 (3)	0.015 (3)	−0.007 (2)	−0.005 (2)

Geometric parameters (Å, º)

S1—O2	1.426 (4)	C4—C5	1.381 (8)
S1—O1	1.443 (4)	C5—C6	1.405 (9)
S1—N1	1.628 (5)	C5—H5	0.9500
S1—C1	1.757 (6)	C6—H6	0.9500
Br1—C10	1.896 (6)	C7—C12	1.377 (8)
Cl1—C4	1.730 (6)	C7—C8	1.379 (8)
N1—C7	1.422 (7)	C8—C9	1.400 (9)
N1—H1N	0.893 (15)	C8—H8	0.9500
C1—C6	1.381 (8)	C9—C10	1.371 (9)
C1—C2	1.387 (8)	C9—H9	0.9500
C2—C3	1.387 (8)	C10—C11	1.371 (9)
C2—H2	0.9500	C11—C12	1.385 (8)
C3—C4	1.392 (8)	C11—H11	0.9500
C3—H3	0.9500	C12—H12	0.9500
O2—S1—O1	118.2 (2)	C6—C5—H5	120.3
O2—S1—N1	110.3 (3)	C1—C6—C5	118.8 (6)
O1—S1—N1	105.1 (3)	C1—C6—H6	120.6
O2—S1—C1	108.1 (3)	C5—C6—H6	120.6
O1—S1—C1	108.9 (3)	C12—C7—C8	120.6 (5)
N1—S1—C1	105.7 (3)	C12—C7—N1	121.2 (5)
C7—N1—S1	122.1 (4)	C8—C7—N1	118.1 (5)
C7—N1—H1N	115 (4)	C7—C8—C9	119.7 (6)
S1—N1—H1N	112 (4)	C7—C8—H8	120.2
C6—C1—C2	121.7 (6)	C9—C8—H8	120.2
C6—C1—S1	119.1 (5)	C10—C9—C8	119.0 (6)
C2—C1—S1	119.2 (5)	C10—C9—H9	120.5
C3—C2—C1	119.7 (6)	C8—C9—H9	120.5
C3—C2—H2	120.1	C11—C10—C9	121.2 (6)
C1—C2—H2	120.1	C11—C10—Br1	119.0 (5)
C2—C3—C4	118.8 (6)	C9—C10—Br1	119.8 (5)
C2—C3—H3	120.6	C10—C11—C12	120.0 (6)
C4—C3—H3	120.6	C10—C11—H11	120.0
C5—C4—C3	121.6 (6)	C12—C11—H11	120.0
C5—C4—Cl1	119.1 (5)	C7—C12—C11	119.5 (6)
C3—C4—Cl1	119.2 (5)	C7—C12—H12	120.2
C4—C5—C6	119.3 (6)	C11—C12—H12	120.3
C4—C5—H5	120.3
C2—C1—S1—N1	−47.1 (5)	S1—N1—C7—C8	135.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.89 (2)	1.98 (2)	2.860 (6)	171 (6)

Symmetry code: (i) −x+2, −y+1, −z+1.

(Cl~CCH)

Crystal data

C14H10ClNO2S	F(000) = 2700
Mr = 291.74	Dx = 1.456 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.3848 (15) Å	µ = 0.44 mm^−1
c = 9.2241 (7) Å	T = 120 K
V = 5990.6 (6) Å^3	0.20 × 0.15 × 0.15 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2006 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1620 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.091
φ & ω scans	θmax = 25.1°, θmin = 3.2°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −30→32
Tmin = 0.917, Tmax = 0.937	k = −32→32
4127 measured reflections	l = −10→10

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)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.176	w = 1/[σ^2(Fo^2) + (0.0199P)^2 + 97.2664P] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max = 0.025
2006 reflections	Δρmax = 1.31 e Å^−3
180 parameters	Δρmin = −0.43 e Å^−3
2 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0004 (3)

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
S1	0.76082 (5)	0.08631 (5)	0.06992 (13)	0.0285 (4)
Cl1	0.75459 (6)	−0.10596 (6)	0.44698 (14)	0.0435 (4)
O1	0.76499 (14)	0.13075 (14)	0.1621 (4)	0.0355 (9)
O2	0.71551 (14)	0.06115 (14)	−0.0319 (4)	0.0340 (8)
N1	0.82107 (16)	0.11396 (16)	−0.0133 (4)	0.0296 (9)
H1N	0.8468 (17)	0.1422 (15)	0.042 (5)	0.036*
C1	0.75767 (19)	0.03184 (19)	0.1791 (5)	0.0280 (10)
C2	0.7118 (2)	−0.0221 (2)	0.1693 (5)	0.0321 (11)
H2	0.6816	−0.0299	0.1051	0.039*
C3	0.7103 (2)	−0.0647 (2)	0.2543 (6)	0.0364 (12)
H3	0.6789	−0.1019	0.2498	0.044*
C4	0.7551 (2)	−0.0521 (2)	0.3454 (5)	0.0330 (11)
C5	0.8008 (2)	0.0018 (2)	0.3566 (5)	0.0358 (11)
H5	0.8309	0.0098	0.4210	0.043*
C6	0.8016 (2)	0.0441 (2)	0.2715 (5)	0.0351 (11)
H6	0.8326	0.0815	0.2772	0.042*
C7	0.8396 (2)	0.07990 (19)	−0.0843 (5)	0.0290 (10)
C8	0.8045 (2)	0.0364 (2)	−0.1759 (5)	0.0362 (11)
H8	0.7674	0.0294	−0.1945	0.043*
C9	0.8227 (2)	0.0032 (2)	−0.2400 (6)	0.0402 (13)
H9	0.7979	−0.0272	−0.3007	0.048*
C10	0.8767 (2)	0.0135 (2)	−0.2175 (6)	0.0402 (12)
C11	0.9125 (2)	0.0575 (3)	−0.1275 (6)	0.0448 (13)
H11	0.9498	0.0647	−0.1113	0.054*
C12	0.8943 (2)	0.0915 (2)	−0.0603 (6)	0.0368 (12)
H12	0.9190	0.1219	0.0006	0.044*
C13	0.8947 (2)	−0.0225 (2)	−0.2870 (7)	0.0467 (14)
C14	0.9095 (3)	−0.0513 (2)	−0.3413 (7)	0.0449 (13)
H14	0.922 (4)	−0.069 (4)	−0.399 (9)	0.12 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0258 (6)	0.0268 (6)	0.0312 (7)	0.0119 (5)	−0.0029 (4)	−0.0047 (5)
Cl1	0.0624 (9)	0.0430 (8)	0.0343 (7)	0.0333 (7)	0.0047 (6)	0.0026 (5)
O1	0.0301 (18)	0.0354 (18)	0.041 (2)	0.0164 (15)	−0.0004 (15)	−0.0102 (16)
O2	0.0342 (18)	0.0327 (18)	0.0348 (19)	0.0164 (15)	−0.0075 (14)	−0.0042 (14)
N1	0.026 (2)	0.0218 (19)	0.033 (2)	0.0065 (16)	−0.0009 (16)	−0.0045 (16)
C1	0.027 (2)	0.030 (2)	0.025 (2)	0.013 (2)	0.0055 (18)	−0.0032 (18)
C2	0.031 (2)	0.031 (2)	0.030 (2)	0.013 (2)	−0.0031 (19)	−0.006 (2)
C3	0.039 (3)	0.028 (2)	0.036 (3)	0.012 (2)	0.004 (2)	0.000 (2)
C4	0.042 (3)	0.039 (3)	0.024 (2)	0.024 (2)	0.009 (2)	−0.001 (2)
C5	0.035 (3)	0.042 (3)	0.028 (3)	0.017 (2)	−0.002 (2)	0.000 (2)
C6	0.030 (2)	0.032 (2)	0.033 (3)	0.007 (2)	−0.004 (2)	−0.002 (2)
C7	0.034 (2)	0.027 (2)	0.025 (2)	0.014 (2)	0.0054 (19)	0.0032 (18)
C8	0.035 (3)	0.030 (2)	0.034 (3)	0.010 (2)	0.006 (2)	−0.002 (2)
C9	0.039 (3)	0.033 (3)	0.038 (3)	0.010 (2)	0.013 (2)	0.001 (2)
C10	0.048 (3)	0.033 (3)	0.037 (3)	0.018 (2)	0.013 (2)	0.006 (2)
C11	0.037 (3)	0.059 (4)	0.044 (3)	0.028 (3)	0.006 (2)	0.004 (3)
C12	0.035 (3)	0.042 (3)	0.035 (3)	0.020 (2)	0.001 (2)	0.002 (2)
C13	0.045 (3)	0.044 (3)	0.048 (3)	0.020 (3)	0.010 (3)	0.004 (3)
C14	0.051 (3)	0.032 (3)	0.049 (3)	0.020 (3)	0.008 (3)	−0.002 (2)

Geometric parameters (Å, º)

S1—O2	1.429 (3)	C4—C5	1.381 (7)
S1—O1	1.441 (3)	C5—C6	1.389 (7)
S1—N1	1.624 (4)	C7—C12	1.383 (7)
S1—C1	1.766 (5)	C7—C8	1.384 (7)
Cl1—C4	1.742 (5)	C8—C9	1.371 (7)
N1—C7	1.425 (6)	C9—C10	1.376 (8)
C1—C6	1.372 (7)	C10—C11	1.386 (8)
C1—C2	1.383 (7)	C10—C13	1.452 (8)
C2—C3	1.390 (7)	C11—C12	1.401 (8)
C3—C4	1.381 (7)	C13—C14	1.163 (8)
O2—S1—O1	118.5 (2)	C5—C4—Cl1	119.0 (4)
O2—S1—N1	110.4 (2)	C4—C5—C6	118.5 (5)
O1—S1—N1	104.6 (2)	C1—C6—C5	120.0 (5)
O2—S1—C1	107.7 (2)	C12—C7—C8	120.2 (5)
O1—S1—C1	109.1 (2)	C12—C7—N1	118.4 (4)
N1—S1—C1	105.8 (2)	C8—C7—N1	121.4 (4)
C7—N1—S1	121.6 (3)	C9—C8—C7	120.4 (5)
C6—C1—C2	121.3 (5)	C8—C9—C10	120.7 (5)
C6—C1—S1	118.8 (4)	C9—C10—C11	119.1 (5)
C2—C1—S1	119.9 (4)	C9—C10—C13	119.3 (5)
C1—C2—C3	119.3 (5)	C11—C10—C13	121.6 (5)
C4—C3—C2	118.9 (5)	C10—C11—C12	120.8 (5)
C3—C4—C5	122.0 (5)	C7—C12—C11	118.7 (5)
C3—C4—Cl1	119.0 (4)	C14—C13—C10	179.2 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.90 (1)	1.99 (1)	2.882 (5)	177 (5)

Symmetry code: (i) −x+5/3, −y+1/3, −z+1/3.

(Cl~CF3)

Crystal data

C13H9ClF3NO2S	F(000) = 3060
Mr = 335.72	Dx = 1.585 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.805 (3) Å	µ = 0.46 mm^−1
c = 9.4583 (12) Å	T = 293 K
V = 6332.8 (12) Å^3	0.30 × 0.30 × 0.20 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2745 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1421 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.147
φ & ω scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −34→27
Tmin = 0.875, Tmax = 0.914	k = −34→34
9157 measured reflections	l = −11→11

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.0649P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max = 0.001
2745 reflections	Δρmax = 0.21 e Å^−3
257 parameters	Δρmin = −0.28 e Å^−3
136 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00099 (17)

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)
S1	0.41864 (4)	0.99152 (4)	0.08753 (10)	0.0575 (4)
Cl1	0.22578 (5)	0.81126 (6)	−0.27517 (12)	0.0979 (5)
O1	0.46236 (11)	1.03036 (10)	−0.0033 (3)	0.0717 (8)
O2	0.39526 (11)	1.01244 (10)	0.1873 (3)	0.0683 (8)
N1	0.44584 (12)	0.95927 (12)	0.1691 (3)	0.0556 (8)
H1N	0.4725 (12)	0.9576 (14)	0.115 (3)	0.061 (11)*
C1	0.36432 (15)	0.94098 (16)	−0.0161 (4)	0.0548 (9)
C2	0.31196 (17)	0.93497 (19)	−0.0078 (5)	0.0704 (12)
H2	0.3052	0.9574	0.0525	0.108 (17)*
C3	0.26968 (19)	0.8952 (2)	−0.0904 (5)	0.0796 (13)
H3	0.2344	0.8911	−0.0865	0.110 (17)*
C4	0.27971 (18)	0.86209 (19)	−0.1778 (4)	0.0695 (12)
C5	0.33146 (19)	0.8682 (2)	−0.1857 (4)	0.0782 (13)
H5	0.3380	0.8457	−0.2458	0.078 (13)*
C6	0.37400 (19)	0.90774 (18)	−0.1049 (4)	0.0711 (12)
H6	0.4093	0.9119	−0.1105	0.091 (15)*
C7	0.41346 (14)	0.90833 (15)	0.2438 (3)	0.0485 (9)
C8	0.42671 (16)	0.86718 (16)	0.2288 (4)	0.0593 (10)
H8	0.4565	0.8731	0.1721	0.053 (10)*
C9	0.39616 (17)	0.81755 (17)	0.2971 (4)	0.0664 (11)
H9	0.4055	0.7899	0.2873	0.079 (13)*
C10	0.35154 (16)	0.80830 (16)	0.3807 (4)	0.0568 (10)
C11	0.33936 (16)	0.85036 (17)	0.3966 (4)	0.0596 (10)
H11	0.3098	0.8447	0.4538	0.099 (15)*
C12	0.37018 (15)	0.90032 (16)	0.3293 (4)	0.0564 (10)
H12	0.3618	0.9285	0.3415	0.072 (12)*
C13	0.31758 (17)	0.75483 (19)	0.4521 (5)	0.0818 (14)
F1	0.3088 (4)	0.7134 (3)	0.3528 (8)	0.084 (3)	0.40
F2	0.3421 (5)	0.7450 (5)	0.5576 (10)	0.097 (4)	0.40
F3	0.2667 (3)	0.7429 (5)	0.4873 (12)	0.084 (3)	0.40
F1'	0.2888 (6)	0.7586 (5)	0.5681 (13)	0.101 (3)	0.35
F2'	0.2786 (6)	0.7156 (4)	0.3707 (13)	0.121 (5)	0.35
F3'	0.3463 (4)	0.7323 (5)	0.5100 (12)	0.072 (3)	0.35
F1"	0.3224 (7)	0.7618 (6)	0.5950 (9)	0.101 (5)	0.25
F2"	0.2630 (4)	0.7348 (7)	0.4250 (15)	0.066 (4)	0.25
F3"	0.3281 (7)	0.7146 (5)	0.420 (2)	0.116 (6)	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0543 (6)	0.0468 (6)	0.0758 (6)	0.0286 (5)	0.0138 (5)	0.0103 (5)
Cl1	0.0836 (9)	0.0992 (10)	0.0877 (8)	0.0284 (8)	−0.0174 (6)	0.0041 (7)
O1	0.0662 (18)	0.0517 (16)	0.0978 (18)	0.0298 (15)	0.0288 (16)	0.0245 (14)
O2	0.0697 (18)	0.0611 (17)	0.0860 (17)	0.0415 (15)	0.0171 (14)	0.0004 (14)
N1	0.0475 (19)	0.0485 (19)	0.0729 (19)	0.0256 (16)	0.0118 (16)	0.0086 (16)
C1	0.056 (2)	0.054 (2)	0.060 (2)	0.032 (2)	0.0107 (18)	0.0151 (18)
C2	0.061 (3)	0.075 (3)	0.081 (3)	0.039 (3)	0.014 (2)	0.012 (2)
C3	0.052 (3)	0.090 (4)	0.094 (3)	0.034 (3)	0.002 (2)	0.016 (3)
C4	0.067 (3)	0.072 (3)	0.065 (2)	0.031 (3)	−0.004 (2)	0.013 (2)
C5	0.085 (4)	0.093 (4)	0.073 (3)	0.056 (3)	−0.006 (2)	−0.012 (3)
C6	0.065 (3)	0.085 (3)	0.079 (3)	0.050 (3)	0.002 (2)	−0.006 (2)
C7	0.043 (2)	0.050 (2)	0.0530 (18)	0.0227 (18)	−0.0001 (17)	−0.0013 (17)
C8	0.060 (3)	0.062 (3)	0.066 (2)	0.038 (2)	0.009 (2)	0.000 (2)
C9	0.071 (3)	0.056 (3)	0.082 (3)	0.039 (2)	0.008 (2)	0.007 (2)
C10	0.048 (2)	0.049 (2)	0.070 (2)	0.0223 (19)	−0.0058 (19)	0.0063 (18)
C11	0.052 (2)	0.070 (3)	0.064 (2)	0.036 (2)	0.008 (2)	0.013 (2)
C12	0.057 (2)	0.056 (3)	0.065 (2)	0.035 (2)	0.0081 (19)	0.0057 (19)
C13	0.068 (3)	0.075 (3)	0.103 (4)	0.035 (3)	0.006 (3)	0.017 (3)
F1	0.066 (5)	0.051 (4)	0.125 (6)	0.023 (4)	−0.013 (5)	0.027 (4)
F2	0.107 (7)	0.109 (8)	0.090 (7)	0.064 (5)	−0.005 (6)	0.036 (6)
F3	0.062 (5)	0.088 (6)	0.081 (7)	0.021 (4)	0.007 (4)	0.020 (6)
F1'	0.106 (8)	0.086 (6)	0.122 (8)	0.057 (6)	0.042 (6)	0.041 (6)
F2'	0.101 (8)	0.080 (7)	0.132 (8)	0.008 (6)	−0.041 (7)	0.009 (6)
F3'	0.093 (6)	0.066 (6)	0.065 (5)	0.045 (5)	0.005 (5)	0.011 (5)
F1"	0.097 (9)	0.095 (8)	0.104 (8)	0.043 (7)	−0.015 (7)	0.050 (6)
F2"	0.059 (6)	0.065 (7)	0.053 (7)	0.015 (5)	0.012 (5)	0.011 (6)
F3"	0.120 (10)	0.099 (9)	0.161 (12)	0.079 (8)	0.000 (8)	0.035 (8)

Geometric parameters (Å, º)

S1—O2	1.424 (2)	C8—C9	1.368 (5)
S1—O1	1.438 (2)	C9—C10	1.382 (5)
S1—N1	1.628 (3)	C10—C11	1.379 (5)
S1—C1	1.759 (4)	C10—C13	1.468 (6)
Cl1—C4	1.725 (4)	C11—C12	1.370 (5)
N1—C7	1.429 (4)	C13—F2	1.313 (7)
C1—C6	1.372 (5)	C13—F3	1.325 (6)
C1—C2	1.382 (5)	C13—F3"	1.326 (7)
C2—C3	1.383 (6)	C13—F2'	1.333 (7)
C3—C4	1.367 (6)	C13—F3'	1.353 (7)
C4—C5	1.363 (6)	C13—F2"	1.354 (7)
C5—C6	1.375 (6)	C13—F1"	1.362 (8)
C7—C12	1.373 (5)	C13—F1'	1.392 (7)
C7—C8	1.374 (5)	C13—F1	1.410 (6)
O2—S1—O1	118.41 (16)	F2'—C13—F3'	106.4 (6)
O2—S1—N1	110.11 (16)	F2—C13—F2"	130.6 (9)
O1—S1—N1	104.20 (16)	F3—C13—F2"	26.8 (5)
O2—S1—C1	108.08 (17)	F3"—C13—F2"	106.6 (7)
O1—S1—C1	109.46 (16)	F2'—C13—F2"	42.9 (7)
N1—S1—C1	105.89 (17)	F3'—C13—F2"	133.3 (9)
C7—N1—S1	123.0 (2)	F2—C13—F1"	41.4 (6)
C6—C1—C2	120.2 (4)	F3—C13—F1"	78.7 (7)
C6—C1—S1	120.0 (3)	F3"—C13—F1"	107.2 (6)
C2—C1—S1	119.8 (3)	F2'—C13—F1"	132.2 (8)
C1—C2—C3	119.2 (4)	F3'—C13—F1"	67.9 (7)
C4—C3—C2	120.1 (4)	F2"—C13—F1"	104.9 (6)
C5—C4—C3	120.4 (4)	F2—C13—F1'	78.2 (6)
C5—C4—Cl1	120.3 (4)	F3—C13—F1'	40.4 (5)
C3—C4—Cl1	119.2 (4)	F3"—C13—F1'	128.3 (9)
C4—C5—C6	120.2 (4)	F2'—C13—F1'	104.7 (6)
C1—C6—C5	119.9 (4)	F3'—C13—F1'	102.1 (6)
C12—C7—C8	120.3 (3)	F2"—C13—F1'	67.2 (6)
C12—C7—N1	121.3 (3)	F1"—C13—F1'	39.4 (5)
C8—C7—N1	118.4 (3)	F2—C13—F1	103.4 (5)
C9—C8—C7	120.1 (3)	F3—C13—F1	103.7 (5)
C8—C9—C10	120.3 (4)	F3"—C13—F1	34.9 (7)
C11—C10—C9	118.8 (4)	F2'—C13—F1	37.7 (6)
C11—C10—C13	120.2 (4)	F3'—C13—F1	78.0 (5)
C9—C10—C13	121.0 (4)	F2"—C13—F1	80.6 (7)
C12—C11—C10	121.0 (4)	F1"—C13—F1	137.8 (7)
C11—C12—C7	119.4 (4)	F1'—C13—F1	135.7 (7)
F2—C13—F3	111.1 (6)	F2—C13—C10	115.0 (7)
F2—C13—F3"	68.8 (8)	F3—C13—C10	115.7 (6)
F3—C13—F3"	120.4 (10)	F3"—C13—C10	116.7 (8)
F2—C13—F2'	124.3 (9)	F2'—C13—C10	114.3 (6)
F3—C13—F2'	67.1 (7)	F3'—C13—C10	115.2 (6)
F3"—C13—F2'	67.1 (8)	F2"—C13—C10	110.5 (7)
F2—C13—F3'	26.7 (6)	F1"—C13—C10	110.2 (7)
F3—C13—F3'	126.0 (8)	F1'—C13—C10	112.9 (5)
F3"—C13—F3'	43.1 (8)	F1—C13—C10	106.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.92 (2)	1.97 (2)	2.885 (4)	169 (3)

Symmetry code: (i) −x+1, −y+2, −z.

(Cl~Cl0.2Cl~F0.8)

Crystal data

C12H9Cl1.80F0.20NO2S	F(000) = 2743
Mr = 298.87	Dx = 1.574 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 26.4119 (8) Å	µ = 0.63 mm^−1
c = 9.3936 (5) Å	T = 120 K
V = 5674.9 (4) Å^3	0.25 × 0.20 × 0.20 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2455 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2114 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
φ & ω scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −28→26
Tmin = 0.858, Tmax = 0.884	k = −32→24
5704 measured reflections	l = −11→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0562P)^2 + 8.7408P] where P = (Fo^2 + 2Fc^2)/3
2455 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 0.52 e Å^−3
14 restraints	Δρmin = −0.64 e Å^−3

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)
S1	0.76279 (3)	0.67797 (3)	0.06403 (6)	0.0310 (2)
Cl1	0.75615 (3)	0.86447 (3)	0.45725 (6)	0.0389 (2)
Cl2	0.91212 (6)	0.93455 (6)	−0.32520 (17)	0.0505 (3)	0.80
F1	0.9065 (4)	0.9245 (3)	−0.2816 (14)	0.074 (6)	0.20
O1	0.76548 (8)	0.63453 (7)	0.15124 (19)	0.0375 (4)
O2	0.71623 (8)	0.65901 (8)	−0.03620 (18)	0.0363 (4)
N1	0.82563 (10)	0.71143 (9)	−0.0159 (2)	0.0333 (5)
H1N	0.8508 (10)	0.7053 (13)	0.034 (3)	0.048 (9)*
C1	0.76047 (10)	0.73070 (11)	0.1760 (2)	0.0302 (5)
C2	0.71111 (11)	0.73663 (11)	0.1757 (3)	0.0326 (6)
H2	0.6790	0.7132	0.1150	0.031 (7)*
C3	0.70963 (11)	0.77746 (11)	0.2658 (3)	0.0346 (6)
H3	0.6760	0.7818	0.2691	0.041 (7)*
C4	0.75726 (11)	0.81167 (11)	0.3504 (2)	0.0328 (6)
C5	0.80666 (11)	0.80584 (12)	0.3510 (3)	0.0352 (6)
H5	0.8390	0.8297	0.4107	0.038 (7)*
C6	0.80780 (11)	0.76466 (12)	0.2629 (3)	0.0352 (6)
H6	0.8410	0.7596	0.2620	0.035 (7)*
C7	0.84551 (11)	0.76579 (11)	−0.0879 (2)	0.0308 (5)
C8	0.80908 (12)	0.77390 (12)	−0.1798 (2)	0.0350 (6)
H8	0.7701	0.7433	−0.1952	0.040 (7)*
C9	0.82996 (12)	0.82704 (12)	−0.2490 (3)	0.0379 (6)
H9	0.8051	0.8335	−0.3102	0.041 (8)*
C10	0.88670 (13)	0.87000 (11)	−0.2283 (3)	0.0415 (7)
C11	0.92386 (12)	0.86262 (12)	−0.1378 (3)	0.0408 (6)
H11	0.9632	0.8930	−0.1253	0.054 (9)*
C12	0.90273 (11)	0.81043 (12)	−0.0664 (3)	0.0362 (6)
H12	0.9273	0.8049	−0.0021	0.050 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0289 (3)	0.0308 (3)	0.0340 (4)	0.0155 (3)	−0.0038 (2)	−0.0004 (2)
Cl1	0.0475 (4)	0.0394 (4)	0.0363 (4)	0.0265 (3)	0.0015 (3)	0.0007 (3)
Cl2	0.0466 (6)	0.0370 (5)	0.0669 (8)	0.0202 (5)	0.0106 (5)	0.0183 (6)
F1	0.074 (8)	0.049 (7)	0.089 (9)	0.022 (5)	0.024 (5)	0.038 (5)
O1	0.0337 (10)	0.0323 (10)	0.0467 (10)	0.0165 (8)	−0.0044 (8)	0.0046 (8)
O2	0.0327 (9)	0.0383 (10)	0.0371 (9)	0.0172 (8)	−0.0069 (8)	−0.0056 (8)
N1	0.0344 (12)	0.0360 (12)	0.0346 (11)	0.0212 (10)	−0.0018 (9)	0.0008 (9)
C1	0.0291 (12)	0.0322 (13)	0.0284 (11)	0.0148 (11)	0.0022 (10)	0.0033 (10)
C2	0.0277 (13)	0.0333 (13)	0.0358 (13)	0.0146 (11)	−0.0029 (10)	0.0030 (11)
C3	0.0293 (13)	0.0380 (14)	0.0397 (13)	0.0192 (12)	0.0029 (11)	0.0080 (11)
C4	0.0391 (14)	0.0329 (13)	0.0287 (12)	0.0198 (12)	0.0037 (11)	0.0052 (10)
C5	0.0319 (13)	0.0421 (15)	0.0316 (12)	0.0185 (12)	−0.0028 (11)	0.0005 (11)
C6	0.0324 (13)	0.0447 (15)	0.0336 (13)	0.0232 (12)	−0.0022 (11)	0.0010 (11)
C7	0.0346 (13)	0.0349 (13)	0.0268 (11)	0.0203 (11)	0.0022 (10)	0.0000 (10)
C8	0.0357 (14)	0.0433 (15)	0.0310 (12)	0.0234 (12)	−0.0007 (11)	−0.0015 (11)
C9	0.0408 (15)	0.0496 (16)	0.0321 (13)	0.0292 (14)	0.0024 (11)	0.0039 (12)
C10	0.0463 (16)	0.0394 (15)	0.0443 (15)	0.0254 (14)	0.0107 (13)	0.0088 (13)
C11	0.0353 (15)	0.0373 (15)	0.0472 (15)	0.0163 (12)	0.0029 (12)	0.0030 (12)
C12	0.0358 (14)	0.0422 (15)	0.0352 (13)	0.0228 (12)	−0.0027 (11)	−0.0021 (11)

Geometric parameters (Å, º)

S1—O2	1.4260 (18)	C4—C5	1.388 (4)
S1—O1	1.4402 (18)	C5—C6	1.379 (4)
S1—N1	1.623 (2)	C5—H5	0.9500
S1—C1	1.771 (3)	C6—H6	0.9500
Cl1—C4	1.730 (3)	C7—C8	1.387 (3)
Cl2—C10	1.744 (3)	C7—C12	1.390 (4)
F1—C10	1.357 (4)	C8—C9	1.387 (4)
N1—C7	1.428 (3)	C8—H8	0.9500
N1—H1N	0.894 (10)	C9—C10	1.368 (4)
C1—C6	1.383 (3)	C9—H9	0.9500
C1—C2	1.389 (3)	C10—C11	1.384 (4)
C2—C3	1.387 (4)	C11—C12	1.376 (4)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.376 (3)	C12—H12	0.9500
C3—H3	0.9500
O2—S1—O1	118.25 (11)	C5—C6—C1	119.8 (2)
O2—S1—N1	110.69 (11)	C5—C6—H6	120.1
O1—S1—N1	104.64 (11)	C1—C6—H6	120.1
O2—S1—C1	107.80 (11)	C8—C7—C12	120.2 (2)
O1—S1—C1	108.87 (11)	C8—C7—N1	121.0 (2)
N1—S1—C1	105.95 (11)	C12—C7—N1	118.8 (2)
C7—N1—S1	121.89 (18)	C9—C8—C7	119.5 (3)
C7—N1—H1N	120 (2)	C9—C8—H8	120.2
S1—N1—H1N	107.9 (19)	C7—C8—H8	120.2
C6—C1—C2	121.6 (2)	C10—C9—C8	119.3 (2)
C6—C1—S1	119.04 (19)	C10—C9—H9	120.4
C2—C1—S1	119.40 (19)	C8—C9—H9	120.4
C3—C2—C1	118.7 (2)	F1—C10—C9	120.6 (4)
C3—C2—H2	120.7	F1—C10—C11	116.8 (4)
C1—C2—H2	120.7	C9—C10—C11	122.1 (2)
C4—C3—C2	119.4 (2)	F1—C10—Cl2	10.0 (7)
C4—C3—H3	120.3	C9—C10—Cl2	117.6 (2)
C2—C3—H3	120.3	C11—C10—Cl2	120.3 (2)
C3—C4—C5	122.0 (2)	C12—C11—C10	118.7 (3)
C3—C4—Cl1	119.1 (2)	C12—C11—H11	120.7
C5—C4—Cl1	118.9 (2)	C10—C11—H11	120.7
C6—C5—C4	118.5 (2)	C11—C12—C7	120.2 (2)
C6—C5—H5	120.7	C11—C12—H12	119.9
C4—C5—H5	120.7	C7—C12—H12	119.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.89 (1)	1.99 (1)	2.867 (3)	167 (3)

Symmetry code: (i) −x+5/3, −y+4/3, −z+1/3.

(Cl~I)

Crystal data

C12H9ClINO2S	F(000) = 3420
Mr = 393.61	Dx = 1.950 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.812 (4) Å	µ = 2.74 mm^−1
c = 9.0055 (18) Å	T = 120 K
V = 6032.6 (17) Å^3	0.25 × 0.20 × 0.10 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2603 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2375 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
φ & ω scans	θmax = 26.1°, θmin = 3.2°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −33→34
Tmin = 0.544, Tmax = 0.764	k = −34→25
8871 measured reflections	l = −10→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0251P)^2 + 12.9105P] where P = (Fo^2 + 2Fc^2)/3
2603 reflections	(Δ/σ)max = 0.004
173 parameters	Δρmax = 0.56 e Å^−3
1 restraint	Δρmin = −1.03 e Å^−3

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
I1	0.270075 (6)	0.701252 (6)	0.992224 (18)	0.02321 (8)
Cl1	0.19376 (3)	0.77742 (3)	0.21811 (7)	0.02653 (15)
N1	0.04113 (8)	0.55491 (8)	0.6726 (2)	0.0170 (4)
H1N	0.0400 (12)	0.5255 (8)	0.629 (3)	0.021 (7)*
S1	0.00913 (2)	0.58227 (2)	0.58634 (6)	0.01596 (13)
O1	−0.02924 (7)	0.53891 (7)	0.4883 (2)	0.0222 (4)
O2	−0.01268 (7)	0.60528 (7)	0.68991 (19)	0.0205 (4)
C1	0.06054 (9)	0.63740 (10)	0.4802 (2)	0.0168 (5)
C2	0.06528 (10)	0.68953 (10)	0.4870 (3)	0.0209 (5)
H2	0.0409	0.6955	0.5479	0.017 (6)*
C3	0.10614 (11)	0.73276 (10)	0.4038 (3)	0.0230 (5)
H3	0.1098	0.7686	0.4065	0.030 (8)*
C4	0.14118 (10)	0.72291 (10)	0.3175 (3)	0.0198 (5)
C5	0.13665 (11)	0.67107 (11)	0.3100 (3)	0.0231 (5)
H5	0.1612	0.6652	0.2492	0.028*
C6	0.09602 (11)	0.62814 (11)	0.3919 (3)	0.0220 (5)
H6	0.0923	0.5923	0.3879	0.027 (8)*
C7	0.09262 (9)	0.58829 (9)	0.7475 (2)	0.0147 (4)
C8	0.10086 (10)	0.63239 (10)	0.8370 (3)	0.0177 (5)
H8	0.0717	0.6403	0.8514	0.027 (8)*
C9	0.15157 (10)	0.66467 (10)	0.9052 (3)	0.0178 (5)
H9	0.1577	0.6953	0.9652	0.022 (7)*
C10	0.19359 (9)	0.65215 (10)	0.8859 (3)	0.0171 (5)
C11	0.18530 (10)	0.60734 (10)	0.7986 (3)	0.0198 (5)
H11	0.2140	0.5985	0.7875	0.034 (8)*
C12	0.13472 (10)	0.57570 (10)	0.7281 (3)	0.0187 (5)
H12	0.1288	0.5455	0.6666	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01629 (10)	0.01729 (10)	0.03220 (13)	0.00551 (7)	−0.00809 (6)	−0.00003 (6)
Cl1	0.0259 (3)	0.0243 (3)	0.0242 (3)	0.0087 (3)	0.0005 (2)	0.0024 (2)
N1	0.0174 (10)	0.0137 (9)	0.0201 (10)	0.0078 (8)	−0.0047 (8)	−0.0043 (8)
S1	0.0131 (3)	0.0155 (3)	0.0201 (3)	0.0077 (2)	−0.0038 (2)	−0.0048 (2)
O1	0.0170 (8)	0.0211 (9)	0.0293 (10)	0.0102 (7)	−0.0097 (7)	−0.0107 (7)
O2	0.0158 (8)	0.0223 (9)	0.0252 (9)	0.0107 (7)	0.0004 (7)	−0.0039 (7)
C1	0.0164 (11)	0.0196 (12)	0.0168 (11)	0.0108 (10)	−0.0059 (9)	−0.0041 (9)
C2	0.0204 (12)	0.0218 (12)	0.0237 (13)	0.0129 (10)	−0.0020 (9)	−0.0047 (10)
C3	0.0264 (13)	0.0173 (12)	0.0270 (13)	0.0123 (10)	−0.0018 (10)	−0.0021 (10)
C4	0.0198 (12)	0.0226 (12)	0.0166 (11)	0.0104 (10)	−0.0032 (9)	0.0008 (9)
C5	0.0280 (13)	0.0284 (13)	0.0207 (12)	0.0199 (11)	0.0021 (10)	0.0012 (10)
C6	0.0303 (13)	0.0213 (12)	0.0213 (12)	0.0181 (11)	0.0003 (10)	−0.0006 (9)
C7	0.0143 (11)	0.0123 (10)	0.0151 (11)	0.0049 (9)	−0.0013 (8)	0.0016 (8)
C8	0.0200 (12)	0.0180 (11)	0.0194 (11)	0.0127 (10)	−0.0006 (9)	−0.0005 (9)
C9	0.0216 (12)	0.0141 (11)	0.0184 (11)	0.0095 (10)	−0.0037 (9)	−0.0007 (9)
C10	0.0140 (11)	0.0165 (11)	0.0173 (11)	0.0049 (9)	−0.0029 (9)	0.0020 (9)
C11	0.0169 (11)	0.0232 (12)	0.0227 (12)	0.0126 (10)	−0.0015 (9)	−0.0008 (10)
C12	0.0205 (12)	0.0174 (11)	0.0206 (12)	0.0113 (10)	−0.0005 (9)	−0.0030 (9)

Geometric parameters (Å, º)

I1—C10	2.098 (2)	C3—C4	1.377 (4)
Cl1—C4	1.738 (2)	C4—C5	1.385 (4)
N1—C7	1.428 (3)	C5—C6	1.377 (4)
N1—S1	1.628 (2)	C7—C8	1.388 (3)
S1—O2	1.4268 (17)	C7—C12	1.391 (3)
S1—O1	1.4440 (17)	C8—C9	1.381 (3)
S1—C1	1.765 (2)	C9—C10	1.387 (3)
C1—C6	1.388 (3)	C10—C11	1.392 (3)
C1—C2	1.390 (3)	C11—C12	1.385 (3)
C2—C3	1.390 (4)
C7—N1—S1	121.75 (16)	C5—C4—Cl1	118.81 (19)
O2—S1—O1	118.16 (10)	C6—C5—C4	119.0 (2)
O2—S1—N1	110.62 (10)	C5—C6—C1	119.8 (2)
O1—S1—N1	104.45 (10)	C8—C7—C12	120.5 (2)
O2—S1—C1	107.80 (11)	C8—C7—N1	121.2 (2)
O1—S1—C1	109.50 (11)	C12—C7—N1	118.3 (2)
N1—S1—C1	105.62 (11)	C9—C8—C7	119.8 (2)
C6—C1—C2	120.9 (2)	C8—C9—C10	119.7 (2)
C6—C1—S1	119.43 (18)	C9—C10—C11	120.8 (2)
C2—C1—S1	119.67 (18)	C9—C10—I1	119.12 (17)
C1—C2—C3	119.2 (2)	C11—C10—I1	120.05 (17)
C4—C3—C2	119.1 (2)	C12—C11—C10	119.2 (2)
C3—C4—C5	122.0 (2)	C11—C12—C7	119.9 (2)
C3—C4—Cl1	119.20 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.90 (1)	1.97 (1)	2.855 (3)	171 (3)

Symmetry code: (i) −x, −y+1, −z+1.

(CN~Br)

Crystal data

C13H9BrN2O2S	F(000) = 3024
Mr = 337.19	Dx = 1.674 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.0722 (8) Å	µ = 3.23 mm^−1
c = 9.4838 (8) Å	T = 120 K
V = 6019.5 (6) Å^3	0.25 × 0.12 × 0.10 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2569 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2043 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.111
φ & ω scans	θmax = 26.0°, θmin = 3.8°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −29→33
Tmin = 0.489, Tmax = 0.717	k = −33→29
7964 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 3.062P] where P = (Fo^2 + 2Fc^2)/3
2569 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.97 e Å^−3
1 restraint	Δρmin = −1.11 e Å^−3

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
S1	0.99449 (3)	0.57001 (3)	0.38468 (8)	0.0200 (2)
Br1	0.732531 (16)	0.427210 (17)	0.00518 (5)	0.04421 (19)
O1	1.03511 (9)	0.56558 (9)	0.4732 (3)	0.0253 (5)
O2	1.01499 (9)	0.61401 (9)	0.2799 (3)	0.0253 (5)
N1	0.95814 (11)	0.50752 (11)	0.3104 (3)	0.0219 (6)
H1N	0.9594 (16)	0.4810 (12)	0.365 (3)	0.029 (10)*
N2	0.78894 (12)	0.58785 (13)	0.8118 (3)	0.0322 (7)
C1	0.94497 (13)	0.57680 (13)	0.4914 (3)	0.0212 (6)
C2	0.91371 (14)	0.53361 (13)	0.5893 (4)	0.0255 (7)
H2	0.9197	0.5020	0.5982	0.027 (9)*
C3	0.87404 (14)	0.53752 (14)	0.6726 (4)	0.0250 (7)
H3	0.8522	0.5085	0.7393	0.034 (10)*
C4	0.86619 (12)	0.58449 (13)	0.6580 (3)	0.0216 (6)
C5	0.89773 (14)	0.62772 (14)	0.5621 (4)	0.0258 (7)
H5	0.8922	0.6596	0.5545	0.035 (11)*
C6	0.93763 (13)	0.62370 (12)	0.4769 (4)	0.0210 (6)
H6	0.9594	0.6527	0.4100	0.017 (8)*
C7	0.90499 (13)	0.48982 (13)	0.2403 (4)	0.0220 (7)
C8	0.85978 (14)	0.43540 (14)	0.2646 (4)	0.0285 (7)
H8	0.8640	0.4111	0.3298	0.037 (11)*
C9	0.80855 (15)	0.41613 (15)	0.1951 (4)	0.0341 (8)
H9	0.7780	0.3784	0.2099	0.050 (13)*
C10	0.80233 (14)	0.45253 (14)	0.1033 (4)	0.0291 (8)
C11	0.84708 (15)	0.50738 (14)	0.0802 (4)	0.0279 (7)
H11	0.8423	0.5321	0.0179	0.038 (11)*
C12	0.89860 (14)	0.52605 (13)	0.1479 (4)	0.0257 (7)
H12	0.9295	0.5635	0.1314	0.030 (10)*
C13	0.82349 (14)	0.58678 (14)	0.7440 (4)	0.0265 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0189 (4)	0.0189 (4)	0.0232 (4)	0.0103 (3)	0.0015 (3)	0.0016 (3)
Br1	0.0321 (2)	0.0385 (2)	0.0645 (3)	0.01948 (18)	−0.01914 (17)	−0.01296 (18)
O1	0.0205 (11)	0.0230 (11)	0.0330 (14)	0.0115 (9)	0.0008 (9)	0.0033 (9)
O2	0.0271 (11)	0.0210 (10)	0.0269 (13)	0.0113 (9)	0.0050 (9)	0.0046 (9)
N1	0.0231 (13)	0.0201 (13)	0.0261 (15)	0.0136 (11)	0.0006 (10)	0.0010 (11)
N2	0.0285 (15)	0.0397 (17)	0.0326 (18)	0.0201 (14)	0.0005 (13)	−0.0055 (13)
C1	0.0216 (15)	0.0226 (15)	0.0195 (18)	0.0111 (12)	−0.0032 (12)	−0.0039 (12)
C2	0.0303 (16)	0.0233 (15)	0.0278 (19)	0.0171 (14)	0.0043 (13)	0.0050 (13)
C3	0.0292 (16)	0.0248 (16)	0.0223 (18)	0.0145 (13)	0.0044 (13)	0.0016 (12)
C4	0.0204 (15)	0.0288 (15)	0.0179 (17)	0.0140 (13)	−0.0027 (11)	−0.0056 (12)
C5	0.0260 (16)	0.0249 (16)	0.031 (2)	0.0161 (14)	−0.0019 (13)	−0.0032 (13)
C6	0.0202 (14)	0.0203 (14)	0.0223 (18)	0.0099 (12)	−0.0021 (12)	0.0020 (12)
C7	0.0236 (15)	0.0217 (15)	0.0232 (18)	0.0131 (13)	0.0016 (12)	−0.0018 (12)
C8	0.0284 (17)	0.0275 (17)	0.030 (2)	0.0145 (14)	−0.0009 (14)	0.0029 (14)
C9	0.0286 (18)	0.0235 (17)	0.046 (2)	0.0097 (14)	0.0031 (15)	0.0025 (15)
C10	0.0272 (17)	0.0286 (17)	0.034 (2)	0.0157 (14)	−0.0024 (14)	−0.0064 (14)
C11	0.0363 (18)	0.0260 (16)	0.0278 (19)	0.0203 (15)	−0.0062 (14)	−0.0050 (14)
C12	0.0264 (16)	0.0217 (15)	0.0282 (19)	0.0115 (13)	0.0000 (13)	0.0001 (13)
C13	0.0255 (16)	0.0274 (17)	0.0283 (19)	0.0146 (14)	−0.0043 (13)	−0.0039 (13)

Geometric parameters (Å, º)

S1—O2	1.433 (2)	C3—C4	1.397 (4)
S1—O1	1.435 (2)	C4—C5	1.388 (5)
S1—N1	1.632 (3)	C4—C13	1.441 (5)
S1—C1	1.761 (3)	C5—C6	1.396 (5)
Br1—C10	1.900 (3)	C7—C8	1.385 (5)
N1—C7	1.433 (4)	C7—C12	1.389 (5)
N2—C13	1.147 (5)	C8—C9	1.381 (5)
C1—C6	1.387 (4)	C9—C10	1.387 (5)
C1—C2	1.398 (5)	C10—C11	1.386 (5)
C2—C3	1.380 (5)	C11—C12	1.381 (5)
O2—S1—O1	118.72 (13)	C3—C4—C13	118.3 (3)
O2—S1—N1	110.15 (14)	C4—C5—C6	119.2 (3)
O1—S1—N1	104.84 (13)	C1—C6—C5	119.0 (3)
O2—S1—C1	108.08 (14)	C8—C7—C12	120.0 (3)
O1—S1—C1	109.13 (14)	C8—C7—N1	118.9 (3)
N1—S1—C1	105.10 (14)	C12—C7—N1	121.0 (3)
C7—N1—S1	122.1 (2)	C9—C8—C7	120.6 (3)
C6—C1—C2	121.8 (3)	C8—C9—C10	119.1 (3)
C6—C1—S1	120.2 (2)	C11—C10—C9	120.6 (3)
C2—C1—S1	117.9 (2)	C11—C10—Br1	119.2 (3)
C3—C2—C1	119.0 (3)	C9—C10—Br1	120.2 (3)
C2—C3—C4	119.5 (3)	C12—C11—C10	120.0 (3)
C5—C4—C3	121.5 (3)	C11—C12—C7	119.6 (3)
C5—C4—C13	120.2 (3)	N2—C13—C4	179.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.90 (1)	2.04 (1)	2.920 (3)	166 (4)

Symmetry code: (i) −x+2, −y+1, −z+1.

(CN~CF3)

Crystal data

C14H9F3N2O2S	F(000) = 2988
Mr = 326.29	Dx = 1.564 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.6017 (8) Å	µ = 0.28 mm^−1
c = 9.4505 (3) Å	T = 120 K
V = 6235.3 (3) Å^3	0.20 × 0.10 × 0.07 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2439 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2065 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
φ & ω scans	θmax = 25.1°, θmin = 3.0°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −32→22
Tmin = 0.947, Tmax = 0.981	k = −31→32
9968 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.21	w = 1/[σ^2(Fo^2) + (0.0657P)^2 + 31.8537P] where P = (Fo^2 + 2Fc^2)/3
2439 reflections	(Δ/σ)max = 0.001
268 parameters	Δρmax = 1.31 e Å^−3
115 restraints	Δρmin = −0.81 e Å^−3

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)
S1	0.90890 (4)	0.67087 (4)	0.05835 (10)	0.0219 (3)
O1	0.86487 (11)	0.63190 (11)	0.1500 (3)	0.0277 (6)
O2	0.93101 (11)	0.64957 (11)	−0.0452 (3)	0.0269 (6)
N1	0.88326 (13)	0.70618 (13)	−0.0175 (3)	0.0240 (7)
H1N	0.8562 (14)	0.706 (2)	0.036 (4)	0.041 (13)*
N2	1.13295 (15)	0.87428 (15)	0.4718 (4)	0.0365 (9)
C1	0.96510 (16)	0.71997 (15)	0.1627 (4)	0.0210 (8)
C2	1.01801 (16)	0.72702 (16)	0.1455 (4)	0.0259 (9)
H2	1.0243	0.7051	0.0785	0.043 (13)*
C3	1.06185 (17)	0.76647 (17)	0.2270 (4)	0.0271 (9)
H3	1.0985	0.7719	0.2167	0.035 (12)*
C4	1.05133 (16)	0.79797 (16)	0.3240 (4)	0.0247 (8)
C5	0.99779 (17)	0.79024 (17)	0.3430 (4)	0.0283 (9)
H5	0.9913	0.8117	0.4108	0.042 (13)*
C6	0.95438 (17)	0.75072 (17)	0.2613 (4)	0.0268 (9)
H6	0.9176	0.7447	0.2726	0.055 (15)*
C7	0.91753 (16)	0.75755 (16)	−0.0890 (4)	0.0243 (8)
C8	0.96022 (17)	0.76437 (18)	−0.1792 (4)	0.0292 (9)
H8	0.9670	0.7343	−0.1948	0.037 (12)*
C9	0.99286 (17)	0.81506 (18)	−0.2462 (4)	0.0329 (10)
H9	1.0225	0.8200	−0.3065	0.041 (13)*
C10	0.98248 (18)	0.85856 (19)	−0.2256 (5)	0.0380 (11)
C11	0.93895 (19)	0.85134 (18)	−0.1369 (5)	0.0395 (11)
H11	0.9315	0.8811	−0.1236	0.037 (12)*
C12	0.90673 (18)	0.80101 (17)	−0.0685 (5)	0.0312 (9)
H12	0.8772	0.7961	−0.0076	0.036 (12)*
C13	1.09722 (17)	0.84059 (18)	0.4063 (4)	0.0295 (9)
C14	1.01944 (15)	0.91268 (16)	−0.3027 (4)	0.0540 (14)
F1	1.0284 (4)	0.9021 (3)	−0.4386 (6)	0.044 (2)	0.37
F2	0.9971 (3)	0.9453 (3)	−0.3194 (10)	0.050 (3)	0.37
F3	1.0705 (2)	0.9432 (3)	−0.2492 (8)	0.038 (2)	0.37
F1'	1.0544 (5)	0.9108 (5)	−0.3980 (12)	0.081 (4)	0.36
F2'	0.9897 (3)	0.9312 (3)	−0.3711 (7)	0.0207 (16)	0.36
F3'	1.0470 (5)	0.9510 (3)	−0.2007 (9)	0.085 (4)	0.36
F1"	0.9987 (10)	0.9198 (8)	−0.4237 (13)	0.125 (8)	0.27
F2"	1.0171 (6)	0.9496 (5)	−0.2116 (14)	0.091 (5)	0.27
F3"	1.0735 (2)	0.9267 (5)	−0.3013 (16)	0.046 (3)	0.27

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0198 (5)	0.0209 (5)	0.0251 (5)	0.0102 (4)	0.0008 (3)	−0.0010 (4)
O1	0.0238 (14)	0.0230 (14)	0.0344 (15)	0.0104 (12)	0.0072 (12)	0.0044 (11)
O2	0.0276 (15)	0.0260 (14)	0.0292 (14)	0.0149 (12)	0.0016 (11)	−0.0043 (11)
N1	0.0187 (16)	0.0262 (17)	0.0275 (17)	0.0115 (14)	−0.0009 (13)	−0.0001 (13)
N2	0.033 (2)	0.034 (2)	0.035 (2)	0.0107 (18)	−0.0061 (17)	0.0004 (16)
C1	0.0238 (19)	0.0231 (19)	0.0182 (17)	0.0132 (16)	0.0002 (14)	0.0034 (14)
C2	0.025 (2)	0.027 (2)	0.026 (2)	0.0131 (17)	0.0033 (16)	0.0018 (16)
C3	0.023 (2)	0.033 (2)	0.027 (2)	0.0152 (18)	0.0021 (15)	0.0040 (16)
C4	0.024 (2)	0.024 (2)	0.0227 (19)	0.0090 (17)	−0.0028 (15)	0.0050 (15)
C5	0.031 (2)	0.032 (2)	0.026 (2)	0.0180 (18)	−0.0027 (16)	−0.0040 (16)
C6	0.024 (2)	0.030 (2)	0.028 (2)	0.0149 (18)	−0.0002 (16)	−0.0030 (16)
C7	0.0207 (19)	0.025 (2)	0.0245 (19)	0.0089 (16)	−0.0062 (15)	−0.0021 (15)
C8	0.029 (2)	0.033 (2)	0.030 (2)	0.0183 (19)	0.0020 (17)	0.0053 (17)
C9	0.026 (2)	0.040 (2)	0.037 (2)	0.019 (2)	0.0013 (17)	0.0111 (19)
C10	0.024 (2)	0.032 (2)	0.056 (3)	0.0126 (19)	−0.002 (2)	0.014 (2)
C11	0.036 (3)	0.026 (2)	0.059 (3)	0.018 (2)	−0.003 (2)	0.001 (2)
C12	0.028 (2)	0.030 (2)	0.038 (2)	0.0162 (18)	−0.0020 (18)	−0.0038 (18)
C13	0.027 (2)	0.031 (2)	0.027 (2)	0.0121 (19)	−0.0008 (17)	0.0052 (17)
C14	0.041 (3)	0.043 (3)	0.083 (4)	0.025 (3)	−0.001 (3)	0.012 (3)
F1	0.046 (5)	0.035 (4)	0.045 (4)	0.016 (4)	0.013 (3)	0.011 (3)
F2	0.056 (5)	0.045 (5)	0.056 (5)	0.029 (4)	−0.007 (4)	0.016 (4)
F3	0.015 (4)	0.031 (4)	0.046 (5)	−0.004 (3)	0.008 (3)	0.009 (4)
F1'	0.044 (6)	0.070 (7)	0.136 (9)	0.033 (5)	0.045 (6)	0.039 (7)
F2'	0.030 (3)	0.018 (3)	0.009 (2)	0.008 (2)	−0.006 (2)	0.003 (2)
F3'	0.065 (6)	0.054 (5)	0.072 (6)	−0.019 (4)	−0.042 (5)	0.030 (4)
F1"	0.128 (10)	0.121 (10)	0.130 (10)	0.066 (7)	−0.005 (6)	0.019 (6)
F2"	0.067 (7)	0.095 (7)	0.111 (8)	0.041 (6)	0.002 (6)	0.037 (6)
F3"	0.040 (5)	0.041 (6)	0.054 (6)	0.018 (4)	0.008 (5)	0.003 (5)

Geometric parameters (Å, º)

S1—O2	1.427 (3)	C8—C9	1.382 (6)
S1—O1	1.441 (3)	C9—C10	1.380 (6)
S1—N1	1.629 (3)	C10—C11	1.395 (7)
S1—C1	1.764 (4)	C10—C14	1.509 (6)
N1—C7	1.422 (5)	C11—C12	1.379 (6)
N2—C13	1.142 (5)	C14—F3	1.328 (3)
C1—C2	1.383 (5)	C14—F2	1.330 (3)
C1—C6	1.388 (5)	C14—F2'	1.332 (3)
C2—C3	1.388 (6)	C14—F1"	1.337 (3)
C3—C4	1.391 (6)	C14—F1'	1.339 (3)
C4—C5	1.395 (6)	C14—F3"	1.340 (3)
C4—C13	1.450 (6)	C14—F3'	1.350 (3)
C5—C6	1.384 (6)	C14—F2"	1.360 (3)
C7—C12	1.387 (6)	C14—F1	1.367 (3)
C7—C8	1.389 (6)
O2—S1—O1	118.66 (16)	F1"—C14—F1'	78.4 (10)
O2—S1—N1	110.38 (16)	F3—C14—F3"	30.6 (5)
O1—S1—N1	104.73 (17)	F2—C14—F3"	129.1 (7)
O2—S1—C1	107.89 (17)	F2'—C14—F3"	134.7 (8)
O1—S1—C1	109.08 (17)	F1"—C14—F3"	117.5 (12)
N1—S1—C1	105.32 (17)	F1'—C14—F3"	45.5 (7)
C7—N1—S1	122.3 (3)	F3—C14—F3'	39.4 (6)
C2—C1—C6	121.7 (4)	F2—C14—F3'	79.9 (5)
C2—C1—S1	120.2 (3)	F2'—C14—F3'	105.1 (4)
C6—C1—S1	118.1 (3)	F1"—C14—F3'	127.6 (9)
C1—C2—C3	119.3 (4)	F1'—C14—F3'	112.1 (8)
C2—C3—C4	118.9 (4)	F3"—C14—F3'	69.9 (6)
C3—C4—C5	121.7 (4)	F3—C14—F2"	73.5 (5)
C3—C4—C13	119.3 (4)	F2—C14—F2"	49.9 (6)
C5—C4—C13	119.0 (4)	F2'—C14—F2"	75.5 (6)
C6—C5—C4	118.9 (4)	F1"—C14—F2"	104.3 (5)
C5—C6—C1	119.4 (4)	F1'—C14—F2"	139.4 (8)
C12—C7—C8	120.2 (4)	F3"—C14—F2"	103.9 (4)
C12—C7—N1	118.2 (4)	F3'—C14—F2"	35.0 (6)
C8—C7—N1	121.6 (4)	F3—C14—F1	104.2 (4)
C9—C8—C7	119.9 (4)	F2—C14—F1	103.1 (4)
C10—C9—C8	120.2 (4)	F2'—C14—F1	80.6 (4)
C9—C10—C11	119.9 (4)	F1"—C14—F1	50.5 (8)
C9—C10—C14	117.5 (4)	F1'—C14—F1	31.7 (5)
C11—C10—C14	122.6 (4)	F3"—C14—F1	77.1 (6)
C12—C11—C10	120.1 (4)	F3'—C14—F1	138.3 (7)
C11—C12—C7	119.8 (4)	F2"—C14—F1	146.7 (8)
N2—C13—C4	179.2 (5)	F3—C14—C10	115.0 (4)
F3—C14—F2	108.6 (4)	F2—C14—C10	114.5 (5)
F3—C14—F2'	127.1 (5)	F2'—C14—C10	111.9 (4)
F2—C14—F2'	25.8 (4)	F1"—C14—C10	115.5 (11)
F3—C14—F1"	128.9 (12)	F1'—C14—C10	115.5 (6)
F2—C14—F1"	54.6 (7)	F3"—C14—C10	112.7 (7)
F2'—C14—F1"	30.3 (8)	F3'—C14—C10	105.6 (5)
F3—C14—F1'	74.0 (6)	F2"—C14—C10	100.0 (7)
F2—C14—F1'	122.1 (6)	F1—C14—C10	110.3 (4)
F2'—C14—F1'	106.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.90 (1)	2.01 (1)	2.895 (4)	170 (4)

Symmetry code: (i) −x+5/3, −y+4/3, −z+1/3.

(CN~Cl)

Crystal data

C13H9ClN2O2S	F(000) = 2700
Mr = 292.73	Dx = 1.473 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 26.8055 (15) Å	µ = 0.45 mm^−1
c = 9.5489 (6) Å	T = 120 K
V = 5942.0 (6) Å^3	0.20 × 0.15 × 0.15 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2482 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2069 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.099
φ & ω scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −28→32
Tmin = 0.916, Tmax = 0.936	k = −29→31
6911 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0615P)^2 + 4.1597P] where P = (Fo^2 + 2Fc^2)/3
2482 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.51 e Å^−3
1 restraint	Δρmin = −0.60 e Å^−3

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
S1	0.00597 (2)	0.43050 (2)	0.11824 (5)	0.02083 (18)
Cl1	0.26643 (3)	0.57654 (3)	0.47870 (9)	0.0564 (3)
N1	0.04278 (8)	0.49414 (7)	0.19068 (17)	0.0234 (4)
H1N	0.0406 (13)	0.5201 (10)	0.135 (2)	0.044 (8)*
N2	0.21147 (8)	0.41325 (9)	−0.3148 (2)	0.0334 (5)
O1	−0.03578 (6)	0.43414 (6)	0.03067 (15)	0.0264 (3)
O2	−0.01378 (7)	0.38643 (6)	0.22254 (15)	0.0268 (3)
C1	0.05571 (9)	0.42379 (8)	0.00987 (19)	0.0206 (4)
C2	0.06300 (9)	0.37610 (9)	0.0231 (2)	0.0230 (4)
H2	0.0412	0.3467	0.0895	0.039 (7)*
C3	0.10283 (9)	0.37245 (9)	−0.0628 (2)	0.0247 (4)
H3	0.1085	0.3403	−0.0563	0.021 (6)*
C4	0.13423 (9)	0.41608 (9)	−0.15801 (19)	0.0224 (4)
C5	0.12604 (9)	0.46335 (9)	−0.1713 (2)	0.0265 (5)
H5	0.1476	0.4926	−0.2380	0.030 (6)*
C6	0.08640 (9)	0.46710 (9)	−0.0868 (2)	0.0260 (5)
H6	0.0802	0.4989	−0.0946	0.038 (7)*
C7	0.09647 (9)	0.51213 (9)	0.2583 (2)	0.0230 (4)
C8	0.10417 (10)	0.47681 (9)	0.3521 (2)	0.0266 (5)
H8	0.0733	0.4391	0.3710	0.030 (6)*
C9	0.15673 (10)	0.49659 (10)	0.4176 (2)	0.0306 (5)
H9	0.1624	0.4722	0.4799	0.042 (7)*
C10	0.20093 (10)	0.55181 (11)	0.3924 (2)	0.0341 (5)
C11	0.19391 (10)	0.58780 (11)	0.3006 (3)	0.0385 (6)
H11	0.2246	0.6259	0.2845	0.052 (8)*
C12	0.14161 (10)	0.56759 (10)	0.2323 (2)	0.0307 (5)
H12	0.1366	0.5917	0.1677	0.044 (8)*
C13	0.17711 (9)	0.41396 (9)	−0.2451 (2)	0.0252 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0216 (3)	0.0204 (3)	0.0226 (3)	0.0120 (2)	0.00264 (18)	0.00141 (18)
Cl1	0.0389 (4)	0.0480 (4)	0.0815 (6)	0.0211 (3)	−0.0264 (3)	−0.0131 (3)
N1	0.0268 (9)	0.0227 (9)	0.0240 (9)	0.0147 (8)	0.0018 (7)	−0.0011 (7)
N2	0.0285 (10)	0.0416 (12)	0.0336 (10)	0.0202 (9)	−0.0008 (8)	−0.0069 (8)
O1	0.0227 (7)	0.0251 (8)	0.0334 (8)	0.0134 (6)	−0.0004 (6)	0.0010 (6)
O2	0.0290 (8)	0.0255 (8)	0.0265 (8)	0.0141 (7)	0.0063 (6)	0.0055 (6)
C1	0.0226 (10)	0.0234 (10)	0.0177 (9)	0.0129 (8)	−0.0016 (7)	−0.0013 (7)
C2	0.0254 (10)	0.0216 (10)	0.0232 (10)	0.0128 (9)	−0.0011 (8)	0.0009 (8)
C3	0.0270 (11)	0.0237 (10)	0.0278 (10)	0.0161 (9)	−0.0031 (8)	−0.0041 (8)
C4	0.0231 (10)	0.0285 (11)	0.0208 (10)	0.0168 (9)	−0.0040 (8)	−0.0060 (8)
C5	0.0325 (11)	0.0294 (11)	0.0219 (10)	0.0187 (10)	0.0045 (8)	0.0038 (8)
C6	0.0331 (12)	0.0262 (11)	0.0264 (11)	0.0206 (10)	0.0034 (8)	0.0022 (8)
C7	0.0276 (11)	0.0237 (10)	0.0203 (10)	0.0147 (9)	0.0035 (8)	−0.0021 (8)
C8	0.0313 (12)	0.0236 (11)	0.0270 (11)	0.0154 (9)	0.0008 (8)	−0.0013 (8)
C9	0.0407 (13)	0.0312 (12)	0.0278 (11)	0.0238 (11)	−0.0052 (9)	−0.0054 (9)
C10	0.0304 (12)	0.0345 (13)	0.0391 (12)	0.0176 (10)	−0.0064 (9)	−0.0093 (10)
C11	0.0287 (12)	0.0282 (12)	0.0529 (15)	0.0100 (10)	−0.0019 (10)	−0.0005 (10)
C12	0.0316 (12)	0.0284 (12)	0.0331 (12)	0.0158 (10)	0.0006 (9)	0.0014 (9)
C13	0.0257 (11)	0.0287 (11)	0.0238 (10)	0.0156 (9)	−0.0043 (8)	−0.0044 (8)

Geometric parameters (Å, º)

S1—O2	1.4291 (14)	C3—C4	1.385 (3)
S1—O1	1.4388 (15)	C4—C5	1.395 (3)
S1—N1	1.6367 (18)	C4—C13	1.443 (3)
S1—C1	1.766 (2)	C5—C6	1.378 (3)
Cl1—C10	1.743 (2)	C7—C8	1.391 (3)
N1—C7	1.424 (3)	C7—C12	1.392 (3)
N2—C13	1.144 (3)	C8—C9	1.382 (3)
C1—C6	1.386 (3)	C9—C10	1.378 (4)
C1—C2	1.392 (3)	C10—C11	1.384 (3)
C2—C3	1.388 (3)	C11—C12	1.387 (3)
O2—S1—O1	118.80 (9)	C5—C4—C13	118.25 (19)
O2—S1—N1	110.37 (9)	C6—C5—C4	119.35 (19)
O1—S1—N1	105.01 (9)	C5—C6—C1	119.04 (18)
O2—S1—C1	108.10 (9)	C8—C7—C12	119.7 (2)
O1—S1—C1	108.58 (9)	C8—C7—N1	122.01 (19)
N1—S1—C1	105.15 (9)	C12—C7—N1	118.20 (19)
C7—N1—S1	121.69 (14)	C9—C8—C7	120.0 (2)
C6—C1—C2	122.19 (18)	C10—C9—C8	119.8 (2)
C6—C1—S1	117.83 (15)	C9—C10—C11	121.1 (2)
C2—C1—S1	119.98 (15)	C9—C10—Cl1	119.17 (19)
C3—C2—C1	118.49 (19)	C11—C10—Cl1	119.77 (19)
C4—C3—C2	119.50 (19)	C10—C11—C12	119.2 (2)
C3—C4—C5	121.42 (18)	C11—C12—C7	120.2 (2)
C3—C4—C13	120.32 (18)	N2—C13—C4	178.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.90 (1)	2.05 (1)	2.926 (2)	165 (2)

Symmetry code: (i) −x, −y+1, −z.

(CN~I)

Crystal data

C13H9IN2O2S	F(000) = 3348
Mr = 384.18	Dx = 1.868 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.4867 (7) Å	µ = 2.50 mm^−1
c = 9.3972 (7) Å	T = 120 K
V = 6148.6 (5) Å^3	0.35 × 0.10 × 0.10 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2357 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1683 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
φ & ω scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −33→33
Tmin = 0.476, Tmax = 0.789	k = −33→33
6654 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0734P)^2] where P = (Fo^2 + 2Fc^2)/3
2357 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 1.98 e Å^−3
2 restraints	Δρmin = −0.81 e Å^−3

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
I1	0.731333 (17)	0.297802 (17)	0.00126 (5)	0.0355 (2)
S1	0.99562 (5)	0.42454 (5)	0.39053 (16)	0.0190 (3)
O1	1.03475 (16)	0.46856 (16)	0.4831 (4)	0.0230 (8)
O2	1.01693 (16)	0.40207 (16)	0.2864 (4)	0.0235 (8)
N1	0.96000 (19)	0.45005 (19)	0.3158 (5)	0.0212 (10)
H1N	0.9558 (19)	0.4732 (18)	0.375 (5)	0.025*
N2	0.7914 (2)	0.2009 (2)	0.8055 (6)	0.0337 (13)
C1	0.9466 (2)	0.3682 (2)	0.4954 (6)	0.0169 (10)
C2	0.9381 (2)	0.3145 (2)	0.4747 (6)	0.0228 (12)
H2	0.9591	0.3079	0.4047	0.027*
C3	0.8990 (2)	0.2710 (2)	0.5568 (6)	0.0239 (12)
H3	0.8935	0.2343	0.5458	0.029*
C4	0.8675 (2)	0.2812 (2)	0.6565 (6)	0.0206 (11)
C5	0.8767 (2)	0.3353 (2)	0.6771 (6)	0.0223 (11)
H5	0.8560	0.3419	0.7477	0.016 (14)*
C6	0.9156 (2)	0.3793 (2)	0.5960 (6)	0.0234 (12)
H6	0.9214	0.4161	0.6079	0.028*
C7	0.9084 (2)	0.4149 (2)	0.2436 (6)	0.0223 (12)
C8	0.9034 (2)	0.3742 (2)	0.1501 (6)	0.0240 (12)
H8	0.9347	0.3694	0.1319	0.029*
C9	0.8522 (3)	0.3400 (2)	0.0820 (7)	0.0275 (13)
H9	0.8483	0.3114	0.0184	0.033*
C10	0.8075 (2)	0.3483 (2)	0.1083 (6)	0.0258 (13)
C11	0.8122 (3)	0.3901 (3)	0.2011 (7)	0.0287 (13)
H11	0.7813	0.3960	0.2169	0.034*
C12	0.8640 (2)	0.4233 (2)	0.2707 (7)	0.0267 (13)
H12	0.8682	0.4515	0.3362	0.032*
C13	0.8248 (2)	0.2364 (2)	0.7399 (6)	0.0227 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0285 (3)	0.0256 (3)	0.0488 (3)	0.01074 (18)	−0.01399 (18)	−0.00218 (17)
S1	0.0172 (6)	0.0167 (6)	0.0222 (8)	0.0078 (5)	−0.0001 (5)	−0.0003 (5)
O1	0.0146 (17)	0.0206 (19)	0.033 (2)	0.0082 (15)	−0.0020 (16)	−0.0073 (16)
O2	0.023 (2)	0.022 (2)	0.025 (2)	0.0115 (17)	0.0023 (16)	0.0020 (16)
N1	0.022 (2)	0.018 (2)	0.025 (3)	0.0111 (19)	−0.0003 (19)	−0.0001 (19)
N2	0.028 (3)	0.027 (3)	0.036 (3)	0.006 (2)	−0.003 (2)	0.007 (2)
C1	0.019 (3)	0.017 (2)	0.014 (3)	0.009 (2)	−0.005 (2)	0.000 (2)
C2	0.024 (3)	0.019 (3)	0.026 (3)	0.011 (2)	0.003 (2)	−0.005 (2)
C3	0.028 (3)	0.019 (3)	0.028 (3)	0.014 (2)	−0.001 (2)	−0.003 (2)
C4	0.021 (3)	0.023 (3)	0.016 (3)	0.009 (2)	−0.004 (2)	0.001 (2)
C5	0.025 (3)	0.026 (3)	0.019 (3)	0.015 (2)	0.003 (2)	0.000 (2)
C6	0.029 (3)	0.020 (3)	0.025 (3)	0.015 (2)	0.003 (2)	0.001 (2)
C7	0.022 (3)	0.014 (2)	0.029 (3)	0.008 (2)	0.002 (2)	0.013 (2)
C8	0.026 (3)	0.024 (3)	0.024 (3)	0.015 (2)	−0.003 (2)	−0.002 (2)
C9	0.035 (3)	0.018 (3)	0.029 (3)	0.012 (2)	−0.001 (3)	0.003 (2)
C10	0.026 (3)	0.024 (3)	0.028 (3)	0.012 (2)	−0.008 (2)	0.007 (2)
C11	0.025 (3)	0.032 (3)	0.032 (4)	0.016 (3)	0.000 (2)	0.001 (3)
C12	0.030 (3)	0.022 (3)	0.031 (3)	0.015 (2)	−0.001 (2)	−0.002 (2)
C13	0.021 (3)	0.023 (3)	0.022 (3)	0.009 (2)	−0.003 (2)	0.001 (2)

Geometric parameters (Å, º)

I1—C10	2.102 (6)	C3—C4	1.396 (8)
S1—O2	1.429 (4)	C4—C5	1.391 (8)
S1—O1	1.441 (4)	C4—C13	1.437 (7)
S1—N1	1.622 (4)	C5—C6	1.377 (8)
S1—C1	1.759 (5)	C7—C12	1.374 (8)
N1—C7	1.427 (7)	C7—C8	1.374 (8)
N2—C13	1.130 (8)	C8—C9	1.396 (8)
C1—C2	1.388 (7)	C9—C10	1.380 (8)
C1—C6	1.404 (8)	C10—C11	1.396 (8)
C2—C3	1.377 (8)	C11—C12	1.410 (8)
O2—S1—O1	118.7 (2)	C5—C4—C13	118.3 (5)
O2—S1—N1	110.9 (2)	C6—C5—C4	120.6 (5)
O1—S1—N1	104.9 (2)	C5—C6—C1	118.1 (5)
O2—S1—C1	107.6 (2)	C12—C7—C8	121.3 (5)
O1—S1—C1	108.8 (3)	C12—C7—N1	117.7 (5)
N1—S1—C1	105.1 (2)	C8—C7—N1	121.1 (5)
C7—N1—S1	121.6 (4)	C7—C8—C9	119.9 (5)
C2—C1—C6	121.8 (5)	C10—C9—C8	119.1 (6)
C2—C1—S1	120.3 (4)	C9—C10—C11	121.7 (5)
C6—C1—S1	117.9 (4)	C9—C10—I1	118.7 (4)
C3—C2—C1	119.2 (5)	C11—C10—I1	119.5 (4)
C2—C3—C4	119.7 (5)	C10—C11—C12	118.0 (5)
C3—C4—C5	120.5 (5)	C7—C12—C11	120.0 (6)
C3—C4—C13	121.2 (5)	N2—C13—C4	179.4 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.90 (1)	2.00 (1)	2.877 (6)	167 (4)

Symmetry code: (i) −x+2, −y+1, −z+1.

(CN~Me)

Crystal data

C14H12N2O2S	F(000) = 2556
Mr = 272.32	Dx = 1.345 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 26.9964 (6) Å	µ = 0.24 mm^−1
c = 9.5869 (5) Å	T = 120 K
V = 6050.9 (4) Å^3	0.20 × 0.15 × 0.14 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2632 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1943 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.102
φ & ω scans	θmax = 26.0°, θmin = 3.8°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −32→33
Tmin = 0.954, Tmax = 0.966	k = −33→32
11791 measured reflections	l = −11→11

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0597P)^2 + 0.2548P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2632 reflections	Δρmax = 0.37 e Å^−3
192 parameters	Δρmin = −0.41 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0012 (3)

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)
S1	0.00497 (2)	0.43001 (2)	0.11753 (5)	0.02410 (19)
O1	−0.03660 (5)	0.43383 (5)	0.02997 (15)	0.0286 (4)
O2	−0.01469 (6)	0.38656 (5)	0.22189 (14)	0.0292 (4)
N1	0.04170 (7)	0.49317 (7)	0.18941 (17)	0.0261 (4)
H1N	0.0401 (9)	0.5183 (7)	0.1315 (19)	0.039 (6)*
N2	0.21013 (8)	0.41434 (8)	−0.31327 (19)	0.0395 (5)
C1	0.05387 (8)	0.42272 (8)	0.0093 (2)	0.0224 (4)
C2	0.06388 (8)	0.37756 (8)	0.0280 (2)	0.0269 (5)
H2	0.0439	0.3496	0.0979	0.047 (7)*
C3	0.10330 (8)	0.37374 (8)	−0.0563 (2)	0.0283 (5)
H3	0.1105	0.3429	−0.0455	0.036 (6)*
C4	0.13240 (8)	0.41540 (8)	−0.1572 (2)	0.0255 (4)
C5	0.12116 (8)	0.46014 (8)	−0.1771 (2)	0.0285 (5)
H5	0.1405	0.4878	−0.2479	0.031 (5)*
C6	0.08178 (8)	0.46364 (8)	−0.0930 (2)	0.0277 (5)
H6	0.0738	0.4939	−0.1050	0.039 (6)*
C7	0.09526 (8)	0.51112 (8)	0.2566 (2)	0.0257 (4)
C8	0.10257 (9)	0.47652 (9)	0.3515 (2)	0.0312 (5)
H8	0.0716	0.4395	0.3729	0.052 (7)*
C9	0.15503 (9)	0.49610 (9)	0.4148 (2)	0.0344 (5)
H9	0.1598	0.4718	0.4783	0.043 (6)*
C10	0.20086 (9)	0.55000 (10)	0.3887 (2)	0.0390 (5)
C11	0.19260 (10)	0.58444 (10)	0.2943 (3)	0.0437 (6)
H11	0.2232	0.6219	0.2755	0.053 (7)*
C12	0.14076 (9)	0.56519 (8)	0.2274 (2)	0.0344 (5)
H12	0.1363	0.5890	0.1616	0.039 (6)*
C13	0.17527 (8)	0.41377 (9)	−0.2434 (2)	0.0293 (5)
C14	0.25763 (11)	0.57048 (13)	0.4612 (4)	0.0645 (9)
H14A	0.2849	0.6094	0.4303	0.07 (2)*	0.51 (6)
H14B	0.2724	0.5449	0.4379	0.057 (19)*	0.51 (6)
H14C	0.2523	0.5704	0.5624	0.12 (3)*	0.51 (6)
H14D	0.2549	0.5404	0.5234	0.045 (18)*	0.49 (6)
H14E	0.2673	0.6049	0.5158	0.09 (2)*	0.49 (6)
H14F	0.2875	0.5794	0.3914	0.050 (19)*	0.49 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0259 (3)	0.0243 (3)	0.0242 (3)	0.0142 (2)	0.0036 (2)	0.00197 (19)
O1	0.0248 (7)	0.0298 (7)	0.0335 (8)	0.0154 (6)	−0.0002 (6)	0.0031 (6)
O2	0.0334 (8)	0.0268 (7)	0.0270 (8)	0.0147 (6)	0.0077 (6)	0.0069 (6)
N1	0.0323 (9)	0.0239 (9)	0.0262 (10)	0.0171 (8)	0.0026 (7)	−0.0003 (7)
N2	0.0342 (10)	0.0556 (12)	0.0342 (11)	0.0267 (9)	−0.0047 (8)	−0.0119 (9)
C1	0.0248 (10)	0.0227 (9)	0.0212 (10)	0.0131 (8)	−0.0015 (8)	−0.0019 (8)
C2	0.0313 (11)	0.0254 (10)	0.0256 (11)	0.0154 (9)	−0.0008 (9)	0.0015 (8)
C3	0.0353 (11)	0.0296 (11)	0.0285 (11)	0.0228 (9)	−0.0033 (9)	−0.0035 (9)
C4	0.0253 (10)	0.0332 (11)	0.0222 (11)	0.0177 (9)	−0.0057 (8)	−0.0073 (8)
C5	0.0331 (11)	0.0290 (11)	0.0253 (11)	0.0169 (9)	0.0050 (9)	0.0035 (9)
C6	0.0326 (11)	0.0277 (11)	0.0284 (11)	0.0193 (9)	0.0021 (9)	0.0026 (8)
C7	0.0287 (10)	0.0281 (11)	0.0234 (10)	0.0164 (9)	0.0023 (8)	−0.0044 (8)
C8	0.0393 (12)	0.0300 (11)	0.0258 (11)	0.0186 (10)	−0.0005 (9)	−0.0029 (9)
C9	0.0456 (13)	0.0357 (12)	0.0302 (12)	0.0265 (11)	−0.0071 (10)	−0.0064 (9)
C10	0.0359 (12)	0.0414 (13)	0.0441 (14)	0.0225 (11)	−0.0078 (11)	−0.0104 (11)
C11	0.0362 (13)	0.0341 (13)	0.0517 (16)	0.0107 (11)	−0.0010 (11)	−0.0023 (11)
C12	0.0350 (12)	0.0280 (11)	0.0400 (13)	0.0156 (10)	0.0042 (10)	0.0028 (9)
C13	0.0288 (11)	0.0384 (12)	0.0262 (11)	0.0209 (10)	−0.0067 (9)	−0.0075 (9)
C14	0.0421 (16)	0.0575 (19)	0.088 (3)	0.0205 (14)	−0.0196 (16)	−0.0078 (17)

Geometric parameters (Å, º)

S1—O2	1.4268 (13)	C4—C5	1.398 (3)
S1—O1	1.4459 (14)	C4—C13	1.440 (3)
S1—N1	1.6355 (17)	C5—C6	1.374 (3)
S1—C1	1.7657 (18)	C7—C8	1.387 (3)
N1—C7	1.428 (2)	C7—C12	1.387 (3)
N2—C13	1.149 (3)	C8—C9	1.380 (3)
C1—C6	1.385 (3)	C9—C10	1.382 (3)
C1—C2	1.386 (3)	C10—C11	1.393 (3)
C2—C3	1.381 (3)	C10—C14	1.513 (3)
C3—C4	1.391 (3)	C11—C12	1.383 (3)
O2—S1—O1	118.87 (8)	C5—C4—C13	118.26 (18)
O2—S1—N1	110.12 (9)	C6—C5—C4	119.30 (18)
O1—S1—N1	104.94 (8)	C5—C6—C1	119.45 (17)
O2—S1—C1	108.19 (8)	C8—C7—C12	119.44 (19)
O1—S1—C1	108.48 (8)	C8—C7—N1	121.87 (18)
N1—S1—C1	105.45 (9)	C12—C7—N1	118.68 (18)
C7—N1—S1	121.80 (13)	C9—C8—C7	119.65 (19)
C6—C1—C2	121.70 (18)	C8—C9—C10	122.1 (2)
C6—C1—S1	117.81 (14)	C9—C10—C11	117.5 (2)
C2—C1—S1	120.49 (15)	C9—C10—C14	120.8 (2)
C3—C2—C1	119.12 (18)	C11—C10—C14	121.7 (2)
C2—C3—C4	119.45 (17)	C12—C11—C10	121.3 (2)
C3—C4—C5	120.96 (17)	C11—C12—C7	119.9 (2)
C3—C4—C13	120.78 (17)	N2—C13—C4	177.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.90 (1)	2.05 (1)	2.932 (2)	169 (2)

Symmetry code: (i) −x, −y+1, −z.

(F~Br)

Crystal data

C12H9BrFNO2S	F(000) = 2952
Mr = 330.17	Dx = 1.759 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 26.5333 (4) Å	µ = 3.47 mm^−1
c = 9.2014 (3) Å	T = 120 K
V = 5610.1 (2) Å^3	Block, colourless
Z = 18	0.3 × 0.2 × 0.1 mm

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2449 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2094 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ & ω scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −31→29
Tmin = 0.423, Tmax = 0.723	k = −28→32
12683 measured reflections	l = −11→11

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0507P)^2 + 1.966P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2449 reflections	Δρmax = 0.42 e Å^−3
176 parameters	Δρmin = −1.04 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00044 (8)

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
Br1	0.698790 (11)	0.271028 (11)	−0.00303 (3)	0.03248 (14)
S1	0.58295 (3)	0.01029 (3)	0.40204 (7)	0.02476 (17)
O1	0.53763 (8)	−0.03152 (8)	0.4955 (2)	0.0316 (4)
O2	0.60847 (8)	−0.01049 (8)	0.29902 (19)	0.0284 (4)
N1	0.55297 (9)	0.04293 (9)	0.3181 (2)	0.0254 (5)
H1	0.5236 (12)	0.0411 (12)	0.365 (3)	0.027 (7)*
F1	0.76760 (8)	0.18456 (8)	0.76793 (19)	0.0502 (5)
C1	0.63936 (11)	0.06370 (11)	0.5096 (3)	0.0255 (5)
C2	0.69438 (11)	0.07032 (11)	0.5027 (3)	0.0288 (6)
H2	0.7021	0.0470	0.4383	0.035 (7)*
C3	0.73823 (12)	0.11129 (12)	0.5905 (3)	0.0340 (6)
H3	0.7763	0.1165	0.5877	0.041 (8)*
C4	0.72510 (13)	0.14427 (12)	0.6819 (3)	0.0367 (7)
C5	0.67060 (14)	0.13857 (13)	0.6897 (3)	0.0382 (7)
H5	0.6632	0.1623	0.7536	0.064 (11)*
C6	0.62717 (12)	0.09774 (12)	0.6028 (3)	0.0329 (6)
H6	0.5891	0.0928	0.6063	0.045 (9)*
C7	0.58758 (10)	0.09640 (10)	0.2430 (3)	0.0215 (5)
C8	0.57795 (11)	0.14252 (11)	0.2683 (3)	0.0260 (5)
H8	0.5491	0.1383	0.3359	0.036 (8)*
C9	0.61059 (11)	0.19475 (11)	0.1946 (3)	0.0274 (6)
H9	0.6038	0.2263	0.2098	0.032 (8)*
C10	0.65316 (10)	0.20015 (10)	0.0988 (3)	0.0242 (5)
C11	0.66357 (11)	0.15485 (11)	0.0739 (3)	0.0252 (5)
H11	0.6935	0.1596	0.0090	0.030 (7)*
C12	0.62977 (10)	0.10220 (11)	0.1450 (3)	0.0239 (5)
H12	0.6356	0.0703	0.1264	0.020 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02741 (18)	0.02598 (18)	0.0395 (2)	0.00996 (12)	0.00077 (10)	0.00971 (10)
S1	0.0278 (3)	0.0241 (3)	0.0260 (4)	0.0158 (3)	0.0085 (2)	0.0063 (2)
O1	0.0344 (10)	0.0267 (9)	0.0367 (11)	0.0175 (8)	0.0150 (8)	0.0127 (8)
O2	0.0337 (10)	0.0286 (9)	0.0286 (10)	0.0200 (8)	0.0080 (7)	0.0031 (7)
N1	0.0238 (11)	0.0286 (11)	0.0268 (12)	0.0153 (9)	0.0060 (9)	0.0066 (9)
F1	0.0569 (11)	0.0456 (10)	0.0414 (11)	0.0207 (9)	−0.0162 (8)	−0.0055 (8)
C1	0.0315 (13)	0.0278 (13)	0.0209 (13)	0.0177 (11)	0.0048 (10)	0.0075 (10)
C2	0.0330 (14)	0.0310 (14)	0.0266 (14)	0.0192 (12)	0.0089 (11)	0.0096 (11)
C3	0.0307 (15)	0.0356 (15)	0.0338 (16)	0.0152 (12)	0.0036 (12)	0.0102 (12)
C4	0.0447 (17)	0.0347 (15)	0.0269 (15)	0.0169 (13)	−0.0061 (12)	0.0048 (12)
C5	0.0577 (19)	0.0442 (17)	0.0266 (15)	0.0358 (15)	−0.0059 (13)	−0.0026 (12)
C6	0.0390 (16)	0.0428 (16)	0.0270 (15)	0.0281 (14)	0.0009 (11)	0.0021 (12)
C7	0.0211 (12)	0.0240 (12)	0.0200 (12)	0.0119 (10)	−0.0004 (9)	0.0019 (9)
C8	0.0271 (13)	0.0305 (13)	0.0238 (13)	0.0171 (11)	0.0040 (10)	0.0004 (10)
C9	0.0343 (14)	0.0253 (13)	0.0280 (14)	0.0189 (11)	−0.0006 (11)	−0.0005 (10)
C10	0.0221 (12)	0.0264 (13)	0.0208 (13)	0.0098 (10)	−0.0044 (9)	0.0024 (10)
C11	0.0245 (13)	0.0316 (13)	0.0212 (13)	0.0154 (11)	0.0034 (10)	0.0041 (10)
C12	0.0265 (13)	0.0262 (13)	0.0229 (13)	0.0161 (11)	0.0013 (10)	0.0011 (10)

Geometric parameters (Å, º)

Br1—C10	1.898 (2)	C4—C5	1.379 (4)
S1—O2	1.4263 (17)	C5—C6	1.376 (4)
S1—O1	1.4432 (18)	C5—H5	0.9500
S1—N1	1.633 (2)	C6—H6	0.9500
S1—C1	1.763 (3)	C7—C12	1.385 (3)
N1—C7	1.425 (3)	C7—C8	1.389 (3)
N1—H1	0.87 (3)	C8—C9	1.389 (4)
F1—C4	1.355 (3)	C8—H8	0.9500
C1—C2	1.382 (4)	C9—C10	1.382 (4)
C1—C6	1.396 (4)	C9—H9	0.9500
C2—C3	1.387 (4)	C10—C11	1.381 (4)
C2—H2	0.9500	C11—C12	1.389 (3)
C3—C4	1.379 (4)	C11—H11	0.9500
C3—H3	0.9500	C12—H12	0.9500
O2—S1—O1	118.23 (11)	C4—C5—H5	120.8
O2—S1—N1	110.00 (11)	C5—C6—C1	119.5 (3)
O1—S1—N1	104.48 (11)	C5—C6—H6	120.2
O2—S1—C1	107.92 (11)	C1—C6—H6	120.2
O1—S1—C1	109.23 (11)	C12—C7—C8	120.4 (2)
N1—S1—C1	106.39 (11)	C12—C7—N1	120.6 (2)
C7—N1—S1	120.99 (17)	C8—C7—N1	119.0 (2)
C7—N1—H1	114.2 (18)	C7—C8—C9	120.0 (2)
S1—N1—H1	113.2 (18)	C7—C8—H8	120.0
C2—C1—C6	121.2 (2)	C9—C8—H8	120.0
C2—C1—S1	119.6 (2)	C10—C9—C8	118.9 (2)
C6—C1—S1	119.1 (2)	C10—C9—H9	120.5
C1—C2—C3	119.4 (2)	C8—C9—H9	120.5
C1—C2—H2	120.3	C11—C10—C9	121.6 (2)
C3—C2—H2	120.3	C11—C10—Br1	118.32 (18)
C4—C3—C2	118.3 (3)	C9—C10—Br1	120.05 (19)
C4—C3—H3	120.9	C10—C11—C12	119.2 (2)
C2—C3—H3	120.9	C10—C11—H11	120.4
F1—C4—C3	118.9 (3)	C12—C11—H11	120.4
F1—C4—C5	118.0 (3)	C7—C12—C11	119.9 (2)
C3—C4—C5	123.1 (3)	C7—C12—H12	120.1
C6—C5—C4	118.4 (3)	C11—C12—H12	120.1
C6—C5—H5	120.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.87 (3)	1.98 (3)	2.843 (3)	169 (3)

Symmetry code: (i) −x+1, −y, −z+1.

(F~CF3)

Crystal data

C13H9F4NO2S	F(000) = 2916
Mr = 319.27	Dx = 1.540 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.4403 (4) Å	µ = 0.28 mm^−1
c = 9.5034 (3) Å	T = 293 K
V = 6197.1 (2) Å^3	0.35 × 0.20 × 0.15 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2654 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
φ & ω scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −32→32
Tmin = 0.907, Tmax = 0.959	k = −30→32
13733 measured reflections	l = −9→11

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.140	w = 1/[σ^2(Fo^2) + (0.0827P)^2 + 2.9799P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.008
2654 reflections	Δρmax = 0.32 e Å^−3
249 parameters	Δρmin = −0.42 e Å^−3
100 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0027 (4)

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)
S1	0.41929 (3)	0.99225 (3)	0.09262 (8)	0.0669 (3)
O1	0.46308 (9)	1.03138 (8)	0.0012 (2)	0.0853 (7)
O2	0.39627 (9)	1.01362 (8)	0.1929 (2)	0.0787 (6)
N1	0.44718 (10)	0.95974 (9)	0.1736 (3)	0.0667 (7)
H1N	0.4764 (9)	0.9610 (12)	0.129 (3)	0.077 (9)*
C1	0.36388 (14)	0.94171 (12)	−0.0097 (3)	0.0694 (8)
C2	0.31087 (15)	0.93482 (15)	0.0027 (4)	0.0833 (9)
H2	0.3040	0.9564	0.0664	0.100*
C3	0.26801 (18)	0.8956 (2)	−0.0803 (5)	0.1076 (13)
H3	0.2319	0.8906	−0.0744	0.129*
C4	0.2798 (2)	0.86446 (19)	−0.1712 (5)	0.1082 (14)
C5	0.3313 (2)	0.8702 (2)	−0.1843 (4)	0.1145 (14)
H5	0.3376	0.8480	−0.2475	0.137*
C6	0.37395 (19)	0.90900 (17)	−0.1033 (4)	0.0926 (10)
H6	0.4098	0.9136	−0.1106	0.111*
C7	0.41432 (10)	0.90903 (10)	0.2489 (3)	0.0533 (6)
C8	0.42506 (12)	0.86548 (12)	0.2301 (3)	0.0662 (7)
H8	0.4538	0.8700	0.1702	0.079*
C9	0.39346 (13)	0.81564 (12)	0.2997 (3)	0.0745 (8)
H9	0.4006	0.7862	0.2866	0.089*
C10	0.35058 (11)	0.80894 (11)	0.3901 (3)	0.0644 (7)
C11	0.34097 (12)	0.85294 (12)	0.4092 (3)	0.0679 (7)
H11	0.3124	0.8487	0.4693	0.081*
C12	0.37283 (12)	0.90286 (12)	0.3411 (3)	0.0653 (7)
H12	0.3666	0.9327	0.3570	0.078*
C13	0.31469 (13)	0.75498 (14)	0.4630 (3)	0.0901 (11)
F1	0.23728 (15)	0.82560 (13)	−0.2512 (3)	0.1622 (13)
F2	0.3416 (4)	0.7369 (4)	0.5443 (7)	0.073 (2)	0.42
F3	0.2903 (5)	0.7141 (3)	0.3652 (8)	0.130 (4)	0.42
F4	0.2752 (3)	0.7553 (3)	0.5467 (11)	0.109 (3)	0.42
F2'	0.3149 (6)	0.7131 (4)	0.3891 (14)	0.152 (5)	0.35
F3'	0.3351 (6)	0.7537 (5)	0.5887 (11)	0.160 (6)	0.35
F4'	0.2602 (2)	0.7376 (5)	0.4620 (15)	0.117 (4)	0.35
F2"	0.3002 (7)	0.7635 (5)	0.5940 (8)	0.084 (3)	0.23
F3"	0.2657 (3)	0.7200 (6)	0.4011 (15)	0.091 (4)	0.23
F4"	0.3413 (6)	0.7270 (6)	0.4947 (13)	0.060 (3)	0.23

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0716 (5)	0.0556 (5)	0.0843 (6)	0.0398 (4)	0.0271 (4)	0.0191 (3)
O1	0.0874 (14)	0.0643 (12)	0.1148 (17)	0.0459 (11)	0.0461 (13)	0.0374 (11)
O2	0.0903 (14)	0.0666 (12)	0.0946 (15)	0.0506 (11)	0.0281 (11)	0.0106 (10)
N1	0.0602 (13)	0.0593 (13)	0.0868 (17)	0.0344 (11)	0.0200 (12)	0.0167 (11)
C1	0.087 (2)	0.0690 (17)	0.0678 (17)	0.0511 (16)	0.0174 (15)	0.0228 (14)
C2	0.080 (2)	0.090 (2)	0.087 (2)	0.0474 (19)	0.0190 (18)	0.0231 (18)
C3	0.089 (3)	0.114 (3)	0.115 (3)	0.047 (3)	0.002 (2)	0.037 (3)
C4	0.127 (4)	0.094 (3)	0.096 (3)	0.049 (3)	−0.030 (3)	0.010 (2)
C5	0.157 (4)	0.121 (3)	0.095 (3)	0.091 (3)	−0.020 (3)	−0.010 (2)
C6	0.114 (3)	0.104 (3)	0.087 (2)	0.075 (2)	−0.002 (2)	0.000 (2)
C7	0.0538 (14)	0.0520 (14)	0.0580 (14)	0.0293 (12)	0.0030 (11)	0.0034 (11)
C8	0.0698 (17)	0.0653 (17)	0.0760 (18)	0.0431 (15)	0.0113 (14)	0.0047 (14)
C9	0.084 (2)	0.0605 (17)	0.092 (2)	0.0458 (16)	0.0021 (17)	0.0049 (15)
C10	0.0543 (15)	0.0598 (16)	0.0754 (18)	0.0256 (12)	−0.0066 (13)	0.0138 (13)
C11	0.0630 (16)	0.0780 (18)	0.0733 (18)	0.0433 (15)	0.0132 (14)	0.0214 (14)
C12	0.0713 (17)	0.0646 (16)	0.0738 (17)	0.0443 (14)	0.0165 (14)	0.0118 (13)
C13	0.083 (2)	0.071 (2)	0.113 (3)	0.0364 (19)	−0.003 (2)	0.023 (2)
F1	0.176 (3)	0.141 (2)	0.144 (2)	0.060 (2)	−0.063 (2)	−0.0094 (19)
F2	0.102 (4)	0.077 (4)	0.044 (4)	0.048 (3)	0.007 (3)	0.007 (3)
F3	0.118 (7)	0.066 (4)	0.131 (6)	−0.011 (4)	−0.058 (6)	0.024 (4)
F4	0.054 (4)	0.097 (5)	0.170 (7)	0.032 (4)	0.029 (4)	0.057 (5)
F2'	0.136 (9)	0.091 (6)	0.210 (11)	0.044 (6)	0.001 (7)	0.048 (7)
F3'	0.157 (9)	0.144 (8)	0.132 (8)	0.039 (6)	−0.050 (7)	0.064 (6)
F4'	0.062 (4)	0.120 (7)	0.136 (8)	0.022 (4)	−0.004 (5)	0.036 (6)
F2"	0.084 (7)	0.081 (6)	0.093 (6)	0.046 (6)	0.020 (6)	0.032 (4)
F3"	0.045 (5)	0.087 (7)	0.111 (8)	0.009 (5)	0.008 (5)	0.016 (6)
F4"	0.088 (5)	0.067 (6)	0.045 (6)	0.055 (5)	0.002 (5)	0.016 (5)

Geometric parameters (Å, º)

S1—O2	1.422 (2)	C8—C9	1.369 (4)
S1—O1	1.436 (2)	C9—C10	1.393 (4)
S1—N1	1.630 (2)	C10—C11	1.371 (4)
S1—C1	1.753 (4)	C10—C13	1.478 (4)
N1—C7	1.417 (3)	C11—C12	1.364 (4)
C1—C2	1.375 (4)	C13—F4'	1.324 (4)
C1—C6	1.386 (4)	C13—F2	1.325 (4)
C2—C3	1.377 (6)	C13—F3'	1.327 (5)
C3—C4	1.364 (6)	C13—F4"	1.332 (5)
C4—C5	1.348 (7)	C13—F3"	1.336 (5)
C4—F1	1.353 (5)	C13—F4	1.348 (4)
C5—C6	1.361 (6)	C13—F3	1.349 (4)
C7—C8	1.378 (4)	C13—F2'	1.350 (5)
C7—C12	1.379 (4)	C13—F2"	1.362 (5)
O2—S1—O1	118.38 (12)	F4"—C13—F3"	109.3 (9)
O2—S1—N1	109.67 (13)	F4'—C13—F4	40.5 (5)
O1—S1—N1	104.40 (12)	F2—C13—F4	105.0 (6)
O2—S1—C1	108.03 (14)	F3'—C13—F4	79.6 (8)
O1—S1—C1	109.06 (14)	F4"—C13—F4	122.9 (7)
N1—S1—C1	106.72 (13)	F3"—C13—F4	75.0 (6)
C7—N1—S1	122.25 (18)	F4'—C13—F3	72.2 (7)
C2—C1—C6	120.4 (4)	F2—C13—F3	103.2 (6)
C2—C1—S1	120.0 (3)	F3'—C13—F3	129.7 (8)
C6—C1—S1	119.6 (3)	F4"—C13—F3	82.2 (7)
C1—C2—C3	119.4 (4)	F3"—C13—F3	36.5 (6)
C4—C3—C2	118.3 (4)	F4—C13—F3	110.2 (6)
C5—C4—F1	118.7 (5)	F4'—C13—F2'	100.1 (7)
C5—C4—C3	123.3 (4)	F2—C13—F2'	75.2 (6)
F1—C4—C3	117.9 (5)	F3'—C13—F2'	105.3 (8)
C4—C5—C6	118.7 (4)	F4"—C13—F2'	52.4 (7)
C5—C6—C1	119.9 (4)	F3"—C13—F2'	65.8 (8)
C8—C7—C12	119.8 (2)	F4—C13—F2'	131.2 (7)
C8—C7—N1	118.6 (2)	F3—C13—F2'	31.2 (5)
C12—C7—N1	121.5 (2)	F4'—C13—F2"	72.2 (7)
C9—C8—C7	120.0 (3)	F2—C13—F2"	78.2 (7)
C8—C9—C10	120.1 (2)	F3'—C13—F2"	49.0 (7)
C11—C10—C9	119.2 (2)	F4"—C13—F2"	100.5 (7)
C11—C10—C13	119.7 (3)	F3"—C13—F2"	104.5 (7)
C9—C10—C13	121.1 (3)	F4—C13—F2"	32.3 (5)
C12—C11—C10	120.9 (3)	F3—C13—F2"	134.9 (7)
C11—C12—C7	120.0 (2)	F2'—C13—F2"	138.4 (8)
F4'—C13—F2	127.6 (7)	F4'—C13—C10	115.1 (6)
F4'—C13—F3'	114.4 (8)	F2—C13—C10	115.6 (5)
F2—C13—F3'	31.1 (8)	F3'—C13—C10	111.7 (6)
F4'—C13—F4"	129.8 (9)	F4"—C13—C10	113.7 (7)
F2—C13—F4"	23.5 (5)	F3"—C13—C10	116.1 (7)
F3'—C13—F4"	54.6 (9)	F4—C13—C10	113.9 (4)
F4'—C13—F3"	35.7 (6)	F3—C13—C10	108.4 (5)
F2—C13—F3"	122.5 (9)	F2'—C13—C10	109.0 (6)
F3'—C13—F3"	131.6 (9)	F2"—C13—C10	111.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.89 (1)	2.00 (1)	2.878 (3)	169 (3)

Symmetry code: (i) −x+1, −y+2, −z.

(F~Cl)

Crystal data

C12H9ClFNO2S	F(000) = 2628
Mr = 285.71	Dx = 1.569 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 25.9241 (8) Å	µ = 0.49 mm^−1
c = 9.3533 (5) Å	T = 120 K
V = 5443.8 (4) Å^3	0.20 × 0.15 × 0.15 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2048 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1870 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.115
φ & ω scans	θmax = 25.1°, θmin = 3.1°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −30→19
Tmin = 0.908, Tmax = 0.930	k = −23→28
5545 measured reflections	l = −10→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1006P)^2 + 9.2341P] where P = (Fo^2 + 2Fc^2)/3
2048 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

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
Cl1	0.69377 (3)	0.27002 (3)	−0.00278 (8)	0.0359 (3)
S1	0.58367 (3)	0.01178 (3)	0.39892 (7)	0.0247 (3)
O1	0.53721 (9)	−0.03205 (9)	0.4882 (2)	0.0310 (5)
O2	0.61125 (9)	−0.00812 (9)	0.2972 (2)	0.0296 (5)
N1	0.55278 (10)	0.04483 (10)	0.3173 (2)	0.0251 (5)
H1	0.5232 (18)	0.0432 (19)	0.371 (4)	0.057 (12)*
F1	0.76709 (9)	0.18713 (9)	0.77503 (19)	0.0452 (5)
C1	0.63981 (12)	0.06579 (12)	0.5087 (3)	0.0241 (6)
C2	0.69662 (12)	0.07336 (12)	0.5058 (3)	0.0285 (6)
H2	0.7058	0.0506	0.4417	0.030 (8)*
C3	0.73976 (13)	0.11409 (13)	0.5963 (3)	0.0323 (7)
H3	0.7789	0.1197	0.5966	0.036 (8)*
C4	0.72463 (14)	0.14635 (13)	0.6861 (3)	0.0336 (7)
C5	0.66925 (14)	0.14066 (15)	0.6904 (3)	0.0353 (7)
H5	0.6610	0.1644	0.7531	0.034 (9)*
C6	0.62572 (13)	0.09940 (14)	0.6011 (3)	0.0313 (7)
H6	0.5866	0.0939	0.6024	0.044 (10)*
C7	0.58759 (12)	0.09919 (12)	0.2412 (3)	0.0223 (6)
C8	0.57812 (12)	0.14673 (12)	0.2663 (3)	0.0266 (6)
H8	0.5495	0.1430	0.3352	0.046 (10)*
C9	0.61005 (13)	0.19918 (12)	0.1914 (3)	0.0287 (6)
H9	0.6031	0.2314	0.2068	0.030 (8)*
C10	0.65251 (12)	0.20429 (12)	0.0935 (3)	0.0252 (6)
C11	0.66324 (12)	0.15810 (12)	0.0694 (3)	0.0249 (6)
H11	0.6933	0.1627	0.0040	0.025 (7)*
C12	0.62968 (12)	0.10475 (12)	0.1417 (3)	0.0243 (6)
H12	0.6355	0.0720	0.1230	0.031 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0306 (4)	0.0282 (4)	0.0443 (5)	0.0114 (3)	0.0031 (3)	0.0108 (3)
S1	0.0257 (4)	0.0245 (4)	0.0269 (4)	0.0148 (3)	0.0065 (2)	0.0045 (2)
O1	0.0311 (11)	0.0273 (10)	0.0366 (11)	0.0161 (9)	0.0129 (8)	0.0091 (8)
O2	0.0343 (11)	0.0294 (10)	0.0302 (10)	0.0199 (9)	0.0083 (8)	0.0016 (8)
N1	0.0244 (12)	0.0264 (12)	0.0270 (11)	0.0146 (10)	0.0048 (9)	0.0042 (9)
F1	0.0431 (11)	0.0431 (11)	0.0400 (10)	0.0145 (9)	−0.0106 (8)	−0.0030 (8)
C1	0.0263 (14)	0.0242 (13)	0.0251 (12)	0.0150 (11)	0.0041 (10)	0.0068 (10)
C2	0.0304 (15)	0.0290 (15)	0.0276 (13)	0.0161 (13)	0.0076 (11)	0.0083 (11)
C3	0.0250 (14)	0.0331 (16)	0.0358 (15)	0.0123 (12)	0.0038 (11)	0.0129 (12)
C4	0.0386 (17)	0.0324 (16)	0.0255 (14)	0.0145 (14)	−0.0050 (12)	0.0038 (11)
C5	0.0474 (19)	0.0440 (18)	0.0261 (14)	0.0315 (16)	−0.0022 (12)	−0.0006 (12)
C6	0.0345 (16)	0.0433 (17)	0.0256 (13)	0.0265 (14)	0.0012 (11)	0.0028 (11)
C7	0.0217 (12)	0.0247 (13)	0.0188 (12)	0.0104 (11)	−0.0023 (9)	0.0007 (10)
C8	0.0276 (14)	0.0330 (15)	0.0243 (13)	0.0189 (13)	0.0025 (10)	−0.0001 (11)
C9	0.0327 (15)	0.0277 (14)	0.0298 (14)	0.0182 (13)	−0.0010 (11)	−0.0004 (11)
C10	0.0236 (13)	0.0218 (13)	0.0261 (13)	0.0082 (11)	−0.0053 (10)	0.0018 (10)
C11	0.0222 (13)	0.0308 (14)	0.0222 (12)	0.0135 (12)	0.0019 (10)	0.0044 (10)
C12	0.0258 (14)	0.0276 (14)	0.0234 (13)	0.0163 (12)	0.0000 (10)	0.0002 (10)

Geometric parameters (Å, º)

Cl1—C10	1.742 (3)	C4—C5	1.368 (5)
S1—O2	1.4324 (19)	C5—C6	1.381 (4)
S1—O1	1.4390 (19)	C5—H5	0.9500
S1—N1	1.626 (2)	C6—H6	0.9500
S1—C1	1.760 (3)	C7—C12	1.386 (4)
N1—C7	1.427 (3)	C7—C8	1.392 (4)
N1—H1	0.90 (4)	C8—C9	1.378 (4)
F1—C4	1.363 (3)	C8—H8	0.9500
C1—C2	1.385 (4)	C9—C10	1.387 (4)
C1—C6	1.399 (4)	C9—H9	0.9500
C2—C3	1.379 (4)	C10—C11	1.377 (4)
C2—H2	0.9500	C11—C12	1.387 (4)
C3—C4	1.373 (4)	C11—H11	0.9500
C3—H3	0.9500	C12—H12	0.9500
O2—S1—O1	118.21 (12)	C6—C5—H5	120.9
O2—S1—N1	110.13 (11)	C5—C6—C1	119.3 (3)
O1—S1—N1	104.48 (12)	C5—C6—H6	120.4
O2—S1—C1	108.13 (12)	C1—C6—H6	120.4
O1—S1—C1	108.79 (12)	C12—C7—C8	120.0 (2)
N1—S1—C1	106.50 (12)	C12—C7—N1	121.0 (2)
C7—N1—S1	121.32 (19)	C8—C7—N1	119.1 (2)
C7—N1—H1	115 (3)	C9—C8—C7	120.2 (2)
S1—N1—H1	110 (3)	C9—C8—H8	119.9
C2—C1—C6	121.0 (3)	C7—C8—H8	119.9
C2—C1—S1	119.9 (2)	C8—C9—C10	119.1 (2)
C6—C1—S1	119.1 (2)	C8—C9—H9	120.4
C3—C2—C1	119.6 (3)	C10—C9—H9	120.4
C3—C2—H2	120.2	C11—C10—C9	121.4 (2)
C1—C2—H2	120.2	C11—C10—Cl1	118.3 (2)
C4—C3—C2	118.2 (3)	C9—C10—Cl1	120.3 (2)
C4—C3—H3	120.9	C10—C11—C12	119.3 (2)
C2—C3—H3	120.9	C10—C11—H11	120.4
F1—C4—C5	117.6 (3)	C12—C11—H11	120.4
F1—C4—C3	118.7 (3)	C7—C12—C11	120.0 (2)
C5—C4—C3	123.8 (3)	C7—C12—H12	120.0
C4—C5—C6	118.2 (3)	C11—C12—H12	120.0
C4—C5—H5	120.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.90 (4)	1.95 (4)	2.844 (3)	170 (4)

Symmetry code: (i) −x+1, −y, −z+1.

(F~F)

Crystal data

C12H9F2NO2S	F(000) = 2484
Mr = 269.26	Dx = 1.553 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 24.9922 (5) Å	µ = 0.30 mm^−1
c = 9.5804 (4) Å	T = 120 K
V = 5182.3 (3) Å^3	0.20 × 0.15 × 0.15 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2157 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1777 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ & ω scans	θmax = 26.0°, θmin = 3.3°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −30→29
Tmin = 0.943, Tmax = 0.956	k = −26→30
5887 measured reflections	l = −10→11

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0506P)^2 + 2.923P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2157 reflections	Δρmax = 0.27 e Å^−3
176 parameters	Δρmin = −0.46 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0011 (2)

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
S1	0.584114 (19)	0.01450 (2)	0.39034 (5)	0.02333 (18)
O1	0.53549 (6)	−0.03382 (6)	0.47128 (15)	0.0286 (3)
O2	0.61532 (6)	−0.00209 (6)	0.28974 (15)	0.0305 (3)
N1	0.55130 (7)	0.04889 (7)	0.31291 (18)	0.0249 (4)
H1	0.5203 (11)	0.0464 (10)	0.368 (3)	0.032 (6)*
F1	0.76488 (5)	0.18786 (6)	0.78665 (13)	0.0413 (3)
F2	0.68290 (7)	0.26899 (6)	0.02636 (16)	0.0501 (4)
C1	0.63972 (8)	0.06866 (8)	0.5063 (2)	0.0234 (4)
C2	0.69889 (8)	0.07712 (8)	0.5067 (2)	0.0258 (4)
H2	0.7103	0.0558	0.4417	0.032 (6)*
C3	0.74133 (8)	0.11727 (9)	0.6035 (2)	0.0299 (4)
H3	0.7820	0.1234	0.6075	0.036 (6)*
C4	0.72324 (9)	0.14789 (9)	0.6932 (2)	0.0306 (4)
C5	0.66482 (9)	0.14079 (10)	0.6932 (2)	0.0331 (5)
H5	0.6542	0.1633	0.7564	0.051 (7)*
C6	0.62233 (9)	0.10000 (9)	0.5987 (2)	0.0290 (4)
H6	0.5815	0.0934	0.5969	0.025 (5)*
C7	0.58660 (8)	0.10595 (8)	0.2397 (2)	0.0230 (4)
C8	0.57599 (9)	0.15445 (9)	0.2680 (2)	0.0278 (4)
H8	0.5470	0.1500	0.3378	0.033 (6)*
C9	0.60762 (9)	0.20929 (9)	0.1943 (2)	0.0324 (5)
H9	0.5999	0.2423	0.2108	0.052 (7)*
C10	0.65042 (9)	0.21479 (9)	0.0969 (2)	0.0327 (5)
C11	0.66227 (9)	0.16797 (10)	0.0684 (2)	0.0301 (4)
H11	0.6926	0.1735	0.0014	0.033 (6)*
C12	0.62915 (8)	0.11241 (9)	0.1390 (2)	0.0262 (4)
H12	0.6356	0.0789	0.1185	0.026 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0195 (2)	0.0242 (3)	0.0282 (3)	0.01231 (19)	0.00158 (17)	0.00012 (17)
O1	0.0228 (6)	0.0232 (6)	0.0399 (8)	0.0116 (5)	0.0049 (6)	0.0036 (6)
O2	0.0285 (7)	0.0336 (7)	0.0351 (8)	0.0196 (6)	0.0030 (6)	−0.0032 (6)
N1	0.0190 (7)	0.0291 (8)	0.0285 (9)	0.0133 (7)	0.0000 (6)	0.0004 (7)
F1	0.0322 (6)	0.0446 (7)	0.0334 (7)	0.0089 (5)	−0.0100 (5)	−0.0018 (6)
F2	0.0474 (8)	0.0399 (7)	0.0571 (9)	0.0174 (6)	0.0094 (7)	0.0194 (6)
C1	0.0194 (8)	0.0263 (9)	0.0241 (10)	0.0110 (7)	0.0018 (7)	0.0064 (7)
C2	0.0228 (9)	0.0262 (9)	0.0302 (10)	0.0135 (7)	0.0053 (7)	0.0095 (8)
C3	0.0197 (9)	0.0320 (10)	0.0358 (11)	0.0112 (8)	0.0009 (8)	0.0125 (8)
C4	0.0260 (9)	0.0313 (10)	0.0251 (10)	0.0073 (8)	−0.0040 (8)	0.0061 (8)
C5	0.0333 (10)	0.0408 (11)	0.0247 (10)	0.0182 (9)	0.0009 (8)	−0.0007 (9)
C6	0.0240 (9)	0.0369 (10)	0.0284 (10)	0.0169 (8)	−0.0001 (8)	0.0001 (8)
C7	0.0197 (8)	0.0273 (9)	0.0213 (9)	0.0112 (7)	−0.0067 (7)	−0.0031 (7)
C8	0.0262 (9)	0.0328 (10)	0.0267 (10)	0.0166 (8)	−0.0023 (8)	−0.0045 (8)
C9	0.0340 (10)	0.0319 (10)	0.0337 (11)	0.0181 (9)	−0.0036 (9)	0.0002 (8)
C10	0.0303 (10)	0.0312 (10)	0.0315 (11)	0.0115 (8)	−0.0046 (8)	0.0055 (8)
C11	0.0247 (9)	0.0408 (11)	0.0245 (10)	0.0160 (8)	−0.0012 (7)	0.0015 (8)
C12	0.0246 (9)	0.0334 (10)	0.0226 (9)	0.0159 (8)	−0.0040 (7)	−0.0043 (8)

Geometric parameters (Å, º)

S1—O2	1.4257 (14)	C4—C5	1.380 (3)
S1—O1	1.4384 (14)	C5—C6	1.380 (3)
S1—N1	1.6328 (16)	C5—H5	0.9500
S1—C1	1.7655 (19)	C6—H6	0.9500
N1—C7	1.430 (3)	C7—C12	1.384 (3)
N1—H1	0.91 (2)	C7—C8	1.391 (3)
F1—C4	1.357 (2)	C8—C9	1.385 (3)
F2—C10	1.360 (2)	C8—H8	0.9500
C1—C2	1.385 (3)	C9—C10	1.374 (3)
C1—C6	1.388 (3)	C9—H9	0.9500
C2—C3	1.389 (3)	C10—C11	1.371 (3)
C2—H2	0.9500	C11—C12	1.386 (3)
C3—C4	1.369 (3)	C11—H11	0.9500
C3—H3	0.9500	C12—H12	0.9500
O2—S1—O1	118.40 (8)	C6—C5—H5	121.0
O2—S1—N1	109.74 (9)	C5—C6—C1	119.54 (18)
O1—S1—N1	104.54 (8)	C5—C6—H6	120.2
O2—S1—C1	108.24 (8)	C1—C6—H6	120.2
O1—S1—C1	108.37 (8)	C12—C7—C8	120.29 (18)
N1—S1—C1	107.00 (8)	C12—C7—N1	120.87 (17)
C7—N1—S1	121.72 (12)	C8—C7—N1	118.81 (16)
C7—N1—H1	115.5 (14)	C9—C8—C7	120.00 (18)
S1—N1—H1	109.6 (15)	C9—C8—H8	120.0
C2—C1—C6	121.61 (18)	C7—C8—H8	120.0
C2—C1—S1	119.31 (15)	C10—C9—C8	118.41 (19)
C6—C1—S1	119.04 (14)	C10—C9—H9	120.8
C1—C2—C3	118.89 (18)	C8—C9—H9	120.8
C1—C2—H2	120.6	F2—C10—C11	118.37 (19)
C3—C2—H2	120.6	F2—C10—C9	118.97 (19)
C4—C3—C2	118.49 (17)	C11—C10—C9	122.66 (19)
C4—C3—H3	120.8	C10—C11—C12	118.83 (18)
C2—C3—H3	120.8	C10—C11—H11	120.6
F1—C4—C3	118.63 (18)	C12—C11—H11	120.6
F1—C4—C5	117.86 (19)	C7—C12—C11	119.76 (18)
C3—C4—C5	123.51 (18)	C7—C12—H12	120.1
C4—C5—C6	117.95 (19)	C11—C12—H12	120.1
C4—C5—H5	121.0
C2—C1—S1—N1	−131.86 (15)	S1—N1—C7—C12	51.9 (2)
C6—C1—S1—N1	50.60 (17)	S1—N1—C7—C8	−130.25 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.91 (2)	2.00 (3)	2.882 (2)	164 (2)

Symmetry code: (i) −x+1, −y, −z+1.

(F~I)

Crystal data

C12H9FINO2S	F(000) = 3276
Mr = 377.16	Dx = 1.911 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.3131 (5) Å	µ = 2.61 mm^−1
c = 9.1331 (2) Å	T = 120 K
V = 5900.5 (2) Å^3	0.40 × 0.30 × 0.20 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2564 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2369 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ & ω scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −32→33
Tmin = 0.401, Tmax = 0.593	k = −31→33
14479 measured reflections	l = −11→11

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0409P)^2 + 43.0642P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.002
2564 reflections	Δρmax = 0.77 e Å^−3
176 parameters	Δρmin = −1.06 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00014 (4)

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
I1	0.270779 (11)	0.565882 (11)	1.00037 (3)	0.03077 (13)
S1	0.00782 (4)	0.42666 (4)	0.59438 (10)	0.0218 (2)
O1	−0.03146 (11)	0.43128 (11)	0.4975 (3)	0.0302 (6)
O2	−0.01406 (11)	0.38165 (10)	0.6988 (3)	0.0243 (6)
N1	0.04032 (13)	0.48755 (12)	0.6785 (3)	0.0217 (6)
H1N	0.039 (2)	0.5164 (14)	0.637 (5)	0.039 (13)*
F1	0.17821 (13)	0.41137 (14)	0.2434 (3)	0.0589 (9)
C1	0.05949 (15)	0.42207 (15)	0.4896 (4)	0.0233 (8)
C2	0.09338 (19)	0.46584 (17)	0.3936 (4)	0.0346 (10)
H2	0.0889	0.4980	0.3851	0.058 (17)*
C3	0.1333 (2)	0.46169 (19)	0.3115 (5)	0.0437 (12)
H3	0.1570	0.4911	0.2460	0.049 (15)*
C4	0.13850 (19)	0.4146 (2)	0.3253 (5)	0.0411 (11)
C5	0.10631 (19)	0.37111 (19)	0.4189 (5)	0.0359 (10)
H5	0.1113	0.3392	0.4262	0.067 (19)*
C6	0.06591 (17)	0.37509 (16)	0.5035 (4)	0.0284 (8)
H6	0.0429	0.3458	0.5701	0.054 (16)*
C7	0.09232 (14)	0.50529 (14)	0.7534 (4)	0.0181 (7)
C8	0.13704 (16)	0.55971 (15)	0.7288 (4)	0.0226 (7)
H8	0.1325	0.5845	0.6644	0.020 (10)*
C9	0.18817 (15)	0.57761 (15)	0.7986 (4)	0.0244 (8)
H9	0.2189	0.6147	0.7825	0.022 (10)*
C10	0.19415 (15)	0.54094 (15)	0.8925 (4)	0.0199 (7)
C11	0.14917 (16)	0.48671 (15)	0.9175 (4)	0.0226 (7)
H11	0.1537	0.4618	0.9812	0.028 (11)*
C12	0.09816 (15)	0.46933 (15)	0.8496 (4)	0.0218 (7)
H12	0.0670	0.4328	0.8687	0.034 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02298 (17)	0.03045 (18)	0.0414 (2)	0.01528 (12)	−0.00982 (10)	−0.01101 (11)
S1	0.0177 (4)	0.0147 (4)	0.0272 (5)	0.0039 (3)	−0.0081 (3)	0.0029 (3)
O1	0.0218 (13)	0.0198 (13)	0.0419 (16)	0.0050 (11)	−0.0174 (12)	0.0053 (12)
O2	0.0205 (13)	0.0152 (12)	0.0310 (14)	0.0043 (10)	−0.0035 (10)	0.0074 (10)
N1	0.0185 (15)	0.0141 (14)	0.0301 (16)	0.0064 (12)	−0.0083 (12)	0.0012 (12)
F1	0.0452 (17)	0.069 (2)	0.0525 (17)	0.0211 (15)	0.0112 (14)	−0.0202 (15)
C1	0.0229 (18)	0.0169 (17)	0.0207 (17)	0.0029 (15)	−0.0086 (14)	−0.0027 (14)
C2	0.045 (3)	0.0177 (19)	0.0280 (19)	0.0056 (18)	0.0010 (18)	−0.0012 (15)
C3	0.050 (3)	0.027 (2)	0.031 (2)	0.002 (2)	0.008 (2)	−0.0047 (18)
C4	0.031 (2)	0.046 (3)	0.033 (2)	0.008 (2)	−0.0008 (18)	−0.018 (2)
C5	0.037 (2)	0.036 (2)	0.034 (2)	0.018 (2)	−0.0086 (18)	−0.0061 (18)
C6	0.028 (2)	0.0249 (19)	0.0279 (19)	0.0105 (17)	−0.0079 (16)	0.0015 (15)
C7	0.0180 (16)	0.0169 (16)	0.0188 (16)	0.0082 (14)	−0.0019 (13)	−0.0022 (13)
C8	0.0242 (18)	0.0153 (16)	0.0256 (17)	0.0078 (15)	−0.0015 (14)	0.0030 (14)
C9	0.0198 (18)	0.0156 (17)	0.0301 (19)	0.0031 (14)	−0.0029 (15)	−0.0015 (14)
C10	0.0195 (17)	0.0210 (17)	0.0223 (17)	0.0123 (14)	−0.0058 (13)	−0.0089 (14)
C11	0.0273 (19)	0.0171 (17)	0.0242 (17)	0.0116 (15)	−0.0062 (15)	−0.0022 (14)
C12	0.0215 (18)	0.0158 (16)	0.0236 (17)	0.0059 (14)	−0.0034 (14)	0.0007 (14)

Geometric parameters (Å, º)

I1—C10	2.095 (3)	C3—C4	1.370 (7)
S1—O2	1.429 (3)	C4—C5	1.367 (7)
S1—O1	1.444 (3)	C5—C6	1.395 (6)
S1—N1	1.633 (3)	C7—C12	1.385 (5)
S1—C1	1.761 (4)	C7—C8	1.392 (5)
N1—C7	1.426 (4)	C8—C9	1.383 (5)
F1—C4	1.356 (5)	C9—C10	1.389 (5)
C1—C6	1.385 (6)	C10—C11	1.391 (5)
C1—C2	1.396 (5)	C11—C12	1.374 (5)
C2—C3	1.374 (7)
O2—S1—O1	118.32 (16)	C5—C4—C3	123.3 (4)
O2—S1—N1	110.05 (16)	C4—C5—C6	118.0 (4)
O1—S1—N1	104.39 (16)	C1—C6—C5	119.5 (4)
O2—S1—C1	107.84 (17)	C12—C7—C8	120.6 (3)
O1—S1—C1	109.29 (18)	C12—C7—N1	120.8 (3)
N1—S1—C1	106.34 (16)	C8—C7—N1	118.6 (3)
C7—N1—S1	120.9 (2)	C9—C8—C7	119.7 (3)
C6—C1—C2	120.9 (4)	C8—C9—C10	119.5 (3)
C6—C1—S1	119.6 (3)	C9—C10—C11	120.6 (3)
C2—C1—S1	119.5 (3)	C9—C10—I1	121.0 (3)
C3—C2—C1	119.1 (4)	C11—C10—I1	118.4 (3)
C4—C3—C2	119.1 (4)	C12—C11—C10	119.8 (3)
F1—C4—C5	118.5 (5)	C11—C12—C7	119.8 (3)
F1—C4—C3	118.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.89 (1)	1.98 (2)	2.845 (4)	166 (5)

Symmetry code: (i) −x, −y+1, −z+1.

(Me~Br)

Crystal data

C13H12BrNO2S	F(000) = 2952
Mr = 326.21	Dx = 1.611 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.1912 (10) Å	µ = 3.21 mm^−1
c = 9.4503 (7) Å	T = 120 K
V = 6051.1 (5) Å^3	0.20 × 0.20 × 0.10 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2334 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1711 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.113
φ & ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −28→32
Tmin = 0.567, Tmax = 0.740	k = −32→32
6656 measured reflections	l = −11→11

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0408P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.016
2334 reflections	Δρmax = 0.39 e Å^−3
177 parameters	Δρmin = −0.51 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00047 (8)

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)
Br1	0.691128 (18)	0.266053 (18)	0.01078 (5)	0.0465 (2)
S1	0.58069 (4)	0.00886 (4)	0.40513 (9)	0.0266 (2)
O1	0.53488 (11)	−0.03284 (10)	0.4921 (3)	0.0320 (6)
O2	0.60640 (10)	−0.01102 (11)	0.3046 (3)	0.0324 (6)
N1	0.55210 (12)	0.04142 (12)	0.3233 (3)	0.0267 (7)
H1N	0.5232 (10)	0.0395 (15)	0.371 (3)	0.028 (10)*
C1	0.71970 (16)	0.14299 (16)	0.6821 (3)	0.0303 (9)
C2	0.66455 (17)	0.13397 (17)	0.6869 (4)	0.0343 (9)
H2	0.6561	0.1565	0.7481	0.039 (11)*
C3	0.62195 (17)	0.09274 (17)	0.6038 (4)	0.0354 (9)
H3	0.5845	0.0869	0.6082	0.035 (11)*
C4	0.63425 (15)	0.05994 (15)	0.5140 (3)	0.0275 (8)
C5	0.68890 (15)	0.06793 (16)	0.5076 (4)	0.0317 (9)
H5	0.6974	0.0456	0.4462	0.030 (9)*
C6	0.73052 (17)	0.10906 (17)	0.5925 (4)	0.0378 (10)
H6	0.7678	0.1143	0.5894	0.059 (13)*
C7	0.58638 (14)	0.09439 (14)	0.2508 (3)	0.0236 (8)
C8	0.57351 (16)	0.13768 (16)	0.2695 (4)	0.0309 (9)
H8	0.5436	0.1322	0.3312	0.039 (11)*
C9	0.60440 (16)	0.18875 (16)	0.1979 (4)	0.0338 (9)
H9	0.5953	0.2180	0.2086	0.033 (10)*
C10	0.64834 (15)	0.19650 (15)	0.1114 (4)	0.0300 (8)
C11	0.66189 (15)	0.15395 (16)	0.0931 (4)	0.0309 (8)
H11	0.6925	0.1600	0.0334	0.037 (10)*
C12	0.63040 (15)	0.10276 (16)	0.1623 (3)	0.0293 (8)
H12	0.6390	0.0732	0.1492	0.026 (9)*
C13	0.76655 (16)	0.18917 (17)	0.7691 (4)	0.0379 (10)
H13A	0.7511	0.2085	0.8256	0.057*	0.69 (5)
H13B	0.7962	0.2166	0.7060	0.057*	0.69 (5)
H13C	0.7828	0.1724	0.8322	0.057*	0.69 (5)
H13D	0.8023	0.1898	0.7503	0.057*	0.31 (5)
H13E	0.7572	0.1817	0.8698	0.057*	0.31 (5)
H13F	0.7706	0.2260	0.7437	0.057*	0.31 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0367 (3)	0.0342 (3)	0.0646 (3)	0.0148 (2)	0.0083 (2)	0.0186 (2)
S1	0.0254 (5)	0.0240 (5)	0.0324 (4)	0.0137 (4)	0.0048 (4)	0.0022 (4)
O1	0.0292 (14)	0.0227 (14)	0.0432 (14)	0.0122 (11)	0.0083 (12)	0.0071 (11)
O2	0.0350 (15)	0.0307 (14)	0.0365 (13)	0.0202 (13)	0.0067 (11)	−0.0014 (11)
N1	0.0232 (16)	0.0272 (17)	0.0317 (15)	0.0143 (14)	0.0018 (14)	0.0013 (14)
C1	0.031 (2)	0.031 (2)	0.0250 (17)	0.0132 (18)	0.0019 (16)	0.0126 (16)
C2	0.036 (2)	0.041 (2)	0.0328 (18)	0.024 (2)	0.0013 (17)	−0.0037 (18)
C3	0.030 (2)	0.045 (2)	0.0348 (19)	0.022 (2)	0.0054 (17)	−0.0005 (18)
C4	0.029 (2)	0.0258 (19)	0.0277 (17)	0.0135 (17)	0.0058 (16)	0.0068 (16)
C5	0.029 (2)	0.035 (2)	0.0354 (19)	0.0184 (18)	0.0046 (17)	0.0025 (18)
C6	0.027 (2)	0.044 (2)	0.047 (2)	0.021 (2)	0.0022 (19)	0.007 (2)
C7	0.0212 (18)	0.0225 (18)	0.0260 (16)	0.0102 (15)	−0.0031 (15)	−0.0016 (15)
C8	0.035 (2)	0.033 (2)	0.0313 (18)	0.0222 (19)	0.0034 (17)	0.0017 (17)
C9	0.036 (2)	0.025 (2)	0.043 (2)	0.0176 (18)	−0.0012 (18)	−0.0008 (17)
C10	0.0231 (19)	0.029 (2)	0.0352 (19)	0.0109 (17)	−0.0015 (16)	0.0062 (16)
C11	0.0220 (19)	0.039 (2)	0.0343 (18)	0.0169 (18)	0.0005 (16)	0.0045 (18)
C12	0.028 (2)	0.034 (2)	0.0333 (18)	0.0208 (18)	0.0028 (16)	0.0052 (17)
C13	0.031 (2)	0.038 (2)	0.036 (2)	0.0108 (18)	−0.0002 (17)	0.0105 (18)

Geometric parameters (Å, º)

Br1—C10	1.906 (3)	C6—H6	0.9500
S1—O2	1.436 (2)	C7—C12	1.382 (5)
S1—O1	1.449 (2)	C7—C8	1.397 (5)
S1—N1	1.635 (3)	C8—C9	1.387 (5)
S1—C4	1.756 (4)	C8—H8	0.9500
N1—C7	1.438 (4)	C9—C10	1.374 (5)
N1—H1N	0.84 (4)	C9—H9	0.9500
C1—C6	1.388 (5)	C10—C11	1.389 (5)
C1—C2	1.394 (5)	C11—C12	1.381 (5)
C1—C13	1.508 (5)	C11—H11	0.9500
C2—C3	1.385 (5)	C12—H12	0.9500
C2—H2	0.9500	C13—H13A	0.9800
C3—C4	1.388 (5)	C13—H13B	0.9800
C3—H3	0.9500	C13—H13C	0.9800
C4—C5	1.392 (5)	C13—H13D	0.9800
C5—C6	1.382 (5)	C13—H13E	0.9800
C5—H5	0.9500	C13—H13F	0.9800
O2—S1—O1	118.06 (15)	C10—C9—C8	119.2 (3)
O2—S1—N1	110.05 (15)	C10—C9—H9	120.4
O1—S1—N1	103.74 (16)	C8—C9—H9	120.4
O2—S1—C4	108.53 (17)	C9—C10—C11	121.2 (3)
O1—S1—C4	109.58 (15)	C9—C10—Br1	120.1 (3)
N1—S1—C4	106.23 (16)	C11—C10—Br1	118.7 (3)
C7—N1—S1	121.5 (2)	C12—C11—C10	119.4 (3)
C7—N1—H1N	114 (2)	C12—C11—H11	120.3
S1—N1—H1N	112 (2)	C10—C11—H11	120.3
C6—C1—C2	118.0 (4)	C11—C12—C7	120.1 (3)
C6—C1—C13	120.9 (4)	C11—C12—H12	119.9
C2—C1—C13	121.0 (3)	C7—C12—H12	119.9
C3—C2—C1	121.0 (4)	C1—C13—H13A	109.5
C3—C2—H2	119.5	C1—C13—H13B	109.5
C1—C2—H2	119.5	H13A—C13—H13B	109.5
C2—C3—C4	119.6 (4)	C1—C13—H13C	109.5
C2—C3—H3	120.2	H13A—C13—H13C	109.5
C4—C3—H3	120.2	H13B—C13—H13C	109.5
C3—C4—C5	120.5 (3)	C1—C13—H13D	109.5
C3—C4—S1	119.7 (3)	H13A—C13—H13D	141.1
C5—C4—S1	119.8 (3)	H13B—C13—H13D	56.3
C6—C5—C4	118.7 (3)	H13C—C13—H13D	56.3
C6—C5—H5	120.7	C1—C13—H13E	109.5
C4—C5—H5	120.7	H13A—C13—H13E	56.3
C5—C6—C1	122.2 (4)	H13B—C13—H13E	141.1
C5—C6—H6	118.9	H13C—C13—H13E	56.3
C1—C6—H6	118.9	H13D—C13—H13E	109.5
C12—C7—C8	119.9 (3)	C1—C13—H13F	109.5
C12—C7—N1	121.8 (3)	H13A—C13—H13F	56.3
C8—C7—N1	118.3 (3)	H13B—C13—H13F	56.3
C9—C8—C7	120.0 (3)	H13C—C13—H13F	141.1
C9—C8—H8	120.0	H13D—C13—H13F	109.5
C7—C8—H8	120.0	H13E—C13—H13F	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.84 (4)	2.02 (4)	2.855 (4)	170 (3)

Symmetry code: (i) −x+1, −y, −z+1.

(Me~CF3)

Crystal data

C14H12F3NO2S	F(000) = 2916
Mr = 315.31	Dx = 1.443 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.7243 (7) Å	µ = 0.26 mm^−1
c = 9.8101 (5) Å	T = 293 K
V = 6530.2 (4) Å^3	0.20 × 0.12 × 0.10 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2548 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1849 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
φ & ω scans	θmax = 25.1°, θmin = 3.7°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −32→32
Tmin = 0.950, Tmax = 0.975	k = −31→33
11133 measured reflections	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0813P)^2 + 1.837P] where P = (Fo^2 + 2Fc^2)/3
2548 reflections	(Δ/σ)max = 0.007
222 parameters	Δρmax = 0.29 e Å^−3
44 restraints	Δρmin = −0.38 e Å^−3

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)
S1	0.00568 (3)	0.42769 (3)	0.09295 (8)	0.0582 (3)
O1	−0.03369 (9)	0.43272 (9)	0.0075 (2)	0.0712 (7)
O2	−0.01517 (10)	0.38396 (9)	0.1908 (2)	0.0713 (7)
N1	0.03880 (11)	0.48765 (10)	0.1707 (3)	0.0579 (7)
H1N	0.0383 (14)	0.5143 (10)	0.121 (3)	0.070*
C1	0.05516 (13)	0.42292 (12)	−0.0085 (3)	0.0560 (8)
C2	0.06265 (16)	0.37787 (15)	0.0044 (4)	0.0724 (9)
H2	0.0415	0.3497	0.0663	0.087*
C3	0.10171 (18)	0.37496 (18)	−0.0752 (4)	0.0838 (11)
H3	0.1064	0.3441	−0.0672	0.101*
C4	0.13418 (15)	0.41609 (17)	−0.1665 (3)	0.0726 (10)
C5	0.12542 (18)	0.46066 (17)	−0.1777 (4)	0.0844 (11)
H5	0.1466	0.4889	−0.2394	0.101*
C6	0.08635 (16)	0.46440 (15)	−0.1004 (3)	0.0757 (10)
H6	0.0810	0.4947	−0.1099	0.091*
C7	0.08947 (12)	0.50525 (12)	0.2415 (3)	0.0520 (7)
C8	0.09638 (14)	0.47003 (13)	0.3291 (3)	0.0645 (8)
H8	0.0676	0.4337	0.3426	0.077*
C9	0.14605 (15)	0.48913 (13)	0.3956 (3)	0.0699 (9)
H9	0.1508	0.4653	0.4536	0.084*
C10	0.18900 (14)	0.54282 (14)	0.3782 (3)	0.0663 (9)
C11	0.18099 (14)	0.57805 (15)	0.2940 (4)	0.0734 (10)
H11	0.2094	0.6148	0.2835	0.088*
C12	0.13201 (14)	0.55967 (14)	0.2260 (3)	0.0654 (9)
H12	0.1272	0.5838	0.1691	0.079*
C13	0.17859 (19)	0.4135 (2)	−0.2505 (4)	0.1005 (14)
H13A	0.1789	0.3798	−0.2296	0.151*	0.43 (6)
H13B	0.2143	0.4450	−0.2295	0.151*	0.43 (6)
H13C	0.1708	0.4140	−0.3456	0.151*	0.43 (6)
H13D	0.1971	0.4460	−0.3069	0.151*	0.57 (6)
H13E	0.1616	0.3808	−0.3070	0.151*	0.57 (6)
H13F	0.2052	0.4118	−0.1909	0.151*	0.57 (6)
C14	0.24129 (17)	0.56192 (15)	0.4505 (4)	0.0942 (13)
F1	0.2616 (4)	0.5280 (4)	0.4382 (11)	0.102 (3)	0.387 (10)
F2	0.2347 (4)	0.5651 (7)	0.5856 (6)	0.139 (4)	0.387 (10)
F3	0.2839 (4)	0.6070 (4)	0.3938 (15)	0.152 (5)	0.387 (10)
F1'	0.2839 (2)	0.5787 (5)	0.3620 (7)	0.167 (4)	0.613 (10)
F2'	0.2443 (3)	0.5242 (3)	0.5287 (12)	0.168 (4)	0.613 (10)
F3'	0.2601 (2)	0.6080 (2)	0.5217 (6)	0.109 (2)	0.613 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0479 (5)	0.0451 (5)	0.0778 (6)	0.0203 (4)	−0.0066 (3)	0.0056 (3)
O1	0.0521 (13)	0.0542 (13)	0.1023 (16)	0.0228 (11)	−0.0189 (11)	0.0039 (11)
O2	0.0650 (14)	0.0527 (13)	0.0873 (15)	0.0227 (11)	0.0030 (11)	0.0169 (10)
N1	0.0554 (15)	0.0487 (15)	0.0721 (16)	0.0278 (13)	−0.0046 (12)	0.0011 (11)
C1	0.0585 (18)	0.0452 (16)	0.0627 (16)	0.0247 (14)	−0.0141 (13)	−0.0061 (13)
C2	0.080 (2)	0.061 (2)	0.084 (2)	0.0416 (19)	−0.0076 (18)	0.0032 (17)
C3	0.102 (3)	0.080 (3)	0.093 (3)	0.064 (2)	−0.012 (2)	−0.008 (2)
C4	0.072 (2)	0.087 (3)	0.069 (2)	0.046 (2)	−0.0197 (17)	−0.0257 (19)
C5	0.095 (3)	0.079 (3)	0.078 (2)	0.043 (2)	0.014 (2)	0.0080 (19)
C6	0.091 (3)	0.060 (2)	0.083 (2)	0.043 (2)	0.0104 (19)	0.0100 (17)
C7	0.0543 (18)	0.0492 (17)	0.0568 (15)	0.0291 (15)	−0.0004 (12)	−0.0015 (12)
C8	0.072 (2)	0.0434 (17)	0.0755 (19)	0.0265 (16)	−0.0104 (16)	−0.0007 (14)
C9	0.081 (2)	0.0516 (19)	0.084 (2)	0.0380 (19)	−0.0240 (18)	−0.0092 (16)
C10	0.061 (2)	0.061 (2)	0.081 (2)	0.0332 (17)	−0.0128 (16)	−0.0157 (16)
C11	0.059 (2)	0.054 (2)	0.091 (2)	0.0161 (17)	−0.0039 (18)	0.0039 (17)
C12	0.061 (2)	0.0526 (19)	0.0745 (19)	0.0225 (16)	−0.0037 (16)	0.0092 (15)
C13	0.097 (3)	0.136 (4)	0.089 (3)	0.074 (3)	−0.013 (2)	−0.030 (3)
C14	0.079 (3)	0.089 (3)	0.112 (3)	0.040 (3)	−0.025 (2)	−0.014 (3)
F1	0.095 (5)	0.112 (6)	0.137 (6)	0.079 (5)	−0.039 (4)	−0.022 (4)
F2	0.109 (6)	0.199 (10)	0.113 (5)	0.081 (6)	−0.055 (4)	−0.065 (6)
F3	0.105 (6)	0.111 (6)	0.222 (10)	0.040 (5)	−0.057 (6)	0.000 (6)
F1'	0.080 (4)	0.229 (8)	0.181 (5)	0.069 (5)	−0.026 (3)	−0.074 (6)
F2'	0.129 (5)	0.135 (5)	0.219 (7)	0.052 (4)	−0.079 (5)	0.030 (5)
F3'	0.103 (4)	0.092 (3)	0.120 (4)	0.039 (3)	−0.055 (3)	−0.049 (3)

Geometric parameters (Å, º)

S1—O2	1.423 (2)	C10—C11	1.379 (5)
S1—O1	1.437 (2)	C10—C14	1.455 (5)
S1—N1	1.631 (3)	C11—C12	1.363 (4)
S1—C1	1.753 (3)	C14—F3'	1.314 (4)
N1—C7	1.417 (4)	C14—F1	1.322 (4)
C1—C2	1.371 (4)	C14—F2'	1.332 (4)
C1—C6	1.374 (4)	C14—F3	1.337 (5)
C2—C3	1.370 (5)	C14—F2	1.347 (4)
C3—C4	1.373 (6)	C14—F1'	1.348 (4)
C4—C5	1.378 (5)	F1—F2'	0.990 (10)
C4—C13	1.513 (5)	F1—F1'	1.431 (11)
C5—C6	1.368 (5)	F2—F3'	1.212 (12)
C7—C12	1.382 (4)	F2—F2'	1.402 (11)
C7—C8	1.384 (4)	F3—F1'	0.845 (13)
C8—C9	1.368 (4)	F3—F3'	1.425 (13)
C9—C10	1.375 (5)
O2—S1—O1	118.13 (13)	F3'—C14—F2	54.2 (6)
O2—S1—N1	109.57 (14)	F1—C14—F2	104.8 (6)
O1—S1—N1	103.98 (14)	F2'—C14—F2	63.1 (6)
O2—S1—C1	108.58 (15)	F3—C14—F2	115.7 (8)
O1—S1—C1	109.71 (14)	F3'—C14—F1'	98.9 (5)
N1—S1—C1	106.21 (14)	F1—C14—F1'	64.8 (6)
C7—N1—S1	122.4 (2)	F2'—C14—F1'	104.7 (6)
C2—C1—C6	120.3 (3)	F3—C14—F1'	36.7 (6)
C2—C1—S1	119.8 (3)	F2—C14—F1'	137.4 (6)
C6—C1—S1	119.9 (3)	F3'—C14—C10	116.8 (4)
C3—C2—C1	119.0 (3)	F1—C14—C10	113.4 (5)
C2—C3—C4	122.1 (3)	F2'—C14—C10	115.9 (4)
C3—C4—C5	117.4 (3)	F3—C14—C10	113.0 (6)
C3—C4—C13	121.7 (4)	F2—C14—C10	111.1 (4)
C5—C4—C13	120.8 (4)	F1'—C14—C10	110.7 (4)
C6—C5—C4	121.7 (4)	F2'—F1—C14	68.6 (4)
C5—C6—C1	119.4 (3)	F2'—F1—F1'	121.3 (7)
C12—C7—C8	119.7 (3)	C14—F1—F1'	58.4 (4)
C12—C7—N1	118.7 (3)	F3'—F2—C14	61.5 (4)
C8—C7—N1	121.6 (3)	F3'—F2—F2'	109.7 (6)
C9—C8—C7	119.4 (3)	C14—F2—F2'	57.9 (3)
C8—C9—C10	121.3 (3)	F1'—F3—C14	72.3 (5)
C9—C10—C11	118.8 (3)	F1'—F3—F3'	124.1 (9)
C9—C10—C14	120.0 (3)	C14—F3—F3'	56.7 (4)
C11—C10—C14	121.2 (3)	F3—F1'—C14	71.0 (5)
C12—C11—C10	120.8 (3)	F3—F1'—F1	121.2 (9)
C11—C12—C7	120.1 (3)	C14—F1'—F1	56.7 (3)
F3'—C14—F1	129.7 (5)	F1—F2'—C14	67.6 (4)
F3'—C14—F2'	107.9 (5)	F1—F2'—F2	123.4 (7)
F1—C14—F2'	43.8 (5)	C14—F2'—F2	59.0 (4)
F3'—C14—F3	65.0 (7)	F2—F3'—C14	64.3 (3)
F1—C14—F3	97.8 (7)	F2—F3'—F3	118.8 (6)
F2'—C14—F3	126.9 (7)	C14—F3'—F3	58.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.89 (1)	1.99 (1)	2.874 (3)	173 (3)

Symmetry code: (i) −x, −y+1, −z.

(Me~Cl)

Crystal data

C13H12ClNO2S	F(000) = 2628
Mr = 281.75	Dx = 1.427 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 26.7454 (4) Å	µ = 0.44 mm^−1
c = 9.5265 (3) Å	T = 120 K
V = 5901.5 (2) Å^3	0.25 × 0.20 × 0.20 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2577 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1945 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ & ω scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −32→28
Tmin = 0.897, Tmax = 0.917	k = −32→28
13967 measured reflections	l = −11→11

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0583P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
2577 reflections	Δρmax = 0.27 e Å^−3
179 parameters	Δρmin = −0.39 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00051 (13)

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
S1	0.01008 (2)	0.58133 (2)	0.09746 (5)	0.02612 (17)
Cl1	0.26491 (3)	0.68723 (3)	0.48191 (7)	0.0500 (2)
O1	−0.03311 (6)	0.53481 (6)	0.01283 (13)	0.0310 (4)
O2	−0.00911 (6)	0.60819 (6)	0.19643 (14)	0.0318 (3)
N1	0.04277 (7)	0.55197 (7)	0.17945 (16)	0.0258 (4)
H1N	0.0407 (10)	0.5229 (6)	0.1285 (18)	0.038 (6)*
C1	0.06179 (8)	0.63487 (8)	−0.01260 (18)	0.0251 (4)
C2	0.06960 (9)	0.69000 (9)	−0.0102 (2)	0.0298 (5)
H2	0.0471	0.6992	0.0501	0.032 (5)*
C3	0.11116 (9)	0.73176 (9)	−0.0978 (2)	0.0333 (5)
H3	0.1164	0.7696	−0.0980	0.043 (6)*
C4	0.14511 (9)	0.71932 (9)	−0.18485 (19)	0.0288 (5)
C5	0.13624 (9)	0.66352 (9)	−0.1857 (2)	0.0322 (5)
H5	0.1589	0.6543	−0.2455	0.041 (6)*
C6	0.09479 (9)	0.62127 (9)	−0.10075 (19)	0.0313 (5)
H6	0.0888	0.5832	−0.1025	0.037 (6)*
C7	0.09642 (8)	0.58612 (8)	0.25014 (18)	0.0246 (4)
C8	0.14004 (9)	0.57269 (9)	0.2318 (2)	0.0306 (5)
H8	0.1342	0.5423	0.1702	0.044 (6)*
C9	0.19193 (9)	0.60350 (9)	0.3034 (2)	0.0345 (5)
H9	0.2215	0.5940	0.2925	0.044 (6)*
C10	0.20006 (9)	0.64834 (9)	0.3907 (2)	0.0320 (5)
C11	0.15730 (9)	0.66229 (9)	0.4076 (2)	0.0318 (5)
H11	0.1637	0.6935	0.4670	0.039 (6)*
C12	0.10530 (9)	0.63110 (8)	0.33867 (19)	0.0285 (5)
H12	0.0756	0.6403	0.3517	0.029 (5)*
C13	0.19137 (9)	0.76578 (9)	−0.2746 (2)	0.0368 (5)
H13A	0.2111	0.7495	−0.3284	0.076 (9)*
H13B	0.2193	0.7970	−0.2144	0.062 (8)*
H13C	0.1738	0.7810	−0.3393	0.057 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0243 (3)	0.0244 (3)	0.0309 (3)	0.0131 (2)	−0.00134 (19)	−0.0036 (2)
Cl1	0.0365 (4)	0.0417 (4)	0.0679 (4)	0.0168 (3)	−0.0203 (3)	−0.0123 (3)
O1	0.0238 (8)	0.0280 (8)	0.0403 (8)	0.0123 (6)	−0.0067 (6)	−0.0094 (6)
O2	0.0316 (8)	0.0340 (8)	0.0353 (8)	0.0205 (7)	0.0021 (6)	−0.0063 (6)
N1	0.0287 (9)	0.0209 (9)	0.0293 (9)	0.0135 (8)	−0.0020 (7)	−0.0024 (7)
C1	0.0269 (11)	0.0239 (10)	0.0266 (10)	0.0141 (9)	−0.0055 (8)	−0.0045 (8)
C2	0.0320 (12)	0.0286 (11)	0.0334 (10)	0.0186 (10)	−0.0048 (9)	−0.0056 (9)
C3	0.0364 (12)	0.0226 (11)	0.0425 (12)	0.0161 (10)	−0.0072 (9)	−0.0004 (9)
C4	0.0296 (11)	0.0272 (11)	0.0263 (9)	0.0118 (9)	−0.0095 (8)	−0.0008 (8)
C5	0.0390 (12)	0.0308 (12)	0.0280 (10)	0.0184 (10)	0.0032 (9)	−0.0011 (9)
C6	0.0410 (13)	0.0252 (11)	0.0312 (10)	0.0193 (10)	0.0017 (9)	−0.0020 (8)
C7	0.0265 (11)	0.0213 (10)	0.0235 (9)	0.0102 (9)	0.0015 (8)	0.0023 (8)
C8	0.0337 (12)	0.0305 (11)	0.0297 (10)	0.0176 (10)	0.0002 (9)	−0.0030 (9)
C9	0.0287 (12)	0.0359 (13)	0.0419 (12)	0.0184 (10)	0.0028 (9)	0.0015 (10)
C10	0.0295 (11)	0.0270 (11)	0.0364 (11)	0.0116 (10)	−0.0048 (9)	0.0011 (9)
C11	0.0406 (13)	0.0245 (11)	0.0318 (11)	0.0174 (10)	−0.0056 (9)	−0.0028 (8)
C12	0.0332 (12)	0.0290 (11)	0.0292 (10)	0.0201 (10)	−0.0013 (9)	0.0005 (8)
C13	0.0379 (13)	0.0296 (12)	0.0335 (11)	0.0099 (11)	−0.0093 (10)	0.0014 (9)

Geometric parameters (Å, º)

S1—O2	1.4272 (13)	C4—C5	1.389 (3)
S1—O1	1.4473 (13)	C4—C13	1.506 (3)
S1—N1	1.6363 (16)	C5—C6	1.382 (3)
S1—C1	1.756 (2)	C7—C12	1.389 (3)
Cl1—C10	1.744 (2)	C7—C8	1.393 (3)
N1—C7	1.427 (2)	C8—C9	1.388 (3)
C1—C2	1.382 (3)	C9—C10	1.385 (3)
C1—C6	1.392 (3)	C10—C11	1.378 (3)
C2—C3	1.392 (3)	C11—C12	1.379 (3)
C3—C4	1.388 (3)
O2—S1—O1	117.87 (8)	C5—C4—C13	120.77 (19)
O2—S1—N1	109.82 (8)	C6—C5—C4	120.75 (19)
O1—S1—N1	103.98 (8)	C5—C6—C1	119.61 (19)
O2—S1—C1	108.59 (9)	C12—C7—C8	119.79 (18)
O1—S1—C1	109.45 (8)	C12—C7—N1	121.53 (18)
N1—S1—C1	106.52 (9)	C8—C7—N1	118.66 (17)
C7—N1—S1	121.71 (13)	C9—C8—C7	120.22 (18)
C2—C1—C6	120.77 (19)	C10—C9—C8	119.12 (19)
C2—C1—S1	119.83 (15)	C11—C10—C9	120.83 (19)
C6—C1—S1	119.40 (15)	C11—C10—Cl1	119.51 (16)
C1—C2—C3	118.69 (19)	C9—C10—Cl1	119.65 (16)
C4—C3—C2	121.43 (19)	C10—C11—C12	120.19 (19)
C3—C4—C5	118.73 (19)	C11—C12—C7	119.83 (19)
C3—C4—C13	120.49 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.89 (1)	1.98 (1)	2.865 (2)	170 (2)

Symmetry code: (i) −x, −y+1, −z.

(Me~I)

Crystal data

C13H12INO2S	F(000) = 3276
Mr = 373.20	Dx = 1.787 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.7443 (14) Å	µ = 2.45 mm^−1
c = 9.3639 (9) Å	T = 120 K
V = 6242.2 (7) Å^3	0.15 × 0.05 × 0.05 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2338 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1906 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
φ & ω scans	θmax = 25.1°, θmin = 3.1°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −33→32
Tmin = 0.710, Tmax = 0.887	k = −33→31
6287 measured reflections	l = −10→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0571P)^2 + 16.9078P] where P = (Fo^2 + 2Fc^2)/3
2338 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.82 e Å^−3
0 restraints	Δρmin = −1.14 e Å^−3

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
I1	0.032009 (14)	0.097932 (14)	0.17467 (4)	0.03352 (19)
S1	−0.08776 (5)	0.23926 (5)	0.57360 (13)	0.0218 (3)
O1	−0.13223 (15)	0.23445 (15)	0.6634 (4)	0.0283 (8)
O2	−0.06471 (15)	0.28381 (15)	0.4722 (4)	0.0287 (8)
N1	−0.11513 (17)	0.17905 (17)	0.4911 (4)	0.0233 (9)
H1N	−0.139 (3)	0.153 (3)	0.551 (6)	0.028*
C1	0.0533 (2)	0.2482 (2)	0.8407 (5)	0.0264 (11)
C2	−0.0009 (2)	0.2028 (2)	0.8525 (5)	0.0303 (12)
H2	−0.0080	0.1733	0.9161	0.036*
C3	−0.0441 (2)	0.2002 (2)	0.7735 (6)	0.0287 (11)
H3	−0.0807	0.1695	0.7834	0.034*
C4	−0.0333 (2)	0.24350 (19)	0.6786 (5)	0.0213 (10)
C5	0.0200 (2)	0.2891 (2)	0.6647 (6)	0.0272 (11)
H5	0.0270	0.3184	0.6005	0.033*
C6	0.0629 (2)	0.2912 (2)	0.7459 (6)	0.0326 (12)
H6	0.0993	0.3223	0.7371	0.039*
C7	−0.0808 (2)	0.1620 (2)	0.4202 (5)	0.0223 (10)
C8	−0.0922 (2)	0.1073 (2)	0.4411 (6)	0.0283 (11)
H8	−0.1215	0.0830	0.5030	0.034*
C9	−0.0602 (2)	0.0888 (2)	0.3705 (6)	0.0273 (11)
H9	−0.0680	0.0516	0.3824	0.033*
C10	−0.0168 (2)	0.1252 (2)	0.2825 (5)	0.0238 (10)
C11	−0.0060 (2)	0.1794 (2)	0.2613 (5)	0.0278 (11)
H11	0.0236	0.2038	0.2003	0.033*
C12	−0.0380 (2)	0.1976 (2)	0.3289 (5)	0.0244 (10)
H12	−0.0310	0.2344	0.3132	0.029*
C13	0.1003 (2)	0.2501 (3)	0.9259 (6)	0.0354 (13)
H13A	0.1352	0.2836	0.9005	0.053*
H13B	0.1032	0.2171	0.9045	0.053*
H13C	0.0930	0.2508	1.0280	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0249 (2)	0.0319 (3)	0.0457 (3)	0.01565 (17)	0.00122 (13)	−0.01073 (14)
S1	0.0213 (6)	0.0166 (6)	0.0282 (6)	0.0101 (5)	0.0051 (5)	0.0028 (5)
O1	0.0277 (19)	0.0248 (18)	0.036 (2)	0.0161 (16)	0.0093 (15)	0.0034 (15)
O2	0.0281 (19)	0.0241 (18)	0.034 (2)	0.0131 (15)	0.0039 (14)	0.0051 (15)
N1	0.019 (2)	0.020 (2)	0.029 (2)	0.0085 (18)	0.0058 (17)	0.0012 (17)
C1	0.028 (3)	0.034 (3)	0.021 (2)	0.018 (2)	−0.0002 (19)	−0.005 (2)
C2	0.031 (3)	0.025 (3)	0.030 (3)	0.011 (2)	0.000 (2)	−0.002 (2)
C3	0.026 (3)	0.017 (2)	0.038 (3)	0.007 (2)	−0.001 (2)	0.002 (2)
C4	0.021 (2)	0.020 (2)	0.021 (2)	0.008 (2)	−0.0013 (18)	−0.0038 (18)
C5	0.030 (3)	0.021 (3)	0.030 (3)	0.013 (2)	0.012 (2)	0.0052 (19)
C6	0.022 (3)	0.030 (3)	0.038 (3)	0.007 (2)	0.005 (2)	−0.005 (2)
C7	0.023 (2)	0.025 (3)	0.020 (2)	0.013 (2)	−0.0023 (19)	−0.0024 (18)
C8	0.027 (3)	0.025 (3)	0.031 (3)	0.012 (2)	0.005 (2)	0.005 (2)
C9	0.029 (3)	0.021 (3)	0.034 (3)	0.014 (2)	−0.002 (2)	−0.002 (2)
C10	0.019 (2)	0.022 (2)	0.029 (3)	0.009 (2)	−0.0013 (19)	−0.0029 (19)
C11	0.021 (2)	0.023 (3)	0.027 (3)	0.001 (2)	0.0032 (19)	0.0000 (19)
C12	0.024 (2)	0.014 (2)	0.030 (3)	0.005 (2)	0.003 (2)	−0.0033 (18)
C13	0.035 (3)	0.047 (3)	0.035 (3)	0.028 (3)	−0.005 (2)	−0.009 (2)

Geometric parameters (Å, º)

I1—C10	2.111 (5)	C5—H5	0.9500
S1—O2	1.431 (4)	C6—H6	0.9500
S1—O1	1.443 (4)	C7—C12	1.394 (7)
S1—N1	1.642 (4)	C7—C8	1.400 (7)
S1—C4	1.757 (5)	C8—C9	1.394 (7)
N1—C7	1.421 (6)	C8—H8	0.9500
N1—H1N	0.90 (6)	C9—C10	1.391 (7)
C1—C2	1.401 (8)	C9—H9	0.9500
C1—C6	1.401 (8)	C10—C11	1.390 (8)
C1—C13	1.506 (7)	C11—C12	1.377 (7)
C2—C3	1.379 (8)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.401 (7)	C13—H13A	0.9800
C3—H3	0.9500	C13—H13B	0.9800
C4—C5	1.391 (7)	C13—H13C	0.9800
C5—C6	1.388 (8)
O2—S1—O1	117.3 (2)	C1—C6—H6	119.4
O2—S1—N1	110.3 (2)	C12—C7—C8	120.2 (5)
O1—S1—N1	103.9 (2)	C12—C7—N1	121.8 (4)
O2—S1—C4	108.4 (2)	C8—C7—N1	118.0 (4)
O1—S1—C4	110.3 (2)	C9—C8—C7	119.6 (5)
N1—S1—C4	106.0 (2)	C9—C8—H8	120.2
C7—N1—S1	120.8 (3)	C7—C8—H8	120.2
C7—N1—H1N	112 (4)	C10—C9—C8	119.5 (5)
S1—N1—H1N	108 (4)	C10—C9—H9	120.3
C2—C1—C6	118.5 (5)	C8—C9—H9	120.3
C2—C1—C13	120.7 (5)	C11—C10—C9	120.8 (5)
C6—C1—C13	120.9 (5)	C11—C10—I1	119.2 (4)
C3—C2—C1	121.2 (5)	C9—C10—I1	120.0 (4)
C3—C2—H2	119.4	C12—C11—C10	120.0 (5)
C1—C2—H2	119.4	C12—C11—H11	120.0
C2—C3—C4	119.2 (5)	C10—C11—H11	120.0
C2—C3—H3	120.4	C11—C12—C7	120.0 (5)
C4—C3—H3	120.4	C11—C12—H12	120.0
C5—C4—C3	120.8 (5)	C7—C12—H12	120.0
C5—C4—S1	119.8 (4)	C1—C13—H13A	109.5
C3—C4—S1	119.4 (4)	C1—C13—H13B	109.5
C6—C5—C4	119.1 (5)	H13A—C13—H13B	109.5
C6—C5—H5	120.4	C1—C13—H13C	109.5
C4—C5—H5	120.4	H13A—C13—H13C	109.5
C5—C6—C1	121.2 (5)	H13B—C13—H13C	109.5
C5—C6—H6	119.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.90 (6)	1.96 (6)	2.852 (5)	170 (5)

Symmetry code: (i) −x−1/3, −y+1/3, −z+4/3.

(MeO~I)

Crystal data

C13H12INO3S	F(000) = 3420
Mr = 389.20	Dx = 1.810 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 27.3759 (8) Å	µ = 2.39 mm^−1
c = 9.9002 (4) Å	T = 120 K
V = 6425.6 (4) Å^3	0.20 × 0.20 × 0.10 mm
Z = 18

Data collection

Bruker-Nonius 95mm CCD camera on κ-goniostat diffractometer	2769 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1964 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.140
φ & ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	h = −33→30
Tmin = 0.646, Tmax = 0.796	k = −33→33
30339 measured reflections	l = −12→12

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0447P)^2 + 35.0384P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.017
2769 reflections	Δρmax = 0.86 e Å^−3
176 parameters	Δρmin = −0.85 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00036 (5)

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
I1	0.598461 (19)	0.235936 (19)	1.15099 (7)	0.0822 (3)
S1	0.33388 (6)	0.09557 (6)	0.77826 (17)	0.0569 (4)
O1	0.29451 (18)	0.10062 (18)	0.6899 (5)	0.0702 (13)
O2	0.31122 (18)	0.05280 (17)	0.8793 (5)	0.0641 (12)
O3	0.4975 (3)	0.0575 (3)	0.4710 (6)	0.1007 (19)
N1	0.3692 (2)	0.1580 (2)	0.8486 (6)	0.0570 (13)
H1N	0.375 (3)	0.181 (2)	0.778 (4)	0.068*
C1	0.3826 (3)	0.0856 (3)	0.6834 (7)	0.0627 (17)
C2	0.3865 (3)	0.0380 (3)	0.7020 (8)	0.073 (2)
H2	0.3627	0.0105	0.7660	0.088*
C3	0.4248 (5)	0.0295 (4)	0.6288 (9)	0.093 (3)
H3	0.4271	−0.0037	0.6410	0.111*
C4	0.4584 (4)	0.0690 (4)	0.5407 (9)	0.085 (3)
C5	0.4561 (3)	0.1163 (3)	0.5165 (8)	0.075 (2)
H5	0.4803	0.1428	0.4513	0.089*
C6	0.4171 (3)	0.1260 (3)	0.5895 (8)	0.0712 (19)
H6	0.4146	0.1590	0.5747	0.085*
C7	0.4211 (2)	0.1746 (2)	0.9173 (7)	0.0535 (14)
C8	0.4261 (3)	0.1392 (2)	1.0095 (7)	0.0593 (16)
H8	0.3948	0.1031	1.0289	0.071*
C9	0.4768 (3)	0.1570 (2)	1.0723 (7)	0.0566 (15)
H9	0.4806	0.1324	1.1336	0.068*
C10	0.5226 (3)	0.2098 (3)	1.0484 (7)	0.0586 (16)
C11	0.5175 (3)	0.2459 (3)	0.9571 (8)	0.0630 (17)
H11	0.5487	0.2824	0.9401	0.076*
C12	0.4667 (3)	0.2280 (3)	0.8916 (7)	0.0603 (16)
H12	0.4630	0.2522	0.8290	0.072*
C13	0.5342 (4)	0.0980 (5)	0.3824 (11)	0.113 (3)
H13A	0.5581	0.0851	0.3398	0.170*
H13B	0.5579	0.1332	0.4315	0.170*
H13C	0.5126	0.1045	0.3127	0.170*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0602 (3)	0.0595 (3)	0.1317 (5)	0.0335 (2)	−0.0291 (3)	−0.0267 (3)
S1	0.0480 (8)	0.0445 (8)	0.0630 (10)	0.0118 (6)	−0.0084 (7)	0.0115 (7)
O1	0.054 (2)	0.052 (2)	0.084 (3)	0.011 (2)	−0.018 (2)	0.019 (2)
O2	0.060 (2)	0.049 (2)	0.066 (3)	0.0142 (19)	−0.005 (2)	0.014 (2)
O3	0.132 (5)	0.120 (5)	0.080 (4)	0.085 (5)	−0.027 (4)	−0.009 (4)
N1	0.051 (3)	0.041 (2)	0.071 (4)	0.018 (2)	−0.009 (3)	0.013 (2)
C1	0.060 (4)	0.055 (4)	0.056 (4)	0.016 (3)	−0.018 (3)	0.000 (3)
C2	0.093 (5)	0.071 (4)	0.059 (4)	0.044 (4)	−0.018 (4)	−0.011 (4)
C3	0.136 (8)	0.074 (5)	0.077 (6)	0.059 (5)	−0.030 (6)	−0.004 (5)
C4	0.120 (7)	0.091 (6)	0.074 (5)	0.076 (5)	−0.051 (5)	−0.030 (5)
C5	0.057 (4)	0.081 (5)	0.059 (4)	0.015 (4)	−0.011 (3)	0.004 (4)
C6	0.063 (4)	0.065 (4)	0.072 (5)	0.022 (3)	−0.003 (4)	0.010 (4)
C7	0.052 (3)	0.047 (3)	0.060 (4)	0.024 (3)	0.003 (3)	−0.002 (3)
C8	0.061 (4)	0.040 (3)	0.068 (4)	0.019 (3)	−0.009 (3)	−0.004 (3)
C9	0.062 (4)	0.038 (3)	0.068 (4)	0.024 (3)	−0.011 (3)	−0.004 (3)
C10	0.053 (3)	0.050 (3)	0.077 (5)	0.029 (3)	−0.010 (3)	−0.020 (3)
C11	0.046 (3)	0.048 (3)	0.083 (5)	0.014 (3)	0.008 (3)	0.000 (3)
C12	0.057 (4)	0.057 (4)	0.064 (4)	0.025 (3)	0.003 (3)	0.013 (3)
C13	0.103 (7)	0.168 (11)	0.080 (7)	0.076 (8)	−0.016 (6)	−0.010 (7)

Geometric parameters (Å, º)

I1—C10	2.092 (6)	C2—C3	1.388 (12)
S1—O2	1.424 (4)	C3—C4	1.334 (13)
S1—O1	1.447 (5)	C4—C5	1.347 (11)
S1—N1	1.640 (5)	C5—C6	1.420 (11)
S1—C1	1.760 (8)	C7—C8	1.387 (9)
O3—C13	1.376 (12)	C7—C12	1.392 (8)
O3—C4	1.437 (10)	C8—C9	1.369 (9)
N1—C7	1.428 (8)	C9—C10	1.380 (9)
C1—C2	1.372 (10)	C10—C11	1.395 (9)
C1—C6	1.391 (10)	C11—C12	1.383 (9)
O2—S1—O1	117.6 (3)	C3—C4—O3	114.9 (8)
O2—S1—N1	110.3 (3)	C5—C4—O3	121.5 (9)
O1—S1—N1	103.7 (3)	C4—C5—C6	119.3 (8)
O2—S1—C1	107.4 (3)	C1—C6—C5	117.8 (7)
O1—S1—C1	110.5 (3)	C8—C7—C12	120.2 (6)
N1—S1—C1	106.9 (3)	C8—C7—N1	121.4 (5)
C13—O3—C4	116.9 (8)	C12—C7—N1	118.4 (6)
C7—N1—S1	120.5 (4)	C9—C8—C7	119.2 (6)
C2—C1—C6	119.9 (7)	C8—C9—C10	121.5 (6)
C2—C1—S1	120.1 (6)	C9—C10—C11	119.6 (6)
C6—C1—S1	120.0 (6)	C9—C10—I1	120.0 (5)
C1—C2—C3	121.0 (8)	C11—C10—I1	120.3 (5)
C4—C3—C2	118.4 (8)	C12—C11—C10	119.3 (6)
C3—C4—C5	123.5 (9)	C11—C12—C7	120.2 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.90 (1)	1.98 (2)	2.855 (6)	166 (6)

Symmetry code: (i) −x+2/3, −y+1/3, −z+4/3.

(Cl~Cl)

Crystal data

C12H9Cl2NO2S	F(000) = 2772
Mr = 302.16	Dx = 1.584 Mg m^−3
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
a = 26.5773 (11) Å	µ = 0.67 mm^−1
c = 9.3206 (4) Å	T = 120 K
V = 5701.6 (4) Å^3	0.15 × 0.15 × 0.05 mm
Z = 18

Data collection

Radiation source: fine-focus sealed tube	1979 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.153
Absorption correction: empirical (using intensity measurements) SADABS V2.10 (Sheldrick, G.M., 2003)	θmax = 26.0°, θmin = 3.1°
Tmin = 0.906, Tmax = 0.967	h = −13→31
5243 measured reflections	k = −28→30
2451 independent reflections	l = −11→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0523P)^2 + 13.450P] where P = (Fo^2 + 2Fc^2)/3
2451 reflections	(Δ/σ)max = 0.008
175 parameters	Δρmax = 0.45 e Å^−3
1 restraint	Δρmin = −0.64 e Å^−3

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
S1	0.76239 (3)	0.67788 (3)	0.06637 (7)	0.0201 (2)
Cl1	0.75570 (3)	0.86466 (3)	0.45679 (7)	0.0280 (2)
Cl2	0.91072 (4)	0.93432 (3)	−0.32405 (9)	0.0375 (2)
O1	0.76544 (8)	0.63498 (8)	0.1552 (2)	0.0254 (5)
O2	0.71604 (8)	0.65833 (8)	−0.0349 (2)	0.0246 (5)
N1	0.82485 (10)	0.71126 (10)	−0.0151 (2)	0.0207 (5)
H1N	0.8517 (10)	0.7095 (14)	0.038 (3)	0.028 (9)*
C1	0.75986 (12)	0.73022 (12)	0.1776 (3)	0.0198 (6)
C2	0.80761 (12)	0.76526 (13)	0.2643 (3)	0.0243 (6)
H2	0.8409	0.7608	0.2634	0.032 (9)*
C3	0.80610 (13)	0.80642 (13)	0.3514 (3)	0.0253 (6)
H3	0.8383	0.8307	0.4107	0.031 (9)*
C4	0.75690 (12)	0.81171 (12)	0.3508 (3)	0.0216 (6)
C5	0.70909 (13)	0.77709 (13)	0.2661 (3)	0.0250 (6)
H5	0.6756	0.7812	0.2687	0.038 (9)*
C6	0.71100 (12)	0.73607 (12)	0.1771 (3)	0.0234 (6)
H6	0.6790	0.7123	0.1165	0.026 (8)*
C7	0.84423 (12)	0.76512 (12)	−0.0884 (3)	0.0190 (6)
C8	0.90141 (12)	0.80927 (13)	−0.0675 (3)	0.0238 (6)
H8	0.9261	0.8036	−0.0038	0.035 (9)*
C9	0.92226 (13)	0.86167 (13)	−0.1404 (3)	0.0273 (6)
H9	0.9614	0.8918	−0.1284	0.031 (9)*
C10	0.88545 (13)	0.86941 (12)	−0.2305 (3)	0.0250 (6)
C11	0.82829 (12)	0.82609 (13)	−0.2500 (3)	0.0233 (6)
H11	0.8033	0.8323	−0.3110	0.035 (9)*
C12	0.80791 (12)	0.77321 (12)	−0.1792 (3)	0.0217 (6)
H12	0.7691	0.7428	−0.1936	0.030 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0185 (4)	0.0201 (4)	0.0216 (4)	0.0096 (3)	−0.0018 (2)	0.0018 (3)
Cl1	0.0356 (4)	0.0294 (4)	0.0253 (4)	0.0210 (3)	0.0013 (3)	0.0008 (3)
Cl2	0.0349 (5)	0.0280 (4)	0.0497 (5)	0.0158 (4)	0.0069 (3)	0.0140 (3)
O1	0.0230 (10)	0.0217 (10)	0.0307 (11)	0.0105 (9)	−0.0019 (8)	0.0064 (8)
O2	0.0194 (10)	0.0251 (11)	0.0272 (10)	0.0094 (9)	−0.0060 (8)	−0.0009 (8)
N1	0.0188 (12)	0.0241 (12)	0.0215 (12)	0.0124 (10)	0.0006 (9)	0.0032 (9)
C1	0.0219 (14)	0.0203 (14)	0.0189 (13)	0.0118 (12)	0.0018 (10)	0.0027 (11)
C2	0.0227 (14)	0.0342 (16)	0.0214 (13)	0.0184 (13)	−0.0014 (11)	0.0013 (12)
C3	0.0226 (15)	0.0319 (16)	0.0209 (13)	0.0132 (13)	−0.0017 (11)	0.0003 (12)
C4	0.0272 (15)	0.0200 (14)	0.0179 (13)	0.0120 (12)	0.0045 (11)	0.0049 (10)
C5	0.0212 (14)	0.0284 (15)	0.0279 (15)	0.0144 (13)	0.0027 (11)	0.0054 (12)
C6	0.0184 (14)	0.0257 (15)	0.0233 (14)	0.0089 (12)	−0.0007 (11)	0.0045 (11)
C7	0.0222 (14)	0.0225 (14)	0.0143 (12)	0.0127 (12)	0.0020 (10)	−0.0014 (10)
C8	0.0220 (14)	0.0298 (16)	0.0227 (14)	0.0152 (13)	−0.0026 (11)	0.0005 (12)
C9	0.0215 (15)	0.0272 (16)	0.0310 (15)	0.0105 (13)	−0.0025 (12)	−0.0022 (12)
C10	0.0317 (16)	0.0234 (15)	0.0242 (14)	0.0169 (13)	0.0058 (12)	0.0033 (11)
C11	0.0224 (14)	0.0308 (16)	0.0207 (14)	0.0164 (13)	0.0032 (11)	0.0044 (11)
C12	0.0207 (14)	0.0240 (14)	0.0222 (13)	0.0126 (12)	0.0022 (11)	−0.0002 (11)

Geometric parameters (Å, º)

S1—O2	1.428 (2)	C3—C4	1.383 (4)
S1—O1	1.4436 (19)	C4—C5	1.384 (4)
S1—N1	1.627 (2)	C5—C6	1.391 (4)
S1—C1	1.763 (3)	C7—C12	1.380 (4)
Cl1—C4	1.733 (3)	C7—C8	1.393 (4)
Cl2—C10	1.741 (3)	C8—C9	1.391 (4)
N1—C7	1.430 (3)	C9—C10	1.380 (4)
C1—C6	1.383 (4)	C10—C11	1.385 (4)
C1—C2	1.396 (4)	C11—C12	1.394 (4)
C2—C3	1.378 (4)
O2—S1—O1	118.06 (12)	C5—C4—Cl1	118.8 (2)
O2—S1—N1	110.47 (12)	C4—C5—C6	118.7 (3)
O1—S1—N1	104.67 (12)	C1—C6—C5	119.4 (3)
O2—S1—C1	108.02 (13)	C12—C7—C8	120.5 (3)
O1—S1—C1	109.00 (12)	C12—C7—N1	121.3 (2)
N1—S1—C1	105.97 (12)	C8—C7—N1	118.2 (2)
C7—N1—S1	121.84 (19)	C9—C8—C7	119.7 (3)
C6—C1—C2	121.2 (3)	C10—C9—C8	119.3 (3)
C6—C1—S1	119.7 (2)	C9—C10—C11	121.4 (3)
C2—C1—S1	119.1 (2)	C9—C10—Cl2	120.1 (2)
C3—C2—C1	119.5 (3)	C11—C10—Cl2	118.5 (2)
C2—C3—C4	118.9 (3)	C10—C11—C12	119.2 (3)
C3—C4—C5	122.3 (3)	C7—C12—C11	119.9 (3)
C3—C4—Cl1	118.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.89 (1)	1.98 (1)	2.860 (3)	171 (3)

Symmetry code: (i) −x+5/3, −y+4/3, −z+1/3.