Eight isostructural 4,4'-disubstituted N-phenyl­benzene­sulfonamides

The isostructural crystals of 4-cyano-N-(4-meth­oxy­phenyl)benzene­sulfonamide, C₁₄H₁₂N₂O₃S, (I), N-(4-meth­oxy­phenyl)-4-(trifluoro­methyl)benzene­sulfonamide, C₁₄H₁₂F₃NO₃S, (II), 4-iodo-N-(4-meth­oxy­phenyl)benzene­sulfonamide, C₁₃H₁₂INO₃S, (III), 4-bromo-N-(4-meth­oxy­phenyl)benzene­sulfonamide, C₁₃H₁₂BrNO₃S, (IV), 4-chloro-N-(4-meth­oxy­phenyl)benzene­sulfonamide, C₁₃H₁₂ClNO₃S, (V), 4-fluoro-N-(4-meth­oxy­phenyl)benzene­sulfonamide, C₁₃H₁₂FNO₃S, (VI), N-(4-chloro­phenyl)-4-meth­oxy­benzene­sulfonamide, C₁₃H₁₂ClNO₃S, (VII), and 4-cyano-N-phenyl­benzene­sulfonamide, C₁₃H₁₀N₂O₂S, (VIII), contain infinite chains composed of N-H...O(sulfonyl) hydrogen-bonded mol­ecules. The crystal structures of (I)-(VIII) have been compared using the XPac software and quanti­tative descriptors of isostructurality were generated [Gelbrich, Threlfall & Hursthouse (2012). Cryst­EngComm, 14, 5454-5464]. Certain isostructural relationships in this series involve mol­ecules with substantially different spatial demands, e.g. (VI) and (VIII) are related by the simultaneous inter­change of F[rightwards arrow]CN on the benzene­sul­fon­amide ring and OMe[rightwards arrow]H on the N-phenyl ring, which indicates that the geometry of the three-dimensional crystal-packing mode of (I)-(VIII) is unusually adaptable to different mol­ecular shapes.

S1. Comment

We have investigated families of crystal structures of closely related organic compounds in order to examine the effect of incremental changes in molecular shape, van der Waals interactions and other, more directed, intermolecular forces on the crystal packing (Hursthouse, 2004; Gelbrich & Hursthouse, 2006; Gelbrich et al., 2007, 2012; Hursthouse et al., 2010, 2011). One such family comprises a 10 × 10 matrix of 4,4'-substituted N-phenylbenzenesulfonamides, XC₆H₄–SO₂–NH–C₆H₄Y, denoted X/Y, where X and Y are NO₂, CN, CF₃, I, Br, Cl, F, Me, OMe and H. A general overview of this set has been given previously (Gelbrich et al., 2007) and it was reported that all investigated crystal structures contain N—H···A bonded molecules (A = hydrogen-bond acceptor). The crystal structures of the X/Y set were classified according to: (i) the type of A site employed; (ii) the connectivity type of the resulting N—H···A bonded structure; (iii) the spatial arrangement of the molecules forming this hydrogen-bonded structure; (iv) the complete three-dimensional crystal-packing arrangement (`structure type'). A subset of 22 isostructural X/Y compounds has been discussed in detail (Gelbrich et al., 2007). This particular structure type, denoted A1.1, is characterized by the presence of centrosymmetric N—H···O(sulfonyl) bonded dimers, which are arranged around a 3 axis.

In this contribution, we report another eight crystal structures of the X/Y matrix: CN/OMe, (I), CF₃/OMe, (II), I/OMe, (III), Br/OMe, (IV), Cl/OMe, (V), F/OMe, (VI), OMe/Cl, (VII), and CN/H, (VIII). The crystals of (I)–(VIII) investigated here all have the space group Pna2₁. The asymmetric units of (I)–(VIII) contain a single molecule (Fig. 1). The overlay in Fig. 2 illustrates that the molecular geometries are very similar throughout the series, except for the X and Y substituents. The most significant conformational differences between individual members may be described in terms of a slight rotation of the aromatic rings about the pseudo-axes S1—C1···C4—X and N1—C7···C10—Y. In the following we discuss details of the molecular and crystal structure of Cl/OMe, (V), which is representative of the entire series of structures (I)–(VIII), denoted previously as type B1.10 (Gelbrich et al., 2007), where B indicates the presence of N—H···O(sulfonyl) bonded chains, 1 indicates their specific geometry and 10 is the running number of structure types exhibiting these characteristics. [Is this B1.10 notation different from the A1.1 in the previous paragraph?]

The V-shaped molecular geometry is characterized by the three torsion angles C2—C1—S1—N1 = -88.2 (3)°, C1—S1—N1—C7 = -67.9 (3)° and S1—N1—C7—C8 = 101.1 (3)°. The centroids of the two aromatic rings of (V) are 4.983 (4) Å apart and the mean planes of these two rings form an angle of 42.8 (1)°. The methoxy substituents Y in (I)–(VI) and X in (VII) are oriented in such a way that the OMe group is approximately coplanar with the attached aromatic ring. In (I)–(VI), the terminal O3—C bond is oriented approximately parallel to the C7—C12 bond of the ring, and in (VII) it lies parallel to the C1—C2 bond.

Each molecule is linked to two other molecules via an N1—H···O1(sulfonyl) interaction. The resulting hydrogen-bonded chain (Fig. 3) has a V-shaped cross-section and propagates parallel to the c axis. Neighbouring chains of this kind are arranged into a layer structure, which lies parallel to the bc plane and possesses n-glide symmetry (Fig. 4). The stacking of these two-dimensional structures along [100] is such that the molecules of neighbouring layers are related by 2₁ and glide-symmetry operations.

The crystal structures of (I)–(VIII) were compared with each other using the program XPAC (Gelbrich & Hursthouse, 2005), using geometric parameters generated from all non-H atomic positions, except for those of the substituents X and Y. Each crystal structure was represented by a cluster consisting of a central molecule and its 14 closest neighbours. The complete clusters representing (I)–(VIII) were found to possess fundamentally the same geometry, indicating isostructurality. The isostructurality of the X/OMe series with X = CN, CF₃, I, Br and Cl, i.e. (I)–(V), is not unusual, since the molecular shape varies relatively little in this group. However, each of (VI), (VII) and (VIII) differs quite substantially from these five compounds in the size of either or both of their X and Y substituents, so that their isostructurality with (I)–(V) is rather surprising.

To quantify the isostructural relationships in this set, the XPAC dissimilarity index x (Gelbrich et al., 2012) and distance parameter d were calculated for all 28 comparisons between two individual structures. The results of these calculations are collected in Fig. 5. As expected, the lowest x values (≤ 3.1), indicating the highest degree of similarity, were found for the X/OMe subset (I)–(V). The inclusion of the fluoro analogue, (VI), resulted in somewhat higher values (x ≤ 4.9) because F is considerably smaller than the other X substituents present in this subset. Even larger molecular-shape differences exist between (I)–(V) on the one hand and OMe/Cl, (VII), and in particular CN/H, (VIII), on the other. The modifications of the packing geometry are therefore more pronounced and the dissimilarity parameters for comparisons involving (VII) and (VIII) are systematically higher, at 3.7 ≤ x ≤ 5.2 and 6.8 ≤ x ≤ 7.9, respectively. Overall, the dissimilarity indices x for the B1.10 series are broadly consistent with trends identified in a recent study of close chemical analogues of (I)–(VIII) (Gelbrich et al., 2012).

OMe/Cl, (VII), and CN/H, (VIII), are the two least closely related packing arrangements in this group (x = 10.1). For a more detailed analysis, an individual dissimilarity parameter x_i was calculated for each unit consisting of two next-neighbour molecules in the structures of (VII) and (VIII). The lowest x_i value of 3.2 was obtained for the assembly of two N—H···O linked molecules, while for all other two-molecule units the values were considerably higher (10.0 ≤ x_i ≤ 14.3). This indicates that the geometry of the hydrogen-bonded chain is very rigid. Therefore, adjustment for the different shape requirements of the various X and Y substituents consists mainly of a subtle change in the alignment of neighbouring N—H···O bonded chains relative to one another.

Related literature

For related literature, see: Gelbrich & Hursthouse (2005, 2006); Gelbrich et al. (2007, 2012); Hursthouse (2004); Hursthouse et al. (2010, 2011).

S2. Experimental

Compounds (I)–(VIII) were prepared as described previously (Gelbrich et al., 2007). All XPac (Gelbrich & Hursthouse, 2005; Gelbrich et al., 2012) calculations were carried out with a set of 16 non-H atomic positions per molecule which did not include the substituents X and Y. The dissimilarity parameters collected in Fig. 4 refer to clusters composed of a central molecule and its 14 closest neighbours, which represent complete crystal structures.

S3. Refinement

The structure models of (I) and (IV)–(VIII) were refined using matching sets of atomic coordinates, with the z coordinate of atom S1 at approximately 0.5. The corresponding inverted model was used in the case of (II) and (III). All H atoms were identified in a difference map. Methyl H atoms were idealized and included as rigid groups allowed to rotate but not tip, with C—H = 0.98 Å, and refined with U_iso(H) = 1.5U_eq(C). H atoms attached to aromatic C atoms were positioned geometrically, with C—H = 0.95 Å, and refined with U_iso(H) = 1.2U_eq(C). H atoms attached to the N atoms were refined with restrained distances [N—H = 0.86 (2) Å], and their U_iso parameters were refined freely.

Computing details

For all compounds, data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

	Fig. 1. The asymmetric units of (I)–(VIII), with the atom-numbering schemes. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. An overlay of the molecular structures of (I) (red in the electronic version of the paper), (II) (orange), (III) (purple), (IV) (yellow), (V) (grey), (VI) (dark blue), (VII) (light blue) and (VIII) (green), based on a least-squares fit of 16 atomic positions (all non-H atoms, except those of the substituents X and Y). H atoms have been omitted for clarity.
	Fig. 3. The N—H···O bonded chain in the crystal structure of Cl/OMe, (V). O, N and H atoms directly involved in hydrogen bonding are drawn as spheres.
	Fig. 4. The crystal packing of (V), (VII) and (VIII), viewed parallel to the c axis, with X and Y substituents drawn as spheres. N—H···O bonded chains, which propagate parallel to [001], are represented by a single molecule. The layer structure highlighted by dot-dashed lines (left diagram) is the result of the stacking of these chains via a glide operation. Note that OMe/Cl, (VII), and CN/H, (VIII), show the largest differences (x = 10.1) of all investigated structures.
	Fig. 5. An XPAC map, showing the dissimilarity indices x (lower left section of the matrix) and distance parameters d (upper right section) for the 28 binary structure comparisons in the investigated set.

(I) 4-Cyano-N-(4-methoxyphenyl)benzenesulfonamide

Crystal data

C14H12N2O3S	F(000) = 600
Mr = 288.32	Dx = 1.370 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3975 reflections
a = 22.0249 (7) Å	θ = 2.9–26.0°
b = 12.5626 (5) Å	µ = 0.24 mm^−1
c = 5.0512 (1) Å	T = 293 K
V = 1397.62 (8) Å^3	Block, colourless
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection

Bruker Nonius 95mm CCD camera on κ-goniostat diffractometer	2582 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1990 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 3.2°
ϕ and ω scans	h = −26→24
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −13→15
Tmin = 0.954, Tmax = 0.976	l = −5→6
10978 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0468P)^2 + 0.0123P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.089	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.17 e Å^−3
2582 reflections	Δρmin = −0.18 e Å^−3
187 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.026 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1042 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.02 (9)

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	0.23268 (3)	0.24262 (4)	0.50004 (14)	0.04928 (19)
O1	0.21574 (9)	0.22588 (15)	0.2298 (3)	0.0651 (5)
O2	0.24917 (8)	0.34582 (13)	0.5899 (4)	0.0620 (5)
O3	0.05375 (8)	−0.17783 (13)	0.5305 (4)	0.0672 (5)
N1	0.17517 (10)	0.20608 (17)	0.6802 (4)	0.0512 (5)
H1	0.1825 (12)	0.218 (2)	0.845 (4)	0.068 (9)*
N2	0.46936 (18)	−0.1168 (3)	0.8326 (10)	0.1395 (15)
C1	0.29271 (11)	0.15418 (19)	0.5730 (5)	0.0481 (6)
C6	0.29725 (13)	0.0578 (2)	0.4424 (6)	0.0635 (7)
H6	0.2694	0.0401	0.3111	0.076*
C2	0.33286 (11)	0.1800 (2)	0.7731 (5)	0.0566 (7)
H2	0.3292	0.2444	0.8622	0.068*
C3	0.37872 (13)	0.1092 (2)	0.8404 (7)	0.0663 (8)
H3	0.4062	0.1262	0.9737	0.080*
C4	0.38326 (12)	0.0135 (2)	0.7083 (6)	0.0648 (7)
C5	0.34284 (12)	−0.0116 (2)	0.5071 (7)	0.0707 (8)
H5	0.3467	−0.0756	0.4161	0.085*
C7	0.14547 (10)	0.10587 (19)	0.6299 (5)	0.0464 (6)
C8	0.15769 (10)	0.0179 (2)	0.7840 (5)	0.0532 (6)
H8	0.1873	0.0215	0.9148	0.064*
C9	0.12615 (11)	−0.0753 (2)	0.7449 (5)	0.0574 (7)
H9	0.1340	−0.1340	0.8520	0.069*
C10	0.08287 (10)	−0.08239 (18)	0.5477 (5)	0.0512 (6)
C11	0.07138 (10)	0.0045 (2)	0.3908 (5)	0.0557 (6)
H11	0.0427	0.0000	0.2562	0.067*
C12	0.10245 (11)	0.09931 (19)	0.4321 (5)	0.0518 (6)
H12	0.0943	0.1583	0.3266	0.062*
C13	0.43091 (17)	−0.0595 (3)	0.7789 (8)	0.0903 (10)
C14	0.00815 (14)	−0.1891 (3)	0.3315 (8)	0.0789 (9)
H14A	−0.0083	−0.2598	0.3382	0.118*
H14B	0.0258	−0.1768	0.1604	0.118*
H14C	−0.0236	−0.1383	0.3622	0.118*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0591 (4)	0.0521 (4)	0.0367 (3)	−0.0045 (3)	0.0016 (3)	−0.0008 (3)
O1	0.0819 (12)	0.0799 (13)	0.0334 (10)	−0.0049 (10)	−0.0030 (9)	−0.0006 (9)
O2	0.0774 (11)	0.0436 (10)	0.0650 (12)	−0.0078 (8)	0.0017 (9)	−0.0025 (8)
O3	0.0649 (10)	0.0564 (10)	0.0802 (14)	−0.0060 (8)	−0.0163 (11)	−0.0021 (10)
N1	0.0562 (13)	0.0604 (13)	0.0371 (11)	−0.0037 (10)	0.0016 (9)	−0.0075 (11)
N2	0.143 (3)	0.106 (3)	0.169 (4)	0.047 (2)	−0.036 (3)	0.004 (3)
C1	0.0546 (14)	0.0459 (14)	0.0437 (13)	−0.0079 (10)	0.0067 (10)	−0.0022 (10)
C6	0.0746 (16)	0.0580 (16)	0.0579 (18)	−0.0056 (13)	−0.0065 (13)	−0.0120 (13)
C2	0.0606 (16)	0.0551 (15)	0.0541 (16)	−0.0054 (12)	−0.0027 (13)	−0.0105 (12)
C3	0.0631 (17)	0.0655 (19)	0.0702 (19)	−0.0026 (13)	−0.0086 (15)	−0.0023 (15)
C4	0.0699 (18)	0.0493 (16)	0.075 (2)	0.0022 (13)	−0.0007 (16)	0.0032 (15)
C5	0.0895 (18)	0.0484 (15)	0.074 (2)	0.0026 (13)	0.0004 (18)	−0.0160 (16)
C7	0.0435 (13)	0.0559 (16)	0.0398 (13)	0.0014 (11)	0.0033 (11)	−0.0026 (11)
C8	0.0519 (14)	0.0602 (16)	0.0476 (15)	−0.0037 (12)	−0.0093 (12)	−0.0015 (12)
C9	0.0577 (15)	0.0581 (16)	0.0564 (16)	0.0030 (12)	−0.0131 (13)	0.0079 (13)
C10	0.0462 (12)	0.0514 (14)	0.0560 (17)	0.0026 (10)	0.0016 (11)	−0.0071 (12)
C11	0.0501 (14)	0.0701 (18)	0.0469 (13)	−0.0032 (12)	−0.0079 (12)	−0.0001 (13)
C12	0.0511 (14)	0.0609 (15)	0.0433 (15)	0.0015 (11)	−0.0051 (11)	0.0055 (11)
C13	0.098 (2)	0.071 (2)	0.103 (3)	0.0127 (19)	−0.013 (2)	0.0015 (18)
C14	0.0694 (18)	0.085 (2)	0.082 (2)	−0.0165 (16)	−0.0173 (17)	−0.0129 (19)

Geometric parameters (Å, º)

S1—O2	1.4209 (18)	C4—C5	1.388 (4)
S1—O1	1.4307 (18)	C4—C13	1.439 (4)
S1—N1	1.626 (2)	C5—H5	0.9300
S1—C1	1.766 (3)	C7—C8	1.379 (4)
O3—C10	1.362 (3)	C7—C12	1.379 (3)
O3—C14	1.428 (4)	C8—C9	1.376 (3)
N1—C7	1.441 (3)	C8—H8	0.9300
N1—H1	0.863 (18)	C9—C10	1.382 (3)
N2—C13	1.143 (4)	C9—H9	0.9300
C1—C2	1.381 (3)	C10—C11	1.373 (3)
C1—C6	1.383 (4)	C11—C12	1.389 (3)
C6—C5	1.369 (4)	C11—H11	0.9300
C6—H6	0.9300	C12—H12	0.9300
C2—C3	1.388 (4)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.378 (4)	C14—H14C	0.9600
C3—H3	0.9300
O2—S1—O1	120.37 (11)	C4—C5—H5	120.0
O2—S1—N1	106.14 (11)	C8—C7—C12	119.7 (2)
O1—S1—N1	106.83 (12)	C8—C7—N1	120.8 (2)
O2—S1—C1	108.42 (11)	C12—C7—N1	119.4 (2)
O1—S1—C1	107.56 (12)	C9—C8—C7	120.2 (2)
N1—S1—C1	106.79 (11)	C9—C8—H8	119.9
C10—O3—C14	117.6 (2)	C7—C8—H8	119.9
C7—N1—S1	120.10 (16)	C8—C9—C10	120.4 (2)
C7—N1—H1	113.9 (18)	C8—C9—H9	119.8
S1—N1—H1	110.3 (19)	C10—C9—H9	119.8
C2—C1—C6	120.5 (2)	O3—C10—C11	125.2 (2)
C2—C1—S1	118.96 (19)	O3—C10—C9	115.3 (2)
C6—C1—S1	120.4 (2)	C11—C10—C9	119.5 (2)
C5—C6—C1	119.8 (3)	C10—C11—C12	120.3 (2)
C5—C6—H6	120.1	C10—C11—H11	119.9
C1—C6—H6	120.1	C12—C11—H11	119.9
C1—C2—C3	119.6 (3)	C7—C12—C11	119.9 (2)
C1—C2—H2	120.2	C7—C12—H12	120.0
C3—C2—H2	120.2	C11—C12—H12	120.0
C4—C3—C2	119.5 (3)	N2—C13—C4	179.0 (5)
C4—C3—H3	120.2	O3—C14—H14A	109.5
C2—C3—H3	120.2	O3—C14—H14B	109.5
C3—C4—C5	120.4 (2)	H14A—C14—H14B	109.5
C3—C4—C13	119.3 (3)	O3—C14—H14C	109.5
C5—C4—C13	120.3 (3)	H14A—C14—H14C	109.5
C6—C5—C4	120.0 (2)	H14B—C14—H14C	109.5
C6—C5—H5	120.0

(II) N-(4-Methoxyphenyl)-4-(trifluoromethyl)benzenesulfonamide

Crystal data

C14H12F3NO3S	F(000) = 680
Mr = 331.31	Dx = 1.546 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1615 reflections
a = 22.1833 (14) Å	θ = 2.9–26.0°
b = 12.8024 (8) Å	µ = 0.27 mm^−1
c = 5.0114 (3) Å	T = 120 K
V = 1423.23 (15) Å^3	Block, colourless
Z = 4	0.20 × 0.10 × 0.05 mm

Data collection

Bruker Nonius 95mm CCD camera on κ-goniostat diffractometer	2724 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2003 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 3.2°
ϕ and ω scans	h = −27→26
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −15→15
Tmin = 0.947, Tmax = 0.987	l = −6→6
6994 measured reflections

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0525P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2724 reflections	Δρmax = 0.28 e Å^−3
202 parameters	Δρmin = −0.37 e Å^−3
2 restraints	Absolute structure: Flack (1983), with 1164 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (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	0.77318 (4)	0.78225 (7)	0.50004 (19)	0.0267 (3)
O1	0.78954 (13)	0.7996 (2)	0.7721 (6)	0.0326 (7)
O2	0.75644 (13)	0.6803 (2)	0.4104 (5)	0.0312 (7)
O3	0.94230 (13)	1.20316 (19)	0.4916 (7)	0.0361 (7)
N1	0.83024 (16)	0.8182 (3)	0.3150 (7)	0.0276 (8)
H1	0.8214 (19)	0.810 (3)	0.145 (4)	0.033*
C1	0.71342 (17)	0.8700 (3)	0.4250 (7)	0.0238 (9)
C2	0.67254 (17)	0.8426 (3)	0.2271 (8)	0.0289 (9)
H2	0.6746	0.7763	0.1423	0.035*
C3	0.62850 (19)	0.9149 (3)	0.1564 (9)	0.0307 (10)
H3	0.6002	0.8988	0.0201	0.037*
C4	0.62607 (18)	1.0101 (3)	0.2850 (8)	0.0287 (9)
C5	0.66670 (18)	1.0362 (3)	0.4820 (9)	0.0309 (9)
H5	0.6643	1.1020	0.5691	0.037*
C6	0.71131 (19)	0.9648 (3)	0.5515 (8)	0.0299 (10)
H6	0.7400	0.9816	0.6854	0.036*
C7	0.85891 (18)	0.9182 (3)	0.3672 (8)	0.0271 (9)
C8	0.84404 (19)	1.0046 (3)	0.2187 (8)	0.0298 (9)
H8	0.8140	0.9997	0.0843	0.036*
C9	0.87280 (18)	1.0990 (3)	0.2646 (9)	0.0308 (9)
H9	0.8627	1.1586	0.1611	0.037*
C10	0.91659 (18)	1.1062 (3)	0.4625 (9)	0.0306 (9)
C11	0.93144 (19)	1.0196 (3)	0.6120 (9)	0.0309 (10)
H11	0.9613	1.0243	0.7472	0.037*
C12	0.90220 (18)	0.9251 (3)	0.5630 (8)	0.0282 (10)
H12	0.9122	0.8651	0.6655	0.034*
C13	0.57759 (19)	1.0861 (3)	0.2096 (9)	0.0335 (10)
C14	0.9845 (2)	1.2152 (4)	0.7062 (9)	0.0428 (12)
H14A	0.9997	1.2871	0.7083	0.064*
H14B	1.0182	1.1667	0.6811	0.064*
H14C	0.9644	1.2000	0.8760	0.064*
F1	0.52239 (10)	1.05112 (19)	0.2795 (6)	0.0471 (7)
F2	0.58365 (12)	1.17888 (19)	0.3214 (7)	0.0524 (8)
F3	0.57469 (11)	1.1010 (2)	−0.0541 (5)	0.0497 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0278 (5)	0.0289 (5)	0.0233 (5)	0.0023 (4)	−0.0005 (5)	0.0007 (5)
O1	0.0311 (16)	0.0409 (16)	0.0257 (15)	0.0038 (13)	0.0004 (14)	0.0007 (13)
O2	0.0335 (16)	0.0214 (14)	0.0388 (17)	0.0024 (12)	0.0015 (13)	−0.0008 (11)
O3	0.0317 (16)	0.0339 (15)	0.0427 (16)	−0.0050 (12)	−0.0065 (17)	−0.0019 (15)
N1	0.0277 (19)	0.0320 (17)	0.0229 (17)	0.0004 (15)	−0.0001 (15)	−0.0029 (15)
C1	0.024 (2)	0.026 (2)	0.022 (2)	−0.0010 (16)	0.0027 (16)	0.0035 (15)
C2	0.028 (2)	0.026 (2)	0.032 (2)	−0.0039 (17)	−0.002 (2)	−0.0036 (18)
C3	0.027 (2)	0.030 (2)	0.035 (2)	−0.003 (2)	−0.0051 (18)	0.0000 (17)
C4	0.025 (2)	0.031 (2)	0.030 (2)	−0.0011 (17)	0.005 (2)	0.0039 (18)
C5	0.032 (2)	0.029 (2)	0.032 (2)	−0.0030 (17)	0.004 (2)	−0.0034 (19)
C6	0.028 (2)	0.031 (2)	0.030 (2)	−0.0029 (18)	−0.0061 (18)	−0.0043 (18)
C7	0.025 (2)	0.032 (2)	0.024 (2)	0.0022 (18)	0.0040 (18)	−0.0049 (17)
C8	0.027 (2)	0.036 (2)	0.026 (2)	0.0001 (19)	−0.0030 (19)	−0.0021 (18)
C9	0.029 (2)	0.036 (2)	0.028 (2)	0.0067 (18)	−0.005 (2)	0.0034 (18)
C10	0.024 (2)	0.030 (2)	0.038 (2)	−0.0002 (17)	0.0054 (19)	−0.0035 (19)
C11	0.022 (2)	0.039 (2)	0.032 (2)	0.0004 (19)	−0.0062 (19)	−0.0003 (18)
C12	0.024 (2)	0.033 (2)	0.027 (2)	0.0063 (18)	−0.0030 (18)	0.0010 (17)
C13	0.025 (2)	0.030 (2)	0.046 (3)	0.0018 (19)	0.007 (2)	0.0014 (19)
C14	0.033 (3)	0.049 (3)	0.046 (3)	−0.008 (2)	−0.006 (2)	−0.005 (2)
F1	0.0226 (14)	0.0480 (15)	0.071 (2)	−0.0003 (11)	0.0056 (14)	0.0059 (14)
F2	0.0385 (15)	0.0313 (14)	0.087 (2)	0.0049 (12)	−0.0102 (15)	−0.0038 (14)
F3	0.0382 (15)	0.0664 (17)	0.0444 (17)	0.0173 (13)	0.0012 (13)	0.0184 (13)

Geometric parameters (Å, º)

S1—O1	1.428 (3)	C6—H6	0.9500
S1—O2	1.430 (3)	C7—C8	1.373 (6)
S1—N1	1.635 (4)	C7—C12	1.376 (6)
S1—C1	1.777 (4)	C8—C9	1.386 (5)
O3—C10	1.374 (5)	C8—H8	0.9500
O3—C14	1.434 (5)	C9—C10	1.391 (6)
N1—C7	1.454 (5)	C9—H9	0.9500
N1—H1	0.880 (19)	C10—C11	1.377 (6)
C1—C6	1.370 (6)	C11—C12	1.395 (6)
C1—C2	1.389 (5)	C11—H11	0.9500
C2—C3	1.392 (6)	C12—H12	0.9500
C2—H2	0.9500	C13—F2	1.320 (5)
C3—C4	1.380 (5)	C13—F3	1.337 (5)
C3—H3	0.9500	C13—F1	1.350 (5)
C4—C5	1.378 (6)	C14—H14A	0.9800
C4—C13	1.498 (6)	C14—H14B	0.9800
C5—C6	1.392 (6)	C14—H14C	0.9800
C5—H5	0.9500
O1—S1—O2	120.55 (16)	C8—C7—N1	120.5 (4)
O1—S1—N1	107.50 (18)	C12—C7—N1	119.3 (3)
O2—S1—N1	106.25 (17)	C7—C8—C9	120.1 (4)
O1—S1—C1	107.03 (17)	C7—C8—H8	119.9
O2—S1—C1	108.47 (18)	C9—C8—H8	119.9
N1—S1—C1	106.25 (17)	C8—C9—C10	119.8 (4)
C10—O3—C14	116.6 (3)	C8—C9—H9	120.1
C7—N1—S1	119.0 (3)	C10—C9—H9	120.1
C7—N1—H1	112 (3)	O3—C10—C11	124.8 (4)
S1—N1—H1	110 (3)	O3—C10—C9	115.2 (4)
C6—C1—C2	122.1 (4)	C11—C10—C9	120.1 (4)
C6—C1—S1	119.2 (3)	C10—C11—C12	119.4 (4)
C2—C1—S1	118.6 (3)	C10—C11—H11	120.3
C1—C2—C3	118.2 (4)	C12—C11—H11	120.3
C1—C2—H2	120.9	C7—C12—C11	120.4 (4)
C3—C2—H2	120.9	C7—C12—H12	119.8
C4—C3—C2	119.8 (4)	C11—C12—H12	119.8
C4—C3—H3	120.1	F2—C13—F3	107.2 (4)
C2—C3—H3	120.1	F2—C13—F1	106.3 (3)
C5—C4—C3	121.5 (4)	F3—C13—F1	105.1 (4)
C5—C4—C13	119.5 (4)	F2—C13—C4	113.8 (4)
C3—C4—C13	118.9 (4)	F3—C13—C4	112.1 (4)
C4—C5—C6	119.0 (4)	F1—C13—C4	111.8 (3)
C4—C5—H5	120.5	O3—C14—H14A	109.5
C6—C5—H5	120.5	O3—C14—H14B	109.5
C1—C6—C5	119.4 (4)	H14A—C14—H14B	109.5
C1—C6—H6	120.3	O3—C14—H14C	109.5
C5—C6—H6	120.3	H14A—C14—H14C	109.5
C8—C7—C12	120.2 (4)	H14B—C14—H14C	109.5

(III) 4-Iodo-N-(4-methoxyphenyl)benzenesulfonamide

Crystal data

C13H12INO3S	F(000) = 760
Mr = 389.20	Dx = 1.862 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1619 reflections
a = 21.6853 (8) Å	θ = 2.9–26.0°
b = 12.6570 (5) Å	µ = 2.46 mm^−1
c = 5.0586 (3) Å	T = 120 K
V = 1388.44 (11) Å^3	Block, colourless
Z = 4	0.30 × 0.15 × 0.10 mm

Data collection

Bruker Nonius 95mm CCD camera on κ-goniostat diffractometer	2550 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2294 reflections with I > 2σ(I)
10cm confocal mirrors monochromator	Rint = 0.048
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 3.3°
ϕ and ω scans	h = −26→26
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −15→15
Tmin = 0.526, Tmax = 0.791	l = −5→6
9765 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.0309P)^2 + 1.0095P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.075	(Δ/σ)max = 0.003
S = 1.04	Δρmax = 0.63 e Å^−3
2550 reflections	Δρmin = −0.61 e Å^−3
178 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0038 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1012 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.01 (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	0.549955 (12)	1.104130 (19)	0.15503 (15)	0.03175 (13)
S1	0.76462 (5)	0.76103 (9)	0.4999 (2)	0.0217 (3)
O3	0.94977 (13)	1.1770 (3)	0.4618 (8)	0.0251 (8)
O1	0.78196 (16)	0.7767 (3)	0.7713 (7)	0.0274 (8)
O2	0.74772 (14)	0.6581 (2)	0.4084 (7)	0.0240 (7)
N1	0.82259 (17)	0.7982 (3)	0.3158 (9)	0.0213 (8)
H1	0.817 (2)	0.785 (4)	0.153 (5)	0.034 (14)*
C1	0.70372 (19)	0.8489 (3)	0.4254 (10)	0.0207 (9)
C2	0.6629 (2)	0.8233 (3)	0.2248 (9)	0.0248 (11)
H2	0.6656	0.7570	0.1373	0.030*
C3	0.61815 (18)	0.8959 (3)	0.1541 (18)	0.0253 (8)
H3	0.5892	0.8792	0.0194	0.030*
C4	0.6155 (2)	0.9929 (3)	0.2799 (11)	0.0257 (10)
C5	0.6562 (2)	1.0187 (3)	0.4793 (10)	0.0267 (11)
H5	0.6538	1.0856	0.5640	0.032*
C6	0.7007 (2)	0.9461 (3)	0.5550 (10)	0.0258 (11)
H6	0.7288	0.9623	0.6933	0.031*
C7	0.8529 (2)	0.8976 (3)	0.3679 (10)	0.0199 (9)
C8	0.84161 (19)	0.9839 (3)	0.2041 (10)	0.0247 (12)
H8	0.8116	0.9796	0.0678	0.030*
C9	0.8750 (2)	1.0770 (4)	0.2428 (10)	0.0257 (11)
H9	0.8683	1.1360	0.1305	0.031*
C10	0.9178 (2)	1.0833 (3)	0.4444 (10)	0.0220 (10)
C11	0.92764 (19)	0.9974 (3)	0.6144 (13)	0.0233 (11)
H11	0.9563	1.0026	0.7557	0.028*
C12	0.8950 (2)	0.9050 (3)	0.5736 (10)	0.0230 (11)
H12	0.9015	0.8462	0.6870	0.028*
C13	0.9935 (2)	1.1858 (3)	0.6700 (16)	0.0326 (11)
H13A	1.0149	1.2538	0.6565	0.049*
H13B	1.0235	1.1282	0.6565	0.049*
H13C	0.9722	1.1816	0.8406	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.03164 (18)	0.02122 (17)	0.0424 (2)	0.00334 (10)	−0.0021 (2)	0.0034 (2)
S1	0.0240 (5)	0.0200 (6)	0.0211 (6)	−0.0013 (5)	0.0002 (5)	0.0005 (5)
O3	0.0263 (17)	0.0186 (15)	0.030 (2)	−0.0060 (11)	−0.0063 (14)	−0.0018 (14)
O1	0.0358 (19)	0.0281 (18)	0.0185 (18)	0.0012 (15)	−0.0047 (17)	−0.0023 (14)
O2	0.0283 (15)	0.0141 (16)	0.0297 (18)	−0.0029 (12)	−0.0023 (14)	−0.0008 (14)
N1	0.0233 (19)	0.0186 (18)	0.022 (2)	−0.0016 (14)	0.0014 (18)	−0.0026 (16)
C1	0.022 (2)	0.018 (2)	0.023 (2)	−0.0008 (16)	0.0033 (19)	0.0025 (18)
C2	0.024 (2)	0.023 (2)	0.028 (3)	−0.0022 (16)	−0.0004 (18)	−0.0017 (18)
C3	0.0239 (18)	0.0230 (19)	0.029 (2)	−0.0032 (15)	0.005 (4)	0.001 (3)
C4	0.028 (2)	0.018 (2)	0.031 (3)	0.0000 (18)	0.001 (2)	0.003 (2)
C5	0.032 (2)	0.019 (2)	0.029 (3)	−0.0030 (18)	0.003 (2)	−0.003 (2)
C6	0.028 (2)	0.024 (2)	0.026 (3)	−0.0045 (19)	−0.0064 (19)	−0.0056 (19)
C7	0.018 (2)	0.022 (2)	0.020 (2)	0.0008 (16)	0.001 (2)	−0.0011 (18)
C8	0.0205 (19)	0.026 (2)	0.028 (4)	−0.0004 (16)	−0.003 (2)	−0.001 (2)
C9	0.024 (2)	0.026 (2)	0.027 (3)	0.0019 (18)	−0.003 (2)	0.0025 (19)
C10	0.021 (2)	0.021 (2)	0.025 (3)	0.0011 (17)	0.001 (2)	−0.0033 (19)
C11	0.0168 (18)	0.026 (2)	0.027 (3)	−0.0003 (16)	−0.004 (2)	0.002 (2)
C12	0.021 (2)	0.025 (2)	0.023 (3)	0.0003 (17)	0.0013 (18)	0.0013 (16)
C13	0.036 (2)	0.027 (2)	0.035 (3)	−0.0057 (18)	−0.010 (3)	0.000 (3)

Geometric parameters (Å, º)

I1—C4	2.099 (4)	C5—C6	1.386 (6)
S1—O2	1.430 (3)	C5—H5	0.9500
S1—O1	1.437 (4)	C6—H6	0.9500
S1—N1	1.634 (4)	C7—C12	1.387 (7)
S1—C1	1.767 (4)	C7—C8	1.393 (6)
O3—C10	1.377 (5)	C8—C9	1.396 (6)
O3—C13	1.422 (7)	C8—H8	0.9500
N1—C7	1.443 (5)	C9—C10	1.381 (7)
N1—H1	0.85 (2)	C9—H9	0.9500
C1—C2	1.384 (6)	C10—C11	1.402 (7)
C1—C6	1.396 (7)	C11—C12	1.383 (6)
C2—C3	1.385 (6)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.383 (7)	C13—H13A	0.9800
C3—H3	0.9500	C13—H13B	0.9800
C4—C5	1.379 (7)	C13—H13C	0.9800
O2—S1—O1	120.1 (2)	C5—C6—H6	120.4
O2—S1—N1	106.0 (2)	C1—C6—H6	120.4
O1—S1—N1	107.7 (2)	C12—C7—C8	120.6 (4)
O2—S1—C1	108.2 (2)	C12—C7—N1	119.7 (4)
O1—S1—C1	108.2 (2)	C8—C7—N1	119.7 (4)
N1—S1—C1	105.8 (2)	C7—C8—C9	119.1 (4)
C10—O3—C13	116.8 (4)	C7—C8—H8	120.4
C7—N1—S1	119.8 (3)	C9—C8—H8	120.4
C7—N1—H1	114 (3)	C10—C9—C8	120.1 (4)
S1—N1—H1	113 (3)	C10—C9—H9	120.0
C2—C1—C6	121.4 (4)	C8—C9—H9	120.0
C2—C1—S1	119.1 (3)	O3—C10—C9	115.8 (4)
C6—C1—S1	119.3 (3)	O3—C10—C11	123.5 (4)
C1—C2—C3	118.8 (5)	C9—C10—C11	120.7 (4)
C1—C2—H2	120.6	C12—C11—C10	119.1 (5)
C3—C2—H2	120.6	C12—C11—H11	120.4
C4—C3—C2	119.9 (6)	C10—C11—H11	120.4
C4—C3—H3	120.0	C11—C12—C7	120.4 (4)
C2—C3—H3	120.0	C11—C12—H12	119.8
C5—C4—C3	121.4 (5)	C7—C12—H12	119.8
C5—C4—I1	119.6 (3)	O3—C13—H13A	109.5
C3—C4—I1	119.0 (4)	O3—C13—H13B	109.5
C4—C5—C6	119.3 (4)	H13A—C13—H13B	109.5
C4—C5—H5	120.3	O3—C13—H13C	109.5
C6—C5—H5	120.3	H13A—C13—H13C	109.5
C5—C6—C1	119.2 (4)	H13B—C13—H13C	109.5

(IV) 4-Bromo-N-(4-methoxyphenyl)benzenesulfonamide

Crystal data

C13H12BrNO3S	F(000) = 688
Mr = 342.21	Dx = 1.682 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1563 reflections
a = 21.6210 (7) Å	θ = 2.9–26.0°
b = 12.3720 (3) Å	µ = 3.20 mm^−1
c = 5.0526 (1) Å	T = 120 K
V = 1351.55 (6) Å^3	Block, colourless
Z = 4	0.20 × 0.20 × 0.15 mm

Data collection

Bruker Nonius 95mm CCD camera on κ-goniostat diffractometer	2521 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	2282 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 3.3°
ϕ and ω scans	h = −26→26
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −15→15
Tmin = 0.567, Tmax = 0.646	l = −6→5
9718 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.026	w = 1/[σ^2(Fo^2) + (0.0185P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.057	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.28 e Å^−3
2521 reflections	Δρmin = −0.34 e Å^−3
178 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0049 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1028 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.019 (8)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.448825 (13)	−0.101064 (18)	0.82779 (9)	0.03454 (11)
S1	0.23612 (3)	0.23287 (5)	0.50000 (12)	0.01882 (16)
O1	0.21912 (10)	0.21596 (15)	0.2284 (3)	0.0242 (5)
O2	0.25335 (9)	0.33875 (13)	0.5888 (4)	0.0246 (4)
O3	0.04718 (8)	−0.18819 (14)	0.5352 (4)	0.0239 (5)
N1	0.17747 (12)	0.19744 (17)	0.6820 (4)	0.0191 (5)
H1	0.1840 (13)	0.203 (2)	0.842 (4)	0.026 (8)*
C1	0.29684 (12)	0.1431 (2)	0.5754 (5)	0.0186 (6)
C2	0.33738 (13)	0.1693 (2)	0.7801 (6)	0.0231 (6)
H2	0.3338	0.2367	0.8688	0.028*
C3	0.38296 (13)	0.09650 (17)	0.8537 (7)	0.0250 (6)
H3	0.4111	0.1136	0.9919	0.030*
C4	0.38680 (13)	−0.00142 (19)	0.7226 (6)	0.0231 (7)
C5	0.34724 (13)	−0.02858 (19)	0.5189 (6)	0.0255 (6)
H5	0.3512	−0.0961	0.4311	0.031*
C6	0.30148 (14)	0.0442 (2)	0.4439 (5)	0.0250 (7)
H6	0.2737	0.0268	0.3046	0.030*
C7	0.14618 (13)	0.09554 (18)	0.6294 (5)	0.0169 (6)
C8	0.15674 (13)	0.00683 (17)	0.7915 (6)	0.0199 (6)
H8	0.1871	0.0102	0.9272	0.024*
C9	0.12263 (13)	−0.08656 (19)	0.7534 (5)	0.0216 (6)
H9	0.1291	−0.1471	0.8657	0.026*
C10	0.07923 (13)	−0.09225 (17)	0.5529 (5)	0.0186 (6)
C11	0.07018 (14)	−0.00470 (19)	0.3852 (5)	0.0213 (6)
H11	0.0413	−0.0094	0.2438	0.026*
C12	0.10348 (14)	0.08948 (19)	0.4252 (5)	0.0206 (6)
H12	0.0971	0.1500	0.3127	0.025*
C13	0.00321 (13)	−0.19657 (19)	0.3284 (7)	0.0310 (6)
H13A	−0.0171	−0.2673	0.3371	0.047*
H13B	0.0241	−0.1889	0.1574	0.047*
H13C	−0.0278	−0.1393	0.3476	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0350 (2)	0.02637 (15)	0.04228 (19)	0.00736 (12)	−0.00405 (19)	0.00459 (17)
S1	0.0236 (4)	0.0181 (3)	0.0148 (3)	−0.0011 (3)	−0.0005 (3)	0.0003 (3)
O1	0.0327 (13)	0.0284 (10)	0.0117 (9)	−0.0002 (9)	−0.0024 (9)	−0.0002 (8)
O2	0.0311 (11)	0.0186 (9)	0.0243 (9)	−0.0028 (8)	−0.0014 (9)	0.0000 (8)
O3	0.0255 (12)	0.0203 (9)	0.0259 (11)	−0.0057 (7)	−0.0050 (9)	−0.0015 (8)
N1	0.0228 (14)	0.0215 (12)	0.0129 (11)	0.0008 (9)	0.0001 (10)	−0.0031 (10)
C1	0.0203 (16)	0.0175 (12)	0.0179 (13)	−0.0016 (10)	0.0020 (12)	0.0007 (11)
C2	0.0245 (16)	0.0208 (12)	0.0240 (16)	−0.0031 (11)	−0.0014 (13)	−0.0025 (11)
C3	0.0244 (15)	0.0269 (13)	0.0236 (15)	−0.0027 (11)	−0.0024 (16)	−0.0027 (13)
C4	0.0218 (17)	0.0214 (14)	0.0260 (14)	0.0013 (12)	0.0029 (13)	0.0039 (11)
C5	0.0316 (18)	0.0181 (12)	0.0268 (15)	−0.0032 (12)	0.0056 (15)	−0.0056 (13)
C6	0.0325 (19)	0.0203 (14)	0.0222 (14)	−0.0047 (13)	−0.0012 (13)	−0.0041 (11)
C7	0.0178 (16)	0.0195 (13)	0.0134 (12)	−0.0004 (11)	0.0027 (12)	−0.0038 (10)
C8	0.0206 (14)	0.0235 (12)	0.0156 (14)	0.0020 (10)	−0.0028 (13)	0.0005 (12)
C9	0.0221 (17)	0.0217 (13)	0.0210 (15)	0.0012 (11)	−0.0022 (12)	0.0021 (10)
C10	0.0173 (16)	0.0209 (13)	0.0177 (14)	0.0025 (10)	0.0025 (12)	−0.0029 (10)
C11	0.0174 (15)	0.0289 (14)	0.0175 (15)	0.0018 (11)	−0.0021 (12)	−0.0028 (11)
C12	0.0203 (16)	0.0232 (14)	0.0183 (13)	0.0029 (11)	−0.0003 (12)	0.0023 (10)
C13	0.0297 (17)	0.0353 (14)	0.0281 (14)	−0.0065 (12)	−0.0087 (17)	0.0019 (17)

Geometric parameters (Å, º)

Br1—C4	1.897 (3)	C5—C6	1.390 (4)
S1—O2	1.4338 (18)	C5—H5	0.9500
S1—O1	1.4362 (18)	C6—H6	0.9500
S1—N1	1.627 (3)	C7—C8	1.388 (4)
S1—C1	1.761 (3)	C7—C12	1.386 (4)
O3—C10	1.377 (3)	C8—C9	1.384 (3)
O3—C13	1.416 (4)	C8—H8	0.9500
N1—C7	1.455 (3)	C9—C10	1.383 (4)
N1—H1	0.825 (18)	C9—H9	0.9500
C1—C2	1.394 (4)	C10—C11	1.389 (3)
C1—C6	1.396 (4)	C11—C12	1.384 (4)
C2—C3	1.386 (4)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.383 (3)	C13—H13A	0.9800
C3—H3	0.9500	C13—H13B	0.9800
C4—C5	1.380 (4)	C13—H13C	0.9800
O2—S1—O1	119.92 (12)	C5—C6—H6	120.4
O2—S1—N1	105.77 (11)	C1—C6—H6	120.4
O1—S1—N1	107.54 (12)	C8—C7—C12	120.4 (2)
O2—S1—C1	108.35 (12)	C8—C7—N1	120.1 (3)
O1—S1—C1	107.79 (12)	C12—C7—N1	119.5 (2)
N1—S1—C1	106.79 (12)	C9—C8—C7	119.4 (3)
C10—O3—C13	116.7 (2)	C9—C8—H8	120.3
C7—N1—S1	119.52 (18)	C7—C8—H8	120.3
C7—N1—H1	109.5 (19)	C10—C9—C8	120.4 (2)
S1—N1—H1	113 (2)	C10—C9—H9	119.8
C2—C1—C6	120.8 (2)	C8—C9—H9	119.8
C2—C1—S1	118.85 (19)	O3—C10—C9	115.7 (2)
C6—C1—S1	120.2 (2)	O3—C10—C11	124.2 (3)
C3—C2—C1	119.7 (2)	C9—C10—C11	120.2 (2)
C3—C2—H2	120.2	C12—C11—C10	119.6 (3)
C1—C2—H2	120.2	C12—C11—H11	120.2
C4—C3—C2	118.9 (3)	C10—C11—H11	120.2
C4—C3—H3	120.5	C11—C12—C7	120.0 (2)
C2—C3—H3	120.5	C11—C12—H12	120.0
C5—C4—C3	122.2 (3)	C7—C12—H12	120.0
C5—C4—Br1	119.27 (19)	O3—C13—H13A	109.5
C3—C4—Br1	118.5 (2)	O3—C13—H13B	109.5
C4—C5—C6	119.1 (2)	H13A—C13—H13B	109.5
C4—C5—H5	120.4	O3—C13—H13C	109.5
C6—C5—H5	120.4	H13A—C13—H13C	109.5
C5—C6—C1	119.3 (3)	H13B—C13—H13C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.83 (2)	2.10 (2)	2.913 (3)	169 (3)

Symmetry code: (i) x, y, z+1.

(V) 4-Chloro-N-(4-methoxyphenyl)benzenesulfonamide

Crystal data

C13H12ClNO3S	F(000) = 616
Mr = 297.75	Dx = 1.485 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1510 reflections
a = 21.2580 (15) Å	θ = 2.9–26.0°
b = 12.3967 (5) Å	µ = 0.45 mm^−1
c = 5.0526 (3) Å	T = 120 K
V = 1331.51 (13) Å^3	Block, colourless
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection

Bruker Nonius 95mm CCD camera on κ-goniostat diffractometer	2472 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2028 reflections with I > 2σ(I)
10cm confocal mirrors monochromator	Rint = 0.058
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 3.3°
ϕ and ω scans	h = −26→22
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −15→15
Tmin = 0.916, Tmax = 0.957	l = −6→5
6144 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0321P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.100	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.31 e Å^−3
2472 reflections	Δρmin = −0.30 e Å^−3
177 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0106 (18)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 106 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.08 (9)

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	0.44246 (5)	−0.10433 (7)	0.8254 (2)	0.0462 (3)
S1	0.23039 (4)	0.21692 (6)	0.49918 (17)	0.0260 (2)
O3	0.04598 (11)	−0.21093 (16)	0.5381 (5)	0.0319 (6)
O1	0.21312 (13)	0.19829 (17)	0.2291 (5)	0.0332 (6)
O2	0.24738 (12)	0.32294 (15)	0.5848 (5)	0.0312 (6)
N1	0.17048 (14)	0.1813 (2)	0.6831 (6)	0.0261 (7)
H1	0.1818 (18)	0.186 (3)	0.846 (4)	0.031*
C1	0.29233 (15)	0.1281 (2)	0.5782 (7)	0.0229 (7)
C2	0.33229 (16)	0.1543 (3)	0.7856 (7)	0.0293 (8)
H2	0.3277	0.2212	0.8753	0.035*
C3	0.37857 (17)	0.0832 (2)	0.8609 (8)	0.0300 (8)
H3	0.4063	0.1005	1.0022	0.036*
C4	0.38433 (17)	−0.0144 (2)	0.7278 (7)	0.0321 (9)
C5	0.34506 (16)	−0.0414 (2)	0.5227 (8)	0.0317 (8)
H5	0.3499	−0.1083	0.4334	0.038*
C6	0.29786 (17)	0.0308 (2)	0.4466 (7)	0.0290 (9)
H6	0.2699	0.0132	0.3062	0.035*
C7	0.14028 (16)	0.0780 (2)	0.6324 (7)	0.0243 (8)
C8	0.15330 (16)	−0.0106 (2)	0.7925 (7)	0.0273 (8)
H8	0.1842	−0.0058	0.9278	0.033*
C9	0.12097 (17)	−0.1049 (2)	0.7526 (7)	0.0286 (8)
H9	0.1293	−0.1653	0.8630	0.034*
C10	0.07635 (15)	−0.1135 (2)	0.5537 (7)	0.0262 (8)
C11	0.06396 (17)	−0.0257 (3)	0.3938 (7)	0.0296 (8)
H11	0.0334	−0.0309	0.2571	0.036*
C12	0.09619 (17)	0.0700 (2)	0.4334 (6)	0.0274 (8)
H12	0.0879	0.1304	0.3230	0.033*
C13	0.00328 (19)	−0.2245 (3)	0.3214 (9)	0.0398 (9)
H13A	−0.0122	−0.2990	0.3187	0.060*
H13B	0.0251	−0.2088	0.1548	0.060*
H13C	−0.0323	−0.1749	0.3422	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0454 (6)	0.0411 (5)	0.0521 (7)	0.0130 (4)	−0.0074 (6)	0.0045 (5)
S1	0.0324 (5)	0.0263 (4)	0.0193 (4)	0.0013 (4)	−0.0002 (4)	0.0005 (4)
O3	0.0301 (13)	0.0320 (11)	0.0337 (16)	−0.0038 (10)	−0.0069 (13)	−0.0014 (11)
O1	0.0445 (16)	0.0381 (12)	0.0170 (13)	0.0040 (12)	−0.0038 (12)	−0.0016 (11)
O2	0.0444 (15)	0.0208 (10)	0.0283 (14)	−0.0033 (10)	0.0013 (12)	−0.0018 (10)
N1	0.0294 (17)	0.0284 (13)	0.0204 (15)	0.0012 (12)	0.0012 (13)	−0.0041 (12)
C1	0.0251 (18)	0.0257 (16)	0.0179 (18)	0.0002 (13)	0.0055 (14)	0.0000 (13)
C2	0.032 (2)	0.0313 (16)	0.025 (2)	−0.0016 (15)	0.0016 (17)	−0.0041 (15)
C3	0.029 (2)	0.0378 (18)	0.0230 (19)	−0.0052 (15)	−0.0001 (18)	−0.0004 (16)
C4	0.035 (2)	0.0264 (16)	0.035 (2)	0.0017 (15)	0.0032 (19)	0.0058 (15)
C5	0.038 (2)	0.0274 (15)	0.030 (2)	0.0023 (15)	0.0013 (19)	−0.0017 (17)
C6	0.033 (2)	0.0289 (16)	0.025 (2)	−0.0040 (14)	−0.0016 (15)	−0.0027 (14)
C7	0.0270 (19)	0.0251 (16)	0.0209 (18)	0.0041 (14)	0.0001 (15)	−0.0033 (14)
C8	0.0276 (18)	0.0334 (17)	0.0208 (19)	0.0034 (14)	−0.0040 (16)	−0.0023 (15)
C9	0.0274 (19)	0.0301 (16)	0.028 (2)	0.0011 (15)	−0.0033 (16)	0.0023 (15)
C10	0.0223 (17)	0.0297 (16)	0.027 (2)	0.0040 (13)	−0.0004 (15)	−0.0042 (14)
C11	0.027 (2)	0.0371 (18)	0.024 (2)	0.0034 (15)	−0.0041 (15)	−0.0043 (15)
C12	0.029 (2)	0.0317 (16)	0.021 (2)	0.0043 (16)	−0.0058 (15)	−0.0010 (14)
C13	0.032 (2)	0.053 (2)	0.035 (2)	−0.0107 (17)	−0.0109 (19)	−0.0014 (19)

Geometric parameters (Å, º)

Cl1—C4	1.736 (3)	C5—C6	1.398 (5)
S1—O2	1.430 (2)	C5—H5	0.9500
S1—O1	1.432 (2)	C6—H6	0.9500
S1—N1	1.637 (3)	C7—C12	1.378 (4)
S1—C1	1.762 (3)	C7—C8	1.392 (5)
O3—C10	1.372 (4)	C8—C9	1.371 (4)
O3—C13	1.432 (4)	C8—H8	0.9500
N1—C7	1.455 (4)	C9—C10	1.386 (5)
N1—H1	0.858 (19)	C9—H9	0.9500
C1—C6	1.382 (4)	C10—C11	1.381 (5)
C1—C2	1.388 (5)	C11—C12	1.384 (4)
C2—C3	1.375 (5)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.389 (4)	C13—H13A	0.9800
C3—H3	0.9500	C13—H13B	0.9800
C4—C5	1.372 (5)	C13—H13C	0.9800
O2—S1—O1	120.09 (14)	C1—C6—H6	120.4
O2—S1—N1	105.83 (15)	C5—C6—H6	120.4
O1—S1—N1	107.35 (16)	C12—C7—C8	120.2 (3)
O2—S1—C1	108.47 (15)	C12—C7—N1	119.5 (3)
O1—S1—C1	107.85 (15)	C8—C7—N1	120.3 (3)
N1—S1—C1	106.50 (15)	C9—C8—C7	119.2 (3)
C10—O3—C13	116.5 (3)	C9—C8—H8	120.4
C7—N1—S1	118.7 (2)	C7—C8—H8	120.4
C7—N1—H1	111 (2)	C8—C9—C10	121.0 (3)
S1—N1—H1	108 (3)	C8—C9—H9	119.5
C6—C1—C2	121.0 (3)	C10—C9—H9	119.5
C6—C1—S1	120.0 (3)	O3—C10—C11	124.8 (3)
C2—C1—S1	118.8 (2)	O3—C10—C9	115.5 (3)
C3—C2—C1	119.8 (3)	C11—C10—C9	119.6 (3)
C3—C2—H2	120.1	C10—C11—C12	119.8 (3)
C1—C2—H2	120.1	C10—C11—H11	120.1
C2—C3—C4	119.2 (3)	C12—C11—H11	120.1
C2—C3—H3	120.4	C7—C12—C11	120.3 (3)
C4—C3—H3	120.4	C7—C12—H12	119.9
C5—C4—C3	121.6 (3)	C11—C12—H12	119.9
C5—C4—Cl1	119.4 (3)	O3—C13—H13A	109.5
C3—C4—Cl1	119.0 (3)	O3—C13—H13B	109.5
C4—C5—C6	119.2 (3)	H13A—C13—H13B	109.5
C4—C5—H5	120.4	O3—C13—H13C	109.5
C6—C5—H5	120.4	H13A—C13—H13C	109.5
C1—C6—C5	119.2 (3)	H13B—C13—H13C	109.5

(VI) 4-Fluoro-N-(4-methoxyphenyl)benzenesulfonamide

Crystal data

C13H12FNO3S	F(000) = 584
Mr = 281.30	Dx = 1.453 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1514 reflections
a = 20.7242 (4) Å	θ = 2.9–26.0°
b = 12.3551 (4) Å	µ = 0.27 mm^−1
c = 5.0209 (1) Å	T = 120 K
V = 1285.60 (5) Å^3	Block, colourless
Z = 4	0.22 × 0.14 × 0.10 mm

Data collection

Bruker Nonius 95mm CCD camera on κ-goniostat diffractometer	2239 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2182 reflections with I > 2σ(I)
10cm confocal mirrors monochromator	Rint = 0.041
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 3.3°
ϕ and ω scans	h = −25→25
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −15→15
Tmin = 0.944, Tmax = 0.974	l = −4→6
13397 measured reflections

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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0536P)^2 + 0.2191P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2239 reflections	Δρmax = 0.19 e Å^−3
177 parameters	Δρmin = −0.37 e Å^−3
2 restraints	Absolute structure: Flack (1983), with 823 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (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
F1	0.42758 (6)	−0.12674 (9)	0.8167 (3)	0.0344 (3)
S1	0.229203 (17)	0.18245 (3)	0.50000 (10)	0.01522 (12)
O1	0.21135 (6)	0.16377 (10)	0.2274 (3)	0.0209 (3)
O2	0.24741 (6)	0.28851 (10)	0.5854 (3)	0.0199 (3)
O3	0.04008 (5)	−0.24482 (8)	0.5186 (3)	0.0222 (3)
N1	0.16700 (7)	0.14782 (12)	0.6836 (3)	0.0162 (3)
H1	0.1761 (10)	0.1572 (15)	0.850 (3)	0.016 (5)*
C1	0.29196 (7)	0.09192 (13)	0.5807 (4)	0.0165 (4)
C2	0.33383 (8)	0.11902 (14)	0.7867 (4)	0.0192 (4)
H2	0.3306	0.1874	0.8721	0.023*
C3	0.38040 (8)	0.04508 (14)	0.8662 (4)	0.0220 (4)
H3	0.4099	0.0617	1.0053	0.026*
C4	0.38256 (8)	−0.05388 (14)	0.7363 (4)	0.0221 (4)
C5	0.34214 (8)	−0.08137 (13)	0.5309 (4)	0.0225 (4)
H5	0.3459	−0.1495	0.4446	0.027*
C6	0.29554 (7)	−0.00726 (13)	0.4520 (4)	0.0190 (4)
H6	0.2665	−0.0242	0.3118	0.023*
C7	0.13524 (8)	0.04617 (13)	0.6314 (4)	0.0159 (4)
C8	0.14911 (8)	−0.04427 (13)	0.7868 (4)	0.0181 (4)
H8	0.1809	−0.0400	0.9226	0.022*
C9	0.11645 (8)	−0.14025 (14)	0.7429 (4)	0.0190 (4)
H9	0.1257	−0.2020	0.8489	0.023*
C10	0.07000 (7)	−0.14613 (13)	0.5428 (4)	0.0184 (4)
C11	0.05653 (8)	−0.05685 (13)	0.3864 (4)	0.0190 (4)
H11	0.0253	−0.0615	0.2483	0.023*
C12	0.08911 (8)	0.03992 (13)	0.4330 (4)	0.0180 (4)
H12	0.0796	0.1019	0.3281	0.022*
C13	−0.00404 (9)	−0.25854 (15)	0.3038 (5)	0.0265 (4)
H13A	−0.0201	−0.3331	0.3029	0.040*
H13B	0.0180	−0.2435	0.1351	0.040*
H13C	−0.0403	−0.2085	0.3255	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0326 (6)	0.0323 (6)	0.0383 (8)	0.0143 (5)	−0.0088 (6)	0.0031 (6)
S1	0.0179 (2)	0.01521 (19)	0.0126 (2)	0.00018 (13)	−0.00031 (19)	−0.00045 (17)
O1	0.0248 (6)	0.0248 (6)	0.0130 (8)	0.0012 (5)	−0.0016 (6)	−0.0001 (5)
O2	0.0250 (6)	0.0144 (6)	0.0202 (8)	−0.0011 (5)	0.0014 (6)	−0.0015 (5)
O3	0.0194 (5)	0.0199 (5)	0.0271 (8)	−0.0029 (4)	−0.0045 (6)	−0.0025 (6)
N1	0.0183 (7)	0.0187 (7)	0.0117 (8)	−0.0003 (5)	0.0001 (6)	−0.0027 (6)
C1	0.0156 (7)	0.0174 (8)	0.0163 (10)	−0.0013 (6)	0.0025 (7)	0.0012 (7)
C2	0.0197 (8)	0.0198 (8)	0.0181 (10)	−0.0025 (6)	−0.0002 (7)	−0.0026 (7)
C3	0.0185 (8)	0.0284 (9)	0.0192 (10)	−0.0010 (7)	−0.0036 (7)	−0.0018 (8)
C4	0.0192 (8)	0.0235 (9)	0.0234 (11)	0.0049 (7)	−0.0009 (8)	0.0045 (8)
C5	0.0246 (8)	0.0154 (7)	0.0275 (12)	0.0010 (6)	0.0009 (8)	−0.0005 (8)
C6	0.0200 (8)	0.0190 (7)	0.0180 (10)	−0.0032 (6)	−0.0013 (7)	−0.0025 (7)
C7	0.0153 (7)	0.0175 (8)	0.0150 (10)	0.0010 (6)	0.0008 (7)	−0.0015 (7)
C8	0.0166 (7)	0.0219 (8)	0.0160 (10)	0.0018 (6)	−0.0029 (7)	−0.0005 (7)
C9	0.0190 (8)	0.0198 (8)	0.0183 (10)	0.0018 (6)	−0.0016 (7)	0.0017 (7)
C10	0.0135 (7)	0.0207 (8)	0.0212 (11)	−0.0007 (6)	0.0024 (7)	−0.0029 (8)
C11	0.0140 (7)	0.0276 (9)	0.0154 (10)	0.0012 (6)	−0.0015 (7)	−0.0026 (8)
C12	0.0163 (7)	0.0216 (8)	0.0160 (10)	0.0037 (6)	0.0006 (7)	0.0002 (7)
C13	0.0216 (8)	0.0303 (9)	0.0276 (12)	−0.0065 (7)	−0.0062 (8)	−0.0022 (8)

Geometric parameters (Å, º)

F1—C4	1.358 (2)	C5—C6	1.389 (2)
S1—O2	1.4294 (13)	C5—H5	0.9500
S1—O1	1.4363 (15)	C6—H6	0.9500
S1—N1	1.6414 (16)	C7—C12	1.383 (2)
S1—C1	1.7626 (17)	C7—C8	1.393 (2)
O3—C10	1.373 (2)	C8—C9	1.383 (2)
O3—C13	1.424 (2)	C8—H8	0.9500
N1—C7	1.442 (2)	C9—C10	1.393 (3)
N1—H1	0.865 (16)	C9—H9	0.9500
C1—C6	1.387 (2)	C10—C11	1.382 (3)
C1—C2	1.391 (3)	C11—C12	1.393 (2)
C2—C3	1.388 (2)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.386 (3)	C13—H13A	0.9800
C3—H3	0.9500	C13—H13B	0.9800
C4—C5	1.371 (3)	C13—H13C	0.9800
O2—S1—O1	120.06 (8)	C1—C6—H6	120.4
O2—S1—N1	106.13 (8)	C5—C6—H6	120.4
O1—S1—N1	106.91 (8)	C12—C7—C8	120.09 (16)
O2—S1—C1	108.55 (8)	C12—C7—N1	119.68 (15)
O1—S1—C1	107.89 (8)	C8—C7—N1	120.18 (15)
N1—S1—C1	106.56 (8)	C9—C8—C7	119.83 (17)
C10—O3—C13	117.54 (14)	C9—C8—H8	120.1
C7—N1—S1	118.91 (12)	C7—C8—H8	120.1
C7—N1—H1	113.1 (13)	C8—C9—C10	119.86 (17)
S1—N1—H1	109.7 (14)	C8—C9—H9	120.1
C6—C1—C2	121.71 (16)	C10—C9—H9	120.1
C6—C1—S1	119.53 (14)	O3—C10—C11	124.56 (16)
C2—C1—S1	118.59 (14)	O3—C10—C9	114.95 (16)
C3—C2—C1	119.30 (17)	C11—C10—C9	120.49 (15)
C3—C2—H2	120.4	C10—C11—C12	119.44 (17)
C1—C2—H2	120.4	C10—C11—H11	120.3
C4—C3—C2	117.89 (18)	C12—C11—H11	120.3
C4—C3—H3	121.1	C7—C12—C11	120.28 (16)
C2—C3—H3	121.1	C7—C12—H12	119.9
F1—C4—C5	118.63 (17)	C11—C12—H12	119.9
F1—C4—C3	117.83 (17)	O3—C13—H13A	109.5
C5—C4—C3	123.53 (16)	O3—C13—H13B	109.5
C4—C5—C6	118.43 (17)	H13A—C13—H13B	109.5
C4—C5—H5	120.8	O3—C13—H13C	109.5
C6—C5—H5	120.8	H13A—C13—H13C	109.5
C1—C6—C5	119.13 (18)	H13B—C13—H13C	109.5

(VII) N-(4-Chlorophenyl)-4-methoxybenzenesulfonamide

Crystal data

C13H12ClNO3S	F(000) = 616
Mr = 297.75	Dx = 1.483 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1562 reflections
a = 21.3923 (7) Å	θ = 2.9–26.0°
b = 12.3691 (4) Å	µ = 0.45 mm^−1
c = 5.0386 (2) Å	T = 120 K
V = 1333.23 (8) Å^3	Platelet, colourless
Z = 4	0.40 × 0.15 × 0.15 mm

Data collection

Bruker Nonius 95mm CCD camera on κ-goniostat diffractometer	2413 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2266 reflections with I > 2σ(I)
10cm confocal mirrors monochromator	Rint = 0.048
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 3.4°
ϕ and ω scans	h = −26→24
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −14→15
Tmin = 0.842, Tmax = 0.936	l = −5→6
8878 measured reflections

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) = 0.074	w = 1/[σ^2(Fo^2) + (0.0257P)^2 + 0.4077P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2413 reflections	Δρmax = 0.22 e Å^−3
178 parameters	Δρmin = −0.32 e Å^−3
2 restraints	Absolute structure: Flack (1983), with 945 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.08 (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	0.24485 (2)	0.21722 (4)	0.50004 (14)	0.01787 (13)
Cl1	0.02514 (3)	−0.19323 (5)	0.43434 (15)	0.03181 (18)
O1	0.22594 (8)	0.20626 (13)	0.2279 (3)	0.0246 (4)
O2	0.26687 (7)	0.31889 (13)	0.5983 (4)	0.0237 (4)
O3	0.42998 (8)	−0.12261 (14)	0.7239 (4)	0.0292 (4)
N1	0.18367 (9)	0.18694 (16)	0.6824 (4)	0.0190 (4)
H1	0.1948 (12)	0.189 (2)	0.842 (4)	0.023 (7)*
C1	0.30208 (10)	0.11869 (18)	0.5643 (5)	0.0184 (5)
C2	0.34506 (10)	0.13536 (19)	0.7654 (5)	0.0211 (5)
H2	0.3447	0.2014	0.8614	0.025*
C3	0.38859 (11)	0.0563 (2)	0.8277 (5)	0.0245 (6)
H3	0.4180	0.0674	0.9663	0.029*
C4	0.38842 (11)	−0.03955 (18)	0.6836 (5)	0.0211 (5)
C5	0.34500 (10)	−0.05694 (17)	0.4849 (6)	0.0244 (5)
H5	0.3451	−0.1233	0.3901	0.029*
C6	0.30141 (11)	0.02154 (17)	0.4231 (5)	0.0211 (5)
H6	0.2715	0.0096	0.2869	0.033 (8)*
C7	0.14745 (11)	0.09253 (17)	0.6193 (5)	0.0181 (5)
C8	0.15372 (11)	−0.00200 (18)	0.7633 (5)	0.0215 (5)
H8	0.1837	−0.0059	0.9022	0.026*
C9	0.11688 (11)	−0.09082 (19)	0.7073 (6)	0.0241 (5)
H9	0.1207	−0.1554	0.8080	0.029*
C10	0.07434 (10)	−0.08391 (17)	0.5021 (6)	0.0217 (5)
C11	0.06828 (11)	0.00904 (18)	0.3506 (5)	0.0226 (5)
H11	0.0394	0.0115	0.2076	0.027*
C12	0.10482 (10)	0.09824 (18)	0.4098 (5)	0.0210 (5)
H12	0.1009	0.1628	0.3089	0.025*
C13	0.47298 (12)	−0.1129 (2)	0.9392 (6)	0.0337 (6)
H13A	0.5001	−0.1768	0.9442	0.050*
H13B	0.4498	−0.1074	1.1065	0.050*
H13C	0.4986	−0.0480	0.9148	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0217 (3)	0.0167 (2)	0.0152 (3)	0.0004 (2)	−0.0003 (3)	0.0003 (3)
Cl1	0.0258 (3)	0.0237 (3)	0.0460 (5)	−0.0036 (2)	−0.0010 (3)	−0.0092 (3)
O1	0.0297 (9)	0.0286 (9)	0.0155 (9)	0.0044 (7)	−0.0031 (8)	0.0019 (7)
O2	0.0283 (9)	0.0147 (8)	0.0282 (10)	−0.0025 (7)	−0.0002 (8)	0.0004 (7)
O3	0.0279 (9)	0.0226 (9)	0.0370 (12)	0.0069 (7)	−0.0072 (9)	0.0005 (8)
N1	0.0207 (10)	0.0224 (10)	0.0139 (10)	−0.0005 (8)	−0.0013 (8)	−0.0017 (9)
C1	0.0196 (11)	0.0174 (11)	0.0181 (13)	−0.0019 (8)	0.0011 (9)	0.0005 (9)
C2	0.0232 (12)	0.0185 (12)	0.0217 (13)	−0.0001 (9)	−0.0021 (10)	−0.0067 (10)
C3	0.0214 (12)	0.0264 (13)	0.0258 (14)	0.0000 (10)	−0.0057 (10)	−0.0041 (10)
C4	0.0192 (12)	0.0185 (12)	0.0258 (15)	0.0009 (9)	0.0016 (10)	0.0022 (10)
C5	0.0262 (11)	0.0161 (11)	0.0308 (15)	−0.0020 (8)	0.0005 (12)	−0.0027 (12)
C6	0.0224 (11)	0.0193 (11)	0.0216 (13)	−0.0037 (9)	−0.0015 (10)	−0.0035 (10)
C7	0.0168 (11)	0.0185 (11)	0.0191 (12)	0.0016 (9)	0.0012 (9)	−0.0027 (10)
C8	0.0230 (12)	0.0217 (13)	0.0198 (13)	0.0006 (9)	−0.0041 (10)	0.0011 (10)
C9	0.0249 (12)	0.0195 (12)	0.0278 (14)	0.0005 (9)	0.0008 (11)	0.0019 (11)
C10	0.0172 (10)	0.0196 (11)	0.0282 (13)	−0.0013 (8)	0.0025 (11)	−0.0074 (11)
C11	0.0191 (12)	0.0271 (13)	0.0214 (14)	0.0028 (9)	−0.0042 (10)	−0.0018 (11)
C12	0.0200 (11)	0.0212 (11)	0.0219 (13)	0.0032 (9)	0.0002 (10)	0.0027 (10)
C13	0.0334 (13)	0.0379 (14)	0.0297 (16)	0.0115 (11)	−0.0049 (11)	0.0011 (13)

Geometric parameters (Å, º)

S1—O2	1.4312 (17)	C5—C6	1.381 (3)
S1—O1	1.4363 (18)	C5—H5	0.9500
S1—N1	1.642 (2)	C6—H6	0.9500
S1—C1	1.757 (2)	C7—C8	1.382 (3)
Cl1—C10	1.747 (2)	C7—C12	1.397 (3)
O3—C4	1.374 (3)	C8—C9	1.381 (3)
O3—C13	1.428 (3)	C8—H8	0.9500
N1—C7	1.437 (3)	C9—C10	1.380 (4)
N1—H1	0.839 (17)	C9—H9	0.9500
C1—C2	1.384 (3)	C10—C11	1.386 (3)
C1—C6	1.396 (3)	C11—C12	1.385 (3)
C2—C3	1.386 (3)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.390 (3)	C13—H13A	0.9800
C3—H3	0.9500	C13—H13B	0.9800
C4—C5	1.383 (4)	C13—H13C	0.9800
O2—S1—O1	120.38 (11)	C5—C6—H6	120.6
O2—S1—N1	105.62 (10)	C1—C6—H6	120.6
O1—S1—N1	106.75 (10)	C8—C7—C12	120.2 (2)
O2—S1—C1	108.45 (10)	C8—C7—N1	121.3 (2)
O1—S1—C1	107.86 (11)	C12—C7—N1	118.6 (2)
N1—S1—C1	107.10 (11)	C9—C8—C7	120.7 (2)
C4—O3—C13	117.8 (2)	C9—C8—H8	119.7
C7—N1—S1	119.44 (16)	C7—C8—H8	119.7
C7—N1—H1	113.2 (18)	C10—C9—C8	118.7 (2)
S1—N1—H1	107.6 (18)	C10—C9—H9	120.7
C2—C1—C6	120.5 (2)	C8—C9—H9	120.7
C2—C1—S1	119.62 (17)	C9—C10—C11	121.7 (2)
C6—C1—S1	119.72 (18)	C9—C10—Cl1	119.72 (19)
C1—C2—C3	120.5 (2)	C11—C10—Cl1	118.6 (2)
C1—C2—H2	119.8	C12—C11—C10	119.3 (2)
C3—C2—H2	119.8	C12—C11—H11	120.3
C2—C3—C4	118.8 (2)	C10—C11—H11	120.3
C2—C3—H3	120.6	C11—C12—C7	119.4 (2)
C4—C3—H3	120.6	C11—C12—H12	120.3
O3—C4—C5	115.2 (2)	C7—C12—H12	120.3
O3—C4—C3	124.0 (2)	O3—C13—H13A	109.5
C5—C4—C3	120.8 (2)	O3—C13—H13B	109.5
C6—C5—C4	120.5 (2)	H13A—C13—H13B	109.5
C6—C5—H5	119.8	O3—C13—H13C	109.5
C4—C5—H5	119.8	H13A—C13—H13C	109.5
C5—C6—C1	118.9 (2)	H13B—C13—H13C	109.5

(VIII) 4-Cyano-N-phenylbenzenesulfonamide

Crystal data

C13H10N2O2S	F(000) = 536
Mr = 258.29	Dx = 1.387 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1441 reflections
a = 20.1912 (7) Å	θ = 2.9–26.0°
b = 12.0001 (4) Å	µ = 0.26 mm^−1
c = 5.1055 (1) Å	T = 120 K
V = 1237.04 (6) Å^3	Block, colourless
Z = 4	0.25 × 0.20 × 0.10 mm

Data collection

Bruker Nonius 95mm CCD camera on κ-goniostat diffractometer	2286 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2187 reflections with I > 2σ(I)
10cm confocal mirrors monochromator	Rint = 0.041
Detector resolution: 9.091 pixels mm^-1	θmax = 26.0°, θmin = 3.4°
ϕ and ω scans	h = −24→24
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −14→14
Tmin = 0.939, Tmax = 0.975	l = −6→5
13628 measured reflections

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.067	w = 1/[σ^2(Fo^2) + (0.0313P)^2 + 0.2848P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2286 reflections	Δρmax = 0.13 e Å^−3
169 parameters	Δρmin = −0.28 e Å^−3
2 restraints	Absolute structure: Flack (1983), with 925 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (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	0.22272 (2)	0.20700 (3)	0.49997 (10)	0.02143 (11)
O1	0.20576 (7)	0.18560 (11)	0.2318 (2)	0.0271 (3)
O2	0.23773 (7)	0.31755 (10)	0.5834 (3)	0.0281 (3)
N1	0.16081 (8)	0.16490 (12)	0.6811 (3)	0.0231 (3)
H1	0.1730 (10)	0.1734 (16)	0.840 (3)	0.021 (5)*
N2	0.49107 (10)	−0.14131 (16)	0.8742 (5)	0.0493 (5)
C1	0.29062 (8)	0.12052 (15)	0.5829 (4)	0.0219 (4)
C2	0.33073 (9)	0.15267 (15)	0.7917 (4)	0.0246 (4)
H2	0.3229	0.2209	0.8808	0.029*
C3	0.38211 (9)	0.08373 (15)	0.8672 (4)	0.0269 (4)
H3	0.4101	0.1043	1.0088	0.032*
C4	0.39268 (8)	−0.01634 (15)	0.7340 (4)	0.0271 (4)
C5	0.35239 (9)	−0.04766 (14)	0.5262 (4)	0.0293 (4)
H5	0.3603	−0.1157	0.4363	0.035*
C6	0.30049 (9)	0.02126 (15)	0.4507 (4)	0.0264 (4)
H6	0.2722	0.0005	0.3103	0.032*
C7	0.12937 (8)	0.05963 (15)	0.6267 (4)	0.0221 (4)
C8	0.13993 (9)	−0.03073 (15)	0.7904 (4)	0.0281 (4)
H8	0.1703	−0.0251	0.9319	0.034*
C9	0.10600 (10)	−0.12924 (16)	0.7469 (4)	0.0329 (5)
H9	0.1121	−0.1907	0.8616	0.040*
C10	0.06319 (9)	−0.13808 (15)	0.5366 (4)	0.0304 (5)
H10	0.0400	−0.2058	0.5062	0.027 (5)*
C11	0.05412 (9)	−0.04855 (16)	0.3709 (4)	0.0298 (4)
H11	0.0255	−0.0555	0.2242	0.037 (6)*
C12	0.08647 (8)	0.05149 (15)	0.4169 (4)	0.0259 (4)
H12	0.0792	0.1137	0.3053	0.031*
C13	0.44723 (10)	−0.08700 (17)	0.8124 (4)	0.0345 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0261 (2)	0.0209 (2)	0.0173 (2)	−0.00093 (15)	−0.00005 (19)	−0.00220 (18)
O1	0.0335 (7)	0.0315 (7)	0.0161 (7)	−0.0018 (5)	−0.0015 (6)	−0.0018 (5)
O2	0.0371 (7)	0.0205 (6)	0.0267 (8)	−0.0004 (5)	0.0000 (6)	−0.0039 (5)
N1	0.0248 (8)	0.0280 (8)	0.0165 (8)	−0.0001 (6)	0.0000 (6)	−0.0041 (6)
N2	0.0426 (11)	0.0410 (11)	0.0643 (14)	0.0123 (9)	−0.0087 (10)	−0.0091 (10)
C1	0.0219 (8)	0.0214 (9)	0.0223 (9)	−0.0028 (6)	0.0021 (7)	−0.0017 (7)
C2	0.0260 (9)	0.0228 (9)	0.0249 (10)	−0.0026 (7)	0.0008 (8)	−0.0066 (7)
C3	0.0242 (9)	0.0290 (10)	0.0276 (10)	−0.0041 (7)	−0.0018 (8)	−0.0035 (8)
C4	0.0234 (8)	0.0255 (9)	0.0323 (11)	−0.0018 (7)	0.0047 (9)	−0.0003 (8)
C5	0.0320 (9)	0.0222 (8)	0.0338 (11)	−0.0025 (7)	0.0025 (9)	−0.0068 (9)
C6	0.0297 (9)	0.0236 (9)	0.0259 (11)	−0.0062 (7)	−0.0009 (7)	−0.0063 (7)
C7	0.0205 (8)	0.0254 (9)	0.0204 (9)	0.0011 (7)	0.0039 (7)	−0.0019 (7)
C8	0.0288 (9)	0.0307 (10)	0.0247 (11)	0.0061 (8)	−0.0034 (8)	0.0009 (8)
C9	0.0370 (11)	0.0270 (10)	0.0349 (12)	0.0060 (8)	0.0027 (9)	0.0031 (9)
C10	0.0263 (9)	0.0261 (9)	0.0389 (13)	−0.0003 (7)	0.0074 (9)	−0.0049 (9)
C11	0.0233 (9)	0.0378 (10)	0.0284 (10)	−0.0027 (8)	−0.0007 (8)	−0.0043 (9)
C12	0.0245 (9)	0.0291 (10)	0.0242 (10)	−0.0003 (8)	0.0007 (8)	0.0031 (7)
C13	0.0307 (10)	0.0304 (10)	0.0424 (13)	−0.0009 (9)	0.0014 (9)	−0.0051 (9)

Geometric parameters (Å, º)

S1—O2	1.4259 (13)	C5—C6	1.390 (3)
S1—O1	1.4343 (13)	C5—H5	0.9500
S1—N1	1.6350 (16)	C6—H6	0.9500
S1—C1	1.7707 (18)	C7—C12	1.381 (3)
N1—C7	1.441 (2)	C7—C8	1.385 (3)
N1—H1	0.855 (16)	C8—C9	1.384 (3)
N2—C13	1.144 (3)	C8—H8	0.9500
C1—C6	1.383 (2)	C9—C10	1.383 (3)
C1—C2	1.393 (2)	C9—H9	0.9500
C2—C3	1.382 (3)	C10—C11	1.380 (3)
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.396 (3)	C11—C12	1.387 (3)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.389 (3)	C12—H12	0.9500
C4—C13	1.447 (3)
O2—S1—O1	120.15 (8)	C6—C5—H5	120.2
O2—S1—N1	106.33 (8)	C1—C6—C5	119.07 (17)
O1—S1—N1	107.59 (8)	C1—C6—H6	120.5
O2—S1—C1	108.02 (8)	C5—C6—H6	120.5
O1—S1—C1	107.94 (8)	C12—C7—C8	120.60 (17)
N1—S1—C1	106.00 (8)	C12—C7—N1	119.20 (16)
C7—N1—S1	119.91 (12)	C8—C7—N1	120.14 (17)
C7—N1—H1	114.5 (13)	C9—C8—C7	119.71 (18)
S1—N1—H1	106.3 (14)	C9—C8—H8	120.1
C6—C1—C2	121.86 (17)	C7—C8—H8	120.1
C6—C1—S1	119.97 (14)	C10—C9—C8	119.96 (18)
C2—C1—S1	118.08 (13)	C10—C9—H9	120.0
C3—C2—C1	118.95 (17)	C8—C9—H9	120.0
C3—C2—H2	120.5	C11—C10—C9	119.96 (17)
C1—C2—H2	120.5	C11—C10—H10	120.0
C2—C3—C4	119.59 (18)	C9—C10—H10	120.0
C2—C3—H3	120.2	C10—C11—C12	120.53 (19)
C4—C3—H3	120.2	C10—C11—H11	119.7
C5—C4—C3	121.02 (17)	C12—C11—H11	119.7
C5—C4—C13	119.92 (17)	C7—C12—C11	119.19 (17)
C3—C4—C13	119.05 (18)	C7—C12—H12	120.4
C4—C5—C6	119.51 (17)	C11—C12—H12	120.4
C4—C5—H5	120.2	N2—C13—C4	178.8 (2)