Monoclinic pseudosymmetry in 2-phenoxy­benzene­sulfon­amide, a triclinic structure having Z′ = 4, and spontaneous resolution in monoclinic N-methyl-2-phenoxy­benzene­sulfon­amide

Glidewell, C.; Low, J.N.; Skakle, J.M.S.; Wardell, J.L.

doi:10.1107/S010827010400719X

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 60| Part 5| May 2004| Pages o364-o367

doi:10.1107/S010827010400719X

Monoclinic pseudosymmetry in 2-phenoxybenzenesulfonamide, a triclinic structure having Z′ = 4, and spontaneous resolution in monoclinic N-methyl-2-phenoxybenzenesulfonamide

Christopher Glidewell,^a ^* John N. Low,^b Janet M. S. Skakle ^b and James L. Wardell ^c

^aSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 22 March 2004; accepted 26 March 2004; online 30 April 2004)

2-Phenoxybenzenesulfonamide, C₁₂H₁₁NO₃S, (I), crystallizes in space group P $[\overline 1]$ with Z′ = 4, but the structure closely mimics the monoclinic space group P2₁/b with Z′ = 2. The molecules of (I) are linked by a combination of N—H⋯O and C—H⋯O hydrogen bonds into two independent chains of centrosymmetric edge-fused R $[{_2^2}]$ (18) and R $[{_6^6}]$ (34) rings. N-Methyl-2-phenoxybenzenesulfonamide, C₁₃H₁₃NO₃S, (II), crystallizes in space group P2₁ with Z′ = 1, and is an example of spontaneous resolution. The molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds into chains of spiro-fused R $[{_2^2}]$ (12) rings, and these chains are linked into sheets by a single C—H⋯π(arene) hydrogen bond.

Comment

We report here the structure of two closely related sulfonamides, namely 2-phenoxybenzenesulfonamide, (I), and its N-methyl analogue, (II), which both show interesting crystallization characteristics.

Compound (I) crystallizes in space group P $[\overline 1]$ with four independent molecules in the asymmetric unit (Fig. 1). The choice of the asymmetric unit in cases where Z′ > 1 allows some flexibility, but for (I) the asymmetric unit has been selected such that the molecules labelled A and C act as hydrogen-bond donors to molecules B and D, respectively, within the asymmetric unit. The bond lengths and angles present no unusual values, but the orientation of the sulfonamide groups relative to the adjacent arene rings is very similar in all four molecules (Table 1). These orientations are probably controlled in part by the intramolecular N—H⋯O hydrogen bonds (Table 2), each of which generates an S(6) motif (Bernstein et al., 1995 ).

The overall molecular conformations, which can be defined in terms of five independent torsion angles for each molecule, indicate the occurrence of pseudosymmetry. The values of these torsion angles (Table 1) show that for the selected asymmetric unit, molecules A and D form an approximately enantiomorphous pair and molecules B and C form a second such pair independent of the first. Detailed scrutiny of the atomic coordinates shows that those for molecule D are approximately related to those for molecule A by the transformation (x − 1, y − $[{1 \over 2}]$ , $[{3 \over 2}]$ − z), while those of molecule B are similarly related to those of molecule C by the related transformation (x, y − $[{1 \over 2}]$ , $[{3 \over 2}]$ − z). Overall, therefore, there is a pseudo b-glide plane at z = $[{3 \over 4}]$ . The unit-cell dimensions rule out any symmetry higher than triclinic, and the absence of any additional symmetry was confirmed by examination of the refined structure using PLATON (Spek, 2003 ). However, the structure exhibits a close mimicry of space group P2₁/b, an alternative to the conventional setting, P2₁/c, of space group No. 14. Consistent with this mimicry, the intensities of the 00l reflections are, in general, much weaker when l is odd than when l is even, although there is no obviously consistent pattern amongst the hk0 reflections.

The molecules of (I) are linked by a combination of N—H⋯O and C—H⋯O hydrogen bonds (Table 2) into two independent but very similar chains of edge-fused rings, one built from molecules of types A and B only, the other from molecules of types C and D only. It is necessary to discuss only one of these in any detail. Within the asymmetric unit, atom N1A acts as hydrogen-bond donor, via atom H11A, to atom O11B. In a similar manner, atom N1B at (x, y, z) acts as donor, via atom H11B, to atom O11A at (x − 1, y, z). In this manner, a C $[{_2^2}]$ (8) chain built from type A and B molecules and running parallel to the [100] direction is generated by translation. Within this chain, there is an intermolecular C—H⋯O contact, which is possibly more an adventitious contact consequent upon the N—H⋯O hydrogen bonds than a structurally significant hydrogen bond. Two antiparallel chains of A and B molecules, related to one another by inversion, run through each unit cell and these are linked by a single C—H⋯O hydrogen bond. Atom C25B at (x, y, z) acts as hydrogen-bond donor to atom O12B at (1 − x, 1 − y, 1 − z), and propagation of this interaction by translation and inversion generates a chain of centrosymmetric edge-fused rings along (x, $[{1 \over 2}]$ , $[{1 \over 2}]$ ), with R $[{_2^2}]$ (18) rings centred at (n+ $[{1 \over 2}]$ , $[{1 \over 2}]$ , $[{1 \over 2}]$ ) (n = zero or integer) and R $[{_6^6}]$ (34) rings centred at (n, $[{1 \over 2}]$ , $[{1 \over 2}]$ ) (n = zero or integer) (Fig. 2).

The molecules of types C and D form an entirely similar chain of edge-fused rings running along the line (x, 0, 1). Hence, in projection down a, there is a chain of A and B type molecules at the cell centre and chains of C and D type molecules at the cell vertices. However, there are no direction-specific interactions between adjacent chains. Despite the large number of independent aryl groups in the structure of (I), this contains neither C—H⋯π(arene) hydrogen bonds nor aromatic π–π stacking interactions.

The N-methyl analogue, (II) (Fig. 3), of (I) crystallizes in the chiral space group P2₁ with Z′ = 1. The molecular conformation of (II), as judged from the leading torsion angles (Table 1) bears no particularly close resemblance to those in (I), and there are no intramolecular hydrogen bonds in (II). The resulting molecular point group is C₁, so that the molecules are chiral. Accordingly, each crystal of (II) contains only a single enantiomorph, in contrast with the crystals of (I). Since the bulk sample of (II) is racemic, the crystallization represents an example of spontaneous resolution to form a conglomerate, rather than a racemate as in (I).

The molecules of (II) are linked into sheets by a combination of three hydrogen bonds (Table 3) and it is convenient to analyse the sheet formation in terms of its two one-dimensional substructures. Atoms N1 and C26 in the molecule at (x, y, z) act as hydrogen-bond donors to, respectively, atoms O11 and O12, both in the molecule at (1 + x, y, z), so generating by translation a C(4)C(8)[R $[{_2^2}]$ (12)] chain of rings running parallel to the [100] direction (Fig. 4). In addition, atom C4 at (x, y, z) acts as hydrogen-bond donor to the monosubstituted ring C21–C26 in the molecule at (x, 1 + y, z), so generating by translation a chain running parallel to the [010] direction (Fig. 5). The combination of the [100] and [010] chains generates an (001) sheet (Fig. 6). Two such sheets pass through each unit cell, one each in the domains −0.02 < z < 0.49 and 0.51 < z < 1.02, but there are no direction-specific interactions between adjacent sheets.

The C(4) chain motif in (II) is very characteristic of simple sulfonamides (Vorontsova, 1966 ; Cotton & Stokely, 1970 ; Klug, 1970 ; Brink & Mattes, 1986 ; Lightfoot et al., 1993 ; Tremayne et al., 1999 , 2002 ; Clark et al., 2003 ). The related C $[{_2^2}]$ (8) motif arises in (I) because two independent molecules participate in the formation of a single chain. On the other hand, the other hydrogen-bond motif most characteristic of sulfonamides, the R $[{_2^2}]$ (8) ring (Klug, 1968 ; Blaschette et al., 1986 ; Tremayne et al., 1999, 2002; Kelly et al., 2002 ; Clark et al., 2003), is absent from the structures of both (I) and (II). However, in compound (III) [Cambridge Structural Database (Allen, 2002 ) refcode SUTYOU; Chandramohan & Ravikumar, 1999 ], which is an isomer of (II), pairs of N—H⋯O hydrogen bonds generate centrosymmetric R $[{_2^2}]$ (8) rings, as noted in the original report. In addition, however, the resulting dimers are linked into [110] chains by a single aromatic π–π stacking interaction (Fig. 7).

Figure 1
The four independent molecules in (I

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
A stereoview of part of the crystal structure of (I

), showing the formation of a [100] chain of edge-fused R $[{_2^2}]$ (18) and R $[{_6^6}]$ (34) rings built from molecules of types A and B only. For the sake of clarity, H atoms bonded to C atoms but not involved in the hydrogen-bonding motif shown have been omitted

Figure 3
The molecule of (II

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 4
Part of the crystal structure of (II

), showing the formation of a [100] chain of spiro-fused R $[{_2^2}]$ (12) rings. For the sake of clarity, H atoms bonded to C atoms but not involved in the hydrogen-bonding motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (1 + x, y, z) and (x − 1, y, z), respectively.

Figure 5
Part of the crystal structure of (II

), showing the formation of a C—H⋯π(arene) chain along [010]. For the sake of clarity, H atoms not involved in the hydrogen-bonding motif shown have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, 1 + y, z) and (x, y − 1, z), respectively.

Figure 6
A stereoview of part of the crystal structure of (II

), showing the formation of an (001) sheet by combination of the [100] and [010] chains. For the sake of clarity, H atoms not involved in the hydrogen-bonding motifs shown have been omitted.

Figure 7
A stereoview of part of the crystal structure of (III

) (Chandramohan & Ravikumar, 1999

), showing the formation of a π-stacked [110] chain of centrosymmetric hydrogen-bonded dimers. The original atom coordinates have been used. For the sake of clarity, H atoms not involved in the hydrogen-bonding motif shown have been omitted.

Experimental

Samples of (I) and (II) were prepared by the reaction of 2-phenoxybenzenesulfonyl chloride (Neale et al., 1965 ) with an aqueous ammonia solution for (I) or with an aqueous methylamine solution for (II). Crystals suitable for single-crystal X-ray diffraction were grown from solutions in ethanol. M.p. for (I): 388–389 K [literature value 386–388 K (Abramovitch et al., 1978 )]; m.p. for (II): 354–357 K.

Table 1
Selected torsion angles (°) for (I) and (II)

Parameter	(I, n = A)	(I, n = B)	(I, n = C)	(I, n = D)	(II, n = nil)
C21n—O2n—C2n—C1n	132.0 (4)	−130.1 (4)	132.5 (4)	−130.6 (4)	101.8 (3)
C2n—O2n—C21n—C22n	−26.3 (6)	−98.4 (5)	96.5 (5)	23.7 (6)	−6.1 (4)
C2n—C1n—S1n—N1n	51.5 (4)	−50.2 (4)	50.4 (4)	−50.6 (4)	66.5 (3)
C2n—C1n—S1n—O11n	166.2 (3)	−165.4 (3)	165.4 (3)	−165.8 (3)	−179.0 (2)
C2n—C1n—S1n—O12n	−66.1 (4)	66.3 (4)	−67.0 (4)	66.0 (4)	−48.6 (3)
C1—S1—N1—C11					61.3 (2)

Compound (I)

Crystal data

C₁₂H₁₁NO₃S
M_r = 249.28
Triclinic, $[P\overline 1]$
a = 5.2539 (2) Å
b = 16.2090 (8) Å
c = 26.5417 (9) Å
α = 84.850 (2)°
β = 88.951 (2)°
γ = 87.607 (2)°
V = 2248.98 (16) Å³
Z = 8
D_x = 1.472 Mg m⁻³
Mo Kα radiation
Cell parameters from 9651 reflections
θ = 3.1–27.4°
μ = 0.28 mm⁻¹
T = 120 (2) K
Block, colourless
0.22 × 0.16 × 0.12 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ scans, and ω scans with κ offsets
Absorption correction: multi-scan (SORTAV; Blessing, 1995 , 1997 ) T_min = 0.926, T_max = 0.967
22 883 measured reflections
9651 independent reflections
4912 reflections with I > 2σ(I)
R_int = 0.071
θ_max = 27.4°
h = −6 → 6
k = −20 → 20
l = −34 → 33

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.203
S = 1.05
9651 reflections
614 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0812P)² + 1.7227P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 2
Hydrogen-bonding geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H12A⋯O2A	0.88	2.33	2.897 (5)	122
N1B—H12B⋯O2B	0.88	2.19	2.894 (4)	137
N1C—H12C⋯O2C	0.88	2.37	2.871 (4)	117
N1D—H12D⋯O2D	0.88	2.20	2.915 (4)	138
N1A—H11A⋯O11B	0.88	2.13	2.950 (4)	156
N1B—H11B⋯O11Aⁱ	0.88	2.08	2.945 (4)	165
N1C—H11C⋯O11D	0.88	2.14	2.947 (4)	153
N1D—H11D⋯O11Cⁱ	0.88	2.07	2.931 (4)	165
C25B—H25B⋯O12Bⁱⁱ	0.95	2.47	3.371 (6)	157
C25C—H25C⋯O12Cⁱⁱⁱ	0.95	2.42	3.320 (6)	158
C26A—H26A⋯O12Aⁱ	0.95	2.52	3.410 (5)	156
C26D—H26D⋯O12Dⁱ	0.95	2.46	3.378 (5)	161
Symmetry codes: (i) x-1,y,z; (ii) 1-x,1-y,1-z; (iii) 1-x,-y,2-z.

Compound (II)

Crystal data

C₁₃H₁₃NO₃S
M_r = 263.30
Monoclinic, P2₁
a = 5.3804 (2) Å
b = 7.9959 (4) Å
c = 14.4462 (7) Å
β = 95.226 (2)°
V = 618.91 (5) Å³
Z = 2
D_x = 1.413 Mg m⁻³
Mo Kα radiation
Cell parameters from 2703 reflections
θ = 2.9–27.5°
μ = 0.26 mm⁻¹
T = 120 (2) K
Block, colourless
0.22 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ scans, and ω scans with κ offsets
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) T_min = 0.951, T_max = 0.979
7538 measured reflections
2703 independent reflections
2548 reflections with I > 2σ(I)
R_int = 0.116
θ_max = 27.5°
h = −6 → 6
k = −10 → 10
l = −18 → 17

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.145
S = 1.05
2703 reflections
164 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.062P)² + 0.5323P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.48 e Å⁻³
Absolute structure: Flack (1983 ), with 1188 Friedel pairs
Flack parameter = 0.20 (11)

Table 3
Hydrogen-bonding geometry (Å, °) for (II)

Cg1 is the centroid of ring C21–C26.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O11ⁱ	0.88	2.21	2.953 (3)	141
C26—H26⋯O12ⁱ	0.95	2.43	3.377 (4)	174
C4—H4⋯Cg1ⁱⁱ	0.95	2.83	3.741 (3)	161
Symmetry codes: (i) 1+x,y,z; (ii) x,1+y,z.

Crystals of (I) are triclinic and space group P $[\overline 1]$ was selected and confirmed by the subsequent structure analysis. For (II), the systematic absences permitted P2₁ and P2₁/m as possible space groups. Consideration of the unit-cell volume led to the selection of P2₁, which was confirmed by the successful structure analysis. All Hatoms were located in difference maps and then treated as riding atoms, with C—H distances of 0.95 (aromatic) or 0.98 Å (methyl) and N—H distances of 0.88 Å, and with U_iso(H) = 1.2U_eq(C,N) or1.5U_eq(C) for the methyl group. Examination of the refined structure of (I) using the ADDSYM option in PLATON (Spek, 2003) revealed no possible additional symmetry, but scrutiny of the reflection data suggested the possibility of twinning about c*. Following the use of the TWINROTMAT option in PLATON to generate a HKLF 5-type reflection file, modified to take into account possible reflection overlap, further refinement led to significant reductions in the R indices, although with only trivial changes to the atomic coordinates and hence to the derived geometric parameters, and indicated a twin fraction of ca 8.8 (2)%. The correct absolute configuration of (II) was established by means of the Flack parameter (Flack, 1983).

For both compounds, data collection: KappaCCD Server Software (Nonius, 1997 ); cell refinement and data reduction: DENZO–SMN (Otwinowski & Minor, 1997 ); structure solution: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); structure refinement: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I, II. DOI: 10.1107/S010827010400719X/sk1716sup1.cif

Structure factors: contains datablock 483rt. DOI: 10.1107/S010827010400719X/sk1716Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S010827010400719X/sk1716IIsup3.hkl

Comment top

We report here the structure of two closely-related sulfonamides, 2-phenoxybenzenesulfonamide, (I), and its N-methyl analogue, (II), which both show interesting crystallization characteristics. \sch

Compound (I) crystallizes in space group P1 with four independent molecules in the asymmetric unit (Fig. 1). The choice of the asymmetric unit in cases where Z' > 1 allows some flexibility, but for (I) the asymmetric unit has been selected such that the molecules labelled A and C act as hydrogen-bond donors to molecules B and D, respectively, within the asymmetric unit. The bond lengths and angles present no unusual values, but the orientation of the sulfonamide groups relative to the adjacent arene rings is very similar in all the molecules (Table 1). These orientations are probably controlled in part by the intramolecular N—H···O hydrogen bonds (Table 2), each of which generates an S(6) motif (Bernstein et al., 1995).

The overall molecular conformations, which can be defined in terms of five independent torsion angles for each molecule, indicate the occurrence of pseudosymmetry. The values of these torsion angles (Table 1) show that, for the selected asymmetric unit, molecules A and D form an approximately enantiomorphous pair and molecules B and C form a second such pair, independent of the first. Detailed scrutiny of the atomic coordinates shows that those for molecule D are approximately related to those for molecule A by the transformation (x − 1, y − 1/2, 3/2 − z), while those of molecule B are similarly related to those of molecule C by the related transformation (x, y − 1/2, 3/2 − z). Overall, therefore, there is a pseudo b-glide plane at z = 3/4. The unit-cell dimensions rule out any symmetry higher than triclinic, and the absence of any additional symmetry was confirmed by examination of the refined structure using PLATON (Spek, 2003). However, the structure exhibits a close mimicry of space group P2₁/b, an alternative to the conventional setting, P2₁/c, of space group No. 14. Consistent with this mimicry, the intensities of the (00 l) reflections are, in general, much weaker when l is odd than when l is even, although there is no obviously consistent pattern amongst the (hk0) reflections.

The molecules of (I) are linked by a combination of N—H···O and C—H···O hydrogen bonds (Table 2) into two independent but very similar chains of edge-fused rings, one built from molecules of types A and B only, the other from molecules of types C and D only. It is necessary to discuss only one of these in any detail. Within the asymmetric unit, atom N1A acts as hydrogen-bond donor, via atom H11A, to atom O11B. In a similar manner, atom N1B at (x, y, z) acts as donor, via atom H11B, to atom O11A at (x − 1, y, z). In this manner, a C₂²(8) chain built from type A and B molecules and running parallel to the [100] direction is generated by translation. Within this chain, there is an intermolecular C—H···O contact, which is possibly more an adventitious contact consequent upon the N—H···O hydrogen bonds than a structurally significant hydrogen-bond. Two antiparallel chains of A and B molecules, related to one another by inversion, run through each unit cell and these are linked by a single C—H···O hydrogen bond. Atom C25B at (x, y, z) acts as hydrogen-bond donor to atom O12B at (1 − x, 1 − y, 1 − z), and propagation of this interaction by translation and inversion generates a chain of centrosymmetric edge-fused rings along (x, 1/2, 1/2), with R₂²(18) rings centred at (n+1/2, 1/2, 1/2) (n = zero or integer), and R₆⁶(34) rings centred at (n, 1/2, 1/2) (n = zero or integer) (Fig. 2).

The molecules of types C and D form an entirely similar chain of edge-fused rings running along the line (x, 0, 1). Hence in projection down a, there is a chain of A and B type molecules at the cell centre, and chains of C and D type molecules at the cell vertices. However, there are no direction-specific interactions between adjacent chains. Despite the large number of independent aryl groups in the structure of (I), this contains neither C—H···π(arene) hydrogen bonds nor aromatic π–π stacking interactions.

The N-methyl analogue, (II) (Fig. 3), of (I) crystallizes in the chiral space group P2₁ with Z' = 1. The molecular conformation of (II), as judged from the leading torsion angles (Table 1) bears no particularly close resemblance to those in (I), and there are no intramolecular hydrogen bonds in (II). The resulting molecular point group is C₁, so that the molecules are chiral. Accordingly, each crystal of (II) contains only a single enantiomorph, in contrast with the crystals of (I). Since the bulk sample of (II) is racemic, the crystallization represents an example of spontaneous resolution to form a conglomerate, rather than a racemate as in (I).

The molecules of (II) are linked into sheets by a combination of three hydrogen bonds (Table 3) and it is convenient to analyse the sheet formation in terms of its two one-dimensional sub-structures. Atoms N1 and C26 in the molecule at (x, y, z) act as hydrogen-bond donors to, respectively, atoms O11 and O12, both in the molecule at (1 + x, y, z), so generating by translation a C(4) C(8)[R₂²(12)] chain of rings running parallel to the [100] direction (Fig. 4). In addition, atom C4 at (x, y, z) acts as hydrogen-bond donor to the monosubstituted ring C21—C26 in the molecule at (x, 1 + y, z), so generating by translation a chain running parallel to the [010] direction (Fig. 5). The combination of the [100] and [010] chains generates an (001) sheet (Fig. 6). Two such sheets pass through each unit cell, one each in the domains −0.02 < z < 0.49 and 0.51 < z < 1.02, but there are no direction-specific interactions between adjacent sheets.

The C(4) chain motif in (II) is very characteristic of simple sulfonamides (Vorontsova, 1966; Cotton & Stokely, 1970; Klug, 1970; Brink & Mattes, 1986; Lightfoot et al., 1993; Tremayne et al., 1999, 2002; Clark et al., 2003). The related C₂²(8) motif arises in (I) because two independent molecules participate in the formation of a single chain. On the other hand, the other hydrogen-bond motif most characteristic of sulfonamides, the R₂²(8) ring (Klug, 1968; Blaschette et al., 1986; Tremayne et al., 1999, 2002; Kelly et al., 2002; Clark et al., 2003), is absent from the structures of both (I) and (II). However, in compound (III) [Cambridge Structural Database (Allen, 2002) refcode SUTYOU; Chandramohan & Ravikumar, 1999], which is an isomer of (II), pairs of N—H···O hydrogen bonds generate centrosymmetric R₂²(8) rings, as noted in the original report. In addition, however, the resulting dimers are linked into [110] chains by a single aromatic π–π stacking interaction (Fig. 7).

Table 1. Selected torsional angles (°) for compounds (I) and (II)

Table 2. Hydrogen bond parameters (Å, °) for compound (I)

Table 2. Hydrogen bond parameters (Å, °) for compound (II): Cg1 is the centroid of ring C21—C26

Experimental top

Samples of (I) and (II) were prepared by the reaction of 2-phenoxybenzenesulfonyl chloride (Neale et al., 1965) with aqueous ammonia solution for (I), or with aqueous methylamine solution for (II). Crystals suitable for single-crystal X-ray diffraction were grown from solutions in ethanol. M.p. for (I): 388–389 K [literature value 386–388 K (Abramovitch et al., 1978)]. M.p. for (II): 354–357 K.

Computing details top

For both compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The four independent molecules in (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A stereoview of part of the crystal structure of (I), showing formation of a [100] chain of edge-fused R₂²(18) and R₆⁶(34) rings built from molecules of types A and B only. For the sake of clarity, H atoms bonded to C atoms but not involved in the hydrogen-bonding shown have been omitted
	Fig. 3. The molecule of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 4. Part of the crystal structure of (II), showing formation of a [100] chain of spiro-fused R₂²(12) rings. For the sake of clarity, H atoms bonded to C atoms but not involved in the hydrogen-bonding motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (1 + x, y, z) and (x − 1, y, z), respectively.
	Fig. 5. Part of the crystal structure of (II), showing formation of a C—H···π(arene) chain along [010]. For the sake of clarity, H atoms not involved in the hydrogen-bonding motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x, 1 + y, z) and (x, y − 1, z), respectively.
	Fig. 6. A stereoview of part of the crystal structure of (II), showing formation of an (001) sheet by combination of the [100] and [010] chains. For the sake of clarity, H atoms not involved in the hydrogen-bonding motifs shown have been omitted.
	Fig. 7. A stereoview of part of the crystal structure of (III) (Chandramohan & Ravikumar, 1999), showing formation of a π-stacked [110] chain of centrosymmetric hydrogen-bonded dimers. The original atom coordinates have been used. For the sake of clarity, H atoms not involved in the hydrogen-bonding motif shown have been omitted.

(I) 2-Phenoxybenzenesulfonamide top

Crystal data top

C₁₂H₁₁NO₃S	Z = 8
M_r = 249.28	F(000) = 1040
Triclinic, P1	D_x = 1.472 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2539 (2) Å	Cell parameters from 9651 reflections
b = 16.2090 (8) Å	θ = 3.1–27.4°
c = 26.5417 (9) Å	µ = 0.28 mm⁻¹
α = 84.850 (2)°	T = 120 K
β = 88.951 (2)°	Block, colourless
γ = 87.607 (2)°	0.22 × 0.16 × 0.12 mm
V = 2248.98 (16) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	9651 independent reflections
Radiation source: rotating anode	4912 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
ϕ scans, and ω scans with κ offsets	θ_max = 27.4°, θ_min = 3.1°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −6→6
T_min = 0.926, T_max = 0.967	k = −20→20
22883 measured reflections	l = −34→33

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.203	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0812P)² + 1.7227P] where P = (F_o² + 2F_c²)/3
9651 reflections	(Δ/σ)_max = 0.001
614 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₁₂H₁₁NO₃S	γ = 87.607 (2)°
M_r = 249.28	V = 2248.98 (16) Å³
Triclinic, P1	Z = 8
a = 5.2539 (2) Å	Mo Kα radiation
b = 16.2090 (8) Å	µ = 0.28 mm⁻¹
c = 26.5417 (9) Å	T = 120 K
α = 84.850 (2)°	0.22 × 0.16 × 0.12 mm
β = 88.951 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	9651 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	4912 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.967	R_int = 0.071
22883 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.203	H-atom parameters constrained
S = 1.05	Δρ_max = 0.33 e Å⁻³
9651 reflections	Δρ_min = −0.64 e Å⁻³
614 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1A	0.9210 (2)	0.51997 (7)	0.82938 (4)	0.0198 (3)
O11A	1.0634 (6)	0.50443 (18)	0.78422 (11)	0.0251 (7)
O12A	1.0312 (6)	0.49179 (19)	0.87669 (11)	0.0270 (7)
N1A	0.6529 (7)	0.4766 (2)	0.82568 (13)	0.0226 (8)
C1A	0.8649 (8)	0.6284 (3)	0.82745 (15)	0.0191 (9)
C2A	0.6866 (8)	0.6621 (3)	0.85996 (15)	0.0213 (10)
C3A	0.6413 (9)	0.7466 (3)	0.85754 (18)	0.0297 (11)
C4A	0.7776 (9)	0.7977 (3)	0.82392 (18)	0.0308 (12)
C5A	0.9611 (9)	0.7650 (3)	0.79166 (18)	0.0298 (11)
C6A	1.0011 (9)	0.6801 (3)	0.79349 (16)	0.0241 (10)
O2A	0.5518 (6)	0.60737 (19)	0.89177 (11)	0.0283 (7)
C21A	0.5289 (8)	0.6196 (3)	0.94330 (16)	0.0222 (10)
C22A	0.7088 (8)	0.6612 (3)	0.96774 (17)	0.0280 (11)
C23A	0.6791 (10)	0.6672 (3)	1.01920 (18)	0.0363 (12)
C24A	0.4724 (9)	0.6321 (3)	1.04564 (17)	0.0321 (12)
C25A	0.2981 (9)	0.5914 (3)	1.02017 (17)	0.0301 (11)
C26A	0.3255 (8)	0.5852 (3)	0.96859 (16)	0.0250 (10)
S1B	0.4192 (2)	0.47590 (7)	0.67480 (4)	0.0197 (3)
O11B	0.5758 (6)	0.45312 (19)	0.71816 (10)	0.0248 (7)
O12B	0.5083 (6)	0.45230 (19)	0.62674 (11)	0.0269 (7)
N1B	0.1466 (7)	0.4351 (2)	0.68614 (13)	0.0230 (8)
C1B	0.3736 (8)	0.5853 (3)	0.67105 (14)	0.0179 (9)
C2B	0.1844 (8)	0.6248 (3)	0.64027 (15)	0.0200 (10)
C3B	0.1474 (9)	0.7098 (3)	0.63852 (16)	0.0251 (10)
C4B	0.3062 (9)	0.7555 (3)	0.66545 (17)	0.0263 (11)
C5B	0.4992 (9)	0.7165 (3)	0.69449 (17)	0.0275 (11)
C6B	0.5312 (8)	0.6314 (3)	0.69817 (16)	0.0238 (10)
O2B	0.0314 (6)	0.57638 (18)	0.61448 (10)	0.0240 (7)
C21B	0.0086 (8)	0.6011 (3)	0.56234 (16)	0.0229 (10)
C22B	−0.2019 (8)	0.6484 (3)	0.54527 (17)	0.0280 (11)
C23B	−0.2242 (10)	0.6702 (3)	0.49382 (18)	0.0367 (12)
C24B	−0.0384 (9)	0.6447 (3)	0.46043 (17)	0.0318 (12)
C25B	0.1717 (10)	0.5968 (3)	0.47842 (18)	0.0357 (12)
C26B	0.1940 (9)	0.5752 (3)	0.52960 (17)	0.0308 (11)
S1C	0.4039 (2)	0.01826 (7)	0.82718 (4)	0.0211 (3)
O11C	0.5445 (6)	0.00351 (19)	0.78144 (11)	0.0267 (7)
O12C	0.5152 (6)	−0.01135 (19)	0.87439 (11)	0.0281 (7)
N1C	0.1336 (7)	−0.0237 (2)	0.82357 (13)	0.0239 (9)
C1C	0.3535 (8)	0.1270 (3)	0.82664 (15)	0.0201 (10)
C2C	0.1739 (8)	0.1599 (3)	0.85987 (15)	0.0208 (10)
C3C	0.1398 (9)	0.2450 (3)	0.85989 (17)	0.0265 (11)
C4C	0.2879 (9)	0.2962 (3)	0.82792 (18)	0.0286 (11)
C5C	0.4672 (9)	0.2639 (3)	0.79521 (18)	0.0298 (11)
C6C	0.4982 (9)	0.1789 (3)	0.79464 (16)	0.0264 (11)
O2C	0.0296 (6)	0.10505 (19)	0.88953 (10)	0.0250 (7)
C21C	0.0092 (8)	0.1174 (3)	0.94146 (16)	0.0209 (10)
C22C	−0.1974 (8)	0.1603 (3)	0.95901 (18)	0.0298 (11)
C23C	−0.2170 (9)	0.1705 (3)	1.01029 (18)	0.0348 (12)
C24C	−0.0324 (10)	0.1366 (3)	1.04281 (17)	0.0310 (12)
C25C	0.1738 (9)	0.0930 (3)	1.02408 (18)	0.0338 (12)
C26C	0.1970 (9)	0.0835 (3)	0.97331 (18)	0.0308 (11)
S1D	−0.0949 (2)	−0.02297 (7)	0.67248 (4)	0.0189 (3)
O11D	0.0567 (5)	−0.04790 (18)	0.71626 (10)	0.0243 (7)
O12D	−0.0043 (6)	−0.04732 (19)	0.62480 (10)	0.0266 (7)
N1D	−0.3707 (6)	−0.0615 (2)	0.68270 (13)	0.0205 (8)
C1D	−0.1313 (8)	0.0865 (3)	0.66906 (15)	0.0180 (9)
C2D	−0.3151 (8)	0.1286 (3)	0.63740 (16)	0.0217 (10)
C3D	−0.3519 (8)	0.2129 (3)	0.63762 (17)	0.0282 (11)
C4D	−0.1973 (9)	0.2560 (3)	0.66681 (17)	0.0292 (11)
C5D	−0.0105 (8)	0.2159 (3)	0.69662 (17)	0.0258 (11)
C6D	0.0219 (8)	0.1308 (3)	0.69822 (16)	0.0233 (10)
O2D	−0.4625 (6)	0.08193 (19)	0.60998 (11)	0.0260 (7)
C21D	−0.4872 (8)	0.1048 (3)	0.55804 (15)	0.0206 (10)
C22D	−0.3120 (9)	0.1500 (3)	0.53022 (17)	0.0279 (11)
C23D	−0.3449 (9)	0.1664 (3)	0.47859 (18)	0.0341 (12)
C24D	−0.5506 (9)	0.1358 (3)	0.45535 (17)	0.0307 (12)
C25D	−0.7246 (9)	0.0889 (3)	0.48389 (16)	0.0269 (11)
C26D	−0.6950 (8)	0.0738 (3)	0.53546 (16)	0.0250 (10)
H11A	0.5965	0.4820	0.7945	0.027*
H12A	0.5352	0.4894	0.8480	0.027*
H3A	0.5160	0.7696	0.8791	0.036*
H4A	0.7466	0.8560	0.8226	0.037*
H5A	1.0567	0.8007	0.7689	0.036*
H6A	1.1228	0.6569	0.7713	0.029*
H22A	0.8492	0.6849	0.9496	0.034*
H23A	0.8003	0.6954	1.0367	0.044*
H24A	0.4526	0.6363	1.0810	0.039*
H25A	0.1573	0.5673	1.0380	0.036*
H26A	0.2040	0.5572	0.9510	0.030*
H12B	0.0480	0.4591	0.6622	0.028*
H11B	0.0928	0.4540	0.7147	0.028*
H3B	0.0137	0.7369	0.6190	0.030*
H4B	0.2822	0.8141	0.6639	0.032*
H5B	0.6102	0.7485	0.7120	0.033*
H6B	0.6600	0.6044	0.7191	0.029*
H22B	−0.3292	0.6657	0.5684	0.034*
H23B	−0.3679	0.7029	0.4814	0.044*
H24B	−0.0544	0.6599	0.4252	0.038*
H25B	0.2994	0.5790	0.4555	0.043*
H26B	0.3373	0.5425	0.5421	0.037*
H11C	0.0815	−0.0149	0.7922	0.029*
H12C	0.0414	−0.0217	0.8515	0.029*
H3C	0.0159	0.2680	0.8817	0.032*
H4C	0.2663	0.3546	0.8284	0.034*
H5C	0.5674	0.2998	0.7735	0.036*
H6C	0.6193	0.1561	0.7722	0.032*
H22C	−0.3261	0.1829	0.9365	0.036*
H23C	−0.3586	0.2011	1.0230	0.042*
H24C	−0.0469	0.1431	1.0780	0.037*
H25C	0.3013	0.0694	1.0465	0.041*
H26C	0.3402	0.0539	0.9604	0.037*
H12D	−0.4542	−0.0373	0.6566	0.025*
H11D	−0.4246	−0.0460	0.7121	0.025*
H3D	−0.4824	0.2414	0.6179	0.034*
H4D	−0.2207	0.3145	0.6663	0.035*
H5D	0.0956	0.2467	0.7160	0.031*
H6D	0.1485	0.1026	0.7192	0.028*
H22D	−0.1691	0.1700	0.5461	0.033*
H23D	−0.2260	0.1989	0.4590	0.041*
H24D	−0.5722	0.1469	0.4199	0.037*
H25D	−0.8644	0.0672	0.4680	0.032*
H26D	−0.8154	0.0424	0.5553	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0224 (6)	0.0181 (7)	0.0191 (5)	0.0001 (5)	0.0003 (4)	−0.0033 (4)
O11A	0.0259 (16)	0.0231 (19)	0.0272 (16)	0.0007 (13)	0.0060 (14)	−0.0087 (13)
O12A	0.0348 (18)	0.0218 (19)	0.0244 (16)	−0.0009 (14)	−0.0044 (14)	−0.0008 (13)
N1A	0.026 (2)	0.020 (2)	0.0228 (19)	−0.0059 (16)	0.0031 (16)	−0.0054 (15)
C1A	0.020 (2)	0.016 (3)	0.021 (2)	−0.0022 (18)	−0.0015 (18)	−0.0040 (18)
C2A	0.025 (2)	0.017 (3)	0.023 (2)	−0.0045 (19)	0.0037 (19)	−0.0063 (18)
C3A	0.029 (3)	0.021 (3)	0.040 (3)	0.004 (2)	0.004 (2)	−0.009 (2)
C4A	0.037 (3)	0.013 (3)	0.043 (3)	0.002 (2)	−0.007 (2)	−0.006 (2)
C5A	0.037 (3)	0.020 (3)	0.032 (3)	−0.008 (2)	0.002 (2)	−0.001 (2)
C6A	0.025 (2)	0.024 (3)	0.023 (2)	−0.001 (2)	0.0021 (19)	−0.0057 (19)
O2A	0.0341 (18)	0.027 (2)	0.0256 (16)	−0.0082 (15)	0.0125 (14)	−0.0113 (14)
C21A	0.022 (2)	0.018 (3)	0.027 (2)	0.0066 (19)	0.0054 (19)	−0.0072 (18)
C22A	0.018 (2)	0.030 (3)	0.036 (3)	0.000 (2)	0.003 (2)	−0.007 (2)
C23A	0.040 (3)	0.036 (3)	0.034 (3)	0.001 (2)	−0.007 (2)	−0.009 (2)
C24A	0.039 (3)	0.033 (3)	0.024 (2)	0.010 (2)	−0.004 (2)	−0.002 (2)
C25A	0.031 (3)	0.027 (3)	0.031 (3)	0.004 (2)	0.008 (2)	0.000 (2)
C26A	0.022 (2)	0.025 (3)	0.027 (2)	0.0036 (19)	0.0016 (19)	−0.0049 (19)
S1B	0.0210 (6)	0.0169 (7)	0.0214 (6)	0.0013 (5)	0.0015 (5)	−0.0036 (4)
O11B	0.0250 (16)	0.0243 (19)	0.0249 (16)	0.0043 (13)	−0.0016 (14)	−0.0036 (13)
O12B	0.0297 (17)	0.026 (2)	0.0253 (16)	0.0045 (14)	0.0087 (14)	−0.0063 (13)
N1B	0.026 (2)	0.018 (2)	0.0254 (19)	−0.0020 (16)	0.0032 (16)	−0.0035 (15)
C1B	0.019 (2)	0.020 (3)	0.015 (2)	0.0021 (18)	0.0055 (17)	−0.0006 (17)
C2B	0.018 (2)	0.023 (3)	0.019 (2)	−0.0031 (18)	0.0043 (18)	−0.0036 (18)
C3B	0.029 (2)	0.018 (3)	0.027 (2)	0.002 (2)	0.005 (2)	−0.0003 (19)
C4B	0.031 (3)	0.016 (3)	0.032 (2)	−0.003 (2)	0.010 (2)	−0.0048 (19)
C5B	0.029 (3)	0.023 (3)	0.031 (2)	−0.010 (2)	0.004 (2)	−0.005 (2)
C6B	0.021 (2)	0.026 (3)	0.025 (2)	−0.002 (2)	−0.0014 (19)	−0.0056 (19)
O2B	0.0261 (16)	0.0237 (19)	0.0220 (15)	−0.0056 (13)	−0.0020 (13)	0.0015 (12)
C21B	0.023 (2)	0.019 (3)	0.027 (2)	−0.0074 (19)	−0.005 (2)	0.0001 (18)
C22B	0.023 (2)	0.032 (3)	0.029 (2)	0.003 (2)	0.001 (2)	−0.003 (2)
C23B	0.035 (3)	0.042 (3)	0.032 (3)	0.004 (2)	−0.004 (2)	0.001 (2)
C24B	0.041 (3)	0.035 (3)	0.021 (2)	−0.012 (2)	−0.003 (2)	0.001 (2)
C25B	0.034 (3)	0.042 (4)	0.032 (3)	−0.002 (2)	0.008 (2)	−0.012 (2)
C26B	0.022 (2)	0.036 (3)	0.035 (3)	0.002 (2)	0.000 (2)	−0.007 (2)
S1C	0.0225 (6)	0.0202 (7)	0.0209 (5)	0.0017 (5)	−0.0019 (5)	−0.0035 (4)
O11C	0.0292 (17)	0.026 (2)	0.0259 (16)	−0.0003 (14)	0.0059 (14)	−0.0081 (13)
O12C	0.0336 (18)	0.024 (2)	0.0268 (16)	0.0064 (14)	−0.0086 (14)	−0.0016 (13)
N1C	0.030 (2)	0.021 (2)	0.0208 (18)	−0.0054 (17)	−0.0014 (16)	−0.0031 (15)
C1C	0.020 (2)	0.018 (3)	0.022 (2)	−0.0008 (18)	−0.0035 (19)	−0.0024 (18)
C2C	0.022 (2)	0.019 (3)	0.021 (2)	−0.0027 (19)	−0.0030 (19)	−0.0051 (18)
C3C	0.028 (3)	0.024 (3)	0.029 (2)	0.003 (2)	−0.004 (2)	−0.009 (2)
C4C	0.030 (3)	0.019 (3)	0.037 (3)	0.003 (2)	−0.004 (2)	−0.005 (2)
C5C	0.032 (3)	0.024 (3)	0.033 (3)	−0.008 (2)	0.002 (2)	0.000 (2)
C6C	0.027 (2)	0.028 (3)	0.025 (2)	−0.003 (2)	0.001 (2)	−0.003 (2)
O2C	0.0309 (18)	0.024 (2)	0.0217 (15)	−0.0065 (14)	0.0045 (14)	−0.0063 (13)
C21C	0.020 (2)	0.020 (3)	0.023 (2)	−0.0090 (19)	0.0009 (19)	−0.0036 (18)
C22C	0.020 (2)	0.037 (3)	0.033 (3)	0.001 (2)	−0.001 (2)	−0.003 (2)
C23C	0.030 (3)	0.040 (3)	0.035 (3)	0.002 (2)	0.009 (2)	−0.008 (2)
C24C	0.044 (3)	0.027 (3)	0.023 (2)	−0.009 (2)	0.000 (2)	−0.003 (2)
C25C	0.030 (3)	0.040 (3)	0.030 (3)	0.003 (2)	−0.007 (2)	0.001 (2)
C26C	0.031 (3)	0.024 (3)	0.038 (3)	0.003 (2)	0.000 (2)	−0.005 (2)
S1D	0.0193 (5)	0.0182 (7)	0.0191 (5)	0.0000 (4)	0.0006 (4)	−0.0016 (4)
O11D	0.0259 (16)	0.0235 (19)	0.0233 (16)	0.0026 (13)	−0.0040 (13)	−0.0023 (13)
O12D	0.0331 (18)	0.025 (2)	0.0224 (16)	−0.0007 (14)	0.0068 (14)	−0.0064 (13)
N1D	0.0196 (19)	0.018 (2)	0.0242 (18)	−0.0027 (15)	0.0038 (15)	−0.0012 (15)
C1D	0.020 (2)	0.015 (3)	0.019 (2)	0.0003 (17)	0.0007 (18)	−0.0005 (17)
C2D	0.019 (2)	0.021 (3)	0.025 (2)	−0.0022 (19)	−0.0032 (19)	0.0028 (18)
C3D	0.022 (2)	0.027 (3)	0.035 (3)	0.005 (2)	−0.002 (2)	0.003 (2)
C4D	0.038 (3)	0.016 (3)	0.033 (3)	−0.002 (2)	0.009 (2)	−0.003 (2)
C5D	0.022 (2)	0.022 (3)	0.035 (3)	−0.006 (2)	0.001 (2)	−0.009 (2)
C6D	0.018 (2)	0.028 (3)	0.024 (2)	−0.0030 (19)	0.0009 (19)	−0.0018 (19)
O2D	0.0297 (17)	0.0233 (19)	0.0249 (16)	−0.0060 (14)	−0.0084 (14)	0.0021 (13)
C21D	0.023 (2)	0.016 (3)	0.022 (2)	0.0049 (18)	−0.0037 (19)	0.0006 (17)
C22D	0.022 (2)	0.032 (3)	0.030 (2)	−0.001 (2)	−0.002 (2)	−0.001 (2)
C23D	0.027 (3)	0.038 (3)	0.036 (3)	0.002 (2)	0.007 (2)	0.002 (2)
C24D	0.040 (3)	0.033 (3)	0.018 (2)	0.008 (2)	0.002 (2)	0.0006 (19)
C25D	0.026 (2)	0.029 (3)	0.026 (2)	0.006 (2)	−0.008 (2)	−0.0075 (19)
C26D	0.023 (2)	0.025 (3)	0.027 (2)	−0.0001 (19)	−0.0019 (19)	−0.0016 (19)

Geometric parameters (Å, º) top

S1A—O12A	1.422 (3)	S1C—O12C	1.428 (3)
S1A—O11A	1.437 (3)	S1C—O11C	1.443 (3)
S1A—N1A	1.609 (4)	S1C—N1C	1.608 (4)
S1A—C1A	1.767 (4)	S1C—C1C	1.770 (5)
N1A—H11A	0.88	N1C—H11C	0.88
N1A—H12A	0.88	N1C—H12C	0.88
C1A—C6A	1.384 (6)	C1C—C6C	1.381 (6)
C1A—C2A	1.390 (6)	C1C—C2C	1.402 (6)
C2A—C3A	1.376 (6)	C2C—O2C	1.376 (5)
C2A—O2A	1.378 (5)	C2C—C3C	1.384 (6)
C3A—C4A	1.374 (7)	C3C—C4C	1.385 (7)
C3A—H3A	0.95	C3C—H3C	0.95
C4A—C5A	1.397 (7)	C4C—C5C	1.388 (7)
C4A—H4A	0.95	C4C—H4C	0.95
C5A—C6A	1.381 (6)	C5C—C6C	1.382 (6)
C5A—H5A	0.95	C5C—H5C	0.95
C6A—H6A	0.95	C6C—H6C	0.95
O2A—C21A	1.402 (5)	O2C—C21C	1.412 (5)
C21A—C26A	1.364 (6)	C21C—C22C	1.362 (6)
C21A—C22A	1.387 (6)	C21C—C26C	1.376 (6)
C22A—C23A	1.384 (7)	C22C—C23C	1.387 (7)
C22A—H22A	0.95	C22C—H22C	0.95
C23A—C24A	1.396 (7)	C23C—C24C	1.375 (7)
C23A—H23A	0.95	C23C—H23C	0.95
C24A—C25A	1.372 (7)	C24C—C25C	1.378 (7)
C24A—H24A	0.95	C24C—H24C	0.95
C25A—C26A	1.386 (6)	C25C—C26C	1.373 (7)
C25A—H25A	0.95	C25C—H25C	0.95
C26A—H26A	0.95	C26C—H26C	0.95
S1B—O12B	1.429 (3)	S1D—O12D	1.427 (3)
S1B—O11B	1.439 (3)	S1D—O11D	1.439 (3)
S1B—N1B	1.614 (4)	S1D—N1D	1.611 (3)
S1B—C1B	1.774 (4)	S1D—C1D	1.770 (4)
N1B—H11B	0.88	N1D—H11D	0.88
N1B—H12B	0.88	N1D—H12D	0.88
C1B—C6B	1.389 (6)	C1D—C6D	1.391 (6)
C1B—C2B	1.396 (6)	C1D—C2D	1.406 (6)
C2B—O2B	1.378 (5)	C2D—O2D	1.367 (5)
C2B—C3B	1.380 (6)	C2D—C3D	1.373 (6)
C3B—C4B	1.387 (6)	C3D—C4D	1.384 (6)
C3B—H3B	0.95	C3D—H3D	0.95
C4B—C5B	1.382 (7)	C4D—C5D	1.376 (6)
C4B—H4B	0.95	C4D—H4D	0.95
C5B—C6B	1.378 (6)	C5D—C6D	1.381 (6)
C5B—H5B	0.95	C5D—H5D	0.95
C6B—H6B	0.95	C6D—H6D	0.95
O2B—C21B	1.412 (5)	O2D—C21D	1.402 (5)
C21B—C26B	1.371 (6)	C21D—C22D	1.365 (6)
C21B—C22B	1.379 (6)	C21D—C26D	1.389 (6)
C22B—C23B	1.386 (7)	C22D—C23D	1.385 (7)
C22B—H22B	0.95	C22D—H22D	0.95
C23B—C24B	1.382 (7)	C23D—C24D	1.386 (7)
C23B—H23B	0.95	C23D—H23D	0.95
C24B—C25B	1.389 (7)	C24D—C25D	1.384 (7)
C24B—H24B	0.95	C24D—H24D	0.95
C25B—C26B	1.378 (7)	C25D—C26D	1.379 (6)
C25B—H25B	0.95	C25D—H25D	0.95
C26B—H26B	0.95	C26D—H26D	0.95

O12A—S1A—O11A	117.79 (19)	O12C—S1C—O11C	117.95 (19)
O12A—S1A—N1A	108.24 (19)	O12C—S1C—N1C	108.2 (2)
O11A—S1A—N1A	106.54 (19)	O11C—S1C—N1C	106.81 (19)
O12A—S1A—C1A	108.49 (19)	O12C—S1C—C1C	107.93 (19)
O11A—S1A—C1A	106.62 (19)	O11C—S1C—C1C	106.6 (2)
N1A—S1A—C1A	108.9 (2)	N1C—S1C—C1C	109.1 (2)
S1A—N1A—H11A	111.3	S1C—N1C—H11C	108.3
S1A—N1A—H12A	115.9	S1C—N1C—H12C	112.5
H11A—N1A—H12A	112.7	H11C—N1C—H12C	127.7
C6A—C1A—C2A	119.9 (4)	C6C—C1C—C2C	120.5 (4)
C6A—C1A—S1A	119.6 (3)	C6C—C1C—S1C	119.6 (4)
C2A—C1A—S1A	120.5 (3)	C2C—C1C—S1C	119.9 (3)
C3A—C2A—O2A	122.8 (4)	O2C—C2C—C3C	122.8 (4)
C3A—C2A—C1A	120.0 (4)	O2C—C2C—C1C	117.7 (4)
O2A—C2A—C1A	117.1 (4)	C3C—C2C—C1C	119.4 (4)
C4A—C3A—C2A	119.9 (4)	C2C—C3C—C4C	119.5 (4)
C4A—C3A—H3A	120.1	C2C—C3C—H3C	120.3
C2A—C3A—H3A	120.1	C4C—C3C—H3C	120.3
C3A—C4A—C5A	120.9 (4)	C3C—C4C—C5C	121.3 (5)
C3A—C4A—H4A	119.6	C3C—C4C—H4C	119.4
C5A—C4A—H4A	119.6	C5C—C4C—H4C	119.4
C6A—C5A—C4A	118.9 (4)	C6C—C5C—C4C	119.2 (4)
C6A—C5A—H5A	120.6	C6C—C5C—H5C	120.4
C4A—C5A—H5A	120.6	C4C—C5C—H5C	120.4
C5A—C6A—C1A	120.4 (4)	C1C—C6C—C5C	120.2 (4)
C5A—C6A—H6A	119.8	C1C—C6C—H6C	119.9
C1A—C6A—H6A	119.8	C5C—C6C—H6C	119.9
C2A—O2A—C21A	119.4 (3)	C2C—O2C—C21C	116.6 (3)
C26A—C21A—C22A	121.8 (4)	C22C—C21C—C26C	121.7 (4)
C26A—C21A—O2A	116.3 (4)	C22C—C21C—O2C	119.6 (4)
C22A—C21A—O2A	121.9 (4)	C26C—C21C—O2C	118.6 (4)
C23A—C22A—C21A	118.4 (5)	C21C—C22C—C23C	118.9 (4)
C23A—C22A—H22A	120.8	C21C—C22C—H22C	120.5
C21A—C22A—H22A	120.8	C23C—C22C—H22C	120.5
C22A—C23A—C24A	120.5 (5)	C24C—C23C—C22C	120.3 (5)
C22A—C23A—H23A	119.8	C24C—C23C—H23C	119.9
C24A—C23A—H23A	119.8	C22C—C23C—H23C	119.9
C25A—C24A—C23A	119.5 (4)	C23C—C24C—C25C	119.6 (4)
C25A—C24A—H24A	120.3	C23C—C24C—H24C	120.2
C23A—C24A—H24A	120.3	C25C—C24C—H24C	120.2
C24A—C25A—C26A	120.6 (5)	C26C—C25C—C24C	120.7 (4)
C24A—C25A—H25A	119.7	C26C—C25C—H25C	119.7
C26A—C25A—H25A	119.7	C24C—C25C—H25C	119.7
C21A—C26A—C25A	119.3 (4)	C25C—C26C—C21C	118.8 (5)
C21A—C26A—H26A	120.4	C25C—C26C—H26C	120.6
C25A—C26A—H26A	120.4	C21C—C26C—H26C	120.6
O12B—S1B—O11B	118.08 (18)	O12D—S1D—O11D	117.78 (19)
O12B—S1B—N1B	107.42 (19)	O12D—S1D—N1D	107.15 (19)
O11B—S1B—N1B	107.34 (19)	O11D—S1D—N1D	107.19 (18)
O12B—S1B—C1B	108.86 (18)	O12D—S1D—C1D	109.24 (19)
O11B—S1B—C1B	106.42 (18)	O11D—S1D—C1D	106.64 (18)
N1B—S1B—C1B	108.40 (19)	N1D—S1D—C1D	108.56 (19)
S1B—N1B—H11B	104.8	S1D—N1D—H11D	106.3
S1B—N1B—H12B	104.2	S1D—N1D—H12D	100.4
H11B—N1B—H12B	106.7	H11D—N1D—H12D	114.3
C6B—C1B—C2B	120.4 (4)	C6D—C1D—C2D	120.0 (4)
C6B—C1B—S1B	119.4 (3)	C6D—C1D—S1D	119.6 (3)
C2B—C1B—S1B	120.1 (3)	C2D—C1D—S1D	120.4 (3)
O2B—C2B—C3B	122.1 (4)	O2D—C2D—C3D	122.7 (4)
O2B—C2B—C1B	118.2 (4)	O2D—C2D—C1D	117.6 (4)
C3B—C2B—C1B	119.6 (4)	C3D—C2D—C1D	119.6 (4)
C2B—C3B—C4B	119.7 (4)	C2D—C3D—C4D	119.5 (4)
C2B—C3B—H3B	120.1	C2D—C3D—H3D	120.2
C4B—C3B—H3B	120.1	C4D—C3D—H3D	120.2
C5B—C4B—C3B	120.5 (4)	C5D—C4D—C3D	121.4 (4)
C5B—C4B—H4B	119.7	C5D—C4D—H4D	119.3
C3B—C4B—H4B	119.7	C3D—C4D—H4D	119.3
C6B—C5B—C4B	120.2 (4)	C4D—C5D—C6D	119.6 (4)
C6B—C5B—H5B	119.9	C4D—C5D—H5D	120.2
C4B—C5B—H5B	119.9	C6D—C5D—H5D	120.2
C5B—C6B—C1B	119.5 (4)	C5D—C6D—C1D	119.8 (4)
C5B—C6B—H6B	120.3	C5D—C6D—H6D	120.1
C1B—C6B—H6B	120.3	C1D—C6D—H6D	120.1
C2B—O2B—C21B	114.7 (3)	C2D—O2D—C21D	118.2 (3)
C26B—C21B—C22B	121.5 (4)	C22D—C21D—C26D	121.3 (4)
C26B—C21B—O2B	118.9 (4)	C22D—C21D—O2D	123.0 (4)
C22B—C21B—O2B	119.6 (4)	C26D—C21D—O2D	115.5 (4)
C21B—C22B—C23B	118.8 (4)	C21D—C22D—C23D	119.2 (4)
C21B—C22B—H22B	120.6	C21D—C22D—H22D	120.4
C23B—C22B—H22B	120.6	C23D—C22D—H22D	120.4
C24B—C23B—C22B	120.3 (4)	C22D—C23D—C24D	120.3 (5)
C24B—C23B—H23B	119.8	C22D—C23D—H23D	119.9
C22B—C23B—H23B	119.8	C24D—C23D—H23D	119.9
C23B—C24B—C25B	120.0 (4)	C25D—C24D—C23D	119.9 (4)
C23B—C24B—H24B	120.0	C25D—C24D—H24D	120.1
C25B—C24B—H24B	120.0	C23D—C24D—H24D	120.1
C26B—C25B—C24B	119.7 (5)	C26D—C25D—C24D	120.0 (4)
C26B—C25B—H25B	120.1	C26D—C25D—H25D	120.0
C24B—C25B—H25B	120.1	C24D—C25D—H25D	120.0
C21B—C26B—C25B	119.7 (4)	C25D—C26D—C21D	119.3 (4)
C21B—C26B—H26B	120.1	C25D—C26D—H26D	120.4
C25B—C26B—H26B	120.1	C21D—C26D—H26D	120.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H12A···O2A	0.88	2.33	2.897 (5)	122
N1B—H12B···O2B	0.88	2.19	2.894 (4)	137
N1C—H12C···O2C	0.88	2.37	2.871 (4)	117
N1D—H12D···O2D	0.88	2.20	2.915 (4)	138
N1A—H11A···O11B	0.88	2.13	2.950 (4)	156
N1B—H11B···O11Aⁱ	0.88	2.08	2.945 (4)	165
N1C—H11C···O11D	0.88	2.14	2.947 (4)	153
N1D—H11D···O11Cⁱ	0.88	2.07	2.931 (4)	165
C25B—H25B···O12Bⁱⁱ	0.95	2.47	3.371 (6)	157
C25C—H25C···O12Cⁱⁱⁱ	0.95	2.42	3.320 (6)	158
C26A—H26A···O12Aⁱ	0.95	2.52	3.410 (5)	156
C26D—H26D···O12Dⁱ	0.95	2.46	3.378 (5)	161

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+2.

(II) N-methyl-2-phenoxybenzenesulfonamide top

Crystal data top

C₁₃H₁₃NO₃S	F(000) = 276
M_r = 263.30	D_x = 1.413 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2703 reflections
a = 5.3804 (2) Å	θ = 2.9–27.5°
b = 7.9959 (4) Å	µ = 0.26 mm⁻¹
c = 14.4462 (7) Å	T = 120 K
β = 95.226 (2)°	Block, colourless
V = 618.91 (5) Å³	0.22 × 0.10 × 0.08 mm
Z = 2

Data collection top

Nonius KappaCCD area-detector diffractometer	2703 independent reflections
Radiation source: rotating anode	2548 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.116
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −6→6
T_min = 0.951, T_max = 0.979	k = −10→10
7538 measured reflections	l = −18→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.062P)² + 0.5323P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2703 reflections	Δρ_max = 0.21 e Å⁻³
164 parameters	Δρ_min = −0.48 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1188 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.20 (11)

Crystal data top

C₁₃H₁₃NO₃S	V = 618.91 (5) Å³
M_r = 263.30	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.3804 (2) Å	µ = 0.26 mm⁻¹
b = 7.9959 (4) Å	T = 120 K
c = 14.4462 (7) Å	0.22 × 0.10 × 0.08 mm
β = 95.226 (2)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2703 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	2548 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.979	R_int = 0.116
7538 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.145	Δρ_max = 0.21 e Å⁻³
S = 1.05	Δρ_min = −0.48 e Å⁻³
2703 reflections	Absolute structure: Flack (1983), 1188 Friedel pairs
164 parameters	Absolute structure parameter: 0.20 (11)
1 restraint

Special details top

Experimental. ?.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.06643 (12)	0.66270 (9)	0.88106 (5)	0.0193 (2)
O2	0.4366 (4)	0.7311 (3)	0.74276 (14)	0.0216 (5)
O11	−0.1415 (4)	0.6849 (3)	0.93551 (15)	0.0265 (5)
O12	0.0746 (5)	0.5187 (3)	0.82236 (17)	0.0267 (5)
N1	0.3168 (4)	0.6586 (4)	0.95212 (16)	0.0201 (5)
C1	0.0851 (6)	0.8451 (4)	0.8135 (2)	0.0201 (6)
C2	0.2691 (5)	0.8611 (4)	0.7510 (2)	0.0192 (6)
C3	0.2937 (6)	1.0089 (4)	0.7025 (2)	0.0234 (6)
C4	0.1366 (6)	1.1431 (4)	0.7163 (2)	0.0255 (6)
C5	−0.0479 (6)	1.1285 (4)	0.7776 (2)	0.0257 (7)
C6	−0.0715 (6)	0.9809 (4)	0.8265 (2)	0.0231 (6)
C11	0.3562 (6)	0.7982 (5)	1.0182 (2)	0.0287 (7)
C21	0.3989 (5)	0.6245 (3)	0.6670 (2)	0.0187 (6)
C22	0.1886 (6)	0.6314 (4)	0.6029 (2)	0.0230 (7)
C23	0.1702 (6)	0.5181 (4)	0.5290 (2)	0.0254 (7)
C24	0.3555 (6)	0.4008 (4)	0.5197 (2)	0.0272 (7)
C25	0.5635 (6)	0.3962 (4)	0.5845 (2)	0.0268 (7)
C26	0.5858 (6)	0.5074 (4)	0.6584 (2)	0.0231 (6)
H1	0.4508	0.6401	0.9229	0.024*
H11A	0.3841	0.9015	0.9841	0.043*
H11B	0.5022	0.7749	1.0619	0.043*
H11C	0.2085	0.8112	1.0525	0.043*
H3	0.4174	1.0185	0.6599	0.028*
H4	0.1551	1.2450	0.6839	0.031*
H5	−0.1572	1.2195	0.7858	0.031*
H6	−0.1951	0.9721	0.8692	0.028*
H22	0.0608	0.7114	0.6095	0.028*
H23	0.0288	0.5216	0.4845	0.030*
H24	0.3409	0.3239	0.4694	0.033*
H25	0.6912	0.3162	0.5780	0.032*
H26	0.7275	0.5036	0.7027	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0177 (3)	0.0157 (3)	0.0243 (3)	−0.0019 (3)	0.0015 (2)	0.0018 (3)
O2	0.0201 (10)	0.0217 (10)	0.0226 (10)	0.0034 (8)	−0.0008 (8)	−0.0045 (9)
O11	0.0176 (10)	0.0281 (13)	0.0346 (11)	−0.0010 (9)	0.0073 (8)	0.0084 (10)
O12	0.0340 (13)	0.0166 (11)	0.0287 (12)	−0.0044 (9)	−0.0010 (10)	0.0006 (10)
N1	0.0167 (11)	0.0196 (11)	0.0238 (11)	0.0007 (12)	0.0013 (8)	−0.0008 (12)
C1	0.0208 (15)	0.0179 (14)	0.0214 (14)	0.0003 (12)	0.0003 (11)	0.0002 (11)
C2	0.0178 (14)	0.0177 (13)	0.0220 (14)	0.0008 (11)	0.0007 (11)	−0.0014 (12)
C3	0.0231 (15)	0.0249 (16)	0.0227 (14)	−0.0030 (12)	0.0040 (11)	−0.0007 (13)
C4	0.0331 (16)	0.0184 (15)	0.0249 (13)	−0.0021 (13)	0.0024 (11)	0.0027 (13)
C5	0.0294 (16)	0.0212 (17)	0.0271 (15)	0.0054 (11)	0.0055 (12)	0.0006 (12)
C6	0.0218 (15)	0.0208 (14)	0.0273 (16)	0.0024 (12)	0.0052 (12)	0.0020 (12)
C11	0.0332 (18)	0.0267 (16)	0.0263 (16)	−0.0032 (14)	0.0028 (13)	−0.0058 (14)
C21	0.0202 (14)	0.0186 (16)	0.0179 (13)	−0.0020 (10)	0.0059 (10)	0.0002 (10)
C22	0.0216 (14)	0.0246 (17)	0.0225 (14)	0.0012 (11)	0.0007 (10)	0.0006 (12)
C23	0.0269 (16)	0.0272 (16)	0.0217 (14)	−0.0032 (13)	0.0011 (12)	0.0010 (13)
C24	0.0320 (18)	0.0292 (17)	0.0216 (15)	−0.0076 (13)	0.0085 (13)	−0.0065 (13)
C25	0.0242 (17)	0.0260 (16)	0.0314 (17)	0.0007 (12)	0.0090 (13)	−0.0035 (13)
C26	0.0193 (14)	0.0237 (15)	0.0265 (15)	−0.0001 (11)	0.0035 (11)	−0.0035 (13)

Geometric parameters (Å, º) top

S1—O12	1.433 (2)	C4—H4	0.95
S1—O11	1.436 (2)	C5—C6	1.388 (4)
S1—N1	1.618 (2)	C5—H5	0.95
S1—C1	1.763 (3)	C6—H6	0.95
N1—C11	1.471 (4)	O2—C21	1.388 (3)
N1—H1	0.8802	C21—C26	1.387 (4)
C11—H11A	0.98	C21—C22	1.396 (4)
C11—H11B	0.98	C22—C23	1.397 (4)
C11—H11C	0.98	C22—H22	0.95
C1—C6	1.398 (4)	C23—C24	1.384 (5)
C1—C2	1.405 (4)	C23—H23	0.95
C2—C3	1.386 (4)	C24—C25	1.393 (5)
C2—O2	1.388 (4)	C24—H24	0.95
C3—C4	1.392 (5)	C25—C26	1.386 (4)
C3—H3	0.95	C25—H25	0.95
C4—C5	1.393 (4)	C26—H26	0.95

O12—S1—O11	119.40 (15)	C5—C4—H4	119.9
O12—S1—N1	106.87 (15)	C6—C5—C4	119.9 (3)
O11—S1—N1	107.47 (13)	C6—C5—H5	120.1
O12—S1—C1	109.30 (13)	C4—C5—H5	120.1
O11—S1—C1	106.73 (14)	C5—C6—C1	120.5 (3)
N1—S1—C1	106.38 (15)	C5—C6—H6	119.7
C11—N1—S1	117.3 (2)	C1—C6—H6	119.7
C11—N1—H1	111.2	C21—O2—C2	118.6 (2)
S1—N1—H1	111.7	C26—C21—O2	115.5 (3)
N1—C11—H11A	109.5	C26—C21—C22	121.2 (3)
N1—C11—H11B	109.5	O2—C21—C22	123.4 (3)
H11A—C11—H11B	109.5	C21—C22—C23	118.5 (3)
N1—C11—H11C	109.5	C21—C22—H22	120.7
H11A—C11—H11C	109.5	C23—C22—H22	120.7
H11B—C11—H11C	109.5	C24—C23—C22	120.8 (3)
C6—C1—C2	119.0 (3)	C24—C23—H23	119.6
C6—C1—S1	120.2 (2)	C22—C23—H23	119.6
C2—C1—S1	120.7 (2)	C23—C24—C25	119.6 (3)
C3—C2—O2	120.1 (3)	C23—C24—H24	120.2
C3—C2—C1	120.6 (3)	C25—C24—H24	120.2
O2—C2—C1	119.2 (3)	C26—C25—C24	120.6 (3)
C2—C3—C4	119.8 (3)	C26—C25—H25	119.7
C2—C3—H3	120.1	C24—C25—H25	119.7
C4—C3—H3	120.1	C25—C26—C21	119.3 (3)
C3—C4—C5	120.3 (3)	C25—C26—H26	120.4
C3—C4—H4	119.9	C21—C26—H26	120.4

O12—S1—N1—C11	178.0 (2)	C3—C4—C5—C6	1.4 (5)
O11—S1—N1—C11	−52.7 (3)	C4—C5—C6—C1	−1.3 (5)
C1—S1—N1—C11	61.3 (3)	C2—C1—C6—C5	0.8 (5)
O12—S1—C1—C6	136.2 (3)	S1—C1—C6—C5	176.1 (3)
O11—S1—C1—C6	5.8 (3)	C3—C2—O2—C21	−82.3 (3)
N1—S1—C1—C6	−108.7 (3)	C1—C2—O2—C21	101.8 (3)
O12—S1—C1—C2	−48.6 (3)	C2—O2—C21—C26	174.1 (3)
O11—S1—C1—C2	−179.0 (2)	C2—O2—C21—C22	−6.1 (4)
N1—S1—C1—C2	66.5 (3)	C26—C21—C22—C23	−0.4 (4)
C6—C1—C2—C3	−0.5 (4)	O2—C21—C22—C23	179.8 (3)
S1—C1—C2—C3	−175.8 (2)	C21—C22—C23—C24	0.4 (5)
C6—C1—C2—O2	175.4 (3)	C22—C23—C24—C25	−0.4 (5)
S1—C1—C2—O2	0.2 (4)	C23—C24—C25—C26	0.3 (5)
O2—C2—C3—C4	−175.3 (3)	C24—C25—C26—C21	−0.3 (5)
C1—C2—C3—C4	0.6 (5)	O2—C21—C26—C25	−179.8 (3)
C2—C3—C4—C5	−1.1 (5)	C22—C21—C26—C25	0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O11ⁱ	0.88	2.21	2.953 (3)	141
C26—H26···O12ⁱ	0.95	2.43	3.377 (4)	174
C4—H4···Cg1ⁱⁱ	0.95	2.83	3.741 (3)	161

Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.

Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₂H₁₁NO₃S	C₁₃H₁₃NO₃S
M_r	249.28	263.30
Crystal system, space group	Triclinic, P1	Monoclinic, P2₁
Temperature (K)	120	120
a, b, c (Å)	5.2539 (2), 16.2090 (8), 26.5417 (9)	5.3804 (2), 7.9959 (4), 14.4462 (7)
α, β, γ (°)	84.850 (2), 88.951 (2), 87.607 (2)	90, 95.226 (2), 90
V (Å³)	2248.98 (16)	618.91 (5)
Z	8	2
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.28	0.26
Crystal size (mm)	0.22 × 0.16 × 0.12	0.22 × 0.10 × 0.08

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995, 1997)	Multi-scan (SORTAV; Blessing, 1995, 1997)
T_min, T_max	0.926, 0.967	0.951, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	22883, 9651, 4912	7538, 2703, 2548
R_int	0.071	0.116
(sin θ/λ)_max (Å⁻¹)	0.647	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.203, 1.05	0.055, 0.145, 1.05
No. of reflections	9651	2703
No. of parameters	614	164
No. of restraints	0	1
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.64	0.21, −0.48
Absolute structure	?	Flack (1983), 1188 Friedel pairs
Absolute structure parameter	?	0.20 (11)

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) for (I) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H12A···O2A	0.88	2.33	2.897 (5)	122
N1B—H12B···O2B	0.88	2.19	2.894 (4)	137
N1C—H12C···O2C	0.88	2.37	2.871 (4)	117
N1D—H12D···O2D	0.88	2.20	2.915 (4)	138
N1A—H11A···O11B	0.88	2.13	2.950 (4)	156
N1B—H11B···O11Aⁱ	0.88	2.08	2.945 (4)	165
N1C—H11C···O11D	0.88	2.14	2.947 (4)	153
N1D—H11D···O11Cⁱ	0.88	2.07	2.931 (4)	165
C25B—H25B···O12Bⁱⁱ	0.95	2.47	3.371 (6)	157
C25C—H25C···O12Cⁱⁱⁱ	0.95	2.42	3.320 (6)	158
C26A—H26A···O12Aⁱ	0.95	2.52	3.410 (5)	156
C26D—H26D···O12Dⁱ	0.95	2.46	3.378 (5)	161

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+2.

Selected torsion angles (°) for (I) and (II) top

Parameter	(I, n = A)	(I, n = B)	(I, n = C)	(I, n = D)	(II, n = nil)
C21n-O2n-C2n-C1n	132.0 (4)	-130.1 (4)	132.5 (4)	-130.6 (4)	101.8 (3)
C2n-O2n-C21n-C22n	-26.3 (6)	-98.4 (5)	96.5 (5)	23.7 (6)	-6.1 (4)
C2n-C1n-S1n-N1n	51.5 (4)	-50.2 (4)	50.4 (4)	-50.6 (4)	66.5 (3)
C2n-C1n-S1n-O11n	166.2 (3)	-165.4 (3)	165.4 (3)	-165.8 (3)	-179.0 (2)
C2n-C1n-S1n-O12n	-66.1 (4)	66.3 (4)	-67.0 (4)	66.0 (4)	-48.6 (3)
C1-S1-N1-C11					61.3 (2)

Hydrogen-bond geometry (Å, º) for (II) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O11ⁱ	0.88	2.21	2.953 (3)	141
C26—H26···O12ⁱ	0.95	2.43	3.377 (4)	174
C4—H4···Cg1ⁱⁱ	0.95	2.83	3.741 (3)	161

Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff for all their help and advice. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work. JLW thanks CNPq and FAPERJ for financial support.

References

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Volume 60| Part 5| May 2004| Pages o364-o367

doi:10.1107/S010827010400719X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Monoclinic pseudosymmetry in 2-phen­oxy­benzene­sulfon­amide, a triclinic structure having Z′ = 4, and spontaneous resolution in monoclinic N-methyl-2-phen­oxy­benzene­sulfon­amide

Comment

Experimental

Compound (I)

Crystal data

Data collection

Refinement

Compound (II)

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Monoclinic pseudosymmetry in 2-phenoxybenzenesulfonamide, a triclinic structure having Z′ = 4, and spontaneous resolution in monoclinic N-methyl-2-phenoxybenzenesulfonamide