Positional isomeric effect on the crystallization of chlorine-substituted N-phenyl-2-phthalimido­ethane­sulfonamide derivatives

The ortho-, para- and meta-chloro-substituted N-chloro­phenyl-2-phthalimido­ethane­sulfonamide derivatives, C₁₆H₁₃ClN₂O₄S, have been structurally characterized by single-crystal X-ray crystallography. N-(2-Chloro­phenyl)-2-phthalimido­ethane­sulfonamide, (I), has ortho­rhom­bic (P2₁2₁2₁) symmetry, N-(4-chloro­phenyl)-2-phthalimido­ethane­sulfonamide, (II), has triclinic (P) symmetry and N-(3-chloro­phenyl)-2-phthalimido­ethane­sulfonamide, (III), has monoclinic (P2₁/c) symmetry. The mol­ecules of (I)–(III) are regioisomers which have crystallized in different space groups as a result of the differing intra- and inter­molecular hydrogen-bond inter­actions which are present in each structure. Compounds (I) and (II) are stabilized by N—H...O and C—H...O hydrogen bonds, while (III) is stabilized by N—H...O, C—H...O and C—H...Cl hydrogen-bond inter­actions. The structure of (II) also displays π–π stacking inter­actions between the isoindole and benzene rings. All three structures are of inter­est with respect to their biological activities and have been studied as part of a programme to develop anti­convulsant drugs for the treatment of epilepsy.

S1. Introduction

In the chemical, biological and material sciences, isomers exhibit a variety of properties (Zhang et al., 2009). For instance, although positional isomers display similar functionalities (Park et al., 2005), stereoisomers of pharmaceutical compounds can exhibit profoundly different biological activities (Wermuth et al., 1997; Rebek, 2005), while for molecule-based functional materials, the bulk properties are not only related to a single molecular property but are also influenced to a large extent by inter­molecular inter­actions. Changes in the position of substituent groups can significantly alter the molecular configurations and crystal structures of the isomers (Fan & Yan, 2014). A slight difference in molecular structure can lead to a profound impact on crystal packing.

Various substituted N-phenyl phthalimide derivatives have shown potential anti­convulsant activity (Yadav et al., 2012). Taurine is known to have anti-epileptic activity, but as yet this has not been applied in the clinical setting (Gupta et al., 2005). 2-Phthalimido-N-substituted-phenyl­ethane­sulfonamides have been designed as potent anti­convulsant compounds and evaluated for anti­convulsant activity in animal experiments. Anti­convulsant activity has been shown to be sensitive to the position of the chlorine substituents. Thus, the ortho-chloro substituted isomer (I) is more active than (II) and (III) (Akgul et al., 2007). The para-substituted isomer (II) can be used as a disposable electrochemical biosensor and redox indicator; it reduces guanine base oxidation and can cause mutation (Ozkan-Ariksoysal et al., 2010).

We now report the structures of these three positional isomers of N-chloro­phenyl-2-phthalimido­ethane­sulfonamide derivatives, namely N-(2-chloro­phenyl)-2-phthalimido­ethane­sulfonamide, (I), N-(4-chloro­phenyl)-2-phthalimido­ethane­sulfonamide, (II), and N-(3-chloro­phenyl)-2-phthalimido­ethane­sulfonamide, (III) (see scheme). The purpose of this study is to determine the impact of the chlorine position on the inter­molecular inter­actions and ultimately on the crystal packing.

S2. Experimental

S2.1. Synthesis and crystallization

Synthesis and crystallization processes were reported in a previous study (Akgul et al., 2007).

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. For all three structures, H atoms were refined freely, giving C—H = 0.90 (4)–0.98 (3) Å and N—H = 0.83 (3) Å. [Please check added details and correct as necessary]

S3. Results and discussion

In the molecule of (I) (Fig. 1) there are two C—H···O and N—H···O type intra­molecular inter­actions (Table 2), which generate S(6) and S(8) motifs (Bernstein et al., 1995), respectively. There are also two types of inter­molecular inter­action. A polymeric chain along the b axis is generated by C7—H7A···O4^i_I inter­molecular inter­actions with graph set C(6), while C7—H7B···O2^ii_I inter­molecular inter­actions form a second polymeric chain, with graph set C(4), extending along the a axis [symmetry codes: (i_I) 1 - x, -1/2 + y, 1/2 - z; (ii_I) -1 + x, y, z]. Considering these two inter­actions together, they form a two-dimensional polymeric sheet parallel to the ab plane. In this plane, two graph sets, R₄⁴(18) and R₅⁴(18), can be defined, as shown in Fig 2.

In the molecule of (II) (Fig. 3), although there no significant intra­molecular inter­actions are observed, there do exist N—H···O, C—H···O and π–π type inter­molecular inter­actions (Table 3). The N1–H1···O2^i_II inter­action forms a centrosymmetric dimer between the molecules with fractional coordinates (x, y, z) and (-x, 1 - y, -z), forming an R₂²(8) motif [symmetry code: (i_II) -x, 1 - y, -z]. In addition to this hydrogen bond, the dimer is stabilised by π–π inter­actions between the C1–C6 benzene ring and the C10–C15 ring, with a centroid-to-centroid distance of 3.8723 (18) Å. Finally, there is a C4—H4···O4^ii_II inter­action, which results in the formation of a one-dimensional polymeric chain extending along the b axis with a C(11) motif [symmetry code: (ii_II) x, -1 + y, z]. Considering this chain and the dimeric inter­action generated by the N1—H1···O2^i_II and π–π inter­actions, a one-dimensional bi-chain is formed along the b axis (Fig. 4).

In the molecule of (III) (Fig. 5) there is an intra­molecular C5—H5···O1 hydrogen bond which gives rise to an S(6) motif (Table 4). In addition, the C11—H11···O3^i_III inter­action forms a dimeric structure, which can be described as an R₂²(12) motif, with the inversion-related molecule [symmetry code: (i_III) 1 - x, -y, -z]. The N1—H1···O4^ii_III inter­molecular inter­action gives rise to a one-dimensional polymeric chain, described as a C(8) motif, extending along the a axis (Fig. 6) [symmetry code: (ii_III) 1 + x, y, z]. Considering this C(8) chain and the dimeric inter­action together, they generate a two-dimensional sheet parallel to the (031) plane. Providing further stabilisation to the C(8) chain is a C2—H2···Cl1^iii_III inter­action, which generates a one-dimensional polymeric chain described as a C(5) motif extending along the a axis (Fig. 7) [symmetry code: (iii_III) 1 + x, 1/2 - y, 1/2 + z]. Considering this C(5) chain and the dimeric inter­action together, they form a two-dimensional sheet perpendicular to the b axis. Finally, considering these three inter­actions together, all molecules in the structure of (III) are connected to each other via C—H···O, N—H···O and C—H···Cl type inter­molecular inter­actions.

Intra- and inter­molecular hydrogen bonds play an important role in molecular and crystal structural conformations. To investigate the conformational differences of the three title compounds, the torsion angles around the C7—C8 and S1—C7 bonds were compared (Tables 5–7). The conformations about the S1—C7 bond for (I), (II) and (III) are -sc (-synclinal), +ap (+anti­periplanar) and -sc, respectively. The conformations about the C7—C8 bond for (I), (II) and (III) are -sc, -sc and +sc, respectively. Considering the intra­molecular inter­actions, (I) has an N—H···O type inter­action which folds the molecule into an -sc, -sc conformation.

The conformational differences between the three isomers is highlighted by comparison of the T1 (N1—S1—C7—C8) and T2 (S1—C7—C8—N2) torsion angles. Comparing the conformations of (I) and (II), the T2 angles are similar (-62.7 and -70.9°, respectively), but the T1 angles give rise to the difference, with values of -52.0 and -176.8°, respectively. Comparing (I) and (III), the T1 angles are similar (-52.0 and -70.2°, respectively) but the T2 angles lead to the difference, with values of -62.7 and +64.7°, respectively. In summary, the T1 dihedral angle is responsible for the difference between (I) and (II) and between (II) and (III), while the T2 angle is responsible for the difference between (I) and (III) and between (II) and (III). The bond distances and angles of the flexible linkage between the aromatic systems do not differ significantly between (I), (II) and (III), despite the differing conformations of these linkers.

The molecular structures of the three title compounds consist of two planar/aromatic rings, which are benzene and iso­indole rings. The dihedral angles between the mean planes of these rings for (I), (II) and (III) are 62.7 (1), 12.50 (9) and 8.25 (7)°, respectively.

Positional isomerization not only affects topology and packing differences, but also affects the physicochemical (Liao et al., 2010), kinetic and thermodynamic (Dhalluin et al., 2005) properties and the pharmaceutical activities of compounds (Banba et al., 2013). Considering the drug activity of the title compounds (Akgul et al., 2007), (I) was found to be more active than the others, while (II) and (III) show equal and weak activity compared with (I). In addition, the toxicity of aromatic compounds is higher than that of non-aromatics (Pramanik & Roy, 2014). Although (I) does not show any neurotoxic effect, (II) and (III) do show neurotoxicity.

To compare the efficiency of the title compounds as potential anti­convulsant drugs, their aromaticities were calculated and compared. Hypotetically, because of electron delocalization, the ortho- and para-positions of nitro-substituted benzene are partially negative charged. When an electron-withdrawing group (chlorine) is attached in the para- or ortho-postion, the aromticity of benzene decreases. To compare the aromaticities of these benzene rings, highest occupied molecular orbital (HOMA; Krygowski, 1993) aromaticity indices were calculated. Comparing the HOMA values of these compounds, the obtained values are 0.919, 0.930 and 0.948 for (I), (II) and (III), respectively. Thus, (I) is slightly less aromatic than (II) and (III), and so is a more suitable candidate for anti­convulsant drugs.

Although the main difference between the three title compounds is simply the position of the chlorine substituent, the resulting crystal systems and space groups are different from each other. Compound (I) crystallizes in a noncentrosymmetric chiral orthorhombic space group, while (II) and (III) crystallize in centrosymmetric triclinic and monoclinic space groups. In brief, positional isomerization plays an important role in the packing and structural conformation of the studied compounds.

Related literature

For related literature, see: Ozkan-Ariksoysal et al. (2010); Bernstein et al. (1995); Fan & Yan (2014); Gupta et al. (2005); Park et al. (2005); Rebek (2005); Wermuth et al. (1997); Yadav et al. (2012); Zhang et al. (2009).

Computing details

For all compounds, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. Intramolecular interactions are shown as dotted lines.
	Fig. 2. The crystal structure of (I), viewed along the c axis. Intra- and intermolecular hydrogen bonds are shown as dotted lines. The bond path which generates the graph-set motif is shown in a ball-and-stick drawing style and the other atoms are shown in a wireframe drawing style. For clarity, H atoms which do not play a role in the hydrogen bonding have been omitted. The generated graph-set motif can be represented in two forms, shown on the right-hand side as R5^4(18) and on the left-hand side as R4^4(18).
	Fig. 3. The molecular structure of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 4. The intermolecular intreractions of structure (II), showing the bi-chain constructed by one-dimensional chain and dimeric interactions (dotted lines). The graph set-notations, as shown in the figure, are R2^2(8) and R4^4(26).
	Fig. 5. The molecular structure of (III), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular interaction is shown as a dotted line.
	Fig. 6. The intermolecular interactions of structure (III) (dotted lines), including N—H···O type interactions. Considering the dimeric interaction with this type of interaction, they construct a two-dimensional sheet parallel to the (031) plane. The graph-set notations, as shown in the figure, are R2^2(10) and R4^4(30).
	Fig. 7. The intermolecular interactions of structure (III) (dotted lines), including C—H···Cl type interactions. Considering the dimeric interaction with this type of interaction, they construct a two-dimensional sheet parallel to the (102) plane. The graph-set notations, as shown in the figure, are R2^2(10) and R6^6(58).

(I) N-(2-chlorophenyl)-2-phthalimidoethanesulfonamide

Crystal data

C16H13ClN2O4S	Dx = 1.546 Mg m^−3
Mr = 364.79	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1162 reflections
a = 5.4126 (2) Å	θ = 3.9–24.3°
b = 12.7656 (5) Å	µ = 0.40 mm^−1
c = 22.6827 (8) Å	T = 293 K
V = 1567.26 (11) Å^3	Needle, colourless
Z = 4	0.35 × 0.07 × 0.05 mm
F(000) = 752

Data collection

Agilent Xcalibur Eos diffractometer	2894 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2484 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 16.1333 pixels mm^-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −5→6
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014)	k = −9→15
Tmin = 0.989, Tmax = 0.998	l = −28→28
4676 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0353P)^2 + 0.1242P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.082	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.22 e Å^−3
2894 reflections	Δρmin = −0.29 e Å^−3
269 parameters	Absolute structure: Flack x parameter determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.02 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.1528 (2)	0.56965 (9)	0.18287 (5)	0.0680 (4)
S1	0.55647 (15)	0.26803 (7)	0.19537 (4)	0.0370 (2)
O1	0.5602 (5)	0.1892 (2)	0.15096 (11)	0.0553 (7)
O2	0.7807 (4)	0.2950 (2)	0.22485 (11)	0.0506 (7)
O3	0.4455 (5)	0.2256 (2)	0.40447 (10)	0.0553 (7)
O4	0.5984 (6)	0.49229 (19)	0.27603 (11)	0.0546 (8)
N1	0.4553 (6)	0.3769 (2)	0.16682 (13)	0.0393 (7)
N2	0.4780 (5)	0.3494 (2)	0.33100 (11)	0.0339 (6)
C1	0.1054 (7)	0.4755 (3)	0.12845 (15)	0.0407 (8)
C2	−0.0807 (8)	0.4903 (4)	0.0879 (2)	0.0573 (11)
C3	−0.1259 (9)	0.4152 (4)	0.0464 (2)	0.0661 (14)
C4	0.0144 (9)	0.3270 (4)	0.04528 (19)	0.0670 (14)
C5	0.2043 (8)	0.3126 (4)	0.08425 (17)	0.0541 (11)
C6	0.2538 (6)	0.3869 (3)	0.12702 (14)	0.0372 (8)
C7	0.3380 (7)	0.2312 (3)	0.24945 (15)	0.0338 (7)
C8	0.2735 (6)	0.3148 (3)	0.29420 (15)	0.0360 (8)
C9	0.5444 (7)	0.3021 (3)	0.38401 (14)	0.0374 (8)
C10	0.7535 (6)	0.3651 (3)	0.40753 (14)	0.0354 (8)
C11	0.8922 (8)	0.3531 (3)	0.45783 (16)	0.0490 (10)
C12	1.0798 (8)	0.4249 (4)	0.46783 (17)	0.0527 (11)
C13	1.1236 (8)	0.5051 (4)	0.42894 (19)	0.0522 (11)
C14	0.9833 (7)	0.5175 (3)	0.37819 (17)	0.0466 (10)
C15	0.7968 (6)	0.4469 (3)	0.36876 (14)	0.0354 (8)
C16	0.6205 (6)	0.4376 (3)	0.31878 (14)	0.0350 (8)
H8A	0.142 (5)	0.290 (2)	0.3206 (12)	0.024 (8)*
H7A	0.397 (6)	0.172 (3)	0.2652 (14)	0.039 (10)*
H14	1.007 (7)	0.574 (3)	0.3536 (16)	0.054 (12)*
H5	0.301 (7)	0.250 (3)	0.0823 (16)	0.047 (11)*
H1	0.480 (6)	0.429 (3)	0.1884 (14)	0.035 (10)*
H8B	0.206 (6)	0.379 (3)	0.2774 (14)	0.033 (9)*
H3	−0.238 (7)	0.428 (3)	0.0187 (18)	0.062 (13)*
H7B	0.202 (6)	0.211 (2)	0.2276 (14)	0.038 (10)*
H11	0.862 (7)	0.295 (3)	0.4814 (15)	0.046 (11)*
H13	1.238 (8)	0.554 (3)	0.4382 (17)	0.057 (12)*
H2	−0.165 (7)	0.546 (3)	0.0902 (16)	0.044 (12)*
H12	1.174 (7)	0.417 (3)	0.5054 (17)	0.062 (12)*
H4	−0.017 (8)	0.275 (4)	0.0182 (19)	0.074 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0714 (7)	0.0491 (6)	0.0834 (8)	0.0162 (6)	−0.0174 (6)	−0.0138 (6)
S1	0.0316 (4)	0.0414 (5)	0.0380 (4)	0.0095 (4)	−0.0001 (4)	−0.0008 (4)
O1	0.0665 (17)	0.0525 (17)	0.0468 (14)	0.0235 (15)	0.0072 (14)	−0.0098 (12)
O2	0.0267 (13)	0.067 (2)	0.0581 (16)	0.0053 (12)	−0.0039 (11)	0.0075 (14)
O3	0.0695 (18)	0.0529 (16)	0.0436 (14)	−0.0213 (16)	0.0029 (13)	0.0108 (13)
O4	0.083 (2)	0.0342 (15)	0.0469 (15)	−0.0101 (14)	−0.0184 (14)	0.0089 (12)
N1	0.0435 (17)	0.0360 (18)	0.0383 (15)	0.0020 (15)	−0.0063 (14)	0.0005 (14)
N2	0.0383 (16)	0.0328 (15)	0.0306 (13)	−0.0038 (13)	−0.0022 (12)	−0.0003 (12)
C1	0.037 (2)	0.044 (2)	0.0415 (19)	0.0017 (17)	0.0005 (16)	0.0076 (17)
C2	0.048 (3)	0.060 (3)	0.064 (3)	0.008 (3)	−0.006 (2)	0.016 (2)
C3	0.054 (3)	0.093 (4)	0.052 (3)	0.005 (3)	−0.019 (2)	0.010 (3)
C4	0.073 (3)	0.081 (4)	0.047 (2)	0.005 (3)	−0.019 (2)	−0.011 (2)
C5	0.059 (3)	0.061 (3)	0.042 (2)	0.016 (2)	−0.010 (2)	−0.008 (2)
C6	0.0316 (18)	0.049 (2)	0.0309 (16)	0.0009 (17)	0.0039 (14)	0.0048 (16)
C7	0.0302 (17)	0.0317 (19)	0.0396 (18)	0.0004 (17)	−0.0050 (15)	−0.0012 (17)
C8	0.0323 (18)	0.035 (2)	0.0412 (19)	0.0002 (16)	0.0013 (16)	−0.0032 (16)
C9	0.045 (2)	0.0363 (19)	0.0306 (16)	0.0012 (17)	0.0067 (16)	−0.0005 (15)
C10	0.0393 (19)	0.0348 (19)	0.0323 (16)	0.0024 (16)	0.0041 (15)	−0.0043 (15)
C11	0.059 (3)	0.052 (3)	0.0358 (19)	0.002 (2)	−0.0061 (18)	0.0011 (19)
C12	0.054 (3)	0.062 (3)	0.042 (2)	0.006 (2)	−0.014 (2)	−0.009 (2)
C13	0.046 (2)	0.056 (3)	0.055 (2)	−0.004 (2)	−0.0061 (19)	−0.019 (2)
C14	0.053 (2)	0.039 (2)	0.048 (2)	−0.0068 (19)	0.0028 (18)	−0.0052 (19)
C15	0.0373 (18)	0.0337 (19)	0.0353 (17)	−0.0010 (16)	0.0021 (15)	−0.0064 (15)
C16	0.042 (2)	0.0279 (17)	0.0350 (17)	−0.0016 (16)	−0.0004 (14)	−0.0011 (15)

Geometric parameters (Å, º)

Cl1—C1	1.742 (4)	C5—C6	1.383 (5)
S1—O1	1.424 (3)	C5—H5	0.96 (4)
S1—O2	1.428 (3)	C7—C8	1.514 (5)
S1—N1	1.629 (3)	C7—H7A	0.90 (4)
S1—C7	1.768 (4)	C7—H7B	0.92 (3)
O3—C9	1.207 (4)	C8—H8A	0.98 (3)
O4—C16	1.201 (4)	C8—H8B	0.97 (3)
N1—C6	1.421 (4)	C9—C10	1.487 (5)
N1—H1	0.83 (3)	C10—C11	1.374 (5)
N2—C8	1.455 (4)	C10—C15	1.385 (5)
N2—C9	1.392 (4)	C11—C12	1.386 (6)
N2—C16	1.393 (4)	C11—H11	0.93 (3)
C1—C2	1.378 (5)	C12—C13	1.372 (6)
C1—C6	1.388 (5)	C12—H12	1.00 (4)
C2—C3	1.365 (7)	C13—C14	1.388 (5)
C2—H2	0.85 (4)	C13—H13	0.90 (4)
C3—C4	1.359 (7)	C14—C15	1.370 (5)
C3—H3	0.89 (4)	C14—H14	0.93 (4)
C4—C5	1.368 (6)	C15—C16	1.487 (4)
C4—H4	0.92 (4)
O1—S1—O2	119.32 (15)	C8—C7—H7A	114 (2)
O1—S1—N1	109.09 (16)	C8—C7—H7B	112 (2)
O1—S1—C7	108.21 (17)	H7A—C7—H7B	105 (3)
O2—S1—N1	105.43 (16)	N2—C8—C7	115.0 (3)
O2—S1—C7	107.94 (16)	N2—C8—H8A	107.5 (16)
N1—S1—C7	106.13 (17)	N2—C8—H8B	105.0 (19)
S1—N1—H1	113 (2)	C7—C8—H8A	110.2 (17)
C6—N1—S1	125.9 (3)	C7—C8—H8B	114.5 (19)
C6—N1—H1	115 (2)	H8A—C8—H8B	104 (3)
C9—N2—C8	124.1 (3)	O3—C9—N2	124.6 (3)
C9—N2—C16	112.3 (3)	O3—C9—C10	129.6 (3)
C16—N2—C8	123.5 (3)	N2—C9—C10	105.8 (3)
C2—C1—Cl1	119.1 (3)	C11—C10—C9	130.8 (3)
C2—C1—C6	121.3 (4)	C11—C10—C15	121.2 (3)
C6—C1—Cl1	119.6 (3)	C15—C10—C9	108.0 (3)
C1—C2—H2	118 (3)	C10—C11—C12	117.5 (4)
C3—C2—C1	119.7 (4)	C10—C11—H11	118 (2)
C3—C2—H2	123 (3)	C12—C11—H11	124 (2)
C2—C3—H3	119 (3)	C11—C12—H12	117 (2)
C4—C3—C2	119.7 (4)	C13—C12—C11	120.9 (4)
C4—C3—H3	121 (3)	C13—C12—H12	122 (2)
C3—C4—C5	121.3 (5)	C12—C13—C14	121.6 (4)
C3—C4—H4	120 (3)	C12—C13—H13	119 (3)
C5—C4—H4	118 (3)	C14—C13—H13	119 (3)
C4—C5—C6	120.4 (4)	C13—C14—H14	121 (2)
C4—C5—H5	119 (2)	C15—C14—C13	117.2 (4)
C6—C5—H5	120 (2)	C15—C14—H14	122 (2)
C1—C6—N1	120.1 (3)	C10—C15—C16	108.4 (3)
C5—C6—N1	122.2 (3)	C14—C15—C10	121.4 (3)
C5—C6—C1	117.6 (3)	C14—C15—C16	130.1 (3)
S1—C7—H7A	105 (2)	O4—C16—N2	125.2 (3)
S1—C7—H7B	104 (2)	O4—C16—C15	129.3 (3)
C8—C7—S1	115.6 (3)	N2—C16—C15	105.5 (3)
Cl1—C1—C2—C3	−177.5 (4)	C8—N2—C9—C10	−177.6 (3)
Cl1—C1—C6—N1	−4.8 (4)	C8—N2—C16—O4	−3.1 (5)
Cl1—C1—C6—C5	177.9 (3)	C8—N2—C16—C15	177.0 (3)
S1—N1—C6—C1	146.9 (3)	C9—N2—C8—C7	−88.2 (4)
S1—N1—C6—C5	−36.0 (5)	C9—N2—C16—O4	−179.5 (3)
S1—C7—C8—N2	−62.7 (4)	C9—N2—C16—C15	0.6 (4)
O1—S1—N1—C6	42.2 (3)	C9—C10—C11—C12	179.3 (3)
O1—S1—C7—C8	−169.0 (3)	C9—C10—C15—C14	−178.7 (3)
O2—S1—N1—C6	171.4 (3)	C9—C10—C15—C16	−1.1 (4)
O2—S1—C7—C8	60.6 (3)	C10—C11—C12—C13	0.4 (6)
O3—C9—C10—C11	1.0 (6)	C10—C15—C16—O4	−179.6 (4)
O3—C9—C10—C15	−178.6 (4)	C10—C15—C16—N2	0.3 (4)
N1—S1—C7—C8	−52.0 (3)	C11—C10—C15—C14	1.6 (5)
N2—C9—C10—C11	−179.0 (4)	C11—C10—C15—C16	179.3 (3)
N2—C9—C10—C15	1.4 (3)	C11—C12—C13—C14	−0.2 (6)
C1—C2—C3—C4	−0.6 (7)	C12—C13—C14—C15	0.7 (6)
C2—C1—C6—N1	175.6 (3)	C13—C14—C15—C10	−1.4 (6)
C2—C1—C6—C5	−1.6 (5)	C13—C14—C15—C16	−178.4 (3)
C2—C3—C4—C5	−1.3 (7)	C14—C15—C16—O4	−2.2 (6)
C3—C4—C5—C6	1.8 (7)	C14—C15—C16—N2	177.7 (4)
C4—C5—C6—N1	−177.5 (4)	C15—C10—C11—C12	−1.1 (5)
C4—C5—C6—C1	−0.3 (6)	C16—N2—C8—C7	95.7 (4)
C6—C1—C2—C3	2.1 (6)	C16—N2—C9—O3	178.8 (3)
C7—S1—N1—C6	−74.2 (3)	C16—N2—C9—C10	−1.2 (4)
C8—N2—C9—O3	2.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.84 (4)	2.24 (3)	2.984 (4)	148 (3)
C5—H5···O1	0.96 (4)	2.24 (4)	2.912 (5)	127 (3)
C7—H7A···O4^i	0.90 (4)	2.48 (4)	3.123 (5)	129 (3)
C7—H7B···O2^ii	0.92 (3)	2.52 (3)	3.174 (4)	128 (2)

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

(II) N-(4-chlorophenyl)-2-phthalimidoethanesulfonamide

Crystal data

C16H13ClN2O4S	Z = 2
Mr = 364.79	F(000) = 376
Triclinic, P1	Dx = 1.487 Mg m^−3
a = 7.5484 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9887 (10) Å	Cell parameters from 2152 reflections
c = 11.2112 (10) Å	θ = 3.6–27.6°
α = 100.624 (8)°	µ = 0.39 mm^−1
β = 98.405 (7)°	T = 293 K
γ = 95.661 (8)°	Needle, colourless
V = 815.01 (13) Å^3	0.18 × 0.12 × 0.06 mm

Data collection

Agilent Xcalibur Eos diffractometer	3287 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2245 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.1333 pixels mm^-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −8→9
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014)	k = −12→11
Tmin = 0.974, Tmax = 0.991	l = −13→13
5967 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	All H-atom parameters refined
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.1892P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3287 reflections	Δρmax = 0.36 e Å^−3
269 parameters	Δρmin = −0.37 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.12262 (9)	0.64365 (6)	0.17046 (6)	0.0474 (2)
Cl1	0.40898 (13)	0.21113 (9)	0.55665 (7)	0.0877 (3)
O1	0.1404 (3)	0.74094 (19)	0.28272 (16)	0.0617 (5)
O2	0.0077 (2)	0.66582 (19)	0.06416 (16)	0.0613 (5)
N2	0.3718 (3)	0.8007 (2)	0.00577 (19)	0.0526 (6)
O3	0.4483 (3)	0.6276 (2)	−0.13529 (19)	0.0730 (6)
O4	0.2650 (3)	0.9967 (2)	0.09429 (19)	0.0753 (6)
N1	0.0440 (3)	0.4938 (3)	0.1914 (2)	0.0567 (6)
C15	0.2363 (3)	0.9237 (2)	−0.1272 (2)	0.0449 (6)
C10	0.2968 (3)	0.8135 (2)	−0.1968 (2)	0.0443 (6)
C11	0.2729 (4)	0.7948 (3)	−0.3226 (3)	0.0568 (7)
C5	0.1819 (3)	0.2998 (3)	0.2443 (2)	0.0475 (6)
C1	0.1694 (5)	0.4902 (3)	0.4040 (3)	0.0661 (8)
C6	0.1349 (3)	0.4282 (3)	0.2810 (2)	0.0471 (6)
C4	0.2632 (4)	0.2323 (3)	0.3294 (2)	0.0515 (7)
C3	0.3013 (4)	0.2958 (3)	0.4514 (2)	0.0543 (7)
C9	0.3824 (3)	0.7322 (3)	−0.1123 (2)	0.0503 (6)
C16	0.2867 (4)	0.9181 (3)	0.0042 (3)	0.0522 (7)
C13	0.1220 (4)	0.9958 (3)	−0.3088 (3)	0.0649 (8)
C7	0.3389 (4)	0.6241 (3)	0.1331 (3)	0.0518 (7)
C14	0.1475 (4)	1.0161 (3)	−0.1820 (3)	0.0555 (7)
C8	0.4433 (4)	0.7558 (4)	0.1163 (3)	0.0616 (8)
C2	0.2545 (5)	0.4229 (3)	0.4887 (3)	0.0696 (9)
C12	0.1851 (4)	0.8875 (4)	−0.3776 (3)	0.0664 (8)
H5	0.160 (3)	0.256 (2)	0.159 (2)	0.051 (7)*
H7A	0.401 (3)	0.595 (2)	0.199 (2)	0.046 (7)*
H4	0.298 (3)	0.151 (3)	0.304 (2)	0.058 (8)*
H2	0.282 (4)	0.466 (3)	0.567 (3)	0.069 (9)*
H8A	0.444 (4)	0.833 (3)	0.185 (3)	0.069 (9)*
H14	0.112 (4)	1.085 (3)	−0.133 (3)	0.066 (9)*
H7B	0.325 (3)	0.553 (3)	0.063 (2)	0.056 (7)*
H11	0.315 (4)	0.720 (3)	−0.370 (3)	0.077 (9)*
H12	0.170 (5)	0.881 (4)	−0.463 (3)	0.102 (12)*
H13	0.060 (4)	1.059 (3)	−0.343 (3)	0.063 (8)*
H8B	0.564 (5)	0.739 (4)	0.111 (3)	0.093 (11)*
H1	0.010 (3)	0.448 (3)	0.130 (2)	0.047 (8)*
H1A	0.132 (3)	0.575 (3)	0.428 (2)	0.063 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0565 (4)	0.0443 (4)	0.0406 (3)	0.0169 (3)	−0.0005 (3)	0.0080 (3)
Cl1	0.1223 (7)	0.0831 (6)	0.0596 (5)	0.0158 (5)	−0.0063 (5)	0.0348 (4)
O1	0.0830 (13)	0.0531 (11)	0.0479 (11)	0.0239 (10)	0.0074 (9)	0.0020 (9)
O2	0.0680 (12)	0.0588 (12)	0.0541 (11)	0.0206 (10)	−0.0117 (9)	0.0142 (9)
N2	0.0622 (14)	0.0519 (13)	0.0482 (13)	0.0144 (11)	0.0111 (10)	0.0163 (10)
O3	0.0917 (15)	0.0619 (13)	0.0829 (15)	0.0417 (12)	0.0363 (12)	0.0258 (11)
O4	0.1066 (16)	0.0588 (13)	0.0559 (12)	0.0174 (11)	0.0175 (11)	−0.0068 (10)
N1	0.0596 (15)	0.0568 (15)	0.0479 (14)	0.0016 (12)	−0.0068 (12)	0.0116 (12)
C15	0.0470 (14)	0.0355 (13)	0.0542 (15)	0.0059 (11)	0.0141 (11)	0.0098 (11)
C10	0.0427 (13)	0.0407 (13)	0.0499 (15)	0.0053 (11)	0.0105 (11)	0.0084 (11)
C11	0.0640 (18)	0.0544 (17)	0.0523 (17)	0.0109 (14)	0.0148 (13)	0.0060 (14)
C5	0.0486 (15)	0.0531 (16)	0.0369 (14)	0.0018 (12)	0.0029 (11)	0.0048 (12)
C1	0.101 (2)	0.0536 (18)	0.0443 (16)	0.0170 (17)	0.0117 (15)	0.0075 (14)
C6	0.0484 (14)	0.0503 (15)	0.0424 (14)	0.0023 (12)	0.0057 (11)	0.0125 (12)
C4	0.0583 (17)	0.0480 (16)	0.0488 (15)	0.0087 (13)	0.0087 (12)	0.0104 (13)
C3	0.0639 (17)	0.0545 (17)	0.0456 (15)	−0.0005 (13)	0.0051 (12)	0.0204 (13)
C9	0.0522 (15)	0.0468 (15)	0.0596 (17)	0.0147 (13)	0.0190 (12)	0.0183 (13)
C16	0.0571 (16)	0.0426 (15)	0.0577 (17)	0.0066 (13)	0.0143 (13)	0.0085 (13)
C13	0.0613 (18)	0.066 (2)	0.073 (2)	0.0147 (16)	0.0043 (15)	0.0308 (17)
C7	0.0614 (17)	0.0526 (17)	0.0454 (15)	0.0205 (14)	0.0046 (13)	0.0168 (14)
C14	0.0542 (16)	0.0443 (15)	0.070 (2)	0.0129 (13)	0.0132 (14)	0.0115 (14)
C8	0.062 (2)	0.069 (2)	0.0535 (18)	0.0055 (16)	−0.0020 (14)	0.0211 (16)
C2	0.109 (3)	0.0590 (19)	0.0333 (15)	0.0028 (17)	−0.0019 (15)	0.0049 (14)
C12	0.070 (2)	0.074 (2)	0.0571 (19)	0.0095 (16)	0.0050 (15)	0.0219 (17)

Geometric parameters (Å, º)

S1—O1	1.4214 (18)	C5—C4	1.374 (4)
S1—O2	1.4333 (17)	C5—H5	0.96 (2)
S1—N1	1.626 (3)	C1—C6	1.379 (4)
S1—C7	1.764 (3)	C1—C2	1.381 (4)
Cl1—C3	1.729 (3)	C1—H1A	0.93 (3)
N2—C9	1.391 (3)	C4—C3	1.373 (4)
N2—C16	1.393 (3)	C4—H4	0.88 (3)
N2—C8	1.445 (3)	C3—C2	1.360 (4)
O3—C9	1.203 (3)	C13—C14	1.379 (4)
O4—C16	1.202 (3)	C13—C12	1.377 (5)
N1—C6	1.428 (3)	C13—H13	0.93 (3)
N1—H1	0.75 (2)	C7—C8	1.522 (4)
C15—C10	1.384 (3)	C7—H7A	0.92 (3)
C15—C16	1.480 (4)	C7—H7B	0.94 (3)
C15—C14	1.375 (4)	C14—H14	0.89 (3)
C10—C11	1.372 (4)	C8—H8A	0.98 (3)
C10—C9	1.477 (4)	C8—H8B	0.95 (3)
C11—C12	1.374 (4)	C2—H2	0.89 (3)
C11—H11	0.95 (3)	C12—H12	0.93 (4)
C5—C6	1.371 (4)
O1—S1—O2	118.61 (11)	C4—C3—Cl1	118.9 (2)
O1—S1—N1	108.99 (13)	C2—C3—Cl1	120.7 (2)
O1—S1—C7	109.18 (13)	C2—C3—C4	120.5 (3)
O2—S1—N1	105.52 (12)	N2—C9—C10	105.8 (2)
O2—S1—C7	108.63 (13)	O3—C9—N2	124.6 (3)
N1—S1—C7	105.05 (13)	O3—C9—C10	129.6 (3)
C9—N2—C16	111.9 (2)	N2—C16—C15	105.9 (2)
C9—N2—C8	123.7 (2)	O4—C16—N2	124.8 (3)
C16—N2—C8	124.4 (2)	O4—C16—C15	129.3 (3)
S1—N1—H1	109 (2)	C14—C13—H13	115.8 (18)
C6—N1—S1	122.31 (18)	C12—C13—C14	121.0 (3)
C6—N1—H1	114 (2)	C12—C13—H13	123.1 (18)
C10—C15—C16	108.0 (2)	S1—C7—H7A	105.0 (15)
C14—C15—C10	121.2 (3)	S1—C7—H7B	107.9 (16)
C14—C15—C16	130.8 (2)	C8—C7—S1	114.2 (2)
C15—C10—C9	108.4 (2)	C8—C7—H7A	108.6 (15)
C11—C10—C15	120.8 (3)	C8—C7—H7B	112.4 (17)
C11—C10—C9	130.8 (2)	H7A—C7—H7B	108 (2)
C10—C11—C12	118.1 (3)	C15—C14—C13	117.7 (3)
C10—C11—H11	120.9 (19)	C15—C14—H14	117.4 (19)
C12—C11—H11	121.0 (19)	C13—C14—H14	124.9 (19)
C6—C5—C4	120.4 (2)	N2—C8—C7	113.5 (2)
C6—C5—H5	120.4 (15)	N2—C8—H8A	105.8 (17)
C4—C5—H5	119.2 (15)	N2—C8—H8B	107 (2)
C6—C1—C2	119.4 (3)	C7—C8—H8A	112.4 (18)
C6—C1—H1A	119.1 (17)	C7—C8—H8B	108 (2)
C2—C1—H1A	121.4 (17)	H8A—C8—H8B	110 (3)
C5—C6—N1	119.3 (2)	C1—C2—H2	119 (2)
C5—C6—C1	119.8 (3)	C3—C2—C1	120.3 (3)
C1—C6—N1	120.8 (3)	C3—C2—H2	121.0 (19)
C5—C4—H4	119.7 (18)	C11—C12—C13	121.1 (3)
C3—C4—C5	119.5 (3)	C11—C12—H12	121 (2)
C3—C4—H4	120.7 (18)	C13—C12—H12	118 (2)
S1—N1—C6—C5	−123.3 (2)	C4—C3—C2—C1	−0.6 (5)
S1—N1—C6—C1	59.3 (3)	C9—N2—C16—O4	−178.0 (3)
S1—C7—C8—N2	−70.9 (3)	C9—N2—C16—C15	0.8 (3)
Cl1—C3—C2—C1	179.7 (3)	C9—N2—C8—C7	−69.7 (4)
O1—S1—N1—C6	−58.7 (2)	C9—C10—C11—C12	179.2 (3)
O1—S1—C7—C8	−60.0 (2)	C16—N2—C9—O3	−179.3 (3)
O2—S1—N1—C6	172.9 (2)	C16—N2—C9—C10	0.2 (3)
O2—S1—C7—C8	70.7 (2)	C16—N2—C8—C7	111.3 (3)
N1—S1—C7—C8	−176.8 (2)	C16—C15—C10—C11	−178.2 (2)
C15—C10—C11—C12	−0.8 (4)	C16—C15—C10—C9	1.7 (3)
C15—C10—C9—N2	−1.2 (3)	C16—C15—C14—C13	178.8 (3)
C15—C10—C9—O3	178.2 (3)	C7—S1—N1—C6	58.2 (3)
C10—C15—C16—N2	−1.6 (3)	C14—C15—C10—C11	1.3 (4)
C10—C15—C16—O4	177.2 (3)	C14—C15—C10—C9	−178.8 (2)
C10—C15—C14—C13	−0.5 (4)	C14—C15—C16—N2	179.0 (3)
C10—C11—C12—C13	−0.3 (5)	C14—C15—C16—O4	−2.2 (5)
C11—C10—C9—N2	178.7 (3)	C14—C13—C12—C11	1.1 (5)
C11—C10—C9—O3	−1.8 (5)	C8—N2—C9—O3	1.6 (4)
C5—C4—C3—Cl1	−178.3 (2)	C8—N2—C9—C10	−179.0 (2)
C5—C4—C3—C2	2.0 (4)	C8—N2—C16—O4	1.1 (4)
C6—C5—C4—C3	−1.7 (4)	C8—N2—C16—C15	180.0 (2)
C6—C1—C2—C3	−1.0 (5)	C2—C1—C6—N1	178.7 (3)
C4—C5—C6—N1	−177.4 (2)	C2—C1—C6—C5	1.3 (5)
C4—C5—C6—C1	0.0 (4)	C12—C13—C14—C15	−0.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.75 (2)	2.24 (2)	2.961 (3)	162 (2)
C4—H4···O4^ii	0.89 (3)	2.53 (2)	3.196 (3)	133 (2)

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

(III) N-(3-chlorophenyl)-2-phthalimidoethanesulfonamide

Crystal data

C16H13ClN2O4S	F(000) = 752
Mr = 364.79	Dx = 1.491 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.5652 (2) Å	Cell parameters from 2243 reflections
b = 25.5022 (12) Å	θ = 3.7–28.6°
c = 11.5536 (5) Å	µ = 0.39 mm^−1
β = 97.800 (4)°	T = 293 K
V = 1624.58 (12) Å^3	Needle, colourless
Z = 4	0.50 × 0.15 × 0.09 mm

Data collection

Agilent Xcalibur Eos diffractometer	3298 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2582 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 16.1333 pixels mm^-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −5→6
Absorption correction: analytical (CrysAlis PRO; Agilent, 2014)	k = −31→22
Tmin = 0.982, Tmax = 0.996	l = −12→14
7040 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	All H-atom parameters refined
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 0.3678P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3298 reflections	Δρmax = 0.19 e Å^−3
269 parameters	Δρmin = −0.40 e Å^−3
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	−0.57180 (11)	0.26538 (2)	0.08458 (7)	0.0707 (2)
S1	0.03092 (9)	0.09436 (2)	0.03822 (4)	0.04136 (16)
O1	−0.0363 (3)	0.12447 (7)	−0.06525 (12)	0.0621 (5)
O2	0.2110 (3)	0.05457 (6)	0.03952 (14)	0.0571 (4)
O3	0.2310 (3)	0.00238 (6)	0.31988 (13)	0.0531 (4)
O4	−0.4443 (2)	0.10432 (6)	0.31218 (12)	0.0473 (4)
N1	0.1327 (3)	0.13385 (7)	0.14414 (15)	0.0408 (4)
N2	−0.1244 (3)	0.05004 (6)	0.28675 (13)	0.0367 (4)
C1	0.0852 (4)	0.19565 (9)	0.29543 (19)	0.0489 (5)
C2	−0.0380 (5)	0.23626 (11)	0.3393 (2)	0.0686 (8)
C3	−0.2418 (5)	0.25774 (11)	0.2757 (2)	0.0647 (7)
C4	−0.3173 (4)	0.23846 (8)	0.1670 (2)	0.0472 (5)
C5	−0.1972 (4)	0.19835 (8)	0.11952 (19)	0.0411 (5)
C6	0.0044 (3)	0.17622 (7)	0.18532 (16)	0.0360 (4)
C7	−0.2415 (3)	0.06659 (8)	0.07370 (17)	0.0375 (4)
C8	−0.2175 (4)	0.02790 (8)	0.17376 (18)	0.0412 (5)
C9	0.0935 (3)	0.03358 (7)	0.35299 (17)	0.0380 (4)
C10	0.1084 (3)	0.06212 (7)	0.46552 (16)	0.0375 (4)
C11	0.2853 (4)	0.06133 (9)	0.56105 (19)	0.0487 (5)
C12	0.2481 (5)	0.09233 (10)	0.6556 (2)	0.0558 (6)
C13	0.0431 (5)	0.12297 (10)	0.6528 (2)	0.0567 (6)
C14	−0.1332 (4)	0.12401 (9)	0.55640 (19)	0.0484 (5)
C15	−0.0968 (3)	0.09288 (7)	0.46262 (16)	0.0366 (4)
C16	−0.2489 (3)	0.08511 (7)	0.34885 (16)	0.0360 (4)
H7A	−0.350 (4)	0.0969 (7)	0.0854 (17)	0.036 (5)*
H14	−0.271 (4)	0.1439 (8)	0.5533 (17)	0.042 (6)*
H7B	−0.301 (4)	0.0496 (8)	0.0047 (19)	0.051 (6)*
H8A	−0.381 (4)	0.0139 (8)	0.1790 (18)	0.048 (6)*
H8B	−0.107 (4)	−0.0013 (8)	0.1612 (17)	0.045 (6)*
H1A	0.223 (4)	0.1804 (8)	0.3377 (18)	0.046 (6)*
H11	0.425 (4)	0.0413 (9)	0.562 (2)	0.059 (7)*
H5	−0.246 (4)	0.1862 (8)	0.050 (2)	0.049 (6)*
H1	0.246 (4)	0.1223 (9)	0.1910 (19)	0.045 (6)*
H12	0.366 (5)	0.0923 (10)	0.721 (2)	0.071 (8)*
H3	−0.316 (5)	0.2865 (11)	0.306 (2)	0.078 (8)*
H13	0.022 (4)	0.1425 (9)	0.715 (2)	0.066 (7)*
H2	0.020 (5)	0.2491 (11)	0.413 (3)	0.091 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0515 (3)	0.0599 (4)	0.0954 (5)	0.0073 (3)	−0.0096 (3)	0.0214 (3)
S1	0.0345 (3)	0.0566 (3)	0.0341 (3)	−0.0054 (2)	0.0089 (2)	−0.0095 (2)
O1	0.0704 (11)	0.0859 (12)	0.0308 (8)	−0.0143 (9)	0.0103 (7)	0.0030 (8)
O2	0.0370 (8)	0.0699 (10)	0.0664 (10)	0.0019 (8)	0.0141 (7)	−0.0268 (8)
O3	0.0456 (8)	0.0532 (9)	0.0607 (10)	0.0172 (7)	0.0076 (7)	−0.0016 (7)
O4	0.0358 (8)	0.0567 (9)	0.0484 (8)	0.0123 (7)	0.0021 (6)	−0.0009 (7)
N1	0.0325 (8)	0.0476 (10)	0.0400 (10)	−0.0006 (8)	−0.0035 (8)	−0.0073 (8)
N2	0.0366 (8)	0.0395 (8)	0.0340 (8)	0.0051 (7)	0.0049 (7)	0.0000 (7)
C1	0.0487 (12)	0.0544 (13)	0.0404 (12)	0.0072 (11)	−0.0054 (10)	−0.0044 (10)
C2	0.0779 (18)	0.0743 (18)	0.0486 (14)	0.0214 (15)	−0.0094 (13)	−0.0201 (13)
C3	0.0697 (16)	0.0584 (15)	0.0642 (16)	0.0189 (14)	0.0033 (13)	−0.0112 (13)
C4	0.0420 (11)	0.0422 (12)	0.0557 (13)	0.0009 (10)	0.0010 (10)	0.0108 (10)
C5	0.0423 (11)	0.0429 (11)	0.0361 (11)	−0.0071 (10)	−0.0020 (9)	0.0047 (9)
C6	0.0344 (10)	0.0376 (10)	0.0360 (10)	−0.0044 (9)	0.0048 (8)	0.0018 (8)
C7	0.0286 (9)	0.0482 (12)	0.0348 (10)	−0.0031 (9)	0.0010 (8)	−0.0074 (9)
C8	0.0401 (11)	0.0407 (11)	0.0426 (11)	−0.0017 (10)	0.0048 (9)	−0.0057 (9)
C9	0.0338 (10)	0.0368 (10)	0.0440 (11)	0.0030 (9)	0.0070 (8)	0.0065 (9)
C10	0.0381 (10)	0.0368 (10)	0.0373 (10)	−0.0005 (9)	0.0044 (8)	0.0085 (8)
C11	0.0450 (12)	0.0521 (13)	0.0470 (13)	−0.0003 (11)	−0.0009 (10)	0.0119 (10)
C12	0.0612 (15)	0.0617 (15)	0.0404 (13)	−0.0097 (13)	−0.0080 (11)	0.0089 (11)
C13	0.0752 (17)	0.0573 (14)	0.0382 (12)	−0.0103 (14)	0.0098 (12)	−0.0061 (11)
C14	0.0530 (13)	0.0497 (13)	0.0439 (12)	0.0029 (11)	0.0117 (10)	−0.0018 (10)
C15	0.0374 (10)	0.0381 (10)	0.0351 (10)	−0.0002 (9)	0.0076 (8)	0.0063 (8)
C16	0.0337 (10)	0.0375 (10)	0.0377 (10)	0.0009 (9)	0.0086 (8)	0.0043 (8)

Geometric parameters (Å, º)

Cl1—C4	1.738 (2)	C5—C6	1.387 (3)
S1—O1	1.4274 (16)	C5—H5	0.87 (2)
S1—O2	1.4248 (16)	C7—C8	1.512 (3)
S1—N1	1.6262 (17)	C7—H7A	1.000 (19)
S1—C7	1.7711 (19)	C7—H7B	0.93 (2)
O3—C9	1.202 (2)	C8—H8A	0.99 (2)
O4—C16	1.215 (2)	C8—H8B	0.99 (2)
N1—C6	1.413 (3)	C9—C10	1.482 (3)
N1—H1	0.83 (2)	C10—C11	1.376 (3)
N2—C8	1.452 (2)	C10—C15	1.382 (3)
N2—C9	1.407 (2)	C11—C12	1.386 (3)
N2—C16	1.389 (2)	C11—H11	0.93 (2)
C1—C2	1.376 (3)	C12—C13	1.380 (4)
C1—C6	1.382 (3)	C12—H12	0.93 (3)
C1—H1A	0.94 (2)	C13—C14	1.381 (3)
C2—C3	1.378 (4)	C13—H13	0.90 (2)
C2—H2	0.93 (3)	C14—C15	1.380 (3)
C3—C4	1.360 (3)	C14—H14	0.92 (2)
C3—H3	0.93 (3)	C15—C16	1.477 (3)
C4—C5	1.376 (3)
O1—S1—N1	108.78 (10)	C8—C7—H7A	113.1 (11)
O1—S1—C7	105.89 (10)	C8—C7—H7B	109.7 (13)
O2—S1—O1	119.73 (10)	H7A—C7—H7B	108.9 (17)
O2—S1—N1	105.09 (9)	N2—C8—C7	114.67 (16)
O2—S1—C7	109.62 (10)	N2—C8—H8A	107.8 (12)
N1—S1—C7	107.17 (9)	N2—C8—H8B	105.7 (12)
S1—N1—H1	115.4 (16)	C7—C8—H8A	107.2 (12)
C6—N1—S1	125.93 (14)	C7—C8—H8B	111.8 (11)
C6—N1—H1	115.2 (15)	H8A—C8—H8B	109.5 (16)
C9—N2—C8	123.32 (16)	O3—C9—N2	124.27 (19)
C16—N2—C8	124.91 (17)	O3—C9—C10	129.93 (19)
C16—N2—C9	111.38 (16)	N2—C9—C10	105.80 (15)
C2—C1—C6	119.5 (2)	C11—C10—C9	130.20 (19)
C2—C1—H1A	122.4 (13)	C11—C10—C15	121.77 (19)
C6—C1—H1A	118.1 (13)	C15—C10—C9	108.03 (17)
C1—C2—C3	121.2 (2)	C10—C11—C12	117.2 (2)
C1—C2—H2	118.2 (18)	C10—C11—H11	121.8 (14)
C3—C2—H2	120.6 (18)	C12—C11—H11	121.0 (14)
C2—C3—H3	119.2 (17)	C11—C12—H12	118.4 (16)
C4—C3—C2	118.5 (2)	C13—C12—C11	121.1 (2)
C4—C3—H3	122.1 (17)	C13—C12—H12	120.6 (16)
C3—C4—Cl1	119.33 (18)	C12—C13—C14	121.6 (2)
C3—C4—C5	122.1 (2)	C12—C13—H13	119.5 (16)
C5—C4—Cl1	118.60 (18)	C14—C13—H13	118.9 (16)
C4—C5—C6	119.0 (2)	C13—C14—H14	122.7 (13)
C4—C5—H5	121.7 (14)	C15—C14—C13	117.3 (2)
C6—C5—H5	119.3 (14)	C15—C14—H14	120.0 (13)
C1—C6—N1	117.91 (18)	C10—C15—C16	108.50 (16)
C1—C6—C5	119.76 (19)	C14—C15—C10	121.07 (19)
C5—C6—N1	122.33 (18)	C14—C15—C16	130.43 (19)
S1—C7—H7A	105.8 (11)	O4—C16—N2	124.41 (18)
S1—C7—H7B	101.9 (13)	O4—C16—C15	129.33 (18)
C8—C7—S1	116.65 (14)	N2—C16—C15	106.27 (16)
Cl1—C4—C5—C6	−179.24 (15)	C8—N2—C9—C10	−174.67 (16)
S1—N1—C6—C1	160.96 (16)	C8—N2—C16—O4	−5.5 (3)
S1—N1—C6—C5	−18.8 (3)	C8—N2—C16—C15	174.53 (16)
S1—C7—C8—N2	64.7 (2)	C9—N2—C8—C7	−118.4 (2)
O1—S1—N1—C6	58.08 (18)	C9—N2—C16—O4	−178.48 (18)
O1—S1—C7—C8	173.80 (15)	C9—N2—C16—C15	1.5 (2)
O2—S1—N1—C6	−172.55 (16)	C9—C10—C11—C12	−179.51 (19)
O2—S1—C7—C8	43.34 (18)	C9—C10—C15—C14	179.86 (17)
O3—C9—C10—C11	1.4 (3)	C9—C10—C15—C16	0.0 (2)
O3—C9—C10—C15	−178.81 (19)	C10—C11—C12—C13	−0.6 (3)
N1—S1—C7—C8	−70.20 (18)	C10—C15—C16—O4	179.11 (19)
N2—C9—C10—C11	−178.86 (19)	C10—C15—C16—N2	−0.9 (2)
N2—C9—C10—C15	0.9 (2)	C11—C10—C15—C14	−0.3 (3)
C1—C2—C3—C4	−1.1 (4)	C11—C10—C15—C16	179.78 (17)
C2—C1—C6—N1	−178.8 (2)	C11—C12—C13—C14	0.1 (4)
C2—C1—C6—C5	1.0 (3)	C12—C13—C14—C15	0.3 (3)
C2—C3—C4—Cl1	−179.3 (2)	C13—C14—C15—C10	−0.2 (3)
C2—C3—C4—C5	0.2 (4)	C13—C14—C15—C16	179.7 (2)
C3—C4—C5—C6	1.2 (3)	C14—C15—C16—O4	−0.8 (3)
C4—C5—C6—N1	177.96 (17)	C14—C15—C16—N2	179.24 (19)
C4—C5—C6—C1	−1.8 (3)	C15—C10—C11—C12	0.7 (3)
C6—C1—C2—C3	0.5 (4)	C16—N2—C8—C7	69.4 (2)
C7—S1—N1—C6	−55.98 (19)	C16—N2—C9—O3	178.21 (18)
C8—N2—C9—O3	5.1 (3)	C16—N2—C9—C10	−1.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.87 (2)	2.46 (2)	3.071 (3)	128 (2)
N1—H1···O4^i	0.83 (2)	2.12 (2)	2.939 (2)	172 (2)
C11—H11···O3^ii	0.93 (2)	2.46 (2)	3.282 (3)	147 (2)
C2—H2···Cl1^iii	0.93 (3)	2.83 (3)	3.573 (3)	138 (2)

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