Ethyl 3-[6-(4-meth­oxy­benzene­sulfon­amido)-2H-indazol-2-yl]propano­ate monohydrate

In the title compound, C₁₉H₂₁N₃O₅S·H₂O, the central indazole system is essentially planar (r.m.s. deviation = 0.012 Å), while both the benzene ring and the mean plane defined by the non-H atoms of the ethyl propionic ester unit (r.m.s. deviation = 0.087 Å) are nearly perpendicular to the indazole plane, as indicated by the dihedral angles of 82.45 (8) and 75.62 (8)°, respectively. Consequently, the mol­ecule adopts a U-shaped geometry. In the crystal, the water mol­ecule, which is linked to the indazole system by a strong O—H...N hydrogen bond, is also involved in two additional N—H...O and O—H...O inter­actions, which link the organic mol­ecules into chains along the b-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.077
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...        4.1 Ratio

Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H    Uiso(max)/Uiso(min) ..        4.4 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    --  C12     ..        5.3 su
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         18

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          3
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         20

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

S1. Comment

Sulfonamides constitute an important class of drugs. They possess various types of pharmacological activities such as antibacterial (Gadad et al., 2000), anti-carbonic anhydrase (Brzozowski et al., 2010), hypoglycemic (Drew, 2000), and anticancer activity (Garaj et al., 2005). Recently, our research group has reported the synthesis of some new N-(6(4)-indazolyl)aylsulfonamide derivatives. Some of these compounds showed an important antiproliferative activity against some human and murine cell lines (Abbassi et al., 2012; Bouissane et al., 2006).

The crystal structure of the Ethyl-3-[6-(4-methoxybenzenesulfonamido)-2H- indazol-2-yl]-propanoate monohydrate is built up from two fused five- and six-membered rings (N2 N3 C1 to C7) virtually coplanar, with a maximum deviation of 0.021 (2) A Å for C2 atom as shown in Fig.1. Moreover, the two cycles are nearly perpendicular to the plan through the atoms forming the propionic acid ester group (O3O4 C9 to C11) and to benzene ring (C13 to C18) as indicated by the dihedral angles between them of 75.62 (8)° and 82.45 (8)° respectively. As a matter of fact, the molecule has a U shaped geometry.

The cohesion of the crystal structure is ensured by three classic strong hydrogen bonds between the water and the organic molecules: O6–H6A···N2, N1–H1···O6 and O6–H6B···O1, as shown in Fig.2 and Table 2.

Related literature

For the pharmacological activity of sulfonamides, see: Gadad et al. (2000); Brzozowski et al. (2010); Drew (2000); Garaj et al. (2005). For their antiproliferative activity see: Abbassi et al. (2012); Bouissane et al. (2006).

S2. Experimental

A mixture of ethyl 3-(6-nitro-2H-indazol-2-yl)propanoate 1 (1.22 mmol) and anhydrous SnCl₂ (1.1 g, 6.1 mmol) in 25 ml of absolute ethanol was heated at 333 K for 3 h. After reduction, the starting material disappeared, and the solution was allowed to cool down. The pH was made slightly basic (pH 7–8) by addition of 5% aqueous potassium bicarbonate before extraction with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate. The solvent was removed to afford the amine, which was immediately dissolved in pyridine (5 ml) and then reacted with 4-methoxybenzenesulfonyl chloride (1.25 mmol) at room temperature for 24 h. After the reaction mixture was concentrated in vacuo, the resulting residue was purified by flash chromatography (eluted with Ethyl acetate: Hexane 1:9).

S3. Refinement

The structure is solved by direct method technique and refined by full-matrix least-squares using SHELXS97 and SHELXL97 program packages. H atoms were located in a difference map and treated as riding with C–H = 0.96 Å, C–H = 0.97 Å, C–H = 0.93 Å and N–H = 0.86 Å for methyl, methylene, aromatic CH and NH respectively. All hydrogen with U_iso(H) = 1.2 U_eq (aromatic, methylene)and U_iso(H) = 1.5 U_eq for methyl. The space group is not centro symmetric and the polar axis restraint is generated automatically by SHELXL program. The 1779 Friedel opposites reflections are not merged. The atomic displacement parameters of the C12 atom are quite large because it is a termial methyl that vibrates.

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. A view of crystal packing showing the water units linking the organic molecules in chains along the b axis.

Ethyl 3-[6-(4-methoxybenzenesulfonamido)-2H-indazol-2-yl]propanoate monohydrate

Crystal data

C19H21N3O5S·H2O	F(000) = 444
Mr = 421.46	Dx = 1.369 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2yb	Cell parameters from 4021 reflections
a = 9.0248 (3) Å	θ = 2.3–26.4°
b = 8.7602 (3) Å	µ = 0.20 mm^−1
c = 13.1792 (4) Å	T = 296 K
β = 101.062 (2)°	Block, colourless
V = 1022.58 (6) Å^3	0.42 × 0.37 × 0.28 mm
Z = 2

Data collection

Bruker X8 APEX diffractometer	3887 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 26.4°, θmin = 2.3°
ϕ and ω scans	h = −11→11
10050 measured reflections	k = −10→10
4021 independent reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.037P)^2 + 0.2529P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4021 reflections	Δρmax = 0.28 e Å^−3
262 parameters	Δρmin = −0.28 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1779 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (6)

Special details

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

Refinement. Refinement of F² against all reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on all data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	0.75199 (19)	0.7888 (2)	0.11333 (12)	0.0197 (4)
C2	0.61152 (18)	0.8667 (2)	0.10899 (12)	0.0216 (3)
H2	0.6095	0.9726	0.1039	0.026*
C3	0.4816 (2)	0.7914 (2)	0.11201 (13)	0.0223 (4)
H3	0.3909	0.8438	0.1071	0.027*
C4	0.48733 (19)	0.6302 (2)	0.12290 (12)	0.0202 (3)
C5	0.62772 (18)	0.5536 (2)	0.12955 (12)	0.0191 (3)
C6	0.76182 (19)	0.6328 (2)	0.12325 (13)	0.0214 (4)
H6	0.8528	0.5817	0.1257	0.026*
C7	0.3845 (2)	0.5150 (2)	0.13056 (13)	0.0215 (4)
H7	0.2815	0.5268	0.1283	0.026*
C8	0.4016 (2)	0.2317 (2)	0.15290 (14)	0.0241 (4)
H8A	0.4322	0.1643	0.1022	0.029*
H8B	0.2921	0.2363	0.1386	0.029*
C9	0.4548 (2)	0.1655 (2)	0.25982 (14)	0.0273 (4)
H9A	0.4299	0.0577	0.2586	0.033*
H9B	0.5638	0.1746	0.2782	0.033*
C10	0.3852 (2)	0.2433 (2)	0.34120 (15)	0.0316 (4)
C11	0.3662 (4)	0.2412 (4)	0.5169 (2)	0.0783 (11)
H11A	0.4110	0.3401	0.5363	0.094*
H11B	0.2581	0.2546	0.4950	0.094*
C12	0.3972 (3)	0.1377 (5)	0.6044 (2)	0.0764 (10)
H12A	0.3521	0.1767	0.6594	0.115*
H12B	0.5043	0.1290	0.6277	0.115*
H12C	0.3556	0.0391	0.5839	0.115*
C13	1.07596 (19)	0.8265 (2)	0.27877 (13)	0.0236 (4)
C14	1.1631 (2)	0.7069 (2)	0.32717 (15)	0.0309 (4)
H14	1.2039	0.6351	0.2884	0.037*
C15	1.1882 (2)	0.6960 (3)	0.43361 (15)	0.0355 (5)
H15	1.2487	0.6179	0.4668	0.043*
C16	1.1239 (2)	0.8006 (2)	0.49155 (15)	0.0304 (4)
C17	1.0371 (3)	0.9201 (3)	0.44266 (16)	0.0367 (5)
H17	0.9944	0.9908	0.4812	0.044*
C18	1.0144 (2)	0.9330 (2)	0.33620 (16)	0.0342 (5)
H18	0.9577	1.0136	0.3031	0.041*
C19	1.0760 (3)	0.8738 (3)	0.65678 (15)	0.0430 (6)
H19A	1.0906	0.8351	0.7261	0.065*
H19B	0.9700	0.8764	0.6276	0.065*
H19C	1.1167	0.9751	0.6576	0.065*
N1	0.87396 (16)	0.88540 (16)	0.10220 (11)	0.0222 (3)
H1	0.8609	0.9762	0.1044	0.027*
N2	0.61166 (17)	0.40098 (17)	0.14153 (11)	0.0224 (3)
N3	0.46167 (16)	0.38390 (16)	0.14178 (10)	0.0202 (3)
O1	1.08832 (15)	0.70535 (16)	0.10224 (10)	0.0269 (3)
O2	1.13045 (15)	0.98256 (17)	0.12154 (11)	0.0315 (3)
O3	0.29906 (17)	0.3482 (2)	0.32659 (11)	0.0450 (4)
O4	0.4297 (2)	0.1772 (2)	0.43247 (11)	0.0520 (5)
O5	1.15167 (18)	0.77637 (19)	0.59538 (11)	0.0411 (4)
O6	0.83323 (15)	0.19739 (15)	0.10176 (10)	0.0297 (3)
H6A	0.7633	0.2565	0.1151	0.036*
H6B	0.8488	0.2280	0.0427	0.036*
S1	1.05094 (4)	0.84904 (5)	0.14406 (3)	0.02171 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0167 (9)	0.0247 (8)	0.0181 (8)	0.0017 (7)	0.0040 (7)	−0.0004 (6)
C2	0.0208 (8)	0.0207 (8)	0.0237 (8)	0.0050 (7)	0.0055 (6)	0.0004 (7)
C3	0.0171 (9)	0.0250 (8)	0.0257 (9)	0.0078 (7)	0.0061 (7)	0.0006 (7)
C4	0.0192 (9)	0.0241 (9)	0.0173 (8)	0.0040 (7)	0.0038 (7)	0.0000 (6)
C5	0.0181 (8)	0.0219 (8)	0.0166 (8)	0.0047 (7)	0.0015 (6)	0.0002 (6)
C6	0.0157 (8)	0.0243 (9)	0.0243 (9)	0.0078 (7)	0.0044 (7)	0.0019 (7)
C7	0.0192 (9)	0.0253 (9)	0.0202 (8)	0.0051 (7)	0.0044 (7)	−0.0011 (7)
C8	0.0209 (9)	0.0225 (9)	0.0287 (9)	−0.0006 (7)	0.0043 (7)	−0.0027 (7)
C9	0.0273 (10)	0.0234 (9)	0.0319 (10)	0.0020 (7)	0.0073 (8)	0.0031 (7)
C10	0.0330 (11)	0.0330 (10)	0.0309 (10)	0.0010 (9)	0.0112 (8)	0.0053 (8)
C11	0.110 (3)	0.097 (2)	0.0363 (14)	0.036 (2)	0.0350 (16)	0.0102 (15)
C12	0.0642 (19)	0.129 (3)	0.0388 (14)	−0.015 (2)	0.0174 (13)	0.0096 (17)
C13	0.0187 (8)	0.0259 (9)	0.0256 (8)	−0.0004 (7)	0.0026 (7)	−0.0019 (7)
C14	0.0290 (11)	0.0319 (10)	0.0319 (10)	0.0091 (8)	0.0062 (8)	0.0010 (8)
C15	0.0344 (11)	0.0375 (11)	0.0334 (10)	0.0094 (9)	0.0033 (9)	0.0082 (9)
C16	0.0251 (10)	0.0354 (10)	0.0289 (10)	−0.0046 (7)	0.0010 (8)	0.0003 (7)
C17	0.0404 (12)	0.0377 (11)	0.0321 (10)	0.0088 (9)	0.0072 (9)	−0.0068 (8)
C18	0.0362 (12)	0.0331 (10)	0.0319 (10)	0.0124 (9)	0.0028 (9)	−0.0011 (8)
C19	0.0374 (12)	0.0635 (17)	0.0277 (10)	−0.0016 (11)	0.0051 (8)	−0.0046 (10)
N1	0.0180 (8)	0.0188 (7)	0.0298 (7)	0.0047 (5)	0.0047 (6)	0.0040 (6)
N2	0.0190 (8)	0.0228 (7)	0.0259 (7)	0.0033 (6)	0.0053 (6)	0.0013 (6)
N3	0.0178 (7)	0.0217 (8)	0.0209 (7)	0.0018 (6)	0.0033 (5)	0.0001 (5)
O1	0.0208 (7)	0.0314 (7)	0.0300 (7)	0.0056 (6)	0.0084 (5)	−0.0007 (6)
O2	0.0203 (7)	0.0324 (7)	0.0438 (8)	−0.0005 (6)	0.0114 (6)	0.0073 (6)
O3	0.0536 (9)	0.0433 (8)	0.0434 (8)	0.0182 (9)	0.0227 (7)	0.0073 (8)
O4	0.0646 (11)	0.0640 (11)	0.0303 (8)	0.0236 (9)	0.0165 (8)	0.0126 (7)
O5	0.0444 (9)	0.0506 (9)	0.0262 (8)	0.0047 (7)	0.0020 (6)	0.0013 (6)
O6	0.0334 (8)	0.0249 (7)	0.0335 (7)	0.0082 (6)	0.0133 (6)	0.0030 (5)
S1	0.0152 (2)	0.0246 (2)	0.0263 (2)	0.00303 (17)	0.00648 (15)	0.00187 (18)

Geometric parameters (Å, º)

C1—C6	1.374 (2)	C12—H12A	0.9600
C1—N1	1.418 (2)	C12—H12B	0.9600
C1—C2	1.431 (2)	C12—H12C	0.9600
C2—C3	1.353 (3)	C13—C18	1.383 (2)
C2—H2	0.9300	C13—C14	1.390 (3)
C3—C4	1.419 (2)	C13—S1	1.7572 (17)
C3—H3	0.9300	C14—C15	1.381 (3)
C4—C7	1.387 (2)	C14—H14	0.9300
C4—C5	1.422 (2)	C15—C16	1.389 (3)
C5—N2	1.357 (2)	C15—H15	0.9300
C5—C6	1.411 (2)	C16—O5	1.360 (2)
C6—H6	0.9300	C16—C17	1.390 (3)
C7—N3	1.337 (2)	C17—C18	1.383 (3)
C7—H7	0.9300	C17—H17	0.9300
C8—N3	1.458 (2)	C18—H18	0.9300
C8—C9	1.514 (3)	C19—O5	1.436 (3)
C8—H8A	0.9700	C19—H19A	0.9600
C8—H8B	0.9700	C19—H19B	0.9600
C9—C10	1.506 (3)	C19—H19C	0.9600
C9—H9A	0.9700	N1—S1	1.6183 (14)
C9—H9B	0.9700	N1—H1	0.8050
C10—O3	1.196 (3)	N2—N3	1.363 (2)
C10—O4	1.326 (2)	O1—S1	1.4399 (14)
C11—C12	1.451 (4)	O2—S1	1.4327 (14)
C11—O4	1.458 (3)	O6—H6A	0.8601
C11—H11A	0.9700	O6—H6B	0.8600
C11—H11B	0.9700
C6—C1—N1	124.49 (16)	H12A—C12—H12B	109.5
C6—C1—C2	121.23 (17)	C11—C12—H12C	109.5
N1—C1—C2	114.23 (15)	H12A—C12—H12C	109.5
C3—C2—C1	122.16 (17)	H12B—C12—H12C	109.5
C3—C2—H2	118.9	C18—C13—C14	120.58 (17)
C1—C2—H2	118.9	C18—C13—S1	119.33 (14)
C2—C3—C4	118.27 (17)	C14—C13—S1	120.01 (14)
C2—C3—H3	120.9	C15—C14—C13	119.13 (18)
C4—C3—H3	120.9	C15—C14—H14	120.4
C7—C4—C3	135.97 (17)	C13—C14—H14	120.4
C7—C4—C5	104.64 (15)	C14—C15—C16	120.55 (19)
C3—C4—C5	119.38 (16)	C14—C15—H15	119.7
N2—C5—C6	127.09 (15)	C16—C15—H15	119.7
N2—C5—C4	111.00 (15)	O5—C16—C15	115.76 (18)
C6—C5—C4	121.91 (16)	O5—C16—C17	124.24 (18)
C1—C6—C5	117.01 (16)	C15—C16—C17	120.01 (18)
C1—C6—H6	121.5	C18—C17—C16	119.51 (18)
C5—C6—H6	121.5	C18—C17—H17	120.2
N3—C7—C4	106.95 (15)	C16—C17—H17	120.2
N3—C7—H7	126.5	C17—C18—C13	120.20 (18)
C4—C7—H7	126.5	C17—C18—H18	119.9
N3—C8—C9	112.72 (15)	C13—C18—H18	119.9
N3—C8—H8A	109.0	O5—C19—H19A	109.5
C9—C8—H8A	109.0	O5—C19—H19B	109.5
N3—C8—H8B	109.0	H19A—C19—H19B	109.5
C9—C8—H8B	109.0	O5—C19—H19C	109.5
H8A—C8—H8B	107.8	H19A—C19—H19C	109.5
C10—C9—C8	112.84 (16)	H19B—C19—H19C	109.5
C10—C9—H9A	109.0	C1—N1—S1	125.60 (12)
C8—C9—H9A	109.0	C1—N1—H1	117.6
C10—C9—H9B	109.0	S1—N1—H1	108.9
C8—C9—H9B	109.0	C5—N2—N3	103.70 (13)
H9A—C9—H9B	107.8	C7—N3—N2	113.70 (14)
O3—C10—O4	123.80 (19)	C7—N3—C8	126.97 (15)
O3—C10—C9	125.49 (18)	N2—N3—C8	119.33 (14)
O4—C10—C9	110.70 (17)	C10—O4—C11	115.4 (2)
C12—C11—O4	108.8 (3)	C16—O5—C19	117.30 (17)
C12—C11—H11A	109.9	H6A—O6—H6B	104.5
O4—C11—H11A	109.9	O2—S1—O1	118.09 (7)
C12—C11—H11B	109.9	O2—S1—N1	105.63 (8)
O4—C11—H11B	109.9	O1—S1—N1	109.27 (8)
H11A—C11—H11B	108.3	O2—S1—C13	109.18 (9)
C11—C12—H12A	109.5	O1—S1—C13	107.13 (8)
C11—C12—H12B	109.5	N1—S1—C13	107.07 (8)
C6—C1—C2—C3	−1.5 (3)	C14—C13—C18—C17	−1.1 (3)
N1—C1—C2—C3	175.96 (15)	S1—C13—C18—C17	−177.88 (17)
C1—C2—C3—C4	1.9 (3)	C6—C1—N1—S1	−26.6 (2)
C2—C3—C4—C7	178.80 (18)	C2—C1—N1—S1	155.99 (12)
C2—C3—C4—C5	−0.4 (3)	C6—C5—N2—N3	−179.35 (15)
C7—C4—C5—N2	−0.54 (19)	C4—C5—N2—N3	0.25 (18)
C3—C4—C5—N2	178.89 (15)	C4—C7—N3—N2	−0.50 (19)
C7—C4—C5—C6	179.08 (15)	C4—C7—N3—C8	179.99 (15)
C3—C4—C5—C6	−1.5 (2)	C5—N2—N3—C7	0.16 (18)
N1—C1—C6—C5	−177.59 (14)	C5—N2—N3—C8	179.70 (14)
C2—C1—C6—C5	−0.4 (2)	C9—C8—N3—C7	−111.10 (19)
N2—C5—C6—C1	−178.61 (17)	C9—C8—N3—N2	69.41 (19)
C4—C5—C6—C1	1.8 (2)	O3—C10—O4—C11	0.0 (4)
C3—C4—C7—N3	−178.7 (2)	C9—C10—O4—C11	−178.6 (2)
C5—C4—C7—N3	0.61 (18)	C12—C11—O4—C10	167.3 (3)
N3—C8—C9—C10	70.9 (2)	C15—C16—O5—C19	−174.48 (19)
C8—C9—C10—O3	−1.3 (3)	C17—C16—O5—C19	5.2 (3)
C8—C9—C10—O4	177.17 (17)	C1—N1—S1—O2	−176.12 (14)
C18—C13—C14—C15	−0.3 (3)	C1—N1—S1—O1	55.87 (16)
S1—C13—C14—C15	176.48 (16)	C1—N1—S1—C13	−59.84 (16)
C13—C14—C15—C16	1.8 (3)	C18—C13—S1—O2	66.47 (17)
C14—C15—C16—O5	177.83 (19)	C14—C13—S1—O2	−110.37 (16)
C14—C15—C16—C17	−1.9 (3)	C18—C13—S1—O1	−164.56 (15)
O5—C16—C17—C18	−179.2 (2)	C14—C13—S1—O1	18.60 (18)
C15—C16—C17—C18	0.5 (3)	C18—C13—S1—N1	−47.44 (18)
C16—C17—C18—C13	1.0 (3)	C14—C13—S1—N1	135.72 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···N2	0.86	1.94	2.8029 (19)	176
N1—H1···O6^i	0.81	1.95	2.7575 (19)	177
O6—H6B···O1^ii	0.86	2.10	2.9094 (17)	156

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