2-Hydr­oxy-N-(3-oxo-1-thia-4-aza­spiro­[4.5]dec-4-yl)-2,2-diphenyl­acetamide

Akkurt, M.; Karaca, S.; Şahin, E.; Güzel, Ö.; Salman, A.; İlhan, E.

doi:10.1107/S1600536807031650

2-Hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide

M. Akkurt, S. Karaca, E. Şahin, Ö. Güzel, A. Salman and E. İlhan

In the molecule of the title compound, C₂₂H₂₄N₂O₃S, the dihedral angle between the two phenyl rings is 70.28 (11)°. The cyclohexane ring adopts a chair conformation while the thiazolidine ring assumes an envelope conformation. The crystal packing is stabilized by intramolecular N—H

O and intermolecular C—H

O and O—H

O hydrogen-bonding interactions. The structure also contains C—H

Cg interactions, where Cg is the centroid of the phenyl ring at (

); for this contact, C

Cg = 3.721 (3) Å, H

Cg = 2.82 Å and C—H

Cg = 162°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031650/hb2465sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031650/hb2465Isup2.hkl Contains datablock I

CCDC reference: 657667

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Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R factor = 0.056
wR factor = 0.174
Data-to-parameter ratio = 23.9

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Comment top

4-Thiazolidinones and their spiroheterocyclic analogs have been shown to possess antibacterial (Ateş et al., 1997; Andres et al., 2000), antifungal (Ulusoy et al., 1997; Çapan et al., 1999) and antituberculosis (Ulusoy, 2002; Karalı et al., 1998; Srivastava et al., 2005) activities. In our previous report (Güzel et al., 2006), we have synthesized and evaluated sixteen new 2-hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.4]non-4-yl)/(3-oxo-1-thia-4-αzaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide derivatives, incorporating the thiazolidinone substructure, as potential antimycobacterials. We now report the crystal structure of the title compound, (I), (Fig. 1), which has a non-planar conformation.

All bond lengths and angles in (I) are within normal ranges (Allen et al., 1987). The dihedral angle between the two phenyl rings is 70.28 (11)°. The five-membered ring (S1/N2/C15—C17) is not planar, with puckering parameters (Cremer & Pople, 1975) Q₂ = 0.2791 (18) Å and φ₂ = 171.1 (4) °. The C17—C22 cyclohexane ring has a normal chair conformation [puckering parameters: Q = 0.559 (2) Å, θ = 180.00 (2)° and φ = 341 (9) °].

The molecular conformation and crystal packing (Fig. 2) is stabilized by intramolecular N—H···O and intermolecular C—H···O and O—H···O hydrogen bonds (Table 1). The packing of (I) also features a C–H···π interaction, viz: C10—H10···Cg2(1 - x, -y, 1 - z), where Cg denotes the centre of the C1—C6 phenyl ring [C···Cg = 3.721 (3) Å, H···Cg = 2.82 Å and C–H···Cg = 162 °].

Related literature top

For related literature, see: Allen et al. (1987); Andres et al. (2000); Ateş et al. (1997); Çapan et al. (1999); Cremer & Pople (1975); Güzel et al. (2006); Karalı, Terzioğlu & Gürsoy (1998); Srivastava et al. (2005); Ulusoy (2002); Ulusoy et al. (1997).

Experimental top

A mixture of 2-hydroxy-2,2-diphenylacetohydrazide (0.005 mol), cyclohexanone (0.005 mol) and mercaptoacetic acid or α-mercaptopropionic acid (0.02 mol) was refluxed in 20 ml dry benzene for 5–6 h using a Dean-Stark water separator. Excess benzene was evaporated in vacuo. The resulting residue was titrated with saturated NaHCO₃solution until CO₂ evolution ceased and was allowed to stand overnight or in some cases refrigerated until solidification. The solid thus obtained was recrystallized from ethanol.

Yield 47%; mp 493–495 K; IR(KBr) (ν, cm^-1): 3354 (O—H/N—H), 1685, 1726 (C═O). ¹H-NMR (DMSO-d₆, 500 MHz) δ (p.p.m.): 0.80–1.07 (m, 1H, spirodecane), 1.34–1.38 (m, 2H, spirodecane), 1.49–1.63 (m, 5H, spirodecane), 1.73, 1.76 (2 s, 2H, spirodecane), 3.54 (s, 2H, C₂—H₂), 6.81 (s, 1H, COH), 7.28–7.35 (m, 6H, Ar—H), 7.46 (s, 2H, Ar—H), 7.47–7.48 (m, 2H, Ar—H), 10.21 (s, 1H, CONH). ¹³C-NMR (APT) (DMSO-d₆ / 125 MHz) δ (p.p.m.): 23.56 (C_7,9 spd.), 24.83 (C₈ spd.), 28.64 (C₂ spd.), 37.61 (C_6,10 spd.), 73.30 (C₅ spd.), 81.61 (C—OH), 128.05,128.25,128.30 (ar. CH), 144.40 (ar. C), 167.98 (amide C═O), 173.40 (lactam C═O). Analysis calculated for C₂₂H₂₄N₂O₃S (396.494): C 66.64, H 6.10, N 7.07%. Found: C 66.21, H 6.22, N 6.69%.

Structure description top

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 20% probability level (arbitrary spheres for the H atoms).
	Fig. 2. View of the packing and hydrogen bonding interactions (dashed lines) for (I). H atoms not involved in these bonds have been omitted for clarity.

2-Hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide top

Crystal data top

C₂₂H₂₄N₂O₃S	F(000) = 840
M_r = 396.50	D_x = 1.305 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 9135 reflections
a = 12.1676 (2) Å	θ = 2.1–30.5°
b = 9.3050 (2) Å	µ = 0.19 mm⁻¹
c = 17.9081 (3) Å	T = 294 K
β = 95.4236 (11)°	Prism, pale yellow
V = 2018.47 (6) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	6181 independent reflections
Radiation source: Sealed Tube	3693 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.067
Detector resolution: 10.0000 pixels mm^-1	θ_max = 30.7°, θ_min = 2.3°
ω scans	h = −17→17
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −13→11
T_min = 0.963, T_max = 0.963	l = −25→25
56688 measured reflections

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.174	w = 1/[σ²(F_o²) + (0.0679P)² + 0.3246P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
6181 reflections	Δρ_max = 0.28 e Å⁻³
259 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC²Λ³/sin(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0127 (15)

Crystal data top

C₂₂H₂₄N₂O₃S	V = 2018.47 (6) Å³
M_r = 396.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1676 (2) Å	µ = 0.19 mm⁻¹
b = 9.3050 (2) Å	T = 294 K
c = 17.9081 (3) Å	0.20 × 0.20 × 0.20 mm
β = 95.4236 (11)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	6181 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	3693 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.963	R_int = 0.067
56688 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.174	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.28 e Å⁻³
6181 reflections	Δρ_min = −0.32 e Å⁻³
259 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.80752 (5)	0.06874 (7)	0.00974 (3)	0.0757 (2)
O1	0.60444 (10)	0.26567 (12)	0.31383 (7)	0.0493 (4)
O2	0.57202 (11)	−0.04849 (13)	0.19848 (7)	0.0564 (4)
O3	0.52028 (12)	0.17812 (18)	0.06223 (9)	0.0772 (6)
N1	0.66222 (13)	0.16220 (17)	0.18918 (8)	0.0494 (5)
N2	0.69225 (12)	0.13232 (16)	0.11812 (8)	0.0484 (4)
C1	0.77259 (16)	0.1061 (2)	0.37823 (12)	0.0636 (7)
C2	0.85941 (19)	0.0326 (3)	0.41713 (15)	0.0809 (9)
C3	0.85038 (19)	−0.1121 (3)	0.43089 (13)	0.0778 (9)
C4	0.7553 (2)	−0.1830 (2)	0.40626 (13)	0.0738 (8)
C5	0.66836 (16)	−0.1106 (2)	0.36760 (11)	0.0592 (7)
C6	0.67673 (14)	0.03552 (18)	0.35312 (9)	0.0470 (5)
C7	0.58364 (13)	0.11450 (17)	0.30554 (9)	0.0440 (5)
C8	0.46878 (13)	0.07835 (18)	0.32601 (10)	0.0459 (5)
C9	0.44939 (17)	0.0643 (3)	0.40028 (12)	0.0698 (8)
C10	0.3446 (2)	0.0374 (3)	0.42036 (15)	0.0837 (10)
C11	0.25785 (18)	0.0262 (2)	0.36688 (17)	0.0777 (9)
C12	0.27456 (17)	0.0434 (2)	0.29364 (16)	0.0754 (9)
C13	0.38002 (16)	0.0703 (2)	0.27252 (12)	0.0582 (6)
C14	0.60133 (14)	0.06778 (18)	0.22493 (9)	0.0457 (5)
C15	0.61414 (16)	0.1364 (2)	0.05903 (11)	0.0568 (6)
C16	0.6604 (2)	0.0817 (3)	−0.01015 (12)	0.0760 (9)
C17	0.80025 (14)	0.06507 (18)	0.11158 (10)	0.0490 (5)
C18	0.89297 (16)	0.1561 (2)	0.15033 (12)	0.0604 (7)
C19	1.00600 (17)	0.0872 (2)	0.14582 (15)	0.0733 (8)
C20	1.00933 (19)	−0.0637 (3)	0.17748 (17)	0.0821 (9)
C21	0.91890 (18)	−0.1551 (2)	0.13800 (16)	0.0771 (9)
C22	0.80573 (16)	−0.0880 (2)	0.14201 (13)	0.0617 (7)
H1	0.77930	0.20390	0.36900	0.0760*
H1N	0.6718 (17)	0.247 (2)	0.2053 (11)	0.063 (6)*
H1O	0.54590	0.30960	0.30790	0.0740*
H2	0.92380	0.08140	0.43390	0.0970*
H3	0.90850	−0.16150	0.45680	0.0930*
H4	0.74910	−0.28090	0.41560	0.0890*
H5	0.60410	−0.15990	0.35130	0.0710*
H9	0.50780	0.07310	0.43740	0.0840*
H10	0.33320	0.02680	0.47070	0.1000*
H11	0.18750	0.00690	0.38050	0.0930*
H12	0.21510	0.03720	0.25710	0.0910*
H13	0.39040	0.08290	0.22210	0.0700*
H16A	0.64230	0.14710	−0.05170	0.0910*
H16B	0.62950	−0.01190	−0.02370	0.0910*
H18A	0.88030	0.16900	0.20260	0.0730*
H18B	0.89220	0.25030	0.12700	0.0730*
H19A	1.02250	0.08430	0.09390	0.0880*
H19B	1.06200	0.14530	0.17360	0.0880*
H20A	1.08050	−0.10680	0.17140	0.0990*
H20B	1.00030	−0.06010	0.23070	0.0990*
H21A	0.92010	−0.24960	0.16090	0.0930*
H21B	0.93260	−0.16690	0.08590	0.0930*
H22A	0.78830	−0.08730	0.19380	0.0740*
H22B	0.75070	−0.14630	0.11340	0.0740*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0720 (4)	0.1023 (5)	0.0557 (3)	0.0087 (3)	0.0218 (3)	−0.0021 (3)
O1	0.0509 (6)	0.0392 (6)	0.0576 (7)	0.0011 (5)	0.0048 (5)	−0.0026 (5)
O2	0.0601 (8)	0.0494 (7)	0.0618 (8)	−0.0122 (6)	0.0166 (6)	−0.0119 (6)
O3	0.0611 (9)	0.0903 (12)	0.0788 (10)	0.0182 (8)	−0.0009 (7)	−0.0057 (8)
N1	0.0578 (9)	0.0441 (8)	0.0484 (8)	−0.0049 (7)	0.0164 (6)	−0.0024 (6)
N2	0.0485 (8)	0.0522 (8)	0.0454 (7)	0.0019 (6)	0.0099 (6)	0.0003 (6)
C1	0.0505 (10)	0.0599 (12)	0.0784 (13)	−0.0005 (9)	−0.0039 (9)	0.0031 (10)
C2	0.0538 (12)	0.0871 (17)	0.0981 (18)	0.0035 (11)	−0.0126 (11)	0.0015 (13)
C3	0.0653 (13)	0.0869 (17)	0.0797 (15)	0.0255 (12)	−0.0016 (11)	0.0112 (12)
C4	0.0791 (15)	0.0571 (12)	0.0859 (16)	0.0150 (11)	0.0111 (12)	0.0159 (11)
C5	0.0567 (11)	0.0512 (11)	0.0701 (12)	0.0022 (8)	0.0076 (9)	0.0082 (9)
C6	0.0466 (9)	0.0471 (9)	0.0480 (9)	0.0035 (7)	0.0081 (7)	0.0020 (7)
C7	0.0457 (8)	0.0403 (8)	0.0465 (8)	−0.0020 (6)	0.0070 (6)	−0.0018 (6)
C8	0.0431 (8)	0.0429 (9)	0.0522 (9)	0.0027 (7)	0.0076 (7)	0.0016 (7)
C9	0.0540 (11)	0.1019 (18)	0.0553 (11)	0.0109 (11)	0.0147 (9)	0.0111 (11)
C10	0.0673 (14)	0.1045 (19)	0.0845 (16)	0.0194 (13)	0.0347 (12)	0.0258 (14)
C11	0.0544 (12)	0.0595 (13)	0.124 (2)	0.0012 (10)	0.0337 (13)	0.0064 (13)
C12	0.0468 (11)	0.0693 (14)	0.1084 (19)	0.0029 (10)	−0.0022 (11)	−0.0189 (12)
C13	0.0497 (10)	0.0600 (12)	0.0642 (11)	0.0046 (8)	0.0024 (8)	−0.0040 (9)
C14	0.0440 (8)	0.0449 (9)	0.0487 (9)	−0.0017 (7)	0.0076 (7)	0.0002 (7)
C15	0.0560 (11)	0.0582 (11)	0.0559 (10)	0.0037 (9)	0.0038 (8)	0.0014 (8)
C16	0.0789 (15)	0.0989 (18)	0.0498 (11)	0.0072 (13)	0.0047 (10)	−0.0041 (11)
C17	0.0477 (9)	0.0481 (9)	0.0524 (9)	0.0001 (7)	0.0111 (7)	0.0000 (7)
C18	0.0551 (10)	0.0511 (11)	0.0753 (13)	−0.0055 (8)	0.0079 (9)	−0.0041 (9)
C19	0.0494 (11)	0.0657 (13)	0.1045 (18)	−0.0076 (9)	0.0056 (11)	−0.0074 (12)
C20	0.0539 (12)	0.0706 (15)	0.120 (2)	0.0088 (10)	−0.0015 (12)	0.0030 (13)
C21	0.0608 (12)	0.0522 (12)	0.118 (2)	0.0049 (10)	0.0065 (12)	0.0013 (12)
C22	0.0532 (10)	0.0471 (10)	0.0852 (14)	−0.0025 (8)	0.0086 (9)	0.0042 (9)

Geometric parameters (Å, º) top

S1—C16	1.796 (3)	C17—C18	1.524 (3)
S1—C17	1.8346 (19)	C18—C19	1.526 (3)
O1—C7	1.4344 (19)	C19—C20	1.513 (3)
O2—C14	1.221 (2)	C20—C21	1.512 (3)
O3—C15	1.213 (2)	C21—C22	1.520 (3)
O1—H1O	0.8200	C1—H1	0.9300
N1—N2	1.385 (2)	C2—H2	0.9300
N1—C14	1.349 (2)	C3—H3	0.9300
N2—C15	1.354 (2)	C4—H4	0.9300
N2—C17	1.470 (2)	C5—H5	0.9300
N1—H1N	0.845 (19)	C9—H9	0.9300
C1—C6	1.377 (3)	C10—H10	0.9300
C1—C2	1.389 (3)	C11—H11	0.9300
C2—C3	1.375 (4)	C12—H12	0.9300
C3—C4	1.368 (3)	C13—H13	0.9300
C4—C5	1.383 (3)	C16—H16A	0.9700
C5—C6	1.390 (3)	C16—H16B	0.9700
C6—C7	1.538 (2)	C18—H18A	0.9700
C7—C14	1.542 (2)	C18—H18B	0.9700
C7—C8	1.516 (2)	C19—H19A	0.9700
C8—C13	1.376 (3)	C19—H19B	0.9700
C8—C9	1.379 (3)	C20—H20A	0.9700
C9—C10	1.380 (3)	C20—H20B	0.9700
C10—C11	1.361 (4)	C21—H21A	0.9700
C11—C12	1.356 (4)	C21—H21B	0.9700
C12—C13	1.394 (3)	C22—H22A	0.9700
C15—C16	1.498 (3)	C22—H22B	0.9700
C17—C22	1.524 (3)

C16—S1—C17	93.30 (9)	C6—C1—H1	120.00
C7—O1—H1O	109.00	C1—C2—H2	120.00
N2—N1—C14	120.64 (15)	C3—C2—H2	120.00
N1—N2—C15	119.06 (15)	C2—C3—H3	120.00
N1—N2—C17	118.30 (14)	C4—C3—H3	120.00
C15—N2—C17	121.08 (15)	C3—C4—H4	120.00
N2—N1—H1N	117.5 (13)	C5—C4—H4	120.00
C14—N1—H1N	120.7 (14)	C4—C5—H5	120.00
C2—C1—C6	120.64 (19)	C6—C5—H5	120.00
C1—C2—C3	120.1 (2)	C8—C9—H9	119.00
C2—C3—C4	119.6 (2)	C10—C9—H9	119.00
C3—C4—C5	120.65 (19)	C9—C10—H10	120.00
C4—C5—C6	120.25 (18)	C11—C10—H10	120.00
C1—C6—C5	118.73 (16)	C10—C11—H11	120.00
C1—C6—C7	120.65 (15)	C12—C11—H11	120.00
C5—C6—C7	120.51 (15)	C11—C12—H12	120.00
O1—C7—C6	107.32 (13)	C13—C12—H12	120.00
C6—C7—C14	102.90 (13)	C8—C13—H13	120.00
C8—C7—C14	112.17 (14)	C12—C13—H13	120.00
C6—C7—C8	114.05 (13)	S1—C16—H16A	110.00
O1—C7—C8	110.50 (13)	S1—C16—H16B	110.00
O1—C7—C14	109.54 (13)	C15—C16—H16A	110.00
C7—C8—C9	120.01 (16)	C15—C16—H16B	110.00
C7—C8—C13	121.64 (16)	H16A—C16—H16B	108.00
C9—C8—C13	118.14 (17)	C17—C18—H18A	109.00
C8—C9—C10	121.0 (2)	C17—C18—H18B	109.00
C9—C10—C11	120.3 (2)	C19—C18—H18A	109.00
C10—C11—C12	119.7 (2)	C19—C18—H18B	109.00
C11—C12—C13	120.6 (2)	H18A—C18—H18B	108.00
C8—C13—C12	120.2 (2)	C18—C19—H19A	109.00
O2—C14—N1	123.12 (15)	C18—C19—H19B	109.00
O2—C14—C7	123.48 (15)	C20—C19—H19A	109.00
N1—C14—C7	113.09 (14)	C20—C19—H19B	109.00
N2—C15—C16	110.24 (17)	H19A—C19—H19B	108.00
O3—C15—N2	124.51 (18)	C19—C20—H20A	110.00
O3—C15—C16	125.25 (19)	C19—C20—H20B	110.00
S1—C16—C15	107.72 (15)	C21—C20—H20A	109.00
S1—C17—N2	101.46 (11)	C21—C20—H20B	109.00
S1—C17—C18	109.82 (13)	H20A—C20—H20B	108.00
S1—C17—C22	111.61 (13)	C20—C21—H21A	109.00
N2—C17—C18	110.85 (14)	C20—C21—H21B	109.00
N2—C17—C22	112.24 (14)	C22—C21—H21A	109.00
C18—C17—C22	110.55 (15)	C22—C21—H21B	109.00
C17—C18—C19	111.98 (16)	H21A—C21—H21B	108.00
C18—C19—C20	111.24 (18)	C17—C22—H22A	109.00
C19—C20—C21	110.7 (2)	C17—C22—H22B	109.00
C20—C21—C22	111.67 (18)	C21—C22—H22A	109.00
C17—C22—C21	112.10 (16)	C21—C22—H22B	109.00
C2—C1—H1	120.00	H22A—C22—H22B	108.00

C17—S1—C16—C15	20.49 (17)	O1—C7—C8—C9	−80.3 (2)
C16—S1—C17—N2	−22.19 (14)	O1—C7—C8—C13	94.38 (19)
C16—S1—C17—C18	−139.52 (15)	C6—C7—C8—C9	40.7 (2)
C16—S1—C17—C22	97.53 (15)	C6—C7—C8—C13	−144.64 (16)
C14—N1—N2—C15	71.8 (2)	C14—C7—C8—C9	157.21 (18)
C14—N1—N2—C17	−94.09 (19)	C14—C7—C8—C13	−28.2 (2)
N2—N1—C14—O2	1.9 (3)	O1—C7—C14—O2	−167.35 (15)
N2—N1—C14—C7	175.65 (14)	O1—C7—C14—N1	18.93 (19)
N1—N2—C15—O3	7.5 (3)	C6—C7—C14—O2	78.74 (19)
N1—N2—C15—C16	−172.32 (17)	C6—C7—C14—N1	−94.98 (16)
C17—N2—C15—O3	172.97 (18)	C8—C7—C14—O2	−44.3 (2)
C17—N2—C15—C16	−6.8 (2)	C8—C7—C14—N1	142.02 (15)
N1—N2—C17—S1	−173.39 (12)	C7—C8—C9—C10	177.3 (2)
N1—N2—C17—C18	−56.8 (2)	C13—C8—C9—C10	2.5 (3)
N1—N2—C17—C22	67.3 (2)	C7—C8—C13—C12	−177.01 (16)
C15—N2—C17—S1	21.00 (18)	C9—C8—C13—C12	−2.3 (3)
C15—N2—C17—C18	137.58 (17)	C8—C9—C10—C11	−0.9 (4)
C15—N2—C17—C22	−98.3 (2)	C9—C10—C11—C12	−0.8 (4)
C6—C1—C2—C3	0.1 (4)	C10—C11—C12—C13	1.0 (3)
C2—C1—C6—C5	0.2 (3)	C11—C12—C13—C8	0.6 (3)
C2—C1—C6—C7	−175.90 (19)	O3—C15—C16—S1	168.39 (18)
C1—C2—C3—C4	−0.2 (4)	N2—C15—C16—S1	−11.8 (2)
C2—C3—C4—C5	0.1 (4)	S1—C17—C18—C19	−69.89 (19)
C3—C4—C5—C6	0.2 (3)	N2—C17—C18—C19	178.81 (16)
C4—C5—C6—C1	−0.3 (3)	C22—C17—C18—C19	53.7 (2)
C4—C5—C6—C7	175.79 (18)	S1—C17—C22—C21	69.1 (2)
C1—C6—C7—O1	−16.1 (2)	N2—C17—C22—C21	−177.74 (17)
C1—C6—C7—C8	−138.82 (17)	C18—C17—C22—C21	−53.4 (2)
C1—C6—C7—C14	99.44 (18)	C17—C18—C19—C20	−55.6 (3)
C5—C6—C7—O1	167.93 (15)	C18—C19—C20—C21	56.1 (3)
C5—C6—C7—C8	45.2 (2)	C19—C20—C21—C22	−56.0 (3)
C5—C6—C7—C14	−76.56 (19)	C20—C21—C22—C17	55.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.845 (19)	2.19 (2)	2.5886 (19)	109.1 (16)
O1—H1O···O2ⁱ	0.82	1.95	2.7494 (18)	167
C1—H1···O1	0.93	2.33	2.697 (2)	103
C13—H13···O2	0.93	2.59	3.004 (2)	107
C16—H16A···O1ⁱⁱ	0.97	2.54	3.466 (3)	159
C16—H16B···O3ⁱⁱⁱ	0.97	2.44	3.341 (3)	154

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₄N₂O₃S
M_r	396.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	12.1676 (2), 9.3050 (2), 17.9081 (3)
β (°)	95.4236 (11)
V (Å³)	2018.47 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.963, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	56688, 6181, 3693
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.717

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.174, 1.04
No. of reflections	6181
No. of parameters	259
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.32

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).