3-Cyclo­hexyl­sulfan­yl-2-(4-methyl­phen­yl)-5,7-dinitro-1H-indole

Ramesh, P.; Subbiahpandi, A.; Manikannan, R.; Muthusubramanian, S.; Ponnuswamy, M.N.

doi:10.1107/S1600536808027682

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1890

doi:10.1107/S1600536808027682

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3-Cyclohexylsulfanyl-2-(4-methylphenyl)-5,7-dinitro-1H-indole

P. Ramesh,^a A. Subbiahpandi,^a Ramaiyan Manikannan,^b S. Muthusubramanian ^b and M. N. Ponnuswamy ^c ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 11 August 2008; accepted 28 August 2008; online 6 September 2008)

In the title compound, C₂₁H₂₁N₃O₄S, the cyclohexane ring adopts a chair conformation. The nitro and methylphenyl groups are all coplanar with the indole ring system. Intramolecular N—H⋯O and C—H⋯S hydrogen bonds generate S(6) ring motifs. The molecules form R₂²(20) centrosymmetric dimers via intermolecular C—H⋯O hydrogen bonds. A short O⋯O contact [2.842 (2) Å] is observed in the dimer.

Related literature

For related literature, see: Cordell (1981 ); Farhanullah et al. (2004 ). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₁H₂₁N₃O₄S
M_r = 411.47
Triclinic, $[P \overline 1]$
a = 6.1009 (3) Å
b = 8.5237 (4) Å
c = 19.1522 (10) Å
α = 83.551 (3)°
β = 84.184 (3)°
γ = 81.157 (2)°
V = 974.30 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.953, T_max = 0.969
21439 measured reflections
4586 independent reflections
3424 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.170
S = 1.05
4586 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.82 (2)	2.30 (2)	2.755 (2)	115 (2)
C19—H19⋯S1	0.93	2.62	3.347 (2)	135
C22—H22⋯O2ⁱ	0.93	2.58	3.224 (3)	127
Symmetry code: (i) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, (1997 )); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027682/ci2656sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027682/ci2656Isup2.hkl

checkCIF report

Comment top

Indole, being an integral part of many natural products of therapeutic importance, possesses potentially reactive sites for a variety of chemical reactions to generate molecular diversity (Farhanullah et al., 2004). The spiro-indole ring system is a frequently encountered structural motif in many biologically important and pharmacologically relevant alkaloids, e.g. vincrinstine, vinblastine and spirotypostatins (Cordell, 1981). Against this background and to ascertain the detailed information on its molecular conformation, the structure determination of the title compound was carried out.

The indole ring system is planar and the two nitro groups are coplanar with it. The cyclohexane ring adopts a chair conformation, with puckering parameters (Cremer & Pople, 1975) q₂ = 0.010 (3) Å, q₃ = 0.574 (3) Å and ϕ = 51 (18)°. The methylphenyl group is also coplanar with the indole ring system [dihedral angle 1.98 (9)°]. Each of the intramolecular N1—H1···O1 and C19—H19···S1 hydrogen bonds generates an S(6) ring motif (Bernstein et al. 1995).

In the crystal structure, molecules at (x, y, z) and (-x, 1-y, -z) are linked into a centrosymmetric R₂²(20) dimer by C22—H22···O2 hydrogen bonds. Within the dimer, a short O1···O1 contact [2.842 (2) Å] is observed.

Related literature top

For related literature, see: Cordell (1981); Farhanullah et al. (2004). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

A solution of 2-(cyclohexylsulfanyl)-1-(4-methylphenyl)-1-ethanone- N-(2,4-dinitrophenyl)hydrazone (0.001 mol) in dimethylforamide (5 ml) was allowed to cool in an ice bath with stirring. To this stirred solution, phosphorus oxychloride (0.008 mol) was added dropwise and the mixture was subjected to microwave irritation for 30–60 sec under 40% power with a pulse rate of 15 s. The reaction was monitored by TLC and after completion of the reaction, the reaction mixture was poured onto the crushed ice. The solid was filtered and washed with plenty of water. The different compounds present in the mixture were separated by column chromatography using petroleum ether and ethyl acetate mixture as eluent. The title compound was recrystallized in dichloromethane in 10% yield.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, (1997)); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. Molecular structure of the title compound, showing the atomic numbering and 50% probability displacement ellipsoids. Dashed lines indicate hydrogen bonds.

3-(Cyclohexylsulfanyl)-2-(4-methylphenyl)-5,7-dinitro-1H-indole top

Crystal data top

C₂₁H₂₁N₃O₄S	Z = 2
M_r = 411.47	F(000) = 432
Triclinic, P1	D_x = 1.403 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1009 (3) Å	Cell parameters from 4582 reflections
b = 8.5237 (4) Å	θ = 1.1–27.9°
c = 19.1522 (10) Å	µ = 0.20 mm⁻¹
α = 83.551 (3)°	T = 293 K
β = 84.184 (3)°	Block, colourless
γ = 81.157 (2)°	0.30 × 0.20 × 0.16 mm
V = 974.30 (8) Å³

Data collection top

Bruker Kappa APEXII area-detector diffractometer	4586 independent reflections
Radiation source: fine-focus sealed tube	3424 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω and ϕ scans	θ_max = 27.9°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −7→8
T_min = 0.953, T_max = 0.969	k = −11→11
21439 measured reflections	l = −25→25

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0969P)² + 0.289P] where P = (F_o² + 2F_c²)/3
4586 reflections	(Δ/σ)_max = 0.043
267 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₁H₂₁N₃O₄S	γ = 81.157 (2)°
M_r = 411.47	V = 974.30 (8) Å³
Triclinic, P1	Z = 2
a = 6.1009 (3) Å	Mo Kα radiation
b = 8.5237 (4) Å	µ = 0.20 mm⁻¹
c = 19.1522 (10) Å	T = 293 K
α = 83.551 (3)°	0.30 × 0.20 × 0.16 mm
β = 84.184 (3)°

Data collection top

Bruker Kappa APEXII area-detector diffractometer	4586 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3424 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.969	R_int = 0.036
21439 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.54 e Å⁻³
4586 reflections	Δρ_min = −0.31 e Å⁻³
267 parameters

Special details top

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

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

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

	x	y	z	U_iso*/U_eq
S1	0.37693 (9)	0.57116 (6)	0.32294 (3)	0.04681 (19)
O1	−0.1393 (3)	0.6217 (2)	0.03507 (9)	0.0579 (4)
O2	−0.4543 (3)	0.7672 (3)	0.05530 (10)	0.0796 (7)
O3	−0.6221 (3)	1.0174 (3)	0.26759 (12)	0.0825 (6)
O4	−0.3829 (4)	0.9921 (3)	0.34373 (11)	0.0856 (7)
N1	0.1558 (3)	0.5458 (2)	0.13764 (10)	0.0390 (4)
H1	0.157 (4)	0.513 (3)	0.0989 (13)	0.038 (6)*
C2	−0.0106 (3)	0.6496 (2)	0.16537 (10)	0.0372 (4)
C3	−0.2102 (3)	0.7282 (2)	0.14075 (10)	0.0394 (4)
C4	−0.3508 (3)	0.8295 (2)	0.18166 (12)	0.0442 (5)
H4	−0.4843	0.8820	0.1657	0.053*
C5	−0.2909 (4)	0.8521 (2)	0.24679 (11)	0.0444 (5)
C6	−0.0973 (4)	0.7772 (2)	0.27392 (11)	0.0444 (5)
H6	−0.0619	0.7956	0.3181	0.053*
C7	0.0435 (3)	0.6731 (2)	0.23291 (11)	0.0395 (4)
C8	0.2509 (3)	0.5755 (2)	0.24487 (11)	0.0403 (4)
C9	0.3180 (3)	0.4986 (2)	0.18474 (10)	0.0383 (4)
N10	−0.2723 (3)	0.7050 (2)	0.07243 (10)	0.0481 (4)
N11	−0.4432 (4)	0.9614 (2)	0.28929 (11)	0.0577 (5)
C12	0.3142 (3)	0.3850 (2)	0.37195 (10)	0.0419 (4)
H12	0.4020	0.2959	0.3489	0.050*
C13	0.0732 (4)	0.3632 (3)	0.37755 (15)	0.0607 (6)
H13A	0.0268	0.3586	0.3309	0.073*
H13B	−0.0175	0.4531	0.3981	0.073*
C14	0.0406 (5)	0.2098 (3)	0.42342 (17)	0.0743 (8)
H14A	−0.1161	0.1982	0.4283	0.089*
H14B	0.1219	0.1197	0.4007	0.089*
C15	0.1201 (6)	0.2090 (4)	0.49543 (16)	0.0852 (10)
H15A	0.0299	0.2933	0.5199	0.102*
H15B	0.1024	0.1080	0.5227	0.102*
C16	0.3607 (6)	0.2331 (4)	0.49010 (16)	0.0825 (9)
H16A	0.4528	0.1429	0.4703	0.099*
H16B	0.4052	0.2390	0.5368	0.099*
C17	0.3957 (5)	0.3857 (3)	0.44377 (13)	0.0603 (6)
H17A	0.3161	0.4768	0.4662	0.072*
H17B	0.5528	0.3959	0.4385	0.072*
C18	0.5160 (3)	0.3879 (2)	0.16483 (11)	0.0400 (4)
C19	0.6844 (4)	0.3372 (3)	0.20963 (12)	0.0499 (5)
H19	0.6706	0.3738	0.2540	0.060*
C20	0.8705 (4)	0.2343 (3)	0.18971 (13)	0.0530 (5)
H20	0.9801	0.2029	0.2209	0.064*
C21	0.8985 (3)	0.1762 (3)	0.12438 (13)	0.0467 (5)
C22	0.7331 (4)	0.2260 (3)	0.07958 (14)	0.0560 (6)
H22	0.7480	0.1890	0.0352	0.067*
C23	0.5454 (4)	0.3299 (3)	0.09918 (12)	0.0518 (5)
H23	0.4367	0.3615	0.0677	0.062*
C24	1.1020 (4)	0.0629 (3)	0.10306 (16)	0.0616 (6)
H24A	1.0768	0.0150	0.0621	0.092*
H24B	1.1321	−0.0188	0.1410	0.092*
H24C	1.2269	0.1202	0.0924	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0558 (3)	0.0444 (3)	0.0442 (3)	−0.0110 (2)	−0.0198 (2)	−0.0025 (2)
O1	0.0530 (9)	0.0732 (11)	0.0447 (9)	0.0112 (8)	−0.0118 (7)	−0.0152 (8)
O2	0.0584 (11)	0.1142 (16)	0.0618 (11)	0.0323 (10)	−0.0311 (9)	−0.0277 (11)
O3	0.0664 (12)	0.0930 (15)	0.0803 (14)	0.0314 (11)	−0.0120 (10)	−0.0287 (11)
O4	0.1046 (16)	0.0878 (14)	0.0585 (12)	0.0318 (12)	−0.0201 (11)	−0.0321 (11)
N1	0.0373 (8)	0.0439 (9)	0.0351 (9)	−0.0011 (7)	−0.0091 (7)	−0.0024 (7)
C2	0.0382 (9)	0.0360 (9)	0.0368 (10)	−0.0057 (7)	−0.0047 (7)	0.0006 (7)
C3	0.0396 (10)	0.0408 (10)	0.0368 (10)	−0.0033 (8)	−0.0070 (8)	0.0009 (8)
C4	0.0414 (10)	0.0416 (10)	0.0474 (12)	−0.0011 (8)	−0.0062 (8)	0.0013 (9)
C5	0.0493 (11)	0.0386 (10)	0.0427 (11)	−0.0002 (8)	−0.0021 (9)	−0.0028 (8)
C6	0.0542 (12)	0.0401 (10)	0.0388 (11)	−0.0042 (9)	−0.0080 (9)	−0.0026 (8)
C7	0.0435 (10)	0.0369 (10)	0.0385 (10)	−0.0079 (8)	−0.0080 (8)	0.0020 (8)
C8	0.0425 (10)	0.0386 (10)	0.0406 (11)	−0.0074 (8)	−0.0103 (8)	0.0012 (8)
C9	0.0364 (9)	0.0395 (10)	0.0394 (10)	−0.0065 (7)	−0.0103 (7)	0.0017 (8)
N10	0.0442 (9)	0.0563 (11)	0.0421 (10)	0.0028 (8)	−0.0110 (7)	−0.0045 (8)
N11	0.0683 (13)	0.0500 (11)	0.0498 (12)	0.0095 (9)	−0.0056 (9)	−0.0080 (9)
C12	0.0511 (11)	0.0393 (10)	0.0353 (10)	−0.0009 (8)	−0.0099 (8)	−0.0050 (8)
C13	0.0592 (14)	0.0618 (15)	0.0637 (16)	−0.0165 (12)	−0.0139 (11)	0.0015 (12)
C14	0.0739 (18)	0.0625 (16)	0.086 (2)	−0.0213 (14)	0.0013 (15)	0.0030 (15)
C15	0.123 (3)	0.0659 (18)	0.0593 (18)	−0.0139 (18)	0.0167 (18)	0.0067 (14)
C16	0.117 (3)	0.0775 (19)	0.0515 (16)	−0.0137 (18)	−0.0255 (16)	0.0155 (14)
C17	0.0774 (17)	0.0627 (14)	0.0435 (13)	−0.0102 (12)	−0.0243 (11)	0.0011 (11)
C18	0.0365 (9)	0.0397 (10)	0.0435 (11)	−0.0053 (8)	−0.0088 (8)	0.0022 (8)
C19	0.0439 (11)	0.0604 (13)	0.0445 (12)	−0.0005 (10)	−0.0111 (9)	−0.0040 (10)
C20	0.0392 (11)	0.0626 (14)	0.0554 (13)	−0.0009 (9)	−0.0161 (9)	0.0039 (11)
C21	0.0387 (10)	0.0424 (11)	0.0575 (13)	−0.0035 (8)	−0.0095 (9)	0.0031 (9)
C22	0.0504 (12)	0.0610 (14)	0.0555 (14)	0.0068 (10)	−0.0132 (10)	−0.0142 (11)
C23	0.0463 (11)	0.0566 (13)	0.0514 (13)	0.0081 (9)	−0.0184 (9)	−0.0093 (10)
C24	0.0446 (12)	0.0570 (14)	0.0777 (18)	0.0057 (10)	−0.0055 (11)	−0.0003 (12)

Geometric parameters (Å, º) top

S1—C8	1.744 (2)	C13—H13B	0.97
S1—C12	1.823 (2)	C14—C15	1.507 (4)
O1—N10	1.223 (2)	C14—H14A	0.97
O2—N10	1.215 (2)	C14—H14B	0.97
O3—N11	1.216 (3)	C15—C16	1.505 (5)
O4—N11	1.208 (3)	C15—H15A	0.97
N1—C2	1.347 (2)	C15—H15B	0.97
N1—C9	1.390 (2)	C16—C17	1.521 (4)
N1—H1	0.82 (2)	C16—H16A	0.97
C2—C3	1.396 (3)	C16—H16B	0.97
C2—C7	1.409 (3)	C17—H17A	0.97
C3—C4	1.373 (3)	C17—H17B	0.97
C3—N10	1.441 (3)	C18—C23	1.387 (3)
C4—C5	1.377 (3)	C18—C19	1.392 (3)
C4—H4	0.93	C19—C20	1.373 (3)
C5—C6	1.375 (3)	C19—H19	0.93
C5—N11	1.464 (3)	C20—C21	1.382 (4)
C6—C7	1.388 (3)	C20—H20	0.93
C6—H6	0.93	C21—C22	1.377 (3)
C7—C8	1.427 (3)	C21—C24	1.502 (3)
C8—C9	1.384 (3)	C22—C23	1.383 (3)
C9—C18	1.460 (3)	C22—H22	0.93
C12—C13	1.502 (3)	C23—H23	0.93
C12—C17	1.510 (3)	C24—H24A	0.96
C12—H12	0.98	C24—H24B	0.96
C13—C14	1.519 (4)	C24—H24C	0.96
C13—H13A	0.97

C8—S1—C12	103.22 (9)	C15—C14—H14A	109.3
C2—N1—C9	110.57 (17)	C13—C14—H14A	109.3
C2—N1—H1	124.1 (16)	C15—C14—H14B	109.3
C9—N1—H1	125.3 (16)	C13—C14—H14B	109.3
N1—C2—C3	133.05 (19)	H14A—C14—H14B	108.0
N1—C2—C7	107.39 (17)	C16—C15—C14	111.1 (2)
C3—C2—C7	119.55 (18)	C16—C15—H15A	109.4
C4—C3—C2	120.10 (19)	C14—C15—H15A	109.4
C4—C3—N10	118.89 (18)	C16—C15—H15B	109.4
C2—C3—N10	121.01 (18)	C14—C15—H15B	109.4
C3—C4—C5	118.86 (19)	H15A—C15—H15B	108.0
C3—C4—H4	120.6	C15—C16—C17	110.5 (2)
C5—C4—H4	120.6	C15—C16—H16A	109.5
C6—C5—C4	123.55 (19)	C17—C16—H16A	109.5
C6—C5—N11	118.6 (2)	C15—C16—H16B	109.5
C4—C5—N11	117.81 (19)	C17—C16—H16B	109.5
C5—C6—C7	117.57 (19)	H16A—C16—H16B	108.1
C5—C6—H6	121.2	C12—C17—C16	111.0 (2)
C7—C6—H6	121.2	C12—C17—H17A	109.4
C6—C7—C2	120.35 (18)	C16—C17—H17A	109.4
C6—C7—C8	132.23 (19)	C12—C17—H17B	109.4
C2—C7—C8	107.42 (17)	C16—C17—H17B	109.4
C9—C8—C7	106.84 (17)	H17A—C17—H17B	108.0
C9—C8—S1	131.38 (15)	C23—C18—C19	116.87 (19)
C7—C8—S1	121.76 (16)	C23—C18—C9	120.83 (18)
C8—C9—N1	107.76 (17)	C19—C18—C9	122.3 (2)
C8—C9—C18	132.49 (18)	C20—C19—C18	121.5 (2)
N1—C9—C18	119.74 (18)	C20—C19—H19	119.3
O2—N10—O1	123.43 (19)	C18—C19—H19	119.3
O2—N10—C3	118.61 (18)	C19—C20—C21	121.4 (2)
O1—N10—C3	117.96 (17)	C19—C20—H20	119.3
O4—N11—O3	123.6 (2)	C21—C20—H20	119.3
O4—N11—C5	118.0 (2)	C22—C21—C20	117.5 (2)
O3—N11—C5	118.3 (2)	C22—C21—C24	121.3 (2)
C13—C12—C17	111.4 (2)	C20—C21—C24	121.2 (2)
C13—C12—S1	114.70 (15)	C21—C22—C23	121.4 (2)
C17—C12—S1	105.15 (15)	C21—C22—H22	119.3
C13—C12—H12	108.5	C23—C22—H22	119.3
C17—C12—H12	108.5	C22—C23—C18	121.3 (2)
S1—C12—H12	108.5	C22—C23—H23	119.3
C12—C13—C14	109.6 (2)	C18—C23—H23	119.3
C12—C13—H13A	109.8	C21—C24—H24A	109.5
C14—C13—H13A	109.8	C21—C24—H24B	109.5
C12—C13—H13B	109.8	H24A—C24—H24B	109.5
C14—C13—H13B	109.8	C21—C24—H24C	109.5
H13A—C13—H13B	108.2	H24A—C24—H24C	109.5
C15—C14—C13	111.5 (2)	H24B—C24—H24C	109.5

C9—N1—C2—C3	−178.5 (2)	C2—C3—N10—O2	175.0 (2)
C9—N1—C2—C7	0.4 (2)	C4—C3—N10—O1	175.8 (2)
N1—C2—C3—C4	179.9 (2)	C2—C3—N10—O1	−4.1 (3)
C7—C2—C3—C4	1.1 (3)	C4—C3—N10—O1	175.8 (2)
N1—C2—C3—N10	−0.2 (3)	C2—C3—N10—O1	−4.1 (3)
C7—C2—C3—N10	−179.03 (18)	C6—C5—N11—O4	6.6 (3)
C2—C3—C4—C5	0.2 (3)	C4—C5—N11—O4	−173.8 (2)
N10—C3—C4—C5	−179.71 (19)	C6—C5—N11—O3	−174.2 (2)
C3—C4—C5—C6	−0.6 (3)	C4—C5—N11—O3	5.4 (3)
C3—C4—C5—N11	179.72 (19)	C8—S1—C12—C13	−50.48 (19)
C4—C5—C6—C7	−0.2 (3)	C8—S1—C12—C17	−173.23 (16)
N11—C5—C6—C7	179.44 (19)	C17—C12—C13—C14	−57.0 (3)
C5—C6—C7—C2	1.5 (3)	S1—C12—C13—C14	−176.27 (18)
C5—C6—C7—C8	−178.8 (2)	C12—C13—C14—C15	56.9 (3)
N1—C2—C7—C6	178.97 (18)	C13—C14—C15—C16	−56.9 (3)
C3—C2—C7—C6	−1.9 (3)	C14—C15—C16—C17	55.5 (4)
N1—C2—C7—C8	−0.8 (2)	C13—C12—C17—C16	57.0 (3)
C3—C2—C7—C8	178.26 (17)	S1—C12—C17—C16	−178.1 (2)
C6—C7—C8—C9	−178.8 (2)	C15—C16—C17—C12	−55.6 (3)
C2—C7—C8—C9	1.0 (2)	C8—C9—C18—C23	−178.5 (2)
C6—C7—C8—S1	−0.1 (3)	N1—C9—C18—C23	0.5 (3)
C2—C7—C8—S1	179.67 (14)	C8—C9—C18—C19	0.7 (4)
C12—S1—C8—C9	−79.3 (2)	N1—C9—C18—C19	179.66 (19)
C12—S1—C8—C7	102.35 (17)	C23—C18—C19—C20	−0.1 (3)
C7—C8—C9—N1	−0.7 (2)	C9—C18—C19—C20	−179.3 (2)
S1—C8—C9—N1	−179.26 (15)	C18—C19—C20—C21	−0.2 (4)
C7—C8—C9—C18	178.3 (2)	C19—C20—C21—C22	0.3 (4)
S1—C8—C9—C18	−0.2 (4)	C19—C20—C21—C24	−179.7 (2)
C2—N1—C9—C8	0.2 (2)	C20—C21—C22—C23	−0.2 (4)
C2—N1—C9—C18	−178.97 (17)	C24—C21—C22—C23	179.8 (2)
O1—O1—N10—O2	0.00 (4)	C21—C22—C23—C18	−0.1 (4)
O1—O1—N10—C3	0.00 (14)	C19—C18—C23—C22	0.2 (3)
C4—C3—N10—O2	−5.1 (3)	C9—C18—C23—C22	179.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.82 (2)	2.30 (2)	2.755 (2)	115 (2)
C19—H19···S1	0.93	2.62	3.347 (2)	135
C22—H22···O2ⁱ	0.93	2.58	3.224 (3)	127

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₃O₄S
M_r	411.47
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.1009 (3), 8.5237 (4), 19.1522 (10)
α, β, γ (°)	83.551 (3), 84.184 (3), 81.157 (2)
V (Å³)	974.30 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.953, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	21439, 4586, 3424
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.170, 1.05
No. of reflections	4586
No. of parameters	267
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.31

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, (1997)), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.82 (2)	2.30 (2)	2.755 (2)	115 (2)
C19—H19···S1	0.93	2.62	3.347 (2)	135
C22—H22···O2ⁱ	0.93	2.58	3.224 (3)	127

Symmetry code: (i) −x, −y+1, −z.

Acknowledgements

PR thanks Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for his help with the data collection.

References

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