N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-[4-(methyl­sulfan­yl)phen­yl]acetamide

Fun, H.-K.; Quah, C.K.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812034605

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2677

doi:10.1107/S1600536812034605

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N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-[4-(methylsulfanyl)phenyl]acetamide

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Prakash S. Nayak,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 31 July 2012; accepted 3 August 2012; online 11 August 2012)

In the title compound, C₂₀H₂₁N₃O₂S, the 2,3-dihydro-1H-pyrazole ring is nearly planar (r.m.s. deviation = 0.023 Å) and forms dihedral angles of 16.96 (6) and 38.93 (6)° with the benzene and phenyl rings, respectively. The dihedral angle between the benzene and phenyl rings is 55.54 (6)°. The molecular conformation is consolidated by an intramolecular C—H⋯O hydrogen bond, which forms an S(6) ring. In the crystal, inversion dimers linked by pairs of N—H⋯O_p (p = pyrazole) hydrogen bonds generate R₂²(10) loops. The dimers are linked by C—H⋯O hydrogen bonds into sheets lying parallel to (100).

Related literature

For general background to the title compound and for related structures, see: Fun et al. (2011a ,b , 2012a ,b ). For the stability of the temperature controller used in the the data collection, see: Cosier & Glazer (1986 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₂₁N₃O₂S
M_r = 367.46
Monoclinic, P 2₁ /c
a = 14.9176 (8) Å
b = 6.6527 (4) Å
c = 19.5792 (10) Å
β = 110.689 (1)°
V = 1817.78 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.37 × 0.18 × 0.07 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.931, T_max = 0.987
19714 measured reflections
5302 independent reflections
4231 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.116
S = 1.03
5302 reflections
242 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2ⁱ	0.880 (19)	1.956 (19)	2.7816 (14)	155.7 (19)
C1—H1A⋯O1	0.95	2.38	3.0185 (16)	124
C1—H1A⋯O1ⁱⁱ	0.95	2.51	3.2342 (16)	133
C7—H7A⋯O1ⁱⁱⁱ	0.99	2.57	3.4960 (16)	155
C19—H19B⋯O2^iv	0.98	2.55	3.4470 (17)	152
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034605/hb6925sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034605/hb6925Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034605/hb6925Isup3.cml

checkCIF report

Comment top

In continuation of our work on synthesis of amides (Fun et al., 2011a, 2011b, 2012a, 2012b), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the 1H-pyrazol-4-yl ring (N2/N3/C9-C11) is nearly planar (r.m.s. deviation = 0.023 Å) and it forms dihedral angles of 16.96 (6) and 38.93 (6)° with the benzene (C1-C6) and phenyl (C12-C17) rings, respectively. The dihedral angle between the benzene and phenyl rings is 55.54 (6)°. Bond lengths and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a, 2011b, 2012a, 2012b). The molecular structure is stabilized by intramolecular C1–H1A···O1 hydrogen bond, forming an S(6) ring motif (Bernstein et al., 1995).

In the crystal structure, Fig. 2, molecules are linked via N1–H1N1···O2, C1–H1A···O1, C7–H7A···O1 and C19–H19B···O2 hydrogen bonds (Table 1) into two-dimensional plane parallel to (100) which contains R₂² (10) ring motifs (Bernstein et al., 1995).

Related literature top

For general background to the title compound and for related structures, see: Fun et al. (2011a,b, 2012a,b). For the stability of the temperature controller used in the the data collection, see: Cosier & Glazer (1986). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

[4-(Methylsulfanyl)phenyl]acetic acid (0.182 g, 1 mmol), 4-amino antipyrine (0.205 g, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 ml). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring. The concoction was extracted thrice with dichloromethane. The organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Yellow plates were grown from an acetone and toluene (1:1) solvent mixture by the slow evaporation method (m.p.: 415-418 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms. Intramolecular hydrogen bond is shown as dashed line.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)- 2-[4-(methylsulfanyl)phenyl]acetamide top

Crystal data top

C₂₀H₂₁N₃O₂S	F(000) = 776
M_r = 367.46	D_x = 1.343 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5722 reflections
a = 14.9176 (8) Å	θ = 2.9–30.0°
b = 6.6527 (4) Å	µ = 0.20 mm⁻¹
c = 19.5792 (10) Å	T = 100 K
β = 110.689 (1)°	Plate, yellow
V = 1817.78 (17) Å³	0.37 × 0.18 × 0.07 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	5302 independent reflections
Radiation source: fine-focus sealed tube	4231 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→21
T_min = 0.931, T_max = 0.987	k = −9→9
19714 measured reflections	l = −27→27

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.058P)² + 0.594P] where P = (F_o² + 2F_c²)/3
5302 reflections	(Δ/σ)_max = 0.001
242 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₂₀H₂₁N₃O₂S	V = 1817.78 (17) Å³
M_r = 367.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.9176 (8) Å	µ = 0.20 mm⁻¹
b = 6.6527 (4) Å	T = 100 K
c = 19.5792 (10) Å	0.37 × 0.18 × 0.07 mm
β = 110.689 (1)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	5302 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4231 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.987	R_int = 0.033
19714 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.42 e Å⁻³
5302 reflections	Δρ_min = −0.52 e Å⁻³
242 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.90518 (2)	1.11552 (8)	0.26045 (2)	0.03908 (13)
O1	0.48783 (6)	0.70169 (15)	0.28728 (5)	0.0201 (2)
O2	0.37745 (6)	0.49368 (14)	0.45147 (5)	0.01838 (19)
N1	0.54078 (7)	0.67806 (17)	0.41084 (6)	0.0162 (2)
N2	0.35044 (7)	1.00817 (16)	0.41536 (5)	0.0153 (2)
N3	0.31713 (7)	0.81906 (16)	0.42879 (5)	0.0155 (2)
C1	0.67740 (8)	0.8798 (2)	0.29532 (7)	0.0182 (2)
H1A	0.6135	0.9222	0.2866	0.022*
C2	0.73958 (9)	1.0064 (2)	0.27714 (7)	0.0201 (3)
H2A	0.7178	1.1344	0.2564	0.024*
C3	0.83366 (8)	0.9474 (2)	0.28906 (6)	0.0210 (3)
C4	0.86425 (8)	0.7580 (2)	0.31933 (6)	0.0215 (3)
H4A	0.9278	0.7148	0.3271	0.026*
C5	0.80202 (8)	0.6324 (2)	0.33817 (7)	0.0189 (3)
H5A	0.8240	0.5050	0.3594	0.023*
C6	0.70736 (8)	0.6908 (2)	0.32626 (6)	0.0162 (2)
C7	0.64106 (8)	0.5462 (2)	0.34610 (7)	0.0184 (2)
H7A	0.6251	0.4323	0.3113	0.022*
H7B	0.6750	0.4914	0.3956	0.022*
C8	0.54900 (8)	0.64688 (19)	0.34457 (6)	0.0155 (2)
C9	0.45856 (8)	0.7725 (2)	0.41579 (6)	0.0153 (2)
C10	0.43573 (8)	0.9695 (2)	0.40415 (6)	0.0154 (2)
C11	0.38429 (8)	0.6706 (2)	0.43345 (6)	0.0154 (2)
C12	0.24277 (8)	0.8087 (2)	0.45811 (6)	0.0158 (2)
C13	0.18356 (9)	0.6400 (2)	0.44282 (7)	0.0200 (3)
H13A	0.1934	0.5340	0.4137	0.024*
C14	0.10982 (10)	0.6290 (2)	0.47079 (8)	0.0251 (3)
H14A	0.0696	0.5138	0.4613	0.030*
C15	0.09484 (9)	0.7850 (2)	0.51241 (7)	0.0261 (3)
H15A	0.0439	0.7774	0.5308	0.031*
C16	0.15406 (9)	0.9525 (2)	0.52726 (7)	0.0233 (3)
H16A	0.1435	1.0593	0.5557	0.028*
C17	0.22911 (9)	0.9648 (2)	0.50060 (6)	0.0194 (3)
H17A	0.2704	1.0784	0.5114	0.023*
C18	1.02279 (10)	1.0805 (3)	0.32583 (8)	0.0324 (3)
H18A	1.0649	1.1877	0.3205	0.049*
H18B	1.0478	0.9499	0.3177	0.049*
H18C	1.0203	1.0846	0.3752	0.049*
C19	0.48791 (9)	1.1329 (2)	0.38237 (7)	0.0186 (2)
H19A	0.5565	1.1016	0.3998	0.028*
H19B	0.4779	1.2601	0.4039	0.028*
H19C	0.4638	1.1450	0.3291	0.028*
C20	0.27706 (9)	1.1291 (2)	0.36089 (7)	0.0188 (2)
H20A	0.3065	1.2511	0.3502	0.028*
H20B	0.2270	1.1663	0.3801	0.028*
H20C	0.2488	1.0506	0.3160	0.028*
H1N1	0.5810 (13)	0.620 (3)	0.4501 (10)	0.031 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02042 (17)	0.0570 (3)	0.0355 (2)	−0.00826 (17)	0.00457 (14)	0.0233 (2)
O1	0.0176 (4)	0.0252 (5)	0.0164 (4)	0.0004 (4)	0.0046 (3)	−0.0015 (4)
O2	0.0222 (4)	0.0140 (4)	0.0196 (4)	0.0002 (4)	0.0083 (3)	0.0024 (4)
N1	0.0167 (4)	0.0162 (5)	0.0159 (4)	0.0036 (4)	0.0061 (4)	0.0030 (4)
N2	0.0169 (4)	0.0120 (5)	0.0180 (4)	0.0002 (4)	0.0074 (4)	0.0023 (4)
N3	0.0175 (4)	0.0124 (5)	0.0193 (5)	−0.0008 (4)	0.0098 (4)	0.0018 (4)
C1	0.0162 (5)	0.0194 (6)	0.0187 (5)	0.0012 (5)	0.0058 (4)	−0.0004 (5)
C2	0.0193 (5)	0.0208 (7)	0.0190 (5)	−0.0003 (5)	0.0054 (4)	0.0011 (5)
C3	0.0164 (5)	0.0305 (8)	0.0156 (5)	−0.0043 (5)	0.0049 (4)	0.0005 (5)
C4	0.0148 (5)	0.0324 (8)	0.0169 (5)	0.0016 (5)	0.0051 (4)	0.0004 (5)
C5	0.0181 (5)	0.0220 (7)	0.0163 (5)	0.0031 (5)	0.0056 (4)	−0.0004 (5)
C6	0.0166 (5)	0.0173 (6)	0.0155 (5)	−0.0002 (5)	0.0067 (4)	−0.0020 (5)
C7	0.0181 (5)	0.0166 (6)	0.0232 (6)	0.0017 (5)	0.0104 (4)	0.0003 (5)
C8	0.0155 (5)	0.0132 (6)	0.0188 (5)	−0.0020 (4)	0.0071 (4)	−0.0012 (5)
C9	0.0166 (5)	0.0157 (6)	0.0147 (5)	0.0007 (4)	0.0068 (4)	0.0007 (5)
C10	0.0161 (5)	0.0168 (6)	0.0138 (5)	−0.0003 (4)	0.0058 (4)	−0.0001 (5)
C11	0.0167 (5)	0.0155 (6)	0.0135 (5)	0.0004 (4)	0.0050 (4)	−0.0002 (4)
C12	0.0153 (5)	0.0188 (6)	0.0140 (5)	0.0006 (5)	0.0060 (4)	0.0021 (5)
C13	0.0210 (5)	0.0186 (6)	0.0218 (6)	−0.0016 (5)	0.0092 (4)	−0.0007 (5)
C14	0.0227 (6)	0.0248 (7)	0.0309 (7)	−0.0054 (5)	0.0133 (5)	0.0023 (6)
C15	0.0232 (6)	0.0341 (8)	0.0258 (6)	−0.0004 (6)	0.0147 (5)	0.0036 (6)
C16	0.0245 (6)	0.0299 (8)	0.0180 (5)	0.0018 (6)	0.0108 (5)	−0.0033 (5)
C17	0.0193 (5)	0.0220 (7)	0.0167 (5)	−0.0014 (5)	0.0060 (4)	−0.0024 (5)
C18	0.0195 (6)	0.0420 (10)	0.0339 (7)	−0.0062 (6)	0.0071 (5)	0.0014 (7)
C19	0.0197 (5)	0.0159 (6)	0.0227 (6)	−0.0010 (5)	0.0105 (4)	0.0020 (5)
C20	0.0191 (5)	0.0170 (6)	0.0199 (5)	0.0021 (5)	0.0063 (4)	0.0036 (5)

Geometric parameters (Å, º) top

S1—C3	1.7679 (14)	C7—H7B	0.9900
S1—C18	1.7844 (14)	C9—C10	1.3534 (18)
O1—C8	1.2251 (14)	C9—C11	1.4413 (16)
O2—C11	1.2432 (15)	C10—C19	1.4843 (17)
N1—C8	1.3617 (15)	C12—C17	1.3898 (18)
N1—C9	1.4115 (15)	C12—C13	1.3936 (18)
N1—H1N1	0.878 (19)	C13—C14	1.3933 (17)
N2—C10	1.3893 (14)	C13—H13A	0.9500
N2—N3	1.4112 (14)	C14—C15	1.386 (2)
N2—C20	1.4690 (15)	C14—H14A	0.9500
N3—C11	1.3867 (16)	C15—C16	1.387 (2)
N3—C12	1.4194 (14)	C15—H15A	0.9500
C1—C2	1.3892 (18)	C16—C17	1.3946 (17)
C1—C6	1.3985 (18)	C16—H16A	0.9500
C1—H1A	0.9500	C17—H17A	0.9500
C2—C3	1.3952 (17)	C18—H18A	0.9800
C2—H2A	0.9500	C18—H18B	0.9800
C3—C4	1.399 (2)	C18—H18C	0.9800
C4—C5	1.3919 (18)	C19—H19A	0.9800
C4—H4A	0.9500	C19—H19B	0.9800
C5—C6	1.4024 (16)	C19—H19C	0.9800
C5—H5A	0.9500	C20—H20A	0.9800
C6—C7	1.5252 (17)	C20—H20B	0.9800
C7—C8	1.5187 (16)	C20—H20C	0.9800
C7—H7A	0.9900

C3—S1—C18	103.92 (7)	C9—C10—C19	129.15 (11)
C8—N1—C9	120.41 (10)	N2—C10—C19	120.82 (11)
C8—N1—H1N1	120.2 (12)	O2—C11—N3	124.27 (11)
C9—N1—H1N1	118.4 (12)	O2—C11—C9	131.34 (11)
C10—N2—N3	105.49 (10)	N3—C11—C9	104.36 (10)
C10—N2—C20	118.41 (10)	C17—C12—C13	120.95 (11)
N3—N2—C20	113.73 (9)	C17—C12—N3	120.44 (11)
C11—N3—N2	110.70 (9)	C13—C12—N3	118.60 (11)
C11—N3—C12	126.05 (11)	C14—C13—C12	119.11 (13)
N2—N3—C12	119.72 (10)	C14—C13—H13A	120.4
C2—C1—C6	121.05 (11)	C12—C13—H13A	120.4
C2—C1—H1A	119.5	C15—C14—C13	120.34 (13)
C6—C1—H1A	119.5	C15—C14—H14A	119.8
C1—C2—C3	120.65 (13)	C13—C14—H14A	119.8
C1—C2—H2A	119.7	C14—C15—C16	120.13 (12)
C3—C2—H2A	119.7	C14—C15—H15A	119.9
C2—C3—C4	118.86 (12)	C16—C15—H15A	119.9
C2—C3—S1	116.94 (11)	C15—C16—C17	120.30 (13)
C4—C3—S1	124.14 (9)	C15—C16—H16A	119.8
C5—C4—C3	120.31 (11)	C17—C16—H16A	119.8
C5—C4—H4A	119.8	C12—C17—C16	119.15 (13)
C3—C4—H4A	119.8	C12—C17—H17A	120.4
C4—C5—C6	121.08 (13)	C16—C17—H17A	120.4
C4—C5—H5A	119.5	S1—C18—H18A	109.5
C6—C5—H5A	119.5	S1—C18—H18B	109.5
C1—C6—C5	118.04 (11)	H18A—C18—H18B	109.5
C1—C6—C7	122.72 (10)	S1—C18—H18C	109.5
C5—C6—C7	119.23 (12)	H18A—C18—H18C	109.5
C8—C7—C6	112.33 (11)	H18B—C18—H18C	109.5
C8—C7—H7A	109.1	C10—C19—H19A	109.5
C6—C7—H7A	109.1	C10—C19—H19B	109.5
C8—C7—H7B	109.1	H19A—C19—H19B	109.5
C6—C7—H7B	109.1	C10—C19—H19C	109.5
H7A—C7—H7B	107.9	H19A—C19—H19C	109.5
O1—C8—N1	122.58 (11)	H19B—C19—H19C	109.5
O1—C8—C7	121.68 (11)	N2—C20—H20A	109.5
N1—C8—C7	115.70 (10)	N2—C20—H20B	109.5
C10—C9—N1	126.34 (11)	H20A—C20—H20B	109.5
C10—C9—C11	109.09 (10)	N2—C20—H20C	109.5
N1—C9—C11	124.57 (11)	H20A—C20—H20C	109.5
C9—C10—N2	110.03 (11)	H20B—C20—H20C	109.5

C10—N2—N3—C11	6.12 (12)	N1—C9—C10—C19	1.3 (2)
C20—N2—N3—C11	137.50 (10)	C11—C9—C10—C19	−177.91 (11)
C10—N2—N3—C12	166.16 (10)	N3—N2—C10—C9	−4.81 (12)
C20—N2—N3—C12	−62.45 (13)	C20—N2—C10—C9	−133.47 (11)
C6—C1—C2—C3	0.30 (19)	N3—N2—C10—C19	175.01 (10)
C1—C2—C3—C4	0.31 (19)	C20—N2—C10—C19	46.35 (16)
C1—C2—C3—S1	177.43 (10)	N2—N3—C11—O2	173.15 (11)
C18—S1—C3—C2	146.76 (11)	C12—N3—C11—O2	14.66 (19)
C18—S1—C3—C4	−36.29 (13)	N2—N3—C11—C9	−4.94 (12)
C2—C3—C4—C5	−0.98 (19)	C12—N3—C11—C9	−163.44 (11)
S1—C3—C4—C5	−177.88 (10)	C10—C9—C11—O2	−176.02 (12)
C3—C4—C5—C6	1.06 (19)	N1—C9—C11—O2	4.7 (2)
C2—C1—C6—C5	−0.24 (18)	C10—C9—C11—N3	1.88 (13)
C2—C1—C6—C7	−179.19 (11)	N1—C9—C11—N3	−177.38 (10)
C4—C5—C6—C1	−0.43 (18)	C11—N3—C12—C17	130.20 (13)
C4—C5—C6—C7	178.55 (11)	N2—N3—C12—C17	−26.55 (16)
C1—C6—C7—C8	−12.81 (16)	C11—N3—C12—C13	−50.36 (17)
C5—C6—C7—C8	168.25 (11)	N2—N3—C12—C13	152.89 (11)
C9—N1—C8—O1	1.55 (19)	C17—C12—C13—C14	−0.03 (19)
C9—N1—C8—C7	179.33 (11)	N3—C12—C13—C14	−179.46 (11)
C6—C7—C8—O1	69.15 (15)	C12—C13—C14—C15	0.9 (2)
C6—C7—C8—N1	−108.66 (12)	C13—C14—C15—C16	−0.8 (2)
C8—N1—C9—C10	−72.32 (17)	C14—C15—C16—C17	−0.1 (2)
C8—N1—C9—C11	106.81 (14)	C13—C12—C17—C16	−0.90 (18)
N1—C9—C10—N2	−178.87 (10)	N3—C12—C17—C16	178.52 (11)
C11—C9—C10—N2	1.88 (13)	C15—C16—C17—C12	0.99 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.880 (19)	1.956 (19)	2.7816 (14)	155.7 (19)
C1—H1A···O1	0.95	2.38	3.0185 (16)	124
C1—H1A···O1ⁱⁱ	0.95	2.51	3.2342 (16)	133
C7—H7A···O1ⁱⁱⁱ	0.99	2.57	3.4960 (16)	155
C19—H19B···O2^iv	0.98	2.55	3.4470 (17)	152

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁N₃O₂S
M_r	367.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.9176 (8), 6.6527 (4), 19.5792 (10)
β (°)	110.689 (1)
V (Å³)	1817.78 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.37 × 0.18 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.931, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	19714, 5302, 4231
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.116, 1.03
No. of reflections	5302
No. of parameters	242
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.52

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.880 (19)	1.956 (19)	2.7816 (14)	155.7 (19)
C1—H1A···O1	0.95	2.38	3.0185 (16)	124
C1—H1A···O1ⁱⁱ	0.95	2.51	3.2342 (16)	133
C7—H7A···O1ⁱⁱⁱ	0.99	2.57	3.4960 (16)	155
C19—H19B···O2^iv	0.98	2.55	3.4470 (17)	152

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors would like to thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN also thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS-Phase 1 programme.

References

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