1-Acetyl-3-[4-(methyl­sulfan­yl)phen­yl]-5-(4-nitro­phen­yl)-4,5-dihydro-1H-pyrazole

Thiruvalluvar, A.; Subramanyam, M.; Butcher, R.J.; Mahalinga, M.

doi:10.1107/S1600536807058205

1-Acetyl-3-[4-(methylsulfanyl)phenyl]-5-(4-nitrophenyl)-4,5-dihydro-1H-pyrazole

A. Thiruvalluvar, M. Subramanyam, R. J. Butcher and M. Mahalinga

In the title molecule, C₁₈H₁₇N₃O₃S, the dihedral angle between the two benzene rings is 72.8 (1)°. C—H

O and C—H

N hydrogen bonds are found in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058205/bq2044sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058205/bq2044Isup2.hkl Contains datablock I

CCDC reference: 672986

checkCIF report

Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R factor = 0.071
wR factor = 0.141
Data-to-parameter ratio = 24.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.822     1.000
            Tmin(prime) and Tmax expected:      0.914     0.942
            RR(prime) =      0.847
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.85
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.94

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.942
            Tmax scaled      0.942 Tmin scaled      0.774
PLAT793_ALERT_1_G Check the Absolute Configuration of C5     = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 5 Informative message, check

Comment top

Pyrazolines have been reported to exhibit a broad spectrum of biological activities including antibacterial, antifungal, anti-inflammatory, anti-depressant, antiviral agents (Nauduri & Reddy, 1998; Korgaokar et al., 1996; Udupi et al., 1998 & Bilgin et al., 1993). Some of these compounds have also shown ulcerogenic, anaesthetic and analgesic properties(Mancera et al., 1991; Kumar et al., 2003 & Nugent et al., 1993). For instance, 1-thiocarbonyl-3,5-diphenyl-2-pyrazolines exhibit antidepressant activity(Hiroshi et al., 1970), while (5-benzoyl-2,4-dihydro-3H-pyrazol-3-ylidene) bis phosphonic acid tetraethyl ester has been reported to possess novel anti-inflammatory activity. It also inhibits chronic arthritis and inflammation in animals. 3-Amino-1-[m-(trifluoromethyl)phenyl]-2-pyrazoline, besides acting as dual lipoxygenase/cycloxygenase inhibitor, attenuates postischemic brain hypoperfusion and repercussion injury(Bilgin et al., 1993). Many pyrazolines also find utility as polymer intermediates in industry(Chen et al., 1995).

In the title molecule, C₁₈H₁₇N₃O₃S, Fig.1., the dihedral angle between the two phenyl rings is 72.8 (1)°. The pyrazole ring makes a dihedral angle of 16.0 (1)° and 78.1 (1)°, with that of the methylthiophenyl and nitrophenyl rings respectively. The acetyl group is coplanar with the attached pyrazole ring, except the methyl H atoms. C—H···O, and C—H···N hydrogen bonds are found in the crystal structure; see hydrogen bond table.

Related literature top

For the uses of pyrazolines, see Bilgin et al. (1993); Chen et al. (1995); Hiroshi et al. (1970); Korgaokar et al. (1996); Kumar et al. (2003); Mancera et al., (1991); Nauduri & Reddy, (1998); Nugent et al. (1993); Udupi et al. (1998)

Experimental top

A mixture of 1-[4-(methylthio)phenyl]-3-(4-nitrophenyl)prop-2-en-1-one (5 g, 0.016 mol) and a molar equivalent of hydrazine hydrate (80%) in glacial acetic acid (25 ml) was heated on water bath at 363–5 K for 5–6 hr. The reaction mass was then poured into ice-cold water. The solid obtained was filtered, washed with water, dried and crystallized from methanol to yield the title compound. Yield 5.2 g (88%),

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. Dashed line indicate hydrogen bond.
	Fig. 2. The packing of the title compound, viewed down the c axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

1-Acetyl-3-[4-(methylsulfanyl)phenyl]-5-(4-nitrophenyl)-4,5-dihydro-1H-pyrazole top

Crystal data top

C₁₈H₁₇N₃O₃S	F(000) = 744
M_r = 355.42	D_x = 1.397 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 396(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.2630 (2) Å	Cell parameters from 4988 reflections
b = 35.631 (2) Å	θ = 4.6–32.4°
c = 9.0145 (3) Å	µ = 0.21 mm⁻¹
β = 91.651 (4)°	T = 200 K
V = 1689.76 (13) Å³	Prism, colourless
Z = 4	0.41 × 0.33 × 0.28 mm

Data collection top

Oxford Diffraction Gemini diffractometer	5637 independent reflections
Radiation source: fine-focus sealed tube	3490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 10.5081 pixels mm^-1	θ_max = 32.5°, θ_min = 4.6°
ϕ and ω scans	h = −7→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −43→53
T_min = 0.822, T_max = 1.000	l = −11→12
16654 measured reflections

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.045P)² + 0.9398P] where P = (F_o² + 2F_c²)/3
5637 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₈H₁₇N₃O₃S	V = 1689.76 (13) Å³
M_r = 355.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.2630 (2) Å	µ = 0.21 mm⁻¹
b = 35.631 (2) Å	T = 200 K
c = 9.0145 (3) Å	0.41 × 0.33 × 0.28 mm
β = 91.651 (4)°

Data collection top

Oxford Diffraction Gemini diffractometer	5637 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	3490 reflections with I > 2σ(I)
T_min = 0.822, T_max = 1.000	R_int = 0.038
16654 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.07	Δρ_max = 0.30 e Å⁻³
5637 reflections	Δρ_min = −0.30 e Å⁻³
228 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 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	1.27204 (11)	0.00962 (2)	0.63858 (6)	0.0396 (2)
O1	0.1107 (3)	0.16677 (5)	1.30061 (16)	0.0396 (5)
O4	0.9584 (5)	0.30750 (6)	1.1909 (3)	0.0774 (9)
O5	0.6845 (4)	0.33244 (5)	1.0406 (2)	0.0635 (7)
N1	0.3441 (3)	0.13614 (5)	1.13728 (17)	0.0283 (5)
N2	0.5244 (3)	0.10911 (4)	1.10260 (17)	0.0268 (5)
N4	0.7752 (4)	0.30532 (6)	1.1052 (2)	0.0486 (7)
C1	0.2485 (4)	0.14011 (6)	1.2751 (2)	0.0306 (6)
C2	0.3161 (5)	0.11025 (7)	1.3860 (2)	0.0473 (8)
C3	0.5669 (3)	0.11213 (5)	0.9637 (2)	0.0247 (5)
C4	0.4033 (4)	0.14086 (6)	0.8842 (2)	0.0298 (6)
C5	0.2927 (4)	0.16276 (6)	1.0149 (2)	0.0276 (6)
C6	1.4986 (4)	−0.00883 (6)	0.7715 (3)	0.0365 (7)
C11	0.7510 (3)	0.08801 (5)	0.8899 (2)	0.0237 (5)
C12	0.9297 (3)	0.06650 (6)	0.9694 (2)	0.0262 (5)
C13	1.0945 (4)	0.04292 (6)	0.8973 (2)	0.0286 (6)
C14	1.0853 (3)	0.04011 (5)	0.7425 (2)	0.0269 (6)
C15	0.9118 (4)	0.06228 (6)	0.6628 (2)	0.0288 (6)
C16	0.7480 (4)	0.08588 (6)	0.7351 (2)	0.0285 (6)
C21	0.4226 (4)	0.20011 (6)	1.0414 (2)	0.0269 (5)
C22	0.3251 (4)	0.23200 (6)	0.9717 (2)	0.0366 (7)
C23	0.4400 (4)	0.26651 (6)	0.9913 (3)	0.0393 (7)
C24	0.6563 (4)	0.26848 (6)	1.0810 (2)	0.0358 (7)
C25	0.7595 (4)	0.23736 (6)	1.1511 (2)	0.0377 (7)
C26	0.6407 (4)	0.20312 (6)	1.1311 (2)	0.0319 (6)
H2A	0.25307	0.11740	1.48332	0.0710*
H2B	0.50120	0.10735	1.39278	0.0710*
H2C	0.23819	0.08645	1.35470	0.0710*
H4A	0.26750	0.12880	0.82265	0.0357*
H4B	0.50570	0.15734	0.82069	0.0357*
H5	0.10549	0.16637	0.99905	0.0331*
H6A	1.62916	−0.02295	0.71986	0.0547*
H6B	1.41215	−0.02551	0.84020	0.0547*
H6C	1.57844	0.01188	0.82709	0.0547*
H12	0.93834	0.06808	1.07463	0.0314*
H13	1.21493	0.02850	0.95339	0.0343*
H15	0.90594	0.06116	0.55746	0.0344*
H16	0.63156	0.10090	0.67875	0.0342*
H22	0.17677	0.23001	0.90960	0.0439*
H23	0.37202	0.28832	0.94423	0.0472*
H25	0.90938	0.23945	1.21179	0.0453*
H26	0.70853	0.18145	1.17909	0.0383*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0357 (3)	0.0470 (3)	0.0358 (3)	0.0106 (3)	−0.0015 (2)	−0.0129 (3)
O1	0.0377 (8)	0.0484 (10)	0.0328 (8)	0.0106 (7)	0.0047 (6)	−0.0037 (7)
O4	0.0953 (17)	0.0550 (13)	0.0806 (15)	−0.0236 (12)	−0.0203 (13)	−0.0130 (11)
O5	0.0779 (14)	0.0311 (10)	0.0826 (14)	−0.0010 (9)	0.0200 (11)	−0.0011 (10)
N1	0.0312 (8)	0.0272 (9)	0.0266 (8)	0.0052 (7)	0.0039 (7)	0.0035 (7)
N2	0.0294 (8)	0.0238 (8)	0.0272 (8)	0.0014 (7)	0.0025 (6)	0.0006 (7)
N4	0.0621 (14)	0.0361 (12)	0.0487 (12)	−0.0054 (10)	0.0188 (11)	−0.0128 (10)
C1	0.0326 (10)	0.0350 (11)	0.0242 (10)	−0.0022 (9)	0.0024 (8)	−0.0012 (8)
C2	0.0686 (16)	0.0472 (15)	0.0267 (11)	0.0060 (12)	0.0098 (10)	0.0068 (10)
C3	0.0259 (9)	0.0228 (9)	0.0254 (9)	−0.0027 (8)	−0.0007 (7)	0.0009 (8)
C4	0.0338 (10)	0.0313 (11)	0.0243 (9)	0.0041 (9)	0.0008 (8)	0.0016 (8)
C5	0.0277 (9)	0.0299 (11)	0.0251 (9)	0.0048 (8)	0.0008 (7)	0.0040 (8)
C6	0.0331 (11)	0.0314 (11)	0.0450 (12)	0.0044 (9)	0.0038 (9)	0.0012 (10)
C11	0.0255 (9)	0.0223 (9)	0.0232 (9)	−0.0028 (7)	0.0015 (7)	0.0001 (7)
C12	0.0280 (9)	0.0309 (10)	0.0195 (9)	−0.0020 (8)	−0.0003 (7)	0.0004 (8)
C13	0.0252 (9)	0.0307 (11)	0.0298 (10)	0.0019 (8)	−0.0030 (8)	0.0029 (8)
C14	0.0237 (9)	0.0270 (10)	0.0300 (10)	−0.0027 (8)	0.0025 (7)	−0.0035 (8)
C15	0.0342 (10)	0.0317 (11)	0.0204 (9)	−0.0011 (8)	0.0019 (7)	−0.0004 (8)
C16	0.0302 (10)	0.0272 (10)	0.0280 (10)	0.0014 (8)	−0.0023 (8)	0.0027 (8)
C21	0.0277 (9)	0.0281 (10)	0.0251 (9)	0.0048 (8)	0.0053 (7)	0.0014 (8)
C22	0.0352 (11)	0.0351 (12)	0.0391 (12)	0.0036 (9)	−0.0045 (9)	0.0093 (10)
C23	0.0453 (13)	0.0312 (12)	0.0418 (12)	0.0056 (10)	0.0060 (10)	0.0095 (10)
C24	0.0441 (13)	0.0288 (11)	0.0351 (11)	−0.0019 (9)	0.0138 (9)	−0.0062 (9)
C25	0.0361 (11)	0.0400 (13)	0.0369 (12)	−0.0001 (10)	−0.0015 (9)	−0.0048 (10)
C26	0.0308 (10)	0.0311 (11)	0.0337 (11)	0.0060 (8)	−0.0016 (8)	0.0021 (9)

Geometric parameters (Å, º) top

S1—C6	1.791 (2)	C21—C26	1.389 (3)
S1—C14	1.7541 (18)	C22—C23	1.379 (3)
O1—C1	1.221 (3)	C23—C24	1.379 (3)
O4—N4	1.221 (3)	C24—C25	1.380 (3)
O5—N4	1.219 (3)	C25—C26	1.380 (3)
N1—N2	1.394 (2)	C2—H2A	0.9800
N1—C1	1.361 (2)	C2—H2B	0.9800
N1—C5	1.474 (3)	C2—H2C	0.9800
N2—C3	1.283 (2)	C4—H4A	0.9900
N4—C24	1.468 (3)	C4—H4B	0.9900
C1—C2	1.496 (3)	C5—H5	1.0000
C3—C4	1.506 (3)	C6—H6A	0.9800
C3—C11	1.469 (2)	C6—H6B	0.9800
C4—C5	1.541 (3)	C6—H6C	0.9800
C5—C21	1.512 (3)	C12—H12	0.9500
C11—C12	1.395 (2)	C13—H13	0.9500
C11—C16	1.397 (3)	C15—H15	0.9500
C12—C13	1.383 (3)	C16—H16	0.9500
C13—C14	1.399 (3)	C22—H22	0.9500
C14—C15	1.392 (3)	C23—H23	0.9500
C15—C16	1.381 (3)	C25—H25	0.9500
C21—C22	1.390 (3)	C26—H26	0.9500

S1···S1ⁱ	3.5799 (8)	C13···H6B	3.0100
O1···C21	3.128 (2)	C13···H6Cⁱⁱ	2.9800
O1···C25ⁱⁱ	3.379 (3)	C13···H6C	2.8600
O1···C26ⁱⁱ	3.149 (3)	C14···H6Cⁱⁱ	2.9700
O1···O5ⁱⁱⁱ	3.161 (2)	C15···H6Cⁱⁱ	2.9400
O1···C23^iv	3.382 (3)	C16···H4B	2.9600
O4···C4^v	3.416 (3)	C16···H6Cⁱⁱ	2.9100
O5···C2^vi	3.117 (3)	C16···H4A	3.0800
O5···O1^vii	3.161 (2)	C26···H5^ix	3.0500
O5···C1^vi	3.411 (3)	H2B···N2	2.6200
O5···C16^iv	3.409 (3)	H2B···O5^iv	2.6900
O1···H25ⁱⁱ	2.9000	H2C···N2	2.8800
O1···H26ⁱⁱ	2.4100	H2C···H6A^xii	2.4700
O1···H23^iv	2.4500	H4A···C16	3.0800
O1···H5	2.7200	H4A···H16	2.5500
O4···H22^v	2.6200	H4B···C16	2.9600
O4···H25	2.4500	H4B···H16	2.4800
O5···H23	2.4200	H4B···O5^vi	2.7400
O5···H2B^vi	2.6900	H4B···N4^vi	2.7800
O5···H4B^iv	2.7400	H5···O1	2.7200
O5···H16^iv	2.7000	H5···C26ⁱⁱ	3.0500
N2···C26	3.414 (3)	H5···H22	2.4400
N1···H26	2.5300	H6A···H2C^xii	2.4700
N2···H2B	2.6200	H6B···C13	3.0100
N2···H2C	2.8800	H6B···H13	2.4300
N2···H12	2.6400	H6B···C12^xii	2.9100
N2···H26	2.8300	H6B···H12^xii	2.5200
N4···H4B^iv	2.7800	H6C···C11^ix	2.9100
C1···C26	3.338 (3)	H6C···C12^ix	2.9500
C1···O5^iv	3.411 (3)	H6C···C13	2.8600
C2···O5^iv	3.117 (3)	H6C···C13^ix	2.9800
C3···C26	3.592 (3)	H6C···C14^ix	2.9700
C3···C13ⁱⁱ	3.541 (3)	H6C···C15^ix	2.9400
C4···O4^viii	3.416 (3)	H6C···C16^ix	2.9100
C6···C15^ix	3.497 (3)	H6C···H13	2.3300
C6···C14^ix	3.562 (3)	H12···N2	2.6400
C13···C3^ix	3.541 (3)	H12···H6B^xii	2.5200
C14···C6ⁱⁱ	3.562 (3)	H13···C6	2.6100
C15···C6ⁱⁱ	3.497 (3)	H13···H6B	2.4300
C16···O5^vi	3.409 (3)	H13···H6C	2.3300
C21···O1	3.128 (2)	H13···C6^xi	2.9500
C22···C25ⁱⁱ	3.434 (3)	H16···C2^xiii	3.1000
C23···C25^vi	3.542 (3)	H16···C4	2.6500
C23···O1^vi	3.382 (3)	H16···H4A	2.5500
C25···C23^iv	3.542 (3)	H16···H4B	2.4800
C25···C22^ix	3.434 (3)	H16···O5^vi	2.7000
C25···O1^ix	3.379 (3)	H22···H5	2.4400
C26···N2	3.414 (3)	H22···O4^viii	2.6200
C26···C3	3.592 (3)	H22···H25^viii	2.4900
C26···C1	3.338 (3)	H23···O5	2.4200
C26···O1^ix	3.149 (3)	H23···O1^vi	2.4500
C1···H26	2.9800	H23···C1^vi	3.0300
C1···H23^iv	3.0300	H25···O1^ix	2.9000
C2···H16^x	3.1000	H25···O4	2.4500
C4···H16	2.6500	H25···H22^v	2.4900
C6···H13	2.6100	H26···O1^ix	2.4100
C6···H13^xi	2.9500	H26···N1	2.5300
C11···H6Cⁱⁱ	2.9100	H26···N2	2.8300
C12···H6B^xii	2.9100	H26···C1	2.9800
C12···H6Cⁱⁱ	2.9500

C6—S1—C14	104.04 (10)	C21—C26—C25	120.52 (19)
N2—N1—C1	123.26 (16)	C1—C2—H2A	109.00
N2—N1—C5	112.84 (14)	C1—C2—H2B	109.00
C1—N1—C5	123.48 (17)	C1—C2—H2C	109.00
N1—N2—C3	107.45 (14)	H2A—C2—H2B	109.00
O4—N4—O5	122.9 (2)	H2A—C2—H2C	109.00
O4—N4—C24	118.5 (2)	H2B—C2—H2C	109.00
O5—N4—C24	118.60 (19)	C3—C4—H4A	111.00
O1—C1—N1	119.34 (18)	C3—C4—H4B	111.00
O1—C1—C2	123.96 (18)	C5—C4—H4A	111.00
N1—C1—C2	116.68 (18)	C5—C4—H4B	111.00
N2—C3—C4	114.09 (15)	H4A—C4—H4B	109.00
N2—C3—C11	121.93 (16)	N1—C5—H5	110.00
C4—C3—C11	123.91 (16)	C4—C5—H5	110.00
C3—C4—C5	101.76 (15)	C21—C5—H5	110.00
N1—C5—C4	100.44 (16)	S1—C6—H6A	109.00
N1—C5—C21	112.07 (16)	S1—C6—H6B	109.00
C4—C5—C21	112.79 (17)	S1—C6—H6C	109.00
C3—C11—C12	122.17 (16)	H6A—C6—H6B	109.00
C3—C11—C16	119.71 (16)	H6A—C6—H6C	109.00
C12—C11—C16	118.11 (17)	H6B—C6—H6C	109.00
C11—C12—C13	120.99 (17)	C11—C12—H12	120.00
C12—C13—C14	120.55 (18)	C13—C12—H12	120.00
S1—C14—C13	124.99 (14)	C12—C13—H13	120.00
S1—C14—C15	116.44 (14)	C14—C13—H13	120.00
C13—C14—C15	118.55 (17)	C14—C15—H15	120.00
C14—C15—C16	120.75 (17)	C16—C15—H15	120.00
C11—C16—C15	121.01 (18)	C11—C16—H16	119.00
C5—C21—C22	119.27 (18)	C15—C16—H16	120.00
C5—C21—C26	121.48 (18)	C21—C22—H22	119.00
C22—C21—C26	119.23 (19)	C23—C22—H22	119.00
C21—C22—C23	121.08 (19)	C22—C23—H23	121.00
C22—C23—C24	118.2 (2)	C24—C23—H23	121.00
N4—C24—C23	118.29 (19)	C24—C25—H25	121.00
N4—C24—C25	119.35 (18)	C26—C25—H25	121.00
C23—C24—C25	122.4 (2)	C21—C26—H26	120.00
C24—C25—C26	118.66 (19)	C25—C26—H26	120.00

C6—S1—C14—C13	−9.62 (19)	C3—C4—C5—C21	102.45 (18)
C6—S1—C14—C15	172.01 (15)	N1—C5—C21—C22	−155.98 (17)
C1—N1—N2—C3	177.91 (18)	N1—C5—C21—C26	25.6 (3)
C5—N1—N2—C3	−9.3 (2)	C4—C5—C21—C22	91.5 (2)
N2—N1—C1—O1	172.68 (18)	C4—C5—C21—C26	−86.9 (2)
N2—N1—C1—C2	−8.9 (3)	C3—C11—C12—C13	177.49 (18)
C5—N1—C1—O1	0.7 (3)	C16—C11—C12—C13	−1.8 (3)
C5—N1—C1—C2	179.12 (19)	C3—C11—C16—C15	−177.32 (18)
N2—N1—C5—C4	17.1 (2)	C12—C11—C16—C15	2.0 (3)
N2—N1—C5—C21	−102.86 (18)	C11—C12—C13—C14	−0.1 (3)
C1—N1—C5—C4	−170.11 (18)	C12—C13—C14—S1	−176.62 (15)
C1—N1—C5—C21	69.9 (2)	C12—C13—C14—C15	1.7 (3)
N1—N2—C3—C4	−3.7 (2)	S1—C14—C15—C16	176.95 (16)
N1—N2—C3—C11	179.23 (15)	C13—C14—C15—C16	−1.5 (3)
O4—N4—C24—C23	176.1 (2)	C14—C15—C16—C11	−0.3 (3)
O4—N4—C24—C25	−2.3 (3)	C5—C21—C22—C23	−179.09 (19)
O5—N4—C24—C23	−2.9 (3)	C26—C21—C22—C23	−0.6 (3)
O5—N4—C24—C25	178.8 (2)	C5—C21—C26—C25	178.53 (18)
N2—C3—C4—C5	14.0 (2)	C22—C21—C26—C25	0.1 (3)
C11—C3—C4—C5	−168.96 (16)	C21—C22—C23—C24	0.6 (3)
N2—C3—C11—C12	−14.6 (3)	C22—C23—C24—N4	−178.43 (19)
N2—C3—C11—C16	164.69 (18)	C22—C23—C24—C25	−0.2 (3)
C4—C3—C11—C12	168.59 (18)	N4—C24—C25—C26	177.90 (18)
C4—C3—C11—C16	−12.1 (3)	C23—C24—C25—C26	−0.4 (3)
C3—C4—C5—N1	−17.02 (18)	C24—C25—C26—C21	0.4 (3)

Symmetry codes: (i) −x+3, −y, −z+1; (ii) x−1, y, z; (iii) x−1, −y+1/2, z+1/2; (iv) x, −y+1/2, z+1/2; (v) x+1, −y+1/2, z+1/2; (vi) x, −y+1/2, z−1/2; (vii) x+1, −y+1/2, z−1/2; (viii) x−1, −y+1/2, z−1/2; (ix) x+1, y, z; (x) x, y, z+1; (xi) −x+3, −y, −z+2; (xii) −x+2, −y, −z+2; (xiii) x, y, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O1^vi	0.95	2.45	3.382 (3)	165
C26—H26···O1^ix	0.95	2.41	3.149 (3)	134
C26—H26···N1	0.95	2.53	2.853 (3)	100

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇N₃O₃S
M_r	355.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	5.2630 (2), 35.631 (2), 9.0145 (3)
β (°)	91.651 (4)
V (Å³)	1689.76 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.41 × 0.33 × 0.28

Data collection
Diffractometer	Oxford Diffraction Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.822, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16654, 5637, 3490
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.141, 1.07
No. of reflections	5637
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.30

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).