4-{(4Z)-4-[(2Z)-3-(4-Fluoro­anilino)-1-hy­droxy­but-2-en-1-yl­idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}­benzene­sulfonamide

Asiri, A.M.; Faidallah, H.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812006502

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o762-o763

doi:10.1107/S1600536812006502

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4-{(4Z)-4-[(2Z)-3-(4-Fluoroanilino)-1-hydroxybut-2-en-1-ylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzenesulfonamide

Abdullah M. Asiri,^a,^b ‡ Hassan M. Faidallah,^a Seik Weng Ng ^c and Edward R. T. Tiekink ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, PO Box 80203, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 12 February 2012; accepted 14 February 2012; online 17 February 2012)

In the title compound, C₂₀H₁₉FN₄O₄S, the pyrazole and benzenesulfonamide rings are coplanar [dihedral angle = 5.02 (15)°] but this planarity does not extend over the entire molecule, the dihedral angle between the terminal six-membered rings being 33.24 (14)°. Intramolecular hydroxy–hydroxy O—H⋯O and amine–hydroxy N—H⋯O hydrogen bonds, as a well as a tight C—H⋯O(carbonyl) interaction, lead to a sequence of three fused S(6) rings. Supramolecular chains along the a axis feature in the crystal packing; these chains are stabilized by amine–sulfonamide N—H⋯O and amine–pyrazole N—H⋯N hydrogen bonds.

Related literature

For background to the synthesis, see: Gelin et al. (1983 ); Bendaas et al. (1999 ). For related structures, see: Asiri, Al-Youbi, Alamry et al. (2011 ); Asiri, Al-Youbi, Faidallah et al. (2011 ).

Experimental

Crystal data

C₂₀H₁₉FN₄O₄S
M_r = 430.45
Triclinic, $[P \overline 1]$
a = 7.8121 (5) Å
b = 10.0137 (8) Å
c = 12.6003 (9) Å
α = 97.950 (6)°
β = 104.632 (6)°
γ = 98.394 (6)°
V = 927.58 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.25 × 0.10 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.946, T_max = 0.996
6559 measured reflections
4240 independent reflections
2935 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.146
S = 1.01
4240 reflections
287 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O1	0.85 (1)	1.71 (2)	2.522 (3)	161 (4)
N3—H3⋯O2	0.88 (1)	1.95 (2)	2.662 (3)	137 (3)
C2—H2⋯O1	0.95	2.26	2.917 (4)	126
N4—H41⋯N2ⁱ	0.88 (1)	2.14 (1)	2.999 (3)	167 (3)
N4—H42⋯O3ⁱⁱ	0.88 (1)	2.08 (1)	2.943 (3)	169 (3)
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006502/hg5177sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006502/hg5177Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006502/hg5177Isup3.cml

checkCIF report

Comment top

In connection with a recent structural studies (Asiri, Al-Youbi, Alamry et al., 2011; Asiri, Al-Youbi, Faidallah et al., 2011), the title compound, 4-{4-[3-(4-fluoroanilino)-1-hydroxybut-2-enylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzenesulfonamide (I), was prepared as a part of on-going investigations of reactions between pyrazoles and aniline derivatives based on literature procedures (Gelin et al., 1983; Bendaas et al., 1999).

In (I), Fig. 1, the pyrazolyl and benzenesulfonamide rings are co-planar as seen in dihedral angle of 5.02 (15)°. The planarity extends to the rest of the molecule with the exception of the terminal benzene ring; the dihedral angle between the terminal six-membered rings being 33.24 (14)°. The observed planarity is accounted for by the presence of intramolecular O—H···O and N—H···O hydrogen bonds involving the central hydroxyl-O2 atom functioning as both an acceptor and as a donor, Table 1. These interactions are complemented by a tight C—H···O1 interaction, Table 1. The intramolecular interactions lead to a sequence of three fused S(6) rings.

The molecules are connected into a supramolecular chain along the a axis in the crystal packing, Fig. 2 and Table 1. Both amide-H atoms form hydrogen bonds, one to a sulfonamide-O3 atom and the other to a pyrazolyl-N2 atom. Centrosymmetrically related molecules associate via an eight-membered {···HNSO}₂ synthon. These are linked to translationally related molecules via N–H···N hydrogen bonds which lead to the formation of 22-membered {···HNH···OSC₄N₂}₂ synthons which encompass two of the aforementioned N—H···O hydrogen bonds.

Related literature top

For background to the synthesis, see: Gelin et al. (1983); Bendaas et al. (1999). For related structures, see: Asiri, Al-Youbi, Alamry et al. (2011); Asiri, Al-Youbi, Faidallah et al. (2011).

Experimental top

A solution of 4-acetoacetyl-5-hydroxy-3-methyl-1-p-sulfamylphenypyrazole (1.7 g, 0.005 mol) and 4-fluoroaniline (0.55 g, 0.005 mol) in ethanol (25 ml) was refluxed for 2 h. The precipitate, obtained from the hot solution, was collected, washed with methanol and recrystallized from ethanol-benzene to yield yellow crystals; M.pt: 411–412 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of a supramolecular chain along the a axis in (I) mediated by N—H···O and N—H···N hydrogen bonds shown as orange and blue dashed lines, respectively.

4-{(4Z)-4-[(2Z)-3-(4-Fluoroanilino)-1-hydroxybut-2-en-1-ylidene]- 3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzenesulfonamide top

Crystal data top

C₂₀H₁₉FN₄O₄S	Z = 2
M_r = 430.45	F(000) = 448
Triclinic, P1	D_x = 1.541 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8121 (5) Å	Cell parameters from 1846 reflections
b = 10.0137 (8) Å	θ = 2.4–27.5°
c = 12.6003 (9) Å	µ = 0.22 mm⁻¹
α = 97.950 (6)°	T = 100 K
β = 104.632 (6)°	Prism, yellow
γ = 98.394 (6)°	0.25 × 0.10 × 0.02 mm
V = 927.58 (12) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4240 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2935 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.041
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.4°
ω scan	h = −10→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→13
T_min = 0.946, T_max = 0.996	l = −16→16
6559 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0548P)² + 0.375P] where P = (F_o² + 2F_c²)/3
4240 reflections	(Δ/σ)_max = 0.001
287 parameters	Δρ_max = 0.47 e Å⁻³
4 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₀H₁₉FN₄O₄S	γ = 98.394 (6)°
M_r = 430.45	V = 927.58 (12) Å³
Triclinic, P1	Z = 2
a = 7.8121 (5) Å	Mo Kα radiation
b = 10.0137 (8) Å	µ = 0.22 mm⁻¹
c = 12.6003 (9) Å	T = 100 K
α = 97.950 (6)°	0.25 × 0.10 × 0.02 mm
β = 104.632 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4240 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2935 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.996	R_int = 0.041
6559 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	4 restraints
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.47 e Å⁻³
4240 reflections	Δρ_min = −0.36 e Å⁻³
287 parameters

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

	x	y	z	U_iso*/U_eq
S1	1.14758 (9)	0.18251 (7)	0.13099 (5)	0.01909 (19)
F1	0.3342 (3)	0.78774 (18)	1.20106 (14)	0.0361 (5)
O1	0.7345 (3)	0.41000 (19)	0.53049 (16)	0.0245 (5)
O2	0.5322 (3)	0.4509 (2)	0.65439 (16)	0.0267 (5)
H1	0.608 (4)	0.457 (4)	0.617 (3)	0.057 (12)*
O3	1.0480 (3)	0.17118 (19)	0.01577 (15)	0.0218 (5)
O4	1.2886 (3)	0.2998 (2)	0.18161 (16)	0.0262 (5)
N1	0.6195 (3)	0.2035 (2)	0.39856 (18)	0.0181 (5)
N2	0.4693 (3)	0.0958 (2)	0.37289 (18)	0.0194 (5)
N3	0.3372 (3)	0.4895 (2)	0.7974 (2)	0.0246 (6)
H3	0.429 (3)	0.519 (3)	0.772 (2)	0.026 (9)*
N4	1.2349 (3)	0.0473 (2)	0.13729 (19)	0.0214 (5)
H41	1.299 (3)	0.047 (3)	0.2055 (13)	0.026*
H42	1.156 (3)	−0.025 (2)	0.098 (2)	0.026*
C1	0.7495 (4)	0.1957 (3)	0.3386 (2)	0.0184 (6)
C2	0.8925 (4)	0.3055 (3)	0.3569 (2)	0.0207 (6)
H2	0.9062	0.3844	0.4119	0.025*
C3	1.0138 (4)	0.2982 (3)	0.2943 (2)	0.0208 (6)
H3A	1.1116	0.3725	0.3067	0.025*
C4	0.9944 (4)	0.1833 (3)	0.2133 (2)	0.0183 (6)
C5	0.8533 (4)	0.0721 (3)	0.1959 (2)	0.0198 (6)
H5	0.8402	−0.0066	0.1409	0.024*
C6	0.7327 (4)	0.0778 (3)	0.2596 (2)	0.0185 (6)
H6	0.6385	0.0016	0.2498	0.022*
C7	0.6167 (4)	0.3021 (3)	0.4854 (2)	0.0190 (6)
C8	0.4559 (4)	0.2561 (3)	0.5145 (2)	0.0191 (6)
C9	0.3752 (4)	0.1281 (3)	0.4419 (2)	0.0194 (6)
C10	0.2070 (4)	0.0316 (3)	0.4376 (2)	0.0224 (6)
H10A	0.1031	0.0764	0.4172	0.034*
H10B	0.2166	0.0062	0.5110	0.034*
H10C	0.1914	−0.0512	0.3819	0.034*
C11	0.4130 (4)	0.3362 (3)	0.6027 (2)	0.0215 (6)
C12	0.2592 (4)	0.3066 (3)	0.6396 (2)	0.0252 (7)
H12	0.1707	0.2292	0.5978	0.030*
C13	0.2232 (4)	0.3787 (3)	0.7311 (2)	0.0233 (6)
C14	0.0456 (4)	0.3322 (3)	0.7541 (3)	0.0316 (8)
H14A	−0.0467	0.2940	0.6834	0.047*
H14B	0.0101	0.4107	0.7929	0.047*
H14C	0.0581	0.2617	0.8008	0.047*
C15	0.3261 (4)	0.5620 (3)	0.9014 (2)	0.0273 (7)
C16	0.2655 (4)	0.4976 (3)	0.9798 (3)	0.0288 (7)
H16	0.2238	0.4011	0.9648	0.035*
C17	0.2665 (4)	0.5744 (3)	1.0786 (2)	0.0281 (7)
H17	0.2213	0.5319	1.1315	0.034*
C18	0.3323 (4)	0.7119 (3)	1.1012 (2)	0.0252 (7)
C19	0.3989 (4)	0.7777 (3)	1.0272 (2)	0.0280 (7)
H19	0.4477	0.8733	1.0453	0.034*
C20	0.3932 (4)	0.7016 (3)	0.9259 (2)	0.0257 (7)
H20	0.4356	0.7454	0.8727	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0177 (4)	0.0186 (4)	0.0193 (4)	−0.0007 (3)	0.0069 (3)	−0.0013 (3)
F1	0.0487 (12)	0.0327 (10)	0.0289 (10)	0.0100 (9)	0.0165 (9)	−0.0006 (8)
O1	0.0214 (11)	0.0215 (10)	0.0259 (11)	−0.0032 (9)	0.0089 (9)	−0.0082 (8)
O2	0.0252 (12)	0.0268 (11)	0.0250 (11)	−0.0012 (10)	0.0107 (9)	−0.0059 (9)
O3	0.0224 (10)	0.0235 (11)	0.0189 (10)	0.0035 (9)	0.0055 (8)	0.0029 (8)
O4	0.0244 (11)	0.0233 (11)	0.0281 (11)	−0.0044 (9)	0.0119 (9)	−0.0040 (8)
N1	0.0169 (12)	0.0174 (12)	0.0177 (12)	0.0004 (10)	0.0053 (9)	−0.0020 (9)
N2	0.0171 (12)	0.0186 (12)	0.0197 (12)	−0.0013 (10)	0.0044 (10)	0.0000 (9)
N3	0.0236 (14)	0.0240 (13)	0.0243 (13)	0.0026 (11)	0.0092 (11)	−0.0042 (10)
N4	0.0205 (13)	0.0233 (13)	0.0170 (12)	0.0033 (11)	0.0022 (10)	−0.0009 (10)
C1	0.0181 (14)	0.0220 (14)	0.0156 (13)	0.0053 (12)	0.0053 (11)	0.0018 (11)
C2	0.0246 (15)	0.0169 (14)	0.0172 (14)	0.0033 (12)	0.0045 (12)	−0.0047 (10)
C3	0.0188 (14)	0.0181 (14)	0.0231 (15)	0.0003 (12)	0.0052 (12)	−0.0001 (11)
C4	0.0160 (14)	0.0200 (14)	0.0192 (14)	0.0029 (12)	0.0063 (11)	0.0023 (11)
C5	0.0208 (15)	0.0174 (14)	0.0182 (14)	0.0027 (12)	0.0030 (11)	−0.0018 (10)
C6	0.0164 (14)	0.0174 (14)	0.0185 (14)	−0.0013 (11)	0.0036 (11)	0.0000 (10)
C7	0.0213 (15)	0.0195 (14)	0.0146 (13)	0.0029 (12)	0.0042 (11)	−0.0002 (10)
C8	0.0177 (14)	0.0209 (14)	0.0175 (14)	0.0028 (12)	0.0044 (11)	0.0010 (11)
C9	0.0179 (14)	0.0203 (14)	0.0186 (14)	0.0023 (12)	0.0039 (11)	0.0019 (11)
C10	0.0239 (15)	0.0200 (14)	0.0214 (15)	−0.0005 (12)	0.0070 (12)	0.0012 (11)
C11	0.0226 (15)	0.0211 (14)	0.0176 (14)	0.0021 (12)	0.0036 (12)	−0.0008 (11)
C12	0.0251 (16)	0.0254 (16)	0.0222 (15)	0.0021 (13)	0.0059 (12)	−0.0011 (12)
C13	0.0245 (15)	0.0252 (15)	0.0215 (15)	0.0072 (13)	0.0074 (12)	0.0041 (12)
C14	0.0278 (17)	0.0327 (18)	0.0347 (18)	0.0034 (15)	0.0146 (14)	−0.0008 (13)
C15	0.0244 (16)	0.0315 (17)	0.0254 (16)	0.0072 (14)	0.0083 (13)	−0.0006 (12)
C16	0.0314 (17)	0.0256 (16)	0.0308 (17)	0.0067 (14)	0.0105 (14)	0.0048 (13)
C17	0.0290 (17)	0.0287 (17)	0.0284 (17)	0.0074 (14)	0.0110 (14)	0.0037 (13)
C18	0.0260 (16)	0.0307 (16)	0.0207 (15)	0.0123 (14)	0.0077 (12)	0.0014 (12)
C19	0.0263 (16)	0.0247 (16)	0.0302 (17)	0.0003 (14)	0.0090 (13)	−0.0016 (12)
C20	0.0203 (15)	0.0287 (16)	0.0285 (16)	0.0021 (13)	0.0096 (13)	0.0039 (13)

Geometric parameters (Å, º) top

S1—O4	1.4353 (19)	C6—H6	0.9500
S1—O3	1.4437 (19)	C7—C8	1.427 (4)
S1—N4	1.605 (3)	C8—C11	1.417 (4)
S1—C4	1.770 (3)	C8—C9	1.423 (4)
F1—C18	1.372 (3)	C9—C10	1.497 (4)
O1—C7	1.270 (3)	C10—H10A	0.9800
O2—C11	1.336 (3)	C10—H10B	0.9800
O2—H1	0.848 (10)	C10—H10C	0.9800
N1—C7	1.375 (3)	C11—C12	1.402 (4)
N1—N2	1.410 (3)	C12—C13	1.387 (4)
N1—C1	1.415 (3)	C12—H12	0.9500
N2—C9	1.311 (4)	C13—C14	1.508 (4)
N3—C13	1.342 (4)	C14—H14A	0.9800
N3—C15	1.436 (4)	C14—H14B	0.9800
N3—H3	0.881 (10)	C14—H14C	0.9800
N4—H41	0.878 (10)	C15—C20	1.382 (4)
N4—H42	0.875 (10)	C15—C16	1.393 (4)
C1—C2	1.397 (4)	C16—C17	1.368 (4)
C1—C6	1.401 (4)	C16—H16	0.9500
C2—C3	1.381 (4)	C17—C18	1.361 (4)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.391 (4)	C18—C19	1.375 (4)
C3—H3A	0.9500	C19—C20	1.380 (4)
C4—C5	1.398 (4)	C19—H19	0.9500
C5—C6	1.386 (4)	C20—H20	0.9500
C5—H5	0.9500

O4—S1—O3	118.53 (11)	N2—C9—C10	119.3 (2)
O4—S1—N4	108.00 (13)	C8—C9—C10	128.9 (3)
O3—S1—N4	106.03 (12)	C9—C10—H10A	109.5
O4—S1—C4	106.19 (12)	C9—C10—H10B	109.5
O3—S1—C4	108.51 (13)	H10A—C10—H10B	109.5
N4—S1—C4	109.38 (13)	C9—C10—H10C	109.5
C11—O2—H1	105 (3)	H10A—C10—H10C	109.5
C7—N1—N2	111.1 (2)	H10B—C10—H10C	109.5
C7—N1—C1	129.7 (2)	O2—C11—C12	117.8 (3)
N2—N1—C1	119.2 (2)	O2—C11—C8	115.8 (2)
C9—N2—N1	106.2 (2)	C12—C11—C8	126.4 (2)
C13—N3—C15	127.8 (2)	C13—C12—C11	126.6 (3)
C13—N3—H3	114 (2)	C13—C12—H12	116.7
C15—N3—H3	118 (2)	C11—C12—H12	116.7
S1—N4—H41	111 (2)	N3—C13—C12	122.7 (3)
S1—N4—H42	110 (2)	N3—C13—C14	119.2 (3)
H41—N4—H42	121 (3)	C12—C13—C14	118.1 (3)
C2—C1—C6	120.2 (2)	C13—C14—H14A	109.5
C2—C1—N1	120.2 (2)	C13—C14—H14B	109.5
C6—C1—N1	119.6 (2)	H14A—C14—H14B	109.5
C3—C2—C1	119.3 (3)	C13—C14—H14C	109.5
C3—C2—H2	120.3	H14A—C14—H14C	109.5
C1—C2—H2	120.3	H14B—C14—H14C	109.5
C2—C3—C4	120.7 (2)	C20—C15—C16	119.7 (3)
C2—C3—H3A	119.6	C20—C15—N3	116.5 (2)
C4—C3—H3A	119.6	C16—C15—N3	123.6 (3)
C3—C4—C5	120.2 (3)	C17—C16—C15	119.5 (3)
C3—C4—S1	118.9 (2)	C17—C16—H16	120.2
C5—C4—S1	120.9 (2)	C15—C16—H16	120.2
C6—C5—C4	119.4 (2)	C18—C17—C16	119.9 (3)
C6—C5—H5	120.3	C18—C17—H17	120.0
C4—C5—H5	120.3	C16—C17—H17	120.0
C5—C6—C1	120.1 (2)	C17—C18—F1	119.4 (2)
C5—C6—H6	120.0	C17—C18—C19	122.0 (3)
C1—C6—H6	120.0	F1—C18—C19	118.6 (3)
O1—C7—N1	126.8 (2)	C18—C19—C20	118.4 (3)
O1—C7—C8	127.7 (2)	C18—C19—H19	120.8
N1—C7—C8	105.5 (2)	C20—C19—H19	120.8
C11—C8—C9	134.9 (3)	C19—C20—C15	120.4 (3)
C11—C8—C7	119.6 (2)	C19—C20—H20	119.8
C9—C8—C7	105.5 (2)	C15—C20—H20	119.8
N2—C9—C8	111.8 (2)

C7—N1—N2—C9	0.5 (3)	N1—C7—C8—C9	1.2 (3)
C1—N1—N2—C9	178.6 (2)	N1—N2—C9—C8	0.3 (3)
C7—N1—C1—C2	−7.0 (4)	N1—N2—C9—C10	−178.6 (2)
N2—N1—C1—C2	175.4 (2)	C11—C8—C9—N2	−179.4 (3)
C7—N1—C1—C6	173.8 (3)	C7—C8—C9—N2	−1.0 (3)
N2—N1—C1—C6	−3.8 (4)	C11—C8—C9—C10	−0.6 (6)
C6—C1—C2—C3	1.8 (4)	C7—C8—C9—C10	177.8 (3)
N1—C1—C2—C3	−177.4 (3)	C9—C8—C11—O2	177.0 (3)
C1—C2—C3—C4	0.3 (4)	C7—C8—C11—O2	−1.2 (4)
C2—C3—C4—C5	−1.4 (4)	C9—C8—C11—C12	−3.1 (6)
C2—C3—C4—S1	177.1 (2)	C7—C8—C11—C12	178.6 (3)
O4—S1—C4—C3	10.3 (3)	O2—C11—C12—C13	−5.5 (5)
O3—S1—C4—C3	−118.1 (2)	C8—C11—C12—C13	174.7 (3)
N4—S1—C4—C3	126.6 (2)	C15—N3—C13—C12	−171.6 (3)
O4—S1—C4—C5	−171.2 (2)	C15—N3—C13—C14	10.4 (5)
O3—S1—C4—C5	60.3 (3)	C11—C12—C13—N3	−0.2 (5)
N4—S1—C4—C5	−54.9 (3)	C11—C12—C13—C14	177.9 (3)
C3—C4—C5—C6	0.3 (4)	C13—N3—C15—C20	−148.1 (3)
S1—C4—C5—C6	−178.1 (2)	C13—N3—C15—C16	37.0 (5)
C4—C5—C6—C1	1.8 (4)	C20—C15—C16—C17	2.6 (5)
C2—C1—C6—C5	−2.9 (4)	N3—C15—C16—C17	177.3 (3)
N1—C1—C6—C5	176.3 (3)	C15—C16—C17—C18	−2.3 (5)
N2—N1—C7—O1	178.0 (3)	C16—C17—C18—F1	−179.4 (3)
C1—N1—C7—O1	0.2 (5)	C16—C17—C18—C19	0.0 (5)
N2—N1—C7—C8	−1.1 (3)	C17—C18—C19—C20	1.9 (5)
C1—N1—C7—C8	−178.9 (3)	F1—C18—C19—C20	−178.6 (3)
O1—C7—C8—C11	0.9 (5)	C18—C19—C20—C15	−1.6 (5)
N1—C7—C8—C11	179.9 (2)	C16—C15—C20—C19	−0.6 (5)
O1—C7—C8—C9	−177.8 (3)	N3—C15—C20—C19	−175.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1	0.85 (1)	1.71 (2)	2.522 (3)	161 (4)
N3—H3···O2	0.88 (1)	1.95 (2)	2.662 (3)	137 (3)
C2—H2···O1	0.95	2.26	2.917 (4)	126
N4—H41···N2ⁱ	0.88 (1)	2.14 (1)	2.999 (3)	167 (3)
N4—H42···O3ⁱⁱ	0.88 (1)	2.08 (1)	2.943 (3)	169 (3)

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉FN₄O₄S
M_r	430.45
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.8121 (5), 10.0137 (8), 12.6003 (9)
α, β, γ (°)	97.950 (6), 104.632 (6), 98.394 (6)
V (Å³)	927.58 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.25 × 0.10 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.946, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	6559, 4240, 2935
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.146, 1.01
No. of reflections	4240
No. of parameters	287
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.36

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1	0.85 (1)	1.706 (16)	2.522 (3)	161 (4)
N3—H3···O2	0.88 (1)	1.95 (2)	2.662 (3)	137 (3)
C2—H2···O1	0.95	2.26	2.917 (4)	126
N4—H41···N2ⁱ	0.88 (1)	2.14 (1)	2.999 (3)	167 (3)
N4—H42···O3ⁱⁱ	0.88 (1)	2.08 (1)	2.943 (3)	169 (3)

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

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors are thankful to the Center of Excellence for Advanced Materials Research and the Chemistry Department of King Abdulaziz University for providing research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Asiri, A. M., Al-Youbi, A. O., Alamry, K. A., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2157. Web of Science CSD CrossRef IUCr Journals Google Scholar
Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2353. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bendaas, A., Hamdi, M. & Sellier, N. (1999). J. Heterocycl. Chem. 36, 1291–1294. CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gelin, S., Chantegrel, B. & Nadi, A. I. (1983). J. Org. Chem. 48, 4078–4082. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Pages o762-o763

doi:10.1107/S1600536812006502

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-{(4Z)-4-[(2Z)-3-(4-Fluoro­anilino)-1-hy­dr­oxy­but-2-en-1-yl­­idene]-3-methyl-5-oxo-4,5-di­hydro-1H-pyrazol-1-yl}­benzene­sulfonamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-{(4Z)-4-[(2Z)-3-(4-Fluoroanilino)-1-hydroxybut-2-en-1-ylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzenesulfonamide