(E,E)-4-{4-[3-(4-Chloro­anilino)-1-hydroxy­but-2-enyl­idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}­benzene­sulfonamide

Asiri, A.M.; Faidallah, H.M.; Ng, S.W.

doi:10.1107/S1600536811020617

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1590

doi:10.1107/S1600536811020617

Open

access

(E,E)-4-{4-[3-(4-Chloroanilino)-1-hydroxybut-2-enylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzenesulfonamide

Abdullah M. Asiri,^a Hassan M. Faidallah ^a and Seik Weng Ng ^b ^*

^aChemistry Department, Faculty of Science, King Abdul Aziz University, Jeddah 21589, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 26 May 2011; accepted 30 May 2011; online 4 June 2011)

The molecule of the title compound, C₂₀H₁₉ClN₄O₄S, features a central pyrazole ring that possesses a benzene substituent, as well as a conjugated =C—C=C—C_methyl substituent. The benzene ring is slightly twisted [dihedral angle = 7.7 (2)°] with respect to the five-membered ring; the mean plane of the zigzag =C—C=C—C fragment [torsion angle = 178.0 (4)°] is also slightly twisted [dihedral angle = 10.6 (4)°]. The amine and hydroxy groups form intramolecular hydrogen bonds. The amide group uses one of its H atoms to form a hydrogen bond to the sulfamyl O atom of an inversion-related molecule. Adjacent dimers are further linked by an N—H_amido⋯N_pyrazole hydrogen bond to generate a linear chain. The crystal studied is a nonmerohedral twin with a minor twin component of 25.6 (2)%.

Related literature

For the synthesis of 4-acetoacetyl-3-methyl-5-onyl-1-phenylpyrazole, see: Gelin et al. (1983 ).

Experimental

Crystal data

C₂₀H₁₉ClN₄O₄S
M_r = 446.90
Monoclinic, P 2₁ /c
a = 14.7513 (17) Å
b = 17.545 (2) Å
c = 7.6203 (9) Å
β = 101.496 (2)°
V = 1932.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 100 K
0.20 × 0.02 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (TWINABS; Bruker, 2009 ) T_min = 0.935, T_max = 0.993
32586 measured reflections
3426 independent reflections
2605 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.125
S = 1.04
3426 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2	0.84	1.79	2.498 (4)	141
N1—H1⋯O1	0.88	2.00	2.659 (4)	131
N1—H1⋯O3ⁱ	0.88	2.34	3.093 (4)	143
N4—H41⋯N2ⁱⁱ	0.88	2.16	3.003 (4)	161
N4—H42⋯O4ⁱⁱⁱ	0.88	2.09	2.917 (4)	156
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z-1; (iii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020617/xu5227sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020617/xu5227Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020617/xu5227Isup3.cml

checkCIF report

Comment top

The compound, 4-acetoacetyl-3-methyl-5-onyl-1-phenylpyrazole rearranges under the influence of acetic acid to form functionalized 4-oxopyrano[2,3-c]pyrazoles (Gelin et al., 1983). The addition of a sulfamido unit to the phenyl ring is expected to improve its biological activity; in the present study, the p-sulfamyl analog is reacted with chloroaniline to yield a new p-sulfamylphenylpyrazole derivative (Scheme I). The C₂₀H₁₉ClN₄O₄S (Fig. 1) features a central pyrazole ring that possesses a benzene substituent as well as a conjugated ═ C–C═C–C_methyl substituent. The benzene ring is slightly twisted with respect to the five-membered ring; the mean plane of the zigzag ═ C–C═ C–C fragment is also slightly twisted.

The amino and hydroxy groups are intramolecular hydrogen-bond donors. The amido group uses one of its H atoms to form an hydrogen bond to the sulfamyl O atom of an inversion-related molecule. Adjacent dimers are further linked by an N–H_amido···N_pyrazole hydrogen bond to generate a linear chain motif (Table 2, Fig. 2).

Related literature top

For the synthesis of 4-acetoacetyl-3-methyl-5-onyl-1-phenylpyrazole, see: Gelin et al. (1983).

Experimental top

4-Acetoacetyl-3-methyl-5-onyl-1-p-sulfamylphenylpyrazole was synthesized by using a literature procedure (Gelin et al., 1983). The compound (1.70 g, 0.005 mol) and 4-chloroaniline (0.63 g, 0.005 mol) were heated in ethanol (25 ml) for 2 h. The solid that separated from solution was collected and recrystallized from ethanol to yield yellow prismatic crystals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₀H₁₉ClN₄O₄S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded chain motif.

(E,E)-4-{4-[3-(4-Chloroanilino)-1-hydroxybut-2-enylidene]- 3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzenesulfonamide top

Crystal data top

C₂₀H₁₉ClN₄O₄S	F(000) = 928
M_r = 446.90	D_x = 1.536 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 656 reflections
a = 14.7513 (17) Å	θ = 2.3–20.1°
b = 17.545 (2) Å	µ = 0.34 mm⁻¹
c = 7.6203 (9) Å	T = 100 K
β = 101.496 (2)°	Prism, yellow
V = 1932.6 (4) Å³	0.20 × 0.02 × 0.02 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3426 independent reflections
Radiation source: fine-focus sealed tube	2605 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
ω scans	θ_max = 25.1°, θ_min = 1.4°
Absorption correction: multi-scan (TWINABS; Bruker, 2009)	h = −17→17
T_min = 0.935, T_max = 0.993	k = 0→20
32586 measured reflections	l = 0→9

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0457P)² + 2.8595P] where P = (F_o² + 2F_c²)/3
3426 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₀H₁₉ClN₄O₄S	V = 1932.6 (4) Å³
M_r = 446.90	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.7513 (17) Å	µ = 0.34 mm⁻¹
b = 17.545 (2) Å	T = 100 K
c = 7.6203 (9) Å	0.20 × 0.02 × 0.02 mm
β = 101.496 (2)°

Data collection top

Bruker SMART APEX diffractometer	3426 independent reflections
Absorption correction: multi-scan (TWINABS; Bruker, 2009)	2605 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.993	R_int = 0.099
32586 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	Δρ_max = 0.39 e Å⁻³
3426 reflections	Δρ_min = −0.47 e Å⁻³
275 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	1.06569 (7)	0.72948 (6)	1.73048 (15)	0.0256 (3)
S1	0.14888 (7)	0.47564 (6)	0.00333 (13)	0.0137 (2)
O1	0.58091 (18)	0.59404 (16)	1.0470 (4)	0.0200 (7)
H1O	0.5745	0.5767	0.9424	0.030*
O2	0.48625 (17)	0.55620 (16)	0.7504 (4)	0.0187 (6)
O3	0.22069 (18)	0.43897 (16)	−0.0680 (4)	0.0194 (7)
O4	0.07052 (18)	0.43097 (15)	0.0288 (4)	0.0169 (6)
N1	0.6886 (2)	0.64430 (18)	1.3466 (4)	0.0147 (7)
H1	0.6866	0.6177	1.2480	0.018*
N2	0.2764 (2)	0.63178 (18)	0.8250 (4)	0.0129 (7)
N3	0.3294 (2)	0.59328 (17)	0.7196 (4)	0.0115 (7)
N4	0.1079 (2)	0.54401 (18)	−0.1294 (4)	0.0158 (7)
H41	0.1513	0.5783	−0.1304	0.024*
H42	0.0610	0.5652	−0.0922	0.024*
C1	0.7783 (3)	0.6666 (2)	1.4438 (5)	0.0181 (9)
C2	0.8495 (3)	0.6126 (2)	1.4652 (5)	0.0195 (9)
H2	0.8370	0.5625	1.4200	0.023*
C3	0.9374 (3)	0.6319 (2)	1.5512 (5)	0.0200 (9)
H3	0.9860	0.5955	1.5648	0.024*
C4	0.9541 (3)	0.7048 (2)	1.6175 (5)	0.0187 (9)
C5	0.8863 (3)	0.7590 (2)	1.5964 (5)	0.0214 (10)
H5	0.8998	0.8088	1.6429	0.026*
C6	0.7972 (3)	0.7406 (2)	1.5065 (6)	0.0205 (9)
H6	0.7499	0.7782	1.4880	0.025*
C7	0.6074 (3)	0.6606 (2)	1.3933 (5)	0.0140 (9)
C8	0.6086 (3)	0.6938 (2)	1.5746 (5)	0.0218 (10)
H8A	0.6646	0.6771	1.6577	0.033*
H8B	0.5539	0.6766	1.6182	0.033*
H8C	0.6081	0.7496	1.5666	0.033*
C9	0.5228 (3)	0.6492 (2)	1.2803 (5)	0.0139 (8)
H9	0.4692	0.6617	1.3257	0.017*
C10	0.5088 (3)	0.6208 (2)	1.1047 (5)	0.0149 (8)
C11	0.2967 (3)	0.6930 (2)	1.1153 (5)	0.0172 (9)
H11A	0.2318	0.7065	1.0700	0.026*
H11B	0.3335	0.7397	1.1420	0.026*
H11C	0.3018	0.6626	1.2246	0.026*
C12	0.3320 (3)	0.6480 (2)	0.9771 (5)	0.0118 (8)
C13	0.4237 (3)	0.6199 (2)	0.9796 (5)	0.0141 (8)
C14	0.4195 (3)	0.5859 (2)	0.8100 (5)	0.0133 (8)
C15	0.2875 (2)	0.5682 (2)	0.5466 (5)	0.0113 (8)
C16	0.3375 (3)	0.5229 (2)	0.4485 (5)	0.0148 (8)
H16	0.4003	0.5103	0.4957	0.018*
C17	0.2940 (3)	0.4966 (2)	0.2817 (5)	0.0149 (8)
H17	0.3275	0.4660	0.2137	0.018*
C18	0.2025 (3)	0.5143 (2)	0.2129 (5)	0.0136 (8)
C19	0.1535 (3)	0.5618 (2)	0.3080 (5)	0.0154 (9)
H19	0.0913	0.5754	0.2589	0.018*
C20	0.1966 (3)	0.5890 (2)	0.4746 (5)	0.0134 (8)
H20	0.1641	0.6218	0.5397	0.016*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0176 (5)	0.0285 (6)	0.0281 (6)	−0.0015 (4)	−0.0013 (4)	−0.0037 (5)
S1	0.0109 (5)	0.0185 (5)	0.0116 (5)	0.0000 (4)	0.0020 (4)	−0.0030 (4)
O1	0.0134 (14)	0.0299 (17)	0.0165 (15)	0.0024 (12)	0.0022 (12)	−0.0079 (13)
O2	0.0117 (14)	0.0284 (16)	0.0166 (15)	0.0036 (12)	0.0045 (12)	−0.0071 (12)
O3	0.0152 (14)	0.0258 (16)	0.0168 (15)	0.0035 (12)	0.0022 (12)	−0.0089 (12)
O4	0.0136 (14)	0.0178 (15)	0.0196 (15)	−0.0041 (12)	0.0036 (12)	−0.0012 (12)
N1	0.0106 (16)	0.0211 (18)	0.0110 (17)	0.0011 (14)	−0.0017 (13)	0.0021 (14)
N2	0.0121 (17)	0.0146 (18)	0.0129 (17)	0.0005 (14)	0.0045 (14)	−0.0004 (13)
N3	0.0080 (16)	0.0151 (17)	0.0119 (17)	0.0014 (13)	0.0032 (13)	−0.0041 (13)
N4	0.0108 (16)	0.0227 (19)	0.0133 (17)	−0.0015 (14)	0.0012 (14)	0.0002 (14)
C1	0.018 (2)	0.022 (2)	0.013 (2)	−0.0011 (18)	0.0024 (17)	0.0011 (17)
C2	0.027 (2)	0.016 (2)	0.014 (2)	0.0011 (18)	0.0015 (18)	−0.0009 (17)
C3	0.018 (2)	0.022 (2)	0.020 (2)	0.0026 (18)	0.0022 (19)	0.0029 (18)
C4	0.019 (2)	0.023 (2)	0.014 (2)	0.0006 (18)	0.0035 (17)	0.0010 (17)
C5	0.024 (2)	0.020 (2)	0.020 (2)	−0.0020 (19)	0.0022 (18)	−0.0028 (18)
C6	0.020 (2)	0.018 (2)	0.023 (2)	0.0012 (19)	0.0032 (18)	0.0014 (18)
C7	0.017 (2)	0.010 (2)	0.015 (2)	0.0028 (16)	0.0034 (17)	0.0035 (16)
C8	0.022 (2)	0.026 (2)	0.017 (2)	−0.0044 (19)	0.0022 (18)	−0.0032 (18)
C9	0.0119 (19)	0.018 (2)	0.013 (2)	0.0014 (16)	0.0033 (16)	0.0000 (16)
C10	0.014 (2)	0.014 (2)	0.017 (2)	0.0003 (17)	0.0055 (17)	−0.0001 (17)
C11	0.017 (2)	0.022 (2)	0.014 (2)	0.0027 (18)	0.0042 (17)	−0.0014 (17)
C12	0.013 (2)	0.0102 (19)	0.013 (2)	−0.0018 (16)	0.0026 (16)	0.0002 (15)
C13	0.0119 (19)	0.016 (2)	0.015 (2)	−0.0017 (16)	0.0040 (17)	−0.0009 (16)
C14	0.0120 (19)	0.014 (2)	0.013 (2)	−0.0008 (16)	0.0006 (16)	−0.0002 (16)
C15	0.0139 (19)	0.011 (2)	0.0101 (19)	−0.0040 (15)	0.0037 (16)	0.0020 (15)
C16	0.0108 (19)	0.019 (2)	0.014 (2)	−0.0025 (17)	0.0016 (16)	−0.0009 (17)
C17	0.0153 (19)	0.018 (2)	0.013 (2)	0.0041 (17)	0.0055 (17)	0.0008 (16)
C18	0.015 (2)	0.015 (2)	0.0098 (19)	−0.0024 (17)	0.0006 (16)	−0.0030 (16)
C19	0.0121 (19)	0.018 (2)	0.016 (2)	0.0027 (17)	0.0023 (16)	0.0000 (17)
C20	0.013 (2)	0.015 (2)	0.014 (2)	0.0018 (16)	0.0064 (17)	−0.0009 (16)

Geometric parameters (Å, º) top

Cl1—C4	1.753 (4)	C6—H6	0.9500
S1—O3	1.436 (3)	C7—C9	1.382 (5)
S1—O4	1.441 (3)	C7—C8	1.497 (5)
S1—N4	1.607 (3)	C8—H8A	0.9800
S1—C18	1.770 (4)	C8—H8B	0.9800
O1—C10	1.316 (5)	C8—H8C	0.9800
O1—H1O	0.8400	C9—C10	1.404 (5)
O2—C14	1.275 (5)	C9—H9	0.9500
N1—C7	1.346 (5)	C10—C13	1.418 (5)
N1—C1	1.435 (5)	C11—C12	1.491 (5)
N1—H1	0.8800	C11—H11A	0.9800
N2—C12	1.310 (5)	C11—H11B	0.9800
N2—N3	1.401 (4)	C11—H11C	0.9800
N3—C14	1.376 (5)	C12—C13	1.435 (5)
N3—C15	1.410 (5)	C13—C14	1.414 (5)
N4—H41	0.8800	C15—C20	1.392 (5)
N4—H42	0.8800	C15—C16	1.398 (5)
C1—C6	1.393 (6)	C16—C17	1.383 (5)
C1—C2	1.399 (6)	C16—H16	0.9500
C2—C3	1.374 (6)	C17—C18	1.382 (5)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.379 (6)	C18—C19	1.397 (5)
C3—H3	0.9500	C19—C20	1.387 (5)
C4—C5	1.365 (6)	C19—H19	0.9500
C5—C6	1.393 (5)	C20—H20	0.9500
C5—H5	0.9500

O3—S1—O4	118.65 (17)	H8A—C8—H8C	109.5
O3—S1—N4	108.04 (17)	H8B—C8—H8C	109.5
O4—S1—N4	106.22 (17)	C7—C9—C10	126.0 (4)
O3—S1—C18	106.40 (17)	C7—C9—H9	117.0
O4—S1—C18	108.26 (17)	C10—C9—H9	117.0
N4—S1—C18	109.02 (17)	O1—C10—C9	118.1 (3)
C10—O1—H1O	120.0	O1—C10—C13	116.0 (3)
C7—N1—C1	125.6 (3)	C9—C10—C13	126.0 (4)
C7—N1—H1	117.2	C12—C11—H11A	109.5
C1—N1—H1	117.2	C12—C11—H11B	109.5
C12—N2—N3	106.9 (3)	H11A—C11—H11B	109.5
C14—N3—N2	110.6 (3)	C12—C11—H11C	109.5
C14—N3—C15	129.7 (3)	H11A—C11—H11C	109.5
N2—N3—C15	119.8 (3)	H11B—C11—H11C	109.5
S1—N4—H41	109.5	N2—C12—C13	111.0 (3)
S1—N4—H42	109.5	N2—C12—C11	119.7 (3)
H41—N4—H42	109.5	C13—C12—C11	129.2 (3)
C6—C1—C2	119.7 (4)	C14—C13—C10	119.4 (3)
C6—C1—N1	122.2 (4)	C14—C13—C12	105.3 (3)
C2—C1—N1	118.0 (4)	C10—C13—C12	135.3 (4)
C3—C2—C1	120.3 (4)	O2—C14—N3	126.7 (3)
C3—C2—H2	119.9	O2—C14—C13	127.0 (3)
C1—C2—H2	119.9	N3—C14—C13	106.2 (3)
C2—C3—C4	119.1 (4)	C20—C15—C16	120.5 (3)
C2—C3—H3	120.5	C20—C15—N3	119.6 (3)
C4—C3—H3	120.5	C16—C15—N3	119.9 (3)
C5—C4—C3	121.9 (4)	C17—C16—C15	118.9 (4)
C5—C4—Cl1	118.7 (3)	C17—C16—H16	120.5
C3—C4—Cl1	119.4 (3)	C15—C16—H16	120.5
C4—C5—C6	119.6 (4)	C18—C17—C16	120.8 (4)
C4—C5—H5	120.2	C18—C17—H17	119.6
C6—C5—H5	120.2	C16—C17—H17	119.6
C1—C6—C5	119.3 (4)	C17—C18—C19	120.3 (3)
C1—C6—H6	120.3	C17—C18—S1	118.9 (3)
C5—C6—H6	120.3	C19—C18—S1	120.8 (3)
N1—C7—C9	123.0 (4)	C20—C19—C18	119.3 (4)
N1—C7—C8	118.6 (3)	C20—C19—H19	120.3
C9—C7—C8	118.3 (3)	C18—C19—H19	120.3
C7—C8—H8A	109.5	C19—C20—C15	120.0 (4)
C7—C8—H8B	109.5	C19—C20—H20	120.0
H8A—C8—H8B	109.5	C15—C20—H20	120.0
C7—C8—H8C	109.5

C12—N2—N3—C14	0.0 (4)	C11—C12—C13—C10	2.9 (8)
C12—N2—N3—C15	179.8 (3)	N2—N3—C14—O2	−177.4 (4)
C7—N1—C1—C6	−46.9 (6)	C15—N3—C14—O2	2.8 (7)
C7—N1—C1—C2	137.2 (4)	N2—N3—C14—C13	0.8 (4)
C6—C1—C2—C3	1.5 (6)	C15—N3—C14—C13	−179.0 (4)
N1—C1—C2—C3	177.5 (4)	C10—C13—C14—O2	−2.1 (6)
C1—C2—C3—C4	0.6 (6)	C12—C13—C14—O2	177.0 (4)
C2—C3—C4—C5	−1.6 (6)	C10—C13—C14—N3	179.7 (3)
C2—C3—C4—Cl1	179.0 (3)	C12—C13—C14—N3	−1.2 (4)
C3—C4—C5—C6	0.4 (6)	C14—N3—C15—C20	−173.4 (4)
Cl1—C4—C5—C6	179.7 (3)	N2—N3—C15—C20	6.9 (5)
C2—C1—C6—C5	−2.7 (6)	C14—N3—C15—C16	6.5 (6)
N1—C1—C6—C5	−178.6 (4)	N2—N3—C15—C16	−173.2 (3)
C4—C5—C6—C1	1.8 (6)	C20—C15—C16—C17	−2.4 (6)
C1—N1—C7—C9	168.6 (4)	N3—C15—C16—C17	177.7 (3)
C1—N1—C7—C8	−10.3 (6)	C15—C16—C17—C18	−0.4 (6)
N1—C7—C9—C10	−0.9 (6)	C16—C17—C18—C19	2.7 (6)
C8—C7—C9—C10	178.0 (4)	C16—C17—C18—S1	−177.2 (3)
C7—C9—C10—O1	8.5 (6)	O3—S1—C18—C17	−7.9 (4)
C7—C9—C10—C13	−169.7 (4)	O4—S1—C18—C17	120.6 (3)
N3—N2—C12—C13	−0.8 (4)	N4—S1—C18—C17	−124.2 (3)
N3—N2—C12—C11	176.8 (3)	O3—S1—C18—C19	172.2 (3)
O1—C10—C13—C14	4.9 (6)	O4—S1—C18—C19	−59.2 (4)
C9—C10—C13—C14	−176.9 (4)	N4—S1—C18—C19	56.0 (4)
O1—C10—C13—C12	−173.8 (4)	C17—C18—C19—C20	−2.1 (6)
C9—C10—C13—C12	4.4 (8)	S1—C18—C19—C20	177.7 (3)
N2—C12—C13—C14	1.3 (4)	C18—C19—C20—C15	−0.7 (6)
C11—C12—C13—C14	−176.0 (4)	C16—C15—C20—C19	3.0 (6)
N2—C12—C13—C10	−179.8 (4)	N3—C15—C20—C19	−177.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.84	1.79	2.498 (4)	141
N1—H1···O1	0.88	2.00	2.659 (4)	131
N1—H1···O3ⁱ	0.88	2.34	3.093 (4)	143
N4—H41···N2ⁱⁱ	0.88	2.16	3.003 (4)	161
N4—H42···O4ⁱⁱⁱ	0.88	2.09	2.917 (4)	156

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉ClN₄O₄S
M_r	446.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.7513 (17), 17.545 (2), 7.6203 (9)
β (°)	101.496 (2)
V (Å³)	1932.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.20 × 0.02 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (TWINABS; Bruker, 2009)
T_min, T_max	0.935, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	32586, 3426, 2605
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.125, 1.04
No. of reflections	3426
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.47

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.84	1.79	2.498 (4)	141
N1—H1···O1	0.88	2.00	2.659 (4)	131
N1—H1···O3ⁱ	0.88	2.34	3.093 (4)	143
N4—H41···N2ⁱⁱ	0.88	2.16	3.003 (4)	161
N4—H42···O4ⁱⁱⁱ	0.88	2.09	2.917 (4)	156

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

Acknowledgements

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2, SAINT and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA. 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1590

doi:10.1107/S1600536811020617

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(E,E)-4-{4-[3-(4-Chloro­anilino)-1-hy­droxy­but-2-enyl­­idene]-3-methyl-5-oxo-4,5-di­hydro-1H-pyrazol-1-yl}­benzene­sulfonamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E,E)-4-{4-[3-(4-Chloroanilino)-1-hydroxybut-2-enylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzenesulfonamide