4-(5,3′-Dimethyl-5′-oxo-2-phenyl-2′,5′-dihydro-2H-[3,4′]bipyrazol-1′-yl)benzene­sulfonamide monohydrate

Asiri, A.M.; Al-Youbi, A.O.; Faidallah, H.M.; Alamry, K.A.; Ng, S.W.

doi:10.1107/S1600536811034453

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2474

doi:10.1107/S1600536811034453

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4-(5,3′-Dimethyl-5′-oxo-2-phenyl-2′,5′-dihydro-2H-[3,4′]bipyrazol-1′-yl)benzenesulfonamide monohydrate

Abdullah M. Asiri,^a,^b Abdulrahman O. Al-Youbi,^a Hassan M. Faidallah,^a Khalid A. Alamry ^a and Seik Weng Ng ^c,^a ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, ^bCenter of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 August 2011; accepted 22 August 2011; online 27 August 2011)

In the title compound, C₂₀H₁₉N₅O₃S·H₂O, the pyrazole ring is connected to a pyrazolone ring, and the two five-membered rings are aligned at 45.0 (1)°. The pyrazole ring is connected to a phenyl ring and the two are twisted by 42.7 (1)°. Finally, the pyrazolone ring is connected to a benzene ring and the two are twisted by 19.5 (1)°. The N—H and –NH₂ portions and the solvent water molecules are engaged in N—H⋯N, N—H⋯O and O—H⋯O hydrogen-bonding interactions to generate a three-dimensional network.

Related literature

For related pyrazole–benzenesulfonamides, see: Al-Youbi et al. (2011 ); Asiri et al. (2011 ).

Experimental

Crystal data

C₂₀H₁₉N₅O₃S·H₂O
M_r = 427.48
Monoclinic, P 2₁ /c
a = 11.1570 (5) Å
b = 12.3305 (5) Å
c = 14.9228 (5) Å
β = 107.142 (4)°
V = 1961.75 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.941, T_max = 0.960
9403 measured reflections
4382 independent reflections
3259 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.130
S = 1.01
4382 reflections
288 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2ⁱ	0.88 (1)	2.05 (1)	2.927 (3)	175 (2)
N5—H51⋯O1ⁱ	0.88 (1)	2.05 (1)	2.913 (3)	165 (2)
N5—H52⋯O1Wⁱⁱ	0.88 (1)	2.09 (1)	2.932 (3)	161 (2)
O1W—H11⋯O1	0.84 (1)	1.94 (1)	2.769 (2)	169 (3)
O1W—H12⋯O2ⁱⁱⁱ	0.84 (1)	2.38 (2)	3.158 (2)	154 (3)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); 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: 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/S1600536811034453/xu5305sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034453/xu5305Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034453/xu5305Isup3.cml

checkCIF report

Comment top

This study extends on structural studies (Asiri et al., 2011; Al-Youbi et al., 2011) of compounds having a pyrrole ring as well as a benzesulfonamide unit, the combination of which is expected to lead to enhanced medicinal activity. The present compound is a pyrazole that is connected to a pyrazorolone (Scheme I, Fig. 1). The two five-membered ring-systems are aligned at 45.0 (1)°. The pyrazole ring-system is connected to a phenyl ring and the two are twisted by 42.7 (1)°; the pyrazolone ring-system is connected to a benzene ring and the two are twisted by 19.5 (1)°. The ═N—H and –NH₂ portions and the lattice water molecule are engagd in N—H···N, N—H···O and O—H···O hydrogen bonding interactions to generate a three-dimensional network (Table 1). The amino N atom shows pyramidal coordination.

Related literature top

For related pyrazole–benzenesulfonamides, see: Asiri et al. (2011); Al-Youbi et al. (2011).

Experimental top

4-Acetoacetyl-3-methyl-1-(p-sulpfamylphenyl)-2-pyrazolin-5-one (0.05 mol) and phenylhydrazine (0.05 mol) were heated in a mixture of ethanol (50 ml) and acetic acid (50 ml) for 2 h. The mixture was allowed and the solid was collected and recrystallized from ethanol to give colorless prisms; m.p. 578–579 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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 C₂₀H₂₁N₅O₄S at the 70% probability level; H atoms are drawn as spheres of arbitrary radius. The molecule lies on a center-of-inversion.

4-(5,3'-Dimethyl-5'-oxo-2-phenyl-2',5'-dihydro-2H-[3,4']bipyrazol-1'- yl)benzenesulfonamide monohydrate top

Crystal data top

C₂₀H₁₉N₅O₃S·H₂O	F(000) = 896
M_r = 427.48	D_x = 1.447 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3286 reflections
a = 11.1570 (5) Å	θ = 2.5–29.4°
b = 12.3305 (5) Å	µ = 0.21 mm⁻¹
c = 14.9228 (5) Å	T = 100 K
β = 107.142 (4)°	Prism, colourless
V = 1961.75 (14) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4382 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3259 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.039
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −11→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→15
T_min = 0.941, T_max = 0.960	l = −19→19
9403 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0564P)² + 0.8598P] where P = (F_o² + 2F_c²)/3
4382 reflections	(Δ/σ)_max = 0.001
288 parameters	Δρ_max = 0.51 e Å⁻³
5 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₂₀H₁₉N₅O₃S·H₂O	V = 1961.75 (14) Å³
M_r = 427.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.1570 (5) Å	µ = 0.21 mm⁻¹
b = 12.3305 (5) Å	T = 100 K
c = 14.9228 (5) Å	0.30 × 0.25 × 0.20 mm
β = 107.142 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4382 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3259 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.960	R_int = 0.039
9403 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	5 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.51 e Å⁻³
4382 reflections	Δρ_min = −0.54 e Å⁻³
288 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.71034 (5)	0.80796 (5)	0.74400 (3)	0.01854 (16)
O1	0.42087 (15)	0.58177 (12)	0.31140 (10)	0.0197 (4)
O2	0.73924 (16)	0.92176 (13)	0.75124 (10)	0.0249 (4)
O3	0.80889 (15)	0.73007 (14)	0.75709 (10)	0.0257 (4)
O1W	0.51292 (17)	0.41557 (14)	0.22561 (12)	0.0262 (4)
H11	0.476 (2)	0.4640 (17)	0.2472 (18)	0.039*
H12	0.5866 (13)	0.439 (2)	0.2367 (19)	0.039*
N1	0.17489 (17)	0.67063 (15)	0.04860 (11)	0.0166 (4)
N2	0.15213 (17)	0.59426 (15)	−0.02130 (12)	0.0187 (4)
N3	0.24829 (17)	0.80650 (15)	0.33546 (12)	0.0163 (4)
H3	0.217 (2)	0.8392 (17)	0.3758 (13)	0.020*
N4	0.34314 (17)	0.73153 (15)	0.37024 (11)	0.0161 (4)
N5	0.63792 (19)	0.78264 (16)	0.82054 (13)	0.0209 (4)
H51	0.5824 (19)	0.8327 (16)	0.8217 (17)	0.025*
H52	0.609 (2)	0.7161 (11)	0.8133 (17)	0.025*
C1	0.1501 (2)	0.39583 (19)	−0.03171 (15)	0.0230 (5)
H1A	0.1414	0.4119	−0.0976	0.035*
H1B	0.0744	0.3588	−0.0271	0.035*
H1C	0.2231	0.3489	−0.0063	0.035*
C2	0.1673 (2)	0.49882 (18)	0.02272 (14)	0.0189 (5)
C3	0.1981 (2)	0.51292 (19)	0.11991 (14)	0.0188 (5)
H3A	0.2127	0.4575	0.1661	0.023*
C4	0.2029 (2)	0.62324 (18)	0.13530 (14)	0.0170 (5)
C5	0.1673 (2)	0.78201 (18)	0.02104 (14)	0.0176 (5)
C6	0.0699 (2)	0.81337 (19)	−0.05719 (15)	0.0220 (5)
H6	0.0077	0.7625	−0.0885	0.026*
C7	0.0647 (2)	0.9183 (2)	−0.08844 (17)	0.0293 (6)
H7	−0.0005	0.9399	−0.1424	0.035*
C8	0.1543 (2)	0.9932 (2)	−0.04149 (17)	0.0280 (6)
H8	0.1499	1.0660	−0.0630	0.034*
C9	0.2497 (2)	0.9619 (2)	0.03634 (16)	0.0241 (5)
H9	0.3101	1.0136	0.0688	0.029*
C10	0.2580 (2)	0.85513 (18)	0.06757 (14)	0.0193 (5)
H10	0.3250	0.8329	0.1200	0.023*
C11	0.0624 (2)	0.83177 (19)	0.20154 (15)	0.0220 (5)
H11A	0.0022	0.7821	0.1604	0.033*
H11B	0.0820	0.8907	0.1641	0.033*
H11C	0.0261	0.8621	0.2484	0.033*
C12	0.1786 (2)	0.77221 (19)	0.24935 (13)	0.0173 (5)
C13	0.2349 (2)	0.68339 (18)	0.22385 (14)	0.0160 (5)
C14	0.3403 (2)	0.65484 (18)	0.30161 (14)	0.0164 (5)
C15	0.4352 (2)	0.74994 (18)	0.45697 (13)	0.0157 (5)
C16	0.5117 (2)	0.66528 (18)	0.50240 (14)	0.0167 (5)
H16	0.5053	0.5957	0.4740	0.020*
C17	0.5975 (2)	0.68359 (18)	0.58972 (14)	0.0178 (5)
H17	0.6511	0.6267	0.6211	0.021*
C18	0.6048 (2)	0.78517 (18)	0.63096 (14)	0.0172 (5)
C19	0.5284 (2)	0.86945 (18)	0.58551 (14)	0.0178 (5)
H19	0.5337	0.9386	0.6145	0.021*
C20	0.4444 (2)	0.85223 (18)	0.49786 (14)	0.0176 (5)
H20	0.3932	0.9100	0.4657	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0154 (3)	0.0224 (3)	0.0164 (3)	−0.0013 (2)	0.0024 (2)	−0.0019 (2)
O1	0.0191 (9)	0.0182 (8)	0.0203 (7)	0.0040 (7)	0.0035 (6)	−0.0034 (6)
O2	0.0256 (10)	0.0252 (9)	0.0226 (8)	−0.0094 (7)	0.0052 (7)	−0.0042 (7)
O3	0.0166 (9)	0.0354 (10)	0.0219 (8)	0.0055 (7)	0.0008 (6)	−0.0032 (7)
O1W	0.0283 (10)	0.0204 (9)	0.0329 (9)	−0.0007 (8)	0.0136 (8)	−0.0039 (7)
N1	0.0164 (10)	0.0189 (10)	0.0141 (8)	−0.0023 (8)	0.0039 (7)	−0.0021 (7)
N2	0.0166 (10)	0.0205 (10)	0.0193 (9)	−0.0032 (8)	0.0060 (7)	−0.0062 (8)
N3	0.0176 (10)	0.0160 (10)	0.0156 (8)	0.0046 (8)	0.0054 (7)	0.0000 (7)
N4	0.0158 (10)	0.0163 (9)	0.0152 (8)	0.0036 (8)	0.0033 (7)	0.0001 (7)
N5	0.0233 (11)	0.0198 (10)	0.0197 (9)	−0.0011 (9)	0.0063 (8)	−0.0022 (9)
C1	0.0239 (13)	0.0216 (12)	0.0235 (11)	−0.0024 (10)	0.0069 (9)	−0.0030 (10)
C2	0.0160 (11)	0.0198 (12)	0.0206 (10)	−0.0025 (9)	0.0050 (8)	−0.0009 (9)
C3	0.0169 (11)	0.0201 (12)	0.0188 (10)	0.0000 (9)	0.0045 (8)	0.0023 (9)
C4	0.0127 (11)	0.0219 (12)	0.0156 (10)	−0.0006 (9)	0.0030 (8)	−0.0006 (9)
C5	0.0182 (12)	0.0181 (11)	0.0185 (10)	−0.0005 (9)	0.0083 (9)	−0.0004 (9)
C6	0.0209 (13)	0.0229 (13)	0.0215 (11)	−0.0013 (10)	0.0052 (9)	0.0004 (10)
C7	0.0255 (14)	0.0292 (14)	0.0303 (12)	0.0041 (11)	0.0038 (10)	0.0039 (11)
C8	0.0280 (14)	0.0181 (12)	0.0399 (14)	0.0025 (11)	0.0131 (11)	0.0051 (11)
C9	0.0254 (13)	0.0227 (13)	0.0272 (12)	−0.0071 (10)	0.0124 (10)	−0.0081 (10)
C10	0.0211 (12)	0.0211 (12)	0.0172 (10)	−0.0011 (10)	0.0080 (9)	−0.0036 (9)
C11	0.0210 (13)	0.0243 (13)	0.0186 (10)	0.0051 (10)	0.0026 (9)	0.0012 (10)
C12	0.0172 (12)	0.0220 (12)	0.0132 (9)	−0.0010 (9)	0.0055 (8)	0.0019 (9)
C13	0.0139 (11)	0.0188 (11)	0.0153 (9)	−0.0010 (9)	0.0044 (8)	−0.0009 (9)
C14	0.0198 (12)	0.0148 (11)	0.0164 (10)	−0.0021 (9)	0.0080 (9)	0.0005 (9)
C15	0.0158 (11)	0.0189 (12)	0.0134 (9)	−0.0008 (9)	0.0058 (8)	0.0006 (9)
C16	0.0191 (12)	0.0142 (11)	0.0181 (10)	0.0017 (9)	0.0076 (8)	−0.0012 (9)
C17	0.0179 (12)	0.0184 (12)	0.0169 (10)	0.0033 (9)	0.0051 (8)	0.0012 (9)
C18	0.0145 (11)	0.0221 (12)	0.0147 (9)	−0.0023 (9)	0.0040 (8)	0.0003 (9)
C19	0.0211 (12)	0.0160 (11)	0.0173 (10)	−0.0007 (9)	0.0072 (9)	−0.0014 (9)
C20	0.0183 (12)	0.0150 (11)	0.0198 (10)	0.0017 (9)	0.0061 (9)	0.0021 (9)

Geometric parameters (Å, º) top

S1—O3	1.4293 (17)	C5—C6	1.395 (3)
S1—O2	1.4366 (16)	C6—C7	1.371 (3)
S1—N5	1.612 (2)	C6—H6	0.9500
S1—C18	1.772 (2)	C7—C8	1.390 (3)
O1—C14	1.251 (3)	C7—H7	0.9500
O1W—H11	0.844 (10)	C8—C9	1.379 (3)
O1W—H12	0.840 (10)	C8—H8	0.9500
N1—C4	1.369 (3)	C9—C10	1.391 (3)
N1—N2	1.372 (2)	C9—H9	0.9500
N1—C5	1.429 (3)	C10—H10	0.9500
N2—C2	1.334 (3)	C11—C12	1.477 (3)
N3—C12	1.359 (3)	C11—H11A	0.9800
N3—N4	1.386 (2)	C11—H11B	0.9800
N3—H3	0.880 (9)	C11—H11C	0.9800
N4—C14	1.387 (3)	C12—C13	1.371 (3)
N4—C15	1.413 (3)	C13—C14	1.431 (3)
N5—H51	0.878 (10)	C15—C20	1.392 (3)
N5—H52	0.876 (10)	C15—C16	1.392 (3)
C1—C2	1.489 (3)	C16—C17	1.390 (3)
C1—H1A	0.9800	C16—H16	0.9500
C1—H1B	0.9800	C17—C18	1.387 (3)
C1—H1C	0.9800	C17—H17	0.9500
C2—C3	1.399 (3)	C18—C19	1.388 (3)
C3—C4	1.378 (3)	C19—C20	1.382 (3)
C3—H3A	0.9500	C19—H19	0.9500
C4—C13	1.465 (3)	C20—H20	0.9500
C5—C10	1.381 (3)

O3—S1—O2	119.96 (11)	C8—C7—H7	119.9
O3—S1—N5	107.40 (10)	C9—C8—C7	120.1 (2)
O2—S1—N5	106.50 (10)	C9—C8—H8	120.0
O3—S1—C18	106.98 (10)	C7—C8—H8	120.0
O2—S1—C18	107.33 (10)	C8—C9—C10	120.3 (2)
N5—S1—C18	108.23 (10)	C8—C9—H9	119.8
H11—O1W—H12	104 (3)	C10—C9—H9	119.8
C4—N1—N2	111.40 (18)	C5—C10—C9	118.9 (2)
C4—N1—C5	131.29 (18)	C5—C10—H10	120.5
N2—N1—C5	117.31 (16)	C9—C10—H10	120.5
C2—N2—N1	105.24 (16)	C12—C11—H11A	109.5
C12—N3—N4	107.92 (17)	C12—C11—H11B	109.5
C12—N3—H3	123.8 (16)	H11A—C11—H11B	109.5
N4—N3—H3	117.7 (15)	C12—C11—H11C	109.5
N3—N4—C14	109.23 (16)	H11A—C11—H11C	109.5
N3—N4—C15	120.29 (17)	H11B—C11—H11C	109.5
C14—N4—C15	129.64 (19)	N3—C12—C13	109.25 (19)
S1—N5—H51	112.5 (16)	N3—C12—C11	118.57 (19)
S1—N5—H52	109.6 (17)	C13—C12—C11	132.18 (19)
H51—N5—H52	115 (3)	C12—C13—C14	107.79 (18)
C2—C1—H1A	109.5	C12—C13—C4	130.18 (19)
C2—C1—H1B	109.5	C14—C13—C4	122.0 (2)
H1A—C1—H1B	109.5	O1—C14—N4	123.05 (19)
C2—C1—H1C	109.5	O1—C14—C13	131.5 (2)
H1A—C1—H1C	109.5	N4—C14—C13	105.40 (19)
H1B—C1—H1C	109.5	C20—C15—C16	120.71 (19)
N2—C2—C3	110.95 (19)	C20—C15—N4	119.14 (19)
N2—C2—C1	120.43 (19)	C16—C15—N4	120.09 (19)
C3—C2—C1	128.6 (2)	C17—C16—C15	119.3 (2)
C4—C3—C2	106.32 (19)	C17—C16—H16	120.4
C4—C3—H3A	126.8	C15—C16—H16	120.4
C2—C3—H3A	126.8	C18—C17—C16	119.8 (2)
N1—C4—C3	106.09 (18)	C18—C17—H17	120.1
N1—C4—C13	124.3 (2)	C16—C17—H17	120.1
C3—C4—C13	129.60 (19)	C17—C18—C19	120.79 (19)
C10—C5—C6	121.0 (2)	C17—C18—S1	120.08 (17)
C10—C5—N1	120.7 (2)	C19—C18—S1	119.12 (17)
C6—C5—N1	118.2 (2)	C20—C19—C18	119.7 (2)
C7—C6—C5	119.4 (2)	C20—C19—H19	120.2
C7—C6—H6	120.3	C18—C19—H19	120.2
C5—C6—H6	120.3	C19—C20—C15	119.7 (2)
C6—C7—C8	120.2 (2)	C19—C20—H20	120.1
C6—C7—H7	119.9	C15—C20—H20	120.1

C4—N1—N2—C2	−0.5 (2)	N1—C4—C13—C12	46.1 (4)
C5—N1—N2—C2	178.93 (19)	C3—C4—C13—C12	−136.2 (3)
C12—N3—N4—C14	5.7 (2)	N1—C4—C13—C14	−132.9 (2)
C12—N3—N4—C15	176.18 (18)	C3—C4—C13—C14	44.9 (4)
N1—N2—C2—C3	0.7 (2)	N3—N4—C14—O1	174.80 (19)
N1—N2—C2—C1	−179.8 (2)	C15—N4—C14—O1	5.5 (4)
N2—C2—C3—C4	−0.6 (3)	N3—N4—C14—C13	−2.6 (2)
C1—C2—C3—C4	180.0 (2)	C15—N4—C14—C13	−171.9 (2)
N2—N1—C4—C3	0.1 (2)	C12—C13—C14—O1	−178.5 (2)
C5—N1—C4—C3	−179.2 (2)	C4—C13—C14—O1	0.6 (4)
N2—N1—C4—C13	178.32 (19)	C12—C13—C14—N4	−1.4 (2)
C5—N1—C4—C13	−1.0 (4)	C4—C13—C14—N4	177.73 (19)
C2—C3—C4—N1	0.3 (2)	N3—N4—C15—C20	−12.5 (3)
C2—C3—C4—C13	−177.8 (2)	C14—N4—C15—C20	155.8 (2)
C4—N1—C5—C10	44.3 (3)	N3—N4—C15—C16	164.83 (19)
N2—N1—C5—C10	−135.0 (2)	C14—N4—C15—C16	−26.9 (3)
C4—N1—C5—C6	−139.3 (2)	C20—C15—C16—C17	0.3 (3)
N2—N1—C5—C6	41.4 (3)	N4—C15—C16—C17	−176.93 (19)
C10—C5—C6—C7	0.3 (3)	C15—C16—C17—C18	0.8 (3)
N1—C5—C6—C7	−176.2 (2)	C16—C17—C18—C19	−0.8 (3)
C5—C6—C7—C8	−1.2 (4)	C16—C17—C18—S1	177.88 (17)
C6—C7—C8—C9	0.6 (4)	O3—S1—C18—C17	25.0 (2)
C7—C8—C9—C10	0.9 (4)	O2—S1—C18—C17	154.97 (18)
C6—C5—C10—C9	1.3 (3)	N5—S1—C18—C17	−90.4 (2)
N1—C5—C10—C9	177.60 (19)	O3—S1—C18—C19	−156.30 (18)
C8—C9—C10—C5	−1.9 (3)	O2—S1—C18—C19	−26.3 (2)
N4—N3—C12—C13	−6.7 (2)	N5—S1—C18—C19	88.25 (19)
N4—N3—C12—C11	173.17 (19)	C17—C18—C19—C20	−0.4 (3)
N3—C12—C13—C14	5.0 (2)	S1—C18—C19—C20	−179.08 (17)
C11—C12—C13—C14	−174.8 (2)	C18—C19—C20—C15	1.5 (3)
N3—C12—C13—C4	−174.0 (2)	C16—C15—C20—C19	−1.5 (3)
C11—C12—C13—C4	6.2 (4)	N4—C15—C20—C19	175.77 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2ⁱ	0.88 (1)	2.05 (1)	2.927 (3)	175 (2)
N5—H51···O1ⁱ	0.88 (1)	2.05 (1)	2.913 (3)	165 (2)
N5—H52···O1Wⁱⁱ	0.88 (1)	2.09 (1)	2.932 (3)	161 (2)
O1W—H11···O1	0.84 (1)	1.94 (1)	2.769 (2)	169 (3)
O1W—H12···O2ⁱⁱⁱ	0.84 (1)	2.38 (2)	3.158 (2)	154 (3)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₅O₃S·H₂O
M_r	427.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.1570 (5), 12.3305 (5), 14.9228 (5)
β (°)	107.142 (4)
V (Å³)	1961.75 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.941, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	9403, 4382, 3259
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.130, 1.01
No. of reflections	4382
No. of parameters	288
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.54

Computer programs: CrysAlis PRO (Agilent, 2010), 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
N3—H3···N2ⁱ	0.88 (1)	2.05 (1)	2.927 (3)	175 (2)
N5—H51···O1ⁱ	0.88 (1)	2.05 (1)	2.913 (3)	165 (2)
N5—H52···O1Wⁱⁱ	0.88 (1)	2.09 (1)	2.932 (3)	161 (2)
O1W—H11···O1	0.84 (1)	1.94 (1)	2.769 (2)	169 (3)
O1W—H12···O2ⁱⁱⁱ	0.84 (1)	2.38 (2)	3.158 (2)	154 (3)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+3/2, z−1/2.

Acknowledgements

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Al-Youbi, A. O., Asiri, A. M., Faidallah, H. M., Alamry, K. A. & Ng, S. W. (2011). Acta Cryst. E67, o2428. Google Scholar
Asiri, A. M., Faidallah, H. M., Al-Youbi, A. O. & Ng, S. W. (2011). Acta Cryst. E67, o2427. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS 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 67| Part 9| September 2011| Page o2474

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

4-(5,3′-Di­methyl-5′-oxo-2-phenyl-2′,5′-di­hydro-2H-[3,4′]bipyrazol-1′-yl)benzene­sulfonamide monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(5,3′-Dimethyl-5′-oxo-2-phenyl-2′,5′-dihydro-2H-[3,4′]bipyrazol-1′-yl)benzenesulfonamide monohydrate