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

In the title compound, C(20)H(19)N(5)O(3)S·H(2)O, 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 -NH(2) portions and the solvent water mol-ecules are engaged in N-H⋯N, N-H⋯O and O-H⋯O hydrogen-bonding inter-actions 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 = 427.48

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.130

S = 1.01

4382 reflections

288 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.54 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034453/xu5305sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811034453/xu5305Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H19N5O3S·H2O	F(000) = 896
Mr = 427.48	Dx = 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

Agilent SuperNova Dual diffractometer with Atlas detector	4382 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3259 reflections with I > 2σ(I)
mirror	Rint = 0.039
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −11→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→15
Tmin = 0.941, Tmax = 0.960	l = −19→19
9403 measured reflections

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(Fo2) + (0.0564P)2 + 0.8598P] where P = (Fo2 + 2Fc2)/3
4382 reflections	(Δ/σ)max = 0.001
288 parameters	Δρmax = 0.51 e Å−3
5 restraints	Δρmin = −0.54 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) ; (iii) .