N-[4-(4-Methyl­piperazin-1-yl­sulfonyl)­phenyl]­acet­amide monohydrate

The title compound, C₁₃H₁₉N₃O₃S·H₂O, is V-shaped and entraps a water molecule. In the crystal structure, N—H...O, O—H...O and O—H...N hydrogen bonds and van der Waals forces stabilize the packing of the molecules.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.131
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker 1997); cell refinement: SMART; data reduction: SAINT (Bruker 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-[4-(4-methylpiperazin-1-ylsulfonyl)phenyl]acetamide hydrate

Crystal data

C13H19N3O3S·H2O	F(000) = 672
Mr = 315.39	Dx = 1.332 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 982 reflections
a = 12.851 (6) Å	θ = 3.2–26.3°
b = 11.527 (5) Å	µ = 0.23 mm^−1
c = 10.677 (4) Å	T = 293 K
β = 96.251 (7)°	Block, colorless
V = 1572.2 (11) Å^3	0.24 × 0.22 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3224 independent reflections
Radiation source: fine-focus sealed tube	2430 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→14
Tmin = 0.932, Tmax = 0.965	k = −14→14
8846 measured reflections	l = −7→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0713P)^2 + 0.371P] where P = (Fo^2 + 2Fc^2)/3
3224 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.59062 (4)	0.36092 (5)	0.21885 (5)	0.03761 (17)
N1	0.61685 (13)	0.44980 (14)	0.33795 (15)	0.0365 (4)
N2	0.70156 (14)	0.61127 (16)	0.52380 (17)	0.0432 (4)
N3	0.95045 (14)	0.36740 (17)	−0.08812 (17)	0.0467 (5)
H3	0.9939	0.3117	−0.0693	0.056*
O1	0.58733 (12)	0.24697 (13)	0.27134 (15)	0.0492 (4)
O2	0.50107 (11)	0.40654 (15)	0.14400 (14)	0.0501 (4)
O3	0.92018 (14)	0.52149 (19)	−0.21882 (17)	0.0718 (6)
C1	0.62413 (17)	0.57338 (18)	0.3067 (2)	0.0423 (5)
H1A	0.5669	0.5947	0.2441	0.051*
H1B	0.6894	0.5884	0.2719	0.051*
C2	0.61921 (18)	0.64423 (19)	0.4240 (2)	0.0490 (5)
H2A	0.6266	0.7257	0.4041	0.059*
H2B	0.5513	0.6337	0.4542	0.059*
C3	0.69139 (19)	0.4881 (2)	0.5525 (2)	0.0482 (5)
H3A	0.6243	0.4744	0.5837	0.058*
H3B	0.7460	0.4659	0.6180	0.058*
C4	0.69949 (18)	0.41492 (18)	0.43692 (19)	0.0420 (5)
H4A	0.7677	0.4255	0.4075	0.050*
H4B	0.6916	0.3336	0.4572	0.050*
C5	0.6920 (2)	0.6821 (3)	0.6365 (3)	0.0674 (8)
H5A	0.6991	0.7627	0.6161	0.101*
H5B	0.7460	0.6608	0.7017	0.101*
H5C	0.6247	0.6692	0.6652	0.101*
C6	0.69700 (15)	0.36600 (17)	0.12727 (18)	0.0342 (4)
C7	0.78536 (16)	0.29862 (18)	0.16090 (19)	0.0403 (5)
H7	0.7887	0.2514	0.2318	0.048*
C8	0.86774 (17)	0.30216 (19)	0.0889 (2)	0.0427 (5)
H8	0.9269	0.2572	0.1116	0.051*
C9	0.86364 (16)	0.37226 (18)	−0.01766 (19)	0.0382 (5)
C10	0.77547 (17)	0.4396 (2)	−0.0505 (2)	0.0450 (5)
H10	0.7723	0.4873	−0.1211	0.054*
C11	0.69182 (16)	0.43599 (19)	0.02185 (19)	0.0419 (5)
H11	0.6325	0.4807	−0.0008	0.050*
C12	0.97412 (18)	0.4389 (2)	−0.1812 (2)	0.0480 (6)
C13	1.0743 (2)	0.4107 (3)	−0.2346 (3)	0.0626 (7)
H13A	1.0670	0.4280	−0.3231	0.094*
H13B	1.0899	0.3298	−0.2223	0.094*
H13C	1.1302	0.4562	−0.1927	0.094*
O4	0.92612 (15)	0.84442 (17)	0.05065 (18)	0.0694 (5)
H4C	0.9396	0.8824	0.1187	0.104*
H4D	0.8631	0.8550	0.0197	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0311 (3)	0.0406 (3)	0.0411 (3)	−0.0041 (2)	0.0042 (2)	0.0012 (2)
N1	0.0379 (9)	0.0346 (9)	0.0375 (9)	0.0016 (7)	0.0061 (7)	0.0036 (7)
N2	0.0385 (10)	0.0436 (10)	0.0490 (10)	−0.0026 (8)	0.0115 (8)	−0.0084 (8)
N3	0.0396 (10)	0.0564 (12)	0.0454 (10)	0.0047 (8)	0.0099 (8)	−0.0024 (9)
O1	0.0501 (9)	0.0392 (9)	0.0585 (9)	−0.0111 (7)	0.0076 (7)	0.0042 (7)
O2	0.0319 (8)	0.0654 (10)	0.0519 (9)	−0.0002 (7)	−0.0001 (7)	0.0041 (8)
O3	0.0522 (11)	0.0966 (15)	0.0688 (12)	0.0045 (10)	0.0159 (9)	0.0311 (11)
C1	0.0423 (12)	0.0379 (11)	0.0469 (12)	0.0068 (9)	0.0060 (9)	0.0082 (9)
C2	0.0448 (12)	0.0388 (12)	0.0641 (14)	0.0054 (10)	0.0091 (10)	−0.0047 (11)
C3	0.0516 (13)	0.0534 (14)	0.0399 (11)	−0.0083 (11)	0.0055 (10)	0.0026 (10)
C4	0.0473 (12)	0.0368 (11)	0.0407 (11)	0.0024 (9)	−0.0007 (9)	0.0058 (9)
C5	0.0611 (16)	0.0751 (18)	0.0692 (17)	−0.0074 (14)	0.0219 (13)	−0.0307 (15)
C6	0.0332 (10)	0.0357 (10)	0.0334 (10)	−0.0012 (8)	0.0020 (8)	−0.0032 (8)
C7	0.0406 (11)	0.0396 (11)	0.0402 (11)	0.0034 (9)	0.0021 (9)	0.0031 (9)
C8	0.0359 (11)	0.0458 (12)	0.0458 (11)	0.0088 (9)	0.0017 (9)	−0.0006 (10)
C9	0.0334 (10)	0.0447 (12)	0.0366 (10)	−0.0012 (9)	0.0040 (8)	−0.0065 (9)
C10	0.0452 (12)	0.0535 (13)	0.0365 (11)	0.0050 (10)	0.0057 (9)	0.0080 (10)
C11	0.0344 (11)	0.0495 (13)	0.0415 (11)	0.0066 (9)	0.0025 (8)	0.0027 (9)
C12	0.0400 (12)	0.0637 (15)	0.0403 (12)	−0.0085 (11)	0.0038 (9)	−0.0031 (11)
C13	0.0499 (14)	0.0800 (19)	0.0608 (15)	−0.0131 (13)	0.0202 (12)	−0.0150 (14)
O4	0.0602 (11)	0.0769 (13)	0.0742 (12)	0.0147 (9)	0.0217 (9)	−0.0077 (10)

Geometric parameters (Å, º)

S1—O2	1.4280 (16)	C4—H4A	0.9700
S1—O1	1.4306 (16)	C4—H4B	0.9700
S1—N1	1.6392 (18)	C5—H5A	0.9600
S1—C6	1.766 (2)	C5—H5B	0.9600
N1—C1	1.468 (3)	C5—H5C	0.9600
N1—C4	1.470 (3)	C6—C11	1.381 (3)
N2—C3	1.461 (3)	C6—C7	1.390 (3)
N2—C2	1.468 (3)	C7—C8	1.375 (3)
N2—C5	1.470 (3)	C7—H7	0.9300
N3—C12	1.351 (3)	C8—C9	1.392 (3)
N3—C9	1.413 (3)	C8—H8	0.9300
N3—H3	0.8600	C9—C10	1.387 (3)
O3—C12	1.220 (3)	C10—C11	1.391 (3)
C1—C2	1.502 (3)	C10—H10	0.9300
C1—H1A	0.9700	C11—H11	0.9300
C1—H1B	0.9700	C12—C13	1.500 (3)
C2—H2A	0.9700	C13—H13A	0.9600
C2—H2B	0.9700	C13—H13B	0.9600
C3—C4	1.508 (3)	C13—H13C	0.9600
C3—H3A	0.9700	O4—H4C	0.8502
C3—H3B	0.9700	O4—H4D	0.8498
O2—S1—O1	120.06 (10)	C3—C4—H4B	109.9
O2—S1—N1	106.80 (10)	H4A—C4—H4B	108.3
O1—S1—N1	106.40 (10)	N2—C5—H5A	109.5
O2—S1—C6	107.65 (10)	N2—C5—H5B	109.5
O1—S1—C6	107.76 (10)	H5A—C5—H5B	109.5
N1—S1—C6	107.62 (9)	N2—C5—H5C	109.5
C1—N1—C4	111.69 (16)	H5A—C5—H5C	109.5
C1—N1—S1	116.30 (14)	H5B—C5—H5C	109.5
C4—N1—S1	117.26 (14)	C11—C6—C7	120.17 (19)
C3—N2—C2	109.26 (17)	C11—C6—S1	119.95 (15)
C3—N2—C5	110.5 (2)	C7—C6—S1	119.88 (15)
C2—N2—C5	109.42 (19)	C8—C7—C6	119.73 (19)
C12—N3—C9	128.4 (2)	C8—C7—H7	120.1
C12—N3—H3	115.8	C6—C7—H7	120.1
C9—N3—H3	115.8	C7—C8—C9	120.76 (19)
N1—C1—C2	109.19 (17)	C7—C8—H8	119.6
N1—C1—H1A	109.8	C9—C8—H8	119.6
C2—C1—H1A	109.8	C10—C9—C8	119.29 (19)
N1—C1—H1B	109.8	C10—C9—N3	123.92 (19)
C2—C1—H1B	109.8	C8—C9—N3	116.77 (18)
H1A—C1—H1B	108.3	C9—C10—C11	120.1 (2)
N2—C2—C1	111.84 (17)	C9—C10—H10	119.9
N2—C2—H2A	109.2	C11—C10—H10	119.9
C1—C2—H2A	109.2	C6—C11—C10	119.93 (19)
N2—C2—H2B	109.2	C6—C11—H11	120.0
C1—C2—H2B	109.2	C10—C11—H11	120.0
H2A—C2—H2B	107.9	O3—C12—N3	123.6 (2)
N2—C3—C4	110.86 (18)	O3—C12—C13	121.7 (2)
N2—C3—H3A	109.5	N3—C12—C13	114.8 (2)
C4—C3—H3A	109.5	C12—C13—H13A	109.5
N2—C3—H3B	109.5	C12—C13—H13B	109.5
C4—C3—H3B	109.5	H13A—C13—H13B	109.5
H3A—C3—H3B	108.1	C12—C13—H13C	109.5
N1—C4—C3	109.05 (18)	H13A—C13—H13C	109.5
N1—C4—H4A	109.9	H13B—C13—H13C	109.5
C3—C4—H4A	109.9	H4C—O4—H4D	110.8
N1—C4—H4B	109.9
O2—S1—N1—C1	−50.58 (16)	N1—S1—C6—C11	−97.22 (18)
O1—S1—N1—C1	−179.95 (14)	O2—S1—C6—C7	−161.82 (16)
C6—S1—N1—C1	64.77 (16)	O1—S1—C6—C7	−30.98 (19)
O2—S1—N1—C4	173.50 (15)	N1—S1—C6—C7	83.39 (18)
O1—S1—N1—C4	44.13 (17)	C11—C6—C7—C8	0.2 (3)
C6—S1—N1—C4	−71.15 (17)	S1—C6—C7—C8	179.54 (16)
C4—N1—C1—C2	−56.9 (2)	C6—C7—C8—C9	−0.2 (3)
S1—N1—C1—C2	164.82 (14)	C7—C8—C9—C10	0.4 (3)
C3—N2—C2—C1	−58.1 (2)	C7—C8—C9—N3	−177.98 (19)
C5—N2—C2—C1	−179.23 (19)	C12—N3—C9—C10	13.7 (3)
N1—C1—C2—N2	56.8 (2)	C12—N3—C9—C8	−168.0 (2)
C2—N2—C3—C4	58.7 (2)	C8—C9—C10—C11	−0.6 (3)
C5—N2—C3—C4	179.17 (19)	N3—C9—C10—C11	177.7 (2)
C1—N1—C4—C3	58.0 (2)	C7—C6—C11—C10	−0.4 (3)
S1—N1—C4—C3	−164.19 (14)	S1—C6—C11—C10	−179.74 (17)
N2—C3—C4—N1	−58.7 (2)	C9—C10—C11—C6	0.6 (3)
O2—S1—C6—C11	17.6 (2)	C9—N3—C12—O3	−0.2 (4)
O1—S1—C6—C11	148.40 (16)	C9—N3—C12—C13	178.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O4^i	0.86	2.07	2.915 (3)	167
O4—H4C···O3^ii	0.85	2.10	2.915 (3)	162
O4—H4D···N2^iii	0.85	2.12	2.914 (3)	156

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