Download citation
Download citation
link to html
The title compound, C13H20N4O3S·H2O, is V-shaped and entraps a water mol­ecule via an O—H...N and an O—H...O hydrogen bond. In the crystal structure, the packing of the mol­ecules is stabilized by N—H...N and O—H...N hydrogen bonds and van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804005446/su6081sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804005446/su6081Isup2.hkl
Contains datablock I

CCDC reference: 238790

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.114
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.12 Ratio PLAT480_ALERT_4_C Long H...A H-Bond Reported H4D .. N2 .. 2.64 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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-methylpiperazinyl)-4-acetamidophenylsulfonamide hydrate top
Crystal data top
C13H20N4O3S·H2OF(000) = 1408
Mr = 330.41Dx = 1.319 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 966 reflections
a = 28.637 (14) Åθ = 3.4–26.5°
b = 7.140 (3) ŵ = 0.22 mm1
c = 19.799 (11) ÅT = 293 K
β = 124.688 (14)°Block, colorless
V = 3329 (3) Å30.22 × 0.18 × 0.14 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
3458 independent reflections
Radiation source: fine-focus sealed tube2800 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 26.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3636
Tmin = 0.965, Tmax = 0.980k = 88
13322 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0524P)2 + 3.7269P]
where P = (Fo2 + 2Fc2)/3
3458 reflections(Δ/σ)max = 0.003
201 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.50 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.148345 (18)0.68734 (7)1.03988 (3)0.03528 (15)
O10.16894 (6)0.5581 (2)1.00735 (9)0.0459 (4)
O20.16688 (6)0.6739 (2)1.12361 (8)0.0485 (4)
O30.12821 (6)0.8216 (3)0.90623 (10)0.0579 (4)
N10.13643 (10)1.1763 (3)0.82330 (12)0.0540 (5)
N20.15150 (6)0.9417 (2)0.95093 (9)0.0358 (4)
N30.16698 (6)0.8978 (2)1.03131 (9)0.0371 (4)
H30.18460.97501.07180.045*
N40.10436 (6)0.6871 (2)0.82607 (10)0.0360 (4)
H40.11850.64180.77790.043*
C10.12051 (18)1.1947 (4)0.73864 (17)0.0895 (11)
H1A0.11021.07410.71260.134*
H1B0.15211.24360.73960.134*
H1C0.08881.27850.70850.134*
C20.18597 (12)1.0529 (4)0.87152 (16)0.0589 (6)
H2A0.21821.10810.87500.071*
H2B0.17790.93310.84390.071*
C30.20072 (9)1.0227 (3)0.95659 (14)0.0477 (5)
H3A0.23290.93860.98670.057*
H3B0.21101.14100.98580.057*
C40.10428 (9)1.0753 (3)0.90897 (13)0.0473 (5)
H4A0.11561.19390.93800.057*
H4B0.07201.02730.90750.057*
C50.08844 (11)1.1024 (4)0.82250 (14)0.0585 (6)
H5A0.07660.98350.79370.070*
H5B0.05671.18870.79320.070*
C60.07349 (7)0.6782 (3)0.97735 (11)0.0334 (4)
C70.04394 (8)0.7420 (3)1.00879 (12)0.0439 (5)
H70.06380.78281.06300.053*
C80.01476 (8)0.7459 (3)0.96059 (12)0.0448 (5)
H80.03420.78730.98270.054*
C90.04476 (7)0.6884 (3)0.87933 (11)0.0327 (4)
C100.01466 (8)0.6255 (3)0.84793 (12)0.0417 (5)
H100.03440.58760.79340.050*
C110.04392 (8)0.6185 (3)0.89649 (12)0.0424 (5)
H110.06340.57400.87500.051*
C120.14251 (8)0.7488 (3)0.84144 (13)0.0385 (4)
C130.20374 (8)0.7232 (4)0.77208 (14)0.0515 (6)
H13A0.22320.65780.79160.077*
H13B0.20620.65190.72910.077*
H13C0.22110.84360.75120.077*
O40.14334 (7)0.5663 (2)0.83806 (9)0.0573 (4)
H4C0.14550.44800.84350.069*
H4D0.15130.62950.87970.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0284 (2)0.0458 (3)0.0283 (2)0.00182 (19)0.01405 (19)0.00513 (19)
O10.0400 (7)0.0496 (9)0.0478 (8)0.0084 (6)0.0248 (7)0.0039 (7)
O20.0374 (7)0.0724 (11)0.0287 (7)0.0008 (7)0.0146 (6)0.0111 (7)
O30.0451 (8)0.0784 (12)0.0537 (9)0.0039 (8)0.0302 (8)0.0163 (8)
N10.0883 (15)0.0403 (10)0.0479 (11)0.0035 (10)0.0473 (11)0.0064 (8)
N20.0339 (8)0.0427 (9)0.0320 (8)0.0011 (7)0.0195 (7)0.0036 (7)
N30.0328 (8)0.0469 (10)0.0267 (8)0.0063 (7)0.0140 (7)0.0026 (7)
N40.0305 (8)0.0411 (9)0.0326 (8)0.0011 (7)0.0157 (7)0.0051 (7)
C10.175 (4)0.0523 (16)0.0650 (17)0.0187 (19)0.082 (2)0.0121 (13)
C20.0839 (17)0.0504 (14)0.0728 (16)0.0069 (12)0.0627 (15)0.0106 (12)
C30.0427 (11)0.0542 (13)0.0555 (13)0.0019 (10)0.0334 (10)0.0054 (11)
C40.0399 (11)0.0519 (13)0.0484 (12)0.0049 (10)0.0242 (10)0.0108 (10)
C50.0625 (15)0.0515 (14)0.0423 (12)0.0030 (11)0.0184 (11)0.0100 (10)
C60.0290 (8)0.0387 (10)0.0307 (9)0.0024 (8)0.0159 (7)0.0009 (8)
C70.0359 (10)0.0648 (14)0.0277 (9)0.0024 (10)0.0161 (8)0.0074 (9)
C80.0365 (10)0.0631 (14)0.0379 (11)0.0011 (9)0.0230 (9)0.0097 (10)
C90.0304 (9)0.0328 (9)0.0336 (9)0.0012 (7)0.0173 (8)0.0003 (8)
C100.0346 (10)0.0556 (13)0.0307 (9)0.0037 (9)0.0161 (8)0.0112 (9)
C110.0345 (10)0.0566 (13)0.0385 (11)0.0013 (9)0.0223 (9)0.0089 (9)
C120.0356 (10)0.0375 (10)0.0434 (11)0.0025 (8)0.0230 (9)0.0033 (9)
C130.0328 (10)0.0630 (15)0.0524 (13)0.0052 (10)0.0205 (10)0.0080 (11)
O40.0774 (11)0.0525 (10)0.0393 (8)0.0004 (8)0.0315 (8)0.0010 (7)
Geometric parameters (Å, º) top
S1—O21.4274 (17)C3—H3B0.9700
S1—O11.4306 (16)C4—C51.513 (3)
S1—N31.6356 (19)C4—H4A0.9700
S1—C61.764 (2)C4—H4B0.9700
O3—C121.218 (3)C5—H5A0.9700
N1—C51.463 (3)C5—H5B0.9700
N1—C21.469 (3)C6—C71.382 (3)
N1—C11.472 (3)C6—C111.385 (3)
N2—N31.423 (2)C7—C81.382 (3)
N2—C41.466 (3)C7—H70.9300
N2—C31.467 (3)C8—C91.386 (3)
N3—H30.8600C8—H80.9300
N4—C121.363 (3)C9—C101.393 (3)
N4—C91.406 (2)C10—C111.380 (3)
N4—H40.8600C10—H100.9300
C1—H1A0.9600C11—H110.9300
C1—H1B0.9600C12—C131.501 (3)
C1—H1C0.9600C13—H13A0.9600
C2—C31.501 (3)C13—H13B0.9600
C2—H2A0.9700C13—H13C0.9600
C2—H2B0.9700O4—H4C0.8493
C3—H3A0.9700O4—H4D0.8493
O2—S1—O1120.24 (9)C5—C4—H4A110.1
O2—S1—N3104.74 (9)N2—C4—H4B110.1
O1—S1—N3107.66 (9)C5—C4—H4B110.1
O2—S1—C6108.24 (9)H4A—C4—H4B108.4
O1—S1—C6107.94 (10)N1—C5—C4111.03 (19)
N3—S1—C6107.40 (9)N1—C5—H5A109.4
C5—N1—C2110.16 (18)C4—C5—H5A109.4
C5—N1—C1109.9 (2)N1—C5—H5B109.4
C2—N1—C1110.6 (2)C4—C5—H5B109.4
N3—N2—C4112.14 (15)H5A—C5—H5B108.0
N3—N2—C3109.09 (15)C7—C6—C11119.58 (17)
C4—N2—C3108.86 (17)C7—C6—S1118.86 (15)
N2—N3—S1113.96 (12)C11—C6—S1121.47 (14)
N2—N3—H3123.0C8—C7—C6120.75 (18)
S1—N3—H3123.0C8—C7—H7119.6
C12—N4—C9127.98 (17)C6—C7—H7119.6
C12—N4—H4116.0C7—C8—C9120.15 (18)
C9—N4—H4116.0C7—C8—H8119.9
N1—C1—H1A109.5C9—C8—H8119.9
N1—C1—H1B109.5C8—C9—C10118.75 (17)
H1A—C1—H1B109.5C8—C9—N4123.95 (17)
N1—C1—H1C109.5C10—C9—N4117.29 (17)
H1A—C1—H1C109.5C11—C10—C9121.07 (18)
H1B—C1—H1C109.5C11—C10—H10119.5
N1—C2—C3111.51 (18)C9—C10—H10119.5
N1—C2—H2A109.3C10—C11—C6119.69 (18)
C3—C2—H2A109.3C10—C11—H11120.2
N1—C2—H2B109.3C6—C11—H11120.2
C3—C2—H2B109.3O3—C12—N4122.74 (18)
H2A—C2—H2B108.0O3—C12—C13122.20 (19)
N2—C3—C2109.04 (18)N4—C12—C13115.05 (19)
N2—C3—H3A109.9C12—C13—H13A109.5
C2—C3—H3A109.9C12—C13—H13B109.5
N2—C3—H3B109.9H13A—C13—H13B109.5
C2—C3—H3B109.9C12—C13—H13C109.5
H3A—C3—H3B108.3H13A—C13—H13C109.5
N2—C4—C5108.08 (18)H13B—C13—H13C109.5
N2—C4—H4A110.1H4C—O4—H4D116.5
C4—N2—N3—S1107.40 (17)O2—S1—C6—C11155.47 (17)
C3—N2—N3—S1131.93 (15)O1—S1—C6—C1123.9 (2)
O2—S1—N3—N2179.16 (12)N3—S1—C6—C1191.95 (19)
O1—S1—N3—N251.77 (14)C11—C6—C7—C80.3 (3)
C6—S1—N3—N264.24 (14)S1—C6—C7—C8176.83 (18)
C5—N1—C2—C354.8 (3)C6—C7—C8—C91.0 (4)
C1—N1—C2—C3176.5 (2)C7—C8—C9—C100.6 (3)
N3—N2—C3—C2174.97 (17)C7—C8—C9—N4179.8 (2)
C4—N2—C3—C262.4 (2)C12—N4—C9—C83.9 (3)
N1—C2—C3—N258.2 (3)C12—N4—C9—C10176.93 (19)
N3—N2—C4—C5176.16 (17)C8—C9—C10—C110.6 (3)
C3—N2—C4—C563.0 (2)N4—C9—C10—C11178.7 (2)
C2—N1—C5—C455.8 (3)C9—C10—C11—C61.2 (3)
C1—N1—C5—C4177.9 (2)C7—C6—C11—C100.8 (3)
N2—C4—C5—N160.2 (3)S1—C6—C11—C10175.61 (17)
O2—S1—C6—C728.1 (2)C9—N4—C12—O32.4 (3)
O1—S1—C6—C7159.72 (17)C9—N4—C12—C13178.43 (19)
N3—S1—C6—C784.46 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O3i0.862.392.888 (2)118
N4—H4···O4ii0.862.052.902 (3)170
O4—H4C···N1iii0.851.972.795 (3)164
O4—H4D···O10.852.332.996 (3)135
O4—H4D···N20.852.643.411 (3)152
Symmetry codes: (i) x, y+2, z+2; (ii) x, y, z+3/2; (iii) x, y1, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds