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In the crystal structure of the title compound, C11H12ClN3OS·H2O, the urea derivative mol­ecule, excluding propyl H atoms, displays a roughly planar structure. The water mol­ecules link the urea derivative mol­ecules via O—H...O, O—H...N and N—H...O hydrogen bonding, forming columns parallel to the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026596/ci2092sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026596/ci2092Isup2.hkl
Contains datablock I

CCDC reference: 618159

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.105
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

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Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT731_ALERT_1_C Bond Calc 0.83(2), Rep 0.830(9) ...... 2.22 su-Rat O2 -H2A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.83(2), Rep 0.830(9) ...... 2.22 su-Rat O2 -H2A 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.

1-(4-Chloro-1,3-benzothiazol-2-yl)-3-propylurea monohydrate top
Crystal data top
C11H12ClN3OS·H2OZ = 2
Mr = 287.76F(000) = 300
Triclinic, P1Dx = 1.424 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 6.8742 (15) ÅCell parameters from 2025 reflections
b = 7.2537 (16) Åθ = 1.4–27.9°
c = 14.729 (2) ŵ = 0.44 mm1
α = 97.509 (5)°T = 293 K
β = 94.600 (8)°Block, colourless
γ = 111.419 (8)°0.24 × 0.20 × 0.10 mm
V = 671.3 (2) Å3
Data collection top
Rigaku Saturn
diffractometer
3134 independent reflections
Radiation source: rotating anode2212 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.026
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.8°
ω scansh = 78
Absorption correction: multi-scan
(Jacobson, 1998)
k = 99
Tmin = 0.893, Tmax = 0.958l = 1918
6546 measured reflections
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0605P)2]
where P = (Fo2 + 2Fc2)/3
3134 reflections(Δ/σ)max = 0.001
180 parametersΔρmax = 0.23 e Å3
5 restraintsΔρmin = 0.28 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>2σ(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
Cl10.65745 (8)0.20674 (9)0.34818 (3)0.0739 (2)
S10.18237 (6)0.09879 (6)0.08242 (3)0.04468 (14)
O10.31248 (16)0.21940 (18)0.09797 (8)0.0486 (3)
O20.05218 (19)0.4550 (2)0.11095 (11)0.0631 (4)
H2A0.109 (3)0.372 (3)0.1144 (18)0.112 (10)*
H2B0.150 (3)0.5680 (18)0.1315 (14)0.075 (7)*
N10.53997 (19)0.22033 (19)0.15000 (9)0.0416 (3)
N20.58161 (19)0.2885 (2)0.01096 (9)0.0449 (3)
H20.7187 (15)0.342 (3)0.0103 (13)0.064 (6)*
N30.6492 (2)0.3636 (2)0.16931 (9)0.0459 (3)
H30.7851 (17)0.397 (3)0.1604 (14)0.077 (6)*
C10.4575 (2)0.2114 (2)0.07324 (11)0.0390 (3)
C20.3809 (2)0.1313 (2)0.22443 (11)0.0410 (4)
C30.4061 (3)0.1115 (3)0.31747 (12)0.0482 (4)
C40.2329 (3)0.0166 (3)0.38434 (13)0.0565 (5)
H40.25080.00190.44640.068*
C50.0320 (3)0.0571 (3)0.35931 (13)0.0606 (5)
H50.08360.11980.40520.073*
C60.0004 (3)0.0393 (3)0.26848 (12)0.0532 (4)
H60.13470.08920.25210.064*
C70.1766 (2)0.0556 (2)0.20139 (11)0.0426 (4)
C80.5028 (2)0.2867 (2)0.09500 (11)0.0394 (4)
C90.5905 (2)0.3697 (2)0.26137 (11)0.0441 (4)
H9A0.51990.23350.27230.053*
H9B0.49240.43730.26640.053*
C100.7810 (3)0.4783 (3)0.33358 (12)0.0516 (4)
H10A0.87970.41140.32810.062*
H10B0.85080.61470.32290.062*
C110.7214 (4)0.4835 (4)0.42981 (14)0.0755 (6)
H11A0.84610.55240.47400.113*
H11B0.65340.34860.44080.113*
H11C0.62670.55280.43600.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0660 (3)0.1121 (5)0.0615 (3)0.0452 (3)0.0316 (3)0.0294 (3)
S10.0308 (2)0.0498 (3)0.0485 (3)0.00782 (17)0.00952 (17)0.01140 (17)
O10.0290 (5)0.0601 (7)0.0533 (7)0.0114 (5)0.0107 (5)0.0116 (5)
O20.0364 (6)0.0624 (9)0.0892 (10)0.0162 (7)0.0162 (6)0.0117 (8)
N10.0340 (6)0.0457 (7)0.0482 (8)0.0161 (6)0.0117 (6)0.0131 (6)
N20.0282 (6)0.0553 (8)0.0471 (8)0.0103 (6)0.0089 (6)0.0090 (6)
N30.0318 (7)0.0565 (8)0.0476 (8)0.0148 (6)0.0077 (6)0.0074 (6)
C10.0320 (7)0.0380 (8)0.0485 (9)0.0127 (6)0.0101 (7)0.0118 (6)
C20.0435 (8)0.0377 (8)0.0469 (9)0.0194 (7)0.0091 (7)0.0108 (6)
C30.0562 (10)0.0521 (10)0.0484 (9)0.0311 (8)0.0151 (8)0.0150 (7)
C40.0743 (13)0.0572 (11)0.0460 (10)0.0356 (10)0.0054 (9)0.0072 (8)
C50.0649 (12)0.0545 (11)0.0565 (11)0.0212 (9)0.0077 (9)0.0040 (8)
C60.0444 (9)0.0508 (10)0.0565 (11)0.0103 (8)0.0010 (8)0.0100 (8)
C70.0416 (8)0.0382 (8)0.0474 (9)0.0135 (7)0.0063 (7)0.0102 (7)
C80.0329 (8)0.0383 (8)0.0477 (9)0.0132 (6)0.0074 (7)0.0087 (6)
C90.0391 (8)0.0458 (9)0.0484 (9)0.0159 (7)0.0109 (7)0.0095 (7)
C100.0496 (10)0.0520 (10)0.0532 (10)0.0219 (8)0.0008 (8)0.0049 (8)
C110.0980 (16)0.0853 (15)0.0497 (12)0.0462 (13)0.0042 (11)0.0037 (10)
Geometric parameters (Å, º) top
Cl1—C31.7328 (18)C3—C41.377 (3)
S1—C71.7341 (17)C4—C51.387 (2)
S1—C11.7505 (15)C4—H40.93
O1—C81.2247 (17)C5—C61.370 (3)
O2—H2A0.830 (9)C5—H50.93
O2—H2B0.847 (9)C6—C71.393 (2)
N1—C11.304 (2)C6—H60.93
N1—C21.3861 (19)C9—C101.507 (2)
N2—C11.371 (2)C9—H9A0.97
N2—C81.390 (2)C9—H9B0.97
N2—H20.880 (9)C10—C111.506 (3)
N3—C81.333 (2)C10—H10A0.97
N3—C91.445 (2)C10—H10B0.97
N3—H30.901 (9)C11—H11A0.96
C2—C31.390 (2)C11—H11B0.96
C2—C71.397 (2)C11—H11C0.96
C7—S1—C187.74 (7)C7—C6—H6121.0
H2A—O2—H2B104.6 (17)C6—C7—C2121.95 (15)
C1—N1—C2109.47 (12)C6—C7—S1127.65 (13)
C1—N2—C8123.83 (12)C2—C7—S1110.40 (11)
C1—N2—H2116.6 (12)O1—C8—N3124.19 (14)
C8—N2—H2119.5 (12)O1—C8—N2121.02 (14)
C8—N3—C9120.92 (13)N3—C8—N2114.78 (12)
C8—N3—H3117.6 (13)N3—C9—C10111.27 (13)
C9—N3—H3121.0 (13)N3—C9—H9A109.4
N1—C1—N2121.18 (13)C10—C9—H9A109.4
N1—C1—S1117.21 (12)N3—C9—H9B109.4
N2—C1—S1121.61 (11)C10—C9—H9B109.4
N1—C2—C3126.57 (14)H9A—C9—H9B108.0
N1—C2—C7115.18 (13)C11—C10—C9111.60 (15)
C3—C2—C7118.25 (14)C11—C10—H10A109.3
C4—C3—C2120.25 (16)C9—C10—H10A109.3
C4—C3—Cl1120.48 (14)C11—C10—H10B109.3
C2—C3—Cl1119.27 (13)C9—C10—H10B109.3
C3—C4—C5120.16 (17)H10A—C10—H10B108.0
C3—C4—H4119.9C10—C11—H11A109.5
C5—C4—H4119.9C10—C11—H11B109.5
C6—C5—C4121.39 (17)H11A—C11—H11B109.5
C6—C5—H5119.3C10—C11—H11C109.5
C4—C5—H5119.3H11A—C11—H11C109.5
C5—C6—C7117.99 (16)H11B—C11—H11C109.5
C5—C6—H6121.0
C2—N1—C1—N2179.72 (13)C4—C5—C6—C70.1 (3)
C2—N1—C1—S10.72 (17)C5—C6—C7—C20.1 (3)
C8—N2—C1—N1178.80 (14)C5—C6—C7—S1179.82 (13)
C8—N2—C1—S10.7 (2)N1—C2—C7—C6179.53 (15)
C7—S1—C1—N10.89 (13)C3—C2—C7—C60.5 (2)
C7—S1—C1—N2179.55 (14)N1—C2—C7—S10.55 (17)
C1—N1—C2—C3179.95 (15)C3—C2—C7—S1179.41 (12)
C1—N1—C2—C70.09 (19)C1—S1—C7—C6179.33 (17)
N1—C2—C3—C4179.11 (16)C1—S1—C7—C20.75 (11)
C7—C2—C3—C40.9 (2)C9—N3—C8—O11.0 (3)
N1—C2—C3—Cl10.7 (2)C9—N3—C8—N2179.32 (14)
C7—C2—C3—Cl1179.22 (12)C1—N2—C8—O12.2 (2)
C2—C3—C4—C51.0 (3)C1—N2—C8—N3178.14 (14)
Cl1—C3—C4—C5179.20 (14)C8—N3—C9—C10175.28 (14)
C3—C4—C5—C60.5 (3)N3—C9—C10—C11179.44 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O10.83 (1)2.09 (1)2.891 (2)162 (2)
O2—H2B···N1i0.85 (1)2.09 (1)2.8816 (19)155 (2)
N2—H2···O2ii0.88 (1)2.43 (1)3.164 (2)142 (2)
N3—H3···O2ii0.90 (1)1.95 (1)2.8358 (19)167 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.
 

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