1-Butyl-3-(4-chloro-1,3-benzothia­zol-2-yl)urea monohydrate

In the crystal structure of the title compound, C₁₂H₁₄ClN₃OS·H₂O, the but­yl(chloro­benzo[d]thia­zolyl)urea mol­ecule, excluding butyl H atoms, dis­plays a roughly planar structure. The water mol­ecules link with the urea derivative mol­ecules via O—H...O and N—H...O hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.096
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

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Datablock: I


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 .          ?

   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

   2 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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

1-Butyl-3-(4-chlorobenzo[d]thiazol-2-yl)urea hydrate

Crystal data

C12H14ClN3OS·H2O	Z = 2
Mr = 301.8	F(000) = 316
Triclinic, P1	Dx = 1.406 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0075 (16) Å	Cell parameters from 1660 reflections
b = 7.6324 (18) Å	θ = 2.8–25.0°
c = 14.826 (3) Å	µ = 0.42 mm^−1
α = 96.568 (4)°	T = 293 K
β = 91.451 (4)°	Prism, colourless
γ = 114.775 (4)°	0.30 × 0.26 × 0.20 mm
V = 712.9 (3) Å^3

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	2507 independent reflections
Radiation source: fine-focus sealed tube	1939 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −6→8
Tmin = 0.885, Tmax = 0.921	k = −9→9
3635 measured reflections	l = −17→16

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0458P)^2 + 0.1733P] where P = (Fo^2 + 2Fc^2)/3
2507 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.34 e Å^−3
3 restraints	Δρmin = −0.21 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
Cl1	1.64422 (9)	1.31310 (10)	0.30212 (4)	0.0601 (2)
S1	0.85576 (8)	0.87168 (8)	0.17938 (4)	0.04047 (18)
O1	0.7215 (2)	0.6745 (2)	0.01314 (10)	0.0467 (4)
N1	1.2642 (3)	1.0310 (2)	0.16851 (11)	0.0337 (4)
N2	1.0790 (3)	0.8288 (2)	0.03696 (11)	0.0368 (4)
H2	1.1964	0.8539	0.0129	0.044*
N3	0.9211 (3)	0.6183 (3)	−0.09393 (12)	0.0420 (4)
H3	1.0471	0.6459	−0.1091	0.050*
C1	1.3802 (3)	1.2164 (3)	0.32347 (14)	0.0392 (5)
C2	1.3225 (4)	1.2626 (3)	0.40802 (15)	0.0470 (6)
H2A	1.4255	1.3445	0.4534	0.056*
C3	1.1119 (4)	1.1874 (3)	0.42564 (16)	0.0506 (6)
H3A	1.0751	1.2195	0.4830	0.061*
C4	0.9565 (4)	1.0664 (3)	0.36005 (15)	0.0469 (6)
H4	0.8153	1.0169	0.3720	0.056*
C5	1.0162 (3)	1.0197 (3)	0.27484 (14)	0.0371 (5)
C6	1.2279 (3)	1.0927 (3)	0.25531 (13)	0.0332 (5)
C7	1.0856 (3)	0.9153 (3)	0.12350 (13)	0.0323 (5)
C8	0.8935 (3)	0.7023 (3)	−0.01451 (14)	0.0348 (5)
C9	0.7433 (3)	0.4812 (3)	−0.15551 (14)	0.0408 (5)
H9A	0.6423	0.5357	−0.1635	0.049*
H9B	0.6737	0.3615	−0.1294	0.049*
C10	0.8155 (3)	0.4373 (3)	−0.24681 (13)	0.0378 (5)
H10A	0.8852	0.5578	−0.2724	0.045*
H10B	0.9179	0.3848	−0.2381	0.045*
C11	0.6375 (4)	0.2946 (3)	−0.31352 (15)	0.0440 (5)
H11A	0.5363	0.3482	−0.3232	0.053*
H11B	0.5661	0.1749	−0.2876	0.053*
C12	0.7120 (5)	0.2484 (4)	−0.40465 (16)	0.0625 (7)
H12A	0.7831	0.3664	−0.4307	0.094*
H12B	0.5928	0.1597	−0.4450	0.094*
H12C	0.8073	0.1898	−0.3959	0.094*
O2	0.6166 (2)	0.2439 (2)	0.06225 (11)	0.0519 (4)
H2B	0.5382	0.1697	0.0980	0.062*
H2C	0.5680	0.3147	0.0388	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0349 (3)	0.0696 (4)	0.0619 (4)	0.0130 (3)	−0.0051 (3)	−0.0063 (3)
S1	0.0276 (3)	0.0475 (3)	0.0426 (3)	0.0124 (3)	0.0072 (2)	0.0049 (2)
O1	0.0272 (8)	0.0582 (10)	0.0471 (9)	0.0120 (7)	0.0044 (7)	0.0014 (7)
N1	0.0289 (9)	0.0346 (9)	0.0361 (9)	0.0122 (8)	0.0035 (7)	0.0040 (7)
N2	0.0254 (9)	0.0435 (10)	0.0369 (10)	0.0107 (8)	0.0052 (7)	0.0024 (8)
N3	0.0289 (9)	0.0481 (11)	0.0402 (10)	0.0105 (8)	0.0015 (8)	−0.0038 (8)
C1	0.0384 (12)	0.0363 (12)	0.0440 (12)	0.0176 (10)	−0.0005 (10)	0.0044 (10)
C2	0.0592 (16)	0.0419 (13)	0.0393 (12)	0.0223 (12)	−0.0037 (11)	0.0010 (10)
C3	0.0676 (17)	0.0508 (14)	0.0374 (12)	0.0294 (13)	0.0118 (12)	0.0030 (11)
C4	0.0464 (13)	0.0519 (14)	0.0470 (13)	0.0236 (12)	0.0155 (11)	0.0114 (11)
C5	0.0369 (12)	0.0356 (11)	0.0403 (12)	0.0166 (10)	0.0062 (9)	0.0067 (9)
C6	0.0356 (11)	0.0323 (11)	0.0350 (11)	0.0170 (9)	0.0034 (9)	0.0065 (9)
C7	0.0286 (11)	0.0325 (11)	0.0370 (11)	0.0133 (9)	0.0041 (9)	0.0080 (9)
C8	0.0298 (11)	0.0337 (11)	0.0386 (12)	0.0105 (9)	0.0003 (9)	0.0083 (9)
C9	0.0333 (11)	0.0407 (12)	0.0417 (12)	0.0102 (10)	0.0003 (10)	0.0024 (10)
C10	0.0374 (12)	0.0370 (12)	0.0409 (12)	0.0172 (10)	0.0041 (10)	0.0072 (10)
C11	0.0475 (13)	0.0398 (12)	0.0452 (13)	0.0206 (11)	−0.0016 (11)	0.0006 (10)
C12	0.088 (2)	0.0587 (16)	0.0446 (14)	0.0367 (15)	−0.0008 (14)	−0.0017 (12)
O2	0.0388 (9)	0.0689 (11)	0.0585 (10)	0.0293 (8)	0.0168 (8)	0.0206 (8)

Geometric parameters (Å, º)

Cl1—C1	1.734 (2)	C4—C5	1.395 (3)
S1—C5	1.741 (2)	C4—H4	0.9300
S1—C7	1.753 (2)	C5—C6	1.401 (3)
O1—C8	1.223 (2)	C9—C10	1.508 (3)
N1—C6	1.386 (2)	C9—H9A	0.9700
N1—C7	1.300 (3)	C9—H9B	0.9700
N2—C7	1.365 (3)	C10—C11	1.507 (3)
N2—C8	1.391 (3)	C10—H10A	0.9700
N2—H2	0.8600	C10—H10B	0.9700
N3—C8	1.333 (3)	C11—C12	1.518 (3)
N3—C9	1.453 (3)	C11—H11A	0.9700
N3—H3	0.8600	C11—H11B	0.9700
C1—C2	1.379 (3)	C12—H12A	0.9600
C1—C6	1.390 (3)	C12—H12B	0.9600
C2—C3	1.386 (3)	C12—H12C	0.9600
C2—H2A	0.9300	O2—H2B	0.8525
C3—C4	1.372 (3)	O2—H2C	0.8486
C3—H3A	0.9300
C5—S1—C7	87.86 (10)	O1—C8—N3	124.48 (19)
C7—N1—C6	109.48 (17)	O1—C8—N2	120.86 (19)
C7—N2—C8	123.79 (17)	N3—C8—N2	114.65 (18)
C7—N2—H2	118.1	N3—C9—C10	110.71 (18)
C8—N2—H2	118.1	N3—C9—H9A	109.5
C8—N3—C9	121.55 (18)	C10—C9—H9A	109.5
C8—N3—H3	119.2	N3—C9—H9B	109.5
C9—N3—H3	119.2	C10—C9—H9B	109.5
C2—C1—C6	120.4 (2)	H9A—C9—H9B	108.1
C2—C1—Cl1	119.75 (18)	C11—C10—C9	113.10 (18)
C6—C1—Cl1	119.81 (16)	C11—C10—H10A	109.0
C1—C2—C3	120.3 (2)	C9—C10—H10A	109.0
C1—C2—H2A	119.9	C11—C10—H10B	109.0
C3—C2—H2A	119.9	C9—C10—H10B	109.0
C4—C3—C2	121.2 (2)	H10A—C10—H10B	107.8
C4—C3—H3A	119.4	C10—C11—C12	112.8 (2)
C2—C3—H3A	119.4	C10—C11—H11A	109.0
C3—C4—C5	118.2 (2)	C12—C11—H11A	109.0
C3—C4—H4	120.9	C10—C11—H11B	109.0
C5—C4—H4	120.9	C12—C11—H11B	109.0
C4—C5—C6	121.8 (2)	H11A—C11—H11B	107.8
C4—C5—S1	128.39 (18)	C11—C12—H12A	109.5
C6—C5—S1	109.77 (15)	C11—C12—H12B	109.5
N1—C6—C1	126.35 (19)	H12A—C12—H12B	109.5
N1—C6—C5	115.56 (18)	C11—C12—H12C	109.5
C1—C6—C5	118.08 (18)	H12A—C12—H12C	109.5
N1—C7—N2	120.95 (18)	H12B—C12—H12C	109.5
N1—C7—S1	117.29 (15)	H2B—O2—H2C	115.8
N2—C7—S1	121.75 (15)
C6—C1—C2—C3	−0.6 (3)	C4—C5—C6—C1	−0.6 (3)
Cl1—C1—C2—C3	179.49 (17)	S1—C5—C6—C1	179.29 (15)
C1—C2—C3—C4	−0.1 (4)	C6—N1—C7—N2	−177.55 (17)
C2—C3—C4—C5	0.4 (3)	C6—N1—C7—S1	1.1 (2)
C3—C4—C5—C6	−0.1 (3)	C8—N2—C7—N1	179.38 (18)
C3—C4—C5—S1	−179.91 (17)	C8—N2—C7—S1	0.8 (3)
C7—S1—C5—C4	−178.6 (2)	C5—S1—C7—N1	−1.58 (17)
C7—S1—C5—C6	1.53 (15)	C5—S1—C7—N2	177.04 (17)
C7—N1—C6—C1	179.51 (19)	C9—N3—C8—O1	−0.6 (3)
C7—N1—C6—C5	0.2 (2)	C9—N3—C8—N2	179.55 (17)
C2—C1—C6—N1	−178.38 (19)	C7—N2—C8—O1	6.4 (3)
Cl1—C1—C6—N1	1.6 (3)	C7—N2—C8—N3	−173.81 (18)
C2—C1—C6—C5	0.9 (3)	C8—N3—C9—C10	169.40 (19)
Cl1—C1—C6—C5	−179.16 (15)	N3—C9—C10—C11	179.66 (18)
C4—C5—C6—N1	178.76 (18)	C9—C10—C11—C12	−178.95 (19)
S1—C5—C6—N1	−1.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2^i	0.86	2.05	2.826 (2)	149
N3—H3···O2^i	0.86	2.21	2.962 (2)	147
O2—H2B···N1^ii	0.85	2.13	2.939 (2)	158
O2—H2C···O1^iii	0.85	2.19	2.918 (2)	144

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