1-(1,3-Benzothia­zol-2-yl)-4,5-dihydr­oxy-3-phenyl­imidazolidin-2-one

The title compound, C₁₆H₁₃N₃O₃S, has the two hydroxyl groups anti to each other. The benzothia­zolyl and phenyl ring systems make a dihedral angle of 74.35 (1)°. Relatively strong hydrogen bonds are present between neighboring mol­ecules, stabilizing the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.081
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C
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
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: IPDS Software (Stoe, 1997); cell refinement: IPDS Software; data reduction: IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97.

1-(1,3-Benzothiazol-2-yl)-4,5-dihydroxy-3-phenylimidazolidin-2-one

Crystal data

C16H13N3O3S	F(000) = 680
Mr = 327.35	Dx = 1.459 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11002 reflections
a = 13.6414 (18) Å	θ = 2.1–26.1°
b = 14.170 (2) Å	µ = 0.24 mm^−1
c = 7.9521 (10) Å	T = 290 K
β = 104.113 (15)°	Needle, colourless
V = 1490.7 (4) Å^3	0.5 × 0.15 × 0.1 mm
Z = 4

Data collection

Stoe IPDS diffractometer	2720 independent reflections
Radiation source: fine-focus sealed tube	2027 reflections with I > \2S(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 6.67 pixels mm^-1	θmax = 25.5°, θmin = 2.1°
φ scans	h = −16→16
Absorption correction: numerical (X-RED; Stoe, 1997)	k = −17→17
Tmin = 0.961, Tmax = 0.992	l = −9→9
11002 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	All H-atom parameters refined
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0499P)^2 + 0.07P] where P = (Fo^2 + 2Fc^2)/3
2720 reflections	(Δ/σ)max < 0.001
260 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.16 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	0.52908 (3)	0.83653 (3)	0.10260 (6)	0.04518 (14)
O1	0.69516 (9)	0.77040 (8)	0.35763 (17)	0.0472 (3)
O2	0.79915 (10)	0.57679 (10)	0.03685 (18)	0.0508 (3)
H21	0.775 (2)	0.631 (2)	−0.017 (4)	0.086 (8)*
O3	0.58254 (10)	0.50153 (9)	0.18737 (18)	0.0496 (3)
H31	0.5737 (18)	0.451 (2)	0.130 (3)	0.076 (8)*
N1	0.61327 (10)	0.66108 (9)	0.15689 (18)	0.0368 (3)
N2	0.76969 (10)	0.63018 (10)	0.30308 (19)	0.0417 (3)
N3	0.45328 (10)	0.67701 (9)	−0.03212 (19)	0.0386 (3)
C1	0.86044 (13)	0.63273 (11)	0.4387 (2)	0.0416 (4)
C2	0.95373 (14)	0.62636 (16)	0.3991 (3)	0.0564 (5)
H2	0.9562 (16)	0.6259 (16)	0.276 (3)	0.068 (7)*
C3	1.04027 (16)	0.62465 (19)	0.5341 (3)	0.0674 (6)
H3	1.105 (2)	0.6198 (18)	0.504 (3)	0.084 (8)*
C4	1.03446 (16)	0.63029 (18)	0.7024 (3)	0.0659 (6)
H4	1.096 (2)	0.6296 (19)	0.798 (4)	0.093 (8)*
C5	0.94171 (16)	0.63699 (18)	0.7406 (3)	0.0636 (6)
H5	0.9365 (19)	0.6452 (19)	0.864 (4)	0.085 (8)*
C6	0.85419 (15)	0.63774 (15)	0.6082 (3)	0.0533 (5)
H6	0.7911 (18)	0.6425 (16)	0.634 (3)	0.072 (7)*
C7	0.38476 (12)	0.74759 (11)	−0.1059 (2)	0.0389 (4)
C8	0.29439 (14)	0.73291 (13)	−0.2286 (3)	0.0495 (4)
C9	0.23353 (16)	0.81009 (15)	−0.2890 (3)	0.0576 (5)
H9	0.1716 (17)	0.8006 (15)	−0.370 (3)	0.061 (6)*
C10	0.26156 (17)	0.90039 (14)	−0.2281 (3)	0.0612 (6)
H10	0.2132 (19)	0.9495 (18)	−0.271 (3)	0.082 (7)*
C11	0.35097 (17)	0.91614 (14)	−0.1075 (3)	0.0573 (5)
H11	0.3682 (18)	0.9747 (18)	−0.066 (3)	0.073 (7)*
C12	0.41318 (13)	0.83901 (11)	−0.0476 (2)	0.0429 (4)
C13	0.53039 (11)	0.71418 (10)	0.0753 (2)	0.0353 (4)
H13	0.2737 (15)	0.6677 (14)	−0.271 (3)	0.055 (6)*
C14	0.63224 (13)	0.56574 (11)	0.1029 (2)	0.0390 (4)
H14	0.6103 (12)	0.5603 (11)	−0.025 (2)	0.031 (4)*
C15	0.74810 (13)	0.55963 (11)	0.1661 (2)	0.0405 (4)
H15	0.7667 (12)	0.4964 (12)	0.214 (2)	0.033 (4)*
C16	0.69410 (12)	0.69497 (11)	0.2832 (2)	0.0377 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0485 (3)	0.0290 (2)	0.0573 (3)	−0.00224 (17)	0.0115 (2)	−0.00327 (18)
O1	0.0438 (6)	0.0417 (6)	0.0558 (8)	−0.0039 (5)	0.0115 (6)	−0.0165 (5)
O2	0.0521 (7)	0.0545 (8)	0.0473 (8)	0.0123 (6)	0.0148 (6)	−0.0030 (6)
O3	0.0609 (8)	0.0336 (6)	0.0524 (8)	−0.0111 (5)	0.0101 (6)	−0.0012 (6)
N1	0.0388 (7)	0.0299 (6)	0.0398 (8)	−0.0014 (5)	0.0061 (6)	−0.0032 (5)
N2	0.0383 (7)	0.0422 (7)	0.0422 (9)	0.0015 (6)	0.0050 (6)	−0.0079 (6)
N3	0.0391 (7)	0.0321 (7)	0.0437 (8)	0.0000 (5)	0.0084 (6)	0.0000 (6)
C1	0.0385 (8)	0.0402 (8)	0.0440 (11)	−0.0036 (7)	0.0058 (7)	−0.0041 (7)
C2	0.0419 (10)	0.0760 (13)	0.0511 (13)	−0.0045 (9)	0.0112 (9)	−0.0059 (10)
C3	0.0395 (11)	0.0919 (16)	0.0694 (16)	−0.0024 (10)	0.0104 (10)	−0.0114 (12)
C4	0.0481 (11)	0.0829 (15)	0.0591 (15)	−0.0019 (10)	−0.0016 (10)	−0.0098 (11)
C5	0.0556 (12)	0.0875 (16)	0.0437 (13)	−0.0004 (11)	0.0046 (9)	−0.0073 (10)
C6	0.0444 (10)	0.0685 (12)	0.0468 (12)	−0.0005 (9)	0.0107 (9)	−0.0042 (9)
C7	0.0409 (9)	0.0343 (8)	0.0434 (10)	0.0033 (6)	0.0141 (7)	0.0039 (7)
C8	0.0480 (10)	0.0447 (10)	0.0531 (12)	0.0018 (8)	0.0071 (9)	0.0026 (8)
C9	0.0504 (11)	0.0590 (11)	0.0588 (13)	0.0102 (9)	0.0046 (10)	0.0087 (9)
C10	0.0607 (12)	0.0494 (11)	0.0725 (15)	0.0173 (9)	0.0143 (11)	0.0164 (10)
C11	0.0639 (12)	0.0353 (10)	0.0737 (15)	0.0077 (8)	0.0188 (11)	0.0072 (9)
C12	0.0465 (9)	0.0350 (8)	0.0501 (11)	0.0017 (7)	0.0171 (8)	0.0038 (7)
C13	0.0392 (8)	0.0304 (7)	0.0383 (9)	−0.0016 (6)	0.0135 (7)	0.0000 (6)
C14	0.0471 (9)	0.0302 (8)	0.0378 (10)	−0.0008 (6)	0.0070 (8)	−0.0017 (6)
C15	0.0464 (9)	0.0327 (8)	0.0396 (9)	0.0042 (7)	0.0054 (8)	−0.0020 (7)
C16	0.0375 (8)	0.0360 (8)	0.0407 (10)	−0.0037 (6)	0.0118 (7)	−0.0032 (7)

Geometric parameters (Å, º)

S1—C12	1.7337 (18)	C3—H3	0.96 (3)
S1—C13	1.7479 (15)	C4—C5	1.375 (3)
O1—C16	1.220 (2)	C4—H4	0.98 (3)
O2—C15	1.397 (2)	C5—C6	1.386 (3)
O2—H21	0.90 (3)	C5—H5	1.01 (3)
O3—C14	1.400 (2)	C6—H6	0.94 (2)
O3—H31	0.84 (3)	C7—C8	1.389 (3)
N1—C13	1.381 (2)	C7—C12	1.399 (2)
N1—C16	1.384 (2)	C8—C9	1.386 (3)
N1—C14	1.460 (2)	C8—H13	1.00 (2)
N2—C16	1.361 (2)	C9—C10	1.388 (3)
N2—C1	1.430 (2)	C9—H9	0.94 (2)
N2—C15	1.455 (2)	C10—C11	1.373 (3)
N3—C13	1.294 (2)	C10—H10	0.96 (3)
N3—C7	1.397 (2)	C11—C12	1.395 (3)
C1—C6	1.373 (3)	C11—H11	0.90 (3)
C1—C2	1.387 (3)	C14—C15	1.540 (2)
C2—C3	1.389 (3)	C14—H14	0.988 (17)
C2—H2	0.99 (3)	C15—H15	0.983 (17)
C3—C4	1.362 (4)
C12—S1—C13	88.27 (8)	C9—C8—H13	121.0 (11)
C15—O2—H21	108.1 (18)	C7—C8—H13	120.4 (11)
C14—O3—H31	108.2 (18)	C8—C9—C10	121.0 (2)
C13—N1—C16	124.61 (13)	C8—C9—H9	119.2 (14)
C13—N1—C14	123.34 (13)	C10—C9—H9	119.8 (13)
C16—N1—C14	111.57 (13)	C11—C10—C9	121.02 (18)
C16—N2—C1	124.23 (14)	C11—C10—H10	123.0 (15)
C16—N2—C15	111.55 (13)	C9—C10—H10	115.9 (15)
C1—N2—C15	124.19 (13)	C10—C11—C12	118.31 (19)
C13—N3—C7	109.81 (13)	C10—C11—H11	120.9 (15)
C6—C1—C2	120.44 (17)	C12—C11—H11	120.8 (15)
C6—C1—N2	119.48 (16)	C11—C12—C7	121.06 (17)
C2—C1—N2	120.03 (18)	C11—C12—S1	128.91 (15)
C1—C2—C3	118.7 (2)	C7—C12—S1	110.02 (12)
C1—C2—H2	118.8 (13)	N3—C13—N1	121.93 (13)
C3—C2—H2	122.5 (13)	N3—C13—S1	117.01 (12)
C4—C3—C2	121.1 (2)	N1—C13—S1	120.93 (11)
C4—C3—H3	121.2 (16)	O3—C14—N1	108.60 (14)
C2—C3—H3	117.7 (16)	O3—C14—C15	112.66 (14)
C3—C4—C5	119.9 (2)	N1—C14—C15	101.39 (12)
C3—C4—H4	120.9 (17)	O3—C14—H14	112.4 (9)
C5—C4—H4	119.2 (17)	N1—C14—H14	110.0 (9)
C4—C5—C6	120.1 (2)	C15—C14—H14	111.2 (9)
C4—C5—H5	120.7 (14)	O2—C15—N2	112.65 (14)
C6—C5—H5	119.1 (15)	O2—C15—C14	113.97 (14)
C1—C6—C5	119.8 (2)	N2—C15—C14	102.14 (13)
C1—C6—H6	120.1 (15)	O2—C15—H15	108.6 (10)
C5—C6—H6	120.1 (15)	N2—C15—H15	110.4 (9)
C8—C7—N3	125.21 (15)	C14—C15—H15	109.0 (9)
C8—C7—C12	119.91 (15)	O1—C16—N2	128.00 (15)
N3—C7—C12	114.88 (15)	O1—C16—N1	124.69 (15)
C9—C8—C7	118.64 (18)	N2—C16—N1	107.29 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H21···O1^i	0.90 (3)	1.90 (3)	2.7832 (18)	166 (2)
O3—H31···N3^ii	0.84 (3)	1.97 (3)	2.8053 (18)	170 (3)

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