Crystal structure, Hirshfeld surface analysis and inter­action energy and DFT studies of 1-(1,3-benzo­thia­zol-2-yl)-3-(2-hy­droxy­eth­yl)imidazolidin-2-one

The title mol­ecule is only a few degrees out of planarity except for the 2-hy­droxy­ethyl substituent. In the crystal, O—H...N hydrogen bonds form stepped chains along the c-axis direction, which are formed into layers parallel to the bc plane by weak C—H...O and C—H...π (ring) inter­actions. Completion of the overall layer structure occurs through weak C—H...O, C—H...π (ring) and head-to-tail slipped π-stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.080
• Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         27 Report

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         24 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1-(1,3-Benzothiazol-2-yl)-3-(2-hydroxyethyl)imidazolidin-2-one

Crystal data

C12H13N3O2S	F(000) = 552
Mr = 263.31	Dx = 1.503 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 7.2863 (2) Å	Cell parameters from 7989 reflections
b = 13.9178 (5) Å	θ = 6.2–72.3°
c = 11.6156 (4) Å	µ = 2.47 mm^−1
β = 98.866 (1)°	T = 150 K
V = 1163.85 (7) Å^3	Block, colourless
Z = 4	0.28 × 0.27 × 0.11 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2246 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2160 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.023
Detector resolution: 10.4167 pixels mm^-1	θmax = 72.3°, θmin = 6.2°
ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −17→15
Tmin = 0.69, Tmax = 0.77	l = −14→14
8781 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: difference Fourier map
wR(F^2) = 0.080	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0449P)^2 + 0.4296P] where P = (Fo^2 + 2Fc^2)/3
2246 reflections	(Δ/σ)max = 0.001
215 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.84367 (4)	0.49137 (2)	0.62655 (3)	0.02128 (12)
O1	0.88222 (13)	0.29904 (7)	0.68752 (8)	0.0249 (2)
O2	0.55711 (14)	0.04397 (7)	0.66690 (8)	0.0288 (2)
H2A	0.586 (3)	0.0432 (16)	0.745 (2)	0.055 (6)*
N1	0.67379 (15)	0.47968 (7)	0.41147 (9)	0.0191 (2)
N2	0.74321 (14)	0.33066 (7)	0.49825 (9)	0.0193 (2)
N3	0.78449 (16)	0.17939 (8)	0.55357 (9)	0.0223 (2)
C1	0.69815 (16)	0.57713 (9)	0.43706 (11)	0.0188 (3)
C2	0.63908 (18)	0.65197 (10)	0.35997 (12)	0.0241 (3)
H2	0.570 (2)	0.6355 (13)	0.2837 (16)	0.035 (4)*
C3	0.67664 (19)	0.74589 (10)	0.39635 (13)	0.0267 (3)
H3	0.637 (2)	0.7985 (14)	0.3464 (16)	0.035 (5)*
C4	0.77217 (19)	0.76532 (10)	0.50716 (13)	0.0275 (3)
H4	0.797 (2)	0.8334 (13)	0.5348 (16)	0.035 (4)*
C5	0.82913 (19)	0.69236 (10)	0.58568 (12)	0.0251 (3)
H5	0.891 (2)	0.7065 (13)	0.6624 (16)	0.032 (4)*
C6	0.79036 (17)	0.59783 (9)	0.54928 (11)	0.0201 (3)
C7	0.74425 (16)	0.42847 (9)	0.50177 (10)	0.0177 (3)
C8	0.66402 (19)	0.27650 (9)	0.39448 (11)	0.0217 (3)
H8A	0.528 (2)	0.2896 (12)	0.3761 (15)	0.031 (4)*
H8B	0.725 (2)	0.2958 (12)	0.3310 (15)	0.027 (4)*
C9	0.7093 (2)	0.17217 (10)	0.43041 (11)	0.0274 (3)
H9A	0.597 (3)	0.1309 (13)	0.4205 (16)	0.037 (5)*
H9B	0.801 (2)	0.1427 (13)	0.3901 (15)	0.036 (4)*
C10	0.81190 (17)	0.27069 (9)	0.59095 (11)	0.0189 (3)
C11	0.8591 (2)	0.09704 (10)	0.62142 (11)	0.0250 (3)
H11A	0.900 (2)	0.1210 (12)	0.6983 (15)	0.028 (4)*
H11B	0.972 (2)	0.0720 (13)	0.5935 (15)	0.031 (4)*
C12	0.7190 (2)	0.01623 (9)	0.62181 (12)	0.0256 (3)
H12A	0.784 (2)	−0.0373 (12)	0.6672 (14)	0.026 (4)*
H12B	0.681 (2)	−0.0069 (11)	0.5418 (16)	0.025 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0263 (2)	0.01777 (18)	0.01832 (18)	0.00109 (11)	−0.00106 (13)	−0.00110 (10)
O1	0.0344 (5)	0.0211 (5)	0.0181 (4)	0.0011 (4)	0.0003 (4)	0.0002 (3)
O2	0.0353 (5)	0.0272 (5)	0.0228 (5)	−0.0006 (4)	0.0011 (4)	0.0037 (4)
N1	0.0222 (5)	0.0164 (5)	0.0185 (5)	0.0007 (4)	0.0025 (4)	0.0010 (4)
N2	0.0259 (5)	0.0152 (5)	0.0163 (5)	−0.0001 (4)	0.0012 (4)	0.0004 (4)
N3	0.0319 (6)	0.0153 (5)	0.0183 (5)	−0.0003 (4)	−0.0002 (4)	0.0023 (4)
C1	0.0191 (6)	0.0160 (6)	0.0218 (6)	0.0007 (5)	0.0048 (4)	−0.0003 (5)
C2	0.0284 (7)	0.0198 (6)	0.0237 (6)	0.0030 (5)	0.0027 (5)	0.0023 (5)
C3	0.0312 (7)	0.0181 (6)	0.0316 (7)	0.0048 (5)	0.0073 (5)	0.0036 (5)
C4	0.0300 (7)	0.0174 (6)	0.0361 (7)	0.0016 (5)	0.0081 (6)	−0.0030 (5)
C5	0.0262 (6)	0.0204 (6)	0.0281 (7)	0.0004 (5)	0.0027 (5)	−0.0051 (5)
C6	0.0198 (6)	0.0183 (6)	0.0221 (6)	0.0017 (5)	0.0030 (5)	−0.0006 (5)
C7	0.0180 (6)	0.0166 (6)	0.0188 (6)	−0.0002 (4)	0.0041 (4)	−0.0005 (4)
C8	0.0299 (7)	0.0175 (6)	0.0168 (6)	−0.0019 (5)	0.0005 (5)	−0.0003 (5)
C9	0.0439 (8)	0.0179 (6)	0.0187 (6)	−0.0025 (6)	−0.0008 (5)	0.0003 (5)
C10	0.0220 (6)	0.0172 (6)	0.0180 (6)	0.0006 (5)	0.0046 (5)	0.0021 (5)
C11	0.0333 (7)	0.0167 (6)	0.0243 (7)	0.0038 (5)	0.0022 (5)	0.0033 (5)
C12	0.0399 (8)	0.0153 (6)	0.0210 (7)	0.0011 (5)	0.0023 (6)	0.0003 (5)

Geometric parameters (Å, º)

S1—C6	1.7448 (13)	C3—C4	1.392 (2)
S1—C7	1.7517 (12)	C3—H3	0.952 (19)
O1—C10	1.2246 (16)	C4—C5	1.385 (2)
O2—C12	1.4161 (17)	C4—H4	1.008 (18)
O2—H2A	0.90 (2)	C5—C6	1.3974 (18)
N1—C7	1.3060 (16)	C5—H5	0.954 (19)
N1—C1	1.3940 (16)	C8—C9	1.5327 (18)
N2—C7	1.3619 (17)	C8—H8A	0.997 (17)
N2—C10	1.3930 (16)	C8—H8B	0.958 (17)
N2—C8	1.4628 (16)	C9—H9A	0.993 (19)
N3—C10	1.3477 (16)	C9—H9B	0.967 (18)
N3—C11	1.4485 (16)	C11—C12	1.5194 (19)
N3—C9	1.4543 (17)	C11—H11A	0.957 (18)
C1—C2	1.3975 (18)	C11—H11B	0.992 (17)
C1—C6	1.4013 (18)	C12—H12A	0.991 (17)
C2—C3	1.388 (2)	C12—H12B	0.982 (18)
C2—H2	0.977 (19)
S1···O1	2.7721 (10)	C1···C7^iv	3.4070 (17)
S1···C11^i	3.6700 (14)	C2···C10^iv	3.5859 (18)
S1···C1^ii	3.6552 (12)	C3···C10^iv	3.5928 (19)
S1···H11A^i	3.117 (16)	C4···C10^ii	3.4350 (19)
O1···C9^iii	3.2869 (16)	C4···C8^iv	3.587 (2)
O1···C8^iii	3.2543 (16)	C6···C7^ii	3.5502 (17)
O2···N1^iii	2.8560 (14)	C1···H2A^vi	2.81 (2)
O2···C3^iv	3.4071 (17)	C4···H8A^iv	2.850 (16)
O2···N3	2.9500 (15)	C5···H8A^iv	2.718 (15)
O1···H9B^iii	2.640 (17)	C9···H12B	2.830 (16)
O1···H11A	2.482 (17)	C12···H9A	2.857 (18)
O1···H8B^iii	2.534 (16)	H2···H9A^vii	2.49 (3)
O2···H9A^v	2.804 (19)	H2···H2A^vi	2.53 (3)
O2···H12B^v	2.803 (18)	H2A···H8B^iii	2.59 (3)
O2···H3^iv	2.601 (18)	H4···C12^viii	2.828 (18)
O2···H2^iii	2.838 (18)	H4···H12A^viii	2.38 (2)
N1···C12^vi	3.4313 (17)	H4···H12B^viii	2.38 (2)
N2···C5^ii	3.4204 (17)	H5···O1^i	2.557 (17)
N1···H8B	2.769 (17)	H5···H11A^i	2.36 (2)
N1···H2A^vi	1.97 (2)	H8B···H11A^vi	2.44 (2)
N1···H8A	2.857 (17)	H9A···H12B	2.40 (2)
C6—S1—C7	88.16 (6)	N2—C7—S1	121.60 (9)
C12—O2—H2A	106.8 (13)	N2—C8—C9	102.87 (10)
C7—N1—C1	109.77 (10)	N2—C8—H8A	109.6 (10)
C7—N2—C10	125.18 (10)	C9—C8—H8A	113.3 (10)
C7—N2—C8	122.65 (10)	N2—C8—H8B	108.6 (10)
C10—N2—C8	112.16 (10)	C9—C8—H8B	111.6 (10)
C10—N3—C11	123.10 (11)	H8A—C8—H8B	110.5 (14)
C10—N3—C9	113.37 (10)	N3—C9—C8	103.60 (10)
C11—N3—C9	122.24 (11)	N3—C9—H9A	109.4 (11)
N1—C1—C2	124.89 (12)	C8—C9—H9A	112.1 (10)
N1—C1—C6	115.18 (11)	N3—C9—H9B	108.8 (10)
C2—C1—C6	119.93 (12)	C8—C9—H9B	114.0 (11)
C3—C2—C1	118.69 (13)	H9A—C9—H9B	108.7 (15)
C3—C2—H2	123.1 (10)	O1—C10—N3	128.27 (12)
C1—C2—H2	118.2 (11)	O1—C10—N2	124.38 (11)
C2—C3—C4	120.76 (13)	N3—C10—N2	107.35 (10)
C2—C3—H3	120.8 (11)	N3—C11—C12	113.03 (11)
C4—C3—H3	118.5 (11)	N3—C11—H11A	105.6 (10)
C5—C4—C3	121.51 (13)	C12—C11—H11A	111.7 (10)
C5—C4—H4	117.3 (10)	N3—C11—H11B	111.1 (10)
C3—C4—H4	121.1 (10)	C12—C11—H11B	109.4 (10)
C4—C5—C6	117.70 (13)	H11A—C11—H11B	105.7 (14)
C4—C5—H5	120.9 (11)	O2—C12—C11	113.43 (11)
C6—C5—H5	121.4 (11)	O2—C12—H12A	111.6 (9)
C5—C6—C1	121.38 (12)	C11—C12—H12A	106.8 (9)
C5—C6—S1	128.70 (10)	O2—C12—H12B	108.1 (10)
C1—C6—S1	109.92 (9)	C11—C12—H12B	109.3 (9)
N1—C7—N2	121.45 (11)	H12A—C12—H12B	107.4 (13)
N1—C7—S1	116.94 (10)
C7—N1—C1—C2	−179.95 (12)	C8—N2—C7—S1	−178.90 (9)
C7—N1—C1—C6	0.42 (15)	C6—S1—C7—N1	−1.36 (10)
N1—C1—C2—C3	−178.49 (12)	C6—S1—C7—N2	177.54 (10)
C6—C1—C2—C3	1.12 (19)	C7—N2—C8—C9	175.82 (11)
C1—C2—C3—C4	0.4 (2)	C10—N2—C8—C9	−5.38 (14)
C2—C3—C4—C5	−1.5 (2)	C10—N3—C9—C8	−7.90 (16)
C3—C4—C5—C6	1.1 (2)	C11—N3—C9—C8	−175.30 (11)
C4—C5—C6—C1	0.40 (19)	N2—C8—C9—N3	7.49 (14)
C4—C5—C6—S1	179.83 (10)	C11—N3—C10—O1	−8.4 (2)
N1—C1—C6—C5	178.12 (11)	C9—N3—C10—O1	−175.68 (13)
C2—C1—C6—C5	−1.53 (19)	C11—N3—C10—N2	172.01 (11)
N1—C1—C6—S1	−1.40 (13)	C9—N3—C10—N2	4.74 (15)
C2—C1—C6—S1	178.95 (9)	C7—N2—C10—O1	−0.1 (2)
C7—S1—C6—C5	−178.02 (13)	C8—N2—C10—O1	−178.84 (12)
C7—S1—C6—C1	1.45 (9)	C7—N2—C10—N3	179.53 (11)
C1—N1—C7—N2	−178.10 (11)	C8—N2—C10—N3	0.77 (14)
C1—N1—C7—S1	0.80 (13)	C10—N3—C11—C12	135.47 (13)
C10—N2—C7—N1	−178.69 (11)	C9—N3—C11—C12	−58.36 (17)
C8—N2—C7—N1	−0.05 (18)	N3—C11—C12—O2	−59.05 (15)
C10—N2—C7—S1	2.46 (17)

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

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the benzene ring (A, C1–C6).

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1^iii	0.90 (2)	1.97 (2)	2.8560 (15)	170 (2)
C5—H5···O1^i	0.954 (19)	2.559 (19)	3.4439 (16)	154.3 (14)
C8—H8B···O1^vi	0.958 (17)	2.532 (16)	3.2542 (16)	132.2 (13)
C8—H8A···Cg1^iv	0.997 (17)	2.840 (16)	3.5646 (15)	130.0 (12)

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