5-{[(2-Hy­droxy­eth­yl)sulfan­yl]meth­yl}quinolin-8-ol

In the title mol­ecule, C₁₂H₁₃NO₂S, the quinolinol unit is planar (r.m.s. deviation = 0.0128 Å). In the crystal, O—H...N and O—H...S hydrogen bonds together with π-stacking inter­actions form layers parallel to [100] that are associated through C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.093
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.76 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         15 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 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
   3 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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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: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

5-{[(2-Hydroxyethyl)sulfanyl]methyl}quinolin-8-ol

Crystal data

C12H13NO2S	F(000) = 496
Mr = 235.29	Dx = 1.427 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.8362 (7) Å	Cell parameters from 9809 reflections
b = 11.7958 (7) Å	θ = 2.4–29.2°
c = 7.8459 (5) Å	µ = 0.28 mm^−1
β = 91.673 (1)°	T = 120 K
V = 1094.96 (12) Å^3	Thick plate, colourless
Z = 4	0.44 × 0.43 × 0.23 mm

Data collection

Bruker SMART APEX CCD diffractometer	2961 independent reflections
Radiation source: fine-focus sealed tube	2797 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.3333 pixels mm^-1	θmax = 29.2°, θmin = 1.7°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −15→16
Tmin = 0.86, Tmax = 0.94	l = −10→10
33009 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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F^2) = 0.093	Only H-atom displacement parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 0.4352P] where P = (Fo^2 + 2Fc^2)/3
2961 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 5 sec/frame.

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. The hydrogen atoms attached to oxygen were placed in locations derived from a difference map, their coordinates adjusted to give O—H = 0.87 %A and were included as riding contributions.

The hydrogen atoms attached to oxygen were placed in locations derived from a difference map, their coordinates adjusted to give O—H = 0.87 Å and were included as riding contributions.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.09756 (2)	0.62998 (2)	0.68410 (3)	0.01569 (9)
O1	0.54726 (7)	0.61574 (7)	0.18639 (10)	0.01798 (17)
H1	0.534302	0.568575	0.102876	0.039 (5)*
O2	−0.02097 (7)	0.85612 (7)	0.79986 (11)	0.02225 (18)
H2	0.021957	0.873272	0.888036	0.065 (7)*
N1	0.37596 (7)	0.46007 (7)	0.13362 (11)	0.01481 (18)
C1	0.37994 (8)	0.51945 (8)	0.28340 (12)	0.01271 (19)
C2	0.46902 (8)	0.59965 (9)	0.30686 (13)	0.01415 (19)
C3	0.47685 (9)	0.66206 (9)	0.45413 (13)	0.0163 (2)
H3	0.5355 (13)	0.7169 (13)	0.4712 (19)	0.022 (4)*
C4	0.39811 (9)	0.64610 (9)	0.58290 (13)	0.0157 (2)
H4	0.4071 (13)	0.6887 (13)	0.683 (2)	0.021 (3)*
C5	0.31138 (8)	0.56882 (9)	0.56841 (12)	0.01389 (19)
C6	0.30114 (8)	0.50343 (8)	0.41551 (12)	0.01284 (19)
C7	0.21737 (8)	0.41920 (9)	0.38675 (13)	0.0163 (2)
H7	0.1644 (13)	0.4049 (13)	0.474 (2)	0.021 (4)*
C8	0.21448 (9)	0.35904 (9)	0.23679 (14)	0.0183 (2)
H8	0.1620 (14)	0.3049 (14)	0.216 (2)	0.026 (4)*
C9	0.29511 (9)	0.38318 (9)	0.11339 (14)	0.0173 (2)
H9	0.2941 (13)	0.3434 (13)	0.013 (2)	0.022 (4)*
C10	0.23173 (9)	0.55471 (9)	0.71246 (13)	0.0157 (2)
H10A	0.2690 (13)	0.5808 (13)	0.817 (2)	0.021 (3)*
H10B	0.2087 (13)	0.4760 (14)	0.7278 (19)	0.023 (4)*
C11	0.14715 (9)	0.77525 (9)	0.66999 (14)	0.0182 (2)
H11A	0.1931 (13)	0.7926 (14)	0.771 (2)	0.025 (4)*
H11B	0.1940 (14)	0.7851 (15)	0.568 (2)	0.030 (4)*
C12	0.04781 (10)	0.85674 (10)	0.65398 (15)	0.0210 (2)
H12A	0.0778 (13)	0.9341 (14)	0.633 (2)	0.027 (4)*
H12B	−0.0047 (14)	0.8363 (14)	0.560 (2)	0.025 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01307 (14)	0.01642 (14)	0.01784 (14)	0.00009 (8)	0.00495 (9)	−0.00174 (8)
O1	0.0179 (4)	0.0194 (4)	0.0170 (4)	−0.0042 (3)	0.0076 (3)	−0.0010 (3)
O2	0.0195 (4)	0.0236 (4)	0.0240 (4)	0.0021 (3)	0.0054 (3)	−0.0036 (3)
N1	0.0140 (4)	0.0165 (4)	0.0141 (4)	0.0013 (3)	0.0028 (3)	−0.0006 (3)
C1	0.0118 (4)	0.0129 (4)	0.0135 (4)	0.0023 (3)	0.0021 (3)	0.0009 (3)
C2	0.0128 (4)	0.0143 (4)	0.0155 (4)	0.0014 (3)	0.0038 (3)	0.0025 (3)
C3	0.0145 (4)	0.0160 (4)	0.0184 (5)	−0.0019 (4)	0.0024 (4)	−0.0006 (4)
C4	0.0152 (5)	0.0174 (5)	0.0146 (4)	0.0014 (4)	0.0015 (4)	−0.0017 (3)
C5	0.0126 (4)	0.0159 (4)	0.0132 (4)	0.0031 (3)	0.0027 (3)	0.0008 (3)
C6	0.0109 (4)	0.0140 (4)	0.0137 (4)	0.0025 (3)	0.0023 (3)	0.0012 (3)
C7	0.0130 (4)	0.0178 (5)	0.0185 (5)	−0.0003 (4)	0.0047 (4)	0.0002 (4)
C8	0.0143 (5)	0.0193 (5)	0.0215 (5)	−0.0031 (4)	0.0036 (4)	−0.0030 (4)
C9	0.0161 (5)	0.0192 (5)	0.0167 (5)	−0.0003 (4)	0.0035 (4)	−0.0037 (4)
C10	0.0152 (4)	0.0192 (5)	0.0129 (4)	0.0022 (4)	0.0037 (3)	0.0011 (3)
C11	0.0175 (5)	0.0169 (5)	0.0205 (5)	−0.0015 (4)	0.0061 (4)	−0.0018 (4)
C12	0.0239 (5)	0.0186 (5)	0.0206 (5)	0.0025 (4)	0.0042 (4)	0.0001 (4)

Geometric parameters (Å, º)

S1—C11	1.8158 (11)	C5—C6	1.4284 (13)
S1—C10	1.8273 (11)	C5—C10	1.5021 (13)
O1—C2	1.3558 (12)	C6—C7	1.4171 (14)
O1—H1	0.8698	C7—C8	1.3736 (15)
O2—C12	1.4239 (14)	C7—H7	0.956 (16)
O2—H2	0.8701	C8—C9	1.4082 (15)
N1—C9	1.3246 (14)	C8—H8	0.903 (17)
N1—C1	1.3677 (13)	C9—H9	0.916 (16)
C1—C2	1.4245 (14)	C10—H10A	0.969 (15)
C1—C6	1.4271 (13)	C10—H10B	0.976 (16)
C2—C3	1.3709 (14)	C11—C12	1.5211 (16)
C3—C4	1.4070 (14)	C11—H11A	0.967 (16)
C3—H3	0.955 (16)	C11—H11B	0.993 (17)
C4—C5	1.3751 (14)	C12—H12A	0.994 (17)
C4—H4	0.934 (16)	C12—H12B	0.978 (16)
C11—S1—C10	100.64 (5)	C7—C8—C9	118.95 (10)
C2—O1—H1	109.1	C7—C8—H8	121.5 (10)
C12—O2—H2	107.7	C9—C8—H8	119.6 (10)
C9—N1—C1	117.41 (9)	N1—C9—C8	123.90 (10)
N1—C1—C2	117.26 (9)	N1—C9—H9	116.4 (10)
N1—C1—C6	123.32 (9)	C8—C9—H9	119.7 (10)
C2—C1—C6	119.41 (9)	C5—C10—S1	114.64 (7)
O1—C2—C3	118.79 (9)	C5—C10—H10A	108.7 (9)
O1—C2—C1	121.39 (9)	S1—C10—H10A	108.7 (9)
C3—C2—C1	119.81 (9)	C5—C10—H10B	112.5 (9)
C2—C3—C4	120.23 (10)	S1—C10—H10B	103.4 (9)
C2—C3—H3	120.8 (9)	H10A—C10—H10B	108.7 (12)
C4—C3—H3	118.9 (9)	C12—C11—S1	110.55 (8)
C5—C4—C3	122.54 (9)	C12—C11—H11A	110.4 (9)
C5—C4—H4	119.4 (9)	S1—C11—H11A	109.0 (9)
C3—C4—H4	118.0 (9)	C12—C11—H11B	108.0 (10)
C4—C5—C6	118.18 (9)	S1—C11—H11B	110.4 (10)
C4—C5—C10	119.65 (9)	H11A—C11—H11B	108.5 (13)
C6—C5—C10	122.16 (9)	O2—C12—C11	112.90 (9)
C7—C6—C1	116.51 (9)	O2—C12—H12A	110.5 (9)
C7—C6—C5	123.65 (9)	C11—C12—H12A	108.4 (9)
C1—C6—C5	119.82 (9)	O2—C12—H12B	103.7 (10)
C8—C7—C6	119.89 (9)	C11—C12—H12B	112.3 (10)
C8—C7—H7	121.4 (9)	H12A—C12—H12B	109.1 (13)
C6—C7—H7	118.7 (9)
C9—N1—C1—C2	178.17 (9)	C4—C5—C6—C7	178.35 (10)
C9—N1—C1—C6	−0.86 (15)	C10—C5—C6—C7	−1.01 (15)
N1—C1—C2—O1	−0.60 (14)	C4—C5—C6—C1	0.05 (14)
C6—C1—C2—O1	178.47 (9)	C10—C5—C6—C1	−179.31 (9)
N1—C1—C2—C3	179.65 (9)	C1—C6—C7—C8	−0.74 (15)
C6—C1—C2—C3	−1.28 (15)	C5—C6—C7—C8	−179.09 (10)
O1—C2—C3—C4	−178.96 (9)	C6—C7—C8—C9	−0.43 (16)
C1—C2—C3—C4	0.80 (15)	C1—N1—C9—C8	−0.44 (16)
C2—C3—C4—C5	0.13 (16)	C7—C8—C9—N1	1.10 (17)
C3—C4—C5—C6	−0.55 (15)	C4—C5—C10—S1	99.16 (10)
C3—C4—C5—C10	178.83 (9)	C6—C5—C10—S1	−81.48 (11)
N1—C1—C6—C7	1.44 (14)	C11—S1—C10—C5	−60.60 (8)
C2—C1—C6—C7	−177.57 (9)	C10—S1—C11—C12	−177.29 (8)
N1—C1—C6—C5	179.86 (9)	S1—C11—C12—O2	63.58 (11)
C2—C1—C6—C5	0.85 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.87	2.29	2.7577 (12)	114
O1—H1···N1^i	0.87	2.19	2.8395 (11)	131
O2—H2···S1^ii	0.87	2.47	3.2919 (9)	159
C3—H3···O1^ii	0.955 (16)	2.599 (16)	3.2858 (13)	129.1 (11)
C8—H8···O2^iii	0.903 (17)	2.529 (17)	3.4252 (14)	171.9 (14)
C9—H9···O1^i	0.917 (16)	2.525 (16)	3.0446 (13)	116.3 (12)

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