2-(N,N-Di­methyl­amino­methyl)-4-hydroxy-4-(4-chloro­phenyl)­thia­zoline

The structure of the title compound, C₁₂H₁₅ClN₂OS, comprises a twisted mol­ecule that forms dimers in the solid state via the O—H...N(thia­zole) hydrogen-bonding interaction. The phenyl ring is twisted by 88.65 (9)° with respect to the mean plane of the thia­zoline ring (largest ring deviation <0.05 Å). No close contacts are observed involving the amino N atom, but one of the N-methyl C atoms is 3.367 (3) Å from an adjacent Cl atom, although none of the N-methyl H atoms are appropriately positioned to form a C—H...Cl close contact.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.147
• Data-to-parameter ratio = 17.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.52
         From the CIF: _reflns_number_total               2846
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         3033
         Completeness (_total/calc)             93.83%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

2-(N,N-Dimethylaminomethyl)-4-hydroxy-4-phenyl-2-thiazoline

Crystal data

C12H15ClN2OS	Z = 2
Mr = 270.77	F(000) = 284
Triclinic, P1	Dx = 1.361 Mg m^−3
a = 6.1186 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3865 (9) Å	Cell parameters from 25743 reflections
c = 11.977 (2) Å	θ = 1.0–27.5°
α = 103.473 (4)°	µ = 0.43 mm^−1
β = 97.274 (5)°	T = 120 K
γ = 93.32 (1)°	Needle, colourless
V = 660.8 (1) Å^3	0.34 × 0.07 × 0.04 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer	2846 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	2206 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 1.8°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −12→12
Tmin = 0.867, Tmax = 0.983	l = −15→15
8739 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2846 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.22923 (9)	0.72119 (6)	0.75460 (4)	0.0277 (2)
C2	0.1777 (3)	0.5755 (2)	0.8207 (2)	0.0222 (5)
N3	0.3051 (3)	0.56967 (18)	0.9118 (1)	0.0224 (4)
C4	0.4753 (3)	0.6969 (2)	0.9539 (2)	0.0215 (4)
C5	0.4731 (4)	0.7872 (2)	0.8613 (2)	0.0266 (5)
H51	0.6081	0.7749	0.8236	0.033*
H52	0.4692	0.8929	0.8978	0.033*
C21	−0.0263 (3)	0.4727 (2)	0.7703 (2)	0.0236 (5)
H21	−0.0041	0.3751	0.7859	0.030*
H22	−0.1531	0.5110	0.8080	0.030*
N22	−0.0757 (3)	0.4573 (2)	0.6459 (1)	0.0239 (4)
C23	0.0593 (4)	0.3527 (3)	0.5830 (2)	0.0300 (5)
H23	0.2158	0.3809	0.6140	0.037*
H24	0.0349	0.3528	0.5005	0.037*
H25	0.0178	0.2540	0.5919	0.037*
C24	−0.3104 (4)	0.4151 (3)	0.6038 (2)	0.0346 (6)
H26	−0.3527	0.3206	0.6203	0.043*
H27	−0.3381	0.4058	0.5199	0.043*
H28	−0.3980	0.4904	0.6430	0.043*
O41	0.6874 (2)	0.6473 (2)	0.9664 (1)	0.0235 (4)
H41	0.683 (5)	0.576 (4)	1.006 (3)	0.074 (11)*
C41	0.4171 (3)	0.7879 (2)	1.0682 (2)	0.0222 (5)
C42	0.5688 (3)	0.8203 (2)	1.1691 (2)	0.0241 (5)
H42	0.7088	0.7817	1.1680	0.030*
C43	0.5197 (4)	0.9084 (2)	1.2718 (2)	0.0297 (5)
H43	0.6253	0.9311	1.3402	0.037*
C44	0.3142 (4)	0.9620 (2)	1.2722 (2)	0.0290 (5)
Cl42	0.24870 (12)	1.07436 (7)	1.39897 (5)	0.0484 (2)
C45	0.1591 (3)	0.9306 (2)	1.1735 (2)	0.0277 (5)
H45	0.0190	0.9691	1.1751	0.035*
C46	0.2103 (3)	0.8423 (2)	1.0720 (2)	0.0262 (5)
H46	0.1032	0.8186	1.0042	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0341 (4)	0.0262 (3)	0.0227 (3)	0.0024 (2)	−0.0001 (2)	0.0079 (2)
C2	0.0288 (11)	0.0196 (11)	0.0184 (10)	0.0059 (8)	0.0050 (8)	0.0030 (8)
N3	0.0264 (9)	0.0166 (9)	0.0222 (9)	0.0010 (7)	0.0022 (7)	0.0017 (7)
C4	0.0254 (11)	0.0166 (10)	0.0218 (10)	0.0016 (8)	0.0023 (8)	0.0037 (8)
C5	0.0340 (12)	0.0227 (11)	0.0220 (11)	0.0002 (9)	0.0017 (9)	0.0049 (9)
C21	0.0258 (11)	0.0234 (11)	0.0210 (11)	0.0035 (8)	0.0045 (8)	0.0032 (8)
N22	0.0222 (9)	0.0266 (10)	0.0202 (9)	0.0032 (7)	−0.0002 (7)	0.0021 (7)
C23	0.0319 (12)	0.0325 (13)	0.0222 (11)	0.0062 (9)	0.0041 (9)	−0.0011 (9)
C24	0.0294 (12)	0.0377 (14)	0.0340 (13)	0.0028 (10)	−0.0046 (10)	0.0081 (11)
O41	0.0233 (8)	0.0236 (8)	0.0249 (8)	0.0048 (6)	0.0055 (6)	0.0065 (6)
C41	0.0289 (12)	0.0151 (10)	0.0214 (11)	0.0004 (8)	0.0028 (8)	0.0032 (8)
C42	0.0253 (11)	0.0217 (11)	0.0248 (11)	0.0036 (8)	0.0029 (8)	0.0044 (9)
C43	0.0420 (14)	0.0259 (12)	0.0193 (11)	0.0069 (10)	−0.0002 (9)	0.0030 (9)
C44	0.0450 (14)	0.0192 (11)	0.0237 (11)	0.0062 (9)	0.0121 (9)	0.0028 (9)
Cl42	0.0722 (5)	0.0449 (4)	0.0284 (4)	0.0250 (3)	0.0165 (3)	−0.0003 (3)
C45	0.0249 (12)	0.0221 (11)	0.0371 (13)	0.0041 (8)	0.0106 (9)	0.0051 (9)
C46	0.0253 (11)	0.0222 (11)	0.0280 (12)	0.0016 (8)	0.0012 (9)	0.0012 (9)

Geometric parameters (Å, º)

S1—C2	1.765 (2)	C23—H25	0.98
S1—C5	1.812 (2)	C24—H26	0.98
C2—N3	1.272 (3)	C24—H27	0.98
C2—C21	1.500 (3)	C24—H28	0.98
N3—C4	1.485 (2)	O41—H41	0.91 (3)
C4—O41	1.406 (2)	C41—C42	1.388 (3)
C4—C41	1.530 (3)	C41—C46	1.394 (3)
C4—C5	1.545 (3)	C42—C43	1.391 (3)
C5—H51	0.99	C42—H42	0.95
C5—H52	0.99	C43—C44	1.382 (3)
C21—N22	1.454 (3)	C43—H43	0.95
C21—H21	0.99	C44—C45	1.380 (3)
C21—H22	0.99	C44—Cl42	1.743 (2)
N22—C23	1.456 (3)	C45—C46	1.385 (3)
N22—C24	1.460 (3)	C45—H45	0.95
C23—H23	0.98	C46—H46	0.95
C23—H24	0.98
C2—S1—C5	89.7 (1)	N22—C23—H25	109.5
N3—C2—C21	124.2 (2)	H23—C23—H25	109.5
N3—C2—S1	118.6 (2)	H24—C23—H25	109.5
C21—C2—S1	117.1 (2)	N22—C24—H26	109.5
C2—N3—C4	113.6 (2)	N22—C24—H27	109.5
O41—C4—N3	110.2 (2)	H26—C24—H27	109.5
O41—C4—C41	112.6 (2)	N22—C24—H28	109.5
N3—C4—C41	107.3 (2)	H26—C24—H28	109.5
O41—C4—C5	106.3 (2)	H27—C24—H28	109.5
N3—C4—C5	108.9 (2)	C4—O41—H41	108 (2)
C41—C4—C5	111.6 (2)	C42—C41—C46	118.6 (2)
C4—C5—S1	108.0 (1)	C42—C41—C4	121.2 (2)
C4—C5—H51	110.1	C46—C41—C4	120.2 (2)
S1—C5—H51	110.1	C41—C42—C43	121.3 (2)
C4—C5—H52	110.1	C41—C42—H42	119.4
S1—C5—H52	110.1	C43—C42—H42	119.4
H51—C5—H52	108.4	C44—C43—C42	118.5 (2)
N22—C21—C2	110.8 (2)	C44—C43—H43	120.7
N22—C21—H21	109.5	C42—C43—H43	120.7
C2—C21—H21	109.5	C45—C44—C43	121.5 (2)
N22—C21—H22	109.5	C45—C44—Cl42	118.8 (2)
C2—C21—H22	109.5	C43—C44—Cl42	119.7 (2)
H21—C21—H22	108.1	C44—C45—C46	119.2 (2)
C21—N22—C23	111.3 (2)	C44—C45—H45	120.4
C21—N22—C24	111.5 (2)	C46—C45—H45	120.4
C23—N22—C24	110.6 (2)	C45—C46—C41	120.8 (2)
N22—C23—H23	109.5	C45—C46—H46	119.6
N22—C23—H24	109.5	C41—C46—H46	119.6
H23—C23—H24	109.5
C5—S1—C2—N3	2.8 (2)	N3—C4—C41—C42	124.4 (2)
C5—S1—C2—C21	178.0 (2)	C5—C4—C41—C42	−116.5 (2)
C21—C2—N3—C4	−171.0 (2)	O41—C4—C41—C46	−178.2 (2)
S1—C2—N3—C4	3.8 (2)	N3—C4—C41—C46	−56.9 (2)
C2—N3—C4—O41	−126.0 (2)	C5—C4—C41—C46	62.3 (2)
C2—N3—C4—C41	111.1 (2)	C46—C41—C42—C43	−1.6 (3)
C2—N3—C4—C5	−9.8 (2)	C4—C41—C42—C43	177.2 (2)
O41—C4—C5—S1	129.9 (2)	C41—C42—C43—C44	0.8 (3)
N3—C4—C5—S1	11.2 (2)	C42—C43—C44—C45	−0.3 (3)
C41—C4—C5—S1	−107.0 (2)	C42—C43—C44—Cl42	−179.3 (2)
C2—S1—C5—C4	−8.0 (2)	C43—C44—C45—C46	0.5 (3)
N3—C2—C21—N22	−152.8 (2)	Cl42—C44—C45—C46	179.5 (2)
S1—C2—C21—N22	32.3 (2)	C44—C45—C46—C41	−1.4 (3)
C2—C21—N22—C23	81.0 (2)	C42—C41—C46—C45	1.9 (3)
C2—C21—N22—C24	−155.0 (2)	C4—C41—C46—C45	−176.9 (2)
O41—C4—C41—C42	3.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O41—H41···N3^i	0.91 (3)	1.86 (3)	2.767 (2)	176 (3)
C21—H22···O41^ii	0.99	2.38	3.294 (2)	153
C42—H42···O41	0.95	2.43	2.793 (3)	102

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