Proton tautomerism in 5-di­methyl­amino­methyl­idene-4-(o-,m-,p-hy­droxy­phenyl)­amino-1,3-thia­zol-2(5H)-ones: synthesis, crystal structure and spectro­scopic studies

Three new 5-di­methyl­amino­methyl­idene-4-phenyl­amino-1,3-thia­zol-2(5H)-ones with an hydroxyl group in the ortho, meta and para positions on the phenyl ring were synthesized in order to deduce the structural changes occurring on prototropic tautomerism of the amidine system. The existence of all the title compounds solely in the amino tautomeric form has been established in the solid and liquid (dimethyl sulfoxide solution) phases. The title compounds are analyzed from the point of view of the electronic effects and conformational freedom of their molecules. The intermolecular interactions in the crystals and their supramolecular architecture are highlighted.

Computing details

Data collection: CrysAlis PRO 1.171.37.35 (Rigaku OD, 2014) for (1); CrysAlis PRO 1.171.40.67a (Rigaku OD, 2019) for 2.DMF; CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015) for 3.DMF. Cell refinement: CrysAlis PRO 1.171.37.35 (Rigaku OD, 2014) for (1); CrysAlis PRO 1.171.40.67a (Rigaku OD, 2019) for 2.DMF; CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015) for 3.DMF. Data reduction: CrysAlis PRO 1.171.37.35 (Rigaku OD, 2014) for (1); CrysAlis PRO 1.171.40.67a (Rigaku OD, 2019) for 2.DMF; CrysAlis PRO 1.171.38.41 (Rigaku OD, 2015) for 3.DMF. For all structures, program(s) used to solve structure: SHELXT 2018/2 (Sheldrick, 2018); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012), OLEX2 v1.2-alpha (Dolomanov et al., 2009), PLATON (Spek, 2009).

5-dimethylaminomethylidene-4-(2-hydroxyphenyl)amino-1,3-thiazol-2(5H)-one (1)

Crystal data

C12H13N3O2S	Dx = 1.484 Mg m^−3
Mr = 263.31	Melting point = 517–518 K
Orthorhombic, Fdd2	Cu Kα radiation, λ = 1.54184 Å
a = 46.689 (4) Å	Cell parameters from 6185 reflections
b = 12.2502 (6) Å	θ = 3.7–76.0°
c = 8.2435 (4) Å	µ = 2.44 mm^−1
V = 4714.9 (5) Å^3	T = 130 K
Z = 16	Plate, yellow
F(000) = 2208	0.28 × 0.12 × 0.03 mm

Data collection

SuperNova, Dual, Cu, Atlas diffractometer	2358 independent reflections
Radiation source: sealed X-ray tube	2257 reflections with I > 2σ(I)
Detector resolution: 5.1996 pixels mm^-1	Rint = 0.037
ω scans	θmax = 76.3°, θmin = 3.8°
Absorption correction: multi-scan CrysAlisPro 1.171.37.35 (Rigaku Oxford Diffraction, 2014) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −57→58
Tmin = 0.395, Tmax = 1.000	k = −15→13
12261 measured reflections	l = −10→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0341P)^2 + 5.7549P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2358 reflections	Δρmax = 0.19 e Å^−3
173 parameters	Δρmin = −0.24 e Å^−3
1 restraint	Absolute structure: Flack x determined using 950 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.012 (10)

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.

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

	x	y	z	Uiso*/Ueq
S1	0.58843 (2)	0.32633 (5)	0.60385 (8)	0.02211 (15)
C2	0.62353 (6)	0.2900 (2)	0.6690 (3)	0.0219 (5)
N3	0.64416 (5)	0.33796 (17)	0.5774 (3)	0.0205 (5)
C4	0.63332 (6)	0.3992 (2)	0.4570 (3)	0.0195 (5)
C5	0.60282 (5)	0.4084 (2)	0.4491 (3)	0.0193 (5)
O6	0.62738 (4)	0.22750 (17)	0.7831 (3)	0.0291 (4)
N7	0.65051 (4)	0.44692 (17)	0.3464 (3)	0.0199 (4)
H7	0.6425 (7)	0.475 (3)	0.266 (4)	0.019 (8)*
C8	0.68043 (5)	0.46815 (19)	0.3466 (3)	0.0179 (5)
C9	0.70199 (5)	0.4004 (2)	0.4118 (3)	0.0189 (5)
C10	0.73053 (5)	0.4278 (2)	0.3848 (3)	0.0222 (6)
H10	0.745124	0.383022	0.429839	0.027*
C11	0.73828 (6)	0.5183 (2)	0.2941 (3)	0.0231 (5)
H11	0.757930	0.533830	0.274893	0.028*
C12	0.71714 (6)	0.5865 (2)	0.2311 (3)	0.0231 (5)
H12	0.722191	0.649168	0.169602	0.028*
C13	0.68871 (6)	0.5615 (2)	0.2593 (3)	0.0200 (5)
H13	0.674318	0.608904	0.218469	0.024*
O14	0.69706 (5)	0.30695 (15)	0.4958 (3)	0.0269 (4)
H14	0.6799 (10)	0.305 (3)	0.529 (5)	0.054 (13)*
C15	0.58868 (5)	0.48065 (19)	0.3489 (3)	0.0187 (5)
H15	0.600680	0.528428	0.288710	0.022*
N16	0.56085 (5)	0.49326 (17)	0.3241 (3)	0.0204 (5)
C17	0.55062 (6)	0.5798 (2)	0.2180 (4)	0.0247 (5)
H17A	0.540317	0.634429	0.282281	0.037*
H17B	0.537706	0.548867	0.136328	0.037*
H17C	0.566961	0.614366	0.163855	0.037*
C18	0.53916 (6)	0.4225 (2)	0.3960 (3)	0.0245 (6)
H18A	0.545178	0.346126	0.385779	0.037*
H18B	0.520895	0.432912	0.339530	0.037*
H18C	0.536839	0.440769	0.510983	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0238 (3)	0.0203 (3)	0.0222 (3)	−0.0002 (2)	0.0032 (3)	0.0069 (2)
C2	0.0260 (12)	0.0199 (12)	0.0196 (12)	0.0027 (10)	0.0028 (10)	0.0016 (10)
N3	0.0244 (10)	0.0199 (10)	0.0171 (12)	0.0025 (8)	−0.0003 (9)	0.0028 (8)
C4	0.0251 (12)	0.0161 (11)	0.0172 (12)	−0.0010 (10)	−0.0004 (10)	−0.0002 (9)
C5	0.0226 (12)	0.0157 (11)	0.0195 (13)	−0.0031 (9)	0.0041 (10)	0.0007 (9)
O6	0.0346 (11)	0.0318 (10)	0.0209 (9)	0.0062 (9)	0.0040 (8)	0.0114 (8)
N7	0.0188 (9)	0.0230 (11)	0.0179 (10)	0.0006 (8)	−0.0021 (10)	0.0071 (10)
C8	0.0202 (11)	0.0189 (11)	0.0146 (11)	−0.0002 (9)	0.0020 (10)	−0.0020 (10)
C9	0.0240 (12)	0.0164 (11)	0.0164 (11)	0.0023 (10)	−0.0011 (10)	−0.0016 (9)
C10	0.0230 (12)	0.0244 (13)	0.0192 (14)	0.0038 (10)	−0.0039 (10)	−0.0040 (10)
C11	0.0184 (12)	0.0249 (13)	0.0259 (13)	−0.0031 (10)	0.0029 (10)	−0.0075 (11)
C12	0.0268 (13)	0.0195 (11)	0.0231 (13)	−0.0017 (10)	0.0040 (10)	−0.0009 (10)
C13	0.0230 (13)	0.0177 (12)	0.0194 (12)	0.0021 (9)	−0.0003 (10)	0.0001 (10)
O14	0.0262 (10)	0.0232 (9)	0.0312 (11)	0.0058 (8)	0.0022 (9)	0.0100 (8)
C15	0.0209 (11)	0.0161 (11)	0.0190 (11)	−0.0014 (9)	0.0022 (11)	−0.0012 (9)
N16	0.0212 (10)	0.0172 (10)	0.0228 (12)	0.0004 (8)	−0.0001 (8)	0.0024 (8)
C17	0.0250 (13)	0.0195 (12)	0.0296 (14)	0.0031 (10)	−0.0039 (11)	0.0036 (11)
C18	0.0214 (12)	0.0249 (13)	0.0273 (15)	−0.0038 (10)	−0.0004 (10)	0.0025 (11)

Geometric parameters (Å, º)

S1—C5	1.757 (3)	C11—C12	1.393 (4)
S1—C2	1.781 (3)	C11—H11	0.9500
C2—O6	1.226 (3)	C12—C13	1.382 (4)
C2—N3	1.358 (3)	C12—H12	0.9500
N3—C4	1.343 (3)	C13—H13	0.9500
C4—N7	1.348 (3)	O14—H14	0.85 (5)
C4—C5	1.430 (3)	C15—N16	1.325 (3)
C5—C15	1.379 (4)	C15—H15	0.9500
N7—C8	1.421 (3)	N16—C17	1.455 (3)
N7—H7	0.84 (3)	N16—C18	1.459 (3)
C8—C13	1.405 (3)	C17—H17A	0.9800
C8—C9	1.411 (3)	C17—H17B	0.9800
C9—O14	1.358 (3)	C17—H17C	0.9800
C9—C10	1.392 (4)	C18—H18A	0.9800
C10—C11	1.386 (4)	C18—H18B	0.9800
C10—H10	0.9500	C18—H18C	0.9800
C5—S1—C2	90.57 (12)	C13—C12—C11	119.0 (2)
O6—C2—N3	126.4 (2)	C13—C12—H12	120.5
O6—C2—S1	121.5 (2)	C11—C12—H12	120.5
N3—C2—S1	112.14 (19)	C12—C13—C8	122.1 (2)
C4—N3—C2	112.7 (2)	C12—C13—H13	119.0
N3—C4—N7	121.2 (2)	C8—C13—H13	119.0
N3—C4—C5	116.9 (2)	C9—O14—H14	110 (3)
N7—C4—C5	121.9 (2)	N16—C15—C5	129.6 (2)
C15—C5—C4	123.7 (2)	N16—C15—H15	115.2
C15—C5—S1	128.23 (19)	C5—C15—H15	115.2
C4—C5—S1	107.62 (18)	C15—N16—C17	120.0 (2)
C4—N7—C8	131.6 (2)	C15—N16—C18	123.3 (2)
C4—N7—H7	117 (2)	C17—N16—C18	116.7 (2)
C8—N7—H7	112 (2)	N16—C17—H17A	109.5
C13—C8—C9	118.5 (2)	N16—C17—H17B	109.5
C13—C8—N7	114.8 (2)	H17A—C17—H17B	109.5
C9—C8—N7	126.5 (2)	N16—C17—H17C	109.5
O14—C9—C10	116.5 (2)	H17A—C17—H17C	109.5
O14—C9—C8	124.7 (2)	H17B—C17—H17C	109.5
C10—C9—C8	118.7 (2)	N16—C18—H18A	109.5
C11—C10—C9	121.9 (2)	N16—C18—H18B	109.5
C11—C10—H10	119.0	H18A—C18—H18B	109.5
C9—C10—H10	119.0	N16—C18—H18C	109.5
C10—C11—C12	119.7 (2)	H18A—C18—H18C	109.5
C10—C11—H11	120.1	H18B—C18—H18C	109.5
C12—C11—H11	120.1
C5—S1—C2—O6	−179.3 (2)	C13—C8—C9—O14	−178.7 (2)
C5—S1—C2—N3	−0.1 (2)	N7—C8—C9—O14	−5.0 (4)
O6—C2—N3—C4	177.7 (3)	C13—C8—C9—C10	−1.1 (4)
S1—C2—N3—C4	−1.5 (3)	N7—C8—C9—C10	172.6 (3)
C2—N3—C4—N7	−175.3 (2)	O14—C9—C10—C11	176.9 (2)
C2—N3—C4—C5	2.8 (3)	C8—C9—C10—C11	−1.0 (4)
N3—C4—C5—C15	169.9 (2)	C9—C10—C11—C12	1.8 (4)
N7—C4—C5—C15	−12.0 (4)	C10—C11—C12—C13	−0.6 (4)
N3—C4—C5—S1	−2.8 (3)	C11—C12—C13—C8	−1.4 (4)
N7—C4—C5—S1	175.3 (2)	C9—C8—C13—C12	2.3 (4)
C2—S1—C5—C15	−170.8 (2)	N7—C8—C13—C12	−172.1 (2)
C2—S1—C5—C4	1.49 (19)	C4—C5—C15—N16	176.1 (3)
N3—C4—N7—C8	−16.7 (4)	S1—C5—C15—N16	−12.7 (4)
C5—C4—N7—C8	165.3 (2)	C5—C15—N16—C17	176.7 (3)
C4—N7—C8—C13	−149.5 (3)	C5—C15—N16—C18	−4.7 (4)
C4—N7—C8—C9	36.7 (4)

5-dimethylaminomethylidene-4-(3-hydroxyphenyl)amino-1,3-thiazol-2(5H)-one dimethylformamide solvate (2.DMF)

Crystal data

C12H13N3O2S·C3H7NO	Dx = 1.403 Mg m^−3
Mr = 336.41	Melting point = 492–493 K
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 20.7594 (3) Å	Cell parameters from 9527 reflections
b = 11.8833 (2) Å	θ = 5.1–76.2°
c = 13.3407 (2) Å	µ = 1.99 mm^−1
β = 104.534 (2)°	T = 130 K
V = 3185.70 (9) Å^3	Lath, yellow
Z = 8	0.37 × 0.12 × 0.05 mm
F(000) = 1424

Data collection

SuperNova, Dual, Cu, Atlas diffractometer	11361 independent reflections
Radiation source: micro-focus sealed X-ray tube	9171 reflections with I > 2σ(I)
Detector resolution: 10.3991 pixels mm^-1	θmax = 76.5°, θmin = 2.2°
ω scans	h = −26→26
Absorption correction: multi-scan CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −14→14
Tmin = 0.700, Tmax = 1.000	l = −16→16
11361 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)] = 0.042	Hydrogen site location: mixed
wR(F^2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0911P)^2] where P = (Fo^2 + 2Fc^2)/3
11361 reflections	(Δ/σ)max = 0.001
440 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.38 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. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
S1A	0.27572 (2)	0.45442 (3)	0.40142 (3)	0.01918 (11)
C2A	0.18755 (8)	0.45142 (12)	0.35527 (12)	0.0186 (3)
N3A	0.16237 (6)	0.34635 (11)	0.33595 (10)	0.0181 (3)
C4A	0.21049 (7)	0.26837 (13)	0.35676 (11)	0.0164 (3)
C5A	0.27801 (7)	0.30713 (13)	0.39496 (11)	0.0168 (3)
O6A	0.15573 (6)	0.54030 (10)	0.34412 (10)	0.0256 (3)
N7A	0.19607 (6)	0.15744 (11)	0.34276 (11)	0.0189 (3)
H7A	0.2285 (11)	0.1103 (19)	0.3593 (17)	0.026 (5)*
C8A	0.13379 (7)	0.10260 (13)	0.31353 (12)	0.0180 (3)
C9A	0.07385 (8)	0.15688 (13)	0.27065 (13)	0.0210 (3)
H9A	0.072598	0.236069	0.260579	0.025*
C10A	0.01549 (8)	0.09323 (14)	0.24261 (13)	0.0215 (3)
C11A	0.01615 (8)	−0.02243 (14)	0.25636 (13)	0.0229 (3)
H11A	−0.023888	−0.064748	0.237211	0.027*
C12A	0.07670 (9)	−0.07529 (13)	0.29879 (14)	0.0268 (4)
H12A	0.077962	−0.154586	0.308097	0.032*
C13A	0.13507 (8)	−0.01386 (14)	0.32760 (13)	0.0241 (3)
H13A	0.176002	−0.050936	0.356950	0.029*
O14A	−0.04164 (6)	0.15056 (11)	0.19880 (12)	0.0346 (3)
H14A	−0.0760 (14)	0.108 (2)	0.185 (2)	0.049 (7)*
C15A	0.33181 (7)	0.23765 (13)	0.42911 (11)	0.0178 (3)
H15A	0.321492	0.159847	0.430184	0.021*
N16A	0.39647 (6)	0.26255 (11)	0.46110 (11)	0.0211 (3)
C17A	0.44359 (8)	0.17560 (15)	0.51042 (14)	0.0268 (4)
H17A	0.463886	0.196889	0.582390	0.040*
H17B	0.478362	0.167749	0.472974	0.040*
H17C	0.420116	0.103831	0.508974	0.040*
C18A	0.42462 (8)	0.37346 (14)	0.45306 (14)	0.0247 (3)
H18A	0.396925	0.413356	0.393321	0.037*
H18B	0.469824	0.365294	0.444133	0.037*
H18C	0.426041	0.416371	0.516313	0.037*
O19A	0.30156 (7)	−0.02103 (11)	0.41260 (11)	0.0329 (3)
C20A	0.34020 (8)	−0.09534 (14)	0.40106 (14)	0.0261 (3)
H20A	0.374819	−0.074507	0.369770	0.031*
N21A	0.33769 (7)	−0.20229 (12)	0.42861 (12)	0.0253 (3)
C22A	0.38153 (9)	−0.28700 (15)	0.40389 (18)	0.0348 (4)
H22A	0.354994	−0.344652	0.359450	0.052*
H22B	0.407385	−0.321918	0.467956	0.052*
H22C	0.411861	−0.251711	0.367559	0.052*
C23A	0.28851 (10)	−0.23890 (15)	0.48248 (15)	0.0327 (4)
H23A	0.263319	−0.173632	0.496660	0.049*
H23B	0.311066	−0.275003	0.547925	0.049*
H23C	0.258010	−0.292721	0.439149	0.049*
S1B	0.22457 (2)	0.04882 (3)	0.61134 (3)	0.01959 (12)
C2B	0.31273 (8)	0.04949 (13)	0.65782 (12)	0.0191 (3)
N3B	0.33894 (6)	0.15438 (11)	0.67497 (10)	0.0184 (3)
C4B	0.29151 (7)	0.23335 (13)	0.65326 (11)	0.0161 (3)
C5B	0.22364 (7)	0.19618 (13)	0.61534 (11)	0.0171 (3)
O6B	0.34354 (6)	−0.04012 (10)	0.67248 (11)	0.0263 (3)
N7B	0.30682 (6)	0.34422 (11)	0.66628 (11)	0.0186 (3)
H7B	0.2743 (12)	0.3931 (19)	0.6505 (18)	0.028 (5)*
C8B	0.36972 (7)	0.39727 (13)	0.69251 (12)	0.0177 (3)
C9B	0.42871 (8)	0.34370 (12)	0.74181 (13)	0.0196 (3)
H9B	0.428727	0.265925	0.758289	0.024*
C10B	0.48801 (8)	0.40526 (13)	0.76694 (13)	0.0206 (3)
C11B	0.48908 (8)	0.51897 (13)	0.74193 (12)	0.0213 (3)
H11B	0.529658	0.559990	0.758049	0.026*
C12B	0.42969 (8)	0.57112 (13)	0.69298 (13)	0.0234 (3)
H12B	0.429783	0.648778	0.676097	0.028*
C13B	0.37023 (8)	0.51199 (14)	0.66828 (13)	0.0221 (3)
H13B	0.329990	0.549067	0.635057	0.027*
O14B	0.54386 (6)	0.34904 (10)	0.81743 (11)	0.0300 (3)
H14B	0.5767 (14)	0.390 (2)	0.823 (2)	0.045 (7)*
C15B	0.17048 (7)	0.26684 (13)	0.58059 (12)	0.0183 (3)
H15B	0.181300	0.344468	0.579998	0.022*
N16B	0.10562 (6)	0.24272 (12)	0.54740 (11)	0.0221 (3)
C17B	0.05891 (8)	0.33044 (15)	0.49972 (15)	0.0281 (4)
H17D	0.083446	0.399353	0.493085	0.042*
H17E	0.028088	0.345340	0.543034	0.042*
H17F	0.033780	0.305652	0.430947	0.042*
C18B	0.07701 (8)	0.13208 (14)	0.55468 (14)	0.0258 (3)
H18D	0.078235	0.087721	0.493258	0.039*
H18E	0.030786	0.140489	0.558828	0.039*
H18F	0.102742	0.093565	0.616847	0.039*
O19B	0.20670 (7)	0.52949 (11)	0.62197 (13)	0.0378 (3)
C20B	0.16619 (9)	0.60227 (15)	0.58329 (15)	0.0288 (4)
H20B	0.131981	0.581083	0.524539	0.035*
N21B	0.16554 (7)	0.70770 (12)	0.61558 (12)	0.0267 (3)
C22B	0.11583 (10)	0.78763 (16)	0.56358 (18)	0.0384 (5)
H22D	0.086621	0.752052	0.502614	0.058*
H22E	0.137790	0.852952	0.541870	0.058*
H22F	0.089379	0.812092	0.610988	0.058*
C23B	0.21370 (10)	0.74647 (17)	0.70753 (16)	0.0368 (4)
H23D	0.237825	0.681806	0.744481	0.055*
H23E	0.190596	0.786001	0.752773	0.055*
H23F	0.245245	0.797820	0.687495	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.01365 (19)	0.01486 (19)	0.0266 (2)	−0.00099 (12)	0.00049 (14)	−0.00076 (13)
C2A	0.0156 (7)	0.0179 (7)	0.0211 (7)	−0.0005 (5)	0.0024 (5)	0.0006 (5)
N3A	0.0152 (6)	0.0170 (6)	0.0213 (6)	−0.0007 (5)	0.0029 (5)	0.0005 (5)
C4A	0.0146 (7)	0.0172 (7)	0.0168 (6)	−0.0016 (5)	0.0030 (5)	0.0009 (5)
C5A	0.0148 (7)	0.0161 (7)	0.0185 (7)	−0.0019 (5)	0.0021 (5)	0.0003 (5)
O6A	0.0169 (5)	0.0171 (6)	0.0400 (7)	0.0035 (4)	0.0019 (5)	−0.0002 (5)
N7A	0.0143 (6)	0.0146 (6)	0.0260 (7)	0.0002 (5)	0.0017 (5)	0.0006 (5)
C8A	0.0176 (7)	0.0166 (7)	0.0192 (7)	−0.0031 (6)	0.0036 (5)	−0.0004 (6)
C9A	0.0185 (8)	0.0155 (7)	0.0273 (8)	−0.0031 (6)	0.0024 (6)	0.0006 (6)
C10A	0.0173 (7)	0.0191 (7)	0.0267 (8)	−0.0024 (6)	0.0029 (6)	−0.0005 (6)
C11A	0.0216 (7)	0.0184 (7)	0.0273 (8)	−0.0059 (6)	0.0037 (6)	−0.0020 (6)
C12A	0.0279 (8)	0.0148 (7)	0.0352 (9)	−0.0038 (6)	0.0029 (7)	0.0003 (6)
C13A	0.0221 (8)	0.0165 (7)	0.0310 (8)	0.0010 (6)	0.0017 (6)	0.0011 (6)
O14A	0.0155 (6)	0.0203 (6)	0.0612 (9)	−0.0031 (5)	−0.0027 (5)	0.0026 (6)
C15A	0.0163 (7)	0.0190 (7)	0.0178 (6)	−0.0009 (6)	0.0036 (5)	0.0004 (6)
N16A	0.0151 (6)	0.0223 (7)	0.0244 (6)	0.0015 (5)	0.0021 (5)	0.0004 (5)
C17A	0.0180 (7)	0.0282 (9)	0.0315 (8)	0.0061 (6)	0.0010 (6)	0.0020 (7)
C18A	0.0173 (7)	0.0267 (8)	0.0298 (8)	−0.0049 (6)	0.0052 (6)	−0.0001 (7)
O19A	0.0340 (7)	0.0200 (6)	0.0442 (8)	0.0046 (5)	0.0091 (6)	0.0046 (5)
C20A	0.0249 (8)	0.0218 (8)	0.0294 (8)	−0.0020 (6)	0.0028 (6)	−0.0007 (7)
N21A	0.0230 (7)	0.0185 (6)	0.0321 (7)	0.0016 (5)	0.0028 (5)	0.0006 (6)
C22A	0.0275 (9)	0.0242 (8)	0.0516 (11)	0.0054 (7)	0.0077 (8)	−0.0039 (8)
C23A	0.0375 (9)	0.0243 (8)	0.0382 (10)	−0.0004 (7)	0.0130 (8)	0.0037 (7)
S1B	0.01352 (19)	0.01525 (19)	0.0276 (2)	−0.00083 (12)	0.00062 (14)	−0.00106 (13)
C2B	0.0153 (7)	0.0186 (7)	0.0220 (7)	−0.0001 (5)	0.0018 (5)	0.0005 (5)
N3B	0.0143 (6)	0.0173 (6)	0.0226 (6)	−0.0002 (5)	0.0028 (5)	0.0003 (5)
C4B	0.0145 (7)	0.0171 (7)	0.0166 (6)	−0.0013 (5)	0.0034 (5)	0.0006 (5)
C5B	0.0142 (7)	0.0172 (7)	0.0185 (7)	−0.0021 (5)	0.0014 (5)	0.0006 (5)
O6B	0.0173 (5)	0.0172 (6)	0.0415 (7)	0.0028 (4)	0.0020 (5)	0.0004 (5)
N7B	0.0137 (6)	0.0150 (6)	0.0253 (6)	0.0003 (5)	0.0013 (5)	−0.0001 (5)
C8B	0.0178 (7)	0.0162 (7)	0.0188 (7)	−0.0028 (6)	0.0038 (5)	−0.0015 (5)
C9B	0.0184 (7)	0.0149 (7)	0.0246 (7)	−0.0019 (6)	0.0037 (6)	0.0004 (6)
C10B	0.0184 (7)	0.0179 (7)	0.0249 (7)	−0.0018 (6)	0.0040 (6)	−0.0004 (6)
C11B	0.0214 (7)	0.0172 (7)	0.0247 (7)	−0.0058 (6)	0.0045 (6)	−0.0026 (6)
C12B	0.0274 (8)	0.0157 (7)	0.0255 (8)	−0.0035 (6)	0.0036 (6)	0.0005 (6)
C13B	0.0217 (7)	0.0169 (7)	0.0252 (8)	0.0003 (6)	0.0010 (6)	0.0003 (6)
O14B	0.0149 (5)	0.0206 (6)	0.0504 (8)	−0.0030 (5)	0.0007 (5)	0.0041 (5)
C15B	0.0152 (7)	0.0188 (7)	0.0207 (7)	−0.0003 (6)	0.0043 (5)	0.0006 (6)
N16B	0.0143 (6)	0.0241 (7)	0.0263 (7)	0.0015 (5)	0.0020 (5)	0.0028 (5)
C17B	0.0180 (7)	0.0285 (9)	0.0352 (9)	0.0066 (6)	0.0015 (6)	0.0042 (7)
C18B	0.0171 (7)	0.0272 (8)	0.0322 (9)	−0.0032 (6)	0.0044 (6)	0.0024 (7)
O19B	0.0359 (7)	0.0240 (6)	0.0560 (9)	0.0086 (6)	0.0158 (6)	0.0020 (6)
C20B	0.0286 (8)	0.0225 (8)	0.0357 (9)	−0.0006 (7)	0.0086 (7)	−0.0034 (7)
N21B	0.0225 (7)	0.0202 (6)	0.0346 (8)	0.0014 (5)	0.0020 (6)	0.0008 (6)
C22B	0.0283 (9)	0.0235 (8)	0.0554 (12)	0.0028 (7)	−0.0044 (8)	0.0035 (8)
C23B	0.0382 (10)	0.0311 (9)	0.0341 (9)	0.0012 (8)	−0.0038 (8)	−0.0016 (8)

Geometric parameters (Å, º)

S1A—C5A	1.7537 (16)	S1B—C5B	1.7522 (16)
S1A—C2A	1.7791 (16)	S1B—C2B	1.7790 (16)
C2A—O6A	1.2347 (19)	C2B—O6B	1.232 (2)
C2A—N3A	1.353 (2)	C2B—N3B	1.356 (2)
N3A—C4A	1.340 (2)	N3B—C4B	1.338 (2)
C4A—N7A	1.354 (2)	C4B—N7B	1.356 (2)
C4A—C5A	1.4413 (19)	C4B—C5B	1.4416 (19)
C5A—C15A	1.372 (2)	C5B—C15B	1.371 (2)
N7A—C8A	1.4125 (19)	N7B—C8B	1.4127 (18)
N7A—H7A	0.86 (2)	N7B—H7B	0.87 (2)
C8A—C9A	1.391 (2)	C8B—C9B	1.390 (2)
C8A—C13A	1.396 (2)	C8B—C13B	1.402 (2)
C9A—C10A	1.397 (2)	C9B—C10B	1.399 (2)
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—O14A	1.365 (2)	C10B—O14B	1.3610 (19)
C10A—C11A	1.386 (2)	C10B—C11B	1.393 (2)
C11A—C12A	1.392 (2)	C11B—C12B	1.388 (2)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.384 (2)	C12B—C13B	1.386 (2)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
O14A—H14A	0.86 (3)	O14B—H14B	0.82 (3)
C15A—N16A	1.336 (2)	C15B—N16B	1.339 (2)
C15A—H15A	0.9500	C15B—H15B	0.9500
N16A—C18A	1.457 (2)	N16B—C18B	1.456 (2)
N16A—C17A	1.461 (2)	N16B—C17B	1.457 (2)
C17A—H17A	0.9800	C17B—H17D	0.9800
C17A—H17B	0.9800	C17B—H17E	0.9800
C17A—H17C	0.9800	C17B—H17F	0.9800
C18A—H18A	0.9800	C18B—H18D	0.9800
C18A—H18B	0.9800	C18B—H18E	0.9800
C18A—H18C	0.9800	C18B—H18F	0.9800
O19A—C20A	1.228 (2)	O19B—C20B	1.226 (2)
C20A—N21A	1.328 (2)	C20B—N21B	1.326 (2)
C20A—H20A	0.9500	C20B—H20B	0.9500
N21A—C22A	1.449 (2)	N21B—C22B	1.445 (2)
N21A—C23A	1.455 (2)	N21B—C23B	1.449 (2)
C22A—H22A	0.9800	C22B—H22D	0.9800
C22A—H22B	0.9800	C22B—H22E	0.9800
C22A—H22C	0.9800	C22B—H22F	0.9800
C23A—H23A	0.9800	C23B—H23D	0.9800
C23A—H23B	0.9800	C23B—H23E	0.9800
C23A—H23C	0.9800	C23B—H23F	0.9800
C5A—S1A—C2A	90.07 (7)	C5B—S1B—C2B	90.18 (7)
O6A—C2A—N3A	126.65 (15)	O6B—C2B—N3B	126.66 (14)
O6A—C2A—S1A	119.83 (12)	O6B—C2B—S1B	119.94 (12)
N3A—C2A—S1A	113.52 (11)	N3B—C2B—S1B	113.39 (11)
C4A—N3A—C2A	111.50 (13)	C4B—N3B—C2B	111.45 (12)
N3A—C4A—N7A	121.14 (13)	N3B—C4B—N7B	121.16 (13)
N3A—C4A—C5A	117.43 (14)	N3B—C4B—C5B	117.54 (14)
N7A—C4A—C5A	121.43 (14)	N7B—C4B—C5B	121.30 (14)
C15A—C5A—C4A	124.31 (14)	C15B—C5B—C4B	124.31 (14)
C15A—C5A—S1A	127.90 (12)	C15B—C5B—S1B	127.99 (12)
C4A—C5A—S1A	107.48 (11)	C4B—C5B—S1B	107.44 (11)
C4A—N7A—C8A	129.98 (13)	C4B—N7B—C8B	129.61 (13)
C4A—N7A—H7A	117.8 (15)	C4B—N7B—H7B	118.2 (15)
C8A—N7A—H7A	111.9 (15)	C8B—N7B—H7B	111.8 (15)
C9A—C8A—C13A	120.00 (14)	C9B—C8B—C13B	119.85 (14)
C9A—C8A—N7A	124.19 (14)	C9B—C8B—N7B	124.22 (14)
C13A—C8A—N7A	115.79 (13)	C13B—C8B—N7B	115.91 (13)
C8A—C9A—C10A	119.02 (14)	C8B—C9B—C10B	119.45 (14)
C8A—C9A—H9A	120.5	C8B—C9B—H9B	120.3
C10A—C9A—H9A	120.5	C10B—C9B—H9B	120.3
O14A—C10A—C11A	122.01 (14)	O14B—C10B—C11B	122.13 (14)
O14A—C10A—C9A	116.49 (14)	O14B—C10B—C9B	116.82 (14)
C11A—C10A—C9A	121.48 (15)	C11B—C10B—C9B	121.05 (14)
C10A—C11A—C12A	118.63 (14)	C12B—C11B—C10B	118.69 (14)
C10A—C11A—H11A	120.7	C12B—C11B—H11B	120.7
C12A—C11A—H11A	120.7	C10B—C11B—H11B	120.7
C13A—C12A—C11A	120.88 (15)	C13B—C12B—C11B	121.22 (15)
C13A—C12A—H12A	119.6	C13B—C12B—H12B	119.4
C11A—C12A—H12A	119.6	C11B—C12B—H12B	119.4
C12A—C13A—C8A	119.99 (15)	C12B—C13B—C8B	119.73 (15)
C12A—C13A—H13A	120.0	C12B—C13B—H13B	120.1
C8A—C13A—H13A	120.0	C8B—C13B—H13B	120.1
C10A—O14A—H14A	112.3 (18)	C10B—O14B—H14B	109.9 (18)
N16A—C15A—C5A	129.95 (15)	N16B—C15B—C5B	129.64 (15)
N16A—C15A—H15A	115.0	N16B—C15B—H15B	115.2
C5A—C15A—H15A	115.0	C5B—C15B—H15B	115.2
C15A—N16A—C18A	124.50 (14)	C15B—N16B—C18B	124.37 (14)
C15A—N16A—C17A	119.53 (14)	C15B—N16B—C17B	119.69 (14)
C18A—N16A—C17A	115.95 (13)	C18B—N16B—C17B	115.94 (13)
N16A—C17A—H17A	109.5	N16B—C17B—H17D	109.5
N16A—C17A—H17B	109.5	N16B—C17B—H17E	109.5
H17A—C17A—H17B	109.5	H17D—C17B—H17E	109.5
N16A—C17A—H17C	109.5	N16B—C17B—H17F	109.5
H17A—C17A—H17C	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17C	109.5	H17E—C17B—H17F	109.5
N16A—C18A—H18A	109.5	N16B—C18B—H18D	109.5
N16A—C18A—H18B	109.5	N16B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
N16A—C18A—H18C	109.5	N16B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
O19A—C20A—N21A	125.53 (17)	O19B—C20B—N21B	126.26 (18)
O19A—C20A—H20A	117.2	O19B—C20B—H20B	116.9
N21A—C20A—H20A	117.2	N21B—C20B—H20B	116.9
C20A—N21A—C22A	122.09 (16)	C20B—N21B—C22B	121.95 (16)
C20A—N21A—C23A	120.28 (15)	C20B—N21B—C23B	120.95 (15)
C22A—N21A—C23A	117.60 (15)	C22B—N21B—C23B	117.07 (15)
N21A—C22A—H22A	109.5	N21B—C22B—H22D	109.5
N21A—C22A—H22B	109.5	N21B—C22B—H22E	109.5
H22A—C22A—H22B	109.5	H22D—C22B—H22E	109.5
N21A—C22A—H22C	109.5	N21B—C22B—H22F	109.5
H22A—C22A—H22C	109.5	H22D—C22B—H22F	109.5
H22B—C22A—H22C	109.5	H22E—C22B—H22F	109.5
N21A—C23A—H23A	109.5	N21B—C23B—H23D	109.5
N21A—C23A—H23B	109.5	N21B—C23B—H23E	109.5
H23A—C23A—H23B	109.5	H23D—C23B—H23E	109.5
N21A—C23A—H23C	109.5	N21B—C23B—H23F	109.5
H23A—C23A—H23C	109.5	H23D—C23B—H23F	109.5
H23B—C23A—H23C	109.5	H23E—C23B—H23F	109.5
C5A—S1A—C2A—O6A	179.41 (15)	C5B—S1B—C2B—O6B	179.18 (15)
C5A—S1A—C2A—N3A	−0.44 (12)	C5B—S1B—C2B—N3B	0.09 (13)
O6A—C2A—N3A—C4A	−179.65 (16)	O6B—C2B—N3B—C4B	−178.54 (17)
S1A—C2A—N3A—C4A	0.19 (17)	S1B—C2B—N3B—C4B	0.47 (17)
C2A—N3A—C4A—N7A	180.00 (14)	C2B—N3B—C4B—N7B	179.16 (14)
C2A—N3A—C4A—C5A	0.26 (19)	C2B—N3B—C4B—C5B	−1.0 (2)
N3A—C4A—C5A—C15A	173.41 (15)	N3B—C4B—C5B—C15B	−173.55 (15)
N7A—C4A—C5A—C15A	−6.3 (2)	N7B—C4B—C5B—C15B	6.3 (2)
N3A—C4A—C5A—S1A	−0.58 (17)	N3B—C4B—C5B—S1B	1.02 (17)
N7A—C4A—C5A—S1A	179.68 (12)	N7B—C4B—C5B—S1B	−179.12 (12)
C2A—S1A—C5A—C15A	−173.17 (15)	C2B—S1B—C5B—C15B	173.73 (15)
C2A—S1A—C5A—C4A	0.53 (11)	C2B—S1B—C5B—C4B	−0.57 (11)
N3A—C4A—N7A—C8A	−4.7 (3)	N3B—C4B—N7B—C8B	6.7 (2)
C5A—C4A—N7A—C8A	175.02 (15)	C5B—C4B—N7B—C8B	−173.19 (15)
C4A—N7A—C8A—C9A	15.2 (3)	C4B—N7B—C8B—C9B	−21.5 (3)
C4A—N7A—C8A—C13A	−166.46 (16)	C4B—N7B—C8B—C13B	160.15 (16)
C13A—C8A—C9A—C10A	0.2 (2)	C13B—C8B—C9B—C10B	0.2 (2)
N7A—C8A—C9A—C10A	178.57 (15)	N7B—C8B—C9B—C10B	−178.11 (15)
C8A—C9A—C10A—O14A	−178.60 (15)	C8B—C9B—C10B—O14B	178.40 (15)
C8A—C9A—C10A—C11A	−0.2 (3)	C8B—C9B—C10B—C11B	−1.0 (2)
O14A—C10A—C11A—C12A	178.12 (17)	O14B—C10B—C11B—C12B	−178.19 (16)
C9A—C10A—C11A—C12A	−0.2 (3)	C9B—C10B—C11B—C12B	1.2 (2)
C10A—C11A—C12A—C13A	0.6 (3)	C10B—C11B—C12B—C13B	−0.5 (3)
C11A—C12A—C13A—C8A	−0.5 (3)	C11B—C12B—C13B—C8B	−0.3 (3)
C9A—C8A—C13A—C12A	0.1 (3)	C9B—C8B—C13B—C12B	0.5 (2)
N7A—C8A—C13A—C12A	−178.39 (16)	N7B—C8B—C13B—C12B	178.88 (15)
C4A—C5A—C15A—N16A	176.26 (16)	C4B—C5B—C15B—N16B	−177.34 (16)
S1A—C5A—C15A—N16A	−11.0 (3)	S1B—C5B—C15B—N16B	9.2 (3)
C5A—C15A—N16A—C18A	−8.6 (3)	C5B—C15B—N16B—C18B	8.6 (3)
C5A—C15A—N16A—C17A	169.67 (16)	C5B—C15B—N16B—C17B	−170.98 (16)
O19A—C20A—N21A—C22A	174.32 (18)	O19B—C20B—N21B—C22B	179.24 (19)
O19A—C20A—N21A—C23A	−3.7 (3)	O19B—C20B—N21B—C23B	−3.0 (3)

5-dimethylaminomethylidene-4-(4-hydroxyphenyl)amino-1,3-thiazol-2(5H)-one dimethylformamide solvate (3.DMF)

Crystal data

C12H13N3O2S·C3H7NO	Dx = 1.379 Mg m^−3
Mr = 336.41	Melting point = 553–554 K
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.1630 (2) Å	Cell parameters from 8581 reflections
b = 17.0311 (3) Å	θ = 3.3–76.0°
c = 7.3212 (1) Å	µ = 1.96 mm^−1
β = 99.213 (2)°	T = 130 K
V = 1620.10 (4) Å^3	Rod, yellow
Z = 4	0.22 × 0.11 × 0.06 mm
F(000) = 712

Data collection

SuperNova, Dual, Cu, Atlas diffractometer	3380 independent reflections
Radiation source: micro-focus sealed X-ray tube	3123 reflections with I > 2σ(I)
Detector resolution: 10.3991 pixels mm^-1	Rint = 0.027
ω scans	θmax = 76.4°, θmin = 3.4°
Absorption correction: multi-scan CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −16→16
Tmin = 0.772, Tmax = 1.000	k = −21→21
17034 measured reflections	l = −8→9

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: mixed
wR(F^2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0473P)^2 + 0.6126P] where P = (Fo^2 + 2Fc^2)/3
3380 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.27 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.

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

	x	y	z	Uiso*/Ueq
S1	0.06894 (2)	0.07491 (2)	0.10480 (4)	0.02061 (10)
C2	0.18184 (9)	0.01845 (7)	0.18246 (16)	0.0188 (2)
N3	0.26427 (8)	0.06231 (6)	0.25336 (14)	0.0180 (2)
C4	0.24213 (9)	0.13915 (7)	0.24804 (16)	0.0168 (2)
C5	0.13758 (9)	0.16154 (7)	0.17325 (17)	0.0180 (2)
O6	0.17947 (7)	−0.05377 (5)	0.16760 (13)	0.0236 (2)
N7	0.31564 (8)	0.19212 (6)	0.30740 (15)	0.0192 (2)
H7	0.3001 (13)	0.2406 (11)	0.292 (2)	0.029 (4)*
C8	0.42068 (9)	0.17759 (7)	0.38146 (16)	0.0169 (2)
C9	0.49065 (9)	0.23623 (7)	0.35396 (17)	0.0191 (2)
H9	0.467579	0.280817	0.280951	0.023*
C10	0.59328 (9)	0.23017 (7)	0.43185 (17)	0.0198 (2)
H10	0.640133	0.270578	0.412366	0.024*
C11	0.62801 (9)	0.16516 (7)	0.53848 (17)	0.0177 (2)
C12	0.55942 (9)	0.10534 (7)	0.56223 (16)	0.0172 (2)
H12	0.583336	0.059978	0.631557	0.021*
C13	0.45577 (9)	0.11147 (7)	0.48502 (16)	0.0173 (2)
H13	0.409152	0.070667	0.502944	0.021*
O14	0.72931 (7)	0.16386 (6)	0.61536 (14)	0.0236 (2)
H14	0.7448 (16)	0.1205 (13)	0.682 (3)	0.046 (5)*
C15	0.10348 (9)	0.23773 (7)	0.15785 (17)	0.0194 (2)
H15	0.154477	0.276025	0.199184	0.023*
N16	0.01038 (8)	0.26691 (6)	0.09430 (16)	0.0220 (2)
C17	−0.00242 (11)	0.35206 (8)	0.0797 (2)	0.0267 (3)
H17A	0.058890	0.377937	0.146877	0.040*
H17B	−0.062962	0.367784	0.133187	0.040*
H17C	−0.011756	0.367540	−0.050875	0.040*
C18	−0.07978 (10)	0.22009 (8)	0.0224 (2)	0.0260 (3)
H18A	−0.071538	0.198082	−0.098026	0.039*
H18B	−0.141276	0.253374	0.008069	0.039*
H18C	−0.087192	0.177309	0.108830	0.039*
O19	0.27659 (8)	0.36176 (6)	0.28307 (15)	0.0292 (2)
C20	0.32714 (10)	0.41738 (8)	0.35709 (19)	0.0241 (3)
H20	0.385717	0.405601	0.446601	0.029*
N21	0.30586 (9)	0.49258 (6)	0.32109 (15)	0.0236 (2)
C22	0.21470 (12)	0.51516 (8)	0.1921 (2)	0.0299 (3)
H22A	0.196584	0.473153	0.101258	0.045*
H22B	0.228752	0.563540	0.128132	0.045*
H22C	0.157353	0.523995	0.260098	0.045*
C23	0.36688 (12)	0.55502 (9)	0.4202 (2)	0.0325 (3)
H23A	0.321960	0.589566	0.478727	0.049*
H23B	0.400530	0.585450	0.333280	0.049*
H23C	0.419275	0.532092	0.515502	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01601 (16)	0.01581 (16)	0.02832 (18)	−0.00011 (10)	−0.00163 (12)	−0.00228 (11)
C2	0.0185 (6)	0.0179 (6)	0.0192 (6)	0.0001 (5)	0.0007 (4)	0.0003 (4)
N3	0.0175 (5)	0.0145 (5)	0.0212 (5)	−0.0007 (4)	0.0003 (4)	0.0001 (4)
C4	0.0176 (6)	0.0159 (5)	0.0170 (5)	0.0003 (4)	0.0028 (4)	0.0000 (4)
C5	0.0158 (6)	0.0171 (6)	0.0206 (6)	−0.0003 (4)	0.0013 (4)	−0.0015 (4)
O6	0.0232 (5)	0.0142 (4)	0.0309 (5)	−0.0011 (3)	−0.0034 (4)	0.0001 (4)
N7	0.0163 (5)	0.0122 (5)	0.0274 (5)	0.0005 (4)	−0.0020 (4)	0.0011 (4)
C8	0.0164 (6)	0.0146 (5)	0.0188 (6)	0.0003 (4)	0.0006 (4)	−0.0012 (4)
C9	0.0212 (6)	0.0141 (5)	0.0214 (6)	0.0000 (5)	0.0016 (5)	0.0028 (4)
C10	0.0197 (6)	0.0159 (6)	0.0238 (6)	−0.0029 (5)	0.0036 (5)	0.0015 (5)
C11	0.0159 (6)	0.0169 (6)	0.0201 (6)	0.0015 (4)	0.0020 (4)	−0.0026 (4)
C12	0.0204 (6)	0.0122 (5)	0.0185 (5)	0.0014 (4)	0.0013 (4)	0.0001 (4)
C13	0.0191 (6)	0.0132 (5)	0.0194 (6)	−0.0024 (4)	0.0023 (4)	−0.0009 (4)
O14	0.0151 (4)	0.0201 (4)	0.0339 (5)	−0.0007 (3)	−0.0015 (4)	0.0041 (4)
C15	0.0170 (5)	0.0189 (6)	0.0219 (6)	0.0000 (5)	0.0021 (4)	−0.0014 (5)
N16	0.0174 (5)	0.0177 (5)	0.0300 (6)	0.0029 (4)	0.0007 (4)	−0.0005 (4)
C17	0.0236 (6)	0.0185 (6)	0.0372 (7)	0.0048 (5)	0.0032 (5)	0.0020 (5)
C18	0.0184 (6)	0.0240 (6)	0.0339 (7)	0.0019 (5)	−0.0011 (5)	−0.0039 (5)
O19	0.0271 (5)	0.0174 (4)	0.0434 (6)	−0.0022 (4)	0.0060 (4)	−0.0018 (4)
C20	0.0228 (6)	0.0209 (6)	0.0295 (7)	−0.0003 (5)	0.0073 (5)	0.0009 (5)
N21	0.0280 (6)	0.0181 (5)	0.0252 (5)	−0.0024 (4)	0.0063 (4)	−0.0008 (4)
C22	0.0355 (8)	0.0246 (7)	0.0292 (7)	0.0017 (6)	0.0038 (6)	0.0045 (6)
C23	0.0391 (8)	0.0237 (7)	0.0359 (8)	−0.0097 (6)	0.0097 (6)	−0.0064 (6)

Geometric parameters (Å, º)

S1—C5	1.7606 (12)	C15—N16	1.3350 (16)
S1—C2	1.7849 (12)	C15—H15	0.9500
C2—O6	1.2347 (15)	N16—C18	1.4565 (16)
C2—N3	1.3508 (16)	N16—C17	1.4619 (16)
N3—C4	1.3399 (15)	C17—H17A	0.9800
C4—N7	1.3432 (16)	C17—H17B	0.9800
C4—C5	1.4484 (16)	C17—H17C	0.9800
C5—C15	1.3718 (17)	C18—H18A	0.9800
N7—C8	1.4236 (15)	C18—H18B	0.9800
N7—H7	0.853 (18)	C18—H18C	0.9800
C8—C13	1.3943 (17)	O19—C20	1.2322 (17)
C8—C9	1.3948 (17)	C20—N21	1.3283 (17)
C9—C10	1.3836 (17)	C20—H20	0.9500
C9—H9	0.9500	N21—C23	1.4547 (17)
C10—C11	1.3893 (17)	N21—C22	1.4548 (18)
C10—H10	0.9500	C22—H22A	0.9800
C11—O14	1.3619 (15)	C22—H22B	0.9800
C11—C12	1.3905 (17)	C22—H22C	0.9800
C12—C13	1.3946 (17)	C23—H23A	0.9800
C12—H12	0.9500	C23—H23B	0.9800
C13—H13	0.9500	C23—H23C	0.9800
O14—H14	0.89 (2)
C5—S1—C2	89.87 (6)	C5—C15—H15	114.7
O6—C2—N3	126.31 (11)	C15—N16—C18	124.85 (11)
O6—C2—S1	120.04 (9)	C15—N16—C17	118.90 (11)
N3—C2—S1	113.65 (9)	C18—N16—C17	116.04 (10)
C4—N3—C2	111.80 (10)	N16—C17—H17A	109.5
N3—C4—N7	120.30 (11)	N16—C17—H17B	109.5
N3—C4—C5	117.21 (11)	H17A—C17—H17B	109.5
N7—C4—C5	122.48 (11)	N16—C17—H17C	109.5
C15—C5—C4	123.97 (11)	H17A—C17—H17C	109.5
C15—C5—S1	128.54 (10)	H17B—C17—H17C	109.5
C4—C5—S1	107.47 (9)	N16—C18—H18A	109.5
C4—N7—C8	127.73 (10)	N16—C18—H18B	109.5
C4—N7—H7	117.5 (12)	H18A—C18—H18B	109.5
C8—N7—H7	114.6 (12)	N16—C18—H18C	109.5
C13—C8—C9	119.20 (11)	H18A—C18—H18C	109.5
C13—C8—N7	124.36 (11)	H18B—C18—H18C	109.5
C9—C8—N7	116.36 (11)	O19—C20—N21	124.90 (13)
C10—C9—C8	120.72 (11)	O19—C20—H20	117.6
C10—C9—H9	119.6	N21—C20—H20	117.6
C8—C9—H9	119.6	C20—N21—C23	121.58 (12)
C9—C10—C11	120.19 (11)	C20—N21—C22	120.63 (12)
C9—C10—H10	119.9	C23—N21—C22	117.57 (12)
C11—C10—H10	119.9	N21—C22—H22A	109.5
O14—C11—C10	117.23 (11)	N21—C22—H22B	109.5
O14—C11—C12	123.28 (11)	H22A—C22—H22B	109.5
C10—C11—C12	119.49 (11)	N21—C22—H22C	109.5
C11—C12—C13	120.47 (11)	H22A—C22—H22C	109.5
C11—C12—H12	119.8	H22B—C22—H22C	109.5
C13—C12—H12	119.8	N21—C23—H23A	109.5
C8—C13—C12	119.89 (11)	N21—C23—H23B	109.5
C8—C13—H13	120.1	H23A—C23—H23B	109.5
C12—C13—H13	120.1	N21—C23—H23C	109.5
C11—O14—H14	111.3 (13)	H23A—C23—H23C	109.5
N16—C15—C5	130.60 (12)	H23B—C23—H23C	109.5
N16—C15—H15	114.7
C5—S1—C2—O6	−179.87 (11)	C13—C8—C9—C10	−1.57 (18)
C5—S1—C2—N3	−0.24 (10)	N7—C8—C9—C10	175.38 (11)
O6—C2—N3—C4	179.26 (12)	C8—C9—C10—C11	0.17 (19)
S1—C2—N3—C4	−0.34 (13)	C9—C10—C11—O14	−178.22 (11)
C2—N3—C4—N7	−177.91 (11)	C9—C10—C11—C12	1.68 (18)
C2—N3—C4—C5	0.95 (15)	O14—C11—C12—C13	177.77 (11)
N3—C4—C5—C15	−179.62 (12)	C10—C11—C12—C13	−2.12 (18)
N7—C4—C5—C15	−0.79 (19)	C9—C8—C13—C12	1.12 (18)
N3—C4—C5—S1	−1.10 (13)	N7—C8—C13—C12	−175.57 (11)
N7—C4—C5—S1	177.73 (10)	C11—C12—C13—C8	0.72 (18)
C2—S1—C5—C15	179.13 (12)	C4—C5—C15—N16	−179.26 (12)
C2—S1—C5—C4	0.69 (9)	S1—C5—C15—N16	2.5 (2)
N3—C4—N7—C8	−0.53 (19)	C5—C15—N16—C18	−0.4 (2)
C5—C4—N7—C8	−179.33 (11)	C5—C15—N16—C17	−175.02 (13)
C4—N7—C8—C13	−32.10 (19)	O19—C20—N21—C23	177.34 (13)
C4—N7—C8—C9	151.12 (12)	O19—C20—N21—C22	2.9 (2)