Di­hydro­oxazolones and di­hydro­imidazolo­nes derived from acyl­glycines: syntheses, mol­ecular structures and supra­molecular assembly

Syntheses and structures are described for some alkyl­idene-substituted di­­hydro­oxazolones and di­hydro­imidazoles derived from simple acyl­glycines. A second, triclinic, polymorph of 4-benzyl­idene-2-(4-methyl­phen­yl)-1,3-oxazol-5(4H)-one, C₁₇H₁₃NO₂, (I), has been identified and the structure of 2-methyl-4-[(thio­phen-2-yl)methyl­idene]-1,3-oxazol-5(4H)-one, C₉H₇NO₂S, (II), has been rerefined taking into account the orientational disorder of the thienyl group in each of the two independent mol­ecules. The reactions of phenyl­hydrazine with 2-phenyl-4-[(thio­phen-2-yl)methyl­idene]-1,3-oxazol-5(4H)-one or 2-(4-methyl­phen­yl)-4-[(thio­phen-2-yl)methyl­idene]-1,3-oxazol-5(4H)-one yield, respectively, 3-anilino-2-phenyl-5-[(thio­phen-2-yl)methyl­idene]-3,5-di­hydro-4H-imid­azol-4-one, C₁₀H₁₅N₃OS, (III), and 3-anilino-2-(4-methyl­phen­yl)-5-[(thio­phen-2-yl)methyl­idene]-3,5-di­hydro-4H-imidazol-4-one, C₂₁H₁₇N₃OS, (IV), which both exhibit orientational disorder in their thienyl groups. The reactions of 2-phenyl-4-[(thio­phen-2-yl)methyl­idene]-1,3-oxazol-5(4H)-one with hydrazine hydrate or with water yield, respectively, N-[3-hydrazinyl-3-oxo-1-(thio­phen-2-yl)prop-1-en-2-yl]benzamide and 2-(benzoyl­amino)-3-(thio­phen-2-yl)prop-2-enoic acid, which in turn react, respectively, with thio­phene-2-carbaldehyde to form 2-phenyl-5-[(thio­phen-2-yl)methyl­idene]-3-{[(E)-(thio­phen-2-yl)methyl­idene]­amino}-3,5-di­hydro-4H-imidazol-4-one, C₁₉H₁₃N₃OS₂, (V), which exhibits orientational disorder in only one of its thienyl groups, and with methanol to give methyl (2Z)-2-(benzoyl­amino)-3-(thio­phen-2-yl)prop-2-enoate, C₁₅H₁₃NO₃S, (VI). There are no direction-specific inter­molecular inter­actions in the crystal structure of the triclinic polymorph of (I), but the mol­ecules of (II) are linked by two independent C-H...O hydrogen bonds to form C₂²(14) chains. Compounds (III) and (IV) both form centrosymmetric R₂²(10) dimers built from N-H...O hydrogen bonds, while compound (V) forms a centrosymmetric R₂²(10) dimer built from C-H...O hydrogen bonds. In the structure of compound (VI), a combination of N-H...O and C-H...[pi](arene) hydrogen bonds links the mol­ecules into sheets. Comparisons are made with some similar compounds.

Computing details

For all compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I) 4-Benzylidene-2-(4-methylphenyl)-1,3-oxazol-5(4H)-one

Crystal data

C17H13NO2	Z = 2
Mr = 263.28	F(000) = 276
Triclinic, P1	Dx = 1.304 Mg m^−3
a = 7.9940 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0648 (4) Å	Cell parameters from 3867 reflections
c = 10.7692 (6) Å	θ = 2.2–30.6°
α = 109.136 (4)°	µ = 0.09 mm^−1
β = 109.397 (4)°	T = 296 K
γ = 97.320 (4)°	Block, yellow
V = 670.52 (6) Å^3	0.20 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer	1604 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.043
Graphite monochromator	θmax = 26.6°, θmin = 2.2°
φ and ω scans	h = −10→10
10476 measured reflections	k = −11→11
2677 independent reflections	l = −13→13

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.0761P)^2 + 0.0683P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2677 reflections	Δρmax = 0.16 e Å^−3
182 parameters	Δρmin = −0.21 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.

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

	x	y	z	Uiso*/Ueq
O1	0.70957 (17)	0.40830 (15)	0.36192 (16)	0.0593 (4)
C2	0.6065 (3)	0.5197 (2)	0.3523 (2)	0.0505 (5)
N3	0.4795 (2)	0.48433 (17)	0.22867 (19)	0.0521 (5)
C4	0.4878 (3)	0.3349 (2)	0.1400 (2)	0.0498 (5)
C5	0.6352 (3)	0.2843 (2)	0.2259 (2)	0.0571 (6)
O51	0.6940 (2)	0.16734 (17)	0.19946 (18)	0.0769 (5)
C21	0.6518 (3)	0.6603 (2)	0.4828 (2)	0.0506 (5)
C22	0.8097 (3)	0.6992 (2)	0.6047 (3)	0.0640 (6)
H22	0.8910	0.6344	0.6043	0.077*
C23	0.8463 (3)	0.8339 (3)	0.7263 (3)	0.0694 (7)
H23	0.9528	0.8585	0.8072	0.083*
C24	0.7297 (3)	0.9332 (2)	0.7316 (2)	0.0610 (6)
C25	0.5731 (3)	0.8932 (3)	0.6093 (3)	0.0686 (7)
H25	0.4915	0.9576	0.6100	0.082*
C26	0.5354 (3)	0.7603 (2)	0.4867 (2)	0.0631 (6)
H26	0.4301	0.7373	0.4054	0.076*
C27	0.7713 (3)	1.0800 (3)	0.8651 (3)	0.0835 (8)
H27A	0.9011	1.1308	0.9102	0.125*
H27B	0.7329	1.0478	0.9301	0.125*
H27C	0.7063	1.1551	0.8403	0.125*
C47	0.3884 (3)	0.2493 (2)	−0.0013 (2)	0.0525 (5)
H47	0.4138	0.1510	−0.0395	0.063*
C41	0.2476 (2)	0.2869 (2)	−0.1029 (2)	0.0497 (5)
C42	0.1943 (3)	0.4306 (2)	−0.0667 (2)	0.0588 (6)
H42	0.2483	0.5073	0.0272	0.071*
C43	0.0620 (3)	0.4589 (3)	−0.1697 (3)	0.0688 (7)
H43	0.0268	0.5547	−0.1446	0.083*
C44	−0.0188 (3)	0.3478 (3)	−0.3093 (3)	0.0705 (7)
H44	−0.1075	0.3686	−0.3782	0.085*
C45	0.0319 (3)	0.2058 (3)	−0.3466 (3)	0.0724 (7)
H45	−0.0231	0.1298	−0.4408	0.087*
C46	0.1641 (3)	0.1761 (2)	−0.2448 (2)	0.0616 (6)
H46	0.1983	0.0800	−0.2712	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0652 (8)	0.0530 (8)	0.0530 (10)	0.0193 (6)	0.0151 (7)	0.0203 (7)
C2	0.0557 (11)	0.0453 (10)	0.0510 (14)	0.0127 (8)	0.0189 (10)	0.0223 (10)
N3	0.0572 (9)	0.0476 (9)	0.0458 (12)	0.0134 (7)	0.0154 (9)	0.0169 (8)
C4	0.0553 (10)	0.0444 (10)	0.0512 (14)	0.0145 (8)	0.0225 (10)	0.0189 (10)
C5	0.0609 (12)	0.0518 (11)	0.0528 (15)	0.0142 (9)	0.0203 (11)	0.0163 (10)
O51	0.0874 (10)	0.0625 (9)	0.0763 (13)	0.0387 (8)	0.0253 (9)	0.0226 (9)
C21	0.0559 (11)	0.0461 (10)	0.0479 (14)	0.0108 (8)	0.0186 (10)	0.0197 (10)
C22	0.0701 (13)	0.0583 (12)	0.0551 (16)	0.0209 (10)	0.0151 (12)	0.0210 (11)
C23	0.0726 (13)	0.0659 (13)	0.0496 (16)	0.0127 (11)	0.0085 (11)	0.0167 (12)
C24	0.0724 (14)	0.0551 (11)	0.0496 (15)	0.0060 (10)	0.0262 (12)	0.0160 (10)
C25	0.0724 (14)	0.0641 (13)	0.0654 (17)	0.0230 (11)	0.0273 (13)	0.0192 (12)
C26	0.0596 (12)	0.0622 (12)	0.0503 (15)	0.0141 (10)	0.0116 (11)	0.0129 (11)
C27	0.0981 (18)	0.0723 (15)	0.0578 (18)	0.0059 (13)	0.0320 (15)	0.0044 (13)
C47	0.0583 (11)	0.0435 (10)	0.0524 (15)	0.0128 (8)	0.0234 (11)	0.0141 (10)
C41	0.0510 (10)	0.0472 (10)	0.0471 (14)	0.0094 (8)	0.0190 (9)	0.0159 (9)
C42	0.0680 (12)	0.0519 (11)	0.0491 (15)	0.0159 (10)	0.0180 (11)	0.0163 (10)
C43	0.0787 (14)	0.0605 (13)	0.0659 (18)	0.0239 (11)	0.0233 (13)	0.0269 (13)
C44	0.0684 (13)	0.0759 (15)	0.0623 (18)	0.0145 (11)	0.0135 (12)	0.0360 (13)
C45	0.0837 (15)	0.0652 (14)	0.0479 (15)	0.0101 (12)	0.0119 (12)	0.0161 (12)
C46	0.0682 (13)	0.0528 (11)	0.0501 (15)	0.0139 (10)	0.0164 (11)	0.0120 (11)

Geometric parameters (Å, º)

O1—C2	1.391 (2)	C26—H26	0.9300
O1—C5	1.391 (2)	C27—H27A	0.9600
C2—N3	1.283 (2)	C27—H27B	0.9600
C2—C21	1.449 (3)	C27—H27C	0.9600
N3—C4	1.403 (2)	C47—C41	1.451 (3)
C4—C47	1.346 (3)	C47—H47	0.9300
C4—C5	1.465 (3)	C41—C46	1.391 (3)
C5—O51	1.202 (2)	C41—C42	1.396 (3)
C21—C26	1.380 (3)	C42—C43	1.376 (3)
C21—C22	1.387 (3)	C42—H42	0.9300
C22—C23	1.378 (3)	C43—C44	1.374 (3)
C22—H22	0.9300	C43—H43	0.9300
C23—C24	1.377 (3)	C44—C45	1.373 (3)
C23—H23	0.9300	C44—H44	0.9300
C24—C25	1.382 (3)	C45—C46	1.374 (3)
C24—C27	1.505 (3)	C45—H45	0.9300
C25—C26	1.373 (3)	C46—H46	0.9300
C25—H25	0.9300
C2—O1—C5	105.27 (15)	C21—C26—H26	119.6
N3—C2—O1	115.84 (17)	C24—C27—H27A	109.5
N3—C2—C21	127.46 (17)	C24—C27—H27B	109.5
O1—C2—C21	116.69 (18)	H27A—C27—H27B	109.5
C2—N3—C4	105.54 (16)	C24—C27—H27C	109.5
C47—C4—N3	128.79 (18)	H27A—C27—H27C	109.5
C47—C4—C5	122.91 (18)	H27B—C27—H27C	109.5
N3—C4—C5	108.24 (18)	C4—C47—C41	129.84 (18)
O51—C5—O1	121.5 (2)	C4—C47—H47	115.1
O51—C5—C4	133.4 (2)	C41—C47—H47	115.1
O1—C5—C4	105.09 (16)	C46—C41—C42	118.0 (2)
C26—C21—C22	118.38 (19)	C46—C41—C47	118.48 (18)
C26—C21—C2	119.35 (18)	C42—C41—C47	123.49 (19)
C22—C21—C2	122.26 (18)	C43—C42—C41	120.1 (2)
C23—C22—C21	120.1 (2)	C43—C42—H42	120.0
C23—C22—H22	120.0	C41—C42—H42	120.0
C21—C22—H22	120.0	C44—C43—C42	120.9 (2)
C24—C23—C22	121.9 (2)	C44—C43—H43	119.5
C24—C23—H23	119.1	C42—C43—H43	119.5
C22—C23—H23	119.1	C45—C44—C43	119.7 (2)
C23—C24—C25	117.4 (2)	C45—C44—H44	120.2
C23—C24—C27	121.4 (2)	C43—C44—H44	120.2
C25—C24—C27	121.2 (2)	C44—C45—C46	120.0 (2)
C26—C25—C24	121.4 (2)	C44—C45—H45	120.0
C26—C25—H25	119.3	C46—C45—H45	120.0
C24—C25—H25	119.3	C45—C46—C41	121.3 (2)
C25—C26—C21	120.8 (2)	C45—C46—H46	119.4
C25—C26—H26	119.6	C41—C46—H46	119.4
C5—O1—C2—N3	−1.0 (2)	C22—C23—C24—C25	−0.2 (4)
C5—O1—C2—C21	177.85 (16)	C22—C23—C24—C27	−180.0 (2)
O1—C2—N3—C4	0.5 (2)	C23—C24—C25—C26	−0.4 (3)
C21—C2—N3—C4	−178.25 (18)	C27—C24—C25—C26	179.4 (2)
C2—N3—C4—C47	−177.0 (2)	C24—C25—C26—C21	1.2 (4)
C2—N3—C4—C5	0.2 (2)	C22—C21—C26—C25	−1.3 (3)
C2—O1—C5—O51	−179.17 (19)	C2—C21—C26—C25	179.10 (19)
C2—O1—C5—C4	1.0 (2)	N3—C4—C47—C41	1.3 (4)
C47—C4—C5—O51	−3.2 (4)	C5—C4—C47—C41	−175.50 (18)
N3—C4—C5—O51	179.4 (2)	C4—C47—C41—C46	−179.7 (2)
C47—C4—C5—O1	176.57 (17)	C4—C47—C41—C42	1.9 (3)
N3—C4—C5—O1	−0.8 (2)	C46—C41—C42—C43	0.4 (3)
N3—C2—C21—C26	9.9 (3)	C47—C41—C42—C43	178.81 (19)
O1—C2—C21—C26	−168.84 (17)	C41—C42—C43—C44	−0.4 (3)
N3—C2—C21—C22	−169.7 (2)	C42—C43—C44—C45	0.5 (4)
O1—C2—C21—C22	11.6 (3)	C43—C44—C45—C46	−0.5 (4)
C26—C21—C22—C23	0.7 (3)	C44—C45—C46—C41	0.5 (4)
C2—C21—C22—C23	−179.7 (2)	C42—C41—C46—C45	−0.5 (3)
C21—C22—C23—C24	0.0 (4)	C47—C41—C46—C45	−179.0 (2)

(II) 2-Methyl-4-[(thiophen-2-yl)methylidene]-1,3-oxazol-5(4H)-one

Crystal data

C9H7NO2S	F(000) = 800
Mr = 193.22	Dx = 1.448 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.2264 (11) Å	Cell parameters from 4062 reflections
b = 9.8581 (7) Å	θ = 3.6–29.0°
c = 15.8735 (13) Å	µ = 0.33 mm^−1
β = 112.129 (10)°	T = 293 K
V = 1772.3 (3) Å^3	Block, colourless
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer	3916 independent reflections
Radiation source: sealed tube	2656 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −15→9
Tmin = 0.788, Tmax = 0.937	k = −12→11
7625 measured reflections	l = −20→19

Refinement

Refinement on F^2	26 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0443P)^2 + 0.0864P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3916 reflections	Δρmax = 0.19 e Å^−3
269 parameters	Δρmin = −0.21 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O11	0.45884 (13)	0.83638 (15)	0.00026 (10)	0.0577 (4)
C12	0.5109 (2)	0.7836 (2)	−0.05649 (15)	0.0514 (6)
N13	0.57969 (16)	0.68304 (18)	−0.02544 (12)	0.0489 (5)
C14	0.57965 (18)	0.6603 (2)	0.06207 (14)	0.0439 (5)
C15	0.50141 (19)	0.7585 (2)	0.07886 (16)	0.0511 (6)
O151	0.47253 (14)	0.77891 (18)	0.14172 (11)	0.0687 (5)
C121	0.4771 (2)	0.8499 (3)	−0.14588 (16)	0.0718 (7)
H121	0.5148	0.8044	−0.1812	0.108*
H122	0.5016	0.9431	−0.1376	0.108*
H123	0.3930	0.8454	−0.1771	0.108*
C146	0.64076 (19)	0.5661 (2)	0.12191 (14)	0.0455 (5)	0.974 (2)
H146	0.6310	0.5663	0.1772	0.055*	0.974 (2)
S141	0.74860 (5)	0.44227 (7)	0.01480 (4)	0.0492 (2)	0.974 (2)
C142	0.7189 (2)	0.4654 (2)	0.11224 (14)	0.0415 (5)	0.974 (2)
C143	0.7791 (4)	0.3751 (4)	0.1774 (2)	0.0561 (8)	0.974 (2)
H143	0.7744	0.3714	0.2344	0.067*	0.974 (2)
C144	0.8505 (2)	0.2865 (3)	0.14902 (17)	0.0589 (7)	0.974 (2)
H144	0.8979	0.2187	0.1855	0.071*	0.974 (2)
C145	0.8414 (2)	0.3120 (2)	0.06345 (16)	0.0548 (7)	0.974 (2)
H145	0.8818	0.2633	0.0341	0.066*	0.974 (2)
C346	0.64076 (19)	0.5661 (2)	0.12191 (14)	0.0455 (5)	0.026 (2)
H346	0.6342	0.5606	0.1783	0.055*	0.026 (2)
S341	0.803 (4)	0.353 (4)	0.174 (2)	0.0561 (8)	0.026 (2)
C342	0.716 (5)	0.474 (5)	0.0998 (19)	0.0415 (5)	0.026 (2)
C343	0.712 (7)	0.452 (6)	0.014 (2)	0.0492 (2)	0.026 (2)
H343	0.6828	0.5150	−0.0327	0.059*	0.026 (2)
C344	0.757 (6)	0.323 (5)	0.005 (3)	0.0548 (7)	0.026 (2)
H344	0.7449	0.2811	−0.0502	0.066*	0.026 (2)
C345	0.820 (7)	0.268 (5)	0.087 (3)	0.0589 (7)	0.026 (2)
H345	0.8681	0.1916	0.0944	0.071*	0.026 (2)
O21	0.61441 (14)	0.27829 (16)	0.36265 (9)	0.0560 (4)
C22	0.5544 (2)	0.2366 (2)	0.41703 (15)	0.0498 (5)
N23	0.57899 (16)	0.29992 (18)	0.49180 (11)	0.0465 (4)
C24	0.66416 (19)	0.3967 (2)	0.49388 (13)	0.0435 (5)
C25	0.6873 (2)	0.3832 (2)	0.41010 (15)	0.0526 (6)
O251	0.75112 (16)	0.44151 (18)	0.38069 (11)	0.0743 (6)
C221	0.4696 (2)	0.1256 (2)	0.37882 (16)	0.0659 (7)
H211	0.4011	0.1601	0.3304	0.099*
H212	0.4466	0.0882	0.4255	0.099*
H213	0.5057	0.0562	0.3556	0.099*
C246	0.71702 (18)	0.4874 (2)	0.55878 (13)	0.0441 (5)	0.931 (2)
H246	0.7734	0.5419	0.5492	0.053*	0.931 (2)
S241	0.59525 (6)	0.42819 (7)	0.67194 (4)	0.0498 (3)	0.931 (2)
C242	0.6984 (2)	0.5121 (2)	0.64157 (14)	0.0391 (6)	0.931 (2)
C243	0.7622 (7)	0.6011 (7)	0.7068 (4)	0.0554 (8)	0.931 (2)
H243	0.8227	0.6546	0.7029	0.066*	0.931 (2)
C244	0.7251 (2)	0.6029 (3)	0.78312 (18)	0.0540 (7)	0.931 (2)
H244	0.7588	0.6577	0.8341	0.065*	0.931 (2)
C245	0.6353 (3)	0.5151 (3)	0.77136 (17)	0.0532 (7)	0.931 (2)
H245	0.5995	0.5037	0.8132	0.064*	0.931 (2)
C446	0.71702 (18)	0.4874 (2)	0.55878 (13)	0.0441 (5)	0.069 (2)
H446	0.7604	0.5555	0.5451	0.053*	0.069 (2)
S441	0.769 (3)	0.621 (3)	0.7230 (14)	0.0554 (8)	0.069 (2)
C442	0.713 (3)	0.489 (3)	0.6480 (11)	0.0391 (6)	0.069 (2)
C443	0.639 (3)	0.411 (3)	0.6731 (17)	0.0498 (3)	0.069 (2)
H443	0.6009	0.3339	0.6414	0.060*	0.069 (2)
C444	0.627 (4)	0.460 (3)	0.755 (2)	0.0589 (7)	0.069 (2)
H444	0.5871	0.4143	0.7859	0.071*	0.069 (2)
C445	0.681 (4)	0.582 (4)	0.781 (2)	0.0540 (7)	0.069 (2)
H445	0.6711	0.6368	0.8247	0.065*	0.069 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0541 (10)	0.0528 (10)	0.0627 (10)	0.0129 (8)	0.0181 (8)	−0.0033 (9)
C12	0.0494 (13)	0.0499 (14)	0.0528 (13)	−0.0019 (12)	0.0169 (11)	−0.0059 (12)
N13	0.0529 (11)	0.0462 (11)	0.0487 (10)	0.0041 (10)	0.0205 (9)	−0.0022 (9)
C14	0.0414 (12)	0.0439 (13)	0.0469 (12)	0.0011 (11)	0.0171 (10)	−0.0064 (11)
C15	0.0428 (13)	0.0519 (14)	0.0574 (14)	0.0023 (11)	0.0174 (11)	−0.0089 (12)
O151	0.0661 (11)	0.0806 (12)	0.0675 (11)	0.0155 (10)	0.0343 (9)	−0.0121 (10)
C121	0.0816 (19)	0.0642 (17)	0.0649 (16)	0.0055 (15)	0.0223 (14)	0.0077 (14)
C146	0.0484 (13)	0.0481 (13)	0.0435 (12)	0.0005 (11)	0.0215 (10)	−0.0041 (11)
S141	0.0575 (4)	0.0540 (4)	0.0416 (3)	0.0067 (3)	0.0247 (3)	−0.0014 (3)
C142	0.0430 (11)	0.0434 (12)	0.0403 (11)	0.0003 (10)	0.0180 (10)	−0.0018 (10)
C143	0.063 (2)	0.063 (2)	0.0502 (14)	0.0172 (14)	0.0303 (13)	0.0056 (14)
C144	0.0673 (17)	0.0565 (15)	0.0599 (16)	0.0202 (14)	0.0318 (14)	0.0094 (13)
C145	0.0613 (16)	0.0501 (14)	0.0627 (16)	0.0103 (13)	0.0345 (13)	−0.0021 (13)
C346	0.0484 (13)	0.0481 (13)	0.0435 (12)	0.0005 (11)	0.0215 (10)	−0.0041 (11)
S341	0.063 (2)	0.063 (2)	0.0502 (14)	0.0172 (14)	0.0303 (13)	0.0056 (14)
C342	0.0430 (11)	0.0434 (12)	0.0403 (11)	0.0003 (10)	0.0180 (10)	−0.0018 (10)
C343	0.0575 (4)	0.0540 (4)	0.0416 (3)	0.0067 (3)	0.0247 (3)	−0.0014 (3)
C344	0.0613 (16)	0.0501 (14)	0.0627 (16)	0.0103 (13)	0.0345 (13)	−0.0021 (13)
C345	0.0673 (17)	0.0565 (15)	0.0599 (16)	0.0202 (14)	0.0318 (14)	0.0094 (13)
O21	0.0663 (10)	0.0586 (10)	0.0477 (9)	−0.0045 (9)	0.0268 (8)	−0.0098 (8)
C22	0.0524 (13)	0.0474 (13)	0.0497 (13)	0.0041 (11)	0.0192 (11)	0.0014 (11)
N23	0.0517 (11)	0.0453 (11)	0.0434 (10)	−0.0021 (9)	0.0189 (8)	−0.0014 (9)
C24	0.0466 (12)	0.0454 (12)	0.0420 (11)	0.0016 (11)	0.0206 (10)	0.0011 (11)
C25	0.0605 (15)	0.0536 (14)	0.0495 (13)	0.0044 (13)	0.0274 (12)	−0.0005 (12)
O251	0.0937 (14)	0.0812 (13)	0.0709 (11)	−0.0175 (11)	0.0572 (11)	−0.0084 (10)
C221	0.0703 (17)	0.0592 (16)	0.0636 (15)	−0.0111 (14)	0.0198 (13)	−0.0126 (14)
C246	0.0460 (12)	0.0437 (12)	0.0471 (12)	−0.0014 (11)	0.0226 (10)	0.0021 (11)
S241	0.0488 (4)	0.0555 (4)	0.0489 (4)	−0.0078 (3)	0.0228 (3)	0.0028 (3)
C242	0.0416 (13)	0.0350 (13)	0.0419 (11)	0.0027 (11)	0.0171 (10)	0.0044 (10)
C243	0.0629 (17)	0.056 (3)	0.051 (2)	−0.0061 (17)	0.026 (2)	−0.0113 (14)
C244	0.060 (2)	0.0577 (16)	0.0439 (13)	−0.0067 (14)	0.0190 (14)	−0.0093 (12)
C245	0.0629 (17)	0.0590 (18)	0.0456 (14)	−0.0004 (16)	0.0293 (13)	0.0018 (14)
C446	0.0460 (12)	0.0437 (12)	0.0471 (12)	−0.0014 (11)	0.0226 (10)	0.0021 (11)
S441	0.0629 (17)	0.056 (3)	0.051 (2)	−0.0061 (17)	0.026 (2)	−0.0113 (14)
C442	0.0416 (13)	0.0350 (13)	0.0419 (11)	0.0027 (11)	0.0171 (10)	0.0044 (10)
C443	0.0488 (4)	0.0555 (4)	0.0489 (4)	−0.0078 (3)	0.0228 (3)	0.0028 (3)
C444	0.0673 (17)	0.0565 (15)	0.0599 (16)	0.0202 (14)	0.0318 (14)	0.0094 (13)
C445	0.060 (2)	0.0577 (16)	0.0439 (13)	−0.0067 (14)	0.0190 (14)	−0.0093 (12)

Geometric parameters (Å, º)

O11—C12	1.385 (2)	O21—C25	1.388 (3)
O11—C15	1.388 (3)	O21—C22	1.389 (2)
C12—N13	1.273 (3)	C22—N23	1.273 (3)
C12—C121	1.473 (3)	C22—C221	1.472 (3)
N13—C14	1.407 (2)	N23—C24	1.403 (3)
C14—C146	1.337 (3)	C24—C246	1.333 (3)
C14—C15	1.454 (3)	C24—C25	1.467 (3)
C15—O151	1.194 (2)	C25—O251	1.196 (2)
C121—H121	0.9600	C221—H211	0.9600
C121—H122	0.9600	C221—H212	0.9600
C121—H123	0.9600	C221—H213	0.9600
C146—C142	1.426 (3)	C246—C242	1.437 (2)
C146—H146	0.9300	C246—H246	0.9300
S141—C145	1.695 (2)	S241—C245	1.698 (3)
S141—C142	1.7315 (19)	S241—C242	1.722 (2)
C142—C143	1.353 (4)	C242—C243	1.357 (5)
C143—C144	1.422 (4)	C243—C244	1.444 (5)
C143—H143	0.9300	C243—H243	0.9300
C144—C145	1.344 (3)	C244—C245	1.354 (3)
C144—H144	0.9300	C244—H244	0.9300
C145—H145	0.9300	C245—H245	0.9300
S341—C345	1.695 (5)	S441—C445	1.697 (6)
S341—C342	1.733 (5)	S441—C442	1.723 (5)
C342—C343	1.355 (6)	C442—C443	1.358 (7)
C343—C344	1.424 (6)	C443—C444	1.446 (7)
C343—H343	0.9300	C443—H443	0.9300
C344—C345	1.345 (6)	C444—C445	1.354 (6)
C344—H344	0.9300	C444—H444	0.9300
C345—H345	0.9300	C445—H445	0.9300
C12—O11—C15	105.55 (16)	C25—O21—C22	105.35 (16)
N13—C12—O11	116.05 (19)	N23—C22—O21	116.1 (2)
N13—C12—C121	128.5 (2)	N23—C22—C221	129.1 (2)
O11—C12—C121	115.4 (2)	O21—C22—C221	114.76 (19)
C12—N13—C14	105.09 (17)	C22—N23—C24	105.52 (17)
C146—C14—N13	127.16 (18)	C246—C24—N23	127.86 (17)
C146—C14—C15	124.20 (19)	C246—C24—C25	124.0 (2)
N13—C14—C15	108.64 (19)	N23—C24—C25	108.18 (18)
O151—C15—O11	121.9 (2)	O251—C25—O21	121.8 (2)
O151—C15—C14	133.4 (2)	O251—C25—C24	133.4 (2)
O11—C15—C14	104.67 (18)	O21—C25—C24	104.82 (18)
C12—C121—H121	109.5	C22—C221—H211	109.5
C12—C121—H122	109.5	C22—C221—H212	109.5
H121—C121—H122	109.5	H211—C221—H212	109.5
C12—C121—H123	109.5	C22—C221—H213	109.5
H121—C121—H123	109.5	H211—C221—H213	109.5
H122—C121—H123	109.5	H212—C221—H213	109.5
C14—C146—C142	128.66 (19)	C24—C246—C242	128.5 (2)
C14—C146—H146	115.7	C24—C246—H246	115.7
C142—C146—H146	115.7	C242—C246—H246	115.7
C145—S141—C142	91.29 (10)	C245—S241—C242	91.85 (12)
C143—C142—C146	124.7 (2)	C243—C242—C246	124.4 (3)
C143—C142—S141	111.06 (18)	C243—C242—S241	111.6 (3)
C146—C142—S141	124.23 (17)	C246—C242—S241	124.04 (18)
C142—C143—C144	112.6 (3)	C242—C243—C244	112.1 (4)
C142—C143—H143	123.7	C242—C243—H243	123.9
C144—C143—H143	123.7	C244—C243—H243	123.9
C145—C144—C143	112.2 (2)	C245—C244—C243	111.7 (3)
C145—C144—H144	123.9	C245—C244—H244	124.1
C143—C144—H144	123.9	C243—C244—H244	124.1
C144—C145—S141	112.84 (17)	C244—C245—S241	112.69 (18)
C144—C145—H145	123.6	C244—C245—H245	123.7
S141—C145—H145	123.6	S241—C245—H245	123.7
C345—S341—C342	91.3 (4)	C445—S441—C442	91.8 (4)
C343—C342—S341	110.5 (5)	C443—C442—S441	111.4 (5)
C342—C343—C344	112.0 (8)	C442—C443—C444	111.9 (6)
C342—C343—H343	124.0	C442—C443—H443	124.0
C344—C343—H343	124.0	C444—C443—H443	124.0
C345—C344—C343	111.6 (8)	C445—C444—C443	111.5 (7)
C345—C344—H344	124.2	C445—C444—H444	124.2
C343—C344—H344	124.2	C443—C444—H444	124.2
C344—C345—S341	112.5 (6)	C444—C445—S441	112.1 (6)
C344—C345—H345	123.8	C444—C445—H445	123.9
S341—C345—H345	123.8	S441—C445—H445	123.9
C15—O11—C12—N13	0.4 (3)	C25—O21—C22—N23	0.0 (2)
C15—O11—C12—C121	179.20 (19)	C25—O21—C22—C221	179.19 (19)
O11—C12—N13—C14	−0.7 (3)	O21—C22—N23—C24	−0.1 (2)
C121—C12—N13—C14	−179.3 (2)	C221—C22—N23—C24	−179.1 (2)
C12—N13—C14—C146	−178.8 (2)	C22—N23—C24—C246	179.9 (2)
C12—N13—C14—C15	0.7 (2)	C22—N23—C24—C25	0.1 (2)
C12—O11—C15—O151	−179.9 (2)	C22—O21—C25—O251	−179.8 (2)
C12—O11—C15—C14	0.0 (2)	C22—O21—C25—C24	0.1 (2)
C146—C14—C15—O151	−0.9 (4)	C246—C24—C25—O251	0.0 (4)
N13—C14—C15—O151	179.6 (2)	N23—C24—C25—O251	179.8 (3)
C146—C14—C15—O11	179.08 (19)	C246—C24—C25—O21	−179.9 (2)
N13—C14—C15—O11	−0.4 (2)	N23—C24—C25—O21	−0.1 (2)
N13—C14—C146—C142	−0.9 (4)	N23—C24—C246—C242	−1.9 (4)
C15—C14—C146—C142	179.7 (2)	C25—C24—C246—C242	177.9 (2)
C14—C146—C142—C143	178.7 (3)	C24—C246—C242—C243	175.4 (5)
C14—C146—C142—S141	−1.6 (4)	C24—C246—C242—S241	−2.4 (4)
C145—S141—C142—C143	−0.1 (3)	C245—S241—C242—C243	1.3 (4)
C145—S141—C142—C146	−179.8 (2)	C245—S241—C242—C246	179.3 (2)
C146—C142—C143—C144	180.0 (3)	C246—C242—C243—C244	−179.0 (4)
S141—C142—C143—C144	0.3 (4)	S241—C242—C243—C244	−1.0 (7)
C142—C143—C144—C145	−0.4 (5)	C242—C243—C244—C245	0.0 (7)
C143—C144—C145—S141	0.3 (4)	C243—C244—C245—S241	0.9 (5)
C142—S141—C145—C144	−0.1 (2)	C242—S241—C245—C244	−1.3 (2)
C345—S341—C342—C343	−5 (5)	C445—S441—C442—C443	−6 (3)
S341—C342—C343—C344	13 (5)	S441—C442—C443—C444	1 (4)
C342—C343—C344—C345	−16 (6)	C442—C443—C444—C445	7 (5)
C343—C344—C345—S341	12 (7)	C443—C444—C445—S441	−12 (5)
C342—S341—C345—C344	−4 (6)	C442—S441—C445—C444	10 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C143—H143···O251	0.93	2.54	3.434 (4)	162
C243—H243···O151^i	0.93	2.46	3.329 (9)	155

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

(III) 3-Anilino-2-phenyl-5-[(thiophen-2-yl)methylidene]-3,5-dihydro-4H-imidazol-4-one

Crystal data

C20H15N3OS	Z = 2
Mr = 345.41	F(000) = 360
Triclinic, P1	Dx = 1.382 Mg m^−3
a = 8.8460 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9951 (2) Å	Cell parameters from 7165 reflections
c = 11.2435 (2) Å	θ = 2.1–35.0°
α = 114.481 (1)°	µ = 0.21 mm^−1
β = 98.564 (1)°	T = 296 K
γ = 105.891 (1)°	Block, brown
V = 830.15 (3) Å^3	0.35 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer	4814 independent reflections
Radiation source: sealed tube	3747 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
Tmin = 0.917, Tmax = 0.969	k = −14→14
22029 measured reflections	l = −15→15

Refinement

Refinement on F^2	13 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0543P)^2 + 0.1853P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
4814 reflections	Δρmax = 0.28 e Å^−3
245 parameters	Δρmin = −0.26 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.41790 (14)	0.80484 (13)	0.31353 (12)	0.0397 (2)
C2	0.30862 (16)	0.67408 (14)	0.29313 (12)	0.0360 (3)
N3	0.38134 (14)	0.58656 (12)	0.33594 (11)	0.0372 (2)
C4	0.54988 (17)	0.66946 (15)	0.39106 (13)	0.0375 (3)
O41	0.64869 (13)	0.62777 (12)	0.44060 (11)	0.0479 (2)
C5	0.57126 (17)	0.81115 (15)	0.37355 (13)	0.0380 (3)
C21	0.13212 (16)	0.62953 (15)	0.23374 (13)	0.0382 (3)
C22	0.0814 (2)	0.75186 (18)	0.23843 (15)	0.0481 (3)
H22	0.1582	0.8550	0.2805	0.058*
C23	−0.0814 (2)	0.7210 (2)	0.18129 (19)	0.0597 (4)
H23	−0.1139	0.8031	0.1846	0.072*
C24	−0.1961 (2)	0.5686 (2)	0.1193 (2)	0.0640 (5)
H24	−0.3062	0.5481	0.0818	0.077*
C25	−0.1476 (2)	0.4469 (2)	0.1131 (2)	0.0650 (5)
H25	−0.2251	0.3440	0.0702	0.078*
C26	0.01558 (19)	0.47622 (19)	0.16986 (17)	0.0514 (4)
H26	0.0472	0.3932	0.1653	0.062*
N31	0.29845 (15)	0.44083 (12)	0.32625 (12)	0.0389 (2)
H31	0.3234 (19)	0.4448 (18)	0.4062 (17)	0.047*
C31	0.30355 (16)	0.30661 (14)	0.21529 (13)	0.0363 (3)
C32	0.2177 (2)	0.15893 (17)	0.19915 (17)	0.0532 (4)
H32	0.1654	0.1504	0.2630	0.064*
C33	0.2098 (3)	0.02409 (19)	0.08817 (19)	0.0666 (5)
H33	0.1511	−0.0750	0.0775	0.080*
C34	0.2876 (2)	0.0344 (2)	−0.00687 (17)	0.0620 (4)
H34	0.2820	−0.0569	−0.0812	0.074*
C35	0.3728 (2)	0.1801 (2)	0.00926 (16)	0.0584 (4)
H35	0.4260	0.1877	−0.0544	0.070*
C36	0.3811 (2)	0.31714 (18)	0.11963 (15)	0.0489 (3)
H36	0.4387	0.4158	0.1292	0.059*
C56	0.7166 (2)	0.92665 (15)	0.40655 (13)	0.0395 (3)	0.9005 (19)
H56	0.8101	0.9166	0.4462	0.047*	0.9005 (19)
S51	0.58702 (5)	1.11618 (5)	0.33272 (4)	0.0421 (2)	0.9005 (19)
C52	0.7431 (2)	1.06352 (18)	0.38714 (19)	0.0361 (4)	0.9005 (19)
C53	0.8916 (4)	1.1710 (5)	0.4132 (6)	0.0523 (6)	0.9005 (19)
H53	0.9902	1.1633	0.4457	0.063*	0.9005 (19)
C54	0.8852 (3)	1.2968 (3)	0.3870 (4)	0.0522 (5)	0.9005 (19)
H54	0.9770	1.3778	0.3970	0.063*	0.9005 (19)
C55	0.7272 (2)	1.2830 (2)	0.3453 (3)	0.0497 (4)	0.9005 (19)
H55	0.6978	1.3557	0.3256	0.060*	0.9005 (19)
C66	0.7166 (2)	0.92665 (15)	0.40655 (13)	0.0395 (3)	0.0995 (19)
H66	0.8110	0.9069	0.4284	0.047*	0.0995 (19)
S61	0.9327 (10)	1.1891 (14)	0.4225 (17)	0.0523 (6)	0.0995 (19)
C62	0.7406 (13)	1.0759 (15)	0.411 (2)	0.0361 (4)	0.0995 (19)
C63	0.6243 (15)	1.1204 (18)	0.366 (2)	0.04206 (14)	0.0995 (19)
H63	0.5129	1.0714	0.3527	0.050*	0.0995 (19)
C64	0.6858 (19)	1.248 (2)	0.339 (3)	0.0497 (4)	0.0995 (19)
H64	0.6209	1.2847	0.2966	0.060*	0.0995 (19)
C65	0.8530 (18)	1.311 (3)	0.385 (4)	0.0522 (5)	0.0995 (19)
H65	0.9170	1.4075	0.3941	0.063*	0.0995 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0436 (6)	0.0358 (5)	0.0454 (6)	0.0163 (5)	0.0124 (5)	0.0239 (5)
C2	0.0462 (7)	0.0336 (6)	0.0343 (6)	0.0190 (5)	0.0144 (5)	0.0183 (5)
N3	0.0455 (6)	0.0307 (5)	0.0402 (5)	0.0155 (4)	0.0126 (5)	0.0205 (4)
C4	0.0472 (7)	0.0352 (6)	0.0344 (6)	0.0175 (6)	0.0128 (5)	0.0189 (5)
O41	0.0534 (6)	0.0489 (6)	0.0530 (6)	0.0240 (5)	0.0122 (5)	0.0327 (5)
C5	0.0456 (7)	0.0349 (6)	0.0381 (6)	0.0171 (5)	0.0124 (5)	0.0204 (5)
C21	0.0435 (7)	0.0419 (7)	0.0369 (6)	0.0189 (6)	0.0158 (5)	0.0225 (5)
C22	0.0536 (8)	0.0451 (8)	0.0493 (8)	0.0245 (7)	0.0143 (6)	0.0224 (6)
C23	0.0603 (10)	0.0700 (11)	0.0677 (10)	0.0394 (9)	0.0237 (8)	0.0388 (9)
C24	0.0418 (8)	0.0899 (13)	0.0808 (12)	0.0282 (9)	0.0211 (8)	0.0559 (11)
C25	0.0447 (9)	0.0685 (11)	0.0847 (13)	0.0092 (8)	0.0114 (8)	0.0494 (10)
C26	0.0465 (8)	0.0478 (8)	0.0661 (10)	0.0157 (7)	0.0143 (7)	0.0348 (7)
N31	0.0537 (7)	0.0317 (5)	0.0384 (6)	0.0172 (5)	0.0171 (5)	0.0211 (5)
C31	0.0394 (7)	0.0345 (6)	0.0369 (6)	0.0156 (5)	0.0087 (5)	0.0185 (5)
C32	0.0669 (10)	0.0385 (7)	0.0564 (9)	0.0165 (7)	0.0246 (8)	0.0246 (7)
C33	0.0892 (13)	0.0349 (8)	0.0653 (11)	0.0164 (8)	0.0211 (10)	0.0196 (7)
C34	0.0800 (12)	0.0470 (9)	0.0470 (8)	0.0291 (9)	0.0134 (8)	0.0102 (7)
C35	0.0664 (10)	0.0606 (10)	0.0436 (8)	0.0251 (8)	0.0212 (7)	0.0184 (7)
C36	0.0568 (9)	0.0441 (7)	0.0448 (7)	0.0155 (7)	0.0195 (7)	0.0212 (6)
C56	0.0416 (7)	0.0403 (7)	0.0396 (6)	0.0174 (6)	0.0095 (5)	0.0212 (5)
S51	0.0479 (3)	0.0421 (2)	0.0472 (3)	0.02402 (18)	0.01742 (19)	0.02545 (19)
C52	0.0414 (7)	0.0347 (7)	0.0308 (10)	0.0141 (5)	0.0102 (6)	0.0146 (7)
C53	0.0407 (17)	0.0461 (13)	0.0554 (12)	−0.0009 (13)	0.0075 (18)	0.0241 (12)
C54	0.0605 (12)	0.0340 (8)	0.0524 (9)	0.0067 (8)	0.0166 (11)	0.0190 (7)
C55	0.0698 (14)	0.0323 (11)	0.0527 (9)	0.0202 (10)	0.0234 (11)	0.0232 (10)
C66	0.0416 (7)	0.0403 (7)	0.0396 (6)	0.0174 (6)	0.0095 (5)	0.0212 (5)
S61	0.0407 (17)	0.0461 (13)	0.0554 (12)	−0.0009 (13)	0.0075 (18)	0.0241 (12)
C62	0.0414 (7)	0.0347 (7)	0.0308 (10)	0.0141 (5)	0.0102 (6)	0.0146 (7)
C63	0.0479 (3)	0.0421 (2)	0.0472 (3)	0.02402 (18)	0.01742 (19)	0.02545 (19)
C64	0.0698 (14)	0.0323 (11)	0.0527 (9)	0.0202 (10)	0.0234 (11)	0.0232 (10)
C65	0.0605 (12)	0.0340 (8)	0.0524 (9)	0.0067 (8)	0.0166 (11)	0.0190 (7)

Geometric parameters (Å, º)

N1—C2	1.2996 (16)	C33—C34	1.378 (3)
N1—C5	1.3946 (17)	C33—H33	0.9300
C2—N3	1.4056 (15)	C34—C35	1.364 (2)
C2—C21	1.4643 (19)	C34—H34	0.9300
N3—C4	1.3842 (18)	C35—C36	1.390 (2)
N3—N31	1.3895 (14)	C35—H35	0.9300
C4—O41	1.2225 (15)	C36—H36	0.9300
C4—C5	1.4750 (17)	C56—C52	1.4357 (18)
C5—C56	1.3469 (19)	C56—H56	0.9300
C21—C26	1.389 (2)	S51—C55	1.7197 (17)
C21—C22	1.3977 (18)	S51—C52	1.7233 (18)
C22—C23	1.378 (2)	C52—C53	1.348 (3)
C22—H22	0.9300	C53—C54	1.418 (4)
C23—C24	1.378 (3)	C53—H53	0.9300
C23—H23	0.9300	C54—C55	1.356 (3)
C24—C25	1.376 (3)	C54—H54	0.9300
C24—H24	0.9300	C55—H55	0.9300
C25—C26	1.384 (2)	S61—C62	1.718 (5)
C25—H25	0.9300	S61—C65	1.721 (5)
C26—H26	0.9300	C62—C63	1.343 (6)
N31—C31	1.4216 (16)	C63—C64	1.417 (6)
N31—H31	0.874 (17)	C63—H63	0.9300
C31—C32	1.3825 (19)	C64—C65	1.358 (5)
C31—C36	1.3829 (19)	C64—H64	0.9300
C32—C33	1.381 (2)	C65—H65	0.9300
C32—H32	0.9300
C2—N1—C5	107.05 (10)	C34—C33—C32	120.83 (16)
N1—C2—N3	111.80 (11)	C34—C33—H33	119.6
N1—C2—C21	122.21 (11)	C32—C33—H33	119.6
N3—C2—C21	125.98 (11)	C35—C34—C33	119.25 (15)
C4—N3—N31	125.00 (10)	C35—C34—H34	120.4
C4—N3—C2	109.11 (10)	C33—C34—H34	120.4
N31—N3—C2	125.89 (11)	C34—C35—C36	120.79 (15)
O41—C4—N3	125.65 (12)	C34—C35—H35	119.6
O41—C4—C5	131.83 (13)	C36—C35—H35	119.6
N3—C4—C5	102.52 (10)	C31—C36—C35	119.90 (14)
C56—C5—N1	125.10 (11)	C31—C36—H36	120.1
C56—C5—C4	125.38 (12)	C35—C36—H36	120.1
N1—C5—C4	109.49 (11)	C5—C56—C52	127.09 (14)
C26—C21—C22	118.77 (13)	C5—C56—H56	116.5
C26—C21—C2	124.94 (12)	C52—C56—H56	116.5
C22—C21—C2	116.25 (12)	C55—S51—C52	91.26 (9)
C23—C22—C21	120.60 (15)	C53—C52—C56	125.2 (2)
C23—C22—H22	119.7	C53—C52—S51	110.74 (19)
C21—C22—H22	119.7	C56—C52—S51	124.05 (13)
C24—C23—C22	120.07 (15)	C52—C53—C54	114.5 (3)
C24—C23—H23	120.0	C52—C53—H53	122.8
C22—C23—H23	120.0	C54—C53—H53	122.8
C25—C24—C23	119.91 (16)	C55—C54—C53	110.88 (18)
C25—C24—H24	120.0	C55—C54—H54	124.6
C23—C24—H24	120.0	C53—C54—H54	124.6
C24—C25—C26	120.59 (17)	C54—C55—S51	112.60 (14)
C24—C25—H25	119.7	C54—C55—H55	123.7
C26—C25—H25	119.7	S51—C55—H55	123.7
C25—C26—C21	120.05 (15)	C62—S61—C65	90.7 (4)
C25—C26—H26	120.0	C63—C62—S61	111.1 (5)
C21—C26—H26	120.0	C62—C63—C64	114.2 (6)
N3—N31—C31	115.70 (10)	C62—C63—H63	122.9
N3—N31—H31	110.4 (11)	C64—C63—H63	122.9
C31—N31—H31	115.2 (10)	C65—C64—C63	110.3 (6)
C32—C31—C36	119.27 (13)	C65—C64—H64	124.9
C32—C31—N31	117.51 (12)	C63—C64—H64	124.9
C36—C31—N31	123.09 (12)	C64—C65—S61	112.1 (6)
C33—C32—C31	119.96 (15)	C64—C65—H65	124.0
C33—C32—H32	120.0	S61—C65—H65	124.0
C31—C32—H32	120.0
C5—N1—C2—N3	−0.68 (14)	C4—N3—N31—C31	−79.88 (15)
C5—N1—C2—C21	178.68 (11)	C2—N3—N31—C31	100.78 (14)
N1—C2—N3—C4	1.54 (14)	N3—N31—C31—C32	−177.77 (12)
C21—C2—N3—C4	−177.79 (11)	N3—N31—C31—C36	−1.85 (19)
N1—C2—N3—N31	−179.04 (11)	C36—C31—C32—C33	−0.2 (2)
C21—C2—N3—N31	1.63 (19)	N31—C31—C32—C33	175.89 (15)
N31—N3—C4—O41	−1.2 (2)	C31—C32—C33—C34	0.5 (3)
C2—N3—C4—O41	178.22 (12)	C32—C33—C34—C35	−0.2 (3)
N31—N3—C4—C5	178.98 (11)	C33—C34—C35—C36	−0.3 (3)
C2—N3—C4—C5	−1.59 (13)	C32—C31—C36—C35	−0.3 (2)
C2—N1—C5—C56	177.83 (13)	N31—C31—C36—C35	−176.19 (14)
C2—N1—C5—C4	−0.36 (14)	C34—C35—C36—C31	0.6 (3)
O41—C4—C5—C56	3.2 (2)	N1—C5—C56—C52	−0.1 (2)
N3—C4—C5—C56	−176.96 (12)	C4—C5—C56—C52	177.85 (14)
O41—C4—C5—N1	−178.57 (13)	C5—C56—C52—C53	−175.3 (3)
N3—C4—C5—N1	1.22 (13)	C5—C56—C52—S51	7.2 (2)
N1—C2—C21—C26	158.56 (14)	C55—S51—C52—C53	0.4 (3)
N3—C2—C21—C26	−22.2 (2)	C55—S51—C52—C56	178.24 (17)
N1—C2—C21—C22	−18.88 (18)	C56—C52—C53—C54	−179.4 (3)
N3—C2—C21—C22	160.39 (12)	S51—C52—C53—C54	−1.6 (5)
C26—C21—C22—C23	0.3 (2)	C52—C53—C54—C55	2.3 (6)
C2—C21—C22—C23	177.91 (13)	C53—C54—C55—S51	−1.9 (4)
C21—C22—C23—C24	0.3 (2)	C52—S51—C55—C54	0.9 (2)
C22—C23—C24—C25	−0.8 (3)	C65—S61—C62—C63	7 (2)
C23—C24—C25—C26	0.7 (3)	S61—C62—C63—C64	−1 (3)
C24—C25—C26—C21	−0.1 (3)	C62—C63—C64—C65	−8 (3)
C22—C21—C26—C25	−0.4 (2)	C63—C64—C65—S61	13 (4)
C2—C21—C26—C25	−177.77 (14)	C62—S61—C65—C64	−12 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N31—H31···O41^i	0.875 (17)	2.136 (18)	2.9767 (17)	161.1 (17)
C34—H34···Cg1^ii	0.93	2.90	3.654 (2)	140

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

(IV) 3-Anilino-2-(4-methylphenyl)-5-[(thiophen-2-yl)methylidene]-3,5-dihydro-4H-imidazol-4-one

Crystal data

C21H17N3OS	Z = 2
Mr = 359.44	F(000) = 376
Triclinic, P1	Dx = 1.343 Mg m^−3
a = 9.1697 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7939 (5) Å	Cell parameters from 4395 reflections
c = 11.0837 (6) Å	θ = 3.7–28.4°
α = 66.424 (2)°	µ = 0.20 mm^−1
β = 66.147 (3)°	T = 296 K
γ = 67.934 (2)°	Block, red
V = 889.13 (8) Å^3	0.22 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer	4395 independent reflections
Radiation source: sealed tube	3909 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 28.4°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
Tmin = 0.911, Tmax = 0.971	k = −14→14
33541 measured reflections	l = −14→14

Refinement

Refinement on F^2	13 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0247P)^2 + 0.7161P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
4395 reflections	Δρmax = 0.40 e Å^−3
255 parameters	Δρmin = −0.28 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.24181 (14)	0.75542 (12)	0.76032 (12)	0.0186 (2)
C2	0.40057 (16)	0.73906 (13)	0.70055 (13)	0.0168 (2)
N3	0.47389 (13)	0.61663 (12)	0.65903 (12)	0.0174 (2)
C4	0.35178 (16)	0.55165 (14)	0.69044 (13)	0.0178 (3)
C5	0.20271 (17)	0.64277 (14)	0.75904 (13)	0.0187 (3)
O41	0.37406 (12)	0.44584 (10)	0.66276 (10)	0.0214 (2)
C21	0.48741 (16)	0.83873 (13)	0.67962 (13)	0.0163 (2)
C22	0.39057 (17)	0.97185 (14)	0.69171 (14)	0.0194 (3)
H22	0.2766	0.9924	0.7133	0.023*
C23	0.46361 (18)	1.07287 (14)	0.67168 (14)	0.0216 (3)
H23	0.3978	1.1606	0.6801	0.026*
C24	0.63419 (17)	1.04501 (14)	0.63911 (13)	0.0193 (3)
C25	0.72960 (17)	0.91194 (14)	0.62916 (14)	0.0201 (3)
H25	0.8435	0.8915	0.6084	0.024*
C26	0.65865 (17)	0.80934 (14)	0.64956 (14)	0.0192 (3)
H26	0.7247	0.7211	0.6433	0.023*
C27	0.71468 (19)	1.15417 (15)	0.61646 (16)	0.0256 (3)
H27A	0.6328	1.2411	0.6200	0.038*
H27B	0.7967	1.1664	0.5278	0.038*
H27C	0.7659	1.1246	0.6872	0.038*
N31	0.63758 (14)	0.57185 (12)	0.58565 (12)	0.0175 (2)
H31	0.643 (2)	0.5626 (18)	0.5088 (19)	0.021*
C31	0.73737 (16)	0.45886 (13)	0.66186 (14)	0.0170 (2)
C32	0.88742 (16)	0.38721 (14)	0.58827 (14)	0.0202 (3)
H32	0.9152	0.4101	0.4928	0.024*
C33	0.99472 (18)	0.28207 (16)	0.65751 (16)	0.0265 (3)
H33	1.0945	0.2350	0.6079	0.032*
C34	0.9552 (2)	0.24619 (17)	0.79951 (17)	0.0307 (3)
H34	1.0277	0.1752	0.8452	0.037*
C35	0.8063 (2)	0.31706 (17)	0.87319 (16)	0.0297 (3)
H35	0.7792	0.2934	0.9686	0.036*
C36	0.69714 (18)	0.42357 (15)	0.80490 (15)	0.0232 (3)
H36	0.5978	0.4709	0.8547	0.028*
C56	0.05068 (17)	0.61777 (14)	0.81750 (14)	0.0202 (3)	0.866 (2)
H56	0.0400	0.5388	0.8104	0.024*	0.866 (2)
S51	−0.10269 (6)	0.86039 (5)	0.90082 (6)	0.02351 (14)	0.866 (2)
C52	−0.0945 (10)	0.7026 (17)	0.889 (3)	0.0221 (3)	0.866 (2)
C53	−0.2459 (5)	0.6735 (5)	0.9562 (6)	0.0308 (7)	0.866 (2)
H53	−0.2656	0.5932	0.9604	0.037*	0.866 (2)
C54	−0.3675 (4)	0.7732 (4)	1.0174 (6)	0.0332 (5)	0.866 (2)
H54	−0.4754	0.7669	1.0669	0.040*	0.866 (2)
C55	−0.3082 (3)	0.8815 (4)	0.9956 (5)	0.0289 (5)	0.866 (2)
H55	−0.3717	0.9584	1.0282	0.035*	0.866 (2)
C66	0.05068 (17)	0.61777 (14)	0.81750 (14)	0.0202 (3)	0.134 (2)
H66	0.0405	0.5390	0.8095	0.024*	0.134 (2)
S61	−0.2796 (10)	0.6522 (9)	0.9676 (10)	0.0308 (7)	0.134 (2)
C62	−0.096 (6)	0.701 (11)	0.890 (17)	0.0221 (3)	0.134 (2)
C63	−0.1170 (16)	0.8237 (14)	0.9132 (18)	0.02351 (14)	0.134 (2)
H63	−0.0310	0.8653	0.8822	0.028*	0.134 (2)
C64	−0.276 (2)	0.881 (3)	0.986 (4)	0.0289 (5)	0.134 (2)
H64	−0.3089	0.9651	1.0066	0.035*	0.134 (2)
C65	−0.378 (2)	0.798 (3)	1.023 (5)	0.0332 (5)	0.134 (2)
H65	−0.4886	0.8190	1.0733	0.040*	0.134 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0192 (5)	0.0186 (5)	0.0191 (5)	−0.0041 (4)	−0.0072 (4)	−0.0056 (4)
C2	0.0195 (6)	0.0158 (6)	0.0165 (6)	−0.0016 (5)	−0.0084 (5)	−0.0057 (5)
N3	0.0169 (5)	0.0164 (5)	0.0211 (5)	−0.0023 (4)	−0.0068 (4)	−0.0084 (4)
C4	0.0205 (6)	0.0173 (6)	0.0168 (6)	−0.0051 (5)	−0.0085 (5)	−0.0029 (5)
C5	0.0212 (6)	0.0175 (6)	0.0178 (6)	−0.0030 (5)	−0.0083 (5)	−0.0047 (5)
O41	0.0274 (5)	0.0180 (5)	0.0219 (5)	−0.0065 (4)	−0.0088 (4)	−0.0068 (4)
C21	0.0190 (6)	0.0154 (6)	0.0167 (6)	−0.0029 (5)	−0.0078 (5)	−0.0056 (4)
C22	0.0185 (6)	0.0183 (6)	0.0209 (6)	−0.0015 (5)	−0.0072 (5)	−0.0069 (5)
C23	0.0260 (7)	0.0143 (6)	0.0239 (7)	−0.0014 (5)	−0.0096 (5)	−0.0064 (5)
C24	0.0263 (7)	0.0171 (6)	0.0170 (6)	−0.0066 (5)	−0.0098 (5)	−0.0029 (5)
C25	0.0200 (6)	0.0198 (6)	0.0229 (6)	−0.0043 (5)	−0.0094 (5)	−0.0064 (5)
C26	0.0202 (6)	0.0168 (6)	0.0225 (6)	−0.0015 (5)	−0.0087 (5)	−0.0081 (5)
C27	0.0322 (8)	0.0194 (6)	0.0294 (7)	−0.0092 (6)	−0.0136 (6)	−0.0043 (6)
N31	0.0170 (5)	0.0179 (5)	0.0177 (5)	−0.0014 (4)	−0.0050 (4)	−0.0082 (4)
C31	0.0180 (6)	0.0152 (6)	0.0222 (6)	−0.0057 (5)	−0.0071 (5)	−0.0072 (5)
C32	0.0193 (6)	0.0203 (6)	0.0222 (6)	−0.0061 (5)	−0.0037 (5)	−0.0087 (5)
C33	0.0202 (7)	0.0254 (7)	0.0335 (8)	−0.0002 (5)	−0.0082 (6)	−0.0133 (6)
C34	0.0286 (8)	0.0278 (8)	0.0360 (8)	0.0037 (6)	−0.0195 (7)	−0.0099 (6)
C35	0.0347 (8)	0.0304 (8)	0.0233 (7)	−0.0025 (6)	−0.0137 (6)	−0.0074 (6)
C36	0.0222 (6)	0.0242 (7)	0.0221 (7)	−0.0017 (5)	−0.0060 (5)	−0.0101 (5)
C56	0.0224 (6)	0.0197 (6)	0.0194 (6)	−0.0056 (5)	−0.0104 (5)	−0.0022 (5)
S51	0.0200 (2)	0.0245 (3)	0.0267 (2)	0.00036 (17)	−0.01011 (16)	−0.0106 (2)
C52	0.0211 (7)	0.0244 (8)	0.0189 (8)	−0.0047 (5)	−0.0097 (5)	−0.0017 (7)
C53	0.032 (2)	0.0277 (16)	0.0293 (11)	−0.0071 (10)	−0.0133 (14)	−0.0016 (11)
C54	0.0227 (8)	0.0347 (18)	0.0292 (10)	−0.0041 (10)	−0.0061 (7)	−0.0016 (14)
C55	0.0160 (11)	0.0365 (9)	0.0264 (11)	0.0040 (10)	−0.0057 (13)	−0.0122 (7)
C66	0.0224 (6)	0.0197 (6)	0.0194 (6)	−0.0056 (5)	−0.0104 (5)	−0.0022 (5)
S61	0.032 (2)	0.0277 (16)	0.0293 (11)	−0.0071 (10)	−0.0133 (14)	−0.0016 (11)
C62	0.0211 (7)	0.0244 (8)	0.0189 (8)	−0.0047 (5)	−0.0097 (5)	−0.0017 (7)
C63	0.0200 (2)	0.0245 (3)	0.0267 (2)	0.00036 (17)	−0.01011 (16)	−0.0106 (2)
C64	0.0160 (11)	0.0365 (9)	0.0264 (11)	0.0040 (10)	−0.0057 (13)	−0.0122 (7)
C65	0.0227 (8)	0.0347 (18)	0.0292 (10)	−0.0041 (10)	−0.0061 (7)	−0.0016 (14)

Geometric parameters (Å, º)

N1—C2	1.3075 (17)	C32—C33	1.386 (2)
N1—C5	1.3974 (17)	C32—H32	0.9300
C2—N3	1.4067 (16)	C33—C34	1.384 (2)
C2—C21	1.4628 (18)	C33—H33	0.9300
N3—N31	1.3893 (15)	C34—C35	1.389 (2)
N3—C4	1.3952 (17)	C34—H34	0.9300
C4—O41	1.2225 (16)	C35—C36	1.396 (2)
C4—C5	1.4702 (18)	C35—H35	0.9300
C5—C56	1.3595 (19)	C36—H36	0.9300
C21—C26	1.4016 (18)	C56—C52	1.433 (2)
C21—C22	1.4037 (18)	C56—H56	0.9300
C22—C23	1.3861 (19)	S51—C55	1.724 (2)
C22—H22	0.9300	S51—C52	1.730 (3)
C23—C24	1.394 (2)	C52—C53	1.374 (4)
C23—H23	0.9300	C53—C54	1.390 (5)
C24—C25	1.3947 (19)	C53—H53	0.9300
C24—C27	1.5043 (19)	C54—C55	1.367 (3)
C25—C26	1.3867 (19)	C54—H54	0.9300
C25—H25	0.9300	C55—H55	0.9300
C26—H26	0.9300	S61—C65	1.715 (10)
C27—H27A	0.9600	S61—C62	1.731 (11)
C27—H27B	0.9600	C62—C63	1.374 (10)
C27—H27C	0.9600	C63—C64	1.391 (10)
N31—C31	1.4144 (17)	C63—H63	0.9300
N31—H31	0.876 (18)	C64—C65	1.363 (9)
C31—C36	1.3944 (19)	C64—H64	0.9300
C31—C32	1.3979 (18)	C65—H65	0.9300
C2—N1—C5	106.80 (11)	C33—C32—C31	120.00 (13)
N1—C2—N3	111.74 (11)	C33—C32—H32	120.0
N1—C2—C21	122.93 (12)	C31—C32—H32	120.0
N3—C2—C21	125.32 (12)	C34—C33—C32	120.84 (14)
N31—N3—C4	123.73 (11)	C34—C33—H33	119.6
N31—N3—C2	126.90 (11)	C32—C33—H33	119.6
C4—N3—C2	109.06 (11)	C33—C34—C35	119.43 (14)
O41—C4—N3	125.35 (12)	C33—C34—H34	120.3
O41—C4—C5	132.29 (13)	C35—C34—H34	120.3
N3—C4—C5	102.35 (11)	C34—C35—C36	120.43 (14)
C56—C5—N1	125.10 (13)	C34—C35—H35	119.8
C56—C5—C4	124.86 (13)	C36—C35—H35	119.8
N1—C5—C4	109.99 (11)	C31—C36—C35	119.87 (13)
C26—C21—C22	118.71 (12)	C31—C36—H36	120.1
C26—C21—C2	124.37 (12)	C35—C36—H36	120.1
C22—C21—C2	116.92 (12)	C5—C56—C52	125.57 (18)
C23—C22—C21	120.48 (12)	C5—C56—H56	117.2
C23—C22—H22	119.8	C52—C56—H56	117.2
C21—C22—H22	119.8	C55—S51—C52	90.99 (12)
C22—C23—C24	121.02 (12)	C53—C52—C56	126.0 (3)
C22—C23—H23	119.5	C53—C52—S51	110.2 (2)
C24—C23—H23	119.5	C56—C52—S51	123.8 (2)
C23—C24—C25	118.25 (12)	C52—C53—C54	114.9 (3)
C23—C24—C27	121.42 (13)	C52—C53—H53	122.6
C25—C24—C27	120.33 (13)	C54—C53—H53	122.6
C26—C25—C24	121.54 (13)	C55—C54—C53	111.2 (2)
C26—C25—H25	119.2	C55—C54—H54	124.4
C24—C25—H25	119.2	C53—C54—H54	124.4
C25—C26—C21	119.98 (12)	C54—C55—S51	112.7 (2)
C25—C26—H26	120.0	C54—C55—H55	123.6
C21—C26—H26	120.0	S51—C55—H55	123.6
C24—C27—H27A	109.5	C65—S61—C62	91.3 (6)
C24—C27—H27B	109.5	C63—C62—S61	109.4 (6)
H27A—C27—H27B	109.5	C62—C63—C64	115.4 (9)
C24—C27—H27C	109.5	C62—C63—H63	122.3
H27A—C27—H27C	109.5	C64—C63—H63	122.3
H27B—C27—H27C	109.5	C65—C64—C63	110.8 (11)
N3—N31—C31	116.19 (11)	C65—C64—H64	124.6
N3—N31—H31	110.1 (11)	C63—C64—H64	124.6
C31—N31—H31	115.0 (11)	C64—C65—S61	113.0 (10)
C36—C31—C32	119.44 (12)	C64—C65—H65	123.5
C36—C31—N31	122.61 (12)	S61—C65—H65	123.5
C32—C31—N31	117.79 (12)
C5—N1—C2—N3	−0.76 (14)	C2—C21—C26—C25	178.90 (12)
C5—N1—C2—C21	178.62 (11)	C4—N3—N31—C31	−81.40 (15)
N1—C2—N3—N31	175.90 (11)	C2—N3—N31—C31	105.69 (14)
C21—C2—N3—N31	−3.5 (2)	N3—N31—C31—C36	−21.06 (18)
N1—C2—N3—C4	2.13 (15)	N3—N31—C31—C32	163.55 (11)
C21—C2—N3—C4	−177.23 (12)	C36—C31—C32—C33	0.0 (2)
N31—N3—C4—O41	3.0 (2)	N31—C31—C32—C33	175.57 (12)
C2—N3—C4—O41	177.05 (12)	C31—C32—C33—C34	0.2 (2)
N31—N3—C4—C5	−176.39 (11)	C32—C33—C34—C35	−0.3 (2)
C2—N3—C4—C5	−2.39 (13)	C33—C34—C35—C36	0.0 (3)
C2—N1—C5—C56	176.70 (13)	C32—C31—C36—C35	−0.2 (2)
C2—N1—C5—C4	−0.81 (14)	N31—C31—C36—C35	−175.57 (13)
O41—C4—C5—C56	5.1 (2)	C34—C35—C36—C31	0.2 (2)
N3—C4—C5—C56	−175.52 (13)	N1—C5—C56—C52	0.4 (15)
O41—C4—C5—N1	−177.38 (14)	C4—C5—C56—C52	177.5 (15)
N3—C4—C5—N1	2.00 (14)	C5—C56—C52—C53	−175.5 (16)
N1—C2—C21—C26	162.87 (13)	C5—C56—C52—S51	5 (3)
N3—C2—C21—C26	−17.8 (2)	C55—S51—C52—C53	0.2 (18)
N1—C2—C21—C22	−16.72 (18)	C55—S51—C52—C56	179 (2)
N3—C2—C21—C22	162.58 (12)	C56—C52—C53—C54	−179.7 (19)
C26—C21—C22—C23	1.2 (2)	S51—C52—C53—C54	−1 (2)
C2—C21—C22—C23	−179.19 (12)	C52—C53—C54—C55	0.6 (16)
C21—C22—C23—C24	0.0 (2)	C53—C54—C55—S51	−0.4 (7)
C22—C23—C24—C25	−0.9 (2)	C52—S51—C55—C54	0.1 (11)
C22—C23—C24—C27	179.68 (13)	C65—S61—C62—C63	1 (11)
C23—C24—C25—C26	0.6 (2)	S61—C62—C63—C64	−2 (14)
C27—C24—C25—C26	179.99 (13)	C62—C63—C64—C65	2 (10)
C24—C25—C26—C21	0.6 (2)	C63—C64—C65—S61	−1 (5)
C22—C21—C26—C25	−1.53 (19)	C62—S61—C65—C64	0 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N31—H31···O41^i	0.876 (19)	2.010 (19)	2.8813 (16)	172.9 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

(V) 2-Phenyl-5-[(thiophen-2-yl)methylidene]-3-{[(E)-(thiophen-2-yl)methylidene]amino}-3,5-dihydro-4H-imidazol-4-one

Crystal data

C19H13N3OS2	Dx = 1.432 Mg m^−3
Mr = 363.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 6527 reflections
a = 8.2717 (2) Å	θ = 3.2–33.4°
b = 17.4530 (3) Å	µ = 0.33 mm^−1
c = 23.3501 (5) Å	T = 296 K
V = 3370.96 (12) Å^3	Block, brown
Z = 8	0.45 × 0.45 × 0.45 mm
F(000) = 1504

Data collection

Bruker APEXII CCD diffractometer	4912 independent reflections
Radiation source: sealed tube	3966 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 30.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→10
Tmin = 0.817, Tmax = 0.863	k = −23→24
24050 measured reflections	l = −32→29

Refinement

Refinement on F^2	13 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 1.3618P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
4912 reflections	Δρmax = 0.33 e Å^−3
242 parameters	Δρmin = −0.33 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.54252 (15)	0.55168 (7)	0.56565 (5)	0.0371 (3)
C2	0.51062 (16)	0.49658 (7)	0.60166 (6)	0.0337 (3)
N3	0.63071 (15)	0.44002 (7)	0.60204 (5)	0.0381 (3)
C4	0.75032 (18)	0.46075 (8)	0.56229 (7)	0.0418 (3)
O41	0.87160 (14)	0.42511 (7)	0.55057 (6)	0.0605 (4)
C5	0.68887 (18)	0.53423 (8)	0.54010 (6)	0.0383 (3)
C21	0.35853 (16)	0.49441 (7)	0.63427 (6)	0.0339 (3)
C22	0.2369 (2)	0.54397 (9)	0.61536 (7)	0.0435 (3)
H22	0.2562	0.5761	0.5844	0.052*
C23	0.0887 (2)	0.54564 (10)	0.64220 (8)	0.0519 (4)
H23	0.0085	0.5786	0.6291	0.062*
C24	0.0588 (2)	0.49878 (10)	0.68825 (8)	0.0521 (4)
H24	−0.0416	0.4998	0.7062	0.063*
C25	0.1781 (2)	0.45034 (10)	0.70780 (7)	0.0531 (4)
H25	0.1582	0.4192	0.7394	0.064*
C26	0.3275 (2)	0.44748 (9)	0.68100 (6)	0.0445 (3)
H26	0.4068	0.4142	0.6943	0.053*
N31	0.63111 (15)	0.37886 (7)	0.63997 (5)	0.0402 (3)
C36	0.7208 (2)	0.32114 (8)	0.62697 (7)	0.0435 (3)
H36	0.7806	0.3217	0.5933	0.052*
S31	0.61844 (7)	0.24869 (3)	0.72607 (2)	0.06214 (16)
C32	0.72870 (19)	0.25580 (8)	0.66436 (7)	0.0412 (3)
C33	0.8194 (2)	0.19123 (9)	0.65582 (8)	0.0496 (4)
H33	0.8870	0.1841	0.6245	0.060*
C34	0.7991 (2)	0.13664 (9)	0.69970 (8)	0.0519 (4)
H34	0.8520	0.0896	0.7005	0.062*
C35	0.6957 (2)	0.15988 (10)	0.73985 (8)	0.0561 (4)
H35	0.6686	0.1309	0.7719	0.067*
C56	0.76479 (18)	0.57556 (8)	0.49951 (6)	0.0392 (3)	0.9763 (18)
H56	0.8624	0.5560	0.4862	0.047*	0.9763 (18)
S51	0.54739 (6)	0.69862 (3)	0.49768 (2)	0.0496 (2)	0.9763 (18)
C52	0.71238 (18)	0.64605 (9)	0.47452 (9)	0.0376 (4)	0.9763 (18)
C53	0.7855 (3)	0.68004 (13)	0.42842 (10)	0.0480 (4)	0.9763 (18)
H53	0.8759	0.6603	0.4099	0.058*	0.9763 (18)
C54	0.7063 (2)	0.74942 (10)	0.41224 (8)	0.0547 (4)	0.9763 (18)
H54	0.7382	0.7796	0.3814	0.066*	0.9763 (18)
C55	0.5796 (3)	0.76645 (11)	0.44661 (8)	0.0556 (5)	0.9763 (18)
H55	0.5170	0.8104	0.4428	0.067*	0.9763 (18)
C66	0.76479 (18)	0.57556 (8)	0.49951 (6)	0.0392 (3)	0.0237 (18)
H66	0.8693	0.5630	0.4883	0.047*	0.0237 (18)
S61	0.761 (4)	0.6994 (14)	0.4220 (12)	0.0480 (4)	0.0237 (18)
C62	0.683 (6)	0.639 (4)	0.474 (3)	0.0376 (4)	0.0237 (18)
C63	0.531 (4)	0.662 (3)	0.490 (3)	0.04958 (15)	0.0237 (18)
H63	0.4569	0.6327	0.5101	0.059*	0.0237 (18)
C64	0.504 (6)	0.740 (2)	0.472 (2)	0.0556 (5)	0.0237 (18)
H64	0.4302	0.7729	0.4886	0.067*	0.0237 (18)
C65	0.598 (7)	0.758 (3)	0.426 (3)	0.0547 (4)	0.0237 (18)
H65	0.5756	0.7974	0.4005	0.066*	0.0237 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0380 (6)	0.0322 (5)	0.0411 (6)	−0.0013 (5)	0.0031 (5)	0.0017 (4)
C2	0.0350 (6)	0.0295 (6)	0.0366 (6)	−0.0011 (5)	0.0004 (5)	−0.0032 (5)
N3	0.0371 (6)	0.0324 (5)	0.0447 (6)	0.0010 (5)	0.0040 (5)	0.0036 (5)
C4	0.0360 (7)	0.0372 (7)	0.0522 (8)	−0.0024 (6)	0.0060 (6)	0.0022 (6)
O41	0.0416 (6)	0.0473 (6)	0.0926 (10)	0.0093 (5)	0.0222 (6)	0.0159 (6)
C5	0.0369 (7)	0.0334 (6)	0.0447 (7)	−0.0031 (5)	0.0016 (6)	−0.0007 (5)
C21	0.0368 (6)	0.0304 (6)	0.0344 (6)	−0.0018 (5)	0.0030 (5)	−0.0051 (5)
C22	0.0476 (8)	0.0380 (7)	0.0449 (8)	0.0043 (6)	0.0074 (7)	0.0054 (6)
C23	0.0457 (8)	0.0516 (9)	0.0583 (9)	0.0124 (7)	0.0085 (7)	0.0066 (7)
C24	0.0455 (8)	0.0541 (9)	0.0568 (9)	0.0032 (7)	0.0169 (7)	0.0019 (7)
C25	0.0585 (10)	0.0527 (9)	0.0481 (8)	0.0032 (8)	0.0181 (8)	0.0118 (7)
C26	0.0473 (8)	0.0451 (8)	0.0410 (7)	0.0076 (6)	0.0052 (6)	0.0062 (6)
N31	0.0437 (6)	0.0310 (5)	0.0458 (6)	0.0001 (5)	0.0011 (5)	0.0055 (5)
C36	0.0484 (8)	0.0369 (7)	0.0451 (7)	0.0028 (6)	0.0057 (6)	0.0024 (6)
S31	0.0729 (3)	0.0491 (2)	0.0644 (3)	0.0114 (2)	0.0236 (2)	0.0113 (2)
C32	0.0441 (7)	0.0348 (7)	0.0448 (7)	0.0009 (6)	0.0016 (6)	0.0023 (6)
C33	0.0553 (9)	0.0413 (8)	0.0522 (9)	0.0081 (7)	0.0063 (7)	0.0030 (7)
C34	0.0547 (9)	0.0364 (7)	0.0645 (10)	0.0055 (7)	−0.0056 (8)	0.0069 (7)
C35	0.0652 (11)	0.0453 (8)	0.0578 (10)	−0.0023 (8)	0.0001 (9)	0.0157 (7)
C56	0.0363 (7)	0.0354 (7)	0.0458 (7)	−0.0033 (5)	0.0037 (6)	−0.0012 (6)
S51	0.0520 (2)	0.0488 (3)	0.0480 (2)	0.01105 (18)	0.00475 (18)	0.00530 (17)
C52	0.0382 (8)	0.0343 (7)	0.0402 (7)	−0.0054 (6)	0.0000 (7)	−0.0019 (6)
C53	0.0522 (11)	0.0368 (11)	0.0549 (10)	−0.0043 (8)	0.0021 (8)	0.0057 (8)
C54	0.0653 (11)	0.0440 (9)	0.0549 (10)	−0.0082 (8)	−0.0003 (9)	0.0131 (7)
C55	0.0649 (11)	0.0448 (9)	0.0570 (11)	0.0071 (8)	−0.0069 (10)	0.0097 (8)
C66	0.0363 (7)	0.0354 (7)	0.0458 (7)	−0.0033 (5)	0.0037 (6)	−0.0012 (6)
S61	0.0522 (11)	0.0368 (11)	0.0549 (10)	−0.0043 (8)	0.0021 (8)	0.0057 (8)
C62	0.0382 (8)	0.0343 (7)	0.0402 (7)	−0.0054 (6)	0.0000 (7)	−0.0019 (6)
C63	0.0520 (2)	0.0488 (3)	0.0480 (2)	0.01105 (18)	0.00475 (18)	0.00530 (17)
C64	0.0649 (11)	0.0448 (9)	0.0570 (11)	0.0071 (8)	−0.0069 (10)	0.0097 (8)
C65	0.0653 (11)	0.0440 (9)	0.0549 (10)	−0.0082 (8)	−0.0003 (9)	0.0131 (7)

Geometric parameters (Å, º)

N1—C2	1.3043 (17)	C32—C33	1.368 (2)
N1—C5	1.3836 (19)	C33—C34	1.409 (2)
C2—N3	1.4004 (17)	C33—H33	0.9300
C2—C21	1.4710 (19)	C34—C35	1.332 (3)
N3—N31	1.3872 (16)	C34—H34	0.9300
N3—C4	1.4040 (19)	C35—H35	0.9300
C4—O41	1.2117 (18)	C56—C52	1.429 (2)
C4—C5	1.473 (2)	C56—H56	0.9300
C5—C56	1.347 (2)	S51—C55	1.701 (2)
C21—C26	1.388 (2)	S51—C52	1.7311 (18)
C21—C22	1.399 (2)	C52—C53	1.370 (3)
C22—C23	1.377 (2)	C53—C54	1.428 (3)
C22—H22	0.9300	C53—H53	0.9300
C23—C24	1.373 (2)	C54—C55	1.353 (3)
C23—H23	0.9300	C54—H54	0.9300
C24—C25	1.378 (3)	C55—H55	0.9300
C24—H24	0.9300	S61—C65	1.699 (10)
C25—C26	1.386 (2)	S61—C62	1.732 (10)
C25—H25	0.9300	C62—C63	1.374 (10)
C26—H26	0.9300	C63—C64	1.431 (10)
N31—C36	1.2872 (19)	C63—H63	0.9300
C36—C32	1.438 (2)	C64—C65	1.355 (10)
C36—H36	0.9300	C64—H64	0.9300
S31—C35	1.7071 (18)	C65—H65	0.9300
S31—C32	1.7099 (16)
C2—N1—C5	107.02 (12)	C36—C32—S31	123.03 (11)
N1—C2—N3	112.35 (12)	C32—C33—C34	112.68 (15)
N1—C2—C21	121.71 (12)	C32—C33—H33	123.7
N3—C2—C21	125.82 (12)	C34—C33—H33	123.7
N31—N3—C2	123.24 (12)	C35—C34—C33	112.48 (15)
N31—N3—C4	128.23 (12)	C35—C34—H34	123.8
C2—N3—C4	108.30 (11)	C33—C34—H34	123.8
O41—C4—N3	126.90 (14)	C34—C35—S31	112.59 (13)
O41—C4—C5	130.77 (14)	C34—C35—H35	123.7
N3—C4—C5	102.33 (12)	S31—C35—H35	123.7
C56—C5—N1	126.42 (14)	C5—C56—C52	127.39 (15)
C56—C5—C4	123.57 (14)	C5—C56—H56	116.3
N1—C5—C4	109.98 (12)	C52—C56—H56	116.3
C26—C21—C22	118.68 (13)	C55—S51—C52	91.51 (9)
C26—C21—C2	125.46 (13)	C53—C52—C56	124.03 (17)
C22—C21—C2	115.85 (12)	C53—C52—S51	111.36 (14)
C23—C22—C21	120.66 (14)	C56—C52—S51	124.60 (12)
C23—C22—H22	119.7	C52—C53—C54	111.86 (19)
C21—C22—H22	119.7	C52—C53—H53	124.1
C24—C23—C22	120.26 (16)	C54—C53—H53	124.1
C24—C23—H23	119.9	C55—C54—C53	112.64 (17)
C22—C23—H23	119.9	C55—C54—H54	123.7
C23—C24—C25	119.74 (15)	C53—C54—H54	123.7
C23—C24—H24	120.1	C54—C55—S51	112.59 (14)
C25—C24—H24	120.1	C54—C55—H55	123.7
C24—C25—C26	120.74 (15)	S51—C55—H55	123.7
C24—C25—H25	119.6	C65—S61—C62	91.6 (7)
C26—C25—H25	119.6	C63—C62—S61	110.6 (9)
C25—C26—C21	119.91 (15)	C62—C63—C64	110.1 (14)
C25—C26—H26	120.0	C62—C63—H63	124.9
C21—C26—H26	120.0	C64—C63—H63	124.9
C36—N31—N3	116.94 (13)	C65—C64—C63	111.5 (14)
N31—C36—C32	120.26 (14)	C65—C64—H64	124.2
N31—C36—H36	119.9	C63—C64—H64	124.2
C32—C36—H36	119.9	C64—C65—S61	111.1 (12)
C35—S31—C32	91.44 (8)	C64—C65—H65	124.5
C33—C32—C36	126.15 (15)	S61—C65—H65	124.5
C33—C32—S31	110.81 (12)
C5—N1—C2—N3	−0.36 (16)	C2—N3—N31—C36	162.33 (14)
C5—N1—C2—C21	−176.58 (12)	C4—N3—N31—C36	−23.9 (2)
N1—C2—N3—N31	174.56 (12)	N3—N31—C36—C32	179.49 (13)
C21—C2—N3—N31	−9.4 (2)	N31—C36—C32—C33	−179.62 (17)
N1—C2—N3—C4	−0.32 (16)	N31—C36—C32—S31	1.9 (2)
C21—C2—N3—C4	175.71 (13)	C35—S31—C32—C33	0.32 (14)
N31—N3—C4—O41	6.4 (3)	C35—S31—C32—C36	178.98 (15)
C2—N3—C4—O41	−179.10 (17)	C36—C32—C33—C34	−178.92 (16)
N31—N3—C4—C5	−173.76 (13)	S31—C32—C33—C34	−0.3 (2)
C2—N3—C4—C5	0.80 (15)	C32—C33—C34—C35	0.1 (2)
C2—N1—C5—C56	178.84 (15)	C33—C34—C35—S31	0.1 (2)
C2—N1—C5—C4	0.88 (16)	C32—S31—C35—C34	−0.25 (16)
O41—C4—C5—C56	0.8 (3)	N1—C5—C56—C52	0.6 (3)
N3—C4—C5—C56	−179.06 (14)	C4—C5—C56—C52	178.29 (16)
O41—C4—C5—N1	178.85 (18)	C5—C56—C52—C53	−171.51 (19)
N3—C4—C5—N1	−1.03 (16)	C5—C56—C52—S51	7.5 (3)
N1—C2—C21—C26	−166.60 (14)	C55—S51—C52—C53	−1.11 (18)
N3—C2—C21—C26	17.7 (2)	C55—S51—C52—C56	179.79 (17)
N1—C2—C21—C22	13.90 (19)	C56—C52—C53—C54	179.28 (18)
N3—C2—C21—C22	−161.79 (14)	S51—C52—C53—C54	0.2 (2)
C26—C21—C22—C23	−0.6 (2)	C52—C53—C54—C55	1.2 (3)
C2—C21—C22—C23	178.89 (15)	C53—C54—C55—S51	−2.1 (2)
C21—C22—C23—C24	0.4 (3)	C52—S51—C55—C54	1.82 (17)
C22—C23—C24—C25	0.4 (3)	C65—S61—C62—C63	4 (7)
C23—C24—C25—C26	−1.0 (3)	S61—C62—C63—C64	−16 (8)
C24—C25—C26—C21	0.7 (3)	C62—C63—C64—C65	24 (7)
C22—C21—C26—C25	0.1 (2)	C63—C64—C65—S61	−22 (7)
C2—C21—C26—C25	−179.38 (15)	C62—S61—C65—C64	10 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C56—H56···O41^i	0.93	2.38	3.2270 (19)	151
C35—H35···Cg2^ii	0.93	2.99	3.7477 (19)	149

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

(VI) Methyl (2Z)-2-(benzoylamino)-3-(thiophen-2-yl)prop-2-enoate

Crystal data

C15H13NO3S	Dx = 1.326 Mg m^−3
Mr = 287.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 5464 reflections
a = 16.6123 (3) Å	θ = 2.3–33.3°
b = 9.7589 (2) Å	µ = 0.23 mm^−1
c = 17.7543 (4) Å	T = 296 K
V = 2878.29 (10) Å^3	Plate, yellow
Z = 8	0.45 × 0.25 × 0.15 mm
F(000) = 1200

Data collection

Bruker APEXII CCD diffractometer	3292 independent reflections
Radiation source: sealed tube	2439 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −21→21
Tmin = 0.881, Tmax = 0.966	k = −12→10
18087 measured reflections	l = −23→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.042P)^2 + 1.4284P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
3292 reflections	Δρmax = 0.27 e Å^−3
185 parameters	Δρmin = −0.40 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.

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

	x	y	z	Uiso*/Ueq
C1	0.39384 (11)	0.62770 (18)	0.53738 (11)	0.0442 (4)
C2	0.31535 (10)	0.57995 (17)	0.50811 (10)	0.0384 (4)
C3	0.29934 (11)	0.5682 (2)	0.43467 (10)	0.0455 (4)
H3	0.3406	0.5950	0.4024	0.055*
O1	0.40936 (9)	0.63862 (17)	0.60332 (8)	0.0641 (4)
O2	0.44645 (8)	0.65538 (15)	0.48255 (8)	0.0564 (4)
C4	0.52373 (13)	0.7078 (3)	0.50626 (16)	0.0749 (7)
H4A	0.5486	0.6437	0.5400	0.112*
H4B	0.5164	0.7939	0.5315	0.112*
H4C	0.5575	0.7208	0.4630	0.112*
N21	0.25788 (9)	0.54444 (15)	0.56377 (8)	0.0385 (3)
H21	0.2558 (13)	0.464 (2)	0.5794 (11)	0.046*
C27	0.21473 (10)	0.64027 (17)	0.60024 (10)	0.0381 (4)
O27	0.22034 (9)	0.76190 (13)	0.58389 (9)	0.0590 (4)
C21	0.15897 (11)	0.59269 (19)	0.66080 (10)	0.0409 (4)
C22	0.13345 (11)	0.4583 (2)	0.66694 (11)	0.0459 (4)
H22	0.1503	0.3934	0.6319	0.055*
C23	0.08261 (13)	0.4202 (3)	0.72545 (13)	0.0627 (6)
H23	0.0649	0.3300	0.7291	0.075*
C24	0.05840 (13)	0.5149 (3)	0.77779 (13)	0.0712 (7)
H24	0.0251	0.4885	0.8173	0.085*
C25	0.08327 (16)	0.6481 (3)	0.77185 (13)	0.0749 (8)
H25	0.0667	0.7123	0.8073	0.090*
C26	0.13294 (14)	0.6876 (2)	0.71336 (12)	0.0609 (6)
H26	0.1490	0.7786	0.7093	0.073*
S31	0.14184 (3)	0.46353 (6)	0.44381 (3)	0.05686 (18)
C32	0.22727 (11)	0.5198 (2)	0.39847 (11)	0.0468 (4)
C33	0.21761 (13)	0.5075 (3)	0.32222 (12)	0.0665 (6)
H33	0.2572	0.5320	0.2877	0.080*
C34	0.14263 (14)	0.4544 (3)	0.30099 (14)	0.0694 (7)
H34	0.1270	0.4403	0.2513	0.083*
C35	0.09598 (14)	0.4264 (3)	0.36063 (13)	0.0657 (6)
H35	0.0443	0.3905	0.3569	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0444 (10)	0.0339 (9)	0.0542 (11)	0.0028 (8)	−0.0018 (8)	0.0021 (8)
C2	0.0400 (9)	0.0312 (8)	0.0440 (9)	0.0007 (7)	0.0028 (7)	0.0025 (7)
C3	0.0388 (9)	0.0513 (11)	0.0465 (10)	−0.0001 (8)	0.0046 (8)	0.0021 (9)
O1	0.0583 (9)	0.0797 (11)	0.0541 (8)	−0.0039 (8)	−0.0104 (7)	−0.0067 (8)
O2	0.0411 (7)	0.0644 (9)	0.0637 (9)	−0.0106 (7)	−0.0007 (6)	0.0089 (7)
C4	0.0450 (11)	0.0787 (17)	0.1009 (19)	−0.0156 (12)	−0.0066 (12)	0.0080 (15)
N21	0.0467 (8)	0.0246 (7)	0.0441 (8)	0.0005 (6)	0.0060 (7)	0.0044 (6)
C27	0.0407 (9)	0.0282 (8)	0.0453 (9)	−0.0007 (7)	−0.0055 (7)	−0.0015 (7)
O27	0.0710 (9)	0.0261 (7)	0.0799 (10)	0.0005 (6)	0.0096 (8)	0.0023 (6)
C21	0.0409 (9)	0.0403 (9)	0.0416 (9)	0.0053 (8)	−0.0013 (7)	−0.0015 (8)
C22	0.0408 (9)	0.0486 (11)	0.0484 (10)	−0.0030 (8)	0.0033 (8)	0.0005 (9)
C23	0.0450 (11)	0.0761 (16)	0.0668 (14)	−0.0076 (11)	0.0052 (10)	0.0154 (12)
C24	0.0461 (11)	0.115 (2)	0.0524 (13)	0.0162 (14)	0.0085 (10)	0.0165 (14)
C25	0.0756 (16)	0.098 (2)	0.0515 (13)	0.0335 (16)	0.0116 (12)	−0.0083 (13)
C26	0.0698 (14)	0.0551 (13)	0.0577 (12)	0.0145 (11)	0.0051 (11)	−0.0102 (11)
S31	0.0482 (3)	0.0679 (4)	0.0544 (3)	−0.0136 (3)	−0.0010 (2)	0.0058 (3)
C32	0.0417 (9)	0.0525 (11)	0.0464 (10)	0.0021 (9)	0.0005 (8)	0.0004 (9)
C33	0.0534 (12)	0.0997 (19)	0.0464 (11)	−0.0023 (13)	0.0012 (9)	−0.0019 (12)
C34	0.0644 (14)	0.0890 (18)	0.0547 (13)	−0.0059 (13)	−0.0158 (11)	−0.0020 (12)
C35	0.0551 (12)	0.0722 (15)	0.0697 (14)	−0.0126 (12)	−0.0142 (11)	0.0088 (12)

Geometric parameters (Å, º)

C1—O1	1.204 (2)	C22—C23	1.389 (3)
C1—O2	1.336 (2)	C22—H22	0.9300
C1—C2	1.479 (3)	C23—C24	1.371 (4)
C2—C3	1.336 (2)	C23—H23	0.9300
C2—N21	1.417 (2)	C24—C25	1.368 (4)
C3—C32	1.439 (3)	C24—H24	0.9300
C3—H3	0.9300	C25—C26	1.381 (3)
O2—C4	1.445 (2)	C25—H25	0.9300
C4—H4A	0.9600	C26—H26	0.9300
C4—H4B	0.9600	S31—C35	1.701 (2)
C4—H4C	0.9600	S31—C32	1.7214 (19)
N21—C27	1.345 (2)	C32—C33	1.369 (3)
N21—H21	0.83 (2)	C33—C34	1.401 (3)
C27—O27	1.225 (2)	C33—H33	0.9300
C27—C21	1.493 (3)	C34—C35	1.341 (3)
C21—C22	1.383 (3)	C34—H34	0.9300
C21—C26	1.384 (3)	C35—H35	0.9300
O1—C1—O2	123.42 (18)	C23—C22—H22	120.0
O1—C1—C2	123.96 (18)	C24—C23—C22	120.3 (2)
O2—C1—C2	112.61 (16)	C24—C23—H23	119.8
C3—C2—N21	121.70 (16)	C22—C23—H23	119.8
C3—C2—C1	123.07 (16)	C25—C24—C23	120.0 (2)
N21—C2—C1	115.21 (15)	C25—C24—H24	120.0
C2—C3—C32	129.06 (17)	C23—C24—H24	120.0
C2—C3—H3	115.5	C24—C25—C26	120.2 (2)
C32—C3—H3	115.5	C24—C25—H25	119.9
C1—O2—C4	116.16 (17)	C26—C25—H25	119.9
O2—C4—H4A	109.5	C25—C26—C21	120.5 (2)
O2—C4—H4B	109.5	C25—C26—H26	119.8
H4A—C4—H4B	109.5	C21—C26—H26	119.8
O2—C4—H4C	109.5	C35—S31—C32	91.79 (11)
H4A—C4—H4C	109.5	C33—C32—C3	124.63 (18)
H4B—C4—H4C	109.5	C33—C32—S31	109.75 (15)
C27—N21—C2	121.66 (15)	C3—C32—S31	125.59 (14)
C27—N21—H21	118.2 (14)	C32—C33—C34	113.8 (2)
C2—N21—H21	119.4 (14)	C32—C33—H33	123.1
O27—C27—N21	121.27 (17)	C34—C33—H33	123.1
O27—C27—C21	121.26 (17)	C35—C34—C33	112.1 (2)
N21—C27—C21	117.46 (15)	C35—C34—H34	123.9
C22—C21—C26	119.06 (18)	C33—C34—H34	123.9
C22—C21—C27	122.81 (16)	C34—C35—S31	112.54 (18)
C26—C21—C27	118.12 (18)	C34—C35—H35	123.7
C21—C22—C23	119.9 (2)	S31—C35—H35	123.7
C21—C22—H22	120.0
O1—C1—C2—C3	−179.81 (19)	C27—C21—C22—C23	178.87 (17)
O2—C1—C2—C3	−0.9 (3)	C21—C22—C23—C24	−0.9 (3)
O1—C1—C2—N21	−1.0 (3)	C22—C23—C24—C25	1.0 (3)
O2—C1—C2—N21	177.93 (15)	C23—C24—C25—C26	−0.2 (4)
N21—C2—C3—C32	−0.7 (3)	C24—C25—C26—C21	−0.9 (4)
C1—C2—C3—C32	178.00 (19)	C22—C21—C26—C25	1.1 (3)
O1—C1—O2—C4	−3.4 (3)	C27—C21—C26—C25	−178.04 (19)
C2—C1—O2—C4	177.66 (17)	C2—C3—C32—C33	−177.8 (2)
C3—C2—N21—C27	−101.8 (2)	C2—C3—C32—S31	−0.1 (3)
C1—C2—N21—C27	79.4 (2)	C35—S31—C32—C33	−0.28 (19)
C2—N21—C27—O27	3.9 (3)	C35—S31—C32—C3	−178.27 (19)
C2—N21—C27—C21	−176.77 (15)	C3—C32—C33—C34	178.3 (2)
O27—C27—C21—C22	161.07 (18)	S31—C32—C33—C34	0.3 (3)
N21—C27—C21—C22	−18.2 (3)	C32—C33—C34—C35	−0.2 (3)
O27—C27—C21—C26	−19.8 (3)	C33—C34—C35—S31	0.0 (3)
N21—C27—C21—C26	160.87 (17)	C32—S31—C35—C34	0.2 (2)
C26—C21—C22—C23	−0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O27^i	0.85 (2)	2.01 (2)	2.8038 (19)	158.1 (19)
C33—H33···Cg2^ii	0.93	2.68	3.472 (3)	144
C35—H35···Cg2^iii	0.93	2.92	3.684 (2)	140

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