Crystallographic study of self-organization in the solid state including quasi-aromatic pseudo-ring stacking inter­actions in 1-benzoyl-3-(3,4-di­methoxy­phen­yl)thio­urea and 1-benzoyl-3-(2-hy­droxy­prop­yl)thio­urea

1-Benzoyl­thio­ureas contain both carbonyl and thio­carbonyl functional groups and are of interest for their biological activity, metal coordination ability and involvement in hydrogen-bond formation. Two novel 1-benzoyl­thio­urea derivatives, namely 1-benzoyl-3-(3,4-di­meth­oxy­phen­yl)thio­urea, C₁₆H₁₆N₂O₃S, (I), and 1-benzoyl-3-(2-hy­droxy­prop­yl)thio­urea, C₁₁H₁₄N₂O₂S, (II), have been synthesized and characterized. Compound (I) crystallizes in the space group P, while (II) crystallizes in the space group P2₁/c. In both structures, intra­molecular N—H...O hydrogen bonding is present. The resulting six-membered pseudo-rings are quasi-aromatic and, in each case, inter­act with phenyl rings via stacking-type inter­actions. C—H...O, C—H...S and C—H...π inter­actions are also present. In (I), there is one mol­ecule in the asymmetric unit. Pairs of mol­ecules are connected via two inter­molecular N—H...S hydrogen bonds, forming centrosymmetric dimers. In (II), there are two symmetry-independent mol­ecules that differ mainly in the relative orientations of the phenyl rings with respect to the thiourea cores. Additional strong hydrogen-bond donor and acceptor –OH groups participate in the formation of inter­molecular N—H...O and O—H...S hydrogen bonds that join mol­ecules into chains extending in the [001] direction.

Computing details

For both compounds, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS2016 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

(I) N-[(3,4-Dimethoxyphenyl)carbamothioyl]benzamide

Crystal data

C16H16N2O3S	Z = 2
Mr = 316.37	F(000) = 332
Triclinic, P1	Dx = 1.356 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5450 (4) Å	Cell parameters from 1629 reflections
b = 9.3526 (6) Å	θ = 2.7–26.2°
c = 12.7820 (8) Å	µ = 0.22 mm^−1
α = 94.047 (5)°	T = 293 K
β = 93.143 (5)°	Prism, colourless
γ = 95.735 (5)°	0.73 × 0.41 × 0.27 mm
V = 775.05 (8) Å^3

Data collection

Agilent Xcalibur (Sapphire2, large Be window) diffractometer	3039 independent reflections
Graphite monochromator	1883 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm^-1	Rint = 0.026
ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: analytical [CrysAlis PRO (Agilent, 2013), based on expressions derived by Clark & Reid (1995)]	h = −6→8
Tmin = 0.923, Tmax = 0.959	k = −11→10
4858 measured reflections	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.071	H-atom parameters constrained
wR(F^2) = 0.209	w = 1/[σ^2(Fo^2) + (0.1069P)^2 + 0.0208P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3039 reflections	Δρmax = 0.59 e Å^−3
201 parameters	Δρmin = −0.25 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	0.32892 (14)	0.32856 (10)	0.05322 (7)	0.0746 (4)
C1	0.4131 (5)	0.4076 (3)	0.1704 (2)	0.0525 (8)
N1	0.5964 (4)	0.4994 (3)	0.1768 (2)	0.0573 (7)
H1	0.657793	0.504603	0.119202	0.069*
C10	0.6924 (5)	0.5822 (3)	0.2617 (3)	0.0532 (8)
O1	0.6254 (3)	0.5821 (3)	0.34928 (18)	0.0712 (7)
C11	0.8843 (4)	0.6730 (3)	0.2414 (2)	0.0539 (8)
C12	0.9348 (5)	0.7985 (4)	0.3058 (3)	0.0662 (10)
H12	0.847406	0.823665	0.357432	0.079*
C13	1.1126 (6)	0.8867 (4)	0.2942 (3)	0.0781 (11)
H13	1.145054	0.970734	0.337792	0.094*
C14	1.2425 (5)	0.8490 (5)	0.2174 (3)	0.0797 (12)
H14	1.363019	0.907938	0.209513	0.096*
C15	1.1947 (5)	0.7253 (4)	0.1527 (3)	0.0740 (11)
H15	1.282663	0.701004	0.101048	0.089*
C16	1.0151 (5)	0.6361 (4)	0.1640 (3)	0.0635 (9)
H16	0.982791	0.552392	0.120094	0.076*
N2	0.3251 (4)	0.3968 (3)	0.26128 (19)	0.0560 (7)
H2	0.397118	0.442046	0.313960	0.067*
C21	0.1357 (4)	0.3255 (3)	0.2886 (2)	0.0502 (8)
C22	0.0066 (5)	0.2298 (3)	0.2205 (2)	0.0544 (8)
H22	0.043178	0.207574	0.152455	0.065*
C23	−0.1769 (5)	0.1676 (3)	0.2545 (2)	0.0539 (8)
C24	−0.2322 (5)	0.2002 (3)	0.3560 (3)	0.0537 (8)
C25	−0.1021 (5)	0.2949 (4)	0.4232 (3)	0.0621 (9)
H25	−0.138185	0.317599	0.491289	0.075*
C26	0.0820 (5)	0.3560 (4)	0.3894 (3)	0.0597 (9)
H26	0.169978	0.418272	0.435404	0.072*
C2	−0.2492 (6)	0.0273 (4)	0.0926 (3)	0.0800 (12)
H2A	−0.235014	0.109237	0.051399	0.120*
H2B	−0.351384	−0.044283	0.058549	0.120*
H2C	−0.119844	−0.012469	0.099279	0.120*
O2	−0.3101 (3)	0.0704 (3)	0.19344 (18)	0.0705 (7)
C3	−0.4927 (6)	0.1837 (5)	0.4788 (3)	0.0822 (12)
H3A	−0.402770	0.159968	0.535411	0.123*
H3B	−0.628717	0.137493	0.485211	0.123*
H3C	−0.496586	0.286205	0.481580	0.123*
O3	−0.4187 (3)	0.1352 (3)	0.38104 (18)	0.0715 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0804 (7)	0.0811 (7)	0.0543 (6)	−0.0276 (5)	0.0185 (5)	−0.0112 (5)
C1	0.0475 (18)	0.0529 (19)	0.056 (2)	−0.0036 (14)	0.0098 (14)	0.0031 (15)
N1	0.0499 (15)	0.0656 (18)	0.0532 (16)	−0.0093 (13)	0.0125 (12)	−0.0025 (13)
C10	0.0481 (18)	0.059 (2)	0.0511 (19)	−0.0005 (15)	0.0031 (14)	0.0002 (15)
O1	0.0658 (15)	0.0902 (18)	0.0508 (14)	−0.0209 (12)	0.0091 (11)	−0.0049 (12)
C11	0.0447 (18)	0.059 (2)	0.056 (2)	−0.0046 (14)	0.0013 (14)	0.0027 (15)
C12	0.063 (2)	0.071 (2)	0.061 (2)	−0.0083 (18)	0.0038 (16)	−0.0002 (17)
C13	0.073 (3)	0.073 (3)	0.081 (3)	−0.018 (2)	−0.010 (2)	0.009 (2)
C14	0.051 (2)	0.091 (3)	0.093 (3)	−0.021 (2)	−0.002 (2)	0.026 (2)
C15	0.050 (2)	0.091 (3)	0.083 (3)	0.0012 (19)	0.0157 (18)	0.021 (2)
C16	0.052 (2)	0.067 (2)	0.071 (2)	0.0025 (16)	0.0069 (16)	0.0079 (18)
N2	0.0535 (15)	0.0650 (18)	0.0453 (15)	−0.0131 (13)	0.0068 (12)	−0.0015 (12)
C21	0.0500 (18)	0.0528 (19)	0.0462 (18)	−0.0044 (14)	0.0094 (13)	0.0029 (13)
C22	0.0534 (18)	0.063 (2)	0.0443 (17)	−0.0072 (15)	0.0099 (14)	−0.0006 (14)
C23	0.0507 (19)	0.0526 (19)	0.056 (2)	−0.0052 (14)	0.0073 (14)	0.0011 (15)
C24	0.0498 (18)	0.0535 (19)	0.059 (2)	0.0003 (15)	0.0186 (15)	0.0057 (15)
C25	0.071 (2)	0.061 (2)	0.055 (2)	0.0026 (17)	0.0228 (16)	0.0009 (16)
C26	0.062 (2)	0.063 (2)	0.0510 (19)	−0.0061 (16)	0.0082 (15)	−0.0026 (15)
C2	0.075 (2)	0.097 (3)	0.059 (2)	−0.022 (2)	0.0073 (18)	−0.016 (2)
O2	0.0577 (14)	0.0827 (17)	0.0639 (15)	−0.0223 (12)	0.0134 (11)	−0.0108 (12)
C3	0.066 (2)	0.108 (3)	0.074 (3)	0.001 (2)	0.0301 (19)	0.005 (2)
O3	0.0632 (15)	0.0813 (17)	0.0683 (16)	−0.0092 (12)	0.0278 (12)	−0.0020 (12)

Geometric parameters (Å, º)

S1—C1	1.663 (3)	C21—C26	1.372 (4)
C1—N2	1.330 (4)	C21—C22	1.389 (4)
C1—N1	1.399 (4)	C22—C23	1.387 (4)
N1—C10	1.372 (4)	C22—H22	0.9300
N1—H1	0.8600	C23—O2	1.365 (4)
C10—O1	1.224 (4)	C23—C24	1.387 (4)
C10—C11	1.490 (4)	C24—O3	1.373 (3)
C11—C12	1.386 (4)	C24—C25	1.382 (5)
C11—C16	1.391 (4)	C25—C26	1.386 (4)
C12—C13	1.379 (5)	C25—H25	0.9300
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.384 (6)	C2—O2	1.414 (4)
C13—H13	0.9300	C2—H2A	0.9600
C14—C15	1.373 (5)	C2—H2B	0.9600
C14—H14	0.9300	C2—H2C	0.9600
C15—C16	1.392 (4)	C3—O3	1.426 (4)
C15—H15	0.9300	C3—H3A	0.9600
C16—H16	0.9300	C3—H3B	0.9600
N2—C21	1.421 (3)	C3—H3C	0.9600
N2—H2	0.8600
N2—C1—N1	114.3 (3)	C26—C21—N2	116.0 (3)
N2—C1—S1	127.9 (2)	C22—C21—N2	124.3 (3)
N1—C1—S1	117.8 (2)	C23—C22—C21	119.7 (3)
C10—N1—C1	129.3 (3)	C23—C22—H22	120.1
C10—N1—H1	115.3	C21—C22—H22	120.1
C1—N1—H1	115.3	O2—C23—C22	123.4 (3)
O1—C10—N1	122.4 (3)	O2—C23—C24	116.1 (3)
O1—C10—C11	121.6 (3)	C22—C23—C24	120.4 (3)
N1—C10—C11	116.1 (3)	O3—C24—C25	124.8 (3)
C12—C11—C16	119.3 (3)	O3—C24—C23	115.8 (3)
C12—C11—C10	117.2 (3)	C25—C24—C23	119.4 (3)
C16—C11—C10	123.5 (3)	C24—C25—C26	120.1 (3)
C13—C12—C11	120.9 (3)	C24—C25—H25	119.9
C13—C12—H12	119.5	C26—C25—H25	119.9
C11—C12—H12	119.5	C21—C26—C25	120.6 (3)
C12—C13—C14	119.5 (4)	C21—C26—H26	119.7
C12—C13—H13	120.3	C25—C26—H26	119.7
C14—C13—H13	120.3	O2—C2—H2A	109.5
C15—C14—C13	120.4 (3)	O2—C2—H2B	109.5
C15—C14—H14	119.8	H2A—C2—H2B	109.5
C13—C14—H14	119.8	O2—C2—H2C	109.5
C14—C15—C16	120.3 (3)	H2A—C2—H2C	109.5
C14—C15—H15	119.9	H2B—C2—H2C	109.5
C16—C15—H15	119.9	C23—O2—C2	117.0 (2)
C11—C16—C15	119.6 (3)	O3—C3—H3A	109.5
C11—C16—H16	120.2	O3—C3—H3B	109.5
C15—C16—H16	120.2	H3A—C3—H3B	109.5
C1—N2—C21	132.8 (3)	O3—C3—H3C	109.5
C1—N2—H2	113.6	H3A—C3—H3C	109.5
C21—N2—H2	113.6	H3B—C3—H3C	109.5
C26—C21—C22	119.7 (3)	C24—O3—C3	116.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.90	2.633 (3)	143
N1—H1···S1^i	0.86	2.79	3.485 (3)	139
C22—H22···S1	0.93	2.54	3.203 (3)	129
C14—H14···O2^ii	0.93	2.52	3.453 (4)	178

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

(II) N-[(2-Hydroxypropyl)carbamothioyl]benzamide

Crystal data

C11H14N2O2S	F(000) = 1008
Mr = 238.3	Dx = 1.32 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2940 reflections
a = 22.4150 (17) Å	θ = 3.0–27.0°
b = 8.1479 (5) Å	µ = 0.26 mm^−1
c = 13.4592 (9) Å	T = 293 K
β = 102.618 (7)°	Prism, colourless
V = 2398.8 (3) Å^3	0.52 × 0.46 × 0.14 mm
Z = 8

Data collection

Agilent Xcalibur (Sapphire2, large Be window) diffractometer	4710 independent reflections
Graphite monochromator	2847 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm^-1	Rint = 0.038
ω scans	θmax = 26°, θmin = 2.7°
Absorption correction: analytical [CrysAlis PRO (Agilent, 2013), based on expressions derived by Clark & Reid (1995)]	h = −27→26
Tmin = 0.911, Tmax = 0.971	k = −10→5
8922 measured reflections	l = −12→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.220	w = 1/[σ^2(Fo^2) + (0.1058P)^2 + 0.9789P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4710 reflections	Δρmax = 0.71 e Å^−3
293 parameters	Δρmin = −0.30 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	0.19684 (4)	0.87980 (15)	0.50453 (8)	0.0834 (4)
C1	0.13064 (15)	0.8780 (4)	0.5415 (2)	0.0551 (8)
N1	0.08038 (11)	0.7993 (3)	0.47955 (18)	0.0544 (6)
H1	0.086382	0.757529	0.423876	0.065*
C10	0.02251 (13)	0.7809 (4)	0.4973 (2)	0.0536 (7)
O1	0.00807 (11)	0.8385 (3)	0.57212 (18)	0.0733 (7)
C11	−0.02165 (14)	0.6848 (4)	0.4201 (2)	0.0513 (7)
C12	−0.07310 (15)	0.6253 (4)	0.4510 (3)	0.0628 (9)
H12	−0.078547	0.648068	0.516116	0.075*
C13	−0.11598 (17)	0.5328 (4)	0.3850 (3)	0.0715 (10)
H13	−0.150034	0.492347	0.405936	0.086*
C14	−0.10823 (17)	0.5005 (4)	0.2880 (3)	0.0694 (9)
H14	−0.137038	0.437750	0.243800	0.083*
C15	−0.05831 (17)	0.5604 (4)	0.2565 (3)	0.0691 (9)
H15	−0.053570	0.539344	0.190748	0.083*
C16	−0.01498 (16)	0.6522 (4)	0.3224 (2)	0.0601 (8)
H16	0.018903	0.692269	0.300705	0.072*
N2	0.12153 (12)	0.9439 (3)	0.62596 (19)	0.0591 (7)
H2	0.085767	0.934134	0.638807	0.071*
C21	0.16758 (15)	1.0322 (4)	0.6993 (2)	0.0606 (8)
H21A	0.174053	1.139570	0.672334	0.073*
H21B	0.205956	0.972713	0.710785	0.073*
C22	0.14791 (16)	1.0517 (4)	0.7982 (2)	0.0632 (9)
H22	0.108336	1.108048	0.782686	0.076*
C23	0.19148 (17)	1.1614 (5)	0.8704 (3)	0.0723 (10)
H23A	0.179488	1.166057	0.934629	0.108*
H23B	0.190453	1.269822	0.842165	0.108*
H23C	0.232187	1.118107	0.880391	0.108*
O2	0.13845 (13)	0.9014 (3)	0.8418 (2)	0.0840 (8)
H2A	0.171519	0.861159	0.868999	0.126*
S3	0.31682 (5)	0.65289 (16)	0.35460 (8)	0.0899 (4)
C3	0.38036 (16)	0.6539 (4)	0.4467 (2)	0.0604 (8)
N3	0.43299 (12)	0.7287 (3)	0.42895 (19)	0.0606 (7)
H3	0.429205	0.776266	0.370866	0.073*
C30	0.49006 (15)	0.7366 (4)	0.4918 (2)	0.0583 (8)
O3	0.50078 (11)	0.6740 (4)	0.57620 (19)	0.0813 (8)
C31	0.53756 (15)	0.8255 (4)	0.4511 (2)	0.0577 (8)
C32	0.59318 (17)	0.8526 (5)	0.5187 (3)	0.0763 (11)
H32	0.599071	0.815394	0.585456	0.092*
C33	0.63991 (19)	0.9348 (5)	0.4869 (3)	0.0855 (12)
H33	0.676964	0.953283	0.532325	0.103*
C34	0.63133 (18)	0.9883 (5)	0.3887 (3)	0.0778 (11)
H34	0.662525	1.044306	0.367595	0.093*
C35	0.57669 (18)	0.9599 (5)	0.3207 (3)	0.0820 (11)
H35	0.571295	0.995335	0.253641	0.098*
C36	0.53014 (16)	0.8791 (5)	0.3522 (3)	0.0730 (10)
H36	0.493314	0.860439	0.306177	0.088*
N4	0.38426 (13)	0.5899 (3)	0.5372 (2)	0.0658 (8)
H4	0.419002	0.591900	0.579720	0.079*
C41	0.33257 (17)	0.5161 (5)	0.5688 (3)	0.0723 (10)
H41A	0.317194	0.425266	0.523817	0.087*
H41B	0.300098	0.596451	0.563276	0.087*
C42	0.34964 (17)	0.4567 (5)	0.6734 (3)	0.0744 (10)
H42	0.379516	0.368619	0.674185	0.089*
C43	0.29559 (19)	0.3810 (6)	0.7075 (3)	0.0959 (14)
H43A	0.308436	0.342723	0.776353	0.144*
H43B	0.280074	0.290445	0.663856	0.144*
H43C	0.264075	0.461939	0.703996	0.144*
O4	0.37882 (12)	0.5781 (4)	0.7412 (2)	0.0909 (9)
H4A	0.353521	0.645707	0.750645	0.136*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0569 (6)	0.1220 (9)	0.0779 (7)	−0.0110 (5)	0.0288 (5)	−0.0136 (6)
C1	0.0531 (18)	0.0614 (18)	0.0516 (17)	0.0057 (15)	0.0131 (14)	0.0080 (14)
N1	0.0511 (15)	0.0676 (16)	0.0471 (13)	0.0035 (13)	0.0163 (12)	0.0003 (12)
C10	0.0463 (17)	0.0658 (18)	0.0505 (16)	0.0060 (15)	0.0145 (14)	0.0035 (14)
O1	0.0551 (14)	0.1070 (18)	0.0625 (14)	−0.0042 (13)	0.0234 (11)	−0.0203 (13)
C11	0.0478 (17)	0.0562 (17)	0.0502 (16)	0.0087 (14)	0.0115 (13)	0.0036 (13)
C12	0.0552 (19)	0.077 (2)	0.0576 (19)	0.0030 (17)	0.0150 (16)	0.0076 (16)
C13	0.060 (2)	0.074 (2)	0.080 (2)	−0.0027 (18)	0.0150 (19)	0.0137 (19)
C14	0.067 (2)	0.061 (2)	0.074 (2)	−0.0034 (18)	0.0016 (18)	−0.0027 (17)
C15	0.079 (2)	0.071 (2)	0.059 (2)	−0.001 (2)	0.0166 (18)	−0.0064 (17)
C16	0.064 (2)	0.0615 (18)	0.0571 (18)	0.0009 (16)	0.0192 (16)	−0.0009 (15)
N2	0.0488 (15)	0.0744 (17)	0.0548 (15)	−0.0031 (13)	0.0130 (12)	−0.0024 (13)
C21	0.0554 (19)	0.073 (2)	0.0521 (17)	−0.0063 (16)	0.0102 (15)	0.0043 (15)
C22	0.062 (2)	0.069 (2)	0.0584 (19)	−0.0039 (17)	0.0130 (16)	−0.0015 (16)
C23	0.066 (2)	0.085 (2)	0.063 (2)	0.0008 (19)	0.0075 (17)	−0.0092 (18)
O2	0.0850 (18)	0.0949 (19)	0.0745 (17)	−0.0147 (16)	0.0226 (15)	0.0151 (14)
S3	0.0696 (7)	0.1317 (10)	0.0633 (6)	−0.0337 (6)	0.0031 (5)	0.0118 (6)
C3	0.062 (2)	0.0653 (19)	0.0564 (19)	−0.0084 (16)	0.0195 (16)	−0.0024 (15)
N3	0.0547 (16)	0.0760 (18)	0.0521 (15)	−0.0081 (14)	0.0137 (12)	0.0068 (13)
C30	0.0555 (19)	0.0667 (19)	0.0538 (18)	−0.0005 (16)	0.0141 (15)	0.0007 (16)
O3	0.0641 (16)	0.113 (2)	0.0638 (15)	−0.0126 (14)	0.0075 (12)	0.0215 (14)
C31	0.0533 (19)	0.0629 (19)	0.0570 (18)	−0.0002 (15)	0.0122 (15)	−0.0021 (15)
C32	0.068 (2)	0.098 (3)	0.062 (2)	−0.021 (2)	0.0129 (18)	−0.0093 (19)
C33	0.069 (2)	0.106 (3)	0.081 (3)	−0.028 (2)	0.015 (2)	−0.015 (2)
C34	0.069 (2)	0.070 (2)	0.100 (3)	−0.0127 (19)	0.030 (2)	−0.003 (2)
C35	0.069 (2)	0.097 (3)	0.083 (3)	−0.005 (2)	0.022 (2)	0.026 (2)
C36	0.0507 (19)	0.090 (2)	0.076 (2)	−0.0053 (19)	0.0087 (17)	0.0187 (19)
N4	0.0625 (17)	0.0811 (19)	0.0542 (16)	−0.0181 (15)	0.0138 (13)	0.0022 (13)
C41	0.068 (2)	0.091 (2)	0.059 (2)	−0.022 (2)	0.0153 (17)	−0.0016 (18)
C42	0.067 (2)	0.097 (3)	0.061 (2)	−0.018 (2)	0.0192 (17)	−0.003 (2)
C43	0.074 (3)	0.144 (4)	0.072 (3)	−0.028 (3)	0.022 (2)	0.017 (2)
O4	0.0747 (18)	0.133 (3)	0.0643 (16)	−0.0221 (17)	0.0133 (14)	−0.0206 (16)

Geometric parameters (Å, º)

S1—C1	1.665 (3)	S3—C3	1.671 (4)
C1—N2	1.313 (4)	C3—N4	1.311 (4)
C1—N1	1.402 (4)	C3—N3	1.394 (4)
N1—C10	1.378 (4)	N3—C30	1.373 (4)
N1—H1	0.8600	N3—H3	0.8600
C10—O1	1.217 (4)	C30—O3	1.220 (4)
C10—C11	1.491 (4)	C30—C31	1.488 (4)
C11—C16	1.382 (4)	C31—C36	1.376 (5)
C11—C12	1.395 (4)	C31—C32	1.391 (5)
C12—C13	1.381 (5)	C32—C33	1.387 (5)
C12—H12	0.9300	C32—H32	0.9300
C13—C14	1.379 (5)	C33—C34	1.364 (6)
C13—H13	0.9300	C33—H33	0.9300
C14—C15	1.370 (5)	C34—C35	1.379 (5)
C14—H14	0.9300	C34—H34	0.9300
C15—C16	1.383 (5)	C35—C36	1.377 (5)
C15—H15	0.9300	C35—H35	0.9300
C16—H16	0.9300	C36—H36	0.9300
N2—C21	1.453 (4)	N4—C41	1.449 (4)
N2—H2	0.8600	N4—H4	0.8600
C21—C22	1.500 (4)	C41—C42	1.459 (5)
C21—H21A	0.9700	C41—H41A	0.9700
C21—H21B	0.9700	C41—H41B	0.9700
C22—O2	1.394 (4)	C42—O4	1.407 (4)
C22—C23	1.511 (5)	C42—C43	1.517 (5)
C22—H22	0.9800	C42—H42	0.9800
C23—H23A	0.9600	C43—H43A	0.9600
C23—H23B	0.9600	C43—H43B	0.9600
C23—H23C	0.9600	C43—H43C	0.9600
O2—H2A	0.8200	O4—H4A	0.8200
N2—C1—N1	116.4 (3)	N4—C3—N3	116.5 (3)
N2—C1—S1	124.9 (3)	N4—C3—S3	124.1 (3)
N1—C1—S1	118.7 (2)	N3—C3—S3	119.4 (2)
C10—N1—C1	127.7 (3)	C30—N3—C3	128.7 (3)
C10—N1—H1	116.1	C30—N3—H3	115.7
C1—N1—H1	116.1	C3—N3—H3	115.7
O1—C10—N1	122.2 (3)	O3—C30—N3	121.5 (3)
O1—C10—C11	121.5 (3)	O3—C30—C31	122.3 (3)
N1—C10—C11	116.3 (3)	N3—C30—C31	116.2 (3)
C16—C11—C12	119.0 (3)	C36—C31—C32	118.9 (3)
C16—C11—C10	124.8 (3)	C36—C31—C30	124.5 (3)
C12—C11—C10	116.2 (3)	C32—C31—C30	116.6 (3)
C13—C12—C11	120.2 (3)	C33—C32—C31	120.3 (4)
C13—C12—H12	119.9	C33—C32—H32	119.9
C11—C12—H12	119.9	C31—C32—H32	119.9
C14—C13—C12	119.9 (3)	C34—C33—C32	119.8 (4)
C14—C13—H13	120.0	C34—C33—H33	120.1
C12—C13—H13	120.0	C32—C33—H33	120.1
C15—C14—C13	120.3 (3)	C33—C34—C35	120.4 (4)
C15—C14—H14	119.8	C33—C34—H34	119.8
C13—C14—H14	119.8	C35—C34—H34	119.8
C14—C15—C16	120.1 (3)	C36—C35—C34	119.9 (4)
C14—C15—H15	120.0	C36—C35—H35	120.0
C16—C15—H15	120.0	C34—C35—H35	120.0
C11—C16—C15	120.5 (3)	C31—C36—C35	120.7 (3)
C11—C16—H16	119.8	C31—C36—H36	119.7
C15—C16—H16	119.8	C35—C36—H36	119.7
C1—N2—C21	124.7 (3)	C3—N4—C41	122.9 (3)
C1—N2—H2	117.7	C3—N4—H4	118.6
C21—N2—H2	117.7	C41—N4—H4	118.6
N2—C21—C22	110.6 (3)	N4—C41—C42	111.3 (3)
N2—C21—H21A	109.5	N4—C41—H41A	109.4
C22—C21—H21A	109.5	C42—C41—H41A	109.4
N2—C21—H21B	109.5	N4—C41—H41B	109.4
C22—C21—H21B	109.5	C42—C41—H41B	109.4
H21A—C21—H21B	108.1	H41A—C41—H41B	108.0
O2—C22—C21	112.4 (3)	O4—C42—C41	112.3 (3)
O2—C22—C23	112.7 (3)	O4—C42—C43	112.2 (3)
C21—C22—C23	111.1 (3)	C41—C42—C43	111.6 (3)
O2—C22—H22	106.7	O4—C42—H42	106.7
C21—C22—H22	106.7	C41—C42—H42	106.7
C23—C22—H22	106.7	C43—C42—H42	106.7
C22—C23—H23A	109.5	C42—C43—H43A	109.5
C22—C23—H23B	109.5	C42—C43—H43B	109.5
H23A—C23—H23B	109.5	H43A—C43—H43B	109.5
C22—C23—H23C	109.5	C42—C43—H43C	109.5
H23A—C23—H23C	109.5	H43A—C43—H43C	109.5
H23B—C23—H23C	109.5	H43B—C43—H43C	109.5
C22—O2—H2A	109.5	C42—O4—H4A	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.86	2.20	2.977 (3)	151
N2—H2···O1	0.86	1.94	2.632 (3)	137
O2—H2A···S1^ii	0.82	2.66	3.242 (3)	130
N3—H3···O4^i	0.86	2.21	2.999 (4)	153
N4—H4···O3	0.86	1.96	2.640 (4)	135
O4—H4A···S3^ii	0.82	2.41	3.161 (3)	152
C15—H15···O1^i	0.93	2.53	3.265 (4)	136
C16—H16···O2^i	0.93	2.72	3.420 (5)	132
C35—H35···O3^i	0.93	2.91	3.531 (5)	126
C36—H36···O4^i	0.93	2.57	3.412 (5)	150
C21—H21B···S3^ii	0.97	2.98	3.844 (3)	149
C23—H23C···S3^ii	0.96	2.98	3.842 (4)	150

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