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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\overline{1}, 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616019495/cu3106sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616019495/cu3106Isup2.hkl
Contains datablock I

smi

Smiles format file https://doi.org/10.1107/S2053229616019495/cu3106Isup5.smi
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616019495/cu3106IIsup3.hkl
Contains datablock II

smi

Smiles format file https://doi.org/10.1107/S2053229616019495/cu3106IIsup4.smi
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616019495/cu3106Isup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616019495/cu3106IIsup7.cml
Supplementary material

CCDC references: 1520890; 1520889

Computing details top

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 top
Crystal data top
C16H16N2O3SZ = 2
Mr = 316.37F(000) = 332
Triclinic, P1Dx = 1.356 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5450 (4) ÅCell parameters from 1629 reflections
b = 9.3526 (6) Åθ = 2.7–26.2°
c = 12.7820 (8) ŵ = 0.22 mm1
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) Å3
Data collection top
Agilent Xcalibur (Sapphire2, large Be window)
diffractometer
3039 independent reflections
Graphite monochromator1883 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm-1Rint = 0.026
ω scansθmax = 26.0°, θmin = 2.6°
Absorption correction: analytical
[CrysAlis PRO (Agilent, 2013), based on expressions derived by Clark & Reid (1995)]
h = 68
Tmin = 0.923, Tmax = 0.959k = 1110
4858 measured reflectionsl = 1515
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071H-atom parameters constrained
wR(F2) = 0.209 w = 1/[σ2(Fo2) + (0.1069P)2 + 0.0208P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3039 reflectionsΔρmax = 0.59 e Å3
201 parametersΔρmin = 0.25 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.32892 (14)0.32856 (10)0.05322 (7)0.0746 (4)
C10.4131 (5)0.4076 (3)0.1704 (2)0.0525 (8)
N10.5964 (4)0.4994 (3)0.1768 (2)0.0573 (7)
H10.6577930.5046030.1192020.069*
C100.6924 (5)0.5822 (3)0.2617 (3)0.0532 (8)
O10.6254 (3)0.5821 (3)0.34928 (18)0.0712 (7)
C110.8843 (4)0.6730 (3)0.2414 (2)0.0539 (8)
C120.9348 (5)0.7985 (4)0.3058 (3)0.0662 (10)
H120.8474060.8236650.3574320.079*
C131.1126 (6)0.8867 (4)0.2942 (3)0.0781 (11)
H131.1450540.9707340.3377920.094*
C141.2425 (5)0.8490 (5)0.2174 (3)0.0797 (12)
H141.3630190.9079380.2095130.096*
C151.1947 (5)0.7253 (4)0.1527 (3)0.0740 (11)
H151.2826630.7010040.1010480.089*
C161.0151 (5)0.6361 (4)0.1640 (3)0.0635 (9)
H160.9827910.5523920.1200940.076*
N20.3251 (4)0.3968 (3)0.26128 (19)0.0560 (7)
H20.3971180.4420460.3139600.067*
C210.1357 (4)0.3255 (3)0.2886 (2)0.0502 (8)
C220.0066 (5)0.2298 (3)0.2205 (2)0.0544 (8)
H220.0431780.2075740.1524550.065*
C230.1769 (5)0.1676 (3)0.2545 (2)0.0539 (8)
C240.2322 (5)0.2002 (3)0.3560 (3)0.0537 (8)
C250.1021 (5)0.2949 (4)0.4232 (3)0.0621 (9)
H250.1381850.3175990.4912890.075*
C260.0820 (5)0.3560 (4)0.3894 (3)0.0597 (9)
H260.1699780.4182720.4354040.072*
C20.2492 (6)0.0273 (4)0.0926 (3)0.0800 (12)
H2A0.2350140.1092370.0513990.120*
H2B0.3513840.0442830.0585490.120*
H2C0.1198440.0124690.0992790.120*
O20.3101 (3)0.0704 (3)0.19344 (18)0.0705 (7)
C30.4927 (6)0.1837 (5)0.4788 (3)0.0822 (12)
H3A0.4027700.1599680.5354110.123*
H3B0.6287170.1374930.4852110.123*
H3C0.4965860.2862050.4815800.123*
O30.4187 (3)0.1352 (3)0.38104 (18)0.0715 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0804 (7)0.0811 (7)0.0543 (6)0.0276 (5)0.0185 (5)0.0112 (5)
C10.0475 (18)0.0529 (19)0.056 (2)0.0036 (14)0.0098 (14)0.0031 (15)
N10.0499 (15)0.0656 (18)0.0532 (16)0.0093 (13)0.0125 (12)0.0025 (13)
C100.0481 (18)0.059 (2)0.0511 (19)0.0005 (15)0.0031 (14)0.0002 (15)
O10.0658 (15)0.0902 (18)0.0508 (14)0.0209 (12)0.0091 (11)0.0049 (12)
C110.0447 (18)0.059 (2)0.056 (2)0.0046 (14)0.0013 (14)0.0027 (15)
C120.063 (2)0.071 (2)0.061 (2)0.0083 (18)0.0038 (16)0.0002 (17)
C130.073 (3)0.073 (3)0.081 (3)0.018 (2)0.010 (2)0.009 (2)
C140.051 (2)0.091 (3)0.093 (3)0.021 (2)0.002 (2)0.026 (2)
C150.050 (2)0.091 (3)0.083 (3)0.0012 (19)0.0157 (18)0.021 (2)
C160.052 (2)0.067 (2)0.071 (2)0.0025 (16)0.0069 (16)0.0079 (18)
N20.0535 (15)0.0650 (18)0.0453 (15)0.0131 (13)0.0068 (12)0.0015 (12)
C210.0500 (18)0.0528 (19)0.0462 (18)0.0044 (14)0.0094 (13)0.0029 (13)
C220.0534 (18)0.063 (2)0.0443 (17)0.0072 (15)0.0099 (14)0.0006 (14)
C230.0507 (19)0.0526 (19)0.056 (2)0.0052 (14)0.0073 (14)0.0011 (15)
C240.0498 (18)0.0535 (19)0.059 (2)0.0003 (15)0.0186 (15)0.0057 (15)
C250.071 (2)0.061 (2)0.055 (2)0.0026 (17)0.0228 (16)0.0009 (16)
C260.062 (2)0.063 (2)0.0510 (19)0.0061 (16)0.0082 (15)0.0026 (15)
C20.075 (2)0.097 (3)0.059 (2)0.022 (2)0.0073 (18)0.016 (2)
O20.0577 (14)0.0827 (17)0.0639 (15)0.0223 (12)0.0134 (11)0.0108 (12)
C30.066 (2)0.108 (3)0.074 (3)0.001 (2)0.0301 (19)0.005 (2)
O30.0632 (15)0.0813 (17)0.0683 (16)0.0092 (12)0.0278 (12)0.0020 (12)
Geometric parameters (Å, º) top
S1—C11.663 (3)C21—C261.372 (4)
C1—N21.330 (4)C21—C221.389 (4)
C1—N11.399 (4)C22—C231.387 (4)
N1—C101.372 (4)C22—H220.9300
N1—H10.8600C23—O21.365 (4)
C10—O11.224 (4)C23—C241.387 (4)
C10—C111.490 (4)C24—O31.373 (3)
C11—C121.386 (4)C24—C251.382 (5)
C11—C161.391 (4)C25—C261.386 (4)
C12—C131.379 (5)C25—H250.9300
C12—H120.9300C26—H260.9300
C13—C141.384 (6)C2—O21.414 (4)
C13—H130.9300C2—H2A0.9600
C14—C151.373 (5)C2—H2B0.9600
C14—H140.9300C2—H2C0.9600
C15—C161.392 (4)C3—O31.426 (4)
C15—H150.9300C3—H3A0.9600
C16—H160.9300C3—H3B0.9600
N2—C211.421 (3)C3—H3C0.9600
N2—H20.8600
N2—C1—N1114.3 (3)C26—C21—N2116.0 (3)
N2—C1—S1127.9 (2)C22—C21—N2124.3 (3)
N1—C1—S1117.8 (2)C23—C22—C21119.7 (3)
C10—N1—C1129.3 (3)C23—C22—H22120.1
C10—N1—H1115.3C21—C22—H22120.1
C1—N1—H1115.3O2—C23—C22123.4 (3)
O1—C10—N1122.4 (3)O2—C23—C24116.1 (3)
O1—C10—C11121.6 (3)C22—C23—C24120.4 (3)
N1—C10—C11116.1 (3)O3—C24—C25124.8 (3)
C12—C11—C16119.3 (3)O3—C24—C23115.8 (3)
C12—C11—C10117.2 (3)C25—C24—C23119.4 (3)
C16—C11—C10123.5 (3)C24—C25—C26120.1 (3)
C13—C12—C11120.9 (3)C24—C25—H25119.9
C13—C12—H12119.5C26—C25—H25119.9
C11—C12—H12119.5C21—C26—C25120.6 (3)
C12—C13—C14119.5 (4)C21—C26—H26119.7
C12—C13—H13120.3C25—C26—H26119.7
C14—C13—H13120.3O2—C2—H2A109.5
C15—C14—C13120.4 (3)O2—C2—H2B109.5
C15—C14—H14119.8H2A—C2—H2B109.5
C13—C14—H14119.8O2—C2—H2C109.5
C14—C15—C16120.3 (3)H2A—C2—H2C109.5
C14—C15—H15119.9H2B—C2—H2C109.5
C16—C15—H15119.9C23—O2—C2117.0 (2)
C11—C16—C15119.6 (3)O3—C3—H3A109.5
C11—C16—H16120.2O3—C3—H3B109.5
C15—C16—H16120.2H3A—C3—H3B109.5
C1—N2—C21132.8 (3)O3—C3—H3C109.5
C1—N2—H2113.6H3A—C3—H3C109.5
C21—N2—H2113.6H3B—C3—H3C109.5
C26—C21—C22119.7 (3)C24—O3—C3116.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.861.902.633 (3)143
N1—H1···S1i0.862.793.485 (3)139
C22—H22···S10.932.543.203 (3)129
C14—H14···O2ii0.932.523.453 (4)178
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z.
(II) N-[(2-Hydroxypropyl)carbamothioyl]benzamide top
Crystal data top
C11H14N2O2SF(000) = 1008
Mr = 238.3Dx = 1.32 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2940 reflections
a = 22.4150 (17) Åθ = 3.0–27.0°
b = 8.1479 (5) ŵ = 0.26 mm1
c = 13.4592 (9) ÅT = 293 K
β = 102.618 (7)°Prism, colourless
V = 2398.8 (3) Å30.52 × 0.46 × 0.14 mm
Z = 8
Data collection top
Agilent Xcalibur (Sapphire2, large Be window)
diffractometer
4710 independent reflections
Graphite monochromator2847 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm-1Rint = 0.038
ω scansθmax = 26°, θmin = 2.7°
Absorption correction: analytical
[CrysAlis PRO (Agilent, 2013), based on expressions derived by Clark & Reid (1995)]
h = 2726
Tmin = 0.911, Tmax = 0.971k = 105
8922 measured reflectionsl = 1216
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.220 w = 1/[σ2(Fo2) + (0.1058P)2 + 0.9789P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4710 reflectionsΔρmax = 0.71 e Å3
293 parametersΔρmin = 0.30 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.19684 (4)0.87980 (15)0.50453 (8)0.0834 (4)
C10.13064 (15)0.8780 (4)0.5415 (2)0.0551 (8)
N10.08038 (11)0.7993 (3)0.47955 (18)0.0544 (6)
H10.0863820.7575290.4238760.065*
C100.02251 (13)0.7809 (4)0.4973 (2)0.0536 (7)
O10.00807 (11)0.8385 (3)0.57212 (18)0.0733 (7)
C110.02165 (14)0.6848 (4)0.4201 (2)0.0513 (7)
C120.07310 (15)0.6253 (4)0.4510 (3)0.0628 (9)
H120.0785470.6480680.5161160.075*
C130.11598 (17)0.5328 (4)0.3850 (3)0.0715 (10)
H130.1500340.4923470.4059360.086*
C140.10823 (17)0.5005 (4)0.2880 (3)0.0694 (9)
H140.1370380.4377500.2438000.083*
C150.05831 (17)0.5604 (4)0.2565 (3)0.0691 (9)
H150.0535700.5393440.1907480.083*
C160.01498 (16)0.6522 (4)0.3224 (2)0.0601 (8)
H160.0189030.6922690.3007050.072*
N20.12153 (12)0.9439 (3)0.62596 (19)0.0591 (7)
H20.0857670.9341340.6388070.071*
C210.16758 (15)1.0322 (4)0.6993 (2)0.0606 (8)
H21A0.1740531.1395700.6723340.073*
H21B0.2059560.9727130.7107850.073*
C220.14791 (16)1.0517 (4)0.7982 (2)0.0632 (9)
H220.1083361.1080480.7826860.076*
C230.19148 (17)1.1614 (5)0.8704 (3)0.0723 (10)
H23A0.1794881.1660570.9346290.108*
H23B0.1904531.2698220.8421650.108*
H23C0.2321871.1181070.8803910.108*
O20.13845 (13)0.9014 (3)0.8418 (2)0.0840 (8)
H2A0.1715190.8611590.8689990.126*
S30.31682 (5)0.65289 (16)0.35460 (8)0.0899 (4)
C30.38036 (16)0.6539 (4)0.4467 (2)0.0604 (8)
N30.43299 (12)0.7287 (3)0.42895 (19)0.0606 (7)
H30.4292050.7762660.3708660.073*
C300.49006 (15)0.7366 (4)0.4918 (2)0.0583 (8)
O30.50078 (11)0.6740 (4)0.57620 (19)0.0813 (8)
C310.53756 (15)0.8255 (4)0.4511 (2)0.0577 (8)
C320.59318 (17)0.8526 (5)0.5187 (3)0.0763 (11)
H320.5990710.8153940.5854560.092*
C330.63991 (19)0.9348 (5)0.4869 (3)0.0855 (12)
H330.6769640.9532830.5323250.103*
C340.63133 (18)0.9883 (5)0.3887 (3)0.0778 (11)
H340.6625251.0443060.3675950.093*
C350.57669 (18)0.9599 (5)0.3207 (3)0.0820 (11)
H350.5712950.9953350.2536410.098*
C360.53014 (16)0.8791 (5)0.3522 (3)0.0730 (10)
H360.4933140.8604390.3061770.088*
N40.38426 (13)0.5899 (3)0.5372 (2)0.0658 (8)
H40.4190020.5919000.5797200.079*
C410.33257 (17)0.5161 (5)0.5688 (3)0.0723 (10)
H41A0.3171940.4252660.5238170.087*
H41B0.3000980.5964510.5632760.087*
C420.34964 (17)0.4567 (5)0.6734 (3)0.0744 (10)
H420.3795160.3686190.6741850.089*
C430.29559 (19)0.3810 (6)0.7075 (3)0.0959 (14)
H43A0.3084360.3427230.7763530.144*
H43B0.2800740.2904450.6638560.144*
H43C0.2640750.4619390.7039960.144*
O40.37882 (12)0.5781 (4)0.7412 (2)0.0909 (9)
H4A0.3535210.6457070.7506450.136*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0569 (6)0.1220 (9)0.0779 (7)0.0110 (5)0.0288 (5)0.0136 (6)
C10.0531 (18)0.0614 (18)0.0516 (17)0.0057 (15)0.0131 (14)0.0080 (14)
N10.0511 (15)0.0676 (16)0.0471 (13)0.0035 (13)0.0163 (12)0.0003 (12)
C100.0463 (17)0.0658 (18)0.0505 (16)0.0060 (15)0.0145 (14)0.0035 (14)
O10.0551 (14)0.1070 (18)0.0625 (14)0.0042 (13)0.0234 (11)0.0203 (13)
C110.0478 (17)0.0562 (17)0.0502 (16)0.0087 (14)0.0115 (13)0.0036 (13)
C120.0552 (19)0.077 (2)0.0576 (19)0.0030 (17)0.0150 (16)0.0076 (16)
C130.060 (2)0.074 (2)0.080 (2)0.0027 (18)0.0150 (19)0.0137 (19)
C140.067 (2)0.061 (2)0.074 (2)0.0034 (18)0.0016 (18)0.0027 (17)
C150.079 (2)0.071 (2)0.059 (2)0.001 (2)0.0166 (18)0.0064 (17)
C160.064 (2)0.0615 (18)0.0571 (18)0.0009 (16)0.0192 (16)0.0009 (15)
N20.0488 (15)0.0744 (17)0.0548 (15)0.0031 (13)0.0130 (12)0.0024 (13)
C210.0554 (19)0.073 (2)0.0521 (17)0.0063 (16)0.0102 (15)0.0043 (15)
C220.062 (2)0.069 (2)0.0584 (19)0.0039 (17)0.0130 (16)0.0015 (16)
C230.066 (2)0.085 (2)0.063 (2)0.0008 (19)0.0075 (17)0.0092 (18)
O20.0850 (18)0.0949 (19)0.0745 (17)0.0147 (16)0.0226 (15)0.0151 (14)
S30.0696 (7)0.1317 (10)0.0633 (6)0.0337 (6)0.0031 (5)0.0118 (6)
C30.062 (2)0.0653 (19)0.0564 (19)0.0084 (16)0.0195 (16)0.0024 (15)
N30.0547 (16)0.0760 (18)0.0521 (15)0.0081 (14)0.0137 (12)0.0068 (13)
C300.0555 (19)0.0667 (19)0.0538 (18)0.0005 (16)0.0141 (15)0.0007 (16)
O30.0641 (16)0.113 (2)0.0638 (15)0.0126 (14)0.0075 (12)0.0215 (14)
C310.0533 (19)0.0629 (19)0.0570 (18)0.0002 (15)0.0122 (15)0.0021 (15)
C320.068 (2)0.098 (3)0.062 (2)0.021 (2)0.0129 (18)0.0093 (19)
C330.069 (2)0.106 (3)0.081 (3)0.028 (2)0.015 (2)0.015 (2)
C340.069 (2)0.070 (2)0.100 (3)0.0127 (19)0.030 (2)0.003 (2)
C350.069 (2)0.097 (3)0.083 (3)0.005 (2)0.022 (2)0.026 (2)
C360.0507 (19)0.090 (2)0.076 (2)0.0053 (19)0.0087 (17)0.0187 (19)
N40.0625 (17)0.0811 (19)0.0542 (16)0.0181 (15)0.0138 (13)0.0022 (13)
C410.068 (2)0.091 (2)0.059 (2)0.022 (2)0.0153 (17)0.0016 (18)
C420.067 (2)0.097 (3)0.061 (2)0.018 (2)0.0192 (17)0.003 (2)
C430.074 (3)0.144 (4)0.072 (3)0.028 (3)0.022 (2)0.017 (2)
O40.0747 (18)0.133 (3)0.0643 (16)0.0221 (17)0.0133 (14)0.0206 (16)
Geometric parameters (Å, º) top
S1—C11.665 (3)S3—C31.671 (4)
C1—N21.313 (4)C3—N41.311 (4)
C1—N11.402 (4)C3—N31.394 (4)
N1—C101.378 (4)N3—C301.373 (4)
N1—H10.8600N3—H30.8600
C10—O11.217 (4)C30—O31.220 (4)
C10—C111.491 (4)C30—C311.488 (4)
C11—C161.382 (4)C31—C361.376 (5)
C11—C121.395 (4)C31—C321.391 (5)
C12—C131.381 (5)C32—C331.387 (5)
C12—H120.9300C32—H320.9300
C13—C141.379 (5)C33—C341.364 (6)
C13—H130.9300C33—H330.9300
C14—C151.370 (5)C34—C351.379 (5)
C14—H140.9300C34—H340.9300
C15—C161.383 (5)C35—C361.377 (5)
C15—H150.9300C35—H350.9300
C16—H160.9300C36—H360.9300
N2—C211.453 (4)N4—C411.449 (4)
N2—H20.8600N4—H40.8600
C21—C221.500 (4)C41—C421.459 (5)
C21—H21A0.9700C41—H41A0.9700
C21—H21B0.9700C41—H41B0.9700
C22—O21.394 (4)C42—O41.407 (4)
C22—C231.511 (5)C42—C431.517 (5)
C22—H220.9800C42—H420.9800
C23—H23A0.9600C43—H43A0.9600
C23—H23B0.9600C43—H43B0.9600
C23—H23C0.9600C43—H43C0.9600
O2—H2A0.8200O4—H4A0.8200
N2—C1—N1116.4 (3)N4—C3—N3116.5 (3)
N2—C1—S1124.9 (3)N4—C3—S3124.1 (3)
N1—C1—S1118.7 (2)N3—C3—S3119.4 (2)
C10—N1—C1127.7 (3)C30—N3—C3128.7 (3)
C10—N1—H1116.1C30—N3—H3115.7
C1—N1—H1116.1C3—N3—H3115.7
O1—C10—N1122.2 (3)O3—C30—N3121.5 (3)
O1—C10—C11121.5 (3)O3—C30—C31122.3 (3)
N1—C10—C11116.3 (3)N3—C30—C31116.2 (3)
C16—C11—C12119.0 (3)C36—C31—C32118.9 (3)
C16—C11—C10124.8 (3)C36—C31—C30124.5 (3)
C12—C11—C10116.2 (3)C32—C31—C30116.6 (3)
C13—C12—C11120.2 (3)C33—C32—C31120.3 (4)
C13—C12—H12119.9C33—C32—H32119.9
C11—C12—H12119.9C31—C32—H32119.9
C14—C13—C12119.9 (3)C34—C33—C32119.8 (4)
C14—C13—H13120.0C34—C33—H33120.1
C12—C13—H13120.0C32—C33—H33120.1
C15—C14—C13120.3 (3)C33—C34—C35120.4 (4)
C15—C14—H14119.8C33—C34—H34119.8
C13—C14—H14119.8C35—C34—H34119.8
C14—C15—C16120.1 (3)C36—C35—C34119.9 (4)
C14—C15—H15120.0C36—C35—H35120.0
C16—C15—H15120.0C34—C35—H35120.0
C11—C16—C15120.5 (3)C31—C36—C35120.7 (3)
C11—C16—H16119.8C31—C36—H36119.7
C15—C16—H16119.8C35—C36—H36119.7
C1—N2—C21124.7 (3)C3—N4—C41122.9 (3)
C1—N2—H2117.7C3—N4—H4118.6
C21—N2—H2117.7C41—N4—H4118.6
N2—C21—C22110.6 (3)N4—C41—C42111.3 (3)
N2—C21—H21A109.5N4—C41—H41A109.4
C22—C21—H21A109.5C42—C41—H41A109.4
N2—C21—H21B109.5N4—C41—H41B109.4
C22—C21—H21B109.5C42—C41—H41B109.4
H21A—C21—H21B108.1H41A—C41—H41B108.0
O2—C22—C21112.4 (3)O4—C42—C41112.3 (3)
O2—C22—C23112.7 (3)O4—C42—C43112.2 (3)
C21—C22—C23111.1 (3)C41—C42—C43111.6 (3)
O2—C22—H22106.7O4—C42—H42106.7
C21—C22—H22106.7C41—C42—H42106.7
C23—C22—H22106.7C43—C42—H42106.7
C22—C23—H23A109.5C42—C43—H43A109.5
C22—C23—H23B109.5C42—C43—H43B109.5
H23A—C23—H23B109.5H43A—C43—H43B109.5
C22—C23—H23C109.5C42—C43—H43C109.5
H23A—C23—H23C109.5H43A—C43—H43C109.5
H23B—C23—H23C109.5H43B—C43—H43C109.5
C22—O2—H2A109.5C42—O4—H4A109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.202.977 (3)151
N2—H2···O10.861.942.632 (3)137
O2—H2A···S1ii0.822.663.242 (3)130
N3—H3···O4i0.862.212.999 (4)153
N4—H4···O30.861.962.640 (4)135
O4—H4A···S3ii0.822.413.161 (3)152
C15—H15···O1i0.932.533.265 (4)136
C16—H16···O2i0.932.723.420 (5)132
C35—H35···O3i0.932.913.531 (5)126
C36—H36···O4i0.932.573.412 (5)150
C21—H21B···S3ii0.972.983.844 (3)149
C23—H23C···S3ii0.962.983.842 (4)150
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+3/2, z+1/2.
 

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