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The asymmetric unit of the title compound, C12H17N3O2S, contains two independent mol­ecules, A and B. Both mol­ecules are nearly planar with the dihedral angle between the mean planes of the thio­amide group and benzene ring being 7.5 (1)° in A and 4.3 (2)° in B. In each mol­ecule, the hy­droxy group participates in intra­molecular O—H...N hydrogen bonding, while the amino H atom is not involved in hydrogen bonding because of the steric hinderence caused by two neighboring methyl groups. In the crystal, the individual molecules are linked by weak C—H...O hydrogen bonds, forming AA and BB inversion dimers. The dimers are linked via C—H...π inter­actions which help stabilize the packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015018228/cv5496sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015018228/cv5496Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015018228/cv5496Isup3.cml
Supplementary material

CCDC reference: 1428535

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.078
  • wR factor = 0.224
  • Data-to-parameter ratio = 26.9

checkCIF/PLATON results

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Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.22 Report PLAT414_ALERT_2_C Short Intra D-H..H-X H2 .. H10A .. 1.92 Ang. PLAT414_ALERT_2_C Short Intra D-H..H-X H2A .. H10D .. 1.90 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2 .. Please Check PLAT420_ALERT_2_C D-H Without Acceptor N2A - H2A .. Please Check PLAT480_ALERT_4_C Long H...A H-Bond Reported H11E .. O1A .. 2.68 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 11.582 Check PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.330 Check PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ... 8 Report PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 23 Report
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 4 Report PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large. 0.11 Report PLAT128_ALERT_4_G Alternate Setting for Input Space Group P21/a P21/c Note PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C11 Check PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C11A Check PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 3 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 647 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 2 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 2 Units
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 10 ALERT level C = Check. Ensure it is not caused by an omission or oversight 9 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Comment top

The asymmetric unit of the title compound, C12H17N3O2S, contains two independent molecules A and B, respectively (Fig. 1). Both molecules are nearly planar with the dihedral angle between the mean planes of the thioamide group and benzene ring being 7.5 (1)° in A and 4.3 (2)° in B. In each molecule, the hydroxy group participates in intramolecular O—H···N hydrogen bonding, while the amino H atom is not involved in hydrogen bonding because of the steric hinderence caused by two neighboring methyl groups. In the crystal, weak intermolecular C—H···O and C—H···π (Table 1) interactions are observed which help stabilize the packing (Fig. 2). No ππ stacking interactions are present.

Related literature top

For thiosemicarbazone ligands and metal complexes, see: Lobana et al. (2009, 2012). For biological and antitumor and antifungal activity of palladium complexes with thiosemicarbazone ligands, see: Chellan et al. (2010). For biological activity of a thiosemicarbazone ligand with a terminal dimethyl substitution, see: Kowol et al. (2009). For related structures, see: Anderson et al. (2012, 2013); Kovala-Demertzi et al. (2000).

Experimental top

A 25 mL round bottom flask charged with 2.5 mL of H2O, 2.5 mL ethanol and 0.1499 g (1.26 mmol) of 4,4-dimethyl-3-thiosemicarbazide was dissolved in a water/ethanol mixture and heated. Once the mixture was completely dissolved, 0.2225 g (1.34 mmol) of 2'-hydroxy-5'-methoxyacetophenone was added, and the solution was refluxed for 18 hours resulting in the formation of a yellow solid. After reflux, the slurry was allowed to cool to room temperature, transferred to a separatory funnel and water (15 mL) and dichloromethane (15 mL) was added. The organic layer was separated and the aqueous layer was extracted with an additional 15 mL of DCM. The organic layers were then combined and washed with brine (20 mL), and then dried with magnesium sulfate. The solvent was removed by rotary evaporation. The resulting solid was crystallized from acetonitrile to give 67 mg (18% yield) of yellow crystals. The crystals were observed to decompose above 460 K.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were located in difference maps. The C–H and N–H atoms were treated as riding atoms in geometrically idealized positions with C—H, N—H distances of 0.95 Å, 0.88 Å and refined with Uiso(H) = 1.2Ueq(C, N). The CH3 and O–H atoms were also treated as riding atoms in geometrically idealized positions with the CH3, O—H distances of 0.98 Å, 0.84 Å and refined with Uiso(H) = 1.5Ueq(C, O).

Structure description top

The asymmetric unit of the title compound, C12H17N3O2S, contains two independent molecules A and B, respectively (Fig. 1). Both molecules are nearly planar with the dihedral angle between the mean planes of the thioamide group and benzene ring being 7.5 (1)° in A and 4.3 (2)° in B. In each molecule, the hydroxy group participates in intramolecular O—H···N hydrogen bonding, while the amino H atom is not involved in hydrogen bonding because of the steric hinderence caused by two neighboring methyl groups. In the crystal, weak intermolecular C—H···O and C—H···π (Table 1) interactions are observed which help stabilize the packing (Fig. 2). No ππ stacking interactions are present.

For thiosemicarbazone ligands and metal complexes, see: Lobana et al. (2009, 2012). For biological and antitumor and antifungal activity of palladium complexes with thiosemicarbazone ligands, see: Chellan et al. (2010). For biological activity of a thiosemicarbazone ligand with a terminal dimethyl substitution, see: Kowol et al. (2009). For related structures, see: Anderson et al. (2012, 2013); Kovala-Demertzi et al. (2000).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. Two independent molecules of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A portion of the crystal packing viewed approximately along the a axis.
1-(2-Hydroxy-5-methoxyphenyl)ethanone 4,4-dimethylthiosemicarbazone top
Crystal data top
C12H17N3O2SF(000) = 1136
Mr = 267.34Dx = 1.361 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
a = 15.7097 (12) ÅCell parameters from 7195 reflections
b = 7.8300 (5) Åθ = 3.0–32.8°
c = 21.2351 (19) ŵ = 0.25 mm1
β = 92.635 (8)°T = 173 K
V = 2609.3 (3) Å3Prism, colourless
Z = 80.54 × 0.35 × 0.05 mm
Data collection top
Agilent, Eos, Gemini
diffractometer
8982 independent reflections
Radiation source: Enhance (Mo) X-ray Source6065 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
Detector resolution: 16.0416 pixels mm-1θmax = 32.9°, θmin = 3.0°
ω scansh = 2323
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1111
Tmin = 0.803, Tmax = 1.000l = 3028
33509 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.078H-atom parameters constrained
wR(F2) = 0.224 w = 1/[σ2(Fo2) + (0.1106P)2 + 0.7177P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
8982 reflectionsΔρmax = 1.08 e Å3
334 parametersΔρmin = 0.48 e Å3
0 restraints
Crystal data top
C12H17N3O2SV = 2609.3 (3) Å3
Mr = 267.34Z = 8
Monoclinic, P21/aMo Kα radiation
a = 15.7097 (12) ŵ = 0.25 mm1
b = 7.8300 (5) ÅT = 173 K
c = 21.2351 (19) Å0.54 × 0.35 × 0.05 mm
β = 92.635 (8)°
Data collection top
Agilent, Eos, Gemini
diffractometer
8982 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
6065 reflections with I > 2σ(I)
Tmin = 0.803, Tmax = 1.000Rint = 0.081
33509 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0780 restraints
wR(F2) = 0.224H-atom parameters constrained
S = 1.06Δρmax = 1.08 e Å3
8982 reflectionsΔρmin = 0.48 e Å3
334 parameters
Special details top

Experimental. Absorption correction: CrysAlisPro (Agilent, 2014). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S10.44809 (3)0.09151 (7)1.11976 (3)0.03013 (15)
O10.32782 (10)0.2857 (2)0.99601 (7)0.0293 (3)
H10.37420.24691.01120.044*
O20.35386 (11)0.6134 (2)0.76763 (7)0.0336 (4)
N10.61624 (11)0.0389 (2)1.11969 (8)0.0248 (3)
N20.55831 (11)0.1799 (2)1.03407 (8)0.0246 (3)
H20.60990.18811.01990.030*
N30.48981 (11)0.2446 (2)1.00018 (8)0.0233 (3)
C10.54532 (13)0.1017 (2)1.09064 (9)0.0215 (4)
C20.50099 (12)0.3329 (2)0.94986 (9)0.0220 (4)
C30.42248 (12)0.3932 (2)0.91666 (9)0.0211 (4)
C40.34139 (13)0.3677 (3)0.94099 (9)0.0236 (4)
C50.26923 (14)0.4287 (3)0.90750 (11)0.0295 (4)
H50.21480.41450.92460.035*
C60.27513 (14)0.5088 (3)0.85053 (11)0.0299 (4)
H60.22510.54820.82820.036*
C70.35447 (13)0.5322 (3)0.82530 (10)0.0258 (4)
C80.42704 (13)0.4770 (3)0.85839 (9)0.0247 (4)
H80.48110.49600.84140.030*
C90.43341 (17)0.6297 (4)0.73913 (11)0.0405 (6)
H9A0.42480.68430.69780.061*
H9B0.45850.51620.73390.061*
H9C0.47190.69970.76600.061*
C100.58601 (13)0.3769 (3)0.92477 (10)0.0267 (4)
H10A0.63060.36030.95800.040*
H10B0.58580.49630.91100.040*
H10C0.59710.30260.88890.040*
C110.70021 (13)0.0579 (3)1.09373 (10)0.0292 (4)
H11A0.70030.00291.05230.044*
H11B0.74320.00411.12210.044*
H11C0.71340.17951.08940.044*
C120.61403 (15)0.0437 (3)1.18084 (10)0.0302 (4)
H12A0.62940.03921.21400.045*
H12B0.65470.13861.18280.045*
H12C0.55650.08731.18690.045*
S1A0.56414 (5)0.19363 (10)0.59613 (3)0.0475 (2)
O1A0.66714 (13)0.3267 (2)0.44906 (9)0.0443 (5)
H1A0.63920.25520.46920.066*
O2A0.82584 (12)0.0500 (2)0.24624 (8)0.0411 (4)
N1A0.53156 (14)0.1371 (3)0.61861 (10)0.0413 (5)
N2A0.59826 (13)0.0826 (3)0.52876 (9)0.0357 (4)
H2A0.59700.19350.52200.043*
N3A0.63480 (12)0.0228 (3)0.48627 (9)0.0319 (4)
C1A0.56361 (15)0.0174 (4)0.58155 (11)0.0355 (5)
C2A0.67559 (14)0.0493 (3)0.44166 (10)0.0287 (4)
C3A0.71116 (14)0.0682 (3)0.39541 (10)0.0280 (4)
C4A0.70414 (16)0.2470 (3)0.40023 (11)0.0349 (5)
C5A0.73558 (19)0.3507 (3)0.35358 (12)0.0421 (6)
H5A0.72990.47110.35680.050*
C6A0.77470 (18)0.2826 (3)0.30294 (12)0.0406 (6)
H6A0.79570.35550.27140.049*
C7A0.78354 (16)0.1063 (3)0.29783 (11)0.0334 (5)
C8A0.75226 (15)0.0007 (3)0.34303 (11)0.0311 (4)
H8A0.75840.11950.33900.037*
C9A0.83626 (17)0.1293 (4)0.24074 (12)0.0396 (5)
H9AA0.87010.17200.27730.059*
H9AB0.78020.18450.23890.059*
H9AC0.86560.15500.20210.059*
C10A0.68571 (17)0.2386 (3)0.43561 (12)0.0357 (5)
H10D0.68730.29080.47760.054*
H10E0.63750.28510.41010.054*
H10F0.73890.26370.41510.054*
C11A0.5344 (2)0.3188 (4)0.60277 (14)0.0511 (7)
H11D0.50780.38520.63570.077*
H11E0.50350.33820.56230.077*
H11F0.59390.35470.59980.077*
C12A0.4973 (2)0.0922 (5)0.67918 (14)0.0571 (8)
H12D0.53620.13250.71340.086*
H12E0.49120.03210.68200.086*
H12F0.44140.14620.68280.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0221 (3)0.0347 (3)0.0344 (3)0.0020 (2)0.01022 (19)0.00048 (19)
O10.0209 (7)0.0346 (9)0.0330 (8)0.0050 (6)0.0082 (6)0.0030 (6)
O20.0299 (8)0.0352 (9)0.0358 (8)0.0002 (7)0.0011 (6)0.0072 (6)
N10.0191 (8)0.0243 (8)0.0313 (9)0.0007 (6)0.0058 (6)0.0012 (6)
N20.0204 (8)0.0245 (8)0.0295 (8)0.0024 (6)0.0079 (6)0.0015 (6)
N30.0206 (8)0.0212 (8)0.0284 (8)0.0020 (6)0.0043 (6)0.0025 (6)
C10.0209 (9)0.0178 (8)0.0263 (9)0.0008 (6)0.0050 (7)0.0035 (6)
C20.0208 (9)0.0179 (8)0.0277 (9)0.0001 (7)0.0067 (7)0.0049 (6)
C30.0178 (8)0.0168 (8)0.0290 (9)0.0024 (6)0.0047 (7)0.0040 (6)
C40.0214 (9)0.0196 (8)0.0303 (10)0.0028 (7)0.0053 (7)0.0035 (7)
C50.0184 (9)0.0295 (10)0.0410 (12)0.0021 (8)0.0067 (8)0.0009 (8)
C60.0220 (10)0.0278 (10)0.0396 (12)0.0004 (8)0.0011 (8)0.0004 (8)
C70.0261 (10)0.0195 (9)0.0317 (10)0.0008 (7)0.0020 (7)0.0004 (7)
C80.0219 (9)0.0212 (9)0.0314 (10)0.0013 (7)0.0049 (7)0.0028 (7)
C90.0376 (13)0.0515 (16)0.0330 (12)0.0026 (11)0.0066 (9)0.0089 (10)
C100.0200 (9)0.0272 (10)0.0333 (10)0.0021 (7)0.0050 (7)0.0037 (7)
C110.0197 (9)0.0314 (11)0.0370 (11)0.0006 (8)0.0051 (8)0.0012 (8)
C120.0307 (11)0.0297 (11)0.0300 (10)0.0010 (9)0.0009 (8)0.0034 (8)
S1A0.0435 (4)0.0464 (4)0.0531 (4)0.0001 (3)0.0089 (3)0.0232 (3)
O1A0.0528 (12)0.0284 (9)0.0515 (11)0.0099 (8)0.0010 (8)0.0119 (7)
O2A0.0469 (11)0.0383 (10)0.0388 (9)0.0026 (8)0.0079 (7)0.0008 (7)
N1A0.0350 (12)0.0492 (13)0.0402 (11)0.0032 (10)0.0064 (9)0.0068 (9)
N2A0.0370 (11)0.0329 (10)0.0375 (11)0.0036 (8)0.0050 (8)0.0086 (7)
N3A0.0310 (10)0.0310 (10)0.0336 (10)0.0049 (8)0.0004 (7)0.0070 (7)
C1A0.0237 (11)0.0454 (14)0.0373 (12)0.0057 (9)0.0001 (8)0.0117 (9)
C2A0.0254 (10)0.0248 (10)0.0352 (11)0.0042 (8)0.0036 (8)0.0084 (8)
C3A0.0257 (10)0.0233 (9)0.0343 (11)0.0039 (8)0.0053 (8)0.0055 (7)
C4A0.0356 (12)0.0273 (11)0.0408 (12)0.0071 (9)0.0075 (9)0.0079 (9)
C5A0.0529 (16)0.0243 (11)0.0480 (14)0.0046 (10)0.0079 (11)0.0022 (9)
C6A0.0466 (15)0.0311 (12)0.0432 (13)0.0005 (10)0.0060 (11)0.0047 (9)
C7A0.0342 (12)0.0317 (12)0.0338 (11)0.0026 (9)0.0048 (9)0.0020 (8)
C8A0.0297 (11)0.0268 (10)0.0364 (11)0.0018 (8)0.0026 (8)0.0046 (8)
C9A0.0350 (13)0.0426 (14)0.0416 (13)0.0040 (11)0.0070 (10)0.0037 (10)
C10A0.0385 (13)0.0264 (11)0.0428 (13)0.0029 (9)0.0083 (10)0.0061 (9)
C11A0.0501 (18)0.0504 (18)0.0536 (17)0.0002 (13)0.0090 (13)0.0007 (12)
C12A0.0508 (18)0.079 (2)0.0424 (16)0.0007 (16)0.0133 (13)0.0123 (14)
Geometric parameters (Å, º) top
S1—C11.676 (2)S1A—C1A1.681 (3)
O1—H10.8400O1A—H1A0.8400
O1—C41.359 (2)O1A—C4A1.363 (3)
O2—C71.380 (3)O2A—C7A1.379 (3)
O2—C91.419 (3)O2A—C9A1.419 (3)
N1—C11.342 (3)N1A—C1A1.337 (4)
N1—C111.461 (3)N1A—C11A1.463 (4)
N1—C121.452 (3)N1A—C12A1.460 (3)
N2—H20.8800N2A—H2A0.8800
N2—N31.364 (2)N2A—N3A1.368 (3)
N2—C11.372 (2)N2A—C1A1.367 (3)
N3—C21.292 (3)N3A—C2A1.297 (3)
C2—C31.470 (3)C2A—C3A1.474 (3)
C2—C101.500 (3)C2A—C10A1.496 (3)
C3—C41.411 (3)C3A—C4A1.408 (3)
C3—C81.405 (3)C3A—C8A1.414 (3)
C4—C51.395 (3)C4A—C5A1.389 (4)
C5—H50.9500C5A—H5A0.9500
C5—C61.369 (3)C5A—C6A1.371 (4)
C6—H60.9500C6A—H6A0.9500
C6—C71.391 (3)C6A—C7A1.392 (3)
C7—C81.381 (3)C7A—C8A1.375 (3)
C8—H80.9500C8A—H8A0.9500
C9—H9A0.9800C9A—H9AA0.9800
C9—H9B0.9800C9A—H9AB0.9800
C9—H9C0.9800C9A—H9AC0.9800
C10—H10A0.9800C10A—H10D0.9800
C10—H10B0.9800C10A—H10E0.9800
C10—H10C0.9800C10A—H10F0.9800
C11—H11A0.9800C11A—H11D0.9800
C11—H11B0.9800C11A—H11E0.9800
C11—H11C0.9800C11A—H11F0.9800
C12—H12A0.9800C12A—H12D0.9800
C12—H12B0.9800C12A—H12E0.9800
C12—H12C0.9800C12A—H12F0.9800
C4—O1—H1109.5C4A—O1A—H1A109.5
C7—O2—C9116.72 (17)C7A—O2A—C9A116.31 (19)
C1—N1—C11122.29 (17)C1A—N1A—C11A122.0 (2)
C1—N1—C12121.38 (17)C1A—N1A—C12A121.0 (3)
C12—N1—C11116.23 (17)C12A—N1A—C11A116.9 (3)
N3—N2—H2120.6N3A—N2A—H2A119.6
N3—N2—C1118.84 (17)C1A—N2A—H2A119.6
C1—N2—H2120.6C1A—N2A—N3A120.7 (2)
C2—N3—N2120.09 (17)C2A—N3A—N2A117.1 (2)
N1—C1—S1124.37 (15)N1A—C1A—S1A125.40 (19)
N1—C1—N2114.36 (17)N1A—C1A—N2A113.3 (2)
N2—C1—S1121.27 (15)N2A—C1A—S1A121.3 (2)
N3—C2—C3115.20 (17)N3A—C2A—C3A115.5 (2)
N3—C2—C10125.01 (18)N3A—C2A—C10A123.5 (2)
C3—C2—C10119.79 (17)C3A—C2A—C10A121.05 (19)
C4—C3—C2122.05 (18)C4A—C3A—C2A122.6 (2)
C8—C3—C2119.78 (17)C4A—C3A—C8A118.0 (2)
C8—C3—C4118.16 (18)C8A—C3A—C2A119.43 (19)
O1—C4—C3124.19 (18)O1A—C4A—C3A123.2 (2)
O1—C4—C5116.38 (18)O1A—C4A—C5A116.9 (2)
C5—C4—C3119.43 (19)C5A—C4A—C3A119.8 (2)
C4—C5—H5119.3C4A—C5A—H5A119.4
C6—C5—C4121.38 (19)C6A—C5A—C4A121.3 (2)
C6—C5—H5119.3C6A—C5A—H5A119.4
C5—C6—H6120.0C5A—C6A—H6A120.1
C5—C6—C7119.9 (2)C5A—C6A—C7A119.8 (2)
C7—C6—H6120.0C7A—C6A—H6A120.1
O2—C7—C6115.65 (18)O2A—C7A—C6A115.6 (2)
O2—C7—C8124.61 (19)C8A—C7A—O2A124.3 (2)
C8—C7—C6119.74 (19)C8A—C7A—C6A120.1 (2)
C3—C8—H8119.3C3A—C8A—H8A119.5
C7—C8—C3121.33 (19)C7A—C8A—C3A121.0 (2)
C7—C8—H8119.3C7A—C8A—H8A119.5
O2—C9—H9A109.5O2A—C9A—H9AA109.5
O2—C9—H9B109.5O2A—C9A—H9AB109.5
O2—C9—H9C109.5O2A—C9A—H9AC109.5
H9A—C9—H9B109.5H9AA—C9A—H9AB109.5
H9A—C9—H9C109.5H9AA—C9A—H9AC109.5
H9B—C9—H9C109.5H9AB—C9A—H9AC109.5
C2—C10—H10A109.5C2A—C10A—H10D109.5
C2—C10—H10B109.5C2A—C10A—H10E109.5
C2—C10—H10C109.5C2A—C10A—H10F109.5
H10A—C10—H10B109.5H10D—C10A—H10E109.5
H10A—C10—H10C109.5H10D—C10A—H10F109.5
H10B—C10—H10C109.5H10E—C10A—H10F109.5
N1—C11—H11A109.5N1A—C11A—H11D109.5
N1—C11—H11B109.5N1A—C11A—H11E109.5
N1—C11—H11C109.5N1A—C11A—H11F109.5
H11A—C11—H11B109.5H11D—C11A—H11E109.5
H11A—C11—H11C109.5H11D—C11A—H11F109.5
H11B—C11—H11C109.5H11E—C11A—H11F109.5
N1—C12—H12A109.5N1A—C12A—H12D109.5
N1—C12—H12B109.5N1A—C12A—H12E109.5
N1—C12—H12C109.5N1A—C12A—H12F109.5
H12A—C12—H12B109.5H12D—C12A—H12E109.5
H12A—C12—H12C109.5H12D—C12A—H12F109.5
H12B—C12—H12C109.5H12E—C12A—H12F109.5
O1—C4—C5—C6178.0 (2)O1A—C4A—C5A—C6A179.3 (2)
O2—C7—C8—C3179.22 (18)O2A—C7A—C8A—C3A178.6 (2)
N2—N3—C2—C3178.91 (16)N2A—N3A—C2A—C3A177.70 (18)
N2—N3—C2—C101.7 (3)N2A—N3A—C2A—C10A1.3 (3)
N3—N2—C1—S12.4 (2)N3A—N2A—C1A—S1A0.3 (3)
N3—N2—C1—N1178.56 (17)N3A—N2A—C1A—N1A179.2 (2)
N3—C2—C3—C44.8 (3)N3A—C2A—C3A—C4A2.1 (3)
N3—C2—C3—C8174.23 (17)N3A—C2A—C3A—C8A176.3 (2)
C1—N2—N3—C2173.41 (17)C1A—N2A—N3A—C2A171.6 (2)
C2—C3—C4—O10.5 (3)C2A—C3A—C4A—O1A2.7 (3)
C2—C3—C4—C5179.65 (18)C2A—C3A—C4A—C5A177.1 (2)
C2—C3—C8—C7178.66 (18)C2A—C3A—C8A—C7A177.7 (2)
C3—C4—C5—C61.9 (3)C3A—C4A—C5A—C6A0.9 (4)
C4—C3—C8—C70.4 (3)C4A—C3A—C8A—C7A0.7 (3)
C4—C5—C6—C70.7 (3)C4A—C5A—C6A—C7A0.1 (4)
C5—C6—C7—O2179.7 (2)C5A—C6A—C7A—O2A178.3 (2)
C5—C6—C7—C81.0 (3)C5A—C6A—C7A—C8A0.8 (4)
C6—C7—C8—C31.6 (3)C6A—C7A—C8A—C3A0.3 (3)
C8—C3—C4—O1178.59 (18)C8A—C3A—C4A—O1A178.9 (2)
C8—C3—C4—C51.3 (3)C8A—C3A—C4A—C5A1.3 (3)
C9—O2—C7—C6176.3 (2)C9A—O2A—C7A—C6A179.3 (2)
C9—O2—C7—C84.5 (3)C9A—O2A—C7A—C8A0.3 (3)
C10—C2—C3—C4174.64 (18)C10A—C2A—C3A—C4A178.9 (2)
C10—C2—C3—C86.3 (3)C10A—C2A—C3A—C8A2.8 (3)
C11—N1—C1—S1177.10 (15)C11A—N1A—C1A—S1A179.4 (2)
C11—N1—C1—N21.9 (3)C11A—N1A—C1A—N2A0.0 (3)
C12—N1—C1—S10.7 (3)C12A—N1A—C1A—S1A3.7 (4)
C12—N1—C1—N2178.29 (18)C12A—N1A—C1A—N2A175.7 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C3···C8 and C3A···C8A rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1—H1···N30.841.842.563 (2)143
O1A—H1A···N3A0.841.862.565 (3)141
C11—H11A···O1i0.982.513.315 (3)139
C11A—H11E···O1Aii0.982.683.305 (4)122
C11A—H11E···Cg2iii0.982.733.590 (3)147
C12—H12B···Cg1i0.982.823.530 (3)130
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y, z+1; (iii) x+3/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C3···C8 and C3A···C8A rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1—H1···N30.841.842.563 (2)143
O1A—H1A···N3A0.841.862.565 (3)141
C11—H11A···O1i0.982.513.315 (3)139
C11A—H11E···O1Aii0.982.683.305 (4)122
C11A—H11E···Cg2iii0.982.733.590 (3)147
C12—H12B···Cg1i0.982.823.530 (3)130
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y, z+1; (iii) x+3/2, y+1/2, z+1.
 

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