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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1239–o1240.
Published online 2010 April 30. doi:  10.1107/S160053681001528X
PMCID: PMC2979059

tert-Butyl N-[6-(N,N-dipropyl­carbamo­yl)-1,3-benzothia­zol-2-yl]carbamate

Abstract

The title compound C19H27N3O3S, crystallizes with two unique mol­ecules in the asymmetric unit. The benzene ring of each benzothia­zole unit carries a dipropyl­carbamoyl substituent in the 6-position and a tert-butyl carbamate unit on each thia­zole ring. In the crystal structure, inter­molecular N—H(...)N and weak C—H(...)O hydrogen bonds form centrosymmetric dimers. Additional C—H(...)O contacts construct a three-dimensional network. A very weak C—H(...)π contact is also present.

Related literature

For benzothia­zole derivatives with anti-tumor activity, see: Brantley et al. (2004 [triangle]); Ćaleta et al. (2009 [triangle]); Mortimer et al. (2006 [triangle]) and for benzothia­zolines with anti-tuberculous properties, see: Palmer et al. (1971 [triangle]). For related benzothia­zole structures, see: Lynch (2002 [triangle]); Matković-Čalogović et al. (2003 [triangle]); Lei et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1239-scheme1.jpg

Experimental

Crystal data

  • C19H27N3O3S
  • M r = 377.50
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1239-efi1.jpg
  • a = 14.068 (3) Å
  • b = 20.942 (4) Å
  • c = 26.515 (5) Å
  • V = 7812 (3) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 113 K
  • 0.45 × 0.35 × 0.23 mm

Data collection

  • Rigaku Saturn 724 CCD area-detector diffractometer
  • Absorption correction: numerical (NUMABS; Higashi, 2000 [triangle]) T min = 0.993, T max = 0.995
  • 62834 measured reflections
  • 8937 independent reflections
  • 8783 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.114
  • S = 1.27
  • 8937 reflections
  • 469 parameters
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2007 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEX (McArdle, 1995 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001528X/sj2775sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001528X/sj2775Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors gratefully acknowledge financial support from the Fujian Institute of Research on the Structure of Matter, State Key Laboratory of Structural Chemistry, Chinese Academy of Sciences (Nos. SZD08003 and NSFC– 30811130467), the Fujian Natural Science Foundation (No. 2008 J0330) and the Fujian Terms of Science and Technology (Nos. 2008 F5033, 2008 J1005 and 2009I0016).

supplementary crystallographic information

Comment

A number of benzothiazole derivatives have anti-tuberculous (Brantley et al., 2004; Mortimer et al., 2006; Ćaleta et al., 2009) or anti-microbial activities (Palmer et al., 1971). During our development of 2-aminobenzothiazole-based Urokinase-Type Plasminogen Activator (uPA) inhibitors, the title compound was synthesized as an intermediate while its activity was not tested because it is only a fragment of our target molecule.

There are two benzothiazole molecules in one crystallographically independent unit. The benzothiazole units are similar to previously reported benzothiazole compounds (Lynch, 2002; Matković-Čalogović et al., 2003), except that the two molecules are slightly distorted from a planar conformation with the angles between thiazole and benzene rings of 1.19 (7) ° for molecule 1 (C1 >> C19) and 4.01 (6) ° for molecule 2 (C20 >> C38), respectively. The dihedral angles between the carbonylamino group and the thiazole ring are 5.43 (15) ° for 1 and 18.19 (11) ° for 2, respectively. The dihedral angles between the dipropylcarbamoyl group and the benzene ring are 56.75 (16) ° for 1 and 54.0914 (1) \5 for 2, respectively.

In the crystal, molecules form pairs via N—H···N and C—H···O hydrogen bonds, Table 1. The dimers form a network through weak C—H···O hydrogen bonds. There is also a very weak C22—H22A···Cg contact (Cg is the centroid of the C26···C31 benzene ring). No π - π interactions are found in this structure, seemingly due to the steric hindrance of the dipropylcarbamoyl group. This is in contrast to what was found in the structure of ethyl 2-(tert-butoxycarbonylamino)-1,3-benzothiazole-6-carboxylate (Lei et al., 2010).

Experimental

A solution of ethyl 2-(tert-butoxycarbonylamino)benzo[d]thiazole-6-carboxylate (2.5 g, 7.76 mmol) was refluxed in a solution of EtOH (80 ml) and 2 N aq NaOH (50 ml) for 5 hours. Then the solution was cooled to 0oC and acidified with 1 N aq HCl solution. When pH < 2, white precipitate was collected, washed by water, and dried, afforded white solid of 2-(tert-butoxycarbonylamino)benzo[d]thiazole-6-carboxylic acid, N-Boc acid, (1.96 g, yield: 86%). 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, HBTU (1138 mg, 3 mmol) and N,N-Diisopropylethylamine, DIEA, (310 mg, 2.4 mmol) were added to the solution of N-Boc acid (588 mg, 2 mmol) in dry DMF (20 ml) and stired for 8 hours at room temperature, then dipropylamine (303 mg, 3 mmol) was added dropwise and the reaction continued further for 12 hours. The reaction solution was treated with water (150 ml) and then the precipitate was collected and washed with water. The filter cake was dried to yield a yellow solid and purification was achieved by column chromatography (ethyl acetate/petroleum ether 1 : 2) to yield the final product as a white solid (600 mg, yield: 79.58%). The solid was dissolved again in DMF, and filtered. After the solvent evaporated slowly at room temperature for a week, colourless rhombic crystals suitable for X-ray structure analysis were separated from the solution.

Refinement

All H atoms bound to C and N atoms were refined as riding, with C—H distances in the range of 0.93 to 0.97 Å and N—H distances of 0.86 Å, with Uiso(H) = 1.2Ueq(C, N); 1.5Ueq(Cmethyl).

Figures

Fig. 1.
The asymmetric unit of the title compound with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.

Crystal data

C19H27N3O3SF(000) = 3232
Mr = 377.50Dx = 1.284 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 28185 reflections
a = 14.068 (3) Åθ = 3.0–27.5°
b = 20.942 (4) ŵ = 0.19 mm1
c = 26.515 (5) ÅT = 113 K
V = 7812 (3) Å3Rhombic, colourless
Z = 160.45 × 0.35 × 0.23 mm

Data collection

Rigaku Saturn 724 CCD area-detector diffractometer8937 independent reflections
Radiation source: fine-focus sealed tube8783 reflections with I > 2σ(I)
graphiteRint = 0.049
Detector resolution: 28.5714 pixels mm-1θmax = 27.5°, θmin = 3.0°
dtprofit.ref scansh = −15→18
Absorption correction: numerical (NUMABS; Higashi, 2000)k = −27→27
Tmin = 0.993, Tmax = 0.995l = −30→34
62834 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.26w = 1/[σ2(Fo2) + (0.0264P)2 + 6.2394P] where P = (Fo2 + 2Fc2)/3
8937 reflections(Δ/σ)max = 0.001
469 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.96277 (3)0.24066 (2)0.608747 (17)0.02135 (10)
S20.93248 (3)0.50052 (2)0.403321 (17)0.02120 (10)
O11.05224 (10)0.22536 (6)0.45079 (5)0.0225 (3)
O21.03002 (10)0.17996 (6)0.52814 (5)0.0257 (3)
O60.95635 (10)0.35162 (7)0.20407 (5)0.0278 (3)
O30.91447 (10)0.32656 (7)0.80962 (5)0.0270 (3)
O50.84796 (11)0.56490 (7)0.47992 (5)0.0300 (3)
O40.81103 (10)0.52117 (6)0.55639 (5)0.0242 (3)
N20.92428 (11)0.35382 (7)0.57104 (6)0.0193 (3)
N30.76025 (11)0.35404 (8)0.79978 (6)0.0229 (3)
N50.92687 (11)0.38443 (7)0.43988 (6)0.0200 (3)
N10.98199 (12)0.28194 (7)0.51118 (6)0.0216 (3)
H10.97290.30960.48770.026*
N40.88637 (11)0.46199 (7)0.49931 (6)0.0210 (3)
H40.89360.43520.52360.025*
N61.08841 (11)0.41277 (8)0.21075 (6)0.0218 (3)
C11.18925 (15)0.15247 (12)0.45972 (8)0.0332 (5)
H1A1.23080.18880.46040.050*
H1B1.22160.11690.44460.050*
H1C1.17110.14160.49350.050*
C21.12919 (15)0.19117 (10)0.37669 (7)0.0279 (4)
H2A1.17340.22590.37960.042*
H2B1.07350.20530.35900.042*
H2C1.15830.15670.35850.042*
C31.03136 (16)0.11326 (10)0.42613 (8)0.0322 (5)
H3A0.97730.12590.40640.048*
H3B1.01100.10190.45950.048*
H3C1.06160.07720.41060.048*
C41.10119 (13)0.16828 (9)0.42915 (7)0.0217 (4)
C51.02273 (13)0.22401 (9)0.49879 (7)0.0207 (4)
C60.95554 (13)0.29683 (9)0.55966 (7)0.0190 (3)
C70.90343 (13)0.35638 (9)0.62241 (7)0.0184 (3)
C80.86796 (13)0.40970 (9)0.64792 (7)0.0215 (4)
H80.85800.44800.63100.026*
C90.84795 (14)0.40442 (9)0.69893 (7)0.0224 (4)
H90.82250.43930.71590.027*
C100.86521 (13)0.34754 (9)0.72555 (7)0.0202 (4)
C110.90282 (13)0.29492 (9)0.70073 (7)0.0206 (4)
H110.91610.25740.71810.025*
C120.92015 (13)0.29959 (8)0.64920 (7)0.0191 (3)
C130.84813 (13)0.34180 (9)0.78161 (7)0.0209 (4)
C140.67510 (14)0.35806 (10)0.76828 (7)0.0251 (4)
H14A0.62960.32640.77960.030*
H14B0.69220.34780.73380.030*
C150.62774 (16)0.42374 (10)0.76926 (8)0.0308 (5)
H15A0.58100.42490.79610.037*
H15B0.67530.45600.77630.037*
C160.57946 (17)0.43906 (11)0.71957 (8)0.0336 (5)
H16A0.55060.48050.72160.050*
H16B0.53150.40760.71270.050*
H16C0.62570.43880.69300.050*
C170.74676 (15)0.35034 (10)0.85472 (7)0.0273 (4)
H17A0.69200.37590.86400.033*
H17B0.80200.36840.87130.033*
C180.73213 (17)0.28227 (11)0.87350 (8)0.0346 (5)
H18A0.78270.25530.86070.041*
H18B0.67230.26600.86070.041*
C190.7314 (2)0.27955 (14)0.93096 (9)0.0501 (7)
H19A0.72200.23620.94170.075*
H19B0.68080.30570.94360.075*
H19C0.79110.29500.94370.075*
C200.66237 (15)0.57762 (11)0.53708 (8)0.0319 (5)
H20A0.63060.53710.53680.048*
H20B0.68380.58770.50360.048*
H20C0.61910.61000.54850.048*
C210.71580 (18)0.55301 (12)0.62447 (8)0.0382 (5)
H21A0.68200.51330.62180.057*
H21B0.67510.58480.63910.057*
H21C0.77080.54730.64540.057*
C220.80034 (16)0.63702 (11)0.57473 (10)0.0381 (5)
H22A0.85310.63290.59750.057*
H22B0.75860.67010.58650.057*
H22C0.82340.64780.54170.057*
C230.74685 (14)0.57458 (9)0.57230 (7)0.0238 (4)
C240.84771 (13)0.52107 (9)0.50973 (7)0.0217 (4)
C250.91377 (13)0.44426 (9)0.45142 (7)0.0194 (3)
C260.95101 (13)0.37896 (9)0.38902 (7)0.0187 (3)
C270.96320 (13)0.32156 (9)0.36315 (7)0.0211 (4)
H270.95650.28270.37980.025*
C280.98538 (13)0.32322 (9)0.31227 (7)0.0206 (4)
H280.99140.28510.29450.025*
C290.99895 (12)0.38148 (9)0.28707 (7)0.0191 (3)
C300.98720 (13)0.43903 (9)0.31258 (7)0.0200 (4)
H300.99670.47780.29620.024*
C310.96087 (13)0.43706 (9)0.36330 (7)0.0196 (4)
C321.01427 (13)0.38019 (8)0.23074 (7)0.0196 (4)
C331.09844 (15)0.41331 (10)0.15547 (7)0.0270 (4)
H33A1.03630.40720.14040.032*
H33B1.13820.37770.14540.032*
C341.14122 (19)0.47439 (11)0.13533 (9)0.0399 (5)
H34A1.20480.47980.14890.048*
H34B1.10310.51050.14610.048*
C351.1456 (2)0.47286 (14)0.07794 (9)0.0505 (7)
H35A1.17300.51190.06580.076*
H35B1.08260.46820.06460.076*
H35C1.18410.43750.06730.076*
C361.17332 (14)0.42832 (10)0.24024 (8)0.0268 (4)
H36A1.15670.42920.27570.032*
H36B1.19520.47060.23090.032*
C371.25318 (16)0.38125 (12)0.23238 (9)0.0386 (5)
H37A1.30780.39470.25210.046*
H37B1.27150.38160.19710.046*
C381.2265 (2)0.31399 (13)0.24729 (12)0.0516 (7)
H38A1.27950.28610.24150.077*
H38B1.17330.30010.22740.077*
H38C1.20960.31310.28240.077*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0280 (2)0.0193 (2)0.0168 (2)0.00554 (18)0.00337 (17)0.00088 (16)
S20.0278 (2)0.0174 (2)0.0184 (2)0.00189 (17)0.00406 (17)0.00045 (16)
O10.0295 (7)0.0212 (6)0.0169 (6)0.0050 (5)0.0044 (5)−0.0015 (5)
O20.0333 (8)0.0220 (7)0.0217 (7)0.0055 (6)0.0063 (6)0.0019 (5)
O60.0283 (7)0.0346 (8)0.0204 (7)−0.0086 (6)−0.0001 (6)−0.0030 (6)
O30.0263 (7)0.0340 (8)0.0207 (7)0.0040 (6)−0.0011 (5)0.0021 (6)
O50.0414 (9)0.0227 (7)0.0259 (7)0.0060 (6)0.0078 (6)0.0032 (6)
O40.0314 (7)0.0238 (7)0.0174 (6)0.0085 (6)0.0028 (5)−0.0022 (5)
N20.0209 (7)0.0198 (7)0.0171 (7)0.0013 (6)0.0015 (6)−0.0005 (6)
N30.0233 (8)0.0284 (8)0.0169 (7)0.0039 (7)0.0020 (6)−0.0011 (6)
N50.0234 (8)0.0204 (7)0.0161 (7)0.0008 (6)0.0009 (6)0.0001 (6)
N10.0288 (8)0.0199 (8)0.0162 (7)0.0048 (6)0.0034 (6)0.0014 (6)
N40.0266 (8)0.0194 (7)0.0169 (7)0.0039 (6)0.0019 (6)0.0010 (6)
N60.0234 (8)0.0245 (8)0.0175 (8)−0.0032 (6)0.0020 (6)−0.0011 (6)
C10.0271 (10)0.0465 (13)0.0259 (10)0.0118 (9)−0.0002 (8)−0.0034 (9)
C20.0350 (11)0.0284 (10)0.0203 (9)0.0040 (8)0.0051 (8)−0.0030 (8)
C30.0364 (12)0.0266 (10)0.0336 (11)−0.0032 (9)0.0061 (9)−0.0082 (9)
C40.0237 (9)0.0218 (9)0.0197 (9)0.0048 (7)0.0040 (7)−0.0040 (7)
C50.0224 (9)0.0217 (9)0.0181 (8)0.0017 (7)0.0024 (7)−0.0021 (7)
C60.0192 (8)0.0201 (8)0.0178 (8)0.0002 (7)0.0008 (7)0.0007 (7)
C70.0186 (8)0.0203 (8)0.0163 (8)−0.0008 (7)−0.0004 (6)0.0003 (7)
C80.0249 (9)0.0187 (8)0.0209 (9)0.0008 (7)0.0006 (7)0.0011 (7)
C90.0261 (9)0.0191 (9)0.0218 (9)0.0020 (7)0.0031 (7)−0.0029 (7)
C100.0195 (8)0.0224 (9)0.0187 (9)0.0005 (7)0.0006 (7)−0.0010 (7)
C110.0218 (9)0.0206 (9)0.0194 (9)0.0027 (7)0.0007 (7)0.0014 (7)
C120.0189 (8)0.0183 (8)0.0199 (9)0.0027 (7)0.0011 (7)0.0000 (7)
C130.0243 (9)0.0191 (8)0.0195 (9)0.0005 (7)0.0017 (7)−0.0016 (7)
C140.0242 (9)0.0287 (10)0.0223 (9)0.0013 (8)0.0007 (7)−0.0035 (8)
C150.0342 (11)0.0309 (11)0.0273 (10)0.0078 (9)−0.0028 (9)−0.0054 (8)
C160.0384 (12)0.0335 (11)0.0290 (11)0.0081 (9)−0.0033 (9)−0.0025 (9)
C170.0303 (10)0.0336 (11)0.0180 (9)0.0060 (8)0.0048 (8)−0.0014 (8)
C180.0367 (12)0.0394 (12)0.0277 (11)−0.0024 (10)0.0070 (9)0.0043 (9)
C190.0644 (18)0.0561 (16)0.0300 (12)−0.0062 (14)0.0089 (12)0.0132 (11)
C200.0279 (11)0.0354 (11)0.0323 (11)0.0053 (9)−0.0047 (8)−0.0062 (9)
C210.0460 (13)0.0434 (13)0.0252 (10)0.0162 (11)0.0070 (9)−0.0043 (9)
C220.0303 (11)0.0322 (11)0.0518 (14)−0.0021 (9)0.0020 (10)−0.0180 (10)
C230.0244 (9)0.0229 (9)0.0240 (9)0.0062 (7)0.0009 (7)−0.0059 (7)
C240.0227 (9)0.0225 (9)0.0199 (9)0.0018 (7)0.0001 (7)−0.0018 (7)
C250.0197 (8)0.0205 (8)0.0180 (8)0.0011 (7)0.0008 (7)0.0000 (7)
C260.0194 (8)0.0210 (8)0.0157 (8)0.0002 (7)−0.0003 (6)0.0010 (7)
C270.0255 (9)0.0183 (8)0.0194 (9)−0.0007 (7)−0.0002 (7)0.0019 (7)
C280.0219 (9)0.0195 (9)0.0203 (9)0.0002 (7)−0.0017 (7)−0.0017 (7)
C290.0174 (8)0.0224 (9)0.0174 (8)0.0007 (7)0.0002 (6)−0.0005 (7)
C300.0231 (9)0.0187 (8)0.0183 (8)0.0010 (7)0.0025 (7)0.0030 (7)
C310.0197 (8)0.0191 (8)0.0200 (9)0.0019 (7)0.0001 (7)−0.0005 (7)
C320.0210 (9)0.0176 (8)0.0203 (9)0.0013 (7)0.0007 (7)−0.0005 (7)
C330.0296 (10)0.0330 (11)0.0184 (9)−0.0044 (8)0.0027 (7)0.0008 (8)
C340.0531 (15)0.0351 (12)0.0314 (12)−0.0038 (11)0.0093 (10)0.0054 (10)
C350.0652 (18)0.0556 (16)0.0306 (12)−0.0087 (14)0.0093 (12)0.0127 (11)
C360.0239 (10)0.0316 (10)0.0250 (10)−0.0064 (8)0.0016 (8)−0.0057 (8)
C370.0227 (10)0.0552 (15)0.0378 (12)0.0055 (10)−0.0008 (9)−0.0078 (11)
C380.0442 (15)0.0456 (14)0.0649 (18)0.0216 (12)−0.0073 (13)−0.0014 (13)

Geometric parameters (Å, °)

S1—C121.7416 (18)C15—H15A0.9700
S1—C61.7574 (18)C15—H15B0.9700
S2—C311.7469 (18)C16—H16A0.9600
S2—C251.7563 (19)C16—H16B0.9600
O1—C51.339 (2)C16—H16C0.9600
O1—C41.494 (2)C17—C181.524 (3)
O2—C51.211 (2)C17—H17A0.9700
O6—C321.234 (2)C17—H17B0.9700
O3—C131.235 (2)C18—C191.525 (3)
O5—C241.211 (2)C18—H18A0.9700
O4—C241.341 (2)C18—H18B0.9700
O4—C231.498 (2)C19—H19A0.9600
N2—C61.307 (2)C19—H19B0.9600
N2—C71.394 (2)C19—H19C0.9600
N3—C131.351 (2)C20—C231.513 (3)
N3—C141.463 (2)C20—H20A0.9600
N3—C171.471 (2)C20—H20B0.9600
N5—C251.303 (2)C20—H20C0.9600
N5—C261.395 (2)C21—C231.519 (3)
N1—C61.374 (2)C21—H21A0.9600
N1—C51.381 (2)C21—H21B0.9600
N1—H10.8600C21—H21C0.9600
N4—C251.378 (2)C22—C231.510 (3)
N4—C241.379 (2)C22—H22A0.9600
N4—H40.8600C22—H22B0.9600
N6—C321.354 (2)C22—H22C0.9600
N6—C361.464 (2)C26—C271.395 (2)
N6—C331.473 (2)C26—C311.401 (2)
C1—C41.517 (3)C27—C281.385 (3)
C1—H1A0.9600C27—H270.9300
C1—H1B0.9600C28—C291.404 (3)
C1—H1C0.9600C28—H280.9300
C2—C41.523 (3)C29—C301.392 (3)
C2—H2A0.9600C29—C321.509 (2)
C2—H2B0.9600C30—C311.396 (2)
C2—H2C0.9600C30—H300.9300
C3—C41.516 (3)C33—C341.511 (3)
C3—H3A0.9600C33—H33A0.9700
C3—H3B0.9600C33—H33B0.9700
C3—H3C0.9600C34—C351.523 (3)
C7—C81.398 (2)C34—H34A0.9700
C7—C121.405 (2)C34—H34B0.9700
C8—C91.386 (3)C35—H35A0.9600
C8—H80.9300C35—H35B0.9600
C9—C101.406 (3)C35—H35C0.9600
C9—H90.9300C36—C371.509 (3)
C10—C111.388 (3)C36—H36A0.9700
C10—C131.511 (2)C36—H36B0.9700
C11—C121.391 (2)C37—C381.511 (4)
C11—H110.9300C37—H37A0.9700
C14—C151.528 (3)C37—H37B0.9700
C14—H14A0.9700C38—H38A0.9600
C14—H14B0.9700C38—H38B0.9600
C15—C161.517 (3)C38—H38C0.9600
C12—S1—C687.81 (9)C17—C18—H18B109.4
C31—S2—C2587.99 (9)C19—C18—H18B109.4
C5—O1—C4119.41 (14)H18A—C18—H18B108.0
C24—O4—C23119.54 (14)C18—C19—H19A109.5
C6—N2—C7109.36 (15)C18—C19—H19B109.5
C13—N3—C14123.81 (16)H19A—C19—H19B109.5
C13—N3—C17117.46 (16)C18—C19—H19C109.5
C14—N3—C17117.57 (16)H19A—C19—H19C109.5
C25—N5—C26109.89 (15)H19B—C19—H19C109.5
C6—N1—C5122.29 (15)C23—C20—H20A109.5
C6—N1—H1118.9C23—C20—H20B109.5
C5—N1—H1118.9H20A—C20—H20B109.5
C25—N4—C24122.45 (16)C23—C20—H20C109.5
C25—N4—H4118.8H20A—C20—H20C109.5
C24—N4—H4118.8H20B—C20—H20C109.5
C32—N6—C36122.09 (16)C23—C21—H21A109.5
C32—N6—C33117.85 (16)C23—C21—H21B109.5
C36—N6—C33116.85 (16)H21A—C21—H21B109.5
C4—C1—H1A109.5C23—C21—H21C109.5
C4—C1—H1B109.5H21A—C21—H21C109.5
H1A—C1—H1B109.5H21B—C21—H21C109.5
C4—C1—H1C109.5C23—C22—H22A109.5
H1A—C1—H1C109.5C23—C22—H22B109.5
H1B—C1—H1C109.5H22A—C22—H22B109.5
C4—C2—H2A109.5C23—C22—H22C109.5
C4—C2—H2B109.5H22A—C22—H22C109.5
H2A—C2—H2B109.5H22B—C22—H22C109.5
C4—C2—H2C109.5O4—C23—C22110.99 (16)
H2A—C2—H2C109.5O4—C23—C20109.34 (15)
H2B—C2—H2C109.5C22—C23—C20112.42 (18)
C4—C3—H3A109.5O4—C23—C21101.98 (15)
C4—C3—H3B109.5C22—C23—C21111.22 (18)
H3A—C3—H3B109.5C20—C23—C21110.41 (18)
C4—C3—H3C109.5O5—C24—O4127.02 (17)
H3A—C3—H3C109.5O5—C24—N4123.22 (17)
H3B—C3—H3C109.5O4—C24—N4109.76 (16)
O1—C4—C3109.24 (15)N5—C25—N4121.01 (16)
O1—C4—C1110.23 (15)N5—C25—S2116.96 (14)
C3—C4—C1113.05 (18)N4—C25—S2122.03 (14)
O1—C4—C2102.60 (14)C27—C26—N5125.16 (16)
C3—C4—C2111.01 (17)C27—C26—C31119.80 (16)
C1—C4—C2110.21 (17)N5—C26—C31115.03 (16)
O2—C5—O1126.91 (17)C28—C27—C26119.02 (17)
O2—C5—N1123.45 (17)C28—C27—H27120.5
O1—C5—N1109.64 (15)C26—C27—H27120.5
N2—C6—N1120.96 (16)C27—C28—C29121.05 (17)
N2—C6—S1117.36 (14)C27—C28—H28119.5
N1—C6—S1121.68 (14)C29—C28—H28119.5
N2—C7—C8125.35 (16)C30—C29—C28120.34 (16)
N2—C7—C12115.22 (16)C30—C29—C32120.88 (16)
C8—C7—C12119.44 (16)C28—C29—C32118.35 (16)
C9—C8—C7118.75 (17)C29—C30—C31118.30 (17)
C9—C8—H8120.6C29—C30—H30120.8
C7—C8—H8120.6C31—C30—H30120.8
C8—C9—C10121.50 (17)C30—C31—C26121.38 (17)
C8—C9—H9119.2C30—C31—S2128.57 (14)
C10—C9—H9119.2C26—C31—S2110.02 (13)
C11—C10—C9120.03 (17)O6—C32—N6121.92 (17)
C11—C10—C13117.64 (16)O6—C32—C29118.79 (16)
C9—C10—C13122.28 (16)N6—C32—C29119.22 (16)
C10—C11—C12118.46 (17)N6—C33—C34113.35 (17)
C10—C11—H11120.8N6—C33—H33A108.9
C12—C11—H11120.8C34—C33—H33A108.9
C11—C12—C7121.77 (16)N6—C33—H33B108.9
C11—C12—S1127.97 (14)C34—C33—H33B108.9
C7—C12—S1110.25 (13)H33A—C33—H33B107.7
O3—C13—N3121.74 (17)C33—C34—C35110.6 (2)
O3—C13—C10119.49 (17)C33—C34—H34A109.5
N3—C13—C10118.77 (16)C35—C34—H34A109.5
N3—C14—C15113.52 (16)C33—C34—H34B109.5
N3—C14—H14A108.9C35—C34—H34B109.5
C15—C14—H14A108.9H34A—C34—H34B108.1
N3—C14—H14B108.9C34—C35—H35A109.5
C15—C14—H14B108.9C34—C35—H35B109.5
H14A—C14—H14B107.7H35A—C35—H35B109.5
C16—C15—C14111.76 (17)C34—C35—H35C109.5
C16—C15—H15A109.3H35A—C35—H35C109.5
C14—C15—H15A109.3H35B—C35—H35C109.5
C16—C15—H15B109.3N6—C36—C37112.85 (17)
C14—C15—H15B109.3N6—C36—H36A109.0
H15A—C15—H15B107.9C37—C36—H36A109.0
C15—C16—H16A109.5N6—C36—H36B109.0
C15—C16—H16B109.5C37—C36—H36B109.0
H16A—C16—H16B109.5H36A—C36—H36B107.8
C15—C16—H16C109.5C36—C37—C38112.81 (19)
H16A—C16—H16C109.5C36—C37—H37A109.0
H16B—C16—H16C109.5C38—C37—H37A109.0
N3—C17—C18112.97 (17)C36—C37—H37B109.0
N3—C17—H17A109.0C38—C37—H37B109.0
C18—C17—H17A109.0H37A—C37—H37B107.8
N3—C17—H17B109.0C37—C38—H38A109.5
C18—C17—H17B109.0C37—C38—H38B109.5
H17A—C17—H17B107.8H38A—C38—H38B109.5
C17—C18—C19111.2 (2)C37—C38—H38C109.5
C17—C18—H18A109.4H38A—C38—H38C109.5
C19—C18—H18A109.4H38B—C38—H38C109.5

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C26–C31 benzene ring.
D—H···AD—HH···AD···AD—H···A
N1—H1···N50.862.122.963 (2)168
N4—H4···N20.862.163.006 (2)167
C8—H8···O40.932.593.461 (2)157
C27—H27···O10.932.613.321 (2)134
C11—H11···O6i0.932.383.161 (2)141
C28—H28···O3ii0.932.613.292 (2)131
C37—H37A···O6iii0.972.563.375 (3)142
C16—H16B···O3iv0.962.443.397 (3)177
C20—H20C···O2v0.962.613.460 (3)147
C22—H22A···Cgvi0.962.983.942 (3)176

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2775).

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