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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1200–o1201.
Published online 2010 April 28. doi:  10.1107/S1600536810014947
PMCID: PMC2979233

2-[(1Z)-(9-Ethyl-9H-carbazol-3-yl)methyl­eneamino]-4,5,6,7-tetra­hydro-1-benzothio­phene-3-carbonitrile–benzene (2/1)

Abstract

In the title compound, 2C24H21N3S·C6H6, the two independent Schiff base mol­ecules (A and B) in the asymmetric unit differ in the orientation of the tetra­hydro­benzothio­phene ring system with respect to the carbazole ring system by 180° rotation about the C—C bond in the C—C=N—C linkage. The two mol­ecules also differ in the orientation of the ethyl groups [C—N—C—C torsion angle of 90.7 (3)° in mol­ecule A, and −79.4 (3)° in mol­ecule B]. In mol­ecule B, two methyl­ene C atoms of the cyclo­hexene ring are disordered over two sites with occupancies of 0.58 (1) and 0.42 (1). The cyclo­hexene rings in both mol­ecules adopt half-chair conformations. The dihedral angle between the thio­phene ring and the carbazole ring system is 8.07 (9)° in mol­ecule A [3.10 (9)° in mol­ecule B]. In the crystal structure, the independent mol­ecules are linked into dimers by inter­molecular C—H(...)N hydrogen bonds. In addition, C—H(...)π inter­actions are observed.

Related literature

For biological and other applications of Schiff base compounds, see: Abu-Hussen (2006 [triangle]); Elerman et al. (2002 [triangle]); Panneerselvam et al. (2005 [triangle]); Walsh et al. (1996 [triangle]). For ring puckering parameters, see: Cremer & Pople (1975 [triangle]). For a related structure, see: Elerman & Elmali (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1200-scheme1.jpg

Experimental

Crystal data

  • 2C24H21N3S·C6H6
  • M r = 845.10
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1200-efi1.jpg
  • a = 11.4816 (1) Å
  • b = 13.7322 (2) Å
  • c = 14.8358 (2) Å
  • α = 81.841 (1)°
  • β = 77.083 (1)°
  • γ = 83.864 (1)°
  • V = 2250.00 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.16 mm−1
  • T = 293 K
  • 0.45 × 0.15 × 0.07 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.931, T max = 0.989
  • 48693 measured reflections
  • 13169 independent reflections
  • 6227 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.070
  • wR(F 2) = 0.167
  • S = 1.01
  • 13169 reflections
  • 580 parameters
  • 63 restraints
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014947/ci5065sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014947/ci5065Isup2.hkl

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

Acknowledgments

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship. The authors thank the Department of Chemistry, King Abdulaziz University, for providing research facilities.

supplementary crystallographic information

Comment

Schiff bases are an important class of compounds in medicinal and pharmaceutical field. They show biological applications including anti-bacterial (Abu-Hussen, 2006), anti-fungal (Panneerselvam et al., 2005) and anti-tumor (Walsh et al., 1996) activities. In the field of coordination chemistry, they are used extensively as ligands due to intramolecular hydrogen bonds between O and N atoms, which is applicable for the formation of metal complexes. Schiff bases are also used in the field of photochromism and thermochromism in the solid state (Elerman et al., 2002). In this paper, we report the crystal structure of the title Schiff base compound.

The asymmetric unit of the title compound (Fig. 1) consists of two crystallographically independent Schiff base molecules and a benzene solvent molecule. The two independent main molecules differ in the orientation of the tetrahydrobenzothiophene ring system with respect to the 9H-carbazole ring system by 180° rotation about the C9—C13 bond. The conformation of the ethyl group (C22/C23) also differs in both molecules, with C1A—N1A—C22A—C23A torsion angle of 90.7 (3)° in molecule A, indicating (+)-anti-clinal conformation, whereas C1B—N1B—C22B—C23B torsion angle of -79.4 (3)° in molecule B, indicating (-)-syn-clinal conformation.

In molecule A, the cyclohexene ring (C16A-C21A) adopts a half-chair conformation, with puckering parameters of Q = 0.433 (3) Å, θ = 49.1 (4)° and [var phi] = 145.4 (5)° (Cremer & Pople, 1975). In both the major and minor conformers of molecule B, the cyclohexene rings adopt half-chair conformations; the puckering parameters: Q = 0.508 (7) Å, θ = 50.0 (6)° and [var phi] = 155.0 (7)° for the major conformer and Q = 0.467 (9) Å, θ = 130.4 (7)°, and [var phi] = 330.0 (10)° for the minor conformer. The dihedral angle between the thiophene ring and the carbazole ring system is 8.07 (9)° in molecule A and 3.10 (9)° in molecule B. The bond lengths and angles are comparable to a related 4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile structure (Elerman & Elmali, 1998).

In the crystal structure (Fig. 2), the benzene solvent molecule is not involved in intermolecular hydrogen bonding. The Schiff base molecules are linked into dimers by pairs of intermolecular C22A—H22A···N3B hydrogen bonds (Table 1). The crystal structure is further stabilized by weak intermolecular C—H···π interactions (Table 1).

Experimental

A mixture of carbazolealdehyde (0.50 g, 0.0022 mol) and 2-amino-3-cyanobenzothiophene (0.38 g, 0.0022 mol) in methanol (15 ml) was refluxed for 5 h with stirring to give a light yellow precipitate. It was then filtered and washed with methanol to give the pure Schiff base. Good quality single crystals were recrystallized from a mixture of benzene, chloroform and methanol (4:4:2). (Yield 78 %, M.p. 468 K).

Refinement

Atoms C18B and C19B are both disordered over two positions with occupancies of 0.58 (1) and 0.42 (1). In both disorder components, the C—C distances involving the disordered atoms were restrained to be equal. In the benzene solvent molecule, the C—C distances were restrained to 1.384 (3) Å. The Uij components of atom C18X and all C atoms of the benzene solvent molecule were restrained to an approximate isotropic behaviour. H atoms were placed in their calculated positions [C–H = 0.93–97 Å] and refined using a riding model with Uiso = 1.2 or 1.5 Ueq(C).

Figures

Fig. 1.
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 20 % probability level. For clarity, the benzene solvent molecule is not shown.
Fig. 2.
The crystal structure of the title compound, viewed along the a axis, showing the molecules being linked into dimers. Only the major disordered components are shown. H atoms not involved in intermolecular interactions (dashed lines) have been omitted ...

Crystal data

2C24H21N3S·C6H6Z = 2
Mr = 845.10F(000) = 892
Triclinic, P1Dx = 1.247 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.4816 (1) ÅCell parameters from 6974 reflections
b = 13.7322 (2) Åθ = 2.4–21.2°
c = 14.8358 (2) ŵ = 0.16 mm1
α = 81.841 (1)°T = 293 K
β = 77.083 (1)°Plate, yellow
γ = 83.864 (1)°0.45 × 0.15 × 0.07 mm
V = 2250.00 (5) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer13169 independent reflections
Radiation source: fine-focus sealed tube6227 reflections with I > 2σ(I)
graphiteRint = 0.048
[var phi] and ω scansθmax = 30.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −16→16
Tmin = 0.931, Tmax = 0.989k = −19→19
48693 measured reflectionsl = −20→20

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)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0574P)2 + 0.4624P] where P = (Fo2 + 2Fc2)/3
13169 reflections(Δ/σ)max = 0.001
580 parametersΔρmax = 0.31 e Å3
63 restraintsΔρmin = −0.20 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 > 2sigma(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*/UeqOcc. (<1)
S1A−0.28193 (6)0.58795 (5)0.14257 (5)0.0645 (2)
N1A0.35074 (17)0.81675 (13)−0.21845 (13)0.0532 (5)
N2A−0.03256 (16)0.58008 (14)0.08737 (14)0.0554 (5)
N3A0.0583 (2)0.3886 (2)0.2688 (2)0.0964 (8)
C1A0.4457 (2)0.75882 (16)−0.18956 (15)0.0496 (5)
C2A0.5683 (2)0.76344 (19)−0.22354 (18)0.0622 (7)
H2A0.59830.8120−0.27090.075*
C3A0.6437 (2)0.6938 (2)−0.1847 (2)0.0693 (7)
H3A0.72590.6942−0.20750.083*
C4A0.6002 (2)0.6226 (2)−0.1121 (2)0.0718 (7)
H4A0.65370.5773−0.08640.086*
C5A0.4785 (2)0.61827 (18)−0.07770 (18)0.0630 (7)
H5A0.44970.5709−0.02870.076*
C6A0.39982 (19)0.68584 (16)−0.11748 (15)0.0481 (5)
C7A0.27086 (19)0.69989 (15)−0.10253 (14)0.0452 (5)
C8A0.17748 (19)0.65416 (16)−0.04151 (15)0.0492 (5)
H8A0.19320.60220.00270.059*
C9A0.0596 (2)0.68660 (16)−0.04674 (15)0.0504 (5)
C10A0.0376 (2)0.76495 (18)−0.11427 (17)0.0603 (6)
H10A−0.04130.7849−0.11820.072*
C11A0.1282 (2)0.81317 (17)−0.17470 (16)0.0573 (6)
H11A0.11190.8654−0.21850.069*
C12A0.2451 (2)0.78087 (16)−0.16790 (15)0.0478 (5)
C13A−0.0413 (2)0.64287 (17)0.01630 (17)0.0559 (6)
H13A−0.11730.66150.00450.067*
C14A−0.13382 (19)0.54642 (16)0.14786 (16)0.0514 (6)
C15A−0.13252 (19)0.47652 (16)0.22303 (16)0.0488 (5)
C16A−0.2488 (2)0.45626 (16)0.27752 (15)0.0486 (5)
C17A−0.2730 (2)0.3862 (2)0.36522 (18)0.0672 (7)
H17A−0.21540.39240.40250.081*
H17B−0.26330.31910.34980.081*
C18A−0.3980 (3)0.4065 (2)0.4210 (2)0.0870 (9)
H18A−0.41790.35060.46790.104*
H18B−0.39970.46370.45290.104*
C19A−0.4892 (3)0.4243 (3)0.3640 (2)0.0874 (9)
H19A−0.56690.43670.40440.105*
H19B−0.49170.36500.33610.105*
C20A−0.4682 (2)0.5109 (2)0.28643 (19)0.0695 (7)
H20A−0.51320.50490.23960.083*
H20B−0.49610.57250.31200.083*
C21A−0.3371 (2)0.51130 (17)0.24260 (16)0.0534 (6)
C22A0.3612 (2)0.90256 (18)−0.28954 (17)0.0651 (7)
H22A0.43260.9343−0.28930.078*
H22B0.29260.9494−0.27370.078*
C23A0.3678 (3)0.8773 (2)−0.38548 (18)0.0853 (9)
H23A0.37590.9362−0.42910.128*
H23B0.29590.8483−0.38700.128*
H23C0.43570.8313−0.40190.128*
C24A−0.0248 (2)0.42838 (19)0.24646 (18)0.0624 (7)
S1B0.38291 (6)0.72056 (5)0.14806 (5)0.0707 (2)
N1B0.91999 (18)1.09596 (14)−0.17385 (13)0.0557 (5)
N2B0.50847 (18)0.88652 (15)0.13816 (13)0.0599 (5)
N3B0.3760 (2)0.9764 (2)0.36567 (18)0.0917 (8)
C1B0.9522 (2)1.04208 (17)−0.24963 (16)0.0530 (6)
C2B1.0415 (2)1.05656 (19)−0.32907 (17)0.0618 (7)
H2B1.08981.1089−0.33870.074*
C3B1.0561 (2)0.9905 (2)−0.39332 (18)0.0706 (7)
H3B1.11560.9984−0.44720.085*
C4B0.9841 (2)0.9125 (2)−0.37945 (17)0.0703 (7)
H4B0.99610.8692−0.42410.084*
C5B0.8949 (2)0.8980 (2)−0.30040 (16)0.0605 (6)
H5B0.84670.8457−0.29170.073*
C6B0.87815 (19)0.96298 (17)−0.23398 (15)0.0493 (5)
C7B0.79972 (19)0.96862 (16)−0.14364 (15)0.0482 (5)
C8B0.7109 (2)0.91230 (17)−0.08940 (15)0.0529 (6)
H8B0.68980.8582−0.11180.063*
C9B0.6528 (2)0.93600 (17)−0.00138 (16)0.0535 (6)
C10B0.6838 (2)1.01967 (18)0.03051 (16)0.0593 (6)
H10B0.64391.03620.08880.071*
C11B0.7708 (2)1.07744 (18)−0.02177 (17)0.0594 (6)
H11B0.79021.13240.00030.071*
C12B0.8295 (2)1.05139 (17)−0.10915 (16)0.0517 (6)
C13B0.5630 (2)0.87384 (19)0.05443 (17)0.0596 (6)
H13B0.54350.82170.02840.071*
C14B0.4238 (2)0.82359 (18)0.18658 (16)0.0574 (6)
C15B0.3571 (2)0.83434 (19)0.27491 (16)0.0574 (6)
C16B0.2759 (2)0.7603 (2)0.31164 (17)0.0590 (6)
C17B0.1949 (2)0.7533 (2)0.40691 (18)0.0787 (8)
H17C0.24350.73240.45290.094*0.580 (10)
H17D0.15770.81860.41780.094*0.580 (10)
H17E0.12620.80000.40880.094*0.420 (10)
H17F0.23720.76400.45320.094*0.420 (10)
C18B0.1000 (5)0.6851 (5)0.4213 (6)0.094 (3)0.580 (10)
H18C0.03600.71430.39070.113*0.580 (10)
H18D0.06670.66900.48720.113*0.580 (10)
C19B0.1608 (7)0.5936 (5)0.3786 (4)0.097 (3)0.580 (10)
H19C0.10460.54280.39460.117*0.580 (10)
H19D0.22810.56990.40740.117*0.580 (10)
C18X0.1499 (9)0.6467 (6)0.4240 (7)0.082 (3)0.420 (10)
H18E0.21610.60120.43760.098*0.420 (10)
H18F0.08760.64370.48030.098*0.420 (10)
C19X0.1007 (7)0.6051 (8)0.3504 (5)0.085 (3)0.420 (10)
H19E0.07670.53870.37190.102*0.420 (10)
H19F0.03320.64680.33380.102*0.420 (10)
C20B0.2076 (3)0.6061 (2)0.2700 (2)0.0834 (9)
H20C0.25680.54790.25000.100*0.580 (10)
H20D0.14140.61790.23810.100*0.580 (10)
H20E0.26000.54830.28100.100*0.420 (10)
H20F0.18220.60140.21350.100*0.420 (10)
C21B0.2802 (2)0.6939 (2)0.25154 (19)0.0662 (7)
C22B0.9866 (2)1.17511 (18)−0.1602 (2)0.0675 (7)
H22C0.93461.2166−0.11760.081*
H22D1.01111.2156−0.21930.081*
C23B1.0961 (3)1.1365 (2)−0.1218 (2)0.0892 (9)
H23D1.13881.1909−0.11600.134*
H23E1.14731.0946−0.16330.134*
H23F1.07201.0995−0.06170.134*
C24B0.3697 (2)0.9139 (2)0.32369 (18)0.0665 (7)
C250.3449 (4)0.1706 (3)0.5697 (4)0.1256 (15)
H25A0.39550.11380.57700.151*
C260.3230 (4)0.2345 (4)0.6346 (3)0.1390 (16)
H26A0.35580.22150.68740.167*
C270.2512 (5)0.3183 (4)0.6194 (4)0.1336 (17)
H27A0.23390.36220.66380.160*
C280.2037 (4)0.3403 (3)0.5419 (4)0.1294 (17)
H28A0.15790.39940.53240.155*
C290.2247 (4)0.2739 (4)0.4784 (3)0.1280 (15)
H29A0.19230.28660.42550.154*
C300.2938 (4)0.1888 (4)0.4942 (3)0.1156 (14)
H30A0.30620.14230.45250.139*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S1A0.0501 (4)0.0724 (4)0.0636 (4)0.0010 (3)−0.0070 (3)0.0043 (3)
N1A0.0549 (12)0.0531 (11)0.0460 (11)−0.0064 (9)−0.0053 (9)0.0061 (9)
N2A0.0508 (11)0.0565 (12)0.0528 (12)−0.0063 (9)0.0015 (9)−0.0040 (10)
N3A0.0632 (16)0.099 (2)0.122 (2)0.0068 (14)−0.0265 (16)0.0024 (17)
C1A0.0507 (13)0.0514 (13)0.0442 (13)−0.0043 (10)−0.0036 (11)−0.0068 (10)
C2A0.0581 (15)0.0664 (16)0.0602 (16)−0.0146 (13)−0.0042 (13)−0.0071 (13)
C3A0.0501 (14)0.0766 (18)0.0796 (19)−0.0084 (13)−0.0039 (14)−0.0170 (16)
C4A0.0542 (16)0.0708 (18)0.087 (2)0.0061 (13)−0.0172 (15)−0.0039 (16)
C5A0.0568 (15)0.0598 (15)0.0654 (17)0.0018 (12)−0.0084 (13)0.0039 (13)
C6A0.0492 (13)0.0477 (12)0.0443 (13)0.0010 (10)−0.0049 (10)−0.0069 (10)
C7A0.0499 (12)0.0441 (12)0.0388 (12)0.0029 (9)−0.0065 (10)−0.0051 (10)
C8A0.0545 (14)0.0456 (12)0.0413 (12)0.0009 (10)−0.0029 (11)0.0001 (10)
C9A0.0498 (13)0.0515 (13)0.0450 (13)0.0009 (10)−0.0031 (11)−0.0046 (11)
C10A0.0498 (14)0.0666 (16)0.0590 (15)0.0027 (12)−0.0087 (12)0.0003 (13)
C11A0.0585 (15)0.0568 (14)0.0507 (14)0.0035 (12)−0.0111 (12)0.0068 (11)
C12A0.0520 (13)0.0479 (12)0.0393 (12)−0.0008 (10)−0.0035 (10)−0.0026 (10)
C13A0.0476 (13)0.0606 (15)0.0560 (15)−0.0020 (11)−0.0038 (12)−0.0082 (12)
C14A0.0460 (12)0.0533 (13)0.0516 (14)−0.0049 (10)−0.0014 (11)−0.0090 (11)
C15A0.0439 (12)0.0499 (13)0.0516 (14)−0.0021 (10)−0.0063 (11)−0.0094 (11)
C16A0.0480 (13)0.0509 (13)0.0454 (13)−0.0054 (10)−0.0038 (11)−0.0092 (10)
C17A0.0643 (16)0.0699 (17)0.0602 (16)−0.0107 (13)−0.0016 (13)0.0018 (13)
C18A0.0717 (19)0.101 (2)0.073 (2)−0.0109 (16)0.0082 (17)0.0050 (17)
C19A0.0588 (17)0.122 (3)0.075 (2)−0.0309 (17)0.0083 (16)−0.0096 (19)
C20A0.0441 (13)0.0883 (19)0.0717 (18)−0.0063 (13)0.0000 (13)−0.0132 (15)
C21A0.0463 (13)0.0589 (14)0.0524 (14)−0.0078 (11)−0.0023 (11)−0.0086 (11)
C22A0.0695 (17)0.0569 (15)0.0603 (16)−0.0095 (12)−0.0058 (13)0.0121 (12)
C23A0.111 (2)0.0760 (19)0.0556 (17)−0.0056 (17)−0.0047 (16)0.0147 (14)
C24A0.0514 (15)0.0620 (16)0.0688 (17)−0.0038 (12)−0.0055 (13)−0.0031 (13)
S1B0.0759 (5)0.0701 (4)0.0595 (4)−0.0001 (3)−0.0028 (4)−0.0085 (3)
N1B0.0635 (12)0.0509 (11)0.0520 (12)−0.0042 (9)−0.0134 (10)−0.0024 (9)
N2B0.0579 (12)0.0684 (13)0.0458 (12)0.0043 (10)−0.0037 (10)−0.0002 (10)
N3B0.0908 (19)0.112 (2)0.0738 (17)−0.0163 (16)−0.0070 (14)−0.0249 (16)
C1B0.0545 (14)0.0568 (14)0.0454 (13)0.0036 (11)−0.0163 (11)0.0045 (11)
C2B0.0590 (15)0.0697 (16)0.0511 (15)−0.0039 (12)−0.0111 (12)0.0101 (13)
C3B0.0669 (17)0.094 (2)0.0426 (14)−0.0024 (15)−0.0040 (13)0.0057 (14)
C4B0.0740 (18)0.092 (2)0.0437 (14)0.0003 (16)−0.0083 (13)−0.0153 (14)
C5B0.0610 (15)0.0772 (17)0.0442 (14)−0.0056 (13)−0.0104 (12)−0.0112 (12)
C6B0.0484 (13)0.0581 (14)0.0404 (12)0.0040 (11)−0.0133 (10)−0.0025 (11)
C7B0.0492 (13)0.0524 (13)0.0423 (12)0.0044 (10)−0.0125 (11)−0.0048 (10)
C8B0.0549 (14)0.0572 (14)0.0464 (13)−0.0001 (11)−0.0112 (11)−0.0079 (11)
C9B0.0531 (14)0.0599 (14)0.0447 (13)0.0050 (11)−0.0098 (11)−0.0045 (11)
C10B0.0674 (16)0.0650 (16)0.0416 (13)0.0082 (13)−0.0078 (12)−0.0099 (12)
C11B0.0715 (17)0.0567 (15)0.0525 (15)0.0037 (12)−0.0169 (13)−0.0154 (12)
C12B0.0573 (14)0.0513 (13)0.0450 (13)0.0049 (11)−0.0164 (11)0.0014 (11)
C13B0.0575 (15)0.0661 (16)0.0517 (15)0.0030 (12)−0.0097 (12)−0.0045 (12)
C14B0.0547 (14)0.0641 (15)0.0488 (14)0.0056 (12)−0.0101 (12)0.0002 (12)
C15B0.0531 (14)0.0705 (16)0.0451 (14)0.0077 (12)−0.0115 (12)−0.0023 (12)
C16B0.0460 (13)0.0734 (17)0.0496 (14)0.0070 (12)−0.0062 (11)0.0039 (13)
C17B0.0623 (17)0.102 (2)0.0585 (17)0.0043 (16)−0.0010 (14)0.0067 (16)
C18B0.040 (3)0.157 (7)0.080 (4)−0.020 (4)−0.004 (3)−0.003 (4)
C19B0.061 (4)0.065 (4)0.149 (8)−0.018 (4)0.002 (5)0.016 (4)
C18X0.038 (5)0.145 (8)0.059 (5)−0.020 (5)−0.002 (4)−0.004 (5)
C19X0.051 (5)0.101 (6)0.097 (7)−0.013 (5)0.005 (5)−0.016 (5)
C20B0.078 (2)0.076 (2)0.089 (2)−0.0112 (15)−0.0121 (17)0.0067 (17)
C21B0.0565 (15)0.0678 (17)0.0664 (17)0.0037 (13)−0.0087 (13)0.0050 (14)
C22B0.0768 (18)0.0512 (15)0.0759 (18)−0.0068 (13)−0.0204 (15)−0.0041 (13)
C23B0.081 (2)0.086 (2)0.111 (3)0.0008 (16)−0.0391 (19)−0.0243 (19)
C24B0.0595 (16)0.087 (2)0.0484 (15)−0.0008 (14)−0.0069 (13)−0.0038 (15)
C250.096 (3)0.097 (3)0.156 (4)−0.003 (2)0.014 (3)0.009 (3)
C260.114 (3)0.178 (5)0.132 (4)−0.042 (3)−0.026 (3)−0.022 (4)
C270.128 (4)0.118 (4)0.162 (4)−0.040 (3)0.005 (3)−0.079 (3)
C280.080 (3)0.086 (3)0.196 (5)−0.003 (2)0.011 (3)0.008 (3)
C290.093 (3)0.183 (5)0.098 (3)−0.044 (3)−0.005 (2)0.017 (3)
C300.119 (3)0.121 (3)0.098 (3)−0.038 (3)0.032 (2)−0.051 (3)

Geometric parameters (Å, °)

S1A—C21A1.729 (2)C3B—C4B1.388 (4)
S1A—C14A1.750 (2)C3B—H3B0.93
N1A—C12A1.376 (3)C4B—C5B1.380 (3)
N1A—C1A1.390 (3)C4B—H4B0.93
N1A—C22A1.462 (3)C5B—C6B1.390 (3)
N2A—C13A1.279 (3)C5B—H5B0.93
N2A—C14A1.379 (3)C6B—C7B1.445 (3)
N3A—C24A1.139 (3)C7B—C8B1.382 (3)
C1A—C2A1.390 (3)C7B—C12B1.413 (3)
C1A—C6A1.408 (3)C8B—C9B1.393 (3)
C2A—C3A1.373 (4)C8B—H8B0.93
C2A—H2A0.93C9B—C10B1.409 (3)
C3A—C4A1.388 (4)C9B—C13B1.443 (3)
C3A—H3A0.93C10B—C11B1.370 (3)
C4A—C5A1.381 (3)C10B—H10B0.93
C4A—H4A0.93C11B—C12B1.398 (3)
C5A—C6A1.389 (3)C11B—H11B0.93
C5A—H5A0.93C13B—H13B0.93
C6A—C7A1.443 (3)C14B—C15B1.381 (3)
C7A—C8A1.383 (3)C15B—C16B1.421 (3)
C7A—C12A1.420 (3)C15B—C24B1.430 (4)
C8A—C9A1.394 (3)C16B—C21B1.353 (4)
C8A—H8A0.93C16B—C17B1.505 (3)
C9A—C10A1.405 (3)C17B—C18B1.472 (5)
C9A—C13A1.444 (3)C17B—C18X1.573 (7)
C10A—C11A1.374 (3)C17B—H17C0.97
C10A—H10A0.93C17B—H17D0.97
C11A—C12A1.388 (3)C17B—H17E0.96
C11A—H11A0.93C17B—H17F0.96
C13A—H13A0.93C18B—C19B1.520 (6)
C14A—C15A1.366 (3)C18B—H18C0.97
C15A—C24A1.428 (4)C18B—H18D0.97
C15A—C16A1.430 (3)C19B—C20B1.571 (6)
C16A—C21A1.352 (3)C19B—H19C0.97
C16A—C17A1.495 (3)C19B—H19D0.97
C17A—C18A1.506 (4)C18X—C19X1.535 (7)
C17A—H17A0.97C18X—H18E0.97
C17A—H17B0.97C18X—H18F0.97
C18A—C19A1.467 (4)C19X—C20B1.508 (6)
C18A—H18A0.97C19X—H19E0.97
C18A—H18B0.97C19X—H19F0.97
C19A—C20A1.531 (4)C20B—C21B1.497 (4)
C19A—H19A0.97C20B—H20C0.97
C19A—H19B0.97C20B—H20D0.97
C20A—C21A1.501 (3)C20B—H20E0.96
C20A—H20A0.97C20B—H20F0.96
C20A—H20B0.97C22B—C23B1.510 (4)
C22A—C23A1.496 (4)C22B—H22C0.97
C22A—H22A0.97C22B—H22D0.97
C22A—H22B0.97C23B—H23D0.96
C23A—H23A0.96C23B—H23E0.96
C23A—H23B0.96C23B—H23F0.96
C23A—H23C0.96C25—C261.358 (7)
S1B—C21B1.734 (3)C25—C301.358 (7)
S1B—C14B1.743 (3)C25—H25A0.93
N1B—C12B1.378 (3)C26—C271.364 (8)
N1B—C1B1.393 (3)C26—H26A0.93
N1B—C22B1.455 (3)C27—C281.363 (8)
N2B—C13B1.287 (3)C27—H27A0.93
N2B—C14B1.378 (3)C28—C291.368 (7)
N3B—C24B1.146 (3)C28—H28A0.93
C1B—C2B1.385 (3)C29—C301.363 (7)
C1B—C6B1.412 (3)C29—H29A0.93
C2B—C3B1.379 (4)C30—H30A0.93
C2B—H2B0.93
C21A—S1A—C14A91.75 (11)C7B—C8B—H8B119.8
C12A—N1A—C1A108.65 (18)C9B—C8B—H8B119.8
C12A—N1A—C22A125.6 (2)C8B—C9B—C10B119.1 (2)
C1A—N1A—C22A125.74 (19)C8B—C9B—C13B118.9 (2)
C13A—N2A—C14A120.6 (2)C10B—C9B—C13B122.1 (2)
N1A—C1A—C2A129.5 (2)C11B—C10B—C9B122.0 (2)
N1A—C1A—C6A109.02 (19)C11B—C10B—H10B119.0
C2A—C1A—C6A121.5 (2)C9B—C10B—H10B119.0
C3A—C2A—C1A117.6 (2)C10B—C11B—C12B118.1 (2)
C3A—C2A—H2A121.2C10B—C11B—H11B121.0
C1A—C2A—H2A121.2C12B—C11B—H11B121.0
C2A—C3A—C4A121.7 (2)N1B—C12B—C11B129.4 (2)
C2A—C3A—H3A119.1N1B—C12B—C7B109.3 (2)
C4A—C3A—H3A119.1C11B—C12B—C7B121.3 (2)
C5A—C4A—C3A120.8 (3)N2B—C13B—C9B123.7 (2)
C5A—C4A—H4A119.6N2B—C13B—H13B118.1
C3A—C4A—H4A119.6C9B—C13B—H13B118.1
C4A—C5A—C6A118.9 (2)N2B—C14B—C15B123.8 (2)
C4A—C5A—H5A120.6N2B—C14B—S1B126.62 (18)
C6A—C5A—H5A120.6C15B—C14B—S1B109.55 (19)
C5A—C6A—C1A119.5 (2)C14B—C15B—C16B114.1 (2)
C5A—C6A—C7A133.6 (2)C14B—C15B—C24B122.1 (2)
C1A—C6A—C7A106.86 (19)C16B—C15B—C24B123.8 (2)
C8A—C7A—C12A119.4 (2)C21B—C16B—C15B112.4 (2)
C8A—C7A—C6A134.4 (2)C21B—C16B—C17B122.7 (2)
C12A—C7A—C6A106.16 (18)C15B—C16B—C17B125.0 (3)
C7A—C8A—C9A119.5 (2)C18B—C17B—C16B114.8 (4)
C7A—C8A—H8A120.2C16B—C17B—C18X105.1 (4)
C9A—C8A—H8A120.2C18B—C17B—H17C108.6
C8A—C9A—C10A119.5 (2)C16B—C17B—H17C108.6
C8A—C9A—C13A121.9 (2)C18X—C17B—H17C88.7
C10A—C9A—C13A118.6 (2)C18B—C17B—H17D108.6
C11A—C10A—C9A122.5 (2)C16B—C17B—H17D108.6
C11A—C10A—H10A118.8C18X—C17B—H17D134.9
C9A—C10A—H10A118.8H17C—C17B—H17D107.5
C10A—C11A—C12A117.4 (2)C18B—C17B—H17E80.2
C10A—C11A—H11A121.3C16B—C17B—H17E111.5
C12A—C11A—H11A121.3C18X—C17B—H17E108.0
N1A—C12A—C11A129.0 (2)H17C—C17B—H17E130.0
N1A—C12A—C7A109.28 (19)C18B—C17B—H17F125.3
C11A—C12A—C7A121.7 (2)C16B—C17B—H17F110.9
N2A—C13A—C9A123.9 (2)C18X—C17B—H17F112.0
N2A—C13A—H13A118.0H17D—C17B—H17F82.7
C9A—C13A—H13A118.0H17E—C17B—H17F109.3
C15A—C14A—N2A124.4 (2)C17B—C18B—C19B105.3 (5)
C15A—C14A—S1A109.76 (16)C17B—C18B—H18C110.7
N2A—C14A—S1A125.85 (18)C19B—C18B—H18C110.7
C14A—C15A—C24A123.3 (2)C17B—C18B—H18D110.7
C14A—C15A—C16A114.2 (2)C19B—C18B—H18D110.7
C24A—C15A—C16A122.5 (2)H18C—C18B—H18D108.8
C21A—C16A—C15A112.0 (2)C18B—C19B—C20B116.5 (6)
C21A—C16A—C17A122.6 (2)C18B—C19B—H19C108.2
C15A—C16A—C17A125.3 (2)C20B—C19B—H19C108.2
C16A—C17A—C18A111.3 (2)C18B—C19B—H19D108.2
C16A—C17A—H17A109.4C20B—C19B—H19D108.2
C18A—C17A—H17A109.4H19C—C19B—H19D107.3
C16A—C17A—H17B109.4C19X—C18X—C17B121.8 (7)
C18A—C17A—H17B109.4C19X—C18X—H18E106.9
H17A—C17A—H17B108.0C17B—C18X—H18E106.9
C19A—C18A—C17A113.3 (3)C19X—C18X—H18F106.9
C19A—C18A—H18A108.9C17B—C18X—H18F106.9
C17A—C18A—H18A108.9H18E—C18X—H18F106.7
C19A—C18A—H18B108.9C20B—C19X—C18X101.7 (7)
C17A—C18A—H18B108.9C20B—C19X—H19E111.4
H18A—C18A—H18B107.7C18X—C19X—H19E111.4
C18A—C19A—C20A114.3 (2)C20B—C19X—H19F111.4
C18A—C19A—H19A108.7C18X—C19X—H19F111.4
C20A—C19A—H19A108.7H19E—C19X—H19F109.3
C18A—C19A—H19B108.7C21B—C20B—C19X116.9 (4)
C20A—C19A—H19B108.7C21B—C20B—C19B103.9 (4)
H19A—C19A—H19B107.6C21B—C20B—H20C111.0
C21A—C20A—C19A109.7 (2)C19X—C20B—H20C124.8
C21A—C20A—H20A109.7C19B—C20B—H20C111.0
C19A—C20A—H20A109.7C21B—C20B—H20D111.0
C21A—C20A—H20B109.7C19X—C20B—H20D78.1
C19A—C20A—H20B109.7C19B—C20B—H20D111.0
H20A—C20A—H20B108.2H20C—C20B—H20D109.0
C16A—C21A—C20A124.9 (2)C21B—C20B—H20E107.9
C16A—C21A—S1A112.23 (17)C19X—C20B—H20E108.1
C20A—C21A—S1A122.78 (19)C19B—C20B—H20E85.4
N1A—C22A—C23A113.3 (2)H20D—C20B—H20E131.9
N1A—C22A—H22A108.9C21B—C20B—H20F106.7
C23A—C22A—H22A108.9C19X—C20B—H20F109.8
N1A—C22A—H22B108.9C19B—C20B—H20F141.1
C23A—C22A—H22B108.9H20C—C20B—H20F79.6
H22A—C22A—H22B107.7H20E—C20B—H20F107.0
C22A—C23A—H23A109.5C16B—C21B—C20B125.5 (2)
C22A—C23A—H23B109.5C16B—C21B—S1B112.0 (2)
H23A—C23A—H23B109.5C20B—C21B—S1B122.5 (2)
C22A—C23A—H23C109.5N1B—C22B—C23B112.2 (2)
H23A—C23A—H23C109.5N1B—C22B—H22C109.2
H23B—C23A—H23C109.5C23B—C22B—H22C109.2
N3A—C24A—C15A177.1 (3)N1B—C22B—H22D109.2
C21B—S1B—C14B91.95 (13)C23B—C22B—H22D109.2
C12B—N1B—C1B108.69 (19)H22C—C22B—H22D107.9
C12B—N1B—C22B126.4 (2)C22B—C23B—H23D109.5
C1B—N1B—C22B124.1 (2)C22B—C23B—H23E109.5
C13B—N2B—C14B120.0 (2)H23D—C23B—H23E109.5
C2B—C1B—N1B129.3 (2)C22B—C23B—H23F109.5
C2B—C1B—C6B121.9 (2)H23D—C23B—H23F109.5
N1B—C1B—C6B108.8 (2)H23E—C23B—H23F109.5
C3B—C2B—C1B117.5 (2)N3B—C24B—C15B177.2 (3)
C3B—C2B—H2B121.3C26—C25—C30120.7 (4)
C1B—C2B—H2B121.3C26—C25—H25A119.6
C2B—C3B—C4B121.5 (2)C30—C25—H25A119.6
C2B—C3B—H3B119.2C25—C26—C27117.5 (4)
C4B—C3B—H3B119.2C25—C26—H26A121.3
C5B—C4B—C3B121.0 (3)C27—C26—H26A121.3
C5B—C4B—H4B119.5C28—C27—C26122.7 (4)
C3B—C4B—H4B119.5C28—C27—H27A118.6
C4B—C5B—C6B118.9 (2)C26—C27—H27A118.6
C4B—C5B—H5B120.6C27—C28—C29118.8 (4)
C6B—C5B—H5B120.6C27—C28—H28A120.6
C5B—C6B—C1B119.1 (2)C29—C28—H28A120.6
C5B—C6B—C7B134.2 (2)C30—C29—C28118.9 (4)
C1B—C6B—C7B106.6 (2)C30—C29—H29A120.6
C8B—C7B—C12B119.1 (2)C28—C29—H29A120.6
C8B—C7B—C6B134.4 (2)C25—C30—C29121.3 (4)
C12B—C7B—C6B106.5 (2)C25—C30—H30A119.4
C7B—C8B—C9B120.4 (2)C29—C30—H30A119.4
C12A—N1A—C1A—C2A176.3 (2)C4B—C5B—C6B—C1B0.5 (3)
C22A—N1A—C1A—C2A−4.7 (4)C4B—C5B—C6B—C7B−176.9 (2)
C12A—N1A—C1A—C6A−1.4 (2)C2B—C1B—C6B—C5B−0.4 (3)
C22A—N1A—C1A—C6A177.6 (2)N1B—C1B—C6B—C5B−179.32 (19)
N1A—C1A—C2A—C3A−177.1 (2)C2B—C1B—C6B—C7B177.7 (2)
C6A—C1A—C2A—C3A0.4 (4)N1B—C1B—C6B—C7B−1.3 (2)
C1A—C2A—C3A—C4A−1.8 (4)C5B—C6B—C7B—C8B−0.7 (4)
C2A—C3A—C4A—C5A1.4 (4)C1B—C6B—C7B—C8B−178.4 (2)
C3A—C4A—C5A—C6A0.6 (4)C5B—C6B—C7B—C12B178.0 (2)
C4A—C5A—C6A—C1A−2.0 (4)C1B—C6B—C7B—C12B0.4 (2)
C4A—C5A—C6A—C7A176.8 (2)C12B—C7B—C8B—C9B−0.9 (3)
N1A—C1A—C6A—C5A179.5 (2)C6B—C7B—C8B—C9B177.7 (2)
C2A—C1A—C6A—C5A1.6 (3)C7B—C8B—C9B—C10B1.6 (3)
N1A—C1A—C6A—C7A0.4 (2)C7B—C8B—C9B—C13B−178.2 (2)
C2A—C1A—C6A—C7A−177.5 (2)C8B—C9B—C10B—C11B−1.2 (4)
C5A—C6A—C7A—C8A2.7 (4)C13B—C9B—C10B—C11B178.6 (2)
C1A—C6A—C7A—C8A−178.4 (2)C9B—C10B—C11B—C12B0.0 (4)
C5A—C6A—C7A—C12A−178.2 (3)C1B—N1B—C12B—C11B178.5 (2)
C1A—C6A—C7A—C12A0.7 (2)C22B—N1B—C12B—C11B8.5 (4)
C12A—C7A—C8A—C9A1.7 (3)C1B—N1B—C12B—C7B−1.4 (2)
C6A—C7A—C8A—C9A−179.3 (2)C22B—N1B—C12B—C7B−171.4 (2)
C7A—C8A—C9A—C10A0.3 (3)C10B—C11B—C12B—N1B−179.2 (2)
C7A—C8A—C9A—C13A−178.8 (2)C10B—C11B—C12B—C7B0.7 (3)
C8A—C9A—C10A—C11A−1.6 (4)C8B—C7B—C12B—N1B179.6 (2)
C13A—C9A—C10A—C11A177.5 (2)C6B—C7B—C12B—N1B0.6 (2)
C9A—C10A—C11A—C12A0.8 (4)C8B—C7B—C12B—C11B−0.3 (3)
C1A—N1A—C12A—C11A−177.9 (2)C6B—C7B—C12B—C11B−179.3 (2)
C22A—N1A—C12A—C11A3.1 (4)C14B—N2B—C13B—C9B−180.0 (2)
C1A—N1A—C12A—C7A1.9 (2)C8B—C9B—C13B—N2B176.5 (2)
C22A—N1A—C12A—C7A−177.1 (2)C10B—C9B—C13B—N2B−3.3 (4)
C10A—C11A—C12A—N1A−179.0 (2)C13B—N2B—C14B—C15B−177.0 (2)
C10A—C11A—C12A—C7A1.3 (3)C13B—N2B—C14B—S1B2.7 (3)
C8A—C7A—C12A—N1A177.68 (19)C21B—S1B—C14B—N2B179.4 (2)
C6A—C7A—C12A—N1A−1.6 (2)C21B—S1B—C14B—C15B−0.92 (19)
C8A—C7A—C12A—C11A−2.5 (3)N2B—C14B—C15B—C16B−179.5 (2)
C6A—C7A—C12A—C11A178.2 (2)S1B—C14B—C15B—C16B0.9 (3)
C14A—N2A—C13A—C9A175.7 (2)N2B—C14B—C15B—C24B0.9 (4)
C8A—C9A—C13A—N2A8.2 (4)S1B—C14B—C15B—C24B−178.80 (19)
C10A—C9A—C13A—N2A−170.9 (2)C14B—C15B—C16B—C21B−0.3 (3)
C13A—N2A—C14A—C15A177.1 (2)C24B—C15B—C16B—C21B179.4 (2)
C13A—N2A—C14A—S1A−4.6 (3)C14B—C15B—C16B—C17B178.6 (2)
C21A—S1A—C14A—C15A0.84 (18)C24B—C15B—C16B—C17B−1.8 (4)
C21A—S1A—C14A—N2A−177.6 (2)C21B—C16B—C17B—C18B−14.7 (5)
N2A—C14A—C15A—C24A−1.4 (4)C15B—C16B—C17B—C18B166.5 (4)
S1A—C14A—C15A—C24A−179.89 (19)C21B—C16B—C17B—C18X13.2 (5)
N2A—C14A—C15A—C16A177.8 (2)C15B—C16B—C17B—C18X−165.6 (4)
S1A—C14A—C15A—C16A−0.7 (2)C16B—C17B—C18B—C19B43.5 (8)
C14A—C15A—C16A—C21A0.1 (3)C18X—C17B—C18B—C19B−31.3 (8)
C24A—C15A—C16A—C21A179.3 (2)C17B—C18B—C19B—C20B−66.4 (10)
C14A—C15A—C16A—C17A−177.5 (2)C18B—C17B—C18X—C19X66.9 (11)
C24A—C15A—C16A—C17A1.7 (4)C16B—C17B—C18X—C19X−48.0 (10)
C21A—C16A—C17A—C18A−16.2 (4)C17B—C18X—C19X—C20B61.3 (13)
C15A—C16A—C17A—C18A161.2 (2)C18X—C19X—C20B—C21B−40.4 (10)
C16A—C17A—C18A—C19A44.0 (4)C18X—C19X—C20B—C19B32.8 (6)
C17A—C18A—C19A—C20A−58.4 (4)C18B—C19B—C20B—C21B50.9 (8)
C18A—C19A—C20A—C21A39.9 (3)C18B—C19B—C20B—C19X−67.6 (9)
C15A—C16A—C21A—C20A−176.8 (2)C15B—C16B—C21B—C20B178.8 (2)
C17A—C16A—C21A—C20A0.9 (4)C17B—C16B—C21B—C20B−0.1 (4)
C15A—C16A—C21A—S1A0.6 (3)C15B—C16B—C21B—S1B−0.4 (3)
C17A—C16A—C21A—S1A178.22 (18)C17B—C16B—C21B—S1B−179.31 (19)
C19A—C20A—C21A—C16A−11.9 (4)C19X—C20B—C21B—C16B16.1 (7)
C19A—C20A—C21A—S1A171.02 (19)C19B—C20B—C21B—C16B−16.2 (4)
C14A—S1A—C21A—C16A−0.81 (19)C19X—C20B—C21B—S1B−164.8 (5)
C14A—S1A—C21A—C20A176.6 (2)C19B—C20B—C21B—S1B162.9 (3)
C12A—N1A—C22A—C23A−90.5 (3)C14B—S1B—C21B—C16B0.8 (2)
C1A—N1A—C22A—C23A90.7 (3)C14B—S1B—C21B—C20B−178.4 (2)
C12B—N1B—C1B—C2B−177.2 (2)C12B—N1B—C22B—C23B89.1 (3)
C22B—N1B—C1B—C2B−6.9 (4)C1B—N1B—C22B—C23B−79.4 (3)
C12B—N1B—C1B—C6B1.7 (2)C30—C25—C26—C27−2.0 (7)
C22B—N1B—C1B—C6B171.9 (2)C25—C26—C27—C28−1.3 (7)
N1B—C1B—C2B—C3B178.7 (2)C26—C27—C28—C292.8 (7)
C6B—C1B—C2B—C3B0.0 (3)C27—C28—C29—C30−1.0 (6)
C1B—C2B—C3B—C4B0.2 (4)C26—C25—C30—C293.8 (6)
C2B—C3B—C4B—C5B−0.1 (4)C28—C29—C30—C25−2.2 (6)
C3B—C4B—C5B—C6B−0.3 (4)

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1B–C6B, C7A–C12A and C14A–C16A/C21A/S1A rings, respectively.
D—H···AD—HH···AD···AD—H···A
C22A—H22A···N3Bi0.972.593.487 (3)155
C11A—H11A···Cg1ii0.932.653.499 (3)153
C11B—H11B···Cg2i0.932.823.725 (3)166
C27—H27A···Cg3iii0.932.713.625 (6)169

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5065).

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