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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 9| September 2015| Pages o675-o676
https://doi.org/10.1107/S2056989015014541

Crystal structure of 12-benzyl­sulfanyl-2,9-di­bromo-6H-dibenzo[b,g][1,8]naphthyridin-11-one

CROSSMARK_Color_square_no_text.svg
Sebastian Resch,a Thomas Quell,a Dieter Schollmeyera and Siegfried R. Waldvogela*

aJohannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: waldvogel@uni-mainz.de

Edited by M. Weil, Vienna University of Technology, Austria (Received 25 July 2015; accepted 1 August 2015; online 22 August 2015)

The hetero­tetra­cene skeleton of the title mol­ecule, C23H14Br2N2OS, is defined by linear annulation of four six-membered rings, including two N heteroatoms. This moiety is nearly planar (r.m.s. deviation = 0.055 Å), with a slight twist of 4.1 (2)° between the two halves of the aromatic system. The dihedral angle between the least-squares plane of the skeleton and the benzyl group is 24.5 (3)°; the C—S—C angle involving the benzyl­sulfanyl group is 99.2 (4)°. In the crystal, mol­ecules are π-stacked in an anti­parallel fashion along [110], with a distance between the aromatic planes of 3.47 (2) Å. Inter­molecular N—H⋯O hydrogen bonds form chains extending parallel to [001] and bridge the anti­parallel inter­digitated stacks of mol­ecules.

CCDC reference: 1416554

Similar articles

1. Related literature

The title compound was prepared as part of a study towards sulfur-containing 1,8-naphthyridine derivatives (Resch et al., 2015[Resch, S., Schneider, A.-R., Beichler, R., Spera, M. B. M., Fanous, J., Schollmeyer, D. & Waldvogel, S. R. (2015). Eur. J. Org. Chem. pp. 933-937.]) in which the structure of a dibenzo[b,g][1,2]di­thiolo[3,4,5-d,e][1,8]naphthyridine derivative is reported. For the structure of tetra­cene, see: Holmes et al. (1999[Holmes, D., Kumaraswamy, S., Matzger, A. J. & Vollhardt, K. P. C. (1999). Chem. Eur. J. 5, 3399-3412.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C23H14Br2N2OS

  • Mr = 526.24

  • Monoclinic, P 21 /c

  • a = 15.4915 (10) Å

  • b = 9.3953 (4) Å

  • c = 13.6501 (9) Å

  • β = 101.251 (5)°

  • V = 1948.6 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 4.29 mm−1

  • T = 193 K

  • 0.27 × 0.12 × 0.04 mm

2.2. Data collection

  • Stoe IPDS 2T diffractometer

  • Absorption correction: integration X-RED (Stoe & Cie, 1995[Stoe & Cie (1995). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.363, Tmax = 0.811

  • 10437 measured reflections

  • 4807 independent reflections

  • 2850 reflections with I > 2σ(I)

  • Rint = 0.058

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.222

  • S = 1.05

  • 4807 reflections

  • 262 parameters

  • H-atom parameters constrained

  • Δρmax = 2.29 e Å−3

  • Δρmin = −1.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N5—H5⋯O1i 0.88 2.28 3.001 (7) 140
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 1995[Stoe & Cie (1995). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 1995[Stoe & Cie (1995). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1416554

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015014541/wm5191sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014541/wm5191Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015014541/wm5191Isup3.cml

checkCIF report


Synthesis and crystallization top

In argon atmosphere, 50 mg (2.0 mmol, 3 eq) NaH and 340 mg (2.7 mmol, 4 eq) benzyl thiol were given to 40 ml of anhydrous dioxane and stirred at room temperature for 30 min. 300 mg (0.68 mmol, 1 eq) of 6H-12-chloro-2,9-di­bromo­dibenzo[b,g]-1,8-naphthyridin-11-one were added and the mixture stirred at room temperature for additional 5 h. After completion of the reaction, the solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel using a mixture of di­chloro­methane and acetic acid (97:3). The solvent was removed under reduced pressure and the residue alkalized using 1M ammonium hydroxide solution. Yield: 276 mg (0.52 mmol, 77%) of an orange solid with mp. = > 513 K (decomposition). Suitable single crystals were obtained by slowly diluting a saturated solution of the title compound in di­chloro­methane/methanol (5:1) by cyclo­hexane (diffusion method).

Refinement top

Hydrogen atoms attached to carbon atoms were placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.99 Å (methyl­ene C atom). The H atom bonded to the N atom was placed at calculated positions with N—H = 0.88 Å. All H atoms were refined in the riding-model approximation with isotropic displacement parameters (set at 1.2–1.5Ueq of the parent atom).

Related literature top

The title compound was prepared as part of a study towards sulfur-containing 1,8-naphthyridine derivatives (Resch et al., 2015) in which the structure of a dibenzo[b,g][1,2]dithiolo[3,4,5-d,e][1,8]naphthyridine derivative is reported. For the structure of tetracene, see: Holmes et al. (1999).

Structure description top

The title compound was prepared as part of a study towards sulfur-containing 1,8-naphthyridine derivatives (Resch et al., 2015) in which the structure of a dibenzo[b,g][1,2]dithiolo[3,4,5-d,e][1,8]naphthyridine derivative is reported. For the structure of tetracene, see: Holmes et al. (1999).

Synthesis and crystallization top

In argon atmosphere, 50 mg (2.0 mmol, 3 eq) NaH and 340 mg (2.7 mmol, 4 eq) benzyl thiol were given to 40 ml of anhydrous dioxane and stirred at room temperature for 30 min. 300 mg (0.68 mmol, 1 eq) of 6H-12-chloro-2,9-di­bromo­dibenzo[b,g]-1,8-naphthyridin-11-one were added and the mixture stirred at room temperature for additional 5 h. After completion of the reaction, the solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel using a mixture of di­chloro­methane and acetic acid (97:3). The solvent was removed under reduced pressure and the residue alkalized using 1M ammonium hydroxide solution. Yield: 276 mg (0.52 mmol, 77%) of an orange solid with mp. = > 513 K (decomposition). Suitable single crystals were obtained by slowly diluting a saturated solution of the title compound in di­chloro­methane/methanol (5:1) by cyclo­hexane (diffusion method).

Refinement details top

Hydrogen atoms attached to carbon atoms were placed at calculated positions with C—H = 0.95 Å (aromatic) or 0.99 Å (methyl­ene C atom). The H atom bonded to the N atom was placed at calculated positions with N—H = 0.88 Å. All H atoms were refined in the riding-model approximation with isotropic displacement parameters (set at 1.2–1.5Ueq of the parent atom).

Computing details top

Data collection: X-AREA (Stoe & Cie, 1995); cell refinement: X-AREA (Stoe & Cie, 1995); data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal structure of the title compound in a view along [010]. N—H···O hydrogen bonds are shown as dashed lines.
12-Benzylsulfanyl-2,9-dibromo-6,11-dihydro-5-azatetracen-11-one top
Crystal data top
C23H14Br2N2OSF(000) = 1040
Mr = 526.24Dx = 1.794 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.4915 (10) ÅCell parameters from 7178 reflections
b = 9.3953 (4) Åθ = 2.6–28.2°
c = 13.6501 (9) ŵ = 4.29 mm−1
β = 101.251 (5)°T = 193 K
V = 1948.6 (2) Å3Plate, orange
Z = 40.27 × 0.12 × 0.04 mm
Data collection top
Stoe IPDS 2T
diffractometer		4807 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2850 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.058
rotation method scansθmax = 28.3°, θmin = 2.6°
Absorption correction: integration
X-RED (Stoe & Cie, 1995)		h = −20→20
Tmin = 0.363, Tmax = 0.811k = −10→12
10437 measured reflectionsl = −18→16
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.222 w = 1/[σ2(Fo2) + (0.1106P)2 + 4.6375P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4807 reflectionsΔρmax = 2.29 e Å−3
262 parametersΔρmin = −1.21 e Å−3
Crystal data top
C23H14Br2N2OSV = 1948.6 (2) Å3
Mr = 526.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.4915 (10) ŵ = 4.29 mm−1
b = 9.3953 (4) ÅT = 193 K
c = 13.6501 (9) Å0.27 × 0.12 × 0.04 mm
β = 101.251 (5)°
Data collection top
Stoe IPDS 2T
diffractometer		4807 independent reflections
Absorption correction: integration
X-RED (Stoe & Cie, 1995)		2850 reflections with I > 2σ(I)
Tmin = 0.363, Tmax = 0.811Rint = 0.058
10437 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.222H-atom parameters constrained
S = 1.05Δρmax = 2.29 e Å−3
4807 reflectionsΔρmin = −1.21 e Å−3
262 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.71684 (5)1.08811 (8)0.58620 (5)0.0411 (2)
Br20.08972 (7)0.12934 (12)0.48824 (9)0.0689 (3)
S10.29644 (15)0.5906 (3)0.64477 (16)0.0589 (6)
O10.4597 (3)0.7273 (6)0.6495 (3)0.0438 (12)
C10.5809 (5)0.8812 (7)0.5634 (5)0.0348 (14)
H10.58380.89540.63290.042*
C20.6354 (4)0.9552 (7)0.5144 (5)0.0328 (13)
C30.6323 (5)0.9381 (8)0.4114 (5)0.0377 (15)
H30.66940.99330.37850.045*
C40.5755 (5)0.8415 (8)0.3590 (5)0.0390 (16)
H40.57360.82800.28970.047*
C4A0.5201 (4)0.7624 (8)0.4081 (5)0.0322 (14)
N50.4632 (4)0.6622 (6)0.3565 (4)0.0355 (12)
H50.46520.64760.29330.043*
C5A0.4042 (4)0.5846 (7)0.3968 (5)0.0301 (13)
N60.3543 (4)0.4954 (6)0.3354 (4)0.0347 (12)
C6A0.2948 (4)0.4160 (7)0.3729 (5)0.0315 (13)
C70.2433 (5)0.3168 (8)0.3085 (5)0.0409 (16)
H70.25160.30670.24170.049*
C80.1822 (5)0.2364 (8)0.3411 (6)0.0451 (17)
H80.14720.17130.29700.054*
C90.1706 (5)0.2493 (9)0.4408 (6)0.0477 (18)
C100.2184 (5)0.3449 (8)0.5041 (6)0.0425 (16)
H100.20940.35260.57080.051*
C10A0.2809 (4)0.4321 (7)0.4720 (5)0.0353 (14)
C110.3307 (4)0.5375 (8)0.5332 (5)0.0361 (14)
C11A0.3987 (4)0.6075 (7)0.4993 (5)0.0293 (13)
C120.4597 (4)0.7092 (7)0.5603 (5)0.0335 (14)
C12A0.5203 (4)0.7839 (7)0.5102 (4)0.0319 (14)
C1A0.1824 (6)0.6501 (11)0.5902 (6)0.057 (2)
H1AA0.18410.73340.54620.068*
H1AB0.14970.57260.55000.068*
C1'0.1381 (6)0.6890 (10)0.6749 (6)0.0500 (19)
C2'0.0739 (6)0.6017 (10)0.6987 (7)0.055 (2)
H2'0.05820.51730.66120.066*
C3'0.0318 (6)0.6350 (11)0.7769 (7)0.058 (2)
H3'−0.01280.57460.79250.070*
C4'0.0557 (6)0.7568 (10)0.8311 (7)0.055 (2)
H4'0.02820.77960.88550.066*
C5'0.1175 (6)0.8441 (10)0.8082 (7)0.054 (2)
H5'0.13280.92810.84640.065*
C6'0.1586 (6)0.8136 (9)0.7307 (7)0.052 (2)
H6'0.20140.87740.71460.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0434 (4)0.0406 (4)0.0375 (4)−0.0045 (3)0.0034 (3)−0.0001 (3)
Br20.0683 (6)0.0662 (6)0.0812 (7)−0.0265 (5)0.0367 (5)−0.0144 (5)
S10.0482 (11)0.0958 (18)0.0361 (10)−0.0175 (11)0.0165 (8)−0.0164 (10)
O10.048 (3)0.062 (3)0.022 (2)−0.011 (3)0.008 (2)−0.002 (2)
C10.034 (3)0.041 (4)0.028 (3)0.001 (3)0.005 (3)−0.004 (3)
C20.032 (3)0.037 (3)0.029 (3)−0.005 (3)0.005 (3)0.001 (3)
C30.043 (4)0.043 (4)0.027 (3)−0.006 (3)0.006 (3)0.006 (3)
C40.042 (4)0.049 (4)0.025 (3)−0.002 (3)0.004 (3)0.003 (3)
C4A0.028 (3)0.044 (4)0.024 (3)−0.002 (3)0.004 (2)0.003 (3)
N50.039 (3)0.047 (3)0.022 (3)−0.005 (3)0.010 (2)0.001 (2)
C5A0.031 (3)0.030 (3)0.028 (3)0.003 (3)0.004 (2)0.007 (2)
N60.038 (3)0.038 (3)0.027 (3)0.004 (2)0.003 (2)−0.008 (2)
C6A0.025 (3)0.035 (3)0.033 (3)0.003 (3)0.004 (2)−0.002 (3)
C70.044 (4)0.043 (4)0.035 (4)−0.002 (3)0.007 (3)0.000 (3)
C80.044 (4)0.039 (4)0.050 (4)−0.004 (3)0.005 (3)−0.007 (3)
C90.048 (4)0.050 (5)0.047 (4)0.001 (3)0.015 (4)−0.002 (3)
C100.040 (4)0.049 (4)0.040 (4)0.008 (3)0.012 (3)0.002 (3)
C10A0.031 (3)0.038 (4)0.038 (4)−0.001 (3)0.009 (3)−0.001 (3)
C110.035 (3)0.046 (4)0.029 (3)0.006 (3)0.011 (3)0.003 (3)
C11A0.028 (3)0.033 (3)0.026 (3)0.003 (2)0.003 (2)0.000 (2)
C120.032 (3)0.038 (4)0.028 (3)0.003 (3)0.000 (3)0.003 (3)
C12A0.038 (3)0.039 (4)0.019 (3)0.009 (3)0.007 (2)0.003 (2)
C1A0.055 (5)0.075 (6)0.039 (4)−0.007 (4)0.004 (4)−0.011 (4)
C1'0.056 (5)0.059 (5)0.037 (4)0.010 (4)0.013 (3)0.004 (3)
C2'0.047 (5)0.053 (5)0.067 (6)−0.010 (4)0.013 (4)0.000 (4)
C3'0.042 (4)0.069 (6)0.063 (6)−0.005 (4)0.012 (4)0.004 (5)
C4'0.044 (4)0.064 (6)0.058 (5)0.003 (4)0.011 (4)0.001 (4)
C5'0.053 (5)0.057 (5)0.054 (5)0.006 (4)0.013 (4)−0.016 (4)
C6'0.052 (5)0.045 (4)0.058 (5)−0.010 (4)0.008 (4)−0.008 (4)
Geometric parameters (Å, º) top
Br1—C21.905 (7)C8—C91.413 (11)
Br2—C91.890 (9)C8—H80.9500
S1—C111.779 (7)C9—C101.362 (11)
S1—C1A1.864 (9)C10—C10A1.402 (10)
O1—C121.229 (8)C10—H100.9500
C1—C21.366 (10)C10A—C111.422 (10)
C1—C12A1.406 (10)C11—C11A1.395 (10)
C1—H10.9500C11A—C121.481 (9)
C2—C31.407 (9)C12—C12A1.447 (10)
C3—C41.365 (10)C1A—C1'1.501 (12)
C3—H30.9500C1A—H1AA0.9900
C4—C4A1.400 (10)C1A—H1AB0.9900
C4—H40.9500C1'—C2'1.376 (12)
C4A—N51.385 (9)C1'—C6'1.398 (12)
C4A—C12A1.408 (9)C2'—C3'1.391 (13)
N5—C5A1.366 (8)C2'—H2'0.9500
N5—H50.8800C3'—C4'1.374 (13)
C5A—N61.323 (8)C3'—H3'0.9500
C5A—C11A1.435 (9)C4'—C5'1.342 (13)
N6—C6A1.360 (9)C4'—H4'0.9500
C6A—C71.416 (10)C5'—C6'1.368 (12)
C6A—C10A1.420 (10)C5'—H5'0.9500
C7—C81.352 (11)C6'—H6'0.9500
C7—H70.9500
C11—S1—C1A99.2 (4)C10—C10A—C11123.5 (7)
C2—C1—C12A119.5 (6)C6A—C10A—C11117.9 (6)
C2—C1—H1120.3C11A—C11—C10A119.5 (6)
C12A—C1—H1120.3C11A—C11—S1121.5 (5)
C1—C2—C3121.8 (6)C10A—C11—S1118.6 (5)
C1—C2—Br1119.5 (5)C11—C11A—C5A116.4 (6)
C3—C2—Br1118.7 (5)C11—C11A—C12123.9 (6)
C4—C3—C2119.5 (6)C5A—C11A—C12119.5 (6)
C4—C3—H3120.2O1—C12—C12A121.8 (6)
C2—C3—H3120.2O1—C12—C11A121.5 (6)
C3—C4—C4A119.7 (6)C12A—C12—C11A116.7 (6)
C3—C4—H4120.2C1—C12A—C4A118.5 (6)
C4A—C4—H4120.2C1—C12A—C12120.0 (6)
N5—C4A—C4120.4 (6)C4A—C12A—C12121.5 (6)
N5—C4A—C12A118.6 (6)C1'—C1A—S1107.8 (6)
C4—C4A—C12A120.9 (6)C1'—C1A—H1AA110.1
C5A—N5—C4A124.6 (6)S1—C1A—H1AA110.1
C5A—N5—H5117.7C1'—C1A—H1AB110.1
C4A—N5—H5117.7S1—C1A—H1AB110.1
N6—C5A—N5116.0 (6)H1AA—C1A—H1AB108.5
N6—C5A—C11A125.1 (6)C2'—C1'—C6'117.9 (8)
N5—C5A—C11A119.0 (6)C2'—C1'—C1A119.8 (8)
C5A—N6—C6A117.7 (6)C6'—C1'—C1A122.3 (8)
N6—C6A—C7117.9 (6)C1'—C2'—C3'121.1 (9)
N6—C6A—C10A122.7 (6)C1'—C2'—H2'119.5
C7—C6A—C10A119.3 (6)C3'—C2'—H2'119.5
C8—C7—C6A120.6 (7)C4'—C3'—C2'118.8 (9)
C8—C7—H7119.7C4'—C3'—H3'120.6
C6A—C7—H7119.7C2'—C3'—H3'120.6
C7—C8—C9119.9 (7)C5'—C4'—C3'120.9 (9)
C7—C8—H8120.0C5'—C4'—H4'119.5
C9—C8—H8120.0C3'—C4'—H4'119.5
C10—C9—C8120.8 (8)C4'—C5'—C6'120.8 (9)
C10—C9—Br2119.4 (6)C4'—C5'—H5'119.6
C8—C9—Br2119.8 (6)C6'—C5'—H5'119.6
C9—C10—C10A120.7 (7)C5'—C6'—C1'120.4 (8)
C9—C10—H10119.6C5'—C6'—H6'119.8
C10A—C10—H10119.6C1'—C6'—H6'119.8
C10—C10A—C6A118.5 (6)
C12A—C1—C2—C30.7 (11)C10A—C11—C11A—C5A10.1 (9)
C12A—C1—C2—Br1179.5 (5)S1—C11—C11A—C5A−162.6 (5)
C1—C2—C3—C4−2.3 (11)C10A—C11—C11A—C12−174.3 (6)
Br1—C2—C3—C4178.8 (6)S1—C11—C11A—C1213.0 (9)
C2—C3—C4—C4A1.0 (11)N6—C5A—C11A—C11−5.1 (10)
C3—C4—C4A—N5−178.9 (7)N5—C5A—C11A—C11172.9 (6)
C3—C4—C4A—C12A1.9 (11)N6—C5A—C11A—C12179.0 (6)
C4—C4A—N5—C5A−177.0 (6)N5—C5A—C11A—C12−2.9 (9)
C12A—C4A—N5—C5A2.2 (10)C11—C11A—C12—O17.7 (10)
C4A—N5—C5A—N6179.0 (6)C5A—C11A—C12—O1−176.8 (6)
C4A—N5—C5A—C11A0.8 (10)C11—C11A—C12—C12A−173.5 (6)
N5—C5A—N6—C6A179.9 (6)C5A—C11A—C12—C12A2.0 (9)
C11A—C5A—N6—C6A−2.0 (9)C2—C1—C12A—C4A2.2 (10)
C5A—N6—C6A—C7−177.9 (6)C2—C1—C12A—C12−177.5 (6)
C5A—N6—C6A—C10A4.1 (9)N5—C4A—C12A—C1177.3 (6)
N6—C6A—C7—C8−179.0 (7)C4—C4A—C12A—C1−3.5 (10)
C10A—C6A—C7—C8−1.0 (11)N5—C4A—C12A—C12−3.1 (10)
C6A—C7—C8—C9−1.1 (12)C4—C4A—C12A—C12176.2 (6)
C7—C8—C9—C101.9 (12)O1—C12—C12A—C1−0.5 (10)
C7—C8—C9—Br2−176.6 (6)C11A—C12—C12A—C1−179.4 (6)
C8—C9—C10—C10A−0.5 (12)O1—C12—C12A—C4A179.8 (7)
Br2—C9—C10—C10A178.0 (6)C11A—C12—C12A—C4A1.0 (9)
C9—C10—C10A—C6A−1.7 (11)C11—S1—C1A—C1'175.4 (7)
C9—C10—C10A—C11177.7 (7)S1—C1A—C1'—C2'−107.4 (8)
N6—C6A—C10A—C10−179.7 (6)S1—C1A—C1'—C6'73.6 (10)
C7—C6A—C10A—C102.4 (10)C6'—C1'—C2'—C3'−1.0 (14)
N6—C6A—C10A—C110.9 (10)C1A—C1'—C2'—C3'179.9 (8)
C7—C6A—C10A—C11−177.0 (6)C1'—C2'—C3'—C4'−0.5 (14)
C10—C10A—C11—C11A172.4 (7)C2'—C3'—C4'—C5'1.3 (14)
C6A—C10A—C11—C11A−8.3 (10)C3'—C4'—C5'—C6'−0.4 (14)
C10—C10A—C11—S1−14.7 (10)C4'—C5'—C6'—C1'−1.2 (14)
C6A—C10A—C11—S1164.7 (5)C2'—C1'—C6'—C5'1.9 (13)
C1A—S1—C11—C11A115.4 (6)C1A—C1'—C6'—C5'−179.1 (8)
C1A—S1—C11—C10A−57.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O1i0.882.283.001 (7)140
Symmetry code: (i) x, −y+3/2, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O1i0.882.283.001 (7)139.6
Symmetry code: (i) x, −y+3/2, z−1/2.
 

Acknowledgements

This work was generously supported by the Federal Ministry of Education and Research (BMBF, HE-Lion, 03X4612B) and the German Research Foundation (DFG) in the frame of the research unit FOR1616.

References

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ISSN: 2056-9890
Volume 71| Part 9| September 2015| Pages o675-o676
https://doi.org/10.1107/S2056989015014541
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