organic compounds
H-dibenzo[b,g][1,8]naphthyridin-11-one
of 12-benzylsulfanyl-2,9-dibromo-6aJohannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: waldvogel@uni-mainz.de
The heterotetracene skeleton of the title molecule, C23H14Br2N2OS, is defined by linear 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.
Keywords: crystal structure; 1,8-naphthyridine; heterotetracene.
CCDC reference: 1416554
1. Related literature
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).
2. Experimental
2.1. Crystal data
|
2.3. Refinement
|
Data collection: X-AREA (Stoe & Cie, 1995); cell X-AREA; 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).
Supporting information
CCDC reference: 1416554
https://doi.org/10.1107/S2056989015014541/wm5191sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI: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
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
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 of the title compound in dichloromethane/methanol (5:1) by cyclohexane (diffusion method).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).
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).
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
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 of the title compound in dichloromethane/methanol (5:1) by cyclohexane (diffusion method). detailsHydrogen 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).
Data collection: X-AREA (Stoe & Cie, 1995); cell
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).C23H14Br2N2OS | F(000) = 1040 |
Mr = 526.24 | Dx = 1.794 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.4915 (10) Å | Cell parameters from 7178 reflections |
b = 9.3953 (4) Å | θ = 2.6–28.2° |
c = 13.6501 (9) Å | µ = 4.29 mm−1 |
β = 101.251 (5)° | T = 193 K |
V = 1948.6 (2) Å3 | Plate, orange |
Z = 4 | 0.27 × 0.12 × 0.04 mm |
Stoe IPDS 2T diffractometer | 4807 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2850 reflections with I > 2σ(I) |
Detector resolution: 6.67 pixels mm-1 | Rint = 0.058 |
rotation method scans | θmax = 28.3°, θmin = 2.6° |
Absorption correction: integration X-RED (Stoe & Cie, 1995) | h = −20→20 |
Tmin = 0.363, Tmax = 0.811 | k = −10→12 |
10437 measured reflections | l = −18→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.068 | H-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 reflections | Δρmax = 2.29 e Å−3 |
262 parameters | Δρmin = −1.21 e Å−3 |
C23H14Br2N2OS | V = 1948.6 (2) Å3 |
Mr = 526.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.4915 (10) Å | µ = 4.29 mm−1 |
b = 9.3953 (4) Å | T = 193 K |
c = 13.6501 (9) Å | 0.27 × 0.12 × 0.04 mm |
β = 101.251 (5)° |
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 = 0.811 | Rint = 0.058 |
10437 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
wR(F2) = 0.222 | H-atom parameters constrained |
S = 1.05 | Δρmax = 2.29 e Å−3 |
4807 reflections | Δρmin = −1.21 e Å−3 |
262 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.71684 (5) | 1.08811 (8) | 0.58620 (5) | 0.0411 (2) | |
Br2 | 0.08972 (7) | 0.12934 (12) | 0.48824 (9) | 0.0689 (3) | |
S1 | 0.29644 (15) | 0.5906 (3) | 0.64477 (16) | 0.0589 (6) | |
O1 | 0.4597 (3) | 0.7273 (6) | 0.6495 (3) | 0.0438 (12) | |
C1 | 0.5809 (5) | 0.8812 (7) | 0.5634 (5) | 0.0348 (14) | |
H1 | 0.5838 | 0.8954 | 0.6329 | 0.042* | |
C2 | 0.6354 (4) | 0.9552 (7) | 0.5144 (5) | 0.0328 (13) | |
C3 | 0.6323 (5) | 0.9381 (8) | 0.4114 (5) | 0.0377 (15) | |
H3 | 0.6694 | 0.9933 | 0.3785 | 0.045* | |
C4 | 0.5755 (5) | 0.8415 (8) | 0.3590 (5) | 0.0390 (16) | |
H4 | 0.5736 | 0.8280 | 0.2897 | 0.047* | |
C4A | 0.5201 (4) | 0.7624 (8) | 0.4081 (5) | 0.0322 (14) | |
N5 | 0.4632 (4) | 0.6622 (6) | 0.3565 (4) | 0.0355 (12) | |
H5 | 0.4652 | 0.6476 | 0.2933 | 0.043* | |
C5A | 0.4042 (4) | 0.5846 (7) | 0.3968 (5) | 0.0301 (13) | |
N6 | 0.3543 (4) | 0.4954 (6) | 0.3354 (4) | 0.0347 (12) | |
C6A | 0.2948 (4) | 0.4160 (7) | 0.3729 (5) | 0.0315 (13) | |
C7 | 0.2433 (5) | 0.3168 (8) | 0.3085 (5) | 0.0409 (16) | |
H7 | 0.2516 | 0.3067 | 0.2417 | 0.049* | |
C8 | 0.1822 (5) | 0.2364 (8) | 0.3411 (6) | 0.0451 (17) | |
H8 | 0.1472 | 0.1713 | 0.2970 | 0.054* | |
C9 | 0.1706 (5) | 0.2493 (9) | 0.4408 (6) | 0.0477 (18) | |
C10 | 0.2184 (5) | 0.3449 (8) | 0.5041 (6) | 0.0425 (16) | |
H10 | 0.2094 | 0.3526 | 0.5708 | 0.051* | |
C10A | 0.2809 (4) | 0.4321 (7) | 0.4720 (5) | 0.0353 (14) | |
C11 | 0.3307 (4) | 0.5375 (8) | 0.5332 (5) | 0.0361 (14) | |
C11A | 0.3987 (4) | 0.6075 (7) | 0.4993 (5) | 0.0293 (13) | |
C12 | 0.4597 (4) | 0.7092 (7) | 0.5603 (5) | 0.0335 (14) | |
C12A | 0.5203 (4) | 0.7839 (7) | 0.5102 (4) | 0.0319 (14) | |
C1A | 0.1824 (6) | 0.6501 (11) | 0.5902 (6) | 0.057 (2) | |
H1AA | 0.1841 | 0.7334 | 0.5462 | 0.068* | |
H1AB | 0.1497 | 0.5726 | 0.5500 | 0.068* | |
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' | 0.0582 | 0.5173 | 0.6612 | 0.066* | |
C3' | 0.0318 (6) | 0.6350 (11) | 0.7769 (7) | 0.058 (2) | |
H3' | −0.0128 | 0.5746 | 0.7925 | 0.070* | |
C4' | 0.0557 (6) | 0.7568 (10) | 0.8311 (7) | 0.055 (2) | |
H4' | 0.0282 | 0.7796 | 0.8855 | 0.066* | |
C5' | 0.1175 (6) | 0.8441 (10) | 0.8082 (7) | 0.054 (2) | |
H5' | 0.1328 | 0.9281 | 0.8464 | 0.065* | |
C6' | 0.1586 (6) | 0.8136 (9) | 0.7307 (7) | 0.052 (2) | |
H6' | 0.2014 | 0.8774 | 0.7146 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0434 (4) | 0.0406 (4) | 0.0375 (4) | −0.0045 (3) | 0.0034 (3) | −0.0001 (3) |
Br2 | 0.0683 (6) | 0.0662 (6) | 0.0812 (7) | −0.0265 (5) | 0.0367 (5) | −0.0144 (5) |
S1 | 0.0482 (11) | 0.0958 (18) | 0.0361 (10) | −0.0175 (11) | 0.0165 (8) | −0.0164 (10) |
O1 | 0.048 (3) | 0.062 (3) | 0.022 (2) | −0.011 (3) | 0.008 (2) | −0.002 (2) |
C1 | 0.034 (3) | 0.041 (4) | 0.028 (3) | 0.001 (3) | 0.005 (3) | −0.004 (3) |
C2 | 0.032 (3) | 0.037 (3) | 0.029 (3) | −0.005 (3) | 0.005 (3) | 0.001 (3) |
C3 | 0.043 (4) | 0.043 (4) | 0.027 (3) | −0.006 (3) | 0.006 (3) | 0.006 (3) |
C4 | 0.042 (4) | 0.049 (4) | 0.025 (3) | −0.002 (3) | 0.004 (3) | 0.003 (3) |
C4A | 0.028 (3) | 0.044 (4) | 0.024 (3) | −0.002 (3) | 0.004 (2) | 0.003 (3) |
N5 | 0.039 (3) | 0.047 (3) | 0.022 (3) | −0.005 (3) | 0.010 (2) | 0.001 (2) |
C5A | 0.031 (3) | 0.030 (3) | 0.028 (3) | 0.003 (3) | 0.004 (2) | 0.007 (2) |
N6 | 0.038 (3) | 0.038 (3) | 0.027 (3) | 0.004 (2) | 0.003 (2) | −0.008 (2) |
C6A | 0.025 (3) | 0.035 (3) | 0.033 (3) | 0.003 (3) | 0.004 (2) | −0.002 (3) |
C7 | 0.044 (4) | 0.043 (4) | 0.035 (4) | −0.002 (3) | 0.007 (3) | 0.000 (3) |
C8 | 0.044 (4) | 0.039 (4) | 0.050 (4) | −0.004 (3) | 0.005 (3) | −0.007 (3) |
C9 | 0.048 (4) | 0.050 (5) | 0.047 (4) | 0.001 (3) | 0.015 (4) | −0.002 (3) |
C10 | 0.040 (4) | 0.049 (4) | 0.040 (4) | 0.008 (3) | 0.012 (3) | 0.002 (3) |
C10A | 0.031 (3) | 0.038 (4) | 0.038 (4) | −0.001 (3) | 0.009 (3) | −0.001 (3) |
C11 | 0.035 (3) | 0.046 (4) | 0.029 (3) | 0.006 (3) | 0.011 (3) | 0.003 (3) |
C11A | 0.028 (3) | 0.033 (3) | 0.026 (3) | 0.003 (2) | 0.003 (2) | 0.000 (2) |
C12 | 0.032 (3) | 0.038 (4) | 0.028 (3) | 0.003 (3) | 0.000 (3) | 0.003 (3) |
C12A | 0.038 (3) | 0.039 (4) | 0.019 (3) | 0.009 (3) | 0.007 (2) | 0.003 (2) |
C1A | 0.055 (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) |
Br1—C2 | 1.905 (7) | C8—C9 | 1.413 (11) |
Br2—C9 | 1.890 (9) | C8—H8 | 0.9500 |
S1—C11 | 1.779 (7) | C9—C10 | 1.362 (11) |
S1—C1A | 1.864 (9) | C10—C10A | 1.402 (10) |
O1—C12 | 1.229 (8) | C10—H10 | 0.9500 |
C1—C2 | 1.366 (10) | C10A—C11 | 1.422 (10) |
C1—C12A | 1.406 (10) | C11—C11A | 1.395 (10) |
C1—H1 | 0.9500 | C11A—C12 | 1.481 (9) |
C2—C3 | 1.407 (9) | C12—C12A | 1.447 (10) |
C3—C4 | 1.365 (10) | C1A—C1' | 1.501 (12) |
C3—H3 | 0.9500 | C1A—H1AA | 0.9900 |
C4—C4A | 1.400 (10) | C1A—H1AB | 0.9900 |
C4—H4 | 0.9500 | C1'—C2' | 1.376 (12) |
C4A—N5 | 1.385 (9) | C1'—C6' | 1.398 (12) |
C4A—C12A | 1.408 (9) | C2'—C3' | 1.391 (13) |
N5—C5A | 1.366 (8) | C2'—H2' | 0.9500 |
N5—H5 | 0.8800 | C3'—C4' | 1.374 (13) |
C5A—N6 | 1.323 (8) | C3'—H3' | 0.9500 |
C5A—C11A | 1.435 (9) | C4'—C5' | 1.342 (13) |
N6—C6A | 1.360 (9) | C4'—H4' | 0.9500 |
C6A—C7 | 1.416 (10) | C5'—C6' | 1.368 (12) |
C6A—C10A | 1.420 (10) | C5'—H5' | 0.9500 |
C7—C8 | 1.352 (11) | C6'—H6' | 0.9500 |
C7—H7 | 0.9500 | ||
C11—S1—C1A | 99.2 (4) | C10—C10A—C11 | 123.5 (7) |
C2—C1—C12A | 119.5 (6) | C6A—C10A—C11 | 117.9 (6) |
C2—C1—H1 | 120.3 | C11A—C11—C10A | 119.5 (6) |
C12A—C1—H1 | 120.3 | C11A—C11—S1 | 121.5 (5) |
C1—C2—C3 | 121.8 (6) | C10A—C11—S1 | 118.6 (5) |
C1—C2—Br1 | 119.5 (5) | C11—C11A—C5A | 116.4 (6) |
C3—C2—Br1 | 118.7 (5) | C11—C11A—C12 | 123.9 (6) |
C4—C3—C2 | 119.5 (6) | C5A—C11A—C12 | 119.5 (6) |
C4—C3—H3 | 120.2 | O1—C12—C12A | 121.8 (6) |
C2—C3—H3 | 120.2 | O1—C12—C11A | 121.5 (6) |
C3—C4—C4A | 119.7 (6) | C12A—C12—C11A | 116.7 (6) |
C3—C4—H4 | 120.2 | C1—C12A—C4A | 118.5 (6) |
C4A—C4—H4 | 120.2 | C1—C12A—C12 | 120.0 (6) |
N5—C4A—C4 | 120.4 (6) | C4A—C12A—C12 | 121.5 (6) |
N5—C4A—C12A | 118.6 (6) | C1'—C1A—S1 | 107.8 (6) |
C4—C4A—C12A | 120.9 (6) | C1'—C1A—H1AA | 110.1 |
C5A—N5—C4A | 124.6 (6) | S1—C1A—H1AA | 110.1 |
C5A—N5—H5 | 117.7 | C1'—C1A—H1AB | 110.1 |
C4A—N5—H5 | 117.7 | S1—C1A—H1AB | 110.1 |
N6—C5A—N5 | 116.0 (6) | H1AA—C1A—H1AB | 108.5 |
N6—C5A—C11A | 125.1 (6) | C2'—C1'—C6' | 117.9 (8) |
N5—C5A—C11A | 119.0 (6) | C2'—C1'—C1A | 119.8 (8) |
C5A—N6—C6A | 117.7 (6) | C6'—C1'—C1A | 122.3 (8) |
N6—C6A—C7 | 117.9 (6) | C1'—C2'—C3' | 121.1 (9) |
N6—C6A—C10A | 122.7 (6) | C1'—C2'—H2' | 119.5 |
C7—C6A—C10A | 119.3 (6) | C3'—C2'—H2' | 119.5 |
C8—C7—C6A | 120.6 (7) | C4'—C3'—C2' | 118.8 (9) |
C8—C7—H7 | 119.7 | C4'—C3'—H3' | 120.6 |
C6A—C7—H7 | 119.7 | C2'—C3'—H3' | 120.6 |
C7—C8—C9 | 119.9 (7) | C5'—C4'—C3' | 120.9 (9) |
C7—C8—H8 | 120.0 | C5'—C4'—H4' | 119.5 |
C9—C8—H8 | 120.0 | C3'—C4'—H4' | 119.5 |
C10—C9—C8 | 120.8 (8) | C4'—C5'—C6' | 120.8 (9) |
C10—C9—Br2 | 119.4 (6) | C4'—C5'—H5' | 119.6 |
C8—C9—Br2 | 119.8 (6) | C6'—C5'—H5' | 119.6 |
C9—C10—C10A | 120.7 (7) | C5'—C6'—C1' | 120.4 (8) |
C9—C10—H10 | 119.6 | C5'—C6'—H6' | 119.8 |
C10A—C10—H10 | 119.6 | C1'—C6'—H6' | 119.8 |
C10—C10A—C6A | 118.5 (6) | ||
C12A—C1—C2—C3 | 0.7 (11) | C10A—C11—C11A—C5A | 10.1 (9) |
C12A—C1—C2—Br1 | 179.5 (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—C4 | 178.8 (6) | S1—C11—C11A—C12 | 13.0 (9) |
C2—C3—C4—C4A | 1.0 (11) | N6—C5A—C11A—C11 | −5.1 (10) |
C3—C4—C4A—N5 | −178.9 (7) | N5—C5A—C11A—C11 | 172.9 (6) |
C3—C4—C4A—C12A | 1.9 (11) | N6—C5A—C11A—C12 | 179.0 (6) |
C4—C4A—N5—C5A | −177.0 (6) | N5—C5A—C11A—C12 | −2.9 (9) |
C12A—C4A—N5—C5A | 2.2 (10) | C11—C11A—C12—O1 | 7.7 (10) |
C4A—N5—C5A—N6 | 179.0 (6) | C5A—C11A—C12—O1 | −176.8 (6) |
C4A—N5—C5A—C11A | 0.8 (10) | C11—C11A—C12—C12A | −173.5 (6) |
N5—C5A—N6—C6A | 179.9 (6) | C5A—C11A—C12—C12A | 2.0 (9) |
C11A—C5A—N6—C6A | −2.0 (9) | C2—C1—C12A—C4A | 2.2 (10) |
C5A—N6—C6A—C7 | −177.9 (6) | C2—C1—C12A—C12 | −177.5 (6) |
C5A—N6—C6A—C10A | 4.1 (9) | N5—C4A—C12A—C1 | 177.3 (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—C12 | 176.2 (6) |
C7—C8—C9—C10 | 1.9 (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—C4A | 179.8 (7) |
Br2—C9—C10—C10A | 178.0 (6) | C11A—C12—C12A—C4A | 1.0 (9) |
C9—C10—C10A—C6A | −1.7 (11) | C11—S1—C1A—C1' | 175.4 (7) |
C9—C10—C10A—C11 | 177.7 (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—C10 | 2.4 (10) | C6'—C1'—C2'—C3' | −1.0 (14) |
N6—C6A—C10A—C11 | 0.9 (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—C11A | 172.4 (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—S1 | 164.7 (5) | C2'—C1'—C6'—C5' | 1.9 (13) |
C1A—S1—C11—C11A | 115.4 (6) | C1A—C1'—C6'—C5' | −179.1 (8) |
C1A—S1—C11—C10A | −57.4 (7) |
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+3/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···O1i | 0.88 | 2.28 | 3.001 (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
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Holmes, D., Kumaraswamy, S., Matzger, A. J. & Vollhardt, K. P. C. (1999). Chem. Eur. J. 5, 3399–3412. CrossRef CAS Google Scholar
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. CSD CrossRef Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (1995). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.