Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704562X/gk2104sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704562X/gk2104Isup2.hkl |
CCDC reference: 663797
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.009 Å
- R factor = 0.058
- wR factor = 0.152
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.48 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 200 Ang. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the crystal structures of similar naphthofuran compounds, see: Choi et al. (2006, 2007).
Zinc chloride (273 mg, 2.0 mmol) was added at room temperature to a stirred solution of 6-bromo-2-naphthol (446 mg, 2.0 mmol) and α-chloro-α-(phenylsulfanyl)acetone (401 mg, 2.0 mmol) in dichloromethane (30 ml), and stirred for 1 h. The mixture was quenched with water and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (CCl4) to afford the title compound as a colorless solid [yield 63%, m.p. 436–437 K; Rf = 0.68 (CCl4)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dilute solution of the title compound in chloroform at room temperature.
All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aromatic H atoms and 0.98 Å for methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for aromatic H atoms and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The highest peak in the difference map is 1.13 Å from Br2 and the largest hole is 0.88 Å from Br1.
As part of our ongoing studies on the synthesis and structure of 2-methylnaphtho[2,1-b]furan analogues, we have recently described the crystal structures of 2-methyl-1-(methylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2006) and 2-methyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2007). Herein we report the molecular and crystal structure of the title compound, (Fig. 1).
The phenyl rings (C13—C18 in unit A and C32—C37 in unit B) are tilted towards the plane of the naphthofuran systems [72.9 (9)° (unit A) and 80.5 (1)° (unit B)]. The molecular packing (Fig. 2) is stabilized by two different π···π interactions within each stack of molecules; one between the benzene ring (Cg4) and an adjacent furan ring (Cg1) of benzofuran unit {distance; 3.594 (9) Å}, and a second between the benzene ring (Cg6) and an adjacent furan ring (Cg2) of benzofuran unit {distance; 3.658 (9) Å} (Cg1, Cg2, Cg4, and Cg6 are the centroids of the O1/C12/C1/C2/C11 furan ring, the O2/C31/C20/C21/C30 furan ring, the C22—C27 benzene ring, and the C3—C8 benzene ring, respectively; symmetry code as in Fig. 2). The crystal packing (Fig. 2) is further stabilized by CH2—H···π interactions; one between the methyl group (unit B) and the benzene ring (unit A) of benzofuran unit, with a C38—H38A···Cg5 separation of 2.60 Å, and a second between the methyl group (Unit A) and the benzene ring (Unit B) of benzofuran unit, with a C19—H19C···Cg3 separation of 2.77 Å (Fig. 2 and Table 1; Cg3 and Cg5 are the centroids of the C21/C22/C27/C28/C29/C30 benzene ring and the C2/C3/C8/C9/C10/C11 benzene ring, respectively; symmetry code as in Fig. 2). In addition, the crystal packing (Fig. 2) is further stabilized by weak C—Br···π interactions: one between the Br atom (Unit B) and the phenyl ring (Unit A) with a C25—Br2···Cg8 separation of 3.718 (6) Å, and a second between the Br atom (Unit A) and the phenyl ring (Unit B) with a C6—Br1···Cg7 separation of 4.015 (6) Å (Fig. 2; Cg7 and Cg8 are the centroids of the C32—C37 benzene ring and the C13—C18 benzene ring, respectively; symmetry code as in Fig. 2).
For the crystal structures of similar naphthofuran compounds, see: Choi et al. (2006, 2007).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C19H13BrOS | Z = 4 |
Mr = 369.26 | F(000) = 744 |
Triclinic, P1 | Dx = 1.603 Mg m−3 |
Hall symbol: -p 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.947 (2) Å | Cell parameters from 4034 reflections |
b = 11.130 (2) Å | θ = 2.4–28.1° |
c = 13.636 (2) Å | µ = 2.82 mm−1 |
α = 112.798 (2)° | T = 173 K |
β = 91.999 (3)° | Plate, colorless |
γ = 90.908 (2)° | 0.35 × 0.25 × 0.10 mm |
V = 1529.9 (5) Å3 |
Bruker SMART CCD diffractometer | 5209 independent reflections |
Radiation source: fine-focus sealed tube | 4269 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 10.00 pixels mm-1 | θmax = 25.0°, θmin = 1.9° |
φ and ω scans | h = −12→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | k = −13→13 |
Tmin = 0.442, Tmax = 0.760 | l = −6→16 |
7613 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0494P)2 + 8.0396P] where P = (Fo2 + 2Fc2)/3 |
5209 reflections | (Δ/σ)max < 0.001 |
398 parameters | Δρmax = 1.62 e Å−3 |
0 restraints | Δρmin = −0.65 e Å−3 |
C19H13BrOS | γ = 90.908 (2)° |
Mr = 369.26 | V = 1529.9 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.947 (2) Å | Mo Kα radiation |
b = 11.130 (2) Å | µ = 2.82 mm−1 |
c = 13.636 (2) Å | T = 173 K |
α = 112.798 (2)° | 0.35 × 0.25 × 0.10 mm |
β = 91.999 (3)° |
Bruker SMART CCD diffractometer | 5209 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | 4269 reflections with I > 2σ(I) |
Tmin = 0.442, Tmax = 0.760 | Rint = 0.025 |
7613 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.14 | Δρmax = 1.62 e Å−3 |
5209 reflections | Δρmin = −0.65 e Å−3 |
398 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. |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.30246 (6) | 0.23787 (6) | 1.08462 (5) | 0.0340 (2) | |
Br2 | 0.21489 (7) | 0.73817 (6) | 1.09288 (5) | 0.0372 (2) | |
S1 | −0.03179 (14) | 0.56857 (14) | 0.75823 (13) | 0.0264 (3) | |
S2 | 0.49841 (14) | 1.06833 (14) | 0.75250 (13) | 0.0271 (3) | |
O1 | 0.2948 (4) | 0.5907 (4) | 0.6588 (3) | 0.0273 (9) | |
O2 | 0.1570 (4) | 1.0853 (4) | 0.6640 (3) | 0.0286 (10) | |
C1 | 0.1213 (6) | 0.5505 (5) | 0.7258 (5) | 0.0243 (13) | |
C2 | 0.2219 (5) | 0.5038 (5) | 0.7717 (5) | 0.0232 (12) | |
C3 | 0.2368 (5) | 0.4429 (5) | 0.8456 (5) | 0.0252 (13) | |
C4 | 0.1379 (5) | 0.4037 (6) | 0.8922 (5) | 0.0267 (13) | |
H4 | 0.0565 | 0.4196 | 0.8750 | 0.032* | |
C5 | 0.1577 (6) | 0.3435 (6) | 0.9615 (5) | 0.0304 (14) | |
H5 | 0.0906 | 0.3171 | 0.9917 | 0.036* | |
C6 | 0.2774 (6) | 0.3212 (6) | 0.9875 (5) | 0.0276 (13) | |
C7 | 0.3755 (6) | 0.3548 (6) | 0.9445 (5) | 0.0293 (14) | |
H7 | 0.4557 | 0.3370 | 0.9629 | 0.035* | |
C8 | 0.3579 (5) | 0.4172 (6) | 0.8714 (5) | 0.0256 (13) | |
C9 | 0.4605 (6) | 0.4532 (6) | 0.8254 (5) | 0.0288 (14) | |
H9 | 0.5407 | 0.4365 | 0.8446 | 0.035* | |
C10 | 0.4449 (6) | 0.5118 (6) | 0.7538 (5) | 0.0316 (14) | |
H10 | 0.5126 | 0.5365 | 0.7232 | 0.038* | |
C11 | 0.3257 (6) | 0.5329 (5) | 0.7284 (5) | 0.0253 (13) | |
C12 | 0.1696 (6) | 0.5981 (6) | 0.6569 (5) | 0.0270 (13) | |
C13 | −0.1025 (5) | 0.4098 (6) | 0.6961 (5) | 0.0235 (12) | |
C14 | −0.2286 (6) | 0.4044 (6) | 0.7031 (5) | 0.0302 (14) | |
H14 | −0.2712 | 0.4814 | 0.7403 | 0.036* | |
C15 | −0.2910 (6) | 0.2868 (7) | 0.6559 (6) | 0.0377 (16) | |
H15 | −0.3772 | 0.2831 | 0.6607 | 0.045* | |
C16 | −0.2308 (6) | 0.1740 (6) | 0.6014 (5) | 0.0367 (16) | |
H16 | −0.2749 | 0.0931 | 0.5689 | 0.044* | |
C17 | −0.1065 (7) | 0.1805 (6) | 0.5950 (5) | 0.0353 (16) | |
H17 | −0.0646 | 0.1032 | 0.5568 | 0.042* | |
C18 | −0.0398 (6) | 0.2987 (6) | 0.6434 (5) | 0.0319 (15) | |
H18 | 0.0467 | 0.3020 | 0.6399 | 0.038* | |
C19 | 0.1166 (6) | 0.6575 (6) | 0.5860 (5) | 0.0348 (15) | |
H19A | 0.0272 | 0.6497 | 0.5844 | 0.052* | |
H19B | 0.1454 | 0.6124 | 0.5140 | 0.052* | |
H19C | 0.1421 | 0.7498 | 0.6127 | 0.052* | |
C20 | 0.3396 (5) | 1.0475 (5) | 0.7246 (5) | 0.0228 (12) | |
C21 | 0.2475 (5) | 0.9976 (5) | 0.7729 (5) | 0.0254 (13) | |
C22 | 0.2450 (5) | 0.9334 (5) | 0.8445 (5) | 0.0242 (13) | |
C23 | 0.3499 (6) | 0.8997 (6) | 0.8901 (5) | 0.0300 (14) | |
H23 | 0.4284 | 0.9178 | 0.8705 | 0.036* | |
C24 | 0.3419 (6) | 0.8417 (6) | 0.9618 (5) | 0.0314 (14) | |
H24 | 0.4137 | 0.8187 | 0.9909 | 0.038* | |
C25 | 0.2254 (6) | 0.8166 (6) | 0.9917 (5) | 0.0285 (14) | |
C26 | 0.1205 (6) | 0.8471 (6) | 0.9498 (5) | 0.0308 (14) | |
H26 | 0.0431 | 0.8290 | 0.9713 | 0.037* | |
C27 | 0.1272 (6) | 0.9054 (6) | 0.8748 (5) | 0.0269 (13) | |
C28 | 0.0182 (6) | 0.9375 (6) | 0.8317 (6) | 0.0341 (15) | |
H28 | −0.0588 | 0.9182 | 0.8532 | 0.041* | |
C29 | 0.0217 (6) | 0.9958 (6) | 0.7599 (5) | 0.0320 (15) | |
H29 | −0.0509 | 1.0163 | 0.7302 | 0.038* | |
C30 | 0.1372 (6) | 1.0235 (6) | 0.7324 (5) | 0.0293 (14) | |
C31 | 0.2818 (6) | 1.0986 (6) | 0.6610 (5) | 0.0262 (13) | |
C32 | 0.5543 (5) | 0.9086 (6) | 0.6865 (5) | 0.0251 (13) | |
C33 | 0.6747 (6) | 0.8905 (7) | 0.7109 (5) | 0.0346 (15) | |
H33 | 0.7220 | 0.9607 | 0.7620 | 0.041* | |
C34 | 0.7264 (6) | 0.7704 (7) | 0.6608 (6) | 0.0371 (16) | |
H34 | 0.8091 | 0.7586 | 0.6780 | 0.045* | |
C35 | 0.6599 (7) | 0.6687 (6) | 0.5871 (6) | 0.0372 (16) | |
H35 | 0.6958 | 0.5865 | 0.5530 | 0.045* | |
C36 | 0.5391 (7) | 0.6866 (6) | 0.5625 (6) | 0.0372 (16) | |
H36 | 0.4927 | 0.6163 | 0.5108 | 0.045* | |
C37 | 0.4854 (6) | 0.8059 (6) | 0.6127 (5) | 0.0306 (14) | |
H37 | 0.4022 | 0.8170 | 0.5965 | 0.037* | |
C38 | 0.3258 (6) | 1.1671 (6) | 0.5937 (5) | 0.0328 (15) | |
H38A | 0.3182 | 1.2614 | 0.6317 | 0.049* | |
H38B | 0.2764 | 1.1376 | 0.5268 | 0.049* | |
H38C | 0.4116 | 1.1475 | 0.5784 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0461 (4) | 0.0292 (3) | 0.0315 (4) | 0.0040 (3) | 0.0021 (3) | 0.0168 (3) |
Br2 | 0.0543 (5) | 0.0316 (4) | 0.0308 (4) | −0.0065 (3) | 0.0025 (3) | 0.0180 (3) |
S1 | 0.0264 (8) | 0.0206 (7) | 0.0322 (9) | 0.0028 (6) | 0.0041 (6) | 0.0099 (6) |
S2 | 0.0259 (8) | 0.0203 (7) | 0.0341 (9) | −0.0029 (6) | 0.0014 (6) | 0.0096 (6) |
O1 | 0.033 (2) | 0.026 (2) | 0.026 (2) | −0.0006 (17) | 0.0070 (18) | 0.0125 (18) |
O2 | 0.032 (2) | 0.027 (2) | 0.031 (2) | 0.0031 (18) | −0.0012 (18) | 0.0158 (19) |
C1 | 0.038 (3) | 0.012 (3) | 0.022 (3) | 0.004 (2) | 0.002 (3) | 0.007 (2) |
C2 | 0.028 (3) | 0.017 (3) | 0.023 (3) | 0.000 (2) | 0.006 (2) | 0.006 (2) |
C3 | 0.028 (3) | 0.020 (3) | 0.021 (3) | −0.004 (2) | 0.001 (2) | 0.002 (2) |
C4 | 0.023 (3) | 0.033 (3) | 0.026 (3) | −0.002 (2) | 0.002 (2) | 0.014 (3) |
C5 | 0.032 (3) | 0.032 (3) | 0.028 (3) | −0.006 (3) | 0.005 (3) | 0.012 (3) |
C6 | 0.037 (4) | 0.023 (3) | 0.022 (3) | 0.003 (3) | 0.003 (3) | 0.007 (3) |
C7 | 0.034 (4) | 0.028 (3) | 0.023 (3) | 0.003 (3) | 0.000 (3) | 0.007 (3) |
C8 | 0.027 (3) | 0.027 (3) | 0.018 (3) | 0.001 (2) | 0.001 (2) | 0.004 (2) |
C9 | 0.027 (3) | 0.032 (3) | 0.021 (3) | 0.000 (3) | −0.001 (2) | 0.004 (3) |
C10 | 0.025 (3) | 0.036 (4) | 0.031 (4) | −0.006 (3) | 0.006 (3) | 0.010 (3) |
C11 | 0.037 (4) | 0.021 (3) | 0.016 (3) | −0.001 (2) | 0.005 (3) | 0.005 (2) |
C12 | 0.031 (3) | 0.021 (3) | 0.029 (3) | 0.001 (2) | 0.003 (3) | 0.008 (3) |
C13 | 0.029 (3) | 0.024 (3) | 0.019 (3) | 0.001 (2) | −0.005 (2) | 0.010 (2) |
C14 | 0.026 (3) | 0.031 (3) | 0.031 (4) | 0.002 (3) | 0.004 (3) | 0.009 (3) |
C15 | 0.032 (4) | 0.037 (4) | 0.046 (4) | −0.005 (3) | 0.004 (3) | 0.018 (3) |
C16 | 0.046 (4) | 0.028 (3) | 0.032 (4) | −0.012 (3) | −0.007 (3) | 0.008 (3) |
C17 | 0.052 (4) | 0.021 (3) | 0.030 (4) | 0.001 (3) | −0.008 (3) | 0.008 (3) |
C18 | 0.027 (3) | 0.029 (3) | 0.040 (4) | 0.004 (3) | −0.002 (3) | 0.014 (3) |
C19 | 0.045 (4) | 0.029 (3) | 0.034 (4) | 0.004 (3) | 0.004 (3) | 0.017 (3) |
C20 | 0.027 (3) | 0.016 (3) | 0.022 (3) | −0.005 (2) | 0.000 (2) | 0.004 (2) |
C21 | 0.025 (3) | 0.019 (3) | 0.030 (3) | −0.002 (2) | 0.004 (3) | 0.007 (3) |
C22 | 0.031 (3) | 0.019 (3) | 0.020 (3) | −0.003 (2) | 0.001 (2) | 0.005 (2) |
C23 | 0.032 (3) | 0.026 (3) | 0.036 (4) | −0.002 (3) | 0.004 (3) | 0.016 (3) |
C24 | 0.037 (4) | 0.026 (3) | 0.032 (4) | 0.003 (3) | 0.000 (3) | 0.012 (3) |
C25 | 0.040 (4) | 0.022 (3) | 0.024 (3) | −0.005 (3) | 0.001 (3) | 0.010 (3) |
C26 | 0.034 (4) | 0.029 (3) | 0.027 (3) | −0.004 (3) | 0.007 (3) | 0.007 (3) |
C27 | 0.031 (3) | 0.023 (3) | 0.024 (3) | −0.005 (2) | 0.002 (3) | 0.006 (3) |
C28 | 0.025 (3) | 0.033 (3) | 0.041 (4) | −0.002 (3) | 0.005 (3) | 0.011 (3) |
C29 | 0.022 (3) | 0.030 (3) | 0.040 (4) | 0.003 (3) | 0.000 (3) | 0.010 (3) |
C30 | 0.030 (3) | 0.028 (3) | 0.032 (4) | 0.004 (3) | 0.004 (3) | 0.013 (3) |
C31 | 0.035 (3) | 0.022 (3) | 0.024 (3) | 0.001 (2) | 0.002 (3) | 0.012 (3) |
C32 | 0.025 (3) | 0.023 (3) | 0.033 (3) | 0.002 (2) | 0.010 (3) | 0.017 (3) |
C33 | 0.037 (4) | 0.036 (4) | 0.032 (4) | 0.002 (3) | 0.000 (3) | 0.014 (3) |
C34 | 0.034 (4) | 0.048 (4) | 0.035 (4) | 0.013 (3) | 0.007 (3) | 0.023 (3) |
C35 | 0.054 (4) | 0.028 (3) | 0.035 (4) | 0.011 (3) | 0.015 (3) | 0.017 (3) |
C36 | 0.048 (4) | 0.027 (3) | 0.036 (4) | −0.005 (3) | 0.009 (3) | 0.010 (3) |
C37 | 0.032 (3) | 0.030 (3) | 0.033 (4) | −0.005 (3) | 0.005 (3) | 0.015 (3) |
C38 | 0.048 (4) | 0.022 (3) | 0.034 (4) | −0.001 (3) | 0.002 (3) | 0.017 (3) |
Br1—C6 | 1.904 (6) | C17—H17 | 0.9500 |
Br2—C25 | 1.903 (6) | C18—H18 | 0.9500 |
S1—C1 | 1.743 (6) | C19—H19A | 0.9800 |
S1—C13 | 1.786 (6) | C19—H19B | 0.9800 |
S2—C20 | 1.758 (6) | C19—H19C | 0.9800 |
S2—C32 | 1.782 (6) | C20—C31 | 1.353 (8) |
O1—C11 | 1.373 (7) | C20—C21 | 1.439 (8) |
O1—C12 | 1.374 (7) | C21—C30 | 1.391 (9) |
O2—C31 | 1.376 (8) | C21—C22 | 1.416 (8) |
O2—C30 | 1.378 (7) | C22—C23 | 1.412 (9) |
C1—C12 | 1.362 (8) | C22—C27 | 1.434 (8) |
C1—C2 | 1.447 (8) | C23—C24 | 1.368 (9) |
C2—C11 | 1.389 (8) | C23—H23 | 0.9500 |
C2—C3 | 1.422 (8) | C24—C25 | 1.409 (9) |
C3—C4 | 1.420 (8) | C24—H24 | 0.9500 |
C3—C8 | 1.421 (8) | C25—C26 | 1.371 (9) |
C4—C5 | 1.367 (9) | C26—C27 | 1.411 (9) |
C4—H4 | 0.9500 | C26—H26 | 0.9500 |
C5—C6 | 1.397 (9) | C27—C28 | 1.423 (9) |
C5—H5 | 0.9500 | C28—C29 | 1.37 (1) |
C6—C7 | 1.356 (9) | C28—H28 | 0.9500 |
C7—C8 | 1.428 (9) | C29—C30 | 1.395 (9) |
C7—H7 | 0.9500 | C29—H29 | 0.9500 |
C8—C9 | 1.431 (9) | C31—C38 | 1.489 (8) |
C9—C10 | 1.376 (9) | C32—C33 | 1.385 (9) |
C9—H9 | 0.9500 | C32—C37 | 1.385 (9) |
C10—C11 | 1.385 (9) | C33—C34 | 1.385 (9) |
C10—H10 | 0.9500 | C33—H33 | 0.9500 |
C12—C19 | 1.475 (9) | C34—C35 | 1.37 (1) |
C13—C18 | 1.375 (8) | C34—H34 | 0.9500 |
C13—C14 | 1.389 (9) | C35—C36 | 1.39 (1) |
C14—C15 | 1.371 (9) | C35—H35 | 0.9500 |
C14—H14 | 0.9500 | C36—C37 | 1.387 (9) |
C15—C16 | 1.38 (1) | C36—H36 | 0.9500 |
C15—H15 | 0.9500 | C37—H37 | 0.9500 |
C16—C17 | 1.37 (1) | C38—H38A | 0.9800 |
C16—H16 | 0.9500 | C38—H38B | 0.9800 |
C17—C18 | 1.401 (9) | C38—H38C | 0.9800 |
C1—S1—C13 | 105.9 (3) | H19A—C19—H19C | 109.5 |
C20—S2—C32 | 103.8 (3) | H19B—C19—H19C | 109.5 |
C11—O1—C12 | 106.9 (4) | C31—C20—C21 | 107.7 (5) |
C31—O2—C30 | 106.2 (4) | C31—C20—S2 | 121.9 (5) |
C12—C1—C2 | 107.1 (5) | C21—C20—S2 | 129.7 (5) |
C12—C1—S1 | 122.1 (5) | C30—C21—C22 | 118.7 (5) |
C2—C1—S1 | 130.3 (4) | C30—C21—C20 | 104.6 (5) |
C11—C2—C3 | 118.2 (5) | C22—C21—C20 | 136.7 (6) |
C11—C2—C1 | 105.0 (5) | C23—C22—C21 | 124.5 (6) |
C3—C2—C1 | 136.8 (5) | C23—C22—C27 | 118.4 (5) |
C4—C3—C8 | 118.7 (6) | C21—C22—C27 | 117.0 (5) |
C4—C3—C2 | 123.7 (6) | C24—C23—C22 | 121.9 (6) |
C8—C3—C2 | 117.6 (5) | C24—C23—H23 | 119.0 |
C5—C4—C3 | 121.1 (6) | C22—C23—H23 | 119.0 |
C5—C4—H4 | 119.4 | C23—C24—C25 | 118.8 (6) |
C3—C4—H4 | 119.4 | C23—C24—H24 | 120.6 |
C4—C5—C6 | 119.4 (6) | C25—C24—H24 | 120.6 |
C4—C5—H5 | 120.3 | C26—C25—C24 | 121.7 (6) |
C6—C5—H5 | 120.3 | C26—C25—Br2 | 119.6 (5) |
C7—C6—C5 | 122.2 (6) | C24—C25—Br2 | 118.7 (5) |
C7—C6—Br1 | 119.3 (5) | C25—C26—C27 | 120.1 (6) |
C5—C6—Br1 | 118.5 (5) | C25—C26—H26 | 119.9 |
C6—C7—C8 | 119.8 (6) | C27—C26—H26 | 119.9 |
C6—C7—H7 | 120.1 | C26—C27—C28 | 120.1 (6) |
C8—C7—H7 | 120.1 | C26—C27—C22 | 119.0 (6) |
C3—C8—C7 | 118.8 (6) | C28—C27—C22 | 120.9 (6) |
C3—C8—C9 | 120.8 (6) | C29—C28—C27 | 121.5 (6) |
C7—C8—C9 | 120.4 (6) | C29—C28—H28 | 119.3 |
C10—C9—C8 | 121.1 (6) | C27—C28—H28 | 119.3 |
C10—C9—H9 | 119.4 | C28—C29—C30 | 116.7 (6) |
C8—C9—H9 | 119.4 | C28—C29—H29 | 121.7 |
C9—C10—C11 | 116.7 (6) | C30—C29—H29 | 121.7 |
C9—C10—H10 | 121.6 | O2—C30—C21 | 110.8 (5) |
C11—C10—H10 | 121.6 | O2—C30—C29 | 124.1 (6) |
O1—C11—C10 | 123.9 (5) | C21—C30—C29 | 125.1 (6) |
O1—C11—C2 | 110.5 (5) | C20—C31—O2 | 110.7 (5) |
C10—C11—C2 | 125.5 (6) | C20—C31—C38 | 133.3 (6) |
C1—C12—O1 | 110.4 (5) | O2—C31—C38 | 116.0 (5) |
C1—C12—C19 | 133.8 (6) | C33—C32—C37 | 119.8 (6) |
O1—C12—C19 | 115.7 (5) | C33—C32—S2 | 116.4 (5) |
C18—C13—C14 | 120.8 (6) | C37—C32—S2 | 123.7 (5) |
C18—C13—S1 | 123.9 (5) | C34—C33—C32 | 120.1 (6) |
C14—C13—S1 | 115.4 (4) | C34—C33—H33 | 120.0 |
C15—C14—C13 | 119.4 (6) | C32—C33—H33 | 120.0 |
C15—C14—H14 | 120.3 | C35—C34—C33 | 120.7 (6) |
C13—C14—H14 | 120.3 | C35—C34—H34 | 119.7 |
C14—C15—C16 | 121.1 (6) | C33—C34—H34 | 119.7 |
C14—C15—H15 | 119.4 | C34—C35—C36 | 119.3 (6) |
C16—C15—H15 | 119.4 | C34—C35—H35 | 120.3 |
C17—C16—C15 | 119.0 (6) | C36—C35—H35 | 120.3 |
C17—C16—H16 | 120.5 | C37—C36—C35 | 120.8 (6) |
C15—C16—H16 | 120.5 | C37—C36—H36 | 119.6 |
C16—C17—C18 | 121.4 (6) | C35—C36—H36 | 119.6 |
C16—C17—H17 | 119.3 | C32—C37—C36 | 119.3 (6) |
C18—C17—H17 | 119.3 | C32—C37—H37 | 120.4 |
C13—C18—C17 | 118.3 (6) | C36—C37—H37 | 120.4 |
C13—C18—H18 | 120.8 | C31—C38—H38A | 109.5 |
C17—C18—H18 | 120.8 | C31—C38—H38B | 109.5 |
C12—C19—H19A | 109.5 | H38A—C38—H38B | 109.5 |
C12—C19—H19B | 109.5 | C31—C38—H38C | 109.5 |
H19A—C19—H19B | 109.5 | H38A—C38—H38C | 109.5 |
C12—C19—H19C | 109.5 | H38B—C38—H38C | 109.5 |
C13—S1—C1—C12 | 109.2 (5) | C32—S2—C20—C31 | −111.8 (5) |
C13—S1—C1—C2 | −80.1 (6) | C32—S2—C20—C21 | 79.3 (6) |
C12—C1—C2—C11 | 2.4 (6) | C31—C20—C21—C30 | 0.2 (7) |
S1—C1—C2—C11 | −169.4 (5) | S2—C20—C21—C30 | 170.3 (5) |
C12—C1—C2—C3 | −179.0 (7) | C31—C20—C21—C22 | 179.5 (7) |
S1—C1—C2—C3 | 9.2 (11) | S2—C20—C21—C22 | −10.4 (11) |
C11—C2—C3—C4 | −177.5 (6) | C30—C21—C22—C23 | 179.1 (6) |
C1—C2—C3—C4 | 4.0 (11) | C20—C21—C22—C23 | −0.1 (11) |
C11—C2—C3—C8 | 0.8 (8) | C30—C21—C22—C27 | −3.2 (8) |
C1—C2—C3—C8 | −177.7 (6) | C20—C21—C22—C27 | 177.6 (6) |
C8—C3—C4—C5 | 0.6 (9) | C21—C22—C23—C24 | 177.7 (6) |
C2—C3—C4—C5 | 178.9 (6) | C27—C22—C23—C24 | −0.1 (9) |
C3—C4—C5—C6 | 0.5 (9) | C22—C23—C24—C25 | −0.8 (9) |
C4—C5—C6—C7 | −1.4 (10) | C23—C24—C25—C26 | 0.9 (9) |
C4—C5—C6—Br1 | 179.7 (5) | C23—C24—C25—Br2 | −179.2 (5) |
C5—C6—C7—C8 | 1.0 (9) | C24—C25—C26—C27 | −0.1 (9) |
Br1—C6—C7—C8 | 179.9 (4) | Br2—C25—C26—C27 | 180.0 (5) |
C4—C3—C8—C7 | −1.0 (8) | C25—C26—C27—C28 | −179.7 (6) |
C2—C3—C8—C7 | −179.3 (5) | C25—C26—C27—C22 | −0.8 (9) |
C4—C3—C8—C9 | 179.2 (6) | C23—C22—C27—C26 | 0.9 (8) |
C2—C3—C8—C9 | 0.8 (8) | C21—C22—C27—C26 | −177.0 (5) |
C6—C7—C8—C3 | 0.1 (9) | C23—C22—C27—C28 | 179.8 (6) |
C6—C7—C8—C9 | −180.0 (6) | C21—C22—C27—C28 | 1.9 (8) |
C3—C8—C9—C10 | −1.0 (9) | C26—C27—C28—C29 | 179.1 (6) |
C7—C8—C9—C10 | 179.1 (6) | C22—C27—C28—C29 | 0.2 (9) |
C8—C9—C10—C11 | −0.4 (9) | C27—C28—C29—C30 | −0.9 (10) |
C12—O1—C11—C10 | −178.2 (6) | C31—O2—C30—C21 | 0.1 (7) |
C12—O1—C11—C2 | −0.3 (6) | C31—O2—C30—C29 | 177.8 (6) |
C9—C10—C11—O1 | 179.7 (5) | C22—C21—C30—O2 | −179.6 (5) |
C9—C10—C11—C2 | 2.2 (9) | C20—C21—C30—O2 | −0.2 (7) |
C3—C2—C11—O1 | 179.8 (5) | C22—C21—C30—C29 | 2.7 (9) |
C1—C2—C11—O1 | −1.3 (6) | C20—C21—C30—C29 | −177.9 (6) |
C3—C2—C11—C10 | −2.4 (9) | C28—C29—C30—O2 | −178.0 (6) |
C1—C2—C11—C10 | 176.5 (6) | C28—C29—C30—C21 | −0.6 (10) |
C2—C1—C12—O1 | −2.7 (6) | C21—C20—C31—O2 | −0.2 (7) |
S1—C1—C12—O1 | 169.9 (4) | S2—C20—C31—O2 | −171.2 (4) |
C2—C1—C12—C19 | 179.5 (7) | C21—C20—C31—C38 | 177.8 (6) |
S1—C1—C12—C19 | −7.9 (10) | S2—C20—C31—C38 | 6.7 (10) |
C11—O1—C12—C1 | 1.9 (6) | C30—O2—C31—C20 | 0.1 (6) |
C11—O1—C12—C19 | −179.8 (5) | C30—O2—C31—C38 | −178.3 (5) |
C1—S1—C13—C18 | 5.5 (6) | C20—S2—C32—C33 | −168.5 (5) |
C1—S1—C13—C14 | −173.8 (5) | C20—S2—C32—C37 | 12.8 (6) |
C18—C13—C14—C15 | −0.7 (10) | C37—C32—C33—C34 | 0.6 (10) |
S1—C13—C14—C15 | 178.7 (5) | S2—C32—C33—C34 | −178.1 (5) |
C13—C14—C15—C16 | −0.1 (10) | C32—C33—C34—C35 | 0.0 (10) |
C14—C15—C16—C17 | 0.0 (11) | C33—C34—C35—C36 | 0.0 (10) |
C15—C16—C17—C18 | 0.8 (10) | C34—C35—C36—C37 | −0.6 (10) |
C14—C13—C18—C17 | 1.4 (9) | C33—C32—C37—C36 | −1.2 (9) |
S1—C13—C18—C17 | −177.9 (5) | S2—C32—C37—C36 | 177.4 (5) |
C16—C17—C18—C13 | −1.5 (10) | C35—C36—C37—C32 | 1.3 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19C···Cg3 | 0.98 | 2.77 | 3.551 (6) | 137 |
C38—H38A···Cg5 | 0.98 | 2.60 | 3.498 (6) | 153 |
Experimental details
Crystal data | |
Chemical formula | C19H13BrOS |
Mr | 369.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 10.947 (2), 11.130 (2), 13.636 (2) |
α, β, γ (°) | 112.798 (2), 91.999 (3), 90.908 (2) |
V (Å3) | 1529.9 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.82 |
Crystal size (mm) | 0.35 × 0.25 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1999) |
Tmin, Tmax | 0.442, 0.760 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7613, 5209, 4269 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.152, 1.14 |
No. of reflections | 5209 |
No. of parameters | 398 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.62, −0.65 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19C···Cg3 | 0.98 | 2.77 | 3.551 (6) | 136.5 |
C38—H38A···Cg5 | 0.98 | 2.60 | 3.498 (6) | 152.5 |
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As part of our ongoing studies on the synthesis and structure of 2-methylnaphtho[2,1-b]furan analogues, we have recently described the crystal structures of 2-methyl-1-(methylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2006) and 2-methyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2007). Herein we report the molecular and crystal structure of the title compound, (Fig. 1).
The phenyl rings (C13—C18 in unit A and C32—C37 in unit B) are tilted towards the plane of the naphthofuran systems [72.9 (9)° (unit A) and 80.5 (1)° (unit B)]. The molecular packing (Fig. 2) is stabilized by two different π···π interactions within each stack of molecules; one between the benzene ring (Cg4) and an adjacent furan ring (Cg1) of benzofuran unit {distance; 3.594 (9) Å}, and a second between the benzene ring (Cg6) and an adjacent furan ring (Cg2) of benzofuran unit {distance; 3.658 (9) Å} (Cg1, Cg2, Cg4, and Cg6 are the centroids of the O1/C12/C1/C2/C11 furan ring, the O2/C31/C20/C21/C30 furan ring, the C22—C27 benzene ring, and the C3—C8 benzene ring, respectively; symmetry code as in Fig. 2). The crystal packing (Fig. 2) is further stabilized by CH2—H···π interactions; one between the methyl group (unit B) and the benzene ring (unit A) of benzofuran unit, with a C38—H38A···Cg5 separation of 2.60 Å, and a second between the methyl group (Unit A) and the benzene ring (Unit B) of benzofuran unit, with a C19—H19C···Cg3 separation of 2.77 Å (Fig. 2 and Table 1; Cg3 and Cg5 are the centroids of the C21/C22/C27/C28/C29/C30 benzene ring and the C2/C3/C8/C9/C10/C11 benzene ring, respectively; symmetry code as in Fig. 2). In addition, the crystal packing (Fig. 2) is further stabilized by weak C—Br···π interactions: one between the Br atom (Unit B) and the phenyl ring (Unit A) with a C25—Br2···Cg8 separation of 3.718 (6) Å, and a second between the Br atom (Unit A) and the phenyl ring (Unit B) with a C6—Br1···Cg7 separation of 4.015 (6) Å (Fig. 2; Cg7 and Cg8 are the centroids of the C32—C37 benzene ring and the C13—C18 benzene ring, respectively; symmetry code as in Fig. 2).