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The molecule of the title compound, C30H18, is located on an inversion center and has an almost completely planar geometry.
Supporting information
CCDC reference: 618243
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.137
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for C8 - C9 .. 7.13 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C10 - C11 .. 9.83 su
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C2 .. 6.19 su
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C2 ... 1.44 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. CG2 .. 2.94 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; data reduction: TEXSAN (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN.
Bis(9-phenanthryl)ethyne
top
Crystal data top
C30H18 | F(000) = 396 |
Mr = 378.47 | Dx = 1.309 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 2216 reflections |
a = 9.3403 (8) Å | θ = 4.0–27.5° |
b = 15.2266 (11) Å | µ = 0.07 mm−1 |
c = 6.9007 (5) Å | T = 150 K |
β = 102.0338 (13)° | Prism, colorless |
V = 959.86 (13) Å3 | 0.45 × 0.30 × 0.20 mm |
Z = 2 | |
Data collection top
Rigaku/MSC Mercury CCD diffractometer | Rint = 0.019 |
Detector resolution: 14.63 pixels mm-1 | θmax = 27.5°, θmin = 4.0° |
ω scans | h = −12→12 |
9274 measured reflections | k = −19→19 |
2151 independent reflections | l = −8→8 |
2036 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.0872P)2 + 0.1528P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.137 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.33 e Å−3 |
2151 reflections | Δρmin = −0.19 e Å−3 |
145 parameters | |
Special details top
Experimental. 1H NMR (CDCl3): δ 8.78–8.70 (m, 3H), 8.25 (s, 1H), 7.95
(dd, 1H, J = 7.6, 1.5 Hz), 7.80–7.62 (m, 4H); EI–MS
(m/z, %): 378 (M+, 100). |
Refinement. Refinement was carried out using all reflections. The weighted R-factor
(wR) and goodness of fit (S) are based on F2.
R-factor (gt) are based on F. The threshold expression of
F2 > 2.0 σ(F2) is used only for calculating R-factor
(gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.47993 (11) | 0.01799 (6) | 0.92192 (15) | 0.0240 (2) | |
C2 | 0.43548 (11) | 0.06022 (6) | 0.73302 (14) | 0.0212 (2) | |
C3 | 0.29146 (11) | 0.06268 (6) | 0.64007 (15) | 0.0234 (3) | |
C4 | 0.24495 (11) | 0.10142 (6) | 0.44845 (15) | 0.0213 (2) | |
C5 | 0.09541 (12) | 0.10037 (7) | 0.35211 (17) | 0.0268 (3) | |
C6 | 0.05009 (12) | 0.13640 (7) | 0.16696 (18) | 0.0314 (3) | |
C7 | 0.15306 (13) | 0.17465 (7) | 0.07087 (16) | 0.0312 (3) | |
C8 | 0.29921 (12) | 0.17623 (7) | 0.16138 (16) | 0.0268 (3) | |
C9 | 0.34933 (11) | 0.13988 (6) | 0.35194 (15) | 0.0205 (2) | |
C10 | 0.50284 (11) | 0.14027 (6) | 0.45150 (15) | 0.0201 (2) | |
C11 | 0.61247 (11) | 0.17975 (6) | 0.36754 (16) | 0.0250 (3) | |
C12 | 0.75734 (12) | 0.17803 (7) | 0.46387 (17) | 0.0284 (3) | |
C13 | 0.79952 (11) | 0.13606 (7) | 0.64737 (17) | 0.0283 (3) | |
C14 | 0.69535 (11) | 0.09771 (7) | 0.73422 (15) | 0.0246 (3) | |
C15 | 0.54608 (11) | 0.09947 (6) | 0.63996 (14) | 0.0202 (2) | |
H1 | 0.2203 | 0.0380 | 0.7043 | 0.032 (3)* | |
H2 | 0.0254 | 0.0744 | 0.4165 | 0.041 (4)* | |
H3 | −0.0506 | 0.1354 | 0.1042 | 0.046 (4)* | |
H4 | 0.1218 | 0.1996 | −0.0572 | 0.044 (4)* | |
H5 | 0.3676 | 0.2023 | 0.0944 | 0.039 (4)* | |
H6 | 0.5859 | 0.2080 | 0.2424 | 0.033 (3)* | |
H7 | 0.8292 | 0.2056 | 0.4053 | 0.037 (4)* | |
H8 | 0.8998 | 0.1341 | 0.7117 | 0.041 (4)* | |
H9 | 0.7243 | 0.0697 | 0.8593 | 0.035 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0263 (5) | 0.0253 (5) | 0.0205 (5) | 0.0005 (3) | 0.0054 (4) | 0.0019 (4) |
C2 | 0.0272 (5) | 0.0199 (5) | 0.0167 (5) | 0.0001 (3) | 0.0047 (4) | 0.0023 (3) |
C3 | 0.0259 (5) | 0.0242 (5) | 0.0209 (5) | 0.0021 (4) | 0.0070 (4) | 0.0006 (3) |
C4 | 0.0231 (5) | 0.0199 (5) | 0.0201 (5) | −0.0001 (3) | 0.0029 (4) | 0.0014 (3) |
C5 | 0.0228 (5) | 0.0286 (5) | 0.0282 (6) | 0.0017 (4) | 0.0035 (4) | −0.0009 (4) |
C6 | 0.0252 (5) | 0.0352 (6) | 0.0296 (6) | 0.0015 (4) | −0.0039 (4) | 0.0008 (4) |
C7 | 0.0332 (6) | 0.0338 (6) | 0.0226 (5) | 0.0060 (4) | −0.0030 (4) | 0.0016 (4) |
C8 | 0.0290 (6) | 0.0274 (5) | 0.0232 (6) | 0.0053 (4) | 0.0034 (4) | −0.0001 (4) |
C9 | 0.0242 (5) | 0.0178 (5) | 0.0186 (5) | −0.0007 (3) | 0.0026 (4) | 0.0014 (3) |
C10 | 0.0236 (5) | 0.0170 (4) | 0.0196 (5) | −0.0006 (3) | 0.0038 (4) | 0.0009 (3) |
C11 | 0.0276 (5) | 0.0234 (5) | 0.0239 (5) | 0.0032 (4) | 0.0055 (4) | −0.0001 (4) |
C12 | 0.0258 (5) | 0.0280 (5) | 0.0323 (6) | 0.0019 (4) | 0.0083 (4) | −0.0027 (4) |
C13 | 0.0220 (5) | 0.0308 (5) | 0.0304 (6) | −0.0027 (4) | 0.0016 (4) | 0.0001 (4) |
C14 | 0.0265 (5) | 0.0256 (5) | 0.0200 (5) | −0.0007 (4) | 0.0006 (4) | 0.0021 (4) |
C15 | 0.0240 (5) | 0.0179 (4) | 0.0185 (5) | −0.0013 (3) | 0.0035 (4) | 0.0013 (3) |
Geometric parameters (Å, º) top
C1—C1i | 1.197 (2) | C8—C9 | 1.4135 (14) |
C1—C2 | 1.4351 (13) | C8—H5 | 0.9500 |
C2—C3 | 1.3648 (14) | C9—C10 | 1.4551 (14) |
C2—C15 | 1.4538 (13) | C10—C11 | 1.4116 (14) |
C3—C4 | 1.4303 (14) | C10—C15 | 1.4218 (13) |
C3—H1 | 0.9500 | C11—C12 | 1.3779 (15) |
C4—C5 | 1.4163 (14) | C11—H6 | 0.9500 |
C4—C9 | 1.4169 (14) | C12—C13 | 1.3997 (15) |
C5—C6 | 1.3737 (16) | C12—H7 | 0.9500 |
C5—H2 | 0.9500 | C13—C14 | 1.3748 (15) |
C6—C7 | 1.4034 (17) | C13—H8 | 0.9500 |
C6—H3 | 0.9500 | C14—C15 | 1.4105 (14) |
C7—C8 | 1.3779 (15) | C14—H9 | 0.9500 |
C7—H4 | 0.9500 | | |
| | | |
C1i—C1—C2 | 178.37 (14) | C8—C9—C4 | 118.18 (9) |
C3—C2—C1 | 120.62 (9) | C8—C9—C10 | 122.70 (9) |
C3—C2—C15 | 120.17 (9) | C4—C9—C10 | 119.12 (9) |
C1—C2—C15 | 119.20 (9) | C11—C10—C15 | 118.00 (9) |
C2—C3—C4 | 121.70 (9) | C11—C10—C9 | 122.39 (9) |
C2—C3—H1 | 119.1 | C15—C10—C9 | 119.61 (9) |
C4—C3—H1 | 119.1 | C12—C11—C10 | 121.15 (9) |
C5—C4—C9 | 119.46 (9) | C12—C11—H6 | 119.4 |
C5—C4—C3 | 120.60 (9) | C10—C11—H6 | 119.4 |
C9—C4—C3 | 119.93 (9) | C11—C12—C13 | 120.53 (9) |
C6—C5—C4 | 120.97 (10) | C11—C12—H7 | 119.7 |
C6—C5—H2 | 119.5 | C13—C12—H7 | 119.7 |
C4—C5—H2 | 119.5 | C14—C13—C12 | 119.81 (9) |
C5—C6—C7 | 119.77 (10) | C14—C13—H8 | 120.1 |
C5—C6—H3 | 120.1 | C12—C13—H8 | 120.1 |
C7—C6—H3 | 120.1 | C13—C14—C15 | 120.81 (9) |
C8—C7—C6 | 120.32 (10) | C13—C14—H9 | 119.6 |
C8—C7—H4 | 119.8 | C15—C14—H9 | 119.6 |
C6—C7—H4 | 119.8 | C14—C15—C10 | 119.68 (9) |
C7—C8—C9 | 121.30 (10) | C14—C15—C2 | 120.90 (9) |
C7—C8—H5 | 119.4 | C10—C15—C2 | 119.42 (9) |
C9—C8—H5 | 119.4 | | |
| | | |
C1—C2—C3—C4 | −177.60 (9) | C8—C9—C10—C15 | −177.57 (9) |
C15—C2—C3—C4 | 1.56 (14) | C4—C9—C10—C15 | 2.24 (13) |
C2—C3—C4—C5 | 177.75 (9) | C15—C10—C11—C12 | 0.73 (14) |
C2—C3—C4—C9 | −1.11 (14) | C9—C10—C11—C12 | −179.05 (9) |
C9—C4—C5—C6 | −0.27 (15) | C10—C11—C12—C13 | 0.67 (15) |
C3—C4—C5—C6 | −179.13 (10) | C11—C12—C13—C14 | −1.30 (16) |
C4—C5—C6—C7 | 0.21 (17) | C12—C13—C14—C15 | 0.50 (15) |
C5—C6—C7—C8 | −0.03 (17) | C13—C14—C15—C10 | 0.91 (15) |
C6—C7—C8—C9 | −0.10 (17) | C13—C14—C15—C2 | −178.99 (9) |
C7—C8—C9—C4 | 0.04 (15) | C11—C10—C15—C14 | −1.50 (13) |
C7—C8—C9—C10 | 179.85 (9) | C9—C10—C15—C14 | 178.29 (8) |
C5—C4—C9—C8 | 0.14 (14) | C11—C10—C15—C2 | 178.40 (8) |
C3—C4—C9—C8 | 179.01 (9) | C9—C10—C15—C2 | −1.82 (13) |
C5—C4—C9—C10 | −179.68 (8) | C3—C2—C15—C14 | 179.83 (9) |
C3—C4—C9—C10 | −0.80 (13) | C1—C2—C15—C14 | −1.01 (14) |
C8—C9—C10—C11 | 2.21 (14) | C3—C2—C15—C10 | −0.07 (14) |
C4—C9—C10—C11 | −177.98 (8) | C1—C2—C15—C10 | 179.10 (8) |
Symmetry code: (i) −x+1, −y, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H4···Cg2ii | 0.95 | 2.94 | 3.6512 (12) | 133 |
C11—H6···Cg3ii | 0.95 | 2.82 | 3.5932 (11) | 140 |
Symmetry code: (ii) x, −y+1/2, z−1/2. |
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