Bis(9-phenanthr­yl)ethyne

The molecule of the title compound, C₃₀H₁₈, is located on an inversion center and has an almost completely planar geometry.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.45 × 0.30 × 0.20 mm
Z = 2

Data collection

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

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0872P)^2 + 0.1528P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

C1—C1^i	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
C1^i—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)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H4···Cg2^ii	0.95	2.94	3.6512 (12)	133
C11—H6···Cg3^ii	0.95	2.82	3.5932 (11)	140

Symmetry code: (ii) x, −y+1/2, z−1/2.