9,9-Bis[4-(prop-2-yn-yloxy)phen-yl]-9H-fluorene.

In the title compound, C(31)H(22)O(2), the bond angle at the C atom belonging to the five-membered ring of the fluorene system is opened to 112.64 (12)°. The two benzene rings are twisted with respect to the fluorene ring system at dihedral angles of 72.81 (6) and 81.83 (6)°. One C(ar-yl)-O-C-C  fragment is extended, with a C-O-C-C torsion angle of -178.77 (13)°, but the other C(ar-yl)-O-C-C  fragment is bent, with a C-O-C-C torsion angle of 64.78 (19)°. Inter-molecular weak C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the synthesis of copolyethers having 1,3,4-oxadiazole rings and fluorene groups from the polymerization of 9,9-bis­(4-propargyloxyphen­yl)fluorene, see: Hamciuc et al. (2009 ▶). For a related structure, see: Shah et al. (2010 ▶).

Experimental

Crystal data

C31H22O2

M = 426.49

Orthorhombic,

a = 11.0047 (8) Å

b = 12.9686 (9) Å

c = 15.4371 (11) Å

V = 2203.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

21245 measured reflections

2861 independent reflections

2658 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.082

S = 1.04

2861 reflections

306 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: 2204 Friedel pairs were merged

Flack parameter: ?

Rogers parameter: ?

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025833/xu2792sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025833/xu2792Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C31H22O2	F(000) = 896
Mr = 426.49	Dx = 1.286 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7024 reflections
a = 11.0047 (8) Å	θ = 2.3–27.7°
b = 12.9686 (9) Å	µ = 0.08 mm−1
c = 15.4371 (11) Å	T = 100 K
V = 2203.1 (3) Å3	Block, colorless
Z = 4	0.35 × 0.25 × 0.15 mm

Bruker SMART APEX diffractometer	2658 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 27.5°, θmin = 2.1°
ω scans	h = −14→14
21245 measured reflections	k = −16→16
2861 independent reflections	l = −19→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.3105P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2861 reflections	Δρmax = 0.18 e Å−3
306 parameters	Δρmin = −0.20 e Å−3
2 restraints	Absolute structure: 2204 Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	1.24715 (9)	0.37529 (9)	1.06380 (7)	0.0184 (3)
O2	0.72277 (11)	0.74489 (10)	0.66169 (7)	0.0228 (3)
C1	0.84334 (14)	0.71897 (12)	1.07308 (10)	0.0146 (3)
C2	0.93879 (15)	0.78830 (12)	1.08005 (11)	0.0174 (3)
H2	1.0072	0.7832	1.0428	0.021*
C3	0.93255 (15)	0.86561 (13)	1.14272 (11)	0.0200 (3)
H3	0.9979	0.9130	1.1488	0.024*
C4	0.83115 (16)	0.87398 (13)	1.19668 (11)	0.0205 (3)
H4	0.8278	0.9276	1.2385	0.025*
C5	0.73513 (16)	0.80494 (13)	1.18992 (11)	0.0188 (3)
H5	0.6660	0.8111	1.2264	0.023*
C6	0.74238 (14)	0.72624 (13)	1.12841 (10)	0.0156 (3)
C7	0.65875 (14)	0.64169 (13)	1.10835 (10)	0.0169 (3)
C8	0.54672 (15)	0.61615 (14)	1.14465 (11)	0.0206 (3)
H8	0.5128	0.6565	1.1900	0.025*
C9	0.48567 (15)	0.52999 (15)	1.11285 (12)	0.0226 (4)
H9	0.4097	0.5109	1.1372	0.027*
C10	0.53482 (15)	0.47162 (14)	1.04579 (12)	0.0211 (4)
H10	0.4922	0.4129	1.0251	0.025*
C11	0.64577 (15)	0.49837 (13)	1.00872 (11)	0.0189 (3)
H11	0.6782	0.4593	0.9621	0.023*
C12	0.70800 (14)	0.58268 (13)	1.04078 (10)	0.0157 (3)
C13	0.82912 (13)	0.62794 (12)	1.01042 (10)	0.0143 (3)
C14	0.93668 (14)	0.55407 (12)	1.02154 (10)	0.0145 (3)
C15	0.93030 (15)	0.46837 (13)	1.07548 (11)	0.0167 (3)
H15	0.8553	0.4519	1.1027	0.020*
C16	1.03105 (14)	0.40609 (13)	1.09059 (10)	0.0170 (3)
H16	1.0248	0.3477	1.1275	0.020*
C17	1.14088 (14)	0.43008 (13)	1.05113 (11)	0.0151 (3)
C18	1.14950 (14)	0.51457 (12)	0.99593 (11)	0.0160 (3)
H18	1.2243	0.5303	0.9682	0.019*
C19	1.04803 (14)	0.57562 (12)	0.98172 (10)	0.0160 (3)
H19	1.0542	0.6334	0.9441	0.019*
C20	1.23372 (16)	0.26883 (13)	1.08654 (12)	0.0210 (4)
H20A	1.1907	0.2313	1.0399	0.025*
H20B	1.1859	0.2623	1.1406	0.025*
C21	1.35523 (17)	0.22575 (14)	1.09882 (11)	0.0222 (4)
C22	1.4531 (2)	0.19125 (17)	1.11001 (14)	0.0342 (5)
C23	0.81257 (14)	0.66357 (13)	0.91600 (10)	0.0153 (3)
C24	0.76842 (14)	0.76168 (13)	0.89833 (10)	0.0163 (3)
H24	0.7588	0.8092	0.9447	0.020*
C25	0.73786 (15)	0.79255 (13)	0.81480 (11)	0.0186 (3)
H25	0.7075	0.8600	0.8043	0.022*
C26	0.75237 (15)	0.72339 (14)	0.74710 (10)	0.0182 (3)
C27	0.79946 (15)	0.62612 (15)	0.76239 (11)	0.0210 (4)
H27	0.8119	0.5799	0.7155	0.025*
C28	0.82856 (15)	0.59607 (13)	0.84623 (11)	0.0192 (3)
H28	0.8597	0.5288	0.8563	0.023*
C29	0.67080 (16)	0.84363 (14)	0.64399 (11)	0.0221 (4)
H29A	0.6628	0.8518	0.5805	0.027*
H29B	0.7272	0.8977	0.6649	0.027*
C30	0.55120 (16)	0.86010 (14)	0.68398 (11)	0.0203 (3)
C31	0.45729 (17)	0.87683 (15)	0.71807 (12)	0.0254 (4)
H22	1.5337 (13)	0.167 (2)	1.1183 (19)	0.073 (10)*
H31	0.3818 (13)	0.8907 (17)	0.7453 (13)	0.036 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0141 (5)	0.0153 (6)	0.0257 (6)	0.0011 (5)	0.0006 (5)	0.0027 (5)
O2	0.0289 (6)	0.0249 (6)	0.0146 (5)	0.0056 (5)	−0.0034 (5)	0.0000 (5)
C1	0.0168 (7)	0.0140 (7)	0.0130 (7)	0.0024 (6)	−0.0032 (6)	0.0020 (6)
C2	0.0182 (7)	0.0176 (8)	0.0164 (8)	−0.0001 (6)	−0.0016 (6)	0.0003 (6)
C3	0.0233 (8)	0.0157 (8)	0.0209 (8)	−0.0031 (7)	−0.0052 (7)	0.0008 (7)
C4	0.0292 (8)	0.0168 (8)	0.0154 (7)	0.0034 (7)	−0.0040 (7)	−0.0016 (6)
C5	0.0212 (8)	0.0205 (8)	0.0147 (7)	0.0045 (7)	−0.0007 (6)	0.0001 (7)
C6	0.0161 (7)	0.0167 (8)	0.0140 (7)	0.0031 (6)	−0.0021 (6)	0.0020 (6)
C7	0.0165 (7)	0.0184 (8)	0.0159 (7)	0.0021 (6)	−0.0024 (6)	0.0027 (6)
C8	0.0160 (7)	0.0267 (9)	0.0192 (8)	0.0023 (7)	−0.0003 (6)	0.0019 (7)
C9	0.0140 (7)	0.0283 (9)	0.0256 (9)	−0.0019 (7)	0.0001 (7)	0.0063 (8)
C10	0.0167 (7)	0.0196 (8)	0.0269 (9)	−0.0035 (6)	−0.0053 (7)	0.0031 (7)
C11	0.0171 (7)	0.0181 (8)	0.0215 (8)	0.0007 (6)	−0.0025 (7)	0.0006 (7)
C12	0.0145 (7)	0.0161 (8)	0.0164 (7)	0.0017 (6)	−0.0026 (6)	0.0036 (6)
C13	0.0144 (7)	0.0131 (7)	0.0153 (7)	0.0007 (6)	−0.0004 (6)	0.0003 (6)
C14	0.0146 (7)	0.0151 (8)	0.0138 (7)	0.0007 (6)	−0.0012 (6)	−0.0017 (6)
C15	0.0154 (7)	0.0188 (8)	0.0158 (8)	−0.0021 (6)	0.0008 (6)	0.0007 (6)
C16	0.0186 (7)	0.0163 (8)	0.0159 (8)	−0.0001 (6)	−0.0007 (6)	0.0031 (6)
C17	0.0149 (7)	0.0142 (8)	0.0162 (7)	0.0000 (6)	−0.0018 (6)	−0.0032 (6)
C18	0.0154 (7)	0.0160 (8)	0.0166 (8)	−0.0025 (6)	0.0014 (6)	−0.0009 (6)
C19	0.0192 (7)	0.0126 (7)	0.0160 (8)	−0.0018 (6)	0.0005 (6)	0.0012 (6)
C20	0.0219 (8)	0.0149 (8)	0.0263 (9)	−0.0003 (7)	−0.0036 (7)	0.0033 (7)
C21	0.0292 (9)	0.0181 (8)	0.0195 (8)	0.0046 (7)	0.0028 (7)	0.0010 (7)
C22	0.0337 (10)	0.0411 (12)	0.0279 (10)	0.0200 (10)	0.0063 (9)	0.0081 (9)
C23	0.0137 (7)	0.0172 (8)	0.0151 (7)	−0.0003 (6)	−0.0010 (6)	−0.0002 (6)
C24	0.0173 (7)	0.0151 (8)	0.0165 (7)	0.0005 (6)	−0.0011 (6)	−0.0031 (6)
C25	0.0203 (8)	0.0151 (8)	0.0205 (8)	0.0011 (7)	−0.0041 (7)	0.0005 (7)
C26	0.0172 (7)	0.0227 (8)	0.0149 (7)	−0.0005 (6)	−0.0009 (6)	−0.0002 (7)
C27	0.0224 (8)	0.0235 (9)	0.0169 (8)	0.0036 (7)	−0.0017 (6)	−0.0040 (7)
C28	0.0208 (8)	0.0161 (8)	0.0206 (8)	0.0037 (6)	−0.0023 (7)	−0.0021 (7)
C29	0.0247 (8)	0.0233 (9)	0.0184 (8)	0.0012 (7)	−0.0012 (7)	0.0044 (7)
C30	0.0265 (8)	0.0175 (8)	0.0170 (8)	−0.0020 (7)	−0.0052 (7)	0.0025 (7)
C31	0.0265 (9)	0.0253 (10)	0.0243 (9)	−0.0038 (8)	0.0013 (7)	−0.0011 (8)

O1—C17	1.3824 (18)	C14—C19	1.399 (2)
O1—C20	1.432 (2)	C15—C16	1.391 (2)
O2—C26	1.387 (2)	C15—H15	0.9500
O2—C29	1.429 (2)	C16—C17	1.389 (2)
C1—C2	1.387 (2)	C16—H16	0.9500
C1—C6	1.405 (2)	C17—C18	1.391 (2)
C1—C13	1.534 (2)	C18—C19	1.386 (2)
C2—C3	1.395 (2)	C18—H18	0.9500
C2—H2	0.9500	C19—H19	0.9500
C3—C4	1.397 (2)	C20—C21	1.462 (2)
C3—H3	0.9500	C20—H20A	0.9900
C4—C5	1.389 (2)	C20—H20B	0.9900
C4—H4	0.9500	C21—C22	1.179 (3)
C5—C6	1.396 (2)	C22—H22	0.949 (10)
C5—H5	0.9500	C23—C24	1.389 (2)
C6—C7	1.465 (2)	C23—C28	1.399 (2)
C7—C8	1.394 (2)	C24—C25	1.391 (2)
C7—C12	1.403 (2)	C24—H24	0.9500
C8—C9	1.393 (3)	C25—C26	1.386 (2)
C8—H8	0.9500	C25—H25	0.9500
C9—C10	1.392 (3)	C26—C27	1.384 (2)
C9—H9	0.9500	C27—C28	1.389 (2)
C10—C11	1.392 (2)	C27—H27	0.9500
C10—H10	0.9500	C28—H28	0.9500
C11—C12	1.382 (2)	C29—C30	1.469 (2)
C11—H11	0.9500	C29—H29A	0.9900
C12—C13	1.530 (2)	C29—H29B	0.9900
C13—C14	1.532 (2)	C30—C31	1.180 (3)
C13—C23	1.540 (2)	C31—H31	0.949 (10)
C14—C15	1.390 (2)
C17—O1—C20	116.28 (12)	C14—C15—H15	119.2
C26—O2—C29	117.13 (13)	C16—C15—H15	119.2
C2—C1—C6	120.56 (15)	C17—C16—C15	119.34 (15)
C2—C1—C13	128.68 (14)	C17—C16—H16	120.3
C6—C1—C13	110.75 (13)	C15—C16—H16	120.3
C1—C2—C3	118.85 (15)	O1—C17—C16	124.00 (14)
C1—C2—H2	120.6	O1—C17—C18	115.70 (14)
C3—C2—H2	120.6	C16—C17—C18	120.29 (15)
C2—C3—C4	120.58 (16)	C19—C18—C17	119.46 (15)
C2—C3—H3	119.7	C19—C18—H18	120.3
C4—C3—H3	119.7	C17—C18—H18	120.3
C5—C4—C3	120.86 (15)	C18—C19—C14	121.46 (15)
C5—C4—H4	119.6	C18—C19—H19	119.3
C3—C4—H4	119.6	C14—C19—H19	119.3
C4—C5—C6	118.61 (15)	O1—C20—C21	107.81 (14)
C4—C5—H5	120.7	O1—C20—H20A	110.1
C6—C5—H5	120.7	C21—C20—H20A	110.1
C5—C6—C1	120.52 (15)	O1—C20—H20B	110.1
C5—C6—C7	130.92 (15)	C21—C20—H20B	110.1
C1—C6—C7	108.56 (14)	H20A—C20—H20B	108.5
C8—C7—C12	120.73 (16)	C22—C21—C20	179.0 (2)
C8—C7—C6	130.43 (16)	C21—C22—H22	177 (2)
C12—C7—C6	108.84 (14)	C24—C23—C28	117.77 (15)
C9—C8—C7	118.38 (17)	C24—C23—C13	120.14 (14)
C9—C8—H8	120.8	C28—C23—C13	121.74 (14)
C7—C8—H8	120.8	C23—C24—C25	122.01 (15)
C8—C9—C10	120.73 (16)	C23—C24—H24	119.0
C8—C9—H9	119.6	C25—C24—H24	119.0
C10—C9—H9	119.6	C26—C25—C24	118.99 (15)
C11—C10—C9	120.73 (17)	C26—C25—H25	120.5
C11—C10—H10	119.6	C24—C25—H25	120.5
C9—C10—H10	119.6	C27—C26—O2	115.68 (15)
C12—C11—C10	118.97 (16)	C27—C26—C25	120.28 (15)
C12—C11—H11	120.5	O2—C26—C25	124.04 (15)
C10—C11—H11	120.5	C26—C27—C28	120.06 (16)
C11—C12—C7	120.44 (15)	C26—C27—H27	120.0
C11—C12—C13	128.72 (15)	C28—C27—H27	120.0
C7—C12—C13	110.80 (14)	C27—C28—C23	120.85 (16)
C12—C13—C14	113.50 (13)	C27—C28—H28	119.6
C12—C13—C1	101.01 (12)	C23—C28—H28	119.6
C14—C13—C1	109.36 (12)	O2—C29—C30	114.11 (14)
C12—C13—C23	107.59 (12)	O2—C29—H29A	108.7
C14—C13—C23	112.64 (12)	C30—C29—H29A	108.7
C1—C13—C23	112.21 (13)	O2—C29—H29B	108.7
C15—C14—C19	117.84 (14)	C30—C29—H29B	108.7
C15—C14—C13	121.86 (14)	H29A—C29—H29B	107.6
C19—C14—C13	120.16 (14)	C31—C30—C29	177.1 (2)
C14—C15—C16	121.61 (15)	C30—C31—H31	179.6 (16)
C6—C1—C2—C3	−0.3 (2)	C12—C13—C14—C15	−17.1 (2)
C13—C1—C2—C3	−179.70 (15)	C1—C13—C14—C15	94.84 (17)
C1—C2—C3—C4	−0.9 (2)	C23—C13—C14—C15	−139.66 (15)
C2—C3—C4—C5	0.8 (3)	C12—C13—C14—C19	167.42 (14)
C3—C4—C5—C6	0.5 (2)	C1—C13—C14—C19	−80.65 (17)
C4—C5—C6—C1	−1.7 (2)	C23—C13—C14—C19	44.9 (2)
C4—C5—C6—C7	177.91 (16)	C19—C14—C15—C16	0.7 (2)
C2—C1—C6—C5	1.6 (2)	C13—C14—C15—C16	−174.94 (15)
C13—C1—C6—C5	−178.88 (14)	C14—C15—C16—C17	0.2 (3)
C2—C1—C6—C7	−178.09 (14)	C20—O1—C17—C16	27.2 (2)
C13—C1—C6—C7	1.44 (17)	C20—O1—C17—C18	−153.71 (14)
C5—C6—C7—C8	0.7 (3)	C15—C16—C17—O1	177.96 (15)
C1—C6—C7—C8	−179.64 (16)	C15—C16—C17—C18	−1.1 (2)
C5—C6—C7—C12	−179.73 (16)	O1—C17—C18—C19	−178.06 (14)
C1—C6—C7—C12	−0.10 (18)	C16—C17—C18—C19	1.0 (2)
C12—C7—C8—C9	0.7 (2)	C17—C18—C19—C14	−0.2 (2)
C6—C7—C8—C9	−179.79 (16)	C15—C14—C19—C18	−0.7 (2)
C7—C8—C9—C10	−0.7 (3)	C13—C14—C19—C18	174.99 (14)
C8—C9—C10—C11	−0.3 (3)	C17—O1—C20—C21	−178.77 (13)
C9—C10—C11—C12	1.4 (3)	C12—C13—C23—C24	86.88 (17)
C10—C11—C12—C7	−1.4 (2)	C14—C13—C23—C24	−147.28 (15)
C10—C11—C12—C13	−178.96 (15)	C1—C13—C23—C24	−23.34 (19)
C8—C7—C12—C11	0.3 (2)	C12—C13—C23—C28	−86.21 (17)
C6—C7—C12—C11	−179.24 (14)	C14—C13—C23—C28	39.6 (2)
C8—C7—C12—C13	178.31 (14)	C1—C13—C23—C28	163.57 (15)
C6—C7—C12—C13	−1.28 (18)	C28—C23—C24—C25	1.5 (2)
C11—C12—C13—C14	−63.3 (2)	C13—C23—C24—C25	−171.88 (15)
C7—C12—C13—C14	118.92 (15)	C23—C24—C25—C26	−0.3 (2)
C11—C12—C13—C1	179.74 (16)	C29—O2—C26—C27	178.32 (14)
C7—C12—C13—C1	1.99 (16)	C29—O2—C26—C25	−2.0 (2)
C11—C12—C13—C23	62.0 (2)	C24—C25—C26—C27	−1.6 (2)
C7—C12—C13—C23	−115.75 (15)	C24—C25—C26—O2	178.69 (15)
C2—C1—C13—C12	177.43 (15)	O2—C26—C27—C28	−178.08 (15)
C6—C1—C13—C12	−2.06 (16)	C25—C26—C27—C28	2.2 (3)
C2—C1—C13—C14	57.5 (2)	C26—C27—C28—C23	−0.9 (3)
C6—C1—C13—C14	−121.99 (14)	C24—C23—C28—C27	−0.9 (2)
C2—C1—C13—C23	−68.3 (2)	C13—C23—C28—C27	172.36 (15)
C6—C1—C13—C23	112.26 (14)	C26—O2—C29—C30	−64.78 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29A···O1i	0.99	2.46	3.358 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29A⋯O1i	0.99	2.46	3.358 (2)	151

Symmetry code: (i) .