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In the title compound, C
21H
22O
4, the three fused rings of the fluorene system are almost coplanar. There exists a weak intermolecular C—H
O interaction.
Supporting information
CCDC reference: 287687
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.060
- wR factor = 0.187
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.07 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.57 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C8 .. 6.01 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 5.97 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.02
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 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
8 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
0 ALERT type 4 Improvement, methodology, query or suggestion
A 50 ml three-necked round-bottomed flask was charged with fluorine (4 g) and methyl acrylate (5 ml) and heated to 308 K. Benzyltrimethylammonium methoxide (1 ml) was rapidly added dropwise with stirring, raising the temperature to 353 K. Excess methyl acrylate was evaporated by distillation to a kettle temperature of 343 K at a pressure of 10 m mH g, then cooled to 263 K, and the residue was removed by filteration, air dried and recrystallized from methanol to obtain the compound (I) in 83% yield. Suitable crystals for X-ray analysis were obtained by slow evaporation of methanol solution at room temperature (m.p. 355–356 K). IR (KBr, ν cm−1): 3036 (Ar—H), 2948 (C—H), 1741 (C═O), 1449 (C═C), 1198, 1112 (C—O—C); 1H NMR (CDCl3): δ 7.71–7.31 (m, 8H), 3.46 (s, 6H), 2.43–2.39 (m, 4H), 1.58–1.53 (m, 4H). Elemental analysis calculated for C21H22O4: C 74.54, H 6.55%; found: C 74.66, H 6.41%.
All H atoms were initially located in difference Fourier maps. The methyl H atoms were then constrained to an ideal geometry, with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C—C bond. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å for phenyl H atoms, C—H = 0.97 Å for methylene H atoms and Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.
9,9-bis(methoxycarbonylethyl)fluorene
top
Crystal data top
C21H22O4 | F(000) = 720 |
Mr = 338.39 | Dx = 1.204 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2480 reflections |
a = 12.0711 (18) Å | θ = 2.4–21.9° |
b = 10.0544 (15) Å | µ = 0.08 mm−1 |
c = 15.751 (2) Å | T = 292 K |
β = 102.390 (3)° | Block, colorless |
V = 1867.1 (5) Å3 | 0.30 × 0.24 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2243 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
ϕ and ω scans | h = −13→14 |
9112 measured reflections | k = −11→11 |
3274 independent reflections | l = −13→18 |
Refinement top
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0862P)2 + 0.4752P] where P = (Fo2 + 2Fc2)/3 |
3274 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top
C21H22O4 | V = 1867.1 (5) Å3 |
Mr = 338.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.0711 (18) Å | µ = 0.08 mm−1 |
b = 10.0544 (15) Å | T = 292 K |
c = 15.751 (2) Å | 0.30 × 0.24 × 0.20 mm |
β = 102.390 (3)° | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2243 reflections with I > 2σ(I) |
9112 measured reflections | Rint = 0.025 |
3274 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.31 e Å−3 |
3274 reflections | Δρmin = −0.19 e Å−3 |
228 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.7963 (2) | 0.8785 (2) | 0.07117 (16) | 0.0704 (6) | |
C2 | 0.7584 (3) | 0.8345 (3) | −0.0127 (2) | 0.1052 (10) | |
H2 | 0.6814 | 0.8303 | −0.0379 | 0.126* | |
C3 | 0.8423 (6) | 0.7952 (4) | −0.0596 (3) | 0.1378 (17) | |
H3 | 0.8214 | 0.7632 | −0.1162 | 0.165* | |
C4 | 0.9564 (6) | 0.8063 (4) | −0.0182 (5) | 0.150 (2) | |
H4 | 1.0106 | 0.7810 | −0.0490 | 0.180* | |
C5 | 0.9924 (3) | 0.8506 (3) | 0.0623 (3) | 0.1169 (13) | |
H5 | 1.0694 | 0.8576 | 0.0870 | 0.140* | |
C6 | 0.9121 (2) | 0.8856 (2) | 0.1078 (2) | 0.0783 (8) | |
C7 | 0.92643 (19) | 0.9361 (2) | 0.1967 (2) | 0.0762 (7) | |
C8 | 1.0236 (2) | 0.9615 (4) | 0.2642 (3) | 0.1123 (12) | |
H8 | 1.0966 | 0.9450 | 0.2564 | 0.135* | |
C9 | 1.0047 (4) | 1.0121 (4) | 0.3420 (3) | 0.1276 (14) | |
H9 | 1.0669 | 1.0286 | 0.3869 | 0.153* | |
C10 | 0.9006 (4) | 1.0380 (4) | 0.3551 (2) | 0.1224 (13) | |
H10 | 0.8918 | 1.0736 | 0.4077 | 0.147* | |
C11 | 0.8090 (3) | 1.0123 (3) | 0.29177 (19) | 0.0886 (8) | |
H11 | 0.7369 | 1.0292 | 0.3013 | 0.106* | |
C12 | 0.82057 (19) | 0.9610 (2) | 0.21269 (16) | 0.0646 (6) | |
C13 | 0.72783 (18) | 0.9261 (2) | 0.13542 (16) | 0.0636 (6) | |
C14 | 0.65022 (18) | 0.8163 (2) | 0.15897 (18) | 0.0720 (7) | |
H14A | 0.6160 | 0.8486 | 0.2054 | 0.086* | |
H14B | 0.5895 | 0.7996 | 0.1088 | 0.086* | |
C15 | 0.70962 (19) | 0.6870 (2) | 0.18716 (17) | 0.0686 (6) | |
H15A | 0.7337 | 0.6476 | 0.1379 | 0.082* | |
H15B | 0.7771 | 0.7053 | 0.2315 | 0.082* | |
C16 | 0.6379 (2) | 0.5886 (2) | 0.22227 (17) | 0.0697 (6) | |
C17 | 0.6330 (3) | 0.3709 (3) | 0.2766 (3) | 0.1324 (15) | |
H17A | 0.6093 | 0.4045 | 0.3269 | 0.199* | |
H17B | 0.6830 | 0.2967 | 0.2930 | 0.199* | |
H17C | 0.5678 | 0.3429 | 0.2341 | 0.199* | |
C18 | 0.65472 (19) | 1.0479 (2) | 0.1008 (2) | 0.0792 (7) | |
H18A | 0.5987 | 1.0217 | 0.0497 | 0.095* | |
H18B | 0.6143 | 1.0765 | 0.1446 | 0.095* | |
C19 | 0.7222 (2) | 1.1643 (2) | 0.0773 (2) | 0.0846 (8) | |
H19A | 0.7747 | 1.1944 | 0.1293 | 0.101* | |
H19B | 0.7665 | 1.1341 | 0.0365 | 0.101* | |
C20 | 0.6511 (2) | 1.2780 (2) | 0.03870 (17) | 0.0730 (7) | |
C21 | 0.6501 (3) | 1.4868 (3) | −0.0286 (2) | 0.0964 (9) | |
H21A | 0.6001 | 1.4627 | −0.0824 | 0.145* | |
H21B | 0.7029 | 1.5528 | −0.0394 | 0.145* | |
H21C | 0.6067 | 1.5221 | 0.0106 | 0.145* | |
O1 | 0.54479 (16) | 0.6070 (2) | 0.23306 (16) | 0.1079 (7) | |
O2 | 0.69117 (15) | 0.47347 (17) | 0.24044 (16) | 0.1023 (7) | |
O3 | 0.55127 (16) | 1.2881 (2) | 0.03373 (16) | 0.1089 (8) | |
O4 | 0.71125 (15) | 1.37081 (18) | 0.00951 (14) | 0.0894 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0886 (17) | 0.0488 (12) | 0.0766 (16) | −0.0009 (12) | 0.0242 (13) | 0.0067 (11) |
C2 | 0.161 (3) | 0.0699 (18) | 0.086 (2) | −0.0091 (18) | 0.031 (2) | 0.0071 (16) |
C3 | 0.269 (6) | 0.070 (2) | 0.093 (2) | −0.013 (3) | 0.081 (4) | −0.0017 (18) |
C4 | 0.224 (6) | 0.072 (2) | 0.201 (6) | 0.007 (3) | 0.147 (5) | 0.015 (3) |
C5 | 0.127 (3) | 0.0708 (19) | 0.180 (4) | 0.0110 (18) | 0.094 (3) | 0.015 (2) |
C6 | 0.0701 (16) | 0.0506 (13) | 0.125 (2) | 0.0072 (11) | 0.0457 (15) | 0.0203 (14) |
C7 | 0.0536 (13) | 0.0610 (14) | 0.112 (2) | −0.0069 (11) | 0.0124 (13) | 0.0182 (14) |
C8 | 0.0620 (17) | 0.093 (2) | 0.172 (4) | −0.0194 (15) | 0.004 (2) | 0.030 (2) |
C9 | 0.128 (3) | 0.117 (3) | 0.115 (3) | −0.046 (3) | −0.023 (3) | 0.015 (2) |
C10 | 0.151 (3) | 0.105 (3) | 0.106 (3) | −0.053 (3) | 0.015 (3) | −0.007 (2) |
C11 | 0.104 (2) | 0.0714 (16) | 0.0908 (19) | −0.0210 (15) | 0.0206 (17) | −0.0021 (15) |
C12 | 0.0625 (13) | 0.0508 (12) | 0.0795 (16) | −0.0065 (10) | 0.0131 (11) | 0.0042 (11) |
C13 | 0.0513 (12) | 0.0565 (13) | 0.0824 (15) | 0.0002 (10) | 0.0132 (11) | 0.0050 (11) |
C14 | 0.0538 (12) | 0.0646 (14) | 0.0961 (17) | −0.0057 (11) | 0.0131 (12) | 0.0043 (13) |
C15 | 0.0596 (13) | 0.0618 (14) | 0.0858 (16) | −0.0054 (11) | 0.0186 (12) | 0.0025 (12) |
C16 | 0.0593 (14) | 0.0622 (14) | 0.0914 (17) | −0.0035 (11) | 0.0245 (12) | −0.0010 (12) |
C17 | 0.112 (2) | 0.0732 (18) | 0.234 (4) | −0.0034 (17) | 0.086 (3) | 0.039 (2) |
C18 | 0.0561 (13) | 0.0661 (15) | 0.113 (2) | 0.0038 (11) | 0.0132 (13) | 0.0117 (14) |
C19 | 0.0599 (14) | 0.0678 (15) | 0.125 (2) | 0.0060 (12) | 0.0181 (14) | 0.0218 (15) |
C20 | 0.0631 (15) | 0.0625 (14) | 0.0928 (17) | 0.0030 (12) | 0.0155 (13) | 0.0053 (13) |
C21 | 0.107 (2) | 0.0682 (16) | 0.113 (2) | 0.0065 (16) | 0.0210 (18) | 0.0221 (16) |
O1 | 0.0795 (13) | 0.0884 (13) | 0.172 (2) | 0.0072 (10) | 0.0623 (13) | 0.0246 (13) |
O2 | 0.0792 (12) | 0.0611 (11) | 0.181 (2) | 0.0003 (9) | 0.0607 (13) | 0.0227 (12) |
O3 | 0.0660 (12) | 0.0859 (13) | 0.173 (2) | 0.0126 (10) | 0.0210 (12) | 0.0399 (14) |
O4 | 0.0791 (11) | 0.0674 (11) | 0.1247 (15) | 0.0055 (9) | 0.0287 (10) | 0.0229 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.375 (4) | C14—C15 | 1.504 (3) |
C1—C6 | 1.395 (3) | C14—H14A | 0.9700 |
C1—C13 | 1.515 (3) | C14—H14B | 0.9700 |
C2—C3 | 1.432 (6) | C15—C16 | 1.497 (3) |
C2—H2 | 0.9300 | C15—H15A | 0.9700 |
C3—C4 | 1.396 (6) | C15—H15B | 0.9700 |
C3—H3 | 0.9300 | C16—O1 | 1.187 (3) |
C4—C5 | 1.326 (6) | C16—O2 | 1.325 (3) |
C4—H4 | 0.9300 | C17—O2 | 1.432 (3) |
C5—C6 | 1.370 (4) | C17—H17A | 0.9600 |
C5—H5 | 0.9300 | C17—H17B | 0.9600 |
C6—C7 | 1.463 (4) | C17—H17C | 0.9600 |
C7—C12 | 1.378 (3) | C18—C19 | 1.516 (3) |
C7—C8 | 1.428 (4) | C18—H18A | 0.9700 |
C8—C9 | 1.390 (6) | C18—H18B | 0.9700 |
C8—H8 | 0.9300 | C19—C20 | 1.480 (3) |
C9—C10 | 1.342 (6) | C19—H19A | 0.9700 |
C9—H9 | 0.9300 | C19—H19B | 0.9700 |
C10—C11 | 1.346 (5) | C20—O3 | 1.195 (3) |
C10—H10 | 0.9300 | C20—O4 | 1.324 (3) |
C11—C12 | 1.382 (4) | C21—O4 | 1.440 (3) |
C11—H11 | 0.9300 | C21—H21A | 0.9600 |
C12—C13 | 1.508 (3) | C21—H21B | 0.9600 |
C13—C18 | 1.539 (3) | C21—H21C | 0.9600 |
C13—C14 | 1.544 (3) | | |
| | | |
C2—C1—C6 | 120.7 (3) | C15—C14—H14A | 108.7 |
C2—C1—C13 | 128.8 (3) | C13—C14—H14A | 108.7 |
C6—C1—C13 | 110.4 (2) | C15—C14—H14B | 108.7 |
C1—C2—C3 | 117.3 (4) | C13—C14—H14B | 108.7 |
C1—C2—H2 | 121.3 | H14A—C14—H14B | 107.6 |
C3—C2—H2 | 121.3 | C16—C15—C14 | 113.81 (19) |
C4—C3—C2 | 118.2 (4) | C16—C15—H15A | 108.8 |
C4—C3—H3 | 120.9 | C14—C15—H15A | 108.8 |
C2—C3—H3 | 120.9 | C16—C15—H15B | 108.8 |
C5—C4—C3 | 124.2 (4) | C14—C15—H15B | 108.8 |
C5—C4—H4 | 117.9 | H15A—C15—H15B | 107.7 |
C3—C4—H4 | 117.9 | O1—C16—O2 | 122.4 (2) |
C4—C5—C6 | 117.6 (4) | O1—C16—C15 | 126.2 (2) |
C4—C5—H5 | 121.2 | O2—C16—C15 | 111.45 (19) |
C6—C5—H5 | 121.2 | O2—C17—H17A | 109.5 |
C5—C6—C1 | 121.9 (3) | O2—C17—H17B | 109.5 |
C5—C6—C7 | 129.6 (3) | H17A—C17—H17B | 109.5 |
C1—C6—C7 | 108.4 (2) | O2—C17—H17C | 109.5 |
C12—C7—C8 | 118.5 (3) | H17A—C17—H17C | 109.5 |
C12—C7—C6 | 108.3 (2) | H17B—C17—H17C | 109.5 |
C8—C7—C6 | 133.2 (3) | C19—C18—C13 | 113.79 (19) |
C9—C8—C7 | 117.2 (3) | C19—C18—H18A | 108.8 |
C9—C8—H8 | 121.4 | C13—C18—H18A | 108.8 |
C7—C8—H8 | 121.4 | C19—C18—H18B | 108.8 |
C10—C9—C8 | 122.9 (4) | C13—C18—H18B | 108.8 |
C10—C9—H9 | 118.5 | H18A—C18—H18B | 107.7 |
C8—C9—H9 | 118.5 | C20—C19—C18 | 113.7 (2) |
C9—C10—C11 | 119.8 (4) | C20—C19—H19A | 108.8 |
C9—C10—H10 | 120.1 | C18—C19—H19A | 108.8 |
C11—C10—H10 | 120.1 | C20—C19—H19B | 108.8 |
C10—C11—C12 | 120.9 (3) | C18—C19—H19B | 108.8 |
C10—C11—H11 | 119.5 | H19A—C19—H19B | 107.7 |
C12—C11—H11 | 119.5 | O3—C20—O4 | 122.6 (2) |
C7—C12—C11 | 120.7 (3) | O3—C20—C19 | 125.5 (2) |
C7—C12—C13 | 111.5 (2) | O4—C20—C19 | 112.0 (2) |
C11—C12—C13 | 127.8 (2) | O4—C21—H21A | 109.5 |
C12—C13—C1 | 101.29 (18) | O4—C21—H21B | 109.5 |
C12—C13—C18 | 111.74 (19) | H21A—C21—H21B | 109.5 |
C1—C13—C18 | 111.6 (2) | O4—C21—H21C | 109.5 |
C12—C13—C14 | 110.88 (19) | H21A—C21—H21C | 109.5 |
C1—C13—C14 | 112.41 (19) | H21B—C21—H21C | 109.5 |
C18—C13—C14 | 108.82 (17) | C16—O2—C17 | 117.3 (2) |
C15—C14—C13 | 114.40 (18) | C20—O4—C21 | 116.4 (2) |
| | | |
C6—C1—C2—C3 | 0.7 (4) | C11—C12—C13—C1 | 179.0 (2) |
C13—C1—C2—C3 | 179.9 (2) | C7—C12—C13—C18 | −119.7 (2) |
C1—C2—C3—C4 | −1.1 (5) | C11—C12—C13—C18 | 60.1 (3) |
C2—C3—C4—C5 | 0.2 (6) | C7—C12—C13—C14 | 118.7 (2) |
C3—C4—C5—C6 | 1.0 (6) | C11—C12—C13—C14 | −61.5 (3) |
C4—C5—C6—C1 | −1.5 (4) | C2—C1—C13—C12 | −179.1 (2) |
C4—C5—C6—C7 | 179.6 (3) | C6—C1—C13—C12 | 0.2 (2) |
C2—C1—C6—C5 | 0.6 (4) | C2—C1—C13—C18 | −60.1 (3) |
C13—C1—C6—C5 | −178.7 (2) | C6—C1—C13—C18 | 119.2 (2) |
C2—C1—C6—C7 | 179.8 (2) | C2—C1—C13—C14 | 62.5 (3) |
C13—C1—C6—C7 | 0.4 (3) | C6—C1—C13—C14 | −118.2 (2) |
C5—C6—C7—C12 | 178.2 (3) | C12—C13—C14—C15 | −61.3 (3) |
C1—C6—C7—C12 | −0.9 (3) | C1—C13—C14—C15 | 51.3 (3) |
C5—C6—C7—C8 | −2.0 (5) | C18—C13—C14—C15 | 175.4 (2) |
C1—C6—C7—C8 | 178.9 (3) | C13—C14—C15—C16 | 171.4 (2) |
C12—C7—C8—C9 | −0.9 (4) | C14—C15—C16—O1 | −4.0 (4) |
C6—C7—C8—C9 | 179.3 (3) | C14—C15—C16—O2 | 175.6 (2) |
C7—C8—C9—C10 | −0.5 (6) | C12—C13—C18—C19 | 55.9 (3) |
C8—C9—C10—C11 | 1.4 (6) | C1—C13—C18—C19 | −56.7 (3) |
C9—C10—C11—C12 | −0.9 (5) | C14—C13—C18—C19 | 178.6 (2) |
C8—C7—C12—C11 | 1.4 (4) | C13—C18—C19—C20 | 176.2 (2) |
C6—C7—C12—C11 | −178.7 (2) | C18—C19—C20—O3 | 7.8 (4) |
C8—C7—C12—C13 | −178.8 (2) | C18—C19—C20—O4 | −172.4 (2) |
C6—C7—C12—C13 | 1.0 (3) | O1—C16—O2—C17 | −1.8 (5) |
C10—C11—C12—C7 | −0.6 (4) | C15—C16—O2—C17 | 178.6 (3) |
C10—C11—C12—C13 | 179.7 (3) | O3—C20—O4—C21 | 0.4 (4) |
C7—C12—C13—C1 | −0.7 (2) | C19—C20—O4—C21 | −179.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O2i | 0.93 | 2.57 | 3.462 (3) | 161 |
Symmetry code: (i) −x+2, y+1/2, −z+1/2. |
Experimental details
Crystal data |
Chemical formula | C21H22O4 |
Mr | 338.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 12.0711 (18), 10.0544 (15), 15.751 (2) |
β (°) | 102.390 (3) |
V (Å3) | 1867.1 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.24 × 0.20 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9112, 3274, 2243 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.187, 1.05 |
No. of reflections | 3274 |
No. of parameters | 228 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.19 |
Selected geometric parameters (Å, º) topC1—C6 | 1.395 (3) | C13—C18 | 1.539 (3) |
C1—C13 | 1.515 (3) | C13—C14 | 1.544 (3) |
C6—C7 | 1.463 (4) | C16—O1 | 1.187 (3) |
C7—C12 | 1.378 (3) | C20—O3 | 1.195 (3) |
C12—C13 | 1.508 (3) | | |
| | | |
C6—C1—C13 | 110.4 (2) | C7—C12—C13 | 111.5 (2) |
C1—C6—C7 | 108.4 (2) | C12—C13—C1 | 101.29 (18) |
C12—C7—C6 | 108.3 (2) | C18—C13—C14 | 108.82 (17) |
| | | |
C6—C1—C2—C3 | 0.7 (4) | C7—C12—C13—C1 | −0.7 (2) |
C13—C1—C2—C3 | 179.9 (2) | C11—C12—C13—C18 | 60.1 (3) |
C2—C1—C6—C5 | 0.6 (4) | C2—C1—C13—C14 | 62.5 (3) |
C6—C7—C12—C11 | −178.7 (2) | C1—C13—C14—C15 | 51.3 (3) |
C8—C7—C12—C13 | −178.8 (2) | C12—C13—C18—C19 | 55.9 (3) |
C10—C11—C12—C13 | 179.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O2i | 0.93 | 2.57 | 3.462 (3) | 161 |
Symmetry code: (i) −x+2, y+1/2, −z+1/2. |
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Since the discovery of an electroluminescent (EL) polymer in 1990, EL conjugated polymers and oligomers offer new opportunities for information technology because of potential application in light-emitting diodes (Yang et al., 1996; Komaba et al., 1997). Polyquinolines, polyquinoxalines and polyfluorenes have recently been demonstrated as electron-transport layers light-emitting diodes due to their high thermal and oxidative stability, outstanding mechanical property, and good film-forming ability (Kreyenschmidt et al., 1998). However, polyquinolines, polyquinoxalines and polyfluorenes possess poor solution processability. Fluorene derivatives show interesting and unique chemical and physical properties because they contain a rigid planar biphenyl unit, and the facile substitution at 9-position (atom C13 in Fig. 1) can improve the solubility and processability of polymers without significantly increasing the steric interaction in the polymer backbone (Zhan et al., 2002). As a result, homopolymers and copolymers of fluorene derivatives have emerged as the most attractive blue-emitting materials due to their high effiency and excellent thermal stability (Lee & Tsuysui, 2000; Johansson et al., 2001). The synthesis of monomer (I) was carried out and the structure was determined by X-ray diffraction in order to confirm the molecular structure and to investigate its stereochemistry.
In (I), the three fused rings are essentially coplanar (Fig. 1), the dihedral angles formed by the five-membered ring with both two benzene rings being 0.6 (1)°. The two ester groups are nearly upright with respect to the fused-ring system. Selected bond lengths and angles are listed in Table 1. There is a weak intermolecular C—H···O interaction (Fig. 2 and Table 2).