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In the title compound [systematic name: diethyl 3,3′-(9H-fluorene-9,9-di­yl)dipropionate], C23H26O4, the fluorene ring system is planar. The ethoxy­carbonyl­ethyl groups display extended conformations and are nearly perpendicular to the fluorene plane. A weak inter­molecular C—H...O inter­action occurs in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005733/xu2002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005733/xu2002Isup2.hkl
Contains datablock I

CCDC reference: 601270

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.060
  • wR factor = 0.172
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.70 Ratio 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 C21 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C22 - C23 ... 1.43 Ang.
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 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.

diethyl 3,3'-(9H-fluorene-9,9-diyl)dipropionate top
Crystal data top
C23H26O4Dx = 1.191 Mg m3
Mr = 366.44Melting point: 377 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 6837 reflections
a = 10.8464 (7) Åθ = 2.4–20.7°
b = 16.9377 (11) ŵ = 0.08 mm1
c = 22.2437 (14) ÅT = 292 K
V = 4086.5 (5) Å3Block, colorless
Z = 80.30 × 0.20 × 0.10 mm
F(000) = 1568
Data collection top
Bruker SMART CCD area-detector
diffractometer
2931 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.072
Graphite monochromatorθmax = 26.0°, θmin = 1.8°
φ and ω scansh = 1313
40279 measured reflectionsk = 2020
4005 independent reflectionsl = 2727
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0954P)2 + 0.5495P]
where P = (Fo2 + 2Fc2)/3
4005 reflections(Δ/σ)max < 0.001
246 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.21 e Å3
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
xyzUiso*/Ueq
C10.62224 (17)0.14453 (11)0.37348 (8)0.0435 (4)
C20.5983 (2)0.07400 (12)0.34449 (9)0.0562 (5)
H20.53600.04070.35800.067*
C30.6689 (3)0.05402 (14)0.29488 (11)0.0706 (7)
H30.65330.00690.27490.085*
C40.7612 (2)0.10230 (16)0.27476 (10)0.0737 (7)
H40.80770.08740.24150.088*
C50.7856 (2)0.17245 (15)0.30314 (10)0.0640 (6)
H50.84830.20520.28930.077*
C60.71564 (17)0.19399 (11)0.35273 (9)0.0472 (5)
C70.71827 (17)0.26470 (11)0.39067 (9)0.0477 (5)
C80.7916 (2)0.33230 (13)0.38851 (12)0.0662 (6)
H80.85240.33770.35930.079*
C90.7723 (3)0.39087 (14)0.43034 (13)0.0749 (7)
H90.82140.43590.42960.090*
C100.6823 (3)0.38404 (14)0.47282 (12)0.0723 (7)
H100.67000.42480.50020.087*
C110.6090 (2)0.31715 (12)0.47568 (10)0.0584 (6)
H110.54850.31240.50510.070*
C120.62707 (17)0.25799 (11)0.43443 (8)0.0438 (4)
C130.55825 (16)0.17990 (10)0.42791 (8)0.0425 (4)
C140.57278 (18)0.12776 (12)0.48435 (8)0.0483 (5)
H14A0.53040.15300.51760.058*
H14B0.53260.07750.47700.058*
C150.70480 (18)0.11241 (12)0.50266 (9)0.0511 (5)
H15A0.74700.08620.46980.061*
H15B0.74560.16260.50950.061*
C160.7165 (2)0.06299 (11)0.55797 (9)0.0508 (5)
C170.8568 (3)0.00183 (16)0.62486 (11)0.0798 (8)
H17A0.80450.04460.62410.096*
H17B0.83870.03150.66110.096*
C180.9859 (3)0.0216 (2)0.62445 (16)0.1150 (12)
H18A1.00360.04980.58800.172*
H18B1.00230.05510.65840.172*
H18C1.03710.02450.62670.172*
C190.41959 (17)0.19254 (12)0.41660 (9)0.0502 (5)
H19A0.38140.14160.40940.060*
H19B0.38280.21470.45260.060*
C200.39113 (18)0.24625 (13)0.36412 (9)0.0551 (5)
H20A0.42370.29840.37250.066*
H20B0.43250.22630.32860.066*
C210.2565 (2)0.25268 (15)0.35156 (10)0.0607 (6)
C220.1039 (2)0.31390 (19)0.29289 (16)0.0952 (9)
H22A0.07860.26690.27120.114*
H22B0.05280.31880.32850.114*
C230.0882 (3)0.3820 (2)0.25546 (16)0.1120 (11)
H23A0.11250.42840.27720.168*
H23B0.00320.38650.24390.168*
H23C0.13830.37670.22010.168*
O10.63198 (16)0.03670 (11)0.58596 (8)0.0864 (6)
O20.83327 (14)0.05025 (8)0.57230 (6)0.0616 (4)
O30.17811 (17)0.21310 (15)0.37423 (10)0.1171 (9)
O40.23281 (13)0.30693 (9)0.31032 (8)0.0700 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0429 (10)0.0463 (10)0.0412 (9)0.0010 (8)0.0044 (8)0.0051 (8)
C20.0607 (13)0.0541 (12)0.0539 (12)0.0044 (10)0.0019 (10)0.0025 (10)
C30.0884 (18)0.0662 (14)0.0572 (13)0.0041 (13)0.0023 (12)0.0136 (11)
C40.0775 (17)0.0890 (17)0.0545 (13)0.0124 (14)0.0157 (12)0.0018 (13)
C50.0549 (13)0.0800 (16)0.0571 (13)0.0003 (11)0.0123 (10)0.0075 (12)
C60.0409 (10)0.0547 (11)0.0460 (10)0.0023 (8)0.0012 (8)0.0083 (9)
C70.0402 (10)0.0502 (11)0.0527 (11)0.0043 (8)0.0067 (8)0.0109 (9)
C80.0535 (13)0.0655 (14)0.0796 (16)0.0161 (11)0.0019 (11)0.0162 (13)
C90.0794 (18)0.0519 (13)0.0935 (19)0.0201 (12)0.0233 (15)0.0047 (13)
C100.0886 (18)0.0522 (13)0.0762 (17)0.0052 (12)0.0182 (14)0.0078 (11)
C110.0660 (14)0.0535 (12)0.0557 (12)0.0021 (10)0.0063 (10)0.0030 (10)
C120.0422 (10)0.0436 (10)0.0456 (10)0.0006 (8)0.0094 (8)0.0062 (8)
C130.0400 (10)0.0451 (10)0.0424 (10)0.0037 (8)0.0003 (8)0.0022 (8)
C140.0489 (11)0.0497 (11)0.0462 (11)0.0060 (9)0.0031 (8)0.0076 (8)
C150.0527 (12)0.0507 (11)0.0498 (11)0.0053 (9)0.0017 (9)0.0085 (9)
C160.0591 (13)0.0454 (11)0.0478 (11)0.0066 (9)0.0023 (10)0.0022 (9)
C170.0899 (19)0.0822 (17)0.0674 (15)0.0018 (14)0.0194 (13)0.0257 (13)
C180.096 (2)0.131 (3)0.117 (3)0.016 (2)0.0339 (19)0.040 (2)
C190.0418 (10)0.0578 (12)0.0510 (11)0.0041 (9)0.0022 (8)0.0043 (9)
C200.0413 (11)0.0659 (13)0.0581 (12)0.0002 (9)0.0022 (9)0.0058 (10)
C210.0468 (12)0.0781 (14)0.0572 (12)0.0001 (11)0.0016 (10)0.0072 (11)
C220.0511 (15)0.121 (2)0.114 (2)0.0174 (15)0.0145 (15)0.015 (2)
C230.091 (2)0.128 (3)0.117 (3)0.0334 (19)0.0239 (18)0.024 (2)
O10.0701 (11)0.1107 (14)0.0783 (11)0.0179 (10)0.0016 (9)0.0473 (11)
O20.0620 (10)0.0649 (9)0.0579 (9)0.0012 (7)0.0109 (7)0.0158 (7)
O30.0502 (11)0.177 (2)0.1241 (18)0.0198 (12)0.0061 (10)0.0681 (17)
O40.0461 (9)0.0821 (11)0.0819 (11)0.0084 (7)0.0105 (7)0.0124 (9)
Geometric parameters (Å, º) top
C1—C21.382 (3)C15—C161.493 (3)
C1—C61.393 (3)C15—H15A0.9700
C1—C131.519 (3)C15—H15B0.9700
C2—C31.386 (3)C16—O11.194 (2)
C2—H20.9300C16—O21.324 (2)
C3—C41.367 (3)C17—O21.451 (2)
C3—H30.9300C17—C181.456 (4)
C4—C51.371 (3)C17—H17A0.9700
C4—H40.9300C17—H17B0.9700
C5—C61.388 (3)C18—H18A0.9600
C5—H50.9300C18—H18B0.9600
C6—C71.465 (3)C18—H18C0.9600
C7—C121.392 (3)C19—C201.512 (3)
C7—C81.395 (3)C19—H19A0.9700
C8—C91.376 (3)C19—H19B0.9700
C8—H80.9300C20—C211.491 (3)
C9—C101.363 (4)C20—H20A0.9700
C9—H90.9300C20—H20B0.9700
C10—C111.386 (3)C21—O31.194 (3)
C10—H100.9300C21—O41.324 (3)
C11—C121.373 (3)C22—C231.433 (4)
C11—H110.9300C22—O41.456 (3)
C12—C131.526 (3)C22—H22A0.9700
C13—C191.540 (3)C22—H22B0.9700
C13—C141.543 (2)C23—H23A0.9600
C14—C151.511 (3)C23—H23B0.9600
C14—H14A0.9700C23—H23C0.9600
C14—H14B0.9700
C2—C1—C6120.12 (18)C16—C15—H15A108.9
C2—C1—C13128.82 (17)C14—C15—H15A108.9
C6—C1—C13111.05 (16)C16—C15—H15B108.9
C1—C2—C3118.6 (2)C14—C15—H15B108.9
C1—C2—H2120.7H15A—C15—H15B107.7
C3—C2—H2120.7O1—C16—O2123.22 (19)
C4—C3—C2121.3 (2)O1—C16—C15125.0 (2)
C4—C3—H3119.4O2—C16—C15111.78 (17)
C2—C3—H3119.4O2—C17—C18108.6 (2)
C3—C4—C5120.6 (2)O2—C17—H17A110.0
C3—C4—H4119.7C18—C17—H17A110.0
C5—C4—H4119.7O2—C17—H17B110.0
C4—C5—C6119.2 (2)C18—C17—H17B110.0
C4—C5—H5120.4H17A—C17—H17B108.4
C6—C5—H5120.4C17—C18—H18A109.5
C5—C6—C1120.2 (2)C17—C18—H18B109.5
C5—C6—C7131.45 (19)H18A—C18—H18B109.5
C1—C6—C7108.35 (16)C17—C18—H18C109.5
C12—C7—C8119.7 (2)H18A—C18—H18C109.5
C12—C7—C6108.78 (16)H18B—C18—H18C109.5
C8—C7—C6131.5 (2)C20—C19—C13114.16 (15)
C9—C8—C7118.8 (2)C20—C19—H19A108.7
C9—C8—H8120.6C13—C19—H19A108.7
C7—C8—H8120.6C20—C19—H19B108.7
C10—C9—C8121.1 (2)C13—C19—H19B108.7
C10—C9—H9119.5H19A—C19—H19B107.6
C8—C9—H9119.5C21—C20—C19112.88 (17)
C9—C10—C11120.8 (2)C21—C20—H20A109.0
C9—C10—H10119.6C19—C20—H20A109.0
C11—C10—H10119.6C21—C20—H20B109.0
C12—C11—C10119.0 (2)C19—C20—H20B109.0
C12—C11—H11120.5H20A—C20—H20B107.8
C10—C11—H11120.5O3—C21—O4123.0 (2)
C11—C12—C7120.60 (18)O3—C21—C20125.3 (2)
C11—C12—C13128.80 (18)O4—C21—C20111.76 (19)
C7—C12—C13110.60 (16)C23—C22—O4109.5 (2)
C1—C13—C12101.20 (14)C23—C22—H22A109.8
C1—C13—C19111.78 (15)O4—C22—H22A109.8
C12—C13—C19111.89 (15)C23—C22—H22B109.8
C1—C13—C14112.10 (15)O4—C22—H22B109.8
C12—C13—C14111.64 (15)H22A—C22—H22B108.2
C19—C13—C14108.20 (14)C22—C23—H23A109.5
C15—C14—C13114.49 (15)C22—C23—H23B109.5
C15—C14—H14A108.6H23A—C23—H23B109.5
C13—C14—H14A108.6C22—C23—H23C109.5
C15—C14—H14B108.6H23A—C23—H23C109.5
C13—C14—H14B108.6H23B—C23—H23C109.5
H14A—C14—H14B107.6C16—O2—C17117.05 (18)
C16—C15—C14113.51 (16)C21—O4—C22115.30 (19)
C6—C1—C2—C30.1 (3)C2—C1—C13—C1959.0 (2)
C13—C1—C2—C3179.53 (19)C6—C1—C13—C19120.45 (17)
C1—C2—C3—C40.4 (3)C2—C1—C13—C1462.6 (2)
C2—C3—C4—C50.5 (4)C6—C1—C13—C14117.87 (17)
C3—C4—C5—C60.1 (4)C11—C12—C13—C1178.81 (18)
C4—C5—C6—C10.4 (3)C7—C12—C13—C11.07 (18)
C4—C5—C6—C7178.4 (2)C11—C12—C13—C1959.7 (2)
C2—C1—C6—C50.5 (3)C7—C12—C13—C19120.22 (17)
C13—C1—C6—C5179.99 (18)C11—C12—C13—C1461.8 (2)
C2—C1—C6—C7178.58 (16)C7—C12—C13—C14118.35 (17)
C13—C1—C6—C71.0 (2)C1—C13—C14—C1558.4 (2)
C5—C6—C7—C12179.1 (2)C12—C13—C14—C1554.4 (2)
C1—C6—C7—C120.2 (2)C19—C13—C14—C15177.91 (17)
C5—C6—C7—C80.3 (4)C13—C14—C15—C16179.02 (16)
C1—C6—C7—C8178.6 (2)C14—C15—C16—O10.5 (3)
C12—C7—C8—C90.5 (3)C14—C15—C16—O2179.46 (17)
C6—C7—C8—C9179.2 (2)C1—C13—C19—C2059.0 (2)
C7—C8—C9—C100.9 (4)C12—C13—C19—C2053.7 (2)
C8—C9—C10—C111.1 (4)C14—C13—C19—C20177.12 (16)
C9—C10—C11—C120.9 (3)C13—C19—C20—C21175.83 (18)
C10—C11—C12—C70.5 (3)C19—C20—C21—O39.2 (4)
C10—C11—C12—C13179.33 (19)C19—C20—C21—O4172.54 (18)
C8—C7—C12—C110.3 (3)O1—C16—O2—C170.1 (3)
C6—C7—C12—C11179.32 (17)C15—C16—O2—C17179.10 (18)
C8—C7—C12—C13179.56 (17)C18—C17—O2—C16165.8 (2)
C6—C7—C12—C130.6 (2)O3—C21—O4—C221.7 (4)
C2—C1—C13—C12178.27 (18)C20—C21—O4—C22176.7 (2)
C6—C1—C13—C121.22 (19)C23—C22—O4—C21171.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.573.485 (3)169
Symmetry code: (i) x+1, y, z+1.
 

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