9,9-Bis(ethoxy­carbonyl­ethyl)-9H-fluorene

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.

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

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Computing details

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

Crystal data

C23H26O4	Dx = 1.191 Mg m^−3
Mr = 366.44	Melting point: 377 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6837 reflections
a = 10.8464 (7) Å	θ = 2.4–20.7°
b = 16.9377 (11) Å	µ = 0.08 mm^−1
c = 22.2437 (14) Å	T = 292 K
V = 4086.5 (5) Å^3	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm
F(000) = 1568

Data collection

Bruker SMART CCD area-detector diffractometer	2931 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.072
Graphite monochromator	θmax = 26.0°, θmin = 1.8°
φ and ω scans	h = −13→13
40279 measured reflections	k = −20→20
4005 independent reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0954P)^2 + 0.5495P] where P = (Fo^2 + 2Fc^2)/3
4005 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.62224 (17)	0.14453 (11)	0.37348 (8)	0.0435 (4)
C2	0.5983 (2)	0.07400 (12)	0.34449 (9)	0.0562 (5)
H2	0.5360	0.0407	0.3580	0.067*
C3	0.6689 (3)	0.05402 (14)	0.29488 (11)	0.0706 (7)
H3	0.6533	0.0069	0.2749	0.085*
C4	0.7612 (2)	0.10230 (16)	0.27476 (10)	0.0737 (7)
H4	0.8077	0.0874	0.2415	0.088*
C5	0.7856 (2)	0.17245 (15)	0.30314 (10)	0.0640 (6)
H5	0.8483	0.2052	0.2893	0.077*
C6	0.71564 (17)	0.19399 (11)	0.35273 (9)	0.0472 (5)
C7	0.71827 (17)	0.26470 (11)	0.39067 (9)	0.0477 (5)
C8	0.7916 (2)	0.33230 (13)	0.38851 (12)	0.0662 (6)
H8	0.8524	0.3377	0.3593	0.079*
C9	0.7723 (3)	0.39087 (14)	0.43034 (13)	0.0749 (7)
H9	0.8214	0.4359	0.4296	0.090*
C10	0.6823 (3)	0.38404 (14)	0.47282 (12)	0.0723 (7)
H10	0.6700	0.4248	0.5002	0.087*
C11	0.6090 (2)	0.31715 (12)	0.47568 (10)	0.0584 (6)
H11	0.5485	0.3124	0.5051	0.070*
C12	0.62707 (17)	0.25799 (11)	0.43443 (8)	0.0438 (4)
C13	0.55825 (16)	0.17990 (10)	0.42791 (8)	0.0425 (4)
C14	0.57278 (18)	0.12776 (12)	0.48435 (8)	0.0483 (5)
H14A	0.5304	0.1530	0.5176	0.058*
H14B	0.5326	0.0775	0.4770	0.058*
C15	0.70480 (18)	0.11241 (12)	0.50266 (9)	0.0511 (5)
H15A	0.7470	0.0862	0.4698	0.061*
H15B	0.7456	0.1626	0.5095	0.061*
C16	0.7165 (2)	0.06299 (11)	0.55797 (9)	0.0508 (5)
C17	0.8568 (3)	0.00183 (16)	0.62486 (11)	0.0798 (8)
H17A	0.8045	−0.0446	0.6241	0.096*
H17B	0.8387	0.0315	0.6611	0.096*
C18	0.9859 (3)	−0.0216 (2)	0.62445 (16)	0.1150 (12)
H18A	1.0036	−0.0498	0.5880	0.172*
H18B	1.0023	−0.0551	0.6584	0.172*
H18C	1.0371	0.0245	0.6267	0.172*
C19	0.41959 (17)	0.19254 (12)	0.41660 (9)	0.0502 (5)
H19A	0.3814	0.1416	0.4094	0.060*
H19B	0.3828	0.2147	0.4526	0.060*
C20	0.39113 (18)	0.24625 (13)	0.36412 (9)	0.0551 (5)
H20A	0.4237	0.2984	0.3725	0.066*
H20B	0.4325	0.2263	0.3286	0.066*
C21	0.2565 (2)	0.25268 (15)	0.35156 (10)	0.0607 (6)
C22	0.1039 (2)	0.31390 (19)	0.29289 (16)	0.0952 (9)
H22A	0.0786	0.2669	0.2712	0.114*
H22B	0.0528	0.3188	0.3285	0.114*
C23	0.0882 (3)	0.3820 (2)	0.25546 (16)	0.1120 (11)
H23A	0.1125	0.4284	0.2772	0.168*
H23B	0.0032	0.3865	0.2439	0.168*
H23C	0.1383	0.3767	0.2201	0.168*
O1	0.63198 (16)	0.03670 (11)	0.58596 (8)	0.0864 (6)
O2	0.83327 (14)	0.05025 (8)	0.57230 (6)	0.0616 (4)
O3	0.17811 (17)	0.21310 (15)	0.37423 (10)	0.1171 (9)
O4	0.23281 (13)	0.30693 (9)	0.31032 (8)	0.0700 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0429 (10)	0.0463 (10)	0.0412 (9)	0.0010 (8)	−0.0044 (8)	0.0051 (8)
C2	0.0607 (13)	0.0541 (12)	0.0539 (12)	−0.0044 (10)	−0.0019 (10)	−0.0025 (10)
C3	0.0884 (18)	0.0662 (14)	0.0572 (13)	0.0041 (13)	−0.0023 (12)	−0.0136 (11)
C4	0.0775 (17)	0.0890 (17)	0.0545 (13)	0.0124 (14)	0.0157 (12)	−0.0018 (13)
C5	0.0549 (13)	0.0800 (16)	0.0571 (13)	0.0003 (11)	0.0123 (10)	0.0075 (12)
C6	0.0409 (10)	0.0547 (11)	0.0460 (10)	0.0023 (8)	−0.0012 (8)	0.0083 (9)
C7	0.0402 (10)	0.0502 (11)	0.0527 (11)	−0.0043 (8)	−0.0067 (8)	0.0109 (9)
C8	0.0535 (13)	0.0655 (14)	0.0796 (16)	−0.0161 (11)	−0.0019 (11)	0.0162 (13)
C9	0.0794 (18)	0.0519 (13)	0.0935 (19)	−0.0201 (12)	−0.0233 (15)	0.0047 (13)
C10	0.0886 (18)	0.0522 (13)	0.0762 (17)	−0.0052 (12)	−0.0182 (14)	−0.0078 (11)
C11	0.0660 (14)	0.0535 (12)	0.0557 (12)	−0.0021 (10)	−0.0063 (10)	−0.0030 (10)
C12	0.0422 (10)	0.0436 (10)	0.0456 (10)	0.0006 (8)	−0.0094 (8)	0.0062 (8)
C13	0.0400 (10)	0.0451 (10)	0.0424 (10)	−0.0037 (8)	−0.0003 (8)	0.0022 (8)
C14	0.0489 (11)	0.0497 (11)	0.0462 (11)	−0.0060 (9)	0.0031 (8)	0.0076 (8)
C15	0.0527 (12)	0.0507 (11)	0.0498 (11)	−0.0053 (9)	−0.0017 (9)	0.0085 (9)
C16	0.0591 (13)	0.0454 (11)	0.0478 (11)	−0.0066 (9)	−0.0023 (10)	0.0022 (9)
C17	0.0899 (19)	0.0822 (17)	0.0674 (15)	0.0018 (14)	−0.0194 (13)	0.0257 (13)
C18	0.096 (2)	0.131 (3)	0.117 (3)	0.016 (2)	−0.0339 (19)	0.040 (2)
C19	0.0418 (10)	0.0578 (12)	0.0510 (11)	−0.0041 (9)	0.0022 (8)	0.0043 (9)
C20	0.0413 (11)	0.0659 (13)	0.0581 (12)	−0.0002 (9)	−0.0022 (9)	0.0058 (10)
C21	0.0468 (12)	0.0781 (14)	0.0572 (12)	0.0001 (11)	−0.0016 (10)	0.0072 (11)
C22	0.0511 (15)	0.121 (2)	0.114 (2)	0.0174 (15)	−0.0145 (15)	0.015 (2)
C23	0.091 (2)	0.128 (3)	0.117 (3)	0.0334 (19)	−0.0239 (18)	0.024 (2)
O1	0.0701 (11)	0.1107 (14)	0.0783 (11)	−0.0179 (10)	−0.0016 (9)	0.0473 (11)
O2	0.0620 (10)	0.0649 (9)	0.0579 (9)	−0.0012 (7)	−0.0109 (7)	0.0158 (7)
O3	0.0502 (11)	0.177 (2)	0.1241 (18)	−0.0198 (12)	−0.0061 (10)	0.0681 (17)
O4	0.0461 (9)	0.0821 (11)	0.0819 (11)	0.0084 (7)	−0.0105 (7)	0.0124 (9)

Geometric parameters (Å, º)

C1—C2	1.382 (3)	C15—C16	1.493 (3)
C1—C6	1.393 (3)	C15—H15A	0.9700
C1—C13	1.519 (3)	C15—H15B	0.9700
C2—C3	1.386 (3)	C16—O1	1.194 (2)
C2—H2	0.9300	C16—O2	1.324 (2)
C3—C4	1.367 (3)	C17—O2	1.451 (2)
C3—H3	0.9300	C17—C18	1.456 (4)
C4—C5	1.371 (3)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—C6	1.388 (3)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—C7	1.465 (3)	C18—H18C	0.9600
C7—C12	1.392 (3)	C19—C20	1.512 (3)
C7—C8	1.395 (3)	C19—H19A	0.9700
C8—C9	1.376 (3)	C19—H19B	0.9700
C8—H8	0.9300	C20—C21	1.491 (3)
C9—C10	1.363 (4)	C20—H20A	0.9700
C9—H9	0.9300	C20—H20B	0.9700
C10—C11	1.386 (3)	C21—O3	1.194 (3)
C10—H10	0.9300	C21—O4	1.324 (3)
C11—C12	1.373 (3)	C22—C23	1.433 (4)
C11—H11	0.9300	C22—O4	1.456 (3)
C12—C13	1.526 (3)	C22—H22A	0.9700
C13—C19	1.540 (3)	C22—H22B	0.9700
C13—C14	1.543 (2)	C23—H23A	0.9600
C14—C15	1.511 (3)	C23—H23B	0.9600
C14—H14A	0.9700	C23—H23C	0.9600
C14—H14B	0.9700
C2—C1—C6	120.12 (18)	C16—C15—H15A	108.9
C2—C1—C13	128.82 (17)	C14—C15—H15A	108.9
C6—C1—C13	111.05 (16)	C16—C15—H15B	108.9
C1—C2—C3	118.6 (2)	C14—C15—H15B	108.9
C1—C2—H2	120.7	H15A—C15—H15B	107.7
C3—C2—H2	120.7	O1—C16—O2	123.22 (19)
C4—C3—C2	121.3 (2)	O1—C16—C15	125.0 (2)
C4—C3—H3	119.4	O2—C16—C15	111.78 (17)
C2—C3—H3	119.4	O2—C17—C18	108.6 (2)
C3—C4—C5	120.6 (2)	O2—C17—H17A	110.0
C3—C4—H4	119.7	C18—C17—H17A	110.0
C5—C4—H4	119.7	O2—C17—H17B	110.0
C4—C5—C6	119.2 (2)	C18—C17—H17B	110.0
C4—C5—H5	120.4	H17A—C17—H17B	108.4
C6—C5—H5	120.4	C17—C18—H18A	109.5
C5—C6—C1	120.2 (2)	C17—C18—H18B	109.5
C5—C6—C7	131.45 (19)	H18A—C18—H18B	109.5
C1—C6—C7	108.35 (16)	C17—C18—H18C	109.5
C12—C7—C8	119.7 (2)	H18A—C18—H18C	109.5
C12—C7—C6	108.78 (16)	H18B—C18—H18C	109.5
C8—C7—C6	131.5 (2)	C20—C19—C13	114.16 (15)
C9—C8—C7	118.8 (2)	C20—C19—H19A	108.7
C9—C8—H8	120.6	C13—C19—H19A	108.7
C7—C8—H8	120.6	C20—C19—H19B	108.7
C10—C9—C8	121.1 (2)	C13—C19—H19B	108.7
C10—C9—H9	119.5	H19A—C19—H19B	107.6
C8—C9—H9	119.5	C21—C20—C19	112.88 (17)
C9—C10—C11	120.8 (2)	C21—C20—H20A	109.0
C9—C10—H10	119.6	C19—C20—H20A	109.0
C11—C10—H10	119.6	C21—C20—H20B	109.0
C12—C11—C10	119.0 (2)	C19—C20—H20B	109.0
C12—C11—H11	120.5	H20A—C20—H20B	107.8
C10—C11—H11	120.5	O3—C21—O4	123.0 (2)
C11—C12—C7	120.60 (18)	O3—C21—C20	125.3 (2)
C11—C12—C13	128.80 (18)	O4—C21—C20	111.76 (19)
C7—C12—C13	110.60 (16)	C23—C22—O4	109.5 (2)
C1—C13—C12	101.20 (14)	C23—C22—H22A	109.8
C1—C13—C19	111.78 (15)	O4—C22—H22A	109.8
C12—C13—C19	111.89 (15)	C23—C22—H22B	109.8
C1—C13—C14	112.10 (15)	O4—C22—H22B	109.8
C12—C13—C14	111.64 (15)	H22A—C22—H22B	108.2
C19—C13—C14	108.20 (14)	C22—C23—H23A	109.5
C15—C14—C13	114.49 (15)	C22—C23—H23B	109.5
C15—C14—H14A	108.6	H23A—C23—H23B	109.5
C13—C14—H14A	108.6	C22—C23—H23C	109.5
C15—C14—H14B	108.6	H23A—C23—H23C	109.5
C13—C14—H14B	108.6	H23B—C23—H23C	109.5
H14A—C14—H14B	107.6	C16—O2—C17	117.05 (18)
C16—C15—C14	113.51 (16)	C21—O4—C22	115.30 (19)
C6—C1—C2—C3	0.1 (3)	C2—C1—C13—C19	−59.0 (2)
C13—C1—C2—C3	179.53 (19)	C6—C1—C13—C19	120.45 (17)
C1—C2—C3—C4	0.4 (3)	C2—C1—C13—C14	62.6 (2)
C2—C3—C4—C5	−0.5 (4)	C6—C1—C13—C14	−117.87 (17)
C3—C4—C5—C6	0.1 (4)	C11—C12—C13—C1	178.81 (18)
C4—C5—C6—C1	0.4 (3)	C7—C12—C13—C1	−1.07 (18)
C4—C5—C6—C7	−178.4 (2)	C11—C12—C13—C19	59.7 (2)
C2—C1—C6—C5	−0.5 (3)	C7—C12—C13—C19	−120.22 (17)
C13—C1—C6—C5	−179.99 (18)	C11—C12—C13—C14	−61.8 (2)
C2—C1—C6—C7	178.58 (16)	C7—C12—C13—C14	118.35 (17)
C13—C1—C6—C7	−1.0 (2)	C1—C13—C14—C15	58.4 (2)
C5—C6—C7—C12	179.1 (2)	C12—C13—C14—C15	−54.4 (2)
C1—C6—C7—C12	0.2 (2)	C19—C13—C14—C15	−177.91 (17)
C5—C6—C7—C8	0.3 (4)	C13—C14—C15—C16	179.02 (16)
C1—C6—C7—C8	−178.6 (2)	C14—C15—C16—O1	0.5 (3)
C12—C7—C8—C9	0.5 (3)	C14—C15—C16—O2	179.46 (17)
C6—C7—C8—C9	179.2 (2)	C1—C13—C19—C20	−59.0 (2)
C7—C8—C9—C10	−0.9 (4)	C12—C13—C19—C20	53.7 (2)
C8—C9—C10—C11	1.1 (4)	C14—C13—C19—C20	177.12 (16)
C9—C10—C11—C12	−0.9 (3)	C13—C19—C20—C21	175.83 (18)
C10—C11—C12—C7	0.5 (3)	C19—C20—C21—O3	−9.2 (4)
C10—C11—C12—C13	−179.33 (19)	C19—C20—C21—O4	172.54 (18)
C8—C7—C12—C11	−0.3 (3)	O1—C16—O2—C17	−0.1 (3)
C6—C7—C12—C11	−179.32 (17)	C15—C16—O2—C17	−179.10 (18)
C8—C7—C12—C13	179.56 (17)	C18—C17—O2—C16	165.8 (2)
C6—C7—C12—C13	0.6 (2)	O3—C21—O4—C22	−1.7 (4)
C2—C1—C13—C12	−178.27 (18)	C20—C21—O4—C22	176.7 (2)
C6—C1—C13—C12	1.22 (19)	C23—C22—O4—C21	171.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^i	0.93	2.57	3.485 (3)	169

Symmetry code: (i) −x+1, −y, −z+1.