In the title compound, C
24H
16O
4, the two carboxylate groups are twisted away from the attached of the naphthalene unit ring by 20.4 (2) and 45.2 (1)°. The crystal packing is stabilized by C—H
O hydrogen bonds and C—H
π interactions.
Supporting information
CCDC reference: 608393
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.119
- Data-to-parameter ratio = 10.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc.
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.06 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C22 - C23 .. 5.49 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: DIFRAC (Gabe et al., 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Diphenyl naphthalene-1,4-dicarboxylate
top
Crystal data top
C24H16O4 | F(000) = 768 |
Mr = 368.37 | Dx = 1.360 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 20 reflections |
a = 13.984 (7) Å | θ = 4.5–7.4° |
b = 5.7797 (17) Å | µ = 0.09 mm−1 |
c = 22.283 (6) Å | T = 292 K |
β = 92.15 (3)° | Block, brown |
V = 1799.7 (12) Å3 | 0.30 × 0.30 × 0.23 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.017 |
Radiation source: fine-focus sealed tube | θmax = 25.4°, θmin = 1.8° |
Graphite monochromator | h = −16→16 |
ω/2θ scans | k = 0→6 |
3304 measured reflections | l = −10→26 |
3280 independent reflections | 3 standard reflections every 300 reflections |
1324 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | All H-atom parameters refined |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0493P)2] where P = (Fo2 + 2Fc2)/3 |
3280 reflections | (Δ/σ)max = 0.001 |
317 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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 | |
O1 | 0.44327 (17) | 0.2491 (5) | 0.96387 (10) | 0.1053 (10) | |
O2 | 0.35410 (14) | 0.4573 (4) | 0.90104 (8) | 0.0579 (6) | |
O3 | 0.68080 (15) | 0.4848 (4) | 0.67890 (9) | 0.0745 (8) | |
O4 | 0.79804 (14) | 0.4264 (4) | 0.74845 (7) | 0.0544 (6) | |
C1 | 0.6378 (2) | 0.3882 (5) | 0.77799 (11) | 0.0422 (7) | |
C2 | 0.5625 (2) | 0.5360 (5) | 0.78057 (13) | 0.0467 (8) | |
C3 | 0.4957 (2) | 0.5168 (6) | 0.82579 (13) | 0.0464 (8) | |
C4 | 0.50416 (18) | 0.3427 (5) | 0.86774 (11) | 0.0401 (7) | |
C5 | 0.5902 (2) | −0.0093 (5) | 0.90596 (12) | 0.0475 (8) | |
C6 | 0.6627 (2) | −0.1636 (6) | 0.90165 (13) | 0.0517 (8) | |
C7 | 0.7294 (2) | −0.1427 (6) | 0.85685 (13) | 0.0514 (8) | |
C8 | 0.7224 (2) | 0.0342 (6) | 0.81691 (13) | 0.0502 (8) | |
C9 | 0.64910 (19) | 0.2020 (5) | 0.81986 (10) | 0.0408 (7) | |
C10 | 0.57998 (18) | 0.1798 (5) | 0.86555 (11) | 0.0401 (7) | |
C11 | 0.4338 (2) | 0.3373 (6) | 0.91632 (12) | 0.0527 (8) | |
C12 | 0.2832 (2) | 0.4732 (5) | 0.94402 (11) | 0.0455 (8) | |
C13 | 0.2137 (2) | 0.3077 (6) | 0.94522 (13) | 0.0531 (8) | |
C14 | 0.1416 (2) | 0.3315 (7) | 0.98555 (14) | 0.0612 (9) | |
C15 | 0.1408 (2) | 0.5167 (7) | 1.02360 (14) | 0.0594 (9) | |
C16 | 0.2118 (2) | 0.6810 (6) | 1.02148 (14) | 0.0599 (9) | |
C17 | 0.2841 (2) | 0.6609 (6) | 0.98136 (14) | 0.0566 (9) | |
C18 | 0.7046 (2) | 0.4346 (5) | 0.72894 (13) | 0.0483 (8) | |
C19 | 0.8677 (2) | 0.4540 (5) | 0.70524 (12) | 0.0466 (8) | |
C20 | 0.9286 (2) | 0.6362 (6) | 0.71079 (14) | 0.0574 (9) | |
C21 | 1.0022 (2) | 0.6557 (7) | 0.67104 (16) | 0.0681 (10) | |
C22 | 1.0127 (3) | 0.4951 (8) | 0.62721 (15) | 0.0685 (11) | |
C23 | 0.9513 (3) | 0.3119 (7) | 0.62227 (16) | 0.0678 (10) | |
C24 | 0.8779 (2) | 0.2890 (6) | 0.66174 (14) | 0.0594 (9) | |
H2 | 0.5553 (18) | 0.658 (5) | 0.7513 (11) | 0.068 (10)* | |
H3 | 0.4431 (18) | 0.620 (5) | 0.8268 (11) | 0.055 (9)* | |
H5 | 0.5425 (16) | −0.028 (4) | 0.9347 (10) | 0.035 (7)* | |
H6 | 0.6659 (19) | −0.290 (5) | 0.9318 (12) | 0.076 (10)* | |
H7 | 0.7825 (19) | −0.256 (5) | 0.8555 (11) | 0.067 (9)* | |
H8 | 0.7654 (17) | 0.059 (4) | 0.7863 (10) | 0.040 (8)* | |
H13 | 0.2153 (17) | 0.178 (5) | 0.9178 (11) | 0.059 (9)* | |
H14 | 0.0899 (19) | 0.211 (5) | 0.9874 (11) | 0.066 (10)* | |
H15 | 0.094 (2) | 0.526 (5) | 1.0533 (11) | 0.061 (9)* | |
H16 | 0.2121 (18) | 0.806 (5) | 1.0494 (11) | 0.055 (9)* | |
H17 | 0.3377 (18) | 0.771 (5) | 0.9786 (11) | 0.061 (9)* | |
H20 | 0.9200 (16) | 0.745 (4) | 0.7405 (10) | 0.040 (8)* | |
H21 | 1.044 (2) | 0.783 (5) | 0.6757 (12) | 0.063 (10)* | |
H22 | 1.063 (2) | 0.505 (5) | 0.5999 (12) | 0.070 (10)* | |
H23 | 0.957 (2) | 0.201 (6) | 0.5888 (14) | 0.107 (13)* | |
H24 | 0.8308 (19) | 0.161 (5) | 0.6581 (12) | 0.069 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0957 (19) | 0.161 (3) | 0.0621 (14) | 0.0641 (19) | 0.0372 (13) | 0.0526 (17) |
O2 | 0.0541 (14) | 0.0734 (16) | 0.0471 (11) | 0.0161 (13) | 0.0135 (10) | 0.0091 (11) |
O3 | 0.0552 (14) | 0.116 (2) | 0.0533 (13) | 0.0065 (13) | 0.0076 (10) | 0.0304 (14) |
O4 | 0.0423 (12) | 0.0763 (16) | 0.0449 (11) | −0.0073 (12) | 0.0057 (10) | 0.0041 (10) |
C1 | 0.0382 (17) | 0.0492 (19) | 0.0393 (15) | −0.0034 (16) | 0.0025 (13) | 0.0036 (14) |
C2 | 0.0468 (19) | 0.047 (2) | 0.0462 (17) | −0.0018 (17) | 0.0020 (15) | 0.0068 (17) |
C3 | 0.0405 (19) | 0.051 (2) | 0.0481 (17) | 0.0030 (18) | 0.0047 (14) | 0.0015 (16) |
C4 | 0.0402 (17) | 0.0452 (19) | 0.0351 (14) | −0.0023 (16) | 0.0054 (13) | −0.0013 (14) |
C5 | 0.048 (2) | 0.052 (2) | 0.0425 (17) | −0.0015 (18) | 0.0074 (15) | 0.0005 (16) |
C6 | 0.056 (2) | 0.050 (2) | 0.0484 (18) | −0.0012 (19) | −0.0015 (16) | 0.0047 (17) |
C7 | 0.052 (2) | 0.046 (2) | 0.0554 (19) | 0.0024 (18) | −0.0015 (17) | 0.0006 (17) |
C8 | 0.046 (2) | 0.056 (2) | 0.0495 (19) | −0.0008 (18) | 0.0071 (16) | −0.0029 (17) |
C9 | 0.0409 (18) | 0.046 (2) | 0.0357 (15) | −0.0048 (16) | 0.0012 (13) | −0.0017 (14) |
C10 | 0.0374 (17) | 0.0469 (19) | 0.0358 (15) | 0.0014 (16) | −0.0021 (13) | −0.0017 (14) |
C11 | 0.053 (2) | 0.065 (2) | 0.0408 (18) | 0.0059 (19) | 0.0096 (15) | 0.0052 (17) |
C12 | 0.0445 (19) | 0.056 (2) | 0.0368 (16) | 0.0052 (17) | 0.0085 (14) | 0.0030 (15) |
C13 | 0.061 (2) | 0.048 (2) | 0.0507 (19) | −0.0003 (19) | 0.0060 (17) | −0.0098 (17) |
C14 | 0.053 (2) | 0.067 (2) | 0.064 (2) | −0.009 (2) | 0.0112 (18) | −0.001 (2) |
C15 | 0.047 (2) | 0.075 (3) | 0.057 (2) | 0.001 (2) | 0.0173 (17) | −0.001 (2) |
C16 | 0.061 (2) | 0.057 (2) | 0.062 (2) | 0.005 (2) | 0.0109 (18) | −0.0133 (19) |
C17 | 0.057 (2) | 0.054 (2) | 0.060 (2) | −0.009 (2) | 0.0142 (18) | −0.0031 (18) |
C18 | 0.049 (2) | 0.048 (2) | 0.0474 (18) | −0.0008 (17) | 0.0047 (15) | 0.0050 (15) |
C19 | 0.0426 (18) | 0.056 (2) | 0.0410 (16) | −0.0016 (17) | 0.0026 (14) | 0.0044 (16) |
C20 | 0.059 (2) | 0.062 (2) | 0.052 (2) | −0.007 (2) | 0.0050 (17) | −0.0118 (18) |
C21 | 0.055 (2) | 0.079 (3) | 0.071 (2) | −0.022 (2) | 0.0065 (19) | 0.002 (2) |
C22 | 0.049 (2) | 0.105 (3) | 0.053 (2) | 0.007 (2) | 0.0161 (18) | 0.013 (2) |
C23 | 0.064 (2) | 0.075 (3) | 0.066 (2) | 0.003 (2) | 0.0161 (19) | −0.011 (2) |
C24 | 0.058 (2) | 0.060 (2) | 0.061 (2) | −0.010 (2) | 0.0062 (18) | −0.0036 (19) |
Geometric parameters (Å, º) top
O1—C11 | 1.179 (3) | C9—C10 | 1.436 (3) |
O2—C11 | 1.346 (3) | C12—C13 | 1.365 (4) |
O2—C12 | 1.407 (3) | C12—C17 | 1.367 (4) |
O3—C18 | 1.188 (3) | C13—C14 | 1.382 (4) |
O4—C18 | 1.363 (3) | C13—H13 | 0.97 (3) |
O4—C19 | 1.404 (3) | C14—C15 | 1.366 (4) |
C1—C2 | 1.359 (4) | C14—H14 | 1.01 (3) |
C1—C9 | 1.429 (3) | C15—C16 | 1.375 (4) |
C1—C18 | 1.488 (4) | C15—H15 | 0.95 (3) |
C2—C3 | 1.403 (4) | C16—C17 | 1.379 (4) |
C2—H2 | 0.96 (3) | C16—H16 | 0.95 (3) |
C3—C4 | 1.376 (4) | C17—H17 | 0.99 (3) |
C3—H3 | 0.95 (2) | C19—C20 | 1.357 (4) |
C4—C10 | 1.420 (4) | C19—C24 | 1.371 (4) |
C4—C11 | 1.490 (4) | C20—C21 | 1.388 (4) |
C5—C6 | 1.356 (4) | C20—H20 | 0.92 (2) |
C5—C10 | 1.420 (4) | C21—C22 | 1.359 (5) |
C5—H5 | 0.95 (2) | C21—H21 | 0.95 (3) |
C6—C7 | 1.397 (4) | C22—C23 | 1.366 (5) |
C6—H6 | 0.99 (3) | C22—H22 | 0.95 (3) |
C7—C8 | 1.357 (4) | C23—C24 | 1.383 (4) |
C7—H7 | 0.99 (3) | C23—H23 | 0.99 (3) |
C8—C9 | 1.414 (4) | C24—H24 | 0.99 (3) |
C8—H8 | 0.94 (2) | | |
| | | |
C11—O2—C12 | 117.4 (2) | C17—C12—O2 | 118.4 (3) |
C18—O4—C19 | 117.3 (2) | C12—C13—C14 | 118.7 (3) |
C2—C1—C9 | 120.9 (3) | C12—C13—H13 | 119.8 (16) |
C2—C1—C18 | 115.2 (3) | C14—C13—H13 | 121.5 (16) |
C9—C1—C18 | 123.9 (3) | C15—C14—C13 | 120.3 (4) |
C1—C2—C3 | 121.2 (3) | C15—C14—H14 | 119.6 (15) |
C1—C2—H2 | 119.5 (16) | C13—C14—H14 | 120.1 (16) |
C3—C2—H2 | 119.3 (16) | C14—C15—C16 | 119.8 (3) |
C4—C3—C2 | 120.2 (3) | C14—C15—H15 | 120.0 (18) |
C4—C3—H3 | 119.3 (16) | C16—C15—H15 | 120.1 (17) |
C2—C3—H3 | 120.4 (16) | C15—C16—C17 | 120.8 (4) |
C3—C4—C10 | 120.4 (3) | C15—C16—H16 | 119.1 (16) |
C3—C4—C11 | 117.8 (3) | C17—C16—H16 | 120.0 (16) |
C10—C4—C11 | 121.7 (3) | C12—C17—C16 | 118.1 (3) |
C6—C5—C10 | 121.3 (3) | C12—C17—H17 | 117.6 (15) |
C6—C5—H5 | 121.4 (15) | C16—C17—H17 | 124.2 (15) |
C10—C5—H5 | 117.3 (15) | O3—C18—O4 | 122.6 (3) |
C5—C6—C7 | 121.0 (3) | O3—C18—C1 | 124.9 (3) |
C5—C6—H6 | 116.9 (16) | O4—C18—C1 | 112.4 (2) |
C7—C6—H6 | 122.1 (16) | C20—C19—C24 | 121.5 (3) |
C8—C7—C6 | 120.1 (3) | C20—C19—O4 | 118.3 (3) |
C8—C7—H7 | 121.0 (16) | C24—C19—O4 | 119.9 (3) |
C6—C7—H7 | 119.0 (16) | C19—C20—C21 | 118.9 (3) |
C7—C8—C9 | 121.4 (3) | C19—C20—H20 | 119.6 (15) |
C7—C8—H8 | 124.0 (15) | C21—C20—H20 | 121.5 (15) |
C9—C8—H8 | 114.6 (16) | C22—C21—C20 | 120.4 (4) |
C8—C9—C1 | 123.3 (3) | C22—C21—H21 | 121.8 (17) |
C8—C9—C10 | 118.7 (3) | C20—C21—H21 | 117.8 (17) |
C1—C9—C10 | 118.0 (3) | C21—C22—C23 | 120.2 (4) |
C5—C10—C4 | 123.1 (3) | C21—C22—H22 | 121.4 (19) |
C5—C10—C9 | 117.6 (3) | C23—C22—H22 | 118.3 (19) |
C4—C10—C9 | 119.3 (3) | C22—C23—C24 | 120.2 (4) |
O1—C11—O2 | 121.0 (3) | C22—C23—H23 | 120 (2) |
O1—C11—C4 | 127.4 (3) | C24—C23—H23 | 120 (2) |
O2—C11—C4 | 111.6 (3) | C19—C24—C23 | 118.8 (3) |
C13—C12—C17 | 122.3 (3) | C19—C24—H24 | 119.4 (17) |
C13—C12—O2 | 119.2 (3) | C23—C24—H24 | 121.7 (17) |
| | | |
C9—C1—C2—C3 | 2.7 (4) | C3—C4—C11—O2 | 20.5 (4) |
C18—C1—C2—C3 | −177.9 (3) | C10—C4—C11—O2 | −161.9 (2) |
C1—C2—C3—C4 | −1.7 (5) | C11—O2—C12—C13 | −89.5 (3) |
C2—C3—C4—C10 | −0.4 (4) | C11—O2—C12—C17 | 93.5 (3) |
C2—C3—C4—C11 | 177.3 (3) | C17—C12—C13—C14 | 0.1 (5) |
C10—C5—C6—C7 | −0.6 (5) | O2—C12—C13—C14 | −176.7 (3) |
C5—C6—C7—C8 | 0.2 (5) | C12—C13—C14—C15 | −0.4 (5) |
C6—C7—C8—C9 | 0.8 (5) | C13—C14—C15—C16 | 0.4 (5) |
C7—C8—C9—C1 | −178.6 (3) | C14—C15—C16—C17 | −0.1 (5) |
C7—C8—C9—C10 | −1.3 (4) | C13—C12—C17—C16 | 0.2 (5) |
C2—C1—C9—C8 | 175.7 (3) | O2—C12—C17—C16 | 177.0 (3) |
C18—C1—C9—C8 | −3.7 (4) | C15—C16—C17—C12 | −0.2 (5) |
C2—C1—C9—C10 | −1.6 (4) | C19—O4—C18—O3 | −7.1 (4) |
C18—C1—C9—C10 | 179.0 (3) | C19—O4—C18—C1 | 176.3 (2) |
C6—C5—C10—C4 | 178.7 (3) | C2—C1—C18—O3 | −42.4 (4) |
C6—C5—C10—C9 | 0.0 (4) | C9—C1—C18—O3 | 137.0 (3) |
C3—C4—C10—C5 | −177.3 (3) | C2—C1—C18—O4 | 134.1 (3) |
C11—C4—C10—C5 | 5.2 (4) | C9—C1—C18—O4 | −46.5 (4) |
C3—C4—C10—C9 | 1.4 (4) | C18—O4—C19—C20 | 118.7 (3) |
C11—C4—C10—C9 | −176.2 (2) | C18—O4—C19—C24 | −66.5 (4) |
C8—C9—C10—C5 | 0.9 (4) | C24—C19—C20—C21 | 0.5 (5) |
C1—C9—C10—C5 | 178.3 (2) | O4—C19—C20—C21 | 175.2 (3) |
C8—C9—C10—C4 | −177.9 (2) | C19—C20—C21—C22 | 0.3 (5) |
C1—C9—C10—C4 | −0.4 (4) | C20—C21—C22—C23 | −0.6 (6) |
C12—O2—C11—O1 | 0.2 (5) | C21—C22—C23—C24 | 0.2 (6) |
C12—O2—C11—C4 | −177.7 (2) | C20—C19—C24—C23 | −0.9 (5) |
C3—C4—C11—O1 | −157.2 (3) | O4—C19—C24—C23 | −175.5 (3) |
C10—C4—C11—O1 | 20.5 (5) | C22—C23—C24—C19 | 0.6 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.95 (2) | 2.23 (2) | 2.884 (4) | 125 (2) |
C5—H5···O1i | 0.95 (2) | 2.60 (2) | 3.264 (4) | 128 (2) |
C8—H8···O4 | 0.94 (2) | 2.34 (2) | 2.951 (4) | 123 (2) |
C2—H2···Cg1ii | 0.96 (3) | 2.65 (3) | 3.469 (4) | 143 (2) |
C6—H6···Cg2i | 0.99 (3) | 2.76 (3) | 3.596 (4) | 142 (2) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, y+1/2, −z+3/2. |