Diphenyl naphthalene-1,4-dicarboxyl­ate

In the title compound, C₂₄H₁₆O₄, 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.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.30 × 0.30 × 0.23 mm
Z = 4

Data collection

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

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	All H-atom parameters refined
S = 0.89	w = 1/[σ^2(Fo^2) + (0.0493P)^2] where P = (Fo^2 + 2Fc^2)/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

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
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	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···Cg1^ii	0.96 (3)	2.65 (3)	3.469 (4)	143 (2)
C6—H6···Cg2^i	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.