Crystal structure of dimethyl 1-oxo-2,4-di­phenyl-1,2-dihydronaphthalene-2,3-di­carboxyl­ate

In the title compound, a naphthalene derivative, the cyclo­hexa-1,3-diene ring of the 1,2-di­hydro­naphthalene ring system adopts a half-chair conformation. The mean plane of the 1,2-di­hydro­napthalene ring system make dihedral angles of 86.23 (6) and 64.80 (7)° with two phenyl rings. In the crystal, the mol­ecules are linked by C—H...O, inter­actions and further stabilized by C—H...π and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.108
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT793_ALERT_4_G Model has Chirality at C8          (Centro SPGR)          S Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2018 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   3 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   4 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Dimethyl 1-oxo-2,4-diphenyl-1,2-dihydronaphthalene-2,3-dicarboxylate

Crystal data

C26H20O5	F(000) = 864
Mr = 412.42	Dx = 1.308 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3375 reflections
a = 15.8021 (8) Å	θ = 2.3–27.1°
b = 7.4706 (4) Å	µ = 0.09 mm^−1
c = 17.8599 (9) Å	T = 296 K
β = 96.581 (2)°	Block, colourless
V = 2094.49 (19) Å^3	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer	4614 independent reflections
Radiation source: fine-focus sealed tube	3375 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω & φ scans	θmax = 27.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −20→13
Tmin = 0.969, Tmax = 0.978	k = −9→8
21819 measured reflections	l = −22→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0478P)^2 + 0.4036P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.017
4614 reflections	Δρmax = 0.22 e Å^−3
283 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (8)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.05662 (10)	0.2111 (2)	0.01264 (8)	0.0463 (4)
H1	0.0388	0.1135	0.0391	0.056*
C2	0.00596 (10)	0.2750 (2)	−0.04963 (8)	0.0512 (4)
H2	−0.0464	0.2217	−0.0648	0.061*
C3	0.03304 (10)	0.4172 (2)	−0.08905 (8)	0.0488 (4)
H3	−0.0011	0.4600	−0.1311	0.059*
C4	0.11058 (9)	0.4978 (2)	−0.06695 (7)	0.0433 (3)
H4	0.1284	0.5932	−0.0947	0.052*
C5	0.16244 (8)	0.43761 (18)	−0.00354 (7)	0.0354 (3)
C6	0.13411 (8)	0.29249 (18)	0.03586 (7)	0.0368 (3)
C7	0.18723 (9)	0.22355 (19)	0.10317 (7)	0.0384 (3)
C8	0.24887 (8)	0.35947 (17)	0.14498 (6)	0.0338 (3)
C9	0.28722 (8)	0.48058 (18)	0.08927 (7)	0.0336 (3)
C10	0.24565 (8)	0.52183 (18)	0.02146 (7)	0.0338 (3)
C11	0.19360 (8)	0.46192 (18)	0.19635 (6)	0.0344 (3)
C12	0.18236 (8)	0.64551 (18)	0.19151 (7)	0.0368 (3)
H12	0.2110	0.7110	0.1580	0.044*
C13	0.12938 (9)	0.7325 (2)	0.23568 (8)	0.0447 (3)
H13	0.1228	0.8560	0.2319	0.054*
C14	0.08630 (10)	0.6384 (2)	0.28520 (8)	0.0530 (4)
H14	0.0499	0.6971	0.3145	0.064*
C15	0.09745 (11)	0.4569 (3)	0.29111 (9)	0.0595 (5)
H15	0.0691	0.3926	0.3252	0.071*
C16	0.15022 (10)	0.3687 (2)	0.24720 (8)	0.0505 (4)
H16	0.1568	0.2453	0.2517	0.061*
C17	0.31896 (9)	0.24874 (19)	0.19065 (8)	0.0430 (3)
C18	0.44438 (13)	0.0867 (3)	0.17834 (12)	0.0857 (7)
H18A	0.4743	0.1552	0.2185	0.129*
H18B	0.4820	0.0603	0.1412	0.129*
H18C	0.4246	−0.0231	0.1982	0.129*
C19	0.37168 (9)	0.55771 (19)	0.11799 (7)	0.0387 (3)
C20	0.50781 (11)	0.6419 (3)	0.08805 (11)	0.0783 (6)
H20A	0.5019	0.7671	0.0983	0.117*
H20B	0.5429	0.6268	0.0480	0.117*
H20C	0.5338	0.5825	0.1325	0.117*
C21	0.27693 (8)	0.6601 (2)	−0.02840 (7)	0.0398 (3)
C22	0.28407 (11)	0.8357 (2)	−0.00451 (10)	0.0593 (4)
H22	0.2708	0.8659	0.0433	0.071*
C23	0.31073 (13)	0.9673 (3)	−0.05105 (14)	0.0824 (6)
H23	0.3156	1.0851	−0.0344	0.099*
C24	0.33002 (12)	0.9242 (4)	−0.12164 (13)	0.0846 (7)
H24	0.3474	1.0127	−0.1531	0.102*
C25	0.32355 (11)	0.7507 (4)	−0.14553 (9)	0.0723 (6)
H25	0.3375	0.7214	−0.1932	0.087*
C26	0.29671 (9)	0.6184 (3)	−0.10003 (8)	0.0531 (4)
H26	0.2918	0.5010	−0.1173	0.064*
O1	0.18036 (7)	0.07330 (14)	0.12689 (6)	0.0561 (3)
O2	0.32467 (8)	0.21704 (16)	0.25637 (6)	0.0629 (3)
O3	0.37245 (7)	0.18860 (15)	0.14387 (6)	0.0548 (3)
O4	0.38995 (7)	0.60087 (17)	0.18244 (5)	0.0600 (3)
O5	0.42502 (6)	0.56566 (15)	0.06595 (5)	0.0508 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0517 (8)	0.0388 (8)	0.0475 (8)	−0.0064 (7)	0.0016 (6)	−0.0088 (6)
C2	0.0441 (8)	0.0553 (10)	0.0514 (8)	−0.0034 (7)	−0.0068 (7)	−0.0165 (7)
C3	0.0473 (8)	0.0566 (10)	0.0394 (7)	0.0071 (7)	−0.0084 (6)	−0.0076 (7)
C4	0.0447 (8)	0.0500 (9)	0.0340 (7)	0.0043 (7)	−0.0011 (6)	0.0003 (6)
C5	0.0384 (7)	0.0373 (8)	0.0300 (6)	0.0046 (6)	0.0016 (5)	−0.0049 (5)
C6	0.0422 (7)	0.0334 (7)	0.0338 (6)	0.0010 (6)	0.0006 (5)	−0.0076 (5)
C7	0.0466 (8)	0.0326 (8)	0.0359 (7)	0.0017 (6)	0.0044 (6)	−0.0022 (6)
C8	0.0398 (7)	0.0326 (7)	0.0281 (6)	0.0019 (5)	−0.0006 (5)	0.0004 (5)
C9	0.0361 (6)	0.0361 (7)	0.0288 (6)	0.0026 (5)	0.0041 (5)	−0.0029 (5)
C10	0.0362 (6)	0.0370 (7)	0.0285 (6)	0.0045 (6)	0.0052 (5)	−0.0026 (5)
C11	0.0385 (7)	0.0366 (8)	0.0275 (6)	−0.0022 (6)	0.0013 (5)	−0.0001 (5)
C12	0.0380 (7)	0.0380 (8)	0.0342 (6)	−0.0032 (6)	0.0041 (5)	0.0007 (5)
C13	0.0464 (8)	0.0421 (9)	0.0454 (8)	0.0010 (6)	0.0047 (6)	−0.0078 (6)
C14	0.0490 (9)	0.0658 (12)	0.0463 (8)	−0.0050 (8)	0.0146 (7)	−0.0155 (8)
C15	0.0701 (11)	0.0657 (12)	0.0475 (9)	−0.0119 (9)	0.0272 (8)	0.0014 (8)
C16	0.0668 (10)	0.0416 (9)	0.0452 (8)	−0.0066 (7)	0.0155 (7)	0.0035 (7)
C17	0.0506 (8)	0.0381 (8)	0.0383 (7)	0.0050 (6)	−0.0036 (6)	0.0008 (6)
C18	0.0694 (13)	0.0904 (16)	0.0951 (15)	0.0431 (11)	0.0000 (11)	0.0129 (12)
C19	0.0384 (7)	0.0431 (8)	0.0344 (7)	0.0035 (6)	0.0030 (5)	−0.0026 (6)
C20	0.0424 (9)	0.1093 (17)	0.0855 (13)	−0.0188 (10)	0.0176 (9)	−0.0311 (12)
C21	0.0363 (7)	0.0489 (9)	0.0343 (7)	0.0033 (6)	0.0039 (5)	0.0079 (6)
C22	0.0679 (11)	0.0505 (11)	0.0622 (10)	0.0009 (8)	0.0191 (8)	0.0096 (8)
C23	0.0831 (14)	0.0603 (13)	0.1064 (17)	−0.0032 (10)	0.0224 (12)	0.0306 (12)
C24	0.0596 (12)	0.1074 (19)	0.0883 (15)	−0.0008 (12)	0.0150 (10)	0.0621 (14)
C25	0.0470 (9)	0.128 (2)	0.0429 (9)	0.0034 (11)	0.0090 (7)	0.0312 (11)
C26	0.0438 (8)	0.0809 (12)	0.0347 (7)	0.0026 (8)	0.0045 (6)	0.0059 (7)
O1	0.0767 (8)	0.0338 (6)	0.0554 (6)	−0.0059 (5)	−0.0029 (5)	0.0052 (5)
O2	0.0806 (8)	0.0670 (8)	0.0383 (6)	0.0193 (6)	−0.0058 (5)	0.0116 (5)
O3	0.0531 (6)	0.0581 (7)	0.0521 (6)	0.0213 (5)	0.0011 (5)	−0.0005 (5)
O4	0.0472 (6)	0.0932 (9)	0.0387 (5)	−0.0121 (6)	0.0013 (4)	−0.0186 (6)
O5	0.0362 (5)	0.0741 (8)	0.0430 (5)	−0.0041 (5)	0.0081 (4)	−0.0076 (5)

Geometric parameters (Å, º)

C1—C2	1.379 (2)	C14—H14	0.9300
C1—C6	1.3873 (19)	C15—C16	1.376 (2)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.370 (2)	C16—H16	0.9300
C2—H2	0.9300	C17—O2	1.1905 (16)
C3—C4	1.381 (2)	C17—O3	1.3328 (18)
C3—H3	0.9300	C18—O3	1.4456 (19)
C4—C5	1.3942 (17)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.3940 (19)	C18—H18C	0.9600
C5—C10	1.4796 (18)	C19—O4	1.1985 (15)
C6—C7	1.4777 (18)	C19—O5	1.3256 (17)
C7—O1	1.2090 (17)	C20—O5	1.4399 (19)
C7—C8	1.5397 (18)	C20—H20A	0.9600
C8—C9	1.5212 (18)	C20—H20B	0.9600
C8—C17	1.5392 (17)	C20—H20C	0.9600
C8—C11	1.5408 (18)	C21—C22	1.380 (2)
C9—C10	1.3457 (16)	C21—C26	1.3867 (19)
C9—C19	1.4897 (18)	C22—C23	1.384 (2)
C10—C21	1.4852 (18)	C22—H22	0.9300
C11—C12	1.3844 (19)	C23—C24	1.369 (3)
C11—C16	1.3866 (19)	C23—H23	0.9300
C12—C13	1.3774 (19)	C24—C25	1.365 (3)
C12—H12	0.9300	C24—H24	0.9300
C13—C14	1.371 (2)	C25—C26	1.377 (3)
C13—H13	0.9300	C25—H25	0.9300
C14—C15	1.369 (2)	C26—H26	0.9300
C2—C1—C6	120.04 (15)	C14—C15—C16	120.74 (15)
C2—C1—H1	120.0	C14—C15—H15	119.6
C6—C1—H1	120.0	C16—C15—H15	119.6
C3—C2—C1	119.74 (14)	C15—C16—C11	120.65 (15)
C3—C2—H2	120.1	C15—C16—H16	119.7
C1—C2—H2	120.1	C11—C16—H16	119.7
C2—C3—C4	120.68 (13)	O2—C17—O3	124.69 (13)
C2—C3—H3	119.7	O2—C17—C8	126.72 (14)
C4—C3—H3	119.7	O3—C17—C8	108.57 (11)
C3—C4—C5	120.74 (14)	O3—C18—H18A	109.5
C3—C4—H4	119.6	O3—C18—H18B	109.5
C5—C4—H4	119.6	H18A—C18—H18B	109.5
C6—C5—C4	117.90 (12)	O3—C18—H18C	109.5
C6—C5—C10	120.27 (11)	H18A—C18—H18C	109.5
C4—C5—C10	121.82 (12)	H18B—C18—H18C	109.5
C1—C6—C5	120.89 (12)	O4—C19—O5	123.97 (13)
C1—C6—C7	119.35 (13)	O4—C19—C9	122.85 (13)
C5—C6—C7	119.76 (12)	O5—C19—C9	113.11 (11)
O1—C7—C6	122.90 (12)	O5—C20—H20A	109.5
O1—C7—C8	121.30 (11)	O5—C20—H20B	109.5
C6—C7—C8	115.69 (11)	H20A—C20—H20B	109.5
C9—C8—C17	110.48 (11)	O5—C20—H20C	109.5
C9—C8—C7	110.63 (10)	H20A—C20—H20C	109.5
C17—C8—C7	106.22 (10)	H20B—C20—H20C	109.5
C9—C8—C11	112.92 (10)	C22—C21—C26	118.68 (14)
C17—C8—C11	111.96 (10)	C22—C21—C10	119.79 (12)
C7—C8—C11	104.24 (10)	C26—C21—C10	121.49 (14)
C10—C9—C19	123.16 (12)	C21—C22—C23	120.60 (17)
C10—C9—C8	122.34 (11)	C21—C22—H22	119.7
C19—C9—C8	114.40 (10)	C23—C22—H22	119.7
C9—C10—C5	119.96 (12)	C24—C23—C22	120.1 (2)
C9—C10—C21	122.49 (12)	C24—C23—H23	119.9
C5—C10—C21	117.40 (10)	C22—C23—H23	119.9
C12—C11—C16	117.97 (13)	C25—C24—C23	119.64 (18)
C12—C11—C8	122.16 (11)	C25—C24—H24	120.2
C16—C11—C8	119.81 (12)	C23—C24—H24	120.2
C13—C12—C11	120.92 (13)	C24—C25—C26	120.94 (18)
C13—C12—H12	119.5	C24—C25—H25	119.5
C11—C12—H12	119.5	C26—C25—H25	119.5
C14—C13—C12	120.45 (14)	C25—C26—C21	120.02 (18)
C14—C13—H13	119.8	C25—C26—H26	120.0
C12—C13—H13	119.8	C21—C26—H26	120.0
C15—C14—C13	119.25 (14)	C17—O3—C18	115.77 (13)
C15—C14—H14	120.4	C19—O5—C20	117.16 (12)
C13—C14—H14	120.4
C6—C1—C2—C3	1.0 (2)	C9—C8—C11—C16	176.27 (12)
C1—C2—C3—C4	−0.1 (2)	C17—C8—C11—C16	−58.27 (16)
C2—C3—C4—C5	−0.8 (2)	C7—C8—C11—C16	56.13 (14)
C3—C4—C5—C6	1.0 (2)	C16—C11—C12—C13	−0.28 (18)
C3—C4—C5—C10	−179.82 (13)	C8—C11—C12—C13	176.90 (12)
C2—C1—C6—C5	−0.8 (2)	C11—C12—C13—C14	−0.3 (2)
C2—C1—C6—C7	179.38 (13)	C12—C13—C14—C15	1.0 (2)
C4—C5—C6—C1	−0.2 (2)	C13—C14—C15—C16	−1.0 (2)
C10—C5—C6—C1	−179.37 (12)	C14—C15—C16—C11	0.4 (2)
C4—C5—C6—C7	179.65 (12)	C12—C11—C16—C15	0.2 (2)
C10—C5—C6—C7	0.44 (18)	C8—C11—C16—C15	−177.00 (13)
C1—C6—C7—O1	21.7 (2)	C9—C8—C17—O2	138.57 (16)
C5—C6—C7—O1	−158.09 (14)	C7—C8—C17—O2	−101.40 (17)
C1—C6—C7—C8	−154.54 (12)	C11—C8—C17—O2	11.8 (2)
C5—C6—C7—C8	25.65 (18)	C9—C8—C17—O3	−42.97 (14)
O1—C7—C8—C9	145.22 (13)	C7—C8—C17—O3	77.06 (14)
C6—C7—C8—C9	−38.46 (15)	C11—C8—C17—O3	−169.76 (11)
O1—C7—C8—C17	25.29 (17)	C10—C9—C19—O4	140.82 (15)
C6—C7—C8—C17	−158.39 (11)	C8—C9—C19—O4	−35.58 (19)
O1—C7—C8—C11	−93.12 (15)	C10—C9—C19—O5	−42.04 (18)
C6—C7—C8—C11	83.21 (13)	C8—C9—C19—O5	141.56 (12)
C17—C8—C9—C10	146.53 (12)	C9—C10—C21—C22	−62.17 (19)
C7—C8—C9—C10	29.18 (17)	C5—C10—C21—C22	113.49 (15)
C11—C8—C9—C10	−87.22 (15)	C9—C10—C21—C26	120.02 (15)
C17—C8—C9—C19	−37.04 (15)	C5—C10—C21—C26	−64.33 (17)
C7—C8—C9—C19	−154.38 (11)	C26—C21—C22—C23	−0.2 (2)
C11—C8—C9—C19	89.22 (13)	C10—C21—C22—C23	−178.11 (15)
C19—C9—C10—C5	179.15 (12)	C21—C22—C23—C24	0.3 (3)
C8—C9—C10—C5	−4.73 (19)	C22—C23—C24—C25	−0.6 (3)
C19—C9—C10—C21	−5.3 (2)	C23—C24—C25—C26	0.9 (3)
C8—C9—C10—C21	170.82 (12)	C24—C25—C26—C21	−0.9 (2)
C6—C5—C10—C9	−11.87 (19)	C22—C21—C26—C25	0.6 (2)
C4—C5—C10—C9	168.95 (13)	C10—C21—C26—C25	178.39 (13)
C6—C5—C10—C21	172.36 (12)	O2—C17—O3—C18	−3.7 (2)
C4—C5—C10—C21	−6.82 (18)	C8—C17—O3—C18	177.83 (14)
C9—C8—C11—C12	−0.86 (16)	O4—C19—O5—C20	−4.2 (2)
C17—C8—C11—C12	124.60 (13)	C9—C19—O5—C20	178.73 (14)
C7—C8—C11—C12	−121.00 (12)

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the phenyl C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···O2^i	0.93	2.59	3.449 (3)	155
C20—H20B···O5^ii	0.96	2.59	3.430 (2)	146
C3—H3···Cg3^iii	0.93	2.77	3.6338 (16)	154

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z.