Crystal structure of 1,2-di­benzoyl­ace­naphthyl­ene

Greenberg, F.H.; Nazarenko, A.Y.

doi:10.1107/S2056989015011160

organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o487-o488

doi:10.1107/S2056989015011160

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Crystal structure of 1,2-dibenzoylacenaphthylene

Fred H. Greenberg ^a and Alexander Y. Nazarenko ^a ^*

^aChemistry Department, SUNY Buffalo State, 1300 Elmwood Ave, Buffalo, NY 14222, USA
^*Correspondence e-mail: nazareay@buffalostate.edu

Edited by M. Zeller, Youngstown State University, USA (Received 8 June 2015; accepted 9 June 2015; online 13 June 2015)

The title molecule, C₂₆H₁₆O₂, crystallizes as a molecular crystal with no strong intermolecular interactions (the shortest C—H⋯O contact is longer than 3.4 Å). Two flat acenaphthylene groups of neigboring 1,2-dibenzoylacenaphthylene molecules are related by a crystallographic center of symmetry and are stacked with the distance between their mean planes of 3.37 (1) Å, apparently making an optimal close packing for these bulky aromatic moieties. Both carbonyl groups are oriented towards the same side of the planar acenaphthylene. The angles between the flat acenaphthylene group and the benzoyl groups are 62.6 (1) and 57.8 (1)°. Because rotation of the benzoyl groups is sterically hindered, we expect that the molecules will remain locked in this `pseudo-cis' orientation in solution. As a result, reduction of 1,2-dibenzoylacenaphthylene at low temperature with sodium dithionite yields the cis-isomer of 1,2-dibenzoyl-1,2-dihydroacenaphthylene, which is sterically favorable. This isomer is thermodynamically less favorable than the trans isomer, but it converts to the more stable isomer only on long-term heating (Greenberg & Schenendorf (1980 ).

Keywords: crystal structure; 1,2-dibenzoylacenaphthylene; crystal packing.

CCDC reference: 1405661

1. Related literature

For synthesis and reactions of the title compound, see: Greenberg & Schenendorf (1980); Dilthey et al. (1938 ). For packing in molecular crystals of polyaromatic compounds, see: Kitaigorodsky (1973 ).

2. Experimental

2.1. Crystal data

C₂₆H₁₆O₂
M_r = 360.39
Triclinic, $[P \overline 1]$
a = 9.4578 (4) Å
b = 10.2665 (5) Å
c = 10.9183 (4) Å
α = 71.448 (2)°
β = 66.494 (2)°
γ = 84.269 (2)°
V = 921.21 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.69 × 0.65 × 0.41 mm

2.2. Data collection

Bruker PHOTON-100 CMOS diffractometer
Absorption correction: numerical (SADABS2014/5; Bruker, 2014 ) T_min = 0.867, T_max = 0.951
32789 measured reflections
4661 independent reflections
3721 reflections with I > 2σ(I)
R_int = 0.044

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.119
S = 1.05
4661 reflections
317 parameters
All H-atom parameters refined
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015b ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015a ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1405661

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015011160/zl2628sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015011160/zl2628Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015011160/zl2628Isup3.cdx

Supporting information file. DOI: 10.1107/S2056989015011160/zl2628Isup4.txt

Supporting information file. DOI: 10.1107/S2056989015011160/zl2628Isup5.cml

checkCIF report

Synthesis and crystallization top

Synthesis of the title compound is described in Greenberg & Schenendorf (1980).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

All hydrogen atoms were located in electron difference density Fourier maps and were refined in an isotropic approximation.

Related literature top

For synthesis and reactions of the title compound, see: Greenberg & Schenendorf (1980); Dilthey et al. (1938). For packing in molecular crystals of polyaromatic compounds, see: Kitaigorodsky (1973).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound. Dispalcement elipsoids are drawn at 50% probability level.
	Fig. 2. Two "stacked" molecules of the title compound (symmetry operator -x, 1 - y, 2 - z). View along the perpendicular to the mean plane of acenaphthylene ring. The center of symmetry is shown in blue.

1,2-Dibezoylacenaphthylene top

Crystal data top

C₂₆H₁₆O₂	Z = 2
M_r = 360.39	F(000) = 376
Triclinic, P1	D_x = 1.299 Mg m⁻³
a = 9.4578 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2665 (5) Å	Cell parameters from 9865 reflections
c = 10.9183 (4) Å	θ = 2.9–30.5°
α = 71.448 (2)°	µ = 0.08 mm⁻¹
β = 66.494 (2)°	T = 173 K
γ = 84.269 (2)°	Block, yellow
V = 921.21 (7) Å³	0.69 × 0.65 × 0.41 mm

Data collection top

Bruker PHOTON-100 CMOS diffractometer	3721 reflections with I > 2σ(I)
Radiation source: sealedtube	R_int = 0.044
ϕ and ω scans	θ_max = 28.5°, θ_min = 2.9°
Absorption correction: numerical (SADABS2014/5; Bruker, 2014)	h = −12→12
T_min = 0.867, T_max = 0.951	k = −13→13
32789 measured reflections	l = −14→14
4661 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	All H-atom parameters refined
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.060P)² + 0.1858P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4661 reflections	Δρ_max = 0.29 e Å⁻³
317 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints

Crystal data top

C₂₆H₁₆O₂	γ = 84.269 (2)°
M_r = 360.39	V = 921.21 (7) Å³
Triclinic, P1	Z = 2
a = 9.4578 (4) Å	Mo Kα radiation
b = 10.2665 (5) Å	µ = 0.08 mm⁻¹
c = 10.9183 (4) Å	T = 173 K
α = 71.448 (2)°	0.69 × 0.65 × 0.41 mm
β = 66.494 (2)°

Data collection top

Bruker PHOTON-100 CMOS diffractometer	4661 independent reflections
Absorption correction: numerical (SADABS2014/5; Bruker, 2014)	3721 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.951	R_int = 0.044
32789 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.119	All H-atom parameters refined
S = 1.05	Δρ_max = 0.29 e Å⁻³
4661 reflections	Δρ_min = −0.23 e Å⁻³
317 parameters

Special details top

Experimental. SADABS-2014/5 (Bruker,2014) was used for absorption correction. wR2(int) was 0.0679 before and 0.0587 after correction. The Ratio of minimum to maximum transmission is 0.9117. The λ/2 correction factor is 0.00150.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O2	0.41366 (12)	0.32535 (12)	1.03180 (10)	0.0490 (3)
O1	0.28034 (14)	0.09696 (10)	0.86494 (10)	0.0479 (3)
C21	0.56736 (13)	0.25985 (12)	0.83077 (12)	0.0275 (2)
C8	0.13285 (13)	0.53667 (12)	0.80666 (11)	0.0269 (2)
C3	0.23865 (13)	0.51645 (12)	0.87207 (12)	0.0272 (2)
C1	0.25412 (13)	0.33485 (12)	0.78461 (11)	0.0277 (2)
C12	0.13773 (13)	0.42876 (12)	0.75109 (11)	0.0273 (2)
C7	0.03120 (13)	0.64398 (12)	0.80421 (12)	0.0300 (3)
C13	0.28234 (14)	0.19576 (12)	0.76620 (12)	0.0302 (3)
C2	0.31430 (13)	0.38697 (12)	0.85609 (12)	0.0284 (2)
C22	0.62779 (14)	0.30751 (13)	0.68478 (12)	0.0305 (3)
C14	0.30979 (14)	0.17945 (12)	0.62795 (12)	0.0291 (2)
C4	0.24678 (14)	0.61137 (13)	0.93445 (13)	0.0320 (3)
C20	0.42982 (14)	0.32278 (13)	0.91594 (12)	0.0309 (3)
C9	−0.07298 (14)	0.64151 (14)	0.74029 (13)	0.0351 (3)
C23	0.75990 (15)	0.25202 (14)	0.60792 (14)	0.0367 (3)
C11	0.03456 (14)	0.42815 (14)	0.69073 (13)	0.0326 (3)
C5	0.14578 (16)	0.72285 (14)	0.93168 (14)	0.0361 (3)
C6	0.04105 (15)	0.73975 (13)	0.87001 (13)	0.0355 (3)
C15	0.36243 (15)	0.28826 (14)	0.50418 (13)	0.0344 (3)
C26	0.64006 (16)	0.15492 (14)	0.89884 (14)	0.0353 (3)
C10	−0.06969 (14)	0.53653 (15)	0.68617 (13)	0.0362 (3)
C24	0.83096 (17)	0.14701 (16)	0.67630 (16)	0.0431 (3)
C16	0.39353 (17)	0.26702 (18)	0.37632 (15)	0.0443 (3)
C19	0.28927 (19)	0.04982 (15)	0.62154 (17)	0.0445 (3)
C25	0.77049 (18)	0.09843 (15)	0.82128 (16)	0.0435 (3)
C17	0.3715 (2)	0.1387 (2)	0.37195 (18)	0.0557 (4)
C18	0.3189 (2)	0.03098 (19)	0.4939 (2)	0.0611 (5)
H22	0.5757 (17)	0.3818 (15)	0.6373 (15)	0.034 (4)*
H26	0.5971 (18)	0.1216 (15)	1.0037 (16)	0.039 (4)*
H4	0.3157 (18)	0.6005 (15)	0.9825 (15)	0.039 (4)*
H9	−0.1493 (18)	0.7137 (16)	0.7372 (16)	0.041 (4)*
H6	−0.0302 (18)	0.8170 (16)	0.8721 (16)	0.042 (4)*
H11	0.0326 (17)	0.3519 (16)	0.6527 (16)	0.040 (4)*
H10	−0.1435 (19)	0.5362 (16)	0.6423 (16)	0.043 (4)*
H5	0.1505 (17)	0.7871 (15)	0.9768 (15)	0.039 (4)*
H23	0.7990 (18)	0.2882 (16)	0.5084 (17)	0.043 (4)*
H15	0.3788 (18)	0.3804 (17)	0.5071 (16)	0.043 (4)*
H25	0.819 (2)	0.0269 (18)	0.8685 (18)	0.055 (5)*
H19	0.255 (2)	−0.0233 (19)	0.7089 (19)	0.057 (5)*
H16	0.431 (2)	0.3421 (19)	0.292 (2)	0.059 (5)*
H24	0.923 (2)	0.1070 (19)	0.6230 (19)	0.060 (5)*
H17	0.389 (2)	0.124 (2)	0.282 (2)	0.071 (6)*
H18	0.308 (2)	−0.061 (2)	0.494 (2)	0.077 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0438 (6)	0.0805 (8)	0.0329 (5)	0.0227 (5)	−0.0224 (4)	−0.0272 (5)
O1	0.0768 (7)	0.0321 (5)	0.0347 (5)	0.0000 (5)	−0.0287 (5)	−0.0006 (4)
C21	0.0289 (6)	0.0295 (6)	0.0266 (5)	0.0019 (4)	−0.0131 (5)	−0.0093 (4)
C8	0.0246 (5)	0.0314 (6)	0.0226 (5)	−0.0002 (4)	−0.0083 (4)	−0.0063 (4)
C3	0.0235 (5)	0.0331 (6)	0.0239 (5)	0.0006 (4)	−0.0086 (4)	−0.0081 (4)
C1	0.0299 (6)	0.0307 (6)	0.0223 (5)	0.0015 (4)	−0.0115 (4)	−0.0061 (4)
C12	0.0272 (5)	0.0307 (6)	0.0224 (5)	−0.0006 (4)	−0.0095 (4)	−0.0059 (4)
C7	0.0266 (5)	0.0329 (6)	0.0245 (5)	0.0019 (5)	−0.0070 (4)	−0.0051 (5)
C13	0.0349 (6)	0.0282 (6)	0.0279 (6)	−0.0007 (5)	−0.0148 (5)	−0.0052 (5)
C2	0.0275 (5)	0.0345 (6)	0.0235 (5)	0.0030 (5)	−0.0108 (4)	−0.0088 (4)
C22	0.0332 (6)	0.0300 (6)	0.0281 (6)	−0.0011 (5)	−0.0131 (5)	−0.0063 (5)
C14	0.0320 (6)	0.0290 (6)	0.0304 (6)	0.0035 (5)	−0.0167 (5)	−0.0095 (5)
C4	0.0304 (6)	0.0386 (7)	0.0284 (6)	−0.0030 (5)	−0.0109 (5)	−0.0116 (5)
C20	0.0306 (6)	0.0384 (6)	0.0261 (6)	0.0046 (5)	−0.0137 (5)	−0.0103 (5)
C9	0.0264 (6)	0.0442 (7)	0.0290 (6)	0.0073 (5)	−0.0106 (5)	−0.0060 (5)
C23	0.0363 (7)	0.0428 (7)	0.0301 (6)	−0.0041 (5)	−0.0082 (5)	−0.0144 (5)
C11	0.0326 (6)	0.0394 (7)	0.0277 (6)	−0.0023 (5)	−0.0140 (5)	−0.0086 (5)
C5	0.0403 (7)	0.0340 (6)	0.0335 (6)	−0.0023 (5)	−0.0093 (5)	−0.0153 (5)
C6	0.0347 (6)	0.0319 (6)	0.0325 (6)	0.0048 (5)	−0.0073 (5)	−0.0090 (5)
C15	0.0361 (6)	0.0360 (7)	0.0304 (6)	0.0022 (5)	−0.0138 (5)	−0.0083 (5)
C26	0.0404 (7)	0.0374 (7)	0.0309 (6)	0.0079 (5)	−0.0186 (5)	−0.0102 (5)
C10	0.0272 (6)	0.0519 (8)	0.0301 (6)	0.0009 (5)	−0.0152 (5)	−0.0078 (5)
C24	0.0375 (7)	0.0510 (8)	0.0490 (8)	0.0117 (6)	−0.0163 (6)	−0.0297 (7)
C16	0.0385 (7)	0.0623 (9)	0.0288 (6)	0.0115 (7)	−0.0134 (6)	−0.0124 (6)
C19	0.0616 (9)	0.0323 (7)	0.0502 (8)	0.0017 (6)	−0.0318 (7)	−0.0136 (6)
C25	0.0490 (8)	0.0418 (7)	0.0489 (8)	0.0193 (6)	−0.0280 (7)	−0.0195 (6)
C17	0.0667 (10)	0.0746 (11)	0.0499 (9)	0.0307 (9)	−0.0372 (8)	−0.0401 (9)
C18	0.0911 (14)	0.0492 (9)	0.0738 (12)	0.0163 (9)	−0.0525 (11)	−0.0368 (9)

Geometric parameters (Å, º) top

O2—C20	1.2209 (14)	C9—C10	1.377 (2)
O1—C13	1.2179 (15)	C9—H9	0.984 (16)
C21—C22	1.3927 (16)	C23—C24	1.384 (2)
C21—C20	1.4912 (17)	C23—H23	0.952 (16)
C21—C26	1.3913 (17)	C11—C10	1.4133 (19)
C8—C3	1.4101 (15)	C11—H11	1.001 (15)
C8—C12	1.4118 (16)	C5—C6	1.3740 (19)
C8—C7	1.3888 (17)	C5—H5	0.954 (15)
C3—C2	1.4722 (16)	C6—H6	0.988 (16)
C3—C4	1.3779 (17)	C15—C16	1.3915 (19)
C1—C12	1.4697 (16)	C15—H15	0.986 (16)
C1—C13	1.4882 (17)	C26—C25	1.3825 (19)
C1—C2	1.3784 (16)	C26—H26	1.000 (15)
C12—C11	1.3795 (16)	C10—H10	0.993 (16)
C7—C9	1.4225 (17)	C24—C25	1.383 (2)
C7—C6	1.4187 (18)	C24—H24	0.97 (2)
C13—C14	1.4877 (16)	C16—C17	1.373 (2)
C2—C20	1.4854 (16)	C16—H16	0.954 (19)
C22—C23	1.3841 (18)	C19—C18	1.381 (2)
C22—H22	0.985 (15)	C19—H19	0.962 (19)
C14—C15	1.3913 (17)	C25—H25	0.945 (18)
C14—C19	1.3912 (18)	C17—C18	1.374 (3)
C4—C5	1.4163 (19)	C17—H17	0.99 (2)
C4—H4	0.966 (15)	C18—H18	0.96 (2)

C22—C21—C20	121.34 (11)	C22—C23—H23	118.1 (10)
C26—C21—C22	119.43 (11)	C24—C23—C22	119.88 (12)
C26—C21—C20	119.18 (11)	C24—C23—H23	122.0 (10)
C3—C8—C12	110.88 (10)	C12—C11—C10	118.34 (12)
C7—C8—C3	124.61 (11)	C12—C11—H11	120.7 (9)
C7—C8—C12	124.42 (11)	C10—C11—H11	121.0 (9)
C8—C3—C2	105.75 (10)	C4—C5—H5	117.5 (9)
C4—C3—C8	118.49 (11)	C6—C5—C4	122.90 (12)
C4—C3—C2	135.74 (11)	C6—C5—H5	119.6 (9)
C12—C1—C13	125.18 (10)	C7—C6—H6	118.6 (9)
C2—C1—C12	108.69 (10)	C5—C6—C7	120.21 (12)
C2—C1—C13	125.37 (11)	C5—C6—H6	121.2 (9)
C8—C12—C1	105.88 (10)	C14—C15—C16	120.18 (13)
C11—C12—C8	118.43 (11)	C14—C15—H15	119.9 (9)
C11—C12—C1	135.51 (11)	C16—C15—H15	120.0 (9)
C8—C7—C9	115.99 (11)	C21—C26—H26	119.2 (9)
C8—C7—C6	115.79 (11)	C25—C26—C21	119.86 (12)
C6—C7—C9	128.18 (11)	C25—C26—H26	120.9 (9)
O1—C13—C1	119.54 (11)	C9—C10—C11	122.70 (11)
O1—C13—C14	121.09 (11)	C9—C10—H10	119.0 (9)
C14—C13—C1	119.36 (10)	C11—C10—H10	118.3 (9)
C3—C2—C20	123.98 (10)	C23—C24—H24	120.3 (11)
C1—C2—C3	108.80 (10)	C25—C24—C23	119.95 (13)
C1—C2—C20	127.13 (11)	C25—C24—H24	119.7 (11)
C21—C22—H22	119.0 (8)	C15—C16—H16	119.4 (11)
C23—C22—C21	120.36 (12)	C17—C16—C15	120.08 (15)
C23—C22—H22	120.6 (8)	C17—C16—H16	120.6 (11)
C15—C14—C13	122.05 (11)	C14—C19—H19	116.6 (11)
C19—C14—C13	118.87 (11)	C18—C19—C14	120.02 (15)
C19—C14—C15	119.01 (12)	C18—C19—H19	123.3 (11)
C3—C4—C5	117.97 (11)	C26—C25—C24	120.50 (13)
C3—C4—H4	121.3 (9)	C26—C25—H25	119.2 (11)
C5—C4—H4	120.6 (9)	C24—C25—H25	120.3 (11)
O2—C20—C21	120.85 (11)	C16—C17—C18	120.00 (14)
O2—C20—C2	120.00 (11)	C16—C17—H17	120.5 (12)
C2—C20—C21	119.11 (10)	C18—C17—H17	119.4 (12)
C7—C9—H9	119.8 (9)	C19—C18—H18	117.3 (12)
C10—C9—C7	120.12 (12)	C17—C18—C19	120.70 (15)
C10—C9—H9	120.1 (9)	C17—C18—H18	121.9 (12)

O1—C13—C14—C15	−158.47 (13)	C7—C8—C12—C11	−0.42 (17)
O1—C13—C14—C19	18.35 (19)	C7—C9—C10—C11	−0.05 (19)
C21—C22—C23—C24	1.11 (19)	C13—C1—C12—C8	170.16 (10)
C21—C26—C25—C24	1.1 (2)	C13—C1—C12—C11	−4.8 (2)
C8—C3—C2—C1	−0.11 (13)	C13—C1—C2—C3	−170.17 (10)
C8—C3—C2—C20	−177.02 (11)	C13—C1—C2—C20	6.62 (19)
C8—C3—C4—C5	1.23 (17)	C13—C14—C15—C16	176.96 (12)
C8—C12—C11—C10	0.71 (17)	C13—C14—C19—C18	−177.84 (14)
C8—C7—C9—C10	0.35 (17)	C2—C3—C4—C5	−177.04 (13)
C8—C7—C6—C5	−0.36 (17)	C2—C1—C12—C8	−0.25 (13)
C3—C8—C12—C1	0.19 (13)	C2—C1—C12—C11	−175.18 (13)
C3—C8—C12—C11	176.14 (10)	C2—C1—C13—O1	42.45 (18)
C3—C8—C7—C9	−176.22 (11)	C2—C1—C13—C14	−138.63 (12)
C3—C8—C7—C6	1.77 (17)	C22—C21—C20—O2	−149.50 (13)
C3—C2—C20—O2	38.50 (18)	C22—C21—C20—C2	28.47 (17)
C3—C2—C20—C21	−139.48 (12)	C22—C21—C26—C25	−0.45 (19)
C3—C4—C5—C6	0.07 (19)	C22—C23—C24—C25	−0.5 (2)
C1—C12—C11—C10	175.16 (12)	C14—C15—C16—C17	0.4 (2)
C1—C13—C14—C15	22.63 (17)	C14—C19—C18—C17	1.2 (3)
C1—C13—C14—C19	−160.54 (12)	C4—C3—C2—C1	178.31 (13)
C1—C2—C20—O2	−137.84 (14)	C4—C3—C2—C20	1.4 (2)
C1—C2—C20—C21	44.18 (18)	C4—C5—C6—C7	−0.5 (2)
C12—C8—C3—C2	−0.06 (13)	C20—C21—C22—C23	176.88 (11)
C12—C8—C3—C4	−178.80 (10)	C20—C21—C26—C25	−178.03 (12)
C12—C8—C7—C9	−0.13 (17)	C9—C7—C6—C5	177.34 (12)
C12—C8—C7—C6	177.86 (11)	C23—C24—C25—C26	−0.6 (2)
C12—C1—C13—O1	−126.40 (13)	C6—C7—C9—C10	−177.34 (12)
C12—C1—C13—C14	52.52 (16)	C15—C14—C19—C18	−0.9 (2)
C12—C1—C2—C3	0.22 (13)	C15—C16—C17—C18	−0.1 (2)
C12—C1—C2—C20	177.01 (11)	C26—C21—C22—C23	−0.64 (18)
C12—C11—C10—C9	−0.51 (19)	C26—C21—C20—O2	28.03 (18)
C7—C8—C3—C2	176.50 (11)	C26—C21—C20—C2	−154.00 (12)
C7—C8—C3—C4	−2.25 (18)	C16—C17—C18—C19	−0.7 (3)
C7—C8—C12—C1	−176.37 (11)	C19—C14—C15—C16	0.15 (19)

Experimental details

Crystal data
Chemical formula	C₂₆H₁₆O₂
M_r	360.39
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.4578 (4), 10.2665 (5), 10.9183 (4)
α, β, γ (°)	71.448 (2), 66.494 (2), 84.269 (2)
V (Å³)	921.21 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.69 × 0.65 × 0.41

Data collection
Diffractometer	Bruker PHOTON-100 CMOS diffractometer
Absorption correction	Numerical (SADABS2014/5; Bruker, 2014)
T_min, T_max	0.867, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	32789, 4661, 3721
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.119, 1.05
No. of reflections	4661
No. of parameters	317
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.23

Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2013), SHELXT (Sheldrick, 2015b), SHELXL2014 (Sheldrick, 2015a), OLEX2 (Dolomanov et al., 2009), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

Financial support from State University of New York (IITG grant No.880030) is gratefully acknowledged.

References

Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2014). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Kitaigorodsky, A. I. (1973). In Molecular Crystals and Molecules. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 71| Part 7| July 2015| Pages o487-o488

doi:10.1107/S2056989015011160

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