Crystal structure and Hirshfeld surface analysis of 6-benzoyl-3,5-di­phenyl­cyclo­hex-2-en-1-one

The central cyclo­hexenone ring of the non-planar title compound adopts an envelope conformation. The crystal structure of the compound is stabilized by C—H...O and C—H...π inter­actions, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.149
• Data-to-parameter ratio = 16.8

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Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     19.722 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.387 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         20 Report

Alert level G
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PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          S Verify
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PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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Computing details

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b).

6-Benzoyl-3,5-diphenylcyclohex-2-en-1-one

Crystal data

C25H20O2	F(000) = 744
Mr = 352.41	Dx = 1.238 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.2365 (4) Å	Cell parameters from 3243 reflections
b = 9.7989 (4) Å	θ = 2.5–25.0°
c = 19.3759 (8) Å	µ = 0.08 mm^−1
β = 103.333 (2)°	T = 296 K
V = 1891.14 (13) Å^3	Prism, colourless
Z = 4	0.23 × 0.20 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	2471 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.073
Absorption correction: multi-scan (SADABS; Bruker, 2003)	θmax = 27.0°, θmin = 2.1°
Tmin = 0.660, Tmax = 0.746	h = −13→13
23764 measured reflections	k = −12→12
4102 independent reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0717P)^2 + 0.020P] where P = (Fo^2 + 2Fc^2)/3
4102 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.84873 (15)	0.4571 (2)	0.84508 (9)	0.0662 (5)
O2	0.73311 (16)	0.59881 (16)	0.68577 (9)	0.0556 (4)
C1	0.7327 (2)	0.4250 (2)	0.81963 (11)	0.0432 (5)
C2	0.68555 (19)	0.3941 (2)	0.74035 (11)	0.0377 (5)
H2A	0.703396	0.297799	0.732533	0.045*
C3	0.53461 (19)	0.4203 (2)	0.71377 (10)	0.0380 (5)
H3A	0.519851	0.518223	0.718969	0.046*
C4	0.4572 (2)	0.3451 (3)	0.76099 (11)	0.0471 (6)
H4A	0.362962	0.369151	0.746260	0.056*
H4B	0.464862	0.247638	0.754221	0.056*
C5	0.5064 (2)	0.3775 (2)	0.83834 (10)	0.0388 (5)
C6	0.6339 (2)	0.4151 (2)	0.86315 (11)	0.0442 (5)
H6A	0.661662	0.436354	0.911083	0.053*
C7	0.7682 (2)	0.4818 (2)	0.70074 (11)	0.0401 (5)
C8	0.89014 (19)	0.4261 (2)	0.68142 (11)	0.0403 (5)
C9	0.9499 (2)	0.5025 (3)	0.63619 (12)	0.0532 (6)
H9A	0.912888	0.586024	0.619070	0.064*
C10	1.0629 (2)	0.4558 (3)	0.61664 (13)	0.0612 (7)
H10A	1.101409	0.507482	0.586302	0.073*
C11	1.1189 (2)	0.3329 (3)	0.64180 (13)	0.0580 (7)
H11A	1.194874	0.301126	0.628243	0.070*
C12	1.0623 (2)	0.2568 (3)	0.68717 (13)	0.0570 (6)
H12A	1.101121	0.174324	0.704782	0.068*
C13	0.9480 (2)	0.3026 (2)	0.70664 (12)	0.0486 (6)
H13A	0.909822	0.250122	0.736835	0.058*
C14	0.47921 (18)	0.3846 (2)	0.63661 (10)	0.0375 (5)
C15	0.4852 (2)	0.2530 (3)	0.61136 (12)	0.0515 (6)
H15A	0.529328	0.185343	0.641574	0.062*
C16	0.4257 (2)	0.2214 (3)	0.54103 (13)	0.0604 (7)
H16A	0.429682	0.132362	0.525007	0.073*
C17	0.3615 (2)	0.3190 (3)	0.49526 (13)	0.0620 (7)
H17A	0.322732	0.297407	0.448269	0.074*
C18	0.3552 (3)	0.4496 (3)	0.51981 (13)	0.0625 (7)
H18A	0.311330	0.516816	0.489171	0.075*
C19	0.4131 (2)	0.4825 (2)	0.58944 (12)	0.0491 (6)
H19A	0.407775	0.571668	0.604998	0.059*
C20	0.4106 (2)	0.3634 (2)	0.88513 (11)	0.0398 (5)
C21	0.2742 (2)	0.3877 (3)	0.86040 (13)	0.0550 (6)
H21A	0.241528	0.412364	0.813221	0.066*
C22	0.1862 (2)	0.3760 (3)	0.90421 (15)	0.0667 (8)
H22A	0.095277	0.393434	0.886588	0.080*
C23	0.2324 (3)	0.3389 (3)	0.97356 (15)	0.0662 (7)
H23A	0.173169	0.331066	1.003253	0.079*
C24	0.3663 (3)	0.3132 (3)	0.99904 (14)	0.0625 (7)
H24A	0.397718	0.287297	1.046135	0.075*
C25	0.4553 (2)	0.3253 (3)	0.95566 (12)	0.0516 (6)
H25A	0.545976	0.307812	0.973826	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0359 (9)	0.1016 (15)	0.0586 (10)	−0.0170 (9)	0.0056 (8)	−0.0036 (9)
O2	0.0606 (10)	0.0407 (10)	0.0728 (11)	0.0030 (8)	0.0305 (9)	0.0069 (8)
C1	0.0342 (11)	0.0494 (13)	0.0456 (13)	−0.0024 (10)	0.0084 (9)	0.0009 (10)
C2	0.0310 (10)	0.0410 (12)	0.0426 (12)	−0.0015 (9)	0.0115 (9)	0.0000 (9)
C3	0.0340 (10)	0.0434 (12)	0.0379 (11)	0.0018 (9)	0.0107 (9)	−0.0001 (9)
C4	0.0342 (11)	0.0680 (16)	0.0398 (12)	−0.0073 (10)	0.0101 (9)	0.0004 (11)
C5	0.0367 (11)	0.0434 (13)	0.0376 (12)	0.0024 (9)	0.0112 (9)	0.0001 (9)
C6	0.0398 (12)	0.0545 (14)	0.0378 (12)	0.0003 (10)	0.0074 (9)	−0.0019 (10)
C7	0.0383 (11)	0.0404 (13)	0.0428 (12)	−0.0034 (10)	0.0118 (9)	−0.0003 (9)
C8	0.0354 (11)	0.0432 (12)	0.0434 (12)	−0.0054 (9)	0.0111 (9)	−0.0038 (10)
C9	0.0485 (13)	0.0566 (15)	0.0587 (15)	−0.0081 (11)	0.0211 (11)	0.0045 (12)
C10	0.0459 (14)	0.0793 (19)	0.0643 (17)	−0.0090 (13)	0.0248 (12)	0.0062 (14)
C11	0.0313 (11)	0.082 (2)	0.0644 (16)	−0.0024 (12)	0.0176 (11)	−0.0128 (14)
C12	0.0389 (12)	0.0618 (16)	0.0717 (16)	0.0052 (11)	0.0159 (12)	0.0005 (13)
C13	0.0407 (12)	0.0528 (15)	0.0557 (14)	−0.0018 (10)	0.0183 (10)	0.0054 (11)
C14	0.0298 (10)	0.0491 (13)	0.0365 (11)	−0.0019 (9)	0.0136 (8)	−0.0015 (9)
C15	0.0490 (13)	0.0568 (15)	0.0501 (14)	0.0037 (11)	0.0141 (11)	−0.0028 (12)
C16	0.0615 (16)	0.0654 (17)	0.0603 (16)	−0.0112 (13)	0.0261 (13)	−0.0215 (13)
C17	0.0562 (15)	0.092 (2)	0.0387 (13)	−0.0195 (15)	0.0123 (11)	−0.0051 (14)
C18	0.0600 (16)	0.0763 (19)	0.0468 (14)	−0.0068 (13)	0.0035 (12)	0.0123 (13)
C19	0.0496 (13)	0.0522 (14)	0.0455 (13)	−0.0026 (11)	0.0110 (10)	0.0046 (11)
C20	0.0369 (11)	0.0449 (12)	0.0393 (12)	0.0016 (9)	0.0122 (9)	−0.0039 (9)
C21	0.0421 (12)	0.0775 (18)	0.0470 (14)	0.0041 (12)	0.0137 (11)	−0.0002 (12)
C22	0.0405 (13)	0.099 (2)	0.0657 (18)	0.0000 (13)	0.0214 (12)	−0.0073 (15)
C23	0.0624 (16)	0.083 (2)	0.0653 (18)	0.0023 (14)	0.0404 (14)	−0.0014 (14)
C24	0.0645 (16)	0.0813 (19)	0.0476 (14)	0.0096 (14)	0.0254 (12)	0.0091 (13)
C25	0.0429 (12)	0.0707 (17)	0.0434 (13)	0.0104 (11)	0.0146 (10)	0.0034 (11)

Geometric parameters (Å, º)

O1—C1	1.218 (2)	C12—C13	1.384 (3)
O2—C7	1.217 (2)	C12—H12A	0.9300
C1—C6	1.461 (3)	C13—H13A	0.9300
C1—C2	1.530 (3)	C14—C15	1.385 (3)
C2—C7	1.530 (3)	C14—C19	1.389 (3)
C2—C3	1.533 (3)	C15—C16	1.393 (3)
C2—H2A	0.9800	C15—H15A	0.9300
C3—C14	1.513 (3)	C16—C17	1.366 (4)
C3—C4	1.530 (3)	C16—H16A	0.9300
C3—H3A	0.9800	C17—C18	1.371 (4)
C4—C5	1.501 (3)	C17—H17A	0.9300
C4—H4A	0.9700	C18—C19	1.381 (3)
C4—H4B	0.9700	C18—H18A	0.9300
C5—C6	1.335 (3)	C19—H19A	0.9300
C5—C20	1.487 (3)	C20—C25	1.388 (3)
C6—H6A	0.9300	C20—C21	1.388 (3)
C7—C8	1.487 (3)	C21—C22	1.378 (3)
C8—C13	1.387 (3)	C21—H21A	0.9300
C8—C9	1.396 (3)	C22—C23	1.367 (4)
C9—C10	1.376 (3)	C22—H22A	0.9300
C9—H9A	0.9300	C23—C24	1.370 (3)
C10—C11	1.374 (4)	C23—H23A	0.9300
C10—H10A	0.9300	C24—C25	1.379 (3)
C11—C12	1.378 (3)	C24—H24A	0.9300
C11—H11A	0.9300	C25—H25A	0.9300
O1—C1—C6	121.6 (2)	C11—C12—C13	120.3 (2)
O1—C1—C2	120.64 (19)	C11—C12—H12A	119.8
C6—C1—C2	117.80 (17)	C13—C12—H12A	119.8
C1—C2—C7	108.05 (16)	C12—C13—C8	120.4 (2)
C1—C2—C3	111.34 (16)	C12—C13—H13A	119.8
C7—C2—C3	111.64 (17)	C8—C13—H13A	119.8
C1—C2—H2A	108.6	C15—C14—C19	117.7 (2)
C7—C2—H2A	108.6	C15—C14—C3	121.83 (19)
C3—C2—H2A	108.6	C19—C14—C3	120.35 (19)
C14—C3—C4	110.59 (16)	C14—C15—C16	120.5 (2)
C14—C3—C2	114.35 (16)	C14—C15—H15A	119.7
C4—C3—C2	109.83 (16)	C16—C15—H15A	119.7
C14—C3—H3A	107.2	C17—C16—C15	121.0 (2)
C4—C3—H3A	107.2	C17—C16—H16A	119.5
C2—C3—H3A	107.2	C15—C16—H16A	119.5
C5—C4—C3	113.23 (17)	C16—C17—C18	118.8 (2)
C5—C4—H4A	108.9	C16—C17—H17A	120.6
C3—C4—H4A	108.9	C18—C17—H17A	120.6
C5—C4—H4B	108.9	C17—C18—C19	120.8 (2)
C3—C4—H4B	108.9	C17—C18—H18A	119.6
H4A—C4—H4B	107.7	C19—C18—H18A	119.6
C6—C5—C20	122.24 (19)	C18—C19—C14	121.1 (2)
C6—C5—C4	119.54 (18)	C18—C19—H19A	119.5
C20—C5—C4	118.20 (17)	C14—C19—H19A	119.5
C5—C6—C1	124.03 (19)	C25—C20—C21	117.5 (2)
C5—C6—H6A	118.0	C25—C20—C5	120.77 (18)
C1—C6—H6A	118.0	C21—C20—C5	121.71 (19)
O2—C7—C8	120.30 (19)	C22—C21—C20	121.5 (2)
O2—C7—C2	118.76 (18)	C22—C21—H21A	119.3
C8—C7—C2	120.94 (19)	C20—C21—H21A	119.3
C13—C8—C9	118.4 (2)	C23—C22—C21	120.0 (2)
C13—C8—C7	123.14 (19)	C23—C22—H22A	120.0
C9—C8—C7	118.4 (2)	C21—C22—H22A	120.0
C10—C9—C8	120.8 (2)	C22—C23—C24	119.6 (2)
C10—C9—H9A	119.6	C22—C23—H23A	120.2
C8—C9—H9A	119.6	C24—C23—H23A	120.2
C11—C10—C9	120.2 (2)	C23—C24—C25	120.7 (2)
C11—C10—H10A	119.9	C23—C24—H24A	119.6
C9—C10—H10A	119.9	C25—C24—H24A	119.6
C10—C11—C12	119.9 (2)	C24—C25—C20	120.6 (2)
C10—C11—H11A	120.1	C24—C25—H25A	119.7
C12—C11—H11A	120.1	C20—C25—H25A	119.7
O1—C1—C2—C7	−31.1 (3)	C10—C11—C12—C13	1.0 (4)
C6—C1—C2—C7	148.64 (19)	C11—C12—C13—C8	−0.8 (4)
O1—C1—C2—C3	−154.1 (2)	C9—C8—C13—C12	0.0 (3)
C6—C1—C2—C3	25.7 (3)	C7—C8—C13—C12	−179.4 (2)
C1—C2—C3—C14	−176.81 (17)	C4—C3—C14—C15	−63.8 (2)
C7—C2—C3—C14	62.3 (2)	C2—C3—C14—C15	60.8 (3)
C1—C2—C3—C4	−51.8 (2)	C4—C3—C14—C19	112.4 (2)
C7—C2—C3—C4	−172.67 (17)	C2—C3—C14—C19	−123.0 (2)
C14—C3—C4—C5	−179.34 (18)	C19—C14—C15—C16	−0.4 (3)
C2—C3—C4—C5	53.5 (2)	C3—C14—C15—C16	175.84 (19)
C3—C4—C5—C6	−27.3 (3)	C14—C15—C16—C17	0.7 (3)
C3—C4—C5—C20	153.97 (19)	C15—C16—C17—C18	−0.6 (4)
C20—C5—C6—C1	177.5 (2)	C16—C17—C18—C19	0.3 (4)
C4—C5—C6—C1	−1.2 (3)	C17—C18—C19—C14	−0.1 (4)
O1—C1—C6—C5	−178.4 (2)	C15—C14—C19—C18	0.1 (3)
C2—C1—C6—C5	1.8 (3)	C3—C14—C19—C18	−176.2 (2)
C1—C2—C7—O2	−83.9 (2)	C6—C5—C20—C25	−30.6 (3)
C3—C2—C7—O2	38.9 (3)	C4—C5—C20—C25	148.1 (2)
C1—C2—C7—C8	95.4 (2)	C6—C5—C20—C21	149.3 (2)
C3—C2—C7—C8	−141.80 (19)	C4—C5—C20—C21	−32.0 (3)
O2—C7—C8—C13	169.2 (2)	C25—C20—C21—C22	0.7 (4)
C2—C7—C8—C13	−10.2 (3)	C5—C20—C21—C22	−179.2 (2)
O2—C7—C8—C9	−10.3 (3)	C20—C21—C22—C23	−0.5 (4)
C2—C7—C8—C9	170.39 (19)	C21—C22—C23—C24	−0.1 (4)
C13—C8—C9—C10	0.5 (3)	C22—C23—C24—C25	0.4 (4)
C7—C8—C9—C10	180.0 (2)	C23—C24—C25—C20	−0.2 (4)
C8—C9—C10—C11	−0.3 (4)	C21—C20—C25—C24	−0.4 (4)
C9—C10—C11—C12	−0.5 (4)	C5—C20—C25—C24	179.6 (2)

Hydrogen-bond geometry (Å, º)

Cg2 and Cg3 are the centroids of the C8–C13 and C14–C19 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2^i	0.98	2.50	3.251 (3)	133
C15—H15A···O1^i	0.93	2.55	3.369 (3)	148
C22—H22A···O1^ii	0.93	2.54	3.472 (3)	175
C11—H11A···Cg3^iii	0.93	2.88	3.717 (2)	150
C24—H24A···Cg2^iv	0.93	2.78	3.667 (3)	159

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