trans-2-Benzoyl-1-phenyl­indan

The title compound, C₂₂H₁₈O, was obtained as a single product from a stereoselective reaction. The five-membered ring adopts an envelope conformation. Two intra­molecular C—H...O inter­actions stabilize the mol­ecular conformation. An inter­molecular C—H...O inter­action generates chains of mol­ecules running along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.048
• wR factor = 0.101
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level A
RINTA01_ALERT_3_A  The value of Rint is greater than 0.20
            Rint given   0.240

Author Response: Due to the Rint value obteined in monoclinic system, the data collection was performed in triclinic system, so we are merging a big amount of data. The structure was solved in triclinic system, but after first steps in the refinement, we concluded the crystal system should be monoclinic and the space group P21/n.

PLAT020_ALERT_3_A The value of Rint is greater than 0.10 .........       0.24

Author Response: See the previous response.

PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low ....         27 Perc.

Author Response: 3022 reflections are used in the refinement with 209 parameters. 817 reflections have I>2\s(I). We think we have number of reflections enough to perform a good refinement. We can reduce the number of parameters using a rigid body model for the six membered rings, but we think we have a better model now.

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C18    ..  O23     ..      99.00 Deg.

   3 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: AFC6S Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: AFC6S Diffractometer Control Software; data reduction: AFC6S Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-PC (Sheldrick, 1994); software used to prepare material for publication: SHELXTL-PC.

(I)

Crystal data

C22H18O	F(000) = 632
Mr = 298.36	Dx = 1.218 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 20 reflections
a = 9.085 (1) Å	θ = 14–25°
b = 5.981 (1) Å	µ = 0.07 mm^−1
c = 30.091 (6) Å	T = 293 K
β = 95.66 (3)°	Needle, colourless
V = 1627.1 (6) Å^3	0.5 × 0.2 × 0.1 mm
Z = 4

Data collection

Rigaku AFC6 diffractometer	θmax = 25.5°, θmin = 2.3°
ω scans	h = −1→11
6911 measured reflections	k = −7→7
3022 independent reflections	l = −36→36
817 reflections with I > 2σ(I)	3 standard reflections every 147 reflections
Rint = 0.240	intensity decay: none

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)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0253P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.85	(Δ/σ)max < 0.001
3022 reflections	Δρmax = 0.16 e Å^−3
209 parameters	Δρmin = −0.15 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: 0.0036 (5)

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
C1	0.7481 (4)	0.3985 (5)	0.05643 (11)	0.0441 (10)
C2	0.8181 (4)	0.4342 (7)	0.01818 (11)	0.0569 (11)
H2A	0.8958	0.3429	0.0115	0.068*
C3	0.7705 (5)	0.6078 (7)	−0.00989 (12)	0.0643 (12)
H3A	0.8166	0.6323	−0.0357	0.077*
C4	0.6567 (5)	0.7446 (6)	−0.00042 (12)	0.0674 (13)
H4A	0.6276	0.8628	−0.0194	0.081*
C5	0.5845 (4)	0.7066 (6)	0.03765 (12)	0.0605 (11)
H5A	0.5056	0.7965	0.0439	0.073*
C6	0.6314 (4)	0.5339 (6)	0.06600 (11)	0.0452 (9)
C7	0.5707 (4)	0.4600 (6)	0.10844 (10)	0.0571 (11)
H7A	0.4816	0.3715	0.1022	0.069*
H7B	0.5495	0.5869	0.1268	0.069*
C8	0.6996 (4)	0.3170 (6)	0.13112 (10)	0.0456 (9)
H8A	0.7688	0.4153	0.1489	0.055*
C9	0.7773 (4)	0.2190 (5)	0.09201 (10)	0.0442 (10)
H9A	0.7226	0.0848	0.0815	0.053*
C10	0.9371 (4)	0.1540 (6)	0.10222 (10)	0.0441 (10)
C11	1.0388 (4)	0.2953 (6)	0.12545 (11)	0.0535 (10)
H11A	1.0075	0.4321	0.1358	0.064*
C12	1.1857 (5)	0.2351 (7)	0.13334 (11)	0.0593 (12)
H12A	1.2521	0.3311	0.1492	0.071*
C13	1.2350 (4)	0.0351 (8)	0.11802 (12)	0.0638 (11)
H13A	1.3343	−0.0041	0.1231	0.077*
C14	1.1359 (5)	−0.1058 (6)	0.09514 (12)	0.0638 (12)
H14A	1.1682	−0.2416	0.0846	0.077*
C15	0.9876 (5)	−0.0477 (7)	0.08754 (11)	0.0595 (11)
H15A	0.9214	−0.1462	0.0723	0.071*
C16	0.6426 (4)	0.1415 (7)	0.16157 (11)	0.0535 (11)
C17	0.5796 (4)	0.2122 (6)	0.20327 (11)	0.0501 (10)
C18	0.4918 (4)	0.0627 (6)	0.22353 (11)	0.0661 (12)
H18A	0.4747	−0.0781	0.211	0.079*
C19	0.4293 (5)	0.1171 (7)	0.26180 (13)	0.0834 (15)
H19A	0.3684	0.0154	0.2746	0.1*
C20	0.4575 (5)	0.3243 (8)	0.28116 (13)	0.0854 (15)
H20A	0.417	0.3615	0.3074	0.102*
C21	0.5459 (4)	0.4760 (7)	0.26156 (12)	0.0776 (14)
H21A	0.5651	0.6151	0.2747	0.093*
C22	0.6059 (4)	0.4210 (6)	0.22243 (11)	0.0600 (11)
H22A	0.6639	0.5243	0.209	0.072*
O23	0.6449 (3)	−0.0562 (5)	0.15198 (7)	0.0834 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.040 (2)	0.052 (3)	0.039 (2)	−0.007 (2)	−0.002 (2)	−0.0039 (19)
C2	0.049 (3)	0.077 (3)	0.045 (2)	0.005 (2)	0.005 (2)	−0.001 (2)
C3	0.067 (3)	0.079 (4)	0.045 (2)	−0.004 (3)	−0.002 (2)	0.009 (2)
C4	0.078 (4)	0.060 (3)	0.061 (3)	−0.004 (3)	−0.009 (3)	0.011 (2)
C5	0.054 (3)	0.061 (3)	0.065 (3)	−0.002 (2)	0.001 (2)	−0.002 (2)
C6	0.041 (3)	0.049 (3)	0.044 (2)	−0.004 (2)	−0.003 (2)	−0.003 (2)
C7	0.051 (3)	0.063 (3)	0.060 (2)	−0.008 (2)	0.017 (2)	−0.008 (2)
C8	0.045 (2)	0.051 (2)	0.042 (2)	−0.010 (2)	0.008 (2)	−0.0063 (19)
C9	0.043 (3)	0.046 (2)	0.045 (2)	−0.004 (2)	0.011 (2)	−0.0077 (19)
C10	0.054 (3)	0.045 (3)	0.034 (2)	−0.004 (3)	0.012 (2)	−0.0020 (19)
C11	0.052 (3)	0.053 (3)	0.056 (3)	−0.005 (3)	0.013 (2)	−0.007 (2)
C12	0.048 (3)	0.076 (3)	0.054 (3)	−0.011 (3)	0.007 (2)	−0.003 (2)
C13	0.050 (3)	0.082 (3)	0.061 (3)	0.001 (3)	0.017 (2)	0.012 (2)
C14	0.068 (3)	0.055 (3)	0.070 (3)	−0.001 (3)	0.016 (3)	−0.002 (2)
C15	0.065 (3)	0.056 (3)	0.056 (2)	−0.006 (3)	0.004 (2)	−0.011 (2)
C16	0.060 (3)	0.051 (3)	0.051 (2)	−0.005 (3)	0.011 (2)	−0.001 (2)
C17	0.055 (3)	0.056 (3)	0.040 (2)	−0.006 (3)	0.009 (2)	0.001 (2)
C18	0.074 (3)	0.075 (3)	0.051 (3)	0.000 (3)	0.015 (2)	0.005 (2)
C19	0.100 (4)	0.097 (4)	0.059 (3)	−0.013 (3)	0.034 (3)	0.011 (3)
C20	0.103 (4)	0.109 (4)	0.050 (3)	0.012 (4)	0.034 (3)	0.005 (3)
C21	0.101 (4)	0.077 (4)	0.056 (3)	0.009 (3)	0.015 (3)	−0.012 (2)
C22	0.063 (3)	0.066 (3)	0.053 (3)	−0.003 (3)	0.015 (2)	−0.003 (2)
O23	0.126 (3)	0.0535 (18)	0.078 (2)	−0.0145 (19)	0.0467 (19)	−0.0090 (16)

Geometric parameters (Å, º)

C1—C2	1.386 (4)	C11—C12	1.381 (4)
C1—C6	1.387 (4)	C11—H11A	0.930
C1—C9	1.521 (4)	C12—C13	1.372 (4)
C2—C3	1.380 (4)	C12—H12A	0.930
C2—H2A	0.930	C13—C14	1.368 (4)
C3—C4	1.371 (4)	C13—H13A	0.930
C3—H3A	0.930	C14—C15	1.388 (4)
C4—C5	1.394 (4)	C14—H14A	0.930
C4—H4A	0.930	C15—H15A	0.930
C5—C6	1.380 (4)	C16—O23	1.218 (3)
C5—H5A	0.930	C16—C17	1.491 (4)
C6—C7	1.506 (4)	C17—C18	1.379 (4)
C7—C8	1.552 (4)	C17—C22	1.387 (4)
C7—H7A	0.970	C18—C19	1.373 (4)
C7—H7B	0.970	C18—H18A	0.930
C8—C16	1.518 (4)	C19—C20	1.382 (5)
C8—C9	1.547 (4)	C19—H19A	0.930
C8—H8A	0.980	C20—C21	1.382 (4)
C9—C10	1.505 (4)	C20—H20A	0.930
C9—H9A	0.980	C21—C22	1.385 (4)
C10—C15	1.379 (4)	C21—H21A	0.930
C10—C11	1.389 (4)	C22—H22A	0.930
C2—C1—C6	120.3 (3)	C11—C10—C9	121.7 (4)
C2—C1—C9	129.1 (3)	C12—C11—C10	120.8 (4)
C6—C1—C9	110.5 (3)	C12—C11—H11A	119.6
C3—C2—C1	118.9 (4)	C10—C11—H11A	119.6
C3—C2—H2A	120.6	C13—C12—C11	120.7 (4)
C1—C2—H2A	120.6	C13—C12—H12A	119.6
C4—C3—C2	121.2 (4)	C11—C12—H12A	119.6
C4—C3—H3A	119.4	C14—C13—C12	119.1 (4)
C2—C3—H3A	119.4	C14—C13—H13A	120.5
C3—C4—C5	120.0 (4)	C12—C13—H13A	120.5
C3—C4—H4A	120.0	C13—C14—C15	120.5 (4)
C5—C4—H4A	120.0	C13—C14—H14A	119.7
C6—C5—C4	119.3 (4)	C15—C14—H14A	119.7
C6—C5—H5A	120.4	C10—C15—C14	121.0 (4)
C4—C5—H5A	120.4	C10—C15—H15A	119.5
C5—C6—C1	120.3 (3)	C14—C15—H15A	119.5
C5—C6—C7	128.9 (4)	O23—C16—C17	119.5 (3)
C1—C6—C7	110.8 (3)	O23—C16—C8	120.9 (3)
C6—C7—C8	102.2 (3)	C17—C16—C8	119.6 (3)
C6—C7—H7A	111.3	C18—C17—C22	118.9 (3)
C8—C7—H7A	111.3	C18—C17—C16	118.4 (4)
C6—C7—H7B	111.3	C22—C17—C16	122.7 (3)
C8—C7—H7B	111.3	C19—C18—C17	121.5 (4)
H7A—C7—H7B	109.2	C19—C18—H18A	119.2
C16—C8—C9	113.9 (3)	C17—C18—H18A	119.2
C16—C8—C7	111.0 (3)	C18—C19—C20	119.4 (4)
C9—C8—C7	104.8 (2)	C18—C19—H19A	120.3
C16—C8—H8A	109.0	C20—C19—H19A	120.3
C9—C8—H8A	109.0	C21—C20—C19	120.0 (4)
C7—C8—H8A	109.0	C21—C20—H20A	120.0
C10—C9—C1	115.1 (3)	C19—C20—H20A	120.0
C10—C9—C8	116.5 (3)	C20—C21—C22	120.1 (4)
C1—C9—C8	101.9 (3)	C20—C21—H21A	120.0
C10—C9—H9A	107.6	C22—C21—H21A	120.0
C1—C9—H9A	107.6	C21—C22—C17	120.1 (4)
C8—C9—H9A	107.6	C21—C22—H22A	120.0
C15—C10—C11	117.9 (4)	C17—C22—H22A	120.0
C15—C10—C9	120.4 (4)
C6—C1—C2—C3	0.6 (5)	C8—C9—C10—C11	−47.1 (4)
C9—C1—C2—C3	179.0 (3)	C15—C10—C11—C12	0.2 (5)
C1—C2—C3—C4	0.3 (5)	C9—C10—C11—C12	−178.1 (3)
C2—C3—C4—C5	−1.4 (5)	C10—C11—C12—C13	0.6 (5)
C3—C4—C5—C6	1.6 (5)	C11—C12—C13—C14	−0.7 (5)
C4—C5—C6—C1	−0.6 (5)	C12—C13—C14—C15	−0.1 (5)
C4—C5—C6—C7	−179.5 (3)	C11—C10—C15—C14	−1.0 (5)
C2—C1—C6—C5	−0.5 (5)	C9—C10—C15—C14	177.4 (3)
C9—C1—C6—C5	−179.1 (3)	C13—C14—C15—C10	0.9 (5)
C2—C1—C6—C7	178.6 (3)	C9—C8—C16—O23	−7.9 (5)
C9—C1—C6—C7	−0.1 (4)	C7—C8—C16—O23	110.2 (4)
C5—C6—C7—C8	−162.2 (3)	C9—C8—C16—C17	173.6 (3)
C1—C6—C7—C8	18.9 (3)	C7—C8—C16—C17	−68.4 (4)
C6—C7—C8—C16	−153.2 (3)	O23—C16—C17—C18	−16.7 (5)
C6—C7—C8—C9	−29.7 (3)	C8—C16—C17—C18	161.9 (3)
C2—C1—C9—C10	35.7 (5)	O23—C16—C17—C22	163.1 (4)
C6—C1—C9—C10	−145.8 (3)	C8—C16—C17—C22	−18.3 (5)
C2—C1—C9—C8	162.7 (3)	C22—C17—C18—C19	0.7 (6)
C6—C1—C9—C8	−18.8 (3)	C16—C17—C18—C19	−179.5 (3)
C16—C8—C9—C10	−82.8 (4)	C17—C18—C19—C20	−1.6 (6)
C7—C8—C9—C10	155.7 (3)	C18—C19—C20—C21	1.1 (7)
C16—C8—C9—C1	151.1 (3)	C19—C20—C21—C22	0.2 (6)
C7—C8—C9—C1	29.6 (3)	C20—C21—C22—C17	−1.1 (6)
C1—C9—C10—C15	−106.2 (3)	C18—C17—C22—C21	0.7 (5)
C8—C9—C10—C15	134.5 (3)	C16—C17—C22—C21	−179.1 (3)
C1—C9—C10—C11	72.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O23	0.98	2.45	2.800 (4)	101
C18—H18A···O23	0.93	2.47	2.769 (4)	99
C7—H7B···O23^i	0.97	2.40	3.220 (4)	142

Symmetry code: (i) x, y+1, z.