7-(Biphenyl-4-yl)-6-hy­droxy­indan-1-one

The title compound, C₂₁H₁₆O₂, was isolated from the reaction of 1-(2-meth­oxy­eth­oxy)-1-vinyl­cyclo­propane, 4-ethynylbiphenyl, and CO in a [5 + 1 + 2 + 1] cyclo­addition reaction catalysed by [Rh(CO)₂Cl]₂. The crystals precipitated directly from the crude reaction mixture. A hydrogen-bonding framework between the hy­droxy and carbonyl groups of a symmetry-related neighbour connects the mol­ecules into chains running parallel to the crystallographic c axis. A minor non-merohedral twin component was included in the refinement.

Key indicators

• Single-crystal X-ray study
• T = 125 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.079
• wR factor = 0.233
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00567 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.230 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.11 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 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: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

7-(Biphenyl-4-yl)-6-hydroxyindan-1-one

Crystal data

C21H16O2	F(000) = 632
Mr = 300.34	Dx = 1.332 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.384 (3) Å	Cell parameters from 2589 reflections
b = 11.032 (4) Å	θ = 2.2–24.7°
c = 14.827 (5) Å	µ = 0.09 mm^−1
β = 102.609 (4)°	T = 125 K
V = 1498.0 (9) Å^3	Plate, yellow
Z = 4	0.23 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer	2745 independent reflections
Radiation source: sealed tube	1711 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.117
φ and ω scans	θmax = 25.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.508, Tmax = 0.745	k = −13→13
14915 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.079	Hydrogen site location: mixed
wR(F^2) = 0.233	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.1129P)^2 + 1.384P] where P = (Fo^2 + 2Fc^2)/3
2745 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.37 e Å^−3
1 restraint	Δρmin = −0.31 e Å^−3
0 constraints

Special details

Refinement. Refined as a 2-component twin. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms bonded to carbon were included at geometrically idealized positions and were not refined. The isotropic thermal parameters of the hydrogen atoms were fixed at 1.2U_eq of the parent carbon atom and 1.5U_eq for the hydrogen bonded to oxygen. A bond length restraint was applied to the hydroxyl group, O—H = 0.85 (2) Å, to keep its geometry reasonable.

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

	x	y	z	Uiso*/Ueq
O1	0.1692 (3)	0.6107 (2)	0.01317 (18)	0.0288 (7)
H1	0.172 (5)	0.617 (4)	−0.0462 (15)	0.043*
O2	0.2090 (3)	0.8497 (3)	0.33830 (19)	0.0334 (8)
C1	0.1781 (4)	0.7254 (3)	0.0493 (3)	0.0232 (9)
C2	0.1621 (5)	0.8252 (3)	−0.0101 (3)	0.0261 (10)
H2	0.142119	0.812662	−0.075041	0.031*
C3	0.1749 (5)	0.9418 (4)	0.0245 (3)	0.0282 (10)
H3	0.163642	1.009427	−0.016059	0.034*
C4	0.2041 (4)	0.9583 (3)	0.1182 (3)	0.0240 (9)
C5	0.2194 (5)	1.0771 (4)	0.1702 (3)	0.0334 (11)
H5A	0.125839	1.122054	0.157794	0.040*
H5B	0.295471	1.128578	0.152723	0.040*
C6	0.2631 (6)	1.0398 (4)	0.2708 (3)	0.0355 (11)
H6A	0.205684	1.084921	0.308427	0.043*
H6B	0.368244	1.055469	0.295778	0.043*
C7	0.2303 (5)	0.9043 (4)	0.2713 (3)	0.0269 (10)
C8	0.2171 (4)	0.8599 (3)	0.1774 (3)	0.0221 (9)
C9	0.2065 (4)	0.7385 (3)	0.1440 (3)	0.0211 (9)
C10	0.2317 (4)	0.6321 (3)	0.2074 (3)	0.0229 (9)
C11	0.1350 (5)	0.5348 (3)	0.1952 (3)	0.0258 (9)
H11	0.051340	0.535998	0.145762	0.031*
C12	0.1593 (5)	0.4362 (3)	0.2543 (3)	0.0272 (10)
H12	0.091898	0.370758	0.244835	0.033*
C13	0.2803 (4)	0.4312 (3)	0.3270 (3)	0.0232 (9)
C14	0.3793 (5)	0.5282 (3)	0.3376 (3)	0.0269 (10)
H14	0.464594	0.526389	0.385879	0.032*
C15	0.3534 (5)	0.6263 (3)	0.2783 (3)	0.0262 (10)
H15	0.421510	0.691227	0.286679	0.031*
C16	0.3046 (4)	0.3278 (3)	0.3935 (3)	0.0233 (9)
C17	0.4434 (5)	0.2874 (4)	0.4329 (3)	0.0286 (10)
H17	0.525244	0.323702	0.415471	0.034*
C18	0.4652 (5)	0.1946 (4)	0.4975 (3)	0.0347 (11)
H18	0.561178	0.166813	0.523397	0.042*
C19	0.3472 (5)	0.1429 (4)	0.5239 (3)	0.0308 (10)
H19	0.362012	0.080224	0.568952	0.037*
C20	0.2083 (5)	0.1815 (3)	0.4855 (3)	0.0271 (10)
H20	0.127052	0.144838	0.503248	0.033*
C21	0.1865 (5)	0.2742 (3)	0.4205 (3)	0.0249 (9)
H21	0.090167	0.301150	0.394404	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0458 (19)	0.0126 (14)	0.0283 (16)	−0.0004 (12)	0.0085 (14)	−0.0015 (12)
O2	0.051 (2)	0.0207 (16)	0.0288 (17)	0.0034 (14)	0.0101 (14)	0.0019 (13)
C1	0.025 (2)	0.013 (2)	0.032 (2)	−0.0017 (16)	0.0078 (18)	−0.0009 (17)
C2	0.032 (2)	0.018 (2)	0.028 (2)	0.0003 (17)	0.0057 (18)	0.0013 (17)
C3	0.036 (3)	0.014 (2)	0.036 (3)	0.0034 (17)	0.011 (2)	0.0052 (18)
C4	0.028 (2)	0.0111 (19)	0.036 (2)	0.0009 (16)	0.0123 (18)	0.0054 (17)
C5	0.049 (3)	0.012 (2)	0.039 (3)	0.0012 (19)	0.010 (2)	−0.0014 (18)
C6	0.056 (3)	0.014 (2)	0.039 (3)	−0.0050 (19)	0.016 (2)	−0.0049 (18)
C7	0.028 (2)	0.018 (2)	0.033 (2)	0.0050 (17)	0.0031 (18)	0.0036 (18)
C8	0.028 (2)	0.0136 (19)	0.025 (2)	0.0016 (16)	0.0064 (17)	0.0025 (16)
C9	0.022 (2)	0.0119 (19)	0.029 (2)	0.0003 (15)	0.0060 (17)	0.0005 (16)
C10	0.031 (2)	0.0104 (19)	0.027 (2)	−0.0003 (16)	0.0073 (18)	−0.0016 (16)
C11	0.029 (2)	0.019 (2)	0.029 (2)	−0.0022 (17)	0.0058 (18)	0.0032 (17)
C12	0.033 (2)	0.014 (2)	0.034 (2)	−0.0028 (17)	0.0072 (19)	0.0009 (18)
C13	0.029 (2)	0.0122 (19)	0.029 (2)	0.0008 (17)	0.0084 (18)	0.0007 (16)
C14	0.029 (2)	0.016 (2)	0.034 (2)	0.0016 (17)	0.0028 (18)	0.0014 (17)
C15	0.029 (2)	0.014 (2)	0.035 (2)	−0.0010 (17)	0.0074 (19)	0.0029 (17)
C16	0.030 (2)	0.0128 (19)	0.027 (2)	−0.0001 (17)	0.0055 (18)	−0.0013 (16)
C17	0.028 (2)	0.015 (2)	0.042 (3)	0.0015 (17)	0.007 (2)	0.0038 (18)
C18	0.035 (3)	0.018 (2)	0.047 (3)	0.0020 (19)	0.002 (2)	0.009 (2)
C19	0.043 (3)	0.014 (2)	0.034 (2)	−0.0013 (19)	0.006 (2)	0.0047 (18)
C20	0.036 (3)	0.016 (2)	0.030 (2)	−0.0026 (18)	0.0095 (19)	0.0010 (17)
C21	0.030 (2)	0.013 (2)	0.031 (2)	0.0017 (17)	0.0061 (18)	0.0006 (17)

Geometric parameters (Å, º)

O1—C1	1.369 (5)	C10—C11	1.393 (5)
O1—H1	0.887 (19)	C11—C12	1.384 (5)
O2—C7	1.214 (5)	C11—H11	0.9500
C1—C9	1.380 (6)	C12—C13	1.386 (5)
C1—C2	1.397 (5)	C12—H12	0.9500
C2—C3	1.380 (6)	C13—C14	1.403 (6)
C2—H2	0.9500	C13—C16	1.492 (5)
C3—C4	1.369 (5)	C14—C15	1.383 (5)
C3—H3	0.9500	C14—H14	0.9500
C4—C8	1.384 (5)	C15—H15	0.9500
C4—C5	1.512 (5)	C16—C17	1.381 (6)
C5—C6	1.515 (6)	C16—C21	1.391 (6)
C5—H5A	0.9900	C17—C18	1.386 (6)
C5—H5B	0.9900	C17—H17	0.9500
C6—C7	1.527 (6)	C18—C19	1.377 (6)
C6—H6A	0.9900	C18—H18	0.9500
C6—H6B	0.9900	C19—C20	1.371 (6)
C7—C8	1.456 (6)	C19—H19	0.9500
C8—C9	1.423 (5)	C20—C21	1.389 (6)
C9—C10	1.490 (5)	C20—H20	0.9500
C10—C15	1.374 (5)	C21—H21	0.9500
C1—O1—H1	108 (3)	C15—C10—C9	120.7 (3)
O1—C1—C9	118.5 (3)	C11—C10—C9	121.1 (4)
O1—C1—C2	119.5 (3)	C12—C11—C10	120.7 (4)
C9—C1—C2	122.0 (4)	C12—C11—H11	119.6
C3—C2—C1	120.7 (4)	C10—C11—H11	119.6
C3—C2—H2	119.6	C11—C12—C13	121.2 (4)
C1—C2—H2	119.6	C11—C12—H12	119.4
C4—C3—C2	118.9 (4)	C13—C12—H12	119.4
C4—C3—H3	120.5	C12—C13—C14	117.9 (4)
C2—C3—H3	120.5	C12—C13—C16	121.7 (3)
C3—C4—C8	120.6 (4)	C14—C13—C16	120.5 (4)
C3—C4—C5	127.5 (4)	C15—C14—C13	120.4 (4)
C8—C4—C5	111.8 (3)	C15—C14—H14	119.8
C4—C5—C6	104.0 (3)	C13—C14—H14	119.8
C4—C5—H5A	111.0	C10—C15—C14	121.6 (4)
C6—C5—H5A	111.0	C10—C15—H15	119.2
C4—C5—H5B	111.0	C14—C15—H15	119.2
C6—C5—H5B	111.0	C17—C16—C21	118.6 (4)
H5A—C5—H5B	109.0	C17—C16—C13	121.3 (4)
C5—C6—C7	105.0 (3)	C21—C16—C13	120.0 (4)
C5—C6—H6A	110.7	C16—C17—C18	120.9 (4)
C7—C6—H6A	110.7	C16—C17—H17	119.5
C5—C6—H6B	110.7	C18—C17—H17	119.5
C7—C6—H6B	110.7	C19—C18—C17	119.8 (4)
H6A—C6—H6B	108.8	C19—C18—H18	120.1
O2—C7—C8	128.4 (4)	C17—C18—H18	120.1
O2—C7—C6	123.9 (4)	C20—C19—C18	120.2 (4)
C8—C7—C6	107.4 (3)	C20—C19—H19	119.9
C4—C8—C9	121.9 (4)	C18—C19—H19	119.9
C4—C8—C7	108.7 (3)	C19—C20—C21	120.0 (4)
C9—C8—C7	129.3 (3)	C19—C20—H20	120.0
C1—C9—C8	115.8 (3)	C21—C20—H20	120.0
C1—C9—C10	121.9 (3)	C20—C21—C16	120.5 (4)
C8—C9—C10	122.2 (3)	C20—C21—H21	119.8
C15—C10—C11	118.2 (4)	C16—C21—H21	119.8
O1—C1—C2—C3	−178.1 (4)	C1—C9—C10—C15	127.8 (4)
C9—C1—C2—C3	0.3 (7)	C8—C9—C10—C15	−49.1 (6)
C1—C2—C3—C4	0.2 (6)	C1—C9—C10—C11	−50.5 (6)
C2—C3—C4—C8	−1.5 (6)	C8—C9—C10—C11	132.6 (4)
C2—C3—C4—C5	−178.7 (4)	C15—C10—C11—C12	1.5 (6)
C3—C4—C5—C6	−175.6 (4)	C9—C10—C11—C12	179.9 (4)
C8—C4—C5—C6	7.0 (5)	C10—C11—C12—C13	−0.1 (6)
C4—C5—C6—C7	−14.8 (5)	C11—C12—C13—C14	−1.4 (6)
C5—C6—C7—O2	−157.0 (4)	C11—C12—C13—C16	177.5 (4)
C5—C6—C7—C8	18.0 (5)	C12—C13—C14—C15	1.6 (6)
C3—C4—C8—C9	2.4 (6)	C16—C13—C14—C15	−177.3 (4)
C5—C4—C8—C9	−180.0 (4)	C11—C10—C15—C14	−1.3 (6)
C3—C4—C8—C7	−173.2 (4)	C9—C10—C15—C14	−179.7 (4)
C5—C4—C8—C7	4.4 (5)	C13—C14—C15—C10	−0.2 (6)
O2—C7—C8—C4	160.6 (4)	C12—C13—C16—C17	146.5 (4)
C6—C7—C8—C4	−14.0 (5)	C14—C13—C16—C17	−34.6 (6)
O2—C7—C8—C9	−14.6 (7)	C12—C13—C16—C21	−36.8 (6)
C6—C7—C8—C9	170.8 (4)	C14—C13—C16—C21	142.1 (4)
O1—C1—C9—C8	178.9 (3)	C21—C16—C17—C18	0.5 (6)
C2—C1—C9—C8	0.5 (6)	C13—C16—C17—C18	177.3 (4)
O1—C1—C9—C10	1.8 (6)	C16—C17—C18—C19	−0.9 (7)
C2—C1—C9—C10	−176.6 (4)	C17—C18—C19—C20	1.1 (7)
C4—C8—C9—C1	−1.9 (6)	C18—C19—C20—C21	−0.9 (6)
C7—C8—C9—C1	172.8 (4)	C19—C20—C21—C16	0.5 (6)
C4—C8—C9—C10	175.2 (4)	C17—C16—C21—C20	−0.3 (6)
C7—C8—C9—C10	−10.1 (7)	C13—C16—C21—C20	−177.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.89 (2)	1.86 (2)	2.734 (4)	168 (5)

Symmetry code: (i) x, −y+3/2, z−1/2.