(2RS,3RS,1′SR,2′SR,3′RS)-2-(2′,3′-Di­hydro-1′-hydroxy-3′-phenyl-1H-inden-2′-yl)-2,3-di­hydro-3-phenyl­inden-1-one: isomer (I)

Isomer (I) of the title compound, C₃₀H₂₄O₂, has been obtained as yellow plate-like crystals. The di­hydro­bi­indene skeleton is approximately planar, and there are two phenyl substituents on the same side of the skeleton plane. The mol­ecules are connected via an O—H...O hydrogen bond, forming spiral chains along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.167
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.58 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C12     ..       5.10 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for        C23
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for        C29
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C21

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

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

---

Computing details

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I)

Crystal data

C30H24O2	F(000) = 880
Mr = 416.52	Dx = 1.245 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 17.985 (3) Å	Cell parameters from 25 reflections
b = 9.529 (3) Å	θ = 10.1–12.8°
c = 13.154 (4) Å	µ = 0.08 mm^−1
β = 99.63 (2)°	T = 297 K
V = 2222.6 (10) Å^3	Plate, yellow
Z = 4	0.5 × 0.3 × 0.1 mm

Data collection

Rigaku AFC7R diffractometer	Rint = 0.035
ω–2θ scans	θmax = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = −8→23
Tmin = 0.974, Tmax = 0.993	k = −12→4
6053 measured reflections	l = −17→17
5110 independent reflections	3 standard reflections every 150 reflections
2464 reflections with I > 2σ(I)	intensity decay: 0.5%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.054	w = 1/[σ^2(Fo^2) + (0.0731P)^2 + 0.206P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.167	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.28 e Å^−3
5110 reflections	Δρmin = −0.21 e Å^−3
290 parameters

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	0.7225 (1)	0.0544 (2)	0.3730 (1)	0.0598 (5)
O2	0.6680 (1)	0.5763 (2)	0.2719 (1)	0.0621 (5)
C3	0.6575 (1)	0.1102 (2)	0.3129 (2)	0.0452 (6)
C4	0.6609 (1)	0.2682 (2)	0.2896 (2)	0.0447 (5)
C5	0.6118 (1)	0.2905 (2)	0.1818 (2)	0.0440 (5)
C6	0.6132 (1)	0.1459 (2)	0.1341 (2)	0.0431 (5)
C7	0.6359 (1)	0.0452 (2)	0.2079 (2)	0.0448 (6)
C8	0.6377 (1)	−0.0958 (2)	0.1814 (2)	0.0565 (7)
C9	0.6178 (2)	−0.1326 (3)	0.0790 (2)	0.0633 (8)
C10	0.5965 (2)	−0.0318 (3)	0.0055 (2)	0.0649 (8)
C11	0.5936 (1)	0.1082 (3)	0.0317 (2)	0.0547 (6)
C12	0.6716 (1)	0.5196 (2)	0.3559 (2)	0.0449 (5)
C13	0.6493 (1)	0.3698 (2)	0.3729 (2)	0.0480 (6)
C14	0.6854 (1)	0.3358 (2)	0.4871 (2)	0.0447 (5)
C15	0.7123 (1)	0.4784 (2)	0.5306 (2)	0.0431 (5)
C16	0.7024 (1)	0.5810 (2)	0.4568 (2)	0.0439 (5)
C17	0.7223 (2)	0.7204 (3)	0.4796 (2)	0.0559 (7)
C18	0.7535 (2)	0.7527 (3)	0.5792 (2)	0.0628 (7)
C19	0.7656 (2)	0.6496 (3)	0.6536 (2)	0.0657 (8)
C20	0.7449 (2)	0.5119 (3)	0.6310 (2)	0.0574 (7)
C21	0.5315 (1)	0.3381 (2)	0.1824 (2)	0.0422 (5)
C22	0.5045 (2)	0.4589 (3)	0.1337 (3)	0.0762 (9)
C23	0.4298 (2)	0.4982 (4)	0.1296 (3)	0.109 (1)
C24	0.3821 (2)	0.4193 (4)	0.1755 (3)	0.0844 (10)
C25	0.4076 (2)	0.3017 (3)	0.2251 (3)	0.0725 (8)
C26	0.4813 (1)	0.2603 (3)	0.2279 (2)	0.0625 (7)
C27	0.6304 (1)	0.2658 (3)	0.5471 (2)	0.0469 (6)
C28	0.5741 (2)	0.3407 (3)	0.5812 (3)	0.0771 (9)
C29	0.5224 (2)	0.2750 (4)	0.6328 (3)	0.107 (1)
C30	0.5275 (2)	0.1341 (5)	0.6513 (3)	0.106 (1)
C31	0.5828 (2)	0.0586 (4)	0.6179 (3)	0.090 (1)
C32	0.6345 (2)	0.1230 (3)	0.5671 (2)	0.0620 (7)
H1	0.7571	0.0545	0.3396	0.0598*
H3	0.6168	0.0957	0.3494	0.0542*
H4	0.7112	0.2841	0.2791	0.0536*
H5	0.6362	0.3554	0.1435	0.0527*
H8	0.6523	−0.1653	0.2327	0.0678*
H9	0.6189	−0.2284	0.0592	0.0760*
H10	0.5836	−0.0587	−0.0648	0.0778*
H11	0.5783	0.1772	−0.0197	0.0656*
H13	0.5964	0.3720	0.3722	0.0576*
H14	0.7277	0.2762	0.4873	0.0536*
H17	0.7145	0.7908	0.4278	0.0671*
H18	0.7669	0.8470	0.5970	0.0754*
H19	0.7885	0.6736	0.7218	0.0789*
H20	0.7529	0.4417	0.6830	0.0688*
H22	0.5372	0.5166	0.1022	0.0915*
H23	0.4118	0.5816	0.0943	0.1305*
H24	0.3310	0.4472	0.1725	0.1013*
H25	0.3748	0.2467	0.2585	0.0869*
H26	0.4981	0.1755	0.2622	0.0750*
H28	0.5705	0.4390	0.5692	0.0926*
H29	0.4834	0.3281	0.6552	0.1279*
H30	0.4926	0.0890	0.6873	0.1267*
H31	0.5858	−0.0397	0.6298	0.1084*
H32	0.6733	0.0689	0.5455	0.0744*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.068 (1)	0.050 (1)	0.060 (1)	0.0155 (9)	0.0045 (9)	0.0000 (9)
O2	0.093 (1)	0.0403 (9)	0.053 (1)	−0.0017 (9)	0.0114 (9)	0.0077 (8)
C3	0.055 (1)	0.034 (1)	0.049 (1)	0.000 (1)	0.012 (1)	0.001 (1)
C4	0.045 (1)	0.036 (1)	0.052 (1)	0.0007 (10)	0.005 (1)	−0.004 (1)
C5	0.047 (1)	0.039 (1)	0.048 (1)	−0.005 (1)	0.012 (1)	0.002 (1)
C6	0.036 (1)	0.042 (1)	0.053 (1)	−0.0039 (10)	0.013 (1)	−0.007 (1)
C7	0.043 (1)	0.039 (1)	0.054 (1)	−0.004 (1)	0.015 (1)	−0.010 (1)
C8	0.058 (2)	0.039 (1)	0.075 (2)	−0.003 (1)	0.017 (1)	−0.009 (1)
C9	0.057 (2)	0.050 (2)	0.085 (2)	−0.006 (1)	0.017 (1)	−0.029 (2)
C10	0.054 (2)	0.077 (2)	0.064 (2)	−0.012 (1)	0.010 (1)	−0.033 (2)
C11	0.047 (1)	0.065 (2)	0.052 (2)	−0.004 (1)	0.007 (1)	−0.008 (1)
C12	0.047 (1)	0.035 (1)	0.053 (1)	0.003 (1)	0.009 (1)	−0.002 (1)
C13	0.063 (2)	0.037 (1)	0.045 (1)	−0.009 (1)	0.013 (1)	−0.002 (1)
C14	0.051 (1)	0.037 (1)	0.048 (1)	−0.003 (1)	0.013 (1)	0.000 (1)
C15	0.043 (1)	0.043 (1)	0.047 (1)	−0.006 (1)	0.014 (1)	−0.007 (1)
C16	0.042 (1)	0.036 (1)	0.055 (1)	−0.0028 (10)	0.010 (1)	−0.005 (1)
C17	0.059 (2)	0.038 (1)	0.071 (2)	−0.003 (1)	0.011 (1)	−0.005 (1)
C18	0.061 (2)	0.052 (2)	0.076 (2)	−0.015 (1)	0.013 (1)	−0.022 (2)
C19	0.066 (2)	0.075 (2)	0.056 (2)	−0.011 (2)	0.010 (1)	−0.025 (2)
C20	0.063 (2)	0.058 (2)	0.052 (2)	−0.004 (1)	0.013 (1)	−0.003 (1)
C21	0.049 (1)	0.036 (1)	0.041 (1)	0.004 (1)	0.0048 (10)	0.0005 (10)
C22	0.072 (2)	0.071 (2)	0.091 (2)	0.021 (2)	0.030 (2)	0.042 (2)
C23	0.095 (3)	0.096 (3)	0.143 (3)	0.050 (2)	0.040 (2)	0.071 (3)
C24	0.070 (2)	0.088 (2)	0.099 (2)	0.034 (2)	0.025 (2)	0.024 (2)
C25	0.056 (2)	0.070 (2)	0.095 (2)	0.007 (1)	0.023 (2)	0.016 (2)
C26	0.051 (1)	0.052 (2)	0.086 (2)	0.008 (1)	0.015 (1)	0.021 (1)
C27	0.055 (1)	0.045 (1)	0.041 (1)	−0.006 (1)	0.009 (1)	0.001 (1)
C28	0.073 (2)	0.062 (2)	0.106 (2)	−0.002 (2)	0.043 (2)	0.005 (2)
C29	0.087 (2)	0.101 (3)	0.149 (4)	−0.015 (2)	0.068 (3)	−0.006 (3)
C30	0.116 (3)	0.104 (3)	0.109 (3)	−0.050 (3)	0.055 (3)	0.002 (2)
C31	0.123 (3)	0.067 (2)	0.087 (2)	−0.026 (2)	0.036 (2)	0.016 (2)
C32	0.083 (2)	0.050 (2)	0.055 (2)	−0.008 (1)	0.017 (1)	0.011 (1)

Geometric parameters (Å, º)

O1—C3	1.401 (3)	C16—C17	1.396 (3)
O1—H1	0.820	C17—C18	1.370 (4)
O2—C12	1.222 (3)	C17—H17	0.950
C3—C4	1.541 (3)	C18—C19	1.379 (4)
C3—C7	1.505 (3)	C18—H18	0.950
C3—H3	0.950	C19—C20	1.382 (4)
C4—C5	1.554 (3)	C19—H19	0.950
C4—C13	1.502 (3)	C20—H20	0.950
C4—H4	0.950	C21—C22	1.366 (4)
C5—C6	1.516 (3)	C21—C26	1.379 (4)
C5—C21	1.516 (3)	C22—C23	1.386 (5)
C5—H5	0.950	C22—H22	0.950
C6—C7	1.376 (3)	C23—C24	1.357 (6)
C6—C11	1.383 (3)	C23—H23	0.950
C7—C8	1.390 (3)	C24—C25	1.338 (5)
C8—C9	1.381 (4)	C24—H24	0.950
C8—H8	0.950	C25—C26	1.379 (4)
C9—C10	1.371 (4)	C25—H25	0.950
C9—H9	0.950	C26—H26	0.950
C10—C11	1.381 (4)	C27—C28	1.374 (4)
C10—H10	0.950	C27—C32	1.385 (4)
C11—H11	0.950	C28—C29	1.390 (6)
C12—C13	1.509 (3)	C28—H28	0.950
C12—C16	1.470 (3)	C29—C30	1.365 (6)
C13—C14	1.567 (3)	C29—H29	0.950
C13—H13	0.950	C30—C31	1.359 (6)
C14—C15	1.522 (3)	C30—H30	0.950
C14—C27	1.518 (4)	C31—C32	1.376 (5)
C14—H14	0.950	C31—H31	0.950
C15—C16	1.369 (3)	C32—H32	0.950
C15—C20	1.390 (3)
C3—O1—H1	109.5	C14—C15—C20	128.3 (2)
O1—C3—C4	115.2 (2)	C16—C15—C20	119.6 (2)
O1—C3—C7	115.1 (2)	C12—C16—C15	109.9 (2)
O1—C3—H3	107.5	C12—C16—C17	128.1 (2)
C4—C3—C7	103.4 (2)	C15—C16—C17	121.9 (2)
C4—C3—H3	107.5	C16—C17—C18	117.9 (2)
C7—C3—H3	107.5	C16—C17—H17	121.0
C3—C4—C5	106.3 (2)	C18—C17—H17	121.0
C3—C4—C13	118.0 (2)	C17—C18—C19	120.7 (3)
C3—C4—H4	104.7	C17—C18—H18	119.7
C5—C4—C13	116.9 (2)	C19—C18—H18	119.7
C5—C4—H4	104.7	C18—C19—C20	121.2 (2)
C13—C4—H4	104.7	C18—C19—H19	119.4
C4—C5—C6	102.0 (2)	C20—C19—H19	119.4
C4—C5—C21	115.6 (2)	C15—C20—C19	118.6 (2)
C4—C5—H5	109.4	C15—C20—H20	120.7
C6—C5—C21	110.9 (2)	C19—C20—H20	120.7
C6—C5—H5	109.4	C5—C21—C22	121.0 (2)
C21—C5—H5	109.4	C5—C21—C26	122.3 (2)
C5—C6—C7	111.4 (2)	C22—C21—C26	116.7 (2)
C5—C6—C11	128.3 (2)	C21—C22—C23	120.8 (3)
C7—C6—C11	120.2 (2)	C21—C22—H22	119.6
C3—C7—C6	111.2 (2)	C23—C22—H22	119.6
C3—C7—C8	127.9 (2)	C22—C23—C24	121.0 (3)
C6—C7—C8	120.9 (2)	C22—C23—H23	119.5
C7—C8—C9	118.5 (2)	C24—C23—H23	119.5
C7—C8—H8	120.8	C23—C24—C25	119.3 (3)
C9—C8—H8	120.8	C23—C24—H24	120.3
C8—C9—C10	120.4 (3)	C25—C24—H24	120.3
C8—C9—H9	119.8	C24—C25—C26	120.2 (3)
C10—C9—H9	119.8	C24—C25—H25	119.9
C9—C10—C11	121.3 (3)	C26—C25—H25	119.9
C9—C10—H10	119.4	C21—C26—C25	122.1 (3)
C11—C10—H10	119.4	C21—C26—H26	119.0
C6—C11—C10	118.7 (2)	C25—C26—H26	119.0
C6—C11—H11	120.7	C14—C27—C28	121.4 (2)
C10—C11—H11	120.7	C14—C27—C32	120.8 (2)
O2—C12—C13	125.2 (2)	C28—C27—C32	117.8 (3)
O2—C12—C16	126.5 (2)	C27—C28—C29	121.0 (3)
C13—C12—C16	108.2 (2)	C27—C28—H28	119.5
C4—C13—C12	115.4 (2)	C29—C28—H28	119.5
C4—C13—C14	118.8 (2)	C28—C29—C30	120.0 (4)
C4—C13—H13	105.5	C28—C29—H29	120.0
C12—C13—C14	105.1 (2)	C30—C29—H29	120.0
C12—C13—H13	105.5	C29—C30—C31	119.6 (4)
C14—C13—H13	105.5	C29—C30—H30	120.2
C13—C14—C15	103.3 (2)	C31—C30—H30	120.2
C13—C14—C27	112.8 (2)	C30—C31—C32	120.8 (3)
C13—C14—H14	109.2	C30—C31—H31	119.6
C15—C14—C27	113.0 (2)	C32—C31—H31	119.6
C15—C14—H14	109.2	C27—C32—C31	120.8 (3)
C27—C14—H14	109.2	C27—C32—H32	119.6
C14—C15—C16	112.1 (2)	C31—C32—H32	119.6
O1—C3—C4—C5	148.4 (2)	C11—C6—C5—C21	72.0 (3)
O1—C3—C4—C13	−78.2 (3)	C12—C13—C14—C15	10.4 (2)
O1—C3—C7—C6	−138.2 (2)	C12—C13—C14—C27	132.7 (2)
O1—C3—C7—C8	41.1 (4)	C12—C16—C15—C14	−2.6 (3)
O2—C12—C13—C4	31.5 (3)	C12—C16—C15—C20	176.3 (2)
O2—C12—C13—C14	164.3 (2)	C12—C16—C17—C18	−176.9 (2)
O2—C12—C16—C15	−166.9 (2)	C13—C4—C5—C21	−37.3 (3)
O2—C12—C16—C17	11.1 (4)	C13—C12—C16—C15	9.7 (3)
C3—C4—C5—C6	−23.6 (2)	C13—C12—C16—C17	−172.4 (2)
C3—C4—C5—C21	96.8 (2)	C13—C14—C15—C16	−5.1 (3)
C3—C4—C13—C12	165.8 (2)	C13—C14—C15—C20	176.1 (2)
C3—C4—C13—C14	39.7 (3)	C13—C14—C27—C28	−74.8 (3)
C3—C7—C6—C5	−3.8 (3)	C13—C14—C27—C32	103.6 (2)
C3—C7—C6—C11	177.7 (2)	C14—C13—C12—C16	−12.3 (3)
C3—C7—C8—C9	−177.7 (3)	C14—C15—C16—C17	179.2 (2)
C4—C3—C7—C6	−11.6 (3)	C14—C15—C20—C19	179.7 (2)
C4—C3—C7—C8	167.6 (2)	C14—C27—C28—C29	177.7 (3)
C4—C5—C6—C7	17.2 (3)	C14—C27—C32—C31	−177.4 (2)
C4—C5—C6—C11	−164.4 (2)	C15—C14—C27—C28	41.9 (3)
C4—C5—C21—C22	123.2 (3)	C15—C14—C27—C32	−139.6 (2)
C4—C5—C21—C26	−59.4 (3)	C15—C16—C17—C18	0.9 (4)
C4—C13—C12—C16	−145.1 (2)	C15—C20—C19—C18	0.8 (4)
C4—C13—C14—C15	141.2 (2)	C16—C15—C14—C27	−127.3 (2)
C4—C13—C14—C27	−96.5 (3)	C16—C15—C20—C19	1.0 (4)
C5—C4—C3—C7	21.8 (2)	C16—C17—C18—C19	0.9 (4)
C5—C4—C13—C12	−65.6 (3)	C17—C16—C15—C20	−1.8 (4)
C5—C4—C13—C14	168.4 (2)	C17—C18—C19—C20	−1.7 (5)
C5—C6—C7—C8	176.9 (2)	C20—C15—C14—C27	53.8 (3)
C5—C6—C11—C10	−177.7 (2)	C21—C22—C23—C24	1.2 (5)
C5—C21—C22—C23	176.5 (3)	C21—C26—C25—C24	1.3 (5)
C5—C21—C26—C25	−177.7 (2)	C22—C21—C26—C25	−0.3 (4)
C6—C5—C4—C13	−157.7 (2)	C22—C23—C24—C25	−0.1 (6)
C6—C5—C21—C22	−121.4 (3)	C23—C22—C21—C26	−1.0 (4)
C6—C5—C21—C26	55.9 (3)	C23—C24—C25—C26	−1.1 (5)
C6—C7—C8—C9	1.4 (4)	C27—C28—C29—C30	0.7 (5)
C6—C11—C10—C9	0.6 (4)	C27—C32—C31—C30	−1.2 (5)
C7—C3—C4—C13	155.3 (2)	C28—C27—C32—C31	1.1 (4)
C7—C6—C5—C21	−106.4 (2)	C28—C29—C30—C31	−0.8 (6)
C7—C6—C11—C10	0.6 (4)	C29—C28—C27—C32	−0.8 (4)
C7—C8—C9—C10	−0.3 (4)	C29—C30—C31—C32	1.1 (6)
C8—C7—C6—C11	−1.6 (4)	C29—C30—C31—C32	1.1 (6)
C8—C9—C10—C11	−0.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	2.16	2.969 (3)	168

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.