(2SR,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 (II)

Isomer (II) of the title compound, C₃₀H₂₄O₂, has been obtained as pale-orange needle-shaped crystals. The di­hydro­bi­indene skeleton is approximately planar, and there are two phenyl substituents on different sides of the skeleton plane. There is an intramolecular O—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 300 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.057
• wR factor = 0.170
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         30 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O1     -   C3      ..       8.25 su

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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.

(II)

Crystal data

C30H24O2	F(000) = 880
Mr = 416.52	Dx = 1.248 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.883 (4) Å	Cell parameters from 25 reflections
b = 11.290 (5) Å	θ = 10.3–13.6°
c = 13.418 (4) Å	µ = 0.08 mm^−1
β = 100.52 (2)°	T = 300 K
V = 2216.7 (13) Å^3	Needle, pale orange
Z = 4	0.45 × 0.25 × 0.10 mm

Data collection

Rigaku AFC7R diffractometer	Rint = 0.027
ω–2θ scans	θmax = 27.5°
Absorption correction: integration (Coppens et al., 1965)	h = −7→19
Tmin = 0.982, Tmax = 0.993	k = 0→14
5794 measured reflections	l = −17→17
5088 independent reflections	3 standard reflections every 150 reflections
1507 reflections with I > 2σ(I)	intensity decay: 0.3%

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.057	w = 1/[σ^2(Fo^2) + (0.0548P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.170	(Δ/σ)max < 0.001
S = 0.92	Δρmax = 0.23 e Å^−3
5088 reflections	Δρmin = −0.22 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	−0.0245 (2)	−0.0461 (3)	0.8157 (2)	0.092 (1)
O2	−0.0419 (2)	0.1248 (3)	0.9664 (2)	0.100 (1)
C3	−0.0662 (2)	0.0415 (3)	0.7545 (3)	0.054 (1)
C4	−0.0090 (2)	0.1537 (3)	0.7451 (2)	0.0461 (9)
C5	−0.0396 (2)	0.1965 (3)	0.6335 (2)	0.0448 (9)
C6	−0.0816 (2)	0.0872 (3)	0.5801 (3)	0.0464 (9)
C7	−0.0948 (2)	−0.0007 (3)	0.6472 (3)	0.0487 (9)
C8	−0.1306 (3)	−0.1095 (4)	0.6150 (3)	0.063 (1)
C9	−0.1549 (3)	−0.1295 (4)	0.5116 (3)	0.070 (1)
C10	−0.1440 (3)	−0.0419 (4)	0.4439 (3)	0.066 (1)
C11	−0.1066 (3)	0.0663 (4)	0.4767 (3)	0.057 (1)
C12	0.0009 (3)	0.2058 (4)	0.9370 (3)	0.059 (1)
C13	−0.0066 (2)	0.2466 (3)	0.8275 (2)	0.0446 (9)
C14	0.0666 (2)	0.3463 (3)	0.8318 (2)	0.0487 (9)
C15	0.0832 (2)	0.3821 (3)	0.9424 (3)	0.0486 (9)
C16	0.0482 (2)	0.3013 (3)	1.0009 (3)	0.0472 (9)
C17	0.0578 (3)	0.3146 (4)	1.1055 (3)	0.060 (1)
C18	0.1044 (3)	0.4121 (4)	1.1494 (3)	0.070 (1)
C19	0.1408 (3)	0.4929 (4)	1.0903 (4)	0.070 (1)
C20	0.1306 (3)	0.4792 (3)	0.9865 (3)	0.060 (1)
C21	−0.1040 (2)	0.3021 (3)	0.6181 (2)	0.0443 (9)
C22	−0.0767 (3)	0.4085 (4)	0.5837 (3)	0.055 (1)
C23	−0.1347 (3)	0.5053 (4)	0.5675 (3)	0.069 (1)
C24	−0.2224 (3)	0.4965 (4)	0.5859 (3)	0.066 (1)
C25	−0.2509 (3)	0.3919 (4)	0.6208 (3)	0.063 (1)
C26	−0.1931 (3)	0.2954 (3)	0.6362 (3)	0.0538 (10)
C27	0.1553 (2)	0.3116 (3)	0.7979 (3)	0.0451 (9)
C28	0.2099 (3)	0.2226 (3)	0.8467 (3)	0.055 (1)
C29	0.2913 (3)	0.1951 (4)	0.8176 (4)	0.072 (1)
C30	0.3209 (3)	0.2566 (6)	0.7416 (4)	0.088 (2)
C31	0.2679 (4)	0.3441 (5)	0.6932 (3)	0.088 (2)
C32	0.1852 (3)	0.3719 (4)	0.7209 (3)	0.066 (1)
H1	−0.0296	−0.0325	0.8745	0.0922*
H3	−0.1196	0.0647	0.7789	0.0645*
H4	0.0522	0.1271	0.7500	0.0553*
H5	0.0135	0.2160	0.6070	0.0538*
H8	−0.1383	−0.1694	0.6624	0.0758*
H9	−0.1793	−0.2041	0.4875	0.0837*
H10	−0.1625	−0.0559	0.3733	0.0787*
H11	−0.0980	0.1257	0.4291	0.0687*
H13	−0.0638	0.2861	0.8117	0.0536*
H14	0.0402	0.4113	0.7920	0.0584*
H17	0.0329	0.2581	1.1453	0.0714*
H18	0.1116	0.4240	1.2205	0.0834*
H19	0.1735	0.5593	1.1217	0.0844*
H20	0.1557	0.5353	0.9465	0.0720*
H22	−0.0163	0.4159	0.5707	0.0662*
H23	−0.1139	0.5777	0.5437	0.0833*
H24	−0.2626	0.5624	0.5744	0.0793*
H25	−0.3110	0.3856	0.6347	0.0755*
H26	−0.2145	0.2231	0.6594	0.0645*
H28	0.1912	0.1802	0.9006	0.0663*
H29	0.3276	0.1325	0.8506	0.0860*
H30	0.3779	0.2380	0.7231	0.1061*
H31	0.2876	0.3867	0.6400	0.1057*
H32	0.1486	0.4334	0.6862	0.0795*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.144 (3)	0.069 (2)	0.054 (2)	−0.023 (2)	−0.006 (2)	0.010 (2)
O2	0.154 (3)	0.096 (2)	0.045 (2)	−0.054 (2)	0.009 (2)	0.005 (2)
C3	0.059 (3)	0.049 (2)	0.049 (2)	0.002 (2)	−0.003 (2)	0.001 (2)
C4	0.047 (2)	0.050 (2)	0.040 (2)	−0.003 (2)	0.001 (2)	−0.002 (2)
C5	0.046 (2)	0.050 (2)	0.039 (2)	0.005 (2)	0.008 (2)	0.002 (2)
C6	0.043 (2)	0.055 (3)	0.039 (2)	0.010 (2)	0.003 (2)	−0.009 (2)
C7	0.045 (2)	0.049 (2)	0.049 (2)	0.003 (2)	0.003 (2)	−0.009 (2)
C8	0.064 (3)	0.052 (3)	0.070 (3)	−0.001 (2)	0.003 (2)	−0.011 (2)
C9	0.063 (3)	0.066 (3)	0.073 (3)	0.012 (2)	−0.008 (2)	−0.028 (3)
C10	0.057 (3)	0.078 (3)	0.053 (3)	0.023 (3)	−0.012 (2)	−0.026 (3)
C11	0.056 (3)	0.067 (3)	0.047 (2)	0.022 (2)	0.003 (2)	−0.007 (2)
C12	0.066 (3)	0.065 (3)	0.047 (2)	−0.014 (2)	0.015 (2)	−0.002 (2)
C13	0.044 (2)	0.050 (2)	0.038 (2)	0.000 (2)	0.004 (2)	−0.002 (2)
C14	0.053 (2)	0.045 (2)	0.045 (2)	0.002 (2)	0.002 (2)	0.002 (2)
C15	0.047 (2)	0.044 (2)	0.052 (2)	0.006 (2)	0.003 (2)	−0.007 (2)
C16	0.049 (2)	0.048 (2)	0.042 (2)	0.004 (2)	0.001 (2)	−0.007 (2)
C17	0.064 (3)	0.066 (3)	0.046 (2)	0.014 (2)	0.003 (2)	−0.008 (2)
C18	0.067 (3)	0.084 (3)	0.051 (2)	0.019 (3)	−0.006 (2)	−0.025 (3)
C19	0.051 (3)	0.072 (3)	0.084 (3)	0.008 (2)	0.004 (2)	−0.039 (3)
C20	0.054 (3)	0.053 (3)	0.073 (3)	0.003 (2)	0.011 (2)	−0.016 (2)
C21	0.046 (2)	0.052 (2)	0.034 (2)	0.001 (2)	0.004 (2)	0.003 (2)
C22	0.060 (3)	0.058 (3)	0.049 (2)	0.006 (2)	0.016 (2)	0.011 (2)
C23	0.097 (4)	0.054 (3)	0.060 (3)	0.004 (3)	0.021 (2)	0.013 (2)
C24	0.082 (3)	0.061 (3)	0.052 (3)	0.024 (3)	0.007 (2)	−0.001 (2)
C25	0.050 (3)	0.069 (3)	0.068 (3)	0.009 (3)	0.007 (2)	−0.012 (2)
C26	0.050 (2)	0.055 (3)	0.057 (2)	−0.002 (2)	0.010 (2)	−0.004 (2)
C27	0.046 (2)	0.041 (2)	0.046 (2)	−0.008 (2)	0.004 (2)	−0.003 (2)
C28	0.058 (3)	0.055 (3)	0.053 (2)	0.000 (2)	0.011 (2)	−0.004 (2)
C29	0.057 (3)	0.068 (3)	0.088 (3)	0.006 (2)	0.008 (2)	−0.022 (3)
C30	0.056 (3)	0.129 (5)	0.084 (4)	−0.018 (3)	0.023 (3)	−0.040 (4)
C31	0.074 (4)	0.132 (5)	0.064 (3)	−0.039 (3)	0.029 (3)	−0.005 (3)
C32	0.067 (3)	0.075 (3)	0.057 (2)	−0.023 (2)	0.011 (2)	0.006 (2)

Geometric parameters (Å, º)

O1—C3	1.361 (5)	C16—C17	1.393 (5)
O1—H1	0.820	C17—C18	1.375 (6)
O2—C12	1.219 (6)	C17—H17	0.950
C3—C4	1.544 (5)	C18—C19	1.382 (7)
C3—C7	1.501 (5)	C18—H18	0.950
C3—H3	0.950	C19—C20	1.382 (6)
C4—C5	1.561 (4)	C19—H19	0.950
C4—C13	1.519 (5)	C20—H20	0.950
C4—H4	0.950	C21—C22	1.375 (5)
C5—C6	1.504 (5)	C21—C26	1.392 (5)
C5—C21	1.520 (5)	C22—C23	1.385 (6)
C5—H5	0.950	C22—H22	0.950
C6—C7	1.378 (5)	C23—C24	1.376 (7)
C6—C11	1.390 (5)	C23—H23	0.950
C7—C8	1.377 (5)	C24—C25	1.367 (6)
C8—C9	1.388 (6)	C24—H24	0.950
C8—H8	0.950	C25—C26	1.380 (6)
C9—C10	1.373 (6)	C25—H25	0.950
C9—H9	0.950	C26—H26	0.950
C10—C11	1.380 (6)	C27—C28	1.380 (5)
C10—H10	0.950	C27—C32	1.378 (6)
C11—H11	0.950	C28—C29	1.375 (6)
C12—C13	1.525 (5)	C28—H28	0.950
C12—C16	1.475 (5)	C29—C30	1.371 (8)
C13—C14	1.560 (5)	C29—H29	0.950
C13—H13	0.950	C30—C31	1.354 (8)
C14—C15	1.515 (5)	C30—H30	0.950
C14—C27	1.523 (5)	C31—C32	1.385 (7)
C14—H14	0.950	C31—H31	0.950
C15—C16	1.366 (5)	C32—H32	0.950
C15—C20	1.377 (5)
C3—O1—H1	109.5	C14—C15—C20	127.7 (3)
O1—C3—C4	116.6 (3)	C16—C15—C20	120.3 (3)
O1—C3—C7	111.5 (3)	C12—C16—C15	110.3 (3)
O1—C3—H3	108.1	C12—C16—C17	127.9 (3)
C4—C3—C7	104.3 (3)	C15—C16—C17	121.8 (3)
C4—C3—H3	108.1	C16—C17—C18	118.0 (4)
C7—C3—H3	108.1	C16—C17—H17	121.0
C3—C4—C5	105.2 (3)	C18—C17—H17	121.0
C3—C4—C13	116.6 (3)	C17—C18—C19	120.1 (4)
C3—C4—H4	105.8	C17—C18—H18	119.9
C5—C4—C13	116.6 (3)	C19—C18—H18	119.9
C5—C4—H4	105.8	C18—C19—C20	121.4 (4)
C13—C4—H4	105.8	C18—C19—H19	119.3
C4—C5—C6	103.1 (3)	C20—C19—H19	119.3
C4—C5—C21	116.1 (3)	C15—C20—C19	118.4 (4)
C4—C5—H5	108.3	C15—C20—H20	120.8
C6—C5—C21	112.4 (3)	C19—C20—H20	120.8
C6—C5—H5	108.3	C5—C21—C22	120.9 (3)
C21—C5—H5	108.3	C5—C21—C26	122.0 (3)
C5—C6—C7	112.0 (3)	C22—C21—C26	117.1 (3)
C5—C6—C11	128.9 (3)	C21—C22—C23	121.9 (4)
C7—C6—C11	119.1 (3)	C21—C22—H22	119.1
C3—C7—C6	110.4 (3)	C23—C22—H22	119.0
C3—C7—C8	127.5 (3)	C22—C23—C24	120.0 (4)
C6—C7—C8	122.0 (3)	C22—C23—H23	120.0
C7—C8—C9	118.3 (4)	C24—C23—H23	120.0
C7—C8—H8	120.8	C23—C24—C25	119.2 (4)
C9—C8—H8	120.8	C23—C24—H24	120.4
C8—C9—C10	120.2 (4)	C25—C24—H24	120.4
C8—C9—H9	119.9	C24—C25—C26	120.6 (4)
C10—C9—H9	119.9	C24—C25—H25	119.7
C9—C10—C11	121.1 (4)	C26—C25—H25	119.7
C9—C10—H10	119.4	C21—C26—C25	121.2 (4)
C11—C10—H10	119.5	C21—C26—H26	119.4
C6—C11—C10	119.2 (4)	C25—C26—H26	119.4
C6—C11—H11	120.4	C14—C27—C28	120.8 (3)
C10—C11—H11	120.4	C14—C27—C32	120.9 (3)
O2—C12—C13	126.0 (3)	C28—C27—C32	118.2 (4)
O2—C12—C16	125.6 (3)	C27—C28—C29	120.2 (4)
C13—C12—C16	106.4 (3)	C27—C28—H28	119.9
C4—C13—C12	118.7 (3)	C29—C28—H28	119.9
C4—C13—C14	116.7 (3)	C28—C29—C30	121.1 (4)
C4—C13—H13	105.1	C28—C29—H29	119.5
C12—C13—C14	104.7 (3)	C30—C29—H29	119.4
C12—C13—H13	105.2	C29—C30—C31	119.2 (5)
C14—C13—H13	105.1	C29—C30—H30	120.4
C13—C14—C15	102.5 (3)	C31—C30—H30	120.4
C13—C14—C27	116.1 (3)	C30—C31—C32	120.3 (5)
C13—C14—H14	108.8	C30—C31—H31	119.8
C15—C14—C27	111.5 (3)	C32—C31—H31	119.8
C15—C14—H14	108.8	C27—C32—C31	121.0 (4)
C27—C14—H14	108.8	C27—C32—H32	119.5
C14—C15—C16	111.9 (3)	C31—C32—H32	119.5
O1—C3—C4—C5	145.2 (3)	C11—C6—C5—C21	66.4 (5)
O1—C3—C4—C13	−83.9 (4)	C12—C13—C14—C15	−19.6 (3)
O1—C3—C7—C6	−141.9 (3)	C12—C13—C14—C27	102.2 (3)
O1—C3—C7—C8	38.8 (5)	C12—C16—C15—C14	−2.6 (4)
O2—C12—C13—C4	−44.2 (6)	C12—C16—C15—C20	−179.9 (3)
O2—C12—C13—C14	−176.5 (4)	C12—C16—C17—C18	−179.4 (4)
O2—C12—C16—C15	−175.4 (4)	C13—C4—C5—C21	−27.9 (4)
O2—C12—C16—C17	3.8 (7)	C13—C12—C16—C15	−10.7 (4)
C3—C4—C5—C6	−20.3 (3)	C13—C12—C16—C17	168.5 (4)
C3—C4—C5—C21	103.0 (3)	C13—C14—C15—C16	14.3 (4)
C3—C4—C13—C12	40.5 (4)	C13—C14—C15—C20	−168.7 (4)
C3—C4—C13—C14	167.3 (3)	C13—C14—C27—C28	−59.9 (4)
C3—C7—C6—C5	2.2 (4)	C13—C14—C27—C32	123.2 (3)
C3—C7—C6—C11	−178.2 (3)	C14—C13—C12—C16	18.9 (4)
C3—C7—C8—C9	178.3 (4)	C14—C15—C16—C17	178.2 (3)
C4—C3—C7—C6	−15.3 (4)	C14—C15—C20—C19	−177.4 (4)
C4—C3—C7—C8	165.4 (4)	C14—C27—C28—C29	−177.7 (3)
C4—C5—C6—C7	11.7 (4)	C14—C27—C32—C31	176.9 (4)
C4—C5—C6—C11	−167.9 (4)	C15—C14—C27—C28	57.0 (4)
C4—C5—C21—C22	114.1 (4)	C15—C14—C27—C32	−119.9 (4)
C4—C5—C21—C26	−67.1 (4)	C15—C16—C17—C18	−0.3 (6)
C4—C13—C12—C16	151.2 (3)	C15—C20—C19—C18	−0.2 (6)
C4—C13—C14—C15	−153.1 (3)	C16—C15—C14—C27	−110.7 (3)
C4—C13—C14—C27	−31.2 (4)	C16—C15—C20—C19	−0.7 (5)
C5—C4—C3—C7	21.8 (3)	C16—C17—C18—C19	−0.6 (6)
C5—C4—C13—C12	165.9 (3)	C17—C16—C15—C20	0.9 (6)
C5—C4—C13—C14	−67.3 (4)	C17—C18—C19—C20	0.8 (6)
C5—C6—C7—C8	−178.5 (3)	C20—C15—C14—C27	66.3 (5)
C5—C6—C11—C10	179.6 (4)	C21—C22—C23—C24	0.0 (6)
C5—C21—C22—C23	178.9 (3)	C21—C26—C25—C24	1.0 (6)
C5—C21—C26—C25	−179.4 (3)	C22—C21—C26—C25	−0.5 (5)
C6—C5—C4—C13	−151.3 (3)	C22—C23—C24—C25	0.5 (6)
C6—C5—C21—C22	−127.6 (3)	C23—C22—C21—C26	0.0 (5)
C6—C5—C21—C26	51.3 (4)	C23—C24—C25—C26	−1.0 (6)
C6—C7—C8—C9	−0.9 (6)	C27—C28—C29—C30	1.5 (6)
C6—C11—C10—C9	−1.5 (6)	C27—C32—C31—C30	0.1 (7)
C7—C3—C4—C13	152.8 (3)	C28—C27—C32—C31	−0.1 (6)
C7—C6—C5—C21	−114.1 (3)	C28—C29—C30—C31	−1.5 (7)
C7—C6—C11—C10	0.1 (5)	C29—C28—C27—C32	−0.7 (5)
C7—C8—C9—C10	−0.5 (6)	C29—C30—C31—C32	0.7 (8)
C8—C7—C6—C11	1.1 (6)	C29—C30—C31—C32	0.7 (8)
C8—C9—C10—C11	1.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.19	2.841 (4)	136