1-[(2-Hydr­oxy-1-naphth­yl)(phen­yl)meth­yl]-2-naphthol ethanol solvate

In the title compound, C₂₇H₂₀O₂·C₂H₆O, intra- and inter­molecular O—H...O hydrogen bonds link the mol­ecules and seem to be effective in the stabilization of the crystal structure. All the H atoms in the hydroxyl groups are disordered.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.051
• wR factor = 0.139
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.67 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.50 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O3     -   C29     ..       9.33 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT410_ALERT_2_C Short Intra H...H Contact  H7     ..  H11     ..       1.90 Ang.
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........       H10B
                    O1     H10B
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........       H10B
                    H10B   O1
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........       H10B
                    O1     H10B   O1
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: maXus (Mackay et al., 1999).

(I)

Crystal data

C27H20O2·C2H6O	Z = 2
Mr = 422.5	F(000) = 448
Triclinic, P1	Dx = 1.272 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.691 (2) Å	Cell parameters from 34 reflections
b = 10.8185 (13) Å	θ = 8.5–20.6°
c = 12.492 (4) Å	µ = 0.08 mm^−1
α = 82.20 (2)°	T = 298 K
β = 78.20 (2)°	Fragment, colourless
γ = 73.872 (15)°	0.43 × 0.41 × 0.15 mm
V = 1100.6 (5) Å^3

Data collection

Bruker–Nonius KappaCCD diffractometer	Rint = 0.036
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 4.7°
φ & ω scans	h = −11→11
22213 measured reflections	k = −14→14
5033 independent reflections	l = −16→16
3736 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.0615P)^2 + 0.6659P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
5033 reflections	Δρmax = 0.53 e Å^−3
290 parameters	Δρmin = −0.37 e Å^−3
0 restraints

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	Occ. (<1)
O1	0.38235 (14)	−0.00677 (12)	0.59244 (9)	0.0282 (3)
C5	0.19741 (18)	0.09715 (15)	0.74418 (12)	0.0178 (3)
O2	0.29836 (16)	−0.22355 (14)	0.64516 (10)	0.0383 (3)
C6	0.11896 (18)	0.21702 (14)	0.79199 (12)	0.0179 (3)
C4	0.31213 (18)	0.09982 (15)	0.64980 (12)	0.0196 (3)
C3	0.3619 (2)	0.21205 (16)	0.60582 (13)	0.0243 (4)
C12	0.29202 (18)	−0.14316 (15)	0.81467 (13)	0.0193 (3)
C11	0.15028 (18)	−0.02562 (14)	0.79678 (12)	0.0169 (3)
C1	0.16923 (19)	0.33052 (15)	0.74716 (13)	0.0210 (3)
C22	0.01862 (18)	−0.05710 (15)	0.74846 (12)	0.0201 (3)
C9	−0.0321 (2)	0.45680 (16)	0.88144 (14)	0.0275 (4)
C21	0.35899 (18)	−0.15980 (15)	0.91317 (13)	0.0206 (3)
C20	0.31583 (19)	−0.06402 (17)	0.98853 (13)	0.0234 (4)
C7	−0.01252 (19)	0.23052 (16)	0.88241 (13)	0.0227 (3)
C16	0.4738 (2)	−0.27780 (17)	0.93867 (15)	0.0285 (4)
C2	0.2943 (2)	0.32361 (16)	0.65414 (13)	0.0248 (4)
C8	−0.0853 (2)	0.34649 (16)	0.92522 (14)	0.0260 (4)
C10	0.0927 (2)	0.44850 (16)	0.79379 (14)	0.0259 (4)
C13	0.3491 (2)	−0.23994 (16)	0.74466 (14)	0.0254 (4)
C23	−0.0416 (2)	−0.16229 (17)	0.79492 (15)	0.0275 (4)
C27	−0.0494 (2)	0.01873 (17)	0.66307 (14)	0.0280 (4)
C15	0.5190 (2)	−0.37528 (17)	0.86558 (18)	0.0364 (5)
C19	0.3785 (2)	−0.0850 (2)	1.08351 (14)	0.0321 (4)
C14	0.4597 (2)	−0.35658 (17)	0.77093 (17)	0.0337 (4)
C18	0.4895 (2)	−0.2019 (2)	1.10796 (16)	0.0405 (5)
C17	0.5361 (2)	−0.2948 (2)	1.03740 (17)	0.0392 (5)
C26	−0.1742 (2)	−0.0098 (2)	0.62474 (16)	0.0371 (5)
C24	−0.1645 (2)	−0.19128 (18)	0.75591 (17)	0.0347 (4)
C25	−0.2313 (2)	−0.1148 (2)	0.67066 (17)	0.0366 (4)
O3	0.36306 (17)	−0.40401 (14)	0.50726 (12)	0.0423 (4)
C28	0.0803 (3)	−0.3473 (3)	0.4929 (2)	0.0599 (7)
C29	0.2501 (3)	−0.3911 (3)	0.4351 (2)	0.0620 (7)
H1OA	0.3349	−0.0727	0.5997	0.034*	0.50
H1OB	0.4549	−0.0068	0.5257	0.034*	0.50
H2OA	0.3103	−0.2814	0.5999	0.046*	0.50
H2OB	0.3274	−0.1441	0.6269	0.046*	0.50
H3	0.4472	0.2108	0.5409	0.029*
H11	0.0952	−0.0070	0.8738	0.020*
H9	−0.0815	0.5398	0.9064	0.033*
H20	0.2500	0.0238	0.9654	0.028*
H7	−0.0556	0.1516	0.9110	0.027*
H2	0.3312	0.4016	0.6256	0.030*
H8	−0.1821	0.3538	0.9868	0.031*
H10	0.1343	0.5291	0.7627	0.031*
H23	0.0046	−0.2207	0.8597	0.033*
H27	−0.0211	0.0980	0.6348	0.034*
H15	0.5972	−0.4588	0.8839	0.044*
H19	0.3518	−0.0156	1.1362	0.039*
H14	0.4849	−0.4187	0.7210	0.040*
H18	0.5225	−0.2099	1.1776	0.049*
H17	0.6208	−0.3838	1.0461	0.047*
H26	−0.2207	0.0444	0.5615	0.044*
H24	−0.2035	−0.2704	0.7873	0.042*
H25	−0.3227	−0.1348	0.6417	0.044*
H3A	0.3461	−0.3356	0.5344	0.063*	0.50
H3B	0.4500	−0.4647	0.5028	0.063*	0.50
H28A	0.0590	−0.4096	0.5527	0.090*
H28B	0.0070	−0.3384	0.4427	0.090*
H28C	0.0648	−0.2655	0.5209	0.090*
H29A	0.2656	−0.4736	0.4066	0.074*
H29B	0.2707	−0.3293	0.3735	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0272 (6)	0.0309 (7)	0.0237 (6)	−0.0014 (5)	−0.0008 (5)	−0.0107 (5)
C5	0.0154 (7)	0.0200 (7)	0.0181 (7)	−0.0046 (6)	−0.0045 (6)	−0.0001 (6)
O2	0.0383 (8)	0.0545 (9)	0.0269 (7)	−0.0177 (7)	0.0014 (6)	−0.0181 (6)
C6	0.0159 (7)	0.0197 (7)	0.0180 (7)	−0.0042 (6)	−0.0044 (6)	0.0001 (6)
C4	0.0190 (7)	0.0224 (8)	0.0169 (7)	−0.0040 (6)	−0.0041 (6)	−0.0014 (6)
C3	0.0215 (8)	0.0304 (9)	0.0186 (8)	−0.0080 (7)	0.0009 (6)	0.0024 (7)
C12	0.0163 (7)	0.0190 (7)	0.0214 (8)	−0.0058 (6)	−0.0002 (6)	0.0007 (6)
C11	0.0169 (7)	0.0182 (7)	0.0152 (7)	−0.0046 (6)	−0.0018 (6)	−0.0011 (6)
C1	0.0206 (8)	0.0210 (8)	0.0210 (8)	−0.0055 (6)	−0.0052 (6)	0.0024 (6)
C22	0.0179 (7)	0.0225 (8)	0.0196 (8)	−0.0059 (6)	−0.0016 (6)	−0.0025 (6)
C9	0.0296 (9)	0.0205 (8)	0.0302 (9)	−0.0018 (7)	−0.0053 (7)	−0.0045 (7)
C21	0.0148 (7)	0.0221 (8)	0.0241 (8)	−0.0079 (6)	−0.0021 (6)	0.0056 (6)
C20	0.0202 (8)	0.0293 (9)	0.0215 (8)	−0.0103 (7)	−0.0036 (6)	0.0031 (7)
C7	0.0208 (8)	0.0220 (8)	0.0237 (8)	−0.0064 (6)	0.0002 (6)	−0.0008 (6)
C16	0.0166 (8)	0.0273 (9)	0.0376 (10)	−0.0057 (7)	−0.0039 (7)	0.0096 (7)
C2	0.0247 (8)	0.0241 (8)	0.0247 (8)	−0.0093 (7)	−0.0029 (7)	0.0053 (7)
C8	0.0237 (8)	0.0249 (8)	0.0250 (8)	−0.0031 (7)	0.0021 (6)	−0.0033 (7)
C10	0.0291 (9)	0.0196 (8)	0.0291 (9)	−0.0070 (7)	−0.0060 (7)	0.0011 (7)
C13	0.0212 (8)	0.0253 (8)	0.0288 (9)	−0.0077 (7)	0.0019 (7)	−0.0053 (7)
C23	0.0236 (8)	0.0276 (9)	0.0310 (9)	−0.0089 (7)	−0.0059 (7)	0.0053 (7)
C27	0.0310 (9)	0.0306 (9)	0.0257 (9)	−0.0142 (7)	−0.0099 (7)	0.0067 (7)
C15	0.0207 (9)	0.0217 (9)	0.0586 (13)	−0.0006 (7)	−0.0016 (8)	0.0058 (8)
C19	0.0279 (9)	0.0488 (11)	0.0241 (9)	−0.0184 (8)	−0.0065 (7)	0.0024 (8)
C14	0.0264 (9)	0.0220 (9)	0.0485 (12)	−0.0041 (7)	0.0042 (8)	−0.0098 (8)
C18	0.0306 (10)	0.0620 (14)	0.0314 (10)	−0.0168 (10)	−0.0165 (8)	0.0153 (10)
C17	0.0244 (9)	0.0432 (11)	0.0456 (12)	−0.0078 (8)	−0.0129 (8)	0.0200 (9)
C26	0.0391 (11)	0.0452 (11)	0.0339 (10)	−0.0169 (9)	−0.0204 (8)	0.0070 (8)
C24	0.0288 (9)	0.0315 (10)	0.0480 (11)	−0.0158 (8)	−0.0087 (8)	0.0017 (8)
C25	0.0316 (10)	0.0428 (11)	0.0435 (11)	−0.0163 (9)	−0.0154 (8)	−0.0043 (9)
O3	0.0343 (7)	0.0411 (8)	0.0484 (9)	−0.0081 (6)	−0.0084 (6)	0.0050 (7)
C28	0.0590 (16)	0.0581 (15)	0.0632 (16)	−0.0117 (12)	−0.0228 (13)	0.0037 (12)
C29	0.0693 (17)	0.0573 (15)	0.0512 (15)	0.0045 (13)	−0.0146 (13)	−0.0145 (12)

Geometric parameters (Å, º)

O1—C4	1.3674 (19)	C24—C25	1.380 (3)
C5—C4	1.382 (2)	O3—C29	1.431 (3)
C5—C6	1.434 (2)	C28—C29	1.481 (4)
C5—C11	1.523 (2)	O1—H1OA	0.9046
O2—C13	1.375 (2)	O1—H1OB	0.9371
C6—C1	1.422 (2)	O2—H2OA	0.8705
C6—C7	1.424 (2)	O2—H2OB	0.9477
C4—C3	1.406 (2)	C3—H3	0.9788
C3—C2	1.351 (2)	C11—H11	1.0028
C12—C13	1.375 (2)	C9—H9	0.9460
C12—C21	1.435 (2)	C20—H20	1.0022
C12—C11	1.533 (2)	C7—H7	1.0182
C11—C22	1.531 (2)	C2—H2	0.9819
C1—C10	1.408 (2)	C8—H8	1.0103
C1—C2	1.414 (2)	C10—H10	1.0335
C22—C27	1.382 (2)	C23—H23	1.0336
C22—C23	1.390 (2)	C27—H27	0.9589
C9—C10	1.367 (2)	C15—H15	0.9990
C9—C8	1.401 (2)	C19—H19	1.0131
C21—C20	1.416 (2)	C14—H14	0.9294
C21—C16	1.428 (2)	C18—H18	0.9561
C20—C19	1.370 (2)	C17—H17	1.0447
C7—C8	1.365 (2)	C26—H26	1.0023
C16—C15	1.409 (3)	C24—H24	1.0091
C16—C17	1.416 (3)	C25—H25	1.0203
C13—C14	1.402 (2)	O3—H3A	0.8200
C23—C24	1.384 (3)	O3—H3B	0.8500
C27—C26	1.393 (3)	C28—H28A	0.9600
C15—C14	1.353 (3)	C28—H28B	0.9600
C19—C18	1.400 (3)	C28—H28C	0.9600
C18—C17	1.349 (3)	C29—H29A	0.9700
C26—C25	1.373 (3)	C29—H29B	0.9700
C4—C5—C6	117.39 (14)	H2OA—O2—H2OB	125.7
C4—C5—C11	122.95 (14)	C2—C3—H3	118.7
C6—C5—C11	119.66 (13)	C4—C3—H3	121.1
C1—C6—C7	116.88 (14)	C5—C11—H11	105.7
C1—C6—C5	119.92 (14)	C22—C11—H11	103.1
C7—C6—C5	123.18 (14)	C12—C11—H11	102.5
O1—C4—C5	121.72 (14)	C10—C9—H9	116.6
O1—C4—C3	115.88 (14)	C8—C9—H9	123.8
C5—C4—C3	122.40 (15)	C19—C20—H20	120.6
C2—C3—C4	120.18 (14)	C21—C20—H20	117.5
C13—C12—C21	117.99 (14)	C8—C7—H7	120.8
C13—C12—C11	122.59 (14)	C6—C7—H7	117.5
C21—C12—C11	119.17 (13)	C3—C2—H2	120.7
C5—C11—C22	114.33 (12)	C1—C2—H2	118.5
C5—C11—C12	115.76 (12)	C7—C8—H8	119.6
C22—C11—C12	113.46 (13)	C9—C8—H8	119.6
C10—C1—C2	120.68 (15)	C9—C10—H10	119.7
C10—C1—C6	120.17 (14)	C1—C10—H10	119.3
C2—C1—C6	119.14 (15)	C24—C23—H23	118.5
C27—C22—C23	118.02 (15)	C22—C23—H23	120.5
C27—C22—C11	122.60 (14)	C22—C27—H27	120.6
C23—C22—C11	119.31 (14)	C26—C27—H27	118.1
C10—C9—C8	119.58 (16)	C14—C15—H15	119.9
C20—C21—C16	117.31 (15)	C16—C15—H15	119.1
C20—C21—C12	123.03 (14)	C20—C19—H19	121.8
C16—C21—C12	119.66 (15)	C18—C19—H19	117.5
C19—C20—C21	121.34 (16)	C15—C14—H14	123.8
C8—C7—C6	121.59 (15)	C13—C14—H14	115.8
C15—C16—C17	121.89 (17)	C17—C18—H18	125.0
C15—C16—C21	118.76 (16)	C19—C18—H18	115.0
C17—C16—C21	119.34 (18)	C18—C17—H17	126.2
C3—C2—C1	120.76 (15)	C16—C17—H17	112.3
C7—C8—C9	120.78 (15)	C25—C26—H26	119.2
C9—C10—C1	120.99 (15)	C27—C26—H26	120.2
C12—C13—O2	119.94 (15)	C25—C24—H24	119.0
C12—C13—C14	122.01 (16)	C23—C24—H24	120.6
O2—C13—C14	118.05 (16)	C26—C25—H25	119.7
C24—C23—C22	121.01 (16)	C24—C25—H25	121.1
C22—C27—C26	120.85 (16)	C29—O3—H3A	109.5
C14—C15—C16	121.02 (16)	C29—O3—H3B	120.9
C20—C19—C18	120.65 (19)	H3A—O3—H3B	126.6
C15—C14—C13	120.38 (17)	C29—C28—H28A	109.5
C17—C18—C19	119.90 (17)	C29—C28—H28B	109.5
C18—C17—C16	121.44 (17)	H28A—C28—H28B	109.5
C25—C26—C27	120.50 (17)	C29—C28—H28C	109.5
C25—C24—C23	120.41 (17)	H28A—C28—H28C	109.5
C26—C25—C24	119.19 (17)	H28B—C28—H28C	109.5
O3—C29—C28	111.0 (2)	O3—C29—H29A	109.4
C4—O1—H1OA	121.4	C28—C29—H29A	109.4
C4—O1—H1OB	123.9	O3—C29—H29B	109.4
H1OA—O1—H1OB	110.5	C28—C29—H29B	109.4
C13—O2—H2OA	128.5	H29A—C29—H29B	108.0
C13—O2—H2OB	91.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1OA···O2	0.90	1.75	2.6080 (19)	158
O1—H10B···O1^i	0.94	1.84	2.7713 (17)	170
O2—H2OA···O3	0.87	1.78	2.646 (2)	172
O3—H3B···O3^ii	0.85	1.83	2.6817 (19)	180

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y−1, −z+1.