Download citation
Download citation
link to html
In the title compound, C22H16O5, the two naphthyl units are approximately perpendicular. The 3-naphthyl­carboxyl group and the ortho-hydroxyl group are involved in an inter­molecular O—H...O hydrogen bond with O...O = 2.606 (2) Å. Mol­ecules related by a glide plane are linked by an intermolecular O—H...O hydrogen bond with O...O = 2.747 (2) Å, creating a spiral. A solvent mol­ecule is an acceptor in an O—H...O hydrogen bond with O...O = 2.700 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051889/kp2056sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051889/kp2056Isup2.hkl
Contains datablock I

CCDC reference: 633901

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.040
  • wR factor = 0.119
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Methyl 2,2',7'-trihydroxy-1,1'-binaphthalene-3-carboxylate acetone solvate top
Crystal data top
C22H16O5·C3H6OF(000) = 880
Mr = 418.43Dx = 1.289 Mg m3
Monoclinic, P21/cMelting point: 454 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 13.477 (4) ÅCell parameters from 25 reflections
b = 12.062 (4) Åθ = 12–18°
c = 14.049 (4) ŵ = 0.09 mm1
β = 109.223 (6)°T = 293 K
V = 2156.5 (12) Å3Block, colourless
Z = 40.40 × 0.30 × 0.25 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4184 independent reflections
Radiation source: fine-focus sealed tube2707 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and\ w scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.957, Tmax = 0.971k = 914
11034 measured reflectionsl = 1716
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0542P)2 + 0.4103P]
where P = (Fo2 + 2Fc2)/3
4184 reflections(Δ/σ)max < 0.001
286 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.16 e Å3
Special details top

Experimental. IR (KBr, νcm-1) 3314 (Ar—OH), 3172, 2947, 2910, 1831 (CO), 1690, 1514, 1320, 1216, 825; 1H NMR (DMSO): δ 10.26 (s, 1H), 9.18 (s, 1H), 9.14 (s, 1H), 8.67 (s, 1H), 8.07–8.04 (m, 1H), 7.70 (d, J = 8.7 Hz, 1H), 7.66 (d, J = 8.7 Hz, 1H), 7.38–7.33 (m, 2H), 7.05 (d, J = 8.7 Hz, 1H), 7.01–6.98 (m, 1H), 6.76 (dd, J = 8.7, 2.1 Hz, 1H), 6.16 (s, 1H), 4.01 (s, 3H); 13C NMR (DMSO): δ 170.5, 156.3, 153.9, 137.5, 136.9, 136.2, 132.4, 130.4, 130.3, 129.8, 129.6, 127.6, 125.2, 124.5, 123.5, 119.3, 115.6, 115.1, 113.2, 107.9, 106.3, 53.8; FAB-MS, m*/z* (%): 360 ([M]+, 16). Analysis calculated for C22H16O5: C 73.33, H 4.48%; found: C 72.63, H 4.54.

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 (Å2) top
xyzUiso*/Ueq
C10.38132 (17)0.00879 (16)0.69682 (14)0.0597 (5)
C20.40538 (13)0.06862 (14)0.61593 (12)0.0460 (4)
C30.50706 (13)0.08238 (14)0.61746 (12)0.0470 (4)
H30.56150.05150.66990.056*
C40.53069 (12)0.14155 (13)0.54227 (12)0.0435 (4)
C50.63551 (14)0.15730 (17)0.54455 (15)0.0588 (5)
H50.69010.12420.59540.071*
C60.65771 (16)0.2195 (2)0.47434 (18)0.0742 (6)
H60.72710.23050.47770.089*
C70.57552 (17)0.2673 (2)0.39644 (18)0.0758 (6)
H70.59120.31070.34860.091*
C80.47325 (15)0.25172 (17)0.38902 (15)0.0590 (5)
H80.42020.28320.33560.071*
C90.44692 (13)0.18821 (13)0.46158 (12)0.0427 (4)
C100.34112 (12)0.17120 (13)0.45767 (12)0.0415 (4)
C110.32211 (13)0.11197 (14)0.53332 (13)0.0462 (4)
C120.25168 (12)0.21688 (14)0.37270 (12)0.0426 (4)
C130.22059 (13)0.16622 (15)0.28017 (13)0.0480 (4)
C140.13745 (14)0.20868 (16)0.19849 (13)0.0524 (5)
H140.11920.17430.13580.063*
C150.08415 (14)0.29957 (15)0.21130 (13)0.0527 (5)
H150.02850.32600.15730.063*
C160.11121 (13)0.35473 (14)0.30436 (12)0.0456 (4)
C170.05759 (14)0.44955 (16)0.31990 (14)0.0548 (5)
H170.00020.47540.26740.066*
C180.08707 (15)0.50417 (16)0.40895 (14)0.0575 (5)
H180.05020.56660.41730.069*
C190.17365 (14)0.46595 (14)0.48867 (13)0.0486 (4)
C200.22664 (13)0.37280 (14)0.47824 (12)0.0455 (4)
H200.28270.34760.53250.055*
C210.19743 (12)0.31431 (13)0.38620 (12)0.0421 (4)
C220.4490 (2)0.0765 (3)0.85632 (19)0.1184 (11)
H22A0.39450.04000.87450.178*
H22B0.51280.07630.91290.178*
H22C0.42850.15160.83700.178*
O10.29313 (13)0.01235 (15)0.69627 (12)0.0893 (5)
O20.46592 (12)0.01871 (12)0.77295 (10)0.0758 (4)
O30.22035 (9)0.09608 (13)0.52700 (11)0.0728 (4)
H3A0.21820.06120.57640.109*
O40.27330 (11)0.07307 (11)0.26864 (9)0.0671 (4)
H40.24920.05120.21030.101*
O50.20537 (11)0.52020 (11)0.57979 (9)0.0635 (4)
H5A0.17150.57760.57510.095*
C230.16069 (19)0.7582 (2)0.72903 (18)0.0896 (7)
H23C0.18950.68470.73680.134*
H23B0.11760.76680.77100.134*
H23A0.21680.81130.74850.134*
C240.09660 (15)0.77646 (17)0.62297 (16)0.0573 (5)
C250.03031 (18)0.8766 (2)0.59792 (18)0.0865 (7)
H25C0.00250.88500.52600.130*
H25B0.07180.94050.62690.130*
H25A0.02650.86970.62450.130*
O60.09691 (13)0.71208 (12)0.55727 (12)0.0806 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0650 (13)0.0557 (12)0.0530 (12)0.0068 (10)0.0123 (10)0.0111 (9)
C20.0493 (10)0.0420 (10)0.0423 (9)0.0057 (8)0.0093 (8)0.0021 (8)
C30.0486 (10)0.0414 (10)0.0412 (9)0.0083 (8)0.0013 (8)0.0036 (8)
C40.0424 (9)0.0400 (9)0.0437 (9)0.0020 (7)0.0082 (8)0.0092 (8)
C50.0426 (10)0.0645 (12)0.0629 (12)0.0015 (9)0.0090 (9)0.0109 (10)
C60.0484 (12)0.0900 (16)0.0864 (16)0.0077 (11)0.0250 (12)0.0005 (13)
C70.0684 (14)0.0868 (16)0.0798 (15)0.0072 (12)0.0347 (13)0.0151 (13)
C80.0582 (12)0.0627 (12)0.0566 (11)0.0011 (9)0.0196 (9)0.0095 (10)
C90.0450 (9)0.0391 (9)0.0422 (9)0.0014 (7)0.0117 (8)0.0064 (8)
C100.0430 (9)0.0390 (9)0.0388 (9)0.0055 (7)0.0086 (7)0.0020 (7)
C110.0412 (9)0.0497 (10)0.0451 (10)0.0044 (8)0.0108 (8)0.0038 (8)
C120.0411 (9)0.0458 (10)0.0388 (9)0.0036 (7)0.0103 (7)0.0046 (7)
C130.0481 (10)0.0487 (10)0.0445 (10)0.0050 (8)0.0115 (8)0.0019 (8)
C140.0525 (11)0.0612 (12)0.0378 (9)0.0000 (9)0.0070 (8)0.0010 (8)
C150.0468 (10)0.0627 (12)0.0408 (10)0.0070 (9)0.0040 (8)0.0136 (9)
C160.0444 (9)0.0500 (10)0.0411 (9)0.0036 (8)0.0123 (8)0.0113 (8)
C170.0533 (11)0.0574 (12)0.0488 (11)0.0168 (9)0.0102 (9)0.0170 (9)
C180.0670 (12)0.0492 (11)0.0576 (12)0.0202 (9)0.0225 (10)0.0128 (9)
C190.0613 (11)0.0429 (10)0.0427 (10)0.0045 (8)0.0186 (8)0.0061 (8)
C200.0477 (10)0.0459 (10)0.0401 (9)0.0065 (8)0.0106 (8)0.0076 (8)
C210.0422 (9)0.0431 (9)0.0397 (9)0.0010 (7)0.0116 (7)0.0076 (8)
C220.133 (2)0.132 (2)0.0718 (17)0.008 (2)0.0093 (16)0.0585 (17)
O10.0730 (11)0.1158 (14)0.0815 (11)0.0049 (9)0.0286 (8)0.0449 (10)
O20.0819 (10)0.0786 (10)0.0539 (8)0.0002 (8)0.0046 (7)0.0259 (7)
O30.0447 (7)0.0994 (11)0.0738 (10)0.0069 (7)0.0189 (7)0.0333 (8)
O40.0750 (9)0.0643 (9)0.0498 (8)0.0221 (7)0.0042 (7)0.0106 (7)
O50.0879 (10)0.0495 (8)0.0505 (8)0.0171 (7)0.0196 (7)0.0017 (6)
C230.0765 (16)0.0992 (19)0.0786 (16)0.0050 (14)0.0059 (13)0.0158 (14)
C240.0518 (11)0.0572 (12)0.0639 (12)0.0013 (9)0.0205 (10)0.0012 (10)
C250.0850 (16)0.0784 (16)0.0835 (16)0.0313 (13)0.0107 (13)0.0096 (13)
O60.1014 (12)0.0624 (9)0.0818 (10)0.0230 (8)0.0351 (9)0.0047 (8)
Geometric parameters (Å, º) top
C1—O11.213 (2)C15—H150.9300
C1—O21.323 (2)C16—C171.408 (2)
C1—C21.470 (3)C16—C211.425 (2)
C2—C31.373 (2)C17—C181.353 (3)
C2—C111.422 (2)C17—H170.9300
C3—C41.396 (2)C18—C191.403 (3)
C3—H30.9300C18—H180.9300
C4—C51.415 (2)C19—C201.365 (2)
C4—C91.426 (2)C19—O51.375 (2)
C5—C61.349 (3)C20—C211.411 (2)
C5—H50.9300C20—H200.9300
C6—C71.399 (3)C22—O21.444 (3)
C6—H60.9300C22—H22A0.9600
C7—C81.361 (3)C22—H22B0.9600
C7—H70.9300C22—H22C0.9600
C8—C91.411 (2)O3—H3A0.8200
C8—H80.9300O4—H40.8200
C9—C101.424 (2)O5—H5A0.8200
C10—C111.373 (2)C23—C241.472 (3)
C10—C121.495 (2)C23—H23C0.9600
C11—O31.358 (2)C23—H23B0.9600
C12—C131.371 (2)C23—H23A0.9600
C12—C211.429 (2)C24—O61.207 (2)
C13—O41.367 (2)C24—C251.475 (3)
C13—C141.410 (2)C25—H25C0.9600
C14—C151.355 (2)C25—H25B0.9600
C14—H140.9300C25—H25A0.9600
C15—C161.404 (2)
O1—C1—O2122.29 (19)C16—C15—H15119.3
O1—C1—C2124.29 (17)C15—C16—C17122.70 (16)
O2—C1—C2113.41 (18)C15—C16—C21118.82 (16)
C3—C2—C11118.92 (16)C17—C16—C21118.47 (16)
C3—C2—C1121.34 (16)C18—C17—C16121.98 (16)
C11—C2—C1119.72 (16)C18—C17—H17119.0
C2—C3—C4121.66 (15)C16—C17—H17119.0
C2—C3—H3119.2C17—C18—C19119.48 (17)
C4—C3—H3119.2C17—C18—H18120.3
C3—C4—C5121.75 (16)C19—C18—H18120.3
C3—C4—C9119.03 (15)C20—C19—O5118.59 (16)
C5—C4—C9119.21 (17)C20—C19—C18120.79 (17)
C6—C5—C4121.21 (18)O5—C19—C18120.60 (16)
C6—C5—H5119.4C19—C20—C21120.81 (15)
C4—C5—H5119.4C19—C20—H20119.6
C5—C6—C7119.47 (19)C21—C20—H20119.6
C5—C6—H6120.3C20—C21—C16118.42 (15)
C7—C6—H6120.3C20—C21—C12122.17 (14)
C8—C7—C6121.6 (2)C16—C21—C12119.41 (15)
C8—C7—H7119.2O2—C22—H22A109.5
C6—C7—H7119.2O2—C22—H22B109.5
C7—C8—C9120.59 (19)H22A—C22—H22B109.5
C7—C8—H8119.7O2—C22—H22C109.5
C9—C8—H8119.7H22A—C22—H22C109.5
C8—C9—C10122.51 (15)H22B—C22—H22C109.5
C8—C9—C4117.85 (16)C1—O2—C22116.90 (19)
C10—C9—C4119.63 (15)C11—O3—H3A109.5
C11—C10—C9119.01 (14)C13—O4—H4109.5
C11—C10—C12120.21 (15)C19—O5—H5A109.5
C9—C10—C12120.78 (15)C24—C23—H23C109.5
O3—C11—C10117.68 (14)C24—C23—H23B109.5
O3—C11—C2120.66 (15)H23C—C23—H23B109.5
C10—C11—C2121.66 (15)C24—C23—H23A109.5
C13—C12—C21118.83 (15)H23C—C23—H23A109.5
C13—C12—C10120.48 (15)H23B—C23—H23A109.5
C21—C12—C10120.69 (14)O6—C24—C23122.0 (2)
O4—C13—C12118.04 (15)O6—C24—C25119.93 (19)
O4—C13—C14120.45 (16)C23—C24—C25118.1 (2)
C12—C13—C14121.51 (16)C24—C25—H25C109.5
C15—C14—C13119.99 (17)C24—C25—H25B109.5
C15—C14—H14120.0H25C—C25—H25B109.5
C13—C14—H14120.0C24—C25—H25A109.5
C14—C15—C16121.38 (16)H25C—C25—H25A109.5
C14—C15—H15119.3H25B—C25—H25A109.5
O1—C1—C2—C3174.9 (2)C9—C10—C12—C1376.8 (2)
O2—C1—C2—C36.4 (3)C11—C10—C12—C2177.1 (2)
O1—C1—C2—C114.2 (3)C9—C10—C12—C21102.88 (18)
O2—C1—C2—C11174.54 (16)C21—C12—C13—O4179.95 (15)
C11—C2—C3—C42.6 (2)C10—C12—C13—O40.4 (2)
C1—C2—C3—C4178.31 (16)C21—C12—C13—C140.6 (3)
C2—C3—C4—C5178.99 (16)C10—C12—C13—C14179.07 (16)
C2—C3—C4—C90.4 (2)O4—C13—C14—C15178.50 (17)
C3—C4—C5—C6176.50 (18)C12—C13—C14—C152.1 (3)
C9—C4—C5—C62.9 (3)C13—C14—C15—C161.4 (3)
C4—C5—C6—C71.5 (3)C14—C15—C16—C17179.77 (17)
C5—C6—C7—C80.7 (4)C14—C15—C16—C210.7 (3)
C6—C7—C8—C91.3 (3)C15—C16—C17—C18177.50 (17)
C7—C8—C9—C10179.01 (18)C21—C16—C17—C181.5 (3)
C7—C8—C9—C40.1 (3)C16—C17—C18—C190.1 (3)
C3—C4—C9—C8177.26 (16)C17—C18—C19—C201.7 (3)
C5—C4—C9—C82.1 (2)C17—C18—C19—O5179.80 (17)
C3—C4—C9—C101.7 (2)O5—C19—C20—C21179.78 (15)
C5—C4—C9—C10178.91 (15)C18—C19—C20—C211.7 (3)
C8—C9—C10—C11177.46 (17)C19—C20—C21—C160.1 (2)
C4—C9—C10—C111.4 (2)C19—C20—C21—C12179.65 (16)
C8—C9—C10—C122.5 (2)C15—C16—C21—C20177.55 (15)
C4—C9—C10—C12178.56 (14)C17—C16—C21—C201.5 (2)
C9—C10—C11—O3179.32 (15)C15—C16—C21—C122.2 (2)
C12—C10—C11—O30.7 (2)C17—C16—C21—C12178.77 (15)
C9—C10—C11—C20.8 (2)C13—C12—C21—C20178.21 (16)
C12—C10—C11—C2179.15 (15)C10—C12—C21—C201.5 (2)
C3—C2—C11—O3177.27 (16)C13—C12—C21—C161.5 (2)
C1—C2—C11—O31.8 (3)C10—C12—C21—C16178.83 (15)
C3—C2—C11—C102.9 (3)O1—C1—O2—C220.5 (3)
C1—C2—C11—C10178.04 (16)C2—C1—O2—C22179.2 (2)
C11—C10—C12—C13103.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O60.821.882.700 (2)176
O3—H3A···O10.821.882.606 (2)148
O4—H4···O5i0.821.932.7466 (19)171
Symmetry code: (i) x, y+1/2, z1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds