Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033909/ci2414sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033909/ci2414Isup2.hkl |
CCDC reference: 657774
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.099
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared according to the reported procedure of Georghiou et al. (1996). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane.
H atoms were placed in calculated positions with C—H = 0.95–0.99 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C).
Pamoic acid or its derivatives or analogs are used in the pharmaceutical industry for the preparation of medicaments for the treatment of diseases characterized by deposits of amyloid aggregates. We report here the crystal structure of the title compound.
Bond lengths and angles in the title molecule (Fig. 1) are within normal ranges. Both naphthalene ring systems are slightly non-planar, with the dihedral angle between the two benzene rings being 5.06 (4)° for the C1—C10 ring system and 3.92 (3)° for the C15—C24 ring system. The two naphthalene ring systems are almost perpendicular, with a dihedral angle of 87.77 (2)°.
The molecular structure is stabilized by C—H···O hydrogen bonds (Table 1). The crystal structure is stabilized by π-π interactions between the naphthalene ring systems of the inversion related molecules, with a Cg1···Cg1i distance of 3.6311 (6) Å [symmetry code: (i) 1 - x, 1 - y, 1 - z] where Cg1 is the C4—C9 ring centroid. In addition, weak C—H···O intermolecular hydrogen bonds and C—H···π interactions involving the C15/C16/C21—C24 ring (centroid Cg2) are observed (Table 1).
For synthesis, see: Georghiou et al. (1996). For related structures, see: Haynes et al. (2006) and Liu et al. (2006).
Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. |
C27H24O6 | F(000) = 936 |
Mr = 444.46 | Dx = 1.351 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 19190 reflections |
a = 12.9871 (4) Å | θ = 3.0–27.5° |
b = 20.0999 (5) Å | µ = 0.10 mm−1 |
c = 8.7466 (3) Å | T = 153 K |
β = 106.798 (1)° | Block, colourless |
V = 2185.78 (11) Å3 | 0.59 × 0.58 × 0.58 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 4617 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.021 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −14→16 |
21180 measured reflections | k = −25→26 |
5007 independent reflections | l = −11→11 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.056P)2 + 0.7416P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
5007 reflections | Δρmax = 0.33 e Å−3 |
303 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0128 (11) |
C27H24O6 | V = 2185.78 (11) Å3 |
Mr = 444.46 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.9871 (4) Å | µ = 0.10 mm−1 |
b = 20.0999 (5) Å | T = 153 K |
c = 8.7466 (3) Å | 0.59 × 0.58 × 0.58 mm |
β = 106.798 (1)° |
Rigaku R-AXIS RAPID diffractometer | 4617 reflections with I > 2σ(I) |
21180 measured reflections | Rint = 0.021 |
5007 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.33 e Å−3 |
5007 reflections | Δρmin = −0.20 e Å−3 |
303 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.08724 (6) | 0.39859 (4) | 0.27018 (9) | 0.02037 (17) | |
O2 | 0.25890 (7) | 0.35292 (4) | −0.02411 (9) | 0.02536 (18) | |
O3 | 0.14283 (7) | 0.29602 (4) | 0.07285 (9) | 0.02582 (18) | |
O4 | 0.27501 (6) | 0.52935 (4) | 0.87194 (8) | 0.01955 (16) | |
O5 | 0.42601 (7) | 0.69099 (5) | 0.89705 (11) | 0.0326 (2) | |
O6 | 0.30271 (7) | 0.66608 (4) | 1.02247 (10) | 0.0298 (2) | |
C1 | 0.19780 (8) | 0.39958 (5) | 0.33629 (12) | 0.0168 (2) | |
C2 | 0.26229 (8) | 0.37440 (5) | 0.24159 (12) | 0.0180 (2) | |
C3 | 0.37214 (8) | 0.38001 (5) | 0.29508 (12) | 0.0197 (2) | |
H3 | 0.4143 | 0.3669 | 0.2278 | 0.024* | |
C4 | 0.42325 (8) | 0.40517 (5) | 0.44938 (12) | 0.0184 (2) | |
C5 | 0.53713 (8) | 0.40633 (5) | 0.50967 (13) | 0.0226 (2) | |
H5 | 0.5795 | 0.3926 | 0.4431 | 0.027* | |
C6 | 0.58662 (9) | 0.42690 (6) | 0.66216 (14) | 0.0251 (2) | |
H6 | 0.6629 | 0.4274 | 0.7014 | 0.030* | |
C7 | 0.52378 (9) | 0.44744 (5) | 0.76095 (13) | 0.0235 (2) | |
H7 | 0.5582 | 0.4608 | 0.8677 | 0.028* | |
C8 | 0.41346 (8) | 0.44845 (5) | 0.70490 (12) | 0.0197 (2) | |
H8 | 0.3728 | 0.4629 | 0.7732 | 0.024* | |
C9 | 0.35920 (8) | 0.42820 (5) | 0.54631 (12) | 0.0165 (2) | |
C10 | 0.24400 (8) | 0.42940 (5) | 0.48266 (11) | 0.01613 (19) | |
C11 | 0.03374 (9) | 0.34490 (6) | 0.32574 (15) | 0.0265 (2) | |
H11A | 0.0530 | 0.3025 | 0.2859 | 0.032* | |
H11B | −0.0443 | 0.3513 | 0.2863 | 0.032* | |
H11C | 0.0561 | 0.3444 | 0.4428 | 0.032* | |
C12 | 0.21234 (8) | 0.33737 (5) | 0.09015 (12) | 0.0188 (2) | |
C13 | 0.22256 (10) | 0.31315 (6) | −0.16796 (13) | 0.0273 (2) | |
H13A | 0.2351 | 0.2660 | −0.1407 | 0.033* | |
H13B | 0.2625 | 0.3259 | −0.2429 | 0.033* | |
H13C | 0.1456 | 0.3207 | −0.2175 | 0.033* | |
C14 | 0.17457 (8) | 0.46359 (5) | 0.57397 (12) | 0.01689 (19) | |
H14A | 0.0979 | 0.4546 | 0.5187 | 0.020* | |
H14B | 0.1911 | 0.4441 | 0.6823 | 0.020* | |
C15 | 0.19164 (8) | 0.53865 (5) | 0.58891 (11) | 0.01617 (19) | |
C16 | 0.15427 (8) | 0.58152 (5) | 0.45237 (12) | 0.0166 (2) | |
C17 | 0.08944 (8) | 0.55826 (5) | 0.30175 (12) | 0.0196 (2) | |
H17 | 0.0715 | 0.5124 | 0.2881 | 0.024* | |
C18 | 0.05245 (9) | 0.60128 (6) | 0.17562 (13) | 0.0226 (2) | |
H18 | 0.0080 | 0.5849 | 0.0767 | 0.027* | |
C19 | 0.07947 (9) | 0.66946 (6) | 0.19073 (13) | 0.0247 (2) | |
H19 | 0.0548 | 0.6984 | 0.1018 | 0.030* | |
C20 | 0.14131 (9) | 0.69356 (5) | 0.33394 (13) | 0.0229 (2) | |
H20 | 0.1590 | 0.7395 | 0.3442 | 0.028* | |
C21 | 0.17943 (8) | 0.65081 (5) | 0.46755 (12) | 0.0179 (2) | |
C22 | 0.24206 (8) | 0.67646 (5) | 0.61591 (12) | 0.0192 (2) | |
H22 | 0.2636 | 0.7218 | 0.6244 | 0.023* | |
C23 | 0.27166 (8) | 0.63584 (5) | 0.74749 (12) | 0.0178 (2) | |
C24 | 0.24304 (8) | 0.56738 (5) | 0.73454 (11) | 0.01641 (19) | |
C25 | 0.19433 (9) | 0.52489 (6) | 0.95462 (13) | 0.0262 (2) | |
H25A | 0.1782 | 0.5695 | 0.9866 | 0.031* | |
H25B | 0.2210 | 0.4970 | 1.0498 | 0.031* | |
H25C | 0.1288 | 0.5051 | 0.8839 | 0.031* | |
C26 | 0.33310 (9) | 0.66448 (5) | 0.90516 (13) | 0.0205 (2) | |
C27 | 0.48928 (11) | 0.72350 (7) | 1.04184 (18) | 0.0421 (3) | |
H27A | 0.4460 | 0.7583 | 1.0722 | 0.051* | |
H27B | 0.5534 | 0.7435 | 1.0231 | 0.051* | |
H27C | 0.5112 | 0.6907 | 1.1280 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0163 (4) | 0.0186 (4) | 0.0240 (4) | −0.0002 (3) | 0.0023 (3) | −0.0011 (3) |
O2 | 0.0339 (4) | 0.0249 (4) | 0.0193 (4) | −0.0056 (3) | 0.0107 (3) | −0.0059 (3) |
O3 | 0.0295 (4) | 0.0255 (4) | 0.0205 (4) | −0.0067 (3) | 0.0042 (3) | −0.0030 (3) |
O4 | 0.0234 (4) | 0.0196 (4) | 0.0162 (3) | 0.0032 (3) | 0.0066 (3) | 0.0020 (3) |
O5 | 0.0227 (4) | 0.0363 (5) | 0.0373 (5) | −0.0077 (3) | 0.0063 (3) | −0.0119 (4) |
O6 | 0.0398 (5) | 0.0280 (4) | 0.0219 (4) | −0.0035 (3) | 0.0092 (3) | −0.0062 (3) |
C1 | 0.0170 (5) | 0.0138 (4) | 0.0187 (5) | 0.0009 (3) | 0.0038 (4) | 0.0012 (3) |
C2 | 0.0222 (5) | 0.0144 (4) | 0.0169 (4) | 0.0007 (4) | 0.0050 (4) | −0.0004 (3) |
C3 | 0.0220 (5) | 0.0181 (5) | 0.0209 (5) | 0.0014 (4) | 0.0090 (4) | −0.0018 (4) |
C4 | 0.0187 (5) | 0.0163 (4) | 0.0206 (5) | 0.0009 (4) | 0.0062 (4) | 0.0001 (4) |
C5 | 0.0191 (5) | 0.0242 (5) | 0.0256 (5) | 0.0014 (4) | 0.0082 (4) | −0.0023 (4) |
C6 | 0.0164 (5) | 0.0291 (6) | 0.0278 (5) | 0.0004 (4) | 0.0035 (4) | −0.0014 (4) |
C7 | 0.0228 (5) | 0.0246 (5) | 0.0201 (5) | 0.0008 (4) | 0.0015 (4) | −0.0023 (4) |
C8 | 0.0216 (5) | 0.0185 (5) | 0.0186 (5) | 0.0029 (4) | 0.0051 (4) | −0.0010 (4) |
C9 | 0.0180 (5) | 0.0130 (4) | 0.0183 (5) | 0.0010 (3) | 0.0050 (4) | 0.0007 (3) |
C10 | 0.0185 (5) | 0.0127 (4) | 0.0176 (4) | 0.0010 (3) | 0.0059 (4) | 0.0010 (3) |
C11 | 0.0212 (5) | 0.0240 (5) | 0.0354 (6) | −0.0051 (4) | 0.0101 (4) | −0.0036 (4) |
C12 | 0.0216 (5) | 0.0162 (5) | 0.0173 (5) | 0.0034 (4) | 0.0037 (4) | 0.0006 (3) |
C13 | 0.0348 (6) | 0.0291 (6) | 0.0182 (5) | −0.0013 (5) | 0.0077 (4) | −0.0067 (4) |
C14 | 0.0176 (5) | 0.0156 (4) | 0.0185 (4) | 0.0002 (3) | 0.0067 (4) | −0.0009 (3) |
C15 | 0.0155 (4) | 0.0156 (4) | 0.0189 (5) | 0.0019 (3) | 0.0075 (4) | 0.0000 (3) |
C16 | 0.0149 (4) | 0.0184 (5) | 0.0183 (5) | 0.0031 (3) | 0.0075 (4) | 0.0005 (4) |
C17 | 0.0185 (5) | 0.0200 (5) | 0.0209 (5) | 0.0022 (4) | 0.0066 (4) | −0.0014 (4) |
C18 | 0.0196 (5) | 0.0288 (6) | 0.0187 (5) | 0.0030 (4) | 0.0042 (4) | −0.0001 (4) |
C19 | 0.0238 (5) | 0.0269 (5) | 0.0231 (5) | 0.0041 (4) | 0.0061 (4) | 0.0084 (4) |
C20 | 0.0225 (5) | 0.0204 (5) | 0.0268 (5) | 0.0015 (4) | 0.0084 (4) | 0.0061 (4) |
C21 | 0.0164 (4) | 0.0188 (5) | 0.0204 (5) | 0.0024 (4) | 0.0082 (4) | 0.0020 (4) |
C22 | 0.0194 (5) | 0.0163 (4) | 0.0237 (5) | 0.0003 (4) | 0.0090 (4) | −0.0003 (4) |
C23 | 0.0167 (4) | 0.0179 (5) | 0.0197 (5) | 0.0012 (3) | 0.0068 (4) | −0.0023 (4) |
C24 | 0.0162 (4) | 0.0166 (4) | 0.0176 (4) | 0.0029 (3) | 0.0067 (4) | 0.0007 (3) |
C25 | 0.0307 (6) | 0.0294 (6) | 0.0218 (5) | −0.0025 (4) | 0.0126 (4) | 0.0014 (4) |
C26 | 0.0214 (5) | 0.0146 (4) | 0.0238 (5) | 0.0028 (4) | 0.0037 (4) | −0.0018 (4) |
C27 | 0.0305 (6) | 0.0385 (7) | 0.0486 (8) | −0.0085 (5) | −0.0023 (6) | −0.0164 (6) |
O1—C1 | 1.3843 (12) | C11—H11C | 0.98 |
O1—C11 | 1.4419 (13) | C13—H13A | 0.98 |
O2—C12 | 1.3459 (13) | C13—H13B | 0.98 |
O2—C13 | 1.4497 (12) | C13—H13C | 0.98 |
O3—C12 | 1.2040 (13) | C14—C15 | 1.5250 (13) |
O4—C24 | 1.3829 (11) | C14—H14A | 0.99 |
O4—C25 | 1.4377 (13) | C14—H14B | 0.99 |
O5—C26 | 1.3396 (14) | C15—C24 | 1.3821 (13) |
O5—C27 | 1.4507 (15) | C15—C16 | 1.4385 (13) |
O6—C26 | 1.2015 (13) | C16—C17 | 1.4219 (14) |
C1—C10 | 1.3836 (13) | C16—C21 | 1.4280 (14) |
C1—C2 | 1.4299 (14) | C17—C18 | 1.3745 (14) |
C2—C3 | 1.3715 (14) | C17—H17 | 0.95 |
C2—C12 | 1.4943 (13) | C18—C19 | 1.4114 (16) |
C3—C4 | 1.4142 (14) | C18—H18 | 0.95 |
C3—H3 | 0.95 | C19—C20 | 1.3665 (16) |
C4—C5 | 1.4196 (14) | C19—H19 | 0.95 |
C4—C9 | 1.4257 (14) | C20—C21 | 1.4194 (14) |
C5—C6 | 1.3665 (15) | C20—H20 | 0.95 |
C5—H5 | 0.95 | C21—C22 | 1.4146 (14) |
C6—C7 | 1.4108 (16) | C22—C23 | 1.3724 (14) |
C6—H6 | 0.95 | C22—H22 | 0.95 |
C7—C8 | 1.3738 (15) | C23—C24 | 1.4213 (14) |
C7—H7 | 0.95 | C23—C26 | 1.4946 (14) |
C8—C9 | 1.4217 (14) | C25—H25A | 0.98 |
C8—H8 | 0.95 | C25—H25B | 0.98 |
C9—C10 | 1.4379 (13) | C25—H25C | 0.98 |
C10—C14 | 1.5295 (13) | C27—H27A | 0.98 |
C11—H11A | 0.98 | C27—H27B | 0.98 |
C11—H11B | 0.98 | C27—H27C | 0.98 |
C1—O1—C11 | 114.37 (8) | C15—C14—H14A | 108.9 |
C12—O2—C13 | 114.39 (8) | C10—C14—H14A | 108.9 |
C24—O4—C25 | 113.09 (8) | C15—C14—H14B | 108.9 |
C26—O5—C27 | 115.13 (10) | C10—C14—H14B | 108.9 |
C10—C1—O1 | 120.85 (9) | H14A—C14—H14B | 107.7 |
C10—C1—C2 | 121.29 (9) | C24—C15—C16 | 118.17 (9) |
O1—C1—C2 | 117.60 (9) | C24—C15—C14 | 120.79 (9) |
C3—C2—C1 | 119.93 (9) | C16—C15—C14 | 121.04 (9) |
C3—C2—C12 | 119.05 (9) | C17—C16—C21 | 117.72 (9) |
C1—C2—C12 | 120.86 (9) | C17—C16—C15 | 122.66 (9) |
C2—C3—C4 | 120.66 (9) | C21—C16—C15 | 119.59 (9) |
C2—C3—H3 | 119.7 | C18—C17—C16 | 120.86 (10) |
C4—C3—H3 | 119.7 | C18—C17—H17 | 119.6 |
C3—C4—C5 | 120.78 (9) | C16—C17—H17 | 119.6 |
C3—C4—C9 | 119.34 (9) | C17—C18—C19 | 121.06 (10) |
C5—C4—C9 | 119.86 (9) | C17—C18—H18 | 119.5 |
C6—C5—C4 | 120.88 (10) | C19—C18—H18 | 119.5 |
C6—C5—H5 | 119.6 | C20—C19—C18 | 119.62 (10) |
C4—C5—H5 | 119.6 | C20—C19—H19 | 120.2 |
C5—C6—C7 | 119.61 (10) | C18—C19—H19 | 120.2 |
C5—C6—H6 | 120.2 | C19—C20—C21 | 120.86 (10) |
C7—C6—H6 | 120.2 | C19—C20—H20 | 119.6 |
C8—C7—C6 | 120.93 (10) | C21—C20—H20 | 119.6 |
C8—C7—H7 | 119.5 | C22—C21—C20 | 120.39 (9) |
C6—C7—H7 | 119.5 | C22—C21—C16 | 119.75 (9) |
C7—C8—C9 | 121.04 (9) | C20—C21—C16 | 119.86 (9) |
C7—C8—H8 | 119.5 | C23—C22—C21 | 119.99 (9) |
C9—C8—H8 | 119.5 | C23—C22—H22 | 120.0 |
C8—C9—C4 | 117.60 (9) | C21—C22—H22 | 120.0 |
C8—C9—C10 | 122.67 (9) | C22—C23—C24 | 120.38 (9) |
C4—C9—C10 | 119.72 (9) | C22—C23—C26 | 119.35 (9) |
C1—C10—C9 | 118.39 (9) | C24—C23—C26 | 120.26 (9) |
C1—C10—C14 | 120.95 (9) | C15—C24—O4 | 120.91 (9) |
C9—C10—C14 | 120.66 (8) | C15—C24—C23 | 121.57 (9) |
O1—C11—H11A | 109.5 | O4—C24—C23 | 117.38 (9) |
O1—C11—H11B | 109.5 | O4—C25—H25A | 109.5 |
H11A—C11—H11B | 109.5 | O4—C25—H25B | 109.5 |
O1—C11—H11C | 109.5 | H25A—C25—H25B | 109.5 |
H11A—C11—H11C | 109.5 | O4—C25—H25C | 109.5 |
H11B—C11—H11C | 109.5 | H25A—C25—H25C | 109.5 |
O3—C12—O2 | 123.26 (9) | H25B—C25—H25C | 109.5 |
O3—C12—C2 | 124.95 (9) | O6—C26—O5 | 123.90 (10) |
O2—C12—C2 | 111.68 (9) | O6—C26—C23 | 125.36 (10) |
O2—C13—H13A | 109.5 | O5—C26—C23 | 110.69 (9) |
O2—C13—H13B | 109.5 | O5—C27—H27A | 109.5 |
H13A—C13—H13B | 109.5 | O5—C27—H27B | 109.5 |
O2—C13—H13C | 109.5 | H27A—C27—H27B | 109.5 |
H13A—C13—H13C | 109.5 | O5—C27—H27C | 109.5 |
H13B—C13—H13C | 109.5 | H27A—C27—H27C | 109.5 |
C15—C14—C10 | 113.34 (8) | H27B—C27—H27C | 109.5 |
C11—O1—C1—C10 | −84.36 (11) | C10—C14—C15—C24 | −109.68 (10) |
C11—O1—C1—C2 | 101.37 (10) | C10—C14—C15—C16 | 70.68 (11) |
C10—C1—C2—C3 | −0.43 (15) | C24—C15—C16—C17 | −172.29 (9) |
O1—C1—C2—C3 | 173.81 (9) | C14—C15—C16—C17 | 7.37 (14) |
C10—C1—C2—C12 | 174.96 (9) | C24—C15—C16—C21 | 5.58 (13) |
O1—C1—C2—C12 | −10.80 (13) | C14—C15—C16—C21 | −174.77 (9) |
C1—C2—C3—C4 | 5.60 (15) | C21—C16—C17—C18 | −0.05 (14) |
C12—C2—C3—C4 | −169.88 (9) | C15—C16—C17—C18 | 177.86 (9) |
C2—C3—C4—C5 | 175.19 (10) | C16—C17—C18—C19 | 1.32 (16) |
C2—C3—C4—C9 | −3.41 (15) | C17—C18—C19—C20 | −1.53 (17) |
C3—C4—C5—C6 | −176.06 (10) | C18—C19—C20—C21 | 0.45 (16) |
C9—C4—C5—C6 | 2.54 (16) | C19—C20—C21—C22 | −179.06 (10) |
C4—C5—C6—C7 | −0.18 (17) | C19—C20—C21—C16 | 0.81 (15) |
C5—C6—C7—C8 | −1.44 (17) | C17—C16—C21—C22 | 178.87 (9) |
C6—C7—C8—C9 | 0.66 (16) | C15—C16—C21—C22 | 0.89 (14) |
C7—C8—C9—C4 | 1.67 (15) | C17—C16—C21—C20 | −1.01 (14) |
C7—C8—C9—C10 | −179.14 (10) | C15—C16—C21—C20 | −178.98 (9) |
C3—C4—C9—C8 | 175.39 (9) | C20—C21—C22—C23 | 175.03 (9) |
C5—C4—C9—C8 | −3.22 (14) | C16—C21—C22—C23 | −4.84 (14) |
C3—C4—C9—C10 | −3.82 (14) | C21—C22—C23—C24 | 2.27 (15) |
C5—C4—C9—C10 | 177.56 (9) | C21—C22—C23—C26 | −176.94 (9) |
O1—C1—C10—C9 | 179.26 (8) | C16—C15—C24—O4 | 176.06 (8) |
C2—C1—C10—C9 | −6.68 (14) | C14—C15—C24—O4 | −3.59 (14) |
O1—C1—C10—C14 | −1.45 (14) | C16—C15—C24—C23 | −8.33 (14) |
C2—C1—C10—C14 | 172.60 (9) | C14—C15—C24—C23 | 172.02 (9) |
C8—C9—C10—C1 | −170.44 (9) | C25—O4—C24—C15 | −90.58 (11) |
C4—C9—C10—C1 | 8.74 (14) | C25—O4—C24—C23 | 93.63 (10) |
C8—C9—C10—C14 | 10.28 (14) | C22—C23—C24—C15 | 4.53 (15) |
C4—C9—C10—C14 | −170.55 (9) | C26—C23—C24—C15 | −176.27 (9) |
C13—O2—C12—O3 | −3.15 (15) | C22—C23—C24—O4 | −179.71 (9) |
C13—O2—C12—C2 | 173.30 (9) | C26—C23—C24—O4 | −0.51 (13) |
C3—C2—C12—O3 | 133.10 (11) | C27—O5—C26—O6 | −0.75 (16) |
C1—C2—C12—O3 | −42.33 (15) | C27—O5—C26—C23 | 176.75 (10) |
C3—C2—C12—O2 | −43.28 (13) | C22—C23—C26—O6 | 118.12 (12) |
C1—C2—C12—O2 | 141.29 (9) | C24—C23—C26—O6 | −61.09 (14) |
C1—C10—C14—C15 | −113.78 (10) | C22—C23—C26—O5 | −59.33 (12) |
C9—C10—C14—C15 | 65.48 (12) | C24—C23—C26—O5 | 121.46 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O4 | 0.95 | 2.19 | 3.0871 (13) | 158 |
C11—H11A···O3 | 0.98 | 2.47 | 3.1107 (15) | 123 |
C14—H14A···O1 | 0.99 | 2.42 | 2.8830 (13) | 108 |
C14—H14B···O4 | 0.99 | 2.41 | 2.8768 (12) | 108 |
C17—H17···O1 | 0.95 | 2.31 | 3.2206 (13) | 161 |
C19—H19···O3i | 0.95 | 2.58 | 3.2069 (14) | 124 |
C22—H22···O6ii | 0.95 | 2.53 | 3.4172 (13) | 156 |
C25—H25A···O6 | 0.98 | 2.49 | 3.1471 (15) | 124 |
C5—H5···Cg2iii | 0.95 | 2.82 | 3.6488 (12) | 146 |
C11—H11B···Cg2iv | 0.98 | 2.78 | 3.5780 (13) | 139 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C27H24O6 |
Mr | 444.46 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 153 |
a, b, c (Å) | 12.9871 (4), 20.0999 (5), 8.7466 (3) |
β (°) | 106.798 (1) |
V (Å3) | 2185.78 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.59 × 0.58 × 0.58 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21180, 5007, 4617 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.099, 1.01 |
No. of reflections | 5007 |
No. of parameters | 303 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.20 |
Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O4 | 0.95 | 2.19 | 3.0871 (13) | 158 |
C11—H11A···O3 | 0.98 | 2.47 | 3.1107 (15) | 123 |
C14—H14A···O1 | 0.99 | 2.42 | 2.8830 (13) | 108 |
C14—H14B···O4 | 0.99 | 2.41 | 2.8768 (12) | 108 |
C17—H17···O1 | 0.95 | 2.31 | 3.2206 (13) | 161 |
C19—H19···O3i | 0.95 | 2.58 | 3.2069 (14) | 124 |
C22—H22···O6ii | 0.95 | 2.53 | 3.4172 (13) | 156 |
C25—H25A···O6 | 0.98 | 2.49 | 3.1471 (15) | 124 |
C5—H5···Cg2iii | 0.95 | 2.82 | 3.6488 (12) | 146 |
C11—H11B···Cg2iv | 0.98 | 2.78 | 3.5780 (13) | 139 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1. |
Pamoic acid or its derivatives or analogs are used in the pharmaceutical industry for the preparation of medicaments for the treatment of diseases characterized by deposits of amyloid aggregates. We report here the crystal structure of the title compound.
Bond lengths and angles in the title molecule (Fig. 1) are within normal ranges. Both naphthalene ring systems are slightly non-planar, with the dihedral angle between the two benzene rings being 5.06 (4)° for the C1—C10 ring system and 3.92 (3)° for the C15—C24 ring system. The two naphthalene ring systems are almost perpendicular, with a dihedral angle of 87.77 (2)°.
The molecular structure is stabilized by C—H···O hydrogen bonds (Table 1). The crystal structure is stabilized by π-π interactions between the naphthalene ring systems of the inversion related molecules, with a Cg1···Cg1i distance of 3.6311 (6) Å [symmetry code: (i) 1 - x, 1 - y, 1 - z] where Cg1 is the C4—C9 ring centroid. In addition, weak C—H···O intermolecular hydrogen bonds and C—H···π interactions involving the C15/C16/C21—C24 ring (centroid Cg2) are observed (Table 1).