Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010901751X/fg3097sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010901751X/fg3097I-asup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010901751X/fg3097I-csup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010901751X/fg3097I-dsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010901751X/fg3097II-bsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010901751X/fg3097II-csup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010901751X/fg3097III-dsup7.hkl |
CCDC references: 742236; 742237; 742238; 742239; 742240; 742241
Commercially available reagents were purchased from Aldrich and used without further purification. All inclusion compounds were prepared by mixing stoichiometric amounts of the host and guest compounds in ethyl acetate, followed by slow evaporation to yield crystals of the inclusion compounds.
The host molecules in (I–a) and (I–d) lie on twofold symmetry axes. There are two crystallographic independent guest molecules in (I–c). In (III–d) there are three guest molecules in the asymmetric unit for each host molecule and a water molecule. Two of the guest molecules are ordered, while the third is disordered over two sites related by a rotation axis; the occupancy factors were initially freely refined and then fixed at 76:24. The minor portion was refined with restricted geometry (using DFIX in SHELXL97 software; Sheldrick, 2008). The H-atom positions of the major portion were calculated and fixed during the refinement. The H atoms of the minor portion were not included. The H atoms of the water molecule in (III-d) were refined freely. In the other compounds, all H atoms were refined at idealized positions, riding on the C, N and O atoms, with C—H distances of 0.93 and 0.96 Å, N—H distances of 0.86 Å, and O—H distances of 0.82 Å, and with Uiso(H) values either refined freely or set at 1.2 or 1.5 times Ueq(C,N,O). [Please check changes to descriptions of H-atom treatment made in accordance with data in CIF.]
For all compounds, data collection: Collect (Nonius, 2006); cell refinement: DENZO HKL-2000 (Otwinowski & Minor, 1997); data reduction: DENZO HKL-2000 (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999).
C14H10O4·2C5H5NO | F(000) = 904.0 |
Mr = 432.42 | Dx = 1.339 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6780 reflections |
a = 10.569 (1) Å | θ = 3.2–25.9° |
b = 14.054 (3) Å | µ = 0.10 mm−1 |
c = 15.016 (1) Å | T = 293 K |
β = 105.95 (3)° | Prism, colourless |
V = 2144.6 (6) Å3 | 0.20 × 0.10 × 0.04 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 1489 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 25.0°, θmin = 3.2° |
phi– and ω–scans | h = 0→12 |
6780 measured reflections | k = 0→16 |
2013 independent reflections | l = −17→17 |
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)] = 0.062 | Only H-atom displacement parameters refined |
wR(F2) = 0.200 | w = 1/[σ2(Fo2) + (0.1098P)2 + 1.1226P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.004 |
2013 reflections | Δρmax = 0.56 e Å−3 |
157 parameters | Δρmin = −0.35 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: 0.018 (5) |
C14H10O4·2C5H5NO | V = 2144.6 (6) Å3 |
Mr = 432.42 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 10.569 (1) Å | µ = 0.10 mm−1 |
b = 14.054 (3) Å | T = 293 K |
c = 15.016 (1) Å | 0.20 × 0.10 × 0.04 mm |
β = 105.95 (3)° |
Nonius KappaCCD diffractometer | 1489 reflections with I > 2σ(I) |
6780 measured reflections | Rint = 0.026 |
2013 independent reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.200 | Only H-atom displacement parameters refined |
S = 1.03 | Δρmax = 0.56 e Å−3 |
2013 reflections | Δρmin = −0.35 e Å−3 |
157 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 | 0.1058 (2) | 0.50666 (19) | 0.3779 (2) | 0.1418 (12) | |
O2 | −0.07094 (18) | 0.58007 (13) | 0.39187 (16) | 0.0978 (7) | |
H1O2 | −0.0161 | 0.6197 | 0.4177 | 0.151 (16)* | |
O3 | 0.09147 (17) | 0.71551 (13) | 0.46002 (13) | 0.0837 (6) | |
N1 | 0.14965 (17) | 0.84329 (14) | 0.55304 (13) | 0.0699 (6) | |
H1N1 | 0.2301 | 0.8341 | 0.5532 | 0.075 (7)* | |
C1 | −0.0638 (2) | 0.36367 (17) | 0.26248 (15) | 0.0661 (6) | |
C2 | −0.1501 (3) | 0.2897 (2) | 0.22859 (19) | 0.0845 (8) | |
H2 | −0.1271 | 0.2437 | 0.1913 | 0.104 (10)* | |
C3 | −0.2706 (3) | 0.2825 (2) | 0.2489 (2) | 0.0915 (9) | |
H3 | −0.3272 | 0.2324 | 0.2249 | 0.100 (9)* | |
C4 | −0.3057 (3) | 0.3491 (2) | 0.3039 (2) | 0.0850 (8) | |
H4 | −0.3865 | 0.3450 | 0.3171 | 0.105 (9)* | |
C5 | −0.2209 (2) | 0.42181 (19) | 0.33947 (19) | 0.0776 (7) | |
H5 | −0.2444 | 0.4665 | 0.3778 | 0.091 (8)* | |
C6 | −0.1004 (2) | 0.43056 (16) | 0.31978 (16) | 0.0671 (6) | |
C7 | −0.0121 (2) | 0.50949 (19) | 0.36342 (19) | 0.0803 (8) | |
C8 | 0.0570 (2) | 0.78351 (16) | 0.50250 (16) | 0.0651 (6) | |
C9 | −0.0742 (2) | 0.80481 (18) | 0.50159 (18) | 0.0759 (7) | |
H9 | −0.1425 | 0.7672 | 0.4669 | 0.100 (9)* | |
C10 | −0.1019 (2) | 0.87866 (19) | 0.5502 (2) | 0.0819 (8) | |
H10 | −0.1890 | 0.8916 | 0.5480 | 0.118 (11)* | |
C11 | −0.0025 (3) | 0.93577 (19) | 0.6035 (2) | 0.0831 (8) | |
H11 | −0.0216 | 0.9857 | 0.6382 | 0.099 (9)* | |
C12 | 0.1230 (2) | 0.91696 (19) | 0.60353 (18) | 0.0795 (7) | |
H12 | 0.1912 | 0.9546 | 0.6383 | 0.101 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0598 (12) | 0.159 (2) | 0.214 (3) | −0.0268 (12) | 0.0491 (14) | −0.101 (2) |
O2 | 0.0669 (11) | 0.0765 (12) | 0.1545 (19) | −0.0043 (9) | 0.0381 (11) | −0.0266 (12) |
O3 | 0.0697 (11) | 0.0857 (12) | 0.1036 (13) | −0.0064 (8) | 0.0371 (9) | −0.0243 (10) |
N1 | 0.0515 (10) | 0.0775 (12) | 0.0836 (13) | −0.0006 (8) | 0.0231 (9) | −0.0094 (10) |
C1 | 0.0607 (12) | 0.0736 (13) | 0.0636 (12) | −0.0031 (10) | 0.0167 (10) | 0.0036 (10) |
C2 | 0.0898 (18) | 0.0873 (17) | 0.0803 (16) | −0.0178 (14) | 0.0298 (13) | −0.0164 (13) |
C3 | 0.0850 (18) | 0.099 (2) | 0.0919 (17) | −0.0320 (15) | 0.0262 (15) | −0.0078 (15) |
C4 | 0.0636 (14) | 0.0993 (19) | 0.0962 (18) | −0.0145 (13) | 0.0290 (13) | 0.0038 (15) |
C5 | 0.0593 (13) | 0.0846 (16) | 0.0933 (17) | −0.0050 (11) | 0.0284 (12) | −0.0055 (13) |
C6 | 0.0534 (12) | 0.0718 (14) | 0.0775 (14) | 0.0003 (10) | 0.0204 (10) | −0.0015 (11) |
C7 | 0.0545 (13) | 0.0906 (17) | 0.1001 (18) | −0.0062 (11) | 0.0283 (12) | −0.0227 (14) |
C8 | 0.0584 (12) | 0.0695 (13) | 0.0713 (13) | −0.0032 (10) | 0.0241 (10) | −0.0036 (11) |
C9 | 0.0557 (12) | 0.0844 (16) | 0.0898 (16) | −0.0077 (11) | 0.0235 (11) | −0.0085 (13) |
C10 | 0.0577 (13) | 0.0812 (16) | 0.114 (2) | 0.0029 (11) | 0.0359 (14) | −0.0045 (14) |
C11 | 0.0688 (15) | 0.0802 (16) | 0.1077 (19) | 0.0001 (12) | 0.0367 (14) | −0.0177 (14) |
C12 | 0.0648 (14) | 0.0818 (16) | 0.0936 (17) | −0.0041 (12) | 0.0247 (13) | −0.0154 (14) |
O1—C7 | 1.205 (3) | C4—C5 | 1.368 (4) |
O2—C7 | 1.304 (3) | C4—H4 | 0.9300 |
O2—H1O2 | 0.8200 | C5—C6 | 1.389 (3) |
O3—C8 | 1.257 (3) | C5—H5 | 0.9300 |
N1—C12 | 1.358 (3) | C6—C7 | 1.482 (3) |
N1—C8 | 1.354 (3) | C8—C9 | 1.415 (3) |
N1—H1N1 | 0.8600 | C9—C10 | 1.346 (3) |
C1—C2 | 1.384 (3) | C9—H9 | 0.9300 |
C1—C6 | 1.399 (3) | C10—C11 | 1.388 (4) |
C1—C1i | 1.495 (4) | C10—H10 | 0.9300 |
C2—C3 | 1.392 (4) | C11—C12 | 1.352 (4) |
C2—H2 | 0.9300 | C11—H11 | 0.9300 |
C3—C4 | 1.365 (4) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | ||
C7—O2—H1O2 | 109.5 | C5—C6—C7 | 118.4 (2) |
C12—N1—C8 | 123.85 (19) | C1—C6—C7 | 121.9 (2) |
C12—N1—H1N1 | 118.1 | O1—C7—O2 | 121.9 (2) |
C8—N1—H1N1 | 118.1 | O1—C7—C6 | 123.4 (2) |
C2—C1—C6 | 117.7 (2) | O2—C7—C6 | 114.5 (2) |
C2—C1—C1i | 117.16 (19) | O3—C8—N1 | 119.35 (19) |
C6—C1—C1i | 125.11 (17) | O3—C8—C9 | 125.2 (2) |
C3—C2—C1 | 121.6 (3) | N1—C8—C9 | 115.5 (2) |
C3—C2—H2 | 119.2 | C10—C9—C8 | 121.1 (2) |
C1—C2—H2 | 119.2 | C10—C9—H9 | 119.5 |
C4—C3—C2 | 119.9 (2) | C8—C9—H9 | 119.5 |
C4—C3—H3 | 120.0 | C9—C10—C11 | 121.0 (2) |
C2—C3—H3 | 120.0 | C9—C10—H10 | 119.5 |
C5—C4—C3 | 119.4 (2) | C11—C10—H10 | 119.5 |
C5—C4—H4 | 120.3 | C12—C11—C10 | 118.3 (2) |
C3—C4—H4 | 120.3 | C12—C11—H11 | 120.8 |
C4—C5—C6 | 121.6 (3) | C10—C11—H11 | 120.8 |
C4—C5—H5 | 119.2 | C11—C12—N1 | 120.2 (2) |
C6—C5—H5 | 119.2 | C11—C12—H12 | 119.9 |
C5—C6—C1 | 119.7 (2) | N1—C12—H12 | 119.9 |
C6—C1—C2—C3 | 1.2 (4) | C1—C6—C7—O1 | −24.0 (4) |
C1i—C1—C2—C3 | 179.1 (3) | C5—C6—C7—O2 | −21.0 (4) |
C1—C2—C3—C4 | −0.4 (5) | C1—C6—C7—O2 | 161.2 (2) |
C2—C3—C4—C5 | −0.7 (5) | C12—N1—C8—O3 | −178.0 (2) |
C3—C4—C5—C6 | 1.0 (4) | C12—N1—C8—C9 | 2.7 (3) |
C4—C5—C6—C1 | −0.2 (4) | O3—C8—C9—C10 | 179.2 (3) |
C4—C5—C6—C7 | −178.0 (2) | N1—C8—C9—C10 | −1.5 (4) |
C2—C1—C6—C5 | −0.9 (3) | C8—C9—C10—C11 | −0.6 (4) |
C1i—C1—C6—C5 | −178.6 (2) | C9—C10—C11—C12 | 1.7 (4) |
C2—C1—C6—C7 | 176.8 (2) | C10—C11—C12—N1 | −0.6 (4) |
C1i—C1—C6—C7 | −0.9 (4) | C8—N1—C12—C11 | −1.8 (4) |
C5—C6—C7—O1 | 153.8 (3) |
Symmetry code: (i) −x, y, −z+1/2. |
C14H10O4·2C6H7NO | Z = 2 |
Mr = 460.47 | F(000) = 484.0 |
Triclinic, P1 | Dx = 1.293 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.838 (2) Å | Cell parameters from 9471 reflections |
b = 10.085 (2) Å | θ = 1.5–24.7° |
c = 14.016 (3) Å | µ = 0.09 mm−1 |
α = 89.77 (3)° | T = 293 K |
β = 74.90 (3)° | Prism, colourless |
γ = 62.764 (2)° | 0.20 × 0.20 × 0.10 mm |
V = 1183.0 (5) Å3 |
Nonius KappaCCD diffractometer | 3051 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 24.7°, θmin = 1.5° |
phi– and ω–scans | h = 0→11 |
9471 measured reflections | k = −10→11 |
3998 independent reflections | l = −15→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0881P)2 + 0.2916P] where P = (Fo2 + 2Fc2)/3 |
3998 reflections | (Δ/σ)max < 0.001 |
307 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C14H10O4·2C6H7NO | γ = 62.764 (2)° |
Mr = 460.47 | V = 1183.0 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.838 (2) Å | Mo Kα radiation |
b = 10.085 (2) Å | µ = 0.09 mm−1 |
c = 14.016 (3) Å | T = 293 K |
α = 89.77 (3)° | 0.20 × 0.20 × 0.10 mm |
β = 74.90 (3)° |
Nonius KappaCCD diffractometer | 3051 reflections with I > 2σ(I) |
9471 measured reflections | Rint = 0.022 |
3998 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 0.91 | Δρmax = 0.28 e Å−3 |
3998 reflections | Δρmin = −0.16 e Å−3 |
307 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 | 0.78130 (19) | 0.31011 (17) | 0.36902 (10) | 0.0713 (4) | |
H101 | 0.8129 | 0.3486 | 0.4036 | 0.086* | |
O2 | 0.85147 (19) | 0.44073 (17) | 0.25697 (10) | 0.0704 (4) | |
O11 | 1.2056 (2) | 0.1275 (2) | 0.25137 (11) | 0.0798 (5) | |
H11O | 1.1915 | 0.0889 | 0.3021 | 0.096* | |
O21 | 1.09138 (17) | 0.00628 (16) | 0.20186 (10) | 0.0660 (4) | |
O3A | 1.1422 (2) | 0.02959 (18) | 0.41578 (11) | 0.0744 (4) | |
O3B | 0.88444 (18) | 0.42061 (17) | 0.48227 (10) | 0.0680 (4) | |
N1A | 1.11195 (19) | 0.05334 (18) | 0.58106 (12) | 0.0579 (4) | |
H1NA | 1.0471 | 0.0162 | 0.5898 | 0.069* | |
N1B | 0.89778 (18) | 0.48817 (17) | 0.63171 (11) | 0.0544 (4) | |
H1NB | 0.9628 | 0.5202 | 0.6014 | 0.065* | |
C1 | 0.8583 (2) | 0.2245 (2) | 0.10768 (14) | 0.0537 (5) | |
C2 | 0.8078 (2) | 0.1603 (2) | 0.04568 (17) | 0.0707 (6) | |
H2 | 0.8655 | 0.1295 | −0.0214 | 0.085* | |
C3 | 0.6744 (3) | 0.1418 (3) | 0.08159 (19) | 0.0874 (8) | |
H3 | 0.6425 | 0.0997 | 0.0385 | 0.105* | |
C4 | 0.5880 (3) | 0.1848 (3) | 0.1802 (2) | 0.0826 (7) | |
H4 | 0.4986 | 0.1709 | 0.2045 | 0.099* | |
C5 | 0.6354 (2) | 0.2489 (2) | 0.24313 (16) | 0.0645 (5) | |
H5 | 0.5777 | 0.2775 | 0.3103 | 0.077* | |
C6 | 0.7669 (2) | 0.2712 (2) | 0.20803 (13) | 0.0515 (4) | |
C7 | 0.8048 (2) | 0.3497 (2) | 0.27920 (13) | 0.0524 (4) | |
C11 | 1.0070 (2) | 0.2367 (2) | 0.06315 (13) | 0.0547 (5) | |
C21 | 1.0199 (3) | 0.3048 (3) | −0.02309 (16) | 0.0771 (6) | |
H21 | 0.9358 | 0.3416 | −0.0513 | 0.093* | |
C31 | 1.1546 (4) | 0.3192 (3) | −0.06775 (18) | 0.0948 (9) | |
H31 | 1.1606 | 0.3643 | −0.1256 | 0.114* | |
C41 | 1.2786 (4) | 0.2673 (4) | −0.02724 (19) | 0.0967 (9) | |
H41 | 1.3688 | 0.2778 | −0.0570 | 0.116* | |
C51 | 1.2697 (3) | 0.1996 (3) | 0.05760 (16) | 0.0753 (6) | |
H51 | 1.3541 | 0.1651 | 0.0854 | 0.090* | |
C61 | 1.1364 (2) | 0.1819 (2) | 0.10261 (13) | 0.0531 (4) | |
C71 | 1.1409 (2) | 0.0965 (2) | 0.18959 (13) | 0.0532 (4) | |
C8A | 1.1456 (3) | 0.0898 (3) | 0.66141 (15) | 0.0679 (6) | |
H8A | 1.1002 | 0.0728 | 0.7241 | 0.081* | |
C9A | 1.2440 (3) | 0.1503 (3) | 0.65179 (16) | 0.0681 (6) | |
H9A | 1.2669 | 0.1745 | 0.7076 | 0.082* | |
C10A | 1.3126 (2) | 0.1770 (2) | 0.55759 (15) | 0.0556 (5) | |
C11A | 1.2770 (2) | 0.1386 (2) | 0.47826 (14) | 0.0573 (5) | |
H11A | 1.3209 | 0.1563 | 0.4155 | 0.069* | |
C12A | 1.1754 (2) | 0.0725 (2) | 0.48753 (14) | 0.0546 (5) | |
C13A | 1.4214 (3) | 0.2460 (3) | 0.54707 (18) | 0.0747 (6) | |
H13A | 1.3592 | 0.3515 | 0.5716 | 0.112* | |
H13B | 1.4791 | 0.2329 | 0.4781 | 0.112* | |
H13C | 1.4955 | 0.1978 | 0.5848 | 0.112* | |
C8B | 0.8574 (3) | 0.5010 (3) | 0.73209 (15) | 0.0681 (6) | |
H8B | 0.8998 | 0.5437 | 0.7666 | 0.082* | |
C9B | 0.7560 (3) | 0.4525 (3) | 0.78273 (16) | 0.0714 (6) | |
H9B | 0.7283 | 0.4619 | 0.8520 | 0.086* | |
C10B | 0.6928 (2) | 0.3878 (2) | 0.73083 (16) | 0.0631 (5) | |
C11B | 0.7351 (2) | 0.3761 (2) | 0.62905 (15) | 0.0606 (5) | |
H11B | 0.6933 | 0.3334 | 0.5940 | 0.073* | |
C12B | 0.8411 (2) | 0.42737 (19) | 0.57618 (13) | 0.0494 (4) | |
C13B | 0.5797 (3) | 0.3335 (3) | 0.7880 (2) | 0.0919 (8) | |
H13D | 0.6264 | 0.2689 | 0.8337 | 0.138* | |
H13E | 0.5599 | 0.2786 | 0.7422 | 0.138* | |
H13F | 0.4808 | 0.4182 | 0.8244 | 0.138* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1007 (11) | 0.0957 (11) | 0.0462 (8) | −0.0687 (10) | −0.0240 (7) | 0.0112 (7) |
O2 | 0.1016 (11) | 0.0795 (9) | 0.0500 (8) | −0.0610 (9) | −0.0188 (7) | 0.0064 (7) |
O11 | 0.1022 (12) | 0.1220 (13) | 0.0612 (9) | −0.0798 (11) | −0.0449 (8) | 0.0312 (8) |
O21 | 0.0756 (9) | 0.0782 (9) | 0.0661 (9) | −0.0490 (8) | −0.0312 (7) | 0.0230 (7) |
O3A | 0.0950 (11) | 0.0987 (11) | 0.0580 (9) | −0.0618 (9) | −0.0364 (8) | 0.0187 (8) |
O3B | 0.0856 (10) | 0.0906 (10) | 0.0452 (8) | −0.0566 (9) | −0.0178 (7) | 0.0074 (7) |
N1A | 0.0604 (10) | 0.0669 (10) | 0.0562 (10) | −0.0356 (8) | −0.0220 (8) | 0.0148 (8) |
N1B | 0.0627 (10) | 0.0655 (9) | 0.0444 (9) | −0.0387 (8) | −0.0141 (7) | 0.0071 (7) |
C1 | 0.0532 (10) | 0.0562 (11) | 0.0499 (11) | −0.0200 (9) | −0.0233 (8) | 0.0014 (8) |
C2 | 0.0576 (12) | 0.0815 (14) | 0.0637 (13) | −0.0219 (11) | −0.0238 (10) | −0.0168 (10) |
C3 | 0.0582 (13) | 0.1051 (19) | 0.0949 (19) | −0.0309 (13) | −0.0300 (13) | −0.0309 (14) |
C4 | 0.0536 (12) | 0.1001 (18) | 0.0960 (18) | −0.0377 (12) | −0.0216 (12) | −0.0138 (14) |
C5 | 0.0547 (11) | 0.0739 (13) | 0.0640 (13) | −0.0301 (10) | −0.0160 (9) | −0.0029 (10) |
C6 | 0.0508 (10) | 0.0555 (10) | 0.0481 (10) | −0.0231 (8) | −0.0181 (8) | 0.0023 (8) |
C7 | 0.0559 (11) | 0.0597 (11) | 0.0410 (10) | −0.0283 (9) | −0.0116 (8) | 0.0009 (8) |
C11 | 0.0668 (12) | 0.0606 (11) | 0.0393 (9) | −0.0321 (9) | −0.0155 (8) | 0.0024 (8) |
C21 | 0.1034 (18) | 0.0811 (15) | 0.0484 (12) | −0.0427 (14) | −0.0263 (12) | 0.0138 (10) |
C31 | 0.146 (3) | 0.105 (2) | 0.0459 (13) | −0.078 (2) | −0.0131 (15) | 0.0190 (12) |
C41 | 0.122 (2) | 0.135 (2) | 0.0582 (15) | −0.095 (2) | −0.0016 (15) | 0.0118 (15) |
C51 | 0.0808 (15) | 0.1096 (18) | 0.0558 (13) | −0.0663 (14) | −0.0111 (11) | 0.0074 (12) |
C61 | 0.0599 (11) | 0.0686 (12) | 0.0390 (9) | −0.0393 (9) | −0.0101 (8) | 0.0031 (8) |
C71 | 0.0486 (10) | 0.0711 (12) | 0.0445 (10) | −0.0319 (9) | −0.0141 (8) | 0.0051 (8) |
C8A | 0.0760 (14) | 0.0877 (15) | 0.0485 (11) | −0.0457 (12) | −0.0181 (10) | 0.0138 (10) |
C9A | 0.0767 (14) | 0.0865 (15) | 0.0522 (12) | −0.0448 (12) | −0.0241 (10) | 0.0048 (10) |
C10A | 0.0524 (10) | 0.0520 (10) | 0.0602 (12) | −0.0224 (9) | −0.0173 (9) | 0.0047 (8) |
C11A | 0.0615 (12) | 0.0624 (11) | 0.0502 (11) | −0.0308 (10) | −0.0165 (9) | 0.0121 (9) |
C12A | 0.0575 (11) | 0.0571 (11) | 0.0527 (11) | −0.0260 (9) | −0.0237 (9) | 0.0128 (8) |
C13A | 0.0742 (14) | 0.0748 (14) | 0.0846 (16) | −0.0438 (12) | −0.0211 (12) | 0.0028 (11) |
C8B | 0.0761 (14) | 0.0905 (15) | 0.0464 (11) | −0.0449 (12) | −0.0209 (10) | 0.0063 (10) |
C9B | 0.0718 (14) | 0.0981 (16) | 0.0453 (11) | −0.0423 (13) | −0.0147 (10) | 0.0164 (10) |
C10B | 0.0530 (11) | 0.0679 (12) | 0.0630 (13) | −0.0273 (10) | −0.0107 (9) | 0.0214 (10) |
C11B | 0.0620 (12) | 0.0636 (12) | 0.0654 (13) | −0.0362 (10) | −0.0208 (10) | 0.0096 (9) |
C12B | 0.0549 (10) | 0.0520 (10) | 0.0409 (10) | −0.0250 (8) | −0.0138 (8) | 0.0058 (7) |
C13B | 0.0817 (16) | 0.114 (2) | 0.0912 (18) | −0.0601 (16) | −0.0169 (14) | 0.0406 (15) |
O1—C7 | 1.314 (2) | C31—C41 | 1.363 (4) |
O1—H101 | 0.8200 | C31—H31 | 0.9300 |
O2—C7 | 1.208 (2) | C41—C51 | 1.372 (3) |
O11—C71 | 1.313 (2) | C41—H41 | 0.9300 |
O11—H11O | 0.8200 | C51—C61 | 1.390 (3) |
O21—C71 | 1.206 (2) | C51—H51 | 0.9300 |
O3A—C12A | 1.268 (2) | C61—C71 | 1.488 (3) |
O3B—C12B | 1.265 (2) | C8A—C9A | 1.342 (3) |
N1A—C8A | 1.350 (3) | C8A—H8A | 0.9300 |
N1A—C12A | 1.352 (3) | C9A—C10A | 1.404 (3) |
N1A—H1NA | 0.8600 | C9A—H9A | 0.9300 |
N1B—C8B | 1.348 (3) | C10A—C11A | 1.357 (3) |
N1B—C12B | 1.354 (2) | C10A—C13A | 1.500 (3) |
N1B—H1NB | 0.8600 | C11A—C12A | 1.414 (3) |
C1—C2 | 1.395 (3) | C11A—H11A | 0.9300 |
C1—C6 | 1.403 (3) | C13A—H13A | 0.9600 |
C1—C11 | 1.494 (3) | C13A—H13B | 0.9600 |
C2—C3 | 1.375 (3) | C13A—H13C | 0.9600 |
C2—H2 | 0.9300 | C8B—C9B | 1.346 (3) |
C3—C4 | 1.370 (4) | C8B—H8B | 0.9300 |
C3—H3 | 0.9300 | C9B—C10B | 1.397 (3) |
C4—C5 | 1.381 (3) | C9B—H9B | 0.9300 |
C4—H4 | 0.9300 | C10B—C11B | 1.367 (3) |
C5—C6 | 1.378 (3) | C10B—C13B | 1.506 (3) |
C5—H5 | 0.9300 | C11B—C12B | 1.411 (3) |
C6—C7 | 1.494 (3) | C11B—H11B | 0.9300 |
C11—C21 | 1.394 (3) | C13B—H13D | 0.9600 |
C11—C61 | 1.398 (3) | C13B—H13E | 0.9600 |
C21—C31 | 1.383 (4) | C13B—H13F | 0.9600 |
C21—H21 | 0.9300 | ||
C7—O1—H101 | 109.5 | C11—C61—C71 | 121.91 (16) |
C71—O11—H11O | 109.5 | O21—C71—O11 | 123.07 (18) |
C8A—N1A—C12A | 123.04 (18) | O21—C71—C61 | 123.37 (16) |
C8A—N1A—H1NA | 118.5 | O11—C71—C61 | 113.56 (17) |
C12A—N1A—H1NA | 118.5 | C9A—C8A—N1A | 120.7 (2) |
C8B—N1B—C12B | 123.27 (17) | C9A—C8A—H8A | 119.7 |
C8B—N1B—H1NB | 118.4 | N1A—C8A—H8A | 119.7 |
C12B—N1B—H1NB | 118.4 | C8A—C9A—C10A | 120.06 (19) |
C2—C1—C6 | 117.51 (19) | C8A—C9A—H9A | 120.0 |
C2—C1—C11 | 117.89 (18) | C10A—C9A—H9A | 120.0 |
C6—C1—C11 | 124.60 (16) | C11A—C10A—C9A | 117.86 (19) |
C3—C2—C1 | 121.4 (2) | C11A—C10A—C13A | 122.12 (19) |
C3—C2—H2 | 119.3 | C9A—C10A—C13A | 120.01 (19) |
C1—C2—H2 | 119.3 | C10A—C11A—C12A | 122.42 (18) |
C4—C3—C2 | 120.6 (2) | C10A—C11A—H11A | 118.8 |
C4—C3—H3 | 119.7 | C12A—C11A—H11A | 118.8 |
C2—C3—H3 | 119.7 | O3A—C12A—N1A | 118.86 (18) |
C3—C4—C5 | 119.2 (2) | O3A—C12A—C11A | 125.22 (18) |
C3—C4—H4 | 120.4 | N1A—C12A—C11A | 115.92 (17) |
C5—C4—H4 | 120.4 | C10A—C13A—H13A | 109.5 |
C6—C5—C4 | 121.1 (2) | C10A—C13A—H13B | 109.5 |
C6—C5—H5 | 119.5 | H13A—C13A—H13B | 109.5 |
C4—C5—H5 | 119.5 | C10A—C13A—H13C | 109.5 |
C5—C6—C1 | 120.26 (17) | H13A—C13A—H13C | 109.5 |
C5—C6—C7 | 117.94 (17) | H13B—C13A—H13C | 109.5 |
C1—C6—C7 | 121.78 (17) | C9B—C8B—N1B | 120.5 (2) |
O2—C7—O1 | 123.31 (17) | C9B—C8B—H8B | 119.8 |
O2—C7—C6 | 123.72 (17) | N1B—C8B—H8B | 119.8 |
O1—C7—C6 | 112.97 (17) | C8B—C9B—C10B | 119.7 (2) |
C21—C11—C61 | 117.4 (2) | C8B—C9B—H9B | 120.1 |
C21—C11—C1 | 118.97 (19) | C10B—C9B—H9B | 120.1 |
C61—C11—C1 | 123.63 (17) | C11B—C10B—C9B | 118.84 (18) |
C31—C21—C11 | 121.6 (2) | C11B—C10B—C13B | 121.7 (2) |
C31—C21—H21 | 119.2 | C9B—C10B—C13B | 119.5 (2) |
C11—C21—H21 | 119.2 | C10B—C11B—C12B | 121.28 (18) |
C41—C31—C21 | 120.2 (2) | C10B—C11B—H11B | 119.4 |
C41—C31—H31 | 119.9 | C12B—C11B—H11B | 119.4 |
C21—C31—H31 | 119.9 | O3B—C12B—N1B | 119.15 (16) |
C31—C41—C51 | 119.7 (2) | O3B—C12B—C11B | 124.46 (17) |
C31—C41—H41 | 120.2 | N1B—C12B—C11B | 116.39 (17) |
C51—C41—H41 | 120.2 | C10B—C13B—H13D | 109.5 |
C41—C51—C61 | 120.9 (2) | C10B—C13B—H13E | 109.5 |
C41—C51—H51 | 119.5 | H13D—C13B—H13E | 109.5 |
C61—C51—H51 | 119.5 | C10B—C13B—H13F | 109.5 |
C51—C61—C11 | 120.17 (19) | H13D—C13B—H13F | 109.5 |
C51—C61—C71 | 117.84 (18) | H13E—C13B—H13F | 109.5 |
C6—C1—C2—C3 | −0.8 (3) | C1—C11—C61—C51 | −179.02 (19) |
C11—C1—C2—C3 | 178.4 (2) | C21—C11—C61—C71 | −175.07 (18) |
C1—C2—C3—C4 | −0.7 (4) | C1—C11—C61—C71 | 4.3 (3) |
C2—C3—C4—C5 | 0.8 (4) | C51—C61—C71—O21 | −138.3 (2) |
C3—C4—C5—C6 | 0.5 (4) | C11—C61—C71—O21 | 38.5 (3) |
C4—C5—C6—C1 | −2.0 (3) | C51—C61—C71—O11 | 41.1 (3) |
C4—C5—C6—C7 | 176.35 (19) | C11—C61—C71—O11 | −142.17 (19) |
C2—C1—C6—C5 | 2.1 (3) | C12A—N1A—C8A—C9A | 1.1 (3) |
C11—C1—C6—C5 | −177.02 (18) | N1A—C8A—C9A—C10A | 0.3 (3) |
C2—C1—C6—C7 | −176.21 (17) | C8A—C9A—C10A—C11A | −0.6 (3) |
C11—C1—C6—C7 | 4.7 (3) | C8A—C9A—C10A—C13A | 179.4 (2) |
C5—C6—C7—O2 | −140.6 (2) | C9A—C10A—C11A—C12A | −0.5 (3) |
C1—C6—C7—O2 | 37.8 (3) | C13A—C10A—C11A—C12A | 179.54 (18) |
C5—C6—C7—O1 | 39.0 (2) | C8A—N1A—C12A—O3A | 177.19 (19) |
C1—C6—C7—O1 | −142.65 (18) | C8A—N1A—C12A—C11A | −2.0 (3) |
C2—C1—C11—C21 | 52.4 (3) | C10A—C11A—C12A—O3A | −177.44 (19) |
C6—C1—C11—C21 | −128.5 (2) | C10A—C11A—C12A—N1A | 1.7 (3) |
C2—C1—C11—C61 | −127.0 (2) | C12B—N1B—C8B—C9B | 0.0 (3) |
C6—C1—C11—C61 | 52.1 (3) | N1B—C8B—C9B—C10B | 0.2 (3) |
C61—C11—C21—C31 | −0.5 (3) | C8B—C9B—C10B—C11B | −0.3 (3) |
C1—C11—C21—C31 | −179.9 (2) | C8B—C9B—C10B—C13B | 179.9 (2) |
C11—C21—C31—C41 | −0.6 (4) | C9B—C10B—C11B—C12B | 0.2 (3) |
C21—C31—C41—C51 | 0.6 (4) | C13B—C10B—C11B—C12B | 180.0 (2) |
C31—C41—C51—C61 | 0.5 (4) | C8B—N1B—C12B—O3B | 179.53 (18) |
C41—C51—C61—C11 | −1.6 (3) | C8B—N1B—C12B—C11B | −0.1 (3) |
C41—C51—C61—C71 | 175.2 (2) | C10B—C11B—C12B—O3B | −179.58 (19) |
C21—C11—C61—C51 | 1.6 (3) | C10B—C11B—C12B—N1B | 0.1 (3) |
C14H10O4·2C6H7NO | F(000) = 968.0 |
Mr = 460.47 | Dx = 1.298 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 8254 reflections |
a = 11.415 (2) Å | θ = 2.6–25.0° |
b = 10.957 (2) Å | µ = 0.09 mm−1 |
c = 19.660 (3) Å | T = 293 K |
β = 106.59 (2)° | Prism, colourless |
V = 2356.6 (7) Å3 | 0.30 × 0.25 × 0.10 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 1408 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.055 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
phi– and ω–scans | h = 0→13 |
8025 measured reflections | k = 0→13 |
2063 independent reflections | l = −23→22 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.287 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1715P)2 + 1.7724P] where P = (Fo2 + 2Fc2)/3 |
2063 reflections | (Δ/σ)max < 0.001 |
158 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C14H10O4·2C6H7NO | V = 2356.6 (7) Å3 |
Mr = 460.47 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 11.415 (2) Å | µ = 0.09 mm−1 |
b = 10.957 (2) Å | T = 293 K |
c = 19.660 (3) Å | 0.30 × 0.25 × 0.10 mm |
β = 106.59 (2)° |
Nonius KappaCCD diffractometer | 1408 reflections with I > 2σ(I) |
8025 measured reflections | Rint = 0.055 |
2063 independent reflections |
R[F2 > 2σ(F2)] = 0.078 | 0 restraints |
wR(F2) = 0.287 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.43 e Å−3 |
2063 reflections | Δρmin = −0.21 e Å−3 |
158 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 | 0.1093 (3) | 0.4426 (4) | 0.3399 (2) | 0.1250 (15) | |
O2 | −0.0262 (2) | 0.4960 (3) | 0.39257 (17) | 0.0935 (10) | |
H102 | 0.0261 | 0.5469 | 0.4105 | 0.140* | |
O3 | 0.1146 (3) | 0.6716 (2) | 0.45987 (15) | 0.0841 (9) | |
N1 | 0.1472 (3) | 0.8760 (3) | 0.46155 (15) | 0.0691 (9) | |
H1N1 | 0.2208 | 0.8620 | 0.4869 | 0.083* | |
C1 | −0.0564 (3) | 0.2549 (3) | 0.26170 (16) | 0.0562 (8) | |
C2 | −0.1419 (3) | 0.1643 (3) | 0.23460 (19) | 0.0695 (10) | |
H2 | −0.1285 | 0.1105 | 0.2010 | 0.083* | |
C3 | −0.2461 (4) | 0.1520 (4) | 0.2561 (2) | 0.0797 (11) | |
H3 | −0.3016 | 0.0902 | 0.2370 | 0.096* | |
C4 | −0.2684 (4) | 0.2292 (4) | 0.3049 (2) | 0.0849 (13) | |
H4 | −0.3396 | 0.2215 | 0.3185 | 0.102* | |
C5 | −0.1842 (3) | 0.3195 (3) | 0.3341 (2) | 0.0718 (10) | |
H5 | −0.1990 | 0.3719 | 0.3680 | 0.086* | |
C6 | −0.0780 (3) | 0.3330 (3) | 0.31375 (17) | 0.0572 (9) | |
C7 | 0.0119 (3) | 0.4280 (3) | 0.34861 (18) | 0.0626 (9) | |
C8 | 0.0722 (4) | 0.7795 (4) | 0.4420 (2) | 0.0736 (10) | |
C9 | −0.0475 (4) | 0.8060 (4) | 0.4004 (2) | 0.0859 (13) | |
H9 | −0.1027 | 0.7428 | 0.3839 | 0.103* | |
C10 | −0.0825 (4) | 0.9229 (5) | 0.3843 (3) | 0.0975 (14) | |
H10 | −0.1629 | 0.9393 | 0.3586 | 0.117* | |
C11 | 0.0004 (4) | 1.0201 (4) | 0.4057 (2) | 0.0846 (12) | |
H11 | −0.0239 | 1.1001 | 0.3936 | 0.102* | |
C12 | 0.1150 (4) | 0.9947 (4) | 0.4441 (2) | 0.0765 (11) | |
C13 | 0.2144 (5) | 1.0878 (4) | 0.4696 (3) | 0.0938 (14) | |
H13A | 0.2850 | 1.0637 | 0.4556 | 0.14 (2)* | |
H13B | 0.2355 | 1.0934 | 0.5204 | 0.14 (2)* | |
H13C | 0.1861 | 1.1658 | 0.4492 | 0.125 (19)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.089 (2) | 0.139 (3) | 0.169 (3) | −0.057 (2) | 0.073 (2) | −0.084 (3) |
O2 | 0.0804 (18) | 0.083 (2) | 0.123 (2) | −0.0255 (15) | 0.0385 (17) | −0.0428 (17) |
O3 | 0.0815 (18) | 0.0651 (18) | 0.098 (2) | −0.0143 (13) | 0.0140 (15) | −0.0125 (14) |
N1 | 0.0749 (19) | 0.0593 (18) | 0.0725 (18) | −0.0078 (14) | 0.0201 (15) | −0.0061 (14) |
C1 | 0.0566 (18) | 0.0534 (18) | 0.0566 (17) | −0.0029 (13) | 0.0133 (14) | 0.0016 (13) |
C2 | 0.074 (2) | 0.065 (2) | 0.069 (2) | −0.0145 (17) | 0.0185 (18) | −0.0118 (16) |
C3 | 0.073 (2) | 0.079 (3) | 0.085 (2) | −0.029 (2) | 0.019 (2) | −0.013 (2) |
C4 | 0.064 (2) | 0.094 (3) | 0.105 (3) | −0.024 (2) | 0.037 (2) | −0.015 (2) |
C5 | 0.070 (2) | 0.070 (2) | 0.082 (2) | −0.0143 (17) | 0.0331 (19) | −0.0157 (18) |
C6 | 0.0551 (17) | 0.0498 (18) | 0.0668 (19) | −0.0058 (13) | 0.0175 (15) | −0.0020 (14) |
C7 | 0.0598 (19) | 0.054 (2) | 0.074 (2) | −0.0040 (15) | 0.0197 (16) | −0.0060 (15) |
C8 | 0.072 (2) | 0.067 (2) | 0.082 (2) | −0.0064 (19) | 0.0229 (19) | −0.0092 (19) |
C9 | 0.071 (2) | 0.084 (3) | 0.099 (3) | −0.014 (2) | 0.018 (2) | −0.001 (2) |
C10 | 0.077 (3) | 0.101 (4) | 0.113 (3) | 0.005 (2) | 0.025 (2) | 0.026 (3) |
C11 | 0.089 (3) | 0.082 (3) | 0.086 (3) | 0.001 (2) | 0.031 (2) | 0.015 (2) |
C12 | 0.089 (3) | 0.071 (2) | 0.076 (2) | −0.003 (2) | 0.034 (2) | 0.0003 (18) |
C13 | 0.114 (4) | 0.066 (3) | 0.104 (3) | −0.016 (2) | 0.034 (3) | −0.013 (2) |
O1—C7 | 1.184 (4) | C4—H4 | 0.9300 |
O2—C7 | 1.306 (4) | C5—C6 | 1.389 (5) |
O2—H102 | 0.8200 | C5—H5 | 0.9300 |
O3—C8 | 1.288 (5) | C6—C7 | 1.484 (5) |
N1—C8 | 1.345 (5) | C8—C9 | 1.407 (6) |
N1—C12 | 1.369 (5) | C9—C10 | 1.352 (6) |
N1—H1N1 | 0.8600 | C9—H9 | 0.9300 |
C1—C2 | 1.387 (5) | C10—C11 | 1.407 (7) |
C1—C6 | 1.409 (5) | C10—H10 | 0.9300 |
C1—C1i | 1.486 (7) | C11—C12 | 1.340 (6) |
C2—C3 | 1.378 (6) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—C13 | 1.501 (6) |
C3—C4 | 1.357 (6) | C13—H13A | 0.9600 |
C3—H3 | 0.9300 | C13—H13B | 0.9600 |
C4—C5 | 1.385 (5) | C13—H13C | 0.9600 |
C7—O2—H102 | 109.5 | O1—C7—C6 | 125.6 (3) |
C8—N1—C12 | 124.9 (4) | O2—C7—C6 | 112.9 (3) |
C8—N1—H1N1 | 117.6 | O3—C8—N1 | 119.0 (4) |
C12—N1—H1N1 | 117.6 | O3—C8—C9 | 125.1 (4) |
C2—C1—C6 | 117.7 (3) | N1—C8—C9 | 115.9 (4) |
C2—C1—C1i | 117.2 (3) | C10—C9—C8 | 120.3 (4) |
C6—C1—C1i | 124.9 (3) | C10—C9—H9 | 119.9 |
C3—C2—C1 | 121.8 (3) | C8—C9—H9 | 119.9 |
C3—C2—H2 | 119.1 | C9—C10—C11 | 121.2 (4) |
C1—C2—H2 | 119.1 | C9—C10—H10 | 119.4 |
C4—C3—C2 | 120.5 (3) | C11—C10—H10 | 119.4 |
C4—C3—H3 | 119.7 | C12—C11—C10 | 118.5 (4) |
C2—C3—H3 | 119.7 | C12—C11—H11 | 120.8 |
C3—C4—C5 | 119.4 (4) | C10—C11—H11 | 120.8 |
C3—C4—H4 | 120.3 | C11—C12—N1 | 119.2 (4) |
C5—C4—H4 | 120.3 | C11—C12—C13 | 124.8 (4) |
C4—C5—C6 | 121.0 (3) | N1—C12—C13 | 116.0 (4) |
C4—C5—H5 | 119.5 | C12—C13—H13A | 109.5 |
C6—C5—H5 | 119.5 | C12—C13—H13B | 109.5 |
C5—C6—C1 | 119.5 (3) | H13A—C13—H13B | 109.5 |
C5—C6—C7 | 119.1 (3) | C12—C13—H13C | 109.5 |
C1—C6—C7 | 121.3 (3) | H13A—C13—H13C | 109.5 |
O1—C7—O2 | 121.5 (3) | H13B—C13—H13C | 109.5 |
C6—C1—C2—C3 | 1.6 (5) | C5—C6—C7—O2 | −4.9 (5) |
C1i—C1—C2—C3 | 176.2 (4) | C1—C6—C7—O2 | 176.5 (3) |
C1—C2—C3—C4 | 0.1 (6) | C12—N1—C8—O3 | 177.6 (4) |
C2—C3—C4—C5 | −1.3 (7) | C12—N1—C8—C9 | 0.2 (6) |
C3—C4—C5—C6 | 0.7 (7) | O3—C8—C9—C10 | −179.5 (4) |
C4—C5—C6—C1 | 1.0 (6) | N1—C8—C9—C10 | −2.2 (6) |
C4—C5—C6—C7 | −177.6 (4) | C8—C9—C10—C11 | 2.9 (7) |
C2—C1—C6—C5 | −2.1 (5) | C9—C10—C11—C12 | −1.4 (7) |
C1i—C1—C6—C5 | −176.2 (3) | C10—C11—C12—N1 | −0.6 (6) |
C2—C1—C6—C7 | 176.5 (3) | C10—C11—C12—C13 | 178.8 (4) |
C1i—C1—C6—C7 | 2.4 (5) | C8—N1—C12—C11 | 1.3 (6) |
C5—C6—C7—O1 | 174.1 (4) | C8—N1—C12—C13 | −178.2 (4) |
C1—C6—C7—O1 | −4.5 (6) |
Symmetry code: (i) −x, y, −z+1/2. |
C30H22O2·2C6H7NO | Z = 1 |
Mr = 632.73 | F(000) = 334 |
Triclinic, P1 | Dx = 1.218 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.305 (1) Å | Cell parameters from 8783 reflections |
b = 9.369 (2) Å | θ = 1.6–25.9° |
c = 13.292 (3) Å | µ = 0.08 mm−1 |
α = 77.32 (2)° | T = 293 K |
β = 89.46 (2)° | Block, clourless |
γ = 76.57 (3)° | 0.30 × 0.20 × 0.10 mm |
V = 862.4 (3) Å3 |
Nonius KappaCCD diffractometer | 2398 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 25.9°, θmin = 1.6° |
phi– and ω–scans | h = 0→8 |
8783 measured reflections | k = −10→11 |
3182 independent reflections | l = −15→16 |
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)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0823P)2 + 0.1172P] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.016 |
3182 reflections | Δρmax = 0.16 e Å−3 |
220 parameters | Δρmin = −0.15 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: 0.207 (16) |
C30H22O2·2C6H7NO | γ = 76.57 (3)° |
Mr = 632.73 | V = 862.4 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.305 (1) Å | Mo Kα radiation |
b = 9.369 (2) Å | µ = 0.08 mm−1 |
c = 13.292 (3) Å | T = 293 K |
α = 77.32 (2)° | 0.30 × 0.20 × 0.10 mm |
β = 89.46 (2)° |
Nonius KappaCCD diffractometer | 2398 reflections with I > 2σ(I) |
8783 measured reflections | Rint = 0.027 |
3182 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | Δρmax = 0.16 e Å−3 |
3182 reflections | Δρmin = −0.15 e Å−3 |
220 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 | 0.72411 (14) | 0.31208 (12) | 0.73995 (8) | 0.0458 (3) | |
H101 | 0.7383 | 0.2467 | 0.7065 | 0.079 (7)* | |
O2 | 0.7501 (2) | 0.11080 (15) | 0.62033 (10) | 0.0747 (4) | |
N1 | 0.72456 (19) | 0.04472 (16) | 0.46798 (11) | 0.0546 (4) | |
C1 | 0.9785 (2) | 0.47211 (17) | 0.54999 (11) | 0.0443 (4) | |
C2 | 0.9418 (2) | 0.42336 (17) | 0.63672 (10) | 0.0428 (4) | |
C3 | 0.8938 (2) | 0.36020 (16) | 0.74321 (10) | 0.0363 (4) | |
C4 | 0.8595 (2) | 0.48128 (17) | 0.80710 (10) | 0.0410 (4) | |
C5 | 0.9291 (3) | 0.6085 (2) | 0.77981 (14) | 0.0602 (5) | |
H5 | 0.9951 | 0.6240 | 0.7197 | 0.072* | |
C6 | 0.9024 (3) | 0.7135 (2) | 0.84048 (18) | 0.0796 (6) | |
H6 | 0.9480 | 0.7998 | 0.8202 | 0.095* | |
C7 | 0.8093 (3) | 0.6910 (3) | 0.92987 (18) | 0.0760 (6) | |
H7 | 0.7936 | 0.7608 | 0.9713 | 0.091* | |
C8 | 0.7394 (3) | 0.5655 (3) | 0.95835 (14) | 0.0740 (6) | |
H8 | 0.6756 | 0.5503 | 1.0192 | 0.089* | |
C9 | 0.7629 (3) | 0.4599 (2) | 0.89711 (12) | 0.0579 (5) | |
H9 | 0.7137 | 0.3752 | 0.9167 | 0.070* | |
C10 | 1.05939 (19) | 0.22999 (16) | 0.79430 (9) | 0.0354 (3) | |
C11 | 1.0265 (2) | 0.09593 (17) | 0.85050 (11) | 0.0447 (4) | |
H11 | 0.9041 | 0.0831 | 0.8555 | 0.054* | |
C12 | 1.1750 (3) | −0.01938 (19) | 0.89941 (13) | 0.0555 (5) | |
H12 | 1.1512 | −0.1087 | 0.9373 | 0.067* | |
C13 | 1.3565 (2) | −0.0026 (2) | 0.89226 (13) | 0.0578 (5) | |
H13 | 1.4558 | −0.0805 | 0.9244 | 0.069* | |
C14 | 1.3906 (2) | 0.1303 (2) | 0.83720 (14) | 0.0623 (5) | |
H14 | 1.5133 | 0.1428 | 0.8328 | 0.075* | |
C15 | 1.2431 (2) | 0.2456 (2) | 0.78835 (12) | 0.0515 (4) | |
H15 | 1.2679 | 0.3348 | 0.7510 | 0.062* | |
C16 | 0.7005 (2) | 0.1523 (2) | 0.52692 (13) | 0.0519 (4) | |
C17 | 0.6240 (3) | 0.3025 (2) | 0.47230 (16) | 0.0648 (5) | |
H17 | 0.6052 | 0.3793 | 0.5081 | 0.078* | |
C18 | 0.5777 (3) | 0.3381 (2) | 0.37015 (16) | 0.0710 (6) | |
H18 | 0.5273 | 0.4378 | 0.3369 | 0.085* | |
C19 | 0.6052 (4) | 0.2259 (3) | 0.31494 (17) | 0.0831 (7) | |
H19 | 0.5740 | 0.2492 | 0.2446 | 0.100* | |
C20 | 0.6780 (3) | 0.0826 (3) | 0.36508 (15) | 0.0728 (6) | |
H20 | 0.6970 | 0.0071 | 0.3282 | 0.087* | |
C21 | 0.8020 (3) | −0.1124 (2) | 0.52008 (18) | 0.0745 (6) | |
H21A | 0.9204 | −0.1212 | 0.5545 | 0.112* | |
H21B | 0.8208 | −0.1740 | 0.4701 | 0.112* | |
H21C | 0.7157 | −0.1453 | 0.5698 | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0457 (6) | 0.0496 (7) | 0.0444 (6) | −0.0141 (5) | −0.0007 (4) | −0.0120 (5) |
O2 | 0.1014 (11) | 0.0638 (9) | 0.0615 (9) | −0.0169 (8) | −0.0126 (7) | −0.0213 (7) |
N1 | 0.0515 (8) | 0.0506 (9) | 0.0670 (9) | −0.0102 (6) | 0.0052 (6) | −0.0265 (7) |
C1 | 0.0636 (10) | 0.0373 (8) | 0.0310 (7) | −0.0114 (7) | 0.0023 (6) | −0.0063 (6) |
C2 | 0.0590 (9) | 0.0370 (8) | 0.0317 (8) | −0.0100 (7) | 0.0020 (6) | −0.0077 (6) |
C3 | 0.0451 (8) | 0.0365 (8) | 0.0278 (7) | −0.0123 (6) | 0.0037 (5) | −0.0056 (6) |
C4 | 0.0468 (8) | 0.0408 (9) | 0.0322 (7) | −0.0026 (6) | −0.0038 (6) | −0.0094 (6) |
C5 | 0.0793 (12) | 0.0525 (11) | 0.0566 (10) | −0.0234 (9) | 0.0055 (9) | −0.0203 (8) |
C6 | 0.1010 (17) | 0.0639 (14) | 0.0867 (15) | −0.0223 (12) | −0.0045 (13) | −0.0406 (12) |
C7 | 0.0730 (13) | 0.0749 (15) | 0.0828 (15) | 0.0098 (11) | −0.0186 (11) | −0.0510 (12) |
C8 | 0.0701 (13) | 0.0974 (17) | 0.0495 (11) | 0.0085 (11) | 0.0046 (9) | −0.0361 (11) |
C9 | 0.0651 (11) | 0.0627 (11) | 0.0424 (9) | −0.0036 (9) | 0.0087 (8) | −0.0165 (8) |
C10 | 0.0441 (8) | 0.0392 (8) | 0.0250 (6) | −0.0112 (6) | 0.0052 (5) | −0.0102 (6) |
C11 | 0.0481 (9) | 0.0419 (9) | 0.0428 (8) | −0.0130 (7) | 0.0008 (6) | −0.0041 (7) |
C12 | 0.0701 (12) | 0.0411 (9) | 0.0497 (9) | −0.0089 (8) | −0.0075 (8) | −0.0023 (7) |
C13 | 0.0544 (10) | 0.0590 (11) | 0.0519 (10) | 0.0068 (8) | −0.0118 (8) | −0.0161 (8) |
C14 | 0.0415 (9) | 0.0829 (14) | 0.0619 (11) | −0.0127 (9) | 0.0005 (8) | −0.0169 (10) |
C15 | 0.0505 (9) | 0.0579 (10) | 0.0476 (9) | −0.0212 (8) | 0.0065 (7) | −0.0064 (8) |
C16 | 0.0510 (9) | 0.0521 (10) | 0.0588 (10) | −0.0139 (8) | −0.0012 (7) | −0.0234 (8) |
C17 | 0.0665 (12) | 0.0497 (11) | 0.0795 (13) | −0.0056 (9) | −0.0115 (10) | −0.0253 (10) |
C18 | 0.0672 (12) | 0.0603 (12) | 0.0793 (14) | −0.0095 (10) | −0.0110 (10) | −0.0077 (11) |
C19 | 0.0960 (16) | 0.0921 (18) | 0.0599 (12) | −0.0164 (13) | −0.0069 (11) | −0.0198 (12) |
C20 | 0.0850 (14) | 0.0788 (15) | 0.0631 (12) | −0.0136 (12) | 0.0048 (10) | −0.0397 (11) |
C21 | 0.0712 (13) | 0.0487 (11) | 0.1050 (16) | −0.0083 (9) | 0.0065 (11) | −0.0267 (11) |
O1—C3 | 1.4179 (18) | C10—C15 | 1.383 (2) |
O1—H101 | 0.8200 | C10—C11 | 1.385 (2) |
O2—C16 | 1.247 (2) | C11—C12 | 1.388 (2) |
N1—C20 | 1.361 (2) | C11—H11 | 0.9300 |
N1—C16 | 1.386 (2) | C12—C13 | 1.371 (3) |
N1—C21 | 1.463 (3) | C12—H12 | 0.9300 |
C1—C2 | 1.196 (2) | C13—C14 | 1.374 (3) |
C1—C1i | 1.379 (3) | C13—H13 | 0.9300 |
C2—C3 | 1.482 (2) | C14—C15 | 1.383 (3) |
C3—C4 | 1.535 (2) | C14—H14 | 0.9300 |
C3—C10 | 1.542 (2) | C15—H15 | 0.9300 |
C4—C5 | 1.379 (2) | C16—C17 | 1.419 (3) |
C4—C9 | 1.384 (2) | C17—C18 | 1.352 (3) |
C5—C6 | 1.383 (3) | C17—H17 | 0.9300 |
C5—H5 | 0.9300 | C18—C19 | 1.386 (3) |
C6—C7 | 1.364 (3) | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—C20 | 1.346 (3) |
C7—C8 | 1.367 (3) | C19—H19 | 0.9300 |
C7—H7 | 0.9300 | C20—H20 | 0.9300 |
C8—C9 | 1.394 (3) | C21—H21A | 0.9600 |
C8—H8 | 0.9300 | C21—H21B | 0.9600 |
C9—H9 | 0.9300 | C21—H21C | 0.9600 |
C3—O1—H101 | 109.5 | C12—C11—H11 | 119.8 |
C20—N1—C16 | 121.67 (16) | C13—C12—C11 | 120.48 (16) |
C20—N1—C21 | 120.56 (16) | C13—C12—H12 | 119.8 |
C16—N1—C21 | 117.78 (16) | C11—C12—H12 | 119.8 |
C2—C1—C1i | 179.7 (3) | C12—C13—C14 | 119.51 (16) |
C1—C2—C3 | 178.47 (16) | C12—C13—H13 | 120.2 |
O1—C3—C2 | 109.36 (11) | C14—C13—H13 | 120.2 |
O1—C3—C4 | 107.16 (11) | C13—C14—C15 | 120.24 (16) |
C2—C3—C4 | 110.50 (12) | C13—C14—H14 | 119.9 |
O1—C3—C10 | 111.97 (12) | C15—C14—H14 | 119.9 |
C2—C3—C10 | 108.85 (12) | C14—C15—C10 | 120.94 (16) |
C4—C3—C10 | 109.00 (11) | C14—C15—H15 | 119.5 |
C5—C4—C9 | 118.65 (15) | C10—C15—H15 | 119.5 |
C5—C4—C3 | 121.89 (14) | O2—C16—N1 | 118.57 (16) |
C9—C4—C3 | 119.41 (14) | O2—C16—C17 | 126.20 (16) |
C4—C5—C6 | 120.95 (18) | N1—C16—C17 | 115.22 (16) |
C4—C5—H5 | 119.5 | C18—C17—C16 | 122.36 (18) |
C6—C5—H5 | 119.5 | C18—C17—H17 | 118.8 |
C7—C6—C5 | 120.2 (2) | C16—C17—H17 | 118.8 |
C7—C6—H6 | 119.9 | C17—C18—C19 | 120.0 (2) |
C5—C6—H6 | 119.9 | C17—C18—H18 | 120.0 |
C6—C7—C8 | 119.69 (18) | C19—C18—H18 | 120.0 |
C6—C7—H7 | 120.2 | C20—C19—C18 | 118.7 (2) |
C8—C7—H7 | 120.2 | C20—C19—H19 | 120.6 |
C7—C8—C9 | 120.65 (19) | C18—C19—H19 | 120.6 |
C7—C8—H8 | 119.7 | C19—C20—N1 | 122.06 (18) |
C9—C8—H8 | 119.7 | C19—C20—H20 | 119.0 |
C4—C9—C8 | 119.81 (19) | N1—C20—H20 | 119.0 |
C4—C9—H9 | 120.1 | N1—C21—H21A | 109.5 |
C8—C9—H9 | 120.1 | N1—C21—H21B | 109.5 |
C15—C10—C11 | 118.33 (14) | H21A—C21—H21B | 109.5 |
C15—C10—C3 | 121.14 (13) | N1—C21—H21C | 109.5 |
C11—C10—C3 | 120.49 (13) | H21A—C21—H21C | 109.5 |
C10—C11—C12 | 120.49 (15) | H21B—C21—H21C | 109.5 |
C10—C11—H11 | 119.8 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
C30H22O2·2C6H7NO | Z = 1 |
Mr = 632.73 | F(000) = 334.0 |
Triclinic, P1 | Dx = 1.208 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.640 (2) Å | Cell parameters from 8509 reflections |
b = 10.203 (2) Å | θ = 2.1–25.8° |
c = 11.403 (3) Å | µ = 0.08 mm−1 |
α = 106.71 (3)° | T = 293 K |
β = 111.54 (2)° | Prism, colourless |
γ = 95.87 (2)° | 0.25 × 0.10 × 0.05 mm |
V = 870.8 (4) Å3 |
Nonius KappaCCD diffractometer | 1947 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 25.8°, θmin = 2.1° |
phi– and ω–scans | h = 0→10 |
8509 measured reflections | k = −12→12 |
3215 independent reflections | l = −13→12 |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0731P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
3215 reflections | Δρmax = 0.14 e Å−3 |
220 parameters | Δρmin = −0.15 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: 0.086 (10) |
C30H22O2·2C6H7NO | γ = 95.87 (2)° |
Mr = 632.73 | V = 870.8 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.640 (2) Å | Mo Kα radiation |
b = 10.203 (2) Å | µ = 0.08 mm−1 |
c = 11.403 (3) Å | T = 293 K |
α = 106.71 (3)° | 0.25 × 0.10 × 0.05 mm |
β = 111.54 (2)° |
Nonius KappaCCD diffractometer | 1947 reflections with I > 2σ(I) |
8509 measured reflections | Rint = 0.034 |
3215 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.131 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.14 e Å−3 |
3215 reflections | Δρmin = −0.15 e Å−3 |
220 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 | 0.62987 (16) | 0.15238 (11) | 0.24833 (12) | 0.0502 (4) | |
H1O1 | 0.6312 | 0.1551 | 0.3213 | 0.060* | |
O2 | 0.62699 (18) | 0.13777 (15) | 0.48594 (15) | 0.0700 (4) | |
N1 | 0.7118 (2) | −0.02291 (18) | 0.58322 (17) | 0.0632 (5) | |
H1N1 | 0.6061 | −0.0638 | 0.5547 | 0.076* | |
C1 | 0.9242 (2) | 0.45897 (18) | 0.44718 (17) | 0.0457 (5) | |
C2 | 0.7922 (2) | 0.38783 (18) | 0.35623 (18) | 0.0438 (4) | |
C3 | 0.63810 (19) | 0.29019 (16) | 0.24071 (16) | 0.0377 (4) | |
C4 | 0.65921 (18) | 0.28371 (17) | 0.11167 (16) | 0.0378 (4) | |
C5 | 0.6658 (2) | 0.16042 (19) | 0.02543 (18) | 0.0488 (5) | |
H5 | 0.6560 | 0.0780 | 0.0444 | 0.059* | |
C6 | 0.6869 (3) | 0.1591 (2) | −0.0900 (2) | 0.0619 (6) | |
H6 | 0.6904 | 0.0753 | −0.1482 | 0.074* | |
C7 | 0.7026 (3) | 0.2794 (2) | −0.1192 (2) | 0.0643 (6) | |
H7 | 0.7187 | 0.2780 | −0.1958 | 0.077* | |
C8 | 0.6944 (3) | 0.4029 (2) | −0.0340 (2) | 0.0660 (6) | |
H8 | 0.7039 | 0.4850 | −0.0536 | 0.079* | |
C9 | 0.6723 (2) | 0.4046 (2) | 0.0800 (2) | 0.0553 (5) | |
H9 | 0.6660 | 0.4881 | 0.1366 | 0.066* | |
C10 | 0.4727 (2) | 0.33443 (18) | 0.23599 (17) | 0.0415 (4) | |
C11 | 0.4676 (3) | 0.4546 (2) | 0.3267 (2) | 0.0573 (5) | |
H11 | 0.5691 | 0.5146 | 0.3951 | 0.069* | |
C12 | 0.3115 (3) | 0.4873 (3) | 0.3172 (3) | 0.0781 (7) | |
H12 | 0.3091 | 0.5685 | 0.3792 | 0.094* | |
C13 | 0.1615 (3) | 0.3993 (3) | 0.2161 (3) | 0.0877 (9) | |
H13 | 0.0575 | 0.4209 | 0.2099 | 0.105* | |
C14 | 0.1646 (3) | 0.2806 (3) | 0.1246 (3) | 0.0817 (8) | |
H14 | 0.0626 | 0.2217 | 0.0560 | 0.098* | |
C15 | 0.3185 (2) | 0.2475 (2) | 0.1335 (2) | 0.0595 (6) | |
H15 | 0.3194 | 0.1665 | 0.0704 | 0.071* | |
C16 | 0.8338 (3) | −0.0784 (3) | 0.6539 (2) | 0.0758 (7) | |
H16 | 0.8017 | −0.1597 | 0.6691 | 0.091* | |
C17 | 1.0003 (3) | −0.0172 (3) | 0.7020 (2) | 0.0769 (7) | |
H17 | 1.0832 | −0.0560 | 0.7500 | 0.092* | |
C18 | 1.0489 (3) | 0.1056 (2) | 0.6797 (2) | 0.0676 (6) | |
C19 | 0.9245 (3) | 0.1592 (2) | 0.6076 (2) | 0.0647 (6) | |
H19 | 0.9561 | 0.2406 | 0.5925 | 0.078* | |
C20 | 0.7493 (3) | 0.0947 (2) | 0.5554 (2) | 0.0584 (5) | |
C21 | 1.2355 (3) | 0.1750 (3) | 0.7349 (3) | 0.0949 (8) | |
H21A | 1.2989 | 0.1044 | 0.7211 | 0.142* | |
H22B | 1.2770 | 0.2270 | 0.8294 | 0.142* | |
H21C | 1.2499 | 0.2379 | 0.6892 | 0.142* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0596 (8) | 0.0455 (7) | 0.0488 (8) | 0.0135 (6) | 0.0208 (7) | 0.0233 (6) |
O2 | 0.0747 (9) | 0.0861 (10) | 0.0768 (10) | 0.0380 (8) | 0.0366 (8) | 0.0544 (9) |
N1 | 0.0710 (11) | 0.0750 (12) | 0.0653 (11) | 0.0328 (9) | 0.0340 (9) | 0.0425 (10) |
C1 | 0.0380 (9) | 0.0552 (11) | 0.0386 (10) | 0.0056 (8) | 0.0131 (8) | 0.0147 (9) |
C2 | 0.0403 (10) | 0.0499 (10) | 0.0409 (10) | 0.0101 (8) | 0.0169 (9) | 0.0157 (8) |
C3 | 0.0348 (8) | 0.0365 (9) | 0.0360 (9) | 0.0054 (7) | 0.0092 (7) | 0.0129 (7) |
C4 | 0.0315 (8) | 0.0428 (10) | 0.0339 (9) | 0.0062 (7) | 0.0097 (7) | 0.0122 (8) |
C5 | 0.0491 (10) | 0.0468 (11) | 0.0447 (11) | 0.0092 (8) | 0.0176 (9) | 0.0109 (9) |
C6 | 0.0707 (13) | 0.0618 (13) | 0.0497 (13) | 0.0158 (10) | 0.0303 (11) | 0.0076 (10) |
C7 | 0.0697 (13) | 0.0825 (16) | 0.0487 (13) | 0.0171 (12) | 0.0332 (11) | 0.0234 (12) |
C8 | 0.0867 (15) | 0.0662 (13) | 0.0633 (14) | 0.0204 (11) | 0.0405 (12) | 0.0354 (11) |
C9 | 0.0730 (13) | 0.0471 (11) | 0.0539 (12) | 0.0164 (10) | 0.0331 (11) | 0.0195 (9) |
C10 | 0.0392 (9) | 0.0495 (10) | 0.0433 (10) | 0.0122 (8) | 0.0184 (8) | 0.0247 (9) |
C11 | 0.0589 (12) | 0.0772 (14) | 0.0461 (12) | 0.0286 (10) | 0.0258 (10) | 0.0268 (11) |
C12 | 0.0937 (18) | 0.1131 (19) | 0.0725 (16) | 0.0649 (16) | 0.0554 (15) | 0.0549 (15) |
C13 | 0.0664 (16) | 0.152 (3) | 0.105 (2) | 0.0605 (17) | 0.0569 (16) | 0.091 (2) |
C14 | 0.0372 (11) | 0.115 (2) | 0.103 (2) | 0.0137 (12) | 0.0211 (12) | 0.0647 (18) |
C15 | 0.0391 (10) | 0.0654 (12) | 0.0664 (14) | 0.0049 (9) | 0.0121 (9) | 0.0279 (11) |
C16 | 0.0858 (17) | 0.0876 (16) | 0.0818 (17) | 0.0440 (14) | 0.0394 (14) | 0.0549 (14) |
C17 | 0.0816 (17) | 0.0893 (17) | 0.0742 (16) | 0.0442 (14) | 0.0298 (13) | 0.0443 (14) |
C18 | 0.0713 (14) | 0.0750 (15) | 0.0574 (14) | 0.0292 (12) | 0.0277 (11) | 0.0193 (12) |
C19 | 0.0734 (14) | 0.0650 (13) | 0.0645 (14) | 0.0257 (11) | 0.0330 (12) | 0.0262 (11) |
C20 | 0.0770 (14) | 0.0671 (13) | 0.0517 (12) | 0.0355 (11) | 0.0357 (11) | 0.0317 (11) |
C21 | 0.0763 (16) | 0.0922 (18) | 0.091 (2) | 0.0231 (14) | 0.0173 (14) | 0.0187 (15) |
O1—C3 | 1.430 (2) | C10—C11 | 1.375 (3) |
O1—H1O1 | 0.8200 | C10—C15 | 1.395 (3) |
O2—C20 | 1.272 (3) | C11—C12 | 1.395 (3) |
N1—C16 | 1.357 (3) | C11—H11 | 0.9300 |
N1—C20 | 1.364 (3) | C12—C13 | 1.373 (4) |
N1—H1N1 | 0.8600 | C12—H12 | 0.9300 |
C1—C2 | 1.197 (2) | C13—C14 | 1.362 (4) |
C1—C1i | 1.380 (4) | C13—H13 | 0.9300 |
C2—C3 | 1.479 (3) | C14—C15 | 1.381 (3) |
C3—C10 | 1.529 (3) | C14—H14 | 0.9300 |
C3—C4 | 1.532 (3) | C15—H15 | 0.9300 |
C4—C5 | 1.377 (3) | C16—C17 | 1.342 (3) |
C4—C9 | 1.386 (3) | C16—H16 | 0.9300 |
C5—C6 | 1.391 (3) | C17—C18 | 1.402 (3) |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—C7 | 1.367 (3) | C18—C19 | 1.364 (3) |
C6—H6 | 0.9300 | C18—C21 | 1.504 (3) |
C7—C8 | 1.378 (3) | C19—C20 | 1.410 (3) |
C7—H7 | 0.9300 | C19—H19 | 0.9300 |
C8—C9 | 1.378 (3) | C21—H21A | 0.9600 |
C8—H8 | 0.9300 | C21—H22B | 0.9600 |
C9—H9 | 0.9300 | C21—H21C | 0.9600 |
C3—O1—H1O1 | 109.5 | C12—C11—H11 | 119.7 |
C16—N1—C20 | 123.0 (2) | C13—C12—C11 | 119.9 (2) |
C16—N1—H1N1 | 118.5 | C13—C12—H12 | 120.1 |
C20—N1—H1N1 | 118.5 | C11—C12—H12 | 120.1 |
C2—C1—C1i | 179.5 (2) | C14—C13—C12 | 120.2 (2) |
C1—C2—C3 | 174.69 (19) | C14—C13—H13 | 119.9 |
O1—C3—C2 | 108.84 (15) | C12—C13—H13 | 119.9 |
O1—C3—C10 | 109.47 (12) | C13—C14—C15 | 120.2 (2) |
C2—C3—C10 | 112.85 (15) | C13—C14—H14 | 119.9 |
O1—C3—C4 | 107.53 (14) | C15—C14—H14 | 119.9 |
C2—C3—C4 | 107.83 (15) | C14—C15—C10 | 120.7 (2) |
C10—C3—C4 | 110.17 (13) | C14—C15—H15 | 119.7 |
C5—C4—C9 | 118.68 (18) | C10—C15—H15 | 119.7 |
C5—C4—C3 | 121.74 (16) | C17—C16—N1 | 120.6 (2) |
C9—C4—C3 | 119.58 (16) | C17—C16—H16 | 119.7 |
C4—C5—C6 | 120.04 (19) | N1—C16—H16 | 119.7 |
C4—C5—H5 | 120.0 | C16—C17—C18 | 119.8 (2) |
C6—C5—H5 | 120.0 | C16—C17—H17 | 120.1 |
C7—C6—C5 | 120.82 (19) | C18—C17—H17 | 120.1 |
C7—C6—H6 | 119.6 | C19—C18—C17 | 118.7 (2) |
C5—C6—H6 | 119.6 | C19—C18—C21 | 121.6 (2) |
C6—C7—C8 | 119.5 (2) | C17—C18—C21 | 119.7 (2) |
C6—C7—H7 | 120.3 | C18—C19—C20 | 121.9 (2) |
C8—C7—H7 | 120.3 | C18—C19—H19 | 119.1 |
C9—C8—C7 | 120.0 (2) | C20—C19—H19 | 119.1 |
C9—C8—H8 | 120.0 | O2—C20—N1 | 118.82 (19) |
C7—C8—H8 | 120.0 | O2—C20—C19 | 125.17 (19) |
C8—C9—C4 | 121.03 (19) | N1—C20—C19 | 116.01 (19) |
C8—C9—H9 | 119.5 | C18—C21—H21A | 109.5 |
C4—C9—H9 | 119.5 | C18—C21—H22B | 109.5 |
C11—C10—C15 | 118.40 (19) | H21A—C21—H22B | 109.5 |
C11—C10—C3 | 123.75 (16) | C18—C21—H21C | 109.5 |
C15—C10—C3 | 117.85 (17) | H21A—C21—H21C | 109.5 |
C10—C11—C12 | 120.5 (2) | H22B—C21—H21C | 109.5 |
C10—C11—H11 | 119.7 | ||
C1i—C1—C2—C3 | −123 (32) | O1—C3—C10—C15 | −56.7 (2) |
C1—C2—C3—O1 | 48.3 (19) | C2—C3—C10—C15 | −178.04 (14) |
C1—C2—C3—C10 | 170.1 (18) | C4—C3—C10—C15 | 61.4 (2) |
C1—C2—C3—C4 | −68.0 (19) | C15—C10—C11—C12 | 0.9 (3) |
O1—C3—C4—C5 | 0.6 (2) | C3—C10—C11—C12 | −179.13 (17) |
C2—C3—C4—C5 | 117.78 (17) | C10—C11—C12—C13 | −0.4 (3) |
C10—C3—C4—C5 | −118.67 (17) | C11—C12—C13—C14 | −0.3 (3) |
O1—C3—C4—C9 | −179.40 (14) | C12—C13—C14—C15 | 0.4 (4) |
C2—C3—C4—C9 | −62.2 (2) | C13—C14—C15—C10 | 0.2 (3) |
C10—C3—C4—C9 | 61.36 (19) | C11—C10—C15—C14 | −0.9 (3) |
C9—C4—C5—C6 | 0.7 (3) | C3—C10—C15—C14 | 179.18 (17) |
C3—C4—C5—C6 | −179.30 (15) | C20—N1—C16—C17 | 0.9 (4) |
C4—C5—C6—C7 | 0.5 (3) | N1—C16—C17—C18 | 0.3 (4) |
C5—C6—C7—C8 | −1.1 (3) | C16—C17—C18—C19 | −0.7 (4) |
C6—C7—C8—C9 | 0.7 (3) | C16—C17—C18—C21 | 179.4 (2) |
C7—C8—C9—C4 | 0.5 (3) | C17—C18—C19—C20 | 0.0 (3) |
C5—C4—C9—C8 | −1.1 (3) | C21—C18—C19—C20 | 179.9 (2) |
C3—C4—C9—C8 | 178.83 (17) | C16—N1—C20—O2 | 178.4 (2) |
O1—C3—C10—C11 | 123.40 (19) | C16—N1—C20—C19 | −1.5 (3) |
C2—C3—C10—C11 | 2.0 (2) | C18—C19—C20—O2 | −178.9 (2) |
C4—C3—C10—C11 | −118.6 (2) | C18—C19—C20—N1 | 1.0 (3) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
C20H18O3·3C6H7NO·H2O | F(000) = 1361.6 |
Mr = 651.74 | Dx = 1.239 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 23701 reflections |
a = 10.634 (2) Å | θ = 1.4–25.0° |
b = 11.484 (2) Å | µ = 0.09 mm−1 |
c = 28.574 (4) Å | T = 293 K |
β = 96.43 (2)° | Prism, colorless |
V = 3467.5 (10) Å3 | 0.35 × 0.30 × 0.09 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 3757 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Graphite monochromator | θmax = 25.0°, θmin = 1.4° |
phi– and ω–scans | h = 0→12 |
23701 measured reflections | k = 0→13 |
6109 independent reflections | l = −33→33 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.83 | w = 1/[σ2(Fo2) + (0.1224P)2] where P = (Fo2 + 2Fc2)/3 |
6109 reflections | (Δ/σ)max = 0.002 |
481 parameters | Δρmax = 0.22 e Å−3 |
20 restraints | Δρmin = −0.23 e Å−3 |
C20H18O3·3C6H7NO·H2O | V = 3467.5 (10) Å3 |
Mr = 651.74 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.634 (2) Å | µ = 0.09 mm−1 |
b = 11.484 (2) Å | T = 293 K |
c = 28.574 (4) Å | 0.35 × 0.30 × 0.09 mm |
β = 96.43 (2)° |
Nonius KappaCCD diffractometer | 3757 reflections with I > 2σ(I) |
23701 measured reflections | Rint = 0.062 |
6109 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 20 restraints |
wR(F2) = 0.161 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.83 | Δρmax = 0.22 e Å−3 |
6109 reflections | Δρmin = −0.23 e Å−3 |
481 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 | Occ. (<1) | |
O1 | 0.78769 (16) | 0.88810 (13) | 0.43141 (6) | 0.0540 (5) | |
H101 | 0.7235 | 0.8787 | 0.4444 | 0.065* | |
O2 | 1.23738 (16) | 0.56931 (15) | 0.18889 (6) | 0.0561 (5) | |
H1O2 | 1.2071 | 0.5903 | 0.1626 | 0.067* | |
O3 | 0.39912 (17) | 0.37168 (17) | 0.19938 (7) | 0.0656 (5) | |
H1O3 | 0.3452 | 0.4229 | 0.1989 | 0.079* | |
C1 | 0.8978 (2) | 0.39579 (19) | 0.34566 (9) | 0.0512 (6) | |
H1A | 0.9260 | 0.3320 | 0.3278 | 0.061* | |
H1B | 0.8273 | 0.3713 | 0.3615 | 0.061* | |
H1C | 0.9656 | 0.4207 | 0.3685 | 0.061* | |
C2 | 0.8566 (2) | 0.49856 (17) | 0.31197 (7) | 0.0373 (5) | |
C3 | 0.8394 (2) | 0.60608 (17) | 0.34304 (7) | 0.0356 (5) | |
C4 | 0.8987 (2) | 0.71181 (17) | 0.33791 (8) | 0.0376 (5) | |
H4 | 0.9513 | 0.7205 | 0.3143 | 0.045* | |
C5 | 0.8811 (2) | 0.80530 (18) | 0.36739 (8) | 0.0403 (5) | |
H5 | 0.9220 | 0.8756 | 0.3633 | 0.048* | |
C6 | 0.8037 (2) | 0.79416 (17) | 0.40244 (8) | 0.0386 (5) | |
C7 | 0.7436 (2) | 0.6899 (2) | 0.40835 (8) | 0.0481 (6) | |
H7 | 0.6914 | 0.6814 | 0.4322 | 0.058* | |
C8 | 0.7614 (2) | 0.59797 (19) | 0.37870 (8) | 0.0483 (6) | |
H8 | 0.7196 | 0.5282 | 0.3828 | 0.058* | |
C9 | 0.9564 (2) | 0.51979 (17) | 0.27829 (8) | 0.0364 (5) | |
C10 | 1.0837 (2) | 0.5001 (2) | 0.29213 (9) | 0.0522 (6) | |
H10 | 1.1081 | 0.4745 | 0.3227 | 0.063* | |
C11 | 1.1756 (2) | 0.5172 (2) | 0.26240 (9) | 0.0574 (7) | |
H11 | 1.2599 | 0.5021 | 0.2729 | 0.069* | |
C12 | 1.1427 (2) | 0.55651 (18) | 0.21716 (8) | 0.0421 (6) | |
C13 | 1.0175 (2) | 0.58060 (19) | 0.20285 (8) | 0.0429 (6) | |
H13 | 0.9940 | 0.6094 | 0.1727 | 0.051* | |
C14 | 0.9268 (2) | 0.56221 (18) | 0.23303 (8) | 0.0422 (6) | |
H14 | 0.8427 | 0.5789 | 0.2226 | 0.051* | |
C15 | 0.7301 (2) | 0.46699 (16) | 0.28294 (7) | 0.0362 (5) | |
C16 | 0.6336 (2) | 0.54694 (18) | 0.27213 (8) | 0.0440 (6) | |
H16 | 0.6432 | 0.6222 | 0.2840 | 0.053* | |
C17 | 0.5236 (2) | 0.5178 (2) | 0.24427 (8) | 0.0467 (6) | |
H17 | 0.4608 | 0.5736 | 0.2374 | 0.056* | |
C18 | 0.5062 (2) | 0.4070 (2) | 0.22656 (8) | 0.0453 (6) | |
C19 | 0.6017 (2) | 0.32628 (19) | 0.23592 (9) | 0.0500 (6) | |
H19 | 0.5917 | 0.2513 | 0.2237 | 0.060* | |
C20 | 0.7120 (2) | 0.35640 (18) | 0.26325 (9) | 0.0471 (6) | |
H20 | 0.7761 | 0.3014 | 0.2687 | 0.056* | |
O4 | 0.62796 (19) | 1.19711 (17) | 0.43940 (7) | 0.0703 (6) | |
N1 | 0.4159 (2) | 1.22869 (16) | 0.43493 (8) | 0.0537 (5) | |
H1N1 | 0.4199 | 1.2143 | 0.4646 | 0.064* | |
C21 | 0.1930 (3) | 1.2541 (3) | 0.44175 (13) | 0.0810 (9) | |
H21A | 0.1139 | 1.2578 | 0.4220 | 0.097* | |
H21B | 0.2008 | 1.3204 | 0.4623 | 0.097* | |
H21C | 0.1959 | 1.1841 | 0.4602 | 0.097* | |
C22 | 0.2998 (3) | 1.2538 (2) | 0.41169 (11) | 0.0651 (8) | |
C23 | 0.2909 (4) | 1.2760 (3) | 0.36518 (12) | 0.0802 (10) | |
H23 | 0.2127 | 1.2926 | 0.3485 | 0.096* | |
C24 | 0.4003 (4) | 1.2739 (3) | 0.34212 (13) | 0.0890 (11) | |
H24 | 0.3941 | 1.2891 | 0.3100 | 0.107* | |
C25 | 0.5145 (3) | 1.2504 (3) | 0.36569 (11) | 0.0748 (9) | |
H25 | 0.5861 | 1.2510 | 0.3498 | 0.090* | |
C26 | 0.5261 (3) | 1.2247 (2) | 0.41454 (10) | 0.0591 (7) | |
O5 | 0.57334 (18) | 0.86075 (16) | 0.47216 (6) | 0.0631 (5) | |
N2 | 0.36052 (19) | 0.88775 (16) | 0.46732 (7) | 0.0476 (5) | |
H2N2 | 0.3640 | 0.8652 | 0.4961 | 0.057* | |
C27 | 0.1370 (3) | 0.9128 (3) | 0.47380 (11) | 0.0676 (8) | |
H27A | 0.0589 | 0.9192 | 0.4535 | 0.081* | |
H27B | 0.1432 | 0.9757 | 0.4961 | 0.081* | |
H27C | 0.1389 | 0.8399 | 0.4903 | 0.081* | |
C28 | 0.2447 (3) | 0.9184 (2) | 0.44521 (9) | 0.0532 (7) | |
C29 | 0.2366 (3) | 0.9513 (2) | 0.39996 (10) | 0.0633 (8) | |
H29 | 0.1588 | 0.9715 | 0.3838 | 0.076* | |
C30 | 0.3474 (3) | 0.9549 (2) | 0.37710 (10) | 0.0719 (8) | |
H30 | 0.3419 | 0.9779 | 0.3457 | 0.086* | |
C31 | 0.4605 (3) | 0.9259 (2) | 0.39957 (10) | 0.0640 (7) | |
H31 | 0.5324 | 0.9293 | 0.3838 | 0.077* | |
C32 | 0.4707 (3) | 0.8900 (2) | 0.44735 (9) | 0.0512 (6) | |
O6A | 0.3836 (3) | 0.5162 (3) | 0.53700 (12) | 0.0924 (10) | 0.76 |
N3 | 0.3659 (3) | 0.5580 (2) | 0.46137 (12) | 0.0784 (9) | |
H3N3 | 0.4446 | 0.5390 | 0.4635 | 0.118* | |
C33 | 0.3849 (5) | 0.6035 (3) | 0.38078 (16) | 0.1122 (16) | |
H33A | 0.4687 | 0.5773 | 0.3919 | 0.168* | |
H33B | 0.3884 | 0.6829 | 0.3704 | 0.168* | |
H33C | 0.3504 | 0.5555 | 0.3550 | 0.168* | |
C34A | 0.3114 (5) | 0.5946 (3) | 0.41660 (18) | 0.0792 (14) | 0.76 |
C35 | 0.1848 (5) | 0.6235 (3) | 0.4159 (2) | 0.1020 (16) | |
H35A | 0.1380 | 0.6536 | 0.3892 | 0.153* | 0.76 |
C36A | 0.1246 (6) | 0.6087 (5) | 0.4548 (3) | 0.116 (2) | 0.76 |
H36A | 0.0377 | 0.6214 | 0.4518 | 0.174* | 0.76 |
C37 | 0.1795 (4) | 0.5754 (3) | 0.4982 (2) | 0.1078 (15) | |
H37 | 0.1373 | 0.5704 | 0.5250 | 0.162* | |
C38A | 0.3169 (4) | 0.5477 (3) | 0.49915 (19) | 0.0760 (12) | 0.76 |
O6B | 0.5372 (7) | 0.5195 (7) | 0.4429 (3) | 0.065 (2) | 0.24 |
C34B | 0.2312 (10) | 0.5891 (9) | 0.4628 (4) | 0.056 (3) | 0.24 |
C36B | 0.2511 (15) | 0.6470 (11) | 0.3805 (5) | 0.085 (4) | 0.24 |
C38B | 0.4350 (11) | 0.5558 (9) | 0.4336 (4) | 0.058 (3) | 0.24 |
O1W | 0.8354 (2) | 1.1149 (2) | 0.40034 (7) | 0.0657 (6) | |
H1W | 0.819 (3) | 1.039 (3) | 0.4092 (12) | 0.101 (12)* | |
H2W | 0.780 (3) | 1.154 (3) | 0.4081 (11) | 0.078 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0531 (11) | 0.0545 (9) | 0.0577 (11) | −0.0031 (8) | 0.0203 (9) | −0.0151 (8) |
O2 | 0.0381 (10) | 0.0860 (12) | 0.0468 (10) | −0.0077 (8) | 0.0161 (8) | −0.0075 (8) |
O3 | 0.0430 (11) | 0.0866 (12) | 0.0663 (13) | −0.0133 (9) | 0.0019 (9) | −0.0245 (10) |
C1 | 0.0527 (16) | 0.0504 (13) | 0.0506 (16) | 0.0073 (11) | 0.0068 (13) | 0.0095 (11) |
C2 | 0.0365 (13) | 0.0370 (11) | 0.0393 (13) | 0.0041 (9) | 0.0078 (10) | 0.0019 (9) |
C3 | 0.0309 (12) | 0.0424 (11) | 0.0334 (12) | 0.0015 (9) | 0.0036 (10) | 0.0013 (9) |
C4 | 0.0314 (12) | 0.0456 (12) | 0.0370 (12) | 0.0022 (9) | 0.0095 (10) | 0.0030 (9) |
C5 | 0.0346 (13) | 0.0413 (11) | 0.0461 (14) | −0.0021 (9) | 0.0089 (11) | 0.0022 (9) |
C6 | 0.0334 (13) | 0.0446 (12) | 0.0376 (13) | 0.0031 (9) | 0.0027 (10) | −0.0046 (9) |
C7 | 0.0501 (16) | 0.0563 (14) | 0.0416 (14) | −0.0077 (11) | 0.0219 (12) | −0.0050 (11) |
C8 | 0.0529 (16) | 0.0488 (13) | 0.0459 (14) | −0.0126 (11) | 0.0181 (12) | −0.0037 (10) |
C9 | 0.0323 (13) | 0.0393 (11) | 0.0378 (13) | 0.0045 (9) | 0.0043 (10) | −0.0050 (9) |
C10 | 0.0390 (15) | 0.0809 (17) | 0.0364 (14) | 0.0131 (12) | 0.0034 (12) | 0.0014 (12) |
C11 | 0.0289 (14) | 0.0953 (19) | 0.0481 (16) | 0.0127 (12) | 0.0042 (12) | −0.0008 (13) |
C12 | 0.0363 (14) | 0.0517 (13) | 0.0395 (13) | −0.0053 (10) | 0.0101 (11) | −0.0082 (10) |
C13 | 0.0368 (14) | 0.0553 (13) | 0.0363 (13) | −0.0032 (10) | 0.0035 (11) | 0.0029 (10) |
C14 | 0.0286 (13) | 0.0551 (13) | 0.0425 (14) | 0.0026 (10) | 0.0025 (11) | 0.0059 (10) |
C15 | 0.0349 (13) | 0.0366 (11) | 0.0388 (12) | −0.0012 (9) | 0.0116 (10) | 0.0010 (9) |
C16 | 0.0375 (14) | 0.0427 (12) | 0.0525 (15) | 0.0013 (10) | 0.0081 (11) | −0.0078 (10) |
C17 | 0.0309 (13) | 0.0589 (14) | 0.0507 (15) | 0.0020 (10) | 0.0065 (11) | −0.0095 (11) |
C18 | 0.0367 (14) | 0.0598 (14) | 0.0413 (14) | −0.0132 (11) | 0.0132 (11) | −0.0094 (11) |
C19 | 0.0570 (17) | 0.0389 (12) | 0.0551 (16) | −0.0102 (11) | 0.0112 (13) | −0.0070 (10) |
C20 | 0.0476 (16) | 0.0380 (12) | 0.0566 (15) | 0.0013 (10) | 0.0101 (12) | −0.0001 (10) |
O4 | 0.0592 (14) | 0.0943 (14) | 0.0603 (12) | 0.0130 (10) | 0.0193 (11) | 0.0019 (10) |
N1 | 0.0556 (14) | 0.0577 (12) | 0.0490 (13) | 0.0110 (10) | 0.0113 (11) | 0.0002 (9) |
C21 | 0.057 (2) | 0.086 (2) | 0.101 (3) | 0.0173 (16) | 0.0119 (19) | 0.0005 (18) |
C22 | 0.062 (2) | 0.0554 (15) | 0.076 (2) | 0.0120 (13) | 0.0022 (16) | 0.0033 (13) |
C23 | 0.081 (2) | 0.081 (2) | 0.075 (2) | 0.0169 (17) | −0.009 (2) | 0.0226 (16) |
C24 | 0.104 (3) | 0.100 (2) | 0.063 (2) | 0.017 (2) | 0.011 (2) | 0.0274 (17) |
C25 | 0.086 (2) | 0.085 (2) | 0.0563 (19) | 0.0075 (17) | 0.0227 (18) | 0.0162 (15) |
C26 | 0.0600 (19) | 0.0619 (15) | 0.0569 (18) | 0.0079 (13) | 0.0131 (15) | 0.0016 (12) |
O5 | 0.0522 (12) | 0.0878 (12) | 0.0514 (11) | 0.0112 (9) | 0.0152 (10) | −0.0044 (9) |
N2 | 0.0465 (13) | 0.0594 (12) | 0.0377 (11) | 0.0048 (9) | 0.0074 (10) | −0.0085 (9) |
C27 | 0.0456 (17) | 0.088 (2) | 0.069 (2) | 0.0047 (14) | 0.0073 (15) | −0.0141 (15) |
C28 | 0.0539 (18) | 0.0549 (14) | 0.0504 (16) | 0.0042 (11) | 0.0041 (13) | −0.0115 (11) |
C29 | 0.065 (2) | 0.0734 (17) | 0.0503 (17) | 0.0098 (14) | 0.0003 (15) | −0.0027 (13) |
C30 | 0.086 (2) | 0.0816 (19) | 0.0490 (17) | 0.0112 (17) | 0.0104 (17) | 0.0054 (14) |
C31 | 0.068 (2) | 0.0798 (18) | 0.0478 (17) | 0.0078 (15) | 0.0216 (15) | 0.0010 (13) |
C32 | 0.0509 (17) | 0.0576 (14) | 0.0462 (15) | 0.0050 (12) | 0.0100 (13) | −0.0105 (11) |
O6A | 0.072 (2) | 0.118 (2) | 0.089 (2) | 0.0003 (18) | 0.0161 (19) | 0.0423 (19) |
N3 | 0.069 (2) | 0.0609 (15) | 0.096 (2) | −0.0008 (13) | −0.0327 (19) | 0.0161 (15) |
C33 | 0.132 (4) | 0.085 (2) | 0.106 (3) | −0.013 (2) | −0.048 (3) | 0.018 (2) |
C34A | 0.090 (4) | 0.058 (2) | 0.081 (3) | −0.006 (2) | −0.028 (3) | 0.006 (2) |
C35 | 0.079 (3) | 0.070 (2) | 0.140 (5) | 0.009 (2) | −0.062 (3) | 0.001 (3) |
C36A | 0.066 (4) | 0.082 (3) | 0.193 (8) | 0.006 (3) | −0.021 (5) | −0.028 (4) |
C37 | 0.064 (3) | 0.089 (2) | 0.161 (5) | 0.006 (2) | −0.029 (3) | 0.005 (3) |
C38A | 0.062 (3) | 0.071 (2) | 0.092 (4) | −0.006 (2) | −0.006 (3) | 0.022 (2) |
O6B | 0.025 (4) | 0.109 (6) | 0.058 (5) | 0.012 (4) | −0.006 (4) | 0.054 (4) |
C34B | 0.030 (7) | 0.061 (6) | 0.075 (9) | 0.002 (5) | −0.001 (6) | 0.009 (6) |
C36B | 0.089 (12) | 0.063 (8) | 0.100 (12) | −0.010 (7) | −0.003 (10) | −0.002 (8) |
C38B | 0.078 (10) | 0.064 (7) | 0.033 (6) | −0.021 (6) | 0.017 (7) | 0.024 (5) |
O1W | 0.0719 (15) | 0.0722 (13) | 0.0573 (12) | 0.0069 (12) | 0.0270 (11) | 0.0001 (10) |
O1—C6 | 1.382 (3) | C24—H24 | 0.9300 |
O1—H101 | 0.8200 | C25—C26 | 1.419 (4) |
O2—C12 | 1.368 (3) | C25—H25 | 0.9300 |
O2—H1O2 | 0.8200 | O5—C32 | 1.278 (3) |
O3—C18 | 1.366 (3) | N2—C32 | 1.360 (3) |
O3—H1O3 | 0.8200 | N2—C28 | 1.366 (3) |
C1—C2 | 1.555 (3) | N2—H2N2 | 0.8600 |
C1—H1A | 0.9600 | C27—C28 | 1.481 (4) |
C1—H1B | 0.9600 | C27—H27A | 0.9600 |
C1—H1C | 0.9600 | C27—H27B | 0.9600 |
C2—C9 | 1.530 (3) | C27—H27C | 0.9600 |
C2—C3 | 1.543 (3) | C28—C29 | 1.341 (4) |
C2—C15 | 1.542 (3) | C29—C30 | 1.411 (4) |
C3—C8 | 1.387 (3) | C29—H29 | 0.9300 |
C3—C4 | 1.383 (3) | C30—C31 | 1.341 (4) |
C4—C5 | 1.390 (3) | C30—H30 | 0.9300 |
C4—H4 | 0.9300 | C31—C32 | 1.419 (4) |
C5—C6 | 1.372 (3) | C31—H31 | 0.9300 |
C5—H5 | 0.9300 | O6A—O6Bi | 1.048 (7) |
C6—C7 | 1.377 (3) | O6A—C38A | 1.278 (5) |
C7—C8 | 1.380 (3) | N3—C38B | 1.140 (10) |
C7—H7 | 0.9300 | N3—C38A | 1.256 (5) |
C8—H8 | 0.9300 | N3—C34A | 1.408 (5) |
C9—C10 | 1.386 (3) | N3—C34B | 1.482 (11) |
C9—C14 | 1.385 (3) | N3—H3N3 | 0.8600 |
C10—C11 | 1.378 (4) | C33—C34A | 1.359 (7) |
C10—H10 | 0.9300 | C33—C38B | 1.638 (11) |
C11—C12 | 1.377 (4) | C33—C36B | 1.507 (17) |
C11—H11 | 0.9300 | C33—H33A | 0.9600 |
C12—C13 | 1.376 (3) | C33—H33B | 0.9601 |
C13—C14 | 1.381 (3) | C33—H33C | 0.9601 |
C13—H13 | 0.9300 | C34A—C36B | 1.300 (15) |
C14—H14 | 0.9300 | C34A—C38B | 1.420 (13) |
C15—C16 | 1.386 (3) | C34A—C35 | 1.385 (7) |
C15—C20 | 1.394 (3) | C34A—C34B | 1.652 (14) |
C16—C17 | 1.380 (3) | C35—C36B | 1.324 (14) |
C16—H16 | 0.9300 | C35—C36A | 1.354 (8) |
C17—C18 | 1.374 (3) | C35—C34B | 1.431 (12) |
C17—H17 | 0.9300 | C35—H35A | 0.9300 |
C18—C19 | 1.379 (3) | C36A—C34B | 1.153 (11) |
C19—C20 | 1.378 (3) | C36A—C37 | 1.365 (9) |
C19—H19 | 0.9300 | C36A—H36A | 0.9299 |
C20—H20 | 0.9300 | C37—C34B | 1.215 (12) |
O4—C26 | 1.267 (3) | C37—C38A | 1.493 (6) |
N1—C22 | 1.365 (4) | C37—H37 | 0.9300 |
N1—C26 | 1.367 (4) | C38A—C34B | 1.387 (12) |
N1—H1N1 | 0.8600 | O6B—O6Ai | 1.048 (7) |
C21—C22 | 1.499 (4) | O6B—C38B | 1.167 (12) |
C21—H21A | 0.9600 | O6B—H3N3 | 1.2226 |
C21—H21B | 0.9600 | C36B—H35A | 1.2573 |
C21—H21C | 0.9600 | C38B—H3N3 | 0.8702 |
C22—C23 | 1.346 (4) | C38B—H33A | 1.3064 |
C23—C24 | 1.400 (5) | O1W—H1W | 0.93 (4) |
C23—H23 | 0.9300 | O1W—H2W | 0.79 (3) |
C24—C25 | 1.348 (5) | ||
C6—O1—H101 | 109.5 | C32—C31—H31 | 120.0 |
C12—O2—H1O2 | 109.5 | O5—C32—N2 | 119.0 (2) |
C18—O3—H1O3 | 109.5 | O5—C32—C31 | 125.4 (3) |
C2—C1—H1A | 109.5 | N2—C32—C31 | 115.6 (2) |
C2—C1—H1B | 109.5 | O6Bi—O6A—C38A | 155.5 (6) |
H1A—C1—H1B | 109.5 | C38B—N3—C38A | 163.3 (7) |
C2—C1—H1C | 109.5 | C38B—N3—C34A | 66.8 (7) |
H1A—C1—H1C | 109.5 | C38A—N3—C34A | 129.9 (4) |
H1B—C1—H1C | 109.5 | C38B—N3—C34B | 136.4 (8) |
C9—C2—C3 | 111.68 (16) | C38A—N3—C34B | 60.2 (6) |
C9—C2—C15 | 108.89 (18) | C34A—N3—C34B | 69.7 (5) |
C3—C2—C15 | 110.20 (17) | C38B—N3—H3N3 | 49.2 |
C9—C2—C1 | 110.05 (18) | C38A—N3—H3N3 | 114.2 |
C3—C2—C1 | 107.12 (17) | C34A—N3—H3N3 | 116.0 |
C15—C2—C1 | 108.85 (17) | C34B—N3—H3N3 | 174.4 |
C8—C3—C4 | 116.99 (19) | C34A—C33—C38B | 55.7 (5) |
C8—C3—C2 | 119.20 (18) | C34A—C33—C36B | 53.6 (6) |
C4—C3—C2 | 123.8 (2) | C38B—C33—C36B | 109.0 (8) |
C3—C4—C5 | 121.3 (2) | C34A—C33—H33A | 108.5 |
C3—C4—H4 | 119.3 | C38B—C33—H33A | 52.9 |
C5—C4—H4 | 119.3 | C36B—C33—H33A | 161.1 |
C6—C5—C4 | 120.17 (19) | C34A—C33—H33B | 110.4 |
C6—C5—H5 | 119.9 | C38B—C33—H33B | 125.6 |
C4—C5—H5 | 119.9 | C36B—C33—H33B | 75.7 |
C5—C6—C7 | 119.70 (19) | H33A—C33—H33B | 109.5 |
C5—C6—O1 | 119.27 (19) | C34A—C33—H33C | 109.5 |
C7—C6—O1 | 121.0 (2) | C38B—C33—H33C | 124.9 |
C8—C7—C6 | 119.5 (2) | C36B—C33—H33C | 84.7 |
C8—C7—H7 | 120.2 | H33A—C33—H33C | 109.5 |
C6—C7—H7 | 120.2 | H33B—C33—H33C | 109.5 |
C7—C8—C3 | 122.3 (2) | C33—C34A—C36B | 69.0 (8) |
C7—C8—H8 | 118.9 | C33—C34A—C38B | 72.2 (5) |
C3—C8—H8 | 118.9 | C36B—C34A—C38B | 140.6 (10) |
C10—C9—C14 | 115.8 (2) | C33—C34A—C35 | 127.7 (5) |
C10—C9—C2 | 121.3 (2) | C36B—C34A—C35 | 59.0 (7) |
C14—C9—C2 | 122.9 (2) | C38B—C34A—C35 | 160.2 (7) |
C11—C10—C9 | 122.6 (2) | C33—C34A—N3 | 119.6 (5) |
C11—C10—H10 | 118.7 | C36B—C34A—N3 | 167.3 (8) |
C9—C10—H10 | 118.7 | C38B—C34A—N3 | 47.5 (4) |
C12—C11—C10 | 120.1 (2) | C35—C34A—N3 | 112.6 (5) |
C12—C11—H11 | 119.9 | C33—C34A—C34B | 175.5 (5) |
C10—C11—H11 | 119.9 | C36B—C34A—C34B | 113.5 (9) |
O2—C12—C11 | 117.6 (2) | C38B—C34A—C34B | 104.8 (6) |
O2—C12—C13 | 123.7 (2) | C35—C34A—C34B | 55.4 (5) |
C11—C12—C13 | 118.7 (2) | N3—C34A—C34B | 57.3 (4) |
C12—C13—C14 | 120.3 (2) | C36B—C35—C36A | 173.6 (7) |
C12—C13—H13 | 119.9 | C36B—C35—C34A | 57.3 (7) |
C14—C13—H13 | 119.9 | C36A—C35—C34A | 120.4 (5) |
C13—C14—C9 | 122.4 (2) | C36B—C35—C34B | 127.9 (9) |
C13—C14—H14 | 118.8 | C36A—C35—C34B | 48.8 (5) |
C9—C14—H14 | 118.8 | C34A—C35—C34B | 71.8 (5) |
C16—C15—C20 | 116.6 (2) | C36B—C35—H35A | 65.1 |
C16—C15—C2 | 122.92 (18) | C36A—C35—H35A | 117.5 |
C20—C15—C2 | 120.29 (19) | C34A—C35—H35A | 122.1 |
C17—C16—C15 | 121.8 (2) | C34B—C35—H35A | 165.5 |
C17—C16—H16 | 119.1 | C34B—C36A—C37 | 57.0 (7) |
C15—C16—H16 | 119.1 | C34B—C36A—C35 | 69.1 (8) |
C18—C17—C16 | 120.5 (2) | C37—C36A—C35 | 126.0 (6) |
C18—C17—H17 | 119.8 | C34B—C36A—H36A | 173.5 |
C16—C17—H17 | 119.8 | C37—C36A—H36A | 116.6 |
O3—C18—C17 | 123.6 (2) | C35—C36A—H36A | 117.4 |
O3—C18—C19 | 117.4 (2) | C34B—C37—C36A | 52.7 (6) |
C17—C18—C19 | 119.0 (2) | C34B—C37—C38A | 60.6 (6) |
C20—C19—C18 | 120.2 (2) | C36A—C37—C38A | 113.2 (6) |
C20—C19—H19 | 119.9 | C34B—C37—H37 | 175.8 |
C18—C19—H19 | 119.9 | C36A—C37—H37 | 124.6 |
C19—C20—C15 | 121.9 (2) | C38A—C37—H37 | 122.2 |
C19—C20—H20 | 119.1 | N3—C38A—O6A | 120.6 (4) |
C15—C20—H20 | 119.1 | N3—C38A—C34B | 68.0 (6) |
C22—N1—C26 | 124.8 (3) | O6A—C38A—C34B | 170.8 (7) |
C22—N1—H1N1 | 117.6 | N3—C38A—C37 | 117.7 (4) |
C26—N1—H1N1 | 117.6 | O6A—C38A—C37 | 121.7 (5) |
C22—C21—H21A | 109.5 | C34B—C38A—C37 | 49.7 (5) |
C22—C21—H21B | 109.5 | O6Ai—O6B—C38B | 159.3 (9) |
H21A—C21—H21B | 109.5 | O6Ai—O6B—H3N3 | 116.7 |
C22—C21—H21C | 109.5 | C38B—O6B—H3N3 | 42.6 |
H21A—C21—H21C | 109.5 | C36A—C34B—C37 | 70.4 (8) |
H21B—C21—H21C | 109.5 | C36A—C34B—C38A | 139.8 (13) |
C23—C22—N1 | 118.7 (3) | C37—C34B—C38A | 69.7 (7) |
C23—C22—C21 | 126.2 (3) | C36A—C34B—C35 | 62.1 (7) |
N1—C22—C21 | 115.1 (3) | C37—C34B—C35 | 132.5 (9) |
C22—C23—C24 | 119.4 (3) | C38A—C34B—C35 | 157.6 (10) |
C22—C23—H23 | 120.3 | C36A—C34B—N3 | 166.9 (12) |
C24—C23—H23 | 120.3 | C37—C34B—N3 | 121.4 (9) |
C25—C24—C23 | 121.2 (3) | C38A—C34B—N3 | 51.8 (4) |
C25—C24—H24 | 119.4 | C35—C34B—N3 | 105.9 (9) |
C23—C24—H24 | 119.4 | C36A—C34B—C34A | 114.8 (10) |
C24—C25—C26 | 120.5 (3) | C37—C34B—C34A | 173.5 (9) |
C24—C25—H25 | 119.7 | C38A—C34B—C34A | 104.9 (7) |
C26—C25—H25 | 119.7 | C35—C34B—C34A | 52.8 (5) |
O4—C26—N1 | 119.3 (3) | N3—C34B—C34A | 53.1 (4) |
O4—C26—C25 | 125.4 (3) | C35—C36B—C34A | 63.7 (8) |
N1—C26—C25 | 115.3 (3) | C35—C36B—C33 | 120.8 (10) |
C32—N2—C28 | 125.2 (2) | C34A—C36B—C33 | 57.3 (7) |
C32—N2—H2N2 | 117.4 | C35—C36B—H35A | 42.1 |
C28—N2—H2N2 | 117.4 | C34A—C36B—H35A | 105.7 |
C28—C27—H27A | 109.5 | C33—C36B—H35A | 160.5 |
C28—C27—H27B | 109.5 | N3—C38B—O6B | 120.4 (10) |
H27A—C27—H27B | 109.5 | N3—C38B—C34A | 65.7 (7) |
C28—C27—H27C | 109.5 | O6B—C38B—C34A | 173.0 (11) |
H27A—C27—H27C | 109.5 | N3—C38B—C33 | 117.8 (9) |
H27B—C27—H27C | 109.5 | O6B—C38B—C33 | 121.9 (9) |
C29—C28—N2 | 118.4 (3) | C34A—C38B—C33 | 52.2 (4) |
C29—C28—C27 | 125.0 (3) | N3—C38B—H3N3 | 48.4 |
N2—C28—C27 | 116.5 (2) | O6B—C38B—H3N3 | 72.1 |
C28—C29—C30 | 119.2 (3) | C34A—C38B—H3N3 | 114.1 |
C28—C29—H29 | 120.4 | C33—C38B—H3N3 | 165.7 |
C30—C29—H29 | 120.4 | N3—C38B—H33A | 153.5 |
C31—C30—C29 | 121.5 (3) | O6B—C38B—H33A | 86.1 |
C31—C30—H30 | 119.3 | C34A—C38B—H33A | 88.1 |
C29—C30—H30 | 119.3 | C33—C38B—H33A | 35.9 |
C30—C31—C32 | 120.1 (3) | H3N3—C38B—H33A | 157.4 |
C30—C31—H31 | 120.0 | H1W—O1W—H2W | 107 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
(I-a) | (I-c) | (I-d) | (II-b) | |
Crystal data | ||||
Chemical formula | C14H10O4·2C5H5NO | C14H10O4·2C6H7NO | C14H10O4·2C6H7NO | C30H22O2·2C6H7NO |
Mr | 432.42 | 460.47 | 460.47 | 632.73 |
Crystal system, space group | Monoclinic, C2/c | Triclinic, P1 | Monoclinic, C2/c | Triclinic, P1 |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 10.569 (1), 14.054 (3), 15.016 (1) | 9.838 (2), 10.085 (2), 14.016 (3) | 11.415 (2), 10.957 (2), 19.660 (3) | 7.305 (1), 9.369 (2), 13.292 (3) |
α, β, γ (°) | 90, 105.95 (3), 90 | 89.77 (3), 74.90 (3), 62.764 (2) | 90, 106.59 (2), 90 | 77.32 (2), 89.46 (2), 76.57 (3) |
V (Å3) | 2144.6 (6) | 1183.0 (5) | 2356.6 (7) | 862.4 (3) |
Z | 4 | 2 | 4 | 1 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.09 | 0.09 | 0.08 |
Crystal size (mm) | 0.20 × 0.10 × 0.04 | 0.20 × 0.20 × 0.10 | 0.30 × 0.25 × 0.10 | 0.30 × 0.20 × 0.10 |
Data collection | ||||
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6780, 2013, 1489 | 9471, 3998, 3051 | 8025, 2063, 1408 | 8783, 3182, 2398 |
Rint | 0.026 | 0.022 | 0.055 | 0.027 |
(sin θ/λ)max (Å−1) | 0.594 | 0.588 | 0.595 | 0.614 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.200, 1.03 | 0.045, 0.141, 0.91 | 0.078, 0.287, 1.09 | 0.042, 0.135, 0.98 |
No. of reflections | 2013 | 3998 | 2063 | 3182 |
No. of parameters | 157 | 307 | 158 | 220 |
No. of restraints | 0 | 0 | 0 | 0 |
H-atom treatment | Only H-atom displacement parameters refined | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.56, −0.35 | 0.28, −0.16 | 0.43, −0.21 | 0.16, −0.15 |
(II-c) | (III-d) | |
Crystal data | ||
Chemical formula | C30H22O2·2C6H7NO | C20H18O3·3C6H7NO·H2O |
Mr | 632.73 | 651.74 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 8.640 (2), 10.203 (2), 11.403 (3) | 10.634 (2), 11.484 (2), 28.574 (4) |
α, β, γ (°) | 106.71 (3), 111.54 (2), 95.87 (2) | 90, 96.43 (2), 90 |
V (Å3) | 870.8 (4) | 3467.5 (10) |
Z | 1 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.08 | 0.09 |
Crystal size (mm) | 0.25 × 0.10 × 0.05 | 0.35 × 0.30 × 0.09 |
Data collection | ||
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8509, 3215, 1947 | 23701, 6109, 3757 |
Rint | 0.034 | 0.062 |
(sin θ/λ)max (Å−1) | 0.613 | 0.595 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.131, 0.98 | 0.047, 0.161, 0.83 |
No. of reflections | 3215 | 6109 |
No. of parameters | 220 | 481 |
No. of restraints | 0 | 20 |
H-atom treatment | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.15 | 0.22, −0.23 |
Computer programs: Collect (Nonius, 2006), DENZO HKL-2000 (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1999).
Compound | D—H···A | D—H | H···A | D—H···A | D···A |
(1-a) | |||||
O2—H1O2···O3 | 0.82 | 1.76 | 172 | 2.579 (2) | |
N1—H1N1···O3i | 0.86 | 2.07 | 168 | 2.916 (2) | |
(1-c) | |||||
O1—H101···O3B | 0.82 | 1.77 | 176 | 2.584 (2) | |
O11—H11O···O3A | 0.82 | 1.73 | 173 | 2.543 (2) | |
N1A—H1NA···O3Aii | 0.86 | 2.13 | 163 | 2.968 (2) | |
N1B—H1NB···O3Biii | 0.86 | 1.97 | 173 | 2.828 (2) | |
(1-d) | |||||
O2—H102···O3 | 0.82 | 1.81 | 166 | 2.612 (4) | |
N1—H1N1···O3i | 0.86 | 1.91 | 178 | 2.767 (4) | |
(2-b) | |||||
O1—H101···O2 | 0.82 | 1.88 | 174 | 2.695 (2) | |
(2-c) | |||||
O1—H1O1···O2 | 0.82 | 1.95 | 173 | 2.765 (4) | |
N1—H1N1···O2iv | 0.86 | 1.91 | 172 | 2.763 (2) | |
(3-d) | |||||
O1—H101···O5 | 0.82 | 1.87 | 178 | 2.692 (3) | |
O2—H1O2···O1Wv | 0.82 | 1.83 | 167 | 2.633 (3) | |
O3—H1O3···O2vi | 0.82 | 2.04 | 167 | 2.843 (2) | |
N1—H1N1···O5vii | 0.86 | 2.00 | 165 | 2.837 (3) | |
N2—H2N2···O4vii | 0.86 | 1.97 | 176 | 2.829 (3) | |
N3—H3N3···O6Aviii | 0.86 | 1.94 | 174 | 2.792 (5) | |
O1W—H1W···O1 | 0.93 (3) | 1.89 (3) | 176 (3) | 2.817 (3) | |
O1W—H2W···O4 | 0.79 (3) | 2.00 (3) | 159 (3) | 2.748 (3) |
Symmetry codes: (i) -x + 1/2, -y + 3/2, -z + 1; (ii) -x + 2, -y, -z + 1]; (iii) -x + 2, -y + 1, -z + 1; (iv) -x + 1, -y, -z + 1; (v) -x + 2, y - 1/2, -z + 1/2; (vi) x - 1, y, z; (vii) -x + 1, -y + 2, -z + 1; (viii) -x + 1, -y + 1, -z + 1. |
Compound | Symmetry between molecules | Distance between reactive centers Å | Perpendicular distance Å | Lateral shift between orbitals Å |
Ideal | Inversion | 3.5-4.2 | 3.5-4.2 | 0.0 |
(1-a) | inversion | 4.196 (3) | 3.537 (3) | 2.257 (3) |
(1-c) | inversion | 4.865 (4) | 3.552 (4) | 3.324 (4) |
(1-d) | inversion | 4.007 (6) | 3.512 (6) | 1.929 (6) |
(2-b) | inversion | 4.769 (4) | 3.605 (4) | 3.122 (4) |
(2-c) | inversion | 4.177 (5) | 3.635 (5) | 1.996 (5) |
(3-d)a | none | 4.027 (4) | 3.634 (4) | 1.735 (4) |
(3-d)a | none | 3.909 (4) | 3.507 (4) | 1.727 (4) |
Note: (a) The two distances are not equivalent because of the absence of an inversion center. |
Inducing photochemical reactions in inclusion compounds has proved to be a unique method for synthesizing a large variety of compounds (Tanaka & Toda, 2002). Understanding the mechanism and the geometric requirements needed to enable such reactions depend on our knowledge of the molecular structure and the packing of molecules in the crystal. It would be an advantage to be able to monitor structural changes at different stages along the reaction. However, in most cases the crystal breaks and its crystal structure cannot be determined. Nevertheless there are more than a few examples for such reactions where the crystal integrity remains through the reaction (homogeneous photochemical reaction) (Wegner, 1969; Osaki & Schmidt, 1972; Cheng & Foxman, 1977; Nakanishi et al., 1981; Chang et al., 1982; Ohashi et al., 1982; Braun & Wegner, 1983; Tieke & Chapuis, 1984; Wang & Jones, 1987; Leibovitch et al., 1998). In some cases, the crystal structures of a solid solution containing both the reactant and the product were analyzed structurally (Nakanishi et al., 1981; Chang et al., 1982; Leibovitch et al., 1998; Theocharis & Desiraju, 1984; Turowska-Tyrk, 2003; Turowska-Tyrk & Trzop, 2003, Zouev et al., 2006; Lavy & Kaftory, 2006; Lavy et al., 2008). In a neat, solid, photoreactive compound, the molecular structural changes induced by the reaction affect and interfere with the neighboring molecules. However, the same molecule in inclusion compounds is surrounded by host molecules that are not involved in the reaction, and are thus not expected to undergo structural changes. Therefore, the volume available for the guest molecule to accommodate its structural change determines the homogeneity of the reaction. This volume is also called `reaction cavity', originally introduced and developed by Cohen (1975) to describe reactions in crystals. This model was further developed by Weiss et al. (1993) and Keating & Garcia-Garibay (1998). The (4πs + 4πs) photocycloadditions are among the oldest known and, with the (2πs + 2πs) cycloadditions, constitute an important group of photochemical reactions. The success in showing that photodimerization of pyridone is homogeneous throughout the entire reaction (Lavy et al., 2008) prompted us to examine similar systems. However, we fail to show photodimerization in these systems. We present here the structures of six inclusion compounds and discuss the failure of the systems to undergo solid-state photodimerization.
The six inclusion compounds are: 1,1'-biphenyl-2,2'-dicarboxylic acid–2-(1H)-pyridone (1/2) (I–a) (Fig. 1), 1,1'-biphenyl-2,2'-dicarboxylic acid–4-methyl-2-(1H)-pyridone (1/2) (I–c) (Fig. 2), 1,1'-biphenyl-2,2'-dicarboxylic acid–6-methyl-2-(1H)-pyridone (1/2) (I–d) (Fig. 3), 1,1,6,6-tetraphenyl-2,4-hexdiyne-1,6-diol–1-methyl-2-(1H)-pyridone (1/2) (II–b) (Fig. 4), 1,1,6,6-tetraphenyl-2,4-hexdiyne-1,6-diol–4-methyl-2-(1H)-pyridone (1/2) (II–c) (Fig. 5), and 4,4',4''-(ethane-1,1,1-triyl)triphenol–6-methyl-2-(1H)-pyridone–water (1/3/1) (III–d) (Fig. 6). 1,1'-Biphenyl-2,2'-dicarboxylic acid, (I), has the trivial name diphenic acid. In all six compounds, the guest molecules, (a)–(d), are hydrogen bonded to the host molecules, (I)—(III), through C═O···H—O interactions [the range of O···O distances is 2.543 (2)–2.842 (2) Å; see Table 1 and Figs. 1–6]. In five of the compounds, the guest molecules [(a), (c) and (d)] form dimers by hydrogen bonds of C═O···H—N type through inversion centers. The exception is guest molecule (b), in which the hydrogen donor (N—H) was replaced by N—Me. Such hydrogen-bonding schemes that form dimers are typical of pyridone-like compounds possesing H—N—C═O units. The packing of the guest and host molecules is determined by the hydrogen-bonding schemes. The packing of molecules in the unit cell showing the different schemes of hydrogen bonds together with the mutual geometric realations between pairs of guest molecules are shown in Figs. 7–12 for each of the compounds. In (I–a), (I–c) and (I–d) (Figs. 7–9), each of the host molecules is hydrogen bonded through its hydroxy groups to two guest molecules that form dimers through hydrogen bonds. The molecules are arranged in long zigzag chains. A similar arrangement is observed in (II–c) (Fig. 11). In the absence of a hydrogen donor (N—H) in the guest of (II–b), the dimers are not formed and therefore the chain is cut into isolated host molecules hydrogen bonded to two guest molecules (Fig. 10). The packing of molecules in (III–d) is different (Fig. 12) as a consequence of the presence of three hydrogen donors in the host molecule, and the presence of a water molecule. The latter serve as mediator for hydrogen bonding between two host molecules and a guest. One of the guest molecules does not participate in the hydrogen-bond schemes and its role is filling space. The space available for this molecule is large and the molecule is accommodated in disordered manner.
A search of the Cambridge Structural Database (Allen, 2002) provided 135 compounds containing the pyridone skeleton. The average C═O distance from 169 hits is 1.26 (2) Å, slightly longer than the C═O carbonyl bonds that are not involved in hydrogen bonding. The average O···N intermolecular distance is 2.80 (5) Å, and the average N—H···O angle is 170 (7)°. The ranges of the corresponding parameters in the compounds presented here are 1.257 (3)–1.288 (3) Å [1.247 (2)–1.288 (5)?], 2.763 (2)–2.968 (2) Å and 163–178°, respectively.
The success of [4 + 4] photodimerization in the solid state is highly dependent on the mutual arrangement of the two monomers, on the distances between the reactive centers and on the substituents of the monomer. In the ideal case, the substituents are very small (normally H atoms), the double bonds are parallel, the orbitals of the reacting centers are overlapping and the distances between them are 3.5–4.2 Å. In cases where these requirements are not met, the photoreaction will fail to proceed. The potentially reactive compounds (a)–(d) do not have bulky groups as substituents and therefore it was expected that the other requirements would be fulfilled. It turned out that none of the inclusion compounds was photoactive. The geometric relationships between the guest molecules is summarized in Table 2. As shown in the table, each of the compounds fails to meet one of the requirements. In (I–c) and (II–b), the distances between the reacting centers [4.865 (4) and 4.769 (4) Å, respectively] are above the limit (4.2 Å) set by Schmidt (1965). In (I–a), (I–c), (I–d), (II–b), and (II–c) the lateral shifts between the orbitals are too large [2.257 (4), 3.324 (4), 1.929 (6), 3.122 (4) and 1.996 (5) Å, respectively] to allow the overlap needed for the reaction to take place (Ramamurthy & Venkatesan, 1987; Zolotoy et al., 2002). Compound (III–d) shows the best geometry between the guest molecules, such as the shortest distances between reactive atoms and the shortest lateral shift of the orbitals; nevertheless, irradiation did not reveal the expected results. This behaviour might be attributed to the mutual orientation, namely head-to-head with the methyl groups overlapping each other. It is important to note, however, that irradiation of solid inclusion compounds of diphenic acid with 5-chloro- or 5-methyl-2-pyridone revealed [2 + 2] photodimerization to the corresponding cis–anti dimer (Hirano et al., 2005). However, in the later, the distances between the reacting atoms were very short (3.458 and 3.458 Å) and the methyl groups did not overlap each other. It was expected that the packing would be governed by the π–π interactions between guest molecules, which would determine the mutual geometry enabling photodimerization. However, the stronger intermolecular interactions of hydrogen bonds prevailed and determined the molecular packing. We therefore attribute the geometric relations between the guest molecules to the hydrogen-bonding interactions.