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A series of three biphenyl-based Knoevenagel products (denoted 1a, 1b, 1c) with active methylene groups has been synthesized. Compounds 1a and 1b show strong solid-state fluorescence, whereas 1c displays low emission. Effects of substituent groups in condensed phase packing of the molecules have been investigated and correlated with their photophysical properties. Interestingly, compound 1a exhibits mechanofluorochromism with emission color changes from yellow to green (wavelength shift of 40 nm) after mechanical grinding. Furthermore, fluorescence of 1a and 1b is turned off under alkaline conditions, making them potential candidates for aggregation-enhanced emission-based pH sensors.
Supporting information
CCDC references: 1908695; 1908696; 1908697
For all structures, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXL2016/6 (Sheldrick, 2016); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.
Crystal data top
C16H10N2 | Dx = 1.275 Mg m−3 |
Mr = 230.26 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 1955 reflections |
a = 24.316 (6) Å | θ = 2.3–21.6° |
b = 3.9011 (10) Å | µ = 0.08 mm−1 |
c = 25.297 (7) Å | T = 296 K |
V = 2399.7 (10) Å3 | Needle, yellow |
Z = 8 | 0.25 × 0.10 × 0.07 mm |
F(000) = 960 | |
Data collection top
Bruker APEX-II CCD diffractometer | 3008 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.055 |
φ and ω scans | θmax = 26.6°, θmin = 1.6° |
Absorption correction: multi-scan Bruker AXS SADABS program | h = −29→30 |
| k = −4→4 |
11085 measured reflections | l = −26→31 |
4535 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.077 | w = 1/[σ2(Fo2) + (0.094P)2 + 0.3649P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.196 | (Δ/σ)max = 0.029 |
S = 1.07 | Δρmax = 0.39 e Å−3 |
4535 reflections | Δρmin = −0.26 e Å−3 |
325 parameters | Absolute structure: Flack x determined using 946 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute structure parameter: −2.8 (10) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4350 (3) | 0.7422 (13) | 0.8957 (3) | 0.0302 (16) | |
C2 | 0.4906 (3) | 0.6898 (17) | 0.9117 (3) | 0.0409 (17) | |
H2 | 0.515639 | 0.595017 | 0.888091 | 0.049* | |
C3 | 0.5072 (3) | 0.7758 (16) | 0.9606 (3) | 0.0384 (18) | |
H3 | 0.543815 | 0.739079 | 0.969685 | 0.046* | |
C4 | 0.4722 (2) | 0.9172 (14) | 0.9981 (2) | 0.0346 (13) | |
C5 | 0.4180 (2) | 0.9759 (17) | 0.9828 (3) | 0.0433 (16) | |
H5 | 0.393609 | 1.074794 | 1.006662 | 0.052* | |
C6 | 0.4002 (3) | 0.8900 (18) | 0.9333 (3) | 0.0429 (16) | |
H6 | 0.363696 | 0.931457 | 0.924284 | 0.051* | |
C7 | 0.4910 (2) | 0.9982 (14) | 1.0523 (2) | 0.0380 (15) | |
C8 | 0.5441 (3) | 1.1260 (18) | 1.0618 (3) | 0.0479 (17) | |
H8 | 0.568021 | 1.159058 | 1.033515 | 0.057* | |
C9 | 0.5613 (3) | 1.203 (2) | 1.1120 (4) | 0.059 (2) | |
H9 | 0.596111 | 1.295145 | 1.117388 | 0.070* | |
C10 | 0.5270 (3) | 1.144 (2) | 1.1549 (4) | 0.061 (2) | |
H10 | 0.538831 | 1.189801 | 1.189134 | 0.073* | |
C11 | 0.4733 (3) | 1.011 (2) | 1.1454 (3) | 0.058 (2) | |
H11 | 0.449629 | 0.969104 | 1.173553 | 0.070* | |
C12 | 0.4564 (3) | 0.9433 (19) | 1.0943 (3) | 0.0491 (17) | |
H12 | 0.421169 | 0.859722 | 1.088332 | 0.059* | |
C13 | 0.4116 (2) | 0.6409 (16) | 0.8468 (2) | 0.0385 (14) | |
H13 | 0.375076 | 0.707282 | 0.842635 | 0.046* | |
C14 | 0.4321 (2) | 0.4663 (15) | 0.8049 (3) | 0.0379 (14) | |
C15 | 0.4869 (3) | 0.346 (2) | 0.8000 (3) | 0.0462 (17) | |
C16 | 0.3974 (2) | 0.3796 (19) | 0.7613 (3) | 0.0455 (16) | |
C17 | 0.3174 (3) | 0.1997 (16) | 0.2625 (3) | 0.0371 (17) | |
C18 | 0.3539 (2) | 0.3387 (17) | 0.2272 (3) | 0.0426 (15) | |
H18 | 0.390639 | 0.362630 | 0.236629 | 0.051* | |
C19 | 0.3365 (3) | 0.4447 (17) | 0.1772 (3) | 0.0437 (16) | |
H19 | 0.361883 | 0.536583 | 0.153641 | 0.052* | |
C20 | 0.2818 (2) | 0.4151 (15) | 0.1621 (3) | 0.0387 (15) | |
C21 | 0.2446 (3) | 0.2769 (15) | 0.1988 (3) | 0.0358 (18) | |
H21 | 0.207791 | 0.249680 | 0.189557 | 0.043* | |
C22 | 0.2623 (2) | 0.1816 (17) | 0.2483 (3) | 0.0410 (18) | |
H22 | 0.236739 | 0.103275 | 0.272878 | 0.049* | |
C23 | 0.2637 (2) | 0.5186 (15) | 0.1085 (2) | 0.0379 (15) | |
C24 | 0.2980 (3) | 0.4719 (18) | 0.0652 (3) | 0.0465 (16) | |
H24 | 0.332719 | 0.376398 | 0.070015 | 0.056* | |
C25 | 0.2814 (3) | 0.566 (2) | 0.0149 (3) | 0.059 (2) | |
H25 | 0.304963 | 0.533012 | −0.013615 | 0.071* | |
C26 | 0.2313 (4) | 0.703 (2) | 0.0069 (4) | 0.061 (2) | |
H26 | 0.220758 | 0.769159 | −0.026907 | 0.073* | |
C27 | 0.1955 (3) | 0.7474 (17) | 0.0490 (4) | 0.049 (2) | |
H27 | 0.160671 | 0.838709 | 0.043491 | 0.059* | |
C28 | 0.2123 (3) | 0.6537 (18) | 0.0996 (3) | 0.0482 (17) | |
H28 | 0.188313 | 0.682989 | 0.127844 | 0.058* | |
C29 | 0.3398 (2) | 0.0767 (16) | 0.3127 (3) | 0.0429 (16) | |
H29 | 0.377141 | 0.120898 | 0.317042 | 0.051* | |
C30 | 0.3167 (2) | −0.0883 (15) | 0.3538 (3) | 0.0408 (15) | |
C31 | 0.3504 (3) | −0.2037 (17) | 0.3981 (3) | 0.0450 (17) | |
C32 | 0.2595 (3) | −0.1916 (19) | 0.3582 (3) | 0.0482 (19) | |
N1 | 0.3702 (3) | 0.3032 (17) | 0.7257 (3) | 0.065 (2) | |
N2 | 0.5309 (3) | 0.2468 (16) | 0.7949 (4) | 0.066 (2) | |
N3 | 0.3765 (3) | −0.2855 (17) | 0.4306 (4) | 0.065 (2) | |
N4 | 0.2160 (3) | −0.2705 (19) | 0.3631 (3) | 0.071 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.032 (3) | 0.021 (3) | 0.038 (4) | −0.001 (2) | 0.006 (3) | 0.006 (2) |
C2 | 0.035 (4) | 0.052 (4) | 0.036 (5) | 0.004 (3) | 0.004 (3) | −0.002 (3) |
C3 | 0.031 (4) | 0.040 (4) | 0.044 (5) | 0.004 (3) | −0.007 (3) | 0.001 (3) |
C4 | 0.038 (3) | 0.026 (3) | 0.040 (4) | 0.003 (3) | 0.001 (3) | 0.004 (3) |
C5 | 0.037 (3) | 0.045 (4) | 0.048 (4) | 0.011 (3) | 0.000 (3) | −0.006 (3) |
C6 | 0.035 (3) | 0.047 (4) | 0.046 (4) | 0.006 (3) | 0.002 (3) | −0.001 (3) |
C7 | 0.039 (4) | 0.025 (3) | 0.050 (4) | 0.005 (2) | −0.001 (3) | −0.003 (3) |
C8 | 0.041 (4) | 0.051 (4) | 0.051 (5) | 0.005 (3) | 0.000 (3) | 0.005 (4) |
C9 | 0.048 (4) | 0.059 (5) | 0.068 (7) | −0.002 (4) | −0.014 (4) | −0.006 (4) |
C10 | 0.061 (5) | 0.070 (5) | 0.053 (5) | 0.015 (4) | −0.015 (4) | −0.009 (4) |
C11 | 0.067 (5) | 0.059 (5) | 0.048 (5) | 0.015 (4) | 0.004 (4) | 0.000 (3) |
C12 | 0.050 (4) | 0.054 (4) | 0.044 (4) | 0.001 (3) | −0.001 (3) | 0.002 (3) |
C13 | 0.035 (3) | 0.039 (4) | 0.041 (4) | −0.002 (3) | 0.002 (3) | 0.009 (3) |
C14 | 0.036 (3) | 0.034 (3) | 0.044 (4) | −0.004 (3) | 0.002 (3) | 0.005 (3) |
C15 | 0.044 (4) | 0.053 (4) | 0.041 (5) | 0.009 (3) | 0.004 (3) | −0.011 (3) |
C16 | 0.033 (3) | 0.046 (4) | 0.058 (5) | −0.001 (3) | −0.002 (3) | −0.004 (4) |
C17 | 0.037 (3) | 0.038 (4) | 0.036 (5) | 0.002 (3) | −0.001 (3) | −0.008 (3) |
C18 | 0.022 (3) | 0.055 (4) | 0.051 (4) | −0.003 (3) | 0.006 (3) | −0.004 (3) |
C19 | 0.040 (3) | 0.044 (4) | 0.047 (4) | −0.006 (3) | 0.011 (3) | −0.003 (3) |
C20 | 0.042 (3) | 0.028 (3) | 0.047 (4) | 0.000 (3) | 0.006 (3) | −0.005 (3) |
C21 | 0.023 (3) | 0.037 (4) | 0.047 (6) | 0.002 (2) | 0.010 (3) | 0.001 (3) |
C22 | 0.026 (3) | 0.054 (4) | 0.043 (5) | 0.001 (3) | 0.011 (3) | 0.000 (3) |
C23 | 0.041 (3) | 0.028 (3) | 0.045 (4) | −0.006 (3) | 0.002 (3) | −0.002 (3) |
C24 | 0.045 (4) | 0.046 (4) | 0.049 (4) | 0.002 (3) | 0.006 (3) | 0.000 (3) |
C25 | 0.071 (5) | 0.055 (5) | 0.052 (5) | 0.001 (4) | 0.011 (4) | 0.010 (3) |
C26 | 0.075 (5) | 0.058 (5) | 0.051 (5) | −0.005 (4) | −0.013 (4) | 0.006 (4) |
C27 | 0.048 (4) | 0.043 (4) | 0.057 (6) | 0.006 (3) | −0.009 (4) | 0.001 (3) |
C28 | 0.042 (4) | 0.054 (4) | 0.049 (5) | 0.007 (3) | 0.002 (3) | 0.001 (4) |
C29 | 0.032 (3) | 0.034 (4) | 0.062 (5) | 0.002 (3) | 0.007 (3) | −0.009 (3) |
C30 | 0.040 (3) | 0.032 (3) | 0.050 (4) | 0.006 (3) | 0.004 (3) | −0.003 (3) |
C31 | 0.049 (4) | 0.044 (4) | 0.042 (4) | 0.001 (3) | −0.004 (3) | −0.002 (3) |
C32 | 0.035 (4) | 0.062 (5) | 0.048 (5) | 0.009 (3) | 0.000 (3) | 0.007 (3) |
N1 | 0.056 (4) | 0.083 (5) | 0.056 (5) | 0.000 (3) | −0.015 (4) | −0.007 (4) |
N2 | 0.043 (4) | 0.079 (5) | 0.075 (6) | 0.014 (3) | −0.001 (4) | −0.009 (3) |
N3 | 0.051 (4) | 0.069 (5) | 0.076 (6) | 0.009 (3) | −0.014 (4) | 0.010 (3) |
N4 | 0.042 (4) | 0.105 (7) | 0.068 (6) | −0.006 (3) | 0.009 (4) | 0.026 (4) |
Geometric parameters (Å, º) top
C1—C6 | 1.396 (9) | C17—C18 | 1.372 (9) |
C1—C13 | 1.419 (10) | C17—C22 | 1.388 (9) |
C1—C2 | 1.427 (9) | C17—C29 | 1.464 (10) |
C2—C3 | 1.342 (10) | C18—C19 | 1.397 (9) |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.390 (9) | C19—C20 | 1.388 (8) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.392 (8) | C20—C21 | 1.404 (9) |
C4—C7 | 1.480 (8) | C20—C23 | 1.482 (9) |
C5—C6 | 1.369 (9) | C21—C22 | 1.376 (10) |
C5—H5 | 0.9300 | C21—H21 | 0.9300 |
C6—H6 | 0.9300 | C22—H22 | 0.9300 |
C7—C12 | 1.373 (9) | C23—C28 | 1.375 (9) |
C7—C8 | 1.405 (9) | C23—C24 | 1.390 (8) |
C8—C9 | 1.371 (11) | C24—C25 | 1.384 (9) |
C8—H8 | 0.9300 | C24—H24 | 0.9300 |
C9—C10 | 1.387 (13) | C25—C26 | 1.345 (10) |
C9—H9 | 0.9300 | C25—H25 | 0.9300 |
C10—C11 | 1.427 (11) | C26—C27 | 1.386 (13) |
C10—H10 | 0.9300 | C26—H26 | 0.9300 |
C11—C12 | 1.380 (9) | C27—C28 | 1.392 (11) |
C11—H11 | 0.9300 | C27—H27 | 0.9300 |
C12—H12 | 0.9300 | C28—H28 | 0.9300 |
C13—C14 | 1.354 (9) | C29—C30 | 1.345 (9) |
C13—H13 | 0.9300 | C29—H29 | 0.9300 |
C14—C15 | 1.420 (9) | C30—C32 | 1.453 (9) |
C14—C16 | 1.428 (10) | C30—C31 | 1.459 (10) |
C15—N2 | 1.144 (8) | C31—N3 | 1.088 (9) |
C16—N1 | 1.158 (9) | C32—N4 | 1.109 (8) |
| | | |
C6—C1—C13 | 117.8 (6) | C18—C17—C22 | 118.4 (7) |
C6—C1—C2 | 116.1 (7) | C18—C17—C29 | 117.0 (6) |
C13—C1—C2 | 126.0 (6) | C22—C17—C29 | 124.6 (6) |
C3—C2—C1 | 120.7 (7) | C17—C18—C19 | 120.7 (6) |
C3—C2—H2 | 119.6 | C17—C18—H18 | 119.6 |
C1—C2—H2 | 119.6 | C19—C18—H18 | 119.6 |
C2—C3—C4 | 122.9 (6) | C20—C19—C18 | 121.0 (6) |
C2—C3—H3 | 118.5 | C20—C19—H19 | 119.5 |
C4—C3—H3 | 118.5 | C18—C19—H19 | 119.5 |
C3—C4—C5 | 117.1 (6) | C19—C20—C21 | 117.9 (6) |
C3—C4—C7 | 121.9 (5) | C19—C20—C23 | 120.9 (5) |
C5—C4—C7 | 121.0 (5) | C21—C20—C23 | 121.2 (6) |
C6—C5—C4 | 121.0 (6) | C22—C21—C20 | 120.2 (6) |
C6—C5—H5 | 119.5 | C22—C21—H21 | 119.9 |
C4—C5—H5 | 119.5 | C20—C21—H21 | 119.9 |
C5—C6—C1 | 122.2 (6) | C21—C22—C17 | 121.6 (7) |
C5—C6—H6 | 118.9 | C21—C22—H22 | 119.2 |
C1—C6—H6 | 118.9 | C17—C22—H22 | 119.2 |
C12—C7—C8 | 119.1 (6) | C28—C23—C24 | 117.8 (6) |
C12—C7—C4 | 119.6 (5) | C28—C23—C20 | 121.7 (6) |
C8—C7—C4 | 121.2 (6) | C24—C23—C20 | 120.5 (6) |
C9—C8—C7 | 121.0 (7) | C25—C24—C23 | 121.0 (6) |
C9—C8—H8 | 119.5 | C25—C24—H24 | 119.5 |
C7—C8—H8 | 119.5 | C23—C24—H24 | 119.5 |
C8—C9—C10 | 120.4 (8) | C26—C25—C24 | 120.5 (7) |
C8—C9—H9 | 119.8 | C26—C25—H25 | 119.7 |
C10—C9—H9 | 119.8 | C24—C25—H25 | 119.7 |
C9—C10—C11 | 118.6 (8) | C25—C26—C27 | 120.2 (8) |
C9—C10—H10 | 120.7 | C25—C26—H26 | 119.9 |
C11—C10—H10 | 120.7 | C27—C26—H26 | 119.9 |
C12—C11—C10 | 119.9 (7) | C26—C27—C28 | 119.3 (7) |
C12—C11—H11 | 120.0 | C26—C27—H27 | 120.4 |
C10—C11—H11 | 120.0 | C28—C27—H27 | 120.3 |
C7—C12—C11 | 120.9 (6) | C23—C28—C27 | 121.2 (7) |
C7—C12—H12 | 119.6 | C23—C28—H28 | 119.4 |
C11—C12—H12 | 119.6 | C27—C28—H28 | 119.4 |
C14—C13—C1 | 132.4 (6) | C30—C29—C17 | 132.2 (6) |
C14—C13—H13 | 113.8 | C30—C29—H29 | 113.9 |
C1—C13—H13 | 113.8 | C17—C29—H29 | 113.9 |
C13—C14—C15 | 125.5 (6) | C29—C30—C32 | 126.3 (6) |
C13—C14—C16 | 120.4 (5) | C29—C30—C31 | 120.5 (6) |
C15—C14—C16 | 114.1 (6) | C32—C30—C31 | 113.1 (6) |
N2—C15—C14 | 178.4 (9) | N3—C31—C30 | 178.3 (8) |
N1—C16—C14 | 178.4 (8) | N4—C32—C30 | 178.0 (9) |
Crystal data top
C18H15NO2 | Z = 4 |
Mr = 277.31 | F(000) = 584 |
Triclinic, P1 | Dx = 1.250 Mg m−3 |
a = 7.7437 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.8797 (9) Å | Cell parameters from 7988 reflections |
c = 16.2007 (11) Å | θ = 2.5–26.0° |
α = 108.298 (3)° | µ = 0.08 mm−1 |
β = 102.962 (3)° | T = 296 K |
γ = 94.992 (4)° | Needle, colorless |
V = 1473.21 (17) Å3 | 0.19 × 0.14 × 0.11 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 4020 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
φ and ω scans | θmax = 26.1°, θmin = 1.4° |
Absorption correction: multi-scan Bruker AXS SADABS program | h = −9→9 |
| k = −15→13 |
15452 measured reflections | l = −17→19 |
5786 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.0833P)2 + 0.2424P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.163 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.21 e Å−3 |
5786 reflections | Δρmin = −0.22 e Å−3 |
382 parameters | Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0038 (15) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4144 (2) | 0.52633 (13) | 0.78027 (11) | 0.0453 (4) | |
C2 | 0.4087 (3) | 0.63775 (15) | 0.82229 (12) | 0.0599 (5) | |
H2 | 0.451082 | 0.668846 | 0.884721 | 0.072* | |
C3 | 0.3425 (3) | 0.70303 (14) | 0.77437 (12) | 0.0579 (5) | |
H3 | 0.339057 | 0.776821 | 0.805070 | 0.069* | |
C4 | 0.2804 (2) | 0.66126 (13) | 0.68086 (11) | 0.0438 (4) | |
C5 | 0.2061 (2) | 0.73055 (13) | 0.62844 (12) | 0.0464 (4) | |
C6 | 0.2455 (3) | 0.84554 (16) | 0.66313 (15) | 0.0706 (6) | |
H6 | 0.321142 | 0.880515 | 0.720882 | 0.085* | |
C7 | 0.1745 (4) | 0.90934 (17) | 0.61351 (18) | 0.0821 (7) | |
H7 | 0.203414 | 0.986304 | 0.638154 | 0.099* | |
C8 | 0.0625 (3) | 0.86028 (18) | 0.52887 (16) | 0.0730 (6) | |
H8 | 0.013738 | 0.903304 | 0.495979 | 0.088* | |
C9 | 0.0228 (3) | 0.74745 (18) | 0.49309 (15) | 0.0683 (5) | |
H9 | −0.051939 | 0.713231 | 0.435045 | 0.082* | |
C10 | 0.0929 (3) | 0.68359 (15) | 0.54236 (13) | 0.0588 (5) | |
H10 | 0.062985 | 0.606715 | 0.516894 | 0.071* | |
C11 | 0.2918 (2) | 0.55049 (13) | 0.63862 (11) | 0.0480 (4) | |
H11 | 0.255249 | 0.520513 | 0.575992 | 0.058* | |
C12 | 0.3555 (2) | 0.48415 (13) | 0.68649 (11) | 0.0478 (4) | |
H12 | 0.359122 | 0.410361 | 0.655907 | 0.057* | |
C13 | 0.4821 (2) | 0.46321 (14) | 0.83742 (11) | 0.0506 (4) | |
H13 | 0.536727 | 0.506406 | 0.897274 | 0.061* | |
C14 | 0.4799 (2) | 0.35464 (14) | 0.81936 (11) | 0.0471 (4) | |
C15 | 0.5649 (2) | 0.31544 (15) | 0.89391 (12) | 0.0531 (4) | |
C16 | 0.6407 (3) | 0.16025 (17) | 0.93265 (14) | 0.0772 (6) | |
H16A | 0.768060 | 0.190343 | 0.956880 | 0.093* | |
H16B | 0.584090 | 0.179228 | 0.981859 | 0.093* | |
C17 | 0.6153 (5) | 0.0408 (2) | 0.8908 (2) | 0.1146 (11) | |
H17A | 0.489052 | 0.011130 | 0.870459 | 0.172* | |
H17B | 0.673463 | 0.009473 | 0.933939 | 0.172* | |
H17C | 0.666445 | 0.022717 | 0.840358 | 0.172* | |
C18 | 0.3979 (3) | 0.27084 (14) | 0.73328 (12) | 0.0522 (4) | |
C19 | 0.8292 (2) | 0.49552 (13) | 0.70817 (11) | 0.0442 (4) | |
C20 | 0.9553 (2) | 0.54089 (14) | 0.79141 (12) | 0.0532 (4) | |
H20 | 0.995206 | 0.617158 | 0.815445 | 0.064* | |
C21 | 1.0223 (2) | 0.47474 (14) | 0.83892 (12) | 0.0542 (4) | |
H21 | 1.106697 | 0.507396 | 0.894496 | 0.065* | |
C22 | 0.9668 (2) | 0.36018 (13) | 0.80581 (11) | 0.0452 (4) | |
C23 | 1.0369 (2) | 0.28975 (14) | 0.85800 (12) | 0.0514 (4) | |
C24 | 1.0936 (3) | 0.33176 (18) | 0.95157 (14) | 0.0669 (5) | |
H24 | 1.093138 | 0.406179 | 0.981748 | 0.080* | |
C25 | 1.1506 (3) | 0.2650 (2) | 1.00037 (17) | 0.0851 (7) | |
H25 | 1.188179 | 0.294435 | 1.063006 | 0.102* | |
C26 | 1.1520 (4) | 0.1549 (2) | 0.9566 (2) | 0.0947 (8) | |
H26 | 1.188256 | 0.109550 | 0.989630 | 0.114* | |
C27 | 1.0999 (4) | 0.1120 (2) | 0.8644 (2) | 0.0911 (8) | |
H27 | 1.102019 | 0.037692 | 0.834804 | 0.109* | |
C28 | 1.0443 (3) | 0.17903 (16) | 0.81514 (16) | 0.0688 (5) | |
H28 | 1.011499 | 0.149612 | 0.752475 | 0.083* | |
C29 | 0.8408 (2) | 0.31500 (13) | 0.72280 (12) | 0.0524 (4) | |
H29 | 0.799864 | 0.238837 | 0.699203 | 0.063* | |
C30 | 0.7747 (2) | 0.38087 (14) | 0.67436 (11) | 0.0507 (4) | |
H30 | 0.692262 | 0.348029 | 0.618190 | 0.061* | |
C31 | 0.7510 (2) | 0.55820 (13) | 0.65272 (11) | 0.0457 (4) | |
H31 | 0.680260 | 0.514548 | 0.595592 | 0.055* | |
C32 | 0.7630 (2) | 0.66783 (13) | 0.66955 (11) | 0.0464 (4) | |
C33 | 0.6671 (2) | 0.70753 (14) | 0.59736 (11) | 0.0469 (4) | |
C34 | 0.6084 (3) | 0.86674 (15) | 0.56080 (12) | 0.0602 (5) | |
H34A | 0.478526 | 0.846088 | 0.543027 | 0.072* | |
H34B | 0.652029 | 0.842186 | 0.507379 | 0.072* | |
C35 | 0.6623 (4) | 0.98976 (17) | 0.60648 (16) | 0.0875 (8) | |
H35A | 0.791001 | 1.008961 | 0.623431 | 0.131* | |
H35B | 0.618980 | 1.012743 | 0.659383 | 0.131* | |
H35C | 0.611432 | 1.026445 | 0.565911 | 0.131* | |
C36 | 0.8614 (3) | 0.75165 (14) | 0.75273 (12) | 0.0576 (5) | |
N1 | 0.3304 (3) | 0.20326 (13) | 0.66545 (11) | 0.0749 (5) | |
N2 | 0.9404 (3) | 0.81920 (14) | 0.81881 (12) | 0.0895 (7) | |
O1 | 0.56116 (18) | 0.20697 (10) | 0.86540 (8) | 0.0612 (4) | |
O2 | 0.6296 (2) | 0.37596 (12) | 0.96995 (9) | 0.0799 (5) | |
O3 | 0.68838 (17) | 0.81697 (9) | 0.62557 (8) | 0.0547 (3) | |
O4 | 0.58288 (19) | 0.64713 (10) | 0.52346 (8) | 0.0644 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0484 (9) | 0.0432 (9) | 0.0409 (8) | 0.0079 (7) | 0.0067 (7) | 0.0132 (7) |
C2 | 0.0776 (13) | 0.0488 (10) | 0.0404 (9) | 0.0110 (9) | 0.0014 (9) | 0.0075 (8) |
C3 | 0.0751 (12) | 0.0372 (9) | 0.0515 (10) | 0.0117 (8) | 0.0075 (9) | 0.0077 (8) |
C4 | 0.0430 (8) | 0.0391 (8) | 0.0468 (9) | 0.0043 (7) | 0.0096 (7) | 0.0140 (7) |
C5 | 0.0481 (9) | 0.0404 (9) | 0.0550 (10) | 0.0078 (7) | 0.0166 (8) | 0.0203 (7) |
C6 | 0.0880 (15) | 0.0452 (10) | 0.0715 (13) | 0.0093 (10) | 0.0089 (11) | 0.0195 (9) |
C7 | 0.1039 (18) | 0.0442 (11) | 0.1058 (19) | 0.0184 (11) | 0.0264 (15) | 0.0354 (12) |
C8 | 0.0808 (15) | 0.0701 (14) | 0.0908 (16) | 0.0299 (12) | 0.0284 (13) | 0.0504 (13) |
C9 | 0.0724 (13) | 0.0702 (13) | 0.0691 (13) | 0.0199 (11) | 0.0109 (10) | 0.0366 (11) |
C10 | 0.0645 (11) | 0.0482 (10) | 0.0624 (11) | 0.0099 (9) | 0.0076 (9) | 0.0238 (9) |
C11 | 0.0592 (10) | 0.0414 (9) | 0.0392 (8) | 0.0071 (8) | 0.0071 (7) | 0.0126 (7) |
C12 | 0.0582 (10) | 0.0363 (8) | 0.0447 (9) | 0.0095 (7) | 0.0087 (8) | 0.0112 (7) |
C13 | 0.0565 (10) | 0.0510 (10) | 0.0401 (9) | 0.0114 (8) | 0.0063 (7) | 0.0139 (7) |
C14 | 0.0507 (9) | 0.0505 (10) | 0.0395 (9) | 0.0109 (8) | 0.0068 (7) | 0.0177 (7) |
C15 | 0.0574 (10) | 0.0522 (10) | 0.0451 (10) | 0.0096 (8) | 0.0030 (8) | 0.0177 (8) |
C16 | 0.0912 (16) | 0.0673 (13) | 0.0659 (13) | 0.0158 (12) | −0.0100 (11) | 0.0339 (11) |
C17 | 0.158 (3) | 0.0688 (16) | 0.110 (2) | 0.0329 (17) | −0.0044 (19) | 0.0457 (15) |
C18 | 0.0658 (11) | 0.0453 (10) | 0.0467 (10) | 0.0094 (8) | 0.0072 (8) | 0.0229 (8) |
C19 | 0.0479 (9) | 0.0428 (9) | 0.0450 (9) | 0.0092 (7) | 0.0133 (7) | 0.0184 (7) |
C20 | 0.0562 (10) | 0.0383 (9) | 0.0581 (10) | 0.0019 (8) | 0.0022 (8) | 0.0176 (8) |
C21 | 0.0556 (10) | 0.0472 (10) | 0.0509 (10) | 0.0046 (8) | −0.0012 (8) | 0.0167 (8) |
C22 | 0.0464 (9) | 0.0438 (9) | 0.0481 (9) | 0.0095 (7) | 0.0121 (7) | 0.0195 (7) |
C23 | 0.0469 (9) | 0.0524 (10) | 0.0605 (11) | 0.0109 (8) | 0.0108 (8) | 0.0286 (8) |
C24 | 0.0713 (13) | 0.0701 (13) | 0.0636 (12) | 0.0176 (10) | 0.0097 (10) | 0.0333 (10) |
C25 | 0.0874 (16) | 0.1055 (19) | 0.0774 (15) | 0.0277 (14) | 0.0110 (12) | 0.0565 (14) |
C26 | 0.0909 (17) | 0.104 (2) | 0.116 (2) | 0.0344 (15) | 0.0144 (16) | 0.0795 (18) |
C27 | 0.0947 (18) | 0.0664 (14) | 0.123 (2) | 0.0301 (13) | 0.0168 (16) | 0.0507 (14) |
C28 | 0.0732 (13) | 0.0558 (11) | 0.0798 (14) | 0.0180 (10) | 0.0114 (11) | 0.0310 (10) |
C29 | 0.0625 (11) | 0.0349 (8) | 0.0539 (10) | 0.0052 (8) | 0.0070 (8) | 0.0137 (7) |
C30 | 0.0575 (10) | 0.0451 (9) | 0.0428 (9) | 0.0077 (8) | 0.0035 (8) | 0.0131 (7) |
C31 | 0.0506 (9) | 0.0449 (9) | 0.0436 (9) | 0.0081 (7) | 0.0111 (7) | 0.0188 (7) |
C32 | 0.0530 (9) | 0.0468 (9) | 0.0438 (9) | 0.0105 (8) | 0.0133 (7) | 0.0207 (7) |
C33 | 0.0541 (10) | 0.0464 (9) | 0.0445 (9) | 0.0108 (8) | 0.0143 (8) | 0.0200 (8) |
C34 | 0.0757 (13) | 0.0553 (11) | 0.0503 (10) | 0.0152 (9) | 0.0033 (9) | 0.0274 (8) |
C35 | 0.1162 (19) | 0.0546 (12) | 0.0825 (15) | 0.0138 (12) | −0.0070 (14) | 0.0348 (11) |
C36 | 0.0822 (13) | 0.0420 (9) | 0.0489 (10) | 0.0125 (9) | 0.0092 (9) | 0.0214 (8) |
N1 | 0.1111 (15) | 0.0502 (9) | 0.0491 (9) | 0.0028 (9) | −0.0036 (9) | 0.0178 (8) |
N2 | 0.1392 (19) | 0.0496 (10) | 0.0608 (11) | 0.0097 (11) | −0.0067 (11) | 0.0180 (9) |
O1 | 0.0754 (9) | 0.0507 (7) | 0.0520 (7) | 0.0136 (6) | −0.0023 (6) | 0.0226 (6) |
O2 | 0.1106 (12) | 0.0647 (9) | 0.0464 (8) | 0.0161 (8) | −0.0112 (7) | 0.0166 (7) |
O3 | 0.0738 (8) | 0.0438 (7) | 0.0460 (7) | 0.0128 (6) | 0.0053 (6) | 0.0212 (5) |
O4 | 0.0839 (9) | 0.0515 (7) | 0.0479 (7) | 0.0078 (7) | −0.0003 (6) | 0.0171 (6) |
Geometric parameters (Å, º) top
C1—C2 | 1.391 (2) | C19—C20 | 1.389 (2) |
C1—C12 | 1.393 (2) | C19—C30 | 1.392 (2) |
C1—C13 | 1.457 (2) | C19—C31 | 1.457 (2) |
C2—C3 | 1.371 (2) | C20—C21 | 1.377 (2) |
C2—H2 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.390 (2) | C21—C22 | 1.392 (2) |
C3—H3 | 0.9300 | C21—H21 | 0.9300 |
C4—C11 | 1.396 (2) | C22—C29 | 1.386 (2) |
C4—C5 | 1.481 (2) | C22—C23 | 1.481 (2) |
C5—C10 | 1.382 (3) | C23—C24 | 1.389 (3) |
C5—C6 | 1.387 (2) | C23—C28 | 1.389 (3) |
C6—C7 | 1.385 (3) | C24—C25 | 1.377 (3) |
C6—H6 | 0.9300 | C24—H24 | 0.9300 |
C7—C8 | 1.363 (3) | C25—C26 | 1.374 (4) |
C7—H7 | 0.9300 | C25—H25 | 0.9300 |
C8—C9 | 1.362 (3) | C26—C27 | 1.368 (4) |
C8—H8 | 0.9300 | C26—H26 | 0.9300 |
C9—C10 | 1.380 (2) | C27—C28 | 1.382 (3) |
C9—H9 | 0.9300 | C27—H27 | 0.9300 |
C10—H10 | 0.9300 | C28—H28 | 0.9300 |
C11—C12 | 1.375 (2) | C29—C30 | 1.383 (2) |
C11—H11 | 0.9300 | C29—H29 | 0.9300 |
C12—H12 | 0.9300 | C30—H30 | 0.9300 |
C13—C14 | 1.333 (2) | C31—C32 | 1.342 (2) |
C13—H13 | 0.9300 | C31—H31 | 0.9300 |
C14—C18 | 1.432 (2) | C32—C36 | 1.430 (2) |
C14—C15 | 1.494 (2) | C32—C33 | 1.494 (2) |
C15—O2 | 1.195 (2) | C33—O4 | 1.2002 (19) |
C15—O1 | 1.322 (2) | C33—O3 | 1.3206 (19) |
C16—C17 | 1.448 (3) | C34—O3 | 1.4475 (19) |
C16—O1 | 1.450 (2) | C34—C35 | 1.498 (3) |
C16—H16A | 0.9700 | C34—H34A | 0.9700 |
C16—H16B | 0.9700 | C34—H34B | 0.9700 |
C17—H17A | 0.9600 | C35—H35A | 0.9600 |
C17—H17B | 0.9600 | C35—H35B | 0.9600 |
C17—H17C | 0.9600 | C35—H35C | 0.9600 |
C18—N1 | 1.141 (2) | C36—N2 | 1.143 (2) |
| | | |
C2—C1—C12 | 117.12 (15) | C20—C19—C31 | 125.19 (15) |
C2—C1—C13 | 117.71 (15) | C30—C19—C31 | 117.27 (15) |
C12—C1—C13 | 125.17 (15) | C21—C20—C19 | 121.05 (15) |
C3—C2—C1 | 121.93 (16) | C21—C20—H20 | 119.5 |
C3—C2—H2 | 119.0 | C19—C20—H20 | 119.5 |
C1—C2—H2 | 119.0 | C20—C21—C22 | 121.63 (16) |
C2—C3—C4 | 121.39 (15) | C20—C21—H21 | 119.2 |
C2—C3—H3 | 119.3 | C22—C21—H21 | 119.2 |
C4—C3—H3 | 119.3 | C29—C22—C21 | 117.27 (15) |
C3—C4—C11 | 116.58 (15) | C29—C22—C23 | 121.35 (15) |
C3—C4—C5 | 121.88 (14) | C21—C22—C23 | 121.36 (15) |
C11—C4—C5 | 121.54 (14) | C24—C23—C28 | 117.86 (17) |
C10—C5—C6 | 116.55 (16) | C24—C23—C22 | 120.98 (16) |
C10—C5—C4 | 121.49 (15) | C28—C23—C22 | 121.14 (17) |
C6—C5—C4 | 121.95 (16) | C25—C24—C23 | 121.1 (2) |
C7—C6—C5 | 121.3 (2) | C25—C24—H24 | 119.5 |
C7—C6—H6 | 119.3 | C23—C24—H24 | 119.5 |
C5—C6—H6 | 119.3 | C26—C25—C24 | 120.0 (2) |
C8—C7—C6 | 120.6 (2) | C26—C25—H25 | 120.0 |
C8—C7—H7 | 119.7 | C24—C25—H25 | 120.0 |
C6—C7—H7 | 119.7 | C27—C26—C25 | 120.0 (2) |
C9—C8—C7 | 119.16 (19) | C27—C26—H26 | 120.0 |
C9—C8—H8 | 120.4 | C25—C26—H26 | 120.0 |
C7—C8—H8 | 120.4 | C26—C27—C28 | 120.1 (2) |
C8—C9—C10 | 120.5 (2) | C26—C27—H27 | 120.0 |
C8—C9—H9 | 119.8 | C28—C27—H27 | 120.0 |
C10—C9—H9 | 119.8 | C27—C28—C23 | 120.9 (2) |
C9—C10—C5 | 121.90 (18) | C27—C28—H28 | 119.6 |
C9—C10—H10 | 119.0 | C23—C28—H28 | 119.6 |
C5—C10—H10 | 119.0 | C30—C29—C22 | 121.33 (15) |
C12—C11—C4 | 122.23 (15) | C30—C29—H29 | 119.3 |
C12—C11—H11 | 118.9 | C22—C29—H29 | 119.3 |
C4—C11—H11 | 118.9 | C29—C30—C19 | 121.17 (15) |
C11—C12—C1 | 120.69 (15) | C29—C30—H30 | 119.4 |
C11—C12—H12 | 119.7 | C19—C30—H30 | 119.4 |
C1—C12—H12 | 119.7 | C32—C31—C19 | 131.35 (16) |
C14—C13—C1 | 131.58 (16) | C32—C31—H31 | 114.3 |
C14—C13—H13 | 114.2 | C19—C31—H31 | 114.3 |
C1—C13—H13 | 114.2 | C31—C32—C36 | 124.82 (15) |
C13—C14—C18 | 124.84 (15) | C31—C32—C33 | 118.79 (15) |
C13—C14—C15 | 118.57 (15) | C36—C32—C33 | 116.38 (14) |
C18—C14—C15 | 116.58 (14) | O4—C33—O3 | 124.93 (15) |
O2—C15—O1 | 124.57 (16) | O4—C33—C32 | 123.95 (15) |
O2—C15—C14 | 123.43 (16) | O3—C33—C32 | 111.12 (14) |
O1—C15—C14 | 112.00 (14) | O3—C34—C35 | 106.54 (15) |
C17—C16—O1 | 108.84 (18) | O3—C34—H34A | 110.4 |
C17—C16—H16A | 109.9 | C35—C34—H34A | 110.4 |
O1—C16—H16A | 109.9 | O3—C34—H34B | 110.4 |
C17—C16—H16B | 109.9 | C35—C34—H34B | 110.4 |
O1—C16—H16B | 109.9 | H34A—C34—H34B | 108.6 |
H16A—C16—H16B | 108.3 | C34—C35—H35A | 109.5 |
C16—C17—H17A | 109.5 | C34—C35—H35B | 109.5 |
C16—C17—H17B | 109.5 | H35A—C35—H35B | 109.5 |
H17A—C17—H17B | 109.5 | C34—C35—H35C | 109.5 |
C16—C17—H17C | 109.5 | H35A—C35—H35C | 109.5 |
H17A—C17—H17C | 109.5 | H35B—C35—H35C | 109.5 |
H17B—C17—H17C | 109.5 | N2—C36—C32 | 179.4 (2) |
N1—C18—C14 | 178.7 (2) | C15—O1—C16 | 116.46 (14) |
C20—C19—C30 | 117.54 (14) | C33—O3—C34 | 116.85 (13) |
Crystal data top
C19H16O4 | Dx = 1.291 Mg m−3 |
Mr = 308.32 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 1855 reflections |
a = 9.221 (2) Å | θ = 2.5–26.4° |
b = 9.847 (2) Å | µ = 0.09 mm−1 |
c = 34.947 (6) Å | T = 296 K |
V = 3173.1 (11) Å3 | Block, yellow |
Z = 8 | 0.29 × 0.14 × 0.12 mm |
F(000) = 1296 | |
Data collection top
Bruker APEX-II CCD diffractometer | 1579 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.076 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan Bruker AXS SADABS program | h = −10→4 |
| k = −11→11 |
9956 measured reflections | l = −34→36 |
2666 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.083 | w = 1/[σ2(Fo2) + (0.1085P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.219 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.49 e Å−3 |
2666 reflections | Δρmin = −0.40 e Å−3 |
211 parameters | Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.044 (5) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.0997 (4) | 0.1684 (3) | 0.16936 (9) | 0.0399 (10) | |
C2 | 0.0467 (5) | 0.2609 (4) | 0.19616 (11) | 0.0525 (11) | |
H2 | 0.001824 | 0.339663 | 0.187504 | 0.063* | |
C3 | 0.0586 (5) | 0.2397 (4) | 0.23505 (11) | 0.0541 (12) | |
H3 | 0.019757 | 0.303231 | 0.251852 | 0.065* | |
C4 | 0.1269 (4) | 0.1263 (4) | 0.24954 (10) | 0.0429 (10) | |
C5 | 0.1403 (4) | 0.1015 (4) | 0.29128 (11) | 0.0463 (10) | |
C6 | 0.0397 (6) | 0.1547 (4) | 0.31684 (12) | 0.0691 (14) | |
H6 | −0.035760 | 0.208283 | 0.307691 | 0.083* | |
C7 | 0.0500 (7) | 0.1291 (5) | 0.35575 (13) | 0.0860 (18) | |
H7 | −0.018567 | 0.165176 | 0.372400 | 0.103* | |
C8 | 0.1606 (7) | 0.0511 (6) | 0.36976 (13) | 0.0778 (16) | |
H8 | 0.166926 | 0.033643 | 0.395859 | 0.093* | |
C9 | 0.2609 (6) | −0.0007 (5) | 0.34553 (13) | 0.0745 (15) | |
H9 | 0.336788 | −0.052792 | 0.355123 | 0.089* | |
C10 | 0.2512 (5) | 0.0235 (5) | 0.30611 (12) | 0.0644 (13) | |
H10 | 0.320381 | −0.013318 | 0.289755 | 0.077* | |
C11 | 0.1818 (5) | 0.0337 (4) | 0.22304 (11) | 0.0564 (12) | |
H11 | 0.229173 | −0.043623 | 0.231838 | 0.068* | |
C12 | 0.1677 (5) | 0.0534 (4) | 0.18431 (12) | 0.0586 (13) | |
H12 | 0.204465 | −0.011541 | 0.167606 | 0.070* | |
C13 | 0.0787 (4) | 0.2020 (4) | 0.12939 (10) | 0.0418 (10) | |
H13 | 0.042312 | 0.289302 | 0.126168 | 0.050* | |
C14 | 0.0987 (4) | 0.1383 (3) | 0.09587 (10) | 0.0385 (9) | |
C15 | 0.0632 (5) | 0.2181 (4) | 0.06143 (10) | 0.0441 (10) | |
C16 | 0.2281 (5) | 0.0700 (4) | 0.02827 (10) | 0.0455 (10) | |
C17 | 0.1414 (5) | −0.0042 (4) | 0.09000 (11) | 0.0465 (10) | |
C18 | 0.2297 (5) | 0.0065 (5) | −0.01085 (11) | 0.0650 (13) | |
H18A | 0.136116 | −0.031726 | −0.016266 | 0.097* | |
H18B | 0.301692 | −0.063908 | −0.011630 | 0.097* | |
H18C | 0.252298 | 0.074399 | −0.029624 | 0.097* | |
C19 | 0.3703 (4) | 0.1304 (4) | 0.04038 (11) | 0.0510 (11) | |
H19A | 0.400940 | 0.196167 | 0.021788 | 0.076* | |
H19B | 0.441805 | 0.059837 | 0.042293 | 0.076* | |
H19C | 0.359171 | 0.173733 | 0.064810 | 0.076* | |
O1 | 0.1853 (3) | −0.0365 (2) | 0.05428 (7) | 0.0515 (8) | |
O2 | 0.1308 (4) | −0.0946 (3) | 0.11254 (8) | 0.0715 (11) | |
O3 | −0.0126 (3) | 0.3171 (3) | 0.06076 (7) | 0.0634 (9) | |
O4 | 0.1162 (3) | 0.1719 (3) | 0.02771 (6) | 0.0496 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.044 (2) | 0.032 (2) | 0.044 (2) | −0.0002 (17) | 0.0048 (18) | −0.0025 (17) |
C2 | 0.073 (3) | 0.027 (2) | 0.057 (3) | 0.006 (2) | −0.005 (2) | 0.0001 (18) |
C3 | 0.083 (3) | 0.039 (2) | 0.041 (2) | −0.003 (2) | 0.009 (2) | −0.0082 (18) |
C4 | 0.043 (2) | 0.039 (2) | 0.046 (2) | −0.0070 (19) | 0.0070 (18) | 0.0028 (18) |
C5 | 0.050 (3) | 0.043 (2) | 0.046 (3) | −0.012 (2) | 0.004 (2) | −0.0004 (19) |
C6 | 0.091 (4) | 0.054 (3) | 0.063 (3) | 0.015 (3) | 0.012 (3) | 0.000 (2) |
C7 | 0.143 (6) | 0.072 (3) | 0.043 (3) | 0.009 (4) | 0.025 (3) | 0.001 (3) |
C8 | 0.110 (5) | 0.081 (4) | 0.043 (3) | −0.017 (3) | 0.003 (3) | 0.009 (3) |
C9 | 0.068 (4) | 0.101 (4) | 0.054 (3) | −0.008 (3) | −0.012 (3) | 0.015 (3) |
C10 | 0.049 (3) | 0.088 (3) | 0.056 (3) | −0.003 (3) | −0.003 (2) | 0.006 (2) |
C11 | 0.063 (3) | 0.058 (3) | 0.049 (3) | 0.025 (2) | 0.003 (2) | 0.003 (2) |
C12 | 0.066 (3) | 0.065 (3) | 0.045 (3) | 0.023 (2) | 0.009 (2) | −0.002 (2) |
C13 | 0.044 (3) | 0.033 (2) | 0.049 (2) | 0.0026 (17) | 0.0029 (18) | −0.0006 (18) |
C14 | 0.043 (2) | 0.032 (2) | 0.041 (2) | 0.0005 (17) | 0.0037 (17) | 0.0039 (17) |
C15 | 0.050 (3) | 0.040 (2) | 0.043 (2) | −0.003 (2) | 0.0002 (19) | −0.0023 (19) |
C16 | 0.054 (3) | 0.033 (2) | 0.050 (2) | −0.0069 (19) | 0.0061 (19) | −0.0031 (18) |
C17 | 0.060 (3) | 0.034 (2) | 0.046 (2) | −0.0071 (19) | 0.005 (2) | 0.002 (2) |
C18 | 0.071 (3) | 0.066 (3) | 0.058 (3) | −0.017 (2) | 0.015 (2) | −0.019 (2) |
C19 | 0.050 (3) | 0.038 (2) | 0.066 (3) | −0.0030 (19) | 0.008 (2) | −0.0008 (19) |
O1 | 0.068 (2) | 0.0313 (15) | 0.0551 (17) | −0.0073 (13) | 0.0168 (14) | −0.0052 (12) |
O2 | 0.118 (3) | 0.0352 (17) | 0.0608 (18) | −0.0001 (17) | 0.0168 (17) | 0.0095 (15) |
O3 | 0.076 (2) | 0.0542 (19) | 0.0599 (19) | 0.0273 (17) | −0.0019 (15) | 0.0071 (14) |
O4 | 0.0535 (18) | 0.0541 (17) | 0.0410 (16) | 0.0017 (14) | −0.0029 (13) | 0.0016 (12) |
Geometric parameters (Å, º) top
C1—C2 | 1.394 (5) | C11—H11 | 0.9300 |
C1—C12 | 1.396 (5) | C12—H12 | 0.9300 |
C1—C13 | 1.448 (5) | C13—C14 | 1.342 (5) |
C2—C3 | 1.380 (5) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C17 | 1.472 (5) |
C3—C4 | 1.378 (5) | C14—C15 | 1.474 (5) |
C3—H3 | 0.9300 | C15—O3 | 1.200 (4) |
C4—C11 | 1.395 (5) | C15—O4 | 1.354 (4) |
C4—C5 | 1.484 (5) | C16—O4 | 1.439 (5) |
C5—C10 | 1.380 (6) | C16—O1 | 1.443 (4) |
C5—C6 | 1.390 (6) | C16—C19 | 1.501 (5) |
C6—C7 | 1.386 (6) | C16—C18 | 1.504 (5) |
C6—H6 | 0.9300 | C17—O2 | 1.192 (4) |
C7—C8 | 1.368 (7) | C17—O1 | 1.350 (4) |
C7—H7 | 0.9300 | C18—H18A | 0.9600 |
C8—C9 | 1.353 (7) | C18—H18B | 0.9600 |
C8—H8 | 0.9300 | C18—H18C | 0.9600 |
C9—C10 | 1.401 (6) | C19—H19A | 0.9600 |
C9—H9 | 0.9300 | C19—H19B | 0.9600 |
C10—H10 | 0.9300 | C19—H19C | 0.9600 |
C11—C12 | 1.373 (5) | | |
| | | |
C2—C1—C12 | 115.8 (3) | C11—C12—H12 | 119.1 |
C2—C1—C13 | 116.9 (3) | C1—C12—H12 | 119.1 |
C12—C1—C13 | 127.3 (3) | C14—C13—C1 | 135.8 (3) |
C3—C2—C1 | 122.3 (3) | C14—C13—H13 | 112.1 |
C3—C2—H2 | 118.8 | C1—C13—H13 | 112.1 |
C1—C2—H2 | 118.8 | C13—C14—C17 | 127.2 (3) |
C4—C3—C2 | 121.4 (4) | C13—C14—C15 | 115.7 (3) |
C4—C3—H3 | 119.3 | C17—C14—C15 | 117.0 (3) |
C2—C3—H3 | 119.3 | O3—C15—O4 | 117.8 (3) |
C3—C4—C11 | 116.8 (3) | O3—C15—C14 | 125.3 (3) |
C3—C4—C5 | 122.2 (3) | O4—C15—C14 | 116.8 (3) |
C11—C4—C5 | 121.0 (3) | O4—C16—O1 | 108.6 (3) |
C10—C5—C6 | 117.6 (4) | O4—C16—C19 | 110.7 (3) |
C10—C5—C4 | 121.5 (4) | O1—C16—C19 | 110.4 (3) |
C6—C5—C4 | 121.0 (4) | O4—C16—C18 | 106.6 (3) |
C7—C6—C5 | 121.1 (5) | O1—C16—C18 | 105.8 (3) |
C7—C6—H6 | 119.5 | C19—C16—C18 | 114.4 (3) |
C5—C6—H6 | 119.5 | O2—C17—O1 | 117.4 (3) |
C8—C7—C6 | 120.3 (5) | O2—C17—C14 | 126.7 (4) |
C8—C7—H7 | 119.8 | O1—C17—C14 | 115.7 (3) |
C6—C7—H7 | 119.8 | C16—C18—H18A | 109.5 |
C9—C8—C7 | 119.8 (5) | C16—C18—H18B | 109.5 |
C9—C8—H8 | 120.1 | H18A—C18—H18B | 109.5 |
C7—C8—H8 | 120.1 | C16—C18—H18C | 109.5 |
C8—C9—C10 | 120.5 (5) | H18A—C18—H18C | 109.5 |
C8—C9—H9 | 119.8 | H18B—C18—H18C | 109.5 |
C10—C9—H9 | 119.8 | C16—C19—H19A | 109.5 |
C5—C10—C9 | 120.8 (4) | C16—C19—H19B | 109.5 |
C5—C10—H10 | 119.6 | H19A—C19—H19B | 109.5 |
C9—C10—H10 | 119.6 | C16—C19—H19C | 109.5 |
C12—C11—C4 | 121.8 (4) | H19A—C19—H19C | 109.5 |
C12—C11—H11 | 119.1 | H19B—C19—H19C | 109.5 |
C4—C11—H11 | 119.1 | C17—O1—C16 | 119.6 (3) |
C11—C12—C1 | 121.7 (4) | C15—O4—C16 | 118.7 (3) |
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