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The challenging molecular architecture of spirooxindoles is appealing to chemists because it evokes novel synthetic strategies that address configurational demands and provides platforms for further reaction development. The [3+2] cycloaddition of the carbonyl ylide with arylideneoxindole
via a five-membered cyclic transition state gave a novel class of dispirooxindole derivatives, namely
tert-butyl 4′-(4-bromophenyl)-1′′-methyl-2,2′′-dioxo-5′-phenyl-4′,5′-dihydrodispiro[indoline-3,2′-furan-3′,3′′-indoline]-1-carboxylate, C
36H
31BrN
2O, (I
a), 5′-(4-bromophenyl)-1,1′′-dimethyl-4′-phenyl-4′,5′-dihydrodispiro[indoline-3,2′-furan-3′,3′′-indoline]-2,2′′-dione, C
32H
25BrN
2O
3, (I
b), and
tert-butyl 1′′-methyl-2,2′′-dioxo-4′-phenyl-5′-(
p-tolyl)-4′,5′-dihydrodispiro[indoline-3,2′-furan-3′,3′′-indoline]-1-carboxylate, C
37H
34N
2O
5, (I
c). Crystal structure analyses of these dispirooxindoles revealed the formation of two diastereoisomers selectively and confirmed their relative stereochemistry (
SSSR and
RRRS). In all three structures, intramolecular C—H
O and π–π interactions between oxindole and dihydrofuran rings are the key factors governing the regio- and stereoselectivity, and in the absence of conventional hydrogen bonds, their crystal packings are strengthened by intermolecular C—H
π interactions.
Supporting information
CCDC references: 1411981; 1411980; 1411979
For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXL2014 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).
(Ia)
tert-Butyl
4'-(4-bromophenyl)-1''-methyl-2,2''-dioxo-5'-phenyl-4',5'-dihydrodispiro[indoline-3,2'-furan-3',3''-indoline]-1-carboxylate
top
Crystal data top
C36H31BrN2O5 | Z = 2 |
Mr = 651.54 | F(000) = 672 |
Triclinic, P1 | Dx = 1.379 Mg m−3 |
a = 9.5268 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.0566 (17) Å | Cell parameters from 2532 reflections |
c = 13.4593 (17) Å | θ = 2.3–20.1° |
α = 94.401 (2)° | µ = 1.36 mm−1 |
β = 97.385 (2)° | T = 294 K |
γ = 107.762 (2)° | Needle, colorless |
V = 1569.2 (3) Å3 | 0.15 × 0.07 × 0.05 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3428 reflections with I > 2σ(I) |
ω scans | Rint = 0.041 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.7°, θmin = 1.5° |
Tmin = 0.85, Tmax = 0.91 | h = −11→11 |
16039 measured reflections | k = −15→15 |
5948 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.203 | w = 1/[σ2(Fo2) + (0.120P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
5948 reflections | Δρmax = 0.83 e Å−3 |
401 parameters | Δρmin = −0.50 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.24497 (7) | −0.29204 (5) | 0.42937 (5) | 0.0925 (3) | |
C1 | 0.8083 (5) | 0.3526 (4) | 0.1333 (3) | 0.0501 (11) | |
C2 | 0.9162 (5) | 0.3645 (4) | 0.0712 (4) | 0.0664 (14) | |
H2 | 0.9984 | 0.4269 | 0.0791 | 0.080* | |
C3 | 0.8965 (7) | 0.2798 (6) | −0.0026 (4) | 0.0782 (16) | |
H3 | 0.9671 | 0.2856 | −0.0454 | 0.094* | |
C4 | 0.7772 (7) | 0.1885 (5) | −0.0146 (4) | 0.0727 (15) | |
H4 | 0.7686 | 0.1328 | −0.0647 | 0.087* | |
C5 | 0.6673 (6) | 0.1764 (4) | 0.0463 (3) | 0.0580 (12) | |
H5 | 0.5858 | 0.1134 | 0.0379 | 0.070* | |
C6 | 0.6832 (5) | 0.2611 (3) | 0.1201 (3) | 0.0456 (10) | |
C7 | 0.5938 (4) | 0.2690 (3) | 0.2038 (3) | 0.0422 (10) | |
C8 | 0.6994 (5) | 0.3734 (3) | 0.2709 (4) | 0.0472 (10) | |
C9 | 0.4652 (4) | 0.1735 (3) | 0.3200 (3) | 0.0425 (10) | |
H9 | 0.5097 | 0.2229 | 0.3824 | 0.051* | |
C10 | 0.3481 (4) | 0.2129 (3) | 0.2580 (3) | 0.0435 (10) | |
H10 | 0.2726 | 0.1477 | 0.2208 | 0.052* | |
C11 | 0.4315 (4) | 0.2766 (3) | 0.1767 (3) | 0.0405 (9) | |
C12 | 0.4197 (4) | 0.3870 (3) | 0.1625 (3) | 0.0432 (10) | |
C13 | 0.4541 (5) | 0.4804 (3) | 0.2286 (4) | 0.0560 (12) | |
H13 | 0.4955 | 0.4820 | 0.2954 | 0.067* | |
C14 | 0.4274 (5) | 0.5711 (4) | 0.1964 (4) | 0.0606 (13) | |
H14 | 0.4506 | 0.6336 | 0.2417 | 0.073* | |
C15 | 0.3667 (5) | 0.5702 (4) | 0.0976 (4) | 0.0586 (12) | |
H15 | 0.3502 | 0.6323 | 0.0764 | 0.070* | |
C16 | 0.3305 (5) | 0.4782 (4) | 0.0304 (4) | 0.0539 (11) | |
H16 | 0.2894 | 0.4773 | −0.0363 | 0.065* | |
C17 | 0.3560 (4) | 0.3870 (3) | 0.0633 (3) | 0.0424 (10) | |
C18 | 0.3595 (4) | 0.2115 (4) | 0.0729 (3) | 0.0434 (10) | |
C19 | 0.2659 (5) | 0.2686 (3) | 0.3218 (3) | 0.0496 (11) | |
C20 | 0.3355 (6) | 0.3378 (4) | 0.4099 (4) | 0.0697 (14) | |
H20 | 0.4370 | 0.3519 | 0.4317 | 0.084* | |
C21 | 0.2557 (8) | 0.3853 (5) | 0.4651 (5) | 0.0866 (18) | |
H21 | 0.3044 | 0.4337 | 0.5225 | 0.104* | |
C22 | 0.1040 (9) | 0.3622 (6) | 0.4366 (6) | 0.098 (2) | |
H22 | 0.0502 | 0.3936 | 0.4751 | 0.117* | |
C23 | 0.0343 (7) | 0.2935 (5) | 0.3521 (5) | 0.0859 (18) | |
H23 | −0.0681 | 0.2773 | 0.3326 | 0.103* | |
C24 | 0.1149 (6) | 0.2468 (4) | 0.2940 (4) | 0.0650 (13) | |
H24 | 0.0658 | 0.2003 | 0.2356 | 0.078* | |
C25 | 0.4036 (4) | 0.0591 (3) | 0.3444 (3) | 0.0442 (10) | |
C26 | 0.3964 (5) | −0.0276 (4) | 0.2769 (3) | 0.0499 (11) | |
H26 | 0.4256 | −0.0156 | 0.2144 | 0.060* | |
C27 | 0.3461 (5) | −0.1332 (4) | 0.3009 (4) | 0.0566 (12) | |
H27 | 0.3440 | −0.1914 | 0.2558 | 0.068* | |
C28 | 0.2996 (5) | −0.1496 (4) | 0.3927 (4) | 0.0584 (13) | |
C29 | 0.2968 (6) | −0.0653 (5) | 0.4565 (4) | 0.0712 (15) | |
H29 | 0.2579 | −0.0781 | 0.5160 | 0.085* | |
C30 | 0.3515 (5) | 0.0397 (4) | 0.4340 (3) | 0.0581 (12) | |
H30 | 0.3530 | 0.0974 | 0.4796 | 0.070* | |
C31 | 0.9334 (5) | 0.5177 (4) | 0.2610 (4) | 0.0698 (14) | |
H31A | 0.9120 | 0.5492 | 0.3217 | 0.105* | |
H31B | 0.9461 | 0.5688 | 0.2126 | 0.105* | |
H31C | 1.0234 | 0.4994 | 0.2761 | 0.105* | |
C32 | 0.2545 (5) | 0.2555 (4) | −0.0926 (3) | 0.0487 (11) | |
C33 | 0.1737 (5) | 0.1070 (4) | −0.2289 (3) | 0.0595 (13) | |
C34 | 0.0127 (6) | 0.0809 (5) | −0.2174 (5) | 0.0910 (19) | |
H34A | −0.0014 | 0.0542 | −0.1537 | 0.137* | |
H34B | −0.0477 | 0.0266 | −0.2711 | 0.137* | |
H34C | −0.0160 | 0.1452 | −0.2200 | 0.137* | |
C35 | 0.2145 (9) | 0.1710 (6) | −0.3143 (4) | 0.114 (2) | |
H35A | 0.1738 | 0.2298 | −0.3125 | 0.170* | |
H35B | 0.1746 | 0.1249 | −0.3771 | 0.170* | |
H35C | 0.3212 | 0.1993 | −0.3081 | 0.170* | |
C36 | 0.2130 (7) | 0.0033 (5) | −0.2376 (5) | 0.094 (2) | |
H36A | 0.3163 | 0.0197 | −0.2445 | 0.142* | |
H36B | 0.1520 | −0.0440 | −0.2957 | 0.142* | |
H36C | 0.1956 | −0.0316 | −0.1781 | 0.142* | |
N1 | 0.8105 (4) | 0.4204 (3) | 0.2196 (3) | 0.0502 (9) | |
N2 | 0.3282 (4) | 0.2831 (3) | 0.0084 (2) | 0.0434 (8) | |
O1 | 0.6853 (3) | 0.4047 (2) | 0.3550 (2) | 0.0583 (8) | |
O2 | 0.5763 (3) | 0.1775 (2) | 0.2566 (2) | 0.0453 (7) | |
O3 | 0.3304 (4) | 0.1154 (2) | 0.0533 (2) | 0.0597 (8) | |
O4 | 0.1916 (4) | 0.3108 (3) | −0.1329 (2) | 0.0679 (9) | |
O5 | 0.2686 (3) | 0.1650 (3) | −0.1327 (2) | 0.0591 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0852 (5) | 0.0717 (4) | 0.0959 (5) | −0.0095 (3) | −0.0063 (3) | 0.0390 (3) |
C1 | 0.040 (2) | 0.060 (3) | 0.051 (3) | 0.015 (2) | 0.006 (2) | 0.015 (2) |
C2 | 0.049 (3) | 0.074 (4) | 0.076 (4) | 0.015 (2) | 0.016 (3) | 0.023 (3) |
C3 | 0.070 (4) | 0.110 (5) | 0.067 (4) | 0.040 (4) | 0.026 (3) | 0.020 (4) |
C4 | 0.080 (4) | 0.083 (4) | 0.062 (3) | 0.032 (3) | 0.025 (3) | 0.001 (3) |
C5 | 0.068 (3) | 0.061 (3) | 0.049 (3) | 0.025 (2) | 0.013 (2) | 0.004 (2) |
C6 | 0.047 (2) | 0.048 (2) | 0.043 (2) | 0.019 (2) | 0.0040 (19) | 0.007 (2) |
C7 | 0.042 (2) | 0.039 (2) | 0.044 (2) | 0.0115 (18) | 0.0051 (19) | 0.0027 (18) |
C8 | 0.043 (2) | 0.047 (2) | 0.050 (3) | 0.016 (2) | 0.000 (2) | 0.002 (2) |
C9 | 0.042 (2) | 0.047 (2) | 0.036 (2) | 0.0120 (19) | 0.0046 (18) | 0.0019 (18) |
C10 | 0.043 (2) | 0.044 (2) | 0.042 (2) | 0.0122 (19) | 0.0061 (19) | 0.0044 (19) |
C11 | 0.039 (2) | 0.038 (2) | 0.041 (2) | 0.0107 (17) | 0.0002 (18) | −0.0009 (18) |
C12 | 0.039 (2) | 0.043 (2) | 0.046 (3) | 0.0128 (18) | 0.0053 (19) | 0.0004 (19) |
C13 | 0.062 (3) | 0.045 (3) | 0.056 (3) | 0.013 (2) | 0.002 (2) | 0.000 (2) |
C14 | 0.059 (3) | 0.043 (3) | 0.076 (4) | 0.016 (2) | 0.007 (3) | −0.005 (2) |
C15 | 0.053 (3) | 0.047 (3) | 0.079 (4) | 0.020 (2) | 0.010 (3) | 0.012 (3) |
C16 | 0.049 (3) | 0.058 (3) | 0.057 (3) | 0.019 (2) | 0.011 (2) | 0.015 (2) |
C17 | 0.033 (2) | 0.046 (2) | 0.048 (3) | 0.0111 (18) | 0.0112 (18) | 0.005 (2) |
C18 | 0.036 (2) | 0.048 (3) | 0.046 (2) | 0.0121 (19) | 0.0067 (18) | 0.002 (2) |
C19 | 0.054 (3) | 0.046 (2) | 0.053 (3) | 0.019 (2) | 0.015 (2) | 0.009 (2) |
C20 | 0.073 (3) | 0.074 (4) | 0.065 (3) | 0.027 (3) | 0.019 (3) | −0.003 (3) |
C21 | 0.102 (5) | 0.083 (4) | 0.083 (4) | 0.037 (4) | 0.038 (4) | −0.007 (3) |
C22 | 0.131 (6) | 0.110 (5) | 0.093 (5) | 0.082 (5) | 0.055 (5) | 0.025 (4) |
C23 | 0.080 (4) | 0.110 (5) | 0.096 (5) | 0.063 (4) | 0.030 (4) | 0.028 (4) |
C24 | 0.060 (3) | 0.076 (3) | 0.070 (3) | 0.034 (3) | 0.013 (3) | 0.015 (3) |
C25 | 0.041 (2) | 0.050 (3) | 0.041 (2) | 0.0160 (19) | 0.0023 (18) | 0.006 (2) |
C26 | 0.046 (2) | 0.056 (3) | 0.047 (3) | 0.014 (2) | 0.008 (2) | 0.011 (2) |
C27 | 0.053 (3) | 0.049 (3) | 0.065 (3) | 0.014 (2) | 0.004 (2) | 0.010 (2) |
C28 | 0.044 (3) | 0.062 (3) | 0.058 (3) | 0.004 (2) | −0.007 (2) | 0.021 (3) |
C29 | 0.066 (3) | 0.088 (4) | 0.056 (3) | 0.011 (3) | 0.022 (3) | 0.025 (3) |
C30 | 0.065 (3) | 0.067 (3) | 0.042 (3) | 0.019 (2) | 0.012 (2) | 0.006 (2) |
C31 | 0.058 (3) | 0.052 (3) | 0.081 (4) | −0.001 (2) | −0.005 (3) | 0.004 (3) |
C32 | 0.040 (2) | 0.058 (3) | 0.048 (3) | 0.016 (2) | 0.010 (2) | 0.003 (2) |
C33 | 0.047 (3) | 0.080 (3) | 0.045 (3) | 0.017 (2) | 0.001 (2) | −0.011 (2) |
C34 | 0.051 (3) | 0.114 (5) | 0.095 (4) | 0.024 (3) | −0.007 (3) | −0.025 (4) |
C35 | 0.151 (7) | 0.126 (6) | 0.044 (3) | 0.020 (5) | 0.017 (4) | −0.005 (4) |
C36 | 0.077 (4) | 0.103 (5) | 0.095 (5) | 0.037 (4) | −0.007 (3) | −0.040 (4) |
N1 | 0.043 (2) | 0.046 (2) | 0.052 (2) | 0.0040 (16) | 0.0014 (17) | 0.0028 (18) |
N2 | 0.0427 (19) | 0.046 (2) | 0.041 (2) | 0.0158 (16) | 0.0021 (16) | 0.0025 (16) |
O1 | 0.065 (2) | 0.0557 (19) | 0.0463 (19) | 0.0126 (16) | 0.0026 (15) | −0.0041 (15) |
O2 | 0.0413 (15) | 0.0467 (16) | 0.0493 (17) | 0.0141 (13) | 0.0093 (13) | 0.0104 (13) |
O3 | 0.077 (2) | 0.0405 (19) | 0.0530 (19) | 0.0136 (15) | −0.0039 (16) | −0.0041 (14) |
O4 | 0.080 (2) | 0.078 (2) | 0.052 (2) | 0.040 (2) | −0.0019 (17) | 0.0077 (17) |
O5 | 0.0516 (18) | 0.077 (2) | 0.0485 (18) | 0.0298 (17) | −0.0036 (14) | −0.0129 (16) |
Geometric parameters (Å, º) top
Br1—C28 | 1.895 (5) | C19—C20 | 1.390 (7) |
C1—C2 | 1.387 (6) | C20—C21 | 1.370 (7) |
C1—C6 | 1.387 (6) | C20—H20 | 0.9300 |
C1—N1 | 1.399 (6) | C21—C22 | 1.378 (9) |
C2—C3 | 1.379 (7) | C21—H21 | 0.9300 |
C2—H2 | 0.9300 | C22—C23 | 1.351 (9) |
C3—C4 | 1.355 (8) | C22—H22 | 0.9300 |
C3—H3 | 0.9300 | C23—C24 | 1.393 (7) |
C4—C5 | 1.391 (7) | C23—H23 | 0.9300 |
C4—H4 | 0.9300 | C24—H24 | 0.9300 |
C5—C6 | 1.387 (6) | C25—C30 | 1.375 (6) |
C5—H5 | 0.9300 | C25—C26 | 1.375 (6) |
C6—C7 | 1.512 (6) | C26—C27 | 1.392 (6) |
C7—O2 | 1.413 (5) | C26—H26 | 0.9300 |
C7—C8 | 1.558 (6) | C27—C28 | 1.374 (7) |
C7—C11 | 1.578 (5) | C27—H27 | 0.9300 |
C8—O1 | 1.211 (5) | C28—C29 | 1.352 (7) |
C8—N1 | 1.354 (6) | C29—C30 | 1.383 (7) |
C9—O2 | 1.434 (5) | C29—H29 | 0.9300 |
C9—C25 | 1.507 (6) | C30—H30 | 0.9300 |
C9—C10 | 1.543 (5) | C31—N1 | 1.453 (5) |
C9—H9 | 0.9800 | C31—H31A | 0.9600 |
C10—C19 | 1.518 (6) | C31—H31B | 0.9600 |
C10—C11 | 1.575 (6) | C31—H31C | 0.9600 |
C10—H10 | 0.9800 | C32—O4 | 1.189 (5) |
C11—C12 | 1.504 (5) | C32—O5 | 1.312 (5) |
C11—C18 | 1.536 (6) | C32—N2 | 1.413 (5) |
C12—C13 | 1.378 (6) | C33—O5 | 1.483 (5) |
C12—C17 | 1.394 (6) | C33—C35 | 1.494 (8) |
C13—C14 | 1.375 (6) | C33—C34 | 1.498 (7) |
C13—H13 | 0.9300 | C33—C36 | 1.511 (7) |
C14—C15 | 1.378 (7) | C34—H34A | 0.9600 |
C14—H14 | 0.9300 | C34—H34B | 0.9600 |
C15—C16 | 1.372 (6) | C34—H34C | 0.9600 |
C15—H15 | 0.9300 | C35—H35A | 0.9600 |
C16—C17 | 1.379 (6) | C35—H35B | 0.9600 |
C16—H16 | 0.9300 | C35—H35C | 0.9600 |
C17—N2 | 1.425 (5) | C36—H36A | 0.9600 |
C18—O3 | 1.200 (5) | C36—H36B | 0.9600 |
C18—N2 | 1.395 (5) | C36—H36C | 0.9600 |
C19—C24 | 1.373 (6) | | |
| | | |
C2—C1—C6 | 121.7 (4) | C20—C21—C22 | 120.8 (6) |
C2—C1—N1 | 128.1 (4) | C20—C21—H21 | 119.6 |
C6—C1—N1 | 110.0 (4) | C22—C21—H21 | 119.6 |
C3—C2—C1 | 117.2 (5) | C23—C22—C21 | 119.4 (5) |
C3—C2—H2 | 121.4 | C23—C22—H22 | 120.3 |
C1—C2—H2 | 121.4 | C21—C22—H22 | 120.3 |
C4—C3—C2 | 121.9 (5) | C22—C23—C24 | 120.3 (6) |
C4—C3—H3 | 119.1 | C22—C23—H23 | 119.8 |
C2—C3—H3 | 119.1 | C24—C23—H23 | 119.8 |
C3—C4—C5 | 121.4 (5) | C19—C24—C23 | 120.9 (5) |
C3—C4—H4 | 119.3 | C19—C24—H24 | 119.5 |
C5—C4—H4 | 119.3 | C23—C24—H24 | 119.5 |
C6—C5—C4 | 117.8 (5) | C30—C25—C26 | 118.8 (4) |
C6—C5—H5 | 121.1 | C30—C25—C9 | 120.5 (4) |
C4—C5—H5 | 121.1 | C26—C25—C9 | 120.7 (4) |
C5—C6—C1 | 120.0 (4) | C25—C26—C27 | 121.0 (4) |
C5—C6—C7 | 130.8 (4) | C25—C26—H26 | 119.5 |
C1—C6—C7 | 108.8 (4) | C27—C26—H26 | 119.5 |
O2—C7—C6 | 109.5 (3) | C28—C27—C26 | 118.7 (4) |
O2—C7—C8 | 110.8 (3) | C28—C27—H27 | 120.6 |
C6—C7—C8 | 101.1 (3) | C26—C27—H27 | 120.6 |
O2—C7—C11 | 105.2 (3) | C29—C28—C27 | 120.7 (4) |
C6—C7—C11 | 119.3 (3) | C29—C28—Br1 | 120.7 (4) |
C8—C7—C11 | 110.9 (3) | C27—C28—Br1 | 118.6 (4) |
O1—C8—N1 | 126.6 (4) | C28—C29—C30 | 120.4 (5) |
O1—C8—C7 | 125.6 (4) | C28—C29—H29 | 119.8 |
N1—C8—C7 | 107.8 (4) | C30—C29—H29 | 119.8 |
O2—C9—C25 | 108.8 (3) | C25—C30—C29 | 120.2 (5) |
O2—C9—C10 | 104.7 (3) | C25—C30—H30 | 119.9 |
C25—C9—C10 | 113.5 (3) | C29—C30—H30 | 119.9 |
O2—C9—H9 | 109.9 | N1—C31—H31A | 109.5 |
C25—C9—H9 | 109.9 | N1—C31—H31B | 109.5 |
C10—C9—H9 | 109.9 | H31A—C31—H31B | 109.5 |
C19—C10—C9 | 114.0 (3) | N1—C31—H31C | 109.5 |
C19—C10—C11 | 118.0 (3) | H31A—C31—H31C | 109.5 |
C9—C10—C11 | 105.2 (3) | H31B—C31—H31C | 109.5 |
C19—C10—H10 | 106.2 | O4—C32—O5 | 126.9 (4) |
C9—C10—H10 | 106.2 | O4—C32—N2 | 122.1 (4) |
C11—C10—H10 | 106.2 | O5—C32—N2 | 111.0 (4) |
C12—C11—C18 | 102.6 (3) | O5—C33—C35 | 110.4 (4) |
C12—C11—C10 | 118.6 (3) | O5—C33—C34 | 109.3 (4) |
C18—C11—C10 | 107.3 (3) | C35—C33—C34 | 113.7 (5) |
C12—C11—C7 | 116.8 (3) | O5—C33—C36 | 101.8 (4) |
C18—C11—C7 | 108.8 (3) | C35—C33—C36 | 111.8 (5) |
C10—C11—C7 | 102.2 (3) | C34—C33—C36 | 109.2 (5) |
C13—C12—C17 | 118.3 (4) | C33—C34—H34A | 109.5 |
C13—C12—C11 | 132.1 (4) | C33—C34—H34B | 109.5 |
C17—C12—C11 | 109.6 (3) | H34A—C34—H34B | 109.5 |
C14—C13—C12 | 120.4 (4) | C33—C34—H34C | 109.5 |
C14—C13—H13 | 119.8 | H34A—C34—H34C | 109.5 |
C12—C13—H13 | 119.8 | H34B—C34—H34C | 109.5 |
C13—C14—C15 | 120.5 (4) | C33—C35—H35A | 109.5 |
C13—C14—H14 | 119.7 | C33—C35—H35B | 109.5 |
C15—C14—H14 | 119.7 | H35A—C35—H35B | 109.5 |
C16—C15—C14 | 120.3 (4) | C33—C35—H35C | 109.5 |
C16—C15—H15 | 119.8 | H35A—C35—H35C | 109.5 |
C14—C15—H15 | 119.8 | H35B—C35—H35C | 109.5 |
C15—C16—C17 | 119.0 (4) | C33—C36—H36A | 109.5 |
C15—C16—H16 | 120.5 | C33—C36—H36B | 109.5 |
C17—C16—H16 | 120.5 | H36A—C36—H36B | 109.5 |
C16—C17—C12 | 121.5 (4) | C33—C36—H36C | 109.5 |
C16—C17—N2 | 129.3 (4) | H36A—C36—H36C | 109.5 |
C12—C17—N2 | 109.3 (3) | H36B—C36—H36C | 109.5 |
O3—C18—N2 | 126.8 (4) | C8—N1—C1 | 111.4 (4) |
O3—C18—C11 | 125.4 (4) | C8—N1—C31 | 123.1 (4) |
N2—C18—C11 | 107.8 (3) | C1—N1—C31 | 124.3 (4) |
C24—C19—C20 | 118.0 (4) | C18—N2—C32 | 126.2 (3) |
C24—C19—C10 | 119.0 (4) | C18—N2—C17 | 110.3 (3) |
C20—C19—C10 | 122.9 (4) | C32—N2—C17 | 122.6 (3) |
C21—C20—C19 | 120.5 (5) | C7—O2—C9 | 108.8 (3) |
C21—C20—H20 | 119.7 | C32—O5—C33 | 120.5 (4) |
C19—C20—H20 | 119.7 | | |
| | | |
C6—C1—C2—C3 | −1.9 (7) | C7—C11—C18—O3 | 64.2 (5) |
N1—C1—C2—C3 | 172.4 (4) | C12—C11—C18—N2 | 5.7 (4) |
C1—C2—C3—C4 | −0.1 (8) | C10—C11—C18—N2 | 131.4 (3) |
C2—C3—C4—C5 | 0.9 (9) | C7—C11—C18—N2 | −118.6 (3) |
C3—C4—C5—C6 | 0.2 (8) | C9—C10—C19—C24 | −138.6 (4) |
C4—C5—C6—C1 | −2.1 (6) | C11—C10—C19—C24 | 97.1 (5) |
C4—C5—C6—C7 | −173.1 (4) | C9—C10—C19—C20 | 38.7 (6) |
C2—C1—C6—C5 | 3.0 (6) | C11—C10—C19—C20 | −85.6 (5) |
N1—C1—C6—C5 | −172.2 (4) | C24—C19—C20—C21 | −2.2 (7) |
C2—C1—C6—C7 | 175.8 (4) | C10—C19—C20—C21 | −179.4 (5) |
N1—C1—C6—C7 | 0.6 (5) | C19—C20—C21—C22 | 2.6 (9) |
C5—C6—C7—O2 | 48.9 (6) | C20—C21—C22—C23 | −1.3 (10) |
C1—C6—C7—O2 | −122.8 (4) | C21—C22—C23—C24 | −0.3 (10) |
C5—C6—C7—C8 | 165.9 (4) | C20—C19—C24—C23 | 0.6 (7) |
C1—C6—C7—C8 | −5.8 (4) | C10—C19—C24—C23 | 177.9 (4) |
C5—C6—C7—C11 | −72.2 (6) | C22—C23—C24—C19 | 0.7 (8) |
C1—C6—C7—C11 | 116.0 (4) | O2—C9—C25—C30 | 150.3 (4) |
O2—C7—C8—O1 | −53.1 (5) | C10—C9—C25—C30 | −93.6 (5) |
C6—C7—C8—O1 | −169.1 (4) | O2—C9—C25—C26 | −30.8 (5) |
C11—C7—C8—O1 | 63.3 (5) | C10—C9—C25—C26 | 85.4 (5) |
O2—C7—C8—N1 | 125.3 (4) | C30—C25—C26—C27 | −4.0 (6) |
C6—C7—C8—N1 | 9.3 (4) | C9—C25—C26—C27 | 177.0 (4) |
C11—C7—C8—N1 | −118.2 (4) | C25—C26—C27—C28 | 1.8 (6) |
O2—C9—C10—C19 | −150.8 (3) | C26—C27—C28—C29 | 2.8 (7) |
C25—C9—C10—C19 | 90.7 (4) | C26—C27—C28—Br1 | −175.5 (3) |
O2—C9—C10—C11 | −19.9 (4) | C27—C28—C29—C30 | −5.0 (7) |
C25—C9—C10—C11 | −138.4 (3) | Br1—C28—C29—C30 | 173.2 (4) |
C19—C10—C11—C12 | −2.9 (5) | C26—C25—C30—C29 | 1.8 (7) |
C9—C10—C11—C12 | −131.5 (3) | C9—C25—C30—C29 | −179.2 (4) |
C19—C10—C11—C18 | −118.5 (4) | C28—C29—C30—C25 | 2.7 (8) |
C9—C10—C11—C18 | 113.0 (3) | O1—C8—N1—C1 | 168.7 (4) |
C19—C10—C11—C7 | 127.1 (4) | C7—C8—N1—C1 | −9.7 (5) |
C9—C10—C11—C7 | −1.4 (4) | O1—C8—N1—C31 | 1.0 (7) |
O2—C7—C11—C12 | 153.9 (3) | C7—C8—N1—C31 | −177.4 (4) |
C6—C7—C11—C12 | −82.8 (4) | C2—C1—N1—C8 | −168.8 (4) |
C8—C7—C11—C12 | 34.0 (5) | C6—C1—N1—C8 | 6.0 (5) |
O2—C7—C11—C18 | −90.6 (4) | C2—C1—N1—C31 | −1.3 (7) |
C6—C7—C11—C18 | 32.7 (5) | C6—C1—N1—C31 | 173.6 (4) |
C8—C7—C11—C18 | 149.5 (3) | O3—C18—N2—C32 | 0.6 (6) |
O2—C7—C11—C10 | 22.7 (4) | C11—C18—N2—C32 | −176.4 (3) |
C6—C7—C11—C10 | 146.0 (3) | O3—C18—N2—C17 | 169.9 (4) |
C8—C7—C11—C10 | −97.2 (4) | C11—C18—N2—C17 | −7.2 (4) |
C18—C11—C12—C13 | 174.9 (4) | O4—C32—N2—C18 | 156.5 (4) |
C10—C11—C12—C13 | 56.8 (6) | O5—C32—N2—C18 | −24.6 (5) |
C7—C11—C12—C13 | −66.2 (6) | O4—C32—N2—C17 | −11.6 (6) |
C18—C11—C12—C17 | −2.3 (4) | O5—C32—N2—C17 | 167.4 (3) |
C10—C11—C12—C17 | −120.3 (4) | C16—C17—N2—C18 | −175.2 (4) |
C7—C11—C12—C17 | 116.6 (4) | C12—C17—N2—C18 | 5.8 (4) |
C17—C12—C13—C14 | −0.8 (6) | C16—C17—N2—C32 | −5.5 (6) |
C11—C12—C13—C14 | −177.7 (4) | C12—C17—N2—C32 | 175.5 (3) |
C12—C13—C14—C15 | −0.3 (7) | C6—C7—O2—C9 | −167.3 (3) |
C13—C14—C15—C16 | 0.8 (7) | C8—C7—O2—C9 | 82.0 (4) |
C14—C15—C16—C17 | −0.1 (7) | C11—C7—O2—C9 | −37.9 (4) |
C15—C16—C17—C12 | −1.0 (6) | C25—C9—O2—C7 | 158.5 (3) |
C15—C16—C17—N2 | −179.9 (4) | C10—C9—O2—C7 | 36.8 (4) |
C13—C12—C17—C16 | 1.4 (6) | O4—C32—O5—C33 | −15.0 (7) |
C11—C12—C17—C16 | 179.1 (4) | N2—C32—O5—C33 | 166.2 (3) |
C13—C12—C17—N2 | −179.5 (4) | C35—C33—O5—C32 | 68.5 (6) |
C11—C12—C17—N2 | −1.8 (4) | C34—C33—O5—C32 | −57.3 (6) |
C12—C11—C18—O3 | −171.4 (4) | C36—C33—O5—C32 | −172.7 (4) |
C10—C11—C18—O3 | −45.7 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O4i | 0.93 | 2.52 | 3.439 (7) | 170 |
C5—H5···O3 | 0.93 | 2.48 | 3.078 (6) | 123 |
C9—H9···O1 | 0.98 | 2.54 | 3.066 (5) | 114 |
C10—H10···O3 | 0.98 | 2.42 | 2.907 (5) | 110 |
C13—H13···O1 | 0.93 | 2.41 | 3.057 (6) | 127 |
C16—H16···O4 | 0.93 | 2.30 | 2.848 (6) | 117 |
C21—H21···O1ii | 0.93 | 2.55 | 3.374 (7) | 149 |
C31—H31A···O1 | 0.96 | 2.51 | 2.880 (6) | 103 |
C31—H31B···O4iii | 0.96 | 2.55 | 3.331 (6) | 139 |
C34—H34C···O4 | 0.96 | 2.52 | 3.011 (7) | 111 |
C35—H35A···O4 | 0.96 | 2.53 | 3.006 (7) | 111 |
C15—H15···Cg4(C1-C6)iii | 0.93 | 2.74 | 3.579 (6) | 150 |
C23—H23···Cg2(N1/C1/C6/C7/C8)iv | 0.93 | 2.92 | 3.688 (7) | 140 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z; (iv) x−1, y, z. |
(Ib) 5'-(4-Bromophenyl)-1,1''-dimethyl-4'-phenyl-4',5'-dihydrodispiro[indoline-3,2'-furan-3',3''-indoline]-2,2''-dione
top
Crystal data top
C32H25BrN2O3 | Z = 2 |
Mr = 565.45 | F(000) = 580 |
Triclinic, P1 | Dx = 1.444 Mg m−3 |
a = 9.0986 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.7185 (7) Å | Cell parameters from 5332 reflections |
c = 16.5056 (13) Å | θ = 2.6–26.8° |
α = 78.915 (1)° | µ = 1.62 mm−1 |
β = 75.763 (1)° | T = 294 K |
γ = 67.687 (1)° | Needle, colorless |
V = 1300.77 (17) Å3 | 0.11 × 0.09 × 0.05 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4685 reflections with I > 2σ(I) |
ω scans | Rint = 0.020 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 28.3°, θmin = 2.3° |
Tmin = 0.83, Tmax = 0.94 | h = −11→11 |
15355 measured reflections | k = −12→12 |
6111 independent reflections | l = −21→21 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0527P)2 + 0.4155P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
6111 reflections | Δρmax = 0.65 e Å−3 |
345 parameters | Δρmin = −0.42 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 1.66480 (3) | 0.21132 (3) | 0.44227 (2) | 0.06851 (12) | |
C1 | 0.6702 (3) | 0.1452 (3) | 0.84549 (13) | 0.0462 (5) | |
C2 | 0.6388 (4) | 0.0247 (3) | 0.89643 (17) | 0.0657 (7) | |
H2 | 0.5426 | 0.0088 | 0.9004 | 0.079* | |
C3 | 0.7552 (4) | −0.0712 (3) | 0.94114 (16) | 0.0692 (8) | |
H3 | 0.7367 | −0.1528 | 0.9759 | 0.083* | |
C4 | 0.8963 (4) | −0.0488 (3) | 0.93541 (15) | 0.0630 (7) | |
H4 | 0.9731 | −0.1156 | 0.9658 | 0.076* | |
C5 | 0.9273 (3) | 0.0732 (2) | 0.88450 (13) | 0.0487 (5) | |
H5 | 1.0244 | 0.0877 | 0.8803 | 0.058* | |
C6 | 0.8120 (2) | 0.1715 (2) | 0.84071 (12) | 0.0381 (4) | |
C7 | 0.8160 (2) | 0.3028 (2) | 0.77543 (11) | 0.0363 (4) | |
C8 | 0.6621 (3) | 0.3348 (3) | 0.74014 (14) | 0.0475 (5) | |
C9 | 0.9808 (2) | 0.3854 (2) | 0.66267 (12) | 0.0366 (4) | |
H9 | 0.8998 | 0.4346 | 0.6268 | 0.044* | |
C10 | 0.9549 (2) | 0.4856 (2) | 0.73035 (12) | 0.0359 (4) | |
H10 | 1.0548 | 0.4463 | 0.7530 | 0.043* | |
C11 | 0.8217 (2) | 0.4488 (2) | 0.80256 (12) | 0.0363 (4) | |
C12 | 0.6591 (2) | 0.5724 (2) | 0.82397 (14) | 0.0441 (5) | |
C13 | 0.5463 (3) | 0.6650 (3) | 0.77674 (18) | 0.0611 (6) | |
H13 | 0.5614 | 0.6547 | 0.7201 | 0.073* | |
C14 | 0.4089 (3) | 0.7744 (3) | 0.8148 (3) | 0.0822 (10) | |
H14 | 0.3320 | 0.8369 | 0.7832 | 0.099* | |
C15 | 0.3863 (3) | 0.7906 (3) | 0.8982 (3) | 0.0888 (11) | |
H15 | 0.2941 | 0.8644 | 0.9223 | 0.107* | |
C16 | 0.4969 (4) | 0.7001 (3) | 0.9466 (2) | 0.0742 (9) | |
H16 | 0.4807 | 0.7108 | 1.0033 | 0.089* | |
C17 | 0.6339 (3) | 0.5921 (2) | 0.90840 (15) | 0.0499 (5) | |
C18 | 0.8842 (3) | 0.4132 (2) | 0.88587 (13) | 0.0412 (4) | |
C19 | 0.9279 (2) | 0.6488 (2) | 0.70108 (12) | 0.0392 (4) | |
C20 | 0.8469 (3) | 0.7261 (3) | 0.63616 (16) | 0.0556 (6) | |
H20 | 0.8017 | 0.6785 | 0.6107 | 0.067* | |
C21 | 0.8326 (4) | 0.8749 (3) | 0.6086 (2) | 0.0725 (8) | |
H21 | 0.7790 | 0.9254 | 0.5645 | 0.087* | |
C22 | 0.8962 (4) | 0.9465 (3) | 0.6459 (2) | 0.0759 (9) | |
H22 | 0.8856 | 1.0458 | 0.6275 | 0.091* | |
C23 | 0.9750 (4) | 0.8733 (3) | 0.7096 (2) | 0.0745 (9) | |
H23 | 1.0181 | 0.9227 | 0.7351 | 0.089* | |
C24 | 0.9921 (3) | 0.7249 (3) | 0.73717 (15) | 0.0559 (6) | |
H24 | 1.0478 | 0.6757 | 0.7807 | 0.067* | |
C25 | 1.1477 (2) | 0.3403 (2) | 0.60933 (12) | 0.0392 (4) | |
C26 | 1.2539 (3) | 0.1935 (2) | 0.61442 (14) | 0.0496 (5) | |
H26 | 1.2212 | 0.1206 | 0.6512 | 0.060* | |
C27 | 1.4078 (3) | 0.1541 (3) | 0.56553 (15) | 0.0544 (6) | |
H27 | 1.4782 | 0.0553 | 0.5693 | 0.065* | |
C28 | 1.4557 (3) | 0.2623 (3) | 0.51125 (13) | 0.0463 (5) | |
C29 | 1.3533 (3) | 0.4087 (2) | 0.50493 (13) | 0.0485 (5) | |
H29 | 1.3872 | 0.4814 | 0.4686 | 0.058* | |
C30 | 1.1995 (3) | 0.4465 (2) | 0.55331 (14) | 0.0484 (5) | |
H30 | 1.1290 | 0.5450 | 0.5483 | 0.058* | |
C31 | 0.4337 (4) | 0.2412 (5) | 0.7699 (2) | 0.0915 (10) | |
H31A | 0.3947 | 0.3215 | 0.7277 | 0.137* | |
H31B | 0.3512 | 0.2494 | 0.8197 | 0.137* | |
H31C | 0.4605 | 0.1471 | 0.7491 | 0.137* | |
C32 | 0.7843 (4) | 0.4912 (3) | 1.02949 (15) | 0.0714 (8) | |
H32A | 0.8766 | 0.4062 | 1.0418 | 0.107* | |
H32B | 0.6890 | 0.4843 | 1.0683 | 0.107* | |
H32C | 0.7997 | 0.5813 | 1.0346 | 0.107* | |
N1 | 0.5780 (2) | 0.2495 (2) | 0.78981 (13) | 0.0547 (5) | |
N2 | 0.7654 (2) | 0.4939 (2) | 0.94408 (11) | 0.0506 (5) | |
O1 | 0.6266 (2) | 0.4152 (2) | 0.67712 (11) | 0.0697 (5) | |
O2 | 0.95368 (17) | 0.25538 (15) | 0.71081 (8) | 0.0408 (3) | |
O3 | 1.0189 (2) | 0.33092 (18) | 0.89698 (10) | 0.0530 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.05420 (16) | 0.06142 (17) | 0.07307 (19) | −0.02057 (12) | 0.01993 (12) | −0.00936 (13) |
C1 | 0.0480 (12) | 0.0549 (13) | 0.0406 (11) | −0.0270 (10) | 0.0033 (9) | −0.0130 (9) |
C2 | 0.0751 (17) | 0.0724 (17) | 0.0631 (15) | −0.0534 (15) | 0.0140 (13) | −0.0158 (13) |
C3 | 0.108 (2) | 0.0559 (15) | 0.0510 (14) | −0.0492 (16) | −0.0007 (15) | 0.0018 (12) |
C4 | 0.098 (2) | 0.0447 (13) | 0.0473 (13) | −0.0298 (13) | −0.0154 (13) | 0.0036 (10) |
C5 | 0.0611 (13) | 0.0446 (11) | 0.0430 (11) | −0.0219 (10) | −0.0102 (10) | −0.0034 (9) |
C6 | 0.0443 (10) | 0.0408 (10) | 0.0325 (9) | −0.0215 (8) | −0.0009 (8) | −0.0061 (8) |
C7 | 0.0366 (10) | 0.0405 (10) | 0.0321 (9) | −0.0158 (8) | −0.0028 (7) | −0.0042 (8) |
C8 | 0.0460 (12) | 0.0568 (13) | 0.0415 (11) | −0.0167 (10) | −0.0102 (9) | −0.0097 (10) |
C9 | 0.0422 (10) | 0.0348 (9) | 0.0331 (9) | −0.0168 (8) | −0.0039 (8) | −0.0018 (7) |
C10 | 0.0327 (9) | 0.0367 (9) | 0.0367 (9) | −0.0127 (8) | −0.0035 (7) | −0.0030 (8) |
C11 | 0.0364 (9) | 0.0359 (10) | 0.0351 (9) | −0.0125 (8) | −0.0041 (8) | −0.0042 (8) |
C12 | 0.0359 (10) | 0.0383 (10) | 0.0538 (12) | −0.0149 (8) | 0.0031 (9) | −0.0061 (9) |
C13 | 0.0407 (12) | 0.0518 (13) | 0.0790 (17) | −0.0107 (10) | −0.0069 (12) | 0.0024 (12) |
C14 | 0.0420 (14) | 0.0491 (15) | 0.137 (3) | −0.0053 (11) | −0.0044 (16) | −0.0068 (17) |
C15 | 0.0443 (15) | 0.0573 (17) | 0.155 (3) | −0.0168 (13) | 0.0200 (19) | −0.042 (2) |
C16 | 0.0646 (17) | 0.0729 (18) | 0.091 (2) | −0.0413 (15) | 0.0308 (15) | −0.0465 (16) |
C17 | 0.0516 (12) | 0.0451 (12) | 0.0577 (13) | −0.0300 (10) | 0.0115 (10) | −0.0172 (10) |
C18 | 0.0534 (12) | 0.0393 (10) | 0.0380 (10) | −0.0259 (9) | −0.0075 (9) | −0.0019 (8) |
C19 | 0.0368 (10) | 0.0385 (10) | 0.0408 (10) | −0.0158 (8) | 0.0034 (8) | −0.0093 (8) |
C20 | 0.0573 (14) | 0.0448 (12) | 0.0645 (15) | −0.0177 (11) | −0.0164 (12) | 0.0001 (11) |
C21 | 0.0710 (17) | 0.0464 (14) | 0.0806 (19) | −0.0106 (13) | −0.0088 (15) | 0.0099 (13) |
C22 | 0.0788 (19) | 0.0392 (13) | 0.094 (2) | −0.0218 (13) | 0.0154 (17) | −0.0107 (14) |
C23 | 0.0807 (19) | 0.0606 (16) | 0.090 (2) | −0.0412 (15) | 0.0194 (17) | −0.0376 (16) |
C24 | 0.0618 (14) | 0.0601 (14) | 0.0524 (13) | −0.0303 (12) | 0.0034 (11) | −0.0206 (11) |
C25 | 0.0460 (11) | 0.0402 (10) | 0.0321 (9) | −0.0189 (9) | −0.0017 (8) | −0.0051 (8) |
C26 | 0.0559 (13) | 0.0390 (11) | 0.0458 (11) | −0.0197 (10) | 0.0070 (10) | −0.0010 (9) |
C27 | 0.0525 (13) | 0.0406 (11) | 0.0578 (14) | −0.0134 (10) | 0.0063 (10) | −0.0048 (10) |
C28 | 0.0444 (11) | 0.0521 (12) | 0.0399 (11) | −0.0203 (10) | 0.0057 (9) | −0.0097 (9) |
C29 | 0.0542 (12) | 0.0478 (12) | 0.0410 (11) | −0.0252 (10) | 0.0028 (9) | 0.0010 (9) |
C30 | 0.0524 (12) | 0.0384 (11) | 0.0465 (12) | −0.0152 (9) | −0.0005 (10) | 0.0006 (9) |
C31 | 0.0604 (17) | 0.134 (3) | 0.104 (2) | −0.0541 (19) | −0.0229 (17) | −0.018 (2) |
C32 | 0.108 (2) | 0.0904 (19) | 0.0396 (12) | −0.0664 (18) | 0.0017 (13) | −0.0172 (12) |
N1 | 0.0423 (10) | 0.0720 (13) | 0.0594 (12) | −0.0301 (9) | −0.0057 (9) | −0.0136 (10) |
N2 | 0.0658 (12) | 0.0607 (11) | 0.0362 (9) | −0.0381 (10) | 0.0027 (8) | −0.0127 (8) |
O1 | 0.0662 (11) | 0.0894 (13) | 0.0556 (10) | −0.0253 (10) | −0.0284 (9) | 0.0052 (10) |
O2 | 0.0439 (7) | 0.0390 (7) | 0.0382 (7) | −0.0192 (6) | 0.0037 (6) | −0.0063 (6) |
O3 | 0.0605 (10) | 0.0534 (9) | 0.0527 (9) | −0.0224 (8) | −0.0249 (8) | 0.0001 (7) |
Geometric parameters (Å, º) top
Br1—C28 | 1.896 (2) | C16—C17 | 1.389 (3) |
C1—C2 | 1.385 (3) | C16—H16 | 0.9300 |
C1—C6 | 1.389 (3) | C17—N2 | 1.398 (3) |
C1—N1 | 1.397 (3) | C18—O3 | 1.218 (3) |
C2—C3 | 1.380 (4) | C18—N2 | 1.357 (3) |
C2—H2 | 0.9300 | C19—C24 | 1.383 (3) |
C3—C4 | 1.360 (4) | C19—C20 | 1.384 (3) |
C3—H3 | 0.9300 | C20—C21 | 1.396 (3) |
C4—C5 | 1.395 (3) | C20—H20 | 0.9300 |
C4—H4 | 0.9300 | C21—C22 | 1.357 (5) |
C5—C6 | 1.372 (3) | C21—H21 | 0.9300 |
C5—H5 | 0.9300 | C22—C23 | 1.349 (5) |
C6—C7 | 1.509 (3) | C22—H22 | 0.9300 |
C7—O2 | 1.419 (2) | C23—C24 | 1.386 (4) |
C7—C8 | 1.548 (3) | C23—H23 | 0.9300 |
C7—C11 | 1.590 (3) | C24—H24 | 0.9300 |
C8—O1 | 1.208 (3) | C25—C26 | 1.386 (3) |
C8—N1 | 1.363 (3) | C25—C30 | 1.389 (3) |
C9—O2 | 1.429 (2) | C26—C27 | 1.384 (3) |
C9—C25 | 1.503 (3) | C26—H26 | 0.9300 |
C9—C10 | 1.539 (3) | C27—C28 | 1.376 (3) |
C9—H9 | 0.9800 | C27—H27 | 0.9300 |
C10—C19 | 1.509 (3) | C28—C29 | 1.375 (3) |
C10—C11 | 1.572 (3) | C29—C30 | 1.380 (3) |
C10—H10 | 0.9800 | C29—H29 | 0.9300 |
C11—C12 | 1.521 (3) | C30—H30 | 0.9300 |
C11—C18 | 1.545 (3) | C31—N1 | 1.463 (3) |
C12—C13 | 1.377 (3) | C31—H31A | 0.9600 |
C12—C17 | 1.394 (3) | C31—H31B | 0.9600 |
C13—C14 | 1.396 (4) | C31—H31C | 0.9600 |
C13—H13 | 0.9300 | C32—N2 | 1.456 (3) |
C14—C15 | 1.372 (5) | C32—H32A | 0.9600 |
C14—H14 | 0.9300 | C32—H32B | 0.9600 |
C15—C16 | 1.371 (5) | C32—H32C | 0.9600 |
C15—H15 | 0.9300 | | |
| | | |
C2—C1—C6 | 121.5 (2) | C16—C17—N2 | 127.6 (2) |
C2—C1—N1 | 128.1 (2) | C12—C17—N2 | 110.30 (18) |
C6—C1—N1 | 110.28 (18) | O3—C18—N2 | 125.6 (2) |
C3—C2—C1 | 117.8 (2) | O3—C18—C11 | 126.09 (19) |
C3—C2—H2 | 121.1 | N2—C18—C11 | 108.31 (18) |
C1—C2—H2 | 121.1 | C24—C19—C20 | 117.4 (2) |
C4—C3—C2 | 121.3 (2) | C24—C19—C10 | 119.7 (2) |
C4—C3—H3 | 119.3 | C20—C19—C10 | 122.84 (19) |
C2—C3—H3 | 119.3 | C19—C20—C21 | 120.5 (2) |
C3—C4—C5 | 120.9 (3) | C19—C20—H20 | 119.7 |
C3—C4—H4 | 119.6 | C21—C20—H20 | 119.7 |
C5—C4—H4 | 119.6 | C22—C21—C20 | 120.4 (3) |
C6—C5—C4 | 118.8 (2) | C22—C21—H21 | 119.8 |
C6—C5—H5 | 120.6 | C20—C21—H21 | 119.8 |
C4—C5—H5 | 120.6 | C23—C22—C21 | 119.9 (3) |
C5—C6—C1 | 119.77 (19) | C23—C22—H22 | 120.0 |
C5—C6—C7 | 131.08 (18) | C21—C22—H22 | 120.0 |
C1—C6—C7 | 108.68 (18) | C22—C23—C24 | 120.5 (3) |
O2—C7—C6 | 109.09 (15) | C22—C23—H23 | 119.8 |
O2—C7—C8 | 108.78 (15) | C24—C23—H23 | 119.8 |
C6—C7—C8 | 101.31 (16) | C19—C24—C23 | 121.2 (3) |
O2—C7—C11 | 105.61 (14) | C19—C24—H24 | 119.4 |
C6—C7—C11 | 119.48 (15) | C23—C24—H24 | 119.4 |
C8—C7—C11 | 112.28 (16) | C26—C25—C30 | 118.24 (19) |
O1—C8—N1 | 125.6 (2) | C26—C25—C9 | 121.58 (17) |
O1—C8—C7 | 126.2 (2) | C30—C25—C9 | 120.18 (18) |
N1—C8—C7 | 108.12 (18) | C27—C26—C25 | 120.89 (19) |
O2—C9—C25 | 109.32 (15) | C27—C26—H26 | 119.6 |
O2—C9—C10 | 103.14 (14) | C25—C26—H26 | 119.6 |
C25—C9—C10 | 114.47 (16) | C28—C27—C26 | 119.4 (2) |
O2—C9—H9 | 109.9 | C28—C27—H27 | 120.3 |
C25—C9—H9 | 109.9 | C26—C27—H27 | 120.3 |
C10—C9—H9 | 109.9 | C29—C28—C27 | 121.1 (2) |
C19—C10—C9 | 116.65 (16) | C29—C28—Br1 | 118.53 (16) |
C19—C10—C11 | 116.91 (15) | C27—C28—Br1 | 120.40 (17) |
C9—C10—C11 | 104.28 (15) | C28—C29—C30 | 119.04 (19) |
C19—C10—H10 | 106.0 | C28—C29—H29 | 120.5 |
C9—C10—H10 | 106.0 | C30—C29—H29 | 120.5 |
C11—C10—H10 | 106.0 | C29—C30—C25 | 121.4 (2) |
C12—C11—C18 | 101.64 (16) | C29—C30—H30 | 119.3 |
C12—C11—C10 | 118.59 (16) | C25—C30—H30 | 119.3 |
C18—C11—C10 | 107.71 (16) | N1—C31—H31A | 109.5 |
C12—C11—C7 | 115.86 (16) | N1—C31—H31B | 109.5 |
C18—C11—C7 | 110.95 (15) | H31A—C31—H31B | 109.5 |
C10—C11—C7 | 102.02 (14) | N1—C31—H31C | 109.5 |
C13—C12—C17 | 118.9 (2) | H31A—C31—H31C | 109.5 |
C13—C12—C11 | 132.9 (2) | H31B—C31—H31C | 109.5 |
C17—C12—C11 | 108.09 (19) | N2—C32—H32A | 109.5 |
C12—C13—C14 | 119.3 (3) | N2—C32—H32B | 109.5 |
C12—C13—H13 | 120.4 | H32A—C32—H32B | 109.5 |
C14—C13—H13 | 120.4 | N2—C32—H32C | 109.5 |
C15—C14—C13 | 120.7 (3) | H32A—C32—H32C | 109.5 |
C15—C14—H14 | 119.7 | H32B—C32—H32C | 109.5 |
C13—C14—H14 | 119.7 | C8—N1—C1 | 110.64 (18) |
C16—C15—C14 | 121.3 (3) | C8—N1—C31 | 122.7 (2) |
C16—C15—H15 | 119.4 | C1—N1—C31 | 124.5 (2) |
C14—C15—H15 | 119.4 | C18—N2—C17 | 111.32 (18) |
C15—C16—C17 | 117.9 (3) | C18—N2—C32 | 123.3 (2) |
C15—C16—H16 | 121.1 | C17—N2—C32 | 124.9 (2) |
C17—C16—H16 | 121.1 | C7—O2—C9 | 108.23 (14) |
C16—C17—C12 | 122.0 (3) | | |
| | | |
C6—C1—C2—C3 | −1.4 (4) | C11—C12—C17—C16 | 178.46 (19) |
N1—C1—C2—C3 | 174.5 (2) | C13—C12—C17—N2 | −176.57 (19) |
C1—C2—C3—C4 | −0.2 (4) | C11—C12—C17—N2 | 0.5 (2) |
C2—C3—C4—C5 | 0.6 (4) | C12—C11—C18—O3 | −171.94 (19) |
C3—C4—C5—C6 | 0.6 (4) | C10—C11—C18—O3 | −46.6 (2) |
C4—C5—C6—C1 | −2.2 (3) | C7—C11—C18—O3 | 64.3 (2) |
C4—C5—C6—C7 | −173.4 (2) | C12—C11—C18—N2 | 5.7 (2) |
C2—C1—C6—C5 | 2.7 (3) | C10—C11—C18—N2 | 131.02 (17) |
N1—C1—C6—C5 | −173.91 (19) | C7—C11—C18—N2 | −118.10 (17) |
C2—C1—C6—C7 | 175.6 (2) | C9—C10—C19—C24 | −143.16 (19) |
N1—C1—C6—C7 | −0.9 (2) | C11—C10—C19—C24 | 92.5 (2) |
C5—C6—C7—O2 | 52.6 (3) | C9—C10—C19—C20 | 33.8 (3) |
C1—C6—C7—O2 | −119.34 (17) | C11—C10—C19—C20 | −90.6 (2) |
C5—C6—C7—C8 | 167.2 (2) | C24—C19—C20—C21 | 0.4 (3) |
C1—C6—C7—C8 | −4.7 (2) | C10—C19—C20—C21 | −176.6 (2) |
C5—C6—C7—C11 | −69.0 (3) | C19—C20—C21—C22 | −0.8 (4) |
C1—C6—C7—C11 | 119.14 (19) | C20—C21—C22—C23 | 0.5 (4) |
O2—C7—C8—O1 | −52.7 (3) | C21—C22—C23—C24 | 0.3 (4) |
C6—C7—C8—O1 | −167.5 (2) | C20—C19—C24—C23 | 0.4 (3) |
C11—C7—C8—O1 | 63.8 (3) | C10—C19—C24—C23 | 177.5 (2) |
O2—C7—C8—N1 | 123.82 (18) | C22—C23—C24—C19 | −0.7 (4) |
C6—C7—C8—N1 | 9.0 (2) | O2—C9—C25—C26 | −3.6 (3) |
C11—C7—C8—N1 | −119.66 (19) | C10—C9—C25—C26 | 111.5 (2) |
O2—C9—C10—C19 | −163.22 (16) | O2—C9—C25—C30 | 176.54 (18) |
C25—C9—C10—C19 | 78.1 (2) | C10—C9—C25—C30 | −68.4 (2) |
O2—C9—C10—C11 | −32.66 (18) | C30—C25—C26—C27 | 0.6 (3) |
C25—C9—C10—C11 | −151.31 (16) | C9—C25—C26—C27 | −179.3 (2) |
C19—C10—C11—C12 | 14.2 (3) | C25—C26—C27—C28 | 0.0 (4) |
C9—C10—C11—C12 | −116.24 (19) | C26—C27—C28—C29 | 0.1 (4) |
C19—C10—C11—C18 | −100.38 (19) | C26—C27—C28—Br1 | −179.11 (19) |
C9—C10—C11—C18 | 129.22 (16) | C27—C28—C29—C30 | −0.8 (4) |
C19—C10—C11—C7 | 142.77 (17) | Br1—C28—C29—C30 | 178.43 (17) |
C9—C10—C11—C7 | 12.36 (18) | C28—C29—C30—C25 | 1.4 (4) |
O2—C7—C11—C12 | 142.36 (16) | C26—C25—C30—C29 | −1.3 (3) |
C6—C7—C11—C12 | −94.4 (2) | C9—C25—C30—C29 | 178.6 (2) |
C8—C7—C11—C12 | 24.0 (2) | O1—C8—N1—C1 | 166.3 (2) |
O2—C7—C11—C18 | −102.44 (17) | C7—C8—N1—C1 | −10.2 (2) |
C6—C7—C11—C18 | 20.8 (2) | O1—C8—N1—C31 | 2.5 (4) |
C8—C7—C11—C18 | 139.16 (17) | C7—C8—N1—C31 | −174.0 (2) |
O2—C7—C11—C10 | 12.05 (18) | C2—C1—N1—C8 | −169.0 (2) |
C6—C7—C11—C10 | 135.29 (17) | C6—C1—N1—C8 | 7.2 (3) |
C8—C7—C11—C10 | −106.35 (17) | C2—C1—N1—C31 | −5.6 (4) |
C18—C11—C12—C13 | 172.9 (2) | C6—C1—N1—C31 | 170.7 (2) |
C10—C11—C12—C13 | 55.1 (3) | O3—C18—N2—C17 | 171.83 (19) |
C7—C11—C12—C13 | −66.7 (3) | C11—C18—N2—C17 | −5.8 (2) |
C18—C11—C12—C17 | −3.6 (2) | O3—C18—N2—C32 | −0.5 (3) |
C10—C11—C12—C17 | −121.42 (19) | C11—C18—N2—C32 | −178.16 (19) |
C7—C11—C12—C17 | 116.73 (18) | C16—C17—N2—C18 | −174.4 (2) |
C17—C12—C13—C14 | −0.9 (3) | C12—C17—N2—C18 | 3.4 (2) |
C11—C12—C13—C14 | −177.1 (2) | C16—C17—N2—C32 | −2.1 (3) |
C12—C13—C14—C15 | 0.3 (4) | C12—C17—N2—C32 | 175.6 (2) |
C13—C14—C15—C16 | −0.2 (5) | C6—C7—O2—C9 | −164.37 (15) |
C14—C15—C16—C17 | 0.7 (4) | C8—C7—O2—C9 | 85.95 (18) |
C15—C16—C17—C12 | −1.2 (3) | C11—C7—O2—C9 | −34.76 (18) |
C15—C16—C17—N2 | 176.3 (2) | C25—C9—O2—C7 | 165.08 (15) |
C13—C12—C17—C16 | 1.4 (3) | C10—C9—O2—C7 | 42.91 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O3 | 0.93 | 2.41 | 2.979 (3) | 119 |
C9—H9···O1 | 0.98 | 2.49 | 3.077 (3) | 118 |
C10—H10···O3 | 0.98 | 2.43 | 2.949 (2) | 113 |
C13—H13···O1 | 0.93 | 2.38 | 2.954 (4) | 120 |
C26—H26···O2 | 0.93 | 2.35 | 2.709 (3) | 103 |
C29—H29···O1i | 0.93 | 2.44 | 3.159 (3) | 135 |
C31—H31A···O1 | 0.96 | 2.51 | 2.867 (4) | 102 |
C32—H32A···O3 | 0.96 | 2.52 | 2.873 (3) | 102 |
C32—H32B···Cg5(C12-C17)ii | 0.96 | 2.86 | 3.713 (4) | 148 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+2. |
(Ic)
tert-Butyl
1''-methyl-2,2''-dioxo-4'-phenyl-5'-(
p-tolyl)-4',5'-dihydrodispiro[indoline-3,2'-furan-3',3''-indoline]-1-carboxylate
top
Crystal data top
C37H34N2O5 | F(000) = 1240 |
Mr = 586.66 | Dx = 1.255 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1226 (9) Å | Cell parameters from 5182 reflections |
b = 14.3682 (13) Å | θ = 2.3–26.5° |
c = 21.353 (2) Å | µ = 0.08 mm−1 |
β = 91.799 (2)° | T = 294 K |
V = 3104.1 (5) Å3 | Plate, colorless |
Z = 4 | 0.11 × 0.08 × 0.05 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 5275 reflections with I > 2σ(I) |
ω scans | Rint = 0.026 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 26.4°, θmin = 1.7° |
Tmin = 0.96, Tmax = 0.99 | h = −12→12 |
32699 measured reflections | k = −17→17 |
6337 independent reflections | l = −26→26 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0716P)2 + 0.6349P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6337 reflections | Δρmax = 0.27 e Å−3 |
402 parameters | Δρmin = −0.16 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.78549 (15) | 0.36896 (10) | 0.86336 (7) | 0.0458 (3) | |
C2 | 0.70250 (17) | 0.44115 (12) | 0.87718 (9) | 0.0581 (4) | |
H2 | 0.7139 | 0.5000 | 0.8601 | 0.070* | |
C3 | 0.60125 (18) | 0.42312 (13) | 0.91751 (9) | 0.0638 (5) | |
H3 | 0.5438 | 0.4709 | 0.9277 | 0.077* | |
C4 | 0.58376 (17) | 0.33634 (14) | 0.94275 (9) | 0.0617 (5) | |
H4 | 0.5134 | 0.3256 | 0.9688 | 0.074* | |
C5 | 0.67033 (15) | 0.26431 (12) | 0.92969 (8) | 0.0496 (4) | |
H5 | 0.6594 | 0.2058 | 0.9473 | 0.060* | |
C6 | 0.77230 (14) | 0.28113 (10) | 0.89026 (7) | 0.0416 (3) | |
C7 | 0.88073 (14) | 0.21963 (9) | 0.86692 (7) | 0.0391 (3) | |
C8 | 0.93764 (15) | 0.28068 (10) | 0.81417 (7) | 0.0434 (3) | |
C9 | 0.95012 (15) | 0.07405 (10) | 0.83671 (7) | 0.0428 (3) | |
H9 | 0.9912 | 0.0902 | 0.7972 | 0.051* | |
C10 | 1.04648 (14) | 0.09858 (10) | 0.89213 (6) | 0.0398 (3) | |
H10 | 1.0301 | 0.0532 | 0.9252 | 0.048* | |
C11 | 0.99615 (14) | 0.19452 (9) | 0.91645 (6) | 0.0377 (3) | |
C12 | 1.08584 (14) | 0.27644 (10) | 0.92958 (7) | 0.0404 (3) | |
C13 | 1.18047 (15) | 0.31809 (11) | 0.89351 (8) | 0.0488 (4) | |
H13 | 1.2055 | 0.2908 | 0.8562 | 0.059* | |
C14 | 1.23716 (16) | 0.40056 (12) | 0.91360 (9) | 0.0582 (4) | |
H14 | 1.3005 | 0.4292 | 0.8895 | 0.070* | |
C15 | 1.20104 (18) | 0.44093 (13) | 0.96885 (9) | 0.0636 (5) | |
H15 | 1.2393 | 0.4972 | 0.9811 | 0.076* | |
C16 | 1.10893 (17) | 0.39982 (12) | 1.00669 (8) | 0.0562 (4) | |
H16 | 1.0858 | 0.4267 | 1.0444 | 0.067* | |
C17 | 1.05266 (14) | 0.31709 (10) | 0.98611 (7) | 0.0429 (3) | |
C18 | 0.92993 (14) | 0.18140 (10) | 0.97952 (7) | 0.0410 (3) | |
C19 | 1.19309 (15) | 0.09315 (10) | 0.87948 (7) | 0.0422 (3) | |
C20 | 1.24576 (17) | 0.10531 (14) | 0.82126 (8) | 0.0592 (4) | |
H20 | 1.1895 | 0.1157 | 0.7867 | 0.071* | |
C21 | 1.38137 (19) | 0.10238 (15) | 0.81337 (10) | 0.0690 (5) | |
H21 | 1.4146 | 0.1110 | 0.7737 | 0.083* | |
C22 | 1.46602 (19) | 0.08711 (14) | 0.86290 (11) | 0.0697 (5) | |
H22 | 1.5567 | 0.0850 | 0.8574 | 0.084* | |
C23 | 1.41566 (19) | 0.07485 (15) | 0.92104 (11) | 0.0746 (6) | |
H23 | 1.4727 | 0.0649 | 0.9554 | 0.089* | |
C24 | 1.28000 (17) | 0.07707 (13) | 0.92924 (9) | 0.0593 (4) | |
H24 | 1.2474 | 0.0675 | 0.9690 | 0.071* | |
C25 | 0.90362 (16) | −0.02517 (10) | 0.83374 (7) | 0.0475 (4) | |
C26 | 0.92520 (18) | −0.07851 (12) | 0.78116 (9) | 0.0591 (4) | |
H26 | 0.9704 | −0.0534 | 0.7479 | 0.071* | |
C27 | 0.8794 (2) | −0.16988 (14) | 0.77799 (11) | 0.0747 (6) | |
H27 | 0.8945 | −0.2050 | 0.7423 | 0.090* | |
C28 | 0.8125 (2) | −0.20939 (13) | 0.82614 (12) | 0.0720 (6) | |
C29 | 0.7918 (2) | −0.15548 (14) | 0.87824 (11) | 0.0738 (6) | |
H29 | 0.7469 | −0.1808 | 0.9115 | 0.089* | |
C30 | 0.83600 (19) | −0.06478 (12) | 0.88226 (9) | 0.0630 (5) | |
H30 | 0.8202 | −0.0300 | 0.9180 | 0.076* | |
C31 | 0.9255 (2) | 0.44567 (13) | 0.78159 (10) | 0.0719 (5) | |
H31A | 0.9950 | 0.4267 | 0.7548 | 0.108* | |
H31B | 0.9562 | 0.4958 | 0.8080 | 0.108* | |
H31C | 0.8507 | 0.4661 | 0.7565 | 0.108* | |
C32 | 0.89238 (16) | 0.28703 (12) | 1.07095 (7) | 0.0499 (4) | |
C33 | 0.69765 (18) | 0.24771 (12) | 1.13027 (8) | 0.0559 (4) | |
C34 | 0.5818 (2) | 0.18667 (17) | 1.11165 (11) | 0.0856 (7) | |
H34A | 0.5376 | 0.2119 | 1.0750 | 0.128* | |
H34B | 0.5213 | 0.1842 | 1.1454 | 0.128* | |
H34C | 0.6127 | 0.1251 | 1.1027 | 0.128* | |
C35 | 0.6545 (2) | 0.34648 (14) | 1.14099 (9) | 0.0708 (5) | |
H35A | 0.7298 | 0.3836 | 1.1531 | 0.106* | |
H35B | 0.5913 | 0.3479 | 1.1736 | 0.106* | |
H35C | 0.6147 | 0.3709 | 1.1031 | 0.106* | |
C36 | 0.7755 (2) | 0.20700 (18) | 1.18477 (10) | 0.0832 (7) | |
H36A | 0.8050 | 0.1457 | 1.1741 | 0.125* | |
H36B | 0.7205 | 0.2035 | 1.2205 | 0.125* | |
H36C | 0.8506 | 0.2458 | 1.1945 | 0.125* | |
C37 | 0.7645 (3) | −0.30892 (14) | 0.82249 (14) | 0.1054 (10) | |
H37A | 0.7806 | −0.3336 | 0.7817 | 0.158* | |
H37B | 0.6715 | −0.3108 | 0.8298 | 0.158* | |
H37C | 0.8110 | −0.3456 | 0.8536 | 0.158* | |
N1 | 0.88731 (13) | 0.36766 (9) | 0.82017 (6) | 0.0496 (3) | |
N2 | 0.95503 (12) | 0.26214 (9) | 1.01525 (6) | 0.0438 (3) | |
O1 | 1.01426 (12) | 0.25583 (8) | 0.77495 (5) | 0.0556 (3) | |
O2 | 0.83534 (10) | 0.13260 (7) | 0.84480 (5) | 0.0427 (2) | |
O3 | 0.86937 (12) | 0.11421 (8) | 0.99542 (5) | 0.0548 (3) | |
O4 | 0.93842 (13) | 0.34313 (10) | 1.10674 (6) | 0.0677 (4) | |
O5 | 0.77931 (12) | 0.24267 (9) | 1.07374 (5) | 0.0613 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0444 (8) | 0.0401 (8) | 0.0529 (9) | −0.0030 (6) | −0.0010 (7) | −0.0039 (6) |
C2 | 0.0587 (10) | 0.0405 (9) | 0.0747 (12) | 0.0033 (7) | −0.0041 (9) | −0.0058 (8) |
C3 | 0.0511 (10) | 0.0606 (11) | 0.0796 (12) | 0.0128 (8) | 0.0001 (9) | −0.0168 (9) |
C4 | 0.0421 (9) | 0.0758 (13) | 0.0678 (11) | 0.0038 (8) | 0.0087 (8) | −0.0086 (9) |
C5 | 0.0405 (8) | 0.0536 (9) | 0.0551 (9) | −0.0034 (7) | 0.0058 (7) | −0.0013 (7) |
C6 | 0.0394 (7) | 0.0395 (7) | 0.0457 (8) | −0.0032 (6) | 0.0005 (6) | −0.0044 (6) |
C7 | 0.0415 (7) | 0.0354 (7) | 0.0405 (7) | −0.0042 (6) | 0.0048 (6) | −0.0005 (6) |
C8 | 0.0459 (8) | 0.0423 (8) | 0.0420 (8) | −0.0038 (6) | 0.0039 (6) | 0.0023 (6) |
C9 | 0.0480 (8) | 0.0400 (8) | 0.0408 (7) | 0.0003 (6) | 0.0055 (6) | −0.0043 (6) |
C10 | 0.0460 (8) | 0.0348 (7) | 0.0390 (7) | −0.0024 (6) | 0.0070 (6) | −0.0007 (6) |
C11 | 0.0386 (7) | 0.0358 (7) | 0.0390 (7) | −0.0031 (6) | 0.0071 (6) | −0.0012 (6) |
C12 | 0.0379 (7) | 0.0379 (7) | 0.0454 (8) | −0.0014 (6) | 0.0032 (6) | −0.0029 (6) |
C13 | 0.0420 (8) | 0.0488 (9) | 0.0562 (9) | −0.0055 (7) | 0.0093 (7) | −0.0009 (7) |
C14 | 0.0444 (9) | 0.0548 (10) | 0.0756 (12) | −0.0143 (7) | 0.0060 (8) | 0.0033 (9) |
C15 | 0.0581 (10) | 0.0510 (10) | 0.0815 (13) | −0.0181 (8) | −0.0033 (9) | −0.0097 (9) |
C16 | 0.0588 (10) | 0.0510 (9) | 0.0587 (10) | −0.0083 (8) | −0.0002 (8) | −0.0155 (8) |
C17 | 0.0378 (7) | 0.0437 (8) | 0.0471 (8) | −0.0013 (6) | 0.0003 (6) | −0.0029 (6) |
C18 | 0.0418 (7) | 0.0420 (8) | 0.0393 (7) | −0.0012 (6) | 0.0059 (6) | −0.0018 (6) |
C19 | 0.0460 (8) | 0.0339 (7) | 0.0468 (8) | 0.0012 (6) | 0.0054 (6) | −0.0029 (6) |
C20 | 0.0531 (10) | 0.0718 (11) | 0.0534 (10) | 0.0082 (8) | 0.0124 (8) | −0.0027 (8) |
C21 | 0.0604 (11) | 0.0747 (13) | 0.0734 (12) | 0.0064 (9) | 0.0258 (10) | −0.0070 (10) |
C22 | 0.0460 (10) | 0.0629 (12) | 0.1008 (16) | 0.0013 (8) | 0.0119 (10) | −0.0096 (11) |
C23 | 0.0538 (11) | 0.0818 (14) | 0.0872 (14) | −0.0027 (10) | −0.0128 (10) | 0.0066 (11) |
C24 | 0.0555 (10) | 0.0639 (11) | 0.0584 (10) | −0.0048 (8) | −0.0006 (8) | 0.0067 (8) |
C25 | 0.0504 (8) | 0.0382 (8) | 0.0536 (9) | 0.0012 (6) | −0.0055 (7) | −0.0059 (7) |
C26 | 0.0656 (11) | 0.0509 (10) | 0.0602 (10) | 0.0082 (8) | −0.0094 (8) | −0.0150 (8) |
C27 | 0.0822 (14) | 0.0512 (11) | 0.0887 (15) | 0.0167 (10) | −0.0302 (12) | −0.0301 (10) |
C28 | 0.0721 (12) | 0.0377 (9) | 0.1036 (16) | 0.0014 (9) | −0.0388 (12) | −0.0031 (10) |
C29 | 0.0798 (13) | 0.0513 (11) | 0.0894 (15) | −0.0181 (9) | −0.0124 (11) | 0.0091 (10) |
C30 | 0.0772 (12) | 0.0475 (9) | 0.0645 (11) | −0.0136 (9) | 0.0034 (9) | −0.0039 (8) |
C31 | 0.0816 (13) | 0.0482 (10) | 0.0866 (14) | −0.0062 (9) | 0.0151 (11) | 0.0227 (9) |
C32 | 0.0512 (9) | 0.0581 (9) | 0.0405 (8) | 0.0008 (8) | 0.0043 (7) | −0.0075 (7) |
C33 | 0.0600 (10) | 0.0625 (10) | 0.0465 (9) | 0.0047 (8) | 0.0208 (8) | −0.0037 (7) |
C34 | 0.0783 (14) | 0.0939 (16) | 0.0868 (15) | −0.0199 (12) | 0.0360 (12) | −0.0138 (12) |
C35 | 0.0758 (13) | 0.0701 (12) | 0.0676 (12) | 0.0163 (10) | 0.0193 (10) | 0.0001 (10) |
C36 | 0.0860 (15) | 0.0996 (17) | 0.0654 (12) | 0.0303 (13) | 0.0230 (11) | 0.0172 (12) |
C37 | 0.1113 (19) | 0.0386 (10) | 0.162 (3) | −0.0059 (11) | −0.0653 (18) | −0.0029 (12) |
N1 | 0.0543 (8) | 0.0380 (7) | 0.0567 (8) | −0.0034 (6) | 0.0073 (6) | 0.0073 (6) |
N2 | 0.0455 (7) | 0.0467 (7) | 0.0393 (6) | −0.0040 (5) | 0.0066 (5) | −0.0069 (5) |
O1 | 0.0629 (7) | 0.0569 (7) | 0.0481 (6) | 0.0003 (5) | 0.0180 (5) | 0.0048 (5) |
O2 | 0.0448 (6) | 0.0351 (5) | 0.0480 (6) | −0.0034 (4) | −0.0002 (4) | −0.0036 (4) |
O3 | 0.0676 (7) | 0.0473 (6) | 0.0506 (6) | −0.0141 (5) | 0.0203 (5) | −0.0008 (5) |
O4 | 0.0690 (8) | 0.0815 (9) | 0.0529 (7) | −0.0091 (7) | 0.0081 (6) | −0.0263 (6) |
O5 | 0.0589 (7) | 0.0787 (8) | 0.0473 (6) | −0.0126 (6) | 0.0192 (5) | −0.0182 (6) |
Geometric parameters (Å, º) top
C1—C2 | 1.373 (2) | C20—H20 | 0.9300 |
C1—C6 | 1.395 (2) | C21—C22 | 1.358 (3) |
C1—N1 | 1.405 (2) | C21—H21 | 0.9300 |
C2—C3 | 1.384 (3) | C22—C23 | 1.368 (3) |
C2—H2 | 0.9300 | C22—H22 | 0.9300 |
C3—C4 | 1.372 (3) | C23—C24 | 1.390 (3) |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C4—C5 | 1.390 (2) | C24—H24 | 0.9300 |
C4—H4 | 0.9300 | C25—C30 | 1.382 (2) |
C5—C6 | 1.374 (2) | C25—C26 | 1.382 (2) |
C5—H5 | 0.9300 | C26—C27 | 1.393 (3) |
C6—C7 | 1.506 (2) | C26—H26 | 0.9300 |
C7—O2 | 1.4087 (17) | C27—C28 | 1.371 (3) |
C7—C8 | 1.553 (2) | C27—H27 | 0.9300 |
C7—C11 | 1.593 (2) | C28—C29 | 1.377 (3) |
C8—O1 | 1.2129 (18) | C28—C37 | 1.512 (3) |
C8—N1 | 1.357 (2) | C29—C30 | 1.380 (3) |
C9—O2 | 1.4492 (17) | C29—H29 | 0.9300 |
C9—C25 | 1.502 (2) | C30—H30 | 0.9300 |
C9—C10 | 1.550 (2) | C31—N1 | 1.451 (2) |
C9—H9 | 0.9800 | C31—H31A | 0.9600 |
C10—C19 | 1.519 (2) | C31—H31B | 0.9600 |
C10—C11 | 1.5640 (19) | C31—H31C | 0.9600 |
C10—H10 | 0.9800 | C32—O4 | 1.1952 (19) |
C11—C12 | 1.5074 (19) | C32—O5 | 1.313 (2) |
C11—C18 | 1.5346 (19) | C32—N2 | 1.4114 (19) |
C12—C13 | 1.384 (2) | C33—O5 | 1.4861 (18) |
C12—C17 | 1.392 (2) | C33—C36 | 1.503 (3) |
C13—C14 | 1.379 (2) | C33—C35 | 1.504 (3) |
C13—H13 | 0.9300 | C33—C34 | 1.508 (3) |
C14—C15 | 1.374 (3) | C34—H34A | 0.9600 |
C14—H14 | 0.9300 | C34—H34B | 0.9600 |
C15—C16 | 1.385 (3) | C34—H34C | 0.9600 |
C15—H15 | 0.9300 | C35—H35A | 0.9600 |
C16—C17 | 1.384 (2) | C35—H35B | 0.9600 |
C16—H16 | 0.9300 | C35—H35C | 0.9600 |
C17—N2 | 1.4234 (19) | C36—H36A | 0.9600 |
C18—O3 | 1.1984 (17) | C36—H36B | 0.9600 |
C18—N2 | 1.4072 (19) | C36—H36C | 0.9600 |
C19—C24 | 1.378 (2) | C37—H37A | 0.9600 |
C19—C20 | 1.379 (2) | C37—H37B | 0.9600 |
C20—C21 | 1.389 (3) | C37—H37C | 0.9600 |
| | | |
C2—C1—C6 | 121.88 (15) | C21—C22—C23 | 118.92 (18) |
C2—C1—N1 | 128.15 (15) | C21—C22—H22 | 120.5 |
C6—C1—N1 | 109.89 (13) | C23—C22—H22 | 120.5 |
C1—C2—C3 | 117.55 (16) | C22—C23—C24 | 120.60 (19) |
C1—C2—H2 | 121.2 | C22—C23—H23 | 119.7 |
C3—C2—H2 | 121.2 | C24—C23—H23 | 119.7 |
C4—C3—C2 | 121.46 (16) | C19—C24—C23 | 121.07 (18) |
C4—C3—H3 | 119.3 | C19—C24—H24 | 119.5 |
C2—C3—H3 | 119.3 | C23—C24—H24 | 119.5 |
C3—C4—C5 | 120.52 (16) | C30—C25—C26 | 118.37 (16) |
C3—C4—H4 | 119.7 | C30—C25—C9 | 121.40 (14) |
C5—C4—H4 | 119.7 | C26—C25—C9 | 120.21 (15) |
C6—C5—C4 | 118.85 (16) | C25—C26—C27 | 120.06 (19) |
C6—C5—H5 | 120.6 | C25—C26—H26 | 120.0 |
C4—C5—H5 | 120.6 | C27—C26—H26 | 120.0 |
C5—C6—C1 | 119.67 (14) | C28—C27—C26 | 121.66 (19) |
C5—C6—C7 | 131.99 (14) | C28—C27—H27 | 119.2 |
C1—C6—C7 | 108.33 (12) | C26—C27—H27 | 119.2 |
O2—C7—C6 | 113.48 (11) | C27—C28—C29 | 117.66 (18) |
O2—C7—C8 | 112.50 (11) | C27—C28—C37 | 121.2 (2) |
C6—C7—C8 | 101.51 (11) | C29—C28—C37 | 121.1 (2) |
O2—C7—C11 | 104.26 (11) | C28—C29—C30 | 121.6 (2) |
C6—C7—C11 | 116.13 (11) | C28—C29—H29 | 119.2 |
C8—C7—C11 | 109.18 (11) | C30—C29—H29 | 119.2 |
O1—C8—N1 | 125.89 (14) | C29—C30—C25 | 120.63 (18) |
O1—C8—C7 | 126.48 (14) | C29—C30—H30 | 119.7 |
N1—C8—C7 | 107.62 (12) | C25—C30—H30 | 119.7 |
O2—C9—C25 | 107.74 (12) | N1—C31—H31A | 109.5 |
O2—C9—C10 | 105.34 (11) | N1—C31—H31B | 109.5 |
C25—C9—C10 | 115.91 (12) | H31A—C31—H31B | 109.5 |
O2—C9—H9 | 109.2 | N1—C31—H31C | 109.5 |
C25—C9—H9 | 109.2 | H31A—C31—H31C | 109.5 |
C10—C9—H9 | 109.2 | H31B—C31—H31C | 109.5 |
C19—C10—C9 | 116.58 (12) | O4—C32—O5 | 128.41 (15) |
C19—C10—C11 | 115.76 (11) | O4—C32—N2 | 122.22 (15) |
C9—C10—C11 | 104.49 (11) | O5—C32—N2 | 109.30 (13) |
C19—C10—H10 | 106.4 | O5—C33—C36 | 108.57 (14) |
C9—C10—H10 | 106.4 | O5—C33—C35 | 109.95 (14) |
C11—C10—H10 | 106.4 | C36—C33—C35 | 113.40 (17) |
C12—C11—C18 | 102.11 (11) | O5—C33—C34 | 101.85 (14) |
C12—C11—C10 | 123.33 (12) | C36—C33—C34 | 111.23 (19) |
C18—C11—C10 | 109.82 (11) | C35—C33—C34 | 111.19 (17) |
C12—C11—C7 | 111.81 (11) | C33—C34—H34A | 109.5 |
C18—C11—C7 | 106.20 (11) | C33—C34—H34B | 109.5 |
C10—C11—C7 | 102.65 (11) | H34A—C34—H34B | 109.5 |
C13—C12—C17 | 119.43 (14) | C33—C34—H34C | 109.5 |
C13—C12—C11 | 131.12 (13) | H34A—C34—H34C | 109.5 |
C17—C12—C11 | 109.19 (12) | H34B—C34—H34C | 109.5 |
C14—C13—C12 | 119.15 (15) | C33—C35—H35A | 109.5 |
C14—C13—H13 | 120.4 | C33—C35—H35B | 109.5 |
C12—C13—H13 | 120.4 | H35A—C35—H35B | 109.5 |
C15—C14—C13 | 120.68 (16) | C33—C35—H35C | 109.5 |
C15—C14—H14 | 119.7 | H35A—C35—H35C | 109.5 |
C13—C14—H14 | 119.7 | H35B—C35—H35C | 109.5 |
C14—C15—C16 | 121.52 (16) | C33—C36—H36A | 109.5 |
C14—C15—H15 | 119.2 | C33—C36—H36B | 109.5 |
C16—C15—H15 | 119.2 | H36A—C36—H36B | 109.5 |
C17—C16—C15 | 117.33 (16) | C33—C36—H36C | 109.5 |
C17—C16—H16 | 121.3 | H36A—C36—H36C | 109.5 |
C15—C16—H16 | 121.3 | H36B—C36—H36C | 109.5 |
C16—C17—C12 | 121.86 (15) | C28—C37—H37A | 109.5 |
C16—C17—N2 | 128.48 (14) | C28—C37—H37B | 109.5 |
C12—C17—N2 | 109.64 (12) | H37A—C37—H37B | 109.5 |
O3—C18—N2 | 126.56 (13) | C28—C37—H37C | 109.5 |
O3—C18—C11 | 126.09 (13) | H37A—C37—H37C | 109.5 |
N2—C18—C11 | 107.35 (11) | H37B—C37—H37C | 109.5 |
C24—C19—C20 | 117.45 (15) | C8—N1—C1 | 111.07 (12) |
C24—C19—C10 | 118.39 (14) | C8—N1—C31 | 123.38 (15) |
C20—C19—C10 | 124.15 (14) | C1—N1—C31 | 125.23 (14) |
C19—C20—C21 | 121.13 (18) | C18—N2—C32 | 125.99 (13) |
C19—C20—H20 | 119.4 | C18—N2—C17 | 109.65 (11) |
C21—C20—H20 | 119.4 | C32—N2—C17 | 124.36 (13) |
C22—C21—C20 | 120.82 (18) | C7—O2—C9 | 107.52 (10) |
C22—C21—H21 | 119.6 | C32—O5—C33 | 121.40 (13) |
C20—C21—H21 | 119.6 | | |
| | | |
C6—C1—C2—C3 | −2.2 (3) | C7—C11—C18—O3 | 77.74 (18) |
N1—C1—C2—C3 | 174.15 (16) | C12—C11—C18—N2 | 14.26 (14) |
C1—C2—C3—C4 | −0.2 (3) | C10—C11—C18—N2 | 146.69 (12) |
C2—C3—C4—C5 | 1.8 (3) | C7—C11—C18—N2 | −103.01 (13) |
C3—C4—C5—C6 | −1.1 (3) | C9—C10—C19—C24 | −154.34 (14) |
C4—C5—C6—C1 | −1.2 (2) | C11—C10—C19—C24 | 82.14 (18) |
C4—C5—C6—C7 | −179.85 (15) | C9—C10—C19—C20 | 27.1 (2) |
C2—C1—C6—C5 | 2.9 (2) | C11—C10—C19—C20 | −96.39 (18) |
N1—C1—C6—C5 | −174.04 (13) | C24—C19—C20—C21 | −0.6 (3) |
C2—C1—C6—C7 | −178.17 (14) | C10—C19—C20—C21 | 177.89 (17) |
N1—C1—C6—C7 | 4.91 (17) | C19—C20—C21—C22 | 0.2 (3) |
C5—C6—C7—O2 | 47.5 (2) | C20—C21—C22—C23 | −0.2 (3) |
C1—C6—C7—O2 | −131.27 (13) | C21—C22—C23—C24 | 0.6 (3) |
C5—C6—C7—C8 | 168.45 (16) | C20—C19—C24—C23 | 1.1 (3) |
C1—C6—C7—C8 | −10.32 (15) | C10—C19—C24—C23 | −177.55 (16) |
C5—C6—C7—C11 | −73.3 (2) | C22—C23—C24—C19 | −1.1 (3) |
C1—C6—C7—C11 | 107.93 (14) | O2—C9—C25—C30 | −58.33 (19) |
O2—C7—C8—O1 | −46.5 (2) | C10—C9—C25—C30 | 59.3 (2) |
C6—C7—C8—O1 | −168.11 (15) | O2—C9—C25—C26 | 120.12 (15) |
C11—C7—C8—O1 | 68.75 (19) | C10—C9—C25—C26 | −122.22 (16) |
O2—C7—C8—N1 | 134.19 (13) | C30—C25—C26—C27 | −0.1 (3) |
C6—C7—C8—N1 | 12.57 (15) | C9—C25—C26—C27 | −178.58 (15) |
C11—C7—C8—N1 | −110.57 (13) | C25—C26—C27—C28 | −0.1 (3) |
O2—C9—C10—C19 | −147.11 (12) | C26—C27—C28—C29 | 0.1 (3) |
C25—C9—C10—C19 | 93.91 (16) | C26—C27—C28—C37 | −179.34 (18) |
O2—C9—C10—C11 | −17.96 (14) | C27—C28—C29—C30 | 0.1 (3) |
C25—C9—C10—C11 | −136.94 (13) | C37—C28—C29—C30 | 179.54 (19) |
C19—C10—C11—C12 | −2.51 (19) | C28—C29—C30—C25 | −0.3 (3) |
C9—C10—C11—C12 | −132.14 (14) | C26—C25—C30—C29 | 0.3 (3) |
C19—C10—C11—C18 | −122.76 (13) | C9—C25—C30—C29 | 178.75 (17) |
C9—C10—C11—C18 | 107.60 (12) | O1—C8—N1—C1 | 170.14 (15) |
C19—C10—C11—C7 | 124.60 (13) | C7—C8—N1—C1 | −10.53 (17) |
C9—C10—C11—C7 | −5.04 (13) | O1—C8—N1—C31 | −3.7 (3) |
O2—C7—C11—C12 | 161.28 (11) | C7—C8—N1—C31 | 175.58 (16) |
C6—C7—C11—C12 | −73.10 (15) | C2—C1—N1—C8 | −172.87 (16) |
C8—C7—C11—C12 | 40.85 (15) | C6—C1—N1—C8 | 3.80 (18) |
O2—C7—C11—C18 | −88.13 (12) | C2—C1—N1—C31 | 0.9 (3) |
C6—C7—C11—C18 | 37.49 (15) | C6—C1—N1—C31 | 177.55 (16) |
C8—C7—C11—C18 | 151.44 (11) | O3—C18—N2—C32 | −13.5 (3) |
O2—C7—C11—C10 | 27.14 (13) | C11—C18—N2—C32 | 167.26 (14) |
C6—C7—C11—C10 | 152.77 (11) | O3—C18—N2—C17 | 167.61 (15) |
C8—C7—C11—C10 | −93.29 (12) | C11—C18—N2—C17 | −11.64 (16) |
C18—C11—C12—C13 | 173.94 (16) | O4—C32—N2—C18 | 161.58 (17) |
C10—C11—C12—C13 | 50.2 (2) | O5—C32—N2—C18 | −21.1 (2) |
C7—C11—C12—C13 | −72.90 (19) | O4—C32—N2—C17 | −19.7 (3) |
C18—C11—C12—C17 | −12.20 (15) | O5—C32—N2—C17 | 157.67 (14) |
C10—C11—C12—C17 | −135.98 (14) | C16—C17—N2—C18 | −177.59 (16) |
C7—C11—C12—C17 | 100.96 (14) | C12—C17—N2—C18 | 3.80 (17) |
C17—C12—C13—C14 | −1.8 (2) | C16—C17—N2—C32 | 3.5 (2) |
C11—C12—C13—C14 | 171.51 (16) | C12—C17—N2—C32 | −175.13 (14) |
C12—C13—C14—C15 | 0.3 (3) | C6—C7—O2—C9 | −167.98 (11) |
C13—C14—C15—C16 | 1.2 (3) | C8—C7—O2—C9 | 77.48 (14) |
C14—C15—C16—C17 | −1.2 (3) | C11—C7—O2—C9 | −40.69 (13) |
C15—C16—C17—C12 | −0.4 (3) | C25—C9—O2—C7 | 161.93 (11) |
C15—C16—C17—N2 | −178.84 (16) | C10—C9—O2—C7 | 37.64 (14) |
C13—C12—C17—C16 | 1.9 (2) | O4—C32—O5—C33 | −9.1 (3) |
C11—C12—C17—C16 | −172.81 (14) | N2—C32—O5—C33 | 173.74 (14) |
C13—C12—C17—N2 | −179.40 (13) | C36—C33—O5—C32 | −62.1 (2) |
C11—C12—C17—N2 | 5.91 (17) | C35—C33—O5—C32 | 62.5 (2) |
C12—C11—C18—O3 | −165.00 (15) | C34—C33—O5—C32 | −179.56 (17) |
C10—C11—C18—O3 | −32.6 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O1 | 0.98 | 2.44 | 3.006 (2) | 116 |
C10—H10···O3 | 0.98 | 2.41 | 2.895 (2) | 110 |
C16—H16···O4 | 0.93 | 2.36 | 2.905 (2) | 117 |
C31—H31A···O1 | 0.96 | 2.50 | 2.876 (2) | 103 |
C35—H35A···O4 | 0.96 | 2.43 | 2.989 (2) | 117 |
C36—H36B···O1i | 0.96 | 2.49 | 3.362 (2) | 151 |
C36—H36C···O4 | 0.96 | 2.52 | 3.081 (3) | 117 |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
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