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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, C36H31BrN2O, (Ia), 5′-(4-bromo­phen­yl)-1,1′′-dimethyl-4′-phenyl-4′,5′-di­hydro­dispiro­[indoline-3,2′-furan-3′,3′′-indoline]-2,2′′-dione, C32H25BrN2O3, (Ib), 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, C37H34N2O5, (Ic). 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615013273/lg3172sup1.cif
Contains datablocks Ia, Ib, Ic, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615013273/lg3172Iasup2.hkl
Contains datablock Ia

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615013273/lg3172Ibsup3.hkl
Contains datablock Ib

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615013273/lg3172Icsup4.hkl
Contains datablock Ic

CCDC references: 1411981; 1411980; 1411979

Computing details top

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
C36H31BrN2O5Z = 2
Mr = 651.54F(000) = 672
Triclinic, P1Dx = 1.379 Mg m3
a = 9.5268 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.0566 (17) ÅCell parameters from 2532 reflections
c = 13.4593 (17) Åθ = 2.3–20.1°
α = 94.401 (2)°µ = 1.36 mm1
β = 97.385 (2)°T = 294 K
γ = 107.762 (2)°Needle, colorless
V = 1569.2 (3) Å30.15 × 0.07 × 0.05 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3428 reflections with I > 2σ(I)
ω scansRint = 0.041
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 25.7°, θmin = 1.5°
Tmin = 0.85, Tmax = 0.91h = 1111
16039 measured reflectionsk = 1515
5948 independent reflectionsl = 1616
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-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 reflectionsΔρmax = 0.83 e Å3
401 parametersΔρmin = 0.50 e Å3
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
xyzUiso*/Ueq
Br10.24497 (7)0.29204 (5)0.42937 (5)0.0925 (3)
C10.8083 (5)0.3526 (4)0.1333 (3)0.0501 (11)
C20.9162 (5)0.3645 (4)0.0712 (4)0.0664 (14)
H20.99840.42690.07910.080*
C30.8965 (7)0.2798 (6)0.0026 (4)0.0782 (16)
H30.96710.28560.04540.094*
C40.7772 (7)0.1885 (5)0.0146 (4)0.0727 (15)
H40.76860.13280.06470.087*
C50.6673 (6)0.1764 (4)0.0463 (3)0.0580 (12)
H50.58580.11340.03790.070*
C60.6832 (5)0.2611 (3)0.1201 (3)0.0456 (10)
C70.5938 (4)0.2690 (3)0.2038 (3)0.0422 (10)
C80.6994 (5)0.3734 (3)0.2709 (4)0.0472 (10)
C90.4652 (4)0.1735 (3)0.3200 (3)0.0425 (10)
H90.50970.22290.38240.051*
C100.3481 (4)0.2129 (3)0.2580 (3)0.0435 (10)
H100.27260.14770.22080.052*
C110.4315 (4)0.2766 (3)0.1767 (3)0.0405 (9)
C120.4197 (4)0.3870 (3)0.1625 (3)0.0432 (10)
C130.4541 (5)0.4804 (3)0.2286 (4)0.0560 (12)
H130.49550.48200.29540.067*
C140.4274 (5)0.5711 (4)0.1964 (4)0.0606 (13)
H140.45060.63360.24170.073*
C150.3667 (5)0.5702 (4)0.0976 (4)0.0586 (12)
H150.35020.63230.07640.070*
C160.3305 (5)0.4782 (4)0.0304 (4)0.0539 (11)
H160.28940.47730.03630.065*
C170.3560 (4)0.3870 (3)0.0633 (3)0.0424 (10)
C180.3595 (4)0.2115 (4)0.0729 (3)0.0434 (10)
C190.2659 (5)0.2686 (3)0.3218 (3)0.0496 (11)
C200.3355 (6)0.3378 (4)0.4099 (4)0.0697 (14)
H200.43700.35190.43170.084*
C210.2557 (8)0.3853 (5)0.4651 (5)0.0866 (18)
H210.30440.43370.52250.104*
C220.1040 (9)0.3622 (6)0.4366 (6)0.098 (2)
H220.05020.39360.47510.117*
C230.0343 (7)0.2935 (5)0.3521 (5)0.0859 (18)
H230.06810.27730.33260.103*
C240.1149 (6)0.2468 (4)0.2940 (4)0.0650 (13)
H240.06580.20030.23560.078*
C250.4036 (4)0.0591 (3)0.3444 (3)0.0442 (10)
C260.3964 (5)0.0276 (4)0.2769 (3)0.0499 (11)
H260.42560.01560.21440.060*
C270.3461 (5)0.1332 (4)0.3009 (4)0.0566 (12)
H270.34400.19140.25580.068*
C280.2996 (5)0.1496 (4)0.3927 (4)0.0584 (13)
C290.2968 (6)0.0653 (5)0.4565 (4)0.0712 (15)
H290.25790.07810.51600.085*
C300.3515 (5)0.0397 (4)0.4340 (3)0.0581 (12)
H300.35300.09740.47960.070*
C310.9334 (5)0.5177 (4)0.2610 (4)0.0698 (14)
H31A0.91200.54920.32170.105*
H31B0.94610.56880.21260.105*
H31C1.02340.49940.27610.105*
C320.2545 (5)0.2555 (4)0.0926 (3)0.0487 (11)
C330.1737 (5)0.1070 (4)0.2289 (3)0.0595 (13)
C340.0127 (6)0.0809 (5)0.2174 (5)0.0910 (19)
H34A0.00140.05420.15370.137*
H34B0.04770.02660.27110.137*
H34C0.01600.14520.22000.137*
C350.2145 (9)0.1710 (6)0.3143 (4)0.114 (2)
H35A0.17380.22980.31250.170*
H35B0.17460.12490.37710.170*
H35C0.32120.19930.30810.170*
C360.2130 (7)0.0033 (5)0.2376 (5)0.094 (2)
H36A0.31630.01970.24450.142*
H36B0.15200.04400.29570.142*
H36C0.19560.03160.17810.142*
N10.8105 (4)0.4204 (3)0.2196 (3)0.0502 (9)
N20.3282 (4)0.2831 (3)0.0084 (2)0.0434 (8)
O10.6853 (3)0.4047 (2)0.3550 (2)0.0583 (8)
O20.5763 (3)0.1775 (2)0.2566 (2)0.0453 (7)
O30.3304 (4)0.1154 (2)0.0533 (2)0.0597 (8)
O40.1916 (4)0.3108 (3)0.1329 (2)0.0679 (9)
O50.2686 (3)0.1650 (3)0.1327 (2)0.0591 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0852 (5)0.0717 (4)0.0959 (5)0.0095 (3)0.0063 (3)0.0390 (3)
C10.040 (2)0.060 (3)0.051 (3)0.015 (2)0.006 (2)0.015 (2)
C20.049 (3)0.074 (4)0.076 (4)0.015 (2)0.016 (3)0.023 (3)
C30.070 (4)0.110 (5)0.067 (4)0.040 (4)0.026 (3)0.020 (4)
C40.080 (4)0.083 (4)0.062 (3)0.032 (3)0.025 (3)0.001 (3)
C50.068 (3)0.061 (3)0.049 (3)0.025 (2)0.013 (2)0.004 (2)
C60.047 (2)0.048 (2)0.043 (2)0.019 (2)0.0040 (19)0.007 (2)
C70.042 (2)0.039 (2)0.044 (2)0.0115 (18)0.0051 (19)0.0027 (18)
C80.043 (2)0.047 (2)0.050 (3)0.016 (2)0.000 (2)0.002 (2)
C90.042 (2)0.047 (2)0.036 (2)0.0120 (19)0.0046 (18)0.0019 (18)
C100.043 (2)0.044 (2)0.042 (2)0.0122 (19)0.0061 (19)0.0044 (19)
C110.039 (2)0.038 (2)0.041 (2)0.0107 (17)0.0002 (18)0.0009 (18)
C120.039 (2)0.043 (2)0.046 (3)0.0128 (18)0.0053 (19)0.0004 (19)
C130.062 (3)0.045 (3)0.056 (3)0.013 (2)0.002 (2)0.000 (2)
C140.059 (3)0.043 (3)0.076 (4)0.016 (2)0.007 (3)0.005 (2)
C150.053 (3)0.047 (3)0.079 (4)0.020 (2)0.010 (3)0.012 (3)
C160.049 (3)0.058 (3)0.057 (3)0.019 (2)0.011 (2)0.015 (2)
C170.033 (2)0.046 (2)0.048 (3)0.0111 (18)0.0112 (18)0.005 (2)
C180.036 (2)0.048 (3)0.046 (2)0.0121 (19)0.0067 (18)0.002 (2)
C190.054 (3)0.046 (2)0.053 (3)0.019 (2)0.015 (2)0.009 (2)
C200.073 (3)0.074 (4)0.065 (3)0.027 (3)0.019 (3)0.003 (3)
C210.102 (5)0.083 (4)0.083 (4)0.037 (4)0.038 (4)0.007 (3)
C220.131 (6)0.110 (5)0.093 (5)0.082 (5)0.055 (5)0.025 (4)
C230.080 (4)0.110 (5)0.096 (5)0.063 (4)0.030 (4)0.028 (4)
C240.060 (3)0.076 (3)0.070 (3)0.034 (3)0.013 (3)0.015 (3)
C250.041 (2)0.050 (3)0.041 (2)0.0160 (19)0.0023 (18)0.006 (2)
C260.046 (2)0.056 (3)0.047 (3)0.014 (2)0.008 (2)0.011 (2)
C270.053 (3)0.049 (3)0.065 (3)0.014 (2)0.004 (2)0.010 (2)
C280.044 (3)0.062 (3)0.058 (3)0.004 (2)0.007 (2)0.021 (3)
C290.066 (3)0.088 (4)0.056 (3)0.011 (3)0.022 (3)0.025 (3)
C300.065 (3)0.067 (3)0.042 (3)0.019 (2)0.012 (2)0.006 (2)
C310.058 (3)0.052 (3)0.081 (4)0.001 (2)0.005 (3)0.004 (3)
C320.040 (2)0.058 (3)0.048 (3)0.016 (2)0.010 (2)0.003 (2)
C330.047 (3)0.080 (3)0.045 (3)0.017 (2)0.001 (2)0.011 (2)
C340.051 (3)0.114 (5)0.095 (4)0.024 (3)0.007 (3)0.025 (4)
C350.151 (7)0.126 (6)0.044 (3)0.020 (5)0.017 (4)0.005 (4)
C360.077 (4)0.103 (5)0.095 (5)0.037 (4)0.007 (3)0.040 (4)
N10.043 (2)0.046 (2)0.052 (2)0.0040 (16)0.0014 (17)0.0028 (18)
N20.0427 (19)0.046 (2)0.041 (2)0.0158 (16)0.0021 (16)0.0025 (16)
O10.065 (2)0.0557 (19)0.0463 (19)0.0126 (16)0.0026 (15)0.0041 (15)
O20.0413 (15)0.0467 (16)0.0493 (17)0.0141 (13)0.0093 (13)0.0104 (13)
O30.077 (2)0.0405 (19)0.0530 (19)0.0136 (15)0.0039 (16)0.0041 (14)
O40.080 (2)0.078 (2)0.052 (2)0.040 (2)0.0019 (17)0.0077 (17)
O50.0516 (18)0.077 (2)0.0485 (18)0.0298 (17)0.0036 (14)0.0129 (16)
Geometric parameters (Å, º) top
Br1—C281.895 (5)C19—C201.390 (7)
C1—C21.387 (6)C20—C211.370 (7)
C1—C61.387 (6)C20—H200.9300
C1—N11.399 (6)C21—C221.378 (9)
C2—C31.379 (7)C21—H210.9300
C2—H20.9300C22—C231.351 (9)
C3—C41.355 (8)C22—H220.9300
C3—H30.9300C23—C241.393 (7)
C4—C51.391 (7)C23—H230.9300
C4—H40.9300C24—H240.9300
C5—C61.387 (6)C25—C301.375 (6)
C5—H50.9300C25—C261.375 (6)
C6—C71.512 (6)C26—C271.392 (6)
C7—O21.413 (5)C26—H260.9300
C7—C81.558 (6)C27—C281.374 (7)
C7—C111.578 (5)C27—H270.9300
C8—O11.211 (5)C28—C291.352 (7)
C8—N11.354 (6)C29—C301.383 (7)
C9—O21.434 (5)C29—H290.9300
C9—C251.507 (6)C30—H300.9300
C9—C101.543 (5)C31—N11.453 (5)
C9—H90.9800C31—H31A0.9600
C10—C191.518 (6)C31—H31B0.9600
C10—C111.575 (6)C31—H31C0.9600
C10—H100.9800C32—O41.189 (5)
C11—C121.504 (5)C32—O51.312 (5)
C11—C181.536 (6)C32—N21.413 (5)
C12—C131.378 (6)C33—O51.483 (5)
C12—C171.394 (6)C33—C351.494 (8)
C13—C141.375 (6)C33—C341.498 (7)
C13—H130.9300C33—C361.511 (7)
C14—C151.378 (7)C34—H34A0.9600
C14—H140.9300C34—H34B0.9600
C15—C161.372 (6)C34—H34C0.9600
C15—H150.9300C35—H35A0.9600
C16—C171.379 (6)C35—H35B0.9600
C16—H160.9300C35—H35C0.9600
C17—N21.425 (5)C36—H36A0.9600
C18—O31.200 (5)C36—H36B0.9600
C18—N21.395 (5)C36—H36C0.9600
C19—C241.373 (6)
C2—C1—C6121.7 (4)C20—C21—C22120.8 (6)
C2—C1—N1128.1 (4)C20—C21—H21119.6
C6—C1—N1110.0 (4)C22—C21—H21119.6
C3—C2—C1117.2 (5)C23—C22—C21119.4 (5)
C3—C2—H2121.4C23—C22—H22120.3
C1—C2—H2121.4C21—C22—H22120.3
C4—C3—C2121.9 (5)C22—C23—C24120.3 (6)
C4—C3—H3119.1C22—C23—H23119.8
C2—C3—H3119.1C24—C23—H23119.8
C3—C4—C5121.4 (5)C19—C24—C23120.9 (5)
C3—C4—H4119.3C19—C24—H24119.5
C5—C4—H4119.3C23—C24—H24119.5
C6—C5—C4117.8 (5)C30—C25—C26118.8 (4)
C6—C5—H5121.1C30—C25—C9120.5 (4)
C4—C5—H5121.1C26—C25—C9120.7 (4)
C5—C6—C1120.0 (4)C25—C26—C27121.0 (4)
C5—C6—C7130.8 (4)C25—C26—H26119.5
C1—C6—C7108.8 (4)C27—C26—H26119.5
O2—C7—C6109.5 (3)C28—C27—C26118.7 (4)
O2—C7—C8110.8 (3)C28—C27—H27120.6
C6—C7—C8101.1 (3)C26—C27—H27120.6
O2—C7—C11105.2 (3)C29—C28—C27120.7 (4)
C6—C7—C11119.3 (3)C29—C28—Br1120.7 (4)
C8—C7—C11110.9 (3)C27—C28—Br1118.6 (4)
O1—C8—N1126.6 (4)C28—C29—C30120.4 (5)
O1—C8—C7125.6 (4)C28—C29—H29119.8
N1—C8—C7107.8 (4)C30—C29—H29119.8
O2—C9—C25108.8 (3)C25—C30—C29120.2 (5)
O2—C9—C10104.7 (3)C25—C30—H30119.9
C25—C9—C10113.5 (3)C29—C30—H30119.9
O2—C9—H9109.9N1—C31—H31A109.5
C25—C9—H9109.9N1—C31—H31B109.5
C10—C9—H9109.9H31A—C31—H31B109.5
C19—C10—C9114.0 (3)N1—C31—H31C109.5
C19—C10—C11118.0 (3)H31A—C31—H31C109.5
C9—C10—C11105.2 (3)H31B—C31—H31C109.5
C19—C10—H10106.2O4—C32—O5126.9 (4)
C9—C10—H10106.2O4—C32—N2122.1 (4)
C11—C10—H10106.2O5—C32—N2111.0 (4)
C12—C11—C18102.6 (3)O5—C33—C35110.4 (4)
C12—C11—C10118.6 (3)O5—C33—C34109.3 (4)
C18—C11—C10107.3 (3)C35—C33—C34113.7 (5)
C12—C11—C7116.8 (3)O5—C33—C36101.8 (4)
C18—C11—C7108.8 (3)C35—C33—C36111.8 (5)
C10—C11—C7102.2 (3)C34—C33—C36109.2 (5)
C13—C12—C17118.3 (4)C33—C34—H34A109.5
C13—C12—C11132.1 (4)C33—C34—H34B109.5
C17—C12—C11109.6 (3)H34A—C34—H34B109.5
C14—C13—C12120.4 (4)C33—C34—H34C109.5
C14—C13—H13119.8H34A—C34—H34C109.5
C12—C13—H13119.8H34B—C34—H34C109.5
C13—C14—C15120.5 (4)C33—C35—H35A109.5
C13—C14—H14119.7C33—C35—H35B109.5
C15—C14—H14119.7H35A—C35—H35B109.5
C16—C15—C14120.3 (4)C33—C35—H35C109.5
C16—C15—H15119.8H35A—C35—H35C109.5
C14—C15—H15119.8H35B—C35—H35C109.5
C15—C16—C17119.0 (4)C33—C36—H36A109.5
C15—C16—H16120.5C33—C36—H36B109.5
C17—C16—H16120.5H36A—C36—H36B109.5
C16—C17—C12121.5 (4)C33—C36—H36C109.5
C16—C17—N2129.3 (4)H36A—C36—H36C109.5
C12—C17—N2109.3 (3)H36B—C36—H36C109.5
O3—C18—N2126.8 (4)C8—N1—C1111.4 (4)
O3—C18—C11125.4 (4)C8—N1—C31123.1 (4)
N2—C18—C11107.8 (3)C1—N1—C31124.3 (4)
C24—C19—C20118.0 (4)C18—N2—C32126.2 (3)
C24—C19—C10119.0 (4)C18—N2—C17110.3 (3)
C20—C19—C10122.9 (4)C32—N2—C17122.6 (3)
C21—C20—C19120.5 (5)C7—O2—C9108.8 (3)
C21—C20—H20119.7C32—O5—C33120.5 (4)
C19—C20—H20119.7
C6—C1—C2—C31.9 (7)C7—C11—C18—O364.2 (5)
N1—C1—C2—C3172.4 (4)C12—C11—C18—N25.7 (4)
C1—C2—C3—C40.1 (8)C10—C11—C18—N2131.4 (3)
C2—C3—C4—C50.9 (9)C7—C11—C18—N2118.6 (3)
C3—C4—C5—C60.2 (8)C9—C10—C19—C24138.6 (4)
C4—C5—C6—C12.1 (6)C11—C10—C19—C2497.1 (5)
C4—C5—C6—C7173.1 (4)C9—C10—C19—C2038.7 (6)
C2—C1—C6—C53.0 (6)C11—C10—C19—C2085.6 (5)
N1—C1—C6—C5172.2 (4)C24—C19—C20—C212.2 (7)
C2—C1—C6—C7175.8 (4)C10—C19—C20—C21179.4 (5)
N1—C1—C6—C70.6 (5)C19—C20—C21—C222.6 (9)
C5—C6—C7—O248.9 (6)C20—C21—C22—C231.3 (10)
C1—C6—C7—O2122.8 (4)C21—C22—C23—C240.3 (10)
C5—C6—C7—C8165.9 (4)C20—C19—C24—C230.6 (7)
C1—C6—C7—C85.8 (4)C10—C19—C24—C23177.9 (4)
C5—C6—C7—C1172.2 (6)C22—C23—C24—C190.7 (8)
C1—C6—C7—C11116.0 (4)O2—C9—C25—C30150.3 (4)
O2—C7—C8—O153.1 (5)C10—C9—C25—C3093.6 (5)
C6—C7—C8—O1169.1 (4)O2—C9—C25—C2630.8 (5)
C11—C7—C8—O163.3 (5)C10—C9—C25—C2685.4 (5)
O2—C7—C8—N1125.3 (4)C30—C25—C26—C274.0 (6)
C6—C7—C8—N19.3 (4)C9—C25—C26—C27177.0 (4)
C11—C7—C8—N1118.2 (4)C25—C26—C27—C281.8 (6)
O2—C9—C10—C19150.8 (3)C26—C27—C28—C292.8 (7)
C25—C9—C10—C1990.7 (4)C26—C27—C28—Br1175.5 (3)
O2—C9—C10—C1119.9 (4)C27—C28—C29—C305.0 (7)
C25—C9—C10—C11138.4 (3)Br1—C28—C29—C30173.2 (4)
C19—C10—C11—C122.9 (5)C26—C25—C30—C291.8 (7)
C9—C10—C11—C12131.5 (3)C9—C25—C30—C29179.2 (4)
C19—C10—C11—C18118.5 (4)C28—C29—C30—C252.7 (8)
C9—C10—C11—C18113.0 (3)O1—C8—N1—C1168.7 (4)
C19—C10—C11—C7127.1 (4)C7—C8—N1—C19.7 (5)
C9—C10—C11—C71.4 (4)O1—C8—N1—C311.0 (7)
O2—C7—C11—C12153.9 (3)C7—C8—N1—C31177.4 (4)
C6—C7—C11—C1282.8 (4)C2—C1—N1—C8168.8 (4)
C8—C7—C11—C1234.0 (5)C6—C1—N1—C86.0 (5)
O2—C7—C11—C1890.6 (4)C2—C1—N1—C311.3 (7)
C6—C7—C11—C1832.7 (5)C6—C1—N1—C31173.6 (4)
C8—C7—C11—C18149.5 (3)O3—C18—N2—C320.6 (6)
O2—C7—C11—C1022.7 (4)C11—C18—N2—C32176.4 (3)
C6—C7—C11—C10146.0 (3)O3—C18—N2—C17169.9 (4)
C8—C7—C11—C1097.2 (4)C11—C18—N2—C177.2 (4)
C18—C11—C12—C13174.9 (4)O4—C32—N2—C18156.5 (4)
C10—C11—C12—C1356.8 (6)O5—C32—N2—C1824.6 (5)
C7—C11—C12—C1366.2 (6)O4—C32—N2—C1711.6 (6)
C18—C11—C12—C172.3 (4)O5—C32—N2—C17167.4 (3)
C10—C11—C12—C17120.3 (4)C16—C17—N2—C18175.2 (4)
C7—C11—C12—C17116.6 (4)C12—C17—N2—C185.8 (4)
C17—C12—C13—C140.8 (6)C16—C17—N2—C325.5 (6)
C11—C12—C13—C14177.7 (4)C12—C17—N2—C32175.5 (3)
C12—C13—C14—C150.3 (7)C6—C7—O2—C9167.3 (3)
C13—C14—C15—C160.8 (7)C8—C7—O2—C982.0 (4)
C14—C15—C16—C170.1 (7)C11—C7—O2—C937.9 (4)
C15—C16—C17—C121.0 (6)C25—C9—O2—C7158.5 (3)
C15—C16—C17—N2179.9 (4)C10—C9—O2—C736.8 (4)
C13—C12—C17—C161.4 (6)O4—C32—O5—C3315.0 (7)
C11—C12—C17—C16179.1 (4)N2—C32—O5—C33166.2 (3)
C13—C12—C17—N2179.5 (4)C35—C33—O5—C3268.5 (6)
C11—C12—C17—N21.8 (4)C34—C33—O5—C3257.3 (6)
C12—C11—C18—O3171.4 (4)C36—C33—O5—C32172.7 (4)
C10—C11—C18—O345.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O4i0.932.523.439 (7)170
C5—H5···O30.932.483.078 (6)123
C9—H9···O10.982.543.066 (5)114
C10—H10···O30.982.422.907 (5)110
C13—H13···O10.932.413.057 (6)127
C16—H16···O40.932.302.848 (6)117
C21—H21···O1ii0.932.553.374 (7)149
C31—H31A···O10.962.512.880 (6)103
C31—H31B···O4iii0.962.553.331 (6)139
C34—H34C···O40.962.523.011 (7)111
C35—H35A···O40.962.533.006 (7)111
C15—H15···Cg4(C1-C6)iii0.932.743.579 (6)150
C23—H23···Cg2(N1/C1/C6/C7/C8)iv0.932.923.688 (7)140
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+1; (iii) x+1, y+1, z; (iv) x1, 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
C32H25BrN2O3Z = 2
Mr = 565.45F(000) = 580
Triclinic, P1Dx = 1.444 Mg m3
a = 9.0986 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.7185 (7) ÅCell parameters from 5332 reflections
c = 16.5056 (13) Åθ = 2.6–26.8°
α = 78.915 (1)°µ = 1.62 mm1
β = 75.763 (1)°T = 294 K
γ = 67.687 (1)°Needle, colorless
V = 1300.77 (17) Å30.11 × 0.09 × 0.05 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4685 reflections with I > 2σ(I)
ω scansRint = 0.020
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 28.3°, θmin = 2.3°
Tmin = 0.83, Tmax = 0.94h = 1111
15355 measured reflectionsk = 1212
6111 independent reflectionsl = 2121
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-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 reflectionsΔρmax = 0.65 e Å3
345 parametersΔρmin = 0.42 e Å3
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
xyzUiso*/Ueq
Br11.66480 (3)0.21132 (3)0.44227 (2)0.06851 (12)
C10.6702 (3)0.1452 (3)0.84549 (13)0.0462 (5)
C20.6388 (4)0.0247 (3)0.89643 (17)0.0657 (7)
H20.54260.00880.90040.079*
C30.7552 (4)0.0712 (3)0.94114 (16)0.0692 (8)
H30.73670.15280.97590.083*
C40.8963 (4)0.0488 (3)0.93541 (15)0.0630 (7)
H40.97310.11560.96580.076*
C50.9273 (3)0.0732 (2)0.88450 (13)0.0487 (5)
H51.02440.08770.88030.058*
C60.8120 (2)0.1715 (2)0.84071 (12)0.0381 (4)
C70.8160 (2)0.3028 (2)0.77543 (11)0.0363 (4)
C80.6621 (3)0.3348 (3)0.74014 (14)0.0475 (5)
C90.9808 (2)0.3854 (2)0.66267 (12)0.0366 (4)
H90.89980.43460.62680.044*
C100.9549 (2)0.4856 (2)0.73035 (12)0.0359 (4)
H101.05480.44630.75300.043*
C110.8217 (2)0.4488 (2)0.80256 (12)0.0363 (4)
C120.6591 (2)0.5724 (2)0.82397 (14)0.0441 (5)
C130.5463 (3)0.6650 (3)0.77674 (18)0.0611 (6)
H130.56140.65470.72010.073*
C140.4089 (3)0.7744 (3)0.8148 (3)0.0822 (10)
H140.33200.83690.78320.099*
C150.3863 (3)0.7906 (3)0.8982 (3)0.0888 (11)
H150.29410.86440.92230.107*
C160.4969 (4)0.7001 (3)0.9466 (2)0.0742 (9)
H160.48070.71081.00330.089*
C170.6339 (3)0.5921 (2)0.90840 (15)0.0499 (5)
C180.8842 (3)0.4132 (2)0.88587 (13)0.0412 (4)
C190.9279 (2)0.6488 (2)0.70108 (12)0.0392 (4)
C200.8469 (3)0.7261 (3)0.63616 (16)0.0556 (6)
H200.80170.67850.61070.067*
C210.8326 (4)0.8749 (3)0.6086 (2)0.0725 (8)
H210.77900.92540.56450.087*
C220.8962 (4)0.9465 (3)0.6459 (2)0.0759 (9)
H220.88561.04580.62750.091*
C230.9750 (4)0.8733 (3)0.7096 (2)0.0745 (9)
H231.01810.92270.73510.089*
C240.9921 (3)0.7249 (3)0.73717 (15)0.0559 (6)
H241.04780.67570.78070.067*
C251.1477 (2)0.3403 (2)0.60933 (12)0.0392 (4)
C261.2539 (3)0.1935 (2)0.61442 (14)0.0496 (5)
H261.22120.12060.65120.060*
C271.4078 (3)0.1541 (3)0.56553 (15)0.0544 (6)
H271.47820.05530.56930.065*
C281.4557 (3)0.2623 (3)0.51125 (13)0.0463 (5)
C291.3533 (3)0.4087 (2)0.50493 (13)0.0485 (5)
H291.38720.48140.46860.058*
C301.1995 (3)0.4465 (2)0.55331 (14)0.0484 (5)
H301.12900.54500.54830.058*
C310.4337 (4)0.2412 (5)0.7699 (2)0.0915 (10)
H31A0.39470.32150.72770.137*
H31B0.35120.24940.81970.137*
H31C0.46050.14710.74910.137*
C320.7843 (4)0.4912 (3)1.02949 (15)0.0714 (8)
H32A0.87660.40621.04180.107*
H32B0.68900.48431.06830.107*
H32C0.79970.58131.03460.107*
N10.5780 (2)0.2495 (2)0.78981 (13)0.0547 (5)
N20.7654 (2)0.4939 (2)0.94408 (11)0.0506 (5)
O10.6266 (2)0.4152 (2)0.67712 (11)0.0697 (5)
O20.95368 (17)0.25538 (15)0.71081 (8)0.0408 (3)
O31.0189 (2)0.33092 (18)0.89698 (10)0.0530 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.05420 (16)0.06142 (17)0.07307 (19)0.02057 (12)0.01993 (12)0.00936 (13)
C10.0480 (12)0.0549 (13)0.0406 (11)0.0270 (10)0.0033 (9)0.0130 (9)
C20.0751 (17)0.0724 (17)0.0631 (15)0.0534 (15)0.0140 (13)0.0158 (13)
C30.108 (2)0.0559 (15)0.0510 (14)0.0492 (16)0.0007 (15)0.0018 (12)
C40.098 (2)0.0447 (13)0.0473 (13)0.0298 (13)0.0154 (13)0.0036 (10)
C50.0611 (13)0.0446 (11)0.0430 (11)0.0219 (10)0.0102 (10)0.0034 (9)
C60.0443 (10)0.0408 (10)0.0325 (9)0.0215 (8)0.0009 (8)0.0061 (8)
C70.0366 (10)0.0405 (10)0.0321 (9)0.0158 (8)0.0028 (7)0.0042 (8)
C80.0460 (12)0.0568 (13)0.0415 (11)0.0167 (10)0.0102 (9)0.0097 (10)
C90.0422 (10)0.0348 (9)0.0331 (9)0.0168 (8)0.0039 (8)0.0018 (7)
C100.0327 (9)0.0367 (9)0.0367 (9)0.0127 (8)0.0035 (7)0.0030 (8)
C110.0364 (9)0.0359 (10)0.0351 (9)0.0125 (8)0.0041 (8)0.0042 (8)
C120.0359 (10)0.0383 (10)0.0538 (12)0.0149 (8)0.0031 (9)0.0061 (9)
C130.0407 (12)0.0518 (13)0.0790 (17)0.0107 (10)0.0069 (12)0.0024 (12)
C140.0420 (14)0.0491 (15)0.137 (3)0.0053 (11)0.0044 (16)0.0068 (17)
C150.0443 (15)0.0573 (17)0.155 (3)0.0168 (13)0.0200 (19)0.042 (2)
C160.0646 (17)0.0729 (18)0.091 (2)0.0413 (15)0.0308 (15)0.0465 (16)
C170.0516 (12)0.0451 (12)0.0577 (13)0.0300 (10)0.0115 (10)0.0172 (10)
C180.0534 (12)0.0393 (10)0.0380 (10)0.0259 (9)0.0075 (9)0.0019 (8)
C190.0368 (10)0.0385 (10)0.0408 (10)0.0158 (8)0.0034 (8)0.0093 (8)
C200.0573 (14)0.0448 (12)0.0645 (15)0.0177 (11)0.0164 (12)0.0001 (11)
C210.0710 (17)0.0464 (14)0.0806 (19)0.0106 (13)0.0088 (15)0.0099 (13)
C220.0788 (19)0.0392 (13)0.094 (2)0.0218 (13)0.0154 (17)0.0107 (14)
C230.0807 (19)0.0606 (16)0.090 (2)0.0412 (15)0.0194 (17)0.0376 (16)
C240.0618 (14)0.0601 (14)0.0524 (13)0.0303 (12)0.0034 (11)0.0206 (11)
C250.0460 (11)0.0402 (10)0.0321 (9)0.0189 (9)0.0017 (8)0.0051 (8)
C260.0559 (13)0.0390 (11)0.0458 (11)0.0197 (10)0.0070 (10)0.0010 (9)
C270.0525 (13)0.0406 (11)0.0578 (14)0.0134 (10)0.0063 (10)0.0048 (10)
C280.0444 (11)0.0521 (12)0.0399 (11)0.0203 (10)0.0057 (9)0.0097 (9)
C290.0542 (12)0.0478 (12)0.0410 (11)0.0252 (10)0.0028 (9)0.0010 (9)
C300.0524 (12)0.0384 (11)0.0465 (12)0.0152 (9)0.0005 (10)0.0006 (9)
C310.0604 (17)0.134 (3)0.104 (2)0.0541 (19)0.0229 (17)0.018 (2)
C320.108 (2)0.0904 (19)0.0396 (12)0.0664 (18)0.0017 (13)0.0172 (12)
N10.0423 (10)0.0720 (13)0.0594 (12)0.0301 (9)0.0057 (9)0.0136 (10)
N20.0658 (12)0.0607 (11)0.0362 (9)0.0381 (10)0.0027 (8)0.0127 (8)
O10.0662 (11)0.0894 (13)0.0556 (10)0.0253 (10)0.0284 (9)0.0052 (10)
O20.0439 (7)0.0390 (7)0.0382 (7)0.0192 (6)0.0037 (6)0.0063 (6)
O30.0605 (10)0.0534 (9)0.0527 (9)0.0224 (8)0.0249 (8)0.0001 (7)
Geometric parameters (Å, º) top
Br1—C281.896 (2)C16—C171.389 (3)
C1—C21.385 (3)C16—H160.9300
C1—C61.389 (3)C17—N21.398 (3)
C1—N11.397 (3)C18—O31.218 (3)
C2—C31.380 (4)C18—N21.357 (3)
C2—H20.9300C19—C241.383 (3)
C3—C41.360 (4)C19—C201.384 (3)
C3—H30.9300C20—C211.396 (3)
C4—C51.395 (3)C20—H200.9300
C4—H40.9300C21—C221.357 (5)
C5—C61.372 (3)C21—H210.9300
C5—H50.9300C22—C231.349 (5)
C6—C71.509 (3)C22—H220.9300
C7—O21.419 (2)C23—C241.386 (4)
C7—C81.548 (3)C23—H230.9300
C7—C111.590 (3)C24—H240.9300
C8—O11.208 (3)C25—C261.386 (3)
C8—N11.363 (3)C25—C301.389 (3)
C9—O21.429 (2)C26—C271.384 (3)
C9—C251.503 (3)C26—H260.9300
C9—C101.539 (3)C27—C281.376 (3)
C9—H90.9800C27—H270.9300
C10—C191.509 (3)C28—C291.375 (3)
C10—C111.572 (3)C29—C301.380 (3)
C10—H100.9800C29—H290.9300
C11—C121.521 (3)C30—H300.9300
C11—C181.545 (3)C31—N11.463 (3)
C12—C131.377 (3)C31—H31A0.9600
C12—C171.394 (3)C31—H31B0.9600
C13—C141.396 (4)C31—H31C0.9600
C13—H130.9300C32—N21.456 (3)
C14—C151.372 (5)C32—H32A0.9600
C14—H140.9300C32—H32B0.9600
C15—C161.371 (5)C32—H32C0.9600
C15—H150.9300
C2—C1—C6121.5 (2)C16—C17—N2127.6 (2)
C2—C1—N1128.1 (2)C12—C17—N2110.30 (18)
C6—C1—N1110.28 (18)O3—C18—N2125.6 (2)
C3—C2—C1117.8 (2)O3—C18—C11126.09 (19)
C3—C2—H2121.1N2—C18—C11108.31 (18)
C1—C2—H2121.1C24—C19—C20117.4 (2)
C4—C3—C2121.3 (2)C24—C19—C10119.7 (2)
C4—C3—H3119.3C20—C19—C10122.84 (19)
C2—C3—H3119.3C19—C20—C21120.5 (2)
C3—C4—C5120.9 (3)C19—C20—H20119.7
C3—C4—H4119.6C21—C20—H20119.7
C5—C4—H4119.6C22—C21—C20120.4 (3)
C6—C5—C4118.8 (2)C22—C21—H21119.8
C6—C5—H5120.6C20—C21—H21119.8
C4—C5—H5120.6C23—C22—C21119.9 (3)
C5—C6—C1119.77 (19)C23—C22—H22120.0
C5—C6—C7131.08 (18)C21—C22—H22120.0
C1—C6—C7108.68 (18)C22—C23—C24120.5 (3)
O2—C7—C6109.09 (15)C22—C23—H23119.8
O2—C7—C8108.78 (15)C24—C23—H23119.8
C6—C7—C8101.31 (16)C19—C24—C23121.2 (3)
O2—C7—C11105.61 (14)C19—C24—H24119.4
C6—C7—C11119.48 (15)C23—C24—H24119.4
C8—C7—C11112.28 (16)C26—C25—C30118.24 (19)
O1—C8—N1125.6 (2)C26—C25—C9121.58 (17)
O1—C8—C7126.2 (2)C30—C25—C9120.18 (18)
N1—C8—C7108.12 (18)C27—C26—C25120.89 (19)
O2—C9—C25109.32 (15)C27—C26—H26119.6
O2—C9—C10103.14 (14)C25—C26—H26119.6
C25—C9—C10114.47 (16)C28—C27—C26119.4 (2)
O2—C9—H9109.9C28—C27—H27120.3
C25—C9—H9109.9C26—C27—H27120.3
C10—C9—H9109.9C29—C28—C27121.1 (2)
C19—C10—C9116.65 (16)C29—C28—Br1118.53 (16)
C19—C10—C11116.91 (15)C27—C28—Br1120.40 (17)
C9—C10—C11104.28 (15)C28—C29—C30119.04 (19)
C19—C10—H10106.0C28—C29—H29120.5
C9—C10—H10106.0C30—C29—H29120.5
C11—C10—H10106.0C29—C30—C25121.4 (2)
C12—C11—C18101.64 (16)C29—C30—H30119.3
C12—C11—C10118.59 (16)C25—C30—H30119.3
C18—C11—C10107.71 (16)N1—C31—H31A109.5
C12—C11—C7115.86 (16)N1—C31—H31B109.5
C18—C11—C7110.95 (15)H31A—C31—H31B109.5
C10—C11—C7102.02 (14)N1—C31—H31C109.5
C13—C12—C17118.9 (2)H31A—C31—H31C109.5
C13—C12—C11132.9 (2)H31B—C31—H31C109.5
C17—C12—C11108.09 (19)N2—C32—H32A109.5
C12—C13—C14119.3 (3)N2—C32—H32B109.5
C12—C13—H13120.4H32A—C32—H32B109.5
C14—C13—H13120.4N2—C32—H32C109.5
C15—C14—C13120.7 (3)H32A—C32—H32C109.5
C15—C14—H14119.7H32B—C32—H32C109.5
C13—C14—H14119.7C8—N1—C1110.64 (18)
C16—C15—C14121.3 (3)C8—N1—C31122.7 (2)
C16—C15—H15119.4C1—N1—C31124.5 (2)
C14—C15—H15119.4C18—N2—C17111.32 (18)
C15—C16—C17117.9 (3)C18—N2—C32123.3 (2)
C15—C16—H16121.1C17—N2—C32124.9 (2)
C17—C16—H16121.1C7—O2—C9108.23 (14)
C16—C17—C12122.0 (3)
C6—C1—C2—C31.4 (4)C11—C12—C17—C16178.46 (19)
N1—C1—C2—C3174.5 (2)C13—C12—C17—N2176.57 (19)
C1—C2—C3—C40.2 (4)C11—C12—C17—N20.5 (2)
C2—C3—C4—C50.6 (4)C12—C11—C18—O3171.94 (19)
C3—C4—C5—C60.6 (4)C10—C11—C18—O346.6 (2)
C4—C5—C6—C12.2 (3)C7—C11—C18—O364.3 (2)
C4—C5—C6—C7173.4 (2)C12—C11—C18—N25.7 (2)
C2—C1—C6—C52.7 (3)C10—C11—C18—N2131.02 (17)
N1—C1—C6—C5173.91 (19)C7—C11—C18—N2118.10 (17)
C2—C1—C6—C7175.6 (2)C9—C10—C19—C24143.16 (19)
N1—C1—C6—C70.9 (2)C11—C10—C19—C2492.5 (2)
C5—C6—C7—O252.6 (3)C9—C10—C19—C2033.8 (3)
C1—C6—C7—O2119.34 (17)C11—C10—C19—C2090.6 (2)
C5—C6—C7—C8167.2 (2)C24—C19—C20—C210.4 (3)
C1—C6—C7—C84.7 (2)C10—C19—C20—C21176.6 (2)
C5—C6—C7—C1169.0 (3)C19—C20—C21—C220.8 (4)
C1—C6—C7—C11119.14 (19)C20—C21—C22—C230.5 (4)
O2—C7—C8—O152.7 (3)C21—C22—C23—C240.3 (4)
C6—C7—C8—O1167.5 (2)C20—C19—C24—C230.4 (3)
C11—C7—C8—O163.8 (3)C10—C19—C24—C23177.5 (2)
O2—C7—C8—N1123.82 (18)C22—C23—C24—C190.7 (4)
C6—C7—C8—N19.0 (2)O2—C9—C25—C263.6 (3)
C11—C7—C8—N1119.66 (19)C10—C9—C25—C26111.5 (2)
O2—C9—C10—C19163.22 (16)O2—C9—C25—C30176.54 (18)
C25—C9—C10—C1978.1 (2)C10—C9—C25—C3068.4 (2)
O2—C9—C10—C1132.66 (18)C30—C25—C26—C270.6 (3)
C25—C9—C10—C11151.31 (16)C9—C25—C26—C27179.3 (2)
C19—C10—C11—C1214.2 (3)C25—C26—C27—C280.0 (4)
C9—C10—C11—C12116.24 (19)C26—C27—C28—C290.1 (4)
C19—C10—C11—C18100.38 (19)C26—C27—C28—Br1179.11 (19)
C9—C10—C11—C18129.22 (16)C27—C28—C29—C300.8 (4)
C19—C10—C11—C7142.77 (17)Br1—C28—C29—C30178.43 (17)
C9—C10—C11—C712.36 (18)C28—C29—C30—C251.4 (4)
O2—C7—C11—C12142.36 (16)C26—C25—C30—C291.3 (3)
C6—C7—C11—C1294.4 (2)C9—C25—C30—C29178.6 (2)
C8—C7—C11—C1224.0 (2)O1—C8—N1—C1166.3 (2)
O2—C7—C11—C18102.44 (17)C7—C8—N1—C110.2 (2)
C6—C7—C11—C1820.8 (2)O1—C8—N1—C312.5 (4)
C8—C7—C11—C18139.16 (17)C7—C8—N1—C31174.0 (2)
O2—C7—C11—C1012.05 (18)C2—C1—N1—C8169.0 (2)
C6—C7—C11—C10135.29 (17)C6—C1—N1—C87.2 (3)
C8—C7—C11—C10106.35 (17)C2—C1—N1—C315.6 (4)
C18—C11—C12—C13172.9 (2)C6—C1—N1—C31170.7 (2)
C10—C11—C12—C1355.1 (3)O3—C18—N2—C17171.83 (19)
C7—C11—C12—C1366.7 (3)C11—C18—N2—C175.8 (2)
C18—C11—C12—C173.6 (2)O3—C18—N2—C320.5 (3)
C10—C11—C12—C17121.42 (19)C11—C18—N2—C32178.16 (19)
C7—C11—C12—C17116.73 (18)C16—C17—N2—C18174.4 (2)
C17—C12—C13—C140.9 (3)C12—C17—N2—C183.4 (2)
C11—C12—C13—C14177.1 (2)C16—C17—N2—C322.1 (3)
C12—C13—C14—C150.3 (4)C12—C17—N2—C32175.6 (2)
C13—C14—C15—C160.2 (5)C6—C7—O2—C9164.37 (15)
C14—C15—C16—C170.7 (4)C8—C7—O2—C985.95 (18)
C15—C16—C17—C121.2 (3)C11—C7—O2—C934.76 (18)
C15—C16—C17—N2176.3 (2)C25—C9—O2—C7165.08 (15)
C13—C12—C17—C161.4 (3)C10—C9—O2—C742.91 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O30.932.412.979 (3)119
C9—H9···O10.982.493.077 (3)118
C10—H10···O30.982.432.949 (2)113
C13—H13···O10.932.382.954 (4)120
C26—H26···O20.932.352.709 (3)103
C29—H29···O1i0.932.443.159 (3)135
C31—H31A···O10.962.512.867 (4)102
C32—H32A···O30.962.522.873 (3)102
C32—H32B···Cg5(C12-C17)ii0.962.863.713 (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
C37H34N2O5F(000) = 1240
Mr = 586.66Dx = 1.255 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.1226 (9) ÅCell parameters from 5182 reflections
b = 14.3682 (13) Åθ = 2.3–26.5°
c = 21.353 (2) ŵ = 0.08 mm1
β = 91.799 (2)°T = 294 K
V = 3104.1 (5) Å3Plate, colorless
Z = 40.11 × 0.08 × 0.05 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5275 reflections with I > 2σ(I)
ω scansRint = 0.026
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 26.4°, θmin = 1.7°
Tmin = 0.96, Tmax = 0.99h = 1212
32699 measured reflectionsk = 1717
6337 independent reflectionsl = 2626
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-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 reflectionsΔρmax = 0.27 e Å3
402 parametersΔρmin = 0.16 e Å3
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
xyzUiso*/Ueq
C10.78549 (15)0.36896 (10)0.86336 (7)0.0458 (3)
C20.70250 (17)0.44115 (12)0.87718 (9)0.0581 (4)
H20.71390.50000.86010.070*
C30.60125 (18)0.42312 (13)0.91751 (9)0.0638 (5)
H30.54380.47090.92770.077*
C40.58376 (17)0.33634 (14)0.94275 (9)0.0617 (5)
H40.51340.32560.96880.074*
C50.67033 (15)0.26431 (12)0.92969 (8)0.0496 (4)
H50.65940.20580.94730.060*
C60.77230 (14)0.28113 (10)0.89026 (7)0.0416 (3)
C70.88073 (14)0.21963 (9)0.86692 (7)0.0391 (3)
C80.93764 (15)0.28068 (10)0.81417 (7)0.0434 (3)
C90.95012 (15)0.07405 (10)0.83671 (7)0.0428 (3)
H90.99120.09020.79720.051*
C101.04648 (14)0.09858 (10)0.89213 (6)0.0398 (3)
H101.03010.05320.92520.048*
C110.99615 (14)0.19452 (9)0.91645 (6)0.0377 (3)
C121.08584 (14)0.27644 (10)0.92958 (7)0.0404 (3)
C131.18047 (15)0.31809 (11)0.89351 (8)0.0488 (4)
H131.20550.29080.85620.059*
C141.23716 (16)0.40056 (12)0.91360 (9)0.0582 (4)
H141.30050.42920.88950.070*
C151.20104 (18)0.44093 (13)0.96885 (9)0.0636 (5)
H151.23930.49720.98110.076*
C161.10893 (17)0.39982 (12)1.00669 (8)0.0562 (4)
H161.08580.42671.04440.067*
C171.05266 (14)0.31709 (10)0.98611 (7)0.0429 (3)
C180.92993 (14)0.18140 (10)0.97952 (7)0.0410 (3)
C191.19309 (15)0.09315 (10)0.87948 (7)0.0422 (3)
C201.24576 (17)0.10531 (14)0.82126 (8)0.0592 (4)
H201.18950.11570.78670.071*
C211.38137 (19)0.10238 (15)0.81337 (10)0.0690 (5)
H211.41460.11100.77370.083*
C221.46602 (19)0.08711 (14)0.86290 (11)0.0697 (5)
H221.55670.08500.85740.084*
C231.41566 (19)0.07485 (15)0.92104 (11)0.0746 (6)
H231.47270.06490.95540.089*
C241.28000 (17)0.07707 (13)0.92924 (9)0.0593 (4)
H241.24740.06750.96900.071*
C250.90362 (16)0.02517 (10)0.83374 (7)0.0475 (4)
C260.92520 (18)0.07851 (12)0.78116 (9)0.0591 (4)
H260.97040.05340.74790.071*
C270.8794 (2)0.16988 (14)0.77799 (11)0.0747 (6)
H270.89450.20500.74230.090*
C280.8125 (2)0.20939 (13)0.82614 (12)0.0720 (6)
C290.7918 (2)0.15548 (14)0.87824 (11)0.0738 (6)
H290.74690.18080.91150.089*
C300.83600 (19)0.06478 (12)0.88226 (9)0.0630 (5)
H300.82020.03000.91800.076*
C310.9255 (2)0.44567 (13)0.78159 (10)0.0719 (5)
H31A0.99500.42670.75480.108*
H31B0.95620.49580.80800.108*
H31C0.85070.46610.75650.108*
C320.89238 (16)0.28703 (12)1.07095 (7)0.0499 (4)
C330.69765 (18)0.24771 (12)1.13027 (8)0.0559 (4)
C340.5818 (2)0.18667 (17)1.11165 (11)0.0856 (7)
H34A0.53760.21191.07500.128*
H34B0.52130.18421.14540.128*
H34C0.61270.12511.10270.128*
C350.6545 (2)0.34648 (14)1.14099 (9)0.0708 (5)
H35A0.72980.38361.15310.106*
H35B0.59130.34791.17360.106*
H35C0.61470.37091.10310.106*
C360.7755 (2)0.20700 (18)1.18477 (10)0.0832 (7)
H36A0.80500.14571.17410.125*
H36B0.72050.20351.22050.125*
H36C0.85060.24581.19450.125*
C370.7645 (3)0.30892 (14)0.82249 (14)0.1054 (10)
H37A0.78060.33360.78170.158*
H37B0.67150.31080.82980.158*
H37C0.81100.34560.85360.158*
N10.88731 (13)0.36766 (9)0.82017 (6)0.0496 (3)
N20.95503 (12)0.26214 (9)1.01525 (6)0.0438 (3)
O11.01426 (12)0.25583 (8)0.77495 (5)0.0556 (3)
O20.83534 (10)0.13260 (7)0.84480 (5)0.0427 (2)
O30.86937 (12)0.11421 (8)0.99542 (5)0.0548 (3)
O40.93842 (13)0.34313 (10)1.10674 (6)0.0677 (4)
O50.77931 (12)0.24267 (9)1.07374 (5)0.0613 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0444 (8)0.0401 (8)0.0529 (9)0.0030 (6)0.0010 (7)0.0039 (6)
C20.0587 (10)0.0405 (9)0.0747 (12)0.0033 (7)0.0041 (9)0.0058 (8)
C30.0511 (10)0.0606 (11)0.0796 (12)0.0128 (8)0.0001 (9)0.0168 (9)
C40.0421 (9)0.0758 (13)0.0678 (11)0.0038 (8)0.0087 (8)0.0086 (9)
C50.0405 (8)0.0536 (9)0.0551 (9)0.0034 (7)0.0058 (7)0.0013 (7)
C60.0394 (7)0.0395 (7)0.0457 (8)0.0032 (6)0.0005 (6)0.0044 (6)
C70.0415 (7)0.0354 (7)0.0405 (7)0.0042 (6)0.0048 (6)0.0005 (6)
C80.0459 (8)0.0423 (8)0.0420 (8)0.0038 (6)0.0039 (6)0.0023 (6)
C90.0480 (8)0.0400 (8)0.0408 (7)0.0003 (6)0.0055 (6)0.0043 (6)
C100.0460 (8)0.0348 (7)0.0390 (7)0.0024 (6)0.0070 (6)0.0007 (6)
C110.0386 (7)0.0358 (7)0.0390 (7)0.0031 (6)0.0071 (6)0.0012 (6)
C120.0379 (7)0.0379 (7)0.0454 (8)0.0014 (6)0.0032 (6)0.0029 (6)
C130.0420 (8)0.0488 (9)0.0562 (9)0.0055 (7)0.0093 (7)0.0009 (7)
C140.0444 (9)0.0548 (10)0.0756 (12)0.0143 (7)0.0060 (8)0.0033 (9)
C150.0581 (10)0.0510 (10)0.0815 (13)0.0181 (8)0.0033 (9)0.0097 (9)
C160.0588 (10)0.0510 (9)0.0587 (10)0.0083 (8)0.0002 (8)0.0155 (8)
C170.0378 (7)0.0437 (8)0.0471 (8)0.0013 (6)0.0003 (6)0.0029 (6)
C180.0418 (7)0.0420 (8)0.0393 (7)0.0012 (6)0.0059 (6)0.0018 (6)
C190.0460 (8)0.0339 (7)0.0468 (8)0.0012 (6)0.0054 (6)0.0029 (6)
C200.0531 (10)0.0718 (11)0.0534 (10)0.0082 (8)0.0124 (8)0.0027 (8)
C210.0604 (11)0.0747 (13)0.0734 (12)0.0064 (9)0.0258 (10)0.0070 (10)
C220.0460 (10)0.0629 (12)0.1008 (16)0.0013 (8)0.0119 (10)0.0096 (11)
C230.0538 (11)0.0818 (14)0.0872 (14)0.0027 (10)0.0128 (10)0.0066 (11)
C240.0555 (10)0.0639 (11)0.0584 (10)0.0048 (8)0.0006 (8)0.0067 (8)
C250.0504 (8)0.0382 (8)0.0536 (9)0.0012 (6)0.0055 (7)0.0059 (7)
C260.0656 (11)0.0509 (10)0.0602 (10)0.0082 (8)0.0094 (8)0.0150 (8)
C270.0822 (14)0.0512 (11)0.0887 (15)0.0167 (10)0.0302 (12)0.0301 (10)
C280.0721 (12)0.0377 (9)0.1036 (16)0.0014 (9)0.0388 (12)0.0031 (10)
C290.0798 (13)0.0513 (11)0.0894 (15)0.0181 (9)0.0124 (11)0.0091 (10)
C300.0772 (12)0.0475 (9)0.0645 (11)0.0136 (9)0.0034 (9)0.0039 (8)
C310.0816 (13)0.0482 (10)0.0866 (14)0.0062 (9)0.0151 (11)0.0227 (9)
C320.0512 (9)0.0581 (9)0.0405 (8)0.0008 (8)0.0043 (7)0.0075 (7)
C330.0600 (10)0.0625 (10)0.0465 (9)0.0047 (8)0.0208 (8)0.0037 (7)
C340.0783 (14)0.0939 (16)0.0868 (15)0.0199 (12)0.0360 (12)0.0138 (12)
C350.0758 (13)0.0701 (12)0.0676 (12)0.0163 (10)0.0193 (10)0.0001 (10)
C360.0860 (15)0.0996 (17)0.0654 (12)0.0303 (13)0.0230 (11)0.0172 (12)
C370.1113 (19)0.0386 (10)0.162 (3)0.0059 (11)0.0653 (18)0.0029 (12)
N10.0543 (8)0.0380 (7)0.0567 (8)0.0034 (6)0.0073 (6)0.0073 (6)
N20.0455 (7)0.0467 (7)0.0393 (6)0.0040 (5)0.0066 (5)0.0069 (5)
O10.0629 (7)0.0569 (7)0.0481 (6)0.0003 (5)0.0180 (5)0.0048 (5)
O20.0448 (6)0.0351 (5)0.0480 (6)0.0034 (4)0.0002 (4)0.0036 (4)
O30.0676 (7)0.0473 (6)0.0506 (6)0.0141 (5)0.0203 (5)0.0008 (5)
O40.0690 (8)0.0815 (9)0.0529 (7)0.0091 (7)0.0081 (6)0.0263 (6)
O50.0589 (7)0.0787 (8)0.0473 (6)0.0126 (6)0.0192 (5)0.0182 (6)
Geometric parameters (Å, º) top
C1—C21.373 (2)C20—H200.9300
C1—C61.395 (2)C21—C221.358 (3)
C1—N11.405 (2)C21—H210.9300
C2—C31.384 (3)C22—C231.368 (3)
C2—H20.9300C22—H220.9300
C3—C41.372 (3)C23—C241.390 (3)
C3—H30.9300C23—H230.9300
C4—C51.390 (2)C24—H240.9300
C4—H40.9300C25—C301.382 (2)
C5—C61.374 (2)C25—C261.382 (2)
C5—H50.9300C26—C271.393 (3)
C6—C71.506 (2)C26—H260.9300
C7—O21.4087 (17)C27—C281.371 (3)
C7—C81.553 (2)C27—H270.9300
C7—C111.593 (2)C28—C291.377 (3)
C8—O11.2129 (18)C28—C371.512 (3)
C8—N11.357 (2)C29—C301.380 (3)
C9—O21.4492 (17)C29—H290.9300
C9—C251.502 (2)C30—H300.9300
C9—C101.550 (2)C31—N11.451 (2)
C9—H90.9800C31—H31A0.9600
C10—C191.519 (2)C31—H31B0.9600
C10—C111.5640 (19)C31—H31C0.9600
C10—H100.9800C32—O41.1952 (19)
C11—C121.5074 (19)C32—O51.313 (2)
C11—C181.5346 (19)C32—N21.4114 (19)
C12—C131.384 (2)C33—O51.4861 (18)
C12—C171.392 (2)C33—C361.503 (3)
C13—C141.379 (2)C33—C351.504 (3)
C13—H130.9300C33—C341.508 (3)
C14—C151.374 (3)C34—H34A0.9600
C14—H140.9300C34—H34B0.9600
C15—C161.385 (3)C34—H34C0.9600
C15—H150.9300C35—H35A0.9600
C16—C171.384 (2)C35—H35B0.9600
C16—H160.9300C35—H35C0.9600
C17—N21.4234 (19)C36—H36A0.9600
C18—O31.1984 (17)C36—H36B0.9600
C18—N21.4072 (19)C36—H36C0.9600
C19—C241.378 (2)C37—H37A0.9600
C19—C201.379 (2)C37—H37B0.9600
C20—C211.389 (3)C37—H37C0.9600
C2—C1—C6121.88 (15)C21—C22—C23118.92 (18)
C2—C1—N1128.15 (15)C21—C22—H22120.5
C6—C1—N1109.89 (13)C23—C22—H22120.5
C1—C2—C3117.55 (16)C22—C23—C24120.60 (19)
C1—C2—H2121.2C22—C23—H23119.7
C3—C2—H2121.2C24—C23—H23119.7
C4—C3—C2121.46 (16)C19—C24—C23121.07 (18)
C4—C3—H3119.3C19—C24—H24119.5
C2—C3—H3119.3C23—C24—H24119.5
C3—C4—C5120.52 (16)C30—C25—C26118.37 (16)
C3—C4—H4119.7C30—C25—C9121.40 (14)
C5—C4—H4119.7C26—C25—C9120.21 (15)
C6—C5—C4118.85 (16)C25—C26—C27120.06 (19)
C6—C5—H5120.6C25—C26—H26120.0
C4—C5—H5120.6C27—C26—H26120.0
C5—C6—C1119.67 (14)C28—C27—C26121.66 (19)
C5—C6—C7131.99 (14)C28—C27—H27119.2
C1—C6—C7108.33 (12)C26—C27—H27119.2
O2—C7—C6113.48 (11)C27—C28—C29117.66 (18)
O2—C7—C8112.50 (11)C27—C28—C37121.2 (2)
C6—C7—C8101.51 (11)C29—C28—C37121.1 (2)
O2—C7—C11104.26 (11)C28—C29—C30121.6 (2)
C6—C7—C11116.13 (11)C28—C29—H29119.2
C8—C7—C11109.18 (11)C30—C29—H29119.2
O1—C8—N1125.89 (14)C29—C30—C25120.63 (18)
O1—C8—C7126.48 (14)C29—C30—H30119.7
N1—C8—C7107.62 (12)C25—C30—H30119.7
O2—C9—C25107.74 (12)N1—C31—H31A109.5
O2—C9—C10105.34 (11)N1—C31—H31B109.5
C25—C9—C10115.91 (12)H31A—C31—H31B109.5
O2—C9—H9109.2N1—C31—H31C109.5
C25—C9—H9109.2H31A—C31—H31C109.5
C10—C9—H9109.2H31B—C31—H31C109.5
C19—C10—C9116.58 (12)O4—C32—O5128.41 (15)
C19—C10—C11115.76 (11)O4—C32—N2122.22 (15)
C9—C10—C11104.49 (11)O5—C32—N2109.30 (13)
C19—C10—H10106.4O5—C33—C36108.57 (14)
C9—C10—H10106.4O5—C33—C35109.95 (14)
C11—C10—H10106.4C36—C33—C35113.40 (17)
C12—C11—C18102.11 (11)O5—C33—C34101.85 (14)
C12—C11—C10123.33 (12)C36—C33—C34111.23 (19)
C18—C11—C10109.82 (11)C35—C33—C34111.19 (17)
C12—C11—C7111.81 (11)C33—C34—H34A109.5
C18—C11—C7106.20 (11)C33—C34—H34B109.5
C10—C11—C7102.65 (11)H34A—C34—H34B109.5
C13—C12—C17119.43 (14)C33—C34—H34C109.5
C13—C12—C11131.12 (13)H34A—C34—H34C109.5
C17—C12—C11109.19 (12)H34B—C34—H34C109.5
C14—C13—C12119.15 (15)C33—C35—H35A109.5
C14—C13—H13120.4C33—C35—H35B109.5
C12—C13—H13120.4H35A—C35—H35B109.5
C15—C14—C13120.68 (16)C33—C35—H35C109.5
C15—C14—H14119.7H35A—C35—H35C109.5
C13—C14—H14119.7H35B—C35—H35C109.5
C14—C15—C16121.52 (16)C33—C36—H36A109.5
C14—C15—H15119.2C33—C36—H36B109.5
C16—C15—H15119.2H36A—C36—H36B109.5
C17—C16—C15117.33 (16)C33—C36—H36C109.5
C17—C16—H16121.3H36A—C36—H36C109.5
C15—C16—H16121.3H36B—C36—H36C109.5
C16—C17—C12121.86 (15)C28—C37—H37A109.5
C16—C17—N2128.48 (14)C28—C37—H37B109.5
C12—C17—N2109.64 (12)H37A—C37—H37B109.5
O3—C18—N2126.56 (13)C28—C37—H37C109.5
O3—C18—C11126.09 (13)H37A—C37—H37C109.5
N2—C18—C11107.35 (11)H37B—C37—H37C109.5
C24—C19—C20117.45 (15)C8—N1—C1111.07 (12)
C24—C19—C10118.39 (14)C8—N1—C31123.38 (15)
C20—C19—C10124.15 (14)C1—N1—C31125.23 (14)
C19—C20—C21121.13 (18)C18—N2—C32125.99 (13)
C19—C20—H20119.4C18—N2—C17109.65 (11)
C21—C20—H20119.4C32—N2—C17124.36 (13)
C22—C21—C20120.82 (18)C7—O2—C9107.52 (10)
C22—C21—H21119.6C32—O5—C33121.40 (13)
C20—C21—H21119.6
C6—C1—C2—C32.2 (3)C7—C11—C18—O377.74 (18)
N1—C1—C2—C3174.15 (16)C12—C11—C18—N214.26 (14)
C1—C2—C3—C40.2 (3)C10—C11—C18—N2146.69 (12)
C2—C3—C4—C51.8 (3)C7—C11—C18—N2103.01 (13)
C3—C4—C5—C61.1 (3)C9—C10—C19—C24154.34 (14)
C4—C5—C6—C11.2 (2)C11—C10—C19—C2482.14 (18)
C4—C5—C6—C7179.85 (15)C9—C10—C19—C2027.1 (2)
C2—C1—C6—C52.9 (2)C11—C10—C19—C2096.39 (18)
N1—C1—C6—C5174.04 (13)C24—C19—C20—C210.6 (3)
C2—C1—C6—C7178.17 (14)C10—C19—C20—C21177.89 (17)
N1—C1—C6—C74.91 (17)C19—C20—C21—C220.2 (3)
C5—C6—C7—O247.5 (2)C20—C21—C22—C230.2 (3)
C1—C6—C7—O2131.27 (13)C21—C22—C23—C240.6 (3)
C5—C6—C7—C8168.45 (16)C20—C19—C24—C231.1 (3)
C1—C6—C7—C810.32 (15)C10—C19—C24—C23177.55 (16)
C5—C6—C7—C1173.3 (2)C22—C23—C24—C191.1 (3)
C1—C6—C7—C11107.93 (14)O2—C9—C25—C3058.33 (19)
O2—C7—C8—O146.5 (2)C10—C9—C25—C3059.3 (2)
C6—C7—C8—O1168.11 (15)O2—C9—C25—C26120.12 (15)
C11—C7—C8—O168.75 (19)C10—C9—C25—C26122.22 (16)
O2—C7—C8—N1134.19 (13)C30—C25—C26—C270.1 (3)
C6—C7—C8—N112.57 (15)C9—C25—C26—C27178.58 (15)
C11—C7—C8—N1110.57 (13)C25—C26—C27—C280.1 (3)
O2—C9—C10—C19147.11 (12)C26—C27—C28—C290.1 (3)
C25—C9—C10—C1993.91 (16)C26—C27—C28—C37179.34 (18)
O2—C9—C10—C1117.96 (14)C27—C28—C29—C300.1 (3)
C25—C9—C10—C11136.94 (13)C37—C28—C29—C30179.54 (19)
C19—C10—C11—C122.51 (19)C28—C29—C30—C250.3 (3)
C9—C10—C11—C12132.14 (14)C26—C25—C30—C290.3 (3)
C19—C10—C11—C18122.76 (13)C9—C25—C30—C29178.75 (17)
C9—C10—C11—C18107.60 (12)O1—C8—N1—C1170.14 (15)
C19—C10—C11—C7124.60 (13)C7—C8—N1—C110.53 (17)
C9—C10—C11—C75.04 (13)O1—C8—N1—C313.7 (3)
O2—C7—C11—C12161.28 (11)C7—C8—N1—C31175.58 (16)
C6—C7—C11—C1273.10 (15)C2—C1—N1—C8172.87 (16)
C8—C7—C11—C1240.85 (15)C6—C1—N1—C83.80 (18)
O2—C7—C11—C1888.13 (12)C2—C1—N1—C310.9 (3)
C6—C7—C11—C1837.49 (15)C6—C1—N1—C31177.55 (16)
C8—C7—C11—C18151.44 (11)O3—C18—N2—C3213.5 (3)
O2—C7—C11—C1027.14 (13)C11—C18—N2—C32167.26 (14)
C6—C7—C11—C10152.77 (11)O3—C18—N2—C17167.61 (15)
C8—C7—C11—C1093.29 (12)C11—C18—N2—C1711.64 (16)
C18—C11—C12—C13173.94 (16)O4—C32—N2—C18161.58 (17)
C10—C11—C12—C1350.2 (2)O5—C32—N2—C1821.1 (2)
C7—C11—C12—C1372.90 (19)O4—C32—N2—C1719.7 (3)
C18—C11—C12—C1712.20 (15)O5—C32—N2—C17157.67 (14)
C10—C11—C12—C17135.98 (14)C16—C17—N2—C18177.59 (16)
C7—C11—C12—C17100.96 (14)C12—C17—N2—C183.80 (17)
C17—C12—C13—C141.8 (2)C16—C17—N2—C323.5 (2)
C11—C12—C13—C14171.51 (16)C12—C17—N2—C32175.13 (14)
C12—C13—C14—C150.3 (3)C6—C7—O2—C9167.98 (11)
C13—C14—C15—C161.2 (3)C8—C7—O2—C977.48 (14)
C14—C15—C16—C171.2 (3)C11—C7—O2—C940.69 (13)
C15—C16—C17—C120.4 (3)C25—C9—O2—C7161.93 (11)
C15—C16—C17—N2178.84 (16)C10—C9—O2—C737.64 (14)
C13—C12—C17—C161.9 (2)O4—C32—O5—C339.1 (3)
C11—C12—C17—C16172.81 (14)N2—C32—O5—C33173.74 (14)
C13—C12—C17—N2179.40 (13)C36—C33—O5—C3262.1 (2)
C11—C12—C17—N25.91 (17)C35—C33—O5—C3262.5 (2)
C12—C11—C18—O3165.00 (15)C34—C33—O5—C32179.56 (17)
C10—C11—C18—O332.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O10.982.443.006 (2)116
C10—H10···O30.982.412.895 (2)110
C16—H16···O40.932.362.905 (2)117
C31—H31A···O10.962.502.876 (2)103
C35—H35A···O40.962.432.989 (2)117
C36—H36B···O1i0.962.493.362 (2)151
C36—H36C···O40.962.523.081 (3)117
Symmetry code: (i) x1/2, y+1/2, z+1/2.
 

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