Three structures of di­spiro­oxindole derivatives generated in situ through a three-component one-pot strategy with complete regio- and stereoselectivity

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.

Computing details

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

Crystal data

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) Å^3	0.15 × 0.07 × 0.05 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.203	w = 1/[σ^2(Fo^2) + (0.120P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4^i	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···O1^ii	0.93	2.55	3.374 (7)	149
C31—H31A···O1	0.96	2.51	2.880 (6)	103
C31—H31B···O4^iii	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

Crystal data

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) Å^3	0.11 × 0.09 × 0.05 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 0.4155P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	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

Crystal data

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) Å^3	Plate, colorless
Z = 4	0.11 × 0.08 × 0.05 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0716P)^2 + 0.6349P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	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.