3-(6-Benz-yloxy-2,2-dimethyl-perhydro-furo[2,3-d][1,3]dioxol-5-yl)-5-(4-bromo-phen-yl)-2-phenyl-perhydro-pyrrolo[3,4-d]isoxazole-4,6-dione.

In the title compound, C(31)H(29)BrN(2)O(7), the isoxazolidine ring adopts a twist conformation, while the tetrahydrofuran, dioxolone and pyrrole rings adopt envelope conformations. The structure is stabilized by inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For general background to isoxazolidines, see: Ali et al. (1988 ▶); Goti et al. (1997 ▶); Kumar et al. (2003 ▶); Huisgen (1984 ▶). For ring puckering parameters see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C31H29BrN2O7

M = 621.47

Monoclinic,

a = 15.0680 (12) Å

b = 6.6801 (5) Å

c = 15.8550 (12) Å

β = 117.578 (2)°

V = 1414.57 (19) Å3

Z = 2

Mo Kα radiation

μ = 1.51 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2004 ▶) T min = 0.734, T max = 0.740

20450 measured reflections

9003 independent reflections

5502 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.138

S = 1.00

9003 reflections

372 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), 3886 Friedel pairs

Flack parameter: −0.001 (8)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015104/bt2932sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015104/bt2932Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C31H29BrN2O7	F(000) = 640
Mr = 621.47	Dx = 1.459 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5502 reflections
a = 15.0680 (12) Å	θ = 2.5–25°
b = 6.6801 (5) Å	µ = 1.51 mm−1
c = 15.8550 (12) Å	T = 293 K
β = 117.578 (2)°	Needle, colourless
V = 1414.57 (19) Å3	0.3 × 0.2 × 0.2 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	9003 independent reflections
Radiation source: fine-focus sealed tube	5502 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω and φ scans	θmax = 31.7°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −22→22
Tmin = 0.734, Tmax = 0.740	k = −9→8
20450 measured reflections	l = −23→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.066P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
9003 reflections	Δρmax = 0.66 e Å−3
372 parameters	Δρmin = −0.38 e Å−3
1 restraint	Absolute structure: Flack (1983), 3886 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.001 (8)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.64016 (18)	0.3845 (4)	0.35916 (18)	0.0430 (6)
H1	0.6865	0.4725	0.4028	0.052*
C2	0.5464 (2)	0.4517 (5)	0.2949 (2)	0.0524 (7)
H2	0.5293	0.5853	0.2952	0.063*
C3	0.4785 (2)	0.3213 (5)	0.2304 (2)	0.0557 (7)
C4	0.5020 (2)	0.1225 (5)	0.2294 (2)	0.0576 (8)
H4	0.4553	0.0349	0.1858	0.069*
C5	0.5958 (2)	0.0545 (4)	0.2940 (2)	0.0462 (6)
H5	0.6125	−0.0796	0.2942	0.055*
C6	0.66469 (18)	0.1858 (4)	0.35820 (16)	0.0359 (5)
C7	0.7771 (2)	−0.0588 (4)	0.47898 (17)	0.0415 (5)
C8	0.85005 (18)	0.2249 (4)	0.45433 (17)	0.0381 (5)
C9	0.93114 (18)	0.1327 (4)	0.54302 (17)	0.0370 (5)
H9	0.9931	0.1105	0.5385	0.044*
C10	0.88614 (19)	−0.0602 (4)	0.55592 (17)	0.0427 (5)
H10	0.9220	−0.1772	0.5498	0.051*
C11	0.94837 (17)	0.2561 (3)	0.63122 (16)	0.0340 (5)
H11	0.9266	0.3948	0.6132	0.041*
C12	1.05597 (18)	0.2501 (4)	0.70747 (16)	0.0352 (5)
H12	1.0775	0.1109	0.7240	0.042*
C13	1.07749 (18)	0.3678 (3)	0.79726 (16)	0.0347 (5)
H13	1.0594	0.2926	0.8402	0.042*
C14	1.18993 (18)	0.3982 (4)	0.83916 (16)	0.0379 (5)
H14	1.2135	0.5202	0.8776	0.045*
C15	1.20853 (17)	0.3989 (4)	0.75221 (16)	0.0402 (5)
H15	1.2319	0.5306	0.7437	0.048*
C16	1.3149 (2)	0.1722 (4)	0.86285 (19)	0.0447 (6)
C17	1.3205 (3)	−0.0535 (6)	0.8586 (3)	0.0690 (9)
H17A	1.3361	−0.1092	0.9197	0.104*
H17B	1.3718	−0.0898	0.8415	0.104*
H17C	1.2572	−0.1047	0.8118	0.104*
C18	1.4135 (2)	0.2643 (7)	0.9303 (3)	0.0759 (11)
H18A	1.4063	0.4071	0.9304	0.114*
H18B	1.4629	0.2314	0.9104	0.114*
H18C	1.4342	0.2134	0.9933	0.114*
C19	0.9839 (2)	0.6190 (4)	0.82909 (19)	0.0432 (6)
H19A	0.9439	0.5111	0.8349	0.052*
H19B	0.9392	0.7302	0.7980	0.052*
C20	1.05951 (18)	0.6836 (3)	0.92725 (17)	0.0359 (5)
C21	1.0676 (2)	0.5854 (4)	1.00695 (19)	0.0453 (6)
H21	1.0286	0.4729	1.0005	0.054*
C22	1.1336 (2)	0.6541 (5)	1.0960 (2)	0.0557 (7)
H22	1.1379	0.5884	1.1495	0.067*
C23	1.1925 (2)	0.8162 (5)	1.1073 (2)	0.0600 (8)
H23	1.2366	0.8609	1.1680	0.072*
C24	1.1866 (2)	0.9139 (5)	1.0285 (2)	0.0587 (7)
H24	1.2271	1.0242	1.0356	0.070*
C25	1.1202 (2)	0.8473 (4)	0.9390 (2)	0.0471 (6)
H25	1.1162	0.9134	0.8857	0.057*
C26	0.78715 (19)	0.2237 (4)	0.63967 (16)	0.0380 (5)
C27	0.7611 (2)	0.4255 (5)	0.6230 (2)	0.0486 (6)
H27	0.8081	0.5200	0.6270	0.058*
C28	0.6640 (3)	0.4843 (6)	0.6006 (3)	0.0656 (9)
H28	0.6465	0.6187	0.5886	0.079*
C29	0.5940 (2)	0.3490 (6)	0.5957 (3)	0.0699 (10)
H29	0.5294	0.3901	0.5807	0.084*
C30	0.6209 (2)	0.1490 (6)	0.6135 (2)	0.0645 (9)
H30	0.5737	0.0551	0.6100	0.077*
C31	0.7164 (2)	0.0883 (5)	0.6361 (2)	0.0511 (7)
H31	0.7336	−0.0460	0.6492	0.061*
N1	0.76087 (15)	0.1169 (3)	0.42650 (14)	0.0342 (4)
N2	0.88766 (16)	0.1595 (3)	0.66968 (14)	0.0367 (4)
O1	0.85721 (15)	0.3700 (3)	0.41335 (14)	0.0592 (6)
O2	0.71522 (18)	−0.1839 (3)	0.46666 (16)	0.0608 (6)
O3	0.89191 (14)	−0.0499 (3)	0.64921 (12)	0.0442 (4)
O4	1.11759 (13)	0.3476 (3)	0.67218 (12)	0.0419 (4)
O5	1.28173 (14)	0.2528 (3)	0.77001 (14)	0.0501 (5)
O6	1.23964 (13)	0.2227 (3)	0.88938 (12)	0.0419 (4)
O7	1.02692 (15)	0.5529 (3)	0.77010 (13)	0.0429 (4)
Br1	0.35138 (3)	0.41736 (8)	0.14395 (3)	0.1005 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0417 (13)	0.0400 (13)	0.0428 (13)	−0.0072 (11)	0.0157 (11)	−0.0124 (11)
C2	0.0489 (15)	0.0478 (14)	0.0581 (17)	0.0043 (12)	0.0228 (13)	−0.0084 (13)
C3	0.0343 (14)	0.0731 (19)	0.0541 (18)	0.0086 (13)	0.0158 (13)	−0.0138 (14)
C4	0.0374 (14)	0.0683 (19)	0.0611 (18)	−0.0091 (13)	0.0177 (13)	−0.0319 (15)
C5	0.0384 (13)	0.0423 (12)	0.0578 (17)	−0.0065 (11)	0.0222 (12)	−0.0192 (12)
C6	0.0352 (12)	0.0398 (12)	0.0353 (12)	−0.0065 (9)	0.0185 (10)	−0.0070 (9)
C7	0.0558 (15)	0.0311 (11)	0.0400 (13)	−0.0054 (11)	0.0244 (11)	−0.0081 (10)
C8	0.0340 (12)	0.0461 (13)	0.0338 (12)	−0.0050 (10)	0.0153 (10)	−0.0001 (10)
C9	0.0329 (12)	0.0425 (12)	0.0357 (12)	0.0009 (9)	0.0161 (10)	0.0006 (10)
C10	0.0530 (14)	0.0315 (11)	0.0431 (14)	0.0070 (11)	0.0218 (11)	0.0019 (10)
C11	0.0334 (11)	0.0352 (11)	0.0328 (11)	0.0030 (9)	0.0149 (9)	0.0044 (9)
C12	0.0341 (12)	0.0363 (11)	0.0350 (12)	−0.0004 (9)	0.0158 (10)	0.0014 (9)
C13	0.0381 (12)	0.0349 (11)	0.0329 (11)	0.0004 (9)	0.0181 (10)	0.0045 (9)
C14	0.0393 (11)	0.0383 (11)	0.0316 (11)	−0.0032 (10)	0.0127 (9)	−0.0022 (10)
C15	0.0358 (11)	0.0427 (12)	0.0385 (12)	−0.0072 (10)	0.0142 (10)	0.0027 (11)
C16	0.0345 (13)	0.0587 (15)	0.0402 (13)	0.0000 (11)	0.0166 (11)	0.0047 (12)
C17	0.076 (2)	0.0624 (19)	0.080 (2)	0.0156 (18)	0.0458 (19)	0.0102 (17)
C18	0.0406 (18)	0.111 (3)	0.064 (2)	−0.0090 (18)	0.0140 (16)	−0.008 (2)
C19	0.0424 (14)	0.0470 (14)	0.0435 (14)	0.0091 (11)	0.0227 (12)	0.0013 (11)
C20	0.0380 (12)	0.0380 (12)	0.0371 (12)	0.0077 (10)	0.0219 (10)	0.0018 (10)
C21	0.0496 (15)	0.0464 (14)	0.0456 (15)	0.0005 (12)	0.0268 (13)	0.0069 (11)
C22	0.0602 (18)	0.0670 (18)	0.0401 (15)	0.0136 (15)	0.0234 (14)	0.0121 (13)
C23	0.0455 (16)	0.077 (2)	0.0481 (17)	0.0061 (15)	0.0141 (13)	−0.0170 (15)
C24	0.0553 (16)	0.0568 (16)	0.0696 (19)	−0.0134 (15)	0.0337 (14)	−0.0139 (16)
C25	0.0585 (17)	0.0401 (13)	0.0524 (16)	−0.0017 (11)	0.0338 (14)	0.0016 (11)
C26	0.0387 (13)	0.0487 (13)	0.0282 (11)	−0.0048 (10)	0.0167 (10)	−0.0032 (10)
C27	0.0428 (13)	0.0461 (14)	0.0596 (16)	0.0018 (12)	0.0259 (12)	0.0012 (13)
C28	0.0530 (19)	0.071 (2)	0.078 (2)	0.0156 (15)	0.0347 (17)	0.0065 (17)
C29	0.0366 (15)	0.108 (3)	0.067 (2)	0.0044 (16)	0.0253 (15)	−0.008 (2)
C30	0.0486 (18)	0.088 (3)	0.065 (2)	−0.0179 (17)	0.0339 (16)	−0.0119 (18)
C31	0.0508 (16)	0.0582 (16)	0.0496 (16)	−0.0155 (13)	0.0278 (13)	−0.0062 (13)
N1	0.0341 (10)	0.0343 (9)	0.0339 (10)	−0.0038 (7)	0.0155 (8)	−0.0032 (8)
N2	0.0378 (10)	0.0365 (10)	0.0355 (10)	−0.0027 (8)	0.0166 (8)	−0.0001 (8)
O1	0.0442 (10)	0.0710 (13)	0.0481 (11)	−0.0187 (9)	0.0092 (8)	0.0213 (10)
O2	0.0768 (15)	0.0417 (10)	0.0591 (13)	−0.0238 (10)	0.0274 (12)	−0.0086 (9)
O3	0.0540 (10)	0.0345 (8)	0.0416 (9)	0.0038 (8)	0.0198 (8)	0.0092 (7)
O4	0.0365 (9)	0.0575 (11)	0.0325 (8)	−0.0067 (8)	0.0167 (7)	−0.0015 (7)
O5	0.0431 (11)	0.0668 (12)	0.0457 (10)	0.0046 (9)	0.0250 (9)	0.0085 (9)
O6	0.0403 (10)	0.0494 (10)	0.0364 (9)	0.0036 (8)	0.0180 (8)	0.0072 (7)
O7	0.0575 (11)	0.0388 (9)	0.0350 (9)	0.0079 (8)	0.0235 (8)	0.0037 (7)
Br1	0.0491 (2)	0.1229 (4)	0.0909 (3)	0.0303 (2)	−0.00047 (17)	−0.0247 (3)

C1—C2	1.379 (4)	C16—O6	1.421 (3)
C1—C6	1.380 (4)	C16—O5	1.423 (3)
C1—H1	0.9300	C16—C18	1.502 (4)
C2—C3	1.372 (4)	C16—C17	1.513 (5)
C2—H2	0.9300	C17—H17A	0.9600
C3—C4	1.377 (5)	C17—H17B	0.9600
C3—Br1	1.878 (3)	C17—H17C	0.9600
C4—C5	1.384 (4)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.380 (3)	C18—H18C	0.9600
C5—H5	0.9300	C19—O7	1.433 (3)
C6—N1	1.425 (3)	C19—C20	1.505 (4)
C7—O2	1.198 (3)	C19—H19A	0.9700
C7—N1	1.393 (3)	C19—H19B	0.9700
C7—C10	1.527 (4)	C20—C21	1.378 (3)
C8—O1	1.199 (3)	C20—C25	1.382 (4)
C8—N1	1.405 (3)	C21—C22	1.376 (4)
C8—C9	1.503 (3)	C21—H21	0.9300
C9—C10	1.513 (4)	C22—C23	1.359 (5)
C9—C11	1.538 (3)	C22—H22	0.9300
C9—H9	0.9800	C23—C24	1.375 (5)
C10—O3	1.443 (3)	C23—H23	0.9300
C10—H10	0.9800	C24—C25	1.377 (4)
C11—N2	1.464 (3)	C24—H24	0.9300
C11—C12	1.509 (3)	C25—H25	0.9300
C11—H11	0.9800	C26—C31	1.379 (4)
C12—O4	1.442 (3)	C26—C27	1.395 (4)
C12—C13	1.524 (3)	C26—N2	1.427 (3)
C12—H12	0.9800	C27—C28	1.392 (4)
C13—O7	1.411 (3)	C27—H27	0.9300
C13—C14	1.520 (3)	C28—C29	1.364 (5)
C13—H13	0.9800	C28—H28	0.9300
C14—O6	1.420 (3)	C29—C30	1.386 (6)
C14—C15	1.529 (3)	C29—H29	0.9300
C14—H14	0.9800	C30—C31	1.374 (4)
C15—O5	1.400 (3)	C30—H30	0.9300
C15—O4	1.413 (3)	C31—H31	0.9300
C15—H15	0.9800	N2—O3	1.444 (3)
C2—C1—C6	119.5 (2)	O6—C16—C17	108.6 (2)
C2—C1—H1	120.2	O5—C16—C17	109.3 (3)
C6—C1—H1	120.2	C18—C16—C17	112.5 (3)
C3—C2—C1	120.0 (3)	C16—C17—H17A	109.5
C3—C2—H2	120.0	C16—C17—H17B	109.5
C1—C2—H2	120.0	H17A—C17—H17B	109.5
C2—C3—C4	120.9 (3)	C16—C17—H17C	109.5
C2—C3—Br1	119.0 (2)	H17A—C17—H17C	109.5
C4—C3—Br1	120.2 (2)	H17B—C17—H17C	109.5
C3—C4—C5	119.3 (3)	C16—C18—H18A	109.5
C3—C4—H4	120.4	C16—C18—H18B	109.5
C5—C4—H4	120.4	H18A—C18—H18B	109.5
C6—C5—C4	119.9 (3)	C16—C18—H18C	109.5
C6—C5—H5	120.1	H18A—C18—H18C	109.5
C4—C5—H5	120.1	H18B—C18—H18C	109.5
C1—C6—C5	120.4 (2)	O7—C19—C20	114.1 (2)
C1—C6—N1	119.1 (2)	O7—C19—H19A	108.7
C5—C6—N1	120.5 (2)	C20—C19—H19A	108.7
O2—C7—N1	125.6 (3)	O7—C19—H19B	108.7
O2—C7—C10	126.5 (2)	C20—C19—H19B	108.7
N1—C7—C10	107.9 (2)	H19A—C19—H19B	107.6
O1—C8—N1	123.9 (2)	C21—C20—C25	118.8 (2)
O1—C8—C9	126.9 (2)	C21—C20—C19	121.0 (2)
N1—C8—C9	109.2 (2)	C25—C20—C19	120.2 (2)
C8—C9—C10	104.74 (19)	C22—C21—C20	119.8 (3)
C8—C9—C11	110.7 (2)	C22—C21—H21	120.1
C10—C9—C11	103.35 (19)	C20—C21—H21	120.1
C8—C9—H9	112.5	C23—C22—C21	121.2 (3)
C10—C9—H9	112.5	C23—C22—H22	119.4
C11—C9—H9	112.5	C21—C22—H22	119.4
O3—C10—C9	106.3 (2)	C22—C23—C24	119.7 (3)
O3—C10—C7	110.5 (2)	C22—C23—H23	120.2
C9—C10—C7	105.72 (19)	C24—C23—H23	120.2
O3—C10—H10	111.4	C25—C24—C23	119.5 (3)
C9—C10—H10	111.4	C25—C24—H24	120.2
C7—C10—H10	111.4	C23—C24—H24	120.2
N2—C11—C12	107.55 (18)	C24—C25—C20	120.9 (3)
N2—C11—C9	105.52 (19)	C24—C25—H25	119.5
C12—C11—C9	112.38 (19)	C20—C25—H25	119.5
N2—C11—H11	110.4	C31—C26—C27	118.8 (3)
C12—C11—H11	110.4	C31—C26—N2	119.8 (2)
C9—C11—H11	110.4	C27—C26—N2	121.1 (2)
O4—C12—C11	108.86 (18)	C28—C27—C26	119.5 (3)
O4—C12—C13	103.47 (18)	C28—C27—H27	120.3
C11—C12—C13	114.83 (19)	C26—C27—H27	120.3
O4—C12—H12	109.8	C29—C28—C27	121.3 (3)
C11—C12—H12	109.8	C29—C28—H28	119.3
C13—C12—H12	109.8	C27—C28—H28	119.3
O7—C13—C14	110.6 (2)	C28—C29—C30	118.8 (3)
O7—C13—C12	108.39 (18)	C28—C29—H29	120.6
C14—C13—C12	100.91 (18)	C30—C29—H29	120.6
O7—C13—H13	112.1	C31—C30—C29	120.6 (3)
C14—C13—H13	112.1	C31—C30—H30	119.7
C12—C13—H13	112.1	C29—C30—H30	119.7
O6—C14—C13	109.06 (19)	C30—C31—C26	120.9 (3)
O6—C14—C15	103.8 (2)	C30—C31—H31	119.5
C13—C14—C15	103.82 (17)	C26—C31—H31	119.5
O6—C14—H14	113.1	C7—N1—C8	111.6 (2)
C13—C14—H14	113.1	C7—N1—C6	124.2 (2)
C15—C14—H14	113.1	C8—N1—C6	124.1 (2)
O5—C15—O4	111.0 (2)	C26—N2—O3	111.51 (19)
O5—C15—C14	105.81 (19)	C26—N2—C11	120.00 (19)
O4—C15—C14	107.62 (18)	O3—N2—C11	103.42 (17)
O5—C15—H15	110.8	N2—O3—C10	106.78 (17)
O4—C15—H15	110.8	C15—O4—C12	106.98 (17)
C14—C15—H15	110.8	C15—O5—C16	109.83 (19)
O6—C16—O5	105.7 (2)	C14—O6—C16	108.42 (18)
O6—C16—C18	110.7 (2)	C13—O7—C19	114.50 (18)
O5—C16—C18	109.9 (3)
C6—C1—C2—C3	−0.2 (4)	C19—C20—C25—C24	177.0 (3)
C1—C2—C3—C4	0.7 (5)	C31—C26—C27—C28	−1.9 (4)
C1—C2—C3—Br1	179.9 (2)	N2—C26—C27—C28	−175.4 (3)
C2—C3—C4—C5	−0.5 (5)	C26—C27—C28—C29	0.9 (5)
Br1—C3—C4—C5	−179.7 (2)	C27—C28—C29—C30	−0.1 (6)
C3—C4—C5—C6	−0.3 (5)	C28—C29—C30—C31	0.3 (6)
C2—C1—C6—C5	−0.5 (4)	C29—C30—C31—C26	−1.4 (5)
C2—C1—C6—N1	−178.4 (2)	C27—C26—C31—C30	2.2 (4)
C4—C5—C6—C1	0.8 (4)	N2—C26—C31—C30	175.7 (3)
C4—C5—C6—N1	178.6 (2)	O2—C7—N1—C8	−175.9 (2)
O1—C8—C9—C10	−172.5 (3)	C10—C7—N1—C8	5.6 (3)
N1—C8—C9—C10	9.1 (3)	O2—C7—N1—C6	8.6 (4)
O1—C8—C9—C11	76.7 (3)	C10—C7—N1—C6	−169.94 (19)
N1—C8—C9—C11	−101.7 (2)	O1—C8—N1—C7	172.1 (2)
C8—C9—C10—O3	−123.0 (2)	C9—C8—N1—C7	−9.4 (3)
C11—C9—C10—O3	−7.1 (2)	O1—C8—N1—C6	−12.3 (4)
C8—C9—C10—C7	−5.5 (2)	C9—C8—N1—C6	166.1 (2)
C11—C9—C10—C7	110.4 (2)	C1—C6—N1—C7	134.2 (2)
O2—C7—C10—O3	−63.6 (3)	C5—C6—N1—C7	−43.7 (3)
N1—C7—C10—O3	114.9 (2)	C1—C6—N1—C8	−40.8 (3)
O2—C7—C10—C9	−178.2 (3)	C5—C6—N1—C8	141.3 (2)
N1—C7—C10—C9	0.3 (2)	C31—C26—N2—O3	27.9 (3)
C8—C9—C11—N2	95.2 (2)	C27—C26—N2—O3	−158.7 (2)
C10—C9—C11—N2	−16.4 (2)	C31—C26—N2—C11	149.0 (2)
C8—C9—C11—C12	−147.9 (2)	C27—C26—N2—C11	−37.7 (3)
C10—C9—C11—C12	100.5 (2)	C12—C11—N2—C26	148.6 (2)
N2—C11—C12—O4	−179.02 (17)	C9—C11—N2—C26	−91.2 (2)
C9—C11—C12—O4	65.3 (2)	C12—C11—N2—O3	−86.4 (2)
N2—C11—C12—C13	−63.6 (2)	C9—C11—N2—O3	33.8 (2)
C9—C11—C12—C13	−179.3 (2)	C26—N2—O3—C10	91.0 (2)
O4—C12—C13—O7	75.3 (2)	C11—N2—O3—C10	−39.3 (2)
C11—C12—C13—O7	−43.2 (3)	C9—C10—O3—N2	28.7 (2)
O4—C12—C13—C14	−40.9 (2)	C7—C10—O3—N2	−85.5 (2)
C11—C12—C13—C14	−159.34 (19)	O5—C15—O4—C12	95.9 (2)
O7—C13—C14—O6	163.81 (18)	C14—C15—O4—C12	−19.5 (3)
C12—C13—C14—O6	−81.6 (2)	C11—C12—O4—C15	160.8 (2)
O7—C13—C14—C15	−86.0 (2)	C13—C12—O4—C15	38.2 (2)
C12—C13—C14—C15	28.5 (2)	O4—C15—O5—C16	−120.5 (2)
O6—C14—C15—O5	−11.6 (2)	C14—C15—O5—C16	−4.1 (3)
C13—C14—C15—O5	−125.6 (2)	O6—C16—O5—C15	18.4 (3)
O6—C14—C15—O4	107.1 (2)	C18—C16—O5—C15	−101.0 (3)
C13—C14—C15—O4	−6.9 (3)	C17—C16—O5—C15	135.0 (3)
O7—C19—C20—C21	−118.0 (3)	C13—C14—O6—C16	133.4 (2)
O7—C19—C20—C25	64.0 (3)	C15—C14—O6—C16	23.3 (2)
C25—C20—C21—C22	1.6 (4)	O5—C16—O6—C14	−26.3 (3)
C19—C20—C21—C22	−176.4 (2)	C18—C16—O6—C14	92.6 (3)
C20—C21—C22—C23	−1.0 (4)	C17—C16—O6—C14	−143.4 (2)
C21—C22—C23—C24	−0.1 (5)	C14—C13—O7—C19	−109.0 (2)
C22—C23—C24—C25	0.6 (5)	C12—C13—O7—C19	141.2 (2)
C23—C24—C25—C20	0.0 (4)	C20—C19—O7—C13	70.5 (3)
C21—C20—C25—C24	−1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2i	0.93	2.46	3.273 (3)	145
C5—H5···O5ii	0.93	2.52	3.198 (3)	130
C9—H9···O1ii	0.98	2.58	3.418 (3)	144
C19—H19B···O3i	0.97	2.58	3.360 (3)	137
C17—H17b···Cg1iii	0.96	2.86	3.720 (4)	150
C21—H21···Cg2iv	0.93	2.67	3.559 (7)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2i	0.93	2.46	3.273 (3)	145
C5—H5⋯O5ii	0.93	2.52	3.198 (3)	130
C9—H9⋯O1ii	0.98	2.58	3.418 (3)	144
C19—H19B⋯O3i	0.97	2.58	3.360 (3)	137
C17—H17b⋯Cg1iii	0.96	2.86	3.720 (4)	150
C21—H21⋯Cg2iv	0.93	2.67	3.559 (7)	160

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the C1–C6 and C20–C25 rings, respectively.