1′-Benzyl-1-(2,4-dimethoxy­phenyl)-3-phenoxy­spiro­[azetidine-2,3′(3H)-indole]-2′,4(1H)-dione

The title compound, C₃₁H₂₆N₂O₅, is a compound with a spiro junction between β-lactam and isatin ring systems. Its four- and five-membered rings are nearly planar, with maximum deviations of −0.020 (1) and 0.050 (1) Å for their carbonyl C atoms, respectively. The dihedral angle between these two rings is 86.44 (5)°. The crystal structure is stabilized by intra­molecular C—H...O hydrogen-bonding and van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.102
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1'-Benzyl-1-(2,4-dimethoxyphenyl)-3-phenoxyspiro[azetidine-2,3'(3H)- indole]-2',4(1H)-dione

Crystal data

C31H26N2O5	F(000) = 1064
Mr = 506.54	Dx = 1.323 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 29809 reflections
a = 9.3547 (7) Å	θ = 1.5–27.3°
b = 10.0777 (5) Å	µ = 0.09 mm^−1
c = 28.193 (2) Å	T = 296 K
β = 106.838 (5)°	Prism, colourless
V = 2543.9 (3) Å^3	0.65 × 0.50 × 0.29 mm
Z = 4

Data collection

Stoe IPDS2 diffractometer	3963 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	Rint = 0.042
Plane graphite monochromator	θmax = 26.0°, θmin = 1.5°
Detector resolution: 6.67 pixels mm^-1	h = −11→11
ω scans	k = −12→12
26901 measured reflections	l = −34→32
4995 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.2246P] where P = (Fo^2 + 2Fc^2)/3
4995 reflections	(Δ/σ)max < 0.001
345 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.95416 (14)	0.67625 (14)	0.19705 (4)	0.0786 (5)
O2	0.55625 (10)	0.71175 (11)	0.26976 (3)	0.0596 (3)
O3	0.80723 (12)	0.35519 (10)	0.38761 (4)	0.0621 (3)
O4	0.76729 (10)	0.57925 (10)	0.45598 (3)	0.0544 (3)
O5	0.36250 (10)	0.53244 (10)	0.33181 (4)	0.0583 (3)
N1	0.69568 (11)	0.54774 (10)	0.34503 (4)	0.0442 (3)
N2	0.38854 (12)	0.75608 (11)	0.34947 (4)	0.0496 (3)
C1	0.75775 (13)	0.57277 (12)	0.30565 (4)	0.0427 (3)
C2	0.69042 (14)	0.66317 (13)	0.26816 (4)	0.0469 (4)
C3	0.76040 (16)	0.69623 (15)	0.23289 (5)	0.0550 (5)
C4	0.89409 (16)	0.63559 (15)	0.23342 (5)	0.0552 (5)
C5	0.95712 (16)	0.54108 (15)	0.26855 (5)	0.0555 (4)
C6	0.88915 (15)	0.51206 (13)	0.30494 (5)	0.0501 (4)
C7	0.4928 (2)	0.8191 (2)	0.23834 (7)	0.0902 (8)
C8	1.0946 (2)	0.6237 (2)	0.19742 (7)	0.0877 (8)
C9	0.73437 (14)	0.45600 (13)	0.38230 (5)	0.0479 (4)
C10	0.65669 (14)	0.53296 (13)	0.41431 (4)	0.0478 (4)
C11	0.60872 (13)	0.63263 (12)	0.36927 (4)	0.0427 (3)
C12	0.64376 (13)	0.77630 (13)	0.37747 (4)	0.0443 (4)
C13	0.50926 (14)	0.84504 (13)	0.36617 (5)	0.0481 (4)
C14	0.50455 (17)	0.98114 (14)	0.36987 (6)	0.0620 (5)
C15	0.64002 (19)	1.04751 (15)	0.38574 (6)	0.0672 (6)
C16	0.77351 (17)	0.98085 (15)	0.39705 (6)	0.0623 (5)
C17	0.77726 (15)	0.84352 (14)	0.39294 (5)	0.0527 (4)
C18	0.43872 (14)	0.63018 (13)	0.34634 (4)	0.0453 (4)
C19	0.23167 (15)	0.79080 (15)	0.34186 (5)	0.0564 (4)
C20	0.19641 (14)	0.80358 (14)	0.39054 (5)	0.0531 (4)
C21	0.18966 (17)	0.92623 (16)	0.41186 (7)	0.0661 (5)
C22	0.1649 (2)	0.93601 (19)	0.45779 (7)	0.0764 (6)
C23	0.14289 (19)	0.8231 (2)	0.48240 (7)	0.0743 (6)
C24	0.14658 (18)	0.70103 (18)	0.46115 (6)	0.0689 (6)
C25	0.17384 (16)	0.69098 (15)	0.41587 (6)	0.0600 (5)
C26	0.72311 (15)	0.63499 (13)	0.49433 (5)	0.0494 (4)
C27	0.58004 (17)	0.67325 (16)	0.49109 (5)	0.0612 (5)
C28	0.54888 (19)	0.72269 (17)	0.53283 (6)	0.0695 (6)
C29	0.6591 (2)	0.73257 (17)	0.57692 (6)	0.0709 (6)
C30	0.8030 (2)	0.69784 (16)	0.57925 (6)	0.0682 (5)
C31	0.83645 (17)	0.64991 (14)	0.53810 (5)	0.0580 (4)
H3	0.71800	0.75910	0.20880	0.0660*
H5	1.04400	0.49740	0.26790	0.0670*
H6	0.93310	0.45040	0.32940	0.0600*
H7A	0.47170	0.79190	0.20440	0.1080*
H7B	0.56170	0.89210	0.24450	0.1080*
H7C	0.40180	0.84630	0.24480	0.1080*
H8A	1.08640	0.52940	0.19270	0.1050*
H8B	1.16640	0.64290	0.22870	0.1050*
H8C	1.12640	0.66320	0.17120	0.1050*
H10	0.57390	0.48590	0.42170	0.0570*
H14	0.41430	1.02670	0.36200	0.0740*
H15	0.64030	1.13940	0.38880	0.0810*
H16	0.86250	1.02810	0.40760	0.0750*
H17	0.86770	0.79820	0.40040	0.0630*
H19A	0.16860	0.72290	0.32190	0.0680*
H19B	0.21010	0.87410	0.32400	0.0680*
H21	0.20190	1.00300	0.39510	0.0790*
H22	0.16310	1.01890	0.47210	0.0920*
H23	0.12570	0.82960	0.51320	0.0890*
H24	0.13060	0.62470	0.47740	0.0830*
H25	0.17720	0.60770	0.40200	0.0720*
H27	0.50490	0.66610	0.46120	0.0730*
H28	0.45220	0.74940	0.53090	0.0830*
H29	0.63660	0.76260	0.60510	0.0850*
H30	0.87840	0.70690	0.60890	0.0820*
H31	0.93420	0.62780	0.53970	0.0700*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0800 (8)	0.1029 (9)	0.0666 (7)	0.0120 (7)	0.0429 (6)	0.0176 (6)
O2	0.0524 (5)	0.0734 (7)	0.0540 (5)	0.0198 (5)	0.0172 (4)	0.0191 (5)
O3	0.0726 (6)	0.0502 (6)	0.0650 (6)	0.0150 (5)	0.0222 (5)	0.0123 (4)
O4	0.0477 (5)	0.0716 (6)	0.0419 (5)	0.0029 (4)	0.0099 (4)	0.0010 (4)
O5	0.0511 (5)	0.0541 (6)	0.0667 (6)	−0.0073 (4)	0.0123 (4)	−0.0100 (5)
N1	0.0462 (5)	0.0439 (5)	0.0435 (5)	0.0057 (4)	0.0146 (4)	0.0040 (4)
N2	0.0397 (5)	0.0485 (6)	0.0591 (6)	0.0021 (5)	0.0120 (5)	−0.0014 (5)
C1	0.0437 (6)	0.0441 (6)	0.0398 (6)	−0.0016 (5)	0.0111 (5)	−0.0011 (5)
C2	0.0446 (6)	0.0526 (7)	0.0422 (6)	0.0033 (5)	0.0105 (5)	0.0001 (5)
C3	0.0579 (8)	0.0640 (9)	0.0433 (7)	0.0039 (7)	0.0148 (6)	0.0083 (6)
C4	0.0568 (8)	0.0668 (9)	0.0457 (7)	−0.0028 (7)	0.0208 (6)	−0.0013 (6)
C5	0.0499 (7)	0.0625 (8)	0.0571 (8)	0.0037 (6)	0.0204 (6)	−0.0031 (6)
C6	0.0490 (7)	0.0521 (7)	0.0483 (7)	0.0047 (6)	0.0126 (5)	0.0036 (6)
C7	0.0831 (12)	0.1040 (15)	0.0881 (12)	0.0444 (11)	0.0323 (10)	0.0472 (11)
C8	0.0815 (12)	0.1158 (16)	0.0823 (12)	0.0073 (11)	0.0500 (10)	0.0075 (11)
C9	0.0495 (7)	0.0447 (7)	0.0481 (7)	0.0010 (6)	0.0118 (5)	0.0049 (5)
C10	0.0472 (7)	0.0515 (7)	0.0434 (6)	−0.0008 (6)	0.0112 (5)	0.0045 (5)
C11	0.0424 (6)	0.0445 (6)	0.0413 (6)	0.0018 (5)	0.0124 (5)	0.0006 (5)
C12	0.0438 (6)	0.0462 (7)	0.0433 (6)	0.0001 (5)	0.0131 (5)	0.0004 (5)
C13	0.0462 (7)	0.0462 (7)	0.0534 (7)	−0.0007 (5)	0.0168 (5)	0.0003 (5)
C14	0.0580 (8)	0.0474 (8)	0.0835 (10)	0.0049 (6)	0.0250 (7)	0.0001 (7)
C15	0.0722 (10)	0.0463 (8)	0.0896 (11)	−0.0079 (7)	0.0338 (9)	−0.0055 (7)
C16	0.0567 (8)	0.0584 (9)	0.0746 (10)	−0.0143 (7)	0.0235 (7)	−0.0095 (7)
C17	0.0458 (7)	0.0568 (8)	0.0563 (7)	−0.0041 (6)	0.0162 (6)	−0.0034 (6)
C18	0.0448 (6)	0.0478 (7)	0.0430 (6)	−0.0002 (5)	0.0124 (5)	−0.0010 (5)
C19	0.0410 (7)	0.0602 (8)	0.0642 (8)	0.0062 (6)	0.0091 (6)	0.0021 (7)
C20	0.0367 (6)	0.0543 (8)	0.0663 (8)	0.0034 (5)	0.0119 (6)	−0.0021 (6)
C21	0.0583 (8)	0.0557 (9)	0.0875 (11)	−0.0012 (7)	0.0260 (8)	−0.0057 (8)
C22	0.0713 (10)	0.0709 (11)	0.0906 (12)	−0.0057 (8)	0.0290 (9)	−0.0259 (9)
C23	0.0659 (10)	0.0896 (13)	0.0681 (10)	0.0022 (9)	0.0207 (8)	−0.0080 (9)
C24	0.0636 (9)	0.0708 (10)	0.0734 (10)	0.0080 (8)	0.0214 (8)	0.0089 (8)
C25	0.0528 (8)	0.0527 (8)	0.0746 (9)	0.0056 (6)	0.0185 (7)	0.0003 (7)
C26	0.0550 (7)	0.0491 (7)	0.0430 (6)	0.0016 (6)	0.0127 (5)	0.0050 (5)
C27	0.0543 (8)	0.0751 (10)	0.0517 (7)	0.0049 (7)	0.0116 (6)	0.0020 (7)
C28	0.0687 (10)	0.0733 (10)	0.0703 (10)	0.0088 (8)	0.0263 (8)	−0.0039 (8)
C29	0.0945 (12)	0.0630 (9)	0.0579 (9)	0.0041 (9)	0.0264 (8)	−0.0088 (7)
C30	0.0828 (11)	0.0607 (9)	0.0510 (8)	0.0063 (8)	0.0036 (7)	−0.0058 (7)
C31	0.0578 (8)	0.0565 (8)	0.0524 (7)	0.0035 (6)	0.0044 (6)	−0.0003 (6)

Geometric parameters (Å, º)

O1—C4	1.3671 (19)	C23—C24	1.373 (3)
O1—C8	1.414 (2)	C24—C25	1.376 (2)
O2—C2	1.3601 (17)	C26—C27	1.370 (2)
O2—C7	1.415 (2)	C26—C31	1.383 (2)
O3—C9	1.2083 (17)	C27—C28	1.385 (2)
O4—C10	1.4015 (15)	C28—C29	1.370 (2)
O4—C26	1.3836 (16)	C29—C30	1.374 (3)
O5—C18	1.2154 (16)	C30—C31	1.374 (2)
N1—C1	1.4166 (16)	C3—H3	0.9300
N1—C9	1.3673 (17)	C5—H5	0.9300
N1—C11	1.4774 (16)	C6—H6	0.9300
N2—C13	1.4116 (18)	C7—H7A	0.9600
N2—C18	1.3645 (17)	C7—H7B	0.9600
N2—C19	1.4627 (19)	C7—H7C	0.9600
C1—C2	1.3993 (17)	C8—H8A	0.9600
C1—C6	1.3784 (19)	C8—H8B	0.9600
C2—C3	1.3804 (19)	C8—H8C	0.9600
C3—C4	1.388 (2)	C10—H10	0.9800
C4—C5	1.378 (2)	C14—H14	0.9300
C5—C6	1.386 (2)	C15—H15	0.9300
C9—C10	1.5244 (18)	C16—H16	0.9300
C10—C11	1.5788 (16)	C17—H17	0.9300
C11—C12	1.4877 (18)	C19—H19A	0.9700
C11—C18	1.5336 (18)	C19—H19B	0.9700
C12—C13	1.3901 (19)	C21—H21	0.9300
C12—C17	1.3759 (19)	C22—H22	0.9300
C13—C14	1.3772 (19)	C23—H23	0.9300
C14—C15	1.388 (2)	C24—H24	0.9300
C15—C16	1.372 (2)	C25—H25	0.9300
C16—C17	1.390 (2)	C27—H27	0.9300
C19—C20	1.5071 (19)	C28—H28	0.9300
C20—C21	1.384 (2)	C29—H29	0.9300
C20—C25	1.389 (2)	C30—H30	0.9300
C21—C22	1.383 (3)	C31—H31	0.9300
C22—C23	1.379 (3)
O2···C11	2.8195 (14)	C19···H14	2.8900
O2···N1	2.7079 (14)	C21···H14	3.0200
O2···N2	3.1231 (15)	C22···H16^x	2.9200
O2···C18	2.8145 (15)	C23···H28	2.9200
O2···C12	2.9790 (14)	C23···H17^x	2.9300
O2···C13	3.1746 (16)	C24···H17^x	2.8500
O3···O4	3.0612 (14)	C24···H28	3.0000
O3···C6	3.0909 (18)	C25···H27	3.0000
O3···C31^i	3.3846 (19)	C25···H17^x	2.9700
O4···N1	3.0200 (14)	C26···H24^v	2.9500
O4···O3	3.0612 (14)	C27···H10	2.7100
O4···C17	3.2181 (17)	C28···H10^v	2.8700
O5···N1	3.0338 (15)	C29···H21^xi	2.9700
O1···H30^ii	2.6500	C31···H24^v	2.8300
O3···H15^iii	2.6800	H3···C7	2.5500
O3···H31^i	2.6800	H3···H7A	2.3000
O3···H6	2.4700	H3···H7B	2.4100
O3···H8C^iv	2.7300	H5···C8	2.5200
O4···H24^v	2.7600	H5···H8A	2.2900
O5···H10	2.7700	H5···H8B	2.3300
O5···H19A	2.6000	H6···O3	2.4700
O5···H7B^vi	2.8300	H6···C9	2.7000
N1···O2	2.7079 (14)	H7A···C3	2.7600
N1···O4	3.0200 (14)	H7A···H3	2.3000
N1···O5	3.0338 (15)	H7B···C3	2.7900
N1···C7^vi	3.397 (2)	H7B···H3	2.4100
N2···O2	3.1231 (15)	H7B···O5^vii	2.8300
C1···C7^vi	3.447 (2)	H7C···C1^vii	2.8700
C2···C12	3.4303 (16)	H8A···C5	2.7500
C6···O3	3.0909 (18)	H8A···H5	2.2900
C7···N1^vii	3.397 (2)	H8B···C5	2.7200
C7···C13	3.572 (2)	H8B···H5	2.3300
C7···C1^vii	3.447 (2)	H8C···O3^viii	2.7300
C8···C16^iv	3.549 (3)	H8C···C16^iv	3.0000
C11···C27	3.5453 (18)	H10···O5	2.7700
C11···O2	2.8195 (14)	H10···C27	2.7100
C12···C26	3.4665 (18)	H10···H27	2.3200
C12···C2	3.4303 (16)	H10···C28^v	2.8700
C12···C27	3.5779 (18)	H14···C19	2.8900
C12···O2	2.9790 (14)	H14···C21	3.0200
C13···O2	3.1746 (16)	H14···H19B	2.4400
C13···C7	3.572 (2)	H14···H21	2.4400
C14···C21	3.522 (2)	H14···H29^xi	2.4200
C14···C20	3.581 (2)	H15···O3^xii	2.6800
C16···C8^viii	3.549 (3)	H16···C22^ix	2.9200
C16···C22^ix	3.593 (3)	H17···C23^ix	2.9300
C17···O4	3.2181 (17)	H17···C24^ix	2.8500
C18···O2	2.8145 (15)	H17···C25^ix	2.9700
C20···C14	3.581 (2)	H19A···O5	2.6000
C21···C14	3.522 (2)	H19A···C5^x	2.7900
C22···C16^x	3.593 (3)	H19A···H25	2.5200
C24···C31^v	3.540 (2)	H19B···C14	2.8900
C26···C12	3.4665 (18)	H19B···H14	2.4400
C27···C12	3.5779 (18)	H19B···H21	2.4100
C27···C11	3.5453 (18)	H19B···C4^vii	3.1000
C31···C24^v	3.540 (2)	H21···H14	2.4400
C31···O3^i	3.3846 (19)	H21···H19B	2.4100
C1···H7C^vi	2.8700	H21···C29^xi	2.9700
C3···H7A	2.7600	H23···C16^xi	3.0900
C3···H7B	2.7900	H24···O4^v	2.7600
C4···H19B^vi	3.1000	H24···C26^v	2.9500
C5···H8A	2.7500	H24···C31^v	2.8300
C5···H8B	2.7200	H25···H19A	2.5200
C5···H19A^ix	2.7900	H27···C10	2.5800
C7···H3	2.5500	H27···C11	3.0400
C8···H5	2.5200	H27···C25	3.0000
C9···H6	2.7000	H27···H10	2.3200
C10···H27	2.5800	H28···C23	2.9200
C11···H27	3.0400	H28···C24	3.0000
C14···H19B	2.8900	H29···C14^xi	3.0700
C14···H29^xi	3.0700	H29···H14^xi	2.4200
C16···H23^xi	3.0900	H30···O1^xiii	2.6500
C16···H8C^viii	3.0000	H31···O3^i	2.6800
C4—O1—C8	117.72 (13)	C27—C28—C29	120.61 (17)
C2—O2—C7	118.57 (12)	C28—C29—C30	119.64 (16)
C10—O4—C26	118.37 (11)	C29—C30—C31	120.59 (16)
C1—N1—C9	130.19 (11)	C26—C31—C30	119.25 (15)
C1—N1—C11	131.68 (10)	C2—C3—H3	120.00
C9—N1—C11	95.44 (10)	C4—C3—H3	120.00
C13—N2—C18	110.80 (11)	C4—C5—H5	121.00
C13—N2—C19	124.66 (11)	C6—C5—H5	120.00
C18—N2—C19	124.21 (12)	C1—C6—H6	119.00
N1—C1—C2	120.72 (11)	C5—C6—H6	119.00
N1—C1—C6	120.14 (11)	O2—C7—H7A	109.00
C2—C1—C6	119.09 (11)	O2—C7—H7B	110.00
O2—C2—C1	115.28 (11)	O2—C7—H7C	109.00
O2—C2—C3	124.87 (12)	H7A—C7—H7B	109.00
C1—C2—C3	119.84 (13)	H7A—C7—H7C	109.00
C2—C3—C4	119.99 (13)	H7B—C7—H7C	109.00
O1—C4—C3	115.14 (13)	O1—C8—H8A	109.00
O1—C4—C5	124.28 (14)	O1—C8—H8B	109.00
C3—C4—C5	120.59 (14)	O1—C8—H8C	109.00
C4—C5—C6	119.05 (14)	H8A—C8—H8B	109.00
C1—C6—C5	121.30 (12)	H8A—C8—H8C	110.00
O3—C9—N1	132.69 (13)	H8B—C8—H8C	109.00
O3—C9—C10	134.66 (13)	O4—C10—H10	115.00
N1—C9—C10	92.61 (10)	C9—C10—H10	115.00
O4—C10—C9	107.63 (11)	C11—C10—H10	115.00
O4—C10—C11	115.55 (10)	C13—C14—H14	121.00
C9—C10—C11	85.45 (9)	C15—C14—H14	121.00
N1—C11—C10	86.41 (9)	C14—C15—H15	119.00
N1—C11—C12	120.62 (10)	C16—C15—H15	119.00
N1—C11—C18	116.00 (10)	C15—C16—H16	120.00
C10—C11—C12	119.72 (9)	C17—C16—H16	120.00
C10—C11—C18	110.32 (10)	C12—C17—H17	121.00
C12—C11—C18	103.65 (10)	C16—C17—H17	121.00
C11—C12—C13	107.78 (11)	N2—C19—H19A	109.00
C11—C12—C17	131.86 (12)	N2—C19—H19B	109.00
C13—C12—C17	120.36 (12)	C20—C19—H19A	109.00
N2—C13—C12	110.09 (11)	C20—C19—H19B	109.00
N2—C13—C14	128.15 (13)	H19A—C19—H19B	108.00
C12—C13—C14	121.71 (13)	C20—C21—H21	120.00
C13—C14—C15	117.27 (14)	C22—C21—H21	120.00
C14—C15—C16	121.59 (14)	C21—C22—H22	120.00
C15—C16—C17	120.76 (15)	C23—C22—H22	120.00
C12—C17—C16	118.30 (13)	C22—C23—H23	120.00
O5—C18—N2	126.59 (13)	C24—C23—H23	120.00
O5—C18—C11	126.20 (12)	C23—C24—H24	120.00
N2—C18—C11	106.97 (11)	C25—C24—H24	120.00
N2—C19—C20	111.21 (11)	C20—C25—H25	119.00
C19—C20—C21	121.43 (13)	C24—C25—H25	120.00
C19—C20—C25	120.29 (13)	C26—C27—H27	120.00
C21—C20—C25	118.26 (14)	C28—C27—H27	121.00
C20—C21—C22	120.75 (16)	C27—C28—H28	120.00
C21—C22—C23	120.14 (17)	C29—C28—H28	120.00
C22—C23—C24	119.57 (17)	C28—C29—H29	120.00
C23—C24—C25	120.37 (16)	C30—C29—H29	120.00
C20—C25—C24	120.89 (15)	C29—C30—H30	120.00
O4—C26—C27	124.70 (12)	C31—C30—H30	120.00
O4—C26—C31	114.60 (13)	C26—C31—H31	120.00
C27—C26—C31	120.71 (13)	C30—C31—H31	120.00
C26—C27—C28	119.12 (14)
C8—O1—C4—C3	176.41 (14)	N1—C9—C10—O4	−113.01 (11)
C8—O1—C4—C5	−4.0 (2)	C9—C10—C11—C12	−125.69 (12)
C7—O2—C2—C1	169.83 (13)	C9—C10—C11—C18	114.23 (10)
C7—O2—C2—C3	−10.5 (2)	O4—C10—C11—N1	105.18 (11)
C26—O4—C10—C11	96.20 (13)	C9—C10—C11—N1	−2.20 (9)
C10—O4—C26—C27	−13.86 (19)	O4—C10—C11—C18	−138.39 (11)
C10—O4—C26—C31	165.82 (12)	O4—C10—C11—C12	−18.31 (17)
C26—O4—C10—C9	−170.38 (11)	C10—C11—C18—O5	−53.77 (16)
C9—N1—C11—C18	−108.43 (11)	C12—C11—C18—O5	176.89 (12)
C1—N1—C11—C18	89.26 (15)	N1—C11—C18—N2	−142.96 (10)
C9—N1—C11—C10	2.45 (10)	C12—C11—C18—N2	−8.40 (12)
C11—N1—C9—C10	−2.54 (10)	N1—C11—C12—C13	138.12 (11)
C11—N1—C1—C2	−30.17 (19)	C10—C11—C12—C13	−117.16 (12)
C1—N1—C11—C12	−37.17 (18)	C18—C11—C12—C17	−173.55 (13)
C1—N1—C11—C10	−159.85 (13)	N1—C11—C18—O5	42.33 (17)
C11—N1—C1—C6	147.17 (13)	C10—C11—C12—C17	63.08 (18)
C1—N1—C9—C10	160.18 (12)	N1—C11—C12—C17	−41.64 (18)
C9—N1—C11—C12	125.14 (11)	C10—C11—C18—N2	120.94 (11)
C9—N1—C1—C6	−9.5 (2)	C18—C11—C12—C13	6.21 (12)
C11—N1—C9—O3	179.69 (16)	C13—C12—C17—C16	0.23 (19)
C9—N1—C1—C2	173.16 (13)	C17—C12—C13—C14	0.1 (2)
C1—N1—C9—O3	−17.6 (2)	C17—C12—C13—N2	177.78 (11)
C18—N2—C19—C20	97.83 (14)	C11—C12—C17—C16	179.97 (12)
C19—N2—C13—C14	−12.7 (2)	C11—C12—C13—N2	−2.01 (14)
C13—N2—C19—C20	−74.98 (16)	C11—C12—C13—C14	−179.65 (13)
C19—N2—C18—O5	8.6 (2)	C12—C13—C14—C15	−0.4 (2)
C18—N2—C13—C14	173.70 (14)	N2—C13—C14—C15	−177.62 (14)
C19—N2—C13—C12	169.89 (11)	C13—C14—C15—C16	0.4 (2)
C13—N2—C18—O5	−177.69 (12)	C14—C15—C16—C17	0.0 (3)
C19—N2—C18—C11	−166.05 (11)	C15—C16—C17—C12	−0.3 (2)
C13—N2—C18—C11	7.63 (13)	N2—C19—C20—C25	−78.69 (17)
C18—N2—C13—C12	−3.75 (15)	N2—C19—C20—C21	99.51 (16)
C6—C1—C2—O2	175.79 (11)	C21—C20—C25—C24	−0.5 (2)
N1—C1—C6—C5	−175.93 (12)	C19—C20—C21—C22	−176.59 (15)
C2—C1—C6—C5	1.5 (2)	C19—C20—C25—C24	177.78 (14)
N1—C1—C2—O2	−6.85 (17)	C25—C20—C21—C22	1.6 (2)
N1—C1—C2—C3	173.51 (12)	C20—C21—C22—C23	−1.6 (3)
C6—C1—C2—C3	−3.86 (19)	C21—C22—C23—C24	0.4 (3)
O2—C2—C3—C4	−176.86 (13)	C22—C23—C24—C25	0.8 (3)
C1—C2—C3—C4	2.8 (2)	C23—C24—C25—C20	−0.7 (3)
C2—C3—C4—C5	0.8 (2)	C27—C26—C31—C30	3.1 (2)
C2—C3—C4—O1	−179.61 (13)	O4—C26—C31—C30	−176.60 (13)
C3—C4—C5—C6	−3.2 (2)	C31—C26—C27—C28	−2.4 (2)
O1—C4—C5—C6	177.25 (14)	O4—C26—C27—C28	177.27 (14)
C4—C5—C6—C1	2.1 (2)	C26—C27—C28—C29	−0.4 (2)
O3—C9—C10—O4	64.7 (2)	C27—C28—C29—C30	2.5 (3)
N1—C9—C10—C11	2.37 (10)	C28—C29—C30—C31	−1.8 (3)
O3—C9—C10—C11	−179.93 (17)	C29—C30—C31—C26	−1.0 (2)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x, y−1, z; (iv) −x+2, y−1/2, −z+1/2; (v) −x+1, −y+1, −z+1; (vi) −x+1, y−1/2, −z+1/2; (vii) −x+1, y+1/2, −z+1/2; (viii) −x+2, y+1/2, −z+1/2; (ix) x+1, y, z; (x) x−1, y, z; (xi) −x+1, −y+2, −z+1; (xii) x, y+1, z; (xiii) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3	0.93	2.47	3.0909 (18)	124
C19—H19A···O5	0.97	2.60	2.9254 (18)	100