1-[3-(Morpholin-4-yl)prop-yl]-4-(3-nitro-phen-yl)spiro-[azetidine-3,9'-xanthen]-2-one.

The β-lactam (azetidin-2-one) ring of the title compound, C28H27N3O5, is nearly planar [maximum deviation = 0.010 (1) Å] and makes dihedral angles of 75.77 (5), 52.78 (9) and 88.72 (5)°, respectively, with the benzene ring, the least-squares plane formed by the four C atoms of the morpholine ring, which adopts a chair conformation, and the xanthene ring system. In the crystal, C-H⋯O hydrogen-bond contacts connect neighbouring mol-ecules into infinite zigzag chains running parallel to the b axis.

Related literature

For general background to β-lactams, see: Arumugam et al. (2011 ▶); Jarrahpour et al. (2010 ▶); Chrysselis et al. (2000 ▶); Mehta et al. (2010 ▶); Singh (2003 ▶); Singh et al. (2011 ▶, 2014 ▶). For similar structures, see: Akkurt et al. (2008a ▶,b ▶); Yalçın et al. (2009 ▶); Çelik et al. (2009a ▶,b ▶). For geometric analysis, see: Cremer & Pople (1975 ▶); Nardelli (1995 ▶).

Experimental

Crystal data

C28H27N3O5

M = 485.53

Monoclinic,

a = 9.2637 (6) Å

b = 11.4091 (5) Å

c = 23.3310 (15) Å

β = 96.930 (5)°

V = 2447.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.55 × 0.38 × 0.22 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.957, T max = 0.983

19036 measured reflections

5393 independent reflections

3044 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.093

S = 0.88

5393 reflections

325 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.21 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681400419X/sj5392sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400419X/sj5392Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400419X/sj5392Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C28H27N3O5	F(000) = 1024
Mr = 485.53	Dx = 1.317 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 16797 reflections
a = 9.2637 (6) Å	θ = 1.8–27.6°
b = 11.4091 (5) Å	µ = 0.09 mm−1
c = 23.3310 (15) Å	T = 296 K
β = 96.930 (5)°	Block, light yellow
V = 2447.9 (2) Å3	0.55 × 0.38 × 0.22 mm
Z = 4

Stoe IPDS 2 diffractometer	5393 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3044 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.041
Detector resolution: 6.67 pixels mm-1	θmax = 27.2°, θmin = 1.8°
ω scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
Tmin = 0.957, Tmax = 0.983	l = −29→29
19036 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0457P)2] where P = (Fo2 + 2Fc2)/3
S = 0.88	(Δ/σ)max < 0.001
5393 reflections	Δρmax = 0.15 e Å−3
325 parameters	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.84675 (13)	0.41791 (9)	0.23520 (5)	0.0578 (4)
O2	0.49859 (13)	0.68567 (11)	0.32597 (5)	0.0642 (5)
O3	0.21884 (16)	0.55524 (13)	0.00379 (6)	0.0903 (6)
O4	0.39138 (19)	0.44168 (14)	0.03770 (8)	0.1073 (7)
O5	0.76395 (16)	0.93149 (14)	−0.03119 (7)	0.0914 (6)
N1	0.80288 (13)	0.58505 (10)	0.17769 (5)	0.0425 (4)
N2	0.33075 (18)	0.53649 (15)	0.03527 (6)	0.0641 (6)
N3	0.86873 (15)	0.81179 (12)	0.07346 (6)	0.0539 (5)
C1	0.78855 (17)	0.51133 (13)	0.22163 (6)	0.0424 (5)
C2	0.67968 (16)	0.59013 (12)	0.24776 (6)	0.0406 (5)
C3	0.69833 (16)	0.67310 (12)	0.19331 (6)	0.0405 (4)
C4	0.74121 (18)	0.64401 (13)	0.30441 (6)	0.0447 (5)
C5	0.88946 (19)	0.65055 (15)	0.32229 (7)	0.0566 (6)
C6	0.9422 (2)	0.70557 (18)	0.37322 (8)	0.0727 (7)
C7	0.8472 (3)	0.75553 (18)	0.40659 (8)	0.0746 (8)
C8	0.6998 (2)	0.74905 (16)	0.39060 (7)	0.0667 (7)
C9	0.64771 (19)	0.69209 (14)	0.33962 (7)	0.0512 (5)
C10	0.44594 (19)	0.59521 (15)	0.28968 (7)	0.0533 (6)
C11	0.3044 (2)	0.55984 (18)	0.29314 (9)	0.0704 (8)
C12	0.2471 (2)	0.4687 (2)	0.25963 (10)	0.0783 (8)
C13	0.3315 (2)	0.41067 (18)	0.22397 (9)	0.0729 (8)
C14	0.4725 (2)	0.44662 (15)	0.22061 (7)	0.0588 (6)
C15	0.53121 (18)	0.54190 (14)	0.25249 (6)	0.0465 (5)
C16	0.57100 (16)	0.69479 (13)	0.14871 (6)	0.0405 (4)
C17	0.50680 (17)	0.80495 (14)	0.14408 (6)	0.0484 (5)
C18	0.39007 (18)	0.82805 (15)	0.10310 (7)	0.0557 (6)
C19	0.33281 (18)	0.74088 (16)	0.06655 (7)	0.0535 (6)
C20	0.39514 (17)	0.63143 (14)	0.07194 (6)	0.0462 (5)
C21	0.51418 (17)	0.60747 (13)	0.11139 (6)	0.0454 (5)
C22	0.89002 (19)	0.57752 (15)	0.13018 (7)	0.0534 (6)
C23	1.0149 (2)	0.66323 (17)	0.13299 (8)	0.0672 (7)
C24	0.9716 (2)	0.79100 (17)	0.12441 (8)	0.0637 (7)
C25	0.8098 (3)	0.93061 (16)	0.07274 (10)	0.0799 (8)
C26	0.7015 (3)	0.9490 (2)	0.02030 (12)	0.0950 (10)
C27	0.8214 (2)	0.8171 (2)	−0.03121 (9)	0.0820 (8)
C28	0.9321 (2)	0.79517 (17)	0.02015 (7)	0.0643 (7)
H3	0.74730	0.74660	0.20560	0.0490*
H5	0.95440	0.61730	0.29950	0.0680*
H6	1.04170	0.70870	0.38480	0.0870*
H7	0.88280	0.79430	0.44040	0.0900*
H8	0.63560	0.78240	0.41360	0.0800*
H11	0.24860	0.59770	0.31810	0.0850*
H12	0.15120	0.44600	0.26090	0.0940*
H13	0.29340	0.34720	0.20210	0.0870*
H14	0.52900	0.40660	0.19670	0.0710*
H17	0.54320	0.86430	0.16910	0.0580*
H18	0.35000	0.90290	0.10020	0.0670*
H19	0.25390	0.75550	0.03890	0.0640*
H21	0.55610	0.53330	0.11300	0.0550*
H22A	0.82710	0.59030	0.09440	0.0640*
H22B	0.92870	0.49870	0.12900	0.0640*
H23A	1.07620	0.64180	0.10370	0.0810*
H23B	1.07290	0.65530	0.17030	0.0810*
H24A	0.92910	0.81780	0.15810	0.0760*
H24B	1.05830	0.83720	0.12160	0.0760*
H25A	0.88840	0.98680	0.07270	0.0960*
H25B	0.76320	0.94350	0.10730	0.0960*
H26A	0.62100	0.89510	0.02140	0.1140*
H26B	0.66330	1.02810	0.02080	0.1140*
H27A	0.86620	0.80520	−0.06630	0.0980*
H27B	0.74280	0.76090	−0.03110	0.0980*
H28A	0.96870	0.71570	0.01860	0.0770*
H28B	1.01330	0.84850	0.01920	0.0770*

	U11	U22	U33	U12	U13	U23
O1	0.0719 (8)	0.0442 (6)	0.0557 (6)	0.0105 (6)	0.0012 (6)	0.0086 (5)
O2	0.0646 (8)	0.0644 (8)	0.0658 (8)	−0.0010 (7)	0.0172 (6)	−0.0135 (6)
O3	0.0830 (10)	0.1006 (11)	0.0769 (9)	−0.0037 (8)	−0.0333 (8)	−0.0132 (8)
O4	0.1157 (13)	0.0641 (10)	0.1279 (13)	0.0029 (9)	−0.0430 (11)	−0.0246 (9)
O5	0.0794 (10)	0.0904 (11)	0.1034 (12)	0.0183 (9)	0.0075 (9)	0.0388 (9)
N1	0.0466 (7)	0.0417 (7)	0.0391 (6)	0.0052 (6)	0.0044 (6)	0.0046 (6)
N2	0.0675 (10)	0.0654 (10)	0.0551 (9)	−0.0072 (8)	−0.0104 (8)	−0.0034 (8)
N3	0.0539 (8)	0.0478 (8)	0.0602 (8)	0.0011 (7)	0.0082 (7)	0.0008 (7)
C1	0.0474 (9)	0.0388 (8)	0.0382 (8)	−0.0011 (7)	−0.0061 (7)	0.0026 (7)
C2	0.0480 (9)	0.0383 (8)	0.0347 (7)	−0.0009 (7)	0.0023 (6)	0.0033 (6)
C3	0.0447 (8)	0.0374 (8)	0.0386 (7)	−0.0003 (7)	0.0022 (6)	0.0009 (6)
C4	0.0565 (10)	0.0429 (8)	0.0339 (7)	−0.0037 (8)	0.0020 (7)	0.0043 (6)
C5	0.0568 (11)	0.0641 (11)	0.0469 (9)	−0.0088 (9)	−0.0017 (8)	0.0006 (8)
C6	0.0737 (13)	0.0866 (14)	0.0534 (10)	−0.0198 (12)	−0.0102 (10)	−0.0017 (10)
C7	0.0998 (17)	0.0782 (14)	0.0435 (10)	−0.0289 (12)	−0.0012 (11)	−0.0078 (9)
C8	0.0974 (16)	0.0619 (11)	0.0433 (9)	−0.0142 (11)	0.0190 (10)	−0.0082 (8)
C9	0.0609 (11)	0.0491 (9)	0.0438 (8)	−0.0065 (8)	0.0076 (8)	0.0029 (8)
C10	0.0532 (10)	0.0551 (10)	0.0514 (9)	−0.0036 (9)	0.0054 (8)	0.0052 (8)
C11	0.0551 (12)	0.0800 (14)	0.0777 (13)	−0.0019 (10)	0.0146 (10)	0.0084 (11)
C12	0.0570 (12)	0.0886 (15)	0.0886 (15)	−0.0207 (12)	0.0055 (11)	0.0157 (13)
C13	0.0721 (14)	0.0705 (13)	0.0738 (13)	−0.0266 (11)	0.0000 (11)	0.0004 (11)
C14	0.0647 (12)	0.0560 (10)	0.0551 (10)	−0.0142 (9)	0.0045 (9)	−0.0001 (8)
C15	0.0517 (10)	0.0458 (9)	0.0407 (8)	−0.0045 (8)	0.0009 (7)	0.0075 (7)
C16	0.0445 (8)	0.0419 (8)	0.0353 (7)	0.0014 (7)	0.0053 (6)	0.0033 (7)
C17	0.0565 (10)	0.0451 (9)	0.0433 (8)	0.0069 (8)	0.0045 (8)	−0.0021 (7)
C18	0.0584 (11)	0.0520 (10)	0.0556 (10)	0.0184 (8)	0.0020 (8)	0.0012 (8)
C19	0.0456 (9)	0.0694 (11)	0.0444 (9)	0.0093 (9)	0.0005 (8)	0.0059 (8)
C20	0.0476 (9)	0.0521 (9)	0.0385 (8)	−0.0022 (8)	0.0031 (7)	0.0006 (7)
C21	0.0517 (9)	0.0416 (9)	0.0420 (8)	0.0032 (7)	0.0015 (7)	0.0038 (7)
C22	0.0622 (11)	0.0526 (10)	0.0472 (9)	0.0087 (9)	0.0145 (8)	0.0023 (8)
C23	0.0517 (10)	0.0897 (15)	0.0603 (11)	0.0010 (10)	0.0072 (9)	0.0204 (10)
C24	0.0626 (12)	0.0716 (12)	0.0571 (10)	−0.0203 (10)	0.0085 (9)	0.0010 (9)
C25	0.0907 (15)	0.0502 (11)	0.1043 (16)	0.0055 (11)	0.0337 (14)	−0.0014 (11)
C26	0.0768 (15)	0.0736 (15)	0.136 (2)	0.0262 (12)	0.0188 (16)	0.0281 (15)
C27	0.0839 (15)	0.0882 (16)	0.0705 (13)	0.0121 (12)	−0.0048 (11)	0.0079 (12)
C28	0.0641 (12)	0.0697 (12)	0.0586 (10)	0.0146 (10)	0.0059 (9)	0.0062 (9)

O1—C1	1.2189 (18)	C18—C19	1.374 (2)
O2—C9	1.382 (2)	C19—C20	1.375 (2)
O2—C10	1.386 (2)	C20—C21	1.376 (2)
O3—N2	1.215 (2)	C22—C23	1.510 (3)
O4—N2	1.217 (2)	C23—C24	1.519 (3)
O5—C26	1.409 (3)	C25—C26	1.500 (4)
O5—C27	1.410 (3)	C27—C28	1.501 (3)
N1—C1	1.3449 (18)	C3—H3	0.9800
N1—C3	1.4715 (19)	C5—H5	0.9300
N1—C22	1.450 (2)	C6—H6	0.9300
N2—C20	1.462 (2)	C7—H7	0.9300
N3—C24	1.451 (2)	C8—H8	0.9300
N3—C25	1.461 (2)	C11—H11	0.9300
N3—C28	1.450 (2)	C12—H12	0.9300
C1—C2	1.532 (2)	C13—H13	0.9300
C2—C3	1.610 (2)	C14—H14	0.9300
C2—C4	1.506 (2)	C17—H17	0.9300
C2—C15	1.498 (2)	C18—H18	0.9300
C3—C16	1.496 (2)	C19—H19	0.9300
C4—C5	1.388 (2)	C21—H21	0.9300
C4—C9	1.378 (2)	C22—H22A	0.9700
C5—C6	1.380 (3)	C22—H22B	0.9700
C6—C7	1.368 (3)	C23—H23A	0.9700
C7—C8	1.373 (3)	C23—H23B	0.9700
C8—C9	1.390 (2)	C24—H24A	0.9700
C10—C11	1.384 (3)	C24—H24B	0.9700
C10—C15	1.383 (2)	C25—H25A	0.9700
C11—C12	1.369 (3)	C25—H25B	0.9700
C12—C13	1.378 (3)	C26—H26A	0.9700
C13—C14	1.380 (3)	C26—H26B	0.9700
C14—C15	1.390 (2)	C27—H27A	0.9700
C16—C17	1.389 (2)	C27—H27B	0.9700
C16—C21	1.385 (2)	C28—H28A	0.9700
C17—C18	1.380 (2)	C28—H28B	0.9700
C9—O2—C10	116.66 (13)	C2—C3—H3	111.00
C26—O5—C27	108.99 (17)	C16—C3—H3	111.00
C1—N1—C3	96.30 (11)	C4—C5—H5	119.00
C1—N1—C22	131.36 (13)	C6—C5—H5	119.00
C3—N1—C22	132.33 (12)	C5—C6—H6	120.00
O3—N2—O4	122.68 (17)	C7—C6—H6	120.00
O3—N2—C20	118.78 (16)	C6—C7—H7	120.00
O4—N2—C20	118.54 (16)	C8—C7—H7	120.00
C24—N3—C25	111.64 (15)	C7—C8—H8	120.00
C24—N3—C28	112.80 (14)	C9—C8—H8	120.00
C25—N3—C28	107.51 (15)	C10—C11—H11	120.00
O1—C1—N1	131.57 (14)	C12—C11—H11	120.00
O1—C1—C2	134.57 (14)	C11—C12—H12	120.00
N1—C1—C2	93.82 (11)	C13—C12—H12	120.00
C1—C2—C3	83.83 (10)	C12—C13—H13	120.00
C1—C2—C4	113.04 (12)	C14—C13—H13	120.00
C1—C2—C15	117.93 (12)	C13—C14—H14	120.00
C3—C2—C4	112.78 (11)	C15—C14—H14	120.00
C3—C2—C15	117.45 (12)	C16—C17—H17	119.00
C4—C2—C15	109.82 (12)	C18—C17—H17	119.00
N1—C3—C2	86.02 (10)	C17—C18—H18	120.00
N1—C3—C16	115.33 (12)	C19—C18—H18	120.00
C2—C3—C16	119.69 (12)	C18—C19—H19	121.00
C2—C4—C5	122.79 (14)	C20—C19—H19	121.00
C2—C4—C9	119.16 (15)	C16—C21—H21	120.00
C5—C4—C9	118.02 (14)	C20—C21—H21	120.00
C4—C5—C6	121.18 (16)	N1—C22—H22A	108.00
C5—C6—C7	119.63 (18)	N1—C22—H22B	109.00
C6—C7—C8	120.65 (18)	C23—C22—H22A	109.00
C7—C8—C9	119.26 (17)	C23—C22—H22B	109.00
O2—C9—C4	121.64 (14)	H22A—C22—H22B	108.00
O2—C9—C8	117.15 (15)	C22—C23—H23A	108.00
C4—C9—C8	121.21 (16)	C22—C23—H23B	108.00
O2—C10—C11	116.60 (16)	C24—C23—H23A	108.00
O2—C10—C15	121.69 (15)	C24—C23—H23B	108.00
C11—C10—C15	121.70 (16)	H23A—C23—H23B	107.00
C10—C11—C12	119.55 (18)	N3—C24—H24A	109.00
C11—C12—C13	120.04 (18)	N3—C24—H24B	109.00
C12—C13—C14	120.09 (18)	C23—C24—H24A	109.00
C13—C14—C15	120.91 (17)	C23—C24—H24B	109.00
C2—C15—C10	118.93 (14)	H24A—C24—H24B	108.00
C2—C15—C14	123.45 (14)	N3—C25—H25A	109.00
C10—C15—C14	117.61 (16)	N3—C25—H25B	110.00
C3—C16—C17	119.86 (13)	C26—C25—H25A	110.00
C3—C16—C21	121.75 (13)	C26—C25—H25B	110.00
C17—C16—C21	118.39 (13)	H25A—C25—H25B	108.00
C16—C17—C18	121.28 (14)	O5—C26—H26A	109.00
C17—C18—C19	120.22 (16)	O5—C26—H26B	109.00
C18—C19—C20	118.30 (15)	C25—C26—H26A	109.00
N2—C20—C19	118.82 (14)	C25—C26—H26B	109.00
N2—C20—C21	118.80 (14)	H26A—C26—H26B	108.00
C19—C20—C21	122.37 (14)	O5—C27—H27A	109.00
C16—C21—C20	119.40 (14)	O5—C27—H27B	109.00
N1—C22—C23	115.00 (14)	C28—C27—H27A	109.00
C22—C23—C24	115.28 (15)	C28—C27—H27B	109.00
N3—C24—C23	113.70 (15)	H27A—C27—H27B	108.00
N3—C25—C26	110.57 (17)	N3—C28—H28A	109.00
O5—C26—C25	111.9 (2)	N3—C28—H28B	109.00
O5—C27—C28	112.07 (17)	C27—C28—H28A	110.00
N3—C28—C27	110.76 (15)	C27—C28—H28B	110.00
N1—C3—H3	111.00	H28A—C28—H28B	108.00
C9—O2—C10—C11	155.89 (16)	C1—C2—C15—C14	−19.2 (2)
C10—O2—C9—C4	23.8 (2)	C15—C2—C3—N1	−119.59 (13)
C10—O2—C9—C8	−156.04 (15)	C1—C2—C15—C10	161.87 (14)
C9—O2—C10—C15	−23.2 (2)	C3—C2—C15—C14	78.76 (19)
C27—O5—C26—C25	57.9 (2)	C1—C2—C4—C9	−163.90 (14)
C26—O5—C27—C28	−57.7 (2)	C2—C3—C16—C17	110.27 (15)
C1—N1—C22—C23	−110.50 (18)	C2—C3—C16—C21	−69.70 (18)
C3—N1—C1—O1	−179.56 (17)	N1—C3—C16—C21	30.8 (2)
C22—N1—C1—C2	179.91 (15)	N1—C3—C16—C17	−149.28 (13)
C22—N1—C1—O1	1.9 (3)	C5—C4—C9—O2	−177.71 (14)
C3—N1—C1—C2	−1.50 (12)	C9—C4—C5—C6	−1.3 (2)
C3—N1—C22—C23	71.4 (2)	C2—C4—C5—C6	176.86 (16)
C1—N1—C3—C16	−119.66 (13)	C2—C4—C9—O2	4.1 (2)
C22—N1—C3—C2	180.00 (15)	C5—C4—C9—C8	2.2 (2)
C22—N1—C3—C16	58.9 (2)	C2—C4—C9—C8	−176.06 (15)
C1—N1—C3—C2	1.43 (11)	C4—C5—C6—C7	−0.6 (3)
O3—N2—C20—C21	174.10 (15)	C5—C6—C7—C8	1.6 (3)
O4—N2—C20—C19	175.60 (17)	C6—C7—C8—C9	−0.7 (3)
O4—N2—C20—C21	−5.7 (2)	C7—C8—C9—O2	178.67 (16)
O3—N2—C20—C19	−4.6 (2)	C7—C8—C9—C4	−1.2 (3)
C24—N3—C25—C26	−178.81 (18)	C11—C10—C15—C14	−3.4 (2)
C28—N3—C24—C23	−69.47 (19)	O2—C10—C15—C2	−5.3 (2)
C25—N3—C24—C23	169.34 (17)	C11—C10—C15—C2	175.60 (16)
C28—N3—C25—C26	57.0 (2)	C15—C10—C11—C12	0.9 (3)
C25—N3—C28—C27	−56.8 (2)	O2—C10—C11—C12	−178.17 (18)
C24—N3—C28—C27	179.73 (16)	O2—C10—C15—C14	175.66 (15)
O1—C1—C2—C15	−62.8 (2)	C10—C11—C12—C13	1.8 (3)
O1—C1—C2—C3	179.33 (19)	C11—C12—C13—C14	−2.0 (3)
O1—C1—C2—C4	67.2 (2)	C12—C13—C14—C15	−0.6 (3)
N1—C1—C2—C15	119.25 (13)	C13—C14—C15—C10	3.2 (2)
N1—C1—C2—C4	−110.79 (13)	C13—C14—C15—C2	−175.76 (16)
N1—C1—C2—C3	1.37 (11)	C21—C16—C17—C18	−0.6 (2)
C1—C2—C4—C5	18.0 (2)	C3—C16—C17—C18	179.44 (14)
C15—C2—C3—C16	−2.59 (19)	C3—C16—C21—C20	178.70 (14)
C4—C2—C15—C14	−150.62 (15)	C17—C16—C21—C20	−1.3 (2)
C15—C2—C4—C9	−29.94 (19)	C16—C17—C18—C19	1.4 (2)
C3—C2—C4—C9	103.12 (16)	C17—C18—C19—C20	−0.2 (2)
C15—C2—C4—C5	151.94 (15)	C18—C19—C20—C21	−1.7 (2)
C4—C2—C3—C16	−131.83 (14)	C18—C19—C20—N2	176.99 (15)
C3—C2—C15—C10	−100.18 (16)	C19—C20—C21—C16	2.5 (2)
C4—C2—C3—N1	111.17 (13)	N2—C20—C21—C16	−176.22 (14)
C1—C2—C3—C16	115.75 (13)	N1—C22—C23—C24	−68.6 (2)
C1—C2—C3—N1	−1.25 (10)	C22—C23—C24—N3	−50.6 (2)
C4—C2—C15—C10	30.44 (19)	N3—C25—C26—O5	−59.3 (2)
C3—C2—C4—C5	−75.00 (18)	O5—C27—C28—N3	59.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1i	0.93	2.42	3.2423 (19)	148
C22—H22A···N3	0.97	2.61	2.978 (2)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O1i	0.93	2.42	3.2423 (19)	148

Symmetry code: (i) .