6a-Nitro-6-phenyl-6,6a,6b,7,8,9,10,12a-octa-hydro-spiro-[chromeno[3,4-a]indol-izine-12,3'-indolin]-2'-one.

In the title compound, C28H25N3O4, the central pyrrolidine ring adopts adopts an envelope conformation with the N atom as the flap and the piperidine ring adopts a chair conformation. The pendant pyrrolidine ring is almost planar (r.m.s. deviation = 0.008 Å). An intra-molecular C-H⋯O inter-action closes an S(6) ring. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(8) loops.

Related literature

For biological background to 4H-chromene derivatives, see: Cai (2008 ▶); Valenti et al. (1993 ▶). For applications of indoline-2-one and its derivatives as precursors in the synthesis of pharmaceuticals, see: Colgan et al. (1996 ▶).

Experimental

Crystal data

C28H25N3O4

M = 467.51

Monoclinic,

a = 23.2940 (13) Å

b = 11.2517 (7) Å

c = 19.7702 (10) Å

β = 112.659 (3)°

V = 4781.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.974, T max = 0.983

20735 measured reflections

5804 independent reflections

3892 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.00

5804 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014062/hb7084sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014062/hb7084Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014062/hb7084Isup3.cml

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

C28H25N3O4	F(000) = 1968
Mr = 467.51	Dx = 1.299 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5804 reflections
a = 23.2940 (13) Å	θ = 1.9–28.3°
b = 11.2517 (7) Å	µ = 0.09 mm−1
c = 19.7702 (10) Å	T = 293 K
β = 112.659 (3)°	Block, colourless
V = 4781.8 (5) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	5804 independent reflections
Radiation source: fine-focus sealed tube	3892 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω and φ scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −30→27
Tmin = 0.974, Tmax = 0.983	k = −14→14
20735 measured reflections	l = −25→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0505P)2 + 2.441P] where P = (Fo2 + 2Fc2)/3
5804 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.85609 (7)	−0.07457 (14)	0.50076 (8)	0.0424 (4)
C2	0.86024 (10)	−0.05264 (18)	0.43391 (10)	0.0608 (5)
H2	0.8376	−0.0985	0.3932	0.073*
C3	0.89794 (11)	0.0370 (2)	0.42802 (12)	0.0740 (6)
H3	0.8998	0.0536	0.3828	0.089*
C4	0.93302 (11)	0.1027 (2)	0.48873 (12)	0.0725 (6)
H4	0.9592	0.1624	0.4848	0.087*
C5	0.92917 (8)	0.07964 (16)	0.55536 (10)	0.0530 (4)
H5	0.9531	0.1237	0.5963	0.064*
C6	0.89013 (7)	−0.00828 (13)	0.56210 (8)	0.0384 (3)
C7	0.88197 (6)	−0.02739 (12)	0.63324 (7)	0.0333 (3)
H7	0.9232	−0.0262	0.6731	0.040*
C8	0.85040 (7)	−0.14626 (12)	0.63696 (7)	0.0337 (3)
C9	0.83905 (7)	−0.23119 (13)	0.57169 (8)	0.0383 (3)
H9	0.8051	−0.2843	0.5699	0.046*
C10	0.89189 (7)	−0.30987 (14)	0.57303 (8)	0.0399 (4)
C11	0.95412 (8)	−0.27872 (16)	0.60526 (10)	0.0514 (4)
H11	0.9652	−0.2047	0.6274	0.062*
C12	0.99985 (9)	−0.35599 (18)	0.60498 (10)	0.0592 (5)
H12	1.0415	−0.3343	0.6271	0.071*
C13	0.98385 (11)	−0.46543 (19)	0.57194 (10)	0.0629 (5)
H13	1.0147	−0.5178	0.5718	0.075*
C14	0.92229 (11)	−0.49735 (17)	0.53910 (11)	0.0660 (6)
H14	0.9115	−0.5711	0.5165	0.079*
C15	0.87660 (9)	−0.42018 (15)	0.53967 (9)	0.0505 (4)
H15	0.8350	−0.4423	0.5174	0.061*
C16	0.78884 (7)	−0.11043 (13)	0.64328 (8)	0.0364 (3)
H16	0.7581	−0.0947	0.5938	0.044*
C17	0.75963 (8)	−0.19292 (15)	0.68128 (10)	0.0490 (4)
H17A	0.7892	−0.2104	0.7304	0.059*
H17B	0.7481	−0.2671	0.6544	0.059*
C18	0.70199 (9)	−0.13326 (17)	0.68491 (11)	0.0585 (5)
H18A	0.6715	−0.1204	0.6357	0.070*
H18B	0.6836	−0.1846	0.7105	0.070*
C19	0.71962 (9)	−0.01512 (18)	0.72468 (12)	0.0624 (5)
H19A	0.6825	0.0240	0.7248	0.075*
H19B	0.7474	−0.0288	0.7752	0.075*
C20	0.75132 (8)	0.06411 (15)	0.68767 (11)	0.0535 (4)
H20A	0.7221	0.0850	0.6390	0.064*
H20B	0.7650	0.1369	0.7156	0.064*
C21	0.84106 (6)	0.07028 (12)	0.64953 (7)	0.0335 (3)
C22	0.87723 (7)	0.17155 (12)	0.69677 (8)	0.0339 (3)
C23	0.92160 (7)	0.17261 (14)	0.76717 (8)	0.0420 (4)
H23	0.9341	0.1023	0.7935	0.050*
C24	0.94731 (8)	0.28065 (15)	0.79802 (9)	0.0476 (4)
H24	0.9772	0.2829	0.8456	0.057*
C25	0.92886 (8)	0.38464 (15)	0.75866 (9)	0.0460 (4)
H25	0.9469	0.4561	0.7801	0.055*
C26	0.88421 (7)	0.38502 (14)	0.68819 (9)	0.0422 (4)
H26	0.8716	0.4554	0.6619	0.051*
C27	0.85910 (7)	0.27729 (13)	0.65836 (8)	0.0359 (3)
C28	0.79893 (7)	0.13765 (13)	0.57914 (8)	0.0372 (3)
N1	0.88825 (6)	−0.21232 (12)	0.70783 (7)	0.0411 (3)
N2	0.80488 (6)	0.00268 (11)	0.68254 (7)	0.0375 (3)
N3	0.81272 (6)	0.25411 (11)	0.58899 (7)	0.0435 (3)
H3A	0.7953	0.3079	0.5567	0.052*
O1	0.81579 (5)	−0.16138 (10)	0.50491 (5)	0.0439 (3)
O2	0.92442 (6)	−0.15660 (11)	0.75982 (6)	0.0606 (4)
O3	0.87676 (6)	−0.31771 (10)	0.70992 (6)	0.0546 (3)
O4	0.75833 (5)	0.09239 (9)	0.52555 (6)	0.0476 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0445 (9)	0.0376 (9)	0.0414 (8)	−0.0021 (7)	0.0124 (7)	0.0040 (7)
C2	0.0756 (13)	0.0620 (12)	0.0431 (9)	−0.0079 (10)	0.0209 (9)	−0.0001 (9)
C3	0.1009 (17)	0.0740 (14)	0.0602 (12)	−0.0132 (13)	0.0456 (12)	0.0058 (11)
C4	0.0894 (15)	0.0648 (14)	0.0804 (14)	−0.0232 (12)	0.0516 (13)	0.0011 (11)
C5	0.0565 (11)	0.0469 (10)	0.0600 (10)	−0.0152 (8)	0.0272 (9)	−0.0037 (8)
C6	0.0386 (8)	0.0327 (8)	0.0425 (8)	−0.0006 (6)	0.0141 (7)	0.0027 (6)
C7	0.0309 (7)	0.0269 (7)	0.0351 (7)	−0.0028 (6)	0.0050 (6)	0.0011 (6)
C8	0.0346 (7)	0.0267 (7)	0.0340 (7)	−0.0007 (6)	0.0067 (6)	0.0034 (6)
C9	0.0416 (8)	0.0291 (7)	0.0381 (8)	−0.0055 (6)	0.0085 (7)	0.0004 (6)
C10	0.0484 (9)	0.0334 (8)	0.0350 (7)	−0.0005 (7)	0.0130 (7)	−0.0001 (6)
C11	0.0492 (10)	0.0438 (10)	0.0557 (10)	0.0023 (8)	0.0142 (8)	−0.0056 (8)
C12	0.0548 (11)	0.0661 (13)	0.0552 (10)	0.0120 (10)	0.0195 (9)	0.0024 (9)
C13	0.0809 (14)	0.0625 (13)	0.0500 (10)	0.0290 (11)	0.0305 (10)	0.0065 (9)
C14	0.1004 (17)	0.0413 (10)	0.0585 (11)	0.0087 (11)	0.0328 (12)	−0.0093 (9)
C15	0.0646 (11)	0.0389 (9)	0.0447 (9)	−0.0042 (8)	0.0175 (8)	−0.0054 (7)
C16	0.0354 (8)	0.0300 (8)	0.0397 (8)	−0.0029 (6)	0.0101 (6)	0.0021 (6)
C17	0.0516 (10)	0.0371 (9)	0.0606 (10)	−0.0074 (8)	0.0241 (9)	0.0033 (8)
C18	0.0541 (11)	0.0533 (11)	0.0776 (13)	−0.0084 (9)	0.0360 (10)	0.0040 (10)
C19	0.0634 (12)	0.0560 (12)	0.0832 (13)	−0.0019 (10)	0.0452 (11)	−0.0041 (10)
C20	0.0532 (10)	0.0387 (10)	0.0753 (12)	0.0009 (8)	0.0319 (9)	−0.0037 (8)
C21	0.0341 (7)	0.0262 (7)	0.0345 (7)	−0.0002 (6)	0.0068 (6)	0.0029 (6)
C22	0.0345 (7)	0.0273 (7)	0.0379 (7)	−0.0009 (6)	0.0117 (6)	−0.0001 (6)
C23	0.0423 (9)	0.0351 (8)	0.0399 (8)	0.0034 (7)	0.0063 (7)	0.0011 (6)
C24	0.0427 (9)	0.0447 (10)	0.0441 (9)	0.0005 (8)	0.0041 (7)	−0.0085 (7)
C25	0.0460 (9)	0.0358 (9)	0.0540 (9)	−0.0071 (7)	0.0167 (8)	−0.0114 (7)
C26	0.0504 (9)	0.0266 (8)	0.0491 (9)	−0.0019 (7)	0.0186 (8)	0.0004 (6)
C27	0.0371 (8)	0.0299 (8)	0.0377 (7)	−0.0014 (6)	0.0110 (6)	0.0011 (6)
C28	0.0361 (8)	0.0306 (8)	0.0394 (8)	0.0009 (6)	0.0085 (6)	0.0033 (6)
N1	0.0458 (7)	0.0324 (7)	0.0415 (7)	0.0043 (6)	0.0126 (6)	0.0043 (5)
N2	0.0387 (7)	0.0285 (6)	0.0452 (7)	−0.0016 (5)	0.0159 (6)	0.0010 (5)
N3	0.0499 (8)	0.0264 (7)	0.0408 (7)	0.0003 (6)	0.0026 (6)	0.0066 (5)
O1	0.0446 (6)	0.0399 (6)	0.0360 (5)	−0.0074 (5)	0.0030 (5)	0.0022 (4)
O2	0.0669 (8)	0.0510 (7)	0.0413 (6)	−0.0021 (6)	−0.0040 (6)	0.0037 (6)
O3	0.0733 (8)	0.0299 (6)	0.0580 (7)	0.0041 (6)	0.0225 (6)	0.0117 (5)
O4	0.0451 (6)	0.0350 (6)	0.0431 (6)	−0.0030 (5)	−0.0045 (5)	0.0032 (5)

C1—O1	1.3790 (19)	C16—C17	1.511 (2)
C1—C6	1.384 (2)	C16—H16	0.9800
C1—C2	1.384 (2)	C17—C18	1.527 (2)
C2—C3	1.372 (3)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.378 (3)	C18—C19	1.518 (3)
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.379 (3)	C18—H18B	0.9700
C4—H4	0.9300	C19—C20	1.514 (3)
C5—C6	1.385 (2)	C19—H19A	0.9700
C5—H5	0.9300	C19—H19B	0.9700
C6—C7	1.505 (2)	C20—N2	1.464 (2)
C7—C8	1.5417 (19)	C20—H20A	0.9700
C7—C21	1.567 (2)	C20—H20B	0.9700
C7—H7	0.9800	C21—N2	1.4624 (18)
C8—N1	1.5301 (18)	C21—C22	1.5080 (19)
C8—C16	1.540 (2)	C21—C28	1.5563 (19)
C8—C9	1.544 (2)	C22—C23	1.377 (2)
C9—O1	1.4499 (17)	C22—C27	1.387 (2)
C9—C10	1.508 (2)	C23—C24	1.388 (2)
C9—H9	0.9800	C23—H23	0.9300
C10—C11	1.385 (2)	C24—C25	1.379 (2)
C10—C15	1.386 (2)	C24—H24	0.9300
C11—C12	1.377 (2)	C25—C26	1.381 (2)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.376 (3)	C26—C27	1.376 (2)
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.375 (3)	C27—N3	1.4050 (19)
C13—H13	0.9300	C28—O4	1.2264 (17)
C14—C15	1.377 (3)	C28—N3	1.3454 (19)
C14—H14	0.9300	N1—O3	1.2199 (17)
C15—H15	0.9300	N1—O2	1.2216 (17)
C16—N2	1.4623 (18)	N3—H3A	0.8600
O1—C1—C6	120.19 (14)	C16—C17—H17A	109.9
O1—C1—C2	118.86 (15)	C18—C17—H17A	109.9
C6—C1—C2	120.91 (16)	C16—C17—H17B	109.9
C3—C2—C1	119.64 (18)	C18—C17—H17B	109.9
C3—C2—H2	120.2	H17A—C17—H17B	108.3
C1—C2—H2	120.2	C19—C18—C17	109.99 (15)
C2—C3—C4	120.33 (18)	C19—C18—H18A	109.7
C2—C3—H3	119.8	C17—C18—H18A	109.7
C4—C3—H3	119.8	C19—C18—H18B	109.7
C3—C4—C5	119.73 (18)	C17—C18—H18B	109.7
C3—C4—H4	120.1	H18A—C18—H18B	108.2
C5—C4—H4	120.1	C20—C19—C18	110.49 (15)
C4—C5—C6	120.89 (17)	C20—C19—H19A	109.6
C4—C5—H5	119.6	C18—C19—H19A	109.6
C6—C5—H5	119.6	C20—C19—H19B	109.6
C1—C6—C5	118.47 (15)	C18—C19—H19B	109.6
C1—C6—C7	120.39 (13)	H19A—C19—H19B	108.1
C5—C6—C7	121.06 (14)	N2—C20—C19	110.06 (14)
C6—C7—C8	113.75 (12)	N2—C20—H20A	109.6
C6—C7—C21	113.41 (11)	C19—C20—H20A	109.6
C8—C7—C21	105.04 (11)	N2—C20—H20B	109.6
C6—C7—H7	108.1	C19—C20—H20B	109.6
C8—C7—H7	108.1	H20A—C20—H20B	108.2
C21—C7—H7	108.1	N2—C21—C22	113.40 (12)
N1—C8—C16	106.20 (11)	N2—C21—C28	112.27 (11)
N1—C8—C7	110.35 (11)	C22—C21—C28	101.25 (11)
C16—C8—C7	104.66 (11)	N2—C21—C7	103.15 (11)
N1—C8—C9	108.50 (11)	C22—C21—C7	114.73 (11)
C16—C8—C9	111.39 (12)	C28—C21—C7	112.45 (11)
C7—C8—C9	115.35 (12)	C23—C22—C27	119.84 (13)
O1—C9—C10	110.48 (12)	C23—C22—C21	130.92 (13)
O1—C9—C8	108.02 (11)	C27—C22—C21	109.24 (12)
C10—C9—C8	118.21 (12)	C22—C23—C24	118.71 (14)
O1—C9—H9	106.5	C22—C23—H23	120.6
C10—C9—H9	106.5	C24—C23—H23	120.6
C8—C9—H9	106.5	C25—C24—C23	120.47 (14)
C11—C10—C15	118.49 (16)	C25—C24—H24	119.8
C11—C10—C9	124.19 (14)	C23—C24—H24	119.8
C15—C10—C9	117.32 (15)	C24—C25—C26	121.47 (15)
C12—C11—C10	120.83 (17)	C24—C25—H25	119.3
C12—C11—H11	119.6	C26—C25—H25	119.3
C10—C11—H11	119.6	C27—C26—C25	117.41 (14)
C13—C12—C11	119.90 (19)	C27—C26—H26	121.3
C13—C12—H12	120.0	C25—C26—H26	121.3
C11—C12—H12	120.0	C26—C27—C22	122.11 (14)
C14—C13—C12	120.03 (18)	C26—C27—N3	128.46 (14)
C14—C13—H13	120.0	C22—C27—N3	109.43 (12)
C12—C13—H13	120.0	O4—C28—N3	126.24 (14)
C13—C14—C15	120.03 (18)	O4—C28—C21	125.52 (13)
C13—C14—H14	120.0	N3—C28—C21	108.16 (12)
C15—C14—H14	120.0	O3—N1—O2	124.03 (13)
C14—C15—C10	120.72 (18)	O3—N1—C8	116.53 (12)
C14—C15—H15	119.6	O2—N1—C8	119.25 (12)
C10—C15—H15	119.6	C16—N2—C21	106.81 (11)
N2—C16—C17	110.04 (13)	C16—N2—C20	113.42 (12)
N2—C16—C8	102.43 (11)	C21—N2—C20	116.01 (12)
C17—C16—C8	119.42 (13)	C28—N3—C27	111.91 (12)
N2—C16—H16	108.1	C28—N3—H3A	124.0
C17—C16—H16	108.1	C27—N3—H3A	124.0
C8—C16—H16	108.1	C1—O1—C9	114.45 (11)
C16—C17—C18	109.01 (14)
O1—C1—C2—C3	177.03 (18)	C8—C7—C21—C22	140.86 (12)
C6—C1—C2—C3	−0.9 (3)	C6—C7—C21—C28	20.67 (16)
C1—C2—C3—C4	2.0 (3)	C8—C7—C21—C28	−104.13 (13)
C2—C3—C4—C5	−1.3 (4)	N2—C21—C22—C23	57.8 (2)
C3—C4—C5—C6	−0.5 (3)	C28—C21—C22—C23	178.28 (16)
O1—C1—C6—C5	−178.74 (14)	C7—C21—C22—C23	−60.4 (2)
C2—C1—C6—C5	−0.9 (3)	N2—C21—C22—C27	−121.55 (13)
O1—C1—C6—C7	−2.0 (2)	C28—C21—C22—C27	−1.08 (15)
C2—C1—C6—C7	175.85 (16)	C7—C21—C22—C27	120.27 (13)
C4—C5—C6—C1	1.5 (3)	C27—C22—C23—C24	−0.1 (2)
C4—C5—C6—C7	−175.15 (18)	C21—C22—C23—C24	−179.42 (15)
C1—C6—C7—C8	17.7 (2)	C22—C23—C24—C25	−0.3 (3)
C5—C6—C7—C8	−165.71 (14)	C23—C24—C25—C26	0.6 (3)
C1—C6—C7—C21	−102.30 (16)	C24—C25—C26—C27	−0.5 (2)
C5—C6—C7—C21	74.33 (18)	C25—C26—C27—C22	0.1 (2)
C6—C7—C8—N1	129.79 (13)	C25—C26—C27—N3	178.80 (15)
C21—C7—C8—N1	−105.62 (12)	C23—C22—C27—C26	0.2 (2)
C6—C7—C8—C16	−116.34 (13)	C21—C22—C27—C26	179.63 (14)
C21—C7—C8—C16	8.25 (13)	C23—C22—C27—N3	−178.70 (14)
C6—C7—C8—C9	6.41 (17)	C21—C22—C27—N3	0.74 (17)
C21—C7—C8—C9	131.00 (12)	N2—C21—C28—O4	−54.7 (2)
N1—C8—C9—O1	−167.40 (11)	C22—C21—C28—O4	−175.92 (15)
C16—C8—C9—O1	76.04 (14)	C7—C21—C28—O4	61.14 (19)
C7—C8—C9—O1	−43.05 (16)	N2—C21—C28—N3	122.35 (14)
N1—C8—C9—C10	−41.10 (17)	C22—C21—C28—N3	1.08 (16)
C16—C8—C9—C10	−157.65 (13)	C7—C21—C28—N3	−121.86 (14)
C7—C8—C9—C10	83.25 (16)	C16—C8—N1—O3	83.56 (15)
O1—C9—C10—C11	93.16 (18)	C7—C8—N1—O3	−163.55 (13)
C8—C9—C10—C11	−31.9 (2)	C9—C8—N1—O3	−36.28 (17)
O1—C9—C10—C15	−86.82 (16)	C16—C8—N1—O2	−91.57 (15)
C8—C9—C10—C15	148.08 (14)	C7—C8—N1—O2	21.31 (19)
C15—C10—C11—C12	−0.8 (3)	C9—C8—N1—O2	148.59 (14)
C9—C10—C11—C12	179.26 (16)	C17—C16—N2—C21	171.62 (12)
C10—C11—C12—C13	0.4 (3)	C8—C16—N2—C21	43.60 (13)
C11—C12—C13—C14	0.2 (3)	C17—C16—N2—C20	−59.32 (17)
C12—C13—C14—C15	−0.4 (3)	C8—C16—N2—C20	172.66 (12)
C13—C14—C15—C10	0.1 (3)	C22—C21—N2—C16	−162.76 (11)
C11—C10—C15—C14	0.5 (2)	C28—C21—N2—C16	83.23 (14)
C9—C10—C15—C14	−179.52 (16)	C7—C21—N2—C16	−38.06 (13)
N1—C8—C16—N2	86.17 (12)	C22—C21—N2—C20	69.69 (16)
C7—C8—C16—N2	−30.59 (13)	C28—C21—N2—C20	−44.32 (17)
C9—C8—C16—N2	−155.88 (11)	C7—C21—N2—C20	−165.61 (12)
N1—C8—C16—C17	−35.65 (17)	C19—C20—N2—C16	57.37 (19)
C7—C8—C16—C17	−152.41 (13)	C19—C20—N2—C21	−178.43 (14)
C9—C8—C16—C17	82.30 (16)	O4—C28—N3—C27	176.25 (15)
N2—C16—C17—C18	58.08 (17)	C21—C28—N3—C27	−0.72 (18)
C8—C16—C17—C18	176.04 (14)	C26—C27—N3—C28	−178.79 (16)
C16—C17—C18—C19	−57.7 (2)	C22—C27—N3—C28	0.01 (18)
C17—C18—C19—C20	56.6 (2)	C6—C1—O1—C9	−40.2 (2)
C18—C19—C20—N2	−55.2 (2)	C2—C1—O1—C9	141.90 (16)
C6—C7—C21—N2	141.84 (12)	C10—C9—O1—C1	−69.57 (16)
C8—C7—C21—N2	17.04 (13)	C8—C9—O1—C1	61.14 (16)
C6—C7—C21—C22	−94.34 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O4	0.98	2.50	3.1394 (18)	123
N3—H3A···O4i	0.86	1.97	2.8218 (17)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O4	0.98	2.50	3.1394 (18)	123
N3—H3A⋯O4i	0.86	1.97	2.8218 (17)	168

Symmetry code: (i) .