Di-tert-butyl 2,6,11-trioxo-2,3-dihydro-1H-anthra[1,2-d]imidazole-1,3-diacetate.

The fused-ring system of the title compound, C(27)H(28)N(2)O(7), which comprises one five- and three six-membered rings, is approximately planar (r.m.s. deviation = 0.133 Å), the system being buckled along the axis passing through the O atoms of the anthraquinone portion of the mol-ecule. Within the anthraquinone portion, the two benzene rings are aligned at 7.3 (2)°. In the crystal, one of the tert-butyl groups is disordered over two sets of sites in a 1:1 ratio. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For a related structure, see: Afrakssou et al. (2010 ▶).

Experimental

Crystal data

C27H28N2O7

M = 492.51

Monoclinic,

a = 19.5785 (4) Å

b = 13.0330 (3) Å

c = 9.9269 (2) Å

β = 90.583 (1)°

V = 2532.88 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.50 × 0.10 × 0.10 mm

Data collection

Bruker APEXII diffractometer

37371 measured reflections

5172 independent reflections

2929 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.190

S = 1.04

5172 reflections

353 parameters

48 restraints

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022914/xu5244sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022914/xu5244Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022914/xu5244Isup3.cml

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

C27H28N2O7	F(000) = 1040
Mr = 492.51	Dx = 1.292 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5392 reflections
a = 19.5785 (4) Å	θ = 2.6–23.5°
b = 13.0330 (3) Å	µ = 0.09 mm−1
c = 9.9269 (2) Å	T = 293 K
β = 90.583 (1)°	Prism, orange
V = 2532.88 (9) Å3	0.50 × 0.10 × 0.10 mm
Z = 4

Bruker APEXII diffractometer	2929 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.070
graphite	θmax = 26.4°, θmin = 1.9°
φ and ω scans	h = −24→24
37371 measured reflections	k = −16→16
5172 independent reflections	l = −12→12

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.190	w = 1/[σ2(Fo2) + (0.086P)2 + 1.5472P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
5172 reflections	Δρmax = 0.51 e Å−3
353 parameters	Δρmin = −0.31 e Å−3
48 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (12)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.11503 (11)	0.55465 (16)	0.3982 (2)	0.0529 (6)
O2	0.09491 (12)	0.94796 (16)	0.5443 (2)	0.0529 (6)
O3	0.33296 (11)	0.57044 (16)	0.0875 (2)	0.0468 (6)
O4	0.21612 (11)	0.36402 (15)	0.3971 (2)	0.0435 (5)
O5	0.26519 (12)	0.50970 (17)	0.4779 (2)	0.0504 (6)
O6	0.46459 (11)	0.8677 (2)	0.1416 (2)	0.0636 (7)
O7	0.41731 (15)	0.7703 (3)	0.3008 (3)	0.1046 (13)
N1	0.24308 (12)	0.60746 (17)	0.2331 (2)	0.0347 (6)
N2	0.30396 (12)	0.73659 (18)	0.1509 (2)	0.0365 (6)
C1	0.11879 (14)	0.6422 (2)	0.4430 (3)	0.0368 (7)
C2	0.07265 (14)	0.6734 (2)	0.5542 (3)	0.0358 (7)
C3	0.03615 (15)	0.5987 (3)	0.6220 (3)	0.0452 (8)
H3	0.0414	0.5302	0.5985	0.054*
C4	−0.00819 (16)	0.6249 (3)	0.7246 (3)	0.0484 (8)
H4	−0.0315	0.5743	0.7714	0.058*
C5	−0.01722 (16)	0.7274 (3)	0.7564 (3)	0.0484 (8)
H5	−0.0471	0.7455	0.8247	0.058*
C6	0.01780 (15)	0.8034 (3)	0.6876 (3)	0.0450 (8)
H6	0.0106	0.8721	0.7084	0.054*
C7	0.06374 (14)	0.7765 (2)	0.5873 (3)	0.0357 (7)
C8	0.10414 (14)	0.8571 (2)	0.5187 (3)	0.0381 (7)
C9	0.15721 (14)	0.8242 (2)	0.4211 (3)	0.0336 (6)
C10	0.19751 (15)	0.9009 (2)	0.3665 (3)	0.0392 (7)
H10	0.1901	0.9687	0.3917	0.047*
C11	0.24838 (15)	0.8789 (2)	0.2757 (3)	0.0402 (7)
H11	0.2757	0.9304	0.2403	0.048*
C12	0.25714 (14)	0.7778 (2)	0.2397 (3)	0.0335 (6)
C13	0.21739 (13)	0.6969 (2)	0.2917 (3)	0.0307 (6)
C14	0.16564 (13)	0.7197 (2)	0.3849 (3)	0.0320 (6)
C15	0.29788 (15)	0.6315 (2)	0.1490 (3)	0.0377 (7)
C16	0.22597 (15)	0.4999 (2)	0.2478 (3)	0.0357 (7)
H16A	0.2529	0.4600	0.1852	0.043*
H16B	0.1782	0.4901	0.2246	0.043*
C17	0.23880 (15)	0.4609 (2)	0.3887 (3)	0.0384 (7)
C18	0.21185 (18)	0.3115 (3)	0.5299 (3)	0.0516 (9)
C19	0.2819 (2)	0.2970 (4)	0.5889 (5)	0.0877 (15)
H19A	0.3091	0.2572	0.5283	0.132*
H19B	0.2786	0.2618	0.6736	0.132*
H19C	0.3029	0.3628	0.6028	0.132*
C20	0.1781 (2)	0.2106 (3)	0.4936 (4)	0.0653 (11)
H20A	0.2081	0.1713	0.4377	0.098*
H20B	0.1361	0.2237	0.4458	0.098*
H20C	0.1687	0.1729	0.5744	0.098*
C21	0.1649 (2)	0.3734 (3)	0.6196 (4)	0.0678 (11)
H21A	0.1866	0.4371	0.6431	0.102*
H21B	0.1555	0.3352	0.7000	0.102*
H21C	0.1228	0.3871	0.5723	0.102*
C22	0.36054 (14)	0.7901 (2)	0.0903 (3)	0.0392 (7)
H22A	0.3449	0.8556	0.0554	0.047*
H22B	0.3778	0.7502	0.0157	0.047*
C23	0.41684 (16)	0.8075 (3)	0.1919 (3)	0.0500 (8)
C24	0.5229 (2)	0.9059 (4)	0.2242 (5)	0.0988 (18)
C25	0.4904 (6)	0.9979 (8)	0.3039 (11)	0.111 (4)	0.50
H25A	0.4702	1.0455	0.2415	0.166*	0.50
H25B	0.5253	1.0319	0.3558	0.166*	0.50
H25C	0.4559	0.9722	0.3631	0.166*	0.50
C26	0.5707 (6)	0.9463 (9)	0.1166 (11)	0.088 (4)	0.50
H26A	0.5858	0.8905	0.0615	0.132*	0.50
H26B	0.6094	0.9785	0.1589	0.132*	0.50
H26C	0.5469	0.9956	0.0616	0.132*	0.50
C27	0.5567 (6)	0.8344 (8)	0.3191 (11)	0.113 (4)	0.50
H27A	0.5805	0.7825	0.2695	0.170*	0.50
H27B	0.5229	0.8026	0.3748	0.170*	0.50
H27C	0.5886	0.8715	0.3747	0.170*	0.50
C25'	0.5058 (7)	0.9391 (11)	0.3628 (9)	0.138 (5)	0.50
H25D	0.4839	0.8838	0.4093	0.207*	0.50
H25E	0.4757	0.9971	0.3586	0.207*	0.50
H25F	0.5469	0.9579	0.4102	0.207*	0.50
C26'	0.5574 (8)	0.9876 (8)	0.1401 (13)	0.102 (5)	0.50
H26D	0.5656	0.9613	0.0514	0.153*	0.50
H26E	0.6001	1.0064	0.1817	0.153*	0.50
H26F	0.5284	1.0469	0.1339	0.153*	0.50
C27'	0.5644 (6)	0.8040 (7)	0.2276 (13)	0.125 (4)	0.50
H27D	0.5753	0.7840	0.1373	0.187*	0.50
H27E	0.5376	0.7513	0.2692	0.187*	0.50
H27F	0.6058	0.8141	0.2785	0.187*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0527 (14)	0.0363 (13)	0.0702 (16)	−0.0088 (10)	0.0218 (12)	−0.0110 (11)
O2	0.0533 (14)	0.0369 (13)	0.0689 (16)	0.0024 (10)	0.0138 (12)	−0.0128 (11)
O3	0.0468 (13)	0.0471 (13)	0.0468 (13)	0.0058 (10)	0.0136 (10)	−0.0021 (10)
O4	0.0575 (13)	0.0329 (11)	0.0400 (12)	−0.0022 (10)	0.0018 (10)	0.0040 (9)
O5	0.0556 (14)	0.0515 (14)	0.0441 (13)	−0.0146 (11)	−0.0043 (10)	−0.0006 (10)
O6	0.0410 (13)	0.095 (2)	0.0546 (15)	−0.0213 (13)	−0.0013 (11)	0.0134 (13)
O7	0.0606 (18)	0.197 (4)	0.0563 (18)	−0.043 (2)	−0.0125 (14)	0.055 (2)
N1	0.0357 (13)	0.0299 (12)	0.0385 (13)	−0.0027 (10)	0.0071 (10)	−0.0007 (10)
N2	0.0335 (13)	0.0361 (14)	0.0402 (14)	−0.0039 (10)	0.0071 (11)	0.0026 (10)
C1	0.0338 (15)	0.0302 (16)	0.0465 (17)	−0.0005 (12)	0.0034 (13)	−0.0010 (12)
C2	0.0269 (14)	0.0401 (16)	0.0404 (16)	−0.0015 (12)	0.0031 (12)	0.0001 (12)
C3	0.0384 (17)	0.0448 (18)	0.0526 (19)	−0.0030 (14)	0.0082 (14)	−0.0007 (14)
C4	0.0379 (17)	0.059 (2)	0.0490 (19)	−0.0024 (15)	0.0099 (15)	0.0031 (15)
C5	0.0353 (17)	0.062 (2)	0.0476 (19)	0.0006 (15)	0.0093 (14)	−0.0059 (16)
C6	0.0371 (17)	0.0472 (19)	0.0510 (19)	0.0030 (14)	0.0056 (14)	−0.0123 (15)
C7	0.0283 (15)	0.0378 (16)	0.0408 (16)	0.0007 (12)	0.0013 (12)	−0.0045 (12)
C8	0.0332 (15)	0.0371 (17)	0.0439 (17)	0.0015 (13)	−0.0020 (13)	−0.0062 (13)
C9	0.0297 (14)	0.0293 (15)	0.0417 (16)	−0.0003 (11)	−0.0014 (12)	−0.0023 (12)
C10	0.0399 (16)	0.0287 (15)	0.0489 (18)	−0.0008 (12)	0.0012 (14)	−0.0009 (12)
C11	0.0394 (16)	0.0329 (16)	0.0483 (18)	−0.0050 (13)	0.0043 (13)	0.0045 (13)
C12	0.0295 (14)	0.0347 (15)	0.0363 (15)	0.0004 (12)	0.0014 (12)	0.0012 (12)
C13	0.0287 (14)	0.0285 (14)	0.0348 (14)	−0.0002 (11)	−0.0012 (11)	−0.0012 (11)
C14	0.0282 (14)	0.0313 (15)	0.0366 (15)	−0.0011 (11)	0.0014 (11)	−0.0010 (11)
C15	0.0349 (15)	0.0402 (17)	0.0381 (16)	0.0004 (13)	0.0035 (13)	0.0017 (13)
C16	0.0419 (16)	0.0272 (14)	0.0382 (16)	0.0013 (12)	0.0048 (12)	−0.0029 (11)
C17	0.0384 (16)	0.0365 (17)	0.0405 (17)	−0.0022 (13)	0.0025 (13)	0.0001 (13)
C18	0.061 (2)	0.050 (2)	0.0438 (19)	−0.0059 (16)	−0.0049 (16)	0.0148 (15)
C19	0.071 (3)	0.097 (3)	0.095 (3)	−0.001 (2)	−0.019 (2)	0.048 (3)
C20	0.091 (3)	0.042 (2)	0.063 (2)	−0.0064 (19)	0.004 (2)	0.0163 (17)
C21	0.090 (3)	0.063 (2)	0.051 (2)	−0.023 (2)	0.018 (2)	−0.0003 (18)
C22	0.0337 (15)	0.0465 (18)	0.0377 (16)	−0.0033 (13)	0.0070 (13)	0.0050 (13)
C23	0.0335 (17)	0.073 (2)	0.0437 (19)	−0.0046 (16)	0.0079 (14)	0.0119 (16)
C24	0.052 (3)	0.162 (5)	0.082 (3)	−0.047 (3)	−0.014 (2)	0.022 (3)
C25	0.109 (7)	0.121 (8)	0.101 (7)	−0.027 (6)	−0.020 (6)	−0.020 (6)
C26	0.046 (5)	0.121 (8)	0.097 (7)	−0.038 (6)	0.004 (5)	−0.009 (6)
C27	0.082 (6)	0.139 (8)	0.118 (7)	−0.014 (6)	−0.057 (6)	0.018 (6)
C25'	0.135 (8)	0.171 (9)	0.109 (8)	−0.053 (8)	−0.027 (7)	−0.012 (7)
C26'	0.080 (7)	0.125 (9)	0.102 (8)	−0.050 (7)	−0.002 (6)	0.002 (7)
C27'	0.075 (6)	0.186 (9)	0.112 (8)	−0.012 (7)	−0.016 (6)	0.040 (7)

O1—C1	1.227 (3)	C18—C19	1.498 (5)
O2—C8	1.225 (3)	C18—C20	1.512 (5)
O3—C15	1.220 (3)	C18—C21	1.519 (5)
O4—C17	1.341 (3)	C19—H19A	0.9600
O4—C18	1.488 (4)	C19—H19B	0.9600
O5—C17	1.203 (3)	C19—H19C	0.9600
O6—C23	1.322 (4)	C20—H20A	0.9600
O6—C24	1.484 (5)	C20—H20B	0.9600
O7—C23	1.186 (4)	C20—H20C	0.9600
N1—C13	1.399 (3)	C21—H21A	0.9600
N1—C15	1.402 (4)	C21—H21B	0.9600
N1—C16	1.449 (3)	C21—H21C	0.9600
N2—C15	1.374 (4)	C22—C23	1.503 (4)
N2—C12	1.387 (3)	C22—H22A	0.9700
N2—C22	1.445 (4)	C22—H22B	0.9700
C1—C14	1.485 (4)	C24—C27	1.477 (7)
C1—C2	1.490 (4)	C24—C25'	1.484 (7)
C2—C3	1.386 (4)	C24—C26'	1.516 (7)
C2—C7	1.394 (4)	C24—C26	1.521 (7)
C3—C4	1.387 (4)	C24—C27'	1.557 (8)
C3—H3	0.9300	C24—C25	1.574 (7)
C4—C5	1.384 (5)	C25—H25A	0.9600
C4—H4	0.9300	C25—H25B	0.9600
C5—C6	1.389 (4)	C25—H25C	0.9600
C5—H5	0.9300	C26—H26A	0.9600
C6—C7	1.393 (4)	C26—H26B	0.9600
C6—H6	0.9300	C26—H26C	0.9600
C7—C8	1.484 (4)	C27—H27A	0.9600
C8—C9	1.490 (4)	C27—H27B	0.9600
C9—C10	1.387 (4)	C27—H27C	0.9600
C9—C14	1.419 (4)	C25'—H25D	0.9600
C10—C11	1.380 (4)	C25'—H25E	0.9600
C10—H10	0.9300	C25'—H25F	0.9600
C11—C12	1.376 (4)	C26'—H26D	0.9600
C11—H11	0.9300	C26'—H26E	0.9600
C12—C13	1.412 (4)	C26'—H26F	0.9600
C13—C14	1.410 (4)	C27'—H27D	0.9600
C16—C17	1.507 (4)	C27'—H27E	0.9600
C16—H16A	0.9700	C27'—H27F	0.9600
C16—H16B	0.9700
C17—O4—C18	120.7 (2)	H20A—C20—H20B	109.5
C23—O6—C24	122.3 (3)	C18—C20—H20C	109.5
C13—N1—C15	110.0 (2)	H20A—C20—H20C	109.5
C13—N1—C16	132.8 (2)	H20B—C20—H20C	109.5
C15—N1—C16	117.1 (2)	C18—C21—H21A	109.5
C15—N2—C12	109.7 (2)	C18—C21—H21B	109.5
C15—N2—C22	122.8 (2)	H21A—C21—H21B	109.5
C12—N2—C22	126.3 (2)	C18—C21—H21C	109.5
O1—C1—C14	121.8 (3)	H21A—C21—H21C	109.5
O1—C1—C2	119.2 (3)	H21B—C21—H21C	109.5
C14—C1—C2	119.0 (2)	N2—C22—C23	110.7 (2)
C3—C2—C7	119.7 (3)	N2—C22—H22A	109.5
C3—C2—C1	119.2 (3)	C23—C22—H22A	109.5
C7—C2—C1	121.0 (3)	N2—C22—H22B	109.5
C2—C3—C4	120.9 (3)	C23—C22—H22B	109.5
C2—C3—H3	119.6	H22A—C22—H22B	108.1
C4—C3—H3	119.6	O7—C23—O6	126.0 (3)
C5—C4—C3	119.2 (3)	O7—C23—C22	123.3 (3)
C5—C4—H4	120.4	O6—C23—C22	110.7 (3)
C3—C4—H4	120.4	C27—C24—O6	118.5 (5)
C4—C5—C6	120.7 (3)	C27—C24—C25'	72.3 (6)
C4—C5—H5	119.6	O6—C24—C25'	115.5 (6)
C6—C5—H5	119.6	C27—C24—C26'	126.5 (9)
C5—C6—C7	119.8 (3)	O6—C24—C26'	106.0 (7)
C5—C6—H6	120.1	C25'—C24—C26'	114.3 (7)
C7—C6—H6	120.1	C27—C24—C26	113.1 (6)
C2—C7—C6	119.6 (3)	O6—C24—C26	101.7 (6)
C2—C7—C8	120.3 (2)	C25'—C24—C26	134.1 (8)
C6—C7—C8	120.0 (3)	C26'—C24—C26	24.4 (7)
O2—C8—C7	120.6 (3)	C27—C24—C27'	38.5 (5)
O2—C8—C9	121.2 (3)	O6—C24—C27'	97.1 (6)
C7—C8—C9	118.3 (2)	C25'—C24—C27'	110.5 (6)
C10—C9—C14	121.6 (3)	C26'—C24—C27'	112.1 (6)
C10—C9—C8	116.8 (2)	C26—C24—C27'	89.2 (7)
C14—C9—C8	121.6 (2)	C27—C24—C25	109.9 (6)
C11—C10—C9	121.5 (3)	O6—C24—C25	102.7 (5)
C11—C10—H10	119.3	C25'—C24—C25	38.3 (6)
C9—C10—H10	119.3	C26'—C24—C25	85.8 (7)
C12—C11—C10	117.5 (3)	C26—C24—C25	110.1 (6)
C12—C11—H11	121.3	C27'—C24—C25	148.4 (6)
C10—C11—H11	121.3	C24—C25—H25A	109.5
C11—C12—N2	128.4 (3)	C24—C25—H25B	109.5
C11—C12—C13	123.3 (3)	H25A—C25—H25B	109.5
N2—C12—C13	108.3 (2)	C24—C25—H25C	109.5
N1—C13—C14	135.4 (2)	H25A—C25—H25C	109.5
N1—C13—C12	105.6 (2)	H25B—C25—H25C	109.5
C14—C13—C12	119.0 (2)	C24—C26—H26A	109.5
C13—C14—C9	117.1 (2)	C24—C26—H26B	109.5
C13—C14—C1	124.2 (2)	H26A—C26—H26B	109.5
C9—C14—C1	118.7 (2)	C24—C26—H26C	109.5
O3—C15—N2	127.4 (3)	H26A—C26—H26C	109.5
O3—C15—N1	126.2 (3)	H26B—C26—H26C	109.5
N2—C15—N1	106.4 (2)	C24—C27—H27A	109.5
N1—C16—C17	112.6 (2)	C24—C27—H27B	109.5
N1—C16—H16A	109.1	H27A—C27—H27B	109.5
C17—C16—H16A	109.1	C24—C27—H27C	109.5
N1—C16—H16B	109.1	H27A—C27—H27C	109.5
C17—C16—H16B	109.1	H27B—C27—H27C	109.5
H16A—C16—H16B	107.8	C24—C25'—H25D	109.5
O5—C17—O4	126.3 (3)	C24—C25'—H25E	109.5
O5—C17—C16	124.8 (3)	H25D—C25'—H25E	109.5
O4—C17—C16	108.9 (2)	C24—C25'—H25F	109.5
O4—C18—C19	110.2 (3)	H25D—C25'—H25F	109.5
O4—C18—C20	102.6 (3)	H25E—C25'—H25F	109.5
C19—C18—C20	112.3 (3)	C24—C26'—H26D	109.5
O4—C18—C21	108.3 (3)	C24—C26'—H26E	109.5
C19—C18—C21	113.2 (3)	H26D—C26'—H26E	109.5
C20—C18—C21	109.6 (3)	C24—C26'—H26F	109.5
C18—C19—H19A	109.5	H26D—C26'—H26F	109.5
C18—C19—H19B	109.5	H26E—C26'—H26F	109.5
H19A—C19—H19B	109.5	C24—C27'—H27D	109.5
C18—C19—H19C	109.5	C24—C27'—H27E	109.5
H19A—C19—H19C	109.5	H27D—C27'—H27E	109.5
H19B—C19—H19C	109.5	C24—C27'—H27F	109.5
C18—C20—H20A	109.5	H27D—C27'—H27F	109.5
C18—C20—H20B	109.5	H27E—C27'—H27F	109.5
O1—C1—C2—C3	12.3 (4)	C12—C13—C14—C9	−0.4 (4)
C14—C1—C2—C3	−170.7 (3)	N1—C13—C14—C1	−3.7 (5)
O1—C1—C2—C7	−165.2 (3)	C12—C13—C14—C1	177.7 (3)
C14—C1—C2—C7	11.8 (4)	C10—C9—C14—C13	0.6 (4)
C7—C2—C3—C4	−1.4 (5)	C8—C9—C14—C13	−180.0 (2)
C1—C2—C3—C4	−178.9 (3)	C10—C9—C14—C1	−177.5 (3)
C2—C3—C4—C5	1.8 (5)	C8—C9—C14—C1	1.9 (4)
C3—C4—C5—C6	−0.4 (5)	O1—C1—C14—C13	−11.4 (5)
C4—C5—C6—C7	−1.4 (5)	C2—C1—C14—C13	171.7 (3)
C3—C2—C7—C6	−0.5 (4)	O1—C1—C14—C9	166.6 (3)
C1—C2—C7—C6	177.0 (3)	C2—C1—C14—C9	−10.3 (4)
C3—C2—C7—C8	178.0 (3)	C12—N2—C15—O3	−176.3 (3)
C1—C2—C7—C8	−4.5 (4)	C22—N2—C15—O3	−8.1 (5)
C5—C6—C7—C2	1.9 (4)	C12—N2—C15—N1	3.4 (3)
C5—C6—C7—C8	−176.6 (3)	C22—N2—C15—N1	171.6 (2)
C2—C7—C8—O2	177.6 (3)	C13—N1—C15—O3	177.0 (3)
C6—C7—C8—O2	−3.9 (4)	C16—N1—C15—O3	−0.5 (4)
C2—C7—C8—C9	−4.0 (4)	C13—N1—C15—N2	−2.8 (3)
C6—C7—C8—C9	174.5 (3)	C16—N1—C15—N2	179.8 (2)
O2—C8—C9—C10	3.1 (4)	C13—N1—C16—C17	−62.9 (4)
C7—C8—C9—C10	−175.2 (3)	C15—N1—C16—C17	113.8 (3)
O2—C8—C9—C14	−176.3 (3)	C18—O4—C17—O5	9.9 (5)
C7—C8—C9—C14	5.3 (4)	C18—O4—C17—C16	−170.1 (3)
C14—C9—C10—C11	−0.9 (4)	N1—C16—C17—O5	−5.5 (4)
C8—C9—C10—C11	179.7 (3)	N1—C16—C17—O4	174.5 (2)
C9—C10—C11—C12	0.9 (4)	C17—O4—C18—C19	−65.4 (4)
C10—C11—C12—N2	179.7 (3)	C17—O4—C18—C20	174.8 (3)
C10—C11—C12—C13	−0.6 (4)	C17—O4—C18—C21	59.0 (4)
C15—N2—C12—C11	176.8 (3)	C15—N2—C22—C23	−92.2 (3)
C22—N2—C12—C11	9.2 (5)	C12—N2—C22—C23	73.9 (4)
C15—N2—C12—C13	−2.9 (3)	C24—O6—C23—O7	−6.9 (6)
C22—N2—C12—C13	−170.5 (3)	C24—O6—C23—C22	173.9 (4)
C15—N1—C13—C14	−177.8 (3)	N2—C22—C23—O7	8.9 (5)
C16—N1—C13—C14	−0.9 (5)	N2—C22—C23—O6	−171.9 (3)
C15—N1—C13—C12	1.0 (3)	C23—O6—C24—C27	41.5 (8)
C16—N1—C13—C12	177.9 (3)	C23—O6—C24—C25'	−41.3 (8)
C11—C12—C13—N1	−178.6 (3)	C23—O6—C24—C26'	−169.1 (6)
N2—C12—C13—N1	1.1 (3)	C23—O6—C24—C26	166.2 (6)
C11—C12—C13—C14	0.4 (4)	C23—O6—C24—C27'	75.5 (6)
N2—C12—C13—C14	−179.9 (2)	C23—O6—C24—C25	−79.8 (6)
N1—C13—C14—C9	178.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O2i	0.97	2.54	3.320 (4)	137
C22—H22A···O5i	0.97	2.47	3.391 (3)	159
C22—H22B···O7i	0.97	2.29	3.190 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O2i	0.97	2.54	3.320 (4)	137
C22—H22A⋯O5i	0.97	2.47	3.391 (3)	159
C22—H22B⋯O7i	0.97	2.29	3.190 (4)	154

Symmetry code: (i) .