Crystal structure of meso-tetra-kis-(4-nitro-phen-yl)porphyrin nitro-benzene disolvate.

The porphyrin core of the title centrosymmetric compound, C44H26N8O8·2C6H5NO2, is approximately planar, the maximum deviation being 0.069 (3) Å. The planes of the benzene rings of the nitro-phenyl substituents are almost perpendicular to the porphyrin mean plane, making dihedral angles of 73.89 (9) and 89.24 (9)°. The two pyrrole ring H atoms are equally disordered over the four pyrrole ring N atoms. In the crystal, weak C-H⋯O and C-H⋯N hydrogen bonds link the porphyrin mol-ecules into a three-dimensional supra-molecular network. The nitro-benzene solvent mol-ecules are linked by weak C-H⋯O hydrogen bonds into supra-molecular chains propagating along the a-axis direction.

Related literature

Porphyrins and metalloporphyrins are of inter­est as building blocks for mol­ecular cages (Meng et al., 2011 ▶), catalysts (Odo et al., 2009 ▶) and photofunctional materials (Yan et al., 2009 ▶). For related structures, see: Silvers & Tulinsky (1967 ▶). For related polymeric complexes, see: Seredyuk et al. (2007 ▶); Moroz et al. (2012 ▶); Zha et al. (2013 ▶). For the synthesis of meso-tetra­kis­(4-nitro­phen­yl)porphyrin, see: Bettelheim et al. (1987 ▶).

Experimental

Crystal data

C44H26N8O8·2C6H5NO2

M = 1040.95

Triclinic,

a = 7.949 (4) Å

b = 10.134 (5) Å

c = 16.444 (8) Å

α = 105.43 (5)°

β = 95.37 (4)°

γ = 102.17 (4)°

V = 1232.4 (11) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.13 × 0.09 × 0.03 mm

Data collection

Agilent Xcalibur κ-axis diffractometer with a Ruby CCD detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.981, T max = 1.000

10625 measured reflections

5284 independent reflections

3437 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.275

S = 1.10

5284 reflections

322 parameters

9 restraints

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814021503/xu5821sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814021503/xu5821Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814021503/xu5821Isup3.cdx

Click here for additional data file.

. DOI: 10.1107/S1600536814021503/xu5821fig1.tif

Mol­ecular structure of the title compound with the atom-labeling scheme and 25% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.

Click here for additional data file.

a . DOI: 10.1107/S1600536814021503/xu5821fig2.tif

Projection of the crystal packing along a axis.

CCDC reference: 1026803

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

C44H26N8O8·2C6H5NO2	Z = 1
Mr = 1040.95	F(000) = 538
Triclinic, P1	Dx = 1.403 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.949 (4) Å	Cell parameters from 3566 reflections
b = 10.134 (5) Å	θ = 2.8–28.7°
c = 16.444 (8) Å	µ = 0.10 mm−1
α = 105.43 (5)°	T = 293 K
β = 95.37 (4)°	Plate, violet
γ = 102.17 (4)°	0.13 × 0.09 × 0.03 mm
V = 1232.4 (11) Å3

Agilent Xcalibur κ-axis diffractometer with a Ruby CCD detector	5284 independent reflections
Radiation source: fine-focus sealed tube	3437 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scans	θmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −10→10
Tmin = 0.981, Tmax = 1.000	k = −12→12
10625 measured reflections	l = −20→20

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.275	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.1381P)2 + 0.6248P] where P = (Fo2 + 2Fc2)/3
5284 reflections	(Δ/σ)max = 0.002
322 parameters	Δρmax = 0.60 e Å−3
9 restraints	Δρmin = −0.49 e Å−3

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	Occ. (<1)
O1	1.0682 (3)	1.0348 (3)	−0.1297 (2)	0.0828 (9)
O2	1.1718 (4)	0.8612 (4)	−0.1166 (3)	0.1000 (11)
N1	0.2102 (3)	0.6614 (2)	0.06866 (14)	0.0365 (5)
H1N	0.1178	0.6023	0.0377	0.044*	0.50
N2	1.0538 (4)	0.9210 (4)	−0.11673 (19)	0.0624 (8)
C1	0.2304 (4)	0.7297 (3)	0.15411 (17)	0.0389 (6)
C2	0.4064 (4)	0.8181 (3)	0.18213 (19)	0.0470 (7)
H2	0.4545	0.8742	0.2375	0.056*
C3	0.4871 (4)	0.8038 (3)	0.11299 (18)	0.0447 (7)
H3	0.6008	0.8495	0.1116	0.054*
C4	0.3650 (3)	0.7047 (3)	0.04161 (17)	0.0365 (6)
C5	0.0641 (4)	0.3740 (3)	−0.18184 (17)	0.0419 (7)
C6	0.5738 (3)	0.7244 (3)	−0.06002 (17)	0.0374 (6)
C7	0.6008 (4)	0.8585 (3)	−0.0698 (2)	0.0485 (7)
H7	0.5121	0.9057	−0.0639	0.058*
C8	0.7578 (4)	0.9233 (3)	−0.0882 (2)	0.0515 (8)
H8	0.7754	1.0134	−0.0946	0.062*
C9	0.8864 (4)	0.8526 (3)	−0.09695 (19)	0.0464 (7)
C10	0.8646 (5)	0.7199 (4)	−0.0880 (3)	0.0639 (10)
H10	0.9540	0.6736	−0.0939	0.077*
C11	0.7068 (5)	0.6564 (4)	−0.0701 (3)	0.0628 (10)
H11	0.6898	0.5656	−0.0648	0.075*
O3	−0.2626 (6)	−0.1809 (4)	−0.5712 (2)	0.1246 (15)
O4	−0.3322 (7)	−0.0114 (5)	−0.6082 (2)	0.1343 (16)
N3	0.1296 (3)	0.4707 (2)	−0.10375 (14)	0.0398 (6)
H3N	0.0770	0.4832	−0.0599	0.048*	0.50
N4A	−0.2790 (5)	−0.0618 (4)	−0.5550 (2)	0.0833 (11)
C12	0.4023 (4)	0.6543 (3)	−0.04098 (17)	0.0373 (6)
C13	0.2928 (4)	0.5441 (3)	−0.10724 (17)	0.0397 (6)
C14	0.3327 (4)	0.4883 (3)	−0.1909 (2)	0.0517 (8)
H14	0.4360	0.5183	−0.2104	0.062*
C15	0.1940 (4)	0.3851 (3)	−0.2362 (2)	0.0535 (8)
H15	0.1843	0.3306	−0.2925	0.064*
C16	−0.1031 (4)	0.2835 (3)	−0.20674 (17)	0.0398 (6)
C17	−0.1495 (4)	0.1928 (3)	−0.29832 (18)	0.0439 (7)
C18	−0.1154 (6)	0.0617 (4)	−0.3218 (2)	0.0667 (10)
H18	−0.0624	0.0291	−0.2808	0.080*
C19	−0.1593 (6)	−0.0226 (4)	−0.4062 (2)	0.0733 (11)
H19	−0.1383	−0.1122	−0.4218	0.088*
C20	−0.2330 (5)	0.0277 (4)	−0.4652 (2)	0.0590 (9)
C21	−0.2655 (6)	0.1580 (5)	−0.4446 (2)	0.0796 (12)
H21	−0.3136	0.1917	−0.4863	0.095*
C22	−0.2252 (6)	0.2392 (4)	−0.3599 (2)	0.0731 (11)
H22	−0.2502	0.3273	−0.3445	0.088*
O5	0.9853 (9)	0.2373 (9)	0.3161 (7)	0.233 (4)
O6	1.0580 (9)	0.4623 (10)	0.3993 (6)	0.233 (4)
N5	0.9530 (10)	0.3478 (10)	0.3562 (6)	0.160 (3)
C23	0.7681 (10)	0.3458 (8)	0.3540 (4)	0.1216 (9)
C24	0.7255 (9)	0.4653 (7)	0.4008 (4)	0.1216 (9)
H24	0.8110	0.5438	0.4341	0.146*
C25	0.5530 (9)	0.4635 (8)	0.3964 (4)	0.1216 (9)
H25	0.5192	0.5424	0.4267	0.146*
C26	0.4316 (9)	0.3488 (7)	0.3485 (4)	0.1216 (9)
H26	0.3142	0.3487	0.3468	0.146*
C27	0.4768 (9)	0.2347 (8)	0.3033 (4)	0.1216 (9)
H27	0.3897	0.1569	0.2705	0.146*
C28	0.6424 (9)	0.2289 (8)	0.3038 (4)	0.1216 (9)
H28	0.6724	0.1493	0.2716	0.146*

	U11	U22	U33	U12	U13	U23
O1	0.0524 (16)	0.099 (2)	0.104 (2)	−0.0040 (15)	0.0200 (15)	0.0572 (19)
O2	0.0414 (15)	0.127 (3)	0.145 (3)	0.0250 (17)	0.0367 (17)	0.050 (2)
N1	0.0361 (12)	0.0349 (11)	0.0321 (11)	0.0014 (9)	0.0077 (9)	0.0039 (9)
N2	0.0354 (15)	0.089 (2)	0.0634 (19)	0.0058 (15)	0.0115 (13)	0.0285 (17)
C1	0.0405 (15)	0.0338 (13)	0.0354 (14)	0.0018 (11)	0.0061 (11)	0.0042 (11)
C2	0.0429 (17)	0.0450 (16)	0.0393 (16)	−0.0023 (13)	0.0003 (12)	0.0017 (12)
C3	0.0404 (16)	0.0429 (15)	0.0416 (16)	−0.0006 (12)	0.0056 (12)	0.0057 (12)
C4	0.0353 (14)	0.0331 (13)	0.0382 (14)	0.0038 (11)	0.0064 (11)	0.0093 (11)
C5	0.0469 (17)	0.0419 (15)	0.0324 (14)	0.0054 (13)	0.0103 (12)	0.0061 (11)
C6	0.0349 (14)	0.0410 (14)	0.0348 (14)	0.0072 (11)	0.0076 (11)	0.0093 (11)
C7	0.0362 (16)	0.0450 (16)	0.068 (2)	0.0103 (13)	0.0155 (14)	0.0203 (15)
C8	0.0422 (17)	0.0471 (17)	0.071 (2)	0.0068 (14)	0.0139 (15)	0.0280 (16)
C9	0.0315 (15)	0.0611 (19)	0.0457 (17)	0.0052 (14)	0.0086 (12)	0.0180 (14)
C10	0.0454 (19)	0.070 (2)	0.091 (3)	0.0261 (17)	0.0242 (18)	0.035 (2)
C11	0.053 (2)	0.0543 (19)	0.097 (3)	0.0200 (16)	0.0247 (19)	0.0391 (19)
O3	0.189 (4)	0.089 (2)	0.065 (2)	0.023 (3)	0.023 (2)	−0.0227 (18)
O4	0.194 (5)	0.139 (3)	0.0400 (17)	0.018 (3)	−0.016 (2)	0.0073 (19)
N3	0.0421 (13)	0.0399 (12)	0.0305 (12)	0.0017 (10)	0.0091 (9)	0.0044 (9)
N4A	0.089 (3)	0.088 (3)	0.0426 (19)	−0.008 (2)	0.0128 (17)	−0.0086 (18)
C12	0.0371 (15)	0.0358 (13)	0.0384 (14)	0.0052 (11)	0.0097 (11)	0.0117 (11)
C13	0.0418 (16)	0.0400 (14)	0.0354 (14)	0.0037 (12)	0.0112 (11)	0.0110 (12)
C14	0.0487 (18)	0.0564 (18)	0.0428 (17)	0.0009 (15)	0.0197 (14)	0.0077 (14)
C15	0.059 (2)	0.0539 (18)	0.0362 (15)	0.0014 (15)	0.0201 (14)	−0.0002 (13)
C16	0.0465 (16)	0.0376 (14)	0.0298 (13)	0.0058 (12)	0.0077 (11)	0.0035 (11)
C17	0.0445 (16)	0.0445 (15)	0.0337 (14)	0.0004 (13)	0.0088 (12)	0.0040 (12)
C18	0.102 (3)	0.054 (2)	0.0382 (17)	0.025 (2)	0.0027 (18)	0.0029 (15)
C19	0.102 (3)	0.056 (2)	0.050 (2)	0.019 (2)	0.013 (2)	−0.0049 (17)
C20	0.061 (2)	0.064 (2)	0.0318 (16)	−0.0046 (17)	0.0078 (14)	−0.0035 (14)
C21	0.107 (3)	0.080 (3)	0.042 (2)	0.020 (2)	−0.007 (2)	0.0106 (18)
C22	0.106 (3)	0.064 (2)	0.0422 (19)	0.030 (2)	0.0006 (19)	0.0017 (16)
O5	0.164 (6)	0.203 (7)	0.357 (12)	0.088 (6)	0.022 (6)	0.098 (8)
O6	0.134 (5)	0.259 (9)	0.256 (8)	−0.048 (6)	−0.039 (5)	0.089 (7)
N5	0.129 (6)	0.158 (6)	0.217 (8)	0.055 (5)	0.040 (5)	0.078 (6)
C23	0.128 (2)	0.138 (2)	0.106 (2)	0.0241 (19)	0.0334 (17)	0.0501 (17)
C24	0.128 (2)	0.138 (2)	0.106 (2)	0.0241 (19)	0.0334 (17)	0.0501 (17)
C25	0.128 (2)	0.138 (2)	0.106 (2)	0.0241 (19)	0.0334 (17)	0.0501 (17)
C26	0.128 (2)	0.138 (2)	0.106 (2)	0.0241 (19)	0.0334 (17)	0.0501 (17)
C27	0.128 (2)	0.138 (2)	0.106 (2)	0.0241 (19)	0.0334 (17)	0.0501 (17)
C28	0.128 (2)	0.138 (2)	0.106 (2)	0.0241 (19)	0.0334 (17)	0.0501 (17)

O1—N2	1.212 (4)	C12—C13	1.399 (4)
O2—N2	1.220 (4)	C13—C14	1.435 (4)
N1—C1	1.369 (3)	C14—C15	1.345 (5)
N1—C4	1.372 (3)	C14—H14	0.9300
N1—H1N	0.8600	C15—H15	0.9300
N2—C9	1.472 (4)	C16—C1i	1.399 (4)
C1—C16i	1.399 (4)	C16—C17	1.505 (4)
C1—C2	1.451 (4)	C17—C22	1.366 (5)
C2—C3	1.347 (4)	C17—C18	1.374 (5)
C2—H2	0.9300	C18—C19	1.390 (5)
C3—C4	1.441 (4)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.353 (6)
C4—C12	1.401 (4)	C19—H19	0.9300
C5—N3	1.367 (4)	C20—C21	1.359 (6)
C5—C16	1.400 (4)	C21—C22	1.384 (5)
C5—C15	1.433 (4)	C21—H21	0.9300
C6—C11	1.379 (4)	C22—H22	0.9300
C6—C7	1.386 (4)	O5—N5	1.230 (9)
C6—C12	1.500 (4)	O6—N5	1.260 (9)
C7—C8	1.382 (4)	N5—C23	1.462 (10)
C7—H7	0.9300	C23—C24	1.378 (8)
C8—C9	1.363 (4)	C23—C28	1.382 (8)
C8—H8	0.9300	C24—C25	1.363 (8)
C9—C10	1.368 (5)	C24—H24	0.9300
C10—C11	1.379 (5)	C25—C26	1.342 (8)
C10—H10	0.9300	C25—H25	0.9300
C11—H11	0.9300	C26—C27	1.337 (8)
O3—N4A	1.203 (5)	C26—H26	0.9300
O4—N4A	1.210 (5)	C27—C28	1.329 (8)
N3—C13	1.367 (4)	C27—H27	0.9300
N3—H3N	0.8600	C28—H28	0.9300
N4A—C20	1.477 (4)
C1—N1—C4	107.2 (2)	C12—C13—C14	125.8 (3)
C1—N1—H1N	126.4	C15—C14—C13	107.8 (3)
C4—N1—H1N	126.4	C15—C14—H14	126.1
O1—N2—O2	123.8 (3)	C13—C14—H14	126.1
O1—N2—C9	118.5 (3)	C14—C15—C5	107.6 (3)
O2—N2—C9	117.7 (3)	C14—C15—H15	126.2
N1—C1—C16i	126.0 (3)	C5—C15—H15	126.2
N1—C1—C2	109.0 (2)	C1i—C16—C5	125.8 (3)
C16i—C1—C2	125.0 (3)	C1i—C16—C17	117.4 (3)
C3—C2—C1	107.1 (3)	C5—C16—C17	116.9 (2)
C3—C2—H2	126.4	C22—C17—C18	118.6 (3)
C1—C2—H2	126.4	C22—C17—C16	120.9 (3)
C2—C3—C4	107.4 (3)	C18—C17—C16	120.5 (3)
C2—C3—H3	126.3	C17—C18—C19	120.6 (3)
C4—C3—H3	126.3	C17—C18—H18	119.7
N1—C4—C12	125.5 (2)	C19—C18—H18	119.7
N1—C4—C3	109.2 (2)	C20—C19—C18	118.9 (3)
C12—C4—C3	125.2 (3)	C20—C19—H19	120.6
N3—C5—C16	126.6 (3)	C18—C19—H19	120.6
N3—C5—C15	108.2 (3)	C19—C20—C21	122.1 (3)
C16—C5—C15	125.2 (3)	C19—C20—N4A	118.8 (4)
C11—C6—C7	118.3 (3)	C21—C20—N4A	119.1 (4)
C11—C6—C12	121.2 (3)	C20—C21—C22	118.3 (4)
C7—C6—C12	120.5 (2)	C20—C21—H21	120.9
C8—C7—C6	120.9 (3)	C22—C21—H21	120.9
C8—C7—H7	119.5	C17—C22—C21	121.5 (4)
C6—C7—H7	119.5	C17—C22—H22	119.2
C9—C8—C7	118.9 (3)	C21—C22—H22	119.2
C9—C8—H8	120.6	O5—N5—O6	128.7 (9)
C7—C8—H8	120.6	O5—N5—C23	115.7 (9)
C8—C9—C10	122.0 (3)	O6—N5—C23	115.6 (8)
C8—C9—N2	119.1 (3)	C24—C23—C28	121.9 (7)
C10—C9—N2	118.9 (3)	C24—C23—N5	117.8 (7)
C9—C10—C11	118.5 (3)	C28—C23—N5	120.3 (7)
C9—C10—H10	120.8	C25—C24—C23	117.2 (7)
C11—C10—H10	120.8	C25—C24—H24	121.4
C6—C11—C10	121.5 (3)	C23—C24—H24	121.4
C6—C11—H11	119.3	C26—C25—C24	120.6 (7)
C10—C11—H11	119.3	C26—C25—H25	119.7
C13—N3—C5	108.3 (2)	C24—C25—H25	119.7
C13—N3—H3N	125.8	C27—C26—C25	120.9 (7)
C5—N3—H3N	125.8	C27—C26—H26	119.5
O3—N4A—O4	123.5 (4)	C25—C26—H26	119.5
O3—N4A—C20	118.4 (4)	C28—C27—C26	122.0 (8)
O4—N4A—C20	118.2 (4)	C28—C27—H27	119.0
C13—C12—C4	125.4 (3)	C26—C27—H27	119.0
C13—C12—C6	117.2 (2)	C27—C28—C23	117.4 (7)
C4—C12—C6	117.3 (2)	C27—C28—H28	121.3
N3—C13—C12	126.2 (2)	C23—C28—H28	121.3
N3—C13—C14	108.1 (2)
C4—N1—C1—C16i	179.5 (3)	N3—C13—C14—C15	0.8 (4)
C4—N1—C1—C2	−0.9 (3)	C12—C13—C14—C15	−179.2 (3)
N1—C1—C2—C3	1.3 (3)	C13—C14—C15—C5	0.1 (4)
C16i—C1—C2—C3	−179.1 (3)	N3—C5—C15—C14	−1.0 (4)
C1—C2—C3—C4	−1.2 (3)	C16—C5—C15—C14	176.5 (3)
C1—N1—C4—C12	176.6 (3)	N3—C5—C16—C1i	−3.9 (5)
C1—N1—C4—C3	0.2 (3)	C15—C5—C16—C1i	179.1 (3)
C2—C3—C4—N1	0.7 (3)	N3—C5—C16—C17	176.0 (3)
C2—C3—C4—C12	−175.8 (3)	C15—C5—C16—C17	−1.0 (5)
C11—C6—C7—C8	−0.8 (5)	C1i—C16—C17—C22	89.5 (4)
C12—C6—C7—C8	−179.3 (3)	C5—C16—C17—C22	−90.4 (4)
C6—C7—C8—C9	0.2 (5)	C1i—C16—C17—C18	−90.9 (4)
C7—C8—C9—C10	0.0 (5)	C5—C16—C17—C18	89.2 (4)
C7—C8—C9—N2	179.9 (3)	C22—C17—C18—C19	−0.9 (6)
O1—N2—C9—C8	−4.4 (5)	C16—C17—C18—C19	179.5 (3)
O2—N2—C9—C8	173.5 (3)	C17—C18—C19—C20	1.3 (6)
O1—N2—C9—C10	175.5 (3)	C18—C19—C20—C21	0.0 (6)
O2—N2—C9—C10	−6.6 (5)	C18—C19—C20—N4A	179.8 (4)
C8—C9—C10—C11	0.4 (6)	O3—N4A—C20—C19	6.1 (6)
N2—C9—C10—C11	−179.5 (3)	O4—N4A—C20—C19	−174.3 (4)
C7—C6—C11—C10	1.2 (5)	O3—N4A—C20—C21	−174.1 (4)
C12—C6—C11—C10	179.7 (3)	O4—N4A—C20—C21	5.5 (6)
C9—C10—C11—C6	−1.0 (6)	C19—C20—C21—C22	−1.6 (7)
C16—C5—N3—C13	−176.0 (3)	N4A—C20—C21—C22	178.6 (4)
C15—C5—N3—C13	1.4 (3)	C18—C17—C22—C21	−0.8 (6)
N1—C4—C12—C13	−5.3 (5)	C16—C17—C22—C21	178.8 (4)
C3—C4—C12—C13	170.6 (3)	C20—C21—C22—C17	2.1 (7)
N1—C4—C12—C6	174.7 (2)	O5—N5—C23—C24	177.4 (8)
C3—C4—C12—C6	−9.5 (4)	O6—N5—C23—C24	−2.3 (10)
C11—C6—C12—C13	−71.9 (4)	O5—N5—C23—C28	−4.8 (11)
C7—C6—C12—C13	106.6 (3)	O6—N5—C23—C28	175.5 (7)
C11—C6—C12—C4	108.1 (3)	C28—C23—C24—C25	0.6 (8)
C7—C6—C12—C4	−73.4 (4)	N5—C23—C24—C25	178.3 (6)
C5—N3—C13—C12	178.6 (3)	C23—C24—C25—C26	0.5 (8)
C5—N3—C13—C14	−1.4 (3)	C24—C25—C26—C27	−0.9 (9)
C4—C12—C13—N3	2.5 (5)	C25—C26—C27—C28	0.3 (10)
C6—C12—C13—N3	−177.5 (2)	C26—C27—C28—C23	0.7 (10)
C4—C12—C13—C14	−177.5 (3)	C24—C23—C28—C27	−1.1 (9)
C6—C12—C13—C14	2.5 (4)	N5—C23—C28—C27	−178.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ii	0.93	2.60	3.519 (4)	171
C11—H11···N1iii	0.93	2.57	3.426 (4)	152
C15—H15···O3iv	0.93	2.56	3.453 (5)	161
C18—H18···O1v	0.93	2.58	3.455 (5)	157
C26—H26···O5vi	0.93	2.56	3.432 (10)	156

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C3H3O1i	0.93	2.60	3.519(4)	171
C11H11N1ii	0.93	2.57	3.426(4)	152
C15H15O3iii	0.93	2.56	3.453(5)	161
C18H18O1iv	0.93	2.58	3.455(5)	157
C26H26O5v	0.93	2.56	3.432(10)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .