1-Methyl-piperazine-1,4-diium dipicrate.

IN THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND [SYSTEMATIC NAME: 1-methyl-piperazine-1,4-diium bis-(2,4,6-trinitro-phen-ol-ate)], C(5)H(14)N(2) (2+)·2C(6)H(2)N(3)O(7) (-), the ionic components are connected by relatively strong N-H⋯O hydrogen bonds into centrosymmetric six-membered conglomerates, which comprise two dications and four anions. Besides Coulombic inter-actions, only weak C-H⋯O inter-actions and some stacking between picrates (separation between the planes of ca. 3.4 Å but only a small overlapping) can be identified between these 'building blocks' of the crystal structure. The piperazine ring adopts a chair conformation with the methyl substituent in the equatorial position. In the picrate anions, the twist angles of the nitro groups depend on their positions relative to the phenolate O atom: it is much smaller for the NO(2) groups para to the C-O(-) group [15.23 (9)and 3.92 (14)°] than for the groups in the ortho positions [28.76 (13)-39.84 (11)°].

Related literature

For examples of the biological activity of piperazines: Brockunier et al. (2004 ▶); Bogatcheva et al. (2006 ▶). For the crystal structures of simple n class="Chemical">piperidinium picrates, see: Fun et al. (2010 ▶); Li et al. (2009 ▶); Verdonk et al. (1997 ▶); Wang & Jia (2008 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For asymmetry parameters, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C5H14N2 2+·2C6n class="Species">H2N3O7 −

M = 558.39

Triclinic,

a = 8.2001 (12) Å

b = 10.1780 (15) Å

c = 13.7399 (18) Å

α = 89.798 (12)°

β = 78.130 (11)°

γ = 81.558 (12)°

V = 1109.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.15 mm−1

T = 295 K

0.4 × 0.15 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.936, T max = 1.000

21056 measured reflections

4891 independent reflections

3624 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 0.95

4891 reflections

424 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001024/fl2330sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001024/fl2330Isup2.hkl

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

C5H14N22+·2C6H2N3O7−	Z = 2
Mr = 558.39	F(000) = 576
Triclinic, P1	Dx = 1.671 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2001 (12) Å	Cell parameters from 12041 reflections
b = 10.1780 (15) Å	θ = 3.0–28.0°
c = 13.7399 (18) Å	µ = 0.15 mm−1
α = 89.798 (12)°	T = 295 K
β = 78.130 (11)°	Block, yellow
γ = 81.558 (12)°	0.4 × 0.15 × 0.07 mm
V = 1109.6 (3) Å3

Oxford Diffraction Xcalibur Eos diffractometer	4891 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3624 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 16.1544 pixels mm-1	θmax = 28.0°, θmin = 3.0°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→12
Tmin = 0.936, Tmax = 1.000	l = −18→18
21056 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0725P)2 + 0.3607P] where P = (Fo2 + 2Fc2)/3
4891 reflections	(Δ/σ)max < 0.001
424 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1A	−0.10838 (19)	0.86643 (15)	0.10686 (11)	0.0303 (3)
O1A	−0.02003 (16)	0.75573 (12)	0.08429 (10)	0.0469 (3)
C2A	−0.04660 (18)	0.98367 (16)	0.13439 (12)	0.0309 (3)
N2A	0.12392 (16)	0.97199 (15)	0.15030 (11)	0.0394 (3)
O21A	0.19522 (16)	1.07010 (15)	0.13867 (13)	0.0601 (4)
O22A	0.18805 (16)	0.86647 (14)	0.17951 (12)	0.0568 (4)
C3A	−0.1404 (2)	1.10787 (16)	0.14843 (12)	0.0314 (3)
H3A	−0.091 (3)	1.179 (2)	0.1651 (16)	0.052 (6)*
C4A	−0.30793 (18)	1.12289 (14)	0.14285 (11)	0.0284 (3)
N4A	−0.40990 (18)	1.25160 (13)	0.16554 (10)	0.0350 (3)
O41A	−0.56396 (15)	1.25745 (13)	0.18252 (10)	0.0474 (3)
O42A	−0.33873 (18)	1.34906 (12)	0.16819 (12)	0.0566 (4)
C5A	−0.38244 (19)	1.01553 (15)	0.12063 (11)	0.0288 (3)
H5A	−0.495 (2)	1.0237 (18)	0.1186 (13)	0.036 (5)*
C6A	−0.28521 (19)	0.89319 (14)	0.10388 (11)	0.0294 (3)
N6A	−0.36772 (18)	0.78285 (13)	0.08081 (11)	0.0370 (3)
O61A	−0.3268 (2)	0.67315 (13)	0.11180 (13)	0.0662 (5)
O62A	−0.47823 (18)	0.80553 (14)	0.03359 (11)	0.0557 (4)
C1B	0.29112 (18)	0.24867 (15)	0.41703 (11)	0.0270 (3)
O1B	0.19899 (13)	0.35763 (11)	0.44572 (8)	0.0353 (3)
C2B	0.23173 (18)	0.13264 (16)	0.38650 (12)	0.0299 (3)
N2B	0.05928 (16)	0.14283 (15)	0.37308 (12)	0.0404 (3)
O21B	−0.00902 (16)	0.04406 (15)	0.38274 (15)	0.0690 (5)
O22B	−0.00859 (16)	0.24821 (14)	0.34659 (12)	0.0576 (4)
C3B	0.32794 (19)	0.00995 (16)	0.36639 (12)	0.0315 (3)
H3B	0.279 (2)	−0.0637 (19)	0.3481 (14)	0.040 (5)*
C4B	0.49633 (19)	−0.00422 (15)	0.37139 (11)	0.0301 (3)
N4B	0.59846 (18)	−0.13327 (14)	0.34997 (11)	0.0389 (3)
O41B	0.74541 (16)	−0.14586 (14)	0.35957 (12)	0.0558 (4)
O42B	0.53534 (19)	−0.22459 (14)	0.32327 (14)	0.0652 (4)
C5B	0.56874 (19)	0.10308 (16)	0.39575 (11)	0.0303 (3)
H5B	0.681 (2)	0.0949 (17)	0.3956 (13)	0.033 (4)*
C6B	0.46974 (18)	0.22393 (16)	0.41531 (11)	0.0295 (3)
N6B	0.55497 (17)	0.33587 (15)	0.43280 (12)	0.0414 (4)
O61B	0.5170 (2)	0.44149 (14)	0.39533 (12)	0.0590 (4)
O62B	0.66595 (18)	0.31520 (16)	0.47993 (14)	0.0699 (5)
N11	0.16733 (15)	0.57565 (13)	0.16779 (10)	0.0291 (3)
H11	0.114 (2)	0.6554 (18)	0.1567 (13)	0.030 (4)*
C11A	0.2986 (3)	0.5363 (2)	0.07575 (15)	0.0456 (5)
H11C	0.346 (3)	0.450 (3)	0.0848 (19)	0.071 (7)*
H11B	0.243 (3)	0.539 (2)	0.024 (2)	0.068 (7)*
H11A	0.372 (3)	0.600 (3)	0.068 (2)	0.079 (8)*
C12	0.2433 (2)	0.58588 (17)	0.25660 (13)	0.0348 (4)
H12B	0.300 (2)	0.498 (2)	0.2664 (14)	0.041 (5)*
H12A	0.322 (3)	0.647 (2)	0.2416 (16)	0.053 (6)*
C13	0.1088 (2)	0.63356 (18)	0.34660 (13)	0.0387 (4)
H13B	0.054 (2)	0.7194 (19)	0.3366 (13)	0.035 (5)*
H13A	0.157 (2)	0.636 (2)	0.4042 (16)	0.049 (5)*
N14	−0.02066 (18)	0.54247 (15)	0.36518 (11)	0.0361 (3)
H14B	−0.100 (3)	0.576 (2)	0.4161 (16)	0.044 (5)*
H14A	0.031 (3)	0.460 (2)	0.3783 (15)	0.048 (5)*
C15	−0.0961 (2)	0.52998 (19)	0.27659 (13)	0.0364 (4)
H15B	−0.153 (2)	0.616 (2)	0.2644 (15)	0.042 (5)*
H15A	−0.171 (3)	0.471 (2)	0.2906 (15)	0.047 (5)*
C16	0.0398 (2)	0.48330 (17)	0.18685 (13)	0.0338 (3)
H16B	0.098 (2)	0.3954 (19)	0.1948 (14)	0.036 (5)*
H16A	−0.012 (3)	0.481 (2)	0.1283 (17)	0.056 (6)*

	U11	U22	U33	U12	U13	U23
C1A	0.0339 (8)	0.0278 (8)	0.0286 (8)	0.0045 (6)	−0.0116 (6)	0.0010 (6)
O1A	0.0507 (7)	0.0349 (6)	0.0543 (8)	0.0144 (5)	−0.0239 (6)	−0.0092 (6)
C2A	0.0257 (7)	0.0361 (8)	0.0310 (8)	−0.0019 (6)	−0.0081 (6)	0.0030 (6)
N2A	0.0275 (7)	0.0450 (8)	0.0462 (9)	−0.0034 (6)	−0.0097 (6)	−0.0010 (7)
O21A	0.0355 (7)	0.0566 (9)	0.0925 (12)	−0.0161 (6)	−0.0166 (7)	0.0067 (8)
O22A	0.0422 (7)	0.0511 (8)	0.0820 (11)	0.0035 (6)	−0.0320 (7)	0.0070 (7)
C3A	0.0342 (8)	0.0290 (8)	0.0324 (8)	−0.0068 (6)	−0.0088 (6)	0.0024 (6)
C4A	0.0311 (7)	0.0244 (7)	0.0284 (8)	0.0010 (6)	−0.0072 (6)	0.0014 (6)
N4A	0.0435 (8)	0.0274 (7)	0.0324 (7)	0.0029 (6)	−0.0099 (6)	−0.0003 (5)
O41A	0.0381 (7)	0.0415 (7)	0.0571 (8)	0.0112 (5)	−0.0094 (6)	−0.0042 (6)
O42A	0.0646 (9)	0.0267 (6)	0.0792 (11)	−0.0052 (6)	−0.0174 (8)	−0.0055 (6)
C5A	0.0280 (7)	0.0307 (8)	0.0287 (8)	−0.0012 (6)	−0.0102 (6)	0.0027 (6)
C6A	0.0357 (8)	0.0260 (7)	0.0289 (8)	−0.0037 (6)	−0.0130 (6)	0.0011 (6)
N6A	0.0453 (8)	0.0307 (7)	0.0387 (8)	−0.0068 (6)	−0.0163 (6)	−0.0020 (6)
O61A	0.0923 (11)	0.0293 (7)	0.0920 (12)	−0.0132 (7)	−0.0508 (10)	0.0087 (7)
O62A	0.0606 (8)	0.0531 (8)	0.0682 (9)	−0.0181 (7)	−0.0407 (8)	0.0056 (7)
C1B	0.0256 (7)	0.0315 (8)	0.0221 (7)	0.0001 (6)	−0.0036 (5)	−0.0009 (6)
O1B	0.0338 (6)	0.0350 (6)	0.0336 (6)	0.0054 (5)	−0.0061 (5)	−0.0059 (5)
C2B	0.0227 (7)	0.0359 (8)	0.0308 (8)	−0.0032 (6)	−0.0055 (6)	0.0006 (6)
N2B	0.0265 (7)	0.0434 (8)	0.0523 (9)	−0.0043 (6)	−0.0108 (6)	−0.0032 (7)
O21B	0.0357 (7)	0.0529 (9)	0.1243 (15)	−0.0158 (6)	−0.0236 (8)	0.0045 (9)
O22B	0.0400 (7)	0.0510 (8)	0.0875 (11)	0.0010 (6)	−0.0315 (7)	0.0076 (7)
C3B	0.0312 (8)	0.0310 (8)	0.0331 (8)	−0.0061 (6)	−0.0070 (6)	−0.0003 (6)
C4B	0.0288 (7)	0.0312 (8)	0.0278 (8)	0.0027 (6)	−0.0050 (6)	−0.0014 (6)
N4B	0.0388 (8)	0.0355 (8)	0.0370 (8)	0.0050 (6)	−0.0031 (6)	−0.0023 (6)
O41B	0.0365 (7)	0.0511 (8)	0.0751 (10)	0.0147 (6)	−0.0155 (6)	−0.0074 (7)
O42B	0.0597 (9)	0.0352 (7)	0.0992 (13)	0.0017 (6)	−0.0186 (8)	−0.0210 (8)
C5B	0.0227 (7)	0.0402 (9)	0.0264 (8)	0.0003 (6)	−0.0053 (6)	−0.0026 (6)
C6B	0.0273 (7)	0.0349 (8)	0.0264 (7)	−0.0051 (6)	−0.0056 (6)	−0.0037 (6)
N6B	0.0318 (7)	0.0453 (9)	0.0462 (9)	−0.0065 (6)	−0.0052 (6)	−0.0166 (7)
O61B	0.0718 (9)	0.0448 (8)	0.0644 (9)	−0.0235 (7)	−0.0133 (8)	0.0015 (7)
O62B	0.0495 (8)	0.0688 (10)	0.0995 (13)	0.0001 (7)	−0.0399 (9)	−0.0343 (9)
N11	0.0286 (6)	0.0248 (6)	0.0310 (7)	0.0034 (5)	−0.0047 (5)	−0.0002 (5)
C11A	0.0464 (10)	0.0415 (11)	0.0383 (10)	0.0077 (9)	0.0055 (8)	0.0011 (8)
C12	0.0280 (8)	0.0350 (9)	0.0423 (9)	−0.0012 (7)	−0.0122 (7)	−0.0009 (7)
C13	0.0431 (9)	0.0357 (9)	0.0386 (9)	0.0020 (7)	−0.0169 (8)	−0.0092 (7)
N14	0.0343 (7)	0.0384 (8)	0.0289 (7)	0.0082 (6)	−0.0010 (6)	−0.0024 (6)
C15	0.0271 (8)	0.0411 (9)	0.0403 (9)	−0.0024 (7)	−0.0073 (7)	0.0020 (7)
C16	0.0376 (8)	0.0309 (8)	0.0342 (9)	−0.0054 (7)	−0.0104 (7)	−0.0033 (7)

C1A—O1A	1.2494 (18)	N4B—O42B	1.220 (2)
C1A—C2A	1.443 (2)	N4B—O41B	1.2271 (19)
C1A—C6A	1.445 (2)	C5B—C6B	1.365 (2)
C2A—C3A	1.372 (2)	C5B—H5B	0.913 (18)
C2A—N2A	1.4470 (19)	C6B—N6B	1.466 (2)
N2A—O21A	1.2233 (19)	N6B—O62B	1.215 (2)
N2A—O22A	1.2283 (19)	N6B—O61B	1.217 (2)
C3A—C4A	1.378 (2)	N11—C16	1.490 (2)
C3A—H3A	0.93 (2)	N11—C12	1.490 (2)
C4A—C5A	1.391 (2)	N11—C11A	1.495 (2)
C4A—N4A	1.4445 (19)	N11—H11	0.892 (18)
N4A—O42A	1.2267 (19)	C11A—H11C	0.93 (3)
N4A—O41A	1.2291 (18)	C11A—H11B	0.92 (3)
C5A—C6A	1.369 (2)	C11A—H11A	0.94 (3)
C5A—H5A	0.917 (19)	C12—C13	1.505 (2)
C6A—N6A	1.4605 (19)	C12—H12B	0.97 (2)
N6A—O62A	1.2144 (18)	C12—H12A	0.96 (2)
N6A—O61A	1.2190 (19)	C13—N14	1.493 (2)
C1B—O1B	1.2612 (18)	C13—H13B	0.946 (19)
C1B—C2B	1.437 (2)	C13—H13A	0.96 (2)
C1B—C6B	1.445 (2)	N14—C15	1.488 (2)
C2B—C3B	1.372 (2)	N14—H14B	0.88 (2)
C2B—N2B	1.4521 (19)	N14—H14A	0.92 (2)
N2B—O21B	1.215 (2)	C15—C16	1.507 (2)
N2B—O22B	1.2238 (19)	C15—H15B	0.96 (2)
C3B—C4B	1.383 (2)	C15—H15A	0.92 (2)
C3B—H3B	0.959 (19)	C16—H16B	0.965 (18)
C4B—C5B	1.390 (2)	C16—H16A	0.99 (2)
C4B—N4B	1.446 (2)
O1A—C1A—C2A	124.85 (14)	C5B—C6B—C1B	124.82 (14)
O1A—C1A—C6A	123.25 (15)	C5B—C6B—N6B	116.40 (13)
C2A—C1A—C6A	111.84 (13)	C1B—C6B—N6B	118.76 (13)
C3A—C2A—C1A	124.24 (13)	O62B—N6B—O61B	123.87 (16)
C3A—C2A—N2A	116.59 (14)	O62B—N6B—C6B	117.52 (16)
C1A—C2A—N2A	119.16 (13)	O61B—N6B—C6B	118.50 (14)
O21A—N2A—O22A	122.68 (14)	C16—N11—C12	110.14 (13)
O21A—N2A—C2A	118.32 (14)	C16—N11—C11A	111.97 (14)
O22A—N2A—C2A	118.91 (14)	C12—N11—C11A	111.84 (14)
C2A—C3A—C4A	119.12 (15)	C16—N11—H11	107.5 (11)
C2A—C3A—H3A	118.9 (13)	C12—N11—H11	109.0 (11)
C4A—C3A—H3A	121.8 (13)	C11A—N11—H11	106.2 (11)
C3A—C4A—C5A	121.40 (14)	N11—C11A—H11C	106.1 (16)
C3A—C4A—N4A	119.07 (14)	N11—C11A—H11B	106.3 (15)
C5A—C4A—N4A	119.46 (13)	H11C—C11A—H11B	110 (2)
O42A—N4A—O41A	123.36 (14)	N11—C11A—H11A	106.9 (17)
O42A—N4A—C4A	118.51 (14)	H11C—C11A—H11A	116 (2)
O41A—N4A—C4A	118.12 (14)	H11B—C11A—H11A	111 (2)
C6A—C5A—C4A	118.49 (14)	N11—C12—C13	110.48 (13)
C6A—C5A—H5A	119.2 (11)	N11—C12—H12B	106.7 (11)
C4A—C5A—H5A	122.3 (11)	C13—C12—H12B	110.9 (11)
C5A—C6A—C1A	124.74 (14)	N11—C12—H12A	107.2 (13)
C5A—C6A—N6A	116.96 (13)	C13—C12—H12A	110.5 (13)
C1A—C6A—N6A	118.30 (13)	H12B—C12—H12A	110.9 (16)
O62A—N6A—O61A	122.69 (14)	N14—C13—C12	110.29 (14)
O62A—N6A—C6A	118.18 (13)	N14—C13—H13B	107.8 (11)
O61A—N6A—C6A	119.09 (13)	C12—C13—H13B	110.5 (11)
O1B—C1B—C2B	124.76 (13)	N14—C13—H13A	108.6 (12)
O1B—C1B—C6B	123.54 (14)	C12—C13—H13A	110.3 (12)
C2B—C1B—C6B	111.65 (13)	H13B—C13—H13A	109.3 (16)
C3B—C2B—C1B	124.68 (13)	C15—N14—C13	111.26 (14)
C3B—C2B—N2B	115.96 (14)	C15—N14—H14B	109.5 (13)
C1B—C2B—N2B	119.34 (13)	C13—N14—H14B	107.5 (13)
O21B—N2B—O22B	122.20 (14)	C15—N14—H14A	108.4 (13)
O21B—N2B—C2B	118.69 (14)	C13—N14—H14A	108.3 (12)
O22B—N2B—C2B	118.96 (14)	H14B—N14—H14A	111.8 (18)
C2B—C3B—C4B	118.77 (15)	N14—C15—C16	110.20 (13)
C2B—C3B—H3B	120.1 (11)	N14—C15—H15B	108.1 (12)
C4B—C3B—H3B	121.1 (11)	C16—C15—H15B	109.3 (12)
C3B—C4B—C5B	121.27 (14)	N14—C15—H15A	108.0 (13)
C3B—C4B—N4B	119.00 (14)	C16—C15—H15A	110.7 (13)
C5B—C4B—N4B	119.73 (13)	H15B—C15—H15A	110.4 (16)
O42B—N4B—O41B	122.89 (14)	N11—C16—C15	110.70 (13)
O42B—N4B—C4B	118.86 (14)	N11—C16—H16B	108.1 (10)
O41B—N4B—C4B	118.24 (14)	C15—C16—H16B	112.1 (11)
C6B—C5B—C4B	118.58 (14)	N11—C16—H16A	108.9 (13)
C6B—C5B—H5B	120.0 (11)	C15—C16—H16A	108.8 (13)
C4B—C5B—H5B	121.3 (11)	H16B—C16—H16A	108.2 (16)
O1A—C1A—C2A—C3A	172.55 (16)	C3B—C2B—N2B—O21B	27.4 (2)
C6A—C1A—C2A—C3A	−4.8 (2)	C1B—C2B—N2B—O21B	−153.91 (17)
O1A—C1A—C2A—N2A	−8.5 (2)	C3B—C2B—N2B—O22B	−148.21 (17)
C6A—C1A—C2A—N2A	174.11 (14)	C1B—C2B—N2B—O22B	30.5 (2)
C3A—C2A—N2A—O21A	−26.5 (2)	C1B—C2B—C3B—C4B	−2.8 (2)
C1A—C2A—N2A—O21A	154.53 (16)	N2B—C2B—C3B—C4B	175.80 (14)
C3A—C2A—N2A—O22A	150.03 (16)	C2B—C3B—C4B—C5B	−0.3 (2)
C1A—C2A—N2A—O22A	−29.0 (2)	C2B—C3B—C4B—N4B	−179.82 (14)
C1A—C2A—C3A—C4A	4.6 (2)	C3B—C4B—N4B—O42B	3.6 (2)
N2A—C2A—C3A—C4A	−174.39 (14)	C5B—C4B—N4B—O42B	−175.90 (16)
C2A—C3A—C4A—C5A	−1.8 (2)	C3B—C4B—N4B—O41B	−176.40 (15)
C2A—C3A—C4A—N4A	175.04 (14)	C5B—C4B—N4B—O41B	4.1 (2)
C3A—C4A—N4A—O42A	15.4 (2)	C3B—C4B—C5B—C6B	0.3 (2)
C5A—C4A—N4A—O42A	−167.73 (15)	N4B—C4B—C5B—C6B	179.78 (14)
C3A—C4A—N4A—O41A	−163.68 (14)	C4B—C5B—C6B—C1B	2.9 (2)
C5A—C4A—N4A—O41A	13.2 (2)	C4B—C5B—C6B—N6B	−175.30 (14)
C3A—C4A—C5A—C6A	−0.2 (2)	O1B—C1B—C6B—C5B	172.05 (15)
N4A—C4A—C5A—C6A	−177.01 (14)	C2B—C1B—C6B—C5B	−5.4 (2)
C4A—C5A—C6A—C1A	−0.4 (2)	O1B—C1B—C6B—N6B	−9.8 (2)
C4A—C5A—C6A—N6A	179.97 (13)	C2B—C1B—C6B—N6B	172.77 (14)
O1A—C1A—C6A—C5A	−174.70 (15)	C5B—C6B—N6B—O62B	−38.6 (2)
C2A—C1A—C6A—C5A	2.7 (2)	C1B—C6B—N6B—O62B	143.11 (16)
O1A—C1A—C6A—N6A	4.9 (2)	C5B—C6B—N6B—O61B	137.68 (16)
C2A—C1A—C6A—N6A	−177.70 (13)	C1B—C6B—N6B—O61B	−40.6 (2)
C5A—C6A—N6A—O62A	33.9 (2)	C16—N11—C12—C13	−58.20 (17)
C1A—C6A—N6A—O62A	−145.77 (16)	C11A—N11—C12—C13	176.60 (15)
C5A—C6A—N6A—O61A	−144.12 (17)	N11—C12—C13—N14	57.33 (18)
C1A—C6A—N6A—O61A	36.3 (2)	C12—C13—N14—C15	−56.74 (18)
O1B—C1B—C2B—C3B	−172.05 (15)	C13—N14—C15—C16	56.51 (19)
C6B—C1B—C2B—C3B	5.3 (2)	C12—N11—C16—C15	58.16 (17)
O1B—C1B—C2B—N2B	9.4 (2)	C11A—N11—C16—C15	−176.72 (14)
C6B—C1B—C2B—N2B	−173.25 (14)	N14—C15—C16—N11	−57.15 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1A	0.892 (18)	1.831 (18)	2.6305 (17)	148.1 (16)
N11—H11···O22A	0.892 (18)	2.356 (18)	2.996 (2)	128.8 (14)
N14—H14B···O1Bi	0.88 (2)	1.98 (2)	2.8181 (19)	157.3 (17)
N14—H14A···O1B	0.92 (2)	1.99 (2)	2.7962 (18)	146.4 (18)
N14—H14A···O22B	0.92 (2)	2.28 (2)	2.992 (2)	133.9 (16)
C5A—H5A···O21Aii	0.917 (19)	2.476 (19)	3.383 (2)	170.3 (16)
C5B—H5B···O21Biii	0.913 (18)	2.487 (18)	3.394 (2)	172.3 (15)
C11A—H11C···O41Aiv	0.93 (3)	2.48 (3)	3.345 (2)	155 (2)
C11A—H11A···O62Aiii	0.94 (3)	2.57 (3)	3.496 (3)	168 (2)
C12—H12A···O22A	0.96 (2)	2.56 (2)	3.046 (2)	111.6 (15)
C13—H13A···O62Bv	0.96 (2)	2.46 (2)	3.386 (2)	162.9 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O1A	0.892 (18)	1.831 (18)	2.6305 (17)	148.1 (16)
N11—H11⋯O22A	0.892 (18)	2.356 (18)	2.996 (2)	128.8 (14)
N14—H14B⋯O1Bi	0.88 (2)	1.98 (2)	2.8181 (19)	157.3 (17)
N14—H14A⋯O1B	0.92 (2)	1.99 (2)	2.7962 (18)	146.4 (18)
N14—H14A⋯O22B	0.92 (2)	2.28 (2)	2.992 (2)	133.9 (16)
C5A—H5A⋯O21Aii	0.917 (19)	2.476 (19)	3.383 (2)	170.3 (16)
C5B—H5B⋯O21Biii	0.913 (18)	2.487 (18)	3.394 (2)	172.3 (15)
C11A—H11C⋯O41Aiv	0.93 (3)	2.48 (3)	3.345 (2)	155 (2)
C11A—H11A⋯O62Aiii	0.94 (3)	2.57 (3)	3.496 (3)	168 (2)
C13—H13A⋯O62Bv	0.96 (2)	2.46 (2)	3.386 (2)	162.9 (17)

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