Literature DB >> 21523064

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

Grzegorz Dutkiewicz, S Samshuddin, B Narayana, H S Yathirajan, Maciej Kubicki.

Abstract

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)°].

Entities: Chemical Disease Species

Year: 2011 PMID： 21523064 PMCID： PMC3051773 DOI： 10.1107/S1600536811001024

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For examples of the biological activity of piperazines: Brockunier et al. (2004 ▶); Bogatcheva et al. (2006 ▶). For the crystal structures of simple 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
M_r = 558.39	F(000) = 576
Triclinic, P1	D_x = 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	R_int = 0.021
Detector resolution: 16.1544 pixels mm^-1	θ_max = 28.0°, θ_min = 3.0°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→12
T_min = 0.936, T_max = 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(F_o²) + (0.0725P)² + 0.3607P] where P = (F_o² + 2F_c²)/3
4891 reflections	(Δ/σ)_max < 0.001
424 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −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	U_iso*/U_eq
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···O41A^iv	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···O62B^v	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⋯O41A^iv	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⋯O62B^v	0.96 (2)	2.46 (2)	3.386 (2)	162.9 (17)

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

7 in total

1. The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors: Frank H Allen
Journal: Acta Crystallogr B Date: 2002-05-29

2. Identification of new diamine scaffolds with activity against Mycobacterium tuberculosis.

Authors: Elena Bogatcheva; Colleen Hanrahan; Boris Nikonenko; Rowena Samala; Ping Chen; Jacqueline Gearhart; Francis Barbosa; Leo Einck; Carol A Nacy; Marina Protopopova
Journal: J Med Chem Date: 2006-06-01 Impact factor: 7.446

3. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

4. Structure and serotonin 5-HT2C receptor activity of ortho- and meta-substituted phenylpiperazines.

Authors: M L Verdonk; J W Voogd; J A Kanters; J Kroon; R den Besten; L Brandsma; D Leysen; J Kelder
Journal: Acta Crystallogr B Date: 1997-12-01

5. Substituted piperazines as novel dipeptidyl peptidase IV inhibitors.

Authors: Linda L Brockunier; Jiafang He; Lawrence F Colwell; Bahanu Habulihaz; Huaibing He; Barbara Leiting; Kathryn A Lyons; Frank Marsilio; Reshma A Patel; Yohannes Teffera; Joseph K Wu; Nancy A Thornberry; Ann E Weber; Emma R Parmee
Journal: Bioorg Med Chem Lett Date: 2004-09-20 Impact factor: 2.823

6. Three-dimensional network in piper-azine-1,4-diium-picrate-piperazine (1/2/1).

Authors: Zhong-Long Wang; Li-Hui Jia
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-03-05

7. 4-(3-Carb-oxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-7-quinol-yl)-1-methyl-piper-azin-ium picrate.

Authors: Hoong-Kun Fun; Madhukar Hemamalini; Divya N Shetty; B Narayana; H S Yathirajan
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-02-27